Middle Man Journey



What’s your gender? Woman
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Philadelphia
Highest education received: Some college (currently in college)
What’s your occupation? Caregiver
What’s your current relationship status? Was engaged, but getting back together soon with an ex who lives in another country.
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7-10
How many hookup stories have you here posted before? None

Middle Man Journey

How long ago did this hookup happen? A few days ago

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

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For 1 to 3 years

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? He is a Puerto Rican guy in his late 20s, with dark eyes, and he’s very sexy. I’m 5’3” and he is maybe two inches taller than me. The first time we hooked up, I had just got out of a relationship. He was a bartender and we went to another bar to get to know each other and then spent that night (him drunk, me sober enough to drive) together in a hotel. Now he works for a company as a accountant, and is living a sober life. This time around over a year and a half later and various other hookups between me and him in his apartment, he texted me to come over. I told him a few days earlier about how my fiancé and I split it off because of how things were not working out. He congratulated me on the breakup. He always makes me feel good sexually. I always found him super sexy, and we talk once in a while. This time we met at his apartment again as per our standard, I have a car so I can drive to him while he doesn’t have one and I live outside of the city so he would be unable to get to me.

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 got to his apartment and we cuddled and updated each other or major things that have been happening to us since the last time we saw each other (typically about once a month). I made him aware that I was still on my period, as he knew from a week ago. Then we went and I gave him a blow job, and we agreed to have anal even though I can get very nervous about it since I haven’t done it much. However, he got me to relax and it felt really good. He always goes on top and puts my legs up to his shoulders. Soon after we fell asleep together. He treats me really well, always does and he’s always a great lover and turns me on so much. It ended when I woke up the next day at about 8:30 am and had to go to work.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? It felt good to catch up with him, we are pretty good friends but we do keep our social lives separate. I don’t think he really tells people about me and I don’t really mention him except to my ex-fiancé and a friend. I believe we both want to continue the way we are, meeting up at his place once a month, maybe more now, since my fiancé is out of the picture. I felt great the next day and felt good to have someone to talk to about my ex-fiancé and have them listen and understand the scenario.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To cheer myself up, I was feeling lonely

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? 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

To whom did you talk about the hookup? How did they react? No one yet, but I may mention it to a friend soon who I mentioned about him before.

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? We always have amazing sex, he can pound me and won’t stop even when I ask, but I don’t want him to stop either really. He always makes me feel so good and even thinking about him makes me horny.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I didn’t think about it before that much. But now I feel a lot more confident and I know what I’m looking for in a relationship. Not necessarily would I want to be with him but I know now what I look for in a man as a person and sex wise too, he’s not the kind of man I would want to be with since he already as a daughter and I have no kids, but I want a man with his kind of drive both at work in life and in bed.

All things considered, how POSITIVE was this experience? Fairly 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? It made me a lot more confident, helped me learn who I am as a person, and what I like when having sex. It made me a lot more open to understanding different types of relationships.

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