Sex With My Friend’s Little Sister

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 4

Sex With My Friend’s Little Sister

How long ago did this hookup happen? 25 years

What was your relationship status at the time? Single

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

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? J was the sister of a friend of mine. I had never met her before this party.
She was 18 and I was 27. She was about 5 ft 3, 100 pounds, and had practically no tits. She had been in a bad auto accident a little while before this and had broken her neck. She was in a contraption that went around her chest, had 4 posts sticking up towards her head, and a halo looking contraption that connected to hold her head steady. We met at a party that my friend was having. There were several girls there and I had been making out with many of them through the night. I was about to leave when J came up to me handed me a slip of paper and said to call her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I called her the next day and set up a date for that Friday. I had planned on taking her to a drive-in movie, but it ended up raining. I told her what I had planned and she said: “that’s ok we can find someplace else to do it.” I figured she meant fucking but we hadn’t talked about anything like that. I suggested my place and she said sure.

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 got to my place and when I let her in the door she turned to me and stuck her tongue down my throat. I grabbed her by the ass and lifted her off the ground and carried her to the bedroom. I placed her on her back on the bed and she began undressing immediately. I stripped off my clothes and laid on top of her with my now hard cock between her spread legs. We continued to make out with her holding my ass, pulling me into her and my hands trying to play with her tiny tits.

I gave up on her tits, slid down between her legs, and started eating her pussy. I slid a finger in while I played with her clit. She came pretty fast. I put my cock near her mouth and she grabbed it and sucked the head into her mouth while playing with my balls. She may have only been 18 but she knew how to suck cock. I was getting close but wanted to cum in her pussy so I pulled away and went back to eating her out. I got her off again and placed my cock near her wet lips. I pushed in, expecting to meet some resistance but there was no resistance. She was soaking wet and wide open. I pushed all the way in and it felt like I could only hit one wall of her pussy at a time. She was definitely the loosest pussy I have ever been in. I began to work up a rhythm, fucking her loose pussy, and after a long while, was able to fill her with my cum.
We played some more and she got me hard again. I ate her pussy more (yes I had just cum in her pussy). I was contemplating having her suck me off, but she said to stick it in her ass. At this point, I had never been in an ass but figured it had to be better than her pussy. I wet my cock with her pussy juice and spread her juices into her tight ass. I pushed until my head popped in and slowly pushed in until I was balls deep. She was moaning and her ass was feeling really tight. I began working her ass over until I came. We showered and I took her home.

How sexually satisfying was this hookup? Somewhat

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? I was okay with it. I think her loose pussy may have been as a result of her broken neck. If her pussy had been as tight as her ass it would have been great and I probably would have called her for a repeat performance

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, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Making new friends, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? 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 gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A couple of my friends

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

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? First time in an ass

What was the WORST thing about this hookup? Loose pussy

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Ready for more

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

All things considered, how NEGATIVE was this experience? A little 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 love it!

What do you think about the Casual Sex Project? Great!

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