The Sister

by Damien

Gender: Male
Age: 25
Race/ethnicity: Black
Current location: Houston
Highest education received: Some college (not currently in college)
Occupation: School and Transportation
Relationship status: Single
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 25+
How many hookup stories have you here posted before? 0

The Sister

How long ago did this hookup happen? 4 years

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? I met her through her sister. I was in a college dorm and a friend brought her sister by. Lets call her R. R had a boyfriend but for some reason always wanted to chill with me. I tried to hit it but really nonchalantly. I could have if I tried harder. But we hung out a lot because she was cool. We went out and had a few drinks and then she gave me a blowjob in the car. But we didn’t talk for some months and one day she hit me up out of the blue, saying she was bored. Luckily summer ended and I moved into an apartment and my roommates had a little party. R brought her older sister A with her. A was short and thick in the right places. Not fat at all but she had an ass and boobs but a flat belly.  She was maybe 5’2″ with hair to her shoulders. She introduced herself right away.  She was a little older, she was 25 and I was 20. She was just looking at me for a while feeling me out. I’m mature for my age and I guess since I had an apartment I guess I was old enough in her eyes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When R and A came in they went right to my room because they didn’t know anyone at the party. They were kind of nervous because they were the only black girls. We were chilling in my room.  A asked if she could sit I said of course.  By this point R got some drinks in her and A did too. I was drinking as well. R was so drunk she was dancing with the white guys she didn’t even know. Me and A were in my room talking and R came back in and wanted to dance. I put some twerking music on and they both got loose. R told A to twerk on me and I’m like he’ll yeah. We danced for a little bit and she was into it rubbing her pussy through her jeans as the song got slower. R left with an evil grin and locked my door and went back to the party. I laid on the bed and told her I wanted a lap dance.

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? She was grinding on my dick through my pants. I took her shirt off and licked and sucked her breast while she moaned and grinded. She was hesitant at first but she didn’t want me to stop. Then she snapped and kissed me and we got undressed. We started missionary and she was just a load of ecstasy.  She was working her hips with my stroke to get me deeper. She was scratching my back when I hit her gspot. She wanted me to fuck her harder until she squirted, so I did. She squirted twice in about 7 minutes. Her doggy style was amazing. She had the back arch on point. she could throw it back. Let me pull her hair. She was screaming so loud the party got quiet for a second and I don’t think she cared because she just begged me to fuck her harder.  She was little so I was able to put her up against the wall where she squirted again. I eventually came after about 45 mins or so.  She was unusually mad I came in the condom because she wanted it in her mouth.  She asked me to see the condom but I said no cuz that’s weird. We got into an argument and made up and I got a blowjob and gave her what she wanted. The best sex of my life. Her drive was crazy.

Did you have an orgasm? Did your partner(s)? Yeah I came twice, she squirted three and came 4 more.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom. No questions at anything else

What were your REASONS for having this hookup? She was sexy as hell.  Plus I used to want the sister. So kind of a revenge thing. Her sister turned out to be hotter though

Were alcohol or drugs involved? If so, how much? Alcohol and marijuana

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? Argued my way into another blow job.  She came back a week later and we fucked again. Unfortunately her sister and my friend got stupid drunk and blacked out on my couch they woke up naked not remembering anything so that turned really awkward.

To whom did you talk about the hookup? How did they react? My small circle of friends, her sister knew.  The party heard. And R’s boyfriend somehow found out.

Was this a consensual and/or wanted experience for you? For your partner? Yeah

Do you regret this hookup? If so, why? Hell no. I wish she didn’t get back with her baby daddy

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? Best -probably some of the best sex I’ve had. Worst -I won’t get it anymore.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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