Latest Babysitter Confessions:

 

26614 - I was 13 when my parents went on a two week trip for my dads job. they hired a babysitter to take care of my two younger siblings. the second night I heard a strange noise. I got up to see what it was it was the babysitter watching one of my parents porns and masturbating in the nude I stood there looking at her naked body. I am about average height with large 32c tits for my age. she was 16 about 5'8 185lbs and huge 42ddd tits with large nipples and a shaved bare pussy. I could not take my eye off of her. I reached down and started to play with myself.
I guess I let out a little moan and she saw me standing there with my hand in my panties playing. she told me to come over I did and told her I was sorry for spying on her. she asked if I liked what I saw. I turned red and told her yes she told me to get naked also and sit next to her. I did she told me how she like my body and was go to find a way to see me naked so she could touch it. I said for real, and that I have never had anyone other than the Dr. touch me since I was 12 and always wonder what it would be like to have another girl do it. she reach over and started to fondle my tits and she leaned over and started to suck on one it felt so good I let out a moan. I reach over and started to play with her nipples they where twice the size of mine and it felt so good to do it. she let out a moan and move so I could suck on her nipple.
she slide her hand down to my pussy and started to play with my clit I told her it felt so good she said lets go to bed where we could be more comfortable she lead me to my parents room where she was sleeping. when we got in bed she laid down and told me to get on top with pussy in her face and her at mine then she told me to do what she did to me to her. she started to lick my pussy and stopped she said we had to do something first and that was to shave my pussy.
I told her I did not know about doing that she said If I wanted to go further I would have to. I was so horny I said ok but if my mom saw what do I tell her. she said you saw me naked when I was in the shower and wanted to try it. we went into my parents bathroom where she put me on the counter and cover my pussy with shaving cream and started to shave me bare it felt so good because every time she would get close to my clit she would flick it. when she was down she oiled it with baby oil.
we went back to bed where she eat my pussy and I ate her we both orgasm at the same time. we went to sleep I woke up to her licking my pussy and two finger deep in my very wet pussy. she would work me up till I was about to cum then stop after about 5xs doing that she let me orgasm I came so hard I squirted for the first time ever that I started to apologize thinking I had peed. she laughed and told me I didn't that I had just cummed hard. for the rest of the time she was there when ever we could we would either finger each other or eat each other. one night I had a gf over who told me she and her sister play with each other.
the three of us had sex all night long. then when ever my parents needed a babysitter I told them to call her. she baby sat for us till she went to college when she turned 20.
I did get to do it with her when she would come home for breaks and we would go out to a movie(LOL) or a few times I went to her when she was at college she had a roommate who also a lesbian and we would all had sex all weekend.

 

25873 - My first time doing anything started with my 17yro cousin she had huge 34ddd tits and a small tight ass. she would come and baby sit me and my two sisters. I was 11 and they where 10. one day when my parents went on a five day trip I came in from playing out side to go to the bathroom and walk in on her getting out of the shower. seeing her standing there naked was a shock because she was the first girl I ever saw naked with huge tits. she asked if I liked what I saw. I must had turned red she laugh. I told her yes then turn and peed I was always told not to pull my dick out in front of a girl but ii had to go. when I pulled it out it was so hard I had a hard time hitting the toilet. she sat on the edge of the tub and watched. when I was done I cleaned up where I missed ii still had my dick hanging out. she told me to come over she wanted to see it better. I almost wanted to run out of the room but I turned and went to her. she undid my pants and dropped them to the floor and started to rum my dick up and down it felt so good that my dick got harder and started to throb. she took one of my hand and placed it on one of her tits and told me to squezze the nipple real hard. while I di this she leaned over and took my dick in her mouth and started to suck it and lick it I had my first orgasm I didn't have any cum yet but it felt so good. she told me never tell anyone in the family or another adult and if I kept this secret we could do it any time she baby sat or if she could pick me up and go with her.
later that night after my sister took their bath I took mine she came in and played with my dick while she had me suck on her tits. after that when my sister where asleep she got me up and her to my parents where she was sleeping and taught me how to lick her pussy. after that we would do 69 every chance we could. when I turned 16 she let me fuck her and cum in her.

 

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.