My first experience with another man was nothing I had planned for, but neither did I fight him off when the opportunity -and then my cock- arose.
I was a late bloomer in every sense of the word when it came to sex. It was not until my first year of college that I had ever even scored with a woman, and had only been able to take matters into my own hands when the familiar ache in my balls became too intense. Women had always both fascinated and frightened me. God, I wanted to fuck them but did not have any idea where to begin when it came to the gentle art of seduction. I finally managed to lay a couple of coeds that first year, but it did nothing to take the edge off of my raging hormones, and only made me want to put my cock into almost anything that moved.
My friend and roommate Greg was sympathetic to my problem. He was always ready to lend an ear when I would bitch about the lack of pussy in my life. Little did I know that he had been secretly eyeing my tight ass and jerking off on his own time ever since we moved in together, as he told me later. I came back to the room one afternoon after a home football game, having decided not to go home for the weekend as I had planned but instead to catch up on some calculus homework which had been kicking my ass. Lo and behold, there was Greg, naked, sprawled out asleep on my bed with a copy of Playgirl laying across his hairy chest. He had jerked off and then fallen asleep, thinking I would not be home till the next day. I was startled to say the least, both at realizing that he obviously had to be gay, and at the fact that he had chosen my own bed for his jerkoff session. As I looked at his naked body - long muscular legs, finely muscled chest covered in a thick carpet of curly hair, ball sack as big as a baseball with a now-flaccid cock that must have reached 8 inches when erect - I was unsettled to find that my own cock had stirred to life. I stood only inches from his legs hanging off the end of my bed, and yet I did not move away.
Greg suddenly opened his eyes and saw me standing over him. He did not speak, but only moved the magazine off of him and slowly sat upright. With slow, cautious movements, he placed both hands on my hips and gently pulled me closer to him. There was no longer any question, I had a raging hard-on bulging in my shorts and was about to try something totally new. Greg pulled me to the edge of the bed and moved back slightly, allowing me to put my knees between his naked thighs and ease my weight onto the bed. He carefully pulled me on top of him, and we fell across the bed, my weight completely on his muscular, aroused body. He kissed my cheeks and neck, pulling my shirt free of my shorts and running his powerful hands over my naked back.
Softly, he whispered in my ear "I won't kiss your mouth if you aren't ready." I responded by kissing him firmly, plunging my tongue deep into his delicious mouth. The faint bristly feel of his chin and lips was strangely erotic, and my arousal deepened. I lifted my hips and undid my belt with one hand, and he pushed my shorts and underwear down over my buttocks and across my thighs. The feel of my hard cock against his was almost unbearable. I continued to kiss him as he stroked my naked ass and upper thighs. Our kisses grew more passionate, and our hands roamed all over one another's bodies. With his strong arms, he pulled me upwards until I was sitting astride his shoulders with my hard cock only inches from his mouth. I was in heaven. None of my girlfriends would suck my cock without me having to almost beg for it, and then acting like they were doing me some kind of a heroic favor.
Greg lapped at the base of my cock with his rough tongue, his hand jerking my shaft with short, hard strokes two inches from the tip. I was sure I would come, but managed to hold it together by thinking about what my girlfriend would say if she could have seen me right then. I reached behind to grasp his beautiful cock with one hand. It felt hard and smooth, and very warm. Sure, I had never jerked another guy off before but was pretty familiar with my own pud, and had him moaning in no time. After several glorious minutes, Greg asked me if I wanted to go all the way. I said "sure", not clear what that meant exactly.
Greg reached up to the drawer of my desk and pulled out a condom and a tube of lubricant. "How the hell did that get there?" I asked, incredulous. He just laughed and shrugged. He took out the condom and slowly pulled it down over the length of my erect cock. He then spread lubricant liberally over my aching pecker and then between his legs, way down low. I was beginning to get the idea.
"We can do it this way? I mean, I don't have to be behind you?"
He responded by pushing me off of his chest and raising his legs to my shoulders. The tight circle of his anus was now in position. I took a deep breath, and gently pushed into him. He had obviously done this before, and my cock was buried in his delicious ass in only a moment. It was tighter than any pussy I had ever experienced, and I did not last long. Furiously, I pumped into his ass as he groaned and bucked beneath me. I even got creative and jacked him off with one hand as I fucked him in the ass. All too soon, I came like I never had before, shuddering and thrusting against his buttocks until every last ounce of cum was drained from my swollen nuts. Greg sighed with contentment as my cock softened inside him.
I sucked him off slowly afterwards, kissed him fully on the mouth, and then dressed and left the room. We have had sex a dozen times since then, and each time seems to get better than the last. I am still a lady's man at heart, but do not regret for a minute the times I have spent with Greg locked in a masculine embrace, pleasuring one another as only two men can.