Cheating With a Hot Waitress

by Ripper

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? 1

Cheating With a Hot Waitress

How long ago did this hookup happen? 2 and a half years ago

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

How would you best classify this hookup? Short fling

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

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? I’ve been regularly going to a restaurant in my town that serves good western food.
I would go with my ex about once a week.
There were 3 waitresses, 2 of which weren’t hot while the third was, but I didn’t think much of it.

She’s fairly tall and western looking for a Thai woman with brown hair and fair skin. She’s very beautiful, possibly one of the most beautiful girls I’ve hooked up with. She’s 3 years younger than me but I didn’t know anything about her till we started seeing each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night I was at the bar with some friends when this girl approached me. Initially, I didn’t know who she was until she told me she was the waitress from the restaurant and the penny dropped that she was the hot one. She asked about my girlfriend as she wasn’t with me and I told her she doesn’t go out because she’s boring and we always argue.
The waitress was super flirty and we hit it off well. We didn’t hook up that night but did exchange phone numbers.
The next weekend I was at the same bar and she came again. We stayed talking until closing time. At some point, the conversation shifted to sex. She knew I had a girlfriend that I wasn’t happy with but didn’t seem to care. She said maybe we could have a one-night stand and soon enough we were back at my place.

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?  First, we showered (Thai habits of hygiene with the hot climate but definitely a good habit) and ended up in bed.
I started licking her pussy. She was perfectly shaven. Then she sucked me off. She gave good blowjobs and I was super horny. Then we ended up having sex without condoms (foolish I know but I was foolish).
We banged in every position I could think of and multiple times though the night. I have a foot fetish and at some point she let me suck on her toes and I blew a load on her soles after she gave me a footjob. Another time we were banging cowgirl with her on top and I blew another load deep inside her.
The more we had sex and the more time we were together that night, the more beautiful she became in my eyes and the more I started getting feelings for her.
This was a problem as I still had a girlfriend.

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 was torn with guilt and confusion. I’d cheated on my girlfriend with a couple of other women but this waitress was the only one I got real feelings for.
I tried acting like everything was ok but I knew it wasn’t.
It gave me the kick up the backside I needed and I broke up with my girlfriend (there was a lot of tears on her part but I knew it had to happen and after I felt a lot better).

I saw the waitress several times after that, we went on dates to the cinema, the beach and restaurants and always ended up back at my place. We had a lot of really good sex and we hooked up for about a month. I was over the moon with this girl.

I had a 3 week trip back to England planned and while there were never promises that we’d be a couple, she said we’d “do things” again when I got back and it was implied. She still seemed really into me.

While I was there we chatted every day for about the first 5 days of my trip, then out of nowhere she stopped. After about a week she randomly texted me saying “Sorry, I haven’t texted you but I’m getting a boyfriend. I hope you aren’t hurt”.

When I told her I was hurt, she said, “But I never said we were going to be a couple. I’m sorry you thought that”. I was gutted.
When I got back to Thailand I went straight to one of my other booty calls and spent 2 days with prostitutes from bars in the hopes of getting over her.

I avoided the waitress because I didn’t want to get hurt. A couple of weeks later, I was at the same bar it all began and she came with some guy in tow. He was a fake tan and muscles, jock type dude who I immediately hated. How could she meet someone and decide to put me on the back shelf so quickly? She hugged me and greeted me like an old friend. My heart was breaking all over again.

A couple of weeks later and I’d gotten over her. I was at the same bar again with another girl who I’d started dating who was hotter and better than the waitress. The waitress turned up with that guy and I can see it’s awkward when she greets me and my new chick. That night she sat at the other end of the bar and kept looking over at me.

A few days later she texted me telling me she’d broken up with that guy, she was sorry she’d hurt me and she wanted to be my girlfriend. I was long over her and into my new chick and it felt good politely telling her no.

I stayed friendly with that waitress after all the drama had blown over and I still am. I occasionally see her and she always hugs me and says hi.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, 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? 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? Told me good friends everything.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Amazing sex and the motivation to break up with my ex.

What was the WORST thing about this hookup? Being hurt myself.

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

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? –

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!