Shortly after graduating college I was still dating a young freshmen. She grew up in this insanely strict christian home and had never had sex. She said for home school prom night the boy rubbed her pussy under her dress and that was it. No other man had so much as ever seen her naked before me.

I was the first to take her top off, the first to see her tits and the first to finger her. On this particular occasion I was the first to see her completely naked.

She was a bridesmaid in a friends wedding and had a few too many classes of champagne. Afterwards I took her back to her hotel room and we started making out. She's being insanely aggressive. Like loosing her damn mind.

I unzipped her golden bridemaid dress and watched it hit the floor. All she was wearing was a strapless push up bra and a pink thong. After much more making out she naked and so am I. She fumbles my dick in her hand and I try to coach her on how to stroke it.

Next thing ya know she's on her back laying on the bed. I can tell she's sick and drunk, but she keeps asking for it. Standing between her legs I put the tip of my dick at the mouth of her pussy. As I push a little I can tell it's tight as fuck, but to my dismay she's basically passed out by now.

To this fucking day I can remember exactly what her virgin pussy looked like. It was the sexiest, tightest fucking pussy you could imagine.

So I flip her over and literally jerk off on her ass. A few hours later she's up and sick, and I help her get in the shower. Afterwards she wears nothing but one of my t-shirts and we spend the night snuggling and fingering her a bit.

In the end a part of my regrets not fucking her. We'd been talking about it for weeks and she had already gave me permission, but it still didn't feel right. I didn't want her to wake up having lost her virginity and not remember a damn thing.