What’s your gender? Woman
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Some college (not currently in college)
What’s your occupation? Personal Assistant
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Gay/lesbian
How many sexual partners have you had in your life (including oral sex)? 29
How many hookup stories have you here posted before? 0

Surprising Hookup with Actress

How long ago did this hookup happen? 3 months ago

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

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? Beautiful blonde mid-forties. Has a 1920’s flapper look. Just met her a few hours before because she flew in to L.A. from NYC to meet with my boss about a project. She has a casting couch reputation, but only with male producers. That’s why I was so shocked by this hookup. She’s played lez in a couple of different projects, but she never pinged on my radar as gay or bi.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She met my boss for lunch and they came back to the office. She was real friendly to me and everyone in the office. Very sweet. I was talking with her as my boss stepped out for a minute and the conversation led me in to talking about buying my girlfriend a gift for our one year anniversary. My boss came back and she asked if someone could take her back to her hotel, then she asked “What about her?” and looked at me. I didn’t think much about it so I agreed then I asked if I could take off early to shop for my girlfriend. At that point she suggested we shop together. That was surprising. As I’m driving her to her hotel she was super nice to me and really down to Earth. As we’re pulling up she told me to park and gave a ‘fuck me stare’ and asked me to come up to her room. That got me really confused. I didn’t think she was into women. I paused for a minute before I answered with a casual, “Sure”. I stood in the middle of the room as she’s putting down her purse and kicking off her heels. I’m getting really flustered now. I know what’s going to happen and I wasn’t sure I wanted it to. She’s in her forties, but looks at least fifteen years younger and she’s beautiful. I had not cheated on my girlfriend before and I didn’t want to because I love her, but I kind of wanted this woman.

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 walks right up to me and pressed her breasts against mine and then leaned in and softly kissed me. We started making out while standing in the middle of her room when she said, “Do you want to taste me?” I thought it was charming and a little odd. So, we take our clothes off and I’m top of her and her body is beautiful. I lick and suck on her breasts and she has really long nipples. I LOVE THAT! I moved my way down and licked pussy. She came really fast and I kept doing it. I put two fingers inside her while licking her clit. I moved my way back up and we made out some more. She flipped me over and went down on me for a really long time. She gave me three orgasms before I pulled her head up so I could kiss her some more. Then she started humping me. Grinding her clit against mine and it was wonderful.

We had sex for well over an hour. As I start to get dressed she asked me if I lived with my girlfriend. Guilt set in. I sheepishly nodded. She put her hand under my chin and raised my head up which kind of shocked me. She leaned over and kissed me gently and then said “You better take a shower. You don’t want your girlfriend to know that you’ve been fucking someone else all afternoon.” We took the shower together and it was very sensual. Towards the end she bent over and I licked her pussy from behind and she told me to rub her asshole. I did and then I put my thumb in her ass while eating her out from behind. She let out deep sounding moan which got super hot. After a few minutes of that she moved forward and stood up and turned around while I still on my knees. She placed her hands on the sides of my head and held it still. She then pushed her pussy against my face. She grinded her clit against my tongue for couple of minutes until she came again. And that was 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? The whole experience was weird. There was no sexual buildup before she asked me to come upstairs with her. Even in the elevator there was no flirting just small talk. Afterwards, I got dressed while she put on a robe and checked her phone. She didn’t even kiss me goodbye. We hugged like the way friends do. I felt bad for cheating on my girlfriend, but I did love having sex with this actress. She wasn’t cold afterwards, but she was kind of indifferent. Kind of like it was no big deal. I’m not sure how I feel about her. BTW – she turned down the project.

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

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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

To whom did you talk about the hookup? How did they react? I told no one.

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? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I cheated on someone I love. While the sex was terrific she seemed distant afterwards and that bothered me. Almost like it was business as usual for her.

What was the BEST thing about this hookup? I had a lot of orgasms.

What was the WORST thing about this hookup? The guilt of cheating and the feeling of being used just for someone’s pleasure.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I haven’t cheated since this experience, but I’ve looking at woman a lot more than before. I’m really confused.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

What do you think about the Casual Sex Project? I needed to get this off my chest. This was good for me.

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