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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Asia
What country and/or city do you live in? Thailand
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Teacher
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? –
How many sexual partners have you had in your life (including oral sex)? Around 50
How many hookup stories have you here posted before? None

Cheating with an Asian MILF

How long ago did this hookup happen? 3 years ago

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

How would you best classify this hookup? Fuck-buddies / Booty call

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

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? She was 40 but very small with a body like a 25 year old, small enough for me to carry her with ease. She was Thai so had tan skin and dark hair. She was a single mom to a 16-year daughter who would no doubt be a stunner by now.
I was in a relationship with my ex that I was unhappy in and living in a country that’s basically adult disneyland. I wanted some fun on the side and in secret, I downloaded Tinder and set it as women 18-45 because there’s a lot of really sexy older women in Asia. I matched with her and chatted a bit before planning to meet.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met her at a cafe but we only stayed for a short time before coming back to my place and hooking up almost immediately.

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? She was wild (far wilder than my girlfriend at the time), almost crazy wild. As soon as we got back to my place, we were making out with her tongue down my throat and then showered together before going to bed. I licked her pussy and asshole which tasted great. We had sex multiple times that night. The first time we were together we used condoms and I banged her doggy style then spooned her from behind. She was almost crazy, giggling and laughing during sex. Her English level was low so she’d say things I didn’t understand.
I have a foot fetish and at some point, she gave me a footjob and I sucked on her toes and worshipped her feet while I banged her missionary.
She was very passionate and I was excited at the thrill of sex with another, older woman and the danger of knowing I was cheating made me come fast.
After that round of sex, we had 2 more but I ran out of condoms so banged her raw (she was sterile now) until I couldn’t go anymore. She wanted more and more and I ended up licking her pussy and ass till she came. She ended up sleeping over and we had sex again in the morning before she left.

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? Immediately the next day I felt guilty for cheating on my girlfriend. I ended up cheating on this girlfriend with a couple of different women but this MILF was the first.
She would message me and occasionally sending nude selfies and I saw her one more time while I was still with my ex, about a month after the first time. We went to a short time hotel and had 2 rounds of sex but didn’t sleep together that time.
After, she continued messaging me constantly telling me she missed me and it got too much for me hiding the secret from my girlfriend at the time so I told her I couldn’t see her anymore and she got annoyed and unfriended me on facebook.

6 months later almost immediately after I broke up with my ex, she added me again (she must have been keeping tabs on me) and messaged me. I saw her a few times again and she would stay at my place each time, giving a full night’s worth of great sex. It definitely felt better for the conscience banging her when I was single but there was definitely a thrill to cheating.

She ended up marrying a German guy and moving to Germany. We still like each others posts occasionally, otherwise theres not much contact anymore.

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

What were your motives for this hookup? Fun, pleasure, horniness, To feel better about myself, To feel more confident

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? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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

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? I told my best friend who told me I should break up with my girlfriend. But she was clingy and very controlling and I was a bit scared of her.

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

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The amazing sex.

What was the WORST thing about this hookup? The guilt and hiding secrets

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? –

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

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

Anything else you want to add about this hookup? –

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? –

What do you think about the Casual Sex Project? –

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