Lost my anal virginity to get over my break up

So… yeah. Still kinda freaking out while writing this. I’ve always been a little curious, but this was my first real experience with a guy and it escalated fast. Didn’t expect it to go down the way it did.

I’m a guy, mostly straight (or thought I was lol), but I’ve always had this quiet crossdressing kink. Never told anyone. Just one of those things I’d think about when I was alone and horny. After a rough breakup earlier this year, I kinda spiraled a bit and finally said fuck it — ordered some panties, stockings, a cute skirt off Amazon. When I put them on for the first time… I don’t know how to describe it. It felt right. Not just sexy, like actually comforting. Like a part of me had been waiting for it.

For a while it was just me dressing up alone, jerking off to sissy captions and stuff like that. I’d take pics in the mirror but never posted. I’d make accounts on apps, flirt with guys, then ghost them the second they wanted to meet. I just didn’t think I’d ever have the balls to actually go through with anything.

Then this one guy — older, chill, very confident — messaged me and something about the way he talked just got to me. He didn’t even come off horny right away. Just said I looked pretty in my pics and that if I ever wanted to “be treated like the girl I am inside,” he’d be gentle with me. I was like... holy shit.

So yeah, after a few days of talking, I finally agreed to meet. I told him I’d just give him head, nothing more. He was cool with it. I got dressed — red lace thong, thigh-highs, little black skirt, even did a bit of mascara and gloss. Covered it with a hoodie and left the house shaking lol.

When I got to his place, he opened the door and just said “Wow.” I felt exposed and kinda embarrassed but also insanely turned on. We sat down for like 2 minutes before I got on my knees. I was nervous as hell, hands shaking, about to go down on him — when he stopped me, pulled me up and said, “You don’t have to act. I know what you really want.”

I swear, I froze.

Next thing I know, I’m bent over the armrest, skirt pushed up, thong pulled aside. He kept asking if I was okay — and once I said “yeah”… he took me. Like, really took me.

Started slow, but once he was in, it was like something snapped in both of us. He was calling me his slut, his good girl, moaning in my ear while railing me hard. I was gripping the couch like my life depended on it, face buried in the cushions, moaning like I’d done this a hundred times. I didn’t even touch my dick and still came like a geyser. No joke. It was insane.

After, I was just lying there in a daze, makeup smeared, thong soaked, legs like jelly. He kissed my shoulder and said I was beautiful. I honestly didn’t know what to say.

Still processing all of it. I didn’t think I’d actually enjoy being fucked like that… but here I am, lowkey wanting it again