Learning As She Went


This post is sponsored by Trust.

by Jay-Oh

What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Scientist
What’s your current relationship status? In a serious relationship (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)? 20+
How many hookup stories have you here posted before? 3

Learning As She Went

How long ago did this hookup happen? 6 years ago

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 less than a month

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 a friend I had kind of met by accident, just shopping in the store where she worked. We started talking and the next day I went back to get her phone number. She was average height, with huge boobs and a great figure, brown-blonde hair and an oval, honest face framed by her hair.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It turned out she like hiking, so we agreed to spend a day hiking…at least that was the plan…it started pouring with rain and the ground was awash with dirty water. We sought shelter under tree which for some reason had a plastic sheet in its lower branches. The rain showed no signs of stopping, so we just started talking about anything and everything. We were in theory on an exposed mountainside, but there was no one else around.

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? After I while I kind of noticed how great her breasts were and I said so. She was a little embarrased, but thanked me anyway and leaned back, pushing her boobs out as she unzipped her jacket. She wasn’t showing much cleavage, but it was still really hot. She started talking about her figure, what she liked and didn’t like and as she did she absentmindedly rubbed her right breast, which was incredibly hot. I asked when she’d last been with a man and she surprised me by saying “never, really”…she went on to explain how it has just never felt right.
I started to feel like perhaps I’d done something wrong, but she smiled and grabbed my hand and put in on her breast – through her top it was so warm and firm in my hand. She smiled and closed her eyes as I massaged her for a good 5 minutes. I asked what she wanted and she said she didn’t know how this kind of thing worked, so I told her just to do what came naturally. She responded by taking off her top and sitting there with just her jacket over her shoulders…she really had perfect breasts and she lay back on the ground as I moved down on her to kiss her chest and neck, moving up to her face and with my hand on her bare stomach and hips. After a few minutes she pushed me off, stood up and said “Show me.” She was talking about my dick, so I pulled down my shorts and let her pull down my underwear – of course my dick sprang out. She cood something about its size (I’m not huge, but I’m slim, so I guess it looks quite big) and asked if she could touch it. So she began, the first handjob she’d ever given, crouching in front of me as I stood, her with a bare chest and her huge boobs jiggling as she used her right hand on me, while staring at my dick the whole time…it was so unspeakably hot that I came in about 40 seconds, most of it going on the ground, but some on her hand, arm and jacket sleeve(!)

She seemed satisfied (I certainly was!) and after we’d cleaned up as best we could, we sat down and hugged for a couple of hours, until the rain subsided and we called it a day. I offered to touch her down there, but she said me touching her boobs and kissing her was enough (she was also a virgin), so we left it at that.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? Unfortunately when we met after that there were always other people around and we never got a chance for a follow up. We kind of fell out over something trivial and never made up again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, 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? Somewhat

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? One friend – he was so jealous, as he knows the girl in question.

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The exotic nature of a virgin touching me.
Her huge boobs.

What was the WORST thing about this hookup? That it only happened once.
That she didn’t have an orgasm (but she didn’t want to be touched down there).

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me more confident about making friends with women

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

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

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

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