What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Pennsylvania
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Small Business Owner
What’s your current relationship status? My female companion and I are swingers
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Swinger
How many sexual partners have you had in your life (including oral sex)? 80+
How many hookup stories have you here posted before? 3

Two Hookups in One Day

How long ago did this hookup happen? 1 week ago

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? 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? Ms Afternoon was very attractive mid 40 year old. Nice MILF body, natural breasts, she carried herself well. I met them via a hot date ad that they placed on a life style website. The couple posted hot dates on a regular basis. A life style friend validated that they are legit and players. Ms Evening is an old girlfriend who in recent years has grown strictly into a FWB or in her terms a willing participant. She is in a dead end relationship and seeks my private companionship to boost her ego. She is mid 50’s and has a nice presentation though she is conscious of the fact that she is packing on a few pounds.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On a lifestyle website, I noticed that Ms Afternoon and her partner had posted a hot date. That they were ISO a single male for NSA sex. I responded and we exchanged a few pics before they gave me their address. Within an hour, the man greeted me at the door. We exchanged names and headed to the bedroom where she lounging on the bed with her pants and panties off. We exchanged hellos as the three of us removed our clothes.
Early that evening, I had the urge to make it two hook ups in one day, so I contacted Ms Evening to stop by my place for a quickie. Years ago, I was successful in having three hook ups in one day. More or less, I wanted to relive that adventure.

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? With Ms Afternoon it was more or less straight sex. I started by fondling and kissing her breasts while the other man fingered her. Then she gave him a blow job while I went down on her. At one point, she pushed me away, rubbed herself hard, and squirted a nice flow. The man took her doggy style while encouraging her to give me a blow job. When he came, she assumed the missionary position. I could smell and feel the warmth of his cum as I fucked her. After I started to go limp, I withdrew. The hook up was over. Her name was never stated.
Ms Evening has a habit of wanting a nice micro beer or two to relax. That leads into a photo shoot of her various stages of undress. Depending on her desire we will engage in various levels of play. The majority of the time the goal is to get her to relieve tension by fingering her until she squirts. That night, my goal was to get her to squirt and to fuck her. I accomplished both and added the pics to my collection of her. While Ms Evening knows that I swing; I did not tell her about Ms Afternoon. Generally, she does not want to hear anything about my sex life though she willingly discusses hers.

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? I would like to hook up with Ms Afternoon and her man for another threesome. I hope that is a possibility. Ms Evening and I have a nice little thing going on the side. I am her confidant and she is a wiling participant.

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

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

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? Two hookups in one day with two desirable women. Smelling another man’s cum while I was enjoying sloppy seconds.

What was the WORST thing about this hookup? The possibility that I may not get a chance to hookup with Ms Afternoon again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? These hookups only reinforce my belief that casual sex between consenting adults is healthy.

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? While I am not bi, I have a strong desire to eat a creampie.

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 have been active in the lifestyle for twenty plus years. From my personal experience, I believe more couples would have a healthier marriage if they were open and swung.

What do you think about the Casual Sex Project? The majority of the stories that I have read appear to be legit.

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