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Babysitter

NOBGE said:
Many years ago, when I was in college, one of the gals in the office where I worked and I started flirting. She was about 7 years older than I and had a daughter. One day, she said she wanted to go out with her g'friends but didn't have anyone to watch her daughter. Being the nice guy I am, I offered. She took me up on the offer and went out for the evening. When she came home, she "repaid" me in bed. I "babysat" for her many more times. She'd go out with her friends and come home and we'd spend the next few hours in her bed!
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you lucky dog!
 
My fiance and I "role play" this scenario in bed sometimes....where I'm the "younger, naive babysitter"....yet willing to please. ;)
 
We had a sexy babysitter but nothing ever came from it. She was a good Christian girl. LOL
 
Years back before the kiddies left, there was a recently married women with two daughters. The oldest was our primary babysitter for several years. She and I grew close as friends, mostly because I didn't diss her off as a kid and let her participate my DIY projects.

The step-father of maybe 4 years suddenly died, and the 3 girls soon moved 2000 miles away. I'd always been hot for the babysitter (not to mention her mom) so the day before they left, I got daughter alone to say goodbye.

She fumbled my first (maybe 5 second) kiss but after several moments to get herself centered, she initiated a second kiss. I got the feeling that she was learning as she went, but was a quick study!

At the end, we were lip-locked with my leg between hers and my hands on her butt pulling her bottom against my thigh. She had her hands around my waist, rocking against me.

We stopped after a couple of minutes least our absence from the group become a problem (and I was scared that we were moving too fast!)

About a month after they moved, I got a VERY flirty/suggestive card from daughter. She had crushed on me for a long time and really wished I'd not waited until she left to make my move. She fantasied I would be her first and teach her everything.

My long running fantasy too!
 
I'm so envious of the posters who got a shot at their sitter! (and visa versa)
 
My boyfriend lost his virginity to his babysitter.
It's funny to hear him and his mom joke about it now.
"Well if I had known that that was going on I sure wouldn't have hired her."
 
A guy I used to know once told me that when he was a babysitter, the husband came home with a woman who was not his wife and took her to bed. Eventually, the wife came back and drove him (the babysitter) home. Before she dropped him off, she seduced him. She gave him his first ever blowjob in the front, and then she took his virginity in the back of her van. Unfortunately for him, there was never a repeat.
 
BongoGal said:
A guy I used to know once told me that when he was a babysitter, the husband came home with a woman who was not his wife and took her to bed. Eventually, the wife came back and drove him (the babysitter) home. Before she dropped him off, she seduced him. She gave him his first ever blowjob in the front, and then she took his virginity in the back of her van. Unfortunately for him, there was never a repeat.
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wow...kinky couple...lucky friend!
 
I was a babysitter for many years as well, but nothing ever happened. It has always bee a fantasy of mine tho.
 
Sexy Little Sitter

When I was around 30 years old, we used to get this babysitter for our two little kids whenever we went out. She was in her mid-late teens and was one of those girls that was innocent and a little bit shy. She was built like her Mom ... pear shaped, small waist, nice titties and wide hips. I'm getting excited just thinking about her.

She lived a little ways away from us and I had to pick her up and take her home at the end of the night. Whenever I picked her up, she was always friendly but didn't say too much. But, whenever I drove her home, she was always full of questions and never seemed to quit talking.

"So, where did you go / what did you do tonight?" "Sounds like fun." I wish I could do that." "I wish somebody would take me out." I can't wait to start dating." Always speaking in a soft sensual voice. And I would always get turned on by the time we got to her house.

I guess I was too young or naive to take advantage of the situation. Looking back, I now know that she was flirting with me and who knows where things would have went if I would've seduced her at the time.

I run into her every now & then (it's 25 years later) and we usually just catch up on what each other is doing now. She never had any kids so we usually talk about what's happening with my family etc.

I bumped into her the other day at the mall and she proceeds to tell me that she's now separated, doesn't do too much anymore, stays at home a lot and needs 'something exciting' to happen in her life. She adds that she's changed firms and lets me know where she's working now and where she can be reached during the day. She may as well have said, "Why don't we get together and fuck."

Needless to say, I know what she's saying now, and it gets me hard every time I think about it. I used to fantasize about her sometimes when I jerked, but now I'm thinking about all the things that could have happened back when she was the babysitter.

And, although I would still love to fuck her, nothing has happened between us. But, she's still a great fantasy.
 
vadere said:
When I was around 30 years old, we used to get this babysitter for our two little kids whenever we went out. She was in her mid-late teens and was one of those girls that was innocent and a little bit shy. She was built like her Mom ... pear shaped, small waist, nice titties and wide hips. I'm getting excited just thinking about her.

She lived a little ways away from us and I had to pick her up and take her home at the end of the night. Whenever I picked her up, she was always friendly but didn't say too much. But, whenever I drove her home, she was always full of questions and never seemed to quit talking.

"So, where did you go / what did you do tonight?" "Sounds like fun." I wish I could do that." "I wish somebody would take me out." I can't wait to start dating." Always speaking in a soft sensual voice. And I would always get turned on by the time we got to her house.

I guess I was too young or naive to take advantage of the situation. Looking back, I now know that she was flirting with me and who knows where things would have went if I would've seduced her at the time.

I run into her every now & then (it's 25 years later) and we usually just catch up on what each other is doing now. She never had any kids so we usually talk about what's happening with my family etc.

I bumped into her the other day at the mall and she proceeds to tell me that she's now separated, doesn't do too much anymore, stays at home a lot and needs 'something exciting' to happen in her life. She adds that she's changed firms and lets me know where she's working now and where she can be reached during the day. She may as well have said, "Why don't we get together and fuck."

Needless to say, I know what she's saying now, and it gets me hard every time I think about it. I used to fantasize about her sometimes when I jerked, but now I'm thinking about all the things that could have happened back when she was the babysitter.

And, although I would still love to fuck her, nothing has happened between us. But, she's still a great fantasy.
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So it's not so much a question of your age then or now ... you were just decent (or dumb :D) enough not to exploit the situation
 
vibes said:
So it's not so much a question of your age then or now ... you were just decent (or dumb :D) enough not to exploit the situation
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That's right. Also, I was younger and thought differently back then. I can remember being nervous and maybe a little bit afarid to try anything.
I think something may have happened if she woud've been just a tiny bit more aggressive. But, she was probably waiting for me to do something.
 
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