Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.
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For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.
Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.
We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.
I settled into being (just) best friends and not hooking up...
Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.
This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us
even closer together, but we were thousands of miles apart and each quarantined.
Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:
- Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
- We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
- When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
- We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.
As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.
I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.
I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.
