First Time Cheating

by RJ

What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? U.S.A
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Buddhist
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? None

First Time Cheating

How long ago did this hookup happen? Last month

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

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

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? I knew C from training sessions that we had participated in. She was a cutesy blond, about 5’3, well proportioned from top to bottom. I was immediately attracted to her good looks and high energy. We became good friends and usually found the time to hand out together — always with others. She was married with 4 kids and I was married with 2 kids, and neither of us was looking for an extra-marital relationship. In fact, neither of us had ever cheated on our spouses.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had gone out to dinner with a bunch of friends and participants from the conference we were attending. After dinner, a bunch of us decided to go to a club for dancing. We all danced together in a group, and then a slow song came on and C told me that it was her favorite song and wanted to dance. So we danced — not especially close to begin with — but I as we drifted into the crowd, she moved in closer and I cold feel her breasts pressing against my chest, and I felt her heat from her pussy. I rubbed my hands up and down her back and she didn’t protest so I slid my hands down to her ass and kind of pulled her closer to me. To my surprise, she started grinding her pussy against me and I got hard — which I know she felt. After the song was over, we went back to the group and resumed our group dancing, but you could tell that something was different and the sexual tension was definitely there.

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? After we got done dancing, the group sort of disbanded as people went to their respective hotels. I offered to walk C back to her hotel and she told me that would be nice. When we got to her hotel, she told me she wasn’t sleepy yet and asked if I wanted to chat in the lobby. We chatted for awhile and then she said she better get to bed because she had an early flight the next morning. I told her I’d see her to her room, which she thought was funny and unnecessary, but let me do it anyway.

When we got to her room, I opened her door, and leaned in to kiss her on the cheek to say goodnight, when she turned and kissed me on the lips. Soon we were her room making out like crazy. I massaged her breasts and then slid my hand between her legs and felt her wet pussy. I started massaging her clit as we kissed and she exposed my hard cock and started stroking it using my precum as lubricant. I felt the urge to cum and told her she was going to make me cum. She asked if I stayed hard after I came, or could get hard quickly after I came, and I told her I didn’t know cause my wife and I were one-and-done lovers. She kept stroking and I came hard, spurting my cum on her bedspread. To return the favor, I removed her panties and started to lick her. Her pussy had a slightly vinegary smell probably due to the dancing, but she was wet and tasted good. I felt her starting to rock her hips and moan softly and so I started sucking on her clit — gently at first and then harder as she responded. I dipped my pinky finger in her wet pussy and then gently pushed it into her ass and I sucked her clit. She came hard — bucking against my mouth.

After she calmed down, she pulled me up to her and told me to kiss her cause she wanted to taste herself on me. As we kissed, I felt her guide my hard cock into her pussy and we started fucking missionary style. Because I had cum earlier, I felt in control and we fucked slowly and gently for awhile, and then she started encouraging me to go faster and harder. I started pumping hard and fast as she moaned her encouragement. I felt myself cumming and asked her if I should pull out, but she put her hands on my ass and wrapped her legs around mine and started to help me fuck her. I came in her and stayed there until I got soft and slipped out. I don’t think she came a second time, but she said she enjoyed it. We cuddled for awhile and then I told her I should go because she needed to get up early. We kissed deeply and then I left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 are still in touch with each other and talk and text regularly. We keep everything professional, but we have created secret email addresses that we use for private stuff. We plan to get together ASAP when the opportunity presents itself. She says she has “feelings” for me, and I know I have “feelings” for her too. Not sure when this is headed but we’re going to find out.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

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? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

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? The new experience of being with another woman. Different smell, movements, sounds, rhythm.

What was the WORST thing about this hookup? Nothing yet.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Well, the genie is out of the bottle now — if you know what I mean?

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? Sorry to say, but she is a much better lover than my wife.

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? No thoughts.

What do you think about the Casual Sex Project? Interesting forum. Thank you,

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