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Babysitter

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Has anyone ever has fooled around with your babysitter or your kids babysitter?
 
As a 18 year old girl, I babysit a lot but have never been seduced ;( maybe i'm not pretty enough.
 
Also a big fantasy of mine, but never happened. :(

Maybe I should have hired Hornykitty
 
Hell, after I got a real job at 15 I quit babysitting. lol Didn't look back and continued real jobs at 18!
 
I once had sex with my nieces's babysitter. I stopped by their house, not knowing they were out for the evening. My oldest niece was about 7 at the time, and my favorite, she insisted I stay and play with her. When she finally crashed an hour later, Sandy, the babysitter, and I heated up some dinner and chatted. I opened a bottle of my brother in-law's wine, which he treasures. She was like 15 years younger than I, but seemed to be totally turned on by the situation - who I was to complain???
 
once!

Many years ago I came home on a late flight. Wife out of town at sisters helping her through a rough time. I was trying to be very quiet entering house so as to not wake kids and babysitter. I wear boxers to bed and went to the kitchen to grab a glass of wine (I was still wide awake and wanted to read before I went to bed). Walking out of the kitchen I almost ran directly into the babysitter as she was entering the kitchen to grab some water from the refrigerator. We scared the crap out of each other and then began to laugh. She was wearing a T-Shirt that was slightly above her bottom. I could not tell if she was wearing anything underneath.

We stood there chatting for quite awhile when I finally asked if she wanted a glass of wine. She readily agreed and we sat down in the den. One glass led to another and we were having a fun time chatting away. She said she needed to use the bathroom and got up and left the room. My eyes followed her ass as the t-shirt was bunched up above her ass that was, without panties! I about came in my pants! It was difficult to keep my hard cock from making a major tent in my boxers.

When she returned she filled our glasses with more wine and sat in the chair across from me. She crossed her legs and I caught a slight glance of her bush. I needed to pee but could not get rid of my erection! She reached down to pick up a pillow off the floor and I caught a wonderful look at her tits through the top of her t-shirt.

I could not take it anymore and told her I was going to bed, that I was tired. I stood up and, don't know what possessed me, reached over and pulled her from the chair and gave her a big hug goodnight. I squeezed her tight and was surprised how my cock broke out of the fly in the boxers and felt the smoothness of her stomach. She knew what had happened, pulled her head back, looked at me and smiled. With that smile I came all over her stomach and legs. I felt like a 12 year old! I began apologized like a fool while she just laughed and said not to worry.

She gave me a big kiss and said goodnight and went to her bedroom. In the morning she just smiled when she saw me, gave me a kiss on the cheek and headed home.

She continued to babysit for a few more months and nothing more happened (other than when she was swimming in my pool with the kids and I snuck her panties to sniff and masturbate to! But that is part of another story...)
 
peebudy said:
what kind of real jobs?

hand jobs? blow jobs? rim jobs?

;)
Click to expand...

Um, I worked at a grocery store as a cashier. :rolleyes: Ya know, a better paying job than being a babysitter... Babysitting is a job for considerably younger girls and once someone is of WORKING AGE they can hold normal jobs and receive steady paychecks.
 
minn said:
Many years ago I came home on a late flight. Wife out of town at sisters helping her through a rough time. I was trying to be very quiet entering house so as to not wake kids and babysitter. I wear boxers to bed and went to the kitchen to grab a glass of wine (I was still wide awake and wanted to read before I went to bed). Walking out of the kitchen I almost ran directly into the babysitter as she was entering the kitchen to grab some water from the refrigerator. We scared the crap out of each other and then began to laugh. She was wearing a T-Shirt that was slightly above her bottom. I could not tell if she was wearing anything underneath.

We stood there chatting for quite awhile when I finally asked if she wanted a glass of wine. She readily agreed and we sat down in the den. One glass led to another and we were having a fun time chatting away. She said she needed to use the bathroom and got up and left the room. My eyes followed her ass as the t-shirt was bunched up above her ass that was, without panties! I about came in my pants! It was difficult to keep my hard cock from making a major tent in my boxers.

When she returned she filled our glasses with more wine and sat in the chair across from me. She crossed her legs and I caught a slight glance of her bush. I needed to pee but could not get rid of my erection! She reached down to pick up a pillow off the floor and I caught a wonderful look at her tits through the top of her t-shirt.

I could not take it anymore and told her I was going to bed, that I was tired. I stood up and, don't know what possessed me, reached over and pulled her from the chair and gave her a big hug goodnight. I squeezed her tight and was surprised how my cock broke out of the fly in the boxers and felt the smoothness of her stomach. She knew what had happened, pulled her head back, looked at me and smiled. With that smile I came all over her stomach and legs. I felt like a 12 year old! I began apologized like a fool while she just laughed and said not to worry.

She gave me a big kiss and said goodnight and went to her bedroom. In the morning she just smiled when she saw me, gave me a kiss on the cheek and headed home.

She continued to babysit for a few more months and nothing more happened (other than when she was swimming in my pool with the kids and I snuck her panties to sniff and masturbate to! But that is part of another story...)
Click to expand...


Very hot story! Thanks for sharing! Have you done anything with her since? How old was she at the time of this first encounter?
 
DarkPleasures said:
Um, I worked at a grocery store as a cashier. :rolleyes: Ya know, a better paying job than being a babysitter... Babysitting is a job for considerably younger girls and once someone is of WORKING AGE they can hold normal jobs and receive steady paychecks.
Click to expand...

lighten up Dark...I'm just playin'
 
DarkPleasures said:
Well, the site is strict on their age rule, so I took your comment at face value. *shrugs*
Click to expand...

yikes...didn't mean it that way.

I also see that chargergirl edited my other post, even though there was nothing sexually explicit about it.

I'll be on much better behavior from here on out.

Sorry about that ladies!!!
 
I've had a couple experiences as a babysitter and a couple that almost happened with babysitters of my kids.

Needless to say, babysitter fantasies are some of my favorite to chat about ;)
 
I had a girlfriend who, when she was younger, was a babysitter and had an ongoing tryst with one of the men who hired her. She lost her virginity to him, and it went on a couple years. Mostly it was in the back of his minivan, but occasionally he'd hire her on nights when his wife was out, and take her after the kids fell asleep. She joked once that she was pretty much his call-girl but on minimum wage.
 
minn said:
Many years ago I came home on a late flight. Wife out of town at sisters helping her through a rough time. I was trying to be very quiet entering house so as to not wake kids and babysitter. I wear boxers to bed and went to the kitchen to grab a glass of wine (I was still wide awake and wanted to read before I went to bed). Walking out of the kitchen I almost ran directly into the babysitter as she was entering the kitchen to grab some water from the refrigerator. We scared the crap out of each other and then began to laugh. She was wearing a T-Shirt that was slightly above her bottom. I could not tell if she was wearing anything underneath.

We stood there chatting for quite awhile when I finally asked if she wanted a glass of wine. She readily agreed and we sat down in the den. One glass led to another and we were having a fun time chatting away. She said she needed to use the bathroom and got up and left the room. My eyes followed her ass as the t-shirt was bunched up above her ass that was, without panties! I about came in my pants! It was difficult to keep my hard cock from making a major tent in my boxers.

When she returned she filled our glasses with more wine and sat in the chair across from me. She crossed her legs and I caught a slight glance of her bush. I needed to pee but could not get rid of my erection! She reached down to pick up a pillow off the floor and I caught a wonderful look at her tits through the top of her t-shirt.

I could not take it anymore and told her I was going to bed, that I was tired. I stood up and, don't know what possessed me, reached over and pulled her from the chair and gave her a big hug goodnight. I squeezed her tight and was surprised how my cock broke out of the fly in the boxers and felt the smoothness of her stomach. She knew what had happened, pulled her head back, looked at me and smiled. With that smile I came all over her stomach and legs. I felt like a 12 year old! I began apologized like a fool while she just laughed and said not to worry.

She gave me a big kiss and said goodnight and went to her bedroom. In the morning she just smiled when she saw me, gave me a kiss on the cheek and headed home.

She continued to babysit for a few more months and nothing more happened (other than when she was swimming in my pool with the kids and I snuck her panties to sniff and masturbate to! But that is part of another story...)
Click to expand...

Wow turn on :p
 
minn said:
(other than when she was swimming in my pool with the kids and I snuck her panties to sniff and masturbate to! But that is part of another story...)
Click to expand...

Please do tell...naughty panty sniffing stories always turn me on..
 
A long time ago, I had a regular babysitting job. It was super easy because the kid slept the whole time, and that gave me too much time to nose around. I eventually discovered a homemade sex video made by the couple who were paying me. That sure was an eyeopener! It was a perfectly terrible invasion of privacy, but I must have watched that thing half a dozen times.
 
minn said:
I could not take it anymore and told her I was going to bed, that I was tired. I stood up and, don't know what possessed me, reached over and pulled her from the chair and gave her a big hug goodnight. I squeezed her tight and was surprised how my cock broke out of the fly in the boxers and felt the smoothness of her stomach. She knew what had happened, pulled her head back, looked at me and smiled. With that smile I came all over her stomach and legs. I felt like a 12 year old! I began apologized like a fool while she just laughed and said not to worry.

She gave me a big kiss and said goodnight and went to her bedroom. In the morning she just smiled when she saw me, gave me a kiss on the cheek and headed home.
Click to expand...

I bet she enjoyed it as you did.. when she got up to go the bathroom she could have put on some panties or something.. but she did not. I bet she would of loved it if you offered to clean up... Maybe she had been thinking about this for a while and when she noticed you getting home she planned to accidentally run into you :) Good story
 
lacygirl09 said:
I've had a couple experiences as a babysitter and a couple that almost happened with babysitters of my kids.

Needless to say, babysitter fantasies are some of my favorite to chat about ;)
Click to expand...


Oh no, Lacy! You can't leave us hanging like that. Please give us the details. I'm sure everyone involved was of age. ;)
 
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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