A Very Surprising Night



What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

A very surprising night

How long ago did this hookup happen? 6 months

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

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? The evening was spent with my ex-wife. We had been divorced for 6 years, we share custody of your children. Neither of us date very often, between work, kids, and their schedules— life is busy. My ex-wife is about 5’8 150 pounds with short brown hair.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was absolutely no planning involved. Our oldest had a sleep over planned, and our two middle children were at her mom’s as she was planning on going to a wine tasting event with 2 friends the next day. I was acting as taxi driver that night, driving our oldest to his friend’s house. She asked me to come back to sign some review some summer camp stuff when i was done. Nothing unusual.

She offered coffee, I accepted and we started talking. Somehow the conversation turned to our dating life, or lackthereof, and she said the only sex she is getting is from watching porn and using her toys….

We moved to the couch in the living room and started watching some tv, and it became more flirtatious. As she sat next to me, I started kissing her neck, then her shoulder, and she began to moan softly– then we began kissing and touching— she grabbed me by the hand and led me to the bedroom.

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? Now, this is where it gets interesting. Our sex life while we were together was very vanilla, I often tried to discuss exploring new acts, positions, but my ex-wife (Kim for the sake of this) was always hesitant.

As I moved down her body kissing her, I jokingly asked her “want to tell me about that porn you watch?”, and she said giggled nervously, and said, “oh, there is so much I want to try now…”

I moved between her legs and started to eat her pussy, and to my absolute shock, she said, “put a finger in my asshole”— I was stunned— STUNNED….this was a very very vanilla woman, and she said it again, “finger my ass, I want to see what it feels like”—- Wham– I was there, slowly easing my finger into her ass—-she moaned– as I began to lick her clit, she moved her ass on my finger– moaning, panting….I then decided to get even freakier for her— I rolled her hips back and started to rim her ass-my– she let out a gigantic, “ohhhhh god” as my tongue rolled over her asshole. I asked her if she wanted me to stop, “Fuck no!” she yelled. I licked, teased, ate her ass for the next few minutes while working her clit with my fingers— after 3-4 minutes, she yelled, “I’m cumming”—she pulled my face tight into her asshole and I never stopped——-after the waves calmed down…….she giggled like a teen, and said asked me, “what was that?”

The next 45 minutes was just frantic sexual tension being released. We fucked doggy style– and then she hit me with, “I want it in my ass”, we had never.. NOT ONE TIME, ever tried anal sex in our 8 years of marriage, despite me trying/asking 35,000 times– now here I was, fucking my ex-wife and her asking me to try anal sex……

She did a quick run to the bathroom to find some type of lube— came back and we proceeded with the “no such thing as too much lube” in anal—-

I entered her ass– slowly– very slowly– and 5 seconds into it, Kim was panting like she was in heat—-she stammered– “oh god, this feels soooo good”, “this is what we missed out on…”, and then slowly started to fuck me back–moving harder and faster against my cock.

As I picked up my pace, I knew I would not last much longer. The thought/image of my cock in her ass was driving me nuts– she asked me if I was close, “HELL YEAH!” I said back– and she demanded that I cum in her ass— which was all I needed— I let go into her asshole and then we fell onto the bed– laughing, cuddling– smiling.

We had sex the rest of the night, just relaxing, exploring, trying— it was a brand new world.

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 spent the night.

Showered in the morning and went home.

She went on her wine tasting event.

She texted me throughout the day, with naughty things— said to me, “we can never be married, but we can really have sex, right?”

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? 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? Just to see my ex-wife open up to her sexual potential. She was so reserved and closed to any possibilities– this was nice.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Very interesting.

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