A Fling with the Intern

by RandomGuy

Gender: Male
Age: 29
Race/ethnicity: Caucasian
Current location: Los Angeles
Highest education received: College degree (eg., BA, BS)
Occupation: Management
Relationship status: Single
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 2

A Fling with the Intern

How long ago did this hookup happen? 4 years

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? Karen had short auburn hair. About 5’7″ with B-cups and athletic body from playing volleyball. I think she was half Caucasian half Asian but wasn’t for sure

I had casually known her from passing hello’s and maybe one conversation.

She was always energetic and nice to others.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was a summer intern at our firm in Los Angeles. Karen would often help my boss with his errands and file paper work. During work one day I bumped into her as she was returning from an errand. I asked her about some of files I needed. She said she would get them but had other things needed to be done first. I said ok as I was staying late.

A few hours past and everyone cleared out from our floor. The janitorial staff was about to arrive within the hour so I decided it was time to head out. I had completely forgotten about my request of Karen. She showed up right before I left with the papers. She looked pretty stressed. I thanked her and asked if she was done for the night. She said yes. Asked her if she had plans. She said no so I asked her if she wanted a drink from a pub across the street as a thanks for the hard work. She was reluntant but agreed.

We locked up and went downstairs and walked to the pub. It was kinda dead as it was a tuesday. I bought her something, she downed it pretty quick so I got her another. Asked her if she was ok. Said she was getting off a recent relationship that ended badly and work had been stressing her out recently. I apologized if I was adding to that stress.

A few drinks later and we had a good conversation going. Wasn’t really trying anything with her, was just concerned as I knew what it was like to go through the intern rut. It was pretty late so I asked her where she lived, I would get her a cab. She said she could drive but I told her no. I lived only a few blocks away near little tokyo so I offered my couch to let the alcohol run its course then I’d let her drive home.

I helped her walk to my apartment as she apparently was a light drinker. When I got home I sat her on the couch and gave her some water. I told her I was going to take a shower and if she needed anything to let me know. I jumped in the shower and a few minutes later I heard the bathroom door open. “Did you need something”

Suddenly the curtains opened and their she was naked. I was kinda shocked so I shouted “whoa!” and covered up a little. “What are you doing?” She got into the shower saying, “I wanted to take one too.”

She got under the shower head, washing her face. I was kinda in a weird spot as she was a few years younger than myself and we worked together so I distanced myself. “I’ll jumped out til you finish” She responded “Don’t…” So I stayed.

She turned around and pressed against me. “You know, I’m like 2 seconds from taking advantage here” “Go ahead…” she responded. “You’re drunk….” She wrapped her arms around me “…I want to..”

At this point my dick was at 110% and that was all the consent I needed.

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 tilted my head down and kissed her. She passionately returned it. Pressing her against the wall of the shower our bodies rubbed against each other. I turned off the shower and told her we should go to the bedroom. I picked her up and laid her on the bed. She sprawled out on the sheets. It was really the first time I had really looked at her. She had a pretty face and great body. I went down on her and began to suck on her pussy.

At first she wasn’t too responsive but when I put two fingers in she began to moan. After a few minutes she came. I stood and grabbed a condom. Before I put it on, she began to jerk my dick off. She licked it and asked if we were gonna fuck. I said yes. She said I didn’t need the condom but I never trust a drunk woman so I slipped it on.

I penetrated her passionately. She curled up around me. Moaning loudly. She bit her lower lip as I began to thrust inside. I was making pretty good contact as it wasn’t long before I was close to orgasm. I told her I was cumming and came pretty hard. She told me to keep going which was tough since my dick got sensitive but I lasted another minute…long enough for her second orgasm.

Did you have an orgasm? Did your partner(s)? I came once and she came twice

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Wore a condom. No we didn’t talk STI

What were your REASONS for having this hookup? Moment of passion

Were alcohol or drugs involved? If so, how much? She was drunk and I had a little buzz but nothing major

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? We both passed out afterwards. The next morning we woke, she had a slight hang over. I asked her if she remembered the night before. She said she did. I asked her if she was fine with having sex. She told me she was fine with it. Actually she felt a little relieved of some of the stress she had built up. We got dressed. I offered her breakfast but she wanted to run to her car so she could get home and change before work.

She left. Later that day I bumped into her. I guess we tried to keep out professional modes on. So we kept our greeting casual.

To whom did you talk about the hookup? How did they react? I told a friend but no one from work. Friend was cool with it, as he tends to go for younger women

Was this a consensual and/or wanted experience for you? For your partner? Yes. It was for her as well

Do you regret this hookup? If so, why? No not really.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Having spontaneous passionate sex was definitely the best.

Worst was maybe the awkward morning and worrying if it was consensual.

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

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

Anything else you want to add about this hookup or anything else? I talked with Karen a few days after to make sure she was ok. She said she had calmed down a little and was a little less stressed. I told her to let me know if I could help. She said thanks and that although she enjoyed the night she didn’t think it was more than one night. I said I understood and that I wouldn’t let it affect our work relationship. But if she ever needed someone to talk to, my door was open.

A few years later she got a job at another firm and she got married this year. I met her at a social event and it seems things are going great for her.

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!