Birth of a sissy

I have been watching pornography since I was a child. My first experience involved a comic book. It was terribly boring but one of the panels depicted a woman getting out of a tub of hot water. Her nipples were prudently covered by a towel, but the curves of her breasts were enough to make me come. At some point, I couldn't resist but connecting the lines of her breasts with a marker and drawing her nipples. Needless to say, it was no artistic success and destroyed the attraction of the picture. Luckily, around that moment we first got an internet connection and comic books became obsolete. All alone in my room with the curtains drawn I finally had the opportunity to watch real naked women. The first porn sites I checked out always had a couple of daily pictures on offer: Daily Blonde, Daily Ebony, Daily Brunette. But the one that always turned me on the most were the Daily Asians. Small breasts, soft skin, lush black hair around the vagina. Somehow Asians don't attract me much these days, but at that point in time I was sure I wanted to fuck an Asian girl someday.

I'm not sure what caused it, but when I grew older I became more interested in pictures of people actually doing the deed. That also confronted me with even more **** forms of pornography like cum shots and watersports. Naively I clicked on those links only to be appalled at what I saw. But a gradual process of accommodation led me to come to enjoy watching the images that shocked me at first. I was particularly attracted to cum shots. I kind of remember the picture that converted me. It showed a mature woman taking a thick beam of cum to the face. Since then, pictures of women having their faces filled with the product of the pleasures they just gave always got me going. I'm not really sure what attracted me about cum shots in particular. Maybe it's the combination of pleasure and domination. In any case, since then I've never ceased to enjoy the image of someone being covered in the juices of someone coming all over their faces.

At some point in time, however, I started wondering what cum shots are like from a woman's point of view. So one day when I was particularly horny I got myself in a position with my dick above my face and started masturbating. The moment I came and felt that warm and salty juice on my face I felt ashamed, but that didn't stop me from doing it time and again or from enjoying watching cum shots even more than I used to do. I was fascinating by the prospect of kneeling down in front of some dude, pulling down his pants and seeing that beautiful piece of meat dangling in front of me. I'd imagine first taking the balls in my mouth and softly starting to massage the shaft. Then I'd put my lips around his half-erect penis and feel that smooth and warm thing in my mouth. I'd move my head up and down, sucking on that dick as hard as I could, confident that I could make him come without using my hands. Up, down, up, down, letting that dick run further and further in my mouth until I felt my nose against his stomach and my lower lip against his now shriveled ball sack. I'd move my finger against his anus, slowly pushing until it was inside. I'd hear his moans become more and more intense until he pushed me away from his dick to do the final honors himself. I'd stay there, kneeled in front of him with my mouth open, ready to receive what I had been working on so hard. I'd close my eyes until I felt the same warm and salty juice on my face I experienced before. The first ejaculation would come over my eyes and nose, the second one right into my mouth. I'd feel ecstatic when I swallowed it. I'd wipe the cum from my eyes and put the finger in my mouth, savoring that taste once again. Then I'd open my eyes and see his limpid dick with cum on its tip and all along the shaft. Without thinking I'd again put my lips around his penis, going through the same motions as before until I had swallowed every last bit of cum. At that point, my reverie always ended.

I never intended to put any of these thoughts in practice: I had girlfriends, it was too much explaining, and besides I didn't even know where to begin. Maybe things would have been different if I'd ever had a gay friend. Anyway, when I was about 25, I got a job in a different country. Though I'd travel back to my girlfriend every once in a while, I was alone on my apartment for most of the time. I started making pictures of my dick and ass and posting them on the internet. I loved reading people's comments, especially if they threatened to find me, pull my butt cheeks apart, lick my hole clean, and then fuck my brains out until I came from the sheer pleasure of someone's dick in my ass. Some people seemed to be serious and sent me private messages. One of them was called Roland. We exchanged some pictures but I never thought much of it: I was 25, slim body, round ass, and virgin when it came to sex with guys, while he was 50 or so, fatty, and had an asshole that could take a 3-inch penis without problems. It turned out Roland lived close to where I lived and he asked me if I'd come over so he could fuck me. Obviously I didn't respond to that message---that is, until one day.

I hadn't had sex with my girlfriend for almost two weeks and hadn't watched porn or jacked off either. All alone in my apartment, I started watching porn and felt excitement all over me. I knew this was a special occasion, that I couldn't just come to some video of a fatso masturbating in front of the camera. I wondered what to do. Maybe buy a dildo and see how far I could stretch my ass? Then I remembered Roland's message. I trembled with lust and nerves. Could I? I looked at the pictures he sent me. Something about him turned me on. Maybe that he had almost no hair on his body. Maybe his cute saggy tits. Maybe those massive balls almost touching the floor when he bent over on his knees. Most likely it was just the lust that came over me. I sent him a message, asking him if the offer was still standing. He just replied: "Tomorrow 19.00" along with his address. I didn't sleep that night and didn't go to work the following day. I knew I shouldn't go, but I also knew I couldn't not go. So I that evening I took the bus to his place. I still trembled when I rang his door bell. The door swung open and I went to his apartment. The door stood open. I entered the room. It was what you'd call a bachelor's apartment. Minimalistic in terms of furniture and not particularly clean.

Roland was sitting on the couch. He had lipstick on and a blonde wig. He had a bra over his breasts and a G-string on, as well as a pair of panties. I was surprised because he didn't crossdress on any of the pictures he'd sent me. I said "Hi" but he just motioned for me to take my clothes off. I did what he asked. Then I moved up to him next to the couch. I tried to kiss him but he pushed me down on my knees. He smelled like tobacco smoke. He pushed his G-string out of the way. I looked at his dick: it was small and kind of hidden in his fat belly. Like in my wet dreams, I closed my mouth around his balls. They were enormous. They tasted incredible. I had never been harder in my life. But after a couple of seconds he took my head in his hands, guiding me towards his dick. It wasn't easy to suck it. First I tried to do it without my hands but that didn't work out. I had to push back his belly to be able to suck him properly. Like in my wet dreams I was going up and down, up and down. I sucked with all my might but I couldn't get his dick hard. I tried to finger his anus but he just pushed my hand away. I looked up at him. He was sitting contently, his wig slanting to one side, smoking a cigarette. I kept on sucking. Just when I thought he was getting harder, a cellphone rang. I heard him answer it, so I stopped sucking to wait for him to finish. With one hand, he shoved my head back over his dick and kept it there for a few seconds. So I just continued sucking his little penis while he was phoning whoever it was that called him. When he hung up, he turned around. His asshole looked like he had been fucked by a 3-inch cock just moments ago. I licked his balls, moving up towards his asshole. It smelled terrible but that only turned me on even more. When I touched his asshole with my tongue, he moved backwards and the tip of my tongue slipped right into his ass. I was afraid I'd come. I moved up and down with my tongue in his ass while milking his little dick. Luckily it was growing harder. When he turned around again I recognised that fat stump from the pictures he sent.

Roland moved me on the couch and turned me on my back, face and legs upward. I felt a cold sensation as he poured lube over my ball sack. It dripped towards my asshole. He shoved a finger inside. I couldn't resist but coming. I didn't even enjoy it. The cum just dripped out of my dick. Roland just laughed. Then he pushed another finger inside. Even though I had just come my dick didn't become any less hard. After moving inside me for a little while, Roland removed his fingers from my ass and I prepared for what was coming. When he shoved his dick inside my ass I felt like I was coming apart. It hurt like hell but it was thrilling at the same time. He started out slowly but quickly picked up pace. After going at it madly for a while I thought he was coming but instead he turned me over to fuck me doggy style, keeping his dick in my ass all the while. He slapped my ass so hard it hurt. Then he put both hands over my hips and pushed me over his dick while he thrust his dick forward. I felt like I was going to come a second time. After having been at it for five minutes or so, he slowed down and I thought he was going to come. When he took his dick out of my ass I could feel something out off my ass dripping down on the sofa. Instead of coming, he pushed his dick back inside, pulled it out, and then pushed it inside again. He pulled my ass apart and I could feel him enjoying the sight of my gaping ass. Then he pushed his dick right back in and fucked me for another five minutes or so.

He finally pulled his dick out, turned me around on my back again and moved himself over me. First he sat on my face, moving his ass back on forth over my nose and outstuck tongue. Roland's sweat dripped in big drops on me. Then he shoved his dick in my mouth and started to fuck my mouth. It smelled terrible. At some moment I felt my legs move upward. First I thought it was Roland but when I looked there was a black man standing there, naked. His muscular dick pushed against my asshole. He pushed harder until it gave. I came a second time. I hardly noticed. I don't remember much of what happened afterwards. Roland came in my mouth and I just had a moment to swallow and catch my breath until the black man put one of his legs on the couch near my face. He then moved his big toe right into my mouth. I sucked at it like there was no tomorrow. Whenever he pushed his dick inside me I felt ripped apart. After some minutes going at it he removed his dick from my asshole, came over and masturbated until he came on my face. I thought it was over, but when he was finished he pushed his dick inside my mouth to clean up the mess. Then he moved away. I jacked off and came a third time. This time it felt like ecstacy, but I felt ashamed immediately afterwards. I dressed and left hastily, but when I woke up the next morning I knew I'd visit him again for more.