Compensating My Sitter



What’s your gender? Woman
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Ulster Park, NY
Highest education received: High school diploma
What’s your occupation? Small business owner
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Adventurous
How many sexual partners have you had in your life (including oral sex)? Numerous
How many hookup stories have you here posted before? None

Compensating My Sitter

How long ago did this hookup happen? In 2001

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? I will call him Frankie. He was tall, which was a plus because I’m 5′-9″ and my boyfriend at that time, who was also my son’s father, was short, so I liked that Frankie was tall. Frankie was thin and was very cute, and actually, I was attracted to him from the first time we met. He worked with my then boyfriend, so that’s how I knew him. Frankie was in a serious relationship and a few years younger than me, at that time I was 22 and he was 20.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was close to Christmas and, I, for reasons that are too long to go into, wanted out of my relationship. Though that was not anything new, I stayed in that relationship for our son. I had been tending bar at a place called La Cantina and it was near Saugerties NY. A friend knew I was unhappy and he told me how to go to the local police station and file a complaint and a sheriff would come and have my kid’s dad removed from the house. I wasn’t sure though because my boyfriend was not from that area so it wasn’t like he had anywhere to go other than back to his home state. Finally, though, I did it, I filed a complaint, bought him a bus ticket, and the sheriff came and made him leave. He did go back to his home state which was in the midwest. The only problem was I lost my sitter! I was able to count on a few friends to watch my kid so I could continue to work. A few weeks later, because it was during the holidays, it was getting really hard to find sitters. I was at the local gas station and I heard someone call my name. I look over and it’s Frankie. We started to talk and he says he heard that my boyfriend went home and he asked me how I was and I said great, except I couldn’t find anyone to watch my kid! He volunteered right then and there and I told him to come over at 6 pm since I was scheduled to work. He said sure. He knew where I lived because it was a small town and again, he knew my boyfriend.

The place I was tending bar at was a nicer place so I would almost always wear the same thing which was a black mini skirt, tan pantyhose, black knee high lycra boots, and a white blouse, of which I would leave the top buttons undone for better tips! When Frankie got there he was like WOW you look great. I said thanks, but I knew that I did. I said I would call later to check in and see how things were going, but my son took to him right away. My boyfriend would take our son to where he worked for quick trips, so it wasn’t like Frankie had never seen or interacted with him before. Finally, the last call was announced and knowing that Frankie was at my house made me excited about the possibility of something happening, so my mind was racing on my drive home. It was late, after 2:30 am, so I wasn’t sure if he would be up for hanging out. I came in and he was sitting on the couch. I asked how it went he said fine. I said, “so hey do you need to leave or are you up for hanging out for a little while?” He said yeah he would be up for that, I said ok cool and went over by the couch where he was sitting. I asked him to pull my boots off and he did that right away. Then I said let me go check on the kid. I went into my kid’s room and unfastened the one button on the back of my mini skirt, then I unzipped it. It fell to the floor in my kid’s room and I casually went back out to the living room in just my blouse and pantyhose (I never wear anything under them). I could see his face, he was trying not to show any expression and neither was I, but we were both excited, I got a beer from the fridge and went to the couch and sat next to him. We were just bull shitting while I finished my beer.

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? Finally it was time, so I just learned over and kissed him. He kissed me back and we started to makeout. I reached over and turned the light off. While we were making out, he took my top off then undid my bra. He said I had amazing tits. I undid his pants and pulled out his dick. It was already rock hard so I went down on it, he laid back and I sucked him for at least twenty minutes. Then we got up from the couch. He followed me to my bedroom. I slipped off my pantyhose so we were both totally undressed. We fucked for a long time, starting out in missionary and moving into cowgirl and later to doggy where he pulled out and shot his load all over my back and ass. After I told him he should just stay over but he said he couldn’t, so he got dressed and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? A few weeks later my son’s dad came back. We went to court and the judge said for us to either work things out or separate. We decided to try to make things work. We moved from upstate New York to Illinois. I grew unhappy once again and my dad flew to Illinois and helped me pack and return to my home state which was Massachusetts. Years later I found Frankie on Facebook and friended him.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To cheer myself up

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

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

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

What do you think about the Casual Sex Project? It’s interesting and a good way to share an experience without any embarrassment or judgment.

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