He’s a close friend I’ve known for over 20 years. I had always been a regular straight guy in his eyes (dated some women a long time ago). We just typically chilled and did regular hanging out stuff (sports, hikes, music, bars). Nothing sexual ever. In general he’s a very sought after guy. He kind of looks like Ryan Gosling (no joke) and I’ve seen so many women throw themselves at him throughout the time I’ve known him. I’m 5’5”. He’s 6’3”.

He lived and still lives several states away from me and i hadn’t had the chance to hang out with him as much. Thats what getting older is I guess. Any way he comes to see me and some mutual friends in the city for a few days. Up until this point I had been in the gym working on making my ass nicer and started really trying to make myself look extra femme in my spare time. I dated a guy for a little bit too. This I not something I had shared with him or really any other non-LGBT friends.

He stays at my apartment. No big deal. He’s staying in the living room, sleeping in my couch. We smoke. He calls it a night and I go to my room. I’m still wide awake so I decide to get dolled up while I’m in there. I o it my make up on, I put on lingerie and start taking shitty photos. I have music playing but not loud enough to disturb anyone sleeping outside of my room.

I hear the door open and I panic. I rush to go sit on the edge of my bed. It’s him. He looks kind of shocked but doesn’t look disgusted or anything. He tells me sorry. And I nervously tell him it’s okay. There’s a short silence. Then I say “now you know, please don’t mention this to anyone, ok?”. He says he won’t and I trust him. He assures me it’s cool with him. Mind you I’m dolled up in lingerie and even though I’m sitting he can clearly see all of me. He then asks me for a lighter and I look through my drawer for one for him. He walks over and gets close to me. He puts his hands on my waist and tells me it’s okay. We lock eyes. He pulls me in and we kiss.

I really don’t know what to think because to me this is crazy. This is not something I would have expected from him but he is kind of a touchy feely person in all the right ways. He starts moving his hands all over me and I’m really feeling it. I get really really hard. I’m ready to go and I rub his pants lightly as a test just to make sure he’s cool but I can tell he’s ready to go too.

To my surprise he reaches in my panties and starts stroking me. I’m incredibly hard and leaking. He pushes me back and we lube up. He slides in. And btw he’s like over 8 inch easily. I’m still super hard and dripping at this point and he starts pumping in and out. This goes on for a bit. I tell him I want to go cowgirl.

He’s on his back on the bed and I slide him in. I’m on my knees riding his cock. I lift my body up a little so there’s space between me and my ass and high thighs. He starts pumping in and out from below. It feels amazing. Im so hard and I want to cum so badly. I start stroking and he starts going really concentrated and fast pumping from below. I’m getting closer and closer. I’m stroking faster and faster and I can’t help but moan more and more. I can feel I’m about to cum. I start cumming. It starts shooting out. Some of it hits his chin. I keep cumming and it’s getting all over his chest. He’s still rapidly going in and out. Everything feels amazing and I’m still cumming a little bit. I keep stroking for what feels like an eternity for an orgasm and finally I can feel his dick start to pulsate. He starts cumming inside of me and it feels so warm. I’m still cumming while this is happening. Finally the orgasm does down for me while I’m still stroking and he’s slowing down. He’s covered in my cum. And I’m filled with his.

Some of the best sex I’ve ever had. Honestly I think part of that is because the situation was so interesting. Anyway we’re still friends but I haven’t seen him for a few years now. We talk a lot but not about this stuff lol.

In another life I think we’d be married but things just can’t work out that way.