What’s your gender? Woman
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Perth
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? ~
How many sexual partners have you had in your life (including oral sex)? Probably 30+
How many hookup stories have you here posted before? 0

One-Night with Her

How long ago did this hookup happen? 30th November 2017

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 more than 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? Let’s call her M. She was the oldest daughter of one of my closest friends. I’ve known M for almost 10 years. She’s grown to quite an amazing beauty, nice bum, 36C boobs. She’s 32, recently married.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? M was always a curious one. One night while we were shopping she mentioned to me what it would be liked getting fucked by a strapon rather than her hubby’s dick so I thought to myself, I’ve always wanted her. Immediately brought her to an adult shop, picked a dildo and a strap and went back to my hotel.

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? Push her on the bed, pulled down her shorts. I wear the strap and just gently penetrated her clit and there it was, the first time I fucked a woman more than 25 years younger. She wasn’t the type who enjoyed going down on women, especially someone my age. But she basically enjoyed the strapon fuck and myself going down on her pussy.

Had her all including her anal virginity for the first time. She tasted amazing and we definitely set another date.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? She stayed the night. We fucked again the following day and the day after before we flew back to our husbands. We kept this to ourselves.

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, Attraction to partner(s), Hoping or expecting it would lead to something more, Power / Dominance, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? 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? Shared it with a long-term female friend of mine. She was supportive of me and told me to enjoy myself while I still could.

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? I’ve always wanted to have her. Known her for more than 10 years, each day thinking when will that day come that I could have her.

What was the WORST thing about this hookup? She wasn’t the type that would eat another woman out, especially me since my age and appearance wasn’t her cup of tea. She’s definitely still straight.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, it hasn’t.

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

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

Anything else you want to add about this hookup? Probably for others out there, go out there get what you want before you’re too late.

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? Nothing

What do you think about the Casual Sex Project? I’ve read a couple of lesbian, bi, gay stories. Really enjoyed them. I’m married to a guy but have always preferred sex to a woman. Reading their stories always get me on the mood.

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