Anyone ever fucked the babysitter?

BackwardsBret

Member
Dec 2, 2001
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Toronto
Well, since you asked. Not much to tell really.

Happened about ten hears ago but remember it like it was yesterday. The girl, Cheryl, was 14 and had been babysitting my son for about six months. Very reliable. Always on time. Then one Friday she's late so I called her home. Her mother said she's sick but if I don't mind she can fill in for her daughter. She arrives about 15 minutes later at which time I go HOLLY FUCK! I'd never met her but had heard that she was rather young to have a daughter Cheryl's age but I had no idea how young. When I told her how surprised at how young she looked, Liz blushed and told me she was 29! HOLLY FUCK.

Anyway, I go out on my date which turns out to be a total bust. My car broke down. My date got pissed off and took a cab home. My house was just off the subway line so I walk the last bit from the station, and I end up getting home about two hours earlier than planned. I check on my son, but I didn't see Liz. I had a baby monitor in the basement so I figure she's down there. This is where it pretty much turned into a scene out of a porno. Well, sort of.

Halfway down the stairs I heard some moaning. Being a moron I figure she must be feeling sick so go back upstairs to grab the medicine box. Head back downstairs and this time I'm not so clueless when I heard the moaning. Stop to stoke it a bit and then figured I had to have a look. Stuck my head around the corner into the den and there was Liz, lying on the floor, legs spread with her feet up on the sofa, working a blue dildo in and out. I'm still stroking, leaning on the door frame when my belt buckle hits the door frame and makes a noise even a deaf person couldn't miss. I freeze. She looks over, smiled and licked her lips...

Anyway, it was may months before I had to worry about having a lousy date.
 

simon482

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Feb 8, 2009
9,966
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Well, since you asked. Not much to tell really.

Happened about ten hears ago but remember it like it was yesterday. The girl, Cheryl, was 14 and had been babysitting my son for about six months. Very reliable. Always on time. Then one Friday she's late so I called her home. Her mother said she's sick but if I don't mind she can fill in for her daughter. She arrives about 15 minutes later at which time I go HOLLY FUCK! I'd never met her but had heard that she was rather young to have a daughter Cheryl's age but I had no idea how young. When I told her how surprised at how young she looked, Liz blushed and told me she was 29! HOLLY FUCK.

Anyway, I go out on my date which turns out to be a total bust. My car broke down. My date got pissed off and took a cab home. My house was just off the subway line so I walk the last bit from the station, and I end up getting home about two hours earlier than planned. I check on my son, but I didn't see Liz. I had a baby monitor in the basement so I figure she's down there. This is where it pretty much turned into a scene out of a porno. Well, sort of.

Halfway down the stairs I heard some moaning. Being a moron I figure she must be feeling sick so go back upstairs to grab the medicine box. Head back downstairs and this time I'm not so clueless when I heard the moaning. Stop to stoke it a bit and then figured I had to have a look. Stuck my head around the corner into the den and there was Liz, lying on the floor, legs spread with her feet up on the sofa, working a blue dildo in and out. I'm still stroking, leaning on the door frame when my belt buckle hits the door frame and makes a noise even a deaf person couldn't miss. I freeze. She looks over, smiled and licked her lips...

Anyway, it was may months before I had to worry about having a lousy date.
you forgot to start it with "dear penthouse forum" but otherwise this story is very believable.
 

Thunderballs

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Sep 18, 2002
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Uh, I would avoid hiring a babysitter that feels the need to bring a dildo with them. But then again, that's just me.
 

lomotil

Well-known member
Mar 14, 2004
6,464
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Oblivion
Once I was the babysitter and I copulated with the mother a few days latter.
 

assholee

New member
Aug 12, 2010
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Happened about ten hears ago but remember it like it was yesterday. The girl, Cheryl, was 14 and had been babysitting my son for about six months.

I'd never met her but had heard that she was rather young to have a daughter Cheryl's age but I had no idea how young. When I told her how surprised at how young she looked, Liz blushed and told me she was 29! HOLLY FUCK.
So your telling us that the mom got pregnant at the age of 14 and gave birth at 15? lol
 

bone_man

bone hard and ready
Sep 4, 2004
525
4
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your place
Roflmfao!!
 

SS Sharla

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Nov 1, 2010
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Kitchener
When I was younger and worked as a hostess, the head chef at work would ask me everyday "Are you 16 yet?". The day after my 16th birthday he asked me to babysit because his son was visiting. His son was a year old and he was 39. He went out drinking and when he came home he asked if he could kiss me. I always had a little crush on him so I said yes. We got seriously carried away . . . fucking on the couch, the kitchen table, infront of the mirrors, on the floor. It was amazing. He was the second guy I was ever with. I wouldn't change it for anything. At 16 it was quite an experience to have sex with a man who knew what he was doing. The only downfall is that young girls get attached. I crushed on him hopelessly for months afterwards. Sometimes I wonder, when I visit my home town and see him, if he is worried that I think he's a monster for sleeping with a young girl, but I wasn't really your typical young girl. I will never forget the look on his face, when he worked his way inside me. Like recapturing his youth. I've loved older men ever since.

Disclaimer: You should never rob a young girl of her innocence. Before being with this guy I had a boyfriend my age and we discovered sex the way kids should. Not knowing what the hell we were doing, but it was funny and intimate and loving. I would never give up that experience either.
 
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Don Draper

Cufflinks & Cognac
Nov 24, 2009
6,364
643
113
I must confess that yes, I did bang the baby sitter.

She didn't need to know that neither the house nor the kids weren't mine.

I love travelling in foreign cities!
 

afterhours

New member
Jul 14, 2009
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When I was younger and worked as a hostess, the head chef at work would ask me everyday "Are you 16 yet?". The day after my 16th birthday he asked me to babysit because his son was visiting. His son was a year old and he was 39. He went out drinking and when he came home he asked if he could kiss me. I always had a little crush on him so I said yes. We got seriously carried away . . . fucking on the couch, the kitchen table, infront of the mirrors, on the floor, in the ass. It was amazing. He was the second guy I was ever with. I wouldn't change it for anything. At 16 it was quite an experience to have sex with a man who knew what he was doing. The only downfall is that young girls get attached. I crushed on him hopelessly for months afterwards. Sometimes I wonder, when I visit my home town and see him, if he is worried that I think he's a monster for sleeping with a young girl, but I wasn't really your typical young girl. I will never forget the look on his face, when he worked his way inside me. Like recapturing his youth. I've loved older men ever since.

Disclaimer: You should never rob a young girl of her innocence. Before being with this guy I had a boyfriend my age and we discovered sex the way kids should. Not knowing what the hell we were doing, but it was funny and intimate and loving. I would never give up that experience either.
Nicely put
 

Rockslinger

Banned
Apr 24, 2005
32,776
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For some reason I just knew that this would be an extremely popular thread. We could start another extremely popular thread by replacing "babysitter" with "pizza delivery girl" or "nanny" or "maid".
 
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