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.