by Saul

Gender: Male
Age: 29
Race/ethnicity: White
Location: Pacific Northwest
Highest education received: College degree (eg., BA, BS)
Occupation: Bookkeeper
Relationship status: Single
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? Three

Sex and the Single Mom

How long ago did this hookup happen? Three Years Ago

How would you best classify this hookup? One Time Thing that led to More

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? Vicky is a single Mom, curvy but good looking with long black hair. She was pretty short, only 5’1” and about two years older than me. We met at the supermarket, I am a single Dad and my then three year old daughter was staying with me for a month while her Mom went to take care of her sick Mom.
I was doing some shopping and paying attention to my daughter, back then she was still at an age where everything she did was cute. I was a little confused and Vicky came up to me, she would later tell me she never would have if my daughter had not been with me. Honestly, my daughter works better than a puppy with women. Vicky helped me finish my shopping and told me she had a son about the same age, and she was single too.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Nothing happened between me and Vicky for a little over two months. I got my daughter into the same playgroup as her son for when she was with me, and Vicky and I were around each other a lot. Her house was only a few blocks from my apartment at the time. Ninety percent of the time either one or usually both kids were around though. There was some brushing against each other and light flirting, but we were more friends at first really.
Two months in one of the other moms in the group was taking the kids for the day, Vicky’s was the drop off point and I had stayed to help her with her computer. I can remember she smelled nice and we brushed against each other and were just looking at one another. I can remember wanting to take a chance so I kissed her on the lips and she didn’t resist.

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? Vicky asked me to trust her and undid my belt and pulled my pants down and proceeded to lick my balls and suck my cock. It felt great, I had suffered a back injury about seven months prior and other than a woman who did not react well when I couldn’t preform I had not had sex in a very long time. Vicky however knew full well of my back injury. Vicky asked me to warn her when I was getting close and I did.
I wanted her in that moment, and picked her up and put her on the dining room table. I pulled her pants down, she just had sweats on and stuck my cock in her and fucked her for just a few minutes and I was already very hard from the oral. She started moaning and we both orgasmed very close together and I dumped a load in her. We both sat there a minute and Vicky then pulled her pants up and told me to get dressed and go, she was embarrassed. I then left.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Foolishly none, despite the fact Vicky and I both had unplanned kids. However Vicky took a morning after pill and I went and got tested a week later. Luckily nothing happened.

What were your REASONS for having this hookup? It had been a long time for me and I did like her.

Were alcohol or drugs involved? If so, how much? Not 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? Vicky avoided me for two days and I called her a few times. However she knocked on my door one evening, in a very revealing black dress I would probably call slutty and she had her hair done up and makeup on and a bottle of wine.  She admitted to being very attracted to me but hadn’t really gone near a man since her son’s dad and she had reacted badly. We never did get to that bottle of wine but we went upstairs and spent the night having sex.  
Vicky and I were a couple for a little less than two years after that. I was in a committed and monogamous relationship and able to keep my hands off my daughter’s mom (see Why I Don’t Date Coworkers). Our kids spent a lot of time together and my daughter got pretty attached. I developed strong feelings for Vicky and I will admit I loved her. We moved in together about six months later and things were really good for a long time.
However work changed for me and I began to travel a great deal and spent weeks at a time away. This was very hard on Vicky but we tried to make a go of it. She trusted me and there were no accusations of cheating and I was honestly never tempted, I am not that guy. We decided to break up which was very hard on both of us and our kids and my daughter kept asking me where Vicky was.  
I loved Vicky but I have only seen her twice since the breakup, she moved across town. I still care about her but I have no expectations for the future.

To whom did you talk about the hookup? How did they react? Told my roommate right away bragging a bit and he was impressed. However mostly I have never shared the details of the first time Vicky and I hooked up as to protect her reputation.

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? The sex and relationship part not at all, how it ended and I think that damaged my daughter a bit.

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? Good sex with someone I cared about. Worst part was the fallout with my daughter after Vicky and I split up. I have since decided that someone only meets my daughter once we are seriously involved and it’s going somewhere. To be honest I am not sure there is a such thing as casual sex, there is nothing really casual about sex and the act of making love.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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