It was a dark and stormy night (don’t 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 I’m sure they are almost as big as my mom’s 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 wouldn’t do unless you had an appreciative “audience.” I couldn’t 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 couldn’t 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 “show” 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, “getting ready for bed“ 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 I’ve 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 didn’t have to worry as much about my load blasting all over the place. It wasn’t 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 couldn’t 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 wouldn’t have to put up with the stares and snide comments. I mean, who wants to be called horse cock or donkey boy? I didn’t 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 didn’t 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 “big problem”. 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 didn’t 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 couldn’t 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, that’s 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 “action”, I wanted however, to be able to see more, much more. I came up with a plan. Not long after the nightly “show” 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. Smith’s 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 didn’t 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 didn’t 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 ‘cum bucket’ 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!
I was always a little worried that my mom would come into the room and catch me jerking off. Even if she didn’t catch me red handed (so to speak) there was no mistaking the musty odour of sex emanating from the puddle of precum in the bucket. I used a lot of the precum to grease up my cock to make it nice and slippery and when I did that, the smell got even stronger.
As I pondered all of this I was interrupted in my thought when true to form, Mrs. Smith walked over to her dresser and studied herself in the mirror. She leaned her head first one way and then the other as she took off her earrings. She had already undressed somewhere and was now wearing a burgundy coloured, robe that looked like it was made from silk. This particular robe was one of my favourites (I have seen many of them over the years) because it was so short and because it tied at the waist in a way that left no doubt that Mrs. Smith was packing a world-class set of hooters.
I rarely got to see her change out of her street clothes and assumed she must keep her robes and a laundry hamper in the bathroom or something. Whatever the case, it was nice that we could usually cut to the chase and not waste a lot of time getting completely undressed. (Although, I admit there were times when I wished I could watch her undress from the very beginning.)
And so it was that Mrs. Smith continued her nightly ritual. While she still had the robe on, she would turn this way and that with her hands on her hips as she posed like a model and checked out her figure. She would suck in her gut (she had a very small tummy) and cinch the belt on her robe for a minute to make her waist look as small as possible. Or perhaps she did that to make her huge tits look even bigger that they already did. I had no doubt that Mrs. Smith was proud of her big tits and I’m sure she took great pleasure from their size and shape. She cupped her silk covered tits in her hands and hefted them a few times, still turning this way and that way as she examined herself in the mirror. Then came the moment I always looked forward to. She pulled back the top of her robe until it was off her shoulders and leaned her head back to let her long hair fall over her naked shoulders. Her robe was then lowered just low enough that her big nipples were still hidden from view but you could see about a mile and a half of cleavage. She pressed her big boobs together creating even deeper cleavage. Man, all I wanted to do was shove my face deep into that cleavage and bury myself in mountains of soft breast flesh.
My cock got even harder as she started the cleavage thing. Man it felt good to stroke it my cock. Sometimes, I became worried that I would become obsessed with jerking off. It felt so frickin good! I could only imagine what it might feel like to place the shaft of my cock in between her big tits or maybe even stick it into her mouth. I had no idea what a blowjob or a wet pussy would feel like as it surrounded my cock but I was sure that if I ever got a taste of sex for real, I would be forever addicted.
In the theatre of my mind, I could almost hear some sleazy stripper music playing in the background as I watched Mrs. Smith and stroked my big cock up and down. She slowly started to remove her robe. It was still on her arms but the front opened and dropped enough that her tits came into view. Well, most of her tits came into view. Her tits are so fucking huge that the bottom of each massive tit must have been near her tummy. My view through the window only allowed me to see most of her upper body when she was seated but I couldn’t quite see the bottom of her tits.
Then came one of my favourite parts, she untied the belt on her robe and tossed it over the back of a chair leaving her naked, at least from the waist up. Until she stood up, I couldn’t tell if she was wearing panties or nothing at all. There they were! Huge fucking cannons! Fuck me! I hoped I would never get used to the thrill I got whenever those big babies came into view. Man, this woman has a set of major league funbags. She used both hands to cradle and heft her left tit. She kind of massaged it a bit and then lifted it up as high as she could. I loved this part. She scooped up all that tit flesh and brought the big nipple to her lips. She rolled her tongue around the nipple and thanks to the high-powered binoculars, I could see the big nipple start to erect. As soon as it had extended a half an inch or so, she started to softly suck on it.
I wondered how many women could suck their tits as easily as Mrs. Smith could. It made me think about my mom for a second. I’m pretty sure Mom’s tits are even larger than Mrs. Smith’s and I found myself wondering if mom ever gave her tits a tongue bath similar to the one I was witnessing. Before I knew it, I was stroking my cock harder and faster as I thought about my mom’s huge breasts. I chastised myself for a second or two, gave my head a shake to exit the daydream and returned my focus to the live show that Mrs. Smith was putting on.
She “dropped” her left tit and it went crashing down and wobbled around for a second before coming to rest. She picked it up and dropped it again. She must love the way it feels when that much soft flesh goes crashing down. Or maybe, like me, she just liked watching the big orb flop around.
Then, consistent with her nightly ritual, she started the same treatment with her right breast. I loved the part when she sucked the nipple deep into her mouth. She seemed to be sucking really hard tonight because her cheeks caved in when she sucked. I let my imagination run wild and imagined those cheeks caving in like that as she sucked my cock. What if she liked sucking cock as much as she loved sucking her own tits?
I knew the nightly “show” was coming to a close pretty soon so I started to really pump my fat prick. I got that old familiar feeling that signalled the rush of cum from my balls and I got ready to aim it into the bucket.
I didn’t want to tear my eyes away from Mrs. Smith for even a moment and I watched as she placed a hand under each huge breast, cupping them in her hands as best she could, and then lifted them both as high as she could. Her hands pretty much disappeared into the super-pliant soft breast flesh. She was now standing in profile to me and looked straight into the mirror of her dresser. Now that she was standing, I cast my eyes quickly downward and I could see the thin string of her thong as it headed into the crack of her ass.
Returning my gaze to her huge fucking tits, I saw her bounce her boobs a couple of times and let them fall. She seemed to like watching them flop around. I was really into stroking my bad boy now. I was getting close to cumming and was trying to hold off until she got to my favourite part. Here it comes (so to speak). She grabbed both her nipples and pulled on them, softly at first and then harder and harder. She tugged and yanked on her nipples making her big tits flop up and down wildly on her chest. Then she pulled her nipples up and away from her so that she grossly deformed the shape of her tits and turned them into pointed objects, each larger than a football. That was it! My cock was so hard I couldn’t bend it down to aim at the bucket so as I started to cum, I had to hunch over like a hound dog fucking a football and blasted the first volley of hot cum into the bucket. Splat! Well, most of it got into the bucket. It hit the far side of the plastic bucket with a loud splat that was so loud I thought my mom might hear. Shit!
I pumped a few more ropes of thick cum into the bucket and then took another look into the binoculars hoping Mrs. Smith was still there. She was. And then … at the ripe old age of eighteen, I just about had a heart attack. Just as I zoomed in on Mrs. Smith, she turned towards me, lifted a big tit up so she could kiss the nipple, let it drop heavily back to her chest and then did the same to the other tit. This time however, as she kissed, licked and sucked her own nipple, she maintained suction between her nipple and her lips but then, she looked up and I suddenly became aware that she was looking right at me with smiling eyes. The binoculars made it seem as if she was just a couple of feet away and when she looked right at me, I just about lost it. My cock spewed another couple of thick ropes into the wall as I ducked away from her view. I’m not sure why I ducked but duck I did. A simple reflex from being “caught” I suppose.
I didn’t know what to do or think or how to feel. I felt like a dirty little perv for being caught peeping but at the same time, I felt strangely excited. On balance, I was pretty much scared shitless. What if Mrs. Smith told my mom that I was some form of pond scum low life pervert peeping Tom? Shit!
I went into the bathroom, pumped the last few shots of cum out of my cock and took a big piss. I wet a towel and went back into my bedroom to clean up all the cum that had missed the bucket when I had gone berserk. I had to work in the dark because I didn’t want to let Mrs. Smith see my lights on.
After cleaning up my room as best I could, I got into bed and lay there with my mind racing a mile a minute. Did she really know that I was watching? If she did, would she tell my mom? Was I in deep shit? How could I ever look her in the face again? What would mom say and do if she found out?
On the other hand, what if Mrs. Smith knew I was watching and enjoyed the fact? What if she was putting on a show just for me? My cock started to thicken again and before I knew it, I was even hornier than I was before. Shit! I couldn’t help myself and started beating off again. In my mind’s eye, I imagined that Mrs. Smith wanted me to watch her every night and knew I was spanking my bad boy while watching her. I fantasized that she could see my big cock and wanted it. In this daydream (can it be a daydream at night?) she was lifting up her huge tits and asking me to suck her nipples. Just as I began to think about what it might feel like when she put her hand on my hard cock, I blew another huge load into the handy bucket. I must be out of my fucking mind! I grabbed some paper towels and cleaned up as best I could and fell fast asleep.