Holiday Hookup

by HornyAlgarve

What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

Holiday Hookup

How long ago did this hookup happen? This week

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

How would you best classify this hookup? Short fling

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? Louise is slim with dark hair and is about 5’4. She has an amazing body, you wouldn’t believe that she has kids! Saw her on her couple’s profile on a swingers site while we were both on holiday in Algarve. As soon as I saw her pics I knew that I had to have her, with or without her husband’s permission, so I messaged them straight away. She answered and we moved over to a chat app. From the start, it was clear that she wanted to be filled with my cum. Interestingly, she didn’t tell her husband straight away that she was chatting to me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After chatting for a couple of hours and swapping a few pics, I started asking her to meet up. She was quite evasive at first, saying it would be too difficult because she was there with her family. I kept up the gentle pressure and eventually, she asked to see my cock. I think it was that which finally won her over because she was impressed with how much thicker it was than her husband’s. I persuaded her to pretend she was going shopping for a few hours and picked her up around the corner from her 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? As soon as she got in the car I knew I was in for a treat. She was wearing a bikini under a very thin dress, and as we drove, she started rubbing her clit through the fabric and telling me she wanted my cock. I quickly found a quiet spot to stop, we got out of the car, and she was straight onto her knees in front of me pulling down my shorts so she could take me into her mouth. It was amazing watching her try to fit my whole cock into her mouth and throat. I gave her a bit of encouragement by holding her head quite firmly and forcing her to take more. Eventually, she submitted and I face fucked her until I came down her throat.

Then it was her turn and I pulled down her bikini bottoms and found her clit with my tongue. She was absolutely soaked already and I loved lapping up all of her pussy juices. She had confessed that anal play made her cum hard so I slid two fingers into her pussy to get them wet and then slowly pushed them up her arse while I sucked hard on her clit. Her reaction was amazing, I thought she was going to pass out, and her arse was contracting so hard I was worried about getting both fingers back!

When she recovered, it was time for the main event. I lay on my back and she lowered herself slowly onto my rock hard cock. She came again when she hit bottom and then started to ride, slowly building up the speed. I found her arse again and she frigged her clit as we fucked her to another huge orgasm. She was exhausted after that, but she still wanted my cum inside her. I got behind her and pounded away doggy style for another ten minutes, during which she had a couple more small orgasms. I then warned her that I was ready, just in case she changed her mind and she started begging me to fill up her cheating married cunt with my cum. This dirty talk sent me over the edge and I exploded a huge load inside of her. She quickly put on her bikini bottoms to contain the mess I had made, then sucked me clean and asked me to drive her back.

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? Dropped her at her hotel, where she was walking funny because of the hard fucking and the cum leaking out of her. She told me later that she made her husband fuck her with my cum still inside her. We are still messaging and I am hoping for a repeat performance before our holidays are over.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Making new friends, 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? 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? Nobody, she told her husband.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Bareback sex with a hot married slut.

What was the WORST thing about this hookup? She lives far away from me in the UK so this will be my only chance to fuck her.

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? We have had some fairly hot chat since and I am hoping it continues after holidays, even though we won’t be able to meet again.

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? Love it, just make sure nobody gets hurt.

What do you think about the Casual Sex Project? Great

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