My Wife and Her

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Hey, I'm back. Some themes to expect in this one: feminization, chastity, humiliation, degradation, pegging, ffm, and a very loving wife.

If you don't like these things, you may not like this story. Otherwise, carry on.

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I guess it all started the night of the annual summer party. My work was known for throwing quite an event each year. My wife, Sandy, and I were in the car outside the retreat center. She rubbed her hand against my crotch, causing my cock to try to grow.

Alas, it didn't have a chance. It was encased in the same steel cage that had kept it neutralized going on five days now. My balls were achingly full, and my large member pushed painfully for expansion.

"How does that feel, subby?" Sandy taunted.

"It feels good, ma'am," I lied. It was how I was instructed to answer.

"Aww, good. I just love to make you feel good before we go out. Do you think anyone will notice the bulge of your cage?"

"I hope not, ma'am."

"I kind of hope they do," she said with challenge in her tone. "It's about time everyone found out who's in charge here. Don't you think?"

"Yes, ma'am. If that's what you would prefer then you must be right."

"That's a good answer, pet. I am always right. But hey, let's not push it tonight. If someone sees then someone sees. But if everyone knew then some of your agony would be over. I guess we don't want that just yet."

"You're right, we don't want that ma'am."

"Oooh! You know what I think is much more likely? That someone will see the thong you were just dying to wear. Yep, pretty likely I think. Tell me, honey, why do you think someone might notice the thong?"

"Because of the pants you made me wear, ma'am. They're big on me and you told me not to wear a belt. I'll probably be pulling them up all night."

"That's right! You're such a smart little panty boy. Your pink, satin panties could easily be exposed by your loose-fitting pants. Now, I don't think I'm going to allow you to just pull them up willy nilly. Each time you want to save yourself from embarrassment you'll have to ask permission. You can do that by tapping me twice. Then I will either squeeze your arm giving you permission or I will just look at you and smile. In that case you have to wait at least ten seconds before you ask again. Does that sound good, pet?"

"Yes ma'am, it sounds good to me," I admitted dutifully.

Jeez, I knew she wasn't going to make tonight easy. Reckless is her middle name, and that's definitely part of what makes me so crazy about her. But this was just about going to kill me, I thought to myself as my entrapped member tried to respond to my loss of control.

"Good, this'll be fun! Let's go, pansy boy."

I took my queue and went around the car, opening her door for her. She nonchalantly exited and started walking briskly for the door. At this speed my pants were falling down quickly and I had to catch up so I could give her the signal. I tapped her arm with maybe two seconds to spare and she stopped and paused squeezing my arm affectionately. I could see how her permission system could be easily mistaken for simple romance by anyone watching.

I pulled up my pants quickly, trying to adjust them so they would stay as long as possible. A feeble hope, really.

We continued our walk and made it all the way to the door before I had to tap her arm again. She turned around and smiled at me mischievously.

"Jeez, hun. Are you gonna be bothering me all night?"

"Sorry, ma'am," I said sincerely.

She was clearly joking, having put me in this position. But given my nature, I still took any critique to heart in some small way. This was something I knew she liked about me, and she played into it by continuing to look at me seriously. She squeezed my arm and I pulled up my pants.

"Let's see how long we can go without bothering me this time, okay?"

"Yes ma'am."

We walked into the commotion of the party and went straight for the booze. We made our rounds and I introduced Sandy to my colleagues, pretending not to be in a constant predicament.

Several times I tapped her arm when needed and was favored with a squeeze back before we came upon my boss, Linda. This time was different. I let her know I was close to being exposed and she just looked over at me and smiled. An evil smile, really. So I just smiled back. Linda probably thought we were having a couple moment.

Sandy and Linda seemed to be really chatting it up and my first couple drinks had run right through me. But I knew I couldn't move a muscle without losing my pants, in my state. I tapped Sandy's arm again and she smiled at me again oh so knowingly. At this point it felt like my pants were gonna drop with me just standing there in place. The next ten seconds passed so slowly as I counted them in my head, dreading that my boss was about to see me in panties and a swollen chastity cage.

They were slipping down. Right as I was reaching the count of ten I felt the first cool air of exposure between my sweater and my pants. I tapped frantically, desperately.

The third tap finally brought me relief as Sandy squeezed my arm hard, almost a pinch. I pulled up my pants and excused myself to do the necessary. When I returned a couple minutes later Sandy and Linda were still talking, now over by the drink table. Sandy had Linda's phone in her hand and they were obviously exchanging numbers. I got a bad feeling in the pit of my stomach. It would turn out later that my stomach was right.

The rest of the night was actually kind of fun. Sandy never left me hanging when I tapped her from then on. And after we had a few drinks in us it really did seem more like a party than a work function. At some point Linda even got out on the dance floor and proved to be quite light on her feet.

I did still have the constant reminder that I was at risk of being exposed. I didn't dare try to dance, even when Sandy went over to join Linda and they both encouraged me. I declined, unable to cut a rug and keep my dignity at the same time. So I watched them dance and laugh. I turned quite pink from having to wimp out on them so decisively. I actually do like to dance.

The time eventually came that we said our goodbyes and went on our way. As we left the building Sandy whispered in my ear.

"Last one to the car has to make the other cum when we get home."

She took off running, just for a second. Then she turned around and grinned teasingly, knowing that I couldn't run myself without pulling my pants up. We strode toward the end of the parking lot and I was really sagging. My panties were starting to show a little bit but I couldn't reach Sandy's arm!

"Please come back here! I need your help," I pleaded pitifully.

My wife shook her head and laughed. I stopped walking to try to keep from losing it.

"Oh come on, now. If you keep dawdling there will be consequences," Sandy threatened.

I started again but it really wasn't going well. With every step I was exposed a little more. And then it happened. My pants fell down to my ankles, revealing my skimpy pink thong to the cool night air. I started running, sort of. One might say I started scurrying quickly with my short, pant-bound steps. Sandy laughed ruthlessly as I struggled. But she did walk over and grant me reprieve.

Luckily in this part of the lot we were pretty far from anyone else leaving and it was dark. I don't think anyone saw me and if they did, it wasn't totally clear. I climbed back into the car with relief, several seconds after Sandy had made it of course.

"Well then, I guess it's me who gets to cum again tonight. You didn't even come close, slowpoke!" she teased.

"Yes, ma'am. You won fair and square."

"Oh don't sound so dejected. I'll tell you what. Tonight I'm going to let you out of your cage for a bit. I'll even give you a chance to cum."

"Oh thank you, ma'am. I would like that very much!" I beamed.

"You're pitiful, you know that right?"

The car sped off. When we got home Sandy made me take off my pants entirely before going into the house. I ran from the car like a bat out of hell.

"Where was that athleticism during our little race?" Sandy yelled from the porch.

She took my hand and led me to the bedroom. She stripped off her shirt, revealing her small perky breasts in a smart black lace bra. Then she took off her pants and tiny panties, shoving the wet underwear into my mouth before laying on the bed.

"Since I won fair and square, I get my orgasm first. With your mouth, please."

I got on my knees by the side of the bed and got to work, still in my sweater and thong. I had to work her thong into the side of my mouth to get around it with my tongue. I must have looked like some pathetic, emasculated chipmunk as I licked her quickly to completion. This was something she made sure I had plenty of practice with, so it didn't take long before she came powerfully. She told me to clean out all of her cum and swallow it.

"That was lovely, dear. Thank you. Well, I guess we're done with your mouth for now."

She went to our bedside drawer and pulled out a penis gag. She pulled her thong out of my mouth and spit on it. Then she wrapped it around the dildo and shoved it in my mouth, buckling it in place.

"Lay down"

I did.

She pulled my thong aside and took my caged member into her mouth. I could feel her warmth and even a little tongue through the few slits in the cage. My cock tried with all it's might to get hard. It pushed uncomfortably at its bonds in the velvet cavern of her mouth. I made a couple whimpers at the discomfort but they were mostly lost to the gag.

When she was done with that particularly immaculate torture she took the key out of the pocket of her hanging jacket. I never knew where she would be keeping the thing but was glad to see it was at least zipped in this time. She insisted when the cage had come with two keys that one was much more exciting. I had almost cried when she threw the second out the car window. That was a while back now, but she had really started getting interested in this cage. Sandy pressed the key into the lock and turned.

"Here are the rules, pitiful. From the moment I remove this lock you have exactly two minutes to cum. I'm setting a timer on my phone. You will not be allowed to touch at all. I will be the one doing the touching. Kapeesh?"

"Yes, ma'am. Thank you for this opportunity."

"Don't thank me yet, sweetheart."

She pulled off the lock and started the timer. Then she slowly pulled the cage off of me. By the time my cock was free and able to stand erect 20 seconds had already passed. Sandy mercifully started giving me a sloppy blowjob. She slurped loudly and ran her tongue in circles as she took me in and out of her sweet mouth.

After days of relentless teasing I started getting close after maybe 30 seconds of this. But she could always tell when I was close and she removed me with a pop just in time. I wiggled my hips in frustration and she giggled. Then she put a single finger on my slickened dick. Slowly, evilly she ran it up and down, looking deep into my worried eyes.

The clock was ticking, I knew. But I wasn't allowed to look at it. This is something I knew from experience.

She teased me with her hand gradually more intensely. Counting in my head I figured I had about 25 seconds left. She started jerking me furiously. I was getting so close, so very close! I could feel the orgasm rising up inside me, causing a full body tingle with its intensity. She stopped abruptly, leaving me twitching.

"About 10 seconds now, dear. 9...8...7...6....3...2...1... aaand... zero. Well hun, better luck next time. I think I'll give you another chance in let's say, three more days."

I groaned in disappointment and frustration.

"Oh, don't give me that. Remember, if you want that chance in three days you have to be very good for me. You HAVE to impress me."

Her voice was full of dark, teasing humor.

"Yes, ma'am," I responded dutifully.

And so three days passed. I was extra subservient in hopes of getting free. And also just because being horny and serving go hand in hand for me. I could hardly focus at work that last day, after over a week of being deprived.

When I got home that night, Sandy was all dressed up. She looked gorgeous in her blue wrap dress, with her dark stockings, the slight heels on her black Mary Janes. Her bright red lips were driving me crazy. But something struck me. These were not stay home and be sexy clothes. This was an out on the town outfit.

"Oh, this?" she interrupted, bringing me back from staring. "I'm glad you like it dear, but it's not really for you. I'm going out for dinner and drinks with Linda tonight."

"Linda? Like my boss, Linda?" I asked, shocked. She chuckled.

"Yes, love. The very same. We really got along at the party the other day, so we've decided to have a little girls' night."

"Oh, okay. Well, sounds fun."

I wasn't supposed to ask about release so I held back. The tension in the air was definitely noticeable though.

"You're wondering about your release, aren't you? Well like I said. I'm going to give you a CHANCE at release. As promised. Now strip."

I did as I was told. When I was completely naked she grabbed my caged dick and took me to the bedroom where there were some clothes laid out on the bed. All of them white, with pink frills. There was a thong, miniskirt, sheer lace bra, and a top to go over it. She told me to put them on, so I did it quickly. I didn't want to keep her waiting.

"Very good girl. Oh, you look like such a sexy little slut. Now lay on the bed."

I did as I was told and she pulled out some lengths of pink rope. She wrapped some around my chest, pinning my arms at my sides. Then she used handcuffs to attach my hands to the knot in the middle of my chest. They had just a little mobility. Not nearly enough to reach my caged clit.

Then Sandy tied my feet together. She ran a rope through the reinforced eyelet we had attached to the ceiling (for this purpose) and strung it through the one around my feet. She pulled until my legs began to rise. When they were way up in the air, allowing easy access to my ass she cinched the rope tightly.

"Try to escape," she commanded.

I wiggled and squirmed pitifully as she laughed. It was no use, as she well knew.

"Can't escape, huh? Then you wouldn't mind if I did this."

She pulled out a butt plug and lubed it up. She circled it around my whole, loosening me up.

"Right? You don't mind?"

She kept circling and applied more and more pressure. This plug was big. I slowly stretched to accommodate it. When it was all the way in me at last I felt so full. She gave me a light spank and continued.

"And you wouldn't mind if I did this."

My wife pulled off her panties, straddled my face, and started humping. I could feel her wetness from having me helpless. I stuck out my tongue and started doing what I do best. She moaned loudly, savoring the pleasure of riding my face. Her gyrations became harsher and harder the longer she road me. It got to the point that my neck and jaw were hurting from the relentless assault. But my tongue kept pushing. To stop licking when my dominant wife was riding my face was instant trouble.

She responded to my persistence by orgasming loudly and leaking her juices all over me. The scent of her saturated my world and continued to drive me mad with lust. I could only strain in my cage, restrained to the bed and writhing beneath her. After resting for a bit Sandy got off. She brought out her key to my cage and waved it in front of me.

"Hmm, should I use this to unlock your cock?"

"Yes, please ma'am. Please unlock me!"

"Alright, you desperate little thing. Let's unlock the lock."

She teased over the keyhole, missing on purpose a couple times. Then she pushed it in. She turned it with a click. The lock came off and she set it aside. She brought her face close to my still caged cock and breathed warmly on it. Then she stuck out her tongue. Sandy licked the steel cage, giving me an unbelievable view but no sensation. Then she pulled out another lock! She clicked it on, and I could see that it was a combination lock.

"Ooh, so close. You were almost free. But you're gonna have to work a lot harder if you want to get out."

She left the room. For a minute I wondered if she was gonna just leave me here and go out. I definitely couldn't try any combinations on the lock with my hands bound the way they were. Sandy came back a couple minutes later with a small block of ice in her hands. She put it up against my balls. I jolted back.

"Oooh, cold huh? Yeah this thing should take a good hour or two to melt. And get this, it holds the key to your handcuffs. Any idea what I'm gonna do with it?"

I had an idea what she was up to. I looked up and there was a new apparatus bolted into the ceiling. It was basically a funnel with a hole in the bottom.

"This is your chance for release, doll. When this ice melts it will drop your key right on your stomach. Then you can escape the handcuffs and start trying combinations. Since it has four numbers, there are only about ten thousand possible combinations to try."

I was pretty speechless overall, but it didn't matter anyway. She brought the penis gag out and secured it into my mouth.

"Hmmm, one more thing. If you want to up your chances by getting more time I could melt some of the ice. I would just use your body heat, from a body part of my choice of course. Do you want to try that? Shake your head yes or no, baby."

I nodded my head yes, desperate to give myself the best chance. I didn't know if I could stand any more days of this. Though, I did have a foreboding sense of where she might be taking the body heat from.

"Lovely. Well, as promised here you go sweetie."

She pressed the ice block back against my balls and held it there. It was the part of the block closest to the key inside and as the water dripped down I figured I really was increasing my chances. But the cold was excruciating!

"I'll hold it here as long as you can stand it, baby. You just whimper when you want me to stop."

I held out as long as I could, but after just a minute or two it seemed my balls might actually die. I was beginning to lose feeling, which might have been even worse than the pain! I whimpered naturally and she removed the ice from my scrotum. She climbed on the bed and reached up to slide the block into the funnel. While she was standing up there she tapped my balls with the tip of her shoe. It turns out I could still feel them afterall. I groaned. She kicked at them just a little harder, enough to make them ache. Then she climbed down.

"Well, I guess all set for now. Good luck, hubby. I just know you'll find the right numbers! If you get free before I get home I'll give you an unbelievable reward. But only if you wait to cum until I get back. Now, I should be gone a couple hours at least. Have funn!"

And she left the room, leaving the door open. I lay there, struggling at my bonds a little bit. Though I had no real hope of escape. At least not until the ice finished melting. After a few minutes I heard a knock on the door followed by Sandy's answer.

"Heeyyy!" I heard my boss yell excitedly. "Thanks for inviting me!"

"Of course! It's been a while since I made a new friend. I've been really excited all week."

"Is your wonderful husband home? I wouldn't mind saying hello. I don't want us being friends to be awkward for him, you know?"

If only she knew exactly how awkward I felt at this moment. Hearing myself being talked about while I waited in desperate chastity, bound, helpless, and sissified. And all while my wife and my boss chatted away down the hall. And the door was open!

"Oh, he doesn't mind. He's actually really happy for me. And I think he's looking forward to me being more sociable. Tonight he went out with the boys! Usually he has to worry about leaving me bored at home."

"Oh, okay. I'm really glad you said that. I was kind of worried. Well, shall we go?"

"Yes!"

Both lovely women giggled excitedly and left with a slam of the door.

_____________________________

So there I was, left to wait. And to hope and hope that this ice block would melt quickly. It only took a couple minutes for me to feel the first couple drops fall on my stomach. They were cold, but not unpleasant. The sensation was actually kind of enjoyable, since I knew it came from my lover. But maybe that was just a result of my desperation.

The drops fell hypnotically down onto my stomach, a rhythmic reminder of my predicament. I couldn't move to avoid their icy presence. They just kept falling relentlessly down on me, chilling me and punctuating my submission. I couldn't quite reach where the drops were landing with my bound hands. That made me worry that I wouldn't be able to catch the key when it finally came.

I just lay there for a while, straining in my cage and thinking about my wife out with my boss. I don't know how long I spaced out but there came a time that the dripping became a little more frequent.

I tried to snap out of my trance of submission and think logically. After thinking about where I thought Sandy would put the number I decided to start at 5000 and count down. There was no way I was going to be able to try all of the combinations in the time I had to work with. So it was going to take at least a little bit of luck.

As the ice began to get pretty small my body started tensing. I knew I would have only one chance at catching the key. I watched the ice drip with frantic attention, expecting it to break through the thin frozen barrier at any second. It took longer than I had expected though. It's amazing how long that key stayed in stasis on its paper thin sheet of ice at the end. But then the moment came and it fell!

I lifted my pelvis and it caused the key to bounce in the right direction. It was in my hands. I knew I didn't have any time to waste so I unlocked the cuffs and started work on the combination lock immediately. I tried combos as quickly as I could, getting at least one per second. But the task stretched on and on. And the more it stretched on, the more helpless I felt. The more helpless I felt, well, you know. There wasn't much comfort for my locked up cock.

I don't know how long it took me to try thousands of combinations. I noticed Sandy had purposely moved our alarm clock so I had no concept of real time. But after pretty much forever the lock clicked open. The combination was 0001. I laughed hysterically at the joke of it. She had known I would complicate things so she put the combination right at the beginning.

I took off the lock and then started gently removing my cage. It felt so good to be out after over a week, the longest I had ever been in the cage. I started to stroke myself, careful not to get anywhere near the edge. I was just enjoying the sensation. It was almost just as torturous to now have to wait until Sandy got back to cum if I wanted my "unbelievable reward". I was quite tempted to just give myself relief and end the struggle right there. But I waited. And waited.

Some time later I heard laughter outside followed by a key turning in the door. Somehow the sound of a key turning had taken on a whole new meaning for me.

"Come in, come iiin!" my wife exclaimed quite drunkenly.

"Alright! Just a second! I just need to adjust my---*clunk*-----oh nevermind."

She giggled girlishly some more. I had no clue what was happening out there but it was clear that the two of them were properly sloshed. I heard them sit down in the living room and my worry increased. The door was open and I could hear every little thing. My boss was only a few drunken missteps from discovering me in my bound, feminized state.

"Do you think he's home yet? I wonder if he's here! Oh my God I wouldn't want him to see me like this!"

Likewise, I thought.

"Ohh, it would be fine. You know, your cutest employee likes to have a good time himself now and then. I think it would be endearing. Let me see if he's home really quickly."

Erratic footsteps ambled toward the room and Sandy appeared in the door, smiling wide.

"Hey! You did it!" she whisper yelled. She laughed to herself. "I'll see you soon", she whispered with a wink.

Then she went back to the living room. She informed Linda that I was asleep so they should probably keep it down. Linda figured she had better be going. I heard a rather affectionate drunken goodbye and then footsteps back to the bedroom.

"Well well wellll, it looks like my bound maiden has found herrrself some freedom," she slurred. "I'm gonna give you the most unbelievable reward sweety. But I think it's best if we bind your hands again first. Give me the handcuff keys."

I handed them over, trying not to laugh at her. She was kind of ridiculous right now. She cuffed my hands up by the headboard this time, completely getting them out of the way. Then she leaned down with her face near my engorged cock. She blew on it and it twitched. Sweetly, she put her lips on the tip and kissed. More twitching. She giggled. Then she took the whole thing in her mouth in one motion! It was heaven in there, especially as sensitive as I was.

I could feel her tongue work around my skin as she bobbed with slow speed. I savored the feeling for what must have been only 30 seconds. I started to throb and I knew I was only going to last a few more seconds. Then she stopped. I whimpered and she laughed. Quite cruelly I might add.

"Are you ready for your unbelievable reward?"

"Yes ma'am!" I replied eagerly through my gag.

"Alright, I'll be right back."

She left and came back with the last thing I wanted to see. It was more ice. I complained but she pressed it against my cock until it started shrinking back down. Then she slipped it through the ring of the chastity cage and clicked the rest of it on. Out came the original lock with the key undoubtedly on her person. And just like that I was locked up again, with no release.

"See, unbelievable. Your reward is that you get to become even more desperate for me. You get to be my little cock prisoner for even longer! Maybe we'll even go another week, who knows?"

I was absolutely speechless, and also gagged. I did groan and really almost started to cry.

"Yes, this is the best decision. I think I'm enjoying this too much to let you have release yet. If you would stop being so cute and pitiful I might consider letting you cum. But you are just so entertaining! And so lucky to be locked up by a bombshell like me, don't you think?"

I nodded reluctantly.

"Good girl. Well, I guess we can untie you now that the most important part is locked away. Bet you wish you would have cum when you had the chance, huh?"

I nodded again. God, did I wish I had just done it when I could.

_________________________

The next day was excruciating for me with the amount of tease I had endured with no release. And just the sheer disappointment after all of my hard work the night before. My only consolation was seeing Linda extremely hungover. That gave me a bit of a laugh. She mostly stayed in her office so people wouldn't notice, but I knew.

She even called me in to have a bit of a heart to heart at some point. She just wanted to make sure it was okay that she and my wife were friends. I genuinely appreciated it, sensing her sincerity. I decided she was a pretty cool person. It made me feel glad for my wife, even though it made things a little awkward for me. And of course, the awkwardness for me was a part that Sandy loved.

Every day that week Sandy teased me relentlessly. I served her without question, trying desperately to earn release. She had me clean the whole house in a maid uniform, literally scrubbing the floors with a toothbrush. She made me massage her every night. It drove me absolutely lust drunk to see her beautiful body all oiled up as I ran my fingers over it. It's safe to say that I was sort of zombie-like, in a subspace so deep that I didn't even think of anyone but her.

It really did take a whole week for her to give me another chance at release. And it went like this. She unlocked me and told me to put my hand on my cock. Then she set a timer. I had 15 seconds to make myself cum. The pitiful thing is I actually came close. But I didn't quite make it and she commanded me to take my hands off. I watched with misery as she shrunk me back down into the cage.

Now something happens to a man when he it's denied release for a certain period of time. Yes, he becomes malleable of will and pitifully desperate. He may obey orders more easily and be more willing to please. But there's something else that happens. Something about all that gets pent up inside that just starts to spill over.

It can come out in so many ways, from emotional fits you might expect from a toddler to bouts of angst and rage that harken back to adolescence. It was somewhere a little after the two week mark when it came into me, like a chimney fire swallowing the air jetting through. And it happened in the very worst place it could have, really.

It happened in Linda's office.

_______________________________

"You've been off, John. Just off."

I was starting to fume silently on the inside. Linda had called me in for what she called a mandatory performance evaluation. I thought if I opened my mouth I might explode, so I stayed quiet.

"It's like you're terribly distracted or something. And I don't want you to feel bad, John. I don't. You've been a very reliable member of this company for so long but lately. I just don't know what's up with you."

I had become transfixed by her cleavage. I wasn't openly staring, but those immaculate breasts in my peripheral were dominating my attention. I didn't want to be a pig but at this point it was just impossible to get sex off my mind.

"John.... John are you even listening?!" Her voice rose, showing its first glimpse of true anger.

"I can't take it! The pressure is too much! Maybe you should just focus on your own part of the fucking business and I'll focus on mine! You're not so goddamn perfect yourself you know!" I exploded violently.

Now it was her turn to be quiet. She stared at me, obviously angry but even moreso confused.

"What is wrong with you?" she asked with almost gentle concern in her voice. And tears came to her eyes. "I think you need to go home for the day. Figure your shit out, John. This isn't like you. I'll see you back here tomorrow and you'd better be ready to shape up. Goodbye."

She waved her hand and I left, fuming but also with tears of my own. I knew exactly what was wrong with me but I couldn't tell her. It was complicated and so confusing. So I went back to my cubicle and got my stuff to leave.

When I arrived home the last thing I expected to see was Sandy's car in the driveway. This time of day she should be at work, yet there it was. My stomach clenched. This was no coincidence. I walked up the porch steps gingerly, as if walking on a thinly frozen lake. As I slipped my key into the slot it gave me visions of so many fantasies. Then I opened the door with a creak.

Sandy was standing there, dressed up again. But this was not an outfit for going out on the town. She had dressed in all leather and latex. All black. A corset lifted and squeezed her breasts together. That's where my eyes fell first. She had shiny black latex stockings and as I followed them up her leg I came to something that made me gulp. It was a big, black strapon cock. It was new, and it was bigger than any she'd had before.

It was long, oh yes. But what really gave me frightened goosebumps was the girth. It was a thick, thick cock. And I just knew it was about to impale me. The last detail to mention is her face, which was made up impeccably but crimson with anger. Oh, she knew what had happened.

"Take off your fucking clothes."

I started to strip quickly and desperately. I knew stalling wouldn't help. And maybe if I did so quickly I would have a chance to explain myself.

"On your knees. Put this on."

She tossed me a tube of bright red lipstick. I started applying it. When I was done with a sloppy lipstick job I figured it was my only chance to grovel.

"Sandy, I'm so sorry. If I could just exp----"

"Explain? You can explain yourself with my cock in your throat. You insolent little whore. There is no excuse for the way you acted."

I lowered my head.

"Yes ma'am."

"Crawl over here. Now, open up."

She roughly shoved her cock into my mouth. My angry wife wasted no time putting the cock into my throat, causing me to gag.

"Alright, slut. You wanted to explain yourself? You can explain yourself now."

I hesitated, not sure if she was kidding or what.

"I said explain yourself! Now, bitch!"

I frantically made unintelligible gargling sounds, trying to explain myself. Sandy continued to fuck my throat raw as I made my feeble attempt. When tears streamed down my face and she was satisfied she pulled her cock out.

"Now shut up. And bend over the couch. Put your hands behind your back."

She cuffed my hands. Then she spread my cheeks and started coating me with lube. I moaned with pleasure and she slapped my ass.

"No moaning! This is not for your pleasure. You'll soon find that out."

And so, despite the pleasure I held back my moans as she loosened me up with her slick fingers. She slipped them inside me. First one, then two, three. Despite what she had said she massaged my prostate for just a couple seconds. I had to hold back extra hard. Then she pulled them out and I felt the tip of her cock against me.

"This is the biggest cock you've ever taken, by a long shot. So it might not feel great. But I won't hear any bitching or moaning from you, got it?"

"Yes, ma'am."

"Alright."

And she started to push. At first there was no give. My asshole wasn't used to intruders that were so damn.... large. But she applied more pressure and it started to give. I felt like I was going to split open. Slowly she pushed into me, my tunnel doing its best to accommodate.

She didn't shove it home right away, as someone with less control might do. That would have probably injured me. No, she just continued gradually, relentlessly, and quite uncomfortably until she was buried up to the hilt. I felt all 8 inches of girthy black cock filling me up.

She pulled it out slowly. It pressed hard on my inner walls and slid against me. Then she slid it back in, still slowly but faster this time. She buried it as deep as she possibly could, and waited there, pulling my hips against her.

Then she took two leather straps and wrapped them around both of our thighs on either side. Her hips were held tightly against my ass. When she buckled them into place it effectively bound us together, with no way for me to eject the massive dildo inside me. And no way to fight back. She slapped my ass hard.

"This cock is here just to make sure you stay right where I want you for your punishment. I'm going to give you fifty spanks. After each one you will count it and say 'I'm sorry Linda.'"

"Yes ma'--"

*WHACK"

"1.... I

... I'm sorry Linda," I whimpered.

"Good, just like that. Nice and pitiful. Show me that it hurts."

And so it continued like that, fifty full-handed swats on my ass as I was cock-pinned against the couch. My base instincts often tried to escape the pain, flinching away. But there was just nowhere to go. Any movement stretched my ass painfully.

So I took my punishment, motionless and with eyes full of tears. For the last ten I was sobbing too hard to keep up my counting and reciting but Sandy didn't mind. She took the opportunity to go into overdrive, smacking frantically while verbally berating me.

"How dare you take out your frustration on my sweet friend Linda! When she was only trying to help you! And she said you kept staring at her tits! You know better than to behave like a fucking animal!"

And just like that the room was silent, except for my sobs. My ass was on fire, inside and out. The endorphins from pain and from crying mixed sweetly with the stimulation on my prostate. Even with everything else going on, I was very close to cumming.

"Oh honey," Sandy said softly, lovingly. "You really screwed that one up."

She caressed my tender ass sweetly as she talked.

"Here's the deal. I have already forgiven you. You took the first part of your punishment obediently enough. But the punishment is not over. First of all, I'm calling for another week of chastity. It is okay to be frustrated, but not to take it out on other people. Maybe another week will give you practice at controlling yourself."

"Especially when it's one of the two women who are in charge of your life. At home, you're mine. And at work you do what Linda says. Not that there's a kinky element per say, but it does please me to know you have female control at work too. And from such a good person."

"If you really can't handle the frustration, we have a safe word. And you can use it. But I know you've said you want to avoid that at all costs. That being truly submissive to me is what you want. And that is what I want too. I don't want it to change. But you are responsible for drawing your own boundaries. I will not have you lashing out at anyone else again. Got it?"

"Yes ma'am."

She undid the straps that held us together. As she did the dildo slipped out just a couple inches, giving me both relief and pleasure. She held it in place as she stepped out of the harness. Then she reversed the harness straps to wrap around my waist, my legs. As she cinched it tightly the cock went back in completely.

"Also part of your punishment. You're going to keep this monster in you for the rest of the day, until we go to bed. I'm actually meeting up with Linda later. To keep you honest, I think I'm going to lock it in."

She looped padlocks through the buckle holes on the straps. The giant cock was now completely stuck, deep in my ass.

"Well, get up. see how it feels."

She pulled on my shoulders to help me get up, my arms still cuffed behind me.

"Walk. How is it?"

"It's definitely kind of limiting, ma'am. A little uncomfortable."

"Well that's fine. As long as you can move. I'm planning on keeping you busy while I'm gone you know. Here, let's test your movement. Go get me my shoes."

They were just across the living room by the door. I waddled my way over to them, feeling the full size of the cock in my ass. Bending down for the shoes was almost a relief. I got a shoelace from each shoe in my teeth and lifted. Then I hobbled back over to Sandra who was laughing at me.

"See! You can move just fine. And you're such a cute doggy boy, with my shoes in your mouth. Help me put them on."

That was harder of course, but I managed it. Kneeling at her feet and gyrating my hips with the sensation I pulled her shoes onto her feet one at a time. This of course meant squishing my face against each foot as the shoe slid on. Then I grabbed the backs with my teeth, pulling with my cheek against the underside of her calf.

"Verry goood. You're well on your way to getting back into my good graces. If you complete this list while I'm gone, then you'll be mostly done with your punishment. Except for the added chastity of course."

She unlocked my cuffs, then handed me a piece of paper which I tucked into my pocket for later.

"For now," she decided, "You're gonna give me another massage. I could definitely use a little pick me up."

The afternoon passed by, me sweetly serving her like usual but with the added obstacle of my overfilled hole. When the evening came, I was banished for some free time while Sandra got ready for her night. When she emerged she looked even more done up than the last time she went out! And she was definitely showing more skin.

"What do you think, baby?" she asked in a purposely sultry voice.

"You look," I paused. "Unbelievable."

"Why thank you. You look like a whore. You know, your lipstick is all messed up. You should really do something about that. Actually, maybe you should look at that list I gave you now."

I pulled out the list. It started with detailed instructions about how I was to prepare myself. They involved putting on a ten piece french maid outfit and doing my makeup, as well as removing all of my body hair. All actions for this part of the list were to be done before Sandy left.

When I was done my lipstick was most definitely fixed, but I wasn't so sure I didn't look even more like a whore. Sandy was pleased with my ministrations.

"Look at you! Just as you were told, darling. You're ready to clean the whole house now! Well, stick to the list sweetheart. I've got to go meet Linda!"

So she left and I stayed home. The cleaning instructions were detailed too. There wasn't much of the house she had left out. And many surfaces were to be cleaned using a toothbrush.

It would have been difficult even on a regular day. But in my five inch heels, with a giant dong locked inside of me it was nearly impossible. But I was determined. I knew I had fucked up, and what Sandy had said about responsibility had really stuck with me. It was 1 a. m. and I had just finished up when I got a text.

"Put on some male clothes and take off your makeup. I'm bringing Linda back to the house so you can apologize to her. See you in twenty."

"Yes, ma'am," I replied.

With all of the dolling up I had done it took close to the full twenty minutes to be a regular looking man again. I heard footsteps on the porch and the two ladies walked in. Drunk, but not nearly as drunk as last time.

"Is there something you would like to say to Linda?"

"Yeah."

"You should grovel on your knees."

"Sandy!" Linda balked.

"I was just kidding," lied Sandy with a laugh. "Well, go ahead then John. Say it."

"I'm really sorry I exploded on you today, Linda. I know you were just trying to help, and that you have a job to do. Personal things were coming up for me and I have no excuse. I didn't process them well and misdirected my frustration."

"I accept your apology, John. Though maybe Sandy was right. It would have been better if you groveled."

I was quietly terrified for a second.

"Haha I'm just kidding, John. But that was very thoughtfully put and I forgive you. Just make sure it doesn't happen again. And by the way, I like to think I'm a pretty good person to talk to when you're going through personal things. And if I'm going to keep being a bigger part of your life by being close with Sandy I figure we should be able to be open with each other. Okay?"

"Yeah, you're right. Thanks Linda."

"No problem. you've got a friend here anytime. Alright guys, I'm tired. It's been a long day and we have to work in the morning. I'm gonna head out."

We said our goodbyes, which included a surprisingly long hug between Linda and I. After Linda left Sandy had finally let me remove the giant cock. I was definitely sore from it, but also felt a strong empty feeling. I almost wanted it back, torture that it was.

__________________________

Things improved over the next couple days. Linda and I spoke more at work and Sandy seemed to be in a good mood again. When I got home from work one day Sandy called me into the bedroom. I followed her in and she pulled out my key. My hopes soared. I looked at her expectantly. And she laughed at me for my desperation.

"You can at least pretend to have some poise, silly. I'm not going to let you out right now. I just wanted to show you something."

My hopes returned to their previous method of travel, being dragged along the ground. And Sandy went to the nightstand drawer and pulled out what looked to be a necklace. It had a rather large red jewel in an oval shape. I watched as she moved some pieces around on it, sliding out a panel.

"This is just big enough to fit your key. See?"

She pushed the small key inside and slid the panel back in place. She moved the couple parts that locked it in. And it really didn't look like it opened or anything. Just a regular necklace. She put it around her neck.

"How do I look?"

"Beautiful, of course. It looks great on you."

"Thanks!" She gave me a little smooch. "Power was always flattering for me. Now I can remind you who holds the key and no one else will know. Now why don't you get on your knees and beg me to let you cum some more. Then maybe I'll let you give me a massage."

___________________________

The rest of the week went by excruciatingly slowly. The frustration was back more powerful than ever. Every woman I saw drove me mad. It seemed my libido had given me a break for a couple days but it was back with a vengeance. I tried not to stare, and through serious effort managed to not explode on anyone.

Then it was finally the day. A week ago Sandy had told me she was adding a week to my chastity sentence for my transgressions. That at least had me in a good mood. She would probably at least let me out and give me a chance to cum tonight. When I got back from lunch I went to bring Linda some papers, actually whistling.

Entering her office she asked me to sit down for a minute. I settled into the seat at her desk and almost gasped out loud. The necklace was around her neck. The red jeweled necklace, with the only key to free my cock, sat prettily right between her amazing breasts. She noticed me looking, hopefully just at the necklace.

"Oh, you like? Sandy gave it to me. I think it's my new favorite!"

"Oh, wow! It's very lovely. Sandy does have good taste."

"That she does! It's a bit bulkier than what I usually wear, but somehow feels pretty comfortable for me. Anyway, the reason I wanted to chat was I just wanted to check in. Make sure you knew there are no hard feelings over what happened last week. We all get under pressure sometimes, and I've noticed a serious improvement in your effort this week."

"Well, thanks Linda. I'm glad we can put all that behind us. I've definitely been trying hard to get back on track."

As we talked I couldn't keep my eyes from snapping back down to the necklace, transfixed. Her milky skin and deep cleavage seemed to prop up the pendant for display. My cock strained painfully but I tried my best not to let on. We finished our little heart to heart and Linda mentioned Sandy had wanted to do something this weekend, the three of us. I said that sounded lovely, then excused myself and went back to my desk.

What the fuck?! I screamed in my head. She gave Linda the fucking key! I was supposed to have a chance for release today. I was definitely not happy with Sandy, but I was also so turned on by my helplessness that I couldn't stay too mad. Sandy had such a sense of irony sometimes. I decided to give her a call on my break. She picked up after the first ring.

"Oh hi dear, I didn't expect to hear from you!"

"Yeah right," I said more angrily than I meant to. "You gave it to her? How am I ever supposed to get that back!"

"Well, this is part of your punishment. A reminder that even if it's only professional, Linda is in charge of you just like I am. It's important to me that you obey women everywhere you go."

"But you said today was the day I was going to get a chance for release!"

"That sounds an awful lot like talking back, hun. I would watch your tone if I were you."

"Sorry, ma'am."

"That's alright. I think you just misunderstood. This IS your chance for release. You can earn release by being extra subservient and helpful to Linda. I don't care what it takes but make a noticeable effort. If Linda mentions to me how good you've been unprompted, then I'll invite her to swim with us this weekend. Surely she'll wear the necklace to show me how much she loves it, but she'll take it off to get in the water. Problem solved."

I had to think of what to say. How did she always keep me so off balance?

"Yes, ma'am."

"Yes ma'am, what?"

"Yes ma'am, thank you for the opportunity."

"That's better. That sounds like a boy who wants to cum sometime soon. Now go see Linda again. I want to hear about what a nice boy you are to her."

"Yes, ma'am."

*click*

_________________________

And so began my service days to Linda. I got her coffee, filed her papers, rearranged her desk, cleaned up her desktop. All kinds of stuff really. And I asked her if I could do it all. She looked at me a little funny sometimes, asking to do all of these tasks for her. But each time I did I was favored with a smile and profuse thanks. On Friday night before bed I finally got the feedback I'd been hoping for. Or so I thought.

"Linda called. She says you've been very sweet to her, and helped her organize her office the best it's ever been! She even said you've been like her little secretary. That part made me laugh."

I blinked at her hopefully.

"You've been so good, baby. So I asked Linda if she wanted to come over and swim this weekend. She said she actually can't swim right now, for womanly reasons. So we're going to try again next weekend. This time we're going on a hike! Doesn't that sound fun?"

I groaned.

"Yes, ma'am. I'm looking forward to it."

"Oh don't look so glum. This way you can practice being Linda's little secretary a little more. And hey, if you manage to catch her with the necklace off you can always try to make a move to reclaim your key."

"Yes, ma'am."

"Good boy. You're doing a great job. Timing just wasn't on your side this week. Now let's get some shut eye. We have a long hike tomorrow."

__________________________

In the morning Sandy woke me up by caressing my ass. I heard her pump the lube on her bedside table once. Then her cold wet fingers were sliding against my hole. She toyed with me for a moment. Then she reached again, grabbing for something. I felt it press against my opening.

As it slid inside me I recognized the feeling of a familiar butt plug we often played with. Usually this was what we used if I was going to keep it in for a while. It was a good size to be relatively comfortable for all day wear.

"You're going to wear this for our hike today, dear. What do you think about that?"

"It sounds like a good idea to me, ma'am."

"You're lying for me. How sweet. Well, Linda wants to do at least five miles. Hope you're comfy."

"Five miles? During her time of the month? Is she crazy?"

She chuckled and then picked out a pair of panties for me to wear too. Linda arrived and we all packed into one car. I noticed with a gulp that she was wearing her necklace. The one with the key to my freedom inside. I dreamed wistfully of getting it back as we went down the road. I was the driver of course. Just like I was the pack mule when we finally arrived.

Sandy insisted that Linda not even bring a bag. That I would carry everything we need. Linda joked, asking where she could find a man as good as me. Sandy said that a man as good as me is hard to find and I inwardly beamed at the compliment., laughing nervously. On our hike that day I also suffered quite a bit. The plug was rubbing me all kinds of sensual ways, and I strained in my cage every time I thought of it.

I was back to a sort of delirious obedience it seemed. Just dreaming in subspace as the day went on and I carried everything for the two chatty women. They were having a blast it seemed. Every once in a while I caught a glimpse of the necklace, glinting and taunting me in the sun. Sandy gave me a sly look now and then, and teased my caged cock whenever Linda wasn't looking.

At the end of the day we went back to the house for dinner. I was the cook, while the ladies laughed over wine in the living room. Sandy even made me wear a pink ruffled apron. This was a power move, as it was just normal enough to not be questioned too far. But it did get me a comment from Linda. As I brought out more wine, the ladies stopped talking as if they had been discussing a juicy secret. They looked up at me, both smiling. I poured the wine.

"I like your apron, John. It's very pretty," Linda teased. "You are being such a good house husband tonight. I'm thoroughly impressed!"

"Oh you haven't seen a thing, Linda. Watch this. Honey, my feet are just killing me from the hike today. Will you come over and rub them?"

"Of course, dear."

I kneeled at her feet like I was accustomed to. It was a totally normal thing for me of course. But Linda definitely looked twice as I went to my knees before my wife. I rubbed her feet, throbbing and leaking in my cage the whole time. It was a little bit humiliating, but also enjoyable. Sandy was really making me show off my subservience.

"Ugh, my feet are killing me too. I wish I had a man that would do that for me."

"John will do it. Won't you dear?"

"Oh don't be silly, Sandy! I couldn't make him do that. He's been so good to us already. Besides, he's your man."

"Oh I don't mind sharing. He'd be happy to help. Wouldn't you dear?"

It was heavily implied in her tone that I didn't have a choice.

"Of course, hun. I wouldn't mind."

I moved over, still on my knees, to Linda's bare feet. I looked up at her bashfully, and she at me. Then she lifted her foot toward me. I took it in hand and started to rub. As I looked up at her I saw her enter another world, staring off into space with the pleasant sensation. Her eyes closed lazily. Her necklace hung hypnotically above her breasts. I stared at it as I worked. Eventually I had rubbed both of her feet and she was satisfied.

"Wow, John you're really good at that. Sandy, you've trained him so well," she said with a laugh.

"You don't know the half of it," Sandy said cheekily. They laughed hard at that one.

"Well, I can't say I've ever had such a good foot rub. You are a lucky lady if you can have those any time."

"That I am. But you know, I'm sure he would give you one any time. Wouldn't you dear?"

"Yes, of course."

I knew the only choice was to agree with my wife. If Linda found it uncomfortable to be offered my ongoing foot services, she didn't let on. They were pretty loose from the drinks at this point and it seemed no one was thinking too much about it.

"Alright, chop chop house husband. Is dinner almost ready for us or what?"

"Yes yes, it's almost ready!"

I rushed into the kitchen to check on things. Laughter carried from the living room, clearly about me. I set the table in the dining room and served the plates. When I returned to the living room the girls were whispering and giggling again. They were looking at something on Sandy's phone. When they noticed me they stopped.

"Dinner is ready, ladies. Come and get it."

I turned and left right away, sure that I was becoming red with embarrassment. The two of them came in a few minutes later and we all sat down to eat. It was almost too quiet when Linda spoke up.

"So, John. Sandy told me why you've been so obedient all day."

I gulped, growing very red again. I couldn't believe my secrets had all been aired out. And to my boss!

"She, uh. She did?"

"Yeah. Oh my God. I can't believe you lost a bet and you have to do everything she says for two weeks! Didn't you know that women are better at Yahtzee? They have a woman's intuition."

They both laughed hard. I laughed along, not knowing how to react in this situation. Now Linda did know something was going on, but not exactly what. Linda cleared her throat.

"Anyways, I was telling Sandy that I think she's being too nice to you. I mean, waiting on us hand and foot is nice. I can't help but think of other possibilities though."

"John, from now on you are to think of Linda as an extension of myself. Whatever she tells you, you have to do it just the same. Okay?"

"Okay," I said reluctantly.

"Good. Now that that's sorted out, I might still have just a few hard feelings leftover from the other day. And I thought it would be funny if," she looked at Sandy who nodded her encouragement. "You wore a dress for us."

She laughed maniacally, as if this were the most outlandish request she had ever heard. Little did she know. She looked at me like a cat playing with a mouse. That sort of "I've got you now" look.

"Okay," I hesitated. "Well, if that's what you want."

My cock strained in it's cage.

"But nothing too girly, okay?"

"It's just not up to you hun," Sandy cut in. "Linda will choose which one you wear. To the bedroom!"

Linda literally squealed with glee. I guess she really was excited for this. We got to the bedroom and she looked at her options. There was quite a variety of dresses in the closet. Linda didn't know it, but almost half of them were mine. And mine were the ones she was rifling through.

It made sense. If you were looking for a dress that was feminine, over the top, and emasculating my side of the closet was full of options. She flipped through a variety of sexy dresses and poofed out lolita style gowns. She paused for a moment when she saw the maid outfit before pressing on.

"Wow Sandy, I didn't know you were into all of this. We should play dress up soon, just us girls!

"Yeah, totally!"

I laughed inside knowing that Sandy wouldn't be caught dead in most of the clothes she dressed me in. She was more into class than costume. It seemed Linda had finally made her decision as she pulled out a pink and white, ruffled Lolita gown. Her eyes were smiling with ridicule when she held it out for me to take.

I grabbed it, looking it over hesitantly. My cock begged to expand but met the walls of it's harsh prison once again. I was slipping deep into subspace.

"Well go on! Go in that bathroom and change! I want to see how it fits you," Linda commanded.

I did as I was told, pausing before my return to the bedroom. Here I was, about to go out to my boss in a frilly pink dress. She was never going to forget what that looked like when she saw me at work going forward. I took a deep breath and walked out, feeling bashful and with a pink face to match the dress.

I was met with an uncontrollable laughing fit from Linda. She was laughing at me so hard she couldn't even speak. My cock throbbed and leaked from the humiliation. Her laughter lasted most of a minute before she could form words.

"Oh my God, John! You look so pretty!"

This was followed by another bout of laughter.

"Also, apparently it fits you perfectly? Why do you look like such a natural woman? We could throw a little makeup on your face and I don't think we'd be able to tell the difference!"

"Maybe we should," chimed in Sandy cheerfully.

"Oh can we?!"

"Of course we can. He has to do whatever I say, so he has to do what you say too. Have fun with it! In my opinion he still isn't even close to paying you back for what he pulled the other day."

Linda was delighted to hear this.

"You know what? You're right! John, you've got some serious payback coming this week. Now go sit down at the vanity. It's time for some makeup."

I complied and was surprised to find that Linda was quite an adept makeup artist. The intimacy of her touching my face and giving me the classic makeup commands did nothing to soothe the ache in my downstairs. It was really quite awkward to have my wife just standing there watching this. Linda may not know exactly what she was doing to me but Sandy knew very well. But she looked on with an amused smile until I was ready.

I must admit I looked absolutely gorgeous, though it was very over the top. Especially on the blush! That part was very doll-like, which I supposed Linda did on purpose. She made me stand and turn. I noticed her nipples were poking through her bra and her shirt. Was she getting turned on by this too?

I think the wine was starting to really hit home for her because all of her previous timidness was gone. She threw out command after command, getting carried away.

"You tried to intimidate me with your loud man voice. I even cried you know! Well look at you now, big man. You look like a baby girl doll. You know what? Say it. Say that you're a little baby girl doll."

"I'm a little baby girl doll."

"Make your voice higher pitch! And add that I was right and you were wrong. And spin like a ballerina while you do it."

I did all of that, my girly voice pretty comical. She laughed her ass off as I spun around like a silly girl. She enjoyed it so much she actually made me do the same thing a couple more times. She had become an absolute maniac.

"Now I want you to curtsy. And tell me that you respect me as your superior. And that you'll never yell at me again."

The tormenting, the phrases and girly dances went on for a while. By the end I had done the cancan and even twerked. Linda had applied brutal emasculation to me over and over. And she didn't even know I liked it, which made it all the more authentic. She obviously had a bit of anger toward men in general. And I was the lucky recipient of her catharsis.

Sandy mostly just watched and laughed. But she did put in a suggestion or two at times. When it was late Linda finally decided to go home. We hugged goodbye, a long hug once again. When she was gone I turned to Sandy.

"What the hell just happened?

"I think Linda just made you her bitch."

"Jeez, I guess so. Was it just me or did she seem...."

"Yep, I think you're right. I think she was totally turned on. Maybe she wouldn't have let that on so easily but she was pretty tipsy. It seems we have a natural on our hands."

"And that's okay with you? You're not jealous?" I asked, concerned.

Sandy laughed.

"Nope, on the contrary my little cutie. This is exactly what I was hoping for. I sensed something about her the night we met. But this has just worked out so easily. For her to feminize you of her own volition, with only the smallest nudge? Brilliant."

"Oh, shit," I paused in thought. "You are way beyond me, honey. I didn't see that coming in a million years."

"Well that's why you have me, to show you what to do. You don't even have to worry your silly little head."

She giggled. I throbbed. We both got ready for bed. As we lay there that night a million thoughts swirled through my head. Sandy held me by the cage as we cuddled, eliciting groans and moans full of weeks of frustration. I started to wonder if I would ever be free. The only key to my freedom was unsuspectingly dangling from Linda's neck.

"Are you going to tell her that this isn't just a bet? That this is our dynamic?"

"Yes, but not yet. I want to see what she does. It was pretty entertaining to see her totally lose herself for a while tonight. Just think, tomorrow you get to go work for her. I wonder if she'll have any tricks up her sleeve."

"Oh God," I thought out loud. I wonder.

________________________________

When I arrived at work the next morning there was an envelope on my desk with my name on it. I opened it and read:

"My office, NOW!"

Well that was aggressive. I went immediately, fearing the worst. After knocking I entered to find Linda behind her desk with her fingertips arched. Very super-villain like. She wore a smile as wide as a Cheshire cat, and her eyes were laughing.

"Please, have a seat John."

I sat down nervously.

"Well, I don't know about you but I had a lot of fun last night. I caught myself a couple times thinking I had gone too far, but Sandy assured me it seemed perfect to her. We were texting this morning and she thought I should keep going. And, well, I'm enjoying this too much to decline her offer."

She slid a box with a red bow across the desk to me.

"You were such a good little secretary for me last week, John. And this week you should do the same. But I thought maybe this time you could dress the part. Open it, John."

I undid the bow and Linda was already giggling. At the top of the box I found a pair of lacy red panties and a matching bra, as well as a pair of dark pantyhose. Below them was a short, formal skirt and a white dress blouse.

"They're your size, John. Sandy made sure of that for me. You're going to be wearing them anytime you're inside my office for the rest of the week. Don't worry, you can change when you go outside. But you're going to be spending a lot of time in my office. Now put them on. I'll turn around."

Linda turned and let me change into the clothes. There was a moment where my caged cock was exposed in her office. If she turned around she would discover exactly how far Sandy had taken her advantage. But she continued to face the window as I pulled the panties on, then the pantyhose. My cock complained loudly in my head at the torturous silky pleasure. When I was dressed I told Linda I was ready. She turned around and put her hand over her mouth, stifling her laughter.

"Very nice. How do your panties feel? Are they soft and silky?"

"Yes," I said dejectedly.

She started laughing hysterically again. I guess it wasn't just the booze last night. She really did find this hilarious. My cock reacted to the ridicule strongly. I had to be careful or I would start drooling.

"I love doing this to you. It's just so funny. You don't want to wear panties but you have to. Like a pretty girl. It's too rich."

She thought for a second, her hand nervously fondling the necklace she wore between her breasts. Unknowingly she toyed with the only key to me ever getting relief.

"You know? I really liked that foot rub last night. I think I'll have another. Get under my desk please, and take your time down there. Oh wait!"

She disappeared under her desk for a moment and brought out some red 4 inch heels. She handed them to me and I put them on. I walked shakily on them a bit, pretending I hadn't practiced endlessly at home. This brought another uproar of laughter before she told me to go ahead and get under the desk.

I got on my hands and knees and crawled under right away. Linda slipped off her shoes and stuck her feet out at me. One came dangerously close to brushing my cage and giving me away.

"Hey, careful with those things," I complained amiably.

"I'll be careful if I want to John. And you're not making me want to be very careful." She kicked me lightly in the face. "Now get to work."

I couldn't believe she had done that and paused for a moment. Then I brushed it off and got started. I rubbed her feet until my hands were running out of steam. And then she still wouldn't let me stop. I wondered if she knew I could see up her skirt from down here. Surely that must be on her mind. At some point I thought I caught a whiff of her arousal. My senses for such things were very acute, desperate and deprived as I was. But I kept quiet and tried not to stare too much. Eventually when I truly couldn't squeeze anymore she finally let me crawl out.

"That was just great, John. You really do know how to rub feet. I might have another one of those before the day is up. Now, enough shenanigans. As much as I hate to say it we need to get some work done. Will you go through those papers there and check my work?"

She put her feet up on the desk and donned a sleep mask.

"I think I'm going to take a little nap. Wake me when you get through the stack, okay?"

"Yes ma'am," I replied reflexively.

"Ooh, yes ma'am. I like that. You have to say that from now on."

___________________________

That's pretty much how my week went. I played secretary for Linda during the day and maid for Sandy at night. I gave foot massages to Linda and full body massages to Sandy. With happy endings of course. The absolute stupor caused by my horniness made the days pass quickly. The blood from my brain was constantly trying to go south. Though when it arrived it found nowhere to go and looped around again. I wouldn't be surprised if a man in such a desperate state was down a few IQ points.

Linda was very creative with some of her demands throughout the week. At one point she made me draft an email to her repeating the same phrase 200 times.

"Dear Linda, I'm going to be a good girl from now on."

When it arrived in her inbox she roared with laughter. She made me do it again. Another time she made me write a ten page essay about how I was a good little secretary girl, how it was natural for her to be my superior, and how all insolent men should be humbled by powerful women. She made me print it to the large production printer in the common area and run to get it before anyone could see. I had turned the doorknob halfway before I realized I was in my secretary outfit and turned around to change.

By the end of the week her arousal at all of this dominance was thinly veiled at best. I could tell it was all she could manage to not tell me to get under the desk and eat her pussy. She would often let me don my male attire and banish me from her office suddenly, after she had clearly worked herself up. When the end of the day came on Friday she just smiled a cruel smile.

"See you tomorrow," she said dreamily. " We're going to go swimming. Just us three girls."

She winked. I changed into my male attire (except for the panties) and went home.

_____________________________

Saturday morning the sun in the window was sweet and inviting. I tried to roll over in Sandy's arms but she clenched me tightly from behind.

"Where do you think you're going, slut?"

"I, I was going to start getting the place ready for Linda to come over, ma'am."

"Oh, someone's eager to be exposed. I'm going to show her everything that you are today, hun. From what you've been telling me about your week at work she's game for this. I'm even going to show her how much of a cock loving slut you are."

"Yes, ma'am," I replied nervously.

"You act like you don't want to be her bitch too. Don't you?"

"Yes, ma'am. Very much so, I'm just really nervous."

"Well it's a good thing I like you that way. You're so cute when you're nervous. Anyway, preparing the house is a good idea and you'll definitely get around to it. But first thing is first, my love. Eat me."

I sweetly licked her to an orgasm, once again experiencing powerful pain and pleasure in my cage. When she was done with me I went about my tasks. I checked the pool PH, prepared a charcuterie we had picked up for the occasion, and made sure the fridge was stocked with drinks. I finished with about an hour before her arrival so Sandy and I snuggled up for a while.

When Linda arrived she looked quite lovely. She was wearing a light blue summer dress and the necklace rested gently on her impressive cleavage. She carried a shopping bag. Linda kissed Sandy on the cheek and gave me a warm hug. She told me she had brought me another present. From the bag she pulled a skimpy pink bikini with a thong back, which I was meant to wear. I didn't think it was really going to cover much of anything but I guess that was the point. It was a bold move, but Sandy reassured her it was perfect.

It was agreed, at Sandy's suggestion that the two ladies would go ahead and get ready to swim while I brought out the snacks and drinks. When I came out with the tray both of them were in skimpy bikinis of their own. My eyes just about popped out of my head. Then Sandy made sure I rubbed tanning oil all over them. Both of them. It was a new experience for me, rubbing the oil into Linda's thighs and even on her ass. So very close to her more intimate parts. She was actually shaking as I did it.

It was around this time that I looked down and saw exactly what I'd been waiting for. For well over a week! Linda's necklace was laying on the table next to her phone. I looked at it with unhinged desire as I finished rubbing oil into Linda's back.

"Alright, John. Now we're going to get in and you can go change into your bikini. You're going to look so cute in it!" Sandy instructed. "And when you get back maybe we can rub some of the oil on you." She winked.

"Yes ma'am."

"Oh don't you just love when he says that?" Linda mocked. "It sounds so good coming from him."

"Yeah, I guess I've just been getting pretty used to it! Now c'mon, I want to see if you can cannonball!"

The two gorgeous gals ran toward the pool giggling. I snatched the necklace quickly and made a bee line for the house. I took the bikini to our room and fiddled with the necklace. I had only seen Sandy open it once, so it took me a while to figure it out. But then there it was! My key! I clicked the lock with it and pulled it off my tortured member. Wow, the feeling of freedom. I contemplated jerking off right away but I knew I didn't have permission. So I tucked away the chastity cage and put on my bikini.

Wearing it drove me crazy of course. Especially since I could feel the soft fabric rubbing against me for the first time in weeks. I was so hard that I could barely fit in the bottoms. My rock hard boner was completely visible except for the tip. The more I tried to will it down the worse it got. So I resigned myself to the exposure and humiliation. I was sure it was what Sandy expected anyway. I put the necklace inside of my towel and headed back outside, hesitantly.

My arrival was met with whistles and cheers, followed by profuse laughter. Especially Linda was completely losing her shit. I also caught her biting her lip when she saw me a little closer. It may have spent most of its time recently being pathetic and locked away, but my cock was actually pretty impressive when free.

"Wow, I think someone likes her teeny bikini a little too much!" Linda yelled, humiliating me. She laughed and laughed. "Seriously, you can't tell me you're not enjoying this now. Do you like your pink bikini, John?"

"Yes, ma'am."

"Haha! Yes, what John? Tell me the whole story."

"I like my little pink bikini, ma'am."

"Damn right you do! That much is pretty clear!" More relentless laughter.

I slyly set my towel down next to Linda's stuff and let the necklace roll out next to her phone. Everything was back in it's place and Linda was none the wiser. The girls called me over.

As promised Sandy enlisted Linda's help to oil me up from head to toe. Sandy took care of my front side and Linda the back. They both seemed to linger when they got to my bikini bottoms. Linda rubbed the oil into my ass cheeks, even slipping into the crack as much as she could get away with while keeping it subtle. I tried not to moan. Of course that wasn't super easy because Sandy was in front literally lubing up my cock! Linda couldn't tell from behind but I was really getting it from both ends!

When they finished and stopped the sensation I actually whimpered girlishly. I didn't want it to stop. Linda and Sandy both found that part amusing. I was about to try to get in the pool but before I could Sandy spoke up.

"Hun, could you get us more drinks before we get in."

"Yes, ma'am."

When I got back with drinks I handed them out one at a time. As I placed a mimosa in Linda's hand she grabbed my cock confidently and stared into my startled eyes.

"What? Sandy said I could. She said we can do all kinds of things with you today."

I gulped and nodded. I cracked a smile of my own out of nervousness.

"That's right, you're in trouble now. I have your wife's permission to use you however I want. Did you ever think you would find yourself here, John? In a tiny pink bikini with your boss squeezing your cock?"

"Um, no ma'am. Definitely not."

"Me neither, yet here we are. I kind of like it, don't you?"

"Yes, ma'am."

"Say yes, boss."

"Yes, boss."

"Good boy. Now let's swim."

We got in the pool and adjusted for a bit before Sandy had an idea.

"Let's play Marco Polo! But with a twist. Linda and I will both have our eyes closed, and you'll be on the run, John. Instead of "Marco" we're going to yell "Sissy Girl". And instead of "Polo" you're to going to yell "That's me!" If one of us catches you by the balls you lose and you're punished. If you can survive five minutes without either of us getting a hold of your balls, you get a very lucky reward. But you can't fight us off with your arms. You can only run away."

It took a minute for that to all sink in, but after clarifying the rules we got the game started. Sandy, Linda, and I started in three different corners of the pool. They both closed their eyes and started heading right for me. Linda was trying to make sure she got to me first, obviously excited to get a handful of my balls. I just knew I didn't have a chance, but I instinctively started running as quietly as I could in the water. They were going to the corner where I started, not where I was headed.

"Sissy girrrrrl!" Linda yelled teasingly.

"That's me!" I yelled back.

She doubled over in laughter and it slowed her down a little. But now they both knew where I was. They were heading right for me, just a half of a pools length away. I dove under the water, swimming right between them under the surface. They were heading the wrong way and I started to get hope that I might actually win.

"Oh sissy girl!" yelled Sandy.

"That's me," I said, more quietly and bashfully this time.

"I didn't hear that, sissy girl. Louder please!"

I repeated myself and they headed toward me. This time they were closer together so I had to make a choice. I tried to get around on the side closer to Sandy. She reached and didn't quite get my balls as I passed, but then she tripped me. I fell into the water, and before I could recover I felt a grip around my balls. As I pulled away the grip tightened and I was forced to stay. I got to my feet and looked up. There was Linda with a cruel grin on her face. She squeezed my extra full balls as we locked eyes. They ached in her hand as she kneaded them.

"Looks like someone is in for a punishment."

She looked at Sandy in deferment, wondering what idea she might have for punishment. Sandy asked her what she thought might be suitable. The girls tossed around ideas, maybe some just to freak me out. They could make me run around the block in my pink bikini. They could invite some of our other coworkers over to see me. Maybe take some selfies together and post them on Instagram. I was really nervous that they were actually going to expose me, but they went with something more conventional in the end. A good old fashioned spanking.

I was made to beach myself on the edge of the pool, exposing my thong bikini clad ass. They each claimed a cheek and made me count the slaps. By the end of twenty they had turned my ass about the same shade as my bikini. They asked if I wanted to play again. I obliged obediently, to more of Linda's uproarious laughter.

Well, the second time was similar except it was over faster. Linda hunted me down in mere seconds and squeezed my balls even harder when she caught them. I whimpered in pain and she just stared at me with her evil smile again. This time they decided the punishment should be new and different.

"I know," Sandy said. "How about we make him gag on your foot, Linda?"

"Oh my God can we?!"

"The possibilities are endless, my dear. John, get out of the pool and go kneel in front of the chair."

I did as I was told and Linda took a seat before me. She stuck out a foot, right in front of my face.

"Start slow," Sandy commanded. "Just take her big toe slowly into your mouth. Good girl. Now suck it like a cock. Show Linda how good you're getting at being a little cocksucker."

Linda was absolutely delighted as I obeyed, sucking her big toe desperately. She laughed and laughed. And as I continued she started to moan instead. She got an out of control look on her face. She couldn't get enough of this.

Gradually she pushed her foot harder into my face until all five toes popped into my mouth. It was being stretched, and Linda was giggling again. I could feel her toes on my tonsils as I started to gag. Tears ran down my face but she kept it up. Finally she removed her foot from my mouth, resting the wet toes on my cheek as she looked down, glowing. She noticed I was hard as a rock.

"Sandy, I think he really likes this. Like, look at him! He's as hard as I've ever seen a man! Do you think this bet is the best thing that's ever happened to him?"

There was a slight pause as Sandy decided to let her in on the reality of the situation.

"Alright, I'm gonna tell you straight. There is no bet. My husband gets off on being dominated and he will do whatever I want. I can tell that you like to be dominant too, so I decided to just share him a little bit. I've been having so much fun that I'm thinking of making this a permanent thing. Besides, someone has to make sure he's put in his right place at work."

Linda looked surprised, but very gladly so. She squealed with excitement.

"Oh my God!!! So this isn't going to end this week? I can keep playing with him as my secretary?"

"That and more, hun. You can use him however you want to at work. Just as long as there's no lasting damage and he doesn't cum without my permission. Maybe if you want to try something particularly new and extreme, talk to me about it first. We could have fun brainstorming anyway."

"Oh my fucking God! I'm so happy! Thank you thank you Sandy! Hey, wait. How long has it been since you've let him cum?"

"Oh, I don't know. I guess I haven't been really paying attention. Honey, how long has it been."

"23 days, ma'am."

They both laughed at my quick response. Of course I would know exactly how long it had been.

"Wow, Sandy," Linda pondered aloud. "This is really something. He must be so desperate. No wonder he freaked out on me the other day."

"Yeah, it's pretty hilarious. I think he actually has become more obedient since I've extended his chastity sentence. And he was pretty pliable already."

"Chastity.... you mean like those cages? Do you have one of those?"

"Oh yes, right now is the first time he's been out in weeks. It must be a real relief."

"Well, his dick does look pretty happy right now."

They both giggled. The Q and A session continued for a bit. Sandy told Linda a longer list of the things she had been able to make me do. She also discussed my limits a bit. Twenty minutes later the girls decided to play another game of Sissy Polo, as they now called it. I lost of course, to Sandy this time. My punishment? I was to be bound to the couch, bent over the armrest.

I followed the two gorgeous ladies into the house and took my position. Sandy already had the soft pink shibari rope ready in the living room, and she slowly taught Linda the whole process of artfully incapacitating me. I was bent over the edge of the couch with my feet tied to the legs of it. My arms were behind my back and useless. More ropes crisscrossed decoratively around my back and chest, eventually securing my body bent over forward. Sandy had Linda follow her to our bedroom and I was left to stew in my helpless desperation. I had an idea I knew what was coming next. Now I only had to wait.

The girls returned some time later, Linda giggling uncontrollably as usual. As they came around the couch I knew what she found so funny. This was the first time she had ever had a cock strapped between her legs. She wiggled it back and forth with excitement and laughter. The two goddesses approached me seductively with their strapons as I looked up in a mix of fear and eagerness. They were wearing nothing but the harnesses. This was the first time I had ever seen Linda's giant tits and I looked up in awe.

"Okay, Linda. We're gonna demonstrate our sissy's cocksucking capabilities now. I've had her practicing for a long time and let me tell you, she's gotten quite talented. Of course, she was a natural to start with," she teased with a wink. "Now, we have to get these lips ready. We want them to look extra pretty wrapped around our cocks."

She pulled out a tube of pink lipstick and coated my lips in a generous layer, far more than is classy. Then she got some plumping lip gloss out and slathered the sticky wet stuff on. I could feel the tingle of the plumping agent working.

Linda could only stare mesmerized as Sandy put her cock up to my lips. She didn't shove it in, just presented it to me. I knew what I was supposed to do. And I knew I'd better do it well. I took it into my mouth, slowly at first. Then I went as deep as it could possibly go. This was not a small cock. By the time I had reached the base it was well down my slightly gagging throat.

I held it there for a moment, then backed off and looked up at them. I plunged my head again, more quickly this time, with reckless abandon. Linda had overcome her trance and was laughing at me again, big shocker. I began to bob like a truly talented whore on my wife's cock as Linda watched. Linda wiggled her cock in her hands, stroked it. It was definitely a double ended strapon. I could tell as she teased herself, letting out small moans and watching the show. Then Sandy pulled out. She held it just out of my reach, taunting me with it.

"Get the cock, sissy. C'mon Bella, work for it."

"Oh my God! Is that her name?!" Linda interjected. "It's so cute!"

"Yeah, I think it suits her well," said Sandy nonchalantly as she plunged hard into my eager mouth.

I was caught totally off guard and I started to choke hard. She pulled her cock out again and started tapping my cheek with it.

"Awww, was that mean of me? Poor little Bella got too much cock when she wasn't ready. Well too bad. Always be ready bitch."

She plunged in again and started fucking my face roughly. Linda was brought to silence again as she stared on, pleasuring herself. Sandy was truly showing her how it's done. After using my face as her fuck hole a little longer she pulled out. I gasped for breath as she addressed my boss.

"Okay, Linda. I think it's time for you to take a turn. Are you ready?"

It took a short moment for Linda to snap back into reality. A moan escaped her and she covered her mouth, slightly embarrassed. Then she recovered.

"Wow. Yes. I am so fucking ready."

"Alright, let's start slow. Bella, I want you to lick the head of Linda's cock."

Linda positioned herself and I stuck out my tongue. I lapped sweetly at her cock as she wiggled it around. She giggled, clearly beside herself with the elation of humiliating me this way. It seemed as if she had always wanted this but never quite imagined it happening. She rubbed her cock around my lips, almost as if applying more lipstick.

"Good, you're a natural. Now Linda, I want you to push your cock all the way in, nice and slow. Sissy, open up your throat."

I opened and Linda pushed the cock in. I wrapped my glossy lips tightly around it to give her the best show possible. She made it to my throat and my nose pressed up against her mound. I looked up into her eyes like a good girl as she stared down lustily. She moaned from the pressure against her, then pulled back out. She went in again. Held it there as she looked laughingly into my eyes with a cruel smile. She held it there longer, I didn't know how long I could hold out.

Then Linda got a rhythm and started fucking my face. She was getting wild. Now she was fucking my mouth as hard as Sandy had during her outburst. Now harder. She stayed most of the way in and pushed her mound against my nose over and over. I choked and choked as tears ran down my face. I was at my limit. Sandy stepped in, pulling Linda by the hips gently until she let up.

"Oh, did I go to far?" Linda inquired with genuine worry in her voice.

"Almost," said Sandy. "You were right at the edge of it there. It's important as a dom that you know the limits of your sub. It can take time to learn how much a bitch can take. Don't worry though, I think little Bella had that coming. Don't you think so Bella?"

"Yes, ma'am," I croaked as I regained my composure.

"I'm sorry, Bella. I got a little carried away."

"It's okay, ma'am. You were only doing what you saw fit. I blame my slutty mouth hole."

Linda laughed with surprise. Then Sandy continued her reassurance.

"Yes, it's okay Linda. That's why we're teaching you with such an absolutely filthy slut. She can take a little extra. Now we're going to have to be more careful when we practice with her sissy pussy."

"Oh my God. Oh fuck. We're gonna...."

It seemingly hadn't occurred to Linda what the next step was here. She was trembling with excitement as she tried to form words.

"That's right. We'll get there. But first I want to play with her mouth a little more. I've never had someone to double team her with before."

My boss' expression grew more confident, a knowing smirk coming to her face.

"Let's do this."

And suddenly there were two cocks coming at my face. I would take one deep while the other slapped me on the cheek, waiting its turn. Then I would switch. I went back and forth a couple times. Then Sandy stilled my head.

"Okay, you eager slut. Stop moving so much. I want to try something."

I sat still as the two cocks both came to my lips at the same time. They stretched my lips as I slurped on them both. Then they both started pushing in like crossing swords. This stretched my mouth to it's fullest extent and I whimpered from the slight discomfort. Sandy pulled out, allowing Linda to go in. Then Linda came out and they switched places. It seemed almost choreographed, their timing. They took turns back and forth more and more quickly. Their hips rubbed against one another, giving me a show as I struggled to take all of the cock I was being given.

"Okay," Sandy interrupted as they both pulled out. "We're going to have a look at that sissy pussy. Are you ready, Linda?"

Linda looked over her with equal parts gratitude and lust. There was something heavy to the look as I could see both of their eyes change. Their faces moved closer and I couldn't believe my eyes. Sandy and Linda's lips met. It was hard to tell from my vantage beneath them, but it seemed that sparks were flying in their minds. They made out in earnest for a moment before Linda pulled away, giggling and blushing.

"Okay yes, now I'm ready."

She looked down at me with predatory laughter in her eyes, knowing what she was about to do to me. The two women left from my sight, though I quickly felt their hands on my ass. They caressed it with taunting delicacy.

"Okay Linda, like I said. We have to be more careful with this part. It's a bit more sensitive than Bella's slutty throat. That being said, it's been well stretched compared to a normal man's ass so it can definitely take quite a bit. It's been especially stretched recently, but I'll tell you that story later."

She laughed as I felt her cock against me.

"What's important at first is that we get plenty of lubrication."

I felt cool drops slide down my cheeks to meet her cock where it rubbed small circles.

"We start like this, slowly teasing the hole. We're beckoning sweetly for it to open for us. With a slut like this it shouldn't take too much convincing."

The head popped inside and I whimpered.

"See? She likes it."

Linda started laughing uncontrollably again. Though she quieted with a sort of awe as Sandy started pushing in.

"Now we're in, and the first time in we go nice and slow. We make our little slut crave more. Maybe we even make her beg."

"Oh yes, let's make her beg!"

"You heard the boss lady, Bella. Beg for it."

"Please ma'am, please fill me with your cock."

Linda giggled at my pitiful response. But Sandy wasn't done.

"Hmm, I'm not convinced. Do you need it or not?"

"Yes, ma'am. Pleeease, I need your big cock inside me."

"Hmm, how badly do you need it? What would you do for my cock?"

She pulled it out of me a little more, leaving me wanting. Linda continued to laugh at my torment.

"I need it so badly ma'am! More than anything in the world!! I would do anything to earn your cock."

"Anything?" She started to push in again but stopped quite short. "Would you do Linda's whole job as well as your own this week at work?"

At this Linda squealed in delight.

"Yes ma'am, I would definitely do that!"

She pushed further in, pleased with my answer.

"Very good. But while you did that, you wouldn't neglect her foot massages during the day would you?"

"Of course not, ma'am! I would make sure she gets her foot massages."

"Oh that's very good," she cooed as she pushed all the way in. "But you wouldn't be too exhausted to complete your duties at home, right?"

"No ma'am! Of course not! Serving Linda would only energize me to come serve you!"

"Good girl. I think you have all the right answers. We'll see if you can fulfill all of your lofty promises."

And then she started to really fuck me. I squealed with pleasure, backing up onto her as she gripped me by the cheeks. I moaned as she built her rhythm, and groaned as she slapped my ass hard. She picked up the pace until I was right on the edge of sissygasm. Then she abruptly stopped.

"And that's about as hard as we should go on her for now, you see? I have a feel for this. And our little sissy was very close to having an accident, wasn't she?"

"Yes ma'am," I admitted with embarrassment.

"But I stopped just in time, huh?"

"Yes ma'am," I groaned pitifully.

"Very good. Now Linda, it's your turn."

"Really?!! Yes yes yes, Oh my God this is going to be fun," she beamed, her voice husky with desire.

I could only imagine the way she had been teasing herself as she watched. As I felt my wife pull out I groaned at the emptiness, but I quickly felt Linda's cock replace it at my entrance.

"Ohhh, don't worry Bella. I'm gonna take care of you."

Linda's voice was a little bit evil. I felt more lube drip down my crack. I also heard the slick sound of it being spread on the dildo. I could only imagine the sight of my wife jerking off Linda's cock to get the lube on. I could hear them giggle and even start to make out as it happened.

"Now she's pretty warmed up, Linda. So there's no need to be too slow really. But let's try to be gentle at first."

I felt Linda thrust the dildo in all the way to the hilt. Not exactly gentle. I moaned loudly.

"Whoa! Okay, that was... uh... good. Let's go just a little slower."

"Sorry Sandy it just went in easier than I expected."

She sounded sincerely remorseful.

"It's okay, Linda. We just have to remember that she's a loose-pussied little whore. It's understandable. Besides, it seems like she might have liked it. Isn't that right, Bella?"

"Yes ma'am."

Linda started to slide out before pushing it back again.

"Yeah?? You like that?" she questioned harshly.

"Yes ma'am!"

"Yeah? You like your boss' cock in your slutty pussy?"

"Oh yes ma'am!"

She picked up her pace, driving it in with wreckless abandon. I felt her rubbing against my p spot as she panted heavily. My senses were heightened by lust. Over the wet sounds of her pounding, I could even hear her large breasts slapping down against her chest. Faintly behind me to my right I could hear Sandy's fingers working in her pussy as she watched her new apprentice fuck me.

"Oh yes you do. You! Fucking! Love! It!"

Each word lined up with a hard thrust. I was approaching the edge of orgasm when Sandy stopped her.

"Wait, pull out!"

Linda groaned as she removed her cock. She was clearly very close herself.

"Sorry Linda. I just knew Bella was about to let go. And we can't have her doing that yet. Can we, Bella?"

"No ma'am, not without permission."

Linda started to laugh again.

"Oh my God she sounds so pitiful!"

"Yeah, she's kind of pathetic. Hey, I know you were close there and I would hate to disappoint you. Luckily for you, Bella's skill with her mouth on a cock has only one rival."

"You don't mean...

"Yep, she's the best pussy eater the world has ever seen."

I blushed at the compliment.

"Well then."

Linda came around the front and removed her strap. Her pussy shone with a slick wetness I had never seen, even on my own wife. She was just so turned on. Or maybe it was just a physical tendency of hers. Regardless, she was absolutely sopping. And as she inched closer to my face I felt more lube being dripped onto my ass. I moaned as Sandy entered me slowly from behind. Linda grabbed my hair and pulled my nose hard against her folds.

"Take a deep breath. Good girl. That's the smell of your boss' pussy. And you're going to love it, aren't you?"

I let out a muffled agreement into her lips.

"I'm gonna take that as a yes. Now, lick me! Now bitch!"

I started licking, she started gasping sharp shallow breaths, and Sandy started to fuck me gently all at once. It took me a minute to find where Linda liked it best. She was a whole different woman after all. But my clever tongue found two spots that made her moan. She wasn't shy in letting me know.

So I gave each its fair attention, while now and then teasing her clit. I was driving her crazy and she pulled my hair tightly. I was practically drowning as she rubbed herself against my face. If I was going to be a tease, she was going to make sure her clit got all the simulation it needed. She rubbed my nose on it as I kept licking.

"Sandy, she's being a little tease. She's making me work to get enough on my clit."

Sandy spanked me hard as she slammed into me once.

"Bad girl! Stop being a coy little slut and lick her fucking clit!"

"Yes ma'am," I managed to get out before my hair was yanked again.

I practically couldn't even pull away enough to lap at her clit, but I managed to get my tongue there after Linda made me fight for it. I ran it side to side quickly, with strong pressure. Then I would gently dive into one side between her clit and hood. I repeated this, adding some more variation to my patterns.

I felt her start to tense as she pulled my hair harder than ever before. My boss rubbed her clit roughly against my tongue as her pelvis spasmed, her cum leaking out as she ordered me.

"Lick it all up, slut! Swallow it all!! Ohh fuck."

I slurped up her juices, which tasted sweet to me. I gulped it all down like a good girl. There was near silence now, the only sound that of Sandy pulling out of me with a pop.

Linda leaned against the back of the couch, dwelling in the bliss of her powerful orgasm. She had a far away look to her.

"That was the hardest I've come in my life," she insisted seriously, deliriously.

Sandy chuckled.

"You do look pretty spent. I'm glad my little slave could be such a good girl for you. I've never really had a chance to show her off before."

"You've definitely trained her well. Thank you, thank you so much for letting me in on your little secret."

"It was my pleasure. And Bella's too I think."

She laughed, thinking to herself as she looked at my helpless form. I was clearly exhausted from all of that sucking, fucking, and licking. But I was in deep subspace, my eyes glazed over.

"Speaking of Bella's pleasure," Linda added. "Do you think she's finally earned the release she's been so desperate for?"

"Hmm, I don't know. I think she's pretty close now but I'm curious if she'll be more subservient than ever."

She rubbed my back as I moaned at her hesitance.

"Oh you are so bad Sandy. The little slut doesn't look like she can wait another second."

"I know I know. But that's what's so intriguing. I swear I thought that when I looked at her weeks ago. But here we are with the most pitiful, most obedient little sissy I've ever seen. It's delicious."

"Hahaha alright, so what should we make her do to earn it?"

"I'm thinking for now I could go for another drink by the pool."

I felt her begin to untie me from the sofa.

"Bella, you go put on your maid outfit okay? The pink one. You'll do your makeup just how I like it, maybe go a little heavier on the lipstick. Then you'll bring us our drinks by the pool, okay?"

"Yes ma'am," I replied dutifully as I stretched away the stiffness of my binding.

Linda giggled, and the two ladies walked nude back out into the sunshine hand in hand. I did as I was told, going upstairs to the closet and picking out the maid dress in question. Before I slipped on the panties I looked down at my throbbing cock. It was so tempting to at least rub it a little while I could.

Sandy had proven that she had it in her to just lock me right back up if given the chance. And how much longer could I actually stand this denial? But no. I didn't want to disappoint her, especially in front of her new friend. I pulled the panties up, shivering as my hardness nestled into the soft silky fabric.

I finished getting ready, grabbed a couple drinks from the fridge along with the charcuterie board. As I walked out with the two trays, swaying my hips on four inch heels, I looked every bit the perfect maid.

"Oh good girl. You even brought us a snack," my wife complimented. "That's all for now dear. I think you should go take off your clothes, except the panties, and cuff yourself to the headboard in the bedroom. Throw the keys somewhere out of reach okay? You've been very good so far, but I don't want to risk you touching yourself without permission."

"Yes ma'am."

I curtsied and went inside, Linda's laughter trailing me from the sight of my subservient girlish gesture. I went straight to the bedroom and stripped to my panties. I cuffed my hands to the headboard, then flung the keys away. They landed on the floor with a clink. I lay there for probably an hour before I heard movement in the house.

Sandy and Linda walked into the room still naked. Their hair was wet from a recent swim and they both smiled brightly to see me in my compromising position. Sandy strode right over to me grinning.

"Ooh, someone is still hard. Has it been this way the whole time?"

"Yes ma'am."

"Goood," she cooed, starting to lightly touch me through the panties. "Don't want you softening up on us now. In fact."

She pulled out what looked like a little pill from the drawer, and brought it to my mouth. I looked up at her hesitantly, terrified of being any more desperate than I already was.

"Open up," she chided softly, "It's just a little natural supplement to bring you even more pleasure. You want more pleasure don't you?"

I opened my mouth and let her finger push the pill in. She brought some water to my lips to help me wash it down. I gulped down the unknown aphrodisiac and looked up fearfully.

"Don't worry," teased Linda. "We're going to take good care of you. We've been discussing the best ways to take you to the height of pleasure. But first, we have to wait till that thing kicks in and we were thinking we would start with a little pain."

She smiled evilly and ran her hand along my chest. From either side of the bed the two women each grabbed one of my exposed nipples and pinched hard. I yelped out in pain.

"Thank us."

"Thank you!"

"Do you want more?"

"Yes please!"

They pinched even harder. Sandy let go and walked over to grab a wooden toy box we kept on our dresser. Linda's fingers persisted, twisting and yanking at my delicate nipple flesh. Then she seemed distracted as Sandy handed her a nipple clamp. Her eyes grew wide at the idea.

The two of them each fastened an adjustable clamp onto one of my nipples. They tightened down the screws slowly but relentlessly causing me to whimper. When I had inadvertantly signaled that they were tight enough, they let go, allowing the clamps to hang on their own.

They watched me struggle with the pain for a minute or two, seriously satisfied. I half thought they were going to make popcorn or something. They tightened the clamps a little further, then watched again. The girls giggled as I squirmed, especially each time they jiggled the clamps.

"We're going to leave you like this for a bit. We have to get ready!"

Whatever their plan, they left the room as I struggled against the cuffs, my nipples almost numb by now. Some time later they returned, dressed in black. They had matching lingerie that didn't leave much to the imagination. In fact, they were my imagination. I couldn't imagine a hotter sight. Their lips were painted bright red, their eyes shaded dark. They were a dream and a nightmare all in one.

Sandy got out a flogger and a riding crop and offered Linda a choice. She took the crop. Pleased by this, Sandy began to run the soft leather of the flogger along my thighs, tickling me. The sight of Linda with the crop was maybe the scariest thing I had seen yet. She was wild with anticipation. The man-hating tendency I had sensed before twinkled deviously in her eyes and I audibly gulped when I saw her.

"Awww, is Sissy Bella scared I'm gonna hurt her?"

I nodded shyly.

"Well I am. And you're going to love it, boy."

"Ooh, you're in trouble now, hun.

The two women laughed. They circled me. Or maybe semi circled, with the bed against the wall. I looked back and forth, trying to see who would strike first. It was my wife who took the lead. She brought the flogger down hard on my thighs. I had begun to yelp when Linda followed on the other side with the crop. It stung even more, and cut my little cry in half.

"Ooh, good one Linda. Give her another."

Linda didn't hesitate. She swung three times on my thigh, the last one landing terrifyingly close to the family jewels. I cried out again.

"Wow, I love this. He squeals like a little piggy."

My wife replied with raucous laughter.

"Hmm, you know? We haven't played piggy before. Oink for us piggy."

"Oink oink... oink?"

They both laughed even harder.

"Okay," continued Linda with venom in her voice. "Now squeal!"

She started raining down blows on my stomach and chest with the crop. The last one landed on my nipple, knocking the clamp off painfully. I squealed alright.

"Very good. Yes that was exactly what I was looking for."

She brought the crop down on my cheek, stinging me deeply. There's no way I wouldn't have a visible mark. I cried out again.

"Oh my God! Hahaha. You just did that!"

"Yes I did. That's okay, right?"

"Yeah, but we should probably make that the only one on his face. It's gonna be fun enough for him to explain at work already."

They laughed some more. Sandy ripped off my other clamp and the duo laid down one more heavy barrage of licks from their respective torture devices.

"Alright, my sweet," Sandy fluted gently as she caressed my skin. "That's enough pain for now. It's pleasure time. Besides, I think that pill might be starting to kick in soon."

She pulled my panties aside and flicked my boner, making it wag back and forth like a spring. It didn't move much.

"You know, Linda? I don't think I've ever seen him this hard. Not in years of torment. I think we're really getting to him."

"I think you're right, Sandy. Should we give him relief?"

"Not just yet. I bet you he is just ripe for a little show though."

Linda knew just what she meant. The two women leaned over me from either side of the bed, their bellies pressing against my sides as their lips met. They kissed sweetly, sexily. I moaned just watching them.

"Aww, she likes it. Let's give her some more."

They leaned further into the kiss. Linda's hand went around to pull Sandy's head in. Sandy cupped her breast from beneath, working up to her nipple. Linda moaned into Sandy's mouth.

"John, I think I might have to steal your wife. That would be okay right?"

I groaned as they teased me.

"Oh he wouldn't mind I'm sure. He does whatever makes me happy, and besides, it's not like he's in any position to stop you right now."

They continued to laugh and kiss and tease me for what seemed like forever. There was more fondling, all the while with their bodies pressing up against me from either side. I was so horny I think I could have cried.

All at once they backed up, and started to caress my body all over. It was like they had planned it. And they probably had! This had all seemed too orchestrated to be completely spontaneous. I moaned as they slowly worked their way toward my impossibly hard cock. They lingered along the way, backtracking here and there. Then continuing oh so close.

Sandy got there first, running just a finger along its length as it twitched. Then Linda leaned in close and gave it a tiny kiss. I moaned again weakly. Sandy did the same from the other side. Then they were making out again, every once in a while catching me in the crossfire. Their wet lips felt so immaculate I thought all of my troubles were gone for good.

Then they started to use tongue. Both in their kisses and on me. They twirled them sloppily on all sides of me and I thought I would cum right then and there. But Sandy's sixth sense caught wind of it. She pulled back and smiled.

"Alright Linda, it's time for the finale. Strap on that cock."

I whimpered as Sandy started stroking me. I watched Linda climb into the harness, securing it tightly with one end of the dildo inside her, the more prominent side sticking out menacingly. She looked back at me with a satisfied smile. She pointed at the cock, then at me with a twirl of her finger.

"Watch this!"

Sandy tied my feet together, then ran a rope through the ceiling ring just like the other night. She tightened it down so my legs were suspended, my ass easily presented for Linda's use. Linda clapped and laughed as she approached me, grabbing the lube. Sandy went over to the toy box and brought over a condom and a cock ring.

"You're so pitiful you'd be a two pump chump if we don't do something about it. This condom is extra thick, so it should make you just a little bit less pathetic."

She rolled the condom down my cock, then slid the ring over. It held me snugly at the base.

"There you go, stud. Now, no cumming without permission right? If you do, it's a whole month of chastity after! Got it??"

"Yes, ma'am."

"Good slut."

And so Linda approached me with a smirk, running the head of her cock between my cheeks. She squirted some lube and spread it around with her fingers. I moaned like a desperate whore and she laughed. All the while Sandy was climbing on top of me. I felt her wet pussy start to envelope me gently. The warmth of her slippery walls was heaven. I couldn't quite feel everything because of the condom, which was torturous in its way. But I was still in a heaven I could hardly have imagined without all that came before.

Linda entered me slowly, and I tensed against the dual sensations. As she pushed deeper she reached my prostate and I moaned. My wife leaned down, her breasts meeting my bare chest lazily. She kissed me sweetly as she started to ride me a little faster. Linda was starting to get a pace too and truth is, despite Sandy's precautions it didn't take long. I was on the edge almost the moment Sandy's soft lips met mine.

"Ohhh, please please ma'am I have to cum."

"No no, Bella. It's not time yet. You have to control yourself."

"Ma'am I'm trying! I really am!"

"Keep holding it."

She picked up her pace and Linda slapped my ass. I really did try as hard as I could. I gave it everything in me but there was just no going back. This was a losing battle. I cried out as I came hard into the condom. I spurted and spurted an unbelievable amount as I exploded with greater pleasure than I could have even fathomed. I lay back, completely spent. Sandy grabbed my cheeks roughly with her hand.

"Did you just cum without permission, slut?!"

I nodded in apologetic bliss as Sandy slapped me. I almost didn't even feel it.

"That's a bad, bad girl. After all we did to bring you pleasure and you couldn't even follow a simple order!"

"I'm sorry ma'am, I'm so sorry. I tried, honest!"

My voice was full of genuine remorse mixed with a drunken slurring pleasure.

"You didn't try hard enough!" She climbed off me, and Linda pulled out, leaving me empty. "Do you remember what the consequences are?"

"Yes ma'am," I groaned in despair.

"Say it."

"A full month of chastity."

"That's right. You thought 23 days was hard? You're about to find out how desperate a little slut can get."

As she admonished me she pumped everything out of my softening cock, cleaning me with a soft wet wipe. She pulled out the chastity cage from where I had put it away earlier. Linda looked on at this exchange with all kinds of mixed emotions, but especially laughter.

"You want to help, Linda?"

"Oh yes, definitely!"

"Okay, so you put a little lube on like this. Then you pull one ball through the ring, then pull on the sack until the rest comes through."

As she demonstrated Linda chuckled with delight.

"Okay, now you put her little clit through the ring too. You want to try this part?"

Linda slid my slick, soft cock through the ring so that everything was contained in the ring.

"Good. Now here's the cage part. We have to slide it in as far as it goes. So her little pee hole is right near the end. Good. And now we're ready for the lock!"

"Oh can I do it please?!!"

"Haha, yes. Of course."

Linda looked me in the eye as she slid the lock through the hole where the cage and ring met.

"Are you ready to have your little dick caged by your boss, John?"

I nodded timidly, "Yes, ma'am."

"Good boy. Actually, I want you to try and stop me. C'mon, struggle a little."

I tensed my cuffed hands and went to try and wiggle away from her but there was no chance. She just continued her knowing smile as she locked it in with a click.

"There we go. Right back where you belong."

She patted it mockingly before she and Sandy started to untie my legs. Then they uncuffed me. Sandy walked us over to the closet and let Linda pick my next embarrassing outfit. A schoolgirl outfit of course. As we walked toward the back patio Sandy explained condescendingly.

"Well Bella, you really were being such a good girl for a while there. But you just need more training. When Linda goes home we'll have to discuss your punishments around the house for cumming without permission. I'm sure Linda can think of her own ideas on the work side of things."

She winked at Linda, who agreed profusely. We came to the table by the pool and Sandy picked up Linda's necklace. Linda looked puzzled as she took it apart, placing the key back inside.

"Maybe you should hold onto this for a bit. She's not going to get any chances for release around me this week. That's for sure."

Linda took the necklace with awe.

"You mean.... I...."

"You held it for weeks. I think Bella here loved it. Didn't you, you nasty whore?"

"Yes ma'am."

Linda shivered, as if thinking back on all the times she held me entranced with it.

"Linda, thanks so much for coming. We both had a blast. Let's do something again soon! For now, you both got to cum today, and Bella has some making up to do. Isn't that right, dear?"

I gulped.

"Yes ma'am."

"Sandy, thank you so much for all of this. I can't express how happy you've made me, or how much fun I've been having. Let's have a girls' night this week just the two of us and we can think of some more ideas. Bella? I'll see you at work."

She said it strictly, seriously. Then she cracked an evil smile.