All characters in sexual situations are 18 years of age and older.
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It was a dark and stormy night (donât all stories start like this?) Actually, it was a beautiful, moon lit evening and I was naked from the waist down, peering out of my bedroom window and into the bedroom window of the woman that lived in the house next to us. For the past five years or so, since I was just a snotty little teenager, I had jacked off pretty much every night as I stood at my window and watched our beautiful, large breasted neighbour get ready for bed.
Her name is Mrs. Smith, Cynthia Smith actually, and she is a very beautiful older woman. She has huge tits. Really huge tits! Tits so big that Iâm sure they are almost as big as my momâs massive mammaries. I guessed that she is pretty much about the same age as my mom too. I usually got off watching the way she took care of her big tits almost each and every night as she got ready for bed. To be perfectly honest, I have never seen my mom naked nor have I thought of her in a sexual way but come to think of it, I guess that she looks every bit as hot as Mrs. Smith.
For some time now, I had been suspecting that Mrs. Smith knew that I was watching her undress every night. She never really did anything to let on that she knew I was watching, it was just the way her evening ritual started to get a little more elaborate, provocative and somewhat theatrical. She did things that you probably wouldnât do unless you had an appreciative âaudience.â I couldnât be sure that she knew I was watching her but I had my suspicions.
I, or perhaps we, were very lucky in that the only place that could see into her bedroom at night was from my bedroom. Both our windows had privacy from the street and this meant that we could do our thing without too much worry that we might be seen, interrupted or busted.
When I first started watching her, she just did the normal things you would expect of someone who is getting ready for bed. I would get a brief glimpse of her massive tits just as she slipped out of her bra and turned out the lights. The moment I lived for every night, was when she unhooked her bra and let those big babies hang loose and get some air. They would almost leap out of her big bra and then roll around on her chest for a few seconds before gravity took over completely.
Because my window was higher than hers, I had a pretty good view of her from the waist up as she sat in front of her mirrored dresser. When she sat down, it looked like her huge tits would finally come to rest on her lap. I couldnât tell for sure if they hung all the way to her lap but it looked pretty darned close.
As she slipped off her bra, she would usually give her tits a quick (too quick) massage. It was if they were itchy or something after being cooped up all day in that massive industrial strength garment. As she massaged them, her fingers would almost disappear into the twin-mountains of soft looking breast flesh and then she would turn out the lights and the show would be over. It was hard to see how big her nipples were because she would sit sideways and the whole show would be over in the matter of just a minute or so. This short glimpse of her big tits however, was more than enough brain candy to fuel my nightly jerk off session even though, by the time I was finally ready to cum, I was staring into a dark window unable to see anything. The âshowâ would never last long enough that I was able to cum while actually looking at her big tits.
As time went on, she started to take more and more time as she prepared for bed. Lately, âgetting ready for bedâ was taking her almost an hour every night and I was finally able to jerk off and cum while actually looking at her big tits. So far, my luck has been holding and lately Iâve been treated to great show after great show.
I have a roll of paper towels stashed under my bed and pretty much every night, I blow one or two massive loads into a couple of paper towels. I learned at an early age that it got terribly messy if I tried to blow my load into anything less than at least two or three layers of heavy-duty paper towel. Jerking off with Kleenex was a joke. When I was much younger, I tried jerking off into some Kleenex and my load blasted right through the stuff and hit the wall. Then I tried using a paper towel with the same messy result. The wall was taking quite a beating! Then I tried jerking off into two or three thickness of paper towel and the same frickin thing happened. What a mess! I finally learned that the secret to success was to leave a gap of about two inches from the end of my dick to the paper towel that was held tightly around the end of my cock by one of my hands. This worked better but was still really messy sometimes because I would usually cum so much that I would fill the end of the paper towel and it would start leaking out. And, sometimes I would get a bit carried away and shove the end of my cock right through the paper towel and blow my load all over the place. I was on a search for something I could blow my load into without worrying about where all my cum would go.
When my cock was much smaller, I would sometimes use a condom and really enjoyed the fact that I didnât have to worry as much about my load blasting all over the place. It wasnât too long before I had a hard time (no pun intended) finding condoms large enough to fit my growing penis. It seemed that my cock was getting larger and larger all the time and when I found that I couldnât roll on an extra large condom without it hurting a bit, I sensed I must be getting pretty darned big. In fact, I was getting more and more embarrassed by the size of the damned thing. After gym class at school, I started to try and have my shower after everyone had left so that I wouldnât have to put up with the stares and snide comments. I mean, who wants to be called horse cock or donkey boy? I didnât really know what they meant by that but I knew they thought I was a bit of a freak.
The thought that I just might be a freak of some kind caused enough dread within me that I shunned any attempts by girls at school to get to know me. Some guys thought I was gay because I didnât date girls. The truth was that I was just too damned embarrassed and the last thing I wanted was to have some girl start to like me and then later reject me when she found out about my âbig problemâ. Every time I got near a good-looking girl (usually one with big tits) I would pop a boner and have to go jerk off. These oversized balls of mine produce a lot of cum and it seemed that if I didnât jerk off five or six times a day, it starts to really ache bad down there. I figured that I was in for a pretty lonely life and that the only sex I would ever get would come from the pleasure I got from my own hands. I even sucked myself off a few times but I stopped doing that because it made me feel like a real perv and I told myself that I would only resort to blowing myself if it became obvious that I would never have a girlfriend. Besides, I couldnât swallow fast enough to handle the massive load of cum and I would always make a huge mess all over the place that took a long time to clean up.
Anyway, thatâs enough about my big stupid penis and balls. I should get back to the details of my voyeuristic adventures with Mrs. Smith. Although our windows were only about 20 feet apart and I had a pretty good view of the âactionâ, I wanted however, to be able to see more, much more. I came up with a plan. Not long after the nightly âshowâ started to take longer, I pretended to develop an interest in bird watching (well, it was the truth after a fashion) and I asked my mom for a nice pair of binoculars for Christmas. Fortunately, she bought me a set of really good ones with zoom lenses and now, I could not only see Mrs. Smith better, I could see detail that I never knew existed. Now I could tell when Mrs. Smithâs nipples got hard and I could even see the little bumps on her nipples. When I zoomed in, one of her big tits would almost completely fill the field of vision and it was like I was right in the room with her.
As I spied on Mrs. Smith, I would jack off with one hand and hold the binoculars with the other. This didnât work very well at all. The view got very shaky (if you know what I mean) and I had to put them down when I started to cum so I could use the spare hand to hold some paper towels to help contain the flood of cum. Besides, for years I had developed a two handed technique that was required to properly handle my big stick.
The answer came to me one day as I sat there catching my breath after a massive orgasm. Mrs. Smith had just turned out her light and I when I looked over at the binoculars that had landed on the bed where I tossed them, I noticed a female thread on the bottom. It suddenly dawned on me that it just might be possible to mount the binoculars on a tripod. I dug deep into the back of my closet and sure enough, a tripod for my old camera was there. I quickly set it up and became very excited when I realized that my jerk off sessions might have turned a new corner. Now, it just might be possible to get a clear, steady view of Mrs. Smith and have both hands to mercilessly beat my throbbing meat. Becoming even more innovative, I found that my plastic garbage bucket would fit in between the legs of the tripod and if I leaned it at just the right angle, I was able to pump my loads of cum into it. Sure, it was a bit messy and I had to clean out the bucket all the time but hey, I didnât have to try and catch my big, sticky load with a stupid paper towel. On balance, it was much better because it was a lot less messy that when the head of my cock pushed its way through the soggy end of the paper towel and I ended up cumming all over the place. Have you ever tried to get a big load of cum out of the carpet? This was much better.
I became excited about test-driving the new arrangement. The very next night I was in business and had a whole new lease on life. Mom had gone to bed. She is a doctor at a research facility and starts her day really early so she always goes to bed early. I was butt naked, the tripod was set up, the âcum bucketâ was in place and I was slow stroking my bad boy waiting for Mrs. Smith to come into her bedroom and do her thing. I must have dripped about a half a cup of glistening pre-cum into the bucket by the time she finally turned on her light. Man, was I ready for this!