Older Woman



What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Asia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Transport
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? 0

Older woman

How long ago did this hookup happen? 20 years

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? Reasonably attractive 38 year old blond lady with glasses. We were in a nightclub which allowed dancing on the tables, I was giving her The Eye and she moved her head to indicate I could join her. After a bit of table dancing, we sat down together and chatted, while we were talking I gave her a couple of quick kisses on the lips which she didn’t object to.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I moved my hand between her legs and she tensed and stopped me going any further but didn’t make me take my hand away. After a short time she began looking at me and I knew I could have her. I suggested we go back to my place and she agreed, one of her friends tried to dissuade her and when she couldn’t, followed us out and took my car license plate number.

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? When I got her home I undressed her in the lounge and led her into the bedroom. We kissed and I went down on her. I got up and tried to put my cock between her breasts, she thought I wanted her to suck it and told me she wasn’t into that. I reached for a condom but she told me I didn’t need it, I asked if she was on the pill and she said she was. I gently entered her and I could see a look on her face which said you can go quicker than that, it’s not that big. She had four children already so I wasn’t straining her at all.

I fucked her for a while and then I saw her smile slightly and realised I was about to cum, I think she sensed it before I did. I could feel myself flooding into her, even after multiple births she was still nice and tight and had a good figure. She seemed to enjoy me ejaculating inside her, I was younger than her, quite good looking and fit from the gym. She probably enjoyed knowing she was still attractive and I don’t think she’d been bedded for a few months.

We chatted for a while and ended up doing it twice more that night, doggie style and then with her ontop.

Next morning I drove her home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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? I gave her my number but she never called me, however a few weeks later I met her again in a different nightclub and ended up taking her back to my place again.

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

What were your motives for this hookup? Fun, pleasure, horniness

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? A little bit

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? My next girlfriend who it turned out knew her, I later discovered that I had bedded another of her friends as well and all three of them knew each other. The other friend had invited me in for coffee when I drove her home in my taxi one night. I decided to be honest in case we ended up all meeting together as it was a relatively small town.

My next girlfriend seemed bit surprised but just told me never to fuck around while I was with her.

How would you best summarize people’s reactions about this hookup? Neutral

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? Bareback sex with a woman ten years older.

What was the WORST thing about this hookup? Her not calling me after I gave her my number.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It gave me confidence and taught me to be more persistent

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? As long as its consensual and both parties know the score it’s fine.

What do you think about the Casual Sex Project? Great way to share experiences.

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