Secrets Ch. 56

56

I tried not to let the real truth show on my face as I stood there, helplessly watching my wife's best friend masturbate. She was doing it as much to torment me as she was to pleasure herself, even if she seemed to be doing a very good job of the latter. In my old life, I'd known that Jennifer was very attractive, but I'd done my best not to notice it in too many details. Now, watching her spread herself out, legs splayed as she stroked herself while starting to aggressively stroke and squeeze her own full breasts, there was nothing else to look at.

It was intoxicating to see how intensely and expertly she touched herself. With her eyes fluttering nearly closed, she looked lost in the sensations, but her fingers danced and dove inside with exacting precision. I could see her nipples tighten and her skin flushing red.

Amidst the sounds of sex from above us, and with her trapped audience of one, she brought herself to the crest and over it. She came hard and wet, her fingers moving in a blur at the end, gasping and then crying out with pleasure with moans loud enough that perhaps Jane might have heard upstairs.

Jennifer smiled and winked at me, once she was finished and her breathing slowed again. She stood up and her skirt fell back into place while she adjusted her top. Upstairs, the sounds of sex continued unabated, making me feel some reluctant admiration of this man's youth and stamina.

I watched Jennifer intently as she rose to her feet again. My mind felt so broken and my body was aching. Once again, she reached up under my skirt and into my panties. This time I could feel the warmth and moisture from her pussy coating her fingers. She gripped me tight, and she kept the pressure increasing as she spoke.

"I'm sure this is closer than you've been to a woman in some time," she smiled. "But I'd still bet you were thinking about men, weren't you?"

I nodded, moaning with shame and the throbbing agony of her grip on my tortured balls.

Using her free hand, she managed to reach behind my head and release the buckle on my gag without ever releasing her vise-like grip.

"Say it out loud, Dolly," she instructed.

"I was thinking about men, Miss Jennifer."

"What were you thinking about them?"

"I was thinking about sucking their cocks and feeling them fucking me," I confessed.

"While you were watching me, Dolly? Why is that?"

"Watching you made me think of orgasm, Miss Jennifer, and I know that I don't get to be with women anymore... so my orgasms are more likely to be happening with men."

"Did you cum today, Dolly? When you were pleasing men or having them use you?"

"No, not this time, Miss Jennifer."

"What a shame," she teased. "Well, perhaps you'll get another change to be fucked soon."

"Thank you, Miss Jennifer," was all that I could think of to say.

"You are welcome," she said with a smile. "For now, however, I'd really like a drink, and I'm even starting to wonder about dinner. Are you ready to get back to work?"

"Yes, I am, Miss Jennifer," I answered eagerly.

"Very well," she said, and mercifully started to unbuckle me from the cross.

It was such a relief just to be able to move again, even if that meant having to walk on high heels again.

"Why don't you start by washing up a bit," she said. "The load of cum on your face was amusing, but if you're going to be attending to your maid's duties, I think it best that you are fresh and clean."

"Yes, Miss Jennifer," I agreed, blushing.

I hurried to the downstairs powder room, not wanting to intrude on what was audibly still going on upstairs. It took more scrubbing than I was expecting, as the dried cum was quite stubbornly stuck to me, but eventually I got my face clean and smooth. Jennifer smiled at me when I returned.

"You look much more presentable now, Dolly, but I think once you fetch me a glass of wine, I'm going to give you some pointers on makeup. You'd look much prettier with a bit of colour and contour."

For some reason, the idea of putting on makeup made me blush again. I supposed, as I returned to the kitchen and poured her a glass of chilled white wine, that it was just one more step in becoming Dolly.

Jennifer was ready for me when I returned, with her purse open on the coffee table and its contents starting to be spread out, including a small folding mirror propped up. She patted the cushion on the sofa beside her, so I lowered myself down and sat beside her. Despite having just tormented me by putting on a show of her masturbation and orgasm, now all of a sudden she felt quite sisterly and kind.

"Now, for a girl like you, there's the whole issue of skin care, beard cover and concealer, but I won't get into that for now. I just want to show you what a bit of contouring and colour can do for you. Why don't you just turn to me, and I'll show you this time."

I turned towards her, my knees touching hers.

She pulled out a folding case that seemed to hold two squares of colour, one lighter than the other, but both close to my own skin tone. She brought a makeup brush to the darker colour and then lifted it to my face.

"We just trace a bit of a line from the tip of your mouth to your ear," she said as she did so, "and we accentuate the contours of your face, as though the sun was shining down on you. We use the lighter colour on your forehead, over your cheekbones, and across the bridge of your nose, and then the darker colour below. We use the line I started with to give you the illusion of higher cheekbones than you naturally have. The brush smooths out the transition, making it look as natural as possible."

She was so close to me, just inches from my face. What was happening was intimate, but not sexual.

"Next we use some blush, to give a bit of colour to your cheeks. It doesn't take as much as you might think."

I could feel her dabbing just three or four dots of colour on each cheek and then smoothing them out. She smiled with her eyes as she worked on my face, and it made me feel strangely excited. I was realistic about how much transformation a bit of colour could provide, but I was becoming eager to see the results of her work.

"I'm not going to get into mascara or eyelashes or eyeliner right now, but those will be important too. I'm just going to give you a bit of colour," she said, and brushed something more above my eyes.

"Lastly, and most importantly for now, your lips," she announced.

She reached down into the bottom of her bag and pulled out a tube of lipstick.

"You may remember this," she said. "It's a special plumping lipstick. Not quite FDA approved, but it does such a pretty job of adding colour and fullness. Part your lips for me."

I opened my mouth slightly and I felt her drag the lipstick across my lips, bottom then top. Right away I could feel that tingling again. She was so careful and exact, painting my mouth with it, smiling so widely, and I was so full of sensations that I was positive I could actually feel my lips swelling. She pulled out a thinner tube and gave my lips a coat of a thick gooey gloss, then pronounced my look finished. She turned the mirror to me and had me look.

"Oh, wow," I murmured, feeling the buzz of the words over my tingling lips.

I still looked like me, almost frustratingly so, but I also looked different. I was definitely more feminine-looking, and I could actually witness the effect of the contouring of colour that changed the visual shape of my face. I imagined that if I had a sister, this is what she might look like.

"Yes, it's not bad at all for a start. I'd say that mouth of yours is looking very fuckable," she teased. "It's almost a shame that young Ryan upstairs isn't likely to have much left to give, after Jane's done with him."

Under my makeup, I blushed. All through this experience with Jennifer, the sounds of Jane and this man fucking had oscillated up and down in volume and intensity. Jane was more vocal, either due to her own nature or to wanting to express her pleasure knowing she had an audience, but that didn't mean that Ryan had gone unheard. He was clearly receiving as good as he got.

"It's strange that you're more likely to get lucky with your wife's lover than you are with your wife, isn't it?"

"It is, Miss Jennifer," I confessed. "But I'm starting to get used to it."

"Really? Is that the kind of thing a man can get used to?"

"I... I... I don't know," I answered as honestly as I could. "I accept that she's in control, and I'm so happy that she has taken that control and collared me. I'm so thankful that she is pleased by how I can serve her this way. I know my shortcomings -- the ones in our past that I'm owning up to, and those that I'll always have. I'm honestly happy to see her getting the kind of pleasure that I don't think I could have ever totally given her. But no, I guess there's a part of me inside, that remaining bit of 'man' or 'husband' that will always feel the shame of humiliation of knowing that it takes another man to make her truly happy in bed."

Jennifer smiled at me, perhaps as compassionately as she could.

"I understand, and I'm glad you do too," she said. "Even as hard as it is to still see you as a man, as you currently are, Dolly. For Ken and I, we get different things from the others that we play with or be with, but I still see Ken as a man, and he's still great in bed -- though I guess I don't need to tell you that part."

"Does she talk to you about me, Miss Jennifer? Does she talk about what she still wants from me?"

"She does, yes, but that's not a confidence of hers that I would break by sharing. Those are discussions for you to have with her directly - and I trust that you do, and that you will. I wonder, and I guess I'll just ask you -- do you think there is any wish or desire that you'd deny her at this point?"

"What do you mean?"

"Well, I know that she has forbidden you to have sex with women, other than going down on her when she wishes. I know that she's limited you to orgasms achieved by anal stimulation. She's collared you and given you piercings and marked you as her property and submissive. You aren't allowed to dress like a man anymore, other than the clothes you put on over panties for work. She's fucking men in your bed, and you're getting fucked and blowing guys in between being tied up and on display in your own living room. These things would be unthinkable for most men -- you must know that. Is there anything you wouldn't do, if she asked?"

"I don't know about most men -- other than to say that I've known for a long time that I'm not like them. As hard as some of this is, it's also just as exciting. It's humiliating to have my wife bring a younger man home to have sex with... but I can't explain how it feels so powerfully thrilling at the same time to see that look in her eyes when she does it. I feel embarrassed and silly being dressed like this, but I also love that doing it and obeying pleases both you and her. Obeying feels better than maybe anything else I've ever felt -- that's one thing I know about myself. I can feel the changes she's making, some of which I may have felt starting even before. They are humiliating and mortifying, if I think of having to face other men who might know these secrets -- but I also can't tell you how long I've waited and dreamed about these kinds of things becoming more than fantasy for me."

Jennifer smiled, reaching out to touch my knee.

"I'm really very happy for you -- for you both. I think I know the answer to my question, but I still want you to say it."

"No, Miss Jennifer, I can't think of anything that I could deny my Mistress if she wanted it."

"Good girl, Dolly. Now why don't you get busy in the kitchen. I'm starting to get peckish, and I think they're working up quite an appetite upstairs as well."

"Yes, Miss Jennifer. Would you like me to refresh your drink first?"

"An excellent idea, Dolly. Do that."

I rose up and got to work. Once I refilled Jenn's glass and clicked back into the kitchen atop my high heels, I planned out a meal and began to prepare and cook it. I made plenty, as I wanted to be ready in case Jane and Ryan really were going to be hungry, and I had no idea whether or not Master would appear again either. His wife was here, so I imagined it was at least possible.

I prepared stuffed chicken breasts along with garlic mashed potatoes along with three separate vegetables. I generally liked Sunday dinners to be something special, but today I realized that I was also cooking to impress a stranger. Sure, he had the youth and stamina to fuck my wife all afternoon, but I was going to be the one feeding them.

As things were going in the oven and getting closer to being ready, I heard the shower running upstairs. It started to hit me once more that I was going to have to face this man eye-to-eye, and I was going to have to do so as Dolly. I had to occasionally remind myself how I looked and was dressed, even when my fake breasts kept getting in my way as I cooked. When he'd last seen me, so briefly, I was trapped and displayed in bondage in the living room, but now I was going to be free and moving about, having to engage in conversation while serving dinner. It was a lot to take in, but I knew I had to make my wife and Mistress proud of me.

When the two of them came downstairs, they were glowing. Jane especially was smiling very wide. Ryan looked a touch uneasy, as though he was still finding the situation a bit hard to believe. A pair of beautiful women had picked him up and he'd just spend hours fucking one of them, and now that woman's husband -- in drag -- was welcoming him and offering him drinks and dinner.

He accepted a beer while Jennnifer and Jane continued with wine. I served them their drinks in the living room while I put the finishing touches on dinner. Master arrived just as I was about to bring them all in to eat, so it just seemed natural to place him at the seat I had set for myself, and act as maid and waitress instead.

"This all looks amazing," Master said as he dropped into the chair. "You look very pretty too, Dolly."

"Thank you, Master," I answered, then found myself looking over at Ryan to see how he might react to hearing me address this man in such a fashion.

Ryan didn't say anything about it, but he continued to look a bit in shock.

No longer having a place to sit, there wasn't a natural place for me to remain once I had served everyone's drinks and they had filled their plates and started eating. With a touch of awkwardness, I silently excused myself and waited out of sight in the kitchen, where I could still listen in on the conversation and be ready if called for.

My absence seemed to free Ryan up, and he slowly began engaging in the conversation that circled the table. Master was kind to him, asking him questions to get to know him and reacting with real interest. Ryan had grown up not far out of the city and was now on his own, making his way while working in restaurants and picking up some construction jobs on weekends and after hours.

I listened to them talk and joke and laugh, but then forced myself out into the room once more, to refresh drinks and make sure that they all had everything they needed. Ryan stared at me at first, or at least at my fake breasts, but then kept his eyes down. Jane was beaming to all, and Master and Jen gave me smiling glances. No one, however, talked to me or reacted to me as though I was anything other than a servant or waitress. I watched them, the two couples at my dining room table and imagined that they could be on a double date.

I was not surprised to hear Master be the one to address the reality of the situation first.

"Have you ever been with a married woman before, Ryan?" he asked out of the blue.

"No, no I haven't," Ryan stammered in reply.

"It's exciting, isn't it? Knowing that you're giving her something that she must be finding wanting. It gives you all the pleasure that sex always does, but with that extra kick that you're taking another man's place in her bed and in their sexual relationship."

"I... I hadn't really thought of that before," he answered.

"Don't worry about all that," Jane reassured Ryan. "We had a wonderful experience, and that's really all that matters."

"Is it really the same, when the husband is obviously not the man of the house anymore?" Jennifer asked.

"I guess it is different, since the truth of what is happening is so obvious, when someone like Dolly is kept as she is -- and as she was when you came home," Master answered. "It makes it so much clearer that he can't fill those traditional duties of a man and husband. Did Jane tell you that Dolly is kept in a chastity cage as well, Ryan?"

"She... she didn't, no," he answered. "She just said that they don't have that kind of physical relationship anymore."

"It's true," my Mistress shared with him. "My husband, now called Dolly, is kept locked in a device that keeps him chaste. He can't even get an erection inside of it. I've made it clear to him, with the cage and with my instructions, that he's never going to have sex with a woman ever again."

"And... and he's okay with that?" Ryan asked.

"He is. Dolly is quite happy with the arrangements, and with her new role and her new life. In many ways, I'm coming to find that it's the fulfillment of dreams and fantasies that she's held for a long time," Jane explained.

"Okay but still. No sex. Wow. That's intense," Ryan reacted.

"No sex with women," Master clarified. "Dolly is becoming quite proficient at pleasuring men."

"He's gay?" Ryan asked.

"No, not really," Master answered. "It's more like an understanding that her sexual pleasure comes more from service and obedience than from what might have been her sexual orientation in terms of gender."

"I'm not sure I know what that all means," Ryan said.

"In short," Jennifer explained, "it means that submitting and obeying can make Dolly feel as good or better, even physically, as the sex she used to have ever did."

"But does sex with men turn him... her... on?"

"Yes, it does. Dolly can achieve orgasm from anal sex, but I think she also is really coming to enjoy sucking cock."

"That's... wow... That's hard to believe."

"Let's ask her," Jane volunteered. "Dolly, can you come in here?"

I took a beat and a deep breath, and then walked into the dining room to join them, pretending that I hadn't heard every word."

"Yes Mistress?" I said.

"My new friend Ryan was curious about your new life, and he was wondering if you really like servicing men. Do you, Dolly?"

"Yes, Mistress. I do," I answered.

"You were a straight guy, but now you like dressing up like this and sucking other guys off?" Ryan asked, finally looking me in the eyes and addressing me directly.

"Yes Sir," I answered. "I suppose it just started as obedience to what was asked of me, but I have found to my surprise that I really do like it."

"So you're just gay now, and you're okay with that? While your wife fucks other men instead of you?" he said, letting his surprise and judgement out in the open.

"I don't know if I think of myself as gay exactly," I answered, feeling the burn in my cheeks of this forced honesty in front of a group. "I kind of think of my sexual orientation as submission in addition to my attraction to people, or people of a specific gender. It turns me on to submit and obey. It turns me on to know that my service gives pleasure, even when it's the pleasure of teasing me."

"But don't forget that you just plain love sucking cock," Master teased.

"Yes, Master. I do love to suck cock," I answered, continuing to look at Ryan.

"Do you want to show him, Dolly?" Master asked.

"Master?"

"I should ask our hostess first. You're right," Master smiled. "Jane, would it be alright if, before dessert is served, if Dolly shows Ryan just how much she actually loves to suck cock?"

"I don't mind at all," she answered.

"Thank you," Master replied while Ryan's eyes widened.

"Would you like to suck my cock right now, Dolly? I have a feeling you've been thinking about it ever since you put on lipstick today."

"Yes, Master. I would like to suck your cock very much," I answered as my heart started to pound in my chest.

"Good girl," he answered, and pushed himself back from the table. "You may."

Interlude

Ryan was frozen by shock, watching what seemed to be happening. It has been a strange experience, walking into this house and seeing Jane's supposed husband dressed up like a woman and bound in the living room, but his lust had led him easily past that. The sex had been incredible. She was older than he was, which only seemed to have released a sexual inhibition that he'd never experienced with a sexual partner before. She had made it clear that she was directing things, but she had been up for just about anything. She had taken anal off the table, and she had said that sucking cock wasn't really her thing, but she more than made up for those exceptions with her hunger for everything else.

They'd made their way through multiple positions all over her bed and bedroom. He'd lost track of the amount of orgasms that she had screamed her way through. When he had needed just a few minutes to recharge in between sessions she had kissed him and caressed him and whispered in his ear about how much better a lover he was than her husband. That hit a lot more powerfully, given that said husband was just downstairs and would have had to be deaf not to hear what was happening in his bedroom.

He'd never been with a woman as loud as Jane. She moaned and gasped and made it clear when he was touching her or moving within her the way she liked. She made no secret about it if things could be a bit better if he moved this way or that, and it was encouraging rather than embarrassing. In response, he spoke out too, moaning with bliss when she would reach down and stroke his throbbing cock, or squeeze him tight inside her pussy.

She had quite literally worn him out. It felt as though he could barely walk when they came back downstairs. He held the railing on the stairway, and he flattered himself by imagining that she was walking a bit gingerly as well.

He hung back, not knowing what to say as he realized that Jane's sissified husband had made them dinner and her girlfriend from the restaurant was still there as well. This man was fully dressed up and made up, and his fake, huge breasts were a bit distracting when he served them. They had been joined by another man, apparently Jennifer's husband, who seemed to take the situation he walked into as completely normal.

Even after all of that, Ryan was gobsmacked to see this man, Ken, teasing and verbally tormenting the man they called Dolly, until Ken pushed his chair back and made it clear that he wanted his cock sucked, right then and there.

Dolly seemed more than eager to obey, even though he was blushing. Ryan could see that Dolly was repeatedly looking over at him, perhaps not quite ashamed of what he was doing, but ashamed that it was being made clear how much he wanted to obey these commands in front of this assembled audience.

Ryan watched as Dolly knelt down and opened up Ken's trousers, pulling and tugging and reaching until Ken's cock was exposed. As soon as it was, Dolly dove down onto it, using his hand and tongue and lips to kiss and stroke and caress the shaft and head, getting it all rock hard and throbbing for him to worship and pleasure.

Ryan hadn't seen a blowjob like this outside of porn. Dolly's head bobbed up and down and he moaned and gasped and drooled, seeming to want nothing more than to please Ken and make him cum. Jane and Jennifer seemed to love the show, pulling their chairs out to get a better vantage point on the action. Ryan couldn't look away, even though at one point he made the connection in his mind that, no matter how Dolly was dressed and was acting, he was a man sucking another man's cock, and Ryan was watching it and feeling himself get aroused again. He wasn't gay, he reminded himself, putting all the blame for his body's reactions into how effectively Dolly's uniform, wig and makeup hid the truth. Dolly's lips looked really full and soft, Ryan thought, especially for a man's, making Ryan wonder if there had been some kind of plastic surgery involved.

He forced himself to look away for a moment and when he lifted his eyes up he noticed that Jane was looking at him intensely with a wide smile spread across her lips. She stood up as Ryan met her gaze and walked around the table to his chair.

"It's hot, isn't it?" she whispered into Ryan's ear.

"Yes," Ryan nodded. "Yes, I guess so."

Jane reached down, placing her hand on Ryan's crotch, feeling the bulge of an erection that Ryan hadn't been consciously aware of.

"Stand up, and pull these down," Jane hissed.

Ryan was too dumbfounded to argue. He stood up, loosened his belt and pushed his pants down to his ankles. Jane pushed his underwear down with them, then helped him step out of them. She guided Ryan to turn so that he was watching the action again, then gripped Ryan's cock in her warm hand and began to stroke him.

"Ohhh fuck," Ryan moaned, feeling the almost instant ache.

Ryan felt just a touch sensitive, given the hours of sex they'd already engaged in, but Jane's touch felt just too good.

In front of him, Ken moaned and Dolly slurped. Jane was standing halfway behind him, jerking him faster and faster with her having breasts pressed against him. Jennifer's hands were out of sight under the table, leaving little to the imagination about what she was doing.

When Ken grunted and was clearly starting to cum, Dolly just moaned all the more, as though she was starving for it. The air was electric and stank with sex. Dolly's lips were tightly sealed and she was sucking down every drop.

"Cum on Dolly's face," Jane whispered when they had barely finished in front of him. Dolly was still gasping and licking her lips.

Ryan felt his mind resisting, but Jane's hand was far too effective to argue with. With a grunt of his own he felt his balls tighten and the felt the load rising, impossible to resist. With Jane's hand guiding his aim, he spurted what thin, weak cum he had left over Dolly's lips and cheeks. Jane milked out every drop and Dolly, her face red and her eyes wide, actually extended her tongue out to accept it all.

Ryan collapsed down into his chair, leaning back with a posture that mirrored Ken's. Jennifer and Jane together applauded them with their wet, sticky hands.

Ryan was quite sure it was all too incredible to actually be real.