My crossdressing

I was a straight-acting 24-year old slim and fit man, once upon a time. Then Sally got inside my head and now, I crave cock. I have evolved from being a school-jock and a dick to being fucked by an older man, then on the weekends by a DJ. I had my ass broken in by a big black guy when the club I frequent was closed. Only for a motorbike gang to dress me as a girl and fuck me silly.

At work, I dared not test the waters and dress like a woman but at night I evolved into a full-on gay/bisexual crossdresser, in my house. I think Felicity, suspected something, as I had taken several Mondays off.


To break the path I was going on, I was thinking about trying my luck again with girls once again. I planned on going to a bar and attempt to pick up a girl. Only to see if I can and possibly if I could maybe stop thinking of getting laid by guys. As I was digressing into gayness, my mannerism started to change too, like I started to walk with this queer walk or strut, and wearing make-up in public, with caring about what people thought. Felicity at work loved it, she now had the power and took pleasure in giving me a hard time, about my faggot strut and make-up. I had no comebacks to her taunts. While at home, I usually dressed girly, I would wear oversized sweat tops, socks, and only undies, no boxers. Also, I was exploring, buying casual woman’s clothes and wigs, from eBay.

To break the path I was going on, I was thinking about trying my luck again with girls. I planned on going to a bar and attempt to pick up a girl. Only to see if I can and possibly if I could maybe stop thinking of getting laid by guys. As I was digressing into gayness, my mannerism started to change too, like I started to walk with this queer walk or strut, and wearing make-up in public, with caring about what people thought. Felicity at work loved it, she now had the power and took pleasure in giving me a hard time, about my faggot strut and make-up. I had no comebacks to her taunts. While at home, I usually dressed gurly, I would wear oversized sweat tops, socks, and only undies, no boxers. Also, I was exploring, buying casual woman’s clothes and wigs, from eBay.

At work, I dared not test the waters and dress like a woman but at night I evolved into a full-on gay/bisexual crossdresser, in my house.


I wasn’t yet confident enough to strut around in public, wearing drag. I told Frankie what had happened and why I wasn’t available on Monday and Tuesday, and he saw how rigid I was Wednesday and we didn’t do any sexual acts that week. The Club was shut for a month so I stayed home that weekend. I was back in the grove with Frankie the next week and had another lazy weekend. That’s when I started to scour the internet for more items like clothes, wigs, bracelets, that women wore.

It was Friday I arrived home earlier than normal, as the club was still shut for renovation. I drank some red wine and smoked some weed, listening to music.

So tonight I planned a night at home and to mess around with myself. I played with a dildo in my ass while smoking more weed, before douching out my ass. Then after I poured myself some more wine and I shaved the hair from my balls, and I used NAIR on my legs, arms, and boy-pussy. Then I showered and wiped off the excess hair.

Naked but for my robe, I sat on my sofa and relaxed with more wine, while listening to music. After a while, I felt the urge to dress up in women’s clothing and smoked more weed. I started feeling frisky and horny, so I played with my bare ass and started sliding a glass dildo in and out of it. I kept thinking about tomorrow night I will hit the club scene and try to bag myself a distraction, a MILF or lonely girl, but that was tomorrow.

Soon after I had finished a bottle of red wine, I found myself opening up my trunk of women’s garments and started dressing up. I slid a butt-plug inside my ass, and then dressed in my vinyl red and black mini-skirt, smoked more weed, put on my black bra with fake breasts and pulled on a tight pink tank-top, put on make-up, starting strutting around in my lounge-room, like I was on the catwalk.

Then I went into my bathroom and dyed my shoulder-length hair pink and purple, I couldn’t help myself and admired myself in the mirror. God, I thought to myself, I’m almost passible, except for this, as I waved my cock around.

After smoking some more weed, I removed the butt-plug and cleaned my ass up, and then put on some lingerie knickers and stockings, and then my 3” inch heeled Doctor Martin black boots. By now I decided to risk it and go out on the town, as a girl. So, I tied my hair into puff-ball pigtails, while admiring myself in the mirror. “Damn, I pass as a chick,” I said to myself.

I wasn’t in the right frame of mind when I booked a taxi, I put on a black leather jacket and headed to the Western side of the city. I randomly choose the Westside area because I knew no one in that area and people I knew wouldn’t go there. Rumors of crime and large black communities scared almost everyone I knew away from ever entering. So I was safe that people in my life would spot me, plus it was something different.


I didn’t know much about the area, and I asked the taxi driver to drop me off near the Club district.

When I first got there dressed up as a hooker, thanks to the weed, I started feeling regret. The thing I noticed first was, it was predominately a black area, and they didn’t look like happy people. I changed my mind and wanted to go back home, but the taxi driver took off before I could.

Ok, so I walked towards the clubs, swaying my hips a little and hugging my chest because I was nervous and scared. As I trundled down the pavement a minute or so, I noticed that I was almost ten yards from the crossing to the Red Light Center.

I had to wait for the light to change, but before it did, a hand grabbed me and pulled me into darkness. He covered my mouth, as he dragged me into a picnic area hidden by trees.

He sat me on the picnic table and started kissing me and I kissed him back. Everything was going fine until he noticed my cock under my skirt and froze. He clicked his fingers in the air and a few more guys arrived. Before I knew it, I was surrounded by big black dudes.

They were like a pack of wolves, watching me. I was 5’5 and 125-pounds, but compared to these monsters I was a midget. They were 6-foot plus and 250-to-300 pounds of big monster meat.

Within a minute my knickers were down to my knees, then another minute, knickers and stockings were gone. Then one of the men grabbed a hold of my cock and showed the group. “What’s this thing,” They all broke out in laughter.

He pulled out his cock and compared it to mine. It was six inches, flaccid, while mine was 6-inches erect. Then I looked around at the circling giants and all six had now pulled their cocks out, and all six had monster cocks. I then got shoved to the ground.

If I didn’t feel humiliated before, I was now, dressed like a schoolgirl and bare-assed and cock dangling in front of them.

Then one of them, who might be the ring-leader, ordered me to crawl over to him. I crawled up between his legs and stared at his salami cock, then we made eye contact. I then wrestled his cock out from his jeans and boxers. I lowered my head over his cock and started playing with it.

“Oh my, it’s a beauty and so thick,” I said, complementing it. He just glared at me. I started rubbing it, and licking it like ice cream, on a hot day. It was growing bigger and bigger. It took a real effort to take it inside my mouth, as it was thick as my arm. My mouth was stretched wide, and that was only half of it inside. It was still growing, inside my mouth. I was thinking to myself if I make him cum, and then the others, I might be let go.

“Damn bitch, you can suck really good,” He said. I think he was thinking about something but it wasn’t the same something, I was.

He placed his big black mitt on the back of my head, and then forced me down further into his cock, and then preceded to fuck my face with his large cock. He slapped my head with his cock, before shoving it back in my mouth, so violently it hurt my throat. In the space of five minutes, he fucked my throat so deep and rough, that he did something to my vocal cords.

His friends, called me all sorts of nasty names, like “whore, faggot, cocksucker.” Deep down in my self-consciousness, I felt humiliated and ashamed. I wasn’t all that confident dressing up as a girl in public, but here I was, on my knees in a picnic area, in the woods, with cock being rammed into my throat.

Then one of the men grabbed a hand of mine and put it around his cock, which I did instinctively, started to stroke. That gave another guy an idea, and my spare hand was made to do the same. As I stroke them on instinct, their cocks began to grow in my palms. Their cocks were also huge that by the time they were fully erect and moaning, they had made me barely able to wrap my hands around them.

The boss in my mouth was groaning loudly, which my I lost a bit of my reality enough to maneuver my head, so even more of his cock could go further down my throat. His friends were calling me all sorts of nasty names. He let out another loud moan, and he grabbed my head and pushed his cock even further inside my throat. His salami cock stretching my throat to the max and another two, pulsating in both palms of my hands.

“Oh God, I’m cumming,” He bellowed out as I felt his cock expand. Then his cock filled my mouth with warm cum. Most of his cum went down my throat until it near drowned me and I was gagging for air, and cum splattered out of my mouth when he pulled out. I coughed and gasped for air, with drool and cum dangling out of my mouth.

Once I seemed to recover my breathing, the two big dudes in my hands, started wanting some of my mouth as well. So the next I knew I was going from one cock to the other, like some sort of hungry whore. Until one of them tensed up in my mouth and began to cum. He flooded my mouth with his warm junk, which I tried to swallow, but couldn’t and some leaked out. Then his mate pushed him out and placed his cock in place of his. I licked cum off my lips when he did so. He fucked my face, pretty hard, until he rammed inside very deep, and another donation of cum flowing inside my throat. When he was down, he pulled out and slapped my forehead with his cock, I licked the slobber off it like melting ice-cream. I knew if I pleased them, then maybe they won't hurt me.

I was left alone briefly, squatting down on the grass and still on my knees. It was a good time to catch my breath again.

Another guy behind me flipped up my skirt and started to rub my ass cheeks, while another feed me his fresh cock. He forced his cock deep inside my sore throat. I tried to protest as best I could but complied with him. I was now on my knees with a guy rubbing ass. When he started to lick and finger my asshole, it drove me crazy and made me moan, instead of protesting. Then once he had two fingers inside my ass, I started wiggling my legs wider apart and allowing him more access. I concentrated on the cock in my mouth, while he woke my cock up while lubing up my asshole with Vaseline, without touching it.

Luckily his cock wasn’t as big as the other four, but it was still bigger than mine. Just as he was prying open my ass and entering, his mate in my mouth caused a distraction and started holding my head down tight on his cock.

“Go on, stick it in the bitch’s ass,” he said to his mate about to enter my ass. I was gagging on cock buried deep down my throat and couldn’t struggling to breathe. He slapped my ass hard and almost made me cum. Then I felt the head of his cock pushing at the hole into my ass. When he breached the entrance I felt some pain and discomfort, but I felt more relief than I would have thought.

Then while I was marveling at the fact it didn’t hurt, I was brought back to reality, when my head was made to suck again. My head was forcefully bobbing up and down on a large cock, at this stage, my nicely dyed hair was in tatters. In no time, they soon had their cocks thrusting in and out of my asshole and mouth, in unison with each other.

The guy fucking my ass was giving me a good and proper, pounding. I was left moaning and drooling into the cock buried in my mouth. His hips would slap against my butt-cheeks, causing my earrings to jingle, with every thrust. My cock was left swaying and bouncing, it was intoxicating.

I only wished it was under better circumstances like I never ask for this and I was going along with it, for my personal wellbeing. That’s has been playing in the back of my mind, ever since I reluctantly, accepted that first cock in my mouth. What are their intentions, are they safe to be around, or are they going to beat the shit out of me, or worse. I wish I knew.

“You’re a little whore, you love getting your ass pounded by cock, don’t you?” The guy fucking my ass said. I had been mumbling words and moaning, with a fat cock in my mouth for so long, saliva and pre-cum ran out of it, as I worked on it. My head was moving up and down on his cock with the aid of his hands, that it was like I was headbanging to Motorhead or some band like them.

I was about to touch my cock, when a cock was presented to me to stroke. So I now had a cock in my mouth, ass, and now in one hand. I couldn’t help but start to play with my balls, with my spare hand. They were wet from pre-cum and maybe, from my ejaculation.

If someone was walking their dog, I would have looked a sight. My mini-skirt was up over my hips, stockings were torn to shreds, service black guy’s cock, and on my knees.

Then the mercy call, from the guy in my mouth. “I’m cumming,” he announced. With that being said, he held my head down to his crotch and shot load after load down my throat. I struggled to swallow all of it, and I think some came back through my nostrils. Once he pulls out, I lean my head down and rest it on my arms. My bum was up and my head was down, my jaw ached and I felt tired.

I could smell cum in my nostril and with every breath I took, even my phlegm had a scent of cum in it. The guy pounding my ass started caressing my thighs in a caring manner and was slowing down his thrusts. It was now that I began to enjoy how his cock felt sliding inside of me. Also without the cock in my mouth, my moans became much louder, I didn’t care, they were fucking me and enjoying, why couldn’t I also? The way the slippery thing went in and out of me, plus his soft caressing of my thighs was driving me towards the edge.

Then he gripped my hips again, and his slow methodic thrusts became, hard and fast again. My moans were turning into words of gibberish, he was now fucking me insane. Plus I think I just blew my load, I felt that strange sensation.

“Oh God, feels so good, oh yes fuck my ass,” I was moaning, my voice sounded very husky. He was giving it to me hard and fast, and I was loving it. I was purring with my face in blades of grass, with my ass up skywards, with a cock ramming deep inside it.

I moaned and moaned as he pounded my ass relentlessly. Then suddenly I felt him tense up, his hips began to quiver and then he buried his cock balls deep inside my ass. Then I felt his cum explode in my ass, then he buried his cock deep and held it there.

After a minute, his now shrinking cock withdrew, and strings of cum came out of my mouth with his cock. I was still purring when he gave me a kiss on the neck. I lay there for a few minutes, relaxing, with my bum facing the stars and head down. I had forgotten that there were a few guys, sitting around and chatting.

Suddenly my eyes snapped open, someone, much bigger than the guy before, slid his cock into my gaping hole ass. It felt like it ripped it open, I let out a scream and moved my arms out straight, and trying to claw the grass to get up. It was so sudden, I couldn’t relax my ass muscles, as it tensed up and he drove his monster cock deep inside me.

Oh god, the pain, he had to be 10” inches and thick, and he must have been 300-pounds when he thrust into me. My hole felt torn and his cock felt like it went deep into my stomach.

“Look at you, bent over like a white bitch, with a black man’s cock shoved up your ass,” He bullied me. I whimpered in pain. “Just look at you, pretending to be a chick, well I will make you bitch, bitch!” He admonished me, my ripped ass spasmed.

“OH FUCK,” He bellowed out and started to violently ram my hole. He starts to build up a real pace, my entire body was rocking. My ass clenched around his cock, while he plunged deep and deeper.

“Oh yeah, you like big cock, don’t you? Ahh yeah!” he said, like a bully. I grunted in pain. His cock in my ass felt like a fist not a cock.

“Getting close, getting real close, fag,” he grunted and pushed down on my lower back. He then leaned over to my ear, with the full weight of his torso pushing down. “You like it rough, don’t you bitch? Do you like big cock busting your ass? You fuckin’s little fag!” He continued to rant on. I didn’t feel safe with this mug all over me.

“Need to cum, I’m going to cum in your ass, take my load like a real bitch,” He gloated. “You want my jizz?” I didn’t respond. He seemed angry I didn’t answer, so he started ramming into me harder. “You want me to cum in your ass,” He growled. Again I didn’t answer so he head slammed me into the turf. “Ok, ok, I want it,” I mumbled, but I just wanted him out of me.

“What?” He growled. “I want your big load in my ass, ok,” I said, wanting this ordeal to end. He thumped inside me about another 5-7 times, before his cock swelled up and pumped his cum straight into my stomach. He huffed and puffed and collapsed on top of me.

Then, two of his mates took turns in fucking my mouth and ass, for what seemed like hours. Most of it became a blur, then on.


I must have passed out, as I was now on my jacket on the picnic bench. My legs dangled limply over the edge, and I could barely feel my legs. I reached back to touch my sore ass when another cock slid in my ass. 30-minutes later, he had finished and another four more black dudes fucked my ass. I had no notion or care anymore.

After a few more hours, my capture and sexual abuse were over. Every one of them had a go at busting my ass and choking my sore throat. I felt pleasure and lots of pain from them. When they were gone and I was left alone, I reached back and spread my ass open. Almost immediately, a gallon of cum exited my ass. I then projectile vomited cum I had swallowed, I had cum juices dribbling out both holes.

My mind was in a daze, as I passed out. Before today, I had never even thought about entertaining black guys.

When I slowly started to cum too, I started to cry. I couldn’t move or defend myself, I was fair game for anyone pervert to rape me, more. My ass felt broken and an overstretched disaster area. I had cum running out my ass and down my legs.

Then a flashlight was shining on my head and body, and I could hear a walky-talky. Police had arrived, I was asked a question. My throat was too damaged to answer, all that came out was a raspy, husky squeal. I was then put in a cell and charged with public nudity and indecency.

Much later in the day, I was released without charge, once they found out it was a gang of local thugs that attacked me. I was then sent to a hospital because I had internal bleeding from my ass, and couldn’t walk. At the hospital, they assessed me, and I spent two days there. At the hospital, I found out they had tattooed my back, right next to MC’s tattoo. They inked a picture of a large spade with numbers inside it. When I was discharged, I still couldn’t even talk, as there was damage to my vocal chord that prevented me, it left my voice husky and squeaky, like a teenager's voice.

Once again, I missed time at work, but this time they fired me. Felicity stood there with arms folded and with a satisfied smirk.

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