Staying The Night After Babysitting

by Babysitter

What’s your gender? Woman
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Netherlands
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 45
How many hookup stories have you here posted before? 0

Staying The Night After Babysitting

How long ago did this hookup happen? 2.5 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 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? He was a man at the beginning of his forties and looked it, but also sporty, as he did quite a lot of physical activities in his spare time. I knew him only a little bit. I had been babysitting his and his wife’s kids a couple of times, and of course before and after there were small chats involved to get to know each other. I found him an attractive guy instantly. That was because he was older than me, he had this naughty look in his eyes, and he came across as a young and vibrant soul to me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was babysitting that night. The kids were sleeping and he came home, alone. His wife was gone for the weekend apparently. He asked me whether I wanted a glass of wine, while he was talking about the lecture he had been to that night. It was an interesting subject, so we got into a discussion and I accepted the wine. We talked more and more about several subjects, including love and relationships and why this society is mostly monogamous and why it is so hard to love more than one person without hurting your spouse. I thought it was a very interesting topic and talking about it made me wonder how I saw these things. Also, I was honored that he opened up to me about it and it gave me the exciting feeling that he was attracted to me somehow. Meanwhile, we were drinking more wine, eating cheese and listening to music that came across as very sexy to me. It had this mysterious/dark sound and it gave a boosting effect to our conversation.

It was getting late and I needed to cycle home a long way. It was snowing and he, therefore, asked me if I wanted to stay for the night. First I said no because the snow was not so heavy and I didn’t mind to cycle through. I also thought it was a bit odd to stay. But he convinced me that it was no problem at all: he had a spare bedroom and the kids were used to having friends over from their parents, so it was nothing to worry about. I played being naive and accepted the offer. There was something exciting about this and I think I somehow wanted to know his motives for asking me to stay.

He showed me my bed and he went to his own room. I undressed and put a T-shirt on that he had given to me. As I was lying awake, I was thinking about the evening: ‘Why did he persuade me into sleeping here? Has he got ‘plans’ with me, or is this really just favour, so I don’t have to cycle through the snow?’. As I was thinking over these things it made me feel a little disappointed as well. Those days I was a very sexual person, and whenever I felt a sexual tension with someone, I had the wish to act upon it (although I didn’t want to hurt anyone of course).

Then, he suddenly came back into my room and said he thought it was a special night with me and that he had enjoyed talking to me about such intimate matters. He thought it would be good to give me a hug… Deep inside I was enjoying the fact that I had picked up on his signs and that I was right about his motives.

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? He crept into my bed and we gave each other a big hug. There was this moment where it had to either stop or evolve to something more. Those seconds felt like ages. I can’t remember who started the kissing, but I know we both wanted it. I felt like an animal, feeling those sexual urges. We touched and kissed each other everywhere and he wanted to penetrate me. I wanted that too. He put on a condom and he came as soon as he was in me. I regarded it as a compliment, as we were so into each other that the tension had risen sky high. Then he wanted to please me with his hands and I gave him careful instructions because although I had had many sex partners, I almost never came. But with him I did, and it felt magical… After this, we lay next to each other talking a bit more. He then went back to his own bed and we went to sleep in our separate beds. But only for 3 hours or so, as the kids had to go to school early. I got up and acted normal to them. They didn’t seem surprised, luckily. As they went to school, I went home on my bike, feeling a bit special and bizarre.

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? I started feeling bad about it the next day. I called him to say that I didn’t want this to ever happen again and that I didn’t want to babysit anymore. He reassured me that there was nothing to worry about and that he could explain how these things worked for him and his wife. We met in a cafe to talk things through and he told me that his wife knew he sometimes had sexcapades. It reassured me a lot and we kept on seeing each other sometimes, to have a good conversation or to kiss, but never again I went to his house and never again we had sex. I see him as a special friend now and that is how I like to keep it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? To a close friend. She reacted not so positive. She said she felt bad for his kids. I was disappointed that she couldn’t see the exciting side of the whole experience because I felt the need to share the story from my viewpoint.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I am not sure whether his wife was entirely ok with it, and I still don’t know if she knows about this specific event. It makes me feel bad that I had fun while maybe hurting someone else.

What was the BEST thing about this hookup? The closeness I felt. My hookups before were more about the sex and I didn’t before feel so emotionally close to someone.

What was the WORST thing about this hookup? I was scared someone would find out and that his wife would know it was me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes absolutely. It still makes me think about monogamy, polyamory, and affairs a lot. To what extent can we love more people without hurting others? And to what extent would it be possible to have a sexcapade every once in a while, with your spouse knowing that, but not knowing who/how/etc.? It has given me a more open mind about it, but still, I am monogamous in my relationship now. Although I expect it to become more open as the years go by. But I think we would like to experience new things/people together and not apart. I can’t imagine me feeling totally ok about my current partner doing something sexual without me.

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

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

What do you think about the Casual Sex Project? Very nice! We need to read real and honest stories to understand what is ‘normal’.

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