What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
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 occupation? Marketing Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? 2
Trying To Impregnate A Married Woman
How long ago did this hookup happen? 9 years
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? For less than a month
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? Jill was a BBW with a huge juicy ass, an extremely tight pussy, and massive titties. Jill was quite attractive in her youth, but got married, had a baby, and let herself slide a bit.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jill hit me up on POF. I was monogamously dating at the time to the woman who is now my wife, but at that age, I couldn’t get enough pussy to satisfy my primal urges. We chatted on POF and then we exchanged cell numbers, where we BBM’d each other. We sexted like crazy, and we ended up deciding that I’d come over to her house and fuck her. During our sexting, I found out that she was pissed off because she wanted another baby, but her husband had fertility troubles. Even with that, she wanted protected sex, but I went on a mission to change her mind; I was going to give her the gift of life! We continued to sext, where I told her I’d cum inside her multiple times. She told me that was super hot and got her going. We booked a time to hook up when she was ovulating.
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? Jill’s husband worked in sales as a road warrior, so there were lots of weeknights available to fertilize his wife. I went over after midnight, and she let me in. We proceeded to her marital bedroom, where she invited me into bed. I was on her husband’s side of the bed, all the while her 2-year-old son slept in the next room. We got naked, and I began to eat Jill’s pussy and finger her. She was really tight, and I knew I was going to have to loosen her up. Jill then sucked my dick and got me nice and hard, where she begged me to fuck her. She had second thoughts about unprotected sex and getting pregnant by another man. I advised Jill that either way she was going to get a deep dicking and the decision was 100% hers, and if she wanted me to use a condom, I would. I knew that she wanted me raw and my cum inside her, and I was right. Jill said you can fuck me without a condom. Jackpot! I got her in all fours and mounted her glorious pussy doggy style. Jill was VERY tight, and it took me a number of strokes to open her up. Jill’s pussy was very responsive, and I came right away. It was very quick and didn’t last long. We slept a bit and then I woke up to Jill sucking my cock to get me hard again. I fucked her again, and this time was a better fuck. I came inside her again, gave her ass a spank, and thanked her for letting me fertilize her pussy. I went home to sleep soundly while she pushed the cum deeper into her puss with her fingers.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than 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? She got all freaked out about what she had done the following days. Jill was very conflicted between her primal urges and social norms. She got pissy with me and the relationship eventually petered out.
I ran into her at a wedding party a few months later, and she wouldn’t talk to me at all. I ran into her in a pub three years later, and she gave me the stink eye. I know she couldn’t tell her friends about what happened, as she is the slut police in her friend circle. Funny how that happens.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Jill wanted to have another baby, and I was selected to do that.
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? 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? Never told anyone. Me and Jill’s secret.
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? A little bit
Did your partner get emotionally hurt as a result of this hookup? Very
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? The opportunity to impregnate another man’s wife.
What was the WORST thing about this hookup? That I wasn’t able to impregnate her. And I wanted to fuck her more.
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? Fairly positive
All things considered, how NEGATIVE was this experience? A little negative
Anything else you want to add about this hookup? It was a great experience for me. I don’t care about Jill’s feelings. She’s the one that asked to be fucked and gave me the green light to cum inside her.
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? I think that society needs to be more open to it. I want to participate in casual sex again. I love hearing Katie and Beck’s sex stories of two young women into older gents. It’s reviving me to chase down some young women to have casual sex with.
What do you think about the Casual Sex Project? Thanks for your work.
You have a hookup story to share? Submit it here!