by Lenny



Gender: Male
Age: 44
Race/ethnicity: Mixed
Current location: Columbus, OH
Highest education received: College degree (eg., BA, BS)
Occupation: Personal Trainer/Own a Gym
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? Seven


An Old Flame


How long ago did this hookup happen? Within the Week

How would you best classify this hookup? First of More/Sex with an Ex

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? Renee is a pretty redhead, fit with a big chest and in her early forties.  I went to high school with her and she had tutored me in math and had a huge crush on me but back then she had not been on my radar.  At our twentieth I hooked up with her and it was one of the most intense sexual experiences of my life  (See Two in One).  About a year later we hooked up again.  I really liked her and I think we both wanted a relationship, I would say I pined after her for a while,  but it just never fell together and I lost contact with her during my third marriage.  I do however consider her an ex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Renee got in contact with me a few months ago on Facebook.  We messaged a bit and made plans to meet up again when she was in town.  The biggest reason we never got into a real relationship last time was she does not live where I do.
The day Renee arrived in town we made plans to meet for lunch.  The place was a little high end for my tastes but it was where Renee wanted to eat.  She arrived in a limo and walked in, and was wearing a dark dress and quickly had the attention of most of the men there.  She sat down and we started talking, I quickly learned she had a lot more money than the last time I had seen her.  She had developed some smart phone app years back and I had seen her on the cover of a few tech magazines.  We also talked about our kids, we both have grown children.  I learned she had been single about a year, and I hadn’t really been dating anyone since my last divorce.
Now we rather quickly started touching hands and flirting.  We ended up in a stall in the men’s room making out.  I got pretty hard and Renee was pulling her dress up to mount me when we were interrupted.  We laughed a bit and made plans for her to come by my place that evening.  She arrived in a long coat.

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? Renee was wearing sexy black lingerie, a lace bra and panties and stockings that worked well on her pale skin.  We started making out and quickly made the way to my bedroom.  She took her bra off and asked me to lay back and she pulled my pants down and began to suck my cock.  I had asked when we hooked up in the past but Renee had never been into oral.  She was good at it and I rather enjoyed it and got rather hard before she stopped.
She took her panties off revealing quite the bush.  It was a bit of a turn off for me but not a deal breaker but Renee picked up on it and would later tell me she hadn’t been maintaining herself as much since she was single, she was also about fifteen or twenty pounds or so heavier than the last time I had been with her but still in good shape and had a few more tattoos which I liked.  Everything on her was still also quite firm.
Now she was trying to mount me but I grabbed her and turned her over.  I kissed her a bit and then moved to her breasts and sucked on them a bit.  I then penetrated her and rode Renee and kissed her some.  We both orgasmed about the same time and Renee got pretty loud.  Afterwards we cuddled for a bit and chatted, mostly about our kids and she offered some advice with my oldest who has been having a lot of problems.  She also asked what would have happened if we would have hooked up in high school which really made me reconsider things.
We fell asleep afterwards and in the morning we ate breakfast and took a shower together.  That turned into shower sex, hot and steamy but not that practical since my shower is not really big enough for it so it did not last long.  Afterwards she dressed for work which I rather enjoyed watching and then gave me a kiss goodbye and left for work.

Did you have an orgasm? Did your partner(s)?: We both did in the bed but not in the shower
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not use a condom but I tested clean just a few weeks ago, I am careful and get tested regularly.  Renee has never been into condoms but is on birth control

What were your REASONS for having this hookup? I really liked Renee and enjoyed being with her in the past

Were alcohol or drugs involved? If so, how much? I offered her some wine but Renee turned it down.  Since I had last seen her Renee has quit drinking at all

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? A lot of texting back and forth between me and her including sending some naked picks and a little sexting that has been very dirty.  She sent me one of the Brazilian she had done which I really liked.  We have spent one more night together since and she will be in town a while this time.  I think I am beginning to develop feelings for Renee and I am hopeful for the future.

To whom did you talk about the hookup? How did they react? Wasn’t really planning on telling anyone but Renee came by the gym and after she left my business partner said I was totally fucking that woman and I couldn’t deny it.  She was actually quite impressed with Renee.

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

Do you regret this hookup? If so, why? Not at all

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? Being with Renee again and someone I had really enjoyed in the past and the possibility of maybe having a relationship with her this time.  Renee is the first person I have even considered a relationship with since my last divorce.  Now Renee bringing up what would have happened had we hooked up in high school has made me greatly reconsider things and how I have been in relationships in the past.  I want to think that my sexual history and life would have been very different had I hooked up with Renee when we were young but being honest I think Renee would most likely just be one more of my many ex’s.

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

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

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