My First Sissy Orgasm / page: 191 - Erotic story Collection

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes.

It was my junior year and at the time I was dating a girl named Faith, she was a member of our college band. She was a blue eyed natural redhead. She had an amazing body in great shape with a nice pair of 34C breasts. We had been dating about four months when she told me that she would be going out of town to visit her parents for the weekend. At the time I thought no big deal I'll just go out with friends and party for the weekend.

Everything changed that Monday, however. Through a few friends I discovered that she had actually spent the weekend with one of the stars of our football team. He was a 6'5" black wide receiver. Initially, I was devastated and immediately confronted Faith that day. We broke up right then and there and I thought I would just move on. But, over the next few weeks I couldn't help thinking about her getting fucked by a black guy. I had seen her naked and picturing that milky white skin pressed up against and being penetrated by a black cock was consuming a lot of my thoughts.

I didn't know what to do or how to deal with these feelings at the time, so I tried to move on the best I could. I devoted more time to school and wound up transferring to a more prestigious university. I thought a fresh start where nobody knew me would be exactly what I needed and a great time to reinvent myself. Instead what I found only pushed me deeper into my sissification journey.

My first girlfriend at my new school happened to be on the dominant side and I didn't mind. I found the role reversal rather exciting and let her take control. She was the one that introduced me to pegging. I loved it, but for a number of reasons the relationship was rather short lived. So with my newfound sense of submission I set about learning as much as I could on the subject. This of course led to a lot of porn consumption (in hindsight a bad idea due to how fake the portrayal is) and experimentation.

It wasn't long before I found my way to the sissy hypnosis videos. I don't know what really interested me at first, but I was hooked almost immediately. I bought several pieces of lingerie and a dildo and would follow along to these hypnosis and a few instructional videos. Many of these types of videos also focus on small dick white boys serving very hung black men. While not my initial focus I did have more of a reaction to these videos due to my experience with Faith and they became my go to jerk off videos.

However, at this time I was still in denial and was dating women. Of course none of them ever lasted very long, but one definitely did make a lasting impression. From porn I knew that cocks came in very impressive sizes much larger than mine. I am a somewhat respectable 5" fully erect so on the smaller side of average and average girth. So nothing impressive, but nothing to really be ashamed of either; or so I thought. A woman I met at a party one night changed that.

I went to a frat party around Thanksgiving and had a few drinks. This very attractive blonde named Ashley was there and we started flirting a bit. We hit it off pretty well and decided to leave the party a little early and went back to my place I was renting. We wasted no time and went straight to the bedroom. It wasn't long before she was trying to get my pants off as I ran my hands up her skirt. She was very wet and eager to fuck. But as soon as she got my pants down she dried up almost immediately. She burst into laughter and I was left confused as to what was going on. Eventually she managed to ask me, "Is that really all you've got?" When I managed a "Yes," she started laughing even harder. She even pulled up pictures she kept on her phone of some of her lovers, all of which were very well endowed and most of which were black. The whole time I'm thinking I should be upset or downright angry, but in reality I was getting more excited with every word she said.

She eventually left after giving me a pity handjob after she told me that she would never let anything that small inside her. I was so turned on by what had happened I was masturbating furiously replaying every word she had said. Over the next few days I hardly left my apartment as I played and replayed sissy hypno videos over and over. When I did go out I went and bought my first outfit and a bit of makeup. I practiced my makeup sometimes several times a day just applying, cleaning it off, and applying again. When I finally got my makeup skills to what I thought was an acceptable level I went back to the videos.

Again I focused on small white boys being used by hung black men. Watching that BBC spread open a white boipussy was the only thing that got me off anymore. I finally accepted who I was and I started looking around online and found a couple personals sites for the local area. I created an account and posted several pictures and tried to contact a few of the other posters.

The first to respond was a rather well hung, but also heavy set, black man that was a senior at the same university. He was 9.5" hard and very thick. He wasn't all that attractive, even to sissy me, but he had a BBC so that was enough for me at the time. We agreed to meet up and see what happened. I went out and bought a wig and a new little black dress for the special occasion. I made sure to shave all my body hair and then got all dressed up. I put on that dress with some sheer thigh high stockings, a pair of 4" heels, and a black lace thong. I made sure my makeup was perfect and headed out the door.

We decided to meet up at a bar in town and get to know each other in person first. This was my first time going out completely dressed and I was extremely nervous. He was already there waiting when I arrived so we ordered a few drinks and started talking. It turned out we actually had quite a bit in common and we even had the same major. We really hit it off and decided after a while and a few more drinks to go back to his place.

We started out on the couch watching TV. He made the first move by giving me a very deep, strong kiss that left any sense of manhood I had gone. I reached down and unzipped his pants and started massaging his rapidly growing cock. He reached up my dress and started doing the same to my sissy clit. After a few minutes I pulled his cock completely free of his pants and was in awe. The pictures didn't do it justice as it looked much bigger in person. I immediately started sucking his cock and took as much as I could. He gave me a few pointers and before long I was sucking his BBC like a good little white whore.

My mouth and jaws were sore after a while so I stopped and started stroking him. My hands didn't even wrap completely around his cock. Eventually we moved to the bedroom and he put me on all fours so he could play with my sissy pussy. He started by fingering me and teasing me with the head of his cock. After stretching me out some with his fingers I could feel him start to push against me and I relaxed and let his BBC enter my white boipussy. The first time his head entered me was pure ecstasy and I let out a very soft moan. He inched in until I finally felt him balls deep in me. I couldn't believe how much cock I had in me. It was a very intense mixture of pleasure and pain. He started to fuck me slowly and gradually built up a bit of momentum. A few minutes later and he was pounding me like the slut I knew I had become for his BBC.

It wasn't long before I could feel the urge to have my first true sissygasm. He shoved his massive tool deeper into me a few more times and my sissy clitty sprayed cum all over the bed. As soon as I did he said, "good whores clean up their mess". I immediately got down and started licking up all of my cum. I had eaten my own cum before, but being commanded by a superior BBC made it so much better. When I finished he grabbed me and put me on my knees. He stood over me as he jerked his BBC in my face. He came more than I had ever seen in my life all over my face. I was in sissy heaven as I tried to catch and eat every last drop of his superior cum.

Over the next few weeks we continued to fuck and I let him cum inside me several times. Unfortunately, as the school year was ending we went our separate ways and he graduated. When the next school year started I wasted no time finding a new BBC fuck buddy willing to share me with all of his friends.

I was lucky enough to be introduced to a white woman named Heather not long after that who also has a BBC fetish. We have been together five years now and she has been cuckolding me ever since with BBC. I've never been allowed to enter her beautiful pussy and she keeps me caged nearly 24/7. That's fine with me because she also likes to share her BBC lovers with me and I wouldn't want it any other way.

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