Last summer, I(27M) fell madly in love with a woman(30F) I worked with, let's call her Taylor.. She did not feel the same, but I tried my best to win her favor. One week in August, she had a family friend Rod (55M) visit from out of town. He was much older than us and gay. He had gotten kicked out by his southern family in the 90s and was sort of adopted by Taylor's family. He recently divorced his husband of a decade and was taking some time off work to travel and take his mind off it. One night, Taylor had plans and felt bad leaving Rod alone, so she asked me if I'd go out to dinner with me. I agreed, because I was a simp.
What I didn't know, was that Taylor thought I was bi (or maybe gay, I've heard different things) and thought I was the closest queer guy to Rod's type. Because I didn't know it was a date, I was incredibly relaxed and ever flirted with him a bit (something I admit to doing sometimes when gay men flirt with me, flirting is fun!) and flirted even more after a few drinks. He was a nice guy, pretty funny, chubby but really tall. Wore flannel and had a southern accent that you couldn't quite tell was southern or gay. He scoots closer to me and puts his arm around me a bunch to point to things and I just let it happen because I don't want to me rude. At some point, the conversation turns to porn and he asks me about the kind of dicks I like in porn. He's got this weird look on his face and I think he's just getting turned on, but then he says, “I have a porn star dick” and looks down and his fly was all the down and his dick and balls were hanging over the strap of his underwear. And it was fucking big, thick and soft snake resting on a pair of big balls nestled around black curly hair. I'd never seen a dick like that in person before and it did something to me.
He asked if I wanted to see more of it and I nodded. He put it back in his pants and stood up to go to the bathroom. I followed him in there and we went into a stall together. He had me sit on the seat as he stood in front of me and unzipped his pants again, his dick was now semi hard. At this point, I stammer that I'd never done this before, he nods and puts his finger to his lips for me to be quiet. He grabs my hand and puts it on his dick and moves it for a second before I take over. I'm stroking his dick, I realize. It's way soft than I thought it would be. He grabs my hand again and moves it in front of my mouth and whispers for me to spit. I spit on my hand and then when I realize that doesn't give enough lubrication, I try to spit on his dick. He loves that.
His moan and feeling his dick jerk in my hand from something I did, gave me another surge of confidence. I licked the head. He moaned again and put his hand on my head and sort of pushed my head down on his dick, so I opened my mouth. He says, kinda loudly. “Pretty good for a first timer.” At this point, I realize I'm hard as fuck and close to cumming in my pants. I turn into a slut, or try to. I try to deepthroat is dick but can only take like two inches before I gag. He laughs and says, “I'll help” and he holds my neck in place as he sort of fucks my throat. I alternate between sucking on the head and jerking him off for the next 10 minutes before he cums on my face, I swallow some of it, he wipes some off. At this point, I'm rock fucking hard so much so that he notices as we walk back to where we were sitting.
He starts by asking me, “How long have you known you were gay?” And I have to tell him I'd truthfully never done anything like that before. That I had only dated/fooled around with women before that. At first, he was in disbelief. Once he did realize, he was mortified because he said, “What an awful first time.” For the next hour or so we talked about sexual experiences and how turned on I was and what was going through my head. Real psychological stuff. At the end of the night he goes, “I'm pretty confident you're gay. If you give me a chance, without anything crazy, I think I can help you realize that.” Honestly, at this point, I was so fucking horny and turned on thinking about his huge fucking dick, that I ended up giving him my number so he can “talk me through things.”
Over the rest of the week, we meet up a few more times (always ending the same way) and he sends me questions about my sexuality to think about, gay erotica, gay porn, dick pics, journaling assigments, meditations to do while falling asleep, etc. We keep this up even after he goes back home. It lasts through the winter. Then, he gets back together with his husband and cuts things off.
I thought this whole thing was behind me, but over the last couple months I've tried to date women and it just… hasn't worked. I can't tell if it's because sometimes you go out with women and it doesn't work or if because I'm barking up the wrong tree.