Taking My Roommate's Virginity

About me:

Brazilian parents, lived in the USA most of my life.

Black, 6'3", a ripped athlete on the college soccer team.

Blessed by God with a large penis.

Orientation: I love women, but I occasionally like to top men. Started experimented as a bottom when I was 14, then for whatever reason my desires became more dominant at about 18.

College sophomore.

My roommate Evan:

American white guy from the country, had barely seen a black guy before college.

Homophobic but a good guy, down to earth.

6'0", stocky, ripped, wrestled in college and now does amateur mixed martial arts.

Popular, good looking, but has never been laid. Lacks confidence and has no game.

Freshman.

If you are black, in shape, have a big cock, like to experiment with both sexes, and (most importantly), have a good attitude towards your fellow human beings, you will have as much sex as you want in life. This is the story about my favorite male on male time in college, and the only time I ever fucked my roommate.

I hate labels. If someone tried to define me as gay, straight, bi, or whatever, it would be difficult. I guess "bi" is the best label, if you had to give one. The problem with that particular label is that everyone who calls themselves "bi" is has different tastes. Some are really gay, and some are just really kinky straight guys. It also changes with age. I love women. I always have. I only become emotionally involved with women. After this story and a number of years went by, I was happily married, just as I always knew I would be. I got laid for the first time at 13, when I barely knew what I was doing. When I was 15, I suddenly became curious. My submissive side won out and I gave my first blow job. Within a couple months, I had taken my first penis and tried anal. I loved it. I did it a lot and gained a lot of experience.

When I turned about 18, for reasons I don't understand, my tastes completely changed. Maybe it was a natural reaction to my increasing physical size and dominance on the athletic field. The truth is, I have no idea. While my love for women stayed the same, suddenly I was not turned on at all by the idea of being on my hands and knees. I switched roles, and now I liked to have the men submit to me. It wasn't a relationship thing with men. I have fucked many men, but have never kissed one. I just liked to dominate them. I was very honest about this to my partners, and I had men lining up to take me. I had a certain exotic appeal that contributed to my success, with a Latin accent combined with the risque appeal of taking a big black cock. But it was always just a hobby. I had a few relationships with women over the years, and it was always different; more tender and caring.

The men that turned me on the most were inexperienced, masculine men. I enjoyed being their first time. I easily met a lot of people online while in college that fit this criteria. We were young and horny, and many people were just getting to be a little curious. Having been like them when I was younger, I knew exactly what to do and say to turn on bi-curious, submissive men and put them at ease. After a series of patient email exchanges to get to know them, and maybe a couple meetings to let them try oral, I inevitably was able to persuade them to try anal. I consider this a big deal, because for guys that are becoming curious and experimenting for the first time, taking it in the tailpipe is a huge, very taboo first step, and it changes a person forever. As for the act itself, I was very dominant, and I definitely treated men like the submissive people they were. But I was not disrespectful. If I ever took things to the next level and called someone my bitch or whatever, it's because I knew they wanted to hear it. After the deflowering, we typically parted ways, both satisfied with what we had gotten from the experience, and I moved on to another conquest.

I wanted to fuck my roommate from the moment I met him. He was a typical white, homophobic guy from the country. I loved fucking white men more than any other race. It of course played into my slavery fantasies, and I just found the lower half of their bodies more attractive. I'd apologize for my racial preference, but the submissives certainly had their preferences too, and it improved your sex life to admit this to yourself and move on without guilt. Evan's muscular build combined with the erotic appeal of fucking someone who could beat up every man in school turned me on. If this guy would submit his virginal backside to me, that would be the ultimate experience. Unlike the soft, delicate curves of women that I loved, for a man to make me take notice, his ass needed to be fit and strong. It needed to look like the last thing in the world it would do is allow my penis inside. But with Evan, I knew it would never happen. He was completely straight, and as a Mixed Martial Arts fighter, he had too much to lose if anyone knew he was experimenting. So we were just good friends with a lot of other stuff in common, but our social circles were different. We were both athletic but did different sports, and I kept my bisexual life secret.

This delicate balancing act came to a crashing halt in January at the start of second semester when Evan came back one Saturday afternoon when he was supposed to be out of town. He was supposed to be in DC for a fight, but the event ran into some legal issues and got canceled. I had connected with a couple online who it turns out I knew from the same dorm. This had only happened to me once where I met someone in person who I did not know from emails that I already knew face to face. But we adjusted okay to the surprise. They were the typical "couple seeking Big Black Cock". Since the secret was out about our lifestyle inclinations, I made an exception to my rule and had them over to my dorm room to have fun instead of fucking them at their place. I had the music up loud to ensure my suite mates couldn't hear dialogue. Since it was the middle of the afternoon, nobody would complain of the noise.

I didn't hear the key when he unlocked the door. I froze when I heard the door slam shut, and I saw Evan gaping at us. I was standing next to my cheap college twin bed, gripping Dan's hips and fucking him doggy style. An attractive blonde girl named Jennifer was seated on the opposite side, naked with her legs spread. The lady and I looked up, but Dan waited a few seconds before looking until he wondered why I wasn't driving into his ass anymore. I felt really bad. Dan was on the football team, and he needed to keep this part of his life on the down low.

"What the hell," Evan said, his face turning red. He looked at the woman, then his eyes froze on the part of my penis outside Dan's ass. I slowly slid my dick out. His ass, which if I could trust what he said was taking its first cock, hung wide open. I had been fucking him for 15 minutes, and he was fully dilated and used to the penetration. My large cock stood up, slick with lube and erect. Evan was looking at my dick, amazed by how large it was now that he had seen it hard for the first time. He had seen me naked enough to know I had a huge flaccid dick and a small tattoo of a flag right next to it, which he probably recognized as that of Brazil. My entire pubic area was shaved smooth, making me appear perhaps even larger. When Dan's poor asshole gaped open huge for a few seconds, I know Evan had seen this before too, just with women in porn.

I won't go into detail about what happened, but Evan was an ass about it. He went off, called me racist shit, and stormed out. I stayed cool and tried to put myself in his shoes, mostly apologetic to him and embarrassed, and begged him not to tell anyone. This college was more accepting of this kind of behavior, but if word got out, it would still be bad, especially for Dan.

After the events in this story, Evan relayed to me a lot of his feelings at the time, which I will insert into the story. Evan and I didn't talk much at all for a couple months, then two key things had started to change by March. First, he couldn't get the image out of his head of that guy on his hands and knees, seemingly enjoying the penetration. Secondly, he realized he had been a complete ass to judge me like this. To my surprise he asked me to have a couple beers with him, and he apologized. He even asked a few questions, seemingly unable to understand how he had seen me do so well around the ladies, then be caught fucking a man. I explained as best I could how I could like women and occasionally still fuck men for fun. I had no idea he was a little interested himself, which I would find out later.

I hoped he thought I was a pretty good guy. Maybe I was a kinky sex addict, but I was from a poor family and worked my way through college. I treated people with respect, and I volunteered for a lot of charity work. People seemingly held me in high regard. So without sounding arrogant I hope, let's just say I think I had some redeeming qualities. After a couple beers he asked me. "Bob, I don't get it. Are you gay? Are you bi? You can have any women you want."

After affirming the conversation would stay between us, I explained, "I'm not gay, man. I like to dominate people, and fucking a guy in the ass is a way to appeal to that part of my personality. That girl with me was his girlfriend. He's not gay either, he's just very kinky and submissive. I was helping them with a fantasy of theirs. First I fucked her, then I did him in front of her. There's a whole alternative lifestyle where the lines are blurred, and people like you sometimes just don't get it. You'd also be surprised to know for every one of me, there's three guys like Dan that like to take it. Or at least that's the way it seems here."

We didn't talk more about it, but at least we had an understanding, and I didn't get the cold shoulder treatment from him anymore. We were cordial.

Right about that time in March, we had a bad break-in at the room next to us in the same suite in the dorm. My roommate and I were pissed, because we are both the kind of people that would enjoy having that happen if only we could catch the person doing it. I programmed my web cam to my iPhone in our dorm room. Now my computer could see the entire room, would record a certain amount of the latest footage, and with the IP address I could view it in real time from anywhere with my phone. If anyone broke into our room, they were screwed. To be fair, my roommate knew we had done this. I just didn't tell him when he resumed his masturbation habit and forgot I could see him.

I didn't ever jerk off thinking about men. I thought about women on those rare instances when I did enjoy pleasuring myself. By my sophomore year, I had developed enough connections to where my penis was pretty much always satisfied inside someone else's body versus my hand, whether that body was a woman, her boyfriend, or some bi-curious man giving his first blow job to someone (me) he had met online. My roommate became the first man I jerked off thinking about. I saw him pleasure himself in the room while I was away. He did this once or twice a day, and the timing was very predictable. He had a great body and was very masculine. He did it differently each time, and my favorite was when he faced his bed and stood jerking, so his strong ass faced my web cam I'd fantasize about coming in and bending him over the bed. He had a nice penis. I wasn't particularly attracted to any penis. For me it was the ass and the mind game of fucking a man that turned me on. But I did note he was a little over average size, but still way below my size. A larger penis made him more masculine, which did turn me on. The size of the penis on the man I had bent over taking my cock was irrelevant to the act itself since he wasn't penetrating me, but it still mattered. I liked them big.

The big surprise cam in April. Unknown to me, Evan was very curious after seeing Dan enjoy being anally penetrated, while still seemingly happily heterosexual. He touched his asshole while masturbating in that curious, "I wonder what it would be like to insert something" way for the first time, and I was watching the night he did it. When I was at practice, he made good use of the alone time. Two days later he got drunk one night when I was gone for the night and used soap as a lubricant to insert a finger into his anus. It seemed to hurt but feel great too judging by the look on his face. His ass was so tight the first time, it took forever for him to relax it. I remember how I did the same thing years before. He stuck to one finger while masturbating for a couple weeks, becoming more seasoned at controlling the muscles and accommodating a digit. I didn't see him each time, and one time I looked and noticed he had shaved his asshole and balls for the first time. I didn't know that he had placed an online order for a few key toys needed to really take things to the next level.

In the first week of May, I was supposed to be home for the weekend to study for exams. My parents lived about 30 minutes away, and I returned often. I liked the solitude there to study, and I took the real purpose of college seriously. Evan's package had arrived that Friday, so Saturday night, dateless, he had the room to himself to experiment. He had read a lot about anal sex and was ready. After a few beers to get him primed, he couldn't ignore the package on his desk any more.

I checked my web cam right when he started by taking a disposable enema in the center of the room. I couldn't believe my eyes, and my dick got hard immediately. I was surprised he tried it in the room. We had a common bathroom in a suite with three other rooms. But he apparently got lucky and had no issues getting to the bathroom in time. I got in my car and began to drive, the phone in my GPS mount so I could watch.

He had also ordered real lube, which was much better than the soap and Vaseline he had been using masturbating. After fingering himself, he took out the first toy, a slender vibrator. Despite being the biggest thing ever to enter his ass the wrong way, it slipped in no problem with the help of lube and vibrations. It felt great. I could tell by the look of satisfaction in his face. He just sat there flowing it in and out for about 20 minutes, getting hornier and hornier as his ass loosened. But he knew he had to take the next step to really understand what anal was all about.

To this point, Evan had still not had any thoughts about being with a man. For him, it was just the fun of playing with his asshole. I didn't know this, but I was aware of the possibility. I wasn't yet confident I could pull off the seduction. He didn't want anyone else to do it to his ass, he wanted to be in charge so far and do it to himself. But he was also beginning to realize he did have a strong repressed submissive side also, which grew every minute the vibrator stayed inside his anus.

I was out of the car now and had slipped into the dorm's TV lounge, empty on a weekend night like this. Everyone was out. I sat against the back wall so if someone came in, my roommate would still have privacy.

Evan went to the box and opened the final toy. I enjoyed the view of his asshole before he stood, shiny with lube but still looking tightly quenched and quite virginal. My jaw dropped. Even on the tiny screen, I could see it well. It was a very large, realistic black dildo. It looked huge, as big as me probably. I wondered briefly if he had done this before, but I realized he had not since he just opened it. If he had another toy, he'd be using it already. Evan arched his eyebrows and smiled slightly. While I stared transfixed to the screen, I knew I had to act. This is what Evan would take his cherry with. In minutes he would be squatting or backing up against the large dildo, the suction cup holding it fast to whatever surface he chose as he took his own virginity. I didn't want to miss a chance to get inside him first and do the honors. I was taking a huge risk trying to seduce him, but the fact that the dildo he chose was large and black gave me hopes. I had to try. I had a cleaned out, horny virgin in my room who wanted dick.

The dildo was a little big for his first time, but Evan wanted the experience to be memorable. He made a mental note to hide it well later from me to avoid huge embarrassment. He had been thinking all week about how to do it. He used the suction cup to place it on the side of his twin bed on the rail. He would get in doggie style with his feet under the bed and back onto the large phallus. His ass was plenty well lubed from the half hour of using the vibrator, but he added a lot more to the dong itself. Just as he was about to get into position, he heard my key being inserted into the door lock. I clicked the volume button on my phone, triggering the ring tone and making it seem like someone was calling me, then answered it and had about a thirty second fake conversation before entering. I watched with amusement on my phone as Evan jumped up and grabbed the dildo and threw it in the closet, lubed up and all. His bathrobe was on my bed, so he quickly put it on just as I entered. I made sure he saw me lock the door behind me.

"How you doing?" he asked. We made small talk. He seemed natural, acting like he didn't just get caught jerking off. I started taking off my clothes. I explained to him that I had a hot date at the last minute and was going to shower then leave. He was relaxed and in a good mood I noticed, probably from the alcohol. I pushed my luck and got completely naked, but instead of doing it with a towel by my tiny closet door, I stood in the middle of the room and looked into the mirror at myself. I had just shaved completely bare that morning.

"I am getting laid tonight, buddy," I said enthusiastically. I asked, "What do you think of the shaved look? Will the ladies like it?" I continued to look in the mirror and not at him to keep the pressure off. Of course he had seen me before, prepping for a shower or when he had walked in on me having sex before. But this time he was looking directly at me less than ten feet away in good light. By expertly asking him if the ladies would like it, I was allowing him to look at me and potentially become aroused in a non-threatening way.

He surprised me only a little when he answered the question. "I was thinking of doing that myself. It's a good look. Makes you look huge." He paused. "I mean that in a heterosexual way of course," he added.

"Of course, I know," I said. Then I looked at his desk. He had left out the lube. "Nice lube," I said. He realized his mistake and turned red almost instantly. I was facing the mirror, but I looked at him out of the corner of my eye, and he met my gaze.

"Shit," he said. I knew he was thinking of how to explain this. Maybe as a masturbatory aid. Maybe he was going to be with a woman later who didn't self-lubricate enough. But I acted before he could think of some plausible come-back. I went to his closet and reached in and pulled out the black dildo. He closed his eyes in embarrassment. "I can explain."

"I didn't know you were bi-curious. Remember what we did after we had that break in last month, right?" The realization hit him like a freight train. He knew I had programmed his web cam to be on 24x7 to record everything. He knew I could access it remotely. Hell, that was the point. He knew the web cam was pointed right at his bed where the dildo had been attached. The wide angle lens didn't miss anything. He had to assume I had seen it all.

"I'm not gay," he said.

I laughed at the silly comment. "I of all people know that." He seemed unconvinced. "Seriously, you can have all the dick you want and I won't think you're gay. It's not just what you say every day talking about women, I can also see the sincerity in the way you look at them and long for them." I paused, letting that sink in to convince him a little, then returned my attention to the dildo. "You picked a pretty big one for your first time," I teased and laughed, holding it next to my flaccid cock to compare. He actually lifted his gaze from the floor and looked. "It's even bigger than me, at least until I get hard. Don't worry, it took a while, but you respected me for my life decisions. And you kept a secret, so I can too." He almost looked relieved. "Besides, it is my fault for making you curious about these things. I think you're a lot cooler for this though. You're smart enough to be open-minded about things."