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What’s your gender? Man
How old are you? 66
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: College degree (eg., BA, BS)
What’s your occupation? retired
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 80
How many hookup stories have you here posted before? 2

Strapon From A Bi Girl

How long ago did this hookup happen? 45

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a year

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 had worked with Cathy for several months before anything sexual came up. She was mid 20s, brown hair and big green eyes. She had soft curves and with nice tits and a big round ass. She was living with another woman, and they identified as bi but not as a lesbian couple. Just two women who lived and slept together. Her girlfriend/roommate actively dated men and women, but Cathy seemed happy with her gf alone. I was not getting along with my wife and we hadn’t had sex in months. On a whim one really slow day, I dared her to see if I could lick her pussy as well as her gf. We found a relatively safe place at work and off came her jeans. Over the next couple of months, I have her many orgasms and she said I was at the very good lesbian and vastly better than most guys level.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After one of these sessions, she told me about the new toys she had bought: a strapon harness and dildo. I asked if it was for her pussy or her gf’s or both. She said her gf wasn’t interested in it and that disappointed her. Cathy was “looking forward” to having a dick and laughed about it. I told her my wife had used a small dildo on my ass in the past, and I liked it. So…if she’d like to try her dick out with me, ok. The idea of fucking a guy cranked her intensely. She took her pants off again told me to make her come right now! She said her gf had a date for the next night and I made plans to ‘work late’.

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? When I got to her house, Cathy was in a robe on the couch. She told me to get undressed and handed me some lube. She ignored my semi hard cock as I lubed up my ass. She stood up and dropped the robe off her shoulders dramatically. She was naked with only the harness and a large black ‘realistic’ dildo between her legs. It was probably 7 or 8 inches long, and fairly thick, but looked human rather than porn/cartoon sized. I got on my knees and asked if I could suck her dick. I sucked for a while and did some theatrical moaning and slurping to keep the mood going. I then looked her in the eyes and said, “please fuck me with your big hard dick!” I lubed it up and bent over the end of her couch.

We got deeper into role playing. I said, “Be gentle baby, your dick is so so big.” Cathy laughed at me and said, “you’re going to take it all you slut! And, you know you want it all!” But she was very slow working the head into my ass. My own dildos were much thinner and we had to go very slowly at first.

Once the head was in, I reached around and kept it in while Cathy slowly pushed deeper. It hurt some, but we kept going. She encouraged me, saying, “take more, you know you want it, you know you want my dick.” After we got a couple of inches in, Cathy began to to move in short strokes, slowly moving deeper. At about 6 inches, I told her to just fuck me. It was hot, it hurt and felt very satisfying at the same time. I stroked my dick in rhythm to Cathy’s thrusts.

Cathy kept a constant stream of dirty talk going, saying, “you little bitch, you faggot, you need my dick.” I think the end of the dildo was hitting her clit as she kept moaning and came at least once. We had put a towel over the end of the couch and I suddenly came explosively. She slowly withdrew the dildo and we went back to her shower together and cleaned her ‘dick’ and my ass. Then I licked her pussy to another orgasm.

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? Frankly, we were both embarrassed by the intensity. We really weren’t intimates, just barely fuck buddies, but this was a moving experience.

At work the next day, we didn’t talk for a while. Then went to our usual rendezvous spot. Cathy said she really did love having a dick and I treated it very nicely. I said I enjoyed her dick a lot, and it was a terribly pity her gf wasn’t interested. She then gave me the only blowjob I got from her. She left that job in a couple of weeks, and I never saw her again.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have

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? I’ve never told anyone about it, but I have purchased harness and dildos for my current partner, which we use occasionally.

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was intense and very exciting for both of us.

What was the WORST thing about this hookup? It was too intense and intimate for our very casual relationship to bear.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It confirmed my enjoyment of receiving anal sex, but it warned me to be careful with intensity.

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

All things considered, how NEGATIVE was this experience? A little 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? Wish I had more of it then and now.

What do you think about the Casual Sex Project? It’s fun and exciting to tell these stories and read those of others.

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