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.

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From author: Thanks for reading, and all votes and feedback are appreciated since this is my first story! Have a great day.