by autosome

Gender: male
Age: 48
Race/ethnicity: British Jewish
Location: London
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: parent
Relationship status: married
Religious affiliation: atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 300+
How many hookup stories have you here posted before? three

The Lingerie Model

How long ago did this hookup happen? 23 years

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…)? one night stand

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? Tall, slim, natural very curly red hair, she did lingerie cat-walk modeling. I can’t remember how we first met but we would bump into each other from time to time and always have interesting fun conversations, such as lingerie modeling tips of the trade. I’ d be cheeky and ask for a back stage pass (I’d always be told “no I know what your like”). She had a light blue vintage VW beatle and a VW Carmen Giha.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We bumped into each other at lunch time, and we’re going to go somewhere for coffee and a bite to eat. We were in her beatle driving round looking for somewhere. 

We ended up close to her flat and she suggested rather than spend money, why not a glass of wine and some fruit at her place.

It was a sunny but cool day and we were sitting at a table on her balcony overlooking the street. She was wearing a long split skirt and as she crossed her legs she flash a beige hold up stocking top. I remember it distinctly as the top had rolled over and was showing the white elastic.

She was pretty comfortable with people looking at her body and took her time adjusting it. I said to her how sexy that looked and she commented that she adjust stuff like that so often that she doesn’t notice. She then asked me what was about it that was sexy.

I explained that watching a gorgeous woman adjusting sexy stockings, flashing her thigh was very arousing. The conversation turned to how aroused I was and then touching, kissing and then into her bedroom.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The sex was fun, good. She had a gorgeous body. She hadn’t shaved all her pubic hair so there was a wideish strip of gingerish hair. We had rather athletic sex but I think she faked her orgasm, as she thrashed about a lot and made a lot of noise.

We cleaned up, finished the wine and she gave me a lift back.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms, she had them in her bedside table. I also knew from previous conversations that she was taking the pill almost continuously to prevent periods getting in the way of bookings.

What were your REASONS for having this hookup? We were enjoying each others company and it seemed to be a natural progression.

Were alcohol or drugs involved? If so, how much? Some wine about a glass or two.

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? We went our separate ways, bumped into each other from time to time. We never had sex again because all the subsequent times we met either she or I was with someone.

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? Yes

Do you regret this hookup? If so, why? Not at all

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 very good sex with a very attractive woman, we enjoyed our company and had fun.

The worst thing was that when a few other women I knew found out (not from me I might add) they got angry and jealous and made a few snarky comments about her, which I thought was wrong as it was a private thing.

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

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