The Art Teacher

by Dave

What’s your gender? Man
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA, Maine
Highest education received: Some college (not currently in college)
What’s your occupation? Entrepreneur
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Curious
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

The Art Teacher

How long ago did this hookup happen? 3 months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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 very beautiful woman, but not in the way beauty is projected by the media. Her features were very geometric, but not really angular. She was a very small human. About 5’5″ and maybe 130 pounds. I thought she was very pretty, and she turned out to be an interesting person.

We had met online and arranged a first date about a week before it occurred. She was the first person I actually met in person after meeting them online. I’ve only met one other since then.

She was older by 11 years, so I felt a little nervous having not been with a person that much older before. I was excited for whatever might happen, though.

We went on our first date, just coffee late one morning. We had a nice conversation, but I honestly wasn’t feeling a ton of chemistry. If anything I was fetishizing her for being older which didn’t help me come across genuinely, but it wasn’t something I could very well help.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We hooked up on our second date. We ate dinner at a local sushi place. Again, it was quiet – no connection. It wasn’t an uncomfortable quiet, though. After we ate we started walking back to her cars and I invited her up to the roof of one of the tall buildings in my town (I have a key… doesn’t matter why). We went up there and looked around a bit – it’s a nice view.

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 were sitting on the roof just talking and we stared at each other for a moment and started kissing. We did that for a while before deciding to return to the street. She only lived a block away, so we went to her place. We put on a movie, but didn’t get far into it before she started touching me. I fingered her on the couch for a few minutes and then we moved into the bedroom. From there we had sex multiple times and in different positions. I remember her place smelled like patchouli (and she always did, too), which was interesting because I burn patchouli incense. We slept through the night, woke up and had more sex, then grabbed breakfast.

She gave the best head I’ve ever received in my life. She didn’t shave, either – it was full grown. That was okay, though, it’s my preference anyway. She was a little too small for my satisfaction, though. I like slightly more filled out body.

We got together for a third and final date a week later. She was clearly done at this point though. At the end of the date I found out it’s because the last condom ended up stuck in her body. I was pretty sure I had gotten it off, but there were condoms everywhere and it was dark – just bad luck, but mostly for her. Nothing came of it.

How sexually satisfying was this hookup? Very

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? We sorted out the fact that I definitely didn’t mean to leave that condom there. She felt better about it after. Our romantic relationship had ended, but we still see each other around town and chat. It’s amicable.

It was a good experience for me to be with an older woman. I’ve been going through a phase where that’s where my interest more heavily lies. I also learned the lesson to always check and keep track of the condoms.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have

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? 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

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

To whom did you talk about the hookup? How did they react? Just a handful of my friends.

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

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? Being with a badass, kinky woman who during the day gives the appearance of being not that at all.

What was the WORST thing about this hookup? The way it ended wasn’t great.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was my first real casual hookup with someone I did not know previously. It opened a new door for me into casual dating. I had been in numerous long term committed relationships before.

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

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

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