Adventures in Babysitting

*

When I was 19 years old, I used to babysit for extra money. People thought I was crazy, but I thought it was the perfect way to make money. You can sit around and watch television, usually eat pizza and drink all of the sodas you wanted to. I also only babysat for families that had older kids who didn’t need a whole lot of attention, and even some where I knew the husband had a good stash of porn.

There was one young family directly across the street from me that had two boys who both enjoyed it when I stayed there. We always had a lot of fun, and I always let them stay up past their bed time. I loved babysitting there because I had the hots for the Mom and the Dad had a really good supply of Penthouse. The Mom was extremely sexy I thought. She was 32, had a beautiful face, about a C cup breast and a nice thin waist. Her hips were a little big from having two kids, but she was gorgeous. She also had the most amazing lace bras which I used to love taking out of the hamper and smelling. She smelled wonderful! I think she bought her matching bra and panty sets from Victoria’s Secret, but at 19 I couldn’t tell the difference.

A time came where I think the two of them were having marital problems. He seemed to be gone a lot and she seemed to going out a lot. I know she was going out a lot because I seemed to babysit about once a week. She also had this really good looking friend that went out with her a lot. She was good looking and really slutty looking too. It made the mom seem even that much more hot! She especially looked hot the days I went to babysit because she was going out and she really liked to wear something skimpy and revealing. She dressed for fun and she always seemed like she had fun. She never came home with a guy (I fantasized about her friend spending the night with her), but she always seemed to come home late, always seemed a little tipsy with a smell of alcohol and cigarettes in her clothes. She didn’t smoke, but there was not a No Smoking policy in my hometown then. I always liked it when she came home late because I made more money and it gave me more time with her husband’s porn stash after the kids went to sleep. I was very lucky that since she lived so close and was such good friends with my parents, there were times when I would spend the night there if I would fall asleep on the couch. There were a lot of times where the kids would fall asleep at a decent hour and she wouldn’t get home until late, so I had plenty of time with the magazines. I also liked to go through her drawers and see what I could find. I really enjoyed her underwear drawer because she had such a good selection of things to wear. I could see a lot of her panties and bras in the hamper, but looking in her drawers gave me a chance to see some of the things she wouldn’t put in the washer. She had some really nice garments and just looking at them would give me a hard on.

I realized after several months, I had never looked in what kids think is the greatest hiding spot. I never looked between her mattress and her box spring. One night I looked there and found an envelope with Polaroid’s in it. I was very excited when I opened the envelope. I kind of guessed what type of pictures would be in there, but didn’t want to get my hopes up too much. They were justified in being up. There were about a dozen photos in different poses of the mom and of her best friend. None of them were of the two of them together though. I never did find out if she was bisexual, so that could have explained why they didn’t have pictures together, plus I imagine they may not have had a photographer. Up to that moment, this was the best time I had babysitting for her. Needless to say I used the photos for motivation as I layed on her bed and jacked off two times before she got home. After the second time I put the photos back carefully and went back to the living room to watch television.

For the next month whenever I would babysit for her, I would always get her photos out the first chance I had and jack off often. Some of the times I would pull out a couple of her husband’s Penthouse magazines and read the Forum articles while I looked at her pictures. It was the greatest thing a 19 year old could ask for. I went to look one night after the great month, and the pictures were gone. I don’t know where they went, but began to think that maybe she suspected either myself or her kids had found them. They were way too young to begin to think of anything like that, so if she suspected anybody, she probably suspected me. It was kind of exciting thinking she knew I had seen her naked body. At the same time though, she may not have suspected anything and may just have given the photos to her girlfriend to keep at her place. Either way, I no longer had the pictures to look at. I still did have a good selection of magazines which was all a teenager could ask for. As I lay there that first night, I got excited by the pictures, by what I was reading in Forum, and by the thought that she may have discovered that I would do bad things to myself while I looked at her. In my young mind, I thought she might have been turned on by the idea of me seeing her and by the thought of me fucking her like they did in the magazine stories. I decided to do something about it. I thought if I made it more obvious that I had found the magazines, she would know how horny I was and may want to act on it. After I was done jacking off for the last time that night, I left a couple of the magazines out where they could be seen under the bed. They were kept under the bed, but I left them sticking out so that she could tell somebody had found them. When she finally got back that night, she paid me and I went home. Nothing happened.

The next week she called me to see if I was available on a Friday night. Of course I said yes. I got there about 7 and she and her friend were ready to go. They told me they would probably be late, so I should go ahead and call my Mom and plan on sleeping on the couch. No problem I thought. They left; I played with the kids, fed them some pizza and ice cream, and then watched a little television before they fell asleep. I had them go to bed and looked at the clock. It was only 1000 which was great because it gave me plenty of time with the porn stash. I looked at the magazines for an hour or so, jacked off a couple of times (two times in an hour sounds like a lot, but remember that I was only 19), and then suddenly saw headlights in the window. I had plenty of time before she would come in the house, but was disappointed she was home so early. I had decided I was going to leave the magazines out again which I did before I went into the living room and started watching TV. I saw the headlights back out of the driveway and then heard the keys in the door. The mom came in and I could tell she had been drinking, but hadn’t had too much. We had our normal small talk and then went in to the kids room together to check on the kids. They were sound asleep still. We walked back into the living room, and she said she had to go get some money from her bedroom. I thought uh-oh because I knew she was going to see the magazines. She called my name and asked me to come into the room. I knew what it was about and started getting worried that she was going to be pissed and I was going to be in trouble. She was standing on the side of the bed I had the magazines on and asked me what this was as she pointed at the floor.

I kind of stuttered, and said I had just found them that night. She told me I was lying. She knew I had been looking at the magazines for some time now and had been playing with myself in her bed because I would accidentally leave the lotion out beside the bed and she could see my cum covered tissue in the trash can. Then she asked me if I liked her photos she had under the mattress. I was stunned and didn’t know what to say. She could tell that I guess because she just walked over to me and kissed me. I knew how to kiss and was hoping I was doing a good job. Up to that point, I would have been content with just kissing, but she wasn’t going to stop there. As she was kissing me, she moved her hand down to rub my crotch. I guess she liked the huge lump in my pants because she rubbed it and rubbed it. Then she took one of my hands and placed it on her tits. I had plenty of boob action on dates before so I squeezed them like an expert I thought. One of my girlfriends liked her nipple pinched so I did that and the Mom just squealed. I thought she wanted me to pinch harder but she yelped and told me not to pinch so hard. I guess I had a lot to learn.

I think she obviously wanted more than for me to play with her boobs, because she began kissing my neck and nibbling on my ear lobe. I was taller than her so it worked out perfectly. She eventually reached down and pulled up my shirt and moved to kissing my nipples and my chest. I had never had that done to me before and it felt wonderful. She was kissing one nipple and then began rubbing the other one. She squeezed it kind of hard and it hurt a little so I yelped. She looked up at me and asked me how I liked it. I wanted to tell her I liked it all but nothing came out of my mouth. I had been holding up my shirt which kept my hands occupied. I pulled it up over my head now so that my hands were free. She was kissing my stomach and before I knew it, somehow she loosened the drawstring on my sweatpants. She had gotten all the way down on her knees at that point and she pulled my sweatpants all the way down to my ankles which left my cotton covered cock at eye level for her. She licked the outside of my underwear and got a good taste of my precum. She licked me, and bit down a little on my cock too. I was loving it and she was loving it too.