by Nick


Gender: Male
Age: 35/30 Then
Race/ethnicity: White
Location: Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Psychologist
Relationship status: Single
Religious affiliation: Catholic
How religious are you? A little
What best describes your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 23
How many hookup stories have you here posted before? A Few

Freckles

How long ago did this hookup happen? Five Years Ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? 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? Jane is my ex-fiancée. She was a pretty redhead with pale skin and Freckles, a nickname I used with her for much of our relationship. She was also short but with a good body.  
We had actually lived in the same building for about three years when we got involved. When I had moved in I was dating a Marine and eventually we broke up. Jane and I used to pass at the mail boxes or in the hall once in a while, and I saw her at the gym a few times.  
We actually met through unusual circumstances. We were stuck in an elevator during a blackout for about six hours just me and her. We had spoken briefly and I had given her some water, and settled into doing some reading I needed to catch up on. About forty-five minutes later she asked to talk to me, she was sweating heavily and nervous. Jane confessed to being very claustrophobic and asked if we could talk to distract her.
We actually talked the entire rest of the time.  Jane and I had a lot in common, both from small towns, both the first in our families to graduate college, and so on. She was intelligent and educated, just my type. I liked her, and seen her at her worst at the same time. 
I asked her to dinner two days later and we went out. Took me a while to get her in bed but I did a few weeks later. First time I had her topless and we were making out on the couch but my roommate came home and Jane got very nervous and left. Finally bedded her a few days later after a romantic dinner I cooked. Women like a man who could cook.
Physically Jane wasn’t really my type but she on purpose gained about twenty pounds the first few months we were dating that went all into her chest and butt and gave her more curves which I really liked and she also grew her hair out.
Jane and I were a couple for a little over two years, and lived together for most of it. She was good with my son too (See My Son’s Mom). We both fell in love. 
Eventually I asked Jane to marry me and she said yes, the only woman I ever proposed to. I was planning for the future but anytime I brought setting a date or any wedding stuff up Jane changed the subject. I had reached a point I wanted to get married and start a family. Eventually Jane and I had a huge blowout over this and realized we had far different ideas of the future, I wanted to get married and Jane wanted to just be one of those couples who stays engaged forever. I decided to break off the engagement.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was about two weeks after Jane and I split up. My usual hookup, my son’s mother, was now in a serious relationship and I had struck out the few times with women. My game was seriously off.  
I had gone back to the apartment Jane and I had shared, we had both moved out. Jane was there packing a few things and we got to talking, eventually she brushed my arm and we started kissing leading to making out and some heavy petting.

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? We practically tore each other’s clothes off. I even ripped her blouse a bit and quickly took her bra off to get at her breasts. I licked and sucked her breasts a bit. She then took my shirt off, all while we kept kissing and I worked her back towards a couch we had left there. Jane and I finally had all our clothes off. When we had dated Jane had been less open sexually than many of the women I had been with before. Beyond doggie style and girl on top she wasn’t really willing to try anything. Even oral, she didn’t care for giving but she really did like receiving. However this was different, I got pretty rough with her and she did with me. We were grabbing each other hard and there was some hair pulling by both of us and I pinned her on the couch. I would have said we used to make love but this was fucking. I stuck my cock in her and rode her for about fifteen minutes.  We were always a loud couple and Jane was moaning loudly and screaming. We both orgasmed around the same time. 
A little embarrassed that we had given into passion and lust we both dressed quickly and I left.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Didn’t use protection but Jane and I hadn’t been with anyone else since the breakup, and she was still on the pill.

What were your REASONS for having this hookup? I gave into passion and lust.

Were alcohol or drugs involved? If so, how much? Not by me and I knew Jane rarely even 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? Jane and I didn’t see each other for a long time. Eventually I moved on and started seeing other people. Ran into Jane about a year later and we spoke briefly. Didn’t talk to her again for years.  
About a year ago Jane friended me on Facebook. I was seeing Ruth (See The Cop) at the time and we had an agreement about talking to ex’s on Facebook, just some quick catch up and to let them know we were not single.  
Mostly I look back on my time with Jane fondly, other than the end it was a good relationship and good for me. Honestly if I saw Jane right now I am not sure what I would do or how I would feel.

To whom did you talk about the hookup? How did they react? My roommate, someone I lived with off and on for about ten years. As usual any time I hooked up with an ex he thought this was a bad idea.

Was this a consensual and/or wanted experience for you? For your partner? For both of us very much.

Do you regret this hookup? If so, why? A little, while sex with an ex is always fun and usually great it does bring up a lot of hard feelings.

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? Sex with someone I knew and was familiar with and knew what I liked. Worst part was the feelings it tore back to the surface however if Jane had been like that while we were dating we would maybe still be together.  Not sure this one really changed anything about how I feel about myself or casual sex.

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

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

Anything else you want to add about this hookup or anything else? If I could offer a little advice here, first if you do get involved with someone who lives in the same building you instantly have a live in lover.  Also regarding cooking, in my experience women love a man who can cook and I have more than one woman over with my culinary skills.   Cooking classes are also a great place to meet women, I can count two ex’s and two other women I had casual relationships with that I met at cooking class.

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