The Entourage

by Rachel

Age: 27
Race/ethnicity: White
Location: Portland,  OR
Highest education received: College degree (eg., BA, BS)
Occupation: Sales
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Women are sexy but crazy, I’d never date one
How many hookup stories have you here posted before? None

The Entourage

How long ago did this hookup happen? Always

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, paid sex; something else.)? Normal behavior

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 have an entourage. I have short list of people I trust to have casual sex with. I’ve known some of them since childhood, others only a couple years. Most are old high school/ college friends. Some have been married men. I prefer people who don’t get attached.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was always labeled a cheater so I decided to just be honest about my sex life and it’s worked well. I just love the chase and I haven’t grown up yet.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I have certain people for certain kinks. Not everyone is into everything that I’m into.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Don’t be a fool! Wrap your tool!

What were your REASONS for having this hookup? I can’t handle commitment because as soon as I let anyone in, I get hurt, so I just stopped doing that. I get the sex I need from my friends and the love and acceptance I require from my family.

Were alcohol or drugs involved? If so, how much? I don’t drink much anymore, I do smoke marijuana almost every night though.

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? I feel liberated in my lifestyle and as long as you use condoms and get tested regularly, I feel like I shouldn’t be ashamed. Though many people try to make me feel ashamed.

To whom did you talk about the hookup? How did they react? I‘ll tell anyone about my lifestyle that wants know. I don’t go around flaunting it but if anyone asks, I’m honest about it. Sometimes I’ll ask “do you REALLY want the answer to that?”

Was this a consensual and/or wanted experience for you? For your partner? Always. I have been fortunate never to be the victim of a sexy crime. I can’t imagine what that’s like for women. Disgustingly horrid thing to do.

Do you regret this hookup? If so, why? I don’t regret my life. I always have the ‘what if’ moments. What if I had chosen to just be with him, what kind of person would I be?

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? The best thing is the variety of sex. It’s never boring. The worst is feeling lonely sometimes at night but I’ve gotten over that for the most part over the years.

All things considered, how POSITIVE was this experience? Very 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? Always use protection. There’s literally NO reason not to. And get yourself tested, not just to protect you but to protect your friends too.

What did you think about this story? Tell us in the comments, just be nice!

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