How I Became a Sissy

When I was in high school, my senior year I went to live with an uncle in a small town in California. He was a truck driver and was gone for most of the week, and sometimes over the weekend. It left me with a lot of time to myself. I was 19 years old, so there was nonissue with being by myself. i could take care of myself. He lived in an apartment complex with a pool, which I enjoyed, so it wasn't all bad. I enjoyed the free time and freedom to do what we I wanted. At that age, I was horny all the time and liked the freedom to walk around naked and basically jack off whenever and wherever I wanted. I felt like I had a hard-on all the time!

This was problematic at the pool, to say the least. I was a swimmer and would wear my Speedo suit, so when I got aroused, there was no where to hide. Not that I had a big dick, quite the opposite actually. I have a pretty small dick. When small, it sits nicely in the Speedo pouch and you almost can't even see it! When hard, it gets to about 4 inches and is pretty thin. I was only about 5'5 and pretty thin with long hair. I was definitely not the "macho" male, but rather a bit feminine looking. Being a swimmer, I was usually mostly shaved, and being always horny, I used to enjoy shaving my pubes too. I was very hairless all over; I love the feeling, but it definitely did not make me more manly, haha. My swim mates used to joke that I should put on a girls swimsuit and compete as a female! Oddly, the idea of wearing a girls suit turned me on. One time after swim practice a girl on the team left a suit by accident. I grabbed it on my way out with the plan of bringing it to her at school tomorrow. When I got home, I thought more about the idea and decided to try it on. It felt amazing! It was so tight on my ass and crotch, I got instantly hard! That night, I must have jacked off 10 times while wearing it. The next day, I picked it up off the floor and it was covered in dry cum and was stiff as cardboard. I decided to keep it, couldn't return it in this state, and knew I would have many more stroking sessions in the future.

After school, I decided to use the apartment pool and cool off. There were always some bathing beauties at the pool, and with my quick trigger, I had to be careful and not sport a boner, but I had a solution! I would go into the pool house bathroom almost hourly and relieve myself in the stall. A quick stroking session and I was good for another hour or so, no matter how skimpy the girls suits were.

It was in the stall one time where this story starts to get interesting. I was playing with my little dick one time and must have forgotten to lock the door. As I was doing this, one of the neighbors, a guy in his 20s opened the stall to take a leak. What he got instead was a smallish, hairless, small cocked guy playing with his little pecker. I was stunned and couldn't move, he seemed shocked too- we both stood there for what seemed like a long time. Me with my little dick in my hand and him just staring. I couldn't help but notice that he seemed to be looking me up and down, and definitely spent some time looking at my body. I had been close before he burst in, and the taboo-ness of this was too much for me. I blew a load all over my hand and wall. I was standing there in post orgasmic daze with cum all over me and completely naked in front of a stranger. He closed the door and left and I quickly got dressed and ran to my apartment. I was terrified of what was going to happen. Was he going to rat me out, tell everyone that I masturbate at the pool? I would be banned, no doubt, from returning but even worse, would be so embarrassed I would not be able to show my face ever again.

I saw the guy the next day in the parking lot. Oh shit, what was going to happen. I tried to look down and get away but he called out and ran my way. Luckily, he didn't seem aggressive or that he was going to do anything, but I was scared shitless nonetheless. He came over and started talking, and actually apologized for bursting in. He seemed just as embarrassed as I was. I was still breathing heavy and visibly scared. He tried to console me but I was breathing so hard and with all the adrenaline I started to get real light headed. He caught me before I fell and helped me walk to the apartment. My unit was in the fourth floor so he suggested we go to his as it was a lot closer and easier to get to.

We got to his place and he had me sit on the couch and rest. Eventually I recovered as we were talking and started feeling normal. Seemingly out of nowhere, he brought up the incident in the bathroom and joked that he completely understood. After all, there were some hot girls there and bathing suits seem to get smaller and smaller every year. He asked if I did that often, and I couldn't lie. He started talking about sex and asked if I had a girlfriend. I didn't at the time but definitely jacked off a lot. He didn't have one either and said he watches a lot of porn to ease the desire. All this talk was starting to make me horny again and I inadvertently started rubbing myself. I caught him glancing and noticed a sly smile on his face. All of a sudden he said "I have an idea" and stood up. He went over to the tv area and grabbed a vhs tape and put it in the VCR. He said he thought I'd like this. On the screen appeared a couple ladies poolside with a group of guys with huge cocks. The girls were each playing with a few dicks, sucking them, rubbing them on their face, and more. It was such a turn on! For as horny as I always was, I never really saw explicit porn like this, certainly not with another person in the same room

As we were watching, we eventually both started playing with ourselves through our pants. I was getting really horny, my little 4 inches was raging! He pulled his cock out and I couldn't stop staring at it. It looked huge compared to mine. He noticed it and was really showing it off now. He had already seen my little dick, so I think he was getting off showing me his huge one and making me feel inferior. I didn't mind, and kept looking at his dick while rubbing mine.

He told me that when I got out of school and into the "real world," it was normal for friends to help each other out when they didn't have girlfriends. I didn't know what he meant, then he asked me if I was ready to be like an adult. I didn't want to act like I was didnt know about the real world so I said "yea". He came and sat next to me and told me to grab his cock. I did. It felt huge and warm! He guided my hand up and down to get me started and told me to keep going. I only stroked a few times and he came...a ton! I was proud of myself as he got up and wiped the cum from his stomach and deviantly rubbed it on my face. He said I almost looked like a girl sitting there with a cum covered face. My little dick was aching in my pants- he told me to take care of my little clit, I furiously rubbed it through my shorts and came in my underwear in front of him. He told me a I was a good little girl but that I had better be going. I went home and quickly jacked off myself thinking about all of this!! Even though I had tried on the girls swimsuit and knew I had a feminine build, I had never thought of myself like this before. It was weird, but it was kind of thrilling! I wore the swimsuit to bed that night and came in it at least a dozen times!

The next day I knocked on his door and he welcomed me in. After just a few moments, both knowing why I was there, he asked if I wanted to watch some porn. Of course I did! Again, he said he thought I would like this and chose a different tape. This one started normally, a girl in a black dress came into a room with a guy and started seductively dancing. She eventually got up on a small table and was dancing some more when the guy came and stood in front of her. He was rubbing her legs and moving his hands up her thighs, I was getting excited to see her pussy, she was pretty hot! She lifted her dress and he was petting her panties, then he pulled the panties to the side and out popped a soft little cock!!! I was audibly shocked and started furiously playing with myself as the guy on the video took the little cock into his mouth. My friend was watching me the whole time and told me he KNEW I would like this one! He told me he has a whole bunch of these videos. Apparently there was a series of these Russian CD videos like this and that I was free to watch them anytime, IF I took care of his boner first. I took his cock in my hand again and played with it a bit more this time, not just pumping straight away. After a few minutes of me doing this and watching the guy on screen get a blowjob, he blew a huge load. The way he was facing, it landed all over my face and hair. He loved it, I could tell.

We did this a few more times, then eventually I started doing it to some of his friends too. I would jack off 4-6 guys some afternoons. I was happy, they seemed to like me and I got to watch porn I didn't have other access too. No one ever jacked me off those first times so I was always horny to play with them. I never got the release I needed so I was always eager to do anything they asked. I was like a starving dog- I'd do anything! We watched mostly normal straight porn when there was a group until one day in which my friend put on the Russian CD porn. I started to get comments from the group, more like slights, that I kind of looked like the "girls" on the videos- I had long hair, looked slight, and was kind of short. They goaded me a bit and started asking me to take my shirt off to see my titties. They loved this; it confirmed that I looked like the Russian. My friend chimed in that I even wore "panties" to swim in, referring to my Speedo. Out of sheer coincidence I had been swimming earlier that day and had them on under my shorts. By this point, I was in such a daze and so horny that I slid my shorts down to reveal my little package in my Speedo. They loved this and grabbed me to the couch. I had a guy on each side and gave them both a hand job at the same time. I felt like such a slut, now with feelings of being a girl too. It was weird, but I was loving it!

This happened a few more times and progressed a bit more and eventually they got me little panties to wear when I was over there. I kind of liked it. My little cock was always so hard in them. They felt so soft. I was always clothed, but they could clearly see my dick- it was always so hard! They referred to it only as my clit though, they said I didn't have a real dick.

One day, he asked me if I wanted a beer. I was not yet 21 and couldnt buy it myself so i didnt have normal access to beer yet. He said he would give me one, but I had to do something special for him. I had to use my mouth. I had never done anything like this before but he assured me it would be okay and it was just the two of us. He pulled down his pants and brought my head down. I put the tip in my mouth and he slowly pushed me down more. I'd seen a bunch of BJs on his tv and tried to do what the girls did. He got hard real quick and before too long blew a huge load in my mouth! Half of it dropped out and all over my face but I felt proud! He gave a couple sips of his beer then one of his friends came home and saw me in the panties with cum on me. He said if I wanted more beer I'd have to blow the friend too. He pulled his pants down, and luckily he had a pretty small cock. I actually really liked sucking on it. I started playing with my own cock this time and jacked off while sucking him. It was great! I stood up and they noticed the cum all over my panties. They said I had a sissygasm. This went on for a few weeks, I must have sucked 50 cocks during this time. One night, after a few BJs and about 2 beers, I was kind of drunk.

A new friend came over and said how excited he was to meet me. He had heard a lot about me. His name was Kelly. He did something to me that had never happened before....

Kelly told me it was a special day and that we had to go into the bedroom. I was a little bit scared. I've never gone into the bedrooms before and then he closed the door. He told me to get up on the bed and take my shirt off. I did and was wearing only my panties. My little dick was very hard! He told me to get on all fours, bent over with my butt facing him. I was so afraid he was going to stick his dick up my butt. It would hurt so badly. I did as I was asked though, and he then pulled my panties down to my knees so I was naked in front of him. My little hairless asshole facing him. He started spreading my cheeks and then I got the surprise of my life! It wasn't his cock but rather his tongue!! He was licking my little tight asshole and it felt amazing! I must have groaned or something because he asked if I liked it. I emphatically said yes! No one had ever done anything like this to me. I was always the one serving them, giving hand jobs, blowjobs, jacking off in front of them, cleaning their cocks, and more. This was the best! He said he wanted it to last a long time and that he loved licking assholes, that he wasn't like the other friends.

Next he asked me to lay down on my back. He said he loved little cocks and asked if he could play with mine. It felt so electric as he grabbed me. I was so hard, all four inches of my skinny little cocklett ached as he played. Next he brought his head down and started sucking me! I didn't last long at all and came in his mouth, he said I tasted amazing and let a lot of the cum drip down on to my deflating cock. He asked if I liked that. Of course I did! He told me he wasn't finished yet, that he loved to suck on small, soft cocks. He took my little cum covered cock in his mouth next and cleaned all of the cum off me and just sucked me for a bit. Then he had me bend back over and licked my ass a little more before jacking off onto my ass hole. I could feel the warmth as his spurts landed on me. I laid down on my stomach and he next to me as he started playing with his cum on my ass. It felt so good, he was just rubbing his finger on my hole and going in circles, then slowly started putting pressure on my hole until he got a finger in. He finger fucked my ass for a few minutes then got down to my butt and licked up his cum.

I was getting hard again and he asked if he could give me another blow job. It was the best night of my life! I went home shortly after this, but did see him a few more times. Story for another day...