My (27M) my now ex gf (26F) of mine were always adventurous, there were a few women we'd have regular threesomes with as well as being non-monogamous at various times in our relationship. The sex was, honestly, a big reason we were together despite not agreeing on as much anymore. (Side note: she's like one of those tech people who was anti-trump but then kinda of became anti-anti-trump. Gross)
ANYWAYS, we had this friend R{58M) who had a long time family friend who was gay that she always referred to as her gay uncle because he was married to her aunt decades ago before coming out. They divorced, but he was so beloved by everyone, he kept coming to holidays and etc. So, we T at a party thrown by our friend and we kind of clicked immediately. He's very funny and was a bit sort of stereotypically gay in his interests, but is also like over 6 feet and jacked. He lives out of town and was visiting for a couple weeks but still worked out every morning at 5:00. He has less fat on his body than I do as a normally in shape 27 year old. It's nuts. He's bald, so he shaves his head and always wears workout clothes everywhere he goes — primarily the gym, tanning salon, and his botox woman.
My gf is very proudly bi so when R was visiting our friend, she suggested we get together with T to show him some queer bars in the city. Obviously, we ended up hitting it off incredibly well because eventually the three of us were drunk and high and talking about previous sexually adventures. He talks about how he was with women exclusively until he was 30 and sometimes misses it, so my gf suggests we have a threesome. He sort of laughs it off. But, the last week before he heads back home, we go out again and get drunk and he suggests it this time, so we go back to our place.
Once there, we get naked and fuck me his dick was huge. My gf and I would always joke that he must have a big dick because the guy was so big and muscular and confident, but the way it looked thick as fuck even when it was soft and curled up on his balls. It was just so fucking impressive. I started getting hard and that's when I knew this could get awkward. I realized, looking at his naked body, I was attracted to him.
He and I get naked first and as my gf is undressing he asks if he's the one making me hard since he's the only one naked. I sort of laugh and say it's anticipating my gf, but it feels phony. I'm harder than he is. Finally, he and my gf make out for a minute before she kisses me and R puts his hand on my neck and back. Eventually, he sort of gently nudges us onto our knees in front of him and she starts sucking his dick — I realize I'm starting to go soft, so I try and kiss my gf's neck, but T interprets that as me trying to suck his dick so he goes, “Yeah ____, let your boyfriend have a taste,” and he grabs his dick out of her mouth and sort of presents it to me. And I fucking suck that thing like I'm a porn star. I honestly don't know what came over me, but I was so fucking horny I wanted to suck the paint off of it. He starts laughing and goes, “You trying to embarrass your gf?” “How many dicks have you sucked today?” It was so fucking hot. He see's how into it I'm getting so he starts feeding into it, slapping me, smearing my spit over my face, holding my head in place to get me to choke, things like that.
This probably went on for 2-3 minutes before my gf tried to get involved by reaching down for my dick, because at this point I couldn't reach it if I wanted to the way R had my hands pinned. But, as she does, I sort of pull away and say, “Don't, I'm too close to cumming.” She tried to cover her reaction, but I realized in the moment that it might have been a mistake — publicly recoiling from your gf because getting a facefucking from an older gay gentleman was getting me to close to orgasm. It didn't help that I was literally coughing and choking on cock juice trying to get those words out.
R noticed what I said too and asked me to repeat that. So, I did, and this time he really forced his cock down my throat. I didn't realize he was cumming at first, but I was confused (and sorta scared) when my mouth started to fill up. I instinctually swallowed which caused him to say, “Good boy, swallow that load.” And there was something with the way he talked to me, so confident, so powerful, while I literally swallowed his cum, that made me shoot my load all over myself too. My gf went “Oh my god,” and looked pretty embarrassed. T was a good sport about it. At first, he kept calling me “his little faggot” and told my gf to be careful because “he might get addicted to my cock,” but once he could tell my gf was NOT in the joking mood, he said he was ready to go again and proceeded to fuck her for about 20 minutes.
My gf and I didn't talk about it that night, but did talk about it a week or so later with my gf saying she wanted to just pretend like it never happened because she didn't like thinking about me like that with another guy and felt like it “could be a problem for our sex life if I think of you like that.”
We broke up this week and I'm still pretty fucking heartbroken because love sucks and doesn't make sense.