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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Perth (at the time)
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Teacher
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 5

Fisting fun

How long ago did this hookup happen? In my late twenties

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? Mandy was a redhead, about 41 – so older than me, given that I was in my late twenties. She had a nice, slim, sexy body. She was divorced and lived on her own.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met on a hookup site. She knew I was in a relationship and didn’t mind. We agreed that I’d come to her house and pick her up, to drive us to the nudist beach. We thought it would be fun to do that, but didn’t make any further plans. When I got to her house, I was pleased to see that she looked like her photo. She was wearing a light dress, and had her towel with her – so we went straight back into my car and left.

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? After we’d been in the car for a couple of minutes, Mandy put her hand on my leg. Then she said some words that shocked and turned me on: ‘The only problem with us being like this… is that I’m going to have to suck your cock!’ With that, she took out my hardening erection and began to suck me. I reached my free hand over to her butt, and worked it under her dress. To my pleasure I found she was wearing nothing underneath. I began fingering her asshole as she sucked me, and before long, I delivered a satisfying load of cum into her mouth. She swallowed it and we kept driving. When we got to the beach, we were a little shy about being seen by other people. We got naked and went up to the dunes to get some privacy. She began to suck my cock again and soon I was hard. She got on top and we began to have sex, but we were soon disturbed by other people. One man set up his towel in very close proximity, so he could watch! We kept going for a while, but then decided to go for a swim. After this, we drove back to her house.

At her house, she put on some porn, and we had sex in numerous positions. I came heavily in her pussy. She then guided my hand to her pussy and instructed me to fit as many fingers in as I could. She writhed around in pleasure as I managed to fit four fingers inside her, thrusting them in and out of her soaking wet hole. After a while, I tried to add my thumb, and eventually my whole hand was completely inside her. This drove her wild, and she had a series of orgasms. When she recovered, she asked if I’d like to try double penetrating her, with the help of a dildo. I excitedly agreed. She bent over and stuck her dildo in her pussy, while I entered her ass. I pounded away for quite a while, and was amazed at how sexy this experienced woman was. Unfortunately I didn’t cum in that position, but after a while we decided it was time for a shower. We went into the shower together and as I lathered her body I found my erection growing again. She pushed me down and sucked me hard until I came in her mouth.

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? We hooked up a couple more times, doing similar activities. She never wanted to kiss though, which I found a little strange, given that we did everything else. After a while I decided I wanted to try to work harder on my marriage, so we stopped.

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, To feel better about myself

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? No one

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? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Somewhat

Why do you regret this hookup? I was married, and tried to seek affection outside because I didn’t feel it inside the marriage.

What was the BEST thing about this hookup? The car experience, fisting, anal

What was the WORST thing about this hookup? I was married

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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

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