by AlwaysThinking

Gender: Male
Age: 24 at the time [~45 now]
Race/ethnicity: White/Caucasian
Location: USA
Highest education received: College degree (eg., BA, BS)
Occupation: Engineer
Religious affiliation: Searching at the time, now settled on one of the big ones
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

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The Cat and I Are a Package Deal

How long ago did this hookup happen? 20+ years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, paid sex; something else.)? 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? My ex and I had been in and out of a very intense relationship when we were both in college. She was gorgeous — very curvaceous, wonderful eyes, dark hair. We met through mutual friends, lived together one summer, broke up, got back together, and were together when we graduated. She decided to take the first job offer she got in a part of the country she knew I did not want to live in, which devastated me. I took a job in my dream city, about 10 hours from her. We tried the long distance thing, but we broke up less than a year after graduating. I told people it was mutual but I knew it was really her that broke up with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had a cat at college, and this cat was very shy around people to an extreme degree. Her job would require her to travel a lot and we agreed that it would be best for the cat if I took her. In the break-up, I got the cat. After we had been apart for close to 18 months with no communication whatsoever I got an email from my ex out of the blue saying that she had a business trip to my city, and she wanted to see the cat. She instructed me to leave a key under my mat, exit myself from my apartment at a set time, and then return two hours later. I thought about this for a while, and then I summoned up a ton of courage and replied that the cat and I were a package deal, and she was welcome to come see us both, but I was not getting thrown out of my own apartment.

She accepted. As the visitation day approached, I started to wonder/fantasize about sexy time with her one more time. I decided that if the mood was right, to go for it. I had not had anything approaching a serious relationship since we broke up, and I missed how hard it was to find someone I clicked with, not to mention the intimacy, touching, kissing, and all that.

She showed up on time, and the first thing I noticed was she looked like a wreck. She had put on weight, and her beautiful hair was not flattering at all. Still, we clicked. I was Mr. Charming and as we played with the cat, we talked. I had made dinner for us, but it turns out she had become vegan since I saw her last, and an enduring memory from that night is going to the grocery store together near my apartment and her showing me what foods she would and would not eat, as she bought something for herself.

Back at my apartment we ate, talked, played with the cat, and maybe we had a glass of wine, I don’t remember. Then I leaned into kiss her. “Are you sure you want to do this”, she asked me? I was sure.

We made out, fully clothed, and it was wonderful. She still kissed great. When it started to get late, I told her I did not want to say good night to her. She said she could not stay because she had an early meeting the next day, but if I wanted I could stay with her at her hotel, which was about 30 minutes away in another part of the city. Into our cars we piled.

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? At her hotel room, she got ready for bed, and joined me in her king-sized bed. She told me she was not on birth control so we could not do full intercourse. In all our times together, we had never done that anyway. We had tried several times but it hurt too much for her or she was too conflicted and we had never completed the full traditional sex act. So when this was off the table tonight it wasn’t a big deal. I kissed her all over, I and remember how happy I was to see her freckles, moles, and scars that I had missed so much. I held her and kissed her and tried to rub her vagina as she had taught me years ago. She gently told me that she wasn’t ready to go that far yet , and then gave me a great orgasm with her hands. We lay there in post-sex bliss for a while, and she really opened up to me about her life, and how it was kind of a mess. She had had some disastrous dates with guys her mom set her up with, and some other stuff that I don’t want to share here to protect her privacy. Suffice to say that the stories she told me would have really freaked me out if we had still been dating. I would have been in a place of judgement. But tonight, I could just listen and be there for her. I remember this talk very fondly. I felt like we were truly intimate. More kissing, and this time she let me touch her and I brought her to a great orgasm. I brought myself off one more time and we fell asleep.

She had done something truly awesome and set her alarm for thirty minutes earlier than she needed so we had one more session in the morning before she had to get up. I laid in bed while she showered, and as she got dressed (it is very sexy to watch a lady get dressed for work, I might add) she invited me to come visit her. She told me she no longer had reservations about full-on sex, and she’d go back on the pill. I was walking on air.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? As was our custom, we did not have full intercourse, per a discussion.

What were your REASONS for having this hookup? I missed intimacy, and I missed being with someone who I knew and who knew me.

Were alcohol or drugs involved? If so, how much? Nothing significant.

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? Afterwards I made plans to visit her and have full-on penetrative sex with her. Sadly, the cat that was hers and was now mine ran away just before I was supposed to fly to her city. I cancelled my trip to look for the cat. Besides really wanting to find the cat, I knew my ex would not be happy knowing the cat was lost and the weekend would be ruined anyway. After the cancelled weekend, my ex had a change of heart and I got a letter in the mail from her saying she never wanted to have anything to do with me again. It was written on a napkin that airlines give out in flight. Apparently she wrote it while flying on one of her business trips and she listed everything that was wrong with me. It was actually so comical I did not take it personally. I never saw her or the cat again.

To whom did you talk about the hookup? How did they react? I kept this to myself. I think the people who knew me at the time would have been surprised.

Was this a consensual and/or wanted experience for you? For your partner? Yes all around. There was some premeditation on my part; I don’t know what she had in mind before she came over.

Do you regret this hookup? If so, why? No I don’t. We had a great night of intimacy. The aftermath helped me realize that we could never be together and that I deserved better.

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? The best was some clarity on our on-again-off-again relationship, which was a very significant part of my life for several years. The sex was really good too, which I probably needed.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? The hotel we were in is still there. It is a name-brand high-end business hotel. Every time I go by it I think back to that night. A memory is coming down to the hotel parking lot the morning after in already-worn clothes and thinking that the parking attendants could tell what I had been up to.  I am married with kids now, and according to social media, so is she. And I really miss that cat.

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