What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago, Illinois, US
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Sales Rep
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? Two
How long ago did this hookup happen? Last week
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Fuck-buddies / Booty call
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? I will call her Meg, I referred to her as Partner C in my last post. She is a pretty brunette in her early thirties with a toned fit body but not muscular like my other partner and a nice pair of c cup breasts. She manages a hotel for one of my clients and I had known her for several years before we hooked up. I always thought she was attractive but she was still married when we first met. After she left and divorced her husband I asked her out and we ended up hooking up and have been seeing each other about once a week for the past two months.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had woke up a bit horny that morning and I sent Meg a quick text to see if she might be available. Meg texted me back a short time later saying she was and wanted to see me and said she would be available during lunch and we often hook up during the day time.
So I probably should share some quick background on Meg here. She married her high school boyfriend the first guy she was ever intimate with and was with him a very long time. She also comes from a conservative background so sex strictly for pleasure is new to her, as is enjoying herself and fining out a bit what she likes sexually and being with me just for that.
Meg manages a hotel and can take a room out of rotation for an hour or two for us to use. She texted me the room number shortly before I arrived.
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? I arrived at the room and Meg and I talked for a few minutes. We started kissing and then she let me undress her. We made out naked for a few minutes and Meg stroked my cock a bit and she let me suck on her breasts. I finally gave into my lust and spun her around, pushed her down on the bed, and penetrated her from behind. In charge and busy with people in real life, Meg tends to be a bit submissive in the bedroom and usually willing to do what I want and ask. I penetrated her until I came and then we lay next to each other and I used my fingers to finish her off that way until she had an orgasm.
We cuddled a bit and watched a little TV and talked until we both had to go back to work. We kissed and went our separate ways.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, 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? I felt great and was able to focus on work and felt great the next day. Usually Meg and I hook up at her work during the day and occasionally she comes to my place in the evenings. However I am not sure where I truly stand with her and feel I am some sort of fling to help her get over the divorce. I was there myself following mine so I get it I also have been considering dating someone more recently and that would mean breaking off my casual arrangement with Meg along with my other two partners I have besides her. I wouldn’t mind actually dating Meg but something tells me she is not ready for that.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history, Exchanged recent STI test results
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up
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? Haven’t told anyone and Meg wouldn’t want anyone to find out.
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? Good sex when I wanted it with someone I am attracted to.
What was the WORST thing about this hookup? Realizing that Meg may be using me to get over her divorce.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This hasn’t changed how I feel about casual sex or sexuality all though being with Meg has made me realize that women can use men for sex too, but I find I am kind of ok with that
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
You have a hookup story to share? Submit it here!