Charlotte

I haven’t written a story in a while, even though I have been reading many of them, so I started going through my mind thinking about another notable experience. I have had several anonymous experiences, several bisexual experiences, and had obviously fucked my wife many times, but since I enjoy reading about the extraordinary, I wanted to write about an extraordinary time. I finally came up with a good one.

This particular story isn’t a long story, but it just goes to illustrate how much of a horn dog I was when I am young. I still am, but when I was young, it was the only thing that seemed to occupy my mind. At least now, I have to think about other things.

I told you a story about losing my virginity when I was 16 to a lady across the street I used to babysit for. After that significant event in my life, I seemed to think every woman in the neighborhood I used to babysit for wanted me. I know now I was wrong, but back then I only seemed to do the thinking with one head. The head at the end of my 8” cock was always winning the arguments. When I was 16, there was another lady that lived down the street that had a 10 year old son I used to watch. He was also easy because we could watch TV, play basketball or football or something that kids enjoyed. The difference with his mom was that she was divorced. She was divorced and was a teacher. She also used to like going out with the girls and having a good time so she seemed like she needed a babysitter every weekend. That is probably an exaggeration, but she did go out a lot. She was also a pretty good looking woman.

Now when I would babysit for her and once her son would go to sleep, I would do what every horny teenage boy would do. I would look for some kind of porn to jack off to. I looked in the normal spots; in her nightstand, in her dresser and between her mattresses. I found several different things to read or look at for my “inspiration”. I found one Playboy magazine, and I am not sure why she had that one, but it worked for a little while. I also enjoyed looking at her lacy under garments. She had some pretty nice items and they always smelled very good. I used to look at them and picture her wearing them. I also found an envelope of polaroids in her underwear drawer. They weren’t pictures of her though; I suspect they were pictures of her ex husband. I don’t recall much about the photos except that he was naked in them and I thought it was a turn on that she would have pictures like that around.

I struck my gold when I looked in her nightstand. She didn’t have stacks of magazines or a drawer full of sex toys, but she had some erotic fiction, several rubbers, and a diary. I guess I didn’t really read the diary for the first several nights I babysat and knew it was in there, but I did read the books and even used one or two of the rubbers to jack off with. There were enough in there I didn’t think she would miss one. At least that is what a young mind thought. I still don’t know if she ever noticed, but as an adult now, I am sure she did.

After several nights, I finally got around to reading her journal. It turned out to be a gold mine. She had written about some of her normal thoughts, but most of the writings in this journal were about her night life, sex life and adult encounters. It was almost like reading Penthouse Forum, but from somebody I knew. I remember her writing about going out to some of the nightclubs in town with her friends and the guys they would meet. She spoke more than once about smoking pot before she got to the clubs and how much more fun she would have when she did smoke it. I wasn’t a smoker, but it did make me think she was a wild thing. She also had one story about how she and a girlfriend had met a couple of guys and brought them back to her house because her son was staying with his father. She went on about how they drank some more at the house and started playing strip poker in the basement. By the end of the night, the two couples had paired off and were fucking until the sun came up. They didn’t do any swapping, or the ladies didn’t play with each other, but all 4 of them were naked and in the same basement I watched television in with her son. It was exciting thinking she had been fucked on the same couch I was sitting on. She also wrote about going to the Blue Angels airshow when it was in town and taking one of the pilots home and fucking him all night long. That’s probably more exciting for me now that I am in the Navy though. She was a wild woman and I used to jack off thinking about her seducing me on her big, king sized bed.

Because her son wasn’t too much younger than me, he was fun to hang out with every now and then. I used to like going to his house and shooting basketball with him on his goal because the goal was only 8 feet high and I could dunk the ball, and because I liked to look at his mom. He would take the bus home from school and stay by himself usually until his mom got home. She was a teacher at another school so she rarely worked late, and she had her neighbors keep an eye on him if he needed anything. Sometimes I would pop in to shoot baskets with him too. One day I went down there and he was just leaving to go to his best friend’s house that backed up to his. The kid’s mom was home, and his mom said he could go and stay until she got home. She was going to be a little bit later that afternoon. I stayed a little bit longer after he left, shooting basketball and then decided to leave. I was extremely horny that day though and really wanted to stick around until she got home. I didn’t want to stay out back shooting basketball by myself too long though. I had a problem at that point, because my little head was beginning to do the thinking.

I knew the son had left the front door unlocked because his mom would be coming home in the not too distant future. I knew I had a little bit of time before she got home, so I thought I would go inside and “relieve myself” like I did when I babysat for her. I walked around to the front of the house, went to the front door like I was going to knock, looked around for anybody that might see me, and then went inside as if somebody else was inside. I knew the son was gone, and the mom was not home yet, so I went upstairs right to where I knew her journal was (I wanted to look for any new writings), and the lotion in the bathroom was. I pulled out her journal, pulled down my pants, and sat on the edge of the bed stroking my very hard cock. I wasn’t in there very long, when I heard a car door slam. I quickly sat up, looked out the window and saw that the mom had gotten home. It was obviously sooner than expected for me. I didn’t panic because she was home, but I didn’t know what to do. I knew I had to put her journal away, and put the lotion and toilet paper away I had sitting beside me. I pulled up my pants, which was very hard because of my boner, and put everything away. I probably could have gone around through the bath room and snuck out when she came in the front door and would probably go straight to her room, but I was thinking with the wrong head. I figured she would change out of her work clothes before she did anything and I wanted to see her naked.

I quickly got into the closet as I heard the front door close. I got in the corner of the closet and kind of hid myself with the clothes she had hanging on the rod. I also left the door cracked so I could look out and see the bedroom. I didn’t worry about her having to get a change of clothes out of the closet because she had a pair of slacks and sweat shirt hanging on the hook on the bathroom door. I hoped she would change into them right away so I could see her nakedness. She walked into the room with her purse and the mail she had gotten out of the mailbox. She set her purse down on the dresser along with the mail, but she kept her new issue of Cosmopolitan. She glanced at the cover at which point I thought she was going to go into the bathroom with it to read, but then set it down and took off her sweater and kicked off her shoes. That left her standing there in her sheer white blouse and dark skirt with what I thought then was panty hose. After all, it was still winter. Instead of going into the bathroom, she climbed up on the bed and sat back against the headboard to begin reading her magazine. I guess she realized she could use this time with her son at his friend’s house as her alone time.

She laid back thumbing through the magazine for a while and I just peeked out the crack in the door hoping she would get up soon and change clothes. She wasn’t showing anything, but her sheer blouse and bra I could see, was enough to keep my cock hard so that I could rub it through my sweatpants. I didn’t know how long she was going to be reading so I didn’t know how long I was going to be stuck in her closet. I figured she might go out back to get her son when she was ready for him to come home, at which point I could sneak out the front door. I reached inside of my sweatpants to stroke my cock and noticed she was moving around a little. She scratched her leg a little which resulted in her moving her skirt up her past her knees. She then set the magazine down beside her on the bed and unbuttoned a couple of buttons on her blouse. I didn’t know what she was reading, but it must have been something she liked. She didn’t take her eyes off the magazine as she unbuttoned her blouse and scratched her thigh again. That caused her skirt to go so high on her leg, I could see her panties, and also see that she didn’t have panty hose on; she was wearing stockings instead. She reached over to turn the page in her magazine, but she didn’t fix her skirt. As she brought her hands back up from the magazine, she pulled her skirt all the way up to her waist, and began rubbing her mound through her panties. She had her left hand down her blouse and inside her bra, gently rubbing her nibble. She kept on reading.

While she was doing that, I carefully raised my hips up off the pile of clothes I was sitting on, and pulled my sweats and underwear down a little so I could have free access to my cock. He was standing straight up demanding attention. While I was freeing my snake, I looked out at Charlotte and noticed she had stopped rubbing her mound. I thought maybe she heard me or something. She sat on the edge of the bed and fixed her skirt and stood up. I thought she was coming to see what was in the closet. She didn’t. She walked to the bedroom door and shut it and then locked it and returned to the edge of the bed. While she was standing there, she reached under her skirt and removed her panties, but left her skirt on. She also pulled the tail of her shirt out from her skirt and unfastened her bra in the front. She didn’t take either one of them off. I thought I was in heaven. She stood there for a second at the edge of the bed with her skirt on, her shirt open all the way and her bra unclasped which showed her medium sized boobs, that had extremely dark and large nipples. She started to sit back down on the bed, but she decided to arrange the pillows to make it more comfortable. She propped one pillow up against the headboard, and pulled her skirt up before she sat back down. Now instead of seeing her panties, I could see her pussy and what I thought was weird at the time was that she didn’t have that much hair down there. I thought all adults had a full bush until I was about 21 or so and heard about shaving. Hair or no hair, it was very exciting to see.

Instead of immediately beginning to play with herself again, she picked up her magazine and began reading it. She would look at a page, and if there was something interesting, leave it on that page for a while as she reached down and rubbed herself a little. I could tell she was very excited because her juices made her pussy lips glisten in the light. Every now and then instead of rubbing her pussy, she would pinch one of her nipples instead. I thought she was going to read the entire magazine, but I guess she was just looking for a sexual story. She must have found something she liked because she put both hands on the magazine and seemed to focus on what she was reading. Before I knew it, she set the magazine back down on the bed beside her.

This entire time, I was stroking my cock really slowly. I still had some lotion on it from before and it was very slippery, but I knew I could cum really quickly if I wasn’t careful. It was hard to stroke myself too well though because I had to try to be quiet so she wouldn’t hear me. Eventually I realized she was in her own world, so she couldn’t hear slight noises, but I didn’t want to bang against the door or the wall as I jacked my cock. I watched her now as she was sitting up against the pillow propped against her headboard. She had her right hand rubbing her pussy, and her left hand was alternating between her two tits. I had my entire hand wrapped around my cock as I stroked it. Eventually I rubbed all of the and lotion into my skin so I spit on my hand to use as lube, and then leaned over to spit on my cock with my hand wrapped around it. My dick got very slippery again.

Charlotte was in her own world now. She had her eyes closed most of the time as she leaned backwards and pleasured herself. Every now and then she would open her eyes to take a look down at her magazine. I don’t know what she was reading or looking at, but she must have liked it. She was in her own world, and I was in my own world too. I never closed my eyes though. I kept them glued through the crack in the closet door and kept them focused on her. Eventually, she stopped looking at the magazine and seemed to focus on something else in her mind with her eyes closed as she concentrated on what she was doing. She stopped using her left hand on her tits, and reached down to hold her lips apart. Her pussy glistened in the light and seemed to be begging somebody for a fucking. I really did want to pop open the door and show her my rock hard cock, but I wasn’t that confident of what she would do. I didn’t want to spoil the moment. She held her lips open with her left hand and took her right hand away, placing her fingers in her mouth. She sucked on them and slobbered on them to make them more slippery and to taste herself. She reached back down with her right hand and began furiously rubbing her clit, and sticking a finger in her pussy every once in a while. I began furiously rubbing my cock. I kind of got the feeling it wouldn’t be much longer before I came and before she came. She rubbed faster and faster and I stroked faster and faster. Her hips began bucking and I knew it was time. I quit trying to hold my cum back and just concentrated on my orgasm. She began moaning, quietly at first, but then she got louder and louder. And then it happened. Just as I was spewing cum all over my shirt, she must have cum too. Her furious hand motion had stopped and she just layed there, kind of panting and resting it seemed. I don’t know how long she was in that position, but after a while, she opened her eyes and sat straight up.

She swung her legs over the edge of the bed and began to take her stockings off. I tried not to move so she couldn’t hear me. She removed her stockings and then stood to take her skirt off and lay it on the bed. She was standing there almost naked, and I was in the closet watching as my cock softened a little after cumming. Seeing her stand there made my cock start to get hard again though. Then she took off her blouse and layed it on top of her skirt. I thought she was going to get totally naked, but she fastened her bra instead. She turned and walked right past the closet as I held my breath, and went into the bathroom to get some tissue. I could see her standing in front of the mirror in the bathroom, looking at herself as she wiped herself. She walked back into the room and got a clean pair of panties out of her underwear drawer and then went back into the bathroom to wash her hands and fix her hair after she put her panties on. She walked into the room and I just thought she was beautiful. Standing there, she took her slacks from the hook on the door and put them on, and then put her sweatshirt on. I guess it was time to go get her son. After she pulled her sweatshirt over her head, she fixed her hair again, and went down the stairs to go out the back door. I carefully climbed out of the closet, pulling my sweatpants up and walked quickly into the bathroom to look at myself. I had cum all over my sweatshirt, so I took a wad of toilet paper to wipe the shirt off, and then also took my sweatshirt off and turned it inside out. I had to hurry because I knew they would be back any minute, so I threw my trash into the can, and quickly went out the front door. As I was walking out the door, I turned and waved at the door as if somebody was standing there just in case any of the neighbors saw me leaving. I hoped anybody that saw Charlotte go out the back door, didn’t see me walk out the front door.

I went home that afternoon just having experienced one of the most erotic things I had ever seen in person in my entire life, up to that point. It was the object of my fantasies for a long time whenever I would masturbate. And even though it was only watching her and jacking myself off, I still consider it one of the most exciting things I have ever done or seen. I wonder what she is up to these days, 30 years later?