12 comments/ 124689 views/ 44 favorites Taking My Roommate's Virginity By: joelafayette 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." Taking My Roommate's Virginity "What happens now?" he asked, trembling from the embarrassment and pressure. It was time to push my luck. Evan would either kill me or get fucked in the ass. "I've got a date with a nice lady, so I'm going to shower, and you have a date with a dildo. I'm sure we'll both have a great night." I did call a lady friend for later on my way to the school, so it was actually the truth. I turned the stereo on, similar to how I did it when I had sex to cover any noises for other people in the dorm. I threw my shirt over the web cam, and I pressed firmly and attached the dildo back to his bed frame. "I'll give you two some privacy. Thanks for getting the black one, by the way. I'm very flattered." I took my time in the shower, giving him plenty of time to leave or to at least get dressed. When I came back in, refreshed with a towel around my waist, he was still in the robe, sitting on the bed. That was a good sign. True to his personality, he made a joke when he couldn't think of the right words. "You know, I wanted a white dildo anyway, but they were sold out in this model." I laughed, and it was the perfect way to ease the tension. I could tell the alcohol had relaxed him, or he had just thought, fuck it, I might as well talk about it now. Of course, I didn't believe him. He got the black cock simply because he was more interested in black cock versus white cock. I decided to press the issue. I went over to his desk and got the sturdy chair with arms from his desk. It was a solid chair with no wheels that would support some weight. I put it in the center of the room, facing away from the full length mirror we had on the wall. If I was going to fuck him, I definitely wanted to be able to see the expressions on his face through the mirror. I faced the chair and spread my legs and leaned over, my forearms on the chair with my ass pressed back, just like many years ago as if I was bending over to take a penis. "This would be your position, you'd look hot and powerful like this." Before he could answer that weird insinuation, I changed gears. "Can I ask you a personal question, just between us?" "Oh hell," he said with a nervous laugh. "I guess." I paused for a minute and went to the fridge and opened a beer. "I have to stall for a bit before I meet her, so I have time for one beer. Do you fantasize about submitting to a real man, or are you just curious about how stuff will feel in your ass. I know you're not attracted to men probably, but does a real penis turn you on?" "I don't know, maybe." Wow, honesty. "I'm sorry, I was making assumptions about your experience level. You haven't been broken yet, have you?" He shook his head no, seeming to understand I was asking if he'd had a dick in his ass yet. "Don't worry I'm not going to try to make out with you. You know, I've seen this pattern many times. If you are curious enough to buy the dildo, I know one day you will want to touch a real penis, and you will perform oral and will probably take a real one in the tush also. Seriously." "No, I'll never take it that far," he said, but he looked at my penis while he said it. The towel barely fit around me, and there was a gap that allowed him to see me. I was incredibly turned on, but managed to keep enough self-control to prevent an erection. But I knew my flaccid hang was plump and impressive after the hot shower and the blood already flowing to it in anticipation of a possible climax. I was beginning to become aroused, and he was trying hard to act like he didn't notice. I know I wouldn't be able to hide my true desires much longer. I wanted his hot ass. "I've seen this pattern play out enough to know for sure, and it's okay. You'll try it once or a few times and love it. Then sometime around then you'll meet the right woman, fall in love and get married, and maybe never do it again. But at some point, someone's going to get to fuck you in the ass, buddy." He was shaking his head, and we went back and forth a few times. I handed him his open bottle of whiskey that was sitting on his desk. "Take a hit of this, you deserve it and need it." He took a couple shots of that while I finished my beer. "You're lucky, you know," I continued, trying to disarm him. "Some guys really stress over their first time and have a horrible experience. You have an experienced big black cock right here with a nice, discreet guy that you won't see again ever or at least over the summer." It was time to lay my cards on the table and risk it all. I had been leaning against the dresser about six feet away in a non-threatening manner. I stood confidently and walked over to him, letting the towel fall off me. "Why don't you get a good look before I go, so you can at least imagine a real one you've seen up close when you have that fake one sliding inside you." I stopped about two feet away. He was seated on the bed, so my cock was a little below eye level and right in front of him. God, I hope he didn't freak out and punch me or something. Evan was certainly the most masculine man I have ever tried to seduce, and who knows what his panicking mind might make him do. But for now nothing happened. He really did just look at my dick, and I made no forward motion to intimidate him. We stayed like this for a couple minutes. He even moved his head around and looked at it from different angles. "Put it in your hand," I softly commanded him, getting more confident with every second that passed. His hand reached out tentatively on this defining moment, and he clasped it around my member. I smiled as he slowly pumped it a few times. I knew now he would let me fuck him. If I didn't hit it tonight, it would be my fault for having no game. I remembered when I first was learning how to touch another man, and I didn't rush him. I let him play with it gently for a minute and get used to it. I was growing larger with each pump. After about a minute, when I was almost fully hard and the first shiny drop of precome appeared at the tip, I stopped him. "That's good. Stop teasing me now. I don't want to show up for my date with Julie with a big boner already. I looked at him closely as I backed away, and I could see a bit of regret in his eyes as he lost his new toy. Perhaps he wasn't ready to beg me to fuck him yet, but he didn't like the idea of me leaving either. Of course, I wasn't going anywhere, but he didn't know that. I picked up my pants. "Stand up," I told him. "Come over here, and show me." I patted the chair, and he knew what I wanted. Evan tentatively rose to his feet and came to the chair. He bent over slightly and grabbed the arm rests and arched his butt out a tad. I was standing next to him a few feet away, and I dropped my pants, acting like for the moment I would delay my departure. I could see his erection, a huge bulge pressing against the thin fabric of his robe. He was horny as hell. "Holy shit, buddy. You are turned on big time." I put one hand on his strong upper back. " I don't know..." he said, but he smiled slightly. "Spread your legs a little more." As he complied, I reached in and rubbed where I knew the sensitive underside to his shaft was. He moaned. Rather than push me away, he took one hand and undid the drawstring on his robe, and the middle parted for me and revealed his athletic abs and the hard shaft that waited for me. I grasped the engorged flesh directly to turn him on. His cock twitched and pulsed in my hand. He put his hand up like he was going to stop me, and inhaled sharply, but he just froze for a minute. "Wait, I..." he started, but when he realized how good another hand on his member felt, he couldn't make me stop. I didn't know at the time I was the first man or women to touch him like that, so it's no wonder it felt so good to him. He relaxed and put his hand back on the chair. "The further down this path you go, the more and more turned on you will be. You can't help it. Bend over a little more, and your arousal will grow as you become more and more exposed. Nobody will ever know I saw you like this." "God, what am I doing?" he muttered to himself as I released my grip on his cock and he lowered. Now he was resting on his forearms on the seat of the char, which put his butt more arched into the air. His legs slowly spread more, and suddenly he was in a very erotic position, perfect to get plowed from behind by a lucky stud like me. Still standing next to him, I said, "Let's see what we have here." I slowly moved his open robe to the right side of his ass and let it dangle there in front of him, revealing his entire bare ass to me. I knew Evan would feel a surge of sexual energy as the cool air tickled his exposed hole. I saw the barely-noticeable twitch of his cock growing with excitement, very hard now. I could sense his heart beating faster and his breathing quicken. As an experienced seducer of inexperienced men, I was very alert to the smallest changes in a man's arousal. Sometimes I had to ignore what he said and rely on how his body responded. Evan's body wanted my cock inside it. His ass looked great. Of course I had seen him naked before, being his roommate and all. But I had never seen him in this position, bent over and ready to pleasure me. "That's a nice ass, Evan. The only kind of man that can turn me on has a strong, fit ass like you." I moved into position behind him and firmly gripped his hips. "Mmm, damn that's hot," I said and slapped his ass assertively. I could feel the strong muscles twitching with excitement in my hands. His ass was tight and firm, but not small. He wasn't little. He fought in a higher weight class, and had the muscles on his frame to show for it. It was just how I liked it. If I could picture the perfect male ass to fuck, this was it. "I'd love to get inside this ass. You said this was completely untapped, right?" "Of course. What are you doing back there?" he asked nervously. "I don't think I want to do this." Despite his apprehension, I knew I had him. When he let me pull up his robe and stand behind his unguarded ass, he was telling me for sure he wanted to submit. I went back to his front, and he momentarily had a chance to relax from the imminent moral decision he had to make. But he didn't move from his position, reinforcing with body language what he really wanted. "I suppose I can spare a few more minutes to relieve some stress for us both before I go out." I grabbed the lube on the desk and, with my dick completely hard just inches from his face, squeezed some of it out and generously lubed up. Despite his apprehension, Evan was turned on seeing my hard dick, knowing that it was his body causing my arousal, and it filled him with an odd sort of pride. "God, your dick is really big," he said. My dick had completely hardened while standing behind him and thinking how great it was going to be to fuck him. "I've never met anyone that couldn't take it, male or female. Of course, we'll have to take our time working it in, that's all." I paused before continuing. "Nobody but us will ever know. As long as you give me what I know we both want anyway. Now be honest. You want me to fuck you." He didn't answer, but he closed his eyes and sighed. Of course, we both knew I was not the kind of guy to ever tell anyone about this and betray his trust, but me threatening to helped him go through with this without begging for it. He appreciated me saying it, because it made it easier for him to try the next step. I put my left hand, the one not covered in lube, on his upper back assertively. "You don't have to answer, I'm going to give you the tip of it and see how you like it." I moved to the side of him, and my right hand went back to his ass. I slowly slid my middle finger down the crack of his strong ass until the pad of the finger aligned with his hole. I pressed gently, my lubed finger quickly opening the hole until it pressed against the tight ring of his sphincter. I rested for a second, then gently pressed inside. He gripped me tightly, and I heard him moan throatily. I knew it had been at least 20 minutes since he had taken anything, and it was important to again relax his opening a bit before fucking him, so I left it there for a few seconds, then tunneled it in and out for about a minute. "That's a real nice ass, Evan, so tight and fresh. Don't waste it on a plastic cock when you can honor me with your deflowering and get what you really want at the same time. You took two fingers before, right?" "Yes." As he answered, I was already adding a second finger, and I slipped two inside him with little difficulty, but I could feel his ring very tightly gripping them. "Ooof," he moaned softly as I probed him. While inside his ass, I spread my fingers and tested the walls to his anus. Opening the hole. Going from two fingers to my cock would be too much without this extra preparation. I knew stretching his hole with fingers already inside him like this wouldn't cause much pain, and would quickly relax his muscles. I rotated my hand as I stretched him first from right to left, then top to bottom. After about two minutes of additional prep, it was time. I pulled out my fingers. "Now you are ready." I moved behind him. "Time to man-up. I'm going to take your virginity now, and it might hurt a little at first." Evan shivered in excitement, and he perhaps unconsciously arched his back more and made his butt stick out prominently, and the cheeks contacted the sensitive underside to my cock, which was so hard now it was flat against my belly. Inserting your penis for anal sex is actually an acquired skill, and I was a master. If you don't know what you are doing, there is inevitably a lot of fumbling around, missing the target, sliding off target if you can't immediately penetrate a tight backside, etc. But I knew what I was doing. I could see the hole anyway because I had done such a good job of positioning him in a wide open standing doggy position. My hand gripped my large penis and brought it to his waiting hole while the other hand spread his left cheek to the side. My thumb led the way and found the hole, giving it a quick probe to mark it, then I slid my hand up the shaft a bit as the head poked through my grip and pressed firmly against the hole. My favorite part about taking a male lover is when I first insert my penis. The ass is very tight, and I always get a very submissive response from the recipient of my cock as he struggles to accommodate my size. Their grunts and moans of pain and surprise always excite me, almost as much as watching them turn to pleasure later. But part of what goes on inside my head I keep to myself, because it is a little strange. When I fuck a man, I feel a surge of energy as I feel his manhood transfer to me, the dominant top. This is especially enhanced when the man's ass is virginal. I know there's no real transfer of energy, but because this fantasy builds in my head so much, my mind responds like there is. I get a huge surge of adrenaline that spikes when I first penetrate, then slowly builds throughout the experience until I climax. When I finish in a way that is really dominant, such as a nice facial, (if that is what my partner wants) then I get another energy surge. That is just what goes on in my head. I know in reality a bottom retains his manhood quite well after having the courage to do what turns him on. This is why I could barely contain my enthusiasm as I stood behind Evan's sexy, strong ass. But I took my time, because building things up was good for both our pleasure. In the beginning, Evan was completely closed off to me as expected. I left the lubed head pressed against his pucker with light pressure for about 10 seconds before easing off, then pressing again. I did this a few times, until I was able to feel my head begin to open the hole. His tight sphincter muscle was just inside, and my blunt head now pressed against it. It seemed impossibly small, but I knew better and understood he had the potential to take me. I knew Evan wasn't in any pain yet because I wasn't actually opening him up yet. All that was about to change. I withdrew and re-inserted several times, slowly applying pressure to his tight ring. Each time, I felt the ring's opening expand further up and around the large head of my penis. After about seven of these, his ass was nearly opened, and he began to strain as his sphincter protested from being stretched. "Arrgh, there's no way," Evan protested. "It's not going to fit." "Patience; relax and your body will open to me." I withdrew one more time, then pressed forward a little harder. His ass opened more, and I felt his ring slide up to the ridge of my large head, with most of it now inside the tightest part of his ass. The way was clear for me now. I slowly eased forward and felt the incredibly wonderful sensations as his tight ass enveloped and hugged the head and first inch of my shaft as I slid inside. As soon as the widest part of the head slid past his muscles and opened him up fully, his whole body tensed and jerked. His thighs quivered in pain and excitement, and his butt cheeks clenched in protest. The muscles inside his ass spasmed around the unfamiliar intruder, actually helping suck it further in and providing quality stimulation for me. We had already relaxed the involuntary part of his tight sphincter muscles with careful preparation, but my large size compared with the fingers would reactivate his reflexes for a period of time, causing him some discomfort as he lost his virginity to a larger than average penis. "Arrgh. Fuck me, that's big. Holy shit!" he exclaimed. He lifted an arm and pressed it against my thigh, as if to stop the penetration. But he quickly moved it back to the chair, since after all this athlete was no stranger to the whole "no pain, no gain" concept. It turned me on immensely to see what my size was doing to the virgin. I had prepped him well, but some pain was impossible to avoid when I fucked someone. I could see the look of excitement and pain on Evan's face in the mirror as he surrendered and waited for more penetration. His forehead glistened with sweat. As I expected, I almost got dizzy from the huge surge of energy that flowed from Evan's virgin ass, through my penis and into my body, sending warmth and excitement all over me. I got goosebumps on my flesh, and my muscles surged with energy. I gripped his hips firmly and pulled him to me as I drove forward, sliding a few more inches inside him, barely able to contain my enthusiasm. I could see his erection in the mirror go from fully hard down to a softer half mast as the energy and manhood flowed from him into me as I took him for my pleasure. I sunk my cock in about a third of the way, then slowly backed out an inch, careful to still leave the head and a little shaft past his barrier while his muscles sent waves pleasure across the sensitive underside of my shaft. A withdrawal brought slightly different stimulation than an insertion. I paused for a second, then slowly sunk in further, about two thirds of the way inside as pleasure enveloped more of my shaft now. I backed out again to about halfway this time, then carefully drove forward as far as I could. I was not able to insert my entire cock in most men's rear ends, but Evan did not disappoint. I watched in awe as more and more of my penis disappeared inside the virgin. He briefly resisted, then I felt him open to me deep inside, and my hips finally pressed firmly against his strong butt cheeks. I fought back a sudden urge to come. It felt so good to be balls deep inside his tight ass, with every square inch of surface on my shaft being stimulated at the same time by his hot hole. "Uhhhhh," Evan moaned, this time as if more in a quiet acceptance than a painful protest. His head hung, relaxed and facing the ground. His legs still supported his weight, but every muscle in his body that could relax seemingly did so as much as possible. It was as if all his vitality and energy had been transferred to me. I left my thick penis fully sheathed to give the virgin a little time to get used to my size and reflect on the moment. I knew most of his pain was localized to the tight sphincter muscle, and I needed to wait a few moments before I began more rapid thrusting. Leaving it sheathed would be easier for him than taking it out and reinserting. Taking My Roommate's Virginity "That's nice. You've got my black dick all the way inside your sexy ass now. You are changed forever, and not a virgin to the penis anymore. How does it feel?" "Mmmpf," he grunted. "I can't believe this is happening." "It hurts at first. But you don't want me to stop, do you?" "No, I don't think so," he said. I was not surprised. He had a penis in his ass. He couldn't stop now and say he hadn't done it. He might as well proceed and see what the whole experience was like. This was a pattern I was familiar with. I began my first real withdrawal. Very slowly, I pulled out until just a few inches of penis were inside, then I drove back in. In the beginning of a good de-virginizing, I felt it was best to not completely vacate and reopen the tight ass muscle with each thrust by pulling out too far. I stroked him slowly, feeding him the entire length of my hungry dick. He rewarded me with a soft grunt each time I bottomed out inside him. Before I got too distracted by the urge to come, I was able to enjoy all my senses, which included not just the pleasure his ass delivered to my probing unit, but also I enjoyed the expressions on his face as I fucked him. I could see all the emotions at once: pain, uncertainty, raw lust, confusion, etc. I enjoyed all the sounds he was making. The virgin was very vocal with his expletives and grunting, and I was grateful that we had the stereo up loud since this was a college dorm room after all. I thrilled in the sight of my large black cock slowly sliding in and out between those meaty, unplundered white butt cheeks, the stark contrast enhancing my experience. I stroked Evan's hot ass slowly and deeply for about five minutes. I was in no rush, just enjoying the sensations, using my discipline not to allow myself to build to a climax before he was thoroughly broken in. I used my hands to spread his cheeks wide, and I slowly pulled my penis all the way out. His ass gave sort of a nice popping, squishing sound with the lube mixed in with the tight seal his ass had around my cock as I vacated and left him empty. Spreading the cheeks usually enhanced any gape in the asshole after the muscles relax, but to my surprise, Evan's hole didn't gape open much at all. A small hole appeared for a second, then quickly closed back into a tightly quenched starfish, shiny with lubricant. Most men I fucked, virgin or not, had a hole about two inches in diameter after this much of my ebony tool stroking them. Evan it turns out wouldn't display a real gape for the entire sex session, which was a first for me. Even though he wasn't a tiny, compact little feminine man and didn't have the tightest ass I'd been in at the moment of defloration, he did have the tightest and most pleasure-giving ass I'd had throughout the entire sex session and at the end. He was gifted. But I was a little worried he would enjoy it less if his lack of gape indicated not being able to relax versus just tightness. "Are you able to relax and enjoy it more a little now?" I asked. "Yes," he said. I could tell he was still embarrassed and unsure what to say. "God you fill me up. It still hurts though." "Do you want me to stop, or keep going?" I asked, confident in the answer. I added a bit more lube while I asked the question. He spoke now with confidence in his voice for the first time as he looked at me in the mirror. "It's too late to turn back now. I might as well enjoy myself." He reached back and assertively grabbed my left butt cheek and pulled me back towards him. "Fuck me some more. I want you to." I quickly found his slick hole and reinserted. I found him to be almost as tight as right when I deflowered him. I started the second act with a dominant slap to his butt cheek, causing a startled yelp before driving my cock forward into him. I began a more aggressive campaign on his ass, with the thrusts still deep and powerful, but quicker too. I moved my long arms from his hips to his shoulders. He lifted his upper body so his arms were on the chair's arm rests and not the seat, making him more upright and actually easier to fuck. The loud, "whap whap whap" sounds of my hips crashing into his ass cheeks competed with the grunting he was making as I drove into him over and over. "That's good, give it to me more, like that, yes," he babbled as I fucked him. "I'm getting close," I told him. "I want you to have the full experience. When I tell you, turn and sit in the chair and open your mouth. You know what to do." He didn't respond, so I had no idea what he would actually do when I climaxed. I pushed down on his back, and Evan obeyed and lowered his posture again, which gave me a better view of his hole. I slowed my pace again and went back to the beginning, slowly stroking him deeply. His ass was a little more open now, so I was going slowly not because his ass forced me to, but more because I wanted to feel the sensations as his muscles rippled along the length of my sensitive cock. I needed the correct stimulation to reach my climax. For me, pounding fast had a tendency to dull the senses. I began to withdraw my penis all the way until the head rested, nestled against his hole, before driving back in. He was more used to being anally plundered now, so it wasn't too painful when my dick reinserted each time. But he definitely felt the difference, and his grunting was in perfect time to my re-insertions as I allowed his muscles to first gape then close completely before shocking them with a complete stretch again each time. I loved the sounds his asshole made too as it was vacated then reopened continuously. I knew this was one of the most submissive moments for a bottom. He had little control over the muscles in his fully relaxed bowels, and he could feel the cool air in his asshole to remind him of how stretched out I had made him. "The pleasure your ass is giving me is amazing," I told Evan. "You have such a nice tool at your disposal to please other men, it is a waste not to use it." For a brief second I wondered if Evan would let another man fuck him one day. Then he squeezed my prick at just the right time, and suddenly I was refocused and almost ready to finish. Evan had been thoroughly fucked by this point, and I wasn't holding anything back. I began to give him shallow thrusts, making sure the tight muscle at his opening was directly pleasuring the sensitive head and first few inches of my shaft constantly. I knew this would bring me off quickly, and sure enough, after about 30 seconds, I began to feel the burning sensation of an impending orgasm build up inside me. "Almost there," I told him. Three more thrusts and I was past the point of no return. "Now!" I told him and pulled out of his ass. I used a strong kegel and grip on my shaft to hold off the orgasm and ejaculation. I knew it would only delay by a couple seconds. Fortunately, Evan was quick. It appeared he had made his decision about whether or not to let me ejaculate on his face. I approach his face, my dick at eye level. "Open fast," I told him. I was pleased when he opened his mouth wide. He was clearly nervous in those two seconds, but I didn't give him time to dwell on it. "Arrrghh," I moaned deeply as I released my pent up load. The bottom of the large head of my penis hovered, gently pressed against the top of his tongue as the first high pressure spurt of my ejaculation burst forth from me and deposited itself deep in the back of his mouth. He remained still as I fired off two more thick volleys. He must have inhaled at the wrong time, because he coughed suddenly, partially closing his mouth, causing the fourth spurt to stream across his left cheek. I couldn't see my load after it entered his mouth, because he was not looking up at me, but I knew I was on target, and my plentiful semen was coating the entire inside of his mouth. He quickly swallowed and opened in time for the smaller fifth volley of ejaculate. I then milked my cock and released a few more globs onto his tongue. Sensing I was wrapping up, he pursed his lips and sucked the top of my penis. I milked it a few more times and gave him a little more of my gift, then slowly withdrew. I squeezed it one more time and lewdly slapped my dick on the other cheek, putting one final glob on his face. I had the most amazing feeling of energy surging into me as I saw him kneeling in front of me taking my load. This combined with the explosive release of my ejaculation and all the pent up energy that had building up in me for this climax and left me in a state of total bliss. My mind was incredibly turned on and at full alert, while my body relaxed, for the moment spent. "Whew, that was great!" I said as I took a few steps back. He rose to his feet then sat in the chair he had been bent over earlier. He swallowed a couple times, then used his finger to transfer as much of the semen as he could from his cheeks into his mouth. "That was quite a lot," he joked. "Your first load, right?" I asked. He nodded. "I never even tasted my own before." I went to the fridge to get him a beer and said as I did that, "You have a great ass. I really enjoyed fucking you. You are very tight and masculine, and you didn't whine and complain." "Thanks, I guess," he said sheepishly. I opened the beer for him and handed it to him. "Something to help you wash it down," I said and laughed. "I can't believe I did that. I am ashamed." This was not a surprise, every man felt a little of this after trying anal for the first time. But I also knew he was glad he took the step and tried it. "I personally wish we lived in a world where one could do this and not worry about what other people thought. But I realize we still live in a society where privacy is needed. I give you my word I won't speak of this to anyone." He nodded his head in appreciation. I continued: "You should be happy. Let me ask you something, if there was a really hot woman in here right now that wanted your dick, would you hesitate for one minute just because I fucked you?" "God no, I am horny as hell." "Right, so you don't like women any less because of what you've done. If anything, you desire a woman even more than before. All this does is give you options. You have other outlets for your sexual energy." "But you just totally made me your bitch." I had to smile, recalling the great experience I had just had. "Yes, I did. And you loved every minute of it." "God it hurt," he said. "All the way to the end even. But you're right. What if I want to do it again?" "You and I won't. I mostly have sex with inexperienced men. You were one of my best conquests, but you've lost some of your appeal to me now since you're broken in and I have your manhood already. There will be plenty of other men lining up to take you if you know where to look." This wasn't meant to be an insult to him, it was just how I felt. Plus I knew treating him a little like a used piece of ass that I can discard now that I am done with it would only turn the submissive man on even more. "You are lucky to have found anther way to pleasure yourself besides competing for women. If you don't want to get fucked again and again on moral grounds, then I respect that. Otherwise, the way I see it is, today I just set you free." I finished getting dressed and collected my keys and wallet. "Thanks for a great time. When you jerk off later, it will be one of your best ones, I guarantee it." He took the shirt off the web cam "You can watch if you want if you get bored later. This will be the last one you see." I laughed as I walked out the door. But I wouldn't watch. I was done here and on to the next conquest. I had to admit, I had the coolest roommate at school. "So nobody will find out?" he called out again as I opened the door. "Find out about what?" I asked as I left him to himself and headed off for my date. * From author: Thanks for reading, and all votes and feedback are appreciated since this is my first story! Have a great day.