I had always felt comfortable when around other guys. Secure in my sexuality, I knew I was only into women. Confident with my body and size, I had never been embarrassed in the locker room or when changing around guys. I kept myself in good shape: decent six-pack abs, toned arms ... and a 7" cock with just the right amount of girth. I kept my pubes shaved close to make it look even bigger. So it almost goes without saying that moving into the guy's dorm, at the start of my freshman year of college, was an easy transition.
My roommate Adam and I hit it off right away. He was attractive, outgoing, and girl-crazy; thus, we had a lot in common right off the bat. The dorm rooms were small and privacy was non-existent, so out of necessity we got to know each other pretty quickly. In fact, sometimes when one of us was with a girl in our room, the other would stay and just fake sleep. We were somehow able to pull this off with the help of the dorm room's bunk beds. Adam was on the bottom bunk and I had the top. There were plenty of nights during which I faked sleep while listening to him fuck some drunk co-ed on the bunk below me, and vice versa. It was definitely an open secret that the one not getting laid was jerking off to the action; something about which neither of us - though we might have smiled slightly - ever spoke.
We'd even developed a little bit of a routine on the nights when neither had gotten lucky. Returning to our dorm in the evening, drunk, horny, and without girls, we'd have a stroke session together. We'd just chill, lounge around naked in the room, watch porn, and jerk ourselves off. We never mentioned it when we were sober, nor even while drunk; yet still we found ourselves jerking off together at least once a week. The unspoken cue was when one of us started surfing the net for porn. The other would then sit down next to him, and we'd both watch the action, talking about the girls, what we liked, and what we wanted to do. Eventually our cocks would get hard and we'd jerk ourselves to sleep. Things went on like this for four years with not even a hint of more happening. We parted ways after graduation: I left for grad school in Boston, and Adam left to do the same in Chicago.
About six months after the start of grad school I found some time off, so I flew out to Chicago to chill with Adam. He'd mentioned that he was doing well with the girls out there, and so I was looking forward to seeing what kind of damage I could do in a new city. After I dropped my bag off at his new apartment, we immediately went out to hit the bars. We drank hard and settled in to have a great time.
As the night went on, I found myself on a barstool off to one end of the bar, enjoying a flirty conversation with a very sexy woman named Jane. At thirty years old, she was about eight years older than Adam and me and still as sexy as ever. She had all of the requisite curves and good looks, yet she also had a level of confidence and self-awareness that I hadn't seen in the college-aged girls I was used to picking up. Adam sat a few people down the bar from us, chatting it up with a younger girl named Lauren. She looked smoking hot, was still in college, and was enamored with Adam. So far things were looking perfect for my first night in Chicago.
Unfortunately, Lauren seemed a little too into Adam. He found that he had somehow flirted his way past the 'late night bar fuck' category and into the 'potential boyfriend' category; so when it came time to go back to his apartment she bailed at the last minute, deciding to go home instead, acting like a good girl and not sleeping with him on the first night. She sauntered off into her cab, and Jane and I ... and a dejected Adam got into another.
Too drunk to bother trying to hide his disappointment, he muttered, "I can't fucking believe that just happened," as we drove away.
Jane laughingly said, "I thought you had it." She shook her head, smiling at her new friend's misery. Then she said it ... "I guess I'll just have to work overtime tonight." Her words just hung there in the air.
Had she really just said what I thought she said? I thought to myself. Was it a joke or ... had she just offered us a ... threesome?
The cab got us to Adam's apartment without much fanfare, during which neither Adam nor I attempted to clarify or probe into what Jane had said ... though clearly we both had heard her. As the three of us rode up in the elevator I felt uncharacteristically nervous. This situation just felt different, and I had a sneaking feeling that Adam and I would both be getting laid tonight, after all.
Once we were inside his apartment, Adam proceeded to the kitchen to make us all some vodka tonics while I chose some music and put it on. Jane followed me into the living room, sat down on the couch, and took off her heels. Adam returned with the drinks and we all clinked our glasses together. One round of drinks turned into three ... and now we were all good and drunk again, yet a strange sort of awkwardness hung in the air. Jane had not mentioned anything further so I was beginning to think she had been joking about 'working overtime'.
Of course she had been ... she must have been....
Adam excused himself to use the bathroom, leaving Jane and me alone together. The bathroom was at the other end of the apartment, far enough away so that we had a little bit of privacy. I quickly made my move on Jane and soon we were making out on the couch. I figured Adam would see us as he returned from the bathroom and might just go off into his room so I could fuck Jane on his couch. He had been gone long enough, so at first it seemed like he had been thinking along the same lines ... until I heard him put his glass down on the table. I had been too busy kissing Jane to even notice that he'd returned. So there we were: Jane and me on the couch, still sitting but intertwined in an embrace, and Adam who leaned a little unsteadily against the wall about five feet away.
