His Sissy Boybykeptsissy©
by a kept sissy
As directed, he was waiting for me when I returned home. Seeing him in blouse, skirt, stockings and heels, makeup perfectly done, manicured and painted nails (he does them every morning after his household chores, for the evening ahead), seeing his very sexy hair style, hint of nice perfume, it's hard to tell he's not a real woman. And the body on him, down to 130 lbs. at 5'10″...he's almost every real man's dream girl, very cute, exceptionally cute. His ex-wife and I have done wonders with him. His demure eyes to the floor, he started for his special play room as soon as he took my overcoat and hung it in the hall closet. He's such a good wife.
He's across my lap, one of my favorite things to do with him. And I do love doing this to him, even have a special room for it with mirrors for both me and him to see ourselves in. That's a huge part of it, to be able to have him watch his humiliation. This is now the biggest turn-on for me, to finger fuck the little bitch across my lap, to demonstrate just how much he is truly mine.
I still very much like fucking him, and whipping him too. Like to whip him to the point of tears sometimes, that is beyond erotic. But this is almost unbearably good fun! I can feel him move against my erection, squirm on my lap as I use him like this. All I have to do is manipulate him with my finger.
I usually do this while dressed in business or street clothes. I like the feel of him making me hard inside my pants. And it's more dominant to be dressed in front of him when he 'serves' like this, makes him know his place. Do it sometimes straight home from the office, still in a business suit, I'll have him meet me, like today, at the door waiting for me for hours, not knowing when I'll walk in. To have him spend an hour or two on his hair, makeup, getting dressed so pretty just to be taken across my lap and used like this, I truly love that. And pulling his skirt or dress up real slow, taking down his very feminine sissy like panties, maybe pet him prior to that, well I just can't describe how much this enhances it all. It's like unwrapping a present. And when I slip a finger into him softly or push it in fast and hard into, feel the initial resistance of his tight little hole, it's all I can do not use him to make me cum on the spot.
But the real fun is prolonging this, finger fucking him to the point of distraction, not using his 'other skills' right away. It always does lead to me using his mouth, hands or rear end to make me cum but to make it last is precious, so selfish on my part.
I have his ex-wife to thank for the girly stuff, didn't appreciate that until she made it happen. She was the one that turned him into 'girl'. I liked the sissy slave aspect of being his master but now I have seen another side of him, a side to exploit that keeps me almost constantly erect. And I mean constantly. His wardrobe is large thanks to her, takes him shopping to please me at least once every couple of weeks. Before she talked me into this 'change' he was naked, not allowed to wear any clothing in my home. He had no clothing at all. Had the house caught fire he'd have had to exit nude. I used him sexually but it was never like a man takes a woman, it was pure sadistic sex. Make him suck me to humiliate him, fuck him to prove his status, punish him for the slightest infraction with regard to his slave like house chores, I never knew how much more pleasurable it would be to have a 'little girl' around the house. His ex-wife is to be congratulated on that!
I fuck him sometimes four times a day, now. I'm far more turned on by my 'wife' than I was by my slave. And it truly is like unwrapping a present to use him like this. And taking him to bed now sometimes is like taking a hot little wife to bed, not just a wimp to abuse. He's like a woman to the touch and such submissive lover. He actually does 'make love' when given the opportunity.
And I have to admit, I love the outfits he wears to please me. I've always been more turned on by women, never thought of men as erotic other than this sissy. And that was a fluke, presented itself out of left field. I quickly discovered a sadist in me that I didn't know existed. Given that he was an employee of mine, still is so to speak, still does all my accounting, well it's perfect!
I should say here that this all started a little over a year ago at a company holiday party. His wife was more than a little high toward the end of the night, had been openly flirting with me. They'd both been to my house before nothing ever came from her open flirtatiousness. But this time was different. They were the last two guests at my house, I could tell she was staying until the bitter end, actively waiting for all the others to leave. One thing led to another and we ended up in my bedroom. We were gone for almost an hour before he started looking for her.
When he came upstairs looking for her we'd been making out, she just started French kissing me as soon as we went into my bedroom. We were front of the bedroom mirror, remember how hot her ass was as I pushed my hand up under her dress from behind, watched her push back against my hand in the full length mirror. I kept glancing to the door, trying to make sure that if he came in I could cover with 'the tour of the house' thing. He pushed the door open and looked in. I thought we were busted, so to speak, that he'd start something. She looked up at him and I saw the look of fear on his face, not hers. She was in control, not him. She scolded him for interrupting. Talked to him like he was a bad little boy, she not only scolded him, told him he'd be punished when she got him home. I couldn't believe what I was hearing, found it amusing and a turn-on, said 'why wait until you get home', half joking. I just jumped right in. I was a little high myself. I'd always been somewhat dismissive of him at work but that night is where it all started. I was turned on by saying that, really turned on. I felt myself pull her closer as the two of glared at him.
She told him not to say a word, not one more word, and he didn't. He stood and watched as knelt in front of me. I remember undoing my pants while staring at him, watching him cringe as his wife jacked me off with her mouth. When the two of us finished we took him to my basement. At this point we were both so into this there was no turning back. She made him strip naked in front of me, she whipped him with my belt until he cried. I could not believe what I was seeing but I knew I wanted more of it.
When she finished with him she him dress as she scolded him again, told him to wait in the car for her. She and I went back upstairs and had a drink. We talked about him and what he was to her. She also told me about what he could be for me. She laid it out in detail.
That's where it started.
After that it was all about breaking him, my sadistic side was given free reign. Starting out as a part-time house boy, keeping him naked and wanting, fucking his wife a couple of times a week while he stayed in what would become his slave quarters in my basement, it was all a process. And then a year ago she gave him to me, just said he was "mine to keep". I didn't even blink, just dove right in, I have never looked back. He's been in my home ever since.
But now turning him into a woman, well this is what is best for him and for me. He knows that as much as I do. And he also knows he has no other choice, he has no choice at all about anything anymore. He doesn't want one.
So here he is gorgeously laid out across my lap. I look down at him. I never tire of this, it's always like the first time. "Come on, baby, make that sound for me. You know the one I like, the one that gets my dick hard for you. Come on, baby." I reach down and take his CB-6000 cock restraint and pull it back up between his legs from behind. My hand pushed down between his legs griping it tight, top of my wrist pushed up and softly spreads his cheeks, brushes up against his little hole as I lift his chastity tube up. I hear him whimper, cry out softly. That's it, that's the sound. I love that sound. Never fails to get me rock hard. As I pull it up as far as I can I feel his legs spread. He's trying to ease the pain. I hold his caged and locked penis up almost level with the backs of his exposed thighs. He squirms slightly, whimpers louder. He knows not to close his legs together, not time yet to do that and hold it in place, not until I have it pulled up high enough. He knows that if he doesn't do this right it's off to his restraining horse in the basement for a whipping. "Good girl, such a good little girl." I pat his rear gently as he tries hard to please.
And he knows not to talk, knows that a good sissy wife speaks only when spoken too. I stare down at the beauty displayed across my lap. I have his tight black skirt up over the back of his crisp white blouse. His skirt covers his hands and perfectly painted finger nails, his wrists cuffed behind his back. I cuffed the little bitch as soon as we entered his play room, makes him think, doesn't know what to expect. I love that too.
I see the outline of his bra strap through his sexy blouse. I slowly look back down the full length of the little bitch, eyes wander to his ruffled black lace panties pulled down to the lace tops of his nylon stockings, exposing the backs of his baby smooth thighs. When I pat his rear he lifts on leg up off the floor, high heel shoe raises up like a pin-up girl picture pose. I hear his ear rings as he turns his head toward the floor. The sight of this 'girl' makes me hard, very hard, and that whimpering...it's all I can do not to push him onto the floor and fuck him right there. I let my eyes wander back up to the bottom of the curve of his smooth rear cheeks, see his pathetic little penis in it's cage held by his naked upper thighs, see his tiny sack pushed back tight between the locking ring of his chastity tube and the crack of his rear. His tiny smooth balls turning the most delightful shade of red-meets-purple, I love that too.
I also see the faint stripes of his last whipping across his naked rear end. I run my hand over him, trace one of his fading stripes with the tip of my finger. He purrs like a kitten, see goose bumps rise on his naked rear end as I do that. I smile silently as I watch him quiver trying to keep his legs pushed together, see him slightly struggle, try to avoid letting his restrained penis fall back down onto my leg. He's very pleasing to me with that beautiful round bubble rear end. He works hard to keep it that way, I know that. I feel my cock throb, feel my full erection underneath him, feel the wet spot on the end in my underwear. I think to myself that I'll have to fuck him after this, after I'm done here. Want to do that now, but not quite yet.
"Baby, you are so cute, you make me very happy." I pat his butt, stroke him gently. "I have to thank your wife for that, she's done wonders with you. If it weren't for this little thing..." I reach down and flick his tight pushed up straining balls just outside of the back of his chastity tube, flick them hard. As he whimpers loudly, cries out and flexes his butt from the pain, sends a shock through him, he arches his back slightly, "...nobody would suspect that you are a sissy girl. They'd think you're a real girl. Your wife has done wonders with you. I do have to get her a present of some kind. She's a marvelous woman."
And she is. Since she talked me into letting her feminize the little bitch he's learned to do it all. Style, make up, hair, all the things women do, he does all of it better than any woman I've ever dated. And as she said, she told me she saw his 'potential' years ago, saw that he's a very much passable CD girl. Take him out in public and nobody even suspects he's a sissy boy. I've taken him out and nobody ever seems to suspect that he's a he. Astoundingly girly, my sissy boy wife!
I move my hand to cover the entire curve of his left cheek, let my fingers fall into the crack of his rear. I put my middle finger to his hole and slip it in slowly, full length. He instantly tightens on my finger and then hurries to relax. If he fights my hand he'll be whipped. He knows that, he knows all the rules for being a good girl. I hear his sexy little whimper, stifled little cry, as I push it in deep and hold it in place. I see him look to the floor, see him close his eyes in the mirror, hear him start to moan as I pull out slowly half-way and then push back in. I hold my finger there and flex it at the joint. He starts to squirm, can't help himself. I open and close my finger as I hold it in as deep as it will go. I laugh out loud as I straighten my finger and start to make my little girl move.
"Arch your back, honey, come on. Push that butt up, I want to see." He does as told as best he can, strains to hold his rear up high for me. That's when I start to really concentrate on that tight little hole. Finger him long and slow while he remains perfectly still with his butt pushed up high, feel that tight little ring of his ass close around my finger as my finger moves in and out of him. I hear him start to breath deeply, moan like he always does at this point. Feel him start to get deeply into what is happening to him, I start to work him. With my other hand I hold his cheeks open, using just my thumb and index finger to spread his cheeks apart. I completely expose his very tight little pink hole, see the pink edges of it quiver as it's stretched and held open. I see his tiny penis strained and grow semi-erect in its harness, se it too strain at the end of it's locked cage. The only sounds in the room are his soft whimpering moans and my finger running in and out of the lubricated little hole in front of me. I could do this forever.
I glance over at the clock. I've been finger fucking him for half an hour now. I can make him cum like this if I want to, have done so before. I can actually milk him like this. But not today. I want to cum and as always he's got me so hard I almost do it in my pants. I've been thinking about fucking him since noon at the office. That's what this is all about for now.
"Get up, baby." I pull my finger out of him, slap his rear end with my open hand, finger so slippery from his lubricated hole. "Let me help you, honey." I quickly help him off my lap by his arm, grip him so tight he yelps as he rises off of my lap.
He is panting heavily, looks so sexy with his long hair over one perfectly made up eye. Hear those sexy earrings jangle as he breathes deeply. This is exactly what I wanted, he's more than ready now, the submissive side he dives into so deeply, he's almost out of control in it. He's ready to be taken. He will literally do anything for me when he's like this.
He glances at me and then to the floor. He can't not look at me, sneaks little peaks at me as he tries to keep is eyes down. He has to know how good he looks to me now. Skirt still up over his rear, hands restrained behind his back, panties dangling just above his knees now, little boy dick all caged up above his perfectly baby smooth legs and crotch. Such a picture!
I stand, take him by the arm. I can't resist, lift his head just under his chin with my hand, French kiss him deep. Run my hand down over his naked butt, feel him push up against me, push up against my erection. I know what he needs. I pull away from him, hear him breathing so heavily, unable to compose himself. I take the key to his cuffs from my pocket, unlock his wrists and let the cuffs fall to the floor. I put the finger I used on him into his mouth, watch him suck it so sexy, so soft and gentle—see him tease, so anxious.
"Let's go up to my bedroom, see what a good little wife you can be." I pull my finger out of his mouth, reaching back I pat his rear, taking his arm I start toward the stairs. All I can think about now is him underneath me, want to fuck him in the missionary position, on top of the little bitch, it's all I can think about. I feel my cock throb inside my pants as I picture his mouth on one of my nipples, his eyes closed, his legs wrapped around my back, in deep between his legs. I almost cum thinking about that as I hurry him up the stairs to my bedroom...