On No He Didn't

"Aaaaaagh", he cried out in pain as he pressed back hard against my dickhead and I slipped between his tight sphincter. There was no lubrication except for my pre cum, so he gasped in pain and pleasure as he felt the increased friction of my dickhead stretching him.

"Aaaaaagh", he cried. Deeper lover! "Aaaaaagh", Fuck me I am your bitch, Darnell. I truly want to be your lover, and will never cheat on you again, keep me locked and I will prove it!"

"OK, you sexy sissy, I'll fuck you so hard you may not be able to take it!" And with that said I slammed the last few inches of my dick into him and began sliding in and out slamming him against the countertop with each forward thrust so that he have to hold on tightly to withstand the force of me fucking him.

My dick entered his ass hole easily now gaped from constant wearing larger and larger butt plugs for months now while cleaning the house to prepare him for when he willingly surrendered his virginity. I knew that he felt some slight pain, but instant pleasure as well. It took me only a minute to hit his prostate, it seems the butt plugs he had been forced to wear daily had done their job. With Rick's hole loosened up I started to speed up my strokes.

I could tell from my personal experience being fucked that he was feeling the pleasure getting stronger and stronger as my dick rubbed his prostate more and more. I was certain he was very close to what I was hoping for. I wanted him to willingly surrender and orgasm on my dick proving to me that he was dick whipped.

"Ooooh, ooooh, ooooh! Yes Darnell, give me every inch of your dick", He cried out and moaned, "Aaaaaagh." I was fucking him so hard that his ass hole was crying out with the pain and pleasure of it. I was grunting and moaning behind him with the effort of it and he didn't even have time to press his ass back before I was slamming forward again.

As his pleasure began to grow increasingly stronger and stronger, my strokes got faster and faster, and harder and deeper. I kept pumping knowing his pleasure was building, he tried to relax his ass. Minutes went by that felt like only seconds as the pleasure kept building and building, and as it took him to the peak of pleasure, his body tingled, and his mind went numb as he felt his prostate ooze drops of thin liquid out of his caged dick hitting his long hairless leg.

This was the long-sought moment that I had worked so hard for. This once arrogant seemingly masculine top now willing giving his virgin ass to me. No conditions just absolute surrender for the rest of his life. Never to be release from his chastity cage except for cleaning or to move to a smaller cage until his dick was a nub, shamelessly much less than an inch when released and erect.

Rick was shocked! He didn't expect to ejaculate from being fucked while locked in a chastity cage. His orgasm was incredible as my dick kept massaging his prostate. He thought it would be the same feeling he would get after a normal orgasm just release guilt and the desire to go to sleep, but he was still as horny as he was before, if not more.

As he moaned I still pounded his asshole he felt the pleasure in his prostate growing again. This was incredible! As he reached the edge again, he dribbled another hot stream of thin watery cum from his chastised dick...his body shaking with every thrust.

As he rode out another caged prostate orgasm, he felt the pleasure slowly fading from his hairless body. He figured the fun had ended and was about to finish up...As I was going through a couple slower deep thrusts to finish his session up, he felt that pleasure that was fading returning ever so slowly. I picked up my pace the pleasure built even faster than before his prostate released even more liquid from his dick. At this point Rick was moaning with pleasure and panting like a bitch. He had had three of the most amazing caged prostate orgasms more intense than he ever imagined as I ravaged his now greedy well fucked ass making him my sissy forever.

It was a beautiful scene as I held his hips with my dream man locked in a chastity cage, neutered, skinny, rendered emasculated. He's now just a fucking the boi pussi, a sissy who I own. I know that Rick loves giving his ass to me. I know he loves being my bitch, I love his high-pitched wail when he moans "Yes!" in response to my fucking him. My man is broken fully letting go of all pretense of being a top and has found his real place and role. He's right where he's supposed to be and he's loving it.

He looked so weak and powerless it was like the most exciting of fantasies. Suddenly I felt myself pumping my first spurts of warm cum in his rectum and I cried out as I shuddered and collapsed against him.

I pulled Rick tenderly against me and wrapped my arms around him, I stroked his tender well fucked ass. "You are such a good fuck Rick. I've never been so turned on fucking a man before. I hope I didn't hurt you", I told him as I licked and sucked his neck and ear.

He whispered back telling me, "Don't worry lover you were incredible you are so strong, and I love having you take full control of my life".

I pressed my lips against his and slipped my tongue into his mouth. My dick was straining against him trying to get hard again. "Now I'll let you sleep in my bed tonight.

"Ooooh, Darnell, thank you I would love that more than anything!". I then took him by the hand and we walked to my bedroom, Rick still enjoying the delicious ache in his ass from where I had just fucked him and made him my bitch forever. His weak and totally satisfied body staggered off to the bedroom with cum slowly slipping out his well fucked ass and down his leg as he basked in the afterglow of his fucking. Rick's phony alpha facade had been destroyed forever not believing what he had just experienced. His now total unquestioning submission was obvious.

I knew my plan to let him fuck me first had worked well and I was going to keep him in chastity and shrink his once 11-inch dick down to nothing. He would never be able to fuck me or cheat on me because his dick would be way to small. The only way would be for him to give his precious ass to another top. I enjoy having him ask me to please ride his back.

THE MAILMAN 'CUMETH'

After a few months I had bought him more sexy lingerie than most women. This carried on for some time, with me now getting frequent blowjobs and me fucking his ass. One day when he was doing his usual routine cleaning wearing his maids outfit when the doorbell rang. He was a little scared and started for the bedroom.

"Bitch! get your ass back in here and finish your cleaning," I snapped.

He was really nervous about it, but he went back to his cleaning. I opened the door so he could see that it was the mailman. He was about 28 years old 5' 8" and very good looking. I asked him to step in and sit the large package down in the foyer while I signed for it, I noticed the mailman checking Rick out as if he recognized him, when I said.

Rick after getting a good look at is face tried to vanish into the back ground while he did his cleaning and hoping that he had not been recognized by the mailman.

I said to the mailman, "I can give you a ten-dollar tip, or I can have my sissy maid give you a blow job." Rick was mortified when I said that. His body visibly trembled as he struggled to keep his balance in his heels. I waved him over and he timidly teetered towards over to me and the mail man curtsied, and I said loudly, rub his dick through his pants and encourage him to accept my offer. Don't worry his dick won't bite."

The mailman was stunned but he didn't say a word, but I could tell from his growing bulge that he was interested. I ordered Rick to take his hand and lead him to the couch where he could be more comfortable.

Trembling at the thought of what was about to happen, but even more fearful of what would happen if he didn't do as he was instructed Rick reached out his trembling fingers with his brightly polished fingernails and timidly undid the mailman's uniform pants an eased them and his underwear down to the floor exposing his very nice 7.5-inch dick. He began stroking his dick, fearfully getting reacquainted as he knew what he was expected to do.

"Sit down relax, I commanded, let my sissy make you happy," I said.

It didn't take that long for Rick to take the mailman's dick in his mouth It started with a gentle kiss on the head then Rick licked the sides running his tongue between the veins. Then he paid attention to the balls licking slowly then carefully taking them one at a time in his hot mouth. His head bobbed franticly up and down as Rick knew I expected him to do.

After a few more minutes the mailman started rubbing Rick's head and rolled his eyes back into his head in pleasure. A few minutes later, enthralled the mailman let out a deep moan and shot rope after rope of his hot sticky cum down Rick's throat.

"Woooow, that was great," looking knowingly in Rick's knowing eyes he said. "Errrrr but I have to get back to work" the mailman said.

Before he left I dismissed Rick and had a pleasant chat with the mailman that brought a smile to his face when I gave him a twenty-dollar tip.

Later that night when Rick and I were relaxing on the couch watching a movie he was on the floor at my feet sitting on his long legs curled under him and wearing a red satin lace steel boned corset with matching garters and fishnet stockings, fuck me pumps and his red lacy bikini thong briefs with his usual XXL butt plug in his ass that I made him wear.

"As I sipped my wine I asked him how he liked sucking the mailman's dick?"

He replied sheepishly that, "it was all right."

"Just all right?" I asked again.

"Well it was very nice," he admitted.

"Just nice, that is too bad since you missed out on sucking it all the times you were together and fucking him."

Rick just sat there in stunned silence when he realized that I knew the mailman was David who I had caught him in bed with. I didn't say another word allowing it to sink in knowing that he was quaking in fear of what I might do to him. He was thinking that all he did was do as I instructed hoping that I would not treat him too harshly.

But the side effect was what I really wanted his gripping fear that made him become even more submissive and compliant and attentive to my every need. Allowing me to lock him into and even smaller chastity cage a few short weeks later, and willingly let me up his dose of HRT pills and shots which started to feminized his once athletic masculine body beyond the point of no return. All that remained of the athletic hunk was his height but his body was slim his hips were wide and he was starting to develop some nice sized breasts so he could later accommodate some huge breast implants.

If you are wondering I had the mailman visit often to partake in Rick's mouth and ass. What they both didn't know was that I had plans for both of those cheating bitches.

REVENGE IS A DISH BEST SERVED COLD

As for David, he was later hired after an anonymous complaint got him fired from the post office for having his mail van parked in my neighbors drive way so often and I quickly offered him a job as my handy man and my chauffeur. (You are right it wasn't the neighbor who made the call) When he accepted my offer to move in I knew I had him where I wanted him. This was his punishment for him sleeping with my man, slow feminization which began with hormones.

After 8-months he is now forced to wear strict steel boned corsets, keep his ass plugged, and his dick in a micro cage like my boyfriend's. He has been given multiple surgeries, including facial restructure, the removal of his lower ribs so he could obtain a 16-inch corseted waist, Double 'D' breast implants which he told me hurt his back when he minced around all day in the 7-inch heels I make him wear. This only served to bring me greater pleasure.

His high heels were locked on his feet until his tendons eventually shortened to the point where he cannot wear anything less than 4-inches without crippling pain. Wearing high heels have left him high heel dependent so now he always minces around. I actually felt sorry for him and bought him several pairs of 4-inch shower heels to wear when he is in the shower or off duty.

For his chauffeur's job I insist upon him dressing the part in his tailored sissy chauffeur's uniform which consists of a short tight mini skirt made to fit tightly around his big hormone enhanced ass, black over the thigh 7-inch stiletto heeled boots with silver heels and buckles. He wears a black cap cocked to the left side and thin see thru pink low-cut blouses that show off his chocolate areolas and double 'D' breasts. A black leather waist length jacket that clings to his 16-inch waist.

THE ENDGAME

A year later when Rick was thoroughly broken we were a happy couple. Rick had settled completely in his role as my submissive trophy sissy with a bubble butt and large breasts. He has been doing all of the cooking and cleaning with some assistance from David he is always wearing the most feminine attire he can fine to please me.

For our anniversary as we got dressed to go to our club I was admiring how much Rick had changed. I noticed how the patrons kept tabs on Rick's transformation especially when Rick casually told them that he had gotten breast implants and let them feel.

Rick actually looked like a very tall slim sexy woman especially when he wore heels, and he had a voluptuous figure that was emphasized by his outfit, which consisted of a black leather corset which I made him wear starting a few months ago to emphasize how small his waist was now and 6-inch black high-heeled fuck me pumps and a micro mini skirt.

After 10-months of high doses of estrogen daily which served to make his own male boobs grow large enough for him to accommodate 'double D' implants. He has highly sensitive huge nipples and his shapely ass gives him a curvaceous ultra-feminine look. His tight steel boned corset squeezes and lifts his 'double D' cup boobs perfectly so that the flesh flows over the cups of his low-cut tops and are always on full display.

I was pleased that his 1-inch puffy nipples were always stiff, so much brown flesh was exposed. And his face - his face was beautifully made up, 3-inch thick 18k gold earrings he was movie-star beautiful, smooth dark skin with big, dark eyes, blue eyeshadow; high cheekbones; full, sensual ruby cock sucker lips which matched the bright polish on his 3-inch nails. A long, luxurious black wig that was combed back from his beautiful face and draped alluringly over his left shoulder and invitingly just below his ample implants.

The End