Freebie

by Tom

What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Sydney
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Toey
How many sexual partners have you had in your life (including oral sex)? Quite a few
How many hookup stories have you here posted before? None

Freebie

How long ago did this hookup happen? A couple of weeks

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Paid sex

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? She is stunning. Part African. Flawless skin, great hair, teeth, eyes and all the rest. Healthy sized and toned.
I answered her online ad when I was traveling interstate. It said something like “24, ,DTF size 10, $300, exotic.”

She responded and sent some pictures, and I was in. I wasn’t sure what she’d really be. She has since told me she was 21 when we first met. I don’t know what she thinks of me being 46. Something tells me she likes it. She seems to enjoy sucking my cock and she must have noticed the grey pubes!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I saw her in the lobby and knew she was hot before she took her clothes off. I stammered in the lift. I was very happy and nervous. She was very calm. I thought she was on drugs. I regretted asking her and still do.

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? We had some small talk and got to it. She seemed to enjoy herself but I couldn’t tell. I had to do it doggy style because I knew if I looked at her gorgeous face I wouldn’t last. My plan failed as I could only look at her gorgeous ass and back and could hear her moans. I think I lasted a few minutes.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes

Did your partner have an orgasm? No

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? We’ve met half a dozen times or so since. She surprised me by contacting me when she came to my city. We got a day hotel. She has also let me have my way with her for free one morning too. She came over the next day after visiting me in the evening. We kiss a bit now too. I think she genuinely likes getting nude with me where we both enjoy oral. I also request that she wears particular clothing which she normally does.
I wish I could make her come though. I love trying to. One day soon I will. She smells, looks and sounds fantastic.each time we meet we get more intimate. I am very lucky I met her as she has filled a part of my life that was missing. I often think of ways to get her to visit me or visit her. It’s a tad expensive but the clarity of the financial arrangement means that I can assist a hot woman give me a great deal of pleasure and hopefully I can give her some too

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel better about myself, To cheer myself up, Power / Dominance, Submission / Relinquishing power, Making new friends

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? My friend from high school. We share secrets

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Watching her eyes roll when I put my tongue inside her and hold her breasts

What was the WORST thing about this hookup? I can’t afford to have her at will.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No regrets.

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? Did I mention she’s stunning?

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? Bravo

What do you think about the Casual Sex Project? Bravo

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