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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? canada
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
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)? 12
How many hookup stories have you here posted before? 4

A day hike like never before

How long ago did this hookup happen? 2-3yrs

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For more than 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? She was about 5’5″ 130lbs, redish brown dyed hair with brown eyes, very small A-cups but had legs and an ass to die for, she was a single mom but had a very active lifestyle so her body was very fit. I knew her pretty well, we lived in the same town attended the same school but didn’t get to know each other till our early 20s when one of her friends was my at the time FWB, she was always very shy and awkward but we got along pretty well even after i parted ways with my FWB, I found her cute but not enough to pursue anything with her, she just seemed to always have walls up and her baggage was more than i cared for.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a day hike with friends, i didn’t know she was going to be there until i arrived and i hadn’t talked to her in quite a while, there was 8 of us, me being the most out of shape resulted in me at the back of the pack but i didn’t mind, with 5 girls and 3 guys it gave me a nice view of the girls asses as they all wore shorts or leggings. We reached the lake at the end of the trail and when everyone was having lunch she said she wanted to hike to a view point across the lake, everyone declined but i felt a second wind coming so i said I’d join her, as i said she was always fairly shy even though we knew each other, i managed to get some small talk started but for the most part it was a quiet trek, we got to the look out as another group was leaving, the view was amazing, we just sat there for a while not saying much, i asked if she wanted me to take a picture of her and she quickly declined, saying she looked terrible and so on, which i though was absurd and told her it was quite the opposite and she actually looked very attractive, she immediately started to blush and giggle and with a little more convincing let me take a few shots. She came and sat next to me and that’s when she surprised me with a kiss, at first i pulled back but quickly return the gesture.

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 laid back and continued to make out all the while i couldn’t figure out how this was happening, She was always so shy and quiet and in the time i had known her i don’t think i ever saw her with a guy yet here she was making a move. I was pretty blindsided but i was certain i knew where this was going so i started running my hands all over her, her sports bra and leggings left little to the imagination, she started breathing heavily as i massaged her breasts, then i ran a hand down her body to her butt, by now i was rock hard and it was no secret with the massive tent i was sporting, i wanted things to move along so i slipped a hand between her legs and she let out a big gasp, i could feel her wetness as i rubbed so i brought my hand up and slipped it in her pants, she was smooth and dripping wet, she broke our kiss and moaned out “OH FUCK” as i fingered her slit. Finally what i had been waiting for, she went for my raging erection and pulled it out of my shorts, what i heard next was a definite ego boost as she grasped the base she just stared and said “Fuck…..She was right you are big” , we got up and moved to some trees for a bit of privacy. With her leaning against a tree i slipped her pants down and entered her from behind, i was shocked at how tight she was it was actually a bit of a struggle at first but once i was in she felt amazing, as we went at it i got the feeling she wasn’t used to taking it this hard but she seemed to enjoy it, we didn’t have any condoms so i had planned on pulling out but she had a pretty strong orgasm which left her weak in the knees and me holding her up by her waist, with her pussy trembling and clamping down on me it was too much and i came inside her. Once we caught our breathe i asked what happened to the shy quiet girl i knew, she just laughed and said shy girls get horny too.

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? We talked as we hiked back to the group, she explained she usually stuck to other single parents cause things seemed to work out better but her and her regular fwb had been drifting apart and she hadn’t been laid in a couple months, and when we ended up alone she started thinking bout the stories my old FWB had told her, so she decided to make a move. She made it clear she wasn’t interested in dating at all but despite her normal shy personality she still had needs, we agreed to keep it a secret and become FWB.

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

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

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? no one

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? the thrill that we could be caught

What was the WORST thing about this hookup? nothing

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

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

All things considered, how NEGATIVE was this experience? Not at all 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? This situation is a prime example of how casual sex can work, sometimes life can be too busy to maintain a relationship but we still need some form of connection and sexual release. Relationship wise neither of us see it working, but for sex its nice having someone you can be comfortable enough with to just text and say “come over” , you get each other off and go back to your lives.

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