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What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? 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

Work Fuck Buddy

How long ago did this hookup happen? Ongoing

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 less than 6 months

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? Short, brown haired, MILF, married with kids. We became friends through work. She was very sweet and caring. Always looked out for me and helped me in any way possible.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We began exchanging texts and she would complain about her husband. At times she would jokingly say she would leave him and find someone better. She told me about how abusive he was, etc. As time went on, our texts got bolder and we got even closer. Not sure how it happened, but one day our texts got sexual. We both began sending daring msgs which led to making out at work. I wasn’t working that day but I drove over to see her and met up. I had won a dare and she had to give me a welcoming hug and kiss. At first, she was shy and hesitant but after a few shy attempts, we made out.

Fast forward a week later, we finished work late and we both walked to our cars together. I asked to hang out with me for a bit and she agreed. She knew why because the night before I told her I was going to fuck her and she believed that I wouldn’t dare.

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 we got into the back seat of my car, we began talking. We sensed each other’s nervousness and I leaned forward and kissed her. Our tongues played and I began guiding my hand into her blouse. Her tits were just perfect, nice and firm.
There wasn’t much talking at this point. More of seeing how far we’d go. After breaking the kiss and getting on top of her, she looked into my eyes and asked what I was about to do. I responded back by opening my trousers and pulling out my cock. I saw her eyes widen with shock and amazement. At the same time, she was shaking. We both were, to be honest. I began rubbing my cock on her pussy lips gently and she let out a light moan. She asked what I was doing and I explained I’m just going to rub my cock on her pussy only. She let out some small moans and as her breathing got heavier, I penetrated her with one strong stroke.

Her head flew back in ecstasy and she clenched onto my arm hard giving me assurance that she wanted more. She was tight for a MILF with kids and I expected her to be a lot looser. It felt as though her pussy was a vacuum as my cock was being sucked backed in each time I pulled away.
As I began reaching my point of explosion, I asked where she wanted it. She responded back saying it’s safe to come inside as she had the cup ring put in. At that moment, I emptied my cum inside her with no hesitation.

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? This continued regularly on for the next 2-3 years, even after I changed jobs. We still meet up about 3 times a week after work.

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

What were your motives for this hookup? Fun, pleasure, horniness, I was feeling lonely, Making new friends, Just happened, I don’t know why just went along with it

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? I don’t know / I’m not sure

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Haven’t told anyone.

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? Somewhat

Why do you regret this hookup? She was married with a husband and kids.

What was the BEST thing about this hookup? Fucking my first MILF

What was the WORST thing about this hookup? Fucking someone who was still married

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really

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? No

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

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