by holo

Gender: Male
Age: 39
Race/ethnicity: White
Current location: Iowa
Highest education received: College degree (eg., BA, BS)
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Open
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 0

Cross Dress Anon

How long ago did this hookup happen? 1 year

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Random hookup

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was a very fit, serious, 30s male, met on craigslist
seemed intense, but hot and interested in what I wanted

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I posted on CL a pic of me in some panties and a pushup bra looking to makeout, suck a cock and get fucked. He messaged back and we exchanged pics.
I put a slutty nurse costume and a hot wig on and drove to near his place. I walked the last block. He left the sliding glass door open, and I just let myself in.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I walked in. He said “nice”. He was a bit taller than me, standing in the living room of a condo, very fit, hot body. Wearing only an open bathrobe. His cock was hard, about 7″. I walked up, head down. He was breathing hard. I was surprisingly calm.

I gently took his cock in one hand, and then kissed him. He kissed me back, hard. Felt for my cock. He rubbed my chest, in the bra. I got on my knees and licked, then sucked, his cock while he stood. He was gentle, but firm. I sucked him slowly, and played with his balls. He was moaning. We’d emailed and I said I was noisy. He was ok with that.

After a few minutes of sucking him, having him gently mouth fuck me, I stood up. I unzipped my naughty nurse and said, “do you want to fuck me baby?”. He said “yeah”.

He pulled a condom out, and I put it on him. He had some K-Y jelly in his pocket too – we’d emailed about this – and he lubed up his cock.

I turned and knelt on the couch, and flipped up my skirt. He pulled my lacy panties down and penetrated me, hard. I cried out. He had one hand on my shoulder, the other on my cock. I had one hand on the couch, one around behind me grabbing for him, pulling his cock into me. I moaned and cried out and he pumped away. I lay my head on the couch and moaned and said “fuck me baby, fuck me harder”.

He stroked my cock and I pulled him into my ass. It was only a few minutes, and he came, hard. I slumped over. I had cum while he was fucking and stroking me. He pulled his cock out. I turned, pulled on my panties, and left.

Did you have an orgasm? Did your partner(s)? Yes, from him stroking me and also from having his cock in my ass.
Yes, he came in a condom while he was fucking me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We both claimed we were clean.
He fucked me with a condom, but I sucked him a bit without.

What were your REASONS for having this hookup? I identify as hetero, but I am very turned on by lingerie and also interested in gay sex, though I have zero interest in an emotional relationship with a man. I had never successfully been fucked in the ass. I wanted to do it and be as noisy and nasty as I felt like.

Were alcohol or drugs involved? If so, how much? I was pretty tipsy. No drugs.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I left, no talking. We exchanged “thanks”. That was it.
No future, nothing.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Totally consensual.

Do you regret this hookup? If so, why? Not really. I guess it’s pretty deviant, but also feels quite natural. Nobody got hurt, nobody will ever know or get hurt by it, so no, not really.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was hot as fuck. It felt good, we both came, it was consensual.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Not at all negative

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