[MM] Nearly had sex with my best friend

Hello Reddit! This is my first post, so please excuse any dumb mistakes. I am a bi-sexual male who is introverted and aromantic. I have never been in a relationship, dated or even kissed anyone despite being 24 years old and having gone to (and graduated from) college. I wasn’t a late bloomer or ugly, I just never had the need to be in a relationship with someone. About four months ago I decided I needed to be more active and meet new people so I signed up for a gym membership and started to take classes. The trainer, Tom, is a fairly attractive guy who is 5’6 and 170Lbs with blue eyes, brown hair, fair skin, scruff, and is in much better shape than I am. I am 6’2, 135Lbs with brown eyes, brown hair, fair skin and high cheek bones. I am self-conscience about being underweight so I go to the gym every day and take classes from Tom. After a few months we became friends and grew pretty close. I found out he had a girlfriend in a different city that he visits every weekend and he found out that I was about to go into the Navy as an officer which (to my surprise) made him upset. I thought: “geez, does this guy really care for me that much?” I’m not going to lie, there was some sexual tension between us from the get-go, but it really surprised me.

A month ago I selfishly told him that I was bi: the sexual tension had gotten pretty strong and I wanted to spill my guts to relieve it. I was totally prepared for it to end the friendship before it really took off but I was so glad I did. When I told him, he didn’t make a sound. I stopped what I was doing and looked at him square in the face. I was expecting to see a poker face, but what I saw instead was shock and **enormous pupils**. He was aroused. For the rest of the workout we talked about the porn we watch, who we find attractive, what we do on weekends, kinks, how we masturbate, how many times we masturbate, etc. I have never discussed something so intimate with anyone in my life and it was really exhilarating.

Flash forward to two weeks ago: Tom invites me to a Halloween thing for two off Groupon and I accepted. My day started by going to the gym for 2 ½ hours and doing some yard-work for a family friend (older couple in their 60s that I love to hang out with). The yard-work took 40mins but the conversation and drinks spilled into the evening. So, drunk and ready to party, I went home, showered and met Tom at the rendezvous to carpool to the event across town. The whole night we drank, ate, and had eye sex during intense conversation until we were the only guests left. When we got back to the rendezvous we continued talking for another hour (1am). I told him that I was a virgin and had never dated before, which again shocked him. He then told me he had never kissed nor did anything with a guy before and asked if he could kiss me. I agreed and we French kissed! It was so much better than I expected. My heart was pounding. He said that the air felt electric like it was his first kiss all over again. I asked if we could do it again. Without hesitation we grabbed each other and had a full make out session. After we kissed, we said our goodnights and went home.

About this time I was planning to go to New York to visit my brother in November. Tom is taking off time in November and he said he would love to go to New York. I offered to take him along (which he accepted) and bought airfare and a hotel in Manhattan in the shadow of One World Trade. I have never traveled with friends or gone on a road trip before, so I am really looking forward to it. I spent way more than reasonable to make sure I was close to my brother and in a prime location directly over Fulton Station which is a hub that nearly all subway lines converge on.

Three nights ago Tom invited me to his house to watch TV. I made cocktails and we watched Archer. About two hours in we were sitting directly next to each other on the couch and he lies back on the couch with his legs over my lap. I was immediately horny. I rubbed his legs and lay sideways with my face on his hip and our legs intertwined. We started caressing each other and feeling each other up. He tells me he would hate for his roommate to walk-in on us and that this could go further if I wanted (obviously inviting me to his bed). I was a little nervous but I accepted his offer and we tip toed to his room. We left the lights off and made out, spooned, and kissed each other from head to toe. I am embarrassed to say, but I was shaking like a leaf so bad that he had to hold me and tell me it was ok (I know how cheesy it sounds). Eventually, I stopped shaking and he started to give me a hand job, which was nice, but not really something that was going to get me off really quickly, despite having soaked my underwear in pre. He jerked me for a while, repositioned himself, and started blowing me. It was soft and warm and everything that I could have hoped for in a blowjob, but I started to feel guilty for doing this with someone who already has a significant other. I’ve met her a few times and I liked her; it didn’t feel right to be screwing around with her boyfriend. I went soft and he stopped. It became a little awkward for a second and I told him that I was just nervous. We continued to spoon and kiss for a few more minutes, but it was late, so I left and went home.

We act as if it never happened… any of it. We act as if we are just two good buddies in the gym and we haven’t discussed it yet even though we meet for coffee twice a week on break. I feel conflicted as to what to do and how to act around him when we are alone. How am I supposed to share a hotel room in NYC with him and not feel like a cheating bastard? I feel no desire to become a couple and I’m not jealous of his relationship with his girl, but I feel like he might feel slightly possessive of me if this friendship doesn’t remain platonic. Philosophers of Reddit: can I get your two cents?

Source: reddit.com/r/gonewildstories/comments/79cl0u/mm_nearly_had_sex_with_my_best_friend

2 comments

  1. I think the most important thing would just be honest with him about your reservations. This is a very complicated situation for a first relationship, and he will understand that. Being open and honest about what you want will help to preserve your friendship.

  2. I would tell him, that you don’t want to be the bad guy cause he is cheating around his girlfriend. Think about this, what if you were the girlfriend and this was happening behind your back and you didn’t know about it. That would make you feel unhappy, and felt betrayed. I might want to stop everything your doing with him, and tell him that him being unfaithful to his girlfriend isn’t right. Also, distance yourself. And if he doesn’t be truthful to his girlfriend, the girlfriend would well be angry towards you. In my past relationships, I actually been on the end of being cheated on or threaten to be cheated on by my first and third ex. If, I was the girlfriend my heart will be broken and I would have a hard time trusting the next guy that comes into my life. So, you have two options: do you stay away and be honest or do you become the man that becomes the reason why he and his gf aren’t together anymore?

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