What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Scotland
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Arts
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? With prefernece to women
How many sexual partners have you had in your life (including oral sex)? 37
How many hookup stories have you here posted before? 6

Meeting an older woman for the first time

How long ago did this hookup happen? 7 years ago

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than a month

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? Di was a 40 year old single mother I met online. She large with big boobs and brown hair.

During the summer of my 2nd year at university I was staying in a sublet over in the city. All of my friends had all went home and I was the only one still kicking about the city as I lived alone. During this time I started exploring hook-up websites and although there were plenty of women on them, I was reluctant to pay for a membership as I had never done that before. Eventually though I just thought ‘fuck it’ and bought a one month subscription to an adult dating website.

After a few messages but nothing concrete back, I was messaged by Di, who lives in a village not far from the city. We started talking and exchanging pictures. Once my membership ran out we kept chatting over MSN IM (who remembers that one?). It was very back and forth over the summer, sending each other dirty messages and making a plan to meet up. However we were both really nervous and it showed. One time we got into a fight and I thought it might not happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day I had some time off and remembered Di was free so I messaged her making small talk and something along the lines of ‘If you still want to meet up and have crazy sex I’m still up for it.’ Smooth.

Well, it worked. She agreed to pick me up at the train station while her son was at school and head back to hers for some daytime fun. As I got into her car her first words were ‘Oh my god You’re so young’ while laughing. I was 22 at the time but clean shaven, and when I shave I tend to look like I’m 17 or something. Basically I agree, I look young.

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? We drove to her house and I’ll admit I was absolutely fucking terrified. I sat on her couch while she sat next to me on the armrest, and I found myself suddenly looking at her DVDs and thinking I should go home. That moment she leaned forward and kissed me. I enthusiastically reciprocated, and suddenly all awkwardness was gone.

We went up to her room and I quickly undressed her, giving a lot of attention to her boobs (they were the first pair I’d had all summer). We fooled around in various stages of undress, and she started giving me a blow job, which felt better than the last ones I had had. She even put my dick inbetween her tits (which was new) and started grinding it. She asked how it felt to which I replied playfully ‘It feels like there’s tits around my dick.’ I asked her how it felt and her response was ‘It feels like there’s a dick inbetween my tits.’

We decided to just go for sex since that was what we both really wanted. Always one for foreplay I started fingering her as soon as I could. She told me she sometime’s found it difficult to cum when someone else was pleasuring her – but that didn’t last and she came over my fingers quite surprised.

At this point I just wanted her so we got my condom out and I entered her missionary style. It was awesome, first time having sex with an older milf and I made the most of it. Slow, then fast, I fucked her like someone who hadn’t been laid in months, which was true.

We fucked doggy style and inbetween moans she said ‘I can feel your balls banging against my clit.’ ‘Is it good?’ I said. ‘Interesting.’ She replied. She still came, as did I.

Afterwards we lay in bed fondling each other a bit. My thighs were sticky with the secretions that had come out of her. As it was getting later in the afternoon she offered to make me something to eat before I went home. Steak, chips and eggs. I wasn’t about to pass that up.

She showered before me and then I showered. We kissed a few more times as she was making me something to eat, and afterwards she dropped me back at the station. And then she went to pick up her son from school.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 felt great. It had been a good experience overall. I would have been happy for a repeat but after replying a few times Di never got back to me so I let it go.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? A few friends, who were shocked when they found out I’d fucked a 40 year old milf. They were jealous.

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

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? Getting to have crazy sex with a milf and getting dinner cooked for me afterwards.

What was the WORST thing about this hookup? Nothing really.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve been with a few girls in the past who say it’s usually difficult for them to orgasm with a partner and the majority of the time they end up cumming from what I do to them. So that’s a nice ego boost. Casual sex is awesome.

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? I think casual sex is great and more people should do it, as long as they’re open to it.

What do you think about the Casual Sex Project? I think it’s a great website with great stories and good for educating youself on the culture of casual sex.

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