I have been intending to share this very relatable, interesting phase of my life for a long time. Work and family life keep me very busy so that is my only excuse for not sharing this sooner.
I have always been a closet bisexual since my teen years.
I lived in a shared 3-bedroom house in med school with 2 guys in each room. The arrangement was that if one of our girlfriends spent the night, then the roommate would sleep in the living room. We were all friendly, had good camaraderie, living a hectic school life so the arrangements were all well-respected.
After the first year, my rommmate moved into a new place with his girlfriend and I got a new roommate. Let’s call the new roommate Rob. Rob and I remained as roommates till we graduated from med school (about 4 years) and a year after that as well, became best friends with a deep emotional connection and more.
Rob was handsome, introvert-ish and very intelligent. He also was a big flirt and dated a few girls through med school and after. When he moved in, he was dating this girl. Since she was still living with her parents, they didn’t need our room to spend nights together. I was single at the time. His GF also became a good friend. In fact, we were a part of a close knit group of friends who always spent time together, going out drinking, movies or studying for exams.
Being roommates and having the same classes, Rob and I got to spend a lot of quality time together. We both partied a little more than others so many times it was just the both of us drinking at a bar or at home and getting into deep-meaningful-philosophical conversations. We also talked about our sex lives with no inhibitions like our jerking off routine, likes/dislikes and more.. But I never dared to tell him (or my other friends) about my sexual orientation. I never sought or hooked up with another guy during those years. I lived a straight life dating a couple of girls. My reasons at the time were fear of being outed and possibly risking any distance between the both of us. Our bond and friendship was more important than anything sexual.
I always wondered, fanatsized about getting sexual with him but there was absolutely no way of that becoming a reality. Med school academically is hard, especially exam phases are tiring and exhausting. We hardly had time to hang out with our girlfriends and it was all understandable as they were going through a similar phase.
Rob and I studied together, discussing, testing each other and we used to get pissed drunk during any break that we could get. One night, we were tired, drunk and having our usual conversation. Rob said his body ached and mentioned that he would try and get a massage from his GF when they meet next. I told him that I could give him a body rub if he was up for it. He was mighty glad and readily accepted it. The only extent that we ever saw each other naked was in our underwear. So he had no inhibitions stripping to his undies for the massage. He laid down in a prone position first and I started rubbing his shoulders, back, legs. Next he was supine and I rubbed his chest, thighs and legs. That was it and he really liked it. I was delighted at the chance of getting to do it.
The massages kept happening more frequently without ever being anything sexual. That went on for sometime. There were times where I noticed his underwear bulge would be more prominent than usual. We also laughed it off a few times. One evening, we woke up after a long nap, lazy, and tired. We went out, grabbed some dinner, had a few drinks. We drank some more after we got back home. We turned off the lights to sleep. After a few minutes, Rob asked if I was up for giving a massage. I was fine with it. I was about to turn the light on and he told me not to. I wondered for a quick second but didn’t think much of it. He stripped to his undies and I was completely clothed as usual. I started rubbing his back, legs. He asked me if I was okay if he took his underwear off as he had a hardon and it was getting uncomfortable laying prone on his hard dick. Why would I say no? He took off his underwear. I could feel my heartbeat getting faster but I acted nonchalant. Then he turned around, I gave him the usual massage, taking extra precaution to avoid bumping into his hardon. That was it.
As time went by, Rob became more comfortable stripping naked during a massage but he always hinted at the lights being off and I never wanted to make him feel uncomfortable. So it always happened in the dark at nights. It was also the best time as other housemates would be sleeping so no danger of getting caught.
One night, while getting ready for a massage, the table lamp was on so I asked if I should to turn it off and he said don’t bother. I wondered for a second but again didn’t want to read much into it. He stripped, I started massaging his back, legs and by then he was also comfortable getting his buttocks massaged. He turned around and there it was! I finally saw his erect cock. I was completely mesmerized but had to act nonchalant. We always talked during the massages but this time he became kinda quiet. I noticed his cock throbbing a few times. I never massaged anywhere near his groin area and always tactfully avoided that area. While massaging his thighs, he told me not to mind his erection, that he was just horny and turned on. He specifically told me not to pay any attention to it. I continued on with the massage. My heartbeat was fast, I was getting hard and I could totally feel this endorphin rush inside my body. I went back to massaging his thighs when he grabbed my hand and pulled it towards his cock. He also muttered if I was okay with it. I said I was fine as long as he was comfortable. He was. So he made me grab his cock. Damn! This peak of excitement has been an unforgettable moment of my life. It was obvious what he wanted so I started to jerk him off until he came. The moments after were just silent, he got up, took a T shirt, cleaned off the cum, turned off the lights, said goodnight and slept off.
The next day was very awkward. He seemed upset and easily irritable. We had classes and a busy day, he spent the night at his GF”s place. The following day, a group of friends went out for a movie, dinner and drinks. He still seemed upset so I just let him be and this was not something we could’ve addressed when others were around.
2 days later, he told me that we need to talk. We went out in the evening and talked. He was angry at himself that he went that far. He blamed it on the alcohol, exam stress and the dry spell that he was going through. He blamed me partly and I kinda defended myself that I did not initiate it. His response was I could’ve stopped it. I told him that I was absolutely comfortable doing it only because of our deep emotional connection and it did not bother me at all. I told him that it seemed very organic for me considering how close we were. He said he didn’t want that to ever happen again. I said fine and we hugged it out. We were back to being the small old friends minus the massages.
That pact didn’t last for long. To be continued…….
