by Angie

Gender: Female
Age: 44
Race/ethnicity: Mixed
Location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Lawyer
Relationship status: Divorced
Religious affiliation: Lutheran
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? None

Cougar on the Prowl

How long ago did this hookup happen? A year

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? Tommy was 20 Years old, a fit Latino man with dark brown hair and light brown skin. He is the son of one of my neighbors in the building I moved into after I left my husband, back for the summer to stay with his parents.  We passed each other in the mail room a few times, used the rec room in our building at the same time and I knew he was checking me out while I worked out. We spoke a few times and he was educated and charming. I liked and was attracted to Tommy but I was unsure about going near a boy the same age as my own son.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Circumstances were as follows, I had left my husband a few months prior. The marriage had truly been over for years, he had a girlfriend on the side and little sexual interest in me. It hadn’t always been terrible, we had been financially well off so when our children were young I had not worked. However I returned to the workforce when my daughter was in the sixth grade and started making a lot more money than my husband putting the first real strain on our marriage. After my daughter finished high school and went off to college I told my husband I wanted a divorce and moved out. We were married twenty-one years.
I dated a little bit, nothing serious and didn’t sleep with anyone. However like a lot of women my age my libido was up and I was a lot hornier than I used to be. I was checking out men a lot more.
My friend Abby had been divorced for years and talked me into going on a single’s cruise on the river. It was a cougar cruise, mostly middle aged women like myself and twenty something men and Abby had not told me that. I felt really out of place and Abby took off with some jock type early in the night. I talked to a few boys, so much younger than me they were boys really. I flirted with a few but didn’t feel a connection with any. I headed for the bar planning to drink a bit since I would be stuck on the water at least another hour.
Tommy came up to me and we started talking. He said he liked more mature women but he also felt a bit out of place. We flirted a lot, started kissing and ended up back in my car making out. He had his hand up my dress and we almost had sex right there but I put an end to it. As much as I wanted to and as horny as I was, I have never been one to sleep with a guy on the first date. Second date is something far different in my book. I cooked dinner at my place, went to Victoria’s Secret for some lingerie, and also bought a revealing dress. Tommy and I ate dinner, started kissing, and headed for 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? 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? I was really nervous, I hadn’t been with a man other than my husband in twenty-three years and it had also been about a year since I had sex. Tommy was really patient with me, he took his shirt off and then undressed me slowly. He unzipped my dress and kissed my neck and skin and admired every inch of me. I have had a little work done, had two kids after all. He took my bra and panties off and then asked me to lay down on the bed. I did, and he removed his pants and boxers, and he was quite well endowed.
He started kissing me and working his way down. He licked and sucked my breasts and he was always very fascinated with them. He began to eat me and it felt incredible, no one had given me oral in over a decade. I orgasmed and then he penetrated me. He wasn’t nearly as good at this, I still think Tommy was a bit inexperienced but he got better at pleasing me. He came after a while inside me, and then I asked him to stay as it was pretty late. He did and I fell asleep in his arms.
Next morning I was feeling horny again and I mounted him. Cowgirl has always been my favorite but my husband was never into it. Tommy was and woke up and grabbed by breasts hard and we orgasmed nearly together. We then showered together, a lot of kissing but no intercourse and Tommy went home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Honestly I was really foolish here, we didn’t discuss it at all and did not use protection and I let him finish inside me. A few weeks later even thought I might have been pregnant but I was just sick.  Tommy and I were a lot more careful after that.

What were your REASONS for having this hookup? Being horny and I was really attracted to him and it had also been a long time since a man wanted me.

Were alcohol or drugs involved? If so, how much? The night we hooked up neither of us actually drank

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? Tommy and I were together a few months, until he went back to college in the early fall. He could come over and get it up whenever the mood struck me so we made love a lot. He got a lot better at it well, the next girl is very lucky. I was still on the rebound from my divorce so I was not looking for any sort of relationship still I found myself developing feelings for Tommy. However this was about when he went back to college a thousand miles away.
I was hurt when we split up but I can’t pretend like I didn’t enjoy myself and get exactly what I wanted. For that I am grateful to Tommy. I had hoped to pick things back up when he got off of school again but he came home a month ago with a girlfriend his own age and I could tell they were in love so I have stayed away.

To whom did you talk about the hookup? How did they react? I told Abby who was proud of me. My daughter also caught us together and she was appalled at the idea of her mother having sex and with a boy not much older than her.

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

Do you regret this hookup? If so, why? Honestly, 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? Making love again and being wanted by a man again. Worst part was that it had to end. A lot of things changed for me after this, first of all I have had two other lovers since Tommy that were both a lot younger than me. I was a lot more confident and sure of myself during and since Tommy. I changed how I dressed, a little tighter and more provocatively when I am not working and I also started wearing thongs again, first time since college. At Tommy’s request I also started shaving my private area, not something I had ever done before.
I learned it is ok for me to want and have sex and that I also prefer having much younger men in my bed.

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? I am actually not a fan of the term cougar, I find it degrading and a little offensive however I could not think of a better title.

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