The Weird Guy’s Hot Younger Sister



What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 50, 55-60 if counting oral
How many hookup stories have you here posted before? Tons! This is the only place where I get to organize my thoughts and stroll down memory lane.

The Weird Guy’s Hot Younger Sister

How long ago did this hookup happen? 10 years ago

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

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a week

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 was a junior in college and had finally broken down and agreed to “seriously” date a girl who I had been fuck buddies with for about two years. Big mistake. I couldn’t stop going after other girls!

Anyway, in some of my courses, there was a guy who was- well, really weird. My best friend from college and I sort of got stuck with him for a group project. He would use phrases like “dope” and “bomb diggity” in really emphatic, serious ways, like he was trying to fit in but had no idea how to do it. My friend and I were nice guys (despite how we treated women) so we treated him with a ton of respect and actually became decent friends with him. He loved to throw parties; unfortunately, not a lot of people showed up. In an effort to make him feel good about himself, my friend and I would get a bunch of people to go to his parties with us and we all would wind up having a pretty good time. This became a thing. Once a month or so we’d all get together and help “Crazy Dave” throw a party.

Toward the end of our junior year, Crazy Dave told us how his sister was going to be enrolling in her first year of university and joining us at his parties. Naturally, my ears perked up. Crazy Dave may have been a bit weird, but he wasn’t a bad looking dude; maybe his sister would be cute? It was time to do some detective work.

I went to Crazy Dave’s Facebook page and found his sister. Damn. Hot damn. Holy hell. She was an “alternative” “surfer” “rocker” type of girl. She had a long board, surfer style, and super cute face. She had light brown hair, hazel eyes, and big pouty lips. Damn, she was cute. I knew immediately that I wanted. There was just one problem: she had a boyfriend. I hoped to myself that they would break up by the end of the summer, put her in the back of my mind, and didn’t really think about her again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At the beginning of our senior year, Crazy Dave was really excited for my friend and me to continue the partying tradition we had developed. He was also really excited at the prospect of his sister bringing along her freshman friends for all of us to hook up with.

At the very first party, I met his sister. I played the nice guy roll, acted completely respectful, and kept a close eye on her to see if she’d check me out or give me any signs about being into me. The night went on and I wasn’t getting any signs. I figured she just wasn’t into me. Toward the end of the night, “M.” was wasted. She was stumbling and way too drunk. Crazy Dave was annoyed with her and said she was ruining the party. I sincerely defended her. It wasn’t as if Crazy Dave wasn’t known for puking and passing out.

Anyway, when M. started talking about feeling sick, I offered to take her upstairs. I guided her to the restroom and held her hair for her while she puked her guts out. Half of me was doing it because she was my friend’s sister, but the other half of me was still trying to promote a “nice guy” image so that I could fuck her innocent 18 year old tight body.

I didn’t try anything that night since she was wasted; but, then the next party came. At the next party, M. was a bit embarrassed to see me, but profusely thanked me for taking care of her. As the night went on and the drinks got knocked back, she started giving me the eyes. It worked! When the party ended and M. needed a ride back to her dorm, I happily offered to take her home.

As it turned out, her dorm was about 5 minutes walking distance from my apartment, which was right on the edge of campus. Because of the proximity, I offered to make her some food and then walk her home, given that it was so close. She hesitated for a second, probably knowing what I really meant and thinking about her boyfriend, but agreed. At no point in the time I knew her did she ever mention her boyfriend back home (who, according to Facebook, was still her boyfriend).

When we got to my apartment, I made us some PB&Js, we ate, and we went to my room. M. was really shy- again, presumably knowing I was going to put a move on her- and I wasn’t sure if she was interested or just really thinking we were only there to have a snack.

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 decided to just go for it and leaned in for a kiss. M.  reciprocated my advances and we were soon making out. I laid her back, we took one another’s clothes off, and I positioned myself to slide my dick into her pussy. M. stopped me for a moment, asked if I had a condom, and I lied and told her I didn’t. After telling me that she wasn’t on birth control, I told her I had great control and that I would pull out before cumming inside of her. This was actually a very true statement. But once I slid into her….holy hell.

M. had a very large inner labia. It was like nothing I had ever seen or experienced before. She was definitely an “outie,” but what really astonished me was the way her pussy lips wrapped around my dick and it felt like she was stroking my entire cock with each thrust. It was without question the best sex of my life. Out of all of my partners in the bedroom, M. was the only one I ever fucked who could make me cum while being on the bottom of a missionary position. Her pussy was the champ and my dick didn’t have a prayer.

Because of her unbelievable pussy, I had to pull out in what I have to unfortunately admit was less than a minute. I splashed a huge load across her stomach, cleaned her off, and laid next to her to finger her. She was a screamer. She moaned, screamed, gasped, and was one of the most vocal girls I’d ever been with.

When enough time had gone by for me to get hard again, we went back to fucking. This time, I took out my digital camera which was nearby and started snapping pictures (using the flash) in the pitch black. She didn’t mind at all. I put on video mode (which didn’t utilize the flash) and recorded about 60 seconds of audio of her just moaning and moaning and moaning while I thrust into her. I still listen to that audio clip every few months. Anyway, M. had her orgasm, as signaled by her sudden gasp for air and squealing and I gave up before trying to have my second one.

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? Since I was sort of in a relationship, I had to keep M. my little secret. I also didn’t want Crazy Dave to know I was fucking his sister (nor did she) so we did a great balancing act of being platonic friends out in public or at parties…and completely wild fucking machines behind closed doors.

We fucked at house parties, in people’s back yards, on campus, off campus, in my car, in her brother’s apartment, at my friend’s house, and on a sidewalk next to campus. We had great chemistry.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, Intoxication, To feel more desirable, To feel more confident, To cheer myself up, Power / Dominance

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? My best friend from college knew about it. He knew I was sleeping with anything with a pretty face and/or body. So was he. It wasn’t anything unusual so he didn’t make a big deal out of it. Crazy Dave also sort of caught on after a while, but by then M. and I were so secretive about everything, that he never came right out and said it. I think he was just happy that I was making his sister happy, to be honest. And I was making her really, really happy.

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

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I saw a beautiful girl on Facebook during the spring…and wound up meeting her and fucking her that very same fall.

What was the WORST thing about this hookup? Eventually the girl who thought she was my girlfriend came knocking on my door when M. and I were fucking. I didn’t open the door for her, so M. sort of figured out that she wasn’t the only person I was sleeping with. Afterward, the sex became fewer and far between and by the end of the school year, we had stopped seeing each other. It sucked since the sex with her was absolutely mind-blowing, but at the same time, I was graduating and saw no real future with her anyway.

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

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

Anything else you want to add about this hookup? Crazy Dave had a mental collapse. Poor guy legitimately has crazy thoughts which he broadcasts on Facebook nearly every day. I reached out to his sister, but she basically told me not to get involved at the risk of Crazy Dave incorporating me into his delusions.

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