Lessons Learned That Summer Part One

I love reading about older women seducing young boys, here’s what happened to me. Our next door neighbor, and mom’s best friend is Judy. She practically lives over at our house, but I’m not complaining. You see, Judy is about 25-27 years old, but still looks like a teenager. She has HUGE tits, flat tummy and a perfect ass. I have heard my mom refer to her as being ‘loose’. I think that is because she wears clothes that accentuate her figure. She has been the focal point of almost all of my masturbation. I have only been masturbating for a few months, and Judy kind of got me started. Behind mom’s back, Judy would say things to me like, ”Bobby, you’re going to have to beat the girls off with a stick.” Or “So tell me Bobby, have you started playing with your little we-we yet? I’ll bet you have.” Or “How many girls have you been dipping your little dip-stick in, Bobby?” As I got a little older, and discovered masturbation, I finally understood what she was saying. For her to be asking me questions about my dip-stick was quite a turn on for me. I was always too embarrassed to answer when she would ask those questions, and I think she knew that.

Like I said earlier, Judy lives right next door, and I guess I was always too busy playing to notice that her bedroom and bathroom are right across from mine. I have the only bedroom upstairs, and so I can look right down into Judy’s bedroom and bathroom. I don’t think Judy knew this because she has a high fence all around her house, and she never pulls the curtains closed. From upstairs, I can see just about everything, especially into her shower.

I had saved up all my money from last summer, mowing lawns around the neighborhood. With the money I was going to make this summer, I was planning to buy a mini-bike. After finding out that I could see Judy when she takes showers, I decided to take some of that money and buy some binoculars. I already have a telescope, but it is too powerful for viewing an object that close. I bought the kind of binoculars that can be attached to the telescope’s tripod (have you ever tried to jack-off with one hand and hold binoculars in the other?). I was extremely careful to ensure my light was off when I watched her because I didn’t want to blow the chance of seeing a lot of her. When she was in the shower, she took the longest of any one I know. She spent at least 15 minutes just washing those humongous boobs, but then she spent almost double that amount washing her nookie. She would take the shower nozzle and rinse her pussy for a long time. Usually I would cum while she was still washing her tits! Sometimes my dick would stay hard and I would cum again by the time she was rinsing. One night I was treated to the sight of her shaving her mound, then afterwards she played with herself.

As I grew older, she got a little more risqué with what she would say to me. Then I found out she knew I was watching her. Judy was over having coffee with mom. I came down into the kitchen for a drink and mom asked me to get my sister ready for bed. I said, “Aw mom, you know she won’t listen to me, and I’ve got another hour’s worth of homework.” (I was lying). So mom went upstairs to get Megan ready for bed. I was getting ready to go back upstairs when Judy said, “Hey Bobby, you dating any one?” I told her no, so she said, “Well, I find that hard to believe, a good looking boy like you.” I told her it’s true. Judy then floored me by saying, “Well maybe you should spend more time chasing girls instead of star gazing!” I said, “I don’t spend that much time looking at the stars.” “Well then maybe you should spend less time looking into my bathroom!” I acted like I didn’t know what she was talking about. Then she pushed even farther whispering, “How did you like it the other night when I shaved my pussy? I did that just for you!” I was totally speechless, and extremely turned on. “I’ll bet you just about blasted a hole in the wall with your cum!” I was wearing jogging shorts at the time and my cock was making a very noticeable tent in the front. She said, “I can see you are very excited just thinking about it. When your mom comes back downstairs, tell her I had to go home, then you rush back up to your room”. I asked her why and she said, “You’ll see!” She reached over and gave my erection a squeeze, then she left. I didn’t want mom to see me this way, so I told her as I was going upstairs that Judy went home. I rushed into my room and quickly took the telescope off the tripod and replaced it with the binoculars. Judy’s bedroom light was already on, but the bathroom light was off. I didn’t have a clue as to what she was going to do, but I was sure excited. I locked my door so that mom couldn’t walk in and catch me looking at Judy and especially so she couldn’t catch me jacking-off.

Out of the corner of my eye, I saw movement in the bedroom. From my vantage point, I could see a little over half of the room. I was able to see the vanity, the bed, and a closet. The movement I saw was Judy going into her closet. She brought out what looked like a gown, then she moved out of sight. In a few minutes, she appeared again and sat on her bed facing my direction. There were all kinds of thoughts going through my mind, but I was mostly worried that she would tell my mom that I’m a peeping Tom. Judy bent over and removed her shoes. Then she went into the bathroom. Her shower curtain was closed, so I couldn’t see anything. She was in there a few minutes when the light went off and I saw her reappear in her bedroom. She walked by the window and looked in my direction, she was smiling. I could see her nipples protruding through the thin material of the gown and the short teddy she had underneath. This was one time I wish I could use dad’s camcorder! She went over to her bed and fiddled with a radio, then started dancing around. After a few minutes, she took off her robe, and I was mesmerized by her breasts bouncing around. Her top soon followed and I was getting to see those boobs, the nipples were sticking out like fingers. They were as big around as dimes and were at least an inch long! She began rubbing her tits and then concentrated on her hard nips. When she pinched them, I started cumming. Incredibly, I didn’t go soft, but I couldn’t stroke it because it was too sensitive. All she had on now was red panties. When she turned around I saw they were the type that let you see the whole ass. We call those type ‘butt floss’. Then she bent over and spread her cheeks, I could see the outline of her pussy lips, and I began to stroke my engorged member again. She stayed in that position to remove her panties and I was afforded a fantastic view of her hairless slit. By the time she turned around and moved her hands to the mound, I was cumming again. It was just in time because only a few minutes later she went over to her bed and turned the light off. I was dumbfounded by the events that just occurred, and considered myself very lucky.

The next day, I didn’t get to see Judy at all, which was very disappointing. On Saturday she came over and visited with my mom again. They were having coffee and talking very casually when I walked into the kitchen. Judy tried to carry on a conversation with me about school, but all I could muster for answers were shaking or nodding my head. My mom asked me if I was OK, and I nodded. Megan called for mom, and she went to see what she wanted. Judy looked me in the eyes, and gave me a very sultry look. “So, Bobby, did you like the show the other night?” I nodded and shifted to help relieve the pressure that was building in my shorts. “I thought you would, I kind of enjoyed doing it. In fact, when I turned my light off, I had to play with myself because I got so excited!” I didn’t say anything, so she started again. “Would you like to watch me do that, too? I have an idea, tonight I’ll let you watch how I play with myself, and maybe sometime you’ll let me watch you, whaddya say?” I still didn’t know what to say, but nodded and went upstairs. It seemed like it took her forever to go home. All I could do was wait impatiently for her bedroom light to come on. I was already naked when it finally did. She went straight to her bed and took off all her clothes. Judy spread her legs wide and opened her vaginal lips. She then began to dip a finger inside and bring it up and rub the top of her slit. She dipped in two fingers, then three! I was ready to cum already, so I stopped touching myself. I didn’t want to miss anything. She rose up and opened a drawer in her night stand, and pulled out something pink. It was a penis shaped dildo, about twice the size of mine. She kissed the head of it then sucked it about halfway into her mouth. Judy slowly lowered it to her breasts and rubbed each nipple with it. Again, it moved slowly downward and was rubbed all around the outside of her mound. Finally she moved it to her opening and popped the head in. She moved the other end around in circles, and then started pushing it in deeper. By this time, I was ready to cum and I wasn’t even touching my dick! I decide to help it out and stroked it about three or four times and I exploded. When I was able to concentrate again, I saw that she was plunging that fake penis in and out so quickly, it was just a pink blur! Her head was tossing from side to side and I think she was cumming. Just a few minutes later her light went off.

That was on a Friday night and early the next morning I heard Judy out in her back yard. I looked and couldn’t believe my eyes. She was laying out on a chaise lounge, topless! Like I said earlier, she has a high fence around her house and I’m the only one that can see her. Watching her lie there with no top on was such a turn on and I had the solution in hand, so to speak. I woke up with a hard-on, and seeing her did nothing to squelch that. Needless to say, I had an explosive orgasm.

The following Thursday was the last day of school and I had big plans for the summer. I was going to try to get everyone in the neighborhood to let me take care of their yard work for them, especially Judy. Friday morning I woke up and saw Judy in the shower. Since she already knew I was watching her, I made no attempt to hide. I saw her look at me and smile, I think she knew I was jacking-off. After recovering for a while, I went and knocked on her door. She answered the door with a very sheer robe on and as far as I could tell nothing else! She invited me in and asked me if I wanted a Coke or anything. I asked for a Coke and she asked me what I was going to do with myself now that school was out. I said, “Well, Judy, that’s the reason I stopped by this morning.”

“OH!”
“Uh, yes, I was wondering if you needed anyone to do your yard work for you this summer?”
“I see. You are being the little entrepreneur, huh?”
“I don’t know what that means, I’m just trying to make some money to buy a mini-bike.”
“OK, so little Mr. Business man, how much would you charge for doing my yard work?”
“I can charge you $10 a week, or $3.00 an hour, and you can pick the day of the week you want it done.”
“That doesn’t sound like very much money for all the work you will have to do.”
“My mom told me I couldn’t charge you as much as everyone else, on account of your divorce and all.”
Judy laughed, and said, ”You tell your mom to stay out of your business deals. I will pay you $15.00 a week, and if you could, I would like it to be done on either Thursdays or Fridays. Does that sound OK to you?”
“Yes ma’am. But please don’t tell my mom.”
“You want me to keep secrets from your mom? Well I guess we already do, don’t we?” I turned about three shades of red, and couldn’t answer to save my life.