My god! I didn't think I could take anymore. The massive cock had no mercy, it was ripping me in two, shredding my hole. Inch by inch, unflinching, demonstrating an unstoppable lust to impale my cute little cross -dressed ass. His huge ham-hock hands were gripped on my waist, I felt like a rag doll. He was in complete control with one goal, to completely rape my ass until his savage desire was quenched. Slowly my hole was taking in more of the veiny monster but I stil had 6 inches to go. Suddenly he stopped for a moment and I exhaled, trying hard to relax my sphincter. "You like that, don't ya bitch. Now tell these boys watching, how much like my cock" he ordered. Sheepishly I turned to face the men standing there watching my inpalement on the monster cock. "I, uh..., uhh.. like it, I ... like the cock," What I heard next was condescending laughter. "Damn, bitch likes it, bitch sure do like the cock" I heard back from them. His grip tightened then and he drove me down on it two more painful inches. The watchers laughed some more. In my humiliation, tears started to roll down my cheeks. Again his grip tightened and he slowly drove the monster in deeper.
Before I go further, let me fill you in on the background. I am a thin, mid thirties bisexual man. I have a decent job and live alone. My luck with girls has been sketchy, mainly due to my kink, which is that about once a week I dress up as a woman and have sex with other men. I don't do this because of gender dysphoria or anything like that, I enjoy my cock, I enjoy living as a man and I enjoy fucking both women and men. I do it because dressing gives me a sexual thrill and it is an outlet for my masochism. Being fucked by other men while dressed seems to satisfy my need to be humiliated, it satisfies my deep, unresolved feelings of self hatred. Note, I have deep love and respect for all other trans people, the truth is that everyone's motivation is different. I just need to be honest about mine. Okay, enough of that. Here is how that night began.
Friday night, needing cock, I dressed in black 4 inch heels, fishnets, pink mini, black leather corset with a silk top underneath and falsies, whorish makeup, including cocksucker red lipstick and a red bob wig. I started at the bar of a downtown Marriott hotel. I love hotel bars, men alone on business, away from family, friends, prying eyes and normal gender obligations, with a ready room upstairs, they can usually relax and indulge their interests, especially in girls like me. I bought a drink and sat at a table. I didn't have to wait long. He said he was Michael, mid 40's, 6'1", decent build, salt and pepper hair. He sat down introduced himself, I was bold, I said he had nice hands so that must mean he has a nice cock. He blushed, I licked my lips and said "Show me". Up to his room, a little necking on the bed, while I felt him up. Then down to action, I fell to my knees and undid his pants, he stepped out of them, I started nuzzling around his boxers, licking through the material, all the while, looking right into his eyes like the wanton whore I am. Finally, I needed to touch it, I pulled the boxers down and it sprang to attention in front of me. About 7" long, mid range girth, sticking out straight but bent down at the end, cut, a nice little drop of precum on the tip. "MMMHHH" I moaned, licking it off, and while looking at him, relaxed my throat and took the whole thing down all at once, balls deep. "Ahhh" was all he said. I bobbed on it for a minute or two, then I took it in my hand, stroking it, while I went to work on his balls. Balls a bit small for his size, they smelled like baby powder. I got them both in my mouth easily. Then back to work on the cock, taking the whole thing down, nuzzling my nose in his pubic hair and letting his balls bang on my chin. All the way down again. Then I concentrated on the underside of the head. Flicking my tongue along the sensitive underside up into the piss slit and then suctioning down the whole head hard. All the while, my right hand was gripping it and relvoving up, down then rotating. His moans got deeper, his legs started to get rubbery, he was on the brink of letting loose of hot, salty jets of white nectar. His balls tensed up a bit, he was on the edge. That's when I plopped the raging cock out my mouth and gripped his balls, tugging them down a bit. Whew! he almost came, but I did get a delicious half spurt of his juice. I stopped him because I wanted him to dominate my fuckhole and I didn't think he could cum twice. On my knees, I looked up at him and said while batting my eyelashes "damn stud, this will be sweet, but you own my ass and you should have a piece now."
I sat him down on the bed, and wiggled my pink mini encased ass in front of him. I then then turned and said "grab it, feel it, own it". His hands mauled all over my ass and crotch, violently yanking down the mini, and then my panties which I wore over the garters holding up fishnets. His thumb found my rosebud and toyed with it for a few moments before plunging in. All the while was I wiggling and moaning, savoring the expectaion of the sodomization to come. I turned and said "let me prepare it". He reluctantly let my ass go, I went to my purse for a rubber and lube. With my back to him I ripped the rubber open and put it my mouth. A trick I learned of, the best French whores would put the rubber in their mouths and orally roll it down. If done right, It was said, the men never hardly could tell. I have practised this quite a bit myself and have gotten pretty good at it. I fell to my knees and swallowed his cock whole applying the rubber as I went down. Then I poured a bit of lube into his hand, stood up and turned around for him wiggling my fuckhole. His hand lightly brushed my engorged pink rosebud, the first one finger, then another penetrated me, lubing, stretching and stimulating me.
I was ready to be sodomized by that rock hard cock. I turned, then got onto the bed, kneeling on the edge, legs wide apart, calves and feet dangling over the end. I laid the side of my face against the sheets while holding onto the other side of the mattress for balance. in this postion I was wide open, utterly exposed, truly submissive to his manly desires. The first thing I felt was his head running my entire crack, then he pressed it down at the top of my crack slowlly running it down to my rosebud. Stopping at the rosebud he slowly applied pressure and my fuckhole yielded, opening to bulbous cockhead. I was ready for it, no pain just divine sensations of submission as he penetrated me. Past the sphincter, the sensations changed to a feeling of fullness. Slowly, he entered my boi pussy, I could feel the veins on the side of his man pole throbbing as it powered further into my tranny twat. About 3 inches in he stopped and let out a moan of engrossed pleasure "aaargh" and then"damn, that hole of yours is hot, bitch". Then he greedily rammed it home, balls deep, and I let a sigh of pleasure and slight discomfort. "Aaahhh, yes baby, now fuck my bitch hole hard", I said. He then gripped my waist and began to jackhammer my tranny twat. Like a piston, bang, bang, bang his balls slapped into mine. Then a breather, he pulled it all the way out, my boi booty was tingling in anticipation. He lined up his proud manhood and rammed it home in one stroke, again, and again, it took my breath away. I sensed he was nearing explosion so I took one of my hands off the bed edge and started stroking my cock. Having his beautiful cock dominating my hole, It did not take long for me to get to the edge too. The first convulsion engulfed my entire body causing my tranny twat to vise grip the the cock reaming me, then a momentary release and the next convulsion was even stonger, squeezing that manhood inside me. The convulsions quickened and that put him over the edge too, ribbons of searing, white hot man nectar spurted into my tranny twat. We both shuddered as the waves of orgasm rolled over us. A deep, satisfying completion to the fuck. He was out of breath and fell onto me, his cock still buried to the hilt. Sweating and panting while lying on my back, he whispered in my ear "you wiped me out baby". His breathing got deeper and slower while the cock inside me shrank until it popped out. I wriggled out from under and saw that he was asleep. Damn, I wanted more of his sweet meat, good thing I saved it for the fuck, I thought. I then went to bathroom and cleaned up. A fresh coat of war paint and I was ready for more new and unknown cock.
Back down in the Hotel bar, it had gotten a bit crowded. Strolling up to the bar in my whorish get up, oblivious to the dirty looks and muffled tranny taunts, I ordered another beer and had a good look around. I could "PASS" if I wanted too, but, I don't want to. I am thin enough and my face is soft enough, my height 5'10" is a bit of a drawback, but that is why they made flats. The reason I don't want to "PASS" is that I want everyone to have NO doubt as to what I am. A man dressed in whorish women's clothes. It's part of my masochistic need for humiliation. I get off on the laughter and taunts. Don't get me wrong, I look extremely fuckable, but on the second look you can pretty easily tell that I am a guy. I want the guys that approach me to know, that with me it's like that Lou Reed song "Take a Walk on the Wild Side". The bar was almost full, but I spotted an empty table near the back. Holding my head up high, licking my lips and swaying my ass, I sauntered through the room to the table, gathering looks all the way. Normally, any the guys who are out together will never approach me, no matter how much they are into trannies. They would never want their friends to know that. Those are the guys that usually make a scene out of insulting me, It is a defensive reaction to their homosexual desires. That is why what happened next was truly unusual.
At the table next to me, there were 4 four guys driving from Seattle, UW, down to San Diego for Spring Break. Two black guys, One was about 6'3" muscular, the other was about 6', stockier, but still decent muscles. One white guy 6'2", curly brown hair, swimmers build and one humongous Hawaiian dude. He was 6'4'' Massive Chest, no neck, straight black hair, flat nose, and ham hock hands. As I sat down at the open table one, the stocky black guy made an insulting remark about trannies. I ignored it, and a few moments later the Hawaiian guy a "tank" is the best description of him, he came over and apologized for his friend. I graciously accepted and invited him to sit with me. we started to chat, His name was John, he was indeed from Hawaii, 20 years old, studying to become a veterinarian. I asked him if his friends would give him a hard time for talking to me, since I was so obviously a tranny. He said no, he was openly bi and his friends knew it. I was really warming to John he had a pleasing masculine way about him. He was literally, one of the biggest and storngest men I have ever met. Just looking at his mammoth hands made my boi buns tremble in anticipation of the dimensions of his manpole. I slowly licked my lips in the fashion of a true harlot, while putting my hand on his and asking if he was staying at the hotel. He said yes, but that he was sharing a room with his friends. With a straight face, I said I had never seen the rooms in this hotel and I wondered what what they were like. Would he be kind enough to let me see his room?, I asked vampishly. He just smiled and held out that boulder he called a hand. His friends made rude catcalls as we left the bar, causing all the patrons their to smirk in disapproval. But I was quivering in anticipation.
As soon as the door closed, he was on me. His gigantor hands gripped me and drew my whole body near him as if I were a flimsy toy. He pulled me in for a kiss, and his elephantine tongue forced it way into my mouth. I immediately drew in my mouth trying to suction as much of it as would go, into my mouth. He drew back and said "Whoa, bitch, do you think you are whore enough to handle me?" I bravely said yes, not yet knowing the epic slab of manmeat concealed in his pants. He then brutally pushed me to my knees and forced my head into his pants covered crotch area. Feeling it for the first time, the mass, the heft and outline of it through the cloth of his pants, I shuddered in fear. The word mammoth is inadequate to describe the size of it. "Whoa......." I thought to myself, I love dildoes and I have taken a few of the bigger ones up my carnal boi cunt, but never anything like this. This would hurt. I immediately started working it, sniffing and licking through the material waiting for it's unveiling. While I was working it, he slowly took off his shirt and then unbuckled his belt, unsnapped his pants and drew the zipper down. The pants fell to the floor and It revealed itself. Still flaccid, I revelled in it's glory, my guess, 12 inches long, girth, both hands could barely fit around it, uncut. I rolled back the foreskin and exposed the head. The head was well proportioned for the size, beautiful round crown. He looked down on me, noticing the fear in my eyes and he laughed cruelly, saying, "Oh yeah bitch, you are gonna take every inch of it whether you want to or not. Now get to it". I opened as wide as possible and took the head into my mouth. Nice slightly salty taste, good hygeine. Both hands working it, stroking up and down while turning, trying to stimulate as much area on the monster as possible. As I worked on it, the prodigous pole was slowly growing erect. Again I quivered in fear for what was to come, feeling palpitations in my tranny twat. I really strained to open wider and take more of it, I eventually got in the first 6 inches until the girth was too much. So I just concentrated my mouth on that while my hands continued working it. he slapped one of my hands away and ordered it to work his balls. The balls... man, they were more like dinosaur eggs than balls. But I did as told, using every trick I know, rubbing, light pulling, light scratching style stimulatulation, I licked them, tea bagged what I could and then blew on moist area. After a few minutes of that he said "ahhhh, yeah bitch, that's it, now get ready".
I drew away and there it was, fully erect, like a oak tree root. I then reached into my purse and took out the rubber I never thought I would use, The Double MAXXXUM, It was almost impossible to get on, but after a while It did roll down, more like a ballon than a rubber though. I then stood up, pulled up my mini and pulled off my panties, turning around, I wiggled my trembling twat against it. Whoa.. Onto the bed I climbed, Kneeling on the edge, legs spread wide, calves and feet dangling over the side, my face pressed against the sheets and my hands holding the opposite edge for balance. I was totally exposed and vulnerable, my rosebud at just the right position for him to walk up with that raging root and wreck my rosy ringlet. I could feel it approach, the anticipation, just at that moment his friends burst in. John turned and said "What the fuck?" They said it was boring down in the bar and the show up here might be more fun to watch. "But you guys give me shit about being bi, what the fuck, now you want to watch?" John said. One them replied "Okay, no more shit, but we get to watch". John agreed and then he slapped my exposed ass and said "You better give these boys a good show bitch". They all laughed. I was too scared of the monster cock to care. Then he roughly moved forward to my exposed, tremoring rosebud. It felt like I was trying to fuck a fire hydrant as the head applied pressure to the hole. I breathed deep in and out willing all my concentration to relax my rosy ring. That helped and slowly, my hole expanded. The boys watching were impatient "yelling ram that bitch already", John gave into them and pushed it past my ringlet. the pain was unbearable, I shouted "stop". thank god he stopped and gave me a few minutes to adjust, just as the pain subsided he ploughed in couple more inches, the pain raged again and he waited. then ploughing in a few more inches.
My god! I didn't think I could take anymore. The massive cock had no mercy, it was ripping me in two, shredding my hole. Inch by inch, unflinching, demonstrating an unstoppable lust to impale my cute little cross -dressed ass. His huge ham-hock hands were gripped on my waist, I felt like a rag doll. He was in complete control with one goal, to completely rape my ass until his savage desire was quenched. Slowly my hole was taking in more of the veiny monster but I stil had 6 inches to go. Suddenly he stopped for a moment and I exhaled, trying hard to relax my sphincter. "You like that, don't ya bitch. Now tell these boys watching, how much like my cock" he ordered. Sheepishly I turned to face the men standing there watching my inpalement on the monster cock. "I, uh..., uhh.. like it, I ... like the cock," What I heard next was condescending laughter. "Damn, bitch likes it, bitch sure do like the cock" I heard back from them. His grip tightened then and he drove me down on it two more painful inches. The watchers laughed some more. In my humiliation, tears started to roll down my cheeks. Again his grip tightened and he slowly drove the monster in deeper. I adjusted again, breathing deep, arching my back and concentrating on relaxing. Just then he went for it and rammed the rest of it home, balls deep. I yelped in pain, it was unbearable the tears running down my cheeks, It was all met with laughter from them. "Ha ha, like the cock now bitch?" they all laughed. More concetration, more deep breathing and finally I could take it . John slowly pulled out about 6 inches then rammed it home again. The pain was a little more bearable this time as I adjusted. 6 inches out and then rammed it home again, balls deep, my hole spasming around the prodigious pole. He was fucking me harder than anything I had ever experienced, He started withdrawing more than 6 inches, then 8, and rammed it home, out and back like the log ride at Disney, It was the log and I was the cave. I was stretched to the extreme but still, I knew I had to take it, I knew I had to be fucked like this. No matter how much it hurts, a cock like this is every boi's dream. Then something amazing happened, the pain rolled away only to be replaced the most amazing sensation of fullness. All the nerves in my trembling tranny twat were firing and the epic slab of manmeat was more than jamming my prostate to the max. The sensations started to become electric even as the guys watching started chanting "Ream the bitch, Ream the bitch", John's pace picked up, the massive cock, unstoppable. As the cock twitched it literally moved my entire body in reaction. The guys were now really getting into it. One of them yelled " hey John the bitch really likes it so make her beg for it" He then stopped completely, slapped my ass again and said "beg for it bitch", they all laughed. Overcome with lust, I did just that "I beg you to fuck my bitch ass" I said and they all laughed again. John then held it still and said "fuck yourself, bitch" and I did, rocking myself back and forth on his prodigious pole. At that, they all laughed again and that was it for me, from deep in my bowels I started to convulse, impossible as it seems, my wrecked rosebud even gripped the monster tighter in the convulsion, and again another convulsion, deeper and stronger, the orgasm was coming from the darkest nether regions of my bowels and subconscious self hatred. The convulsions started coming quicker, my entire body spasming, my trembling tranny twat gripping it tighter. Their laughter and my complete humiliation growing, all cumming to a crescendo. This put John over the edge too. He let out a mighty "AHHARGHH". My body jerking around like a eplileptic in seizure as I came and the mammoth burst forth it's searing white lava into my bowels. The orgasm lasted for at least 2 minutes, I was jerking and convulsing all over the mammoth root whilst it rammed itself balls deep into me spurting it's hot white nectar. As the orgasm ended John the human "Tank" felt his legs grow rubbbery. He pulled the moster out of my now gaping, cavernous cunt and he fell onto the bed, bouncing me off on to the floor. They all laughed at this.
As I pulled myself to my feet they ordered me to turn around and show them my gaping hole, I did, they laughed again. I felt physically more empty than I ever had been. Mike Tyson could have fisted me then and I would have hardly noticed. My rosebud was royally reamed, it was still gaping open. I could feel the air on my bowels. I was fucked. The 6'3" black guy then undid his pants and pulled his shorts off, revealing a a very nice 9 inch cock. He said "bitch, if you beg for it, you can suck me off". I looked at luscious black snake and I knew what I wanted. There I was, I had just had the most humiliatingly intense orgasm of my life and I still wanted more. So I begged for it. He then walked over and slapped my face with his cock repeatedly, he told me to close my eyes and open my mouth. I did and then he rammed it all the way in. My nose was in his pubic hair, I relaxed my gag reflex and let him fuck my face. He pulled out before cumming and painted my face with jizz. They gave me a towel I cleaned up and then sucked the other two off as well. After that, I gave them my number, told them to call me when they come back through Portland and then I redid my outfit and makeup as best I could and grabbed a cab home. Never to forget the night I was REAMED. I am not a size queen, I like to be fucked by all sizes of cocks, but that was an especially memorable night.
P.S. -- A week later I got a call from the stocky black guy who made the insults towards me while they were at the bar. Sure enough, he was a closet case and was only acting out to hide it from his friends. Sometimes I top guys and that night I definitely gave it to him every way he could handle. He seemed to enjoy it. I wished him well.