by BenString

Gender: Male
Age: 24
Race/ethnicity: White
Current location: San Francisco
Highest education received: Some college (not currently in college)
Occupation: Model
Relationship status: In a relationship
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 25+
How many hookup stories have you here posted before? 0

House-Sitting

How long ago did this hookup happen? 3 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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 met Clara when we were both acting in an indie film. SheI thought she was really cool and exotic when we first met. Clara was a small woman, with some well placed curves. She had  dark creamy skin and huge beautiful wild frizzy hair. After the first night we filmed together she gave me a ride home. We talked about our relationships, her frustrations with her on-again/off-again, and the two year that had just ended badly for me. Before she dropped me off Clara said ‘be your own hero’. That genuine spirit made her fiercely attractive to me. We started having lunch and going places, but initiating anything, let alone expressing myself was difficult at the time. Clara was also 10 years older than me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was house-sitting my aunt’s huge hill house a few weeks after I had met Clara. The place was massive, and had a hot tub too. I texted Clara, to see if she wanted to come over. Clara came over around 10. We ate, and talked, then Clara and I danced a little, awkwardly. I asked if she wanted to use the hot tub. “Sounds nice,” she said. Clara took off her clothes on the spot and dipped in. I was surprised, but I did the same, and got in too. Her naked body was beautiful, and I had an erection as soon as I was in the tub. We continued to chat for awhile, until she said “I should probably go”. I asked if she had a boyfriend. She wasn’t sure what to say, so I told her I wanted her.

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 made my move. We started making out in the tub. We moved inside soon. We dried off and continued making out in the couch. “Let’s just kiss,” she said. We moved upstairs to a bed. We kept making out until she asked if I had a condom, so I knew she wanted to go further. We fucked in cowgirl, then we changed rooms. Clara started to blow me, then we switched to missionary. She put her finger in my ass while I penetrated her. Although I had experienced this before, with her the experience was amazing. We fucked for at least 2 hours. We were both sliding all over each other by the end we were so sweaty. When we had finished Clara and I talked about our age difference: she thought I was “cool” for hooking up with an older woman.

Did you have an orgasm? Did your partner(s)? Clara had two. I had one.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom.

What were your REASONS for having this hookup? I had ended a relationship of two years a month ago. I needed some. Clara was beautiful and we had chemistry.

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Clara said she should go, and got dressed. I walked her out, kissed her good night.  Although I so wanted to do it again, Clara was in a mess of a relationship and didn’t want further complications. I wasn’t quite sure what I wanted of her either. We continued to meet for lunch dates while I still lived in my hometown. I visited her a few months ago. She’s doing well, living with a good guy she loves.

To whom did you talk about the hookup? How did they react? I told my best friend. “Good” he said. He was glad I was scoring again.

Was this a consensual and/or wanted experience for you? For your partner? Yes for both.

Do you regret this hookup? If so, why? No.

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

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

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!