Sex with Sister-In-Law



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Some college (not currently in college)
What’s your occupation? Production specialist
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
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)? 23
How many hookup stories have you here posted before? None

Sex with Sister-In-Law

How long ago did this hookup happen? 10 years ago

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? 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? She’s a very attractive woman. I’ve known her since my high school days and I’ve always been attracted to her. She’s short, blonde, curvy and has huge breasts. We have never hooked up before, but we used to flirt in high school. I left for the Navy after high school and when I returned she was married, so I didn’t bother her. I then met my future wife and came to find out she was my high school crushes’ younger sister. I never even knew she had a sister. My future wife looked like my crush in the face but my future wife was tall, chunky, and had no breasts at all.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup took place at a Halloween party at my house. My wife and I had decided to throw a party and invite all of our friends and family. My sister-in-law and I both instigated the hookup, as we were a little intoxicated and had been flirting with each other throughout the night.

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? It happened as the party was getting into high gear, and a lot of people were mingling and having fun. I went out to my backyard to have a cigarette, and my sister-in-law showed up towards the end of my smoke break. She brought me a drink and had one for herself as well. We talked for a bit and she told me she wished she had waited for me to get out of the Navy. I told her I wished she had too. We both admitted we regretted not hooking up in high school, and the next thing you know we were kissing and feeling each other up. She was dressed as little bo peep so it was easy to get under her dress. We moved to a darker part of the backyard and she dropped to her knees and started giving me head. I was soooo hard because I had always wanted this to happen with her. After 10 minutes of head, I bent her over, pulled her shirt down and her skirt up, and took her from behind. Her breasts bounced as they hung out, swinging back and forth as we moved. I felt awesome doing it. I thought I would feel guilty because we were both married, but I didn’t. Based on her moans, she was feeling the same way. She was such a better lover than her sister was. After I took her from behind, and after I came, she dropped to her knees once again to clean my dick off with her mouth. We fixed ourselves up and went back into the party. No one even knew we had been missing for an hour.

How sexually satisfying was this hookup? Very

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? We didn’t talk or see each other for about a week. She and her husband came over for dinner a week later and we acted like it had never happened. About a month later she texted me and said she wanted to talk about it because she was feeling guilty. I told her I didn’t feel guilty at all because deep down I felt like we were meant to be together. She agreed but said she felt guilty because she did it behind her sister’s back. We talked for awhile and by the time we hung up we had scheduled a meet up for another sex session. Lol. She said I’ve been her best yet, and she was definitely my best lover at that time.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, Just happened, I don’t know why just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? I told my best friend. He was disappointed in me for cheating on my wife and continuing to do so with her for a year after that first time. He told me I needed to either leave my sister-in-law alone or divorce my wife and be with her sister.

How would you best summarize people’s reactions about this hookup? Relatively negative

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing about it was that it took so long for us to do it. It was exciting and heart pounding when it happened. I’ve always wanted her and she always wanted me, and when it finally happened after all those years it was like the best sexual experience anyone could ever imagine.

What was the WORST thing about this hookup? I ended up divorced, but I was fine with that because I didn’t love my wife. I loved her sister. However, by the time I was divorcing my wife, my sister-in-law was getting married again. So after my divorce, I was hoping she and I would somehow get together and be together forever, but she met a really good guy and she’s happy now, and so is my ex-wife.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I miss the sex with my ex-sister-in-law, but I’ve had better since. I still miss her as a person though.

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? Nope

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? People are gonna have sex. It’s only human. We were made to be attracted to each other and sometimes urges overcome loyalty and trust.

What do you think about the Casual Sex Project? I think it’s a good place to get things off your shoulders anonymously.

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