1. Remebring my first Babysitter


    Date: 4/23/2017, Categories: First Time, Masturbation, Taboo, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    to stop crying. I tried and eventually reduced my bawling to hiccups between words. I hiccupped out all my fears and added that I was so sorry and it would never happen again finishing with a plea, "Just, please don't tell my Mom!" She smiled, her brown eyes seemed very understanding, and promised not to tell. Then she added, "You'll just have to keep a secret for me too." As she said it she winked, gave me a big hug (she sure smelled good) and lay back down on the couch on her side. That was the last thing she would say that evening until she told me to go up to bed. As she lay down, she patted the couch in front of her. I took a step forward and she took my hand and pulled me onto the couch. I sat down in front of her stomach on the edge of the couch so I wouldn't block her view. I figured she was going to keep an eye on me so I wouldn't repeat my transgression. She reached up and pulled me down to lay half on my side, half on my back, spooned up against her. I put my head down on my right arm, so I could see the TV. She had her head on a pillow so she could watch over top of my head. She pulled me in close and we watched the rest of Carol Burnett together with her occasionally ruffling my hair. I was in heaven through the rest of the show, but also couldn't help wondering what secret I was going to have to keep for her. At the end of the show, I started to get up. I knew that bedtime came right after Carol Burnett and that my folks had made a big deal about bed time when ...
    they first hired Bonnie. To my surprise, she put her hand on my shoulder and guided me back down in front of her. The TV switched to another show. I honestly don't remember what it was, as I was just enjoying being close to Bonnie. I figured the secret I was supposed to keep was staying up later than my bed time. At first I barely noticed, but as the TV droned on, she began rubbing the side of my leg, down as far as she could reach without stretching, then back up my side, down and across my chest to my stomach, then up my hip to start over again. I just lay there as she rubbed and not surprisingly, before long was sporting another stiffy. I prayed that she wouldn't notice, almost afraid to breathe. On the next pass, as she brought her hand up my thigh, she reached across to my other leg which meant as she brought her hand up towards my waist, her forearm rubbed across my boner. It was all I could do to keep from pushing up to meet her touch. I was scared stiff (no pun intended) I figured I'd be in even bigger trouble if she knew I'd gotten another boner. She continued to rub me like that through the show. When it was over, she announced I had better get on to bed. The next couple of times she babysat, it was the same thing, except that the rubbing started as soon as I came down from my bath to watch TV. I was totally confused by this. How could she not feel it? I finally decided that she either didn't notice or that she was just too nice to mention my obvious stiffy. Either ...