My Initiation

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.)

*

I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything.

Until now I've never had sex with a man and I didn't consider myself as homosexual either. But I was always fascinated to anal sex. The thought of "Why would someone let herself/himself get fucked in the ass, when there's no actual pleasure of possibility to orgasm in it?" Also the thought of giving up your body for someone else's pleasure was something that always turned me on. And since I've never could get an erection whenever I tried to have sex with a woman, I decided that I should do other things to compensate. Maybe becoming a gay sissy would be the answer? All I knew was that it really made me horny thinking about it ...

As I laid on the bed in the small hotel room I trembled a bit nervous. Was I ready for this? I stopped thinking and got up. Time to prepare myself. So I got into the shower and removed all my body hair. After giving myself an enema I worked a large black butt plug into my ass. It would be better to stretch out a little. Then I attached my fake DD breast forms onto my chest with a huge amount of extra strong adhesive. That took a while, but after the sticky fluid dried I stood up and my tits stayed in place. They wouldn't come off now without using some special chemical. Next I applied some body lotion on my body, so my skin got very soft. I put on black fishnet stockings, a short black top and matching black panties with the words «Fuck my ass» written on my ass. The sluttiest outfit that came to my mind. Then I put on my long black wig and applied some makeup which included heavy mascara, dark eye shadow and a bit of lip gloss. Almost done. As I looked into the mirror, I didn't saw one masculine thing. I was a slutty looking sissy. But that wasn't enough. There was one thing left to do to be completely feminized. Thinking about it gave me a very strong erection and almost like hypnotized I started stroking my member. But then I stopped and proceeded to do what had to be done. I went to the minibar and took some ice and put it on my penis and testicles. I had to get rid of this erection. As my genitalia shrunk I quickly put the CB3000 chastity cage on it and locked it up. This clear plastic device made it impossible to get erect and touch myself. I put it on because I knew exactly that as soon as I would have an orgasm, I wouldn't want to be fucked anymore. So before I could get second thoughts I went to the toilet and flushed the key down. Now it was done. No more erections or possibility of pleasure through my sissified peenie. My ass would be the only thing I could concentrate on. I was ready for servicing men, real men with big erections, with my white asshole. I was ready for total submission.

With my long black coat on and my high heels clicking on the floor I made my way to a major adult bookstore from which I knew it had a large gay area in the basement. Now I really got nervous. I stood in a dark corner and smoked a cigarette. The coat hid my slutty outfit but the people passing by still saw that I had huge tits underneath it.

Entering the book store, I knew that I had to get the peoples attention. So I took off my coat and went looking at the gay DVDs. There were two chicks behind the desk, just grinning. At the same time there were 3 men staring at me with widened eyes. I felt like the biggest whore in the world. And while the butt plug was wiggling inside my ass I felt my caged penis leak a bit pre cum. Seeing all these things made me extremely horny and I didn't want to waste time anymore. The girl behind the desk didn't even require me to talk. She just smiled and said "15 Euros" I handed her the money and nervously went downstairs.

The gay area in the basement was a dark, hot place. There were gay and she-males movies playing in the booths. The ground was dirty and it smelled from sweat, semen and even piss. So this was it. This was the place where I hoped to give my anal and oral virginity to every man who would walk in here. This was where I wanted to loose the rest of my manhood ...

All booths seemed to be open and in the third booth I saw a big black guy slowly stroking his cock. Before I could get any second thoughts, I stopped in front of him and licked my lips as I stared at his very big penis. It was at least three times larger than mine ever was, and I liked that.

Obviously he liked what he saw, because he mentioned without any words that I should come and work that big cock. I never touched another cock than mine. It was so big and hot in comparison to my dildos. I licked the tip of it and got my first taste of pre-cum which isn't mine. My caged dicklet was throbbing and my heart was racing. I couldn't believe that it could happen so fast as I took my very first real cock into my mouth and started sucking. It tasted very strong and I loved it.

After a few moments he started really fucking my mouth and as his cock started throbbing, I thought he was going to cum right into my mouth. But I was wrong. He withdrew his fat rod and grabbed me onto him. He pressed his lips against mine and shoved his tongue deep into my mouth. Oh my god! For the first time I was kissing with a man. I was nervous and very excited as I wrapped my arms around him as he french kissed me like a girl. And I got hornier than ever as I felt his hard black prick rubbing underneath my virgin ass. He told me to grind on it and I'm sure that I blushed as he said "You're one fine ass sissy. You want me to fuck your gay ass? You want that big black cock inside you?" I was breathing very hard but I managed to answer "Yes ... I want you to ... fuck my ... gay ass ... I want that ... big black cock ... inside me ..."

"Good ..."

He made me stand up and take off my panties. "What the fuck is this?" He made me explain what a chastity cage was and why I was wearing it.

Teasing me by moving the base of my butt plug back and forth he asked me "So you wanna get fucked like a girl?" I nodded. And I was getting even more nervous as he laid me on the ground outside the booth. He kissed me again and then made me spread my legs wide. Suddenly, I remarked there was somebody with a camera! I wanted to get away but my black stranger held me still. This was not how I imagined it would be. I felt very uncomfortable being filmed. I looked at the man above me and said "Please, I don't want to ..."

"Shhhh, you know you want it" I closed my eyes and tried not to think about the situation. But there I was, being filmed dressed as a big titted sissy on the ground, my legs spread wide, my locked up peenie in full view and about to get fucked for the first time by a black man I met only minutes ago. I can't describe how humiliated I felt. On the other hand, how could I've been so stupid by thinking everything would happen exactly how I wanted it to happen?

The camera came closer as he slowly pulled the large butt plug out of my ass. I felt immediately empty and I probably blushed even more. Then he said "Now beg me to fuck you"

"..."

"Do it!" He was fingering my ass. "Come on, do it!"

I was afraid but I knew I had no choice. And after all, this was what I wanted to happen for so long. It all got captured on video as I begged him to not just fuck me, but to fuck me like a girl. I held my legs wide apart as I saw his unbelievably big penis slowly move towards my white ass.

And then it finally happened. My own penis was trying to get erect as he shoved his cock all the way inside my sissified asshole. His balls were resting at the entry of my boy-pussy for a moment before he started to slowly fuck my homosexual virginity away. It didn't hurt at all. The rubbing of his very thick cock against my prostate felt so good that I started to moan. He fucked me like I was a girl in the missionary position and I knew I was being filmed, so I tried to keep my voice as high pitched as possible when I moaned. I loved the feminine feeling as he completely emasculated me. My arms were wrapped around him and he pounded my asshole in long hard strokes before he said "Oh yeah, I'm gonna cum!" With that he shot a large amount of his warm sperm inside my bowels. The feeling was amazing. I didn't care about the camera anymore. This man just used my body for his sexual pleasure without caring about mine. I loved every second of it. I felt so submissive, I was in heaven.

As he withdrew and I reopened my eyes there were four other black men standing around us. They all had their erect dicks out. I was getting nervous again but before I could do anything, one guy put me on my knees and shoved his dick inside my mouth. Only seconds later another big cock entered my formerly virgin ass. Was I really going to get gang banged? It was all happening so fast, I couldn't think straight. But I sure liked where this was going. I was getting hornier and hornier ...

A few minutes later I finally got my first taste of a strangers sperm. The guy pulled his dick out of my mouth and ordered me to open up and stick my tongue out. Thick wads of cum shot into my mouth and also a bit on my face. I was so eager that I swallowed immediately. The taste and texture was far better than my own cum, which I used to drink. It was creamy and slightly salty. "Mmmmmh ..." I licked his cock dry and soon another sticky load was shot into my ass.

While they took turns fucking my ass and mouth simultaneously I totally forgot about my own peenie. It was just dangling between my legs. Meanwhile somebody took off my top and my glued on breast forms sprung free. People were fondling them and making comments on how nice they look and how soft they feel. I felt like the biggest whore on earth and I remembered that I was probably still being filmed.

I couldn't really see it because I was constantly sucking someone's cock but I knew that meanwhile even more people were in the room. After I swallowed my fifth load of cum the man with his dick inside my ass grabbed me and changed position. He laid on the ground and made me ride him with my back against his very hairy belly. There were at least nine men around me now. All of them we're looking at my feminized body getting fucked and making comments.

"Ever seen a bitch like that?"

"No way. This faggot's hardcore, man ...."

"Well I ain't gonna wait my turn. Let's see how hardcore he really is!"

A fat middle aged black man came towards me with his erect dick already out. He leaned over me while I was still getting fucked and I knew exactly what was about to happen ... My eyes widened as he put his cock next to the one already in my ass and started to push. Getting fucked by two dicks in my ass at once was something I often fantasized about. But I never thought that double anal penetration would hurt this much. I tried to protest, telling him that my ass is too tight, but he kept pushing. I wanted to clench my teeth but suddenly another cock was shoved straight down my throat. That retracted me for a moment and BANG! It was done. Two big cocks were buried to the hilt inside my ass.

I tried to relax my muscles but before I could get used to the new fullness they started fucking me furiously. My screams were muffled by the cock fucking my mouth. But obviously it wasn't enough. Two other men placed their long dicks in my hands and told me to keep them hard until they get a turn on my ass and mouth.

It was unbelievable. Five men were using my body at once. The pain subsided and I was getting horny again ...

After my mouth got fed another load of cum, I looked down and I saw that my useless little peenie was filling up the whole cage, trying to extend even further. But the hard plastic wouldn't let it. There was no way it could grow larger than 2,5 inches. Looking at all those big black cocks surrounding me made me even hotter. I was clearly inferior to them. The second guy in my ass came and only seconds after he withdrew there was another one sliding his almost 10 inch long and 2 inches thick meat into my already stuffed sissy ass. While I was sucking on a big cock and jerking off two other guys those two giants were fucking my formerly virgin ass so hard that I got in an ecstatic state. I felt so stuffed and used like never before. The rubbing of those two dicks inside my rectum was got me so hot that I started to moan like a bitch in heat. Some of the men surrounding or using my body made comments about how pathetic my small white dicklet looked looked. Not being able to even get erect while a whole bunch of real men we're using my body with big hard erections strangely turned me on beyond my imagination. And as the black man on top of me started to fuck my ass even harder by almost completely pulling in and out with each stroke a strange and warm feeling came over me. My whole body was shuddering and I began to feel something inside the plastic cage around my useless genital. One of the man guys just filled my mouth with a huge load of his salty sperm. After I swallowed his load too I dared to look up and I saw how wads of thick sperm were leaking out of my caged peenie. I was having an anal orgasm.

They started laughing and cheering while pointing at my cum leaking chastity cage.

"Look at that bitch!"

"Holy shit, the little faggot came while getting fucked in the ass"

Actually I didn't really cum. It was impossible to climax the way a man normally would without penile stimulation. The tip of my peenie was tickling a bit and it almost felt a bit like peeing. But after the strangely warm feeling subsided and no more sperm leaked out of the chastity device I felt something like relief. I still felt horny but some of the pressure was gone.

The big guy fucking my ass from on top held my face and said by looking me deep in the eyes "You like that, you little sissy faggot, don't you? Don't lie to me, bitch. You just came while we fucked your white ass, gay boy. So just say it. Say it, so that everybody can hear. Say how much you like getting fucked, baby ..."

Those two giant dicks were still fucking my ass while two other guys reminded me not to stop jerking their cocks off. My well attached breast forms were wobbling in a steady rhythm as this black man repeatedly penetrated me with both his penis and his words and as I saw some camera flashes above me I realized it:

Although I didn't have any real sensation in my peenie, I ejaculated while getting dominated and used by a large group of unknown strange men. I dressed myself up as a female whore for this to happen. This was the moment I clearly lost my complete manhood. It was silly to consider any part of myself heterosexual at this point. I was getting utterly humiliated and I loved it.

So I screamed out "Yes! YESSS! I love it! Please fuck me harder! Use my faggot body for your pleasure! Feed me your delicious sperm! Show me my place!"

With that they both emptied their nuts inside my bowels. But before I could say anything else, a fat hairy man sat on my face and ordered me to lick his asshole. I couldn't see it, but a shiver went through my body as my tongue touched his clearly unwashed asshole. There was no chance to protest, so I just started licking off the shit on his hairy ass. The taste was so strong and disgusting that I had to fight in order not to puke.

But then the dicks pulled out of my abused hole and somebody said something about switching positions. Somebody grabbed me and put me on my feet. It was the first time that I could see what was going on in the room. There were about 15 black men surrounding me. They seemed to be of all kinds of ages, but none of them could be considered as "good locking". Still, their erections were enormous. I could also see two cameras and lots of cell phones pointed at me. My legs were shaking but I didn't knew if it was from the fucking I just received or because I was exposed in front of these cameras in the full light. Besides my long black wig and my CB3000, all I was wearing were my fishnet stockings.

One man grabbed me from behind and pulled me in front of a video camera. His cock entered my ass and then he spread my legs to lift me up. Everybody was looking at me and now all cameras were pointed at me. A camera man asked me: "Does that cock feel good inside your ass?"

Almost breathless I said "Yes, it feels good" The crows started laughing.

"Why does it feel good?"

I didn't knew what to answer. But my caged peenie was leaking pre-cum again.

"Maybe because you're a shameless gay whore?" The man holding me in the air was fucking me even harder now.

"... yes ... because I'm a shameless gay whore ..." Again, everybody was laughing.

"No shit! So there's nothing you wouldn't do?"

Without thinking I said "I would do anything that pleases you ..."

"Okay then..." the guy inside my asshole said as he put me back on the ground "... on your knees, bitch!"

After quickly doing as he told me to, he said "Beg for it. Beg us all to fuck you!"

The humiliation was making me hornier than ever, so I laid my face on the dirty ground so I could spread my used asshole wide open and said "Please, sirs. Fuck my ass. Feed my sissy hole with your big black cocks. I need it, I need it so bad. Fuck me like real men. Fuck me as hard as you can. Please!"

It didn't take long before some black meat entered my already well used rectum. I moaned as feminine as I could. And it really felt good.

I saw two feet in front of me, so I quickly got up to take a new dick into my throat. He was stroking a very long massive tool, but it wasn't hard yet. So I stuck out my tongue and teased him a bit. "Please let me taste your big cock, sir" He just laughed and said "Bitch, you gonna taste something else. You said you'd do anything fo' our pleasure, so I'm tellin you: Swallow everything, you faggot!" This was when a hot stream of yellow piss hit my mouth. I closed my lips but then some other guys grabbed my by the hair and started yelling to me that I should drink it. The man fucking my ass pulled out and got replaced by another one. As he entered in one long push I reluctantly parted my lips and let the urine flood my mouth. The taste was very strong so I started to swallow as fast as I could. I couldn't believe it. Now they also used me as a toilet.

I almost gagged but finally I managed to swallow most of his piss. Exhausted but still being fucked I tried to relax a bit. But suddenly another stream of piss hit my face. And another one. And another one. Some guys we're screaming "Swallow, bitch, swallow" I knew, I had no chance. So I opened my mouth to receive three streams of urine at once and started swallowing. I felt my belly fill with their yellow liquid while someone else was raping my backdoor. Strangely my caged dinky was twitching. Was I really turned on by this?

My mind kinda went blank and I felt a little dizzy when it finally ended. I felt exhausted and for the first time I was thinking of how could I get out of here. But my thoughts were interrupted by someone grabbing my arms and telling me "It ain't over yet, faggot!"

Countless men we're using my body over and over again for their pleasure. There were so many, I wasn't able to see or memorize their faces. All I could see were cocks. Big erect cocks all around me. Most of the time 5 guys we're using me at once. Two in my ass, one in each hand and one down my throat. At one point somebody even fucked my fake tits. I once even begged someone to piss into my mouth again because I felt I was dehydrating. The smell of sweat, sperm and urine was everywhere.

Hours passed and I swallowed the last load of semen being sprayed into my mouth. I was sitting on my knees and I felt so exhausted I almost fell asleep right on this spot. But I still felt kinda horny as I looked down onto my overfilled chastity cage. Most parts of my body we're covered with dried cum. It was also leaking out of my over used asshole. How many man had fucked me? 20? 30? Or even more? How many loads did I swallow? My belly looked a little bloated and I knew it was completely filled with sperm and piss. So many men climaxed inside or on my sissified body. I had only one orgasm myself, if that's what you could call it. I felt abused and unsatisfied. My dicklet was still desperately trying to get erect. But I wasn't unhappy. After all I got what I wanted. What I craved for so long. I lost my homo virginity, the hard way.