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Remebring my first Babysitter

Date: 12/22/2014, Categories: First Time, Masturbation, Taboo, Author: brianbigdogsmith, Rating: 100, Source: xHamster

babysitting. Needless to say, I looked forward to those times when my parents went out. One other thing happened that school year, just before summer vacation. Sadly (for me) it was a one time happening. The TV was on and Bonnie and I were on the couch in the midst of our usual "stuff." I could feel her rubbing herself while she rubbed me which made me picture what I saw occasionally when Tricia was over and made me wish I could see more of. Since Tricia had started "playing" along with us, Bonnie had become more open about stimulating herself but I never got to really watch. She leaned forward a bit, lips at my ear and whispered, asking if I was willing to try something different tonight. I said sure and for the first time, she actually admonished me that I couldn't tell anyone about what we were going to do. She reached into her bag and pulled out a tube. I assume now it was probably KY or something similar. I have often wondered how she got the KY, if she stole it from her folks or what. Anyway, she said she wanted to see if I could "stick my willy into her bottom." This was something totally new. Over the last year and a half, I had not touched her sexually in any way; that just wasn't part of our game. She gave me the tube and told me I would need to rub it all around her hole and then on my "willy" (her word for my dick). With that, she rolled onto her stomach, reached down and pulled her shorts and underwear about half way to her knees. She then rose up onto her knees ... and pushed her hips back towards me. There were no lights on, just the TV, so I couldn't see detail, but I could make out her buns which were spread a little, the pucker of her sphincter and the outline of her labia and some hair below. Needless to say, I was hard as a rock, but also a little scared. I took the cap off the tube and as instructed, lubed her up and myself too. The next series of events probably would have been comical to an observer as there was a height mismatch between her 15 year and my 9 year old legs. I was too tall when I stood behind her and too short when on my knees. We fumbled around making several lame attempts, I even tried standing on the floor and stretching up to her. We finally ended up on the floor with her on her side. In this position, I was able to slide forward enough to make contact, but not enough to put enough pressure to enter her (remember I was working with very few inches). She finally ended up flat on her stomach with a pillow under her hips, her shorts around her ankles and her legs spread. This was the perfect angle as it caused her buns to part slightly. It also gave me a better view as we were closer to the TV. I knelt between her legs and lay forward on top of her her, fumbled around a bit with my hands, found her hole and guided the head of my dick to it. As I pushed down, she pushed back and I very quickly popped all the way in. She gasped a little bit and reached around behind to grab my hip and told me to hold me still. The ...