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Day 12
{Dear Reader, this one is a little slow getting started, but it's important to the story line. Persevere and I'll reward you with some hot scenes. Please comment at the end.
It's also very helpful if you read all the Jenny's List stories in order. I don't spend time with re-introductions.}
We were out late last night at the strip club, so I decided to allow myself to sleep in. For the most part, that means I wasn't going to get out of bed before 7am. I was surprised to hear the doorbell at 6:30.
I threw on a robe and went to answer and it was Jenny. She looked like shit. I brought her in and sat her down on the couch and held her as she cried.
Eventually, she looked up at me and said, "I am so sorry. I am such a bitch. I've been up all night crying and I'm a mess."
"What's going on? What can I do?" I asked.
Through tears and sniffles she replied, "I am really a mess over this last two weeks, our relationship, and the fact that I'm leaving in two days." She paused and then continued, "I can't deny I have some shame over what we've done the last two weeks. At home, I'm an upstanding member of my small community. I'm a teacher who has gained respect and been invited to lead in many different ways. I counsel young girls not to rush into the things that I'm guilty of doing myself this week. I'm such a worthless slut!"
I knew I had to choose my words carefully, but was sure I'd fail no matter what I said. "You know I don't think of you that way. I think of you as fun loving and adventurous. You're not 13, you're 43. You've made decisions about your sexuality and you wanted to explore them in a safe space. I hope I've made it safe for you."
"You have. You have been so kind and gentle; except when I didn't want you to be. You're the other reason I hate myself." She responded. I stared at her with a confused look on my face as she continued, "Yesterday morning, when you found me crying, it was for the same reasons. I really have fallen in love with you, but I also have used you to fulfill my perverted dreams. I'm ashamed of what I've dragged you in to because I have such deep feelings for you. That's why I was intentional about asking you to make love to me," She paused to wipe away tears.
I was going to offer an objection but thought better of it and let her continue.
"You did, and you were magnificent and it made me feel even worse about myself. So the rest of the day I ignored you. You see, I knew you could fuck, I just wasn't sure you could make love. When you did with such tenderness I knew you were going to make it harder for me to say goodbye." I gave her an understanding look but remained quiet.
"You see, I don't want to leave my life in Tennessee. I love who I am there. Which means, I can't take you there. I can't be the slut in Tennessee that I've been in Florida. Do you get that?"
"I think so," I said.
"So I decided to be both a slut and a bitch. I ignored you the rest of the day and I didn't include you in my sexual escapades last night. I even avoided any eye contact with you. And when I needed three cocks, I didn't want one to be yours. I'm such a bitch that I was working hard to piss you off and you responded with such grace. I fucking hate that about you... and that's exactly the reason I love you," she said with exasperation in her voice. "God, I sound like one of the teenage girls with their hormones out of whack. How did I become 16 again?"
I grinned at that and said, "I really wish I knew you then... or maybe not until you were 18. I bet I would have loved you just as much."
"You must hate me now." She both stated and asked at the same time.
"Not at all," I told her. "I was hurt and confused, but this really does explain everything. Look, our time together has been crazy. It's not like I'm doing this all the time either. I just didn't have a reputation to maintain here and really don't give a fuck."
We sat silently and held hands for a while. Then I said, "I'm not sure what happens after this. I really have found myself having feelings for you. Even before the sex started, during the first three days you were here, I loved our conversations and getting to know you." I paused thoughtfully.
Then I added, "In 48 hours you board a plane and go back to your other life. Your slut life is over. You don't have to revisit it ever again. Or you can revisit the parts you liked, just more discreetly."
I continued, "Whether or not I'm part of your life after this, I'd really like to be fully a part of it for the next two days. Why don't you consider playing this out, however you want, and board the plane knowing you had accomplished what you set out to do. Will that work for you?"
Jenny sat quietly. Time passed very slowly. Then, without saying anything, she slid off the couch and parted my knees to kneel between them. She reached up and untied my robe and opened it to find my flaccid cock. There was nothing horny about our conversation so my dick hadn't yet caught up to what I was watching her do.
"I'd like to make love to your cock, just with my mouth. If at any time you feel like you want to take charge, I hope you will. I'd like you to punish me for my poor behavior. I don't mean playful punishment. I mean that I want you to take out yesterday's frustrations on me. If you want me to be a slut for 48 hours, then treat me like a slut. I deserve it and want it."
I don't know what exactly flipped the switch from a crying mess at the door an hour ago, but I did think we had salvaged the next two days for the better. Her mouth sucked my limp cock in and I felt it start to grow. What a feeling to feel it slowly fill her mouth. I decided to start by letting her please me in her own way. There was always time to dominate the way she wanted.
Her mouth was working wonders. Her tongue swirling around my ever swelling cock. When it reached full hardness, she reached a hand up to grasp it. I knew I would come fast if I let her, so I demanded, "No hands! Put them behind your back."
She looked up at me with a smile and complied as she licked and kissed and sucked my cock up and down. "I changed my mind, put your hands in front of you. Play with your pussy, but don't come." I commanded her. And again, she complied with as devilish a grin she could manage with her mouth full.
She was getting me close, but I couldn't seem to come. You know how that happens once in a while? You'll understand when you are older. So I told her to use one hand on me and the other on herself, "Jerk me off into your mouth and keep fingering your clit. But, like I said before, don't come. If you get close to orgasm, back off."
Jenny again complied and took my hardness into her right hand as her left remained out of sight. It only took a little while longer and I told her I had to come. With both hands I pushed her head down onto my member until she gagged. Then I pulled her head away, stood up, and directed my semen on to her tits.
Jenny was gasping and getting very close to coming. I instructed, "Place both hands on your tits and squeeze your nipples until the urge to come subsides." She did and she came very close to going over the edge.
When she settled some I told her, "use two fingers of your left hand to scoop up your wetness between your legs." She did. "Now use the same two fingers to clean the come off your tits." Again, she did. "Now stick your fingers in your mouth." She quickly complied.
"Do you think that's punishment enough, or do you need more." I knew she wouldn't figure out that I was setting her up.
"More, punish me and humiliate me. I've been such a bad girl," she begged.
"Get your phone?" I demanded. She looked at me with a strange questioning stare but she got it. "Now, I know you have been collecting the phone numbers of everyone we've seen this week so I need you to send this group text to them all."
"MY MASTER EVAN INVITES YOU TO AN OPEN HOUSE. ALL DAY LONG THERE WILL BE FOOD AND DRINKS. I WILL BE AVAILABLE FOR FREE USE. ANY WAY YOU DESIRE, I AM HERE TO SERVE. I HOPE YOU WILL COME AND LET ME. YOU DON'T NEED TO BRING ANYTHING BUT FULL BALLS, A FULL BLADDER, AND A DESIRE TO HUMILIATE ME."
Jenny looked at me in surprise. "You said you wanted to be humiliated. I want my friends to join me in living out your fantasy," I told her. "Now hit send!" She did and then laughed in a devious but very unsure way.
Then I told her, "Shower up, but don't you dare play with your pussy. Then go down the street to that boutique and purchase some slutty lingerie. Then grocery shop for some food and drinks. Then get back here to clean my house and prepare the food. You have about an hour I would guess." She got up immediately and headed for the bathroom, showered, then left.
I then took a shower and straightened up around the house so she didn't have too much to do. I wanted her focused on guests when they arrived.
When Jenny returned she had all sorts of groceries and a couple of bags from clothing shops I didn't know existed. We unloaded the groceries and she went to change as I began to organize the food and refrigerate the drinks.
Jenny came out wearing an incredibly hot white, shear and crotcless body suit. Around her neck was a black collar with a ring in the center for a leash. There were also rings in either side of the collar. She was wearing black leather wrist cuffs that had clips that could be attached to the collar on either side. Running down the back of the collar was a strap that connected to a belt that was secured around the waist. The strap down the back also had rings for securing her wrists. As did the belt. I was hard in an instant.
Jenny said, "Honey, can you help me secure my wrists when the guests arrive?"
"It's Master to you. And yes I will do that." Then I headed to the garage. I found an old box that had some of the things we had for when we had a dog. I found a leash. It was dark purple so it wouldn't match perfectly. It was made of a woven strap that was 1" wide and 8' long. Our dog had been big.
I returned to find Jenny working in the kitchen. I gathered up the leash into a short whip, snuck up behind her, and landed a hard smack on her bottom. Jenny yelped and bent down from the hard swat on her ass. It was bright red immediately.
I told her to turn around and she did. "Jenny, I am attaching this leash to your collar. It can be used either as a leash or a whip and you are to tell our guests that as they arrive. Do you understand?"
"Yes," she replied and I turned her around and swatted her again.
"Yes, master," She said with a bit of fear in her face and a tear in her eye.
I attached the leash. Then I pulled it in a downward motion that forced her to her knees. I took out my cock and brushed away the tear with the head. Then I stuck it in her mouth and she sucked on it for a few minutes.
Finally, I said, "I need a beer and you need to finish preparing the food." Pulling off my cock, she went straight to the refrigerator and got me a cold one. I had moved to the couch and she brought it to me. I told her to turn around and hand me the end of the leash. She did, fearing what was coming, and I swatted her again, though I backed off how hard it did it. She was already bright red back there.
"You have never seen me drink a beer from a can in my house. Now go get one of the frozen glasses from the freezer and pour my beer! And there better be a proper head on that beer or you will not enjoy the head you will give me." I demanded.
Jenny hurried to the kitchen and got my glass. She returned with a properly poured beer and a smile. I thanked her and told her to return to her work, "Yes, Master," was her reply.
It was only 10:30am and I was almost done with my first beer when the doorbell rang. Jenny jumped at the sound, realizing the day's games were about to begin. We met at the door and I took hold of one hand. I fastened it to her collar and did the same to the other. Then I reached down and inserted two fingers into her pussy and found her to be very wet.
"You've been over there preparing the meal and dreaming of what would come of this day, haven't you?" I asked.
"Yes, master," she said in a barely audible voice. I took the end of the leash and put it between her teeth.
"Kneel right there," I said pointing to a spot about 10 feet away.
When I opened the door I was thrilled to find Penny and Josh. Penny said, "We both have the day off today. When we got Jenny's text it made us so horny. We fucked right before we came over. Where is that little servant?"
I stepped aside so they could see Jenny in her pose. Penny rushed to her as I shook Josh's hand and invited him in.
Jenny, through the leash in her mouth said, "You may use this as a leash or a whip. Whichever seems best to you."
Penny walked around Jenny and said, "Damn girl, you got yourself in a predicament." Then turning to me, "Can I use her now?"
"Yes, Jenny is free use all day." I responded.
Penny said, "Well we plan to stay all day and into the night. This is going to be fun." Then she added, "In anticipation of what the text meant, I didn't bother to clean Josh's come out of my pussy. It's fresh. Can I use her to clean it up?"
"Free use! You may unclasp her wrists and move them however you want." I stated.
Penny took hold of the leash and pulled Jenny to her feet. She undid her wrists from her neck and re-clasped them to her sides on the belt. Then she lay her on the floor. Penny then took down her shorts and panties and sat directly on Jenny's face.
I could tell Jenny went right to work on her pussy by the arching of Penny's back. I whispered to Josh, "Why don't you go over and finger her. Fuck her if you want. However, the rule is that she isn't allowed to come."
Josh pulled down his shorts, walked over, knelt and without warning shoved his cock in Jenny's wet snatch. She screamed into Penny's crotch as he did. So I knelt over and said to Jenny, "Remember, you are not allowed to come." She nodded her head and kept working on Penny.
Then I upped her anxiety. "Jenny," I yelled at her, "Why haven't you offered a drink to our guests?" Her eyes flew open and she struggled to say something but Penny was barely giving her a chance to breathe. There was no way she was going to be able to talk.
After only a few minutes, Penny had a small orgasm and she rose up off Jenny. Jenny's face was a wet, come coated mess. Josh pulled out and Jenny protested, "No, I was almost there." Then she realized that she wasn't allowed to get "there" and her head dropped downward.
Reluctantly, Jenny returned to her role and said, "If someone would like to unclasp my hands, I would love to take your drink order." Penny helped her out of her clasps and asked for a water.
Josh asked for a beer and Jenny looked straight at me. "Wait, is that a problem?" Josh asked.
"Not if she does it right, it's not. You see her red ass? She learned that, at my house, a beer is served in a chilled glass," I replied. Josh nodded his understanding.
"Come on sweetie," Penny said, "Let me help you get things together. I'm going to be here all day and want to play hostess while you play slut." And they patted off to the kitchen.
Jenny returned with a cold mug of beer with just the perfect amount of head. I noticed Penny had opened the first of many bottles of wine. The prepared a brunch tray and brought it out to the lanai as we all sat out there on a beautiful morning.
We snacked and drank while Jenny sat on her knees waiting instructions. From time to time I'd have her come over and suck my cock. Josh got in on the fun as well. Penny loved reaching into Jenny's pussy from behind and fingering her as she throated one of us. She'd bring her just to the edge of coming and then back off. After about an hour of this, Jenny was flush and she was staring daggers in Penny's direction.
Close to noon the doorbell rang again. I secured Jenny's hands behind her back this time and had her kneel with the leash in her mouth. When I answered, it was a courier for a very high security service my company used. He had papers from my company that I had to sign for. I invited him in and he immediately saw Jenny. I don't know who had the better look on their face; the driver or Jenny. It was priceless. I said, "let me grab a pen. She'll suck your cock if you like."
The driver said, "Oh no sir, that wouldn't be appropriate."
Penny and Josh walked in to see who it was. Penny had no shirt on. She said, "Does anything about this look appropriate? She's free to use and you're not likely to get a better offer today."
So the guy dropped his pants and put his cock in Jenny's face. She looked over at me and I just looked at his cock as if to say, "get to work." So she did.
I think the guy was so surprised by the whole thing that it didn't take him about about a minute and a half to pop. As he zipped up and turned to leave I handed him a hundred dollar bill and expressed how much I appreciated the confidentiality that was a hallmark of his courier service. He nodded his understanding, took the money and the signed receipt and left.
As soon as the door closed, Josh and Penny and I all laughed. Jenny smiled but she wasn't sure whether to laugh or berate me for what just happened. She asked, "Did you know he was coming today?"
I told her, "Not when we first concocted this arrangement. However, he texted me while Penny was on your face and I told him that I was home all day today."
"Bastard," she said. I walked over to her, took the leash and spanked her playfully, and put my cock in her already come coated mouth.
I told her, "We can stop anytime you like. You know the safe word is simply, "Stop" and it will end, no matter who is penetrating you. You can trust me in that. I love you and won't let you get hurt. But to be clear, my little slut, you did not object before that man's cock reached your lips."
Jenny's face flashed red and the rest of us had a knowing laugh at that fact.
We moved back to the lanai and I undid Jenny's wrists. I told her I needed another beer and we needed her to refresh the snacks. Penny followed her into the kitchen and I heard some moaning. Penny was on the kitchen counter with Jenny's nose in her pussy. I yelled out, "Where's my beer," not to be an asshole, just to keep Jenny on edge.
Jenny came running back with a beer in hand, picked up my mug and proceeded to fill it. I told her, "you just put cold beer in a warm mug. So two things are going to happen. Actually three. The first is you are going to chug that beer, right now. The whole thing without a break." Jenny did. She's kinda small so a whole beer fills her belly fast.
"What's next, Master," she asked with a grin of satisfaction that she managed that chore.
"Get me a fucking cold beer in a cold mug," I snarled.
Jenny ran to the kitchen and then came back with a perfectly poured mug of beer. "And now?" She asked with a smug expression.
"Now you have a choice. Since you wasted a perfectly good beer, do you want a hard ass whipping or a hard ass fucking?" I told her.
She looked at me and at Josh, and asked, "Who will be fucking me?" I know she was scared of Josh's cock in her ass. It was huge.
"You don't get to ask questions," I told her.
"I guess I'd like to get ass fucked," she said in both a question and statement to her voice.
I turned to the kitchen and called out, "Penny, I saw you walked in with a large purse. Is there a strap on in there?"
"Of course, silly boy. Do I get to ass fuck you?" Came the reply.
"No, but Jenny needs it," I told her.
"Coming right up," Penny called back.
Josh and I were side by side on the loveseat on the lanai so I told Jenny to kneel on all fours in front of us, facing to the side. We both put our feet up on her back and shoulders and leaned back. Penny came in naked sporting that big cock shaped dildo.
Josh said, "Jenny, you know if you can take this dildo you can take my cock without a problem. This is her big one."
I felt Jenny shudder under my feet. Then I held up my mug in a salute to Penny and she began to lube up Jenny's asshole. After a moment, she guided that dildo in. She took her time and Jenny was very uncomfortable. She moaned, but not in a good way. This thing would take some getting used to. I was kind of amazed when she finally got the head in and wondered how much of the length would fit. It had to be 10" long.
As Penny worked it in and out, applying more lube as she went, I reminded Jenny, "Remember, you are not allowed to come. Don't make that mistake."
Jenny responded with ragged breathing, "No fucking... way ... I'm going to.... Come with all.... This ... pain."
"Baby," I said, "I promise to kiss it when Penny is done."
As we sat there and Penny began to get a rhythm, Josh's hand moved to my lap and massaged my hard on. A hand's a hand. A mouth's a mouth, right? So I got an idea. "Jenny, Josh wants to give me a blowjob. Would you like to see that?"
"Not... right no... now." Came the reply.
"Oh honey, he's got me hard, I think you need to watch this. I know you've wanted to see me with a man all this time." I said. I got up and moved to stand in front of her. I took hold of her leash and pulled her head up as Josh got on his knees in front of me. Penny sat back on her knees and pulled Jenny into her lap, forcing the dildo nearly all the way in. Jenny cried at the pain.
Penny said, "I can't wait. Suck him off honey. Jenny, I think you need to fuck yourself as I watch with you." Jenny kept riding, if only to get that invasive creature out of the depths of her bowels.
Josh pulled my shorts down and proceeded to blow me. Damn he was good at it. I wasn't sure I could last long.
"Ding Dong" came the doorbell. As if she was a dog distracted by a squirrel, Penny jumped up to get the door, yanking the dildo out in a way that caught Jenny by surprise. She reacted with a spasm that wasn't an orgasm. More like someone having her entrails pulled out from behind.
Penny ran to the door and opened it to find Ken standing there. "Come on in, Kenny. We're already playing."
"I can see that," he said looking at her naked form with the impossibly large dildo attached.
"Beer?" she asked.
"No, I'm working until 5. This is my lunch break so I just stopped in to see what was happening." He replied.
"Come on out back," Penny invited and led the way.
"Fuckin A," Kenny said, "That's a hot scene. I didn't know you swung both ways Mr. J."
"I don't, Ken. But Josh does and I was feeling generous. Would you like a blowjob. Jenny isn't busy at the moment," I offered.
"Sure," he replied and got in front of Jenny. Penny moved back in behind her and began to insert that dildo back in. "Holy hell," Ken screamed, "She bit down when you put that thing in. Give a guy a warning next time."
"Sorry," Penny said in a bubbly voice that indicated she wasn't sorry at all.
After Penny got a rhythm going again, Ken offered his cock. Jenny took it and began to work on him, this time without teeth.
I walked away from Josh to sit back on the couch. He was disappointed but I wasn't feeling it. I grabbed my beer and watched Jenny going down on Ken.
Ken said, "Sorry, but I gotta go back to work soon. Let me take over." He grabbed her hair on the back of her head and and his cock with the other hand. Then he began to fuck her face while also jerking his cock. It was only a couple of minutes when he pulled out and jerked his load onto her face.
Jenny, still riding that massive dildo, smiled and licked the come off her fingers as she wiped it from her face.
Ken said, "Hey, someone said something about pissing on someone. I've never done that but really want to. Who do I get to piss on."
Jenny responded, "That would be me too, sir," playing the role so well.
She looked at me and asked, "Can I remove the leather restraints first, so they don't get ruined?"
I nodded my "yes" and then said, "Either on the tile floor of the living room, or the bathroom shower. Not on the carpet. And leave the body suit on. I want to see it get soaked in piss."
We all moved to the bathroom where Jenny opted for the claw-foot tub instead of the shower. She said, "Please all gather around and give me your piss."
I really didn't think I had to go, but the offer was too tempting. We all gathered around as Jenny lay back in the tub. "You may finger yourself as we piss, but you may not come," I instructed.
Ken was the first to let go and he was like any young guy, he had a hard stream that would knock a girl over if she wasn't already laying down. The sight of his yellow piss soaking the white body suit was pretty damn hot. Josh followed and aimed his piss at her face and hair. Jenny was turned on by this and seemed to luxuriate in it. It wasn't my kink, but seeing her enjoy it was. I just couldn't seem to get a stream started.
We were all surprised when Penny stepped into the tub and straddled Jenny's hips with her feet. She had removed the dildo and she began to piss all over Jenny. It went from her face to her tits and then all over her stomach. Jenny was rubbing her clit hard at this so I reached down and took her hand away as a gentle reminder. She moaned her disappointment and writhed in the tub of piss.
I finally was able to piss and when I did, the volume of three beers in the morning came out in a long and constant stream. It didn't have the back pressure of Ken's but it lasted longer and Jenny seemed to really enjoy it as I hosed her up and down. We locked eyes and the smile on her face told me she really wanted this.
I don't know if it was some latent childhood need to be scolded for being a bad girl, or some odd kink from years of viewing porn, but she really did enjoy the humiliation of it. I was only too glad to help.
After I was done, Penny took charge as she tended to do, "You boys go back to your beers while I get Jenny cleaned up. She may have more guests throughout the day and we don't need them feeling like they're getting sloppy seconds... that is unless they want it."
So we obeyed. As we headed out the door, Ken said, "Goodbye Jenny. I hope to be back later. Amber has her lunch break next. When I tell her what happened she will probably stop by."
As he left I called after him, "Take a sandwich. You probably should have something to eat on your lunch break."
As Josh and I sat and chatted, I heard moaning coming from the bathroom. It sounded like Penny, but I wanted to be sure. Besides, I wanted a private conversation with Jenny, just to check in.
I walked in to find Penny standing in the shower and Jenny on her knees, licking Penny's pussy. Penny was moaning and thrashing as her beautiful tits were swaying to the beat of her orgasm. I stood and watched the show until Penny pushed Jenny away and the two finished rinsing off.
As they exited the shower I provided towels for them. Penny wrapped her towel around her waist and headed out the door. As Jenny went to follow, I stopped her and asked her to stay for a moment. She responded, "Yes, master."
I said, "I want to drop the role-play for a moment. I want to be sure you are OK with what's happened so far. Do you have any regrets or would you like to place any limits? Or, maybe even drop the whole thing? It's early afternoon and we made this invitation for the whole evening. I'm just checking in."
Jenny stepped up to me, naked as the day she was born, and embraced me tightly. "This is why I love you so much," she began, "You enjoy the playfulness but are so concerned about my boundaries and well-being. Thank you. I have to admit, the dildo was a bit excessive. I really hurt and I don't think I'd like to do that again... at least not in my ass. And Josh may be off limits there as well. Other than that, the spanking, nipple play, bondage, everything we've done, I've loved it. I want more, including the piss play. I know it's not your favorite kink of mine, but I really do enjoy it. So, I'll remember that "stop" means stop and that you'll reinforce that. But I really would like to keep going... Oh, and by the way, you letting Josh blow you... that's another kink of mine and you knew that. So you let it happen. The gift of that wasn't lost on me. Thank you for today and what's yet to happen."
I reached up with one hand and put it behind her head to draw her into a deep kiss. With the other hand I grabbed a nipple and pinched and twisted. Then I said, "Thank you what?"
"Thank you Master," and we were suddenly back in character.
"Pick up your leathers," I commanded and she did.
I reattached both cuffs, then fitted the belt around her waist and the collar around her neck. I attached her wrists to the strap in the back and said, "Now let's get you something to eat and drink. You must be hungry."
I led her to the kitchen by the leash. Josh and Penny were seated in the living room and watched as we walked by. In the kitchen I asked, "Tell me what you'd like to eat and drink."
Jenny responded, "Maybe just some meat and cheese cubes. Also a few carrots and celery with ranch dressing."
"To drink?" I asked.
"I'd like a bottle of water and also some wine." She said.
While she watched, I pulled three bowls from the cabinet. I filled one with the food, just randomly placed like a mix of dog food. Into the second bowl I poured a bottle of water. The third got about half a bottle of wine. I took all three bowls and put them on the floor in the living room and took Jenny by the leash and led her to them. I made her kneel on the floor and said, "If you're going to make your master prepare your food, you're going to eat it like a dog. Enjoy."
Jenny got a nasty scowl on her face before she obediently bent over and ate and drank from the bowls. She ate about half the food I prepared and drank all of the water. She started on the wine when the doorbell rang again.
Penny jumped up to answer and I told Jenny to keep drinking. Amber walked in and went, "Holy shit, Ken wasn't joking. I love you bunch of perverts. Jenny, you look so hot right now."
I asked Amber what I could get her for lunch and she had about the same answer as Jenny, but without the wine. She had to finish working, too. I asked her to sit down and I prepared a plate for her and brought her ice water in a glass. Jenny noticed the difference and pouted a little.
"Amber, I asked, would you like Jenny to bring you to orgasm while you eat?" I offered.
Amber said, "I would love that. But I don't want all that wine and ranch dressing on my pussy."
"That's OK," I told her, she'll clean herself off.
Jenny struggled but managed to stand up on her own. She looked to me and I shrugged. So she turned around and over her shoulder indicated that her cuffed hands meant she couldn't clean herself off. I shrugged again. She huffed off to the kitchen to figure it out.
When Jenny returned from the kitchen, she was cleaned off, but her hair, which had dried a little, was soaked in spots. I smiled at her and nodded at Amber. She had already pulled her shorts down in anticipation. Jenny clumsily knelt and let her head fall between Amber's thighs and into her pussy.
I sat down next to Amber to watch. As I did, I played with her tits. Amber quickly finished her food and leaned way back on the couch to give Jenny better access. Then she said, "Mr Johnson, I just love your cock. Can I blow you again? Is that OK?"
I didn't respond except to pull my shorts back off and climb on the couch to allow her to suck my cock. Amber wasn't great at sucking cock, though it was clear she had experience. I thought, with a little teaching and her cock sucking enthusiasm, this girl could be great.
Jenny, on the other hand, seemed quite adept at bringing a woman to orgasm as Amber was there in about 5 minutes. As she did, she also grabbed my ass with both hands and pulled me deep down her throat. I had expected the opposite. I was surprised that instead of gasping for air, she was inhaling me. There's nothing much better than deep throat for a guy and this pushed me over an edge I didn't know I was close to. I came down her throat and I don't believe any of it actually touched her tongue. Wow, what a turn on. I thought, if Jenny and I do end up together long term, we're going to have to agree that Amber is our mutual side chick.
I ordered Jenny to stand with her back to me. Then I unclasped her cuffs and ordered her, "Get Amber a bottle of water to go. Get me another beer. And whatever Josh and Penny want."
Penny, ever the one to play along, jumped up and let her towel fall to her feet. Then she grabber the leash and said, "Come on, Pet. I'll help you." It was cute in a playful way.
While they were in there, a text came over my phone. It was Jackson and he wrote, "JUST HOW OPEN DO YOU WANT THIS OPEN HOUSE TO BE? I'D LIKE TO BRING A FEW GUYS WITH US."
I hadn't expected that Jackson would be able to make it, but he seemed to be ready for it. I typed back, "MY HOUSE ISN'T THAT HUGE, BUT WE CAN CERTAINLY ENTERTAIN A FEW EXTRA GUESTS. BRING THEM ALONG."
I was really excited to see what this would mean. We had a bit of a rest for most of the afternoon. We sat around and chatted. Once in a while one of us would molest Jenny just for fun. We'd bring her to the edge of orgasm and then deny her. We'd fuck each other while she watched up close. Or we'd have her fuck-lick us while taking turns with Penny.
When it came closer to supper time, Penny took Jenny to the kitchen to help her put together platters of hors dourves for guests when they arrived.
First through the door were Ken and Amber. They asked if they could my bedroom and bathroom to shower and change in after an day of work. I nodded and asked if they needed Jenny to wash them off. Ken said, "Hell yeah," so I sent her with them. They all three piled in the shower with instructions that Jenny couldn't come yet, but they could come however and how often they would like.
There were moans coming from the bathroom in no time and I knew Jenny was being used well. When they emerged, Ken was wearing a pair of shorts and a linen shirt, unbuttoned all the way down. Amber came out wrapped only in a towel, gushing over how much I must have spent to get such soft towels. She was towing Jenny by the leash and she was cuffed again around back.
I un-cuffed her so she could handle drink orders and sent her off to the kitchen. When she was done, I had her kneel in the center of the room as we all sat around on the chairs and couches, lazily petting one another in what I assumed was a prelude to an orgy.
The door rang again and it was Camden and Paloma from Josh and Penny's restaurant. They were holding hands and Penny whispered to Josh, "Well that's something new. Should we be concerned?"
Josh replied, "Not if we get to watch."
That caught an elbow from Penny. But she did say, "I know, right?"
Paloma looked ravishing and overdressed in a short dress that did little to hide the bulge between her legs, that I now knew to look for. She's transitioning and apparently had caught the attention of her co-worker Camden, who was also a minority owner in the restaurant.
Of course, they noticed what was going on and Camden hesitantly said, "Oh, I didn't know it was going to be that kind of party. Penny failed to tell me about this. Honey," he said turning to Paloma, "Are you OK with this? We can leave if this makes you uncomfortable."
Paloma responded by walking over to Jenny and pinching her nipples very tightly. "No," she said and then continued in her broken English, "I very much want stay." This brought a huge grin to Camdens face and a subdued shout of "hooray" from all of us.
Paloma continued, "I think me too much dress." And Cam was immediately at her side, pulling down the zipper in the back. As she stepped out of her dress we were treated to a mostly naked form. Her breast implants were a healthy B-cup. Her cock, well we couldn't really see because it was encased in a pink plastic cage. She also had a jewel at her asshole indicating a butt plug.
I'll maintain to this day that I'm not gay, but she could convince me to hop in bed with her.
"I see Paloma is in a similar situation as Jenny. For now, we are not allowing her the relief of an orgasm," I mentioned.
"Oh, Paloma is allowed to come. She finds the cage just makes it easier for her to hide her bulge if she gets turned on," he told us. "You're probably getting quite uncomfortable in that right now, aren't you babe?" He asked her.
"Yes, but I like the ... how you say ... uncomfortable.." Paloma told us.
I was seated on the couch next to Josh when Paloma plopped down between us. She barely fit, so there was a lot of skin on skin contact. It was weird to me. She was hot, but had a cock. My brain didn't know what to do with that... so I let Jenny deal with it.
"Paloma, if you let your cock out, Jenny would love to suck it," I told her.
Paloma looked to cam for the key to the little lock that dangled between her legs. He came over, knelt between her knees, and proceeded to un-cage her. When he finished the task, he said, "Me first," and stuck her growing cock in his mouth. I watched as he sucked her and her nipples grew hard.
Cam stood back up and pointed to Jenny, as instructions to get over to that little girl cock. And it was little. My guess is it was about 3" fully erect. It was almost "cute."
I was mesmerized. Watching Jenny give anyone a blowjob is always a turn on. So as I watched, I turned to Paloma and played with her tits. I mean, tits are tits, am I right?
While Jenny was at work, I nodded to Cam to take her from behind. He pulled down his pants to reveal a nice, average sized cock that he gladly buried to the hilt. Jenny moaned in pleasure and I knew she probably had no control over her orgasms at this point.
I told Jenny, in the hearing of everyone else, "You may come on Cam's cock, but know this. As soon as you do, you will experience cock after cock, and tongue after tongue, dildo after dildo, all night long. We won't allow you a time to rest as you orgasm time after time. Do you understand?"
"Yes, Master," Jenny moaned, "I really need to come and I agree to your terms."
"Cam, would you please fuck Jenny as hard as you can?" I said to the man I guessed to be about my age. Cam responded by grasping the leather belt and slamming into Jenny's ass with a hard and fast tempo.
Jenny shuddered as she came and the moaning nearly sent Paloma over the edge. Since she was coming so hard, Jenny pulled her mouth off Paloma. I said, "Paloma, would you like to fuck Jenny next?"
Paloma responded, "I've never fucked a woman before."
"It's probably a lot like fucking a man, I suppose," I conjectured.
"I've never fucked a man before," Paloma responded and I realized she was clearly a bottom when it came to sex.
"Would you like to try?" I asked, as I looked to Cam to make sure I wasn't crossing any boundaries. I had no idea what the proper conventions were in the LGBT community. Josh sucking my cock was as close as I've ever been.
Cam just shrugged his shoulders as he was concentrating on banging Jenny. He was also beginning to sweat as his pace was swift. Jenny began a sincere amount of moaning before face planting back into Paloma's crotch with a spastic orgasm. Her cuffs were still attached at the back so she had no way to support herself.
Her jerking movements, and I assume contracting pussy walls, had Cam coming a moment later. He flooded her womb with a loud groan, which elicited a light applause as everyone in the room was invested in what was happening.
Cam pulled out and Paloma moved behind Jenny. We moved Jenny so her whole chest was on an ottoman with her pussy available in the same doggy style she had just experienced. This also made it possible for her to be face-fucked.
Paloma took hold of her own cock and placed it in the entrance to Jenny's pussy. She had an unsure look on her face. Cam came to her side and hugged her tight as he coaxed her into Jenny. Paloma said, "Oh, that's very warm and soft. I was not sure what it would be like." All the men smiled at that with knowing grins.
Paloma began to pump into her but there weren't any moans that came from either of them. We all kept watching the show of Paloma fucking in very short thrusts. Finally, after quite a bit of time, Paloma said, "Is it supposed to be this...." Then she switched to Spanish, looking at Cam, "perder?"
Cam spit out his beer as he laughed. "She just asked if it was supposed to be this loose." And we all laughed, except Jenny. She looked back in disgust.
Telling a 43 year old woman that her pussy was too loose was the ultimate humiliation. The truth was, it really wasn't loose to most guys. However, Paloma's cock was tiny, she was fucking in sperm-filled sloppy seconds, and she was following a cock that was easily twice as big around.
I explained that to everyone and Jenny growled, "Then put it in my ass you fucking bitch."
I jumped up at the same time as Penny. I was moving to whip Jenny's ass for what she said. Penny was getting the lube.
I moved to Jenny's head and shoved my cock in her mouth. Then I took her leash and started to whip her ass. Not too hard, but enough to drive home the point.
In the mean time, Penny was there with the olive oil she loved to use. She rubbed it all over Paloma's cock and there was a look exchanged between them that was an employer seeking permission and an employee granting it. I'm sure it wouldn't hold up in court, but I also guessed there would be future transgressions in their relationship.
Penny lined up Paloma's little dick to Jenny's ass and Paloma slid it in. Paloma groaned, "Is better!" And we all laughed again.
Penny understood the plan of not letting Jenny come down from her orgasmic hilltop, so she reached underneath to finger Jenny's clit. This worked and Jenny was soon moaning around my cock.
Paloma called out, "I will come soon. Where I come?"
"Anywhere you like sweetheart. Since you've never fucked anyone, I think you'll enjoy coming in her ass, which is just fine." I said to the sweet face looking across Jenny's back at me. Somehow our eyes locked and there was a connection there. Again, without even trying, Jenny was expanding my own sexual identity.
Paloma was a gorgeous, petite, black haired beauty with deep brown eyes. Her tits was so pert and looked like they belonged on a natural young lady. When she came, she and I were locked in a stare. The look on her face was that of joy, relief, triumph and peace. I couldn't help myself. My own orgasm flooded Jenny's mouth. From the sound of Jenny's moans and gags, there was more come than usual.
Paloma, Cam and I sat on the couch. We were tapped out. So Josh jumped in to keep the gang-bang going. The doorbell rang Penny jumped up to answer. She is so funny the way that her short, pudgy, cherub like self is happy to answer the door stark naked.
When she opened it, she suddenly stepped behind it to hide her nakedness. I looked over and there were three huge guys, one white and two black, at the door. I could see how this might frighten Penny but I called out, "Jefferson, Bruce, welcome. Who's your friend?"
These guys were all bouncers at Jackson's strip club. Jefferson responded, "Mr. Jackson and Ms. Valeria send their regrets. The three of us have the night off so they said there was a party we might enjoy attending. Is that OK?"
They were still at the door and I could barely see all three with their football lineman size. Suddenly as small hand appeared between them. Then an arm and a shoulder as Joy pressed through. "Go in or get out of my way," she demanded. It was so funny to see this diminutive figure pushing these guys around.
Joy came inside as Penny shrugged her shoulders in a gesture asking me if it was OK. I made the introductions as I nodded yes. "Everyone, this is Joy, she works for my friend Jackson who owns a restaurant, I'd love to take you to sometime." I said, acknowledging Josh and Penny. "This is Jefferson and Bruce," I said, pointing to one black and one white behemoth at the door. "They are bouncers at the strip club. Hey, I still haven't heard your name," I said nodding to the other black dude.
"You can call me Johnny," he said. "And if you don't mind me saying, this is my kind of party."
Penny took drink orders and Paloma jumped up to help. Two of the guys watched her closely as she made her naked way into the kitchen. I knew we were in for quite a night.
"Guys, our goal here is to keep Jenny coming all night." I told them. "Her safe word is simply 'stop' and I'd like you to honor that." Honestly, there was nothing I could do if they didn't. I suspect Joy knew how to keep them in line. "Other than that, anything you want to do with her, or the others, is fair game. Consent being the important rule, overall."
"So, is there a line to fuck her?" Johnny asked.
"Paloma, the tiny girl you just watched walk by, just came in her ass as I came in her mouth. Cam had already come in her too. That's Josh fucking her now. So you guys showed up just in time." I told them.
Penny and Paloma were coming in with the drinks and Penny said, "Paloma and I just agreed that we'd like to be the fluffers." They handed out the drinks and dropped to their knees. I noticed Johnny shouldered the other two out of the way to get in front of Paloma. Penny began to take down Jefferson's pants as Joy joined them to take down Bruce's.
Over the next couple of hours, Jenny was fucked in a constant train of us. As soon as one of us was done one of the girls (and Josh too) would clean her pussy of come. The next guy would step up and begin fucking her right away.
Jenny was in a relentless state of climax. She alternated from moaning and shuddering, to screaming, writhing and spastically shaking. There were 6 men sharing the rotation. As time went on, I had to let others step in to my spot in the rotation. I had come 3 times that evening and I was having trouble getting hard enough to make a difference.
Penny noticed the potential for a lull and took that opportunity to get out her strap on. While Paloma and Joy continued their efforts as fluffers, Jenny would fuck Penny until the next guy was ready. Except for the potential of a leg cramp, Penny could go all night.
Jenny was a champ. I think we were fulfilling her sluttiest desires. She allowed herself to be doggy fucked for over two hours. I have no doubt she was suffering a lot of cramping in stomach, legs, and pretty much all over.
I called a time out. Jenny didn't say "stop" but I wanted to make sure she was physically able to say it. I asked Paloma to grab her a bottle of water and laid her down on the cool hard floor.
"Honey, are you ok?" I asked.
At first she seemed unable to answer. She was still spasming. It was as if she no longer needed us to cause an orgasm in her. Her body was so flooded with dopamine, oxytocin, endorphins and all other chemicals it produces during an orgasm that it was on overdrive.
I let her lay there a few moments and offered her water. It took a moment but she finally sat up and drank from it. She was covered in sweat. Her hair was a mess. Her eyes looked like they couldn't focus, or didn't want to.
As everyone was looking at her with concern she finally said, "Can you release my arms please."
I took the cuffs off and and removed the collar and belt. Then she curled up into my arms and shivered some more.
With everyone relieved that she could talk, they all began to relax. Most of them went for a beer or something harder. Some opted for water.
Jenny looked up at me and said, "Kiss me?" Which I gladly did. It was a very tender intermingling of our tongues.
Then she said, "I'm very sore and could use a massage. But then, I'd love for all the guys to take one more turn." I was shocked by this revelation.
I went to get some blankets and created something of a mat for her to lay upon. Jenny lay upon it and I began to massage her back, arms, legs. I was quickly joined by a couple of others but then it turned into all of us. Jenny had 9 pairs of hands rubbing her down.
I asked them to avoid her pussy and asshole but to just gently rub the muscles down. Jenny later told me the sensation was amazing and she almost came from the feeling of them all touching her body without the intent of making her come.
Finally, Jenny rolled over on her back and said, I'm ready for each of you to have one more turn on me. Cam was quick to respond and had his cock in her very quickly. Jenny moaned her appreciation.
Instead of the rest of us backing off, we stayed close and kept our hands on her. Breasts, nipples, stomach, legs. We continued to rub her down and it wasn't long before she was coming again. I bent down to kiss her as she did.
Cam finished in her and was replaced by Jefferson, then Johnny, then Bruce, as they mentioned they had to get going. Jenny kept on her orgasmic high as each one finished in her and Joy cleaned up in between.
As they were saying their goodbyes, Paloma stepped back in again. She said, "Is OK in ass?" And Jenny nodded. Of course Penny was right there with the lube. While Paloma fucked, Penny licked Jenny's clit to keep her on that high.
"I think I like fuck ass," Paloma said, having never been a top before. She turned to wink at Cam.
Cam laughed, "I don't know why you're winking at me?"
Josh chimed in, "I'm always here for my employees."
We all laughed at that. Except for Jenny. She was too far gone to laugh. But she did smile. Kinda.
Paloma didn't last long. Jenny's ass was tight and her ongoing orgasms made it even tighter.
Josh stepped up next and plunged that huge rod in Jenny's pussy, with no resistance. This sent Jenny into orbit and she began to writhe. Josh grabbed her hips and began pounding relentlessly.
After a couple of minutes I was concerned that Jenny was again unable to verbalize her need to stop. That's when a nasty side of her came out that I wasn't ready for. Jenny said, "Oh yes, fuck that pussy. Get that horse cock deep in me. Fuck me!"
With that encouragement, I backed away and Josh kept plowing. It took him a long time to come and Jenny's words kept flowing like a team of construction workers. Eventually, Joshed shoved hard and deep and he came with a loud grunt. He went a little too deep and Jenny shrieked in pain and pleasure.
So I knew it was my turn again. I would be the last and I wasn't sure I was up to the task. I was semi-hard but not impressively so. As I moved closer to Jenny, Paloma, who as laying on her side by Jenny's legs, noticed my predicament. She took me in her mouth.
These last two weeks I've said, "A mouth is a mouth." But a mouth connected to tits, a cute ass, and a woman's face. That's no normal mouth. Paloma also had the tongue and lips to go with the rest of the package. I was harder than I was before and she helped insert me into Jenny's pussy.
Jenny's face changed and she said, "Make love to me." I leaned into her and began to calmly and gently enjoy her body.
As Jenny's breathing and shaking got under control, the others took this as a cue to leave. Each one kissed Jenny and me. Not Cam, but Penny and Paloma kissed us both. I also think that Josh may have kissed both of us, but I'm not too sure.
It was close to 2am and Jenny had been coming for about 6 hours. We melted in to each other and simply enjoyed the loving body contact.
At some point we woke up that same way. My cock had shrunk from inside her. I'm not eve sure I had come. It really didn't matter. I picked up Jenny and took her to my bed. She curled into a fetal position and I spooned her from behind. Jenny pulled my arms around and tight too her breasts and she wrapped herself in my like I was a blanket.
We slept a dreamless sleep that lasted until about noon that day.
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