fling

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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? North America
What country and/or city do you live in? Chicago
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
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)? 30
How many hookup stories have you here posted before? 0

Sex with Sister-in-Law

How long ago did this hookup happen? 1 year

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 more than 3 years

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? D. was my wife’s younger sister by 3 years, and had long blonde hair, blue eyes and was fairly slim with D cup breasts. By most accounts, she looked fairly similar to my wife, but had a better ass. I met her when I met my wife of course, but didn’t really get to know her until a few years ago. She’s married as well, and we both had a little bit of a flirty thing going on. I always thought she was cool but never thought I’d ever sleep with her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Everything began after we invited her to come live with us and be a temporary nanny for our kids. Her husband would visit on the weekends. She was a night owl like me, and during the week, we’d stay up chatting. Chatting eventually led to some flirting, which led to an impromptu make out session one night. We both felt a little awkward and didn’t say much about it for a few days. Then one night, my wife, D., and Ihad a little too much to drink. My wife went to bed, but D. and I stayed up to watch a movie. She had the idea to turn on porn. I immediately got hard thinking about it and found something to put on.

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 a few minutes of watching porn, she straddled me and we started making out again. I pulled her bra down to get a better feel of her tits. They were so nice and so suckable. She then started rubbing my cock through my pants, which led me to put my hand down hers and start fingering her pussy. Then she whispered the hottest words I’ve had hit my ear: “I’ve wanted to fuck you since I first saw you.” She then immediately went down, pulled my hard cock out of my pants and started giving me a blowjob. To be honest, her sister was a little better at it, but the taboo aspect of it made it one to remember. After a while, I couldn’t take it and ripped off the rest of her clothes. She did the same. I flung her down on the couch and started going down on her pussy…her soaking wet pussy. Like her sister, she came fairly quickly from oral. That set her off because she immediately pushed me down, got on top, and guided my cock into her still wet pussy. We traded positions for a while until I couldn’t take it anymore and told her I was cumming. She immediately said, “I want you to cum inside me.” I’m sure the fact that she knew I had a vasectomy made that call easier. Anyway, I obliged and shot a huge load inside her while having one of the best orgasms of my life.

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 kept it up for the remaining few weeks she was there, and even tried anal a few times (something her sister hated). After she went back home, we agreed to keep it our secret. I feel guilty of course, but also wish I could keep a relationship with both my wife and her sister.

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), Intoxication, Just happened, I don’t know why, just went along with it, I didn’t want it but was unable to stop it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? The obvious…I don’t want to hurt my wife.

What was the BEST thing about this hookup? The sex. Even without the sister-in-law aspect, it was damn good.

What was the WORST thing about this hookup? The guilt.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little. I’m more convinced that people are not meant to be monogamous.

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

All things considered, how NEGATIVE was this experience? A little negative

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’d like to see society be more open to it. Those that like casual sex tend to be looked down upon. Why? It’s who we are.

What do you think about the Casual Sex Project? Good idea.

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

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