Surprised By Her Preparation



What’s your gender? Man
How old are you? 70
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Manchester
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retired
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? 0

Surprised By Her Preparation

How long ago did this hookup happen? 35 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? The hookup was inevitable but because L had just turned 18, it was still something of a surprise when it happened. She belonged to a musical group I was running at the time and clearly wanted to have a relationship with me. One day, a family friend came to dinner with us and L was also invited along. At the end of the evening, my wife surprised me by volunteering to drive the friend home (a round trip of 40 minutes at least) which left an opportunity for L and me to get together. L was slim, petite, almost flat-chested though her nipples were huge when she became aroused. She didn’t need to wear a bra and because it had been a warm summer day, that night she was wearing just a thin cotton blouse and a long, full skirt.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once my wife and our friend had left, L and I started passionately kissing and fondling each other. As I caressed and pulled gently on her nipples she started squeezing my cock through my trousers. We moved swiftly forward. I slipped my hand under her skirt and she opened her legs to allow me to reach her vagina. L was getting very wet and since it was clear we both wanted to engage in sex, she pulled her skirt up around her waist and pulled her panties off while I dropped my trousers and underpants.

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? Without any further prompting, L lay down on the carpeted floor and spread her legs wide. I knelt between her legs and she reached forward and guided my cock to her vagina. I am uncircumcised and the head of my penis has always been very sensitive. L’s vagina was very small and as she held the end of my cock between her lips she urged me to push hard inside her. The sensation was exquisite but clearly, L wanted more and thrust her hips upwards and almost commanded me to shove my cock inside her. As my foreskin was dragged further back off the head I could feel myself begin to come and told L to hold back. “Don’t hold back, push it and shoot it inside me,” she insisted. Nonetheless concerned that she might be being careless about pregnancy or even trying to get me to make her pregnant, with a supreme effort I withdrew my cock from inside her and shot my seed over her stomach.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? The relationship continues to this day although we have fewer opportunities to sleep together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It led to a very satisfactory mutual relationship

What was the WORST thing about this hookup? Nor coming inside her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? No

What do you think about the Casual Sex Project? Good idea

You have a hookup story to share? Submit it here!