Online Affair



What’s your gender? Man
How old are you? 58
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA, Denver
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business Consultant
What’s your current relationship status? Engaged/Married (open)
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? Horny
How many sexual partners have you had in your life (including oral sex)? 28
How many hookup stories have you here posted before? 0

Online Affair

How long ago did this hookup happen? 2 years

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

How would you best classify this hookup? Short fling

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

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? She is very beautiful, early 50’s but extremely fit, brunette, shaved, a high level career professional. Stylish and very sexy. We met on an online site (AM) where I really had not had any success…most are fakes. She was, like me, just looking for a fling to satisfy an itch. Both of us were concerned about not getting caught and preserving our respective marriages.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We first me for coffee and my heart felt like it was going to jump out of my chest from excitement and fear of being seen. We met at a coffee shop/deli in a business park. It was quite busy and I was fearful of being seen as I am fairly well known and often run into people who know me. We sat at a high top table and continued the hot conversation we had been having online while also getting to know each others condensed life stories. The meeting ended with a light kiss and an agreement to meet again soon. The next meeting was over happy hour and alcohol helped us both relax a bit. That encounter ended in the parking lot (dark this time) and deep kissing against my car. She was pressing her body against my hard cock and it was all I could do to stop it at that and get home to my wife who would have been suspicious had I been home any later. We agreed to meet that weekend at a hotel.

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 made a reservation at a new hotel under the guise that it was for a place to hang out before our flight late in the afternoon. When I arrived and checked in I paid for the room in cash so nothing would show on my credit card statement. She arrived 15 minutes or so after and I texted her the room number. When she came into the room my heart was racing and we stood for a long while, kissing and running our hands over each others still clothed bodies. She brought wine, fruit, cheese etc. so we laid that out and engaged in some small talk on the sofa while feeding each other and staring into each others eyes. This let to kissing and me undressing her slowly. Her breasts were centerfold quality as was the rest of her as I unwrapped this great present. She then lowered herself off the sofa to her knees and took her turn unbuttoning my shirt, unbuckling my pants to reveal my hard cock. While looking me in the eyes she began giving me head and it was very hard to resist cumming on the spot as I had not been with anyone but my wife for 20 years. I stood her up and led her to the bed but she had to pee first. I led her to the bathroom and she peed right in front of me and I found that to be a huge turn on for her to be so open. It was my turn to go down on her so I guided her to the bed and laid her on her back spreading her legs apart and kneeling between them. I slowly kissed my way down her legs from toes to knees to inner thighs. I could see her pussy lips glistening even though I had not yet touched them. When my tongue finally parted her lips her taste was a bit of heaven. I spent about a half an hour going down on her watching several quivering orgasms with the only change being having her straddle my face for the later half. After a short break for some more wine and fruit, she rolled me over and straddled me rubbing her parted wet pussy lips against my rock hard cock sliding the entire length. After a few minutes she came again and positioned herself so that the tip of my cock was pressing against the opening of her now dripping wet pussy lips. Without using hands she managed to get the tip of my cock inside and again it was close to impossible to hold myself back from cumming watching her tight pussy slide down on me. She was equally as excited and started cumming again. Feeling her pulsating made it impossible to stop and I shot my load inside of her like I had not done in years. Cum came dribbling out of her pussy and down the shaft. She quickly went to work licking and swallowing our combined juices and that excitement kept me from going soft. It was not long before I was just as hard as had been minutes before. After a quick sip of wine I rolled her over on to all fours to see her amazing ass up in the air and knelt behind her, slowly at first, sliding my cock in again while I enjoyed the sight. Then, she reached back and inserted her middle finger in her ass…fingering as I fucked. My pace quickened and soon after she had another intense orgasm which caused me to cum again right along with her.

Shortly after, her phone rang, and it was her husband asking where she was. She was very shaken by the call and quickly put herself together saying that he could get violent. Later on she texted me that he was highly suspicious and she thought that we should lay low.

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? A few weeks later she texted and twice we tried to find a time that would work but my schedule did not line up. Later I tried to initiate another meeting but she had decided to recommit herself to her marriage. I regret that we could not have had another meeting.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Birth control pill / patch / ring / injection / implant, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness

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….Only here!

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? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? Only in the slightest amount.

What was the BEST thing about this hookup? Sex with someone other than my wife! I can’t imagine how it could have been more fun. No strings attached and in the end no one was hurt. It was dreamlike.

What was the WORST thing about this hookup? Worrying about her husband doing harm to her. She was able to convince him that nothing had happened. He was suspicious because she did not reply to his text right away.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. It does make me want to do it again but only if the circumstance was just right.

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? I have relived it many times. My favorite movie reel to masturbate to.

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? It’s probably too easy! Not sure that it’s good for marriages or society…but the genie is out of the bottle.

What do you think about the Casual Sex Project? Love reading these stories.

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