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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Manager
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? This is my first

Sex Can Be Easy In Your Twenties

How long ago did this hookup happen? Two years ago

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? Just met that day

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? I just moved into a small city of about 60,000. Since I was single, I went online looking for a date. The choices were pretty limited. Most women were older than me, or they were on the much heavier side. I like women who are slim to athletic in build. I finally decided to connect with “C” a 25-year-old single mom with a 7-year-old son. She was 165 cm (5 feet 5 inches) with a slim build and medium length brown hair and about average looking. She was the best option on that online dating system. I never expected it would go anywhere. I connected with her anyway to set up a date since I wanted to socialize and just meet some new people. Life was pretty lonely having just settled into town. I didn’t expect to be hooking up.

It was raining that night. She called me and asked me to pick her up outside a shopping plaza. She showed up about 25 minutes late. I was about to drive away when she jumped into my car. Since it was pouring outside, she suggested we don’t bother going anywhere and if I can just drive her back to her place. She said we can have a drink there. That sounded a bit odd, as she seemed rather trusting of me, but I look like the trusting type.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was sharing a rented house with some roommate who was working the night shift. Her son was sleeping in the other room. After she unpacked her things in the kitchen, she took some beers out of the refrigerator and we talked a bit on the kitchen table.

At some point, she asked when was the last time I had sex. She also asked what was my favorited sex position. Up to that point, my sexual activity was pretty conventional. I just said missionary. She said she likes it doggy style and missionary is also good when she rests her legs on her partner’s shoulders. It sounded like she was interested in having sex right there, but I couldn’t believe it was that easy. When she said she is a little tired from the long day and wanted to lie down, that’s when I figured she was DTF. We went to her bedroom and relaxed on her bed. At that point, her son woke up and knocked on the door. She went out to say something to him, then sent him off to sleep again.

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 came back into the bedroom and we took off our clothes. We were kissing and we she started stroking my cock. I started stroking her pussy as well. I asked if she wanted to try doggie style first. She siad sure and immediately got on all fours on the bed with her ass pointing right against my cock. I didn’t bring a condom. I told her this, and she said she didn’t have any either. She said she’s not a slut and I don’t look like one either, so she’s fine without a condom. I was a bit hesitant, but my cock was rock hard and its tip was already touching the entrance of her pussy. So I just slid into her and pushed all the way. I fucked her in that position for a while, and she was clearly enjoying it. We tried to be quiet to avoid waking her son who was sleeping in the bedroom down the hall. After a while, I asked to try missionary with her legs against my shoulder. She flipped around and pulled her legs up. I slid into her and she rested her legs on my shoulders. As I started fucking her, she wrapped her legs around my neck and pulled me in closer. The penetration felt really deep and satisfying. I couldn’t hold it for long and pulled out to shoot my cum all over her bed. We rested a bit and fucked a second time that night.

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? I left after we fucked twice. It was about 1 am by then. We talked by phone a few time afterward. She said that she knows she is not the type for me because I want a relationship with someone without children. She introduced me to a friend of hers who is single. I’ll have another story about that later. We basically agreed to be fuck buddies which led to sex 3 more times after that.

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

What were your motives for this hookup? Fun, pleasure, horniness

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? I didn’t tell anyone, but I think she told her friend

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? A little bit

Why do you regret this hookup? I wasn’t interested in her, and it was so spontaneous that we fucked without a condom.

What was the BEST thing about this hookup? Sex after meeting someone on the same day is a huge ego boost. It says they like me enough to have sex with me. It also introduced me to two new sex positions.

What was the WORST thing about this hookup? Doing it without a condom. Doing it with her son sleeping in the bedroom down the hall.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I learned that women are horny at this point in their life and want to be fucked. Having learned that, I became much more forward in my advances afterward, which turned out to get me more sex with more partners.

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

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

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

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