by NigelR

Gender: Male
Age: 33
Race/ethnicity: White
Current location: Minneapolis
Highest education received: College degree (eg., BA, BS)
Occupation: Property Services Manager
Relationship status: Married
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0

My Girlfriend’s Sister

How long ago did this hookup happen? 9 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand

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? My girlfriend’s sister April is white, brown hair, short 5ft 3 and is good looking. She was 18 at the time and we had seen each other many times before. I had no clue or thoughts anything would happen between us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My girlfriend was out of town for a few weeks. My girlfriend’s sister, April, was staying over at our place (she lived an hour away and wanted to see Minneapolis) and had invited some friends to come with. April’s friends brought over some alcohol (mostly beer) and we all began drinking a bit. Her friends started making out and a bit more, so we gave them the privacy of the living room while we went into the bedroom. April laid down on my bed and I did too. Hearing them made me horny and I decided to start making out with April, and she went along with it.

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? We started kissing, then touching, then taking our clothes off. We were naked for a bit, still hearing her friends out in the living room, and I was going to put it in. April said “no we shouldn’t” but also didn’t stop me. We fucked starting missionary, then doggy style. She felt incredible and began moaning pretty loudly. I came and we took a break.

We took a short break, but I also wanted to try anal with her, and she was reluctant. I told her I’d go slow, so she relented. Her sister never let me do her anally.

After, we’d fall asleep naked against each other.

Did you have an orgasm? Did your partner(s)? I had two. She had at least two.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We stupidly didn’t use any condoms or talk about STIs. I had never had an STI and she had a boyfriend as well.

What were your REASONS for having this hookup? I was horny after not seeing my girlfriend for days. Her sister and I were a tipsy and decided to go for each other.

Were alcohol or drugs involved? If so, how much? Just some alcohol. We weren’t wasted but tipsy.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? She felt weird after and didn’t want to talk a lot about it. She said she felt bad about cheating on her bf and her sister.

Personally, I was only worried about getting April pregnant. Other than that, it was pretty fun.

To whom did you talk about the hookup? How did they react? Her friends mentioned it the next morning “You both had some fun!” was what her friend said.

I told a friend of mine. They thought it was crazy to cheat on my gf with her younger sister.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual. I initiated, her sister was a little reluctant but also went for it.

Do you regret this hookup? If so, why? No, other than the potential for pregnancy.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was screwing a teenager (18) when I was 24, and my girlfriend’s sister. This was my first foray into casual sex and I thought it best to use condoms if we hadn’t discussed STIs or anything.

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

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

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