Ex Girlfriend’s Sister

by unholy

What’s your gender? Man
How old are you? 42
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 (open)
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? 2

Ex Girlfriend’s Sister

How long ago did this hookup happen? Last Week

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? Some context: I broke up with my ex girlfriend over a decade ago. I hadn’t seen her or anyone in her family since that time, despite living in the same general area. Fast forward to now. I’ve been trying to get back into shape after having a surgery. I’m by no means overweight, but I hate the feeling of being sluggish. Anyway, the local rec center had a great gym with personal trainers for hire. Since I do better in the gym with someone there to push me, I paid for a few months. On my introductory visit, they introduced me to one of the trainers. As soon as she turned around, I recognized her. It was my ex’s little sister. She had definitely grown up (she was 15 when I broke up with her sister)! Obviously, she was in good shape being a personal trainer, but she was also very attractive, much more so than her sister.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first training session was a bit awkward, but we started talking more and more (thankfully not about her sister) and started to hit it off. On the fourth session, she caught me looking at her ass. I thought I was toast! Instead, she proceeded to tell me how she had a crush on me when I was dating her sister and asked if I’d like to get dinner after her shift. After a nice dinner at the local Italian restaurant, we chatted a bit in the parking lot. I was about to leave for the night when she said, “Wait!” I turn around and she proceeded to kiss me and then she asked: “Want to come to my place?”

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 walked into her apartment and immediately picked up where we left off. Soon, I slid a hand between her jeans and belly and started to rub her pussy through her panties. Not long after, she unbuttoned my pants and slid them and my boxer briefs down to my ankles. I soon felt the warmth of her lips and tongue as they wrapped around my cock. Partly because she was so damn good at it, and partly because of who it was, I felt close to coming. “I’m going to come!” She went faster as I came in her mouth. Wanting to make sure I repaid the favor, I immediately took off her jeans and panties and started to go down on her. It didn’t take long for her to come either. I have to say that, like her sister, she was very orgasmic with oral. We rested a few minutes and chatted more about what she has been doing over the last few years. That led to more oral and me telling her that I wanted to be inside her. She shook her head, laid on her back, and guided my cock into her pussy. We switched positions several times before I realized we had forgotten a condom. She told me she didn’t care because she was on the pill (I had a vasectomy anyway, but was always conscious of STDs). I then felt myself about to come and told her as such. She grabbed my ass and pulled me in tight. After a few more thrusts, she was filled with my cum.

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? Over the last week, we’ve hooked up after every workout. She hasn’t told her family yet and I hope she keeps it that way. The strange thing is, I actually feel a connection to her. She’s not nutty like her sister and is actually fun to be with.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? 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? I haven’t told anyone yet

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The connection and chemistry, the fact that it was unprotected.

What was the WORST thing about this hookup? It was my ex’s sister…at some point that will be an issue.

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? Very positive

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

Anything else you want to add about this hookup? Take away the fact that she was my ex’s sister, and this is a meaningful relationship with a great person.

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? Casual sex should be the norm. We as humans are in denial about what we really are: sexual animals.

What do you think about the Casual Sex Project? Love it!

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