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What’s your gender? Man
How old are you? 44
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Colorado
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 2

Her Big Red Truck

How long ago did this hookup happen? 5 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? 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? Ginger was a young mom who I met through a dating site for married people. We had chatted but never met before this day. She was actually very attractive but had told me that she had recently lost a big amount of weight and was not confident in herself. She was frustrated with her current situation and coworkers had told her about the dating site and were encouraging her to explore her sexuality.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was comfortable meeting in public, so for our first in-person, we decided to grab a coffee. When she walked in, she was wearing a tight black skirt and a red top with a plunging neckline. Her long dark hair perfectly framed her face and her red lipstick was for a night out. She was taller than I expected. We had easy conversation and she told me a little about being unhappy with her home sex life and how the men she worked with knew she was out on a “date” and dared her to fuck me.

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? I was very willing to help her with her dare and suggested we move to one of our cars. We walked out and she offered to show me her big red truck. It was a brand new extended cab truck and she was in a parking garage. She opened the back door and told me to check out how much room it had. She joined me and sat next to me on the leather seats. We began to kiss. Our hands moved all over, but she clearly wanted to keep her clothes on. As my hand crept up her thigh, I found the top of a stocking and then going further, I found that she was not wearing any panties. My fingers found their way inside her wet pussy and she moaned when I rubbed her g-spot. She laid back and put her big black boots up on the edge of the seats and spread her legs, showing me she was shaved bare. I pushed her legs back and licked up her wet juices while I unbuttoned my pants. When she asked me to fuck her, I stuck myself right in and she wrapped her boots around me. She was very wet and loose, but it felt great to have my dick in this hot younger woman. Although she wouldn’t let me take her top off (I think she was still self-conscious and worried she didn’t have the perfect body), I pulled the neckline down far enough to expose huge nipples that I worked on until they were erect and perky. At this point, she began to buck intensely and started the scream with each thrust. Before I knew it, she was squirting all over the place and she couldn’t hold back, soaking both of us and the leather seats. I asked her where I should cum at this point, and she said anywhere, so I pushed hard and deep and emptied my whole load inside of her.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 think she anticipated she would squirt because she actually had a towel and tried to clean up. She straightened things up and drove me to my car. With a kiss, she was gone until our next adventure in her big truck.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

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

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? Very

Do you regret this hookup? Somewhat

Why do you regret this hookup? After meeting a couple of times, I got some odd emails from Ginger that were clearly wanting to “reminisce” about our times together. I finally responded with “say hi to Ginger for me” and the response I got said it was her husband and he knew about all the guys she was fucking (I figured she was finding a lot of fun) he said he would blackmail all of us and that she had a mental breakdown.

What was the BEST thing about this hookup? Was a fun fuck at the moment.

What was the WORST thing about this hookup? Only fucking in a vehicle and not able to ever get Ginger entirely naked. Also feeling guilty that she got caught and was having a hard time.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m more careful with who I hook up with.

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

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

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