My Sugar Baby

by Ian O’Rourke

What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Counselor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Sapiosexual
How many sexual partners have you had in your life (including oral sex)? Dozens
How many hookup stories have you here posted before? 3

My Sugar Baby

How long ago did this hookup happen? 3 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

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? Steph is a blonde, 33-year-old businesswoman. We connected on a website that posts profiles for men and women who are looking for a sugar daddy/sugar baby arrangements. We had never met before, only exchanged messages on the site, and later by text. Although she has a successful career in IT, she lives alone, works from home, lives out in the country, and works odd hours due to her corporate office being in another time zone. Therefore her opportunities to mingle with the opposite sex are limited, and she isn’t interested in being in a real relationship. The SD/SB arrangement satisfies her need for occasional sex with a safe partner and with the opportunity to supplement her income. Her libido is in overdrive, and the thought of fucking for money, given her conventional day job, was an exciting prospect.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After exchanging messages for a couple of weeks, becoming comfortable that we were a good match, and arriving at a mutually agreed-upon arrangement, we scheduled a meeting at a brewery not far from her house. There, we enjoyed a couple of drinks while we got acquainted and confirmed in person that our mutual attraction from the messaging was legit. My wife was out of town, so I had the whole night to be out without generating any questions.

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 got to the point in the conversation where we both knew what we wanted next, and she asked me to follow her back to her house. We stood kind of awkwardly in the kitchen for a while, continuing the conversation from the brewery. During a lull, I leaned in for a kiss, and she responded hungrily. She pulled me by the hand upstairs to her bedroom where we hopped on the bed and continued making out. She was grinding her crotch on my growing hard-on while we kissed passionately. We ripped each other’s clothes off and within seconds, I was on top of her and inside her seriously wet pussy. We fucked for about 30 seconds before she had her first of many orgasms. The next two hours were a whirl of naked, sweaty sex in every position we could think of. She was insatiable. I’ve paid many escorts in the business over the years, but this was some of the best sex I’ve ever had. Eventually exhausted, I dressed and drove home, already impatient for our next rendezvous. We’ve met a total of six times now.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? I couldn’t wait to see her again. The sex was fantastic. A multi-orgasmic nympho with a legit day job who was only interested in a physical relationship. What’s not to love?

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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.

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? Mind-blowing sex that has only gotten better in subsequent hookups as we have learned each other’s bodies and preferences.

What was the WORST thing about this hookup? The ONLY downside is paying for the sex. The money is never mentioned, and I leave it in an envelope on the toilet in her bathroom, so it’s a pretty invisible part of the arrangement. Still, on some level, I know she wouldn’t be spending time with me if I weren’t paying for it.

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

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? No.

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? I wish sex, in general, weren’t so taboo in our public culture.

What do you think about the Casual Sex Project? Great forum for these stories!

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