Dear Sambag,

I (34M) have this coworker (33M) and we’ve been working in the same company (different departments) for 2 years now. I admit that he is an attractive guy, but not really my type. When he joined the company, we became friends but we were not really that close, only getting together when other coworkers would go out drinking on Friday nights.

Fast forward to 5 months ago. He stayed late in the office preparing treats for the kids that would come in the next day for Halloween, and I joined him in this task. We got to talking and by the end of the night, I suddenly found myself developing a crush on him.

After that, we would hang out with other coworkers almost once a week toward Christmas time. By this time, I have already developed deeper feelings for him but never acted on it. From what I knew about him, he was straight and I don’t want to cause trouble. A few days after Christmas, we had drinks at his home. Most of us were ready to go home at around 3 or 4 in the morning, but he asked me to stay because he didn’t feel comfortable about me driving home.

He made me sleep on his bed, and he went back out of the room to clean up. I woke up and found that he was already sleeping beside me with his back turned to me. At that moment I felt so brazen that I wrapped my arm around him and held him close. He didn’t move. Moments later, he took my hand and put it on top of his already hard dong. Lust took over – he pulled his pants down and I went down on him.

When I woke up the next day, he prepared breakfast and we talked like nothing happened. I went home, and later that evening I texted him to tell him I was sorry about what happened. He texted back telling me to not tell anyone about it, especially to our coworkers. I never intended to, so I was like ok no problem.

After that night, we became closer, always talking in the office, always texting at night. This went on for a couple of weeks and one time we hung out (just the two of us), and when I dropped him at his home, I told him what I felt about him. Told him I liked him a lot. He responded by saying that he didn’t see me like that, he apologized, and I was really embarrassed. He gave me a hug, and apologized again. He said, he can’t have a relationship with me because he would want to end up with a girl in the future.

The next day he asked me if it would help if he would distance himself from me. I told him it would, but it was a bit difficult because we would always bump with each other at work. I’m not inexperienced when it comes to this thing, so this was something that I got over easily after a couple of weeks I think. I got to a point when I was comfortable hanging out with him again, sometimes with coworkers, sometimes just the two of us. It helped that he was really fun to be with and I had completely gotten over the fact that I embarrassed myself before.
But, something happened again. He invited me for drinks at his home and when we were done, he led me to his room and he undressed in front of me. Then it happened again. The next day, he texted me again to tell me to never tell anyone about what happened.

So it pretty much became a regular thing (once or twice a week). We made love — it was wild and crazy and very satisfying. When we were lying right after the deed, he suddenly burst into tears. I got really concerned. I asked him what was wrong, but he wouldn’t talk. So I just told him to tell me about it when he’s ready. I figured he was ashamed of what happened, and I told him that he IS a FWB – a FRIEND with benefits – and that I care for him and that if sex is complicated for him then we should just stop because I intend to keep the friendship. He said he would still want to have sex and I told him that the only way it would work is if we are completely honest with each other about everything. He agreed. And so this went on again for a couple more weeks, and we became even closer and we were really enjoying each other’s company even if we were not under the sheets.

For the next couple of weeks I wouldn’t be able to hang out with him because I will be out of the country for a short vacation, and he told me that if he finds out I’d be having sex with anyone while I’m away that he’d be angry and jealous. I was speechless for a while, and I asked him why he felt that way. He didn’t offer any explanation, he just told me that that’s what he was feeling and he apologized. Told him that this is something that we just do for fun, and that we are not a couple, thanked him for his honesty, and asked that if he’s ready to talk more about it then we should when I get back.

Now, I’m thinking of ending the benefits thing and just be friends. Our friendship is something that have grown to be important to me and I don’t want to complicate things between us because of sex.

What should I do? What should I tell him when get to talk again? Honestly I just don’t want the sex to end yet because he is VERY good but that’s just the selfish me that’s talking. I value his friendship a lot, and I don’t know how to approach this yet as this is the first time that I got myself a FWB.

JB

Dear JB,

He sounds like a great guy, as do you. I’d explore the relationship part of all this more than friendship with no sex (if that’s what you’re ultimately looking for) and suggest removing sexual activity, but more so on your end. Don’t initiate anything, let him. If you make it easy for him to act on his feelings, I don’t think that there will much realization for him to make on his own, blindly doing what you say because he has an urge. Instead, I’d let him have urges and let him begin acting upon them himself.

But I’ll stop there and let our readers weigh in. Please share your advice in the Comments below.

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Dear Sambag, I (34M) have this coworker (33M) and we've been working in the same company (different departments) for 2 years now. I admit that he is an attractive guy, but not really my type. When he joined the company, we became friends but we were not really that close,...