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What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Massage Turns Serious

How long ago did this hookup happen? 2 years

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 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? We had been friends for a while. I was never really attracted beyond friends. There were hints she would have liked to be more than friends with me from time to time

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At her house. No planning, just happened.

I was pretty inexperienced. I had slept with 2 other girls before her. But both were very short-term and I had no idea what I was doing really…probably had sex a grand total of 5 times before this. I was so inexperienced the 2nd girl I slept with had to put my dick in because she could tell I couldn’t find it.

Girl in this story knew all of my history…inclusive of all the details of my sexual encounters…like not being able to find the hole.

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 had a 5yo kid with another guy. I used to go around to her place on weekends at night to watch movies etc. We’d sometimes end up play fighting, throwing pillows and things. I do admit occasionally during these tussles letting a hand feel a boob or two, she never minded that much. I’d stay the night sometimes and just sleep in the bed with her and that’s kind of how things happened.

I was giving her a back massage this one night. Because we were using massage oil she’d taken her top off and was just lying face down in a pair of underpants. I’d massaged her lower back and top of her bum pulling her pants down slightly while doing it. We’d done this lots of times before so no big deal. I then rubbed her legs sitting between them. When I got to the top of her legs I accidentally put my fingers on to her pants between her legs while changing from one leg to the other. This was a genuine accident and when I realized where I was I pulled my hand away. I expected her to move or say something but she didn’t so I kept going down her leg. I was suddenly filled with young adult male horniness and started thinking all kinds of things and wondered if she really didn’t mind being touched there and if I could push it as far as at least touching her vag. So I decided to test things out and massaged back up her leg and touched her again. And again no protest was made. I touched again, this time longer and clearly deliberately she giggled slightly into her pillow. I took this as her being fine where things were headed, so I ran my hands up her back and down her sides and when I reached her pants I attempted to remove her underwear completely… She lifted her hips and they came off. She turned over we started kissing feely touchy fingers going everywhere. I’d actually achieved my goal by this stage which was to just have a good curious look at her vagina (previous encounters had been lights off) and to finger her a bit. But things kept going. By this stage, my clothes are gone and she went down on me like I’ve never had since. At some point, she stopped, and said that she’d take care of everything from here. She mounted me and there we stayed for a good while, her in complete control on top.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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 did it again in the morning, next afternoon and night. For a few weekends after we went at it regularly.
Strangely, the last time we did it, she called me to her house, answered the door naked and asked me to take my clothes off as I came in. We had dinner together then had sex. The next morning she said we should stop because she knew I didn’t want any serious relationship with her. It was respectful and we both moved on. We were never as close of friends after that and soon after we both moved towns.

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

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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

Do you regret this hookup? A little bit

Why do you regret this hookup? Friendship wasn’t as close after

What was the BEST thing about this hookup? For a while, it was anything goes. Pretty much it bacame just walk up to that person and start taking clothes off and it was reciprocated

What was the WORST thing about this hookup? Freaked out about having sex without a condom for the first time and cumming inside her. It was all ok after she explained her IUD.

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

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

Anything else you want to add about this hookup? For some reason, even though the complete lack of emotional connection with this girl it still plays out regularly in my mind. It’s years later now, I’ve been in love and had a lot better sex (no disrespect) but this hookup, particularly the first time is burnt into my mind and it’s one of the most memorable sexual experiences I’ve had.

I’d go back there if I could

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

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