Unplanned Evening With An Ex



What’s your gender? Man
How old are you? 50’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Jewish
How religious are you? Not at all
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? 3 or 4

Unplanned Evening With An Ex

How long ago did this hookup happen? Last month

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

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? Together for 15 years. When we were together she had an amazing body. Aged a bit since then, but still great.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a family event. No planning was involved and frankly, it was all her idea, but I didn’t say no.

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 was at a family even in another city. I have a significant other but she rarely travels. Lately, we haven’t been getting along too well, so leaving for a family event was a good way to relax. Since this was a family event I had to attend I knew my ex would be there. We had a bitter divorce that was her idea and not mine. We were very cordial during the event since it was a happy time. Both she and I came alone without respective “dates” or significant others. As the event wound down, I said my goodbyes and went back to my hotel. She was staying at another hotel.

I was in my suite when I received a text from her asking what I was doing. I texted back that I was in my room having a drink and getting some work done. She wanted to know if I wanted to meet for a drink to which I said yes of course. She said she just wanted to talk and I was fine with it and said I would meet her in the lobby bar in an hour. 30-40 minutes later I got a text from her, saying she was early. I said she could wait at the bar for me since I wasn’t done yet, but she insisted she’d rather not wait alone and would come to my room to wait for me. Several minutes later there was a knock at my door. She had on a long trench coat as it was cold outside. I told her to make herself at home and I’d be done in a few minutes. When I came out of the bathroom OMG, she was wearing a miniskirt with some thigh-high pantyhose, a barely-there top covering her DD breasts, which of course, I paid for, and a bottle of my favorite scotch. It was pretty obvious what was on her mind and no wonder she didn’t want to wait at the bar.

She poured me a glass and one for her too even though she isn’t much of a drinker. “Do you miss us”, she said. I told her of course I do, and reminded her the break up was her idea and mine. She began crying and hugging me apologizing for the way she ruined our lives and asked if it was too late. I told her of course not and with that she and I kissed like we were never apart. She threw me on the bed and got on top of me. Under her skirt was that silky smooth shaved pussy I’d missed for so long. We had sex all night long in every position imaginable position only taking a few short naps between sessions. The room was a wreck and smelled like sex the bed was soaked with her cum and mine. There wasn’t a clean towel in sight. It was going to be obvious to housekeeping what happened in that room.

The next morning I ordered room service for us and hung a do not disturb sign on the door. We talked about life, us, and if we could pick up where we left off and sail off into the sunset together. That’s a chapter that hasn’t yet been written. That afternoon, we had to attend the after event, but there was no way she could go like that and didn’t have a change of clothes or makeup, etc. I asked what she wanted to do. She called her niece who was there at the event telling her to come to my hotel and pick up the key to her room so she could get her some things. I guess her niece anticipated this happening as she came to my room with a bag already packed. I asked her if she wanted to come in, but she declined stating she didn’t want to witness the aftermath, but was happy for us. Both of us went to the lunch together with sly grins on our faces. I have a feeling everyone there knew what happened.

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? We both felt great and only time will tell where it goes from gere

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? Didn’t really have to. I think everyone knew and her niece has a big mouth. LOL

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Reconnecting with the love of my life

What was the WORST thing about this hookup? Having to leave that hotel room

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? I love it and look forward to the stories daily.

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