It Was Only Supposed to Be Once



What’s your gender? Man
How old are you? 55
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0

It Was Only Supposed to Be Once

How long ago did this hookup happen? 4 yrs

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 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? We met on Craigslist, she answered my ad for a FWB. We didn’t know each other, so we first met at a local restaurant for a drink. She was gorgeous and wore a sweater that showcased two large, round breasts that I wanted in my hands then in my mouth as soon as possible.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At the restaurant, we both decided we wanted what the other did. We agreed to meet and play at my business the next morning before anyone showed up to work.

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 started off slowly. She had told me she had Herpes but was on meds and hadn’t had a breakout in more than 5 years. I really didn’t care, I wanted her. She showed up at my door and was shaking from nervousness. I took her in my arms, one hand on her incredible ass and another touching her cheek. I kissed her, softly, slowly on her cheek. She wasn’t having any of it, she turned and slid her eager tongue in my mouth, dancing all over as her shaking turned to sobs of pleasure. We fucked for more than 3 hours, each of us cumming at least 5 times. We couldn’t get enough of each other, we were thirsty for what the other offered. She was a blowjob master, getting me off twice. Her pussy was the tightest I’d ever experienced, even having had a child less than a year before.

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? We couldn’t wait to meet again, we wanted to explore what the other offered. Little did we know how far we’d go in our experimentation.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, I was feeling lonely, Power / Dominance, It was easy / convenient

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 has ever found out about this

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? She was a sexual goddess. No holds barred, she took me in all three holes, had sex in the woods, naked in my pool, in public.

What was the WORST thing about this hookup? She wanted more, emotionally. Her husband was distant, they didn’t have sex at all. She got to where she wanted me to leave my wife. It was a tough decision honestly – I had been married 30 years when we parted. But the sex with her was much more satisfying than my marriage was. My love for my wife was what kept from leaving because my fwb was absolutely my sexual soulmate.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have sought out more casual sex since her, seeking a partner anywhere close to what we had!

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? Her willingness to experiment with anal, submission and water sports kept us together for as long as we were. These are things my wife would never do that I want to do with her yet to this day

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 think everyone should have casual sex, as long as their partner agrees and does the same. It opens up the communication and would draw them closer I think. Nothing has changed as far as sex with my wife.

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