Sex With My Babysitter

My wife and I have been going through a dry spell now that she just gave birth to our third kid and we're both working full time. I've been thinking a lot about my old babysitter from childhood as a result, I've never told anyone because it might get her in trouble...

My mom divorced and remarried when I was a kid. I was 14 and my two half siblings were 1 and 2. I hit puberty very early and was involved in sports. My mom got a babysitter since I spent most summer mornings at practice.

Our babysitters name was Ashley. She was 20 and attending a local community college. I thought she was a smokeshow. She had a plump, round ass, C cup breasts and a pretty athletic (but slightly curvy) frame. She'd sit out by our pool in the afternoon and I'd watch her from my room and jerk off into a sock. I'm pretty sure she found my socks and used kleenex when she was cleaning up one day.

One day after showering she confronted me about it matter of factly. I was super embarrassed but got hard. She put my siblings to bed for a nap and then we went to my room. I had no idea what I was doing. She gave me a blowjob and swallowed. She then bent over the bed and let me have sex with her. I came inside her in under a minute.

We continued this for the rest of the year. She showed me what she liked and we even developed a code phrase "Do I need to clean my room?" to hint at going upstairs. She had only ever had one boyfriend but had a pretty high sex drive that pretty much matched mine at 14 years old.

She was usually wet and had really strong orgasms from penetration. I'd get back from practice around noon and shower while she put my siblings to bed for their afternoon nap. We'd sneak down into the basement and I'd fuck her on the couch. I would cum inside her and then keep thrusting and usually cum a second or third time. She would usually cum a few times. She had to get an IUD as emergency contraception because she wasn't on birth control.

Once the school year started she would give me a ride to school so that my mom didn't have to buy a car. On the way to school we'd park behind this warehouse and I'd fuck her quick, and then we'd do the same after she picked me up. Sometimes she'd ride me or I'd bend her over in the backseat. Sometimes I'd sneak into her parents house on the weekends a fuck her in their basement.

Looking back it was basically statutory r**e. I never felt abused though and she was always kind and matter of fact about it. She always told me that we could stop if I wanted, but that it had to be a secret. I'm glad she got an IUD or I would've been a teenage dad. Eventually she went off to state college her junior year and we stopped seeing each other. I found her on facebook and she looks happily married with two kids. I didn't realize at the time, but that was probably the most sexually satisfied I've ever been. Cheers to Ashley, I miss her.

Comments

Anonymous

by Anonymous on Dec 4, 2023 at 6:50 PM

That is a great story!

I had a similar experience when I was 13. My mother's female friend came by to stay for a long weekend with her 18 year old daughter. That night (a Friday), they decided to go out together, planning to return the following day, leaving the daughter to "babysit" me. She was pretty with round breasts and a nice ass and legs, so I didn't mind, though I pretended to be insulted about having a "baby" sitter.

After they left, we hung out, chatting about various things. Horny kid that I was, I couldn't keep my eyes off of her and she noticed. After dinner, she told me I needed to take a shower. I knew that was not really necessary, but I agreed. She stood by as I took off my clothes in the bathroom. As I showered, she stayed in the bathroom, having a casual conversation with me. I didn't mind, but I was getting hard thinking of her in the room with me naked. When I was done, she held the towel and dried me off, paying special attention to my crotch and ass. She smiled at my hard-on, holding it through the towel. Then she told me to go to bed!

I laid in bed, but could not sleep at all. My mind was racing with all sorts of horny thoughts as I stroked my hard cock. Very frustrating. I decided to see what my "babysitter" was doing, so I tip-toed to the living room. The only light was from the tv. I saw her on the couch, wearing only a tee shirt and panties, her legs open, rubbing her pussy and squeezing her breasts. I was fascinated. I held my hard cock as I watched her. Suddenly, she turned her head in my direction. I quickly ran and jumped back into bed.

A few minutes later, she came into my room, still in her tee shirt and panties. I pretended to be asleep as she walked slowly around the bed. The light from the street illuminated her. She pulled down the cover and saw that I was naked. She took hold of my cock and stroked it. Horny me was hard in a second, so there was no point in pretending that I was asleep. She told me "You better not tell." With that, she took her shirt off, revealing her beautiful round breasts. As she sucked me off, I held her breast. Then she straddled me and lowered herself onto my cock. That night and the next day, she showed me the proper way to fuck her, how to lick her pussy and how to satisfy a woman.

I will always treasure that experience which I have put to good use ever since. She was my first and among my best fucks!

- Free Lover 2021 at aol

(9)  (0)

Comment this

Can't read the image? Click here to refresh