Latest Babysitter Confessions:

 

25246 - A few weeks ago I was back in my home town visiting my folks. It had been two years since I'd been back. Since graduation, I got big into working out and didn't look much like the boy I was in high school.
I got there early Friday morning. I dropped my bags off at the house and went to workout at the Rec Center since my folks were at work. The gym was empty when I started working out. About 30 minutes later, a very nice looking older woman came into the gym. We said hello and I went back to my workout. With all the mirrors in the gym, it was easy to check her out. I could see her looking at me too. Between sets, it dawned on me I knew her. She used to babysit me and my sister when we were young. It had been years since I last saw her. She looked amazing. After I finished lifting, I went to the treadmill. A few minutes later she started running next to me.
I told her who I was and she immediately stopped running. I stopped to and we hugged. She couldn't believe how different I looked and I complimented her on how amazing she looked. We talked for a few minutes and I offered to buy her a coffee. We both agreed to take a shower first before going there.
In the showers I rubbed one out because I was so horny. I got dressed and met her outside the showers. We got a coffee and decided to take a walk. We were catching up when I felt I had to say how nice she looked. She said the same about me and made the comment that if she was my age things could be different. I partially joked that age was just a number. She got me back accusing me of being a smooth talker with the girls in college. The flirting continued until we walked through a more secluded area of the park. I went for it, dropping my coffee I put my hands on her face and kissed her. She pushed me back and reminded me she was married, kids, and too old for me. I told her I didn't care and kissed her again. She made a very weak attempt to stop me then started kissing me back.
We both realized we need a more private space to continue. Holding hands we jogged to the back of back of shelter #3. I lifted her up and squeezed her butt cheeks placing her onto the picnic table. We were kissing and I started rubbing her inside thigh. She stopped again and was shaking. She wasn't sure if we should continue. She looked rattled and told her it was OK. I didn't want her to do anything against her will. We sat on the bench and I put my arm around to help calm her.
Not sure what to do, I joked she was my favorite babysitter and it got her laughing. She couldn't get over how much I had changed. We walked back to our cars and I was asked not to say anything.
I got home and hung out with my folks. A friend of mine asked if I wanted to go out later. After my folks went to bed, I went out. There wasn't much to do except go to the bars. We were just playing pool when a couple of girls walked in. My friend knew one of the girls and motioned them over. My friend introduced me to them. The other girl was my babysitter's daughter. She was just as hot as her mom ...only younger. We played some pool together. We decided to go get some food. My friend was trying to hit on my babysitter's daughter but she wasn't feeling it. The four of us agreed to get some beer and drive out to the lake. The lake was chained off so we walked down to the beach. We were sitting around just talking. When my babysitter's daughter motioned me to take her for a walk. It felt a little weird knowing I had almost scored with her mom. We were just talking and I wasn't really feeling her. We were walking back when I saw my friend and the other girl were getting it on. I steered her around and we walked away. She asked why and I told her. She was silent, then just blurts out "wanna bj?" I'm no fool and agreed. I stood up against a tree. She unzipped my pants and went to town. She was very inexperienced but tried hard. She let me squirt on her face and mouth. She asked how it was and I lied. I figured we could head back but she wanted it from me. Not really wanting to do but it was fair play. She had pulled her panties down and I pulled her skirt off. I picked her up easily and had her put her legs over my shoulders. I pinned her up against the tree and went for it. She was over doing the moaning but it tasted sweet and she was a squirted which was cool. When I finished, I put her down. She asked if I had a condom but I didn't. She put her hands on the tree sticking her ass out telling me to make sure to pull out before I cum. This girl was crazy and I was digging it. She reached down between her legs and guided me in. I put my hands on her hips and started slow. The faster I went the louder she was. I got over stimulated and lost control shooting inside her. She knew I had and got pissed. I was over it and zipped up heading to the beach. We got back and dropped the girls off at their car.
I'm back at college when she calls me Friday evening. She missed her period. F***!!!

 

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.