My First Time

A few years after college I visited my old roommate in Chicago, and I had done on an annual basis. We had shared a dorm for two years in college, before moving off campus to a house. We were best friends in college, although senior year a bit of a rift formed as I ended up in a relationship with a woman he really had a crush on. Tom was a rather abrasive kind of guy. His argumentative demeanor put a lot of people off, but we knew each other so well after sharing such impressionable years as college that we managed to get along quite well.

Tom lived in a one room studio apartment in a high rise. He had one large bed that dominated the tiny room. I didn't think much of it, as we shared a dorm room for two years. Privacy was never much of an issue, although now that I think back, I never recall seeing Tom nude when we lived together. The closest thing to encroaching on any boundaries was one night when his girlfriend at the time stayed over, and they had sex in the bunk bed right above me. I was livid, as she has a single room upstairs. I pretended to be asleep. She was the same girlfriend who used to tease him by flirting with me-- once to the point of kissing me in front of him.

The first night, we went out drinking, and the discussion turned to relationships and sex. As we had talked about anything in the past, nothing was taboo. He was talking about the movie 'My Own Private Idaho,' and highly recommended it. He asked if I thought someone could have sex with another man without being gay. I told him I didn't really see that as an issue. He went on to say he had met a guy at a party a month ago-- a gay man, and that he was sort of attracted to him, just to see what it was like, but that he didn't pursue it any further. I replied that society places too much focus on sexuality, and that from a mechanical perspective, it probably mattered little whether someone was with a man or a woman-- if you are getting your cock sucked, you are getting your cock sucked.

Later he brought up how he wanted to clear the air on some unresolved issues between us, that in college he was always jealous how easily I could have women. He said he was jealous of my good looks, and that it took quite some time to get over my 'stealing' of 'his girl.' I told him I was always jealous that his parents were literally millionaires, and that he never had to even think about money. Overall, we had a very good talk.

We ended the night and went to bed. There was a palpable tension between us-- a strange feeling. It was almost sexual. But then again, I thought I could be imagining it. He went to work the next day, and I explored Chicago.

That night we went out to a jazz club. We were out past two and had quite a lot to drink. We returned and headed to bed. Both of us were quite restless. Without saying a word, he put his arm around me and kissed me. It was strange feeling his stubble against my chin.

'I have always wanted to do that,' he said.

I didn't say a word. This was too strange. He pulled the covers back and laid on top of my, kissing me. I could feel his hard cock through his boxers. Before I knew it, he was straddling me, shoving his cock in my face as it poked through his boxers.

'Suck it,' he said.

Without saying a word, I complied.

'You like that, don't you,' he continued. His cock was a little above average thickness, and about an inch and a half longer than mine. I was surprised how big he was. He slipped off his boxers, and removed mine, revealing my hard cock.

I finally spoke, 'Aren't you going to suck my cock?' I asked.

'Um, I would rather not. You've been with a lot of women, and I don't want to catch anything,' he answered curtly. I didn't know what to think.

Without saying another word, he spread my legs, and started rubbing the head of his cock against my asshole.

'This is really turning you on,' he said, as he felt my hard cock. 'I thought you'd be bigger than that, judging by all the women you've fucked.'

He grabbed a condom and some lube from his night stand. The entire situation was surreal. Without saying another word, he slowly penetrated me. What began gently gradually picked up momentum. The feeling was incredible, like I could do anything. He seemed to last forever. Sometimes he thrust too deeply, causing him perverse pleasure as he studied my reaction. He was very much into fucking me, and could feel my anal orgasms. Eventually I felt his head growing harder, until he violently came. I hadn't cum, prompting him to suggest that I jack off. I really didn't feel the need, as I felt as though my whold body had ogasmed. He popped his cock out and went to the bathroom to clean up. I soon followed, and fell into a deep sleep.

A few short hours later, I was awoken by his hard cock pressing against me. We reprised the earlier activities with him taking me from behind. He told me what a beautiful ass I had and how he had fantasized about this for years, after watching me get dressed when we shared a dorm room. It was definitely a weekend to remember, although we have never talked about it since.