Her story

sissy_bois: I am a 21 year old woman, and very much
I am a 21 year old woman, and very much into sexy young transvestites, guys in make up, pretty boys, forced feminisation, strap on sex..
So I wrote a story concerning all the following. I'd like honest opinions if you're interested, but please be kind as its my first story. Hope I'm posting in the right place.

I enter the room quietly, even though I know he can't hear me above the sound of his whimpering.

I gaze at the restrained form of my little transvestite. He has been lying there for an hour, all done up just as I like. Black, sheer, lace topped hold ups cover his smooth shaved, shapely legs, high heeled platforms on his feet. A black pvc maid's outfit fits his contours perfectly, cinched in round the waist by the black satin corset I've tied impossibly tight. The flared skirt only just covers the white lacey petticoat beneath it, a sexy expanse of bare thigh visible between the top of his hold ups and the hem of the petticoat, and it is all to easy to imagine the naked, smooth ass it covers. Above the corset the fake breasts heave, pressing against the restrictive bra and pvc dress. The long hair of the wig lies against his cheek, shielding the beautifully made up face which is at this moment shoved into the pillow.

I walk forward, stepping over the debris on the floor, a result of the earlier struggle to get him into the humiliating outfit. He is face down on the bed, ass high in the air. His ankles have been pulled apart, held tightly in place by a spreader bar which is chained to the bed, leaving his legs spread wide. His pvc clad wrists are secured to the chain tightly encircling his corsetted waist, leaving him utterly unable to break free or even touch any body part. A black leather posture collar holds his head firmly in position; high, looking straight ahead, elongating his throat. A gag is keeping his whimpers to a minimum; a small detachable prosthetic cock keeping his teeth apart and forcing him to suck on it.

I reach out and run a cool hand slowly up his thigh. His entire body jumps, but only a little, the chains make sure of that. I caress his smooth inner thigh and am glad I forced him to shave off all his body hair that morning. His breathing becomes more and more ragged the higher up my fingers travel, stroking him gently.

Suddenly I stop, and walk to the top of the bed. I grab the ring on the posture collar and yank his head up to face me. I gaze into his large, beautiful eyes, filled with tears of humiliation, the perfectly applied make up only slightly smudged from crying in frustration. He stares at me imploringly, and I simply smile at him as I remove the dildo from his mouth, unfastening it from the gag quickly. He struggles to speak, perhaps to thank me, but only manages a moan as there is still a wide metal ring holding his mouth wide open.

I pull up my short skirt and expose my cock. It sticks out seven inches from my body, the black straps barely visible against my black thong. His eyes widen as he stares at it and watches my hand glide up and down the smooth, thick protusion.
"Do you want my cock?" I ask him.

He whimpers and tries to shake his head francically, but the collar holds him steady.
"You're going to suck my big cock, you little slut, and lube me up well so I can fuck your tight little ass," I whisper to him, and shove my cock through the metal ring in his gag, deep into his mouth. He moans, and whimpers, but cannot shut his mouth or spit me out. The ring gag holds his mouth open as I grip the back of his head and force his mouth down, ramming my cock deep into his throat as he chokes and whimpers, the chains rattling as he struggles on the bed.

I moan as I watch him wriggle, sucking me against his will, the latex cock shining with saliva as I push into his straining mouth again and again. Finally, when the tears are streaming down his face and the gagging sounds are becoming more frequent, I pull out and replace my long hard cock with the tiny one, fitting it back onto the ring gag. Moving quickly down to the end of the bed, I push his skirt up round his waist, exposing his smooth, pale, perfect little ass, spread wide before me.

His moans increase in volume, and he tries to kick his legs, to no avail. I lean down and gently lick at his asshole until his moans are less angry and more needy. I soak his hole with saliva, thrusting my tongue in and out of him as he tries to press himself harder against my tongue, groaning and wriggling harder than ever. Finally I pull away, and grab his ass cheekc, spreading them even wider.

He tries to protest as I touch the dripping tip of my cock to his wet slippery asshole, straining towards the top of the bed and getting nowhere.
My hands move up to his waist, gripping around the corset and holding him firmly. I wait until he is practically screaming in hysteria before I plunge the full seven inches of my cock deep into his ass.

As soon as I'm fully inside him his whole body spasms, the screams he is making getting louder and more and more hoarse as I start to thrust, backwards and forwards, moaning myself and feeling how wet I am against the straps of the strap-on, pushing deeper and deeper and imagining the tip of my cock rubbing against his swollen prostate.

His whole body starts to tremble as I cram my cock as far into his tight ass as I can, and with a scream he orgasms against me, bucking in his chains and kicking his legs as I press my breasts against his back and firmly hold him down.

When the final shudders have passed through his limp body, I untie him, kissing away the tears and holding him tightly in my arms until he sleeps.
...
[the only thing I would add is: And then I scooped up all his hot white discharge with my rubber-gloved hand and made him kick it clean.]