Collette's Sissy free porn video

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I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade off in one way or another and being Collette's kept man is tricky. I have to recognize her complete authority as she owns everything, but she's not harsh with me and truthfully I feel like I'm on an amazing ride and until recently I never questioned whether or not I would ever want to get off.

Collette is a sensual vision; long red hair flowing down around her bountiful breasts and almost reaching the alabaster skin of her shaven pussy. As with most women who know exactly what they want, she is very much in control of all situations, and we have sex when she wants, anytime she wants. I learned this fact early on in our relationship, but it's not like fucking this gorgeous woman is a chore, and believe it or not there are even fringe benefits you wouldn't believe.

One of the most interesting and dick-stiffening fringe benefits Collette provides is her slutty slave, Mandy. The shag-cut platinum blonde slave predates me in Collette's life, but what most amazes me is how Collette forces her slave to live a life of complete vaginal chastity. In the four years I've lived in Collette's penthouse apartment I've never even seen Mandy's pussy out of the confines of the shiny stainless steel belt Collette locks her up in. I've fucked Mandy's accessible ass many times, with Collette's eager permission, and Collette insists her slave keep her rear opening clean, exposed, and well lubed whenever she isn't wearing a stretching butt plug. Mandy's ass is a tight fuck which I enjoy, but I feel her chastity is a contributing factor to these feelings I've been having lately. It's like I almost feel guilty fucking Mandy and coming in her ass because I know she can't come.

When I first moved in I thought it strange that Collette never let her orgasm, but it persisted with Collette going as far as to lock me out of the bedroom when she occasionally removes the belt to clean both it and Mandy's genitals. I've always wondered what happens in the bedroom on those occasions. Does Collette get to fuck her slave's cunt in private and allow her to climax on only those occasions? I always listened, for sounds of copulation, but never heard any. Every time I asked Collette what went on she told me it wasn't my business and I got even less out of Mandy on the subject. Still though, I've developed feelings for Mandy which seem to generate from my desire to see her be allowed sexual relief. Don't get me wrong, I'm not angry at Collette I just think she's a bit too cruel to her slave. My problem seems to be getting Collette to see it that way.

* * * *

Tonight is Friday night, a special night, to those of us who enjoy Collette's outrageous Friday night fetish sex parties. On my limo ride home from my stockbroker job, I fantasize about Mandy getting sexual relief at tonight's party and of course I see my cock deep in her pussy giving it to her. The question is, how to get Collette on board?

Taking the elevator to the penthouse, I enter our apartment to be greeted as usual by Mandy. She approaches me in the pink and white latex maid's outfit which is her daily uniform. The uniform leaves little room for modesty as Mandy's pert, stand-up breasts with her rose nipples are displayed in all their glory. To draw attention to her tits, Mandy is equipped with a serving tray strapped around her ribcage just below her breasts. The tray's outer edge has two chains which conveniently clip to her shiny, white leather collar allowing her to serve drinks or snacks without spilling them as long as she maintains an upright posture.

Further inspection of Collette's slave reveals glimpses of the shiny steel chastity belt which entraps her feminine center visible just over the tops of the pink, thigh high stockings she wears and under the short maid's skirt. As I said I've never even seen Mandy's pussy, but I fantasize over how soft, deep, and wet it is nearly every day.

My fantasy is interrupted as Mandy stops in front of me with my favorite brew, Newcastle Ale, in a mug on her tray. For now I forgo the liquid refreshment and reach out to squeeze her soft tits before I let my hand run down the latex and around to her bottom. When I reach her butt, I feel the plug, which is sometimes there and sometimes not depending on Collette's whim, but thankfully Collette has given me permission to remove it if I desire to use the tight passage it stretches. The same would be true if Mandy were ball-gagged, as she often is, as Collette knows how much I savor the oral pleasures Mandy can and does provide.

"You're plugged today. Were you a bad slave?" I'm k**ding with her as I lift the Newcastle from her tray and taste the hoppy nectar.

"No, Master Robert, Mistress just insists my anus be pliable so she requires me to be plugged at least once every 72 hours at the minimum. Of course, you can remove my plug if you desire." Mandy utters the last sentence with such a teasing sensual voice I have no question she wants to be fucked anally. The truth is Mandy has never given me any indication she does anything but crave my sexual use of her body, despite her inability to achieve climax.

Letting my free hand roam her body, I feel the coldly indifferent steel of her belt as I sip and it makes me muse. "I'd love to fuck your hot wet cunt, you horny bitch, but alas your Mistress does not permit it."

Now Mandy reacts with the same awkward silence she enters every time I mention her trapped vagina. To me it seems to be a mixture of shame and perhaps fear and I wonder if Collette has forbidden her to even talk about her pussy to me. After the awkward moment passes, Mandy speaks in a low soft voice. "Please, Master Robert, let me please you in the way I can."

Her plea is so sincere and genuine it makes me feel guilty for having mentioned that which she has no access to. Placing my mug on a nearby table, I look her square in the eye. "Perhaps someday, Mandy, but for now you may serve with your talented mouth." I pause and then add. "Oh and no hands, a good blowjob doesn't require hands."

Mandy squeals with delight and instantly drops to her knees. Not allowed the use of her hands, she must wait for my manual dexterity to unzip my fly and bring out that which she is so anxious for.

Wanting to savor the first touch of her warm mouth, I bend my head back and breathe deeply closing my eyes to await oral heaven, but I have forgotten something. The position of Mandy's tray, jutting out perpendicular from her chest, does makes it difficult for her to get close to my penis in the kneeling position. This might cause confusion in any other slave, but not one as dedicated to serve as Mandy.

After few second's delay, I look down sensing something's wrong, but I see Mandy has already solved the difficulty by standing and bending forward from her erect stance with her head tilted back to change the angle by which her face approaches my penis. She eagerly engulfs my penis and I hiss out my breath to tell her how heavenly her mouth feels. "Oh god, you do that so good."

Collette's little shag-cut, blonde slut worships cock in so many delicious ways, I truly feel she must have been born sucking cock. Sometimes she takes me deep with her tongue stuck out of her mouth just far enough to lick my balls and other times she slobbers and face-fucks herself with a desire I've never seen any female match.

Consequently when she sucks me, I rarely last long before I explode filling her mouth with warm semen which she gratefully swallows before she licks me clean, seemingly greedy to get every last drop of my seed.

"Thank you, Master Robert. How may I continue to serve?" Mandy's voice is now breathless with an excitement and I can only assume the sucking of my organ has given her. She seems to truly be excited to give pleasure and not bothered to not receive it.

It's a shade past five and Collette is still at work, her job as the CEO of a well-known woman's clothing corporation is more demanding and better-compensated than my stockbroker's job. Since it's a party night and I know there is more sexual exploits on the horizon I decide to simply sit, savor my ale, and converse with Mandy.

"Is everything set for tonight?" I know a fetish party means lots of extra work for our maid/slave.

"It's not complete, Master, but it's all on schedule." She smiles proudly at me.

"Well, then you have some time. Come, let's sit and talk. I have some questions I want to ask you." Picking up my mug of ale, I head for the leather sofa where I sit.

Mandy follows, but she refrains from sitting opting to get to her knees on the carpet in front of me. There is a worried look on her face and it reminds me she always seems nervous when I speak to her privately without Collette here.

In an attempt to lessen the barrier between us, I pat the leather sofa beside me. "Won't you sit up here, beside me? I want you to." I don't want to command her to sit beside me as I'd rather she want to do it.

Mandy obeys, but she clearly seems uncomfortable.

"How long have you been Collette's slave, Mandy? I've heard Collette's story, but I've always wanted to ask your story of how that came to be." Strange as it may seem, I had simply accepted Collette's version of how Mandy became her slave.

Immediately Mandy looked stressed. "Ahhh . . . well Mistress must have covered it I'm sure. Nothing more to tell." Mandy was more than a little nervous and I was puzzled about why.

"Ah, but of course there is. What were your feelings, your motivations? Those are things Collette can't know." I was still hoping to gain some insight on how the two most important women in my life met. Collette had told me the initial meeting came at a bondage club, but she had not given many details.

Mandy's big gray eyes looked at me pleadingly. "I am a slave. I am here to serve Mistress and you. I should not speak of my feelings because they are of no importance." She paused and then slipped off the sofa to the carpeted floor with her head down. "Please, Master Robert, don't make me say more. No good will come of it."

I got the immediate sense poor Mandy would be seriously punished by Collette if my lover knew she spoke to me about her feelings and that upsets me. I'm all good with BDSM games, even serious ones, but Mandy was a person and I am feeling more and more close to her each day. "Are you afraid Mistress will punish you if you speak, Mandy?"

Mandy's eyes suddenly looked up as if she'd been misinterpreted. "Mistress would probably punish me for this, but that isn't the worst thing which might happen. You should be careful what you ask, Master. She might . . . not like it." Mandy's voice trailed off leaving me with a startling revelation.

Is she saying it's dangerous for me to ask? Is she insinuating Collette might punish me? I'd never even considered such a possibility. Yes, I let Collette rule the roost and I had no illusions about being a kept man, a gigolo perhaps, but the idea being punished for any misbehavior had never been brought up and Collette had never spoken or even alluded to such a thing. "Are you saying I could be in trouble with Collette for asking you this?"

Now Mandy looked confused, like she'd never anticipated this conversation happening. Her voice was a mere whisper. "I don't know, Master, but there could be trouble from it. I can't say more." Again Mandy bowed her head low after she finished.

I found this all hard to believe, but it was clear Mandy was uncomfortable so I tried to change the subject. "Okay, let's leave your past alone. Let's talk of the future. Surely you don't want to be Collette's slave forever, do you, Mandy? I mean wouldn't you like to have a more normal life. Wouldn't you like to orgasm when you have sex? Wouldn't a three way equal relations between Collette, you, and I be more exciting?"

The worried look on Mandy's face didn't dissipate much. "If Mistress decides I'm ready to be freed she will do so. Until then I must serve her." Mandy's tone was firm on this.

I was frustrated by her deeply submissive attitude, but I pressed on. "I'm not saying you couldn't still be submissive to us, but in the future I see the three of us moving from the city, maybe getting a nice farm in the country. I'd convince Collette to unlock you and you could still be our little slave girl, but when I fucked you, you would experience orgasm which I'm sure would make your life much better. The three of us would be a sort of kinky ménage a trois. I think you'd enjoy it a lot more than this life." To me it seemed like nirvana, sharing a simple country life with two beautiful women and we could still play kinky games when we felt the need. However I did feel a surge of uncertainty as I revealed this future plan to Mandy before I'd said anything to Collette.

The look in Mandy's eyes was unreadable to me, perhaps it was a mixture of fear and shock, but she stood up and began walking quickly to the kitchen as if she had to get away from me. Confused, I demanded an explanation for her behavior.

"Stop, Mandy, why are you leaving? Why does this idea upset you so? Surely these thoughts aren't that frightening, are they?" My voice got loud and angry as I was determined to find out what was at the root of her fear.

Due to her submissive nature, Mandy stopped in her tracks and turned back to me. Her face looked whiter than normal like she'd seen a ghost or something. "I know they seem innocent enough, Master, but I strongly urge you never to speak them to Mistress and for my part I'll try to forget I heard them." She paused and then turned to go, but before she did she added something even more chilling.

"Please, Master, do this for your own sake." As Mandy walked off to the kitchen with her heels clip-clapping and her tight, plugged ass wiggling, I was left to contemplate what she meant.

For my own sake? What the hell can that mean? I spent a while musing about what her warning could mean, but for the life of me I simply couldn't see what danger there would be in telling Collette of my thoughts about our future. Sipping my ale, I passed the time reading until Collette arrived and by that time I had pretty much dismissed Mandy's warning. After I greeted Collette with a kiss, Mandy presented herself and told us she had prepared a snack for us to tide us over until the party began.

* * * *

Collette talked shop during our snack and after that she insisted on getting dressed, so I went to our bedroom to shower first while Collette gave Mandy instructions for tonight. Soon Collette joined me in out shower and we soaped each other in silence until I broke it. "Perhaps Mandy could serve tonight without her belt. I know I'd like that." I let my tone be half serious and half playful as if I was simply joking with my lover.

Collette mused a moment in silence and looked at me with an appraising eye before she smiled. "So you want to fuck her in front of everyone, do you? You want to hear her scream when she comes for the first time in years? Is that what you think is important?" Collette's tone was challenging and it changed my tactics.

"I think it's important to her and I think she deserves it for how well she serves us. I mean you keep her in that belt all the time, dear, even slaves should get some pleasure especially one as obedient as Mandy." I felt more comfortable expressing Mandy's needs rather than my own keen desire to get inside her tight, wet cunt.

"Oh, so you don't care if you're the one to do her? Is that what I'm hearing?" Collette smiled slyly.

"Okay, I'd love to do it, but it's more important to me that she gets what she needs, not that I be the one to give it to her. If you want someone else to do it, it's fine with me." It was sort of a lie, but I think I told it well. Well enough to sound sincere.

"How unselfish of you and how unlike your gender. I suppose you want me to think you aren't getting attached to my bitch, whispering things in her ear." Collette spoke in a syrupy-sweet falsetto, giving me the immediate impression she had spoken to Mandy and knew of our earlier conversation.

In an attempt to defend my action I reacted immediately "Anything I said to Mandy was just to feel her out and I have no problem saying it to you. I'm sure if you listen to me you'll see how my ideas are for the benefit of all of us. Do you want to discuss it now?" I was upset, partly because of how quickly Mandy had told Collette and partly because I had made the tactical error of speaking to Mandy first instead of Collette. It was a foolish mistake.

Collette burst out in laughter. "No, no, we'll talk about it after the party. I was just seeing how much I could pull your chain, dear. You do seem a bit touchy on the subject. As far as her belt, I'll think about removing it tonight, but don't be upset if I don't. The truth is I do want you to be the first to fuck her to orgasm, so I may wait a while to build up both your desires." Collette reached down and grabbed my cock and squeezed it.

"As for tonight, I want this and yes I want it in front of our guests. Fuck me like I'm your bitch slave." Collette pressed her wet soapy body to mine and stoked my cock.

"You're serious, you really want me to take you like you were a slave?" It wasn't usual behavior for my lover so I was more than a little impressed with her willingness to give up her usual control.

Collette responded non-verbally by dropping to her knees and taking my cock deep down her throat as the shower pelted down on her. She'd never done such a thing before, so I let her give my cockhead all the attention she would, but when she kept going, I began thinking about her desire to be fucked as in if I let her make me climax after spurting in Mandy's mouth, would I be able to get hard later?

Gently I touched her head. "If you do that I might not be able to do you later. Mandy did me when I came home." My confession didn't surprise Collette as she knew I used her slave's mouth and ass regularly, with her permission.

"I understand, but I hope you understand I love you, Robert. However as you know I also love sex and all the kinky facets of playing with my slave. Please don't underestimate how much I love this lifestyle, or make me choose between you and my chosen lifestyle. If you do you might regret it." Collette's tone was as serious as I'd ever heard from her and she stood up and left the shower to began toweling off.

Remembering what Mandy had warned me of earlier, I was stunned and I began to consider things I'd never thought of before. Is she so defensive of her lifestyle she'd leave me rather than let me change it in any way? Is that what Mandy meant? Through all of this I had never wanted to get off this amazing ride with Collette, I had just wanted to tweak it a bit to better satisfy my emotional needs and Mandy's sexual needs, but now I wondered. Am I playing with fire?

I'm not sure how long I stood thinking under the spray of the shower, but Collette finally called to me. "Time to get dressed for the party, dear, and after you do would you be a dear and check out how Mandy's doing in the kitchen. Help her out if she needs it because I want everything to go well tonight. I have a feeling this may be a very special night for all of us." Collette's tone was not asking me, she was commanding me and I left the shower to begin toweling off.

Just before I left the bedroom I caught sight of Collette in her white latex cat suit and it reinforced one thought in my head. I must be careful. I don't want to lose her.

* * * *

When the party ended both Collette and I were well sated, but not so Mandy and I felt sorry for her when we retired to our bedroom and Collette set her slave to cleaning up the apartment. After we stripped off our latex and climbed into our king-sized bed, I realized how tired three ales and the robust fucking of Collette had made me. I would easily have been willing to forgo the discussion of my ideas about our future until tomorrow, but to my surprise Collette brought up the subject.

"So . . . tell me about these plans you have for our future. I'm dying to hear all the details." Collette sounded sincere so I felt I had to oblige.

I started with the house, telling her how I imagined us in a large country home in either a modern style or perhaps an old farmhouse. Moving on, I gave her a thumbnail sketch of the three way relationship I envisioned between her, Mandy, and me. Collette didn't voice any verbal objections until I got to the part where I mentioned she might have to step down as CEO of her company for all this to happen.

Collette gave me a sour look and sighed. "You want me to give up my career?" She sounded incredulous. "For what, to make my slave happy?"

Desperately I tried to do damage control. "No, not just that. You'd give it up to establish a sound physical and emotional relationship with two other people which would be very rewarding. You have to give your time to make a deep relationship." I knew as I spoke the words they were having little effect on her.

"What's wrong with our relationship now, you get all the sex you want from me and my slut. I think things are fine as they are, but you must be unhappy or you wouldn't be pushing this." Collette had a point I hadn't considered; was I truly unhappy, or just restless. Is this about the emotional distance I feel from Collette, or is it just about my feelings about liberating Mandy?

I didn't have an answer, but still I pressed forward hoping Collette's resistance would crumble. "I don't think I'm terribly unhappy, but we've lived your full tilt, hedonistic lifestyle for four years now. Isn't it perhaps time to try something else? Doesn't the ultimate ménage a trois sound good?" I was trying to tempt her.

Collette took a moment for thought and I felt like I could see the wheels turning in her head, but I couldn't determine which way they were rolling. "So if I agree to try this we can change back if it doesn't work, if I don't like it?" There was a hint of her sly tone in her voice.

I simply couldn't envision Collette not liking this once she got into it, but I wanted to assure she would give it a fair trial. "Certainly, but you'd have to give it a fair trial. I suggest we lease a place in the country for say a year and at the end of the year you decide, do we stay or come back to the city." I felt a surge of success and I was confident enough in my plan to leave the decision to her as long as she did give it a fair chance.

What happened next may have been fate or well planned by Collette. The truth is I'll never know. There was a knock on the door and Collette instantly gave Mandy permission to enter. It felt to me as if she was relieved to have our conversation interrupted before she gave a final answer.

Mandy entered, did a formal curtsey, and knelt before Collette's side of the bed. "Things are in order, Mistress, how else may I serve."

I expected Collette would send Mandy to bed, she had a small maid's quarters off the kitchen, but Collette surprised me.

"Master Robert and I are discussing changes to our relationship and thus yours too, slave. It seems your time as my full-time slave may be nearing an end. How do you feel about that?" Collette seemed to want Mandy's opinion which very much surprised me.

Mandy seemed unsure how to reply, but she finally did. "So Master Robert told you his plans, Mistress?"

Collette nodded.

"Does he understand all it means?" Mandy's voice seemed excited, but still a little wary which I didn't understand.

"No, not yet, but he will soon. Why don't you go pour us a nightcap as we have a lot to work out? I'll have a shot of Bailey's in decaf coffee and bring Master Robert some of that special scotch I bought for him. You know the one. Go and hurry back now." Collette made a motion to shoe Mandy off and her slave clattered from the room in her spiked heels.

I was beyond shocked. Had Collette actually changed her mind? Was she truly considering my ideas for our relationship and what had Mandy been talking about? Part of me felt this was all too easy, but the other part urged me not to fuck things up. As Mandy prepared the drinks, Collette started expounding about her vision of my future plans for us. It included the large country home, but with a horse barn and lots of land for riding trails for Collette had ridden on the equestrian team in college and missed not having horses here in the city. She went on to suggest instead of Friday night fetish parties, we host fetish weekends for our friends where they would stay with us and have all their fantasies fulfilled as they did.

Soon enough Mandy returned with Collette's coffee and a stiff double shot of Glen Fiddich for me. In light of what had just transpired, I felt like celebrating and so I picked up my glass to make a toast. Raising it to Collette's mug, I noticed even Mandy looked excited, more excited than I'd even seen her. "To all of us and this new adventure we're embarking on. I feel certain this will be a truly wonderful experience." Looking at the shag-cut, blonde slave girl, I couldn't help but feel I'd freed her and her smile was for me.

Collette smiled and proposed her own toast, but what she said only confused me. "My toast is to you, Robert, for finding your true self and having the courage to speak up for what you wanted. I hope your efforts get you all you desire. I know Mandy and I will enjoy what comes next." Collette gave a coy smile in Mandy's direction as if they knew something I did not.

Even though I didn't particularly understand what she meant, I didn't want to ruin the moment so I downed my scotch and felt the warm burn as it passed down my throat. At first Collette simply sipped her coffee, but then she turned away from me and began talking to Mandy. It seemed an odd conversation, like two new girlfriends meeting, women who had known of each other but not known each other intimately.

At first I was amused Collette could so quickly accept Mandy as an equal like she just flipped a switch and it was done, but then I began to wonder if there wasn't more going on here.

After a few moments of watching them interact, I was about to interject when I suddenly felt warm and dizzy. Slightly flushed and disorientated, I soon realized the entire room seemed unstable and I reached out toward Collette for support, but she callously brushed my hand aside and I keeled over onto the bed. After collapsing on the sheets, I seemed unable to rise and I whined pitifully. "What the hell . . . what's wrong . . . what's happening to me?"

Yet there was no answer as Collette and Mandy simply continued to talk as if they didn't even notice my plight. The last thing I heard before I passed out was Collette's voice, loud and clear, but saying something which frightened me to my very core.

"I think he's out. Come, my dear, let's get to work because there's a lot to do." She let out a sinister laugh and added. "For both of you to fulfill your new roles."

* * * *

When I awoke in a very groggy state, but it was immediately apparent I was in trouble because I was confined in a small metal cage. I was in a kneeling upright position in the cage, but my knees and wrists were restrained, held by tight, locked leather cuffs to the sides and bottom on the cage so my movement was limited. The first thing my eyes concentrated on was two rubber dildos attached to the side of the cage right in front of my face. The faux cocks were large, realistically flesh-colored, and had clear plastic tubes leading into them from behind. Following the tubes upward I saw they led to two suspended plastic tubs, one clear like water and the other an unappealing gray color.

Then the sudden realization hit me, I was not only naked, but worse than that there seemed to be something constricting my penis. Instantly I looked down and saw my cock was indeed a prisoner inside a clear plastic chastity device. Having played BDSM games, I knew such devices existed for keeping male slaves chaste, but I had never expected to be confined in one.

My next realization was perhaps more shocking; my body hair was completely gone and so the soft penis confined in the plastic looked more like that of a little boy than a grown man. This was all mind-blowing, making me wonder what Collette intended. It didn't take much to realize my lover had duped me and d**gged me and she likely had bad intentions toward me, but how bad? To avoid complete panic I told myself this was just a punishment because I had pissed her off and once I was taught a lesson about who was in charge she would let me go, yet somehow it didn't feel too comforting.

My thoughts were interrupted by the door opening in the small, almost closet-sized, room I was in. Certain it would be Collette who entered; I actually breathed a sigh of relief in the hope I could reason with her. Surely if she was upset I could get her to forgive me.

It was not Collette, but the person who entered was familiar to me, sort of. She had the soft, voluptuous body and the long, shag-cut, platinum blonde hair I had long linked in my mind to Mandy, but she wasn't wearing her chastity belt and what was revealed was beyond eye opening. As she walked towards me holding a tray my eyes concentrated on her crotch. The juicy pussy I'd long imagined was there simply wasn't, but my mind was having a hard time accepting what was. Oh, my god, that's why Collette kept her locked all the time.

Dangling meekly between Mandy's legs was a tiny penis, looking almost prepubescent and completely hairless, the tiny organ and its minuet balls bobbed cutely as she walked.

"Now that you know my secret, Robert, are you still anxious to fuck my ass or have me suck your cock? Lots of macho men would be disgusted at the thought knowing I'm still technically a man." Mandy, complete naked, set her tray down at a nearby table as it was no longer fastened to her chest like it had been when she was our slave.

After wondering if she knew how much she had just shattered my world, I considered if I was a homophobe. I'd never thought I was, but on the other hand I'd never had any bisexual desire to explore being with another man. Thinking of the many times I'd enjoyed Mandy's mouth and ass, I felt no queasiness about those past actions because I had thought she was a female. However I did wonder if I'd feel the same if she sucked me now, now that I knew what she truly was. "I'm . . . not sure. I mean . . . I was sure you were a girl . . . a hot sexy bitch. You . . . you seemed like you liked it. I felt sorry for you because Collette kept you locked up. I never questioned why she did." So many confusing thoughts were running through my mind now I could barely keep my sanity. The truth was Mandy had been a major reason I had spoken up to Collette and so she was more than a little responsible for me getting being in this situation.

"Oh, I assure you, I did enjoy servicing you. I'm actually a little sad this phase of my life is over as I did love your cock. Of course, six years ago you would never have convinced me I would suck cock, but alas the sissy training changed me completely as Collette said it would. Now I'm ready for the wonderful new future before me and I have you to thank for it all. I just want you to know I'll handle your transformation and training to a sissy maid just as resolutely as Collette handled mine." Mandy's lilting, incredibly sexy, feminine voice sounded truly sincere in its concern for me, but her words had unleashed a new world of horror on me.

Desperately I tried to focus my mind and respond. She's no longer a slave, but she intends to make me one. "A sissy maid? Nooooo, please you can't do that." I wailed like a c***d and struggled against my bonds to no avail.

"Oh, I assure you, I can and I will. Now stop fussing, it's not that bad and I should know, I've lived the life for six years. Collette has charged me with one last task before I receive my transformation; to chastise, feminize, transform, and train you to be our new sissy bitch." Mandy paused and looked at me in my stunned state. "Oh, it was so cute how concerned you were over my lack of orgasms, but now you'll have to bid your own goodbye. The plastic chastity you wear now is just filling in for a new, custom-fitted, steel one we just ordered for you. Soon you won't even be able to see your little penis and believe me locking it away does a job on your male psyche." Mandy smiled and reached into the cage to touch my entrapped penis. "I'm not too proud to admit it; I'll miss your thick stiffness, but you can't imagine how hard it is to continue to believe you're male when you can't simply look down and see a confirming penis."

Frightened out of my mind, I panicked. "Noooo, please, you can't do this. Please let me talk to Collette. I need to talk to Collette." Somehow I hoped Collette could free me from this madhouse.

"No, no, Collette has other things to concentrate on. You won't even see her until you arrive, ready to serve, in our new country home. Yes, she did like your idea of a big place in the country and I believe she's out house shopping right now. Of course your idea is going to create quite a bit more work for you, as opposed to my former duties. Surely a mansion in the country will provide a lot more in the way of cleaning and other household chores than this apartment ever did for me. And then there's those fetish weekends, no doubt they'll be a nightmare for you." Mandy paused and opened the cage door from behind. She ran her hand down my back and patted my bum before parting my rear cheeks and feeling around my anus. "Oh and I just realized the cooking will be doubled too, as you'll be serving all four of us."

"Four of you? I don't understand." I had no idea what she meant.

"Oh yes, Collette and her new male lover and me and mine. Of course that's if we both have only one lover. Truth be told, since we'll have the room I'll probably want to take more than one lover. I plan to have a good time with new vagina. Ummmm, lots of hot sex." Mandy giggled and her lubed finger slipped into my anus.

Perhaps the shock of her finger penetrating me brought it all home to me in the distinctly diabolical fashion they must have planned. My efforts on behalf of Mandy had yielded fruit for her, but it was at my expense. She was leaving her position of sissy slave to be transformed into a real woman and Collette's girlfriend just after she transformed and trained me to take her place. What the hell have I done?

"Oh, you're so tight, just like I was at first, but don't worry I'll use plenty of lube for your first training plug." Mandy giggled as she sent a second finger into my rear passage painfully stretching my rectal ring.

My mind was wading through so much horror I felt it might shut down if I didn't keep talking. "Plug? No, not like . . ." I couldn't finish the sentence, but Mandy knew where I was going.

"Like the ones I wore so often? No, not so big as those at least not yet until we get you stretched properly. Eventually you'll wear those, perhaps even bigger ones, after all you have a slightly larger frame than me so you should be able to accommodate more cock." She paused and picked a medium-sized pink butt plug from the table. "Are you getting hungry yet, you should be as it's been over twenty four hours since you ate."

I tried to think was I hungry as Mandy slowly eased the plug deep in my bowels, but somehow in that situation hunger seemed irrelevant.

She slapped my bottom stingingly hard once she got the plug in. "There, all plugged, but you didn't answer. You must learn that slaves must answer their Mistress all the time. I asked if you're hungry, as in do you want to learn how to eat?"

Learn how to eat? What can that mean? I was mentally adjusting to the feel of the deep anal penetration, but I managed to speak with some coherence. "Ahhh . . . yes, Mistress."

Mandy smiled and reached around me to pull up the long shaft of the clear-tubed false penis. "This is your water cock, you suck it for water. You do need to actually suck, fairly strongly to get the water out, but it will make a fine cock-sucker of you." Mandy giggled again and added. "Well you've already felt the results with my mouth."

Strangely there was some odd comfort in her statement as I realized Mandy had preceded me down this road. She had been male, presumably Collette's lover before me, and she had already experienced all I was to feel. "Ahhh, may I ask, what does the real thing feel like?"

Mandy squealed in delight. "Wonderful, especially if you take it in soft. The feeling of having it grow in your mouth is empowering. Believe it or not the taste isn't bad either, after you get used to it."

This was of some comfort until I thought about the circumstances. I was to be essentially a penis-less slave who would reap no sexual pleasure save for that I felt by pleasing others. My mouth and ass would be turned into appealing female-looking cum receptacles. Is this really going to happen to me?

Mandy easily moved on in my education as she lifted the gray-tubed cock and squeezing it slightly until a sort of gray gruel appeared at the tip. "This is your nourishment cock and I'll let you know it takes even more effort to get the gruel out because it's thicker than the water. It's not very tasty, but the good news is it's quite nutritious, but I won't lie to you as to its effects on your male body. The gruel is heavily laced with anti-androgens which will give your noble cock a look more like my little thingy. I know, it's sad." Mandy reached down and patted my chastised organ and I reacted.

"No . . . I won't. I'll die first." I felt serious, better to waste away and die male than to be what they intended me to be.

"Brave words, so like your gender, but I remember uttering similar words myself. I was resolute when I spoke them, but hunger breaks you down, and then there are the daily injections. When you see your masculinity fading, being replaced by the new female you, the hungry gnaws at you and you eventually give in. I did and frankly I no longer remember why I struggled so." Mandy's last sentence was spoken with a fierce belief I could not ignore Mandy's seeming happiness to be what she was.

"So you did like your service to Collette? It seemed to me you did." I was begging for some spark of hope from my new Mistress.

"Oh yes, I loved sucking you and taking you inside. It felt like those things were reaffirming my desire to be female. You'll accept your transformation and come to terms with it and who knows, you might not have to wait six years until the new boy screws up. You might earn your reward earlier, but you must follow the rules." Mandy's voice sounded upbeat and I suppose I should have understood what she was talking about, but I was so confused and frightened it eluded me.

"What do you mean?" I looked at my new Mistress with wide eyes.

"Oh, Bobbie dear, you should understand, but I do remember how confused I was at your stage." Mandy turned to the table and began to prep an injection.

"Female hormones, to start your new body growing. Now let me explain, you must serve until one of the new males does something to offend or upset either Collette or I, but you must never reveal your true gender to the males you serve or give them any reason to suspect you aren't what you appear to be. If you break the rules you forfeit the right to what I have received; the right to transform and train them to be your replacement when they screw up. Understand, Bobbie, your only way out of sissy slavery is to become a new woman so embrace your femininity." Mandy slipped the needle into my butt and then slapped it. "In other words, be a good little bitch slave and please everyone."

Slowly, I began to absorb the new parameters of my life and I didn't think it coincidental that I craned my neck forward to take my water cock into my mouth. Awkwardly I sucked and sucked until I finally got my first reward of cool, life-giving water.

Mandy saw my action and she moved around the front of the cage to push her crotch right up to the bars near my face. "If you want to move along quicker and impress your Mistress you may suck it. Of course you won't get it hard and I won't feel too much, but it still is warm, live flesh, not rubber.

My eyes must have gone wide with the initial horror of her offer to allow me to suck her hormone-withered organ because Mandy laughed. "No, not ready for that yet, too bad, but you will be. I was begging for live cock before I got out of my training cage and Mistress was wise enough to oblige me. You'll be no different, sweet Bobbie." Mandy took her tiny penis away from the bars and she sashayed across the floor with her round female ass swaying sexily as she left me.

"In time you'll learn to love cock, girl. It really is the only way out of here."

Same as Collette's Sissy Videos

1 year ago
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3 years ago
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I Now Own You Sissy

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2 years ago
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2 years ago
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3 years ago
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2 years ago
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3 years ago
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I Sissy

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3 years ago
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2 years ago
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3 years ago
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2 years ago
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3 years ago
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2 years ago
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4 years ago
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4 years ago
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2 years ago
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3 years ago
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2 years ago
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2 years ago
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4 years ago
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2 years ago
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2 years ago
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2 years ago
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3 years ago
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2 years ago
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4 years ago
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Checkerboard Sissy

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4 years ago
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Trucker Daddy Gets A Sissy

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2 years ago
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Saturday Night Sissy

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3 years ago
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3 years ago
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4 years ago
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Be a Sissy

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3 years ago
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Sissy On Sissy

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2 years ago
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4 years ago
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2 years ago
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4 years ago
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2 years ago
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3 years ago
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A Nasty Daddy gets a Naughty Sissy

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4 years ago
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Sissy Stepson 10 Stepmothers Sissy

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4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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