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What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Auckland, New Zealand
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business Owner
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 32
How many hookup stories have you here posted before? 0

The Filthy Airline Stewardess

How long ago did this hookup happen? 15 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? Michelle is and was gorgeous. A 5’2″ airline stewardess with amazing D-cup breasts, an incredible ass, and beautiful tanned olive skin.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been friends for years, but nothing besides flirting had ever happened because one of us was always in a relationship. That situation changed just before I was moving overseas. I called Michelle up and invited her to my place for a few drinks. She arrived looking stunning in tight white pants that highlighted her ass as well as a tight top. After a few hours of drinking, the chat turned to personal grooming. I told her nothing turned me on more than a woman who was waxed and smooth. Michelle smiled, stood up and undid her pants. “I take care of myself,” she said with a wink. She showed me how smooth she was. My jaw hit the ground. I stood up, licked my fingers and gently rubbed her pussy. Michelle giggled, smiled at me and pulled her pants up again and sat down. At that point, I had a fair idea she wasn’t going home that night.

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 continued talking and flirting as we drank. Michelle told me she was disappointed because she thought I had a jacuzzi and that she’d brought a bathing suit. Sadly I didn’t have one, but I told her I’d love to see her in the bathing suit anyway. She said that could be arranged if I was in only a pair of board shorts. I agreed and we both went and got changed.

When we both came out it was clear we both liked what we saw. She started stroking my biceps and I ran my fingers over her thighs. She admitted she’d had a colorful sex life including threesomes and being treated like a slut. I leaned in for a kiss and said: “I think you need to be my whore tonight.” She groaned in agreement. I slid my fingers between her legs, pulled her bathing suit aside, and slipped two fingers deep into her wet pussy. She groaned louder and started thrusting against my fingers as I fingered her harder and faster, all the while kissing her passionately. Very soon she came really hard all over my hand.

When she calmed down she begged me to get a condom, so I did. I reminded her that she was my whore tonight and she readily agreed. She knew full well, based on our earlier chat, that she was going to get fucked in the ass. We went to the bedroom and I took off my shorts. She looked so hot in a sexy bathing suit so I made her leave it on. I threw her onto her back as she pulled her bathing suit aside, and I sunk my cock deep into her pussy as we groaned together in satisfaction. Our fucking quickly became fast and frantic. Neither of us was gentle as we pounded each other. I told her what a filthy slut she was. She responded by rolling onto all fours and demanding to get fucked hard in the ass. Who was I to argue? I placed my cock against her ass after spitting in it and gently and slowly entered her. It was insane how tight she was but she just purred and begged to be my whore. After sinking my cock in all the way we fucked slowly at first but gradually got harder and rougher. Michelle reached between her legs to play with my balls and finger her clit until she came again. As I pounded her ass she did say “God I wish I had my vibrator here to fill my pussy as you fuck my ass”. She felt incredible and very soon I needed to cum. She begged me to erupt inside her tight ass and that is exactly what I did. We collapsed onto the bed together and passed out wrapped up in each other’s arms.

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 woke in the morning to the sound of Michelle in the shower. Soon she wandered back into the bedroom in a towel. I smiled at her and pulled back the covers so she could see how hard my cock was again. Michelle grinned at me and climbed into bed again demanding her ass be fucked hard again.

I left the country not long after so sadly never got to repeat it. We did occasionally flirt over text message and did catch up when I came home for a holiday but she was seeing someone. We did kiss and touch a little but nothing else. Both of us have said it was the best sex of our lives and if we’re ever both single again, we’re going to a hotel for at least a weekend and we’re going to ruin each other. Our night together is still fondly recalled by me and features high on the list of ”wank bank memories”

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? 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? Not many. Just a few people when I was overseas

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 felt that we were on the same wavelength sexually. We could both be as filthy/dirty/slutty as we wanted because it was clear the other person felt the same way. It was the most uninhibited sexual experience of my life.

What was the WORST thing about this hookup?  I was going overseas so we didn’t get to explore the possibility of this turning into a long-term relationship.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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? I’ve never cheated on my wife. But I possibly would with Michelle.

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? Casual sex seems ‘slutty’ to me, but that is a good thing as I find slutty behavior a huge turn on.

What do you think about the Casual Sex Project? I enjoy reading the stories.

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