Latest Babysitter Confessions:

 

24680 - When I was 17 my mother hired a babysitter to watch us while she went out of town with her boyfriend for the weekend. He was a major alcoholic and would drink himself into outer space once all us kids were home and in bed. He also had a young daughter who was 13 years old who's name was Amy, who instantly took a liking to me.
While her father watched TV or whatever else he did she would hang out with me in my room. At first we would fool around by kissing and touching each other. Soon it progressed to making out with some heavy petting. When I got her panties off I fingered her for a while and she reciprocated by giving me an amazing blow job until I came inside her mouth while she struggled to swallow most of it. When I tried to have sex with her she refused, afraid we would get caught but, she told me if I came to her room that night she would have sex with me. Later that night, there was a big electrical storm. When I left my room I saw that her father was passed out drunk on the couch in front of the TV and quietly made my way to the room she was sleeping in alone that night. When I came into the room she was already awake waiting for me. We made out for a while as the Thunder crashed outside as we slowly worked our way out of our clothes. When we were completely naked I took in her young developing body and noticed her breasts were just little buds sprouting on her chest and, she had very little pubic hair covering her pussy. When she saw the size of my erection I could see some trepidation in her eyes knowing she was going to have a grown man entering her. As we started making out again I slid my cock along her wet slit until the head slipped just inside her causing her to gasp in anticipation. I looked her in the eyes as I plunged nearly half my length inside her and her eyes went wide as she squirmed in discomfort as I worked more and more of my cock inside her until I hit her cervix. She was incredibly tight but I also noticed she was not a virgin either. I was so blinded with lust I pounded away inside her as she moaned while the lightning flashed and the Thunder rolled outside. It wasn't long before I was groaning as I sent rope after rope inside her developing womb. When the last spurts left my cock she asked me if it felt good. Of course it felt good so, I told her and she asked me if I was her girlfriend now. I told her yes but, I knew had no intention of having a 23 year old girlfriend. When I look back now I realize that her father may very well have been abusing her, I was just to young and dumb to see the signs back then.

 

23739 - I can barely remember my baby sitter when I was very little. Her name was Doris. She was in high-school and I was maybe five. I remember taking off her sweater and prompting me to suck her nipples. She was caught by my older brother while she was doing that with me. It never happened again.

I have gotten off so many times thinking about Doris. I only wish she would have had me suck her pussy. I would have done anything she asked.

What a wonderful thing it would have been for her to suck me off to my first cum.

Here's to you Doris!!

 

23720 - It was such a cliche.

I was 15 and babysitting for this couple that lived a couple of blocks away from me. They family friends, and I've known the kiddies (5 and 7) since they were babies.

Anyway, at that age, I had just started masturbating, and I couldn't get enough of it. So of course, an hour after the kids went to bed, and with the parents not due to come home for a couple of hours more, I was peeling off my panties and pushing up my skirt in no time. I did it in the living room, on the sofa in front of the TV which I left on.

As luck would have it, I was on my way to my second orgasm when I opened my eyes and found the kids' dad standing in the doorway, just looking at me. Later, I would find out his wife had stumbled across old girlfriends of her during dinner and decided to stay with them to catch up while he decided to come home early and let me go for the night.

When I shrieked and tried to hid what I was doing, he told me, oh so calmly, to not stop and instead keep going. Said he was really enjoying the show, and then he pulled out his hard cock to show me just how much.

I was really turned on. I was still a virgin, and this much older experienced guy was getting off on watching me. So, feeling reckless, I started touching myself again, eyes glued to his cock, which he started wanking. It didn't take me long before my legs started twitching and I came again. When I opened my eyes, he had crossed the room and kneeled down in front of me to see up close and personal. And before I could stop him, he pushed my legs further apart and just buried his head in there. I was squealing in shock and pleasure, never having even felt someone else's hand there, let alone a tongue.

He got me off like that so quickly I blacked out for a second. When I came too, he told me to help him and wrapped my hand around his cock. After he jizzed, he had me lick it off his hand and I can't believe I actually did that without any hesitation.

Then we fixed ourselves up and he gave me my money and sent me on home.

I came to babysit again a couple of weeks later, and the husband came home early again. Needless to say, things got out of hand again, and a couple of months after starting such an obscene tradition, he took my virginity.

We kept fucking until I was 17 and moved away for college.

 

22188 - I was working out late at my local gym, last week. When I was leaving the young woman that runs the kids care center there, came up to me and said she needed some help, her car needed a jump.

When I went to help her, I needed to clean off the terminals, so I took off my shirt and wiped them down. Being just from the gym with a good pump, my muscles were a bit swollen. Out of the corner of my eye, I noticed her giving me an appreciative smile. I couldn't help but get an instant hard on.

After I was done, and her car was started, she leaned into me, scratched one hand across my bare chest and the other against my swollen cock and said, "You've jumped my car, but could you follow me home just to be sure? I may need another jump" Who could resist?

I followed her home and sure enough, when we got there, she needed another good jump. This time in her bed and I made sure her battery was nice and charged when I left.

We fucked in almost every position we could think of and were good and sweaty when it was all over with. Afterwards she gave me a nice shower with a fantastic thank you BJ.

The real corker is that when I was leaving, I noticed a framed family photo by the door. Turns out she's the youngest daughter of the pastor at the church. She hasn't been around for a few years, thanks to college.

Needless to say, I told her to call me when her battery runs low again.