The Ride of My Life

by Matthew

What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Montreal
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
Religious affiliation: Christian
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)? 40
How many hookup stories have you here posted before? 0

The Ride of My Life

How long ago did this hookup happen? 3 weeks

What was your relationship status at the time? Dating casually

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? She was 33, Spanish, long blonde hair, tattooes, short, small breasts, nice body.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met online

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? I kissed her on the bed and we immediately started using tongues. It was very hot and passionate. She was wearing a sweater, black shirt, black bra and jeans, me a sweater, striped shirt under and jeans, I reached into her pants and felt her butt as we lay down. She teasing slipped her hand down my pants a couple times but did not go all the way. I put my hand down hers and felt some hair and a soft, wet pussy. She kind of moved away so I let that go and continued massaging her butt, then moved my hand up her shirt to her breasts.

I took off her shirt and sweater, then took off mine as well. By now she was reaching into my pants feeling my erection and I unbuttoned my pants to give her better access. I took off her bra and started kissing her nipples, which were small and light colored. Her breasts were small but nice.

She had my penis now firmly and was stroking it hard up and down. We were still kissing passionately. She asked if I had a condom and I said yes so she went to the bathroom, I took my pants and shirt off. When she got out I was standing and we started kissing standing up, she was topless with just her jeans and panties on, I laid her on the bed and took them both off, then took off my boxers.

We laid down on our backs and I began playing with her clit as she did my penis, she cupped my balls which were very firm and her cold hands felt good against them.

We got under the blankets and she got on top of me. She was positioning to begin sex so I put the condom on, and she began riding me. She was very good at it, very wet and moving her hips perfectly in sync with me. She began crying out and covered her mouth to stop it. I told her she could make noise. She let out cries which could probably be heard by neighbors.

I felt her tits as she rode me, then sometimes her ass. For a while, I had my hands behind my head and watched her do her thing. She was upright the whole time and I had a great view. It slipped out so I turned her over and got on top. It was very hot and I was deep inside her. She told me to go stronger so I did. She continued to make a lot of noise, which was amazing,

Finally, she said she was coming and I exploded inside her. It was very sexy.

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? She slept over and left the next morning. Would like to see her again but she doesn’t respond much to texts

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

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

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? She riding me and her covering her mouth to not scream out in pleasure.

What was the WORST thing about this hookup? That it only happened once

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? I think life is short and you should enjoy it as much as possible.

What do you think about the Casual Sex Project? Good idea!

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