What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? atlanta
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business Consultant
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? None

I Hooked up with My Wife’s Sister

How long ago did this hookup happen? 6 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

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 was the sister of my wife. We will call her Susan. Susan and I have known each other for years prior to our hookup. Our families were very close. My older brother was best friends with her older brother, I was dating her sister and she was best friends with my little sister. I started dating her sister when I was 15. I met Susan when she was about 10 and married her older sister when I was 20. I never paid attention to her other then the occasional joking around but I always thought she was cool.

At the time of the hook up she was about 19 years old. Had long black hair DD breast and right on the line between thick and chubby. Had a gorgeous smile and full lips.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About 5 months after my wife and I separated (but not divorced) we started to text each other from time to time. It started out innocent enough. Her family hated me for hurting her sister’s feelings and she was reaching out to let me know that she doesn’t hate me. What started out innocent turned sexual when she admitted to having a huge crush on me for years and that she often thought of me while she pleasures herself. After that we started to sext every day talking about the things we would do to each other. I felt extremely guilty but the excitment pulled me in.

One night at around 2:30am she calls me up and she tells me that she thought she could drive home from a friends house but she can’t because she smoked some weed and just needed a place to rest for a bit and since she was close by my place I was the first person she thought to ask. I assumed she was lying and just wanted to find a reason to come over but I agreed to have her over and made up the guest room for her. Up until this point our only contact was through text. It was more of a fun time killer to sext with each other than actually going through with fucking. I few minutes after the call she knocked on the door. We hung out for a bit watching TV and awkwardly talking until I decided to go to bed. I showed her to her room for the night and went to mine.

I was planning on going to bed, beating off and falling asleep. I was in bed for a little more than a hour before I heard my door opening and she’s standing there in her underwear and a tight tank top (no bra). She climbs in my bed saying that the room she’s in is too creepy to sleep in and sorta just told me that she was sleeping here. I laid there nervous because I knew what was about to go down and I was actually trying to talk myself out of it. She laid flat on her back while I laid on my stomach for a few minutes then she took off her tank top and rolled over grabbed my hand and put it right on her bare tits.

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 started playing with her breast, sucking and kissing her nipples as she moaned softly. My hands found their way down to her clit over her panties and I could feel just how absolutely wet she was. She was literally soaking in her panties. While making out I pulled her underwear off and started to rub her clit and glide my fingers in and out of her while she simultaneously softly stroked my penis. She was so wet and turned on I could feel her juices start to leak down to her asshole while I fingered her while occasionally rubbing her asshole. After a few minutes of doing that she got on top of me and straddled my legs with hers and started blowing me. It was messy with a lot of saliva. Just the way I like it.

She then pulled out a condom that she had secretly brought into the room and stashed under the pillow and as she’s putting it on me she telling me how bad she has wanted to fuck me and that she is going to fuck the hell out of me. She then starts to ride me while kissing on my neck. I started to feel her juices drip down my shaft and onto my balls. I then grabbed her and flipped her onto her stomach and started fucking her from behind. After a few minutes of doggy style she starts breathing heavy and her body starts to shake and she starts saying “I’m cumming” over and over again.

As soon as she cums I flip her back on her back and we fuck missionary for awhile until she cums again. Since its hard for me to cum while wearing a condom she takes it off and gives me a blowjob and lets me finish in her mouth. Immediately after she curls up under the blankets and falls asleep as I’m laying there trying to figure out what the fuck just happend.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? The next morning was awkward. She woke me up and she was fully dressed and told me that she was leaving. I walked her to the door and as we got there she looks at me and says “we go to our graves as the only two people to know that this ever happened” I smiled and agreed and she went on her way. For awhile afterwards I struggled with the guilt of what happened and reached out to her after 2 weeks of no contact. She explained that she has no regrets about it and would actually like to do it again soon. I was not on the same page and that we could never do it again. We still keep in touch to this day and we often recount what took place that night. She admitted to planning the whole thing to go down and said that she wasn’t even drinking much that night. She also told me that she still masturbates to that night.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? 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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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? My brother (her brother’s best friend) he called me an idiot and asked me how was it.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some 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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? Although my wife and I didn’t get along towards the end of our relationship she didn’t deserve for me to bang her sister

What was the BEST thing about this hookup? How into it she was. The moans, the dirty talk and hiw wet she was.

What was the WORST thing about this hookup? She was my wife’s sister.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Somewhat 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 think under the righr conditions casual sex is a great thing. We’re sexual beings and having the ability to explore wach other bodies sexually is in our DNA and perfectly natural.

What do you think about the Casual Sex Project? I love it. I love the stories.

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