by Chachee


Gender: Male
Age: 36
Location: CO
Highest education received: College degree (eg., BA, BS)
Occupation: Sales
Relationship status: Divorced
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? 0

Friend’s Ex Wife

How long ago did this hookup happen? A week ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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? Blonde. 5’5″ tattooed like crazy. We’ve known each other really well for at least 12 years as that is when her husband and I started hanging out. They got divorced and I also got divorced. His ex wife and I had gotten really close to hooking up one night years ago, although it never happened. I feel like over the past few years after we both have raised children and her couple of failed relationships that there has been some sexual tension. In other words, knowing we want to but afraid to make it happen due to how our families and friends would feel. There has always been an attraction.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This hookup began last Wednesday night. I will refer to the hookup as JC had gone to our friends bar for some beers with my sister (who is also one of this hookups friends). My sister left and JC and I tried drinking another beer, but was ready to go. I was also and she said we could walk home together since we live about a block away from each other. On the walk home there was some flirting. We got to her house and sat on the porch swing. Talked for about an hour, she put her toes under my leg to keep them warm. After some time, she extended her leg over my lap. We continued talking and I began to rub her foot. It got quiet for a minute and she just said this is happening and kissed me. We attempted laying on the swing but turned out it was not possible. She sat me up and this is when it happened. She pulled her panties aside and lifted her sundress and sat on my lap – she put it in. I was blown away that this was happening after all these years. So there we are in her front yard having sex on a porch swing. For one I had never had outdoor sex prior to this much less in a front yard. I loved it. I would do it again in a heartbeat now.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We eventually moved into the kitchen with the front door wide open. Here was another first, we went to the kitchen table. At this point she had stripped off everything and I got the opportunity to see all of the tattoos she had talked about for all these years. Amazing body, absolutely beautiful vagina. Probably the most beautiful one I’ve seen to date. I performed oral on her for a while. All while admiring the artwork all over her body. She was ready to go and she put it in again and we went to town. I was shocked at how big her smile was throughout all while keeping eye contact with me.  I didn’t have this kind of connection with my ex wife after 7 years of marriage and 2 beautiful children. This was amazing.

What were your REASONS for having this hookup? I don’t think there was a reason other than pure desire, curiosity and a little bit of danger.

Were alcohol or drugs involved? If so, how much? We had drank beer, I had a few. She had a few.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After, she texted me to apologize. I apologized also, we both agreed that was unnecessary. We now text about every day. She has invited me over a couple of times the last week, it just hasn’t worked out. I’d love to though.

To whom did you talk about the hookup? How did they react? Nobody. Its kind of our own dirty little secret. Something about the two of us at 36 years of age making nobody aware of what’s going on.

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes

Do you regret this hookup? If so, why? Absolutely not.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing – we’ve now done it and its out of the way. The worst part – got nothing. Has not changed my thinking on casual sex.

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 or anything else? JC – here’s to hopefully many more.

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