All characters involved in sex scenes are 18 years of age or older.
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It was a dark and stormy night (isn’t that how all stories start?) In fact, it was a beautiful, moonlit night, and I was naked from the waist down, staring out my bedroom window. For the past five years or so, ever since I was a young teenager with a runny nose, I had stood at the window almost every night and watched my beautiful big-breasted neighbor get ready for bed.
Her name was Mrs. Smith, actually Cynthia Smith, and she was a very beautiful older woman. She has huge breasts. Really huge breasts! The breasts were so huge, I am sure they were almost as big as my mother’s huge breasts. I think she is the same age as my mother. I usually see how she caresses her big breasts almost every night when she gets ready for bed. To be honest, I have never seen my mother naked or thought about her in a sexual way, but when I do, I think she looks just as sexy as Mrs. Smith.
I have suspected for some time that Mrs. Smith knew I watched her undress every night. She never really did anything to show that she knew I was watching, it was just that her evening rituals started to get more complex, provocative and a little dramatic. She did something you probably wouldn’t do unless you had an appreciative “audience”. I’m not sure she knows I’m watching her, but I doubt it.
I, or rather we, were very lucky because the only place I could see her bedroom at night was my bedroom. Both our windows were protected from the street, which meant we could go about our business without worrying that we might be seen, harassed, or caught.
When I first started watching her, she was doing the same normal things one does while getting ready for bed. When she takes off her bra and turns off the lights, I get a brief glimpse of her huge breasts. I look forward to that moment every night when she takes off her bra and lets those big babies relax and get some fresh air. They practically spill out of her big bra and sway around her breasts for a few seconds before gravity completely takes over.
Because my window is higher than hers, I have a clear view of her from the waist up as she sits in front of the mirrored dresser. As she sits, it looks like her huge breasts finally come to rest on her lap. I couldn’t tell if they hung down around her legs, but they looked pretty close.
When she takes off her bra, she usually massages her breasts quickly (very quickly). Like they were itching or something after being locked in that heavy industrial strength garment all day. Her fingers almost disappear into the soft looking mountains of breast muscle as she massages, then she turns off the lights and the show is over. It’s hard to tell how big her nipples are because she’ll be sitting on her side and the whole show is over in less than a minute. However, this brief glimpse of her big breasts was enough for my nightly masturbation sessions, even though by the time I was finally ready to cum, I was looking into a dark window where there was nothing to see. This “show” never goes on long enough for me to be able to cum while looking at her big breasts.
As time went on, she started spending more and more time getting ready for bed. Lately, it’s been taking her about an hour to “get ready for bed” every night, and I’ve finally been able to masturbate and cum while looking at her big tits. My luck has been good so far and I’ve been watching one great show after another lately.
I have a roll of paper towels hidden under my bed, and almost every night, I blow a piece or two into some paper towels. I knew at a very young age that if I tried to blow my load into anything less than at least two or three layers of heavy tissue, things would get very confusing. Masturbating with tissues is a joke. When I was younger, I attempted to masturbate with tissues and as a result, my semen shot straight through the tissue and hit the wall. Then I attempted to use tissues with the same mixed results. Hit the wall hard! Then I attempted to jerk off with two or three layers of tissue and the same thing happened. What a mess! Eventually I discovered that the secret to success was to leave about a two-inch gap between the tip of my dick and the tissue with one hand holding the tip of my dick tightly. This works better but is still sometimes confusing because I usually cum so much that I fill up the end of the tissue and it starts leaking. And, sometimes I get a little carried away, stuff the head of my cock in a tissue and squirt my cum all over the place. I was looking for something that would let my cum flow out without having to worry about where my cum would end up.
When my dick was much smaller I used condoms sometimes and really enjoyed the fact that I didn’t have to worry so much about my penis exploding everywhere. It didn’t take me long to find a condom big enough to fit over my growing penis (no pun intended). My dick kept getting bigger and bigger, and when I discovered I couldn’t put on a king-sized condom without feeling a little pain, I felt like I was really getting bigger. In fact, I started getting a lot more embarrassed about the size of that thing. After gym class at school, I started trying to shower after everyone had left so I wouldn’t have to endure the stares and nasty comments. I mean, who wants to be called a “horse cock” or “donkey boy”? I didn’t really know what they meant, but I knew they thought I was a bit of a freak.
The idea that I might be some kind of freak instilled so much fear in me that I avoided any attempts by girls at school to get to know me. Some people think I’m gay because I haven’t dated girls. The truth is that I’m too embarrassed and the last thing I want is for a girl to like me and then reject me when she finds out about my “big problem.” I get so angry whenever I’m around a pretty girl (usually a girl with big boobs) that I have to jerk off. These extra large testicles of mine produce so much semen that if I don’t jerk off five or six times a day, I’ll literally start to hurt down there. I thought my life would be very lonely and the only sex I’d get would come from the pleasure I’d get from myself. I also gave myself a blowjob a few times, but I stopped doing it because it made me feel like a real pervert, I told myself, and it was only when it became clear to me that I would never have a girlfriend that I resorted to it to brag. Also, I can’t swallow fast enough to handle large amounts of semen, and I always leave a mess that takes a long time to clean up.
Anyway, enough about my big, stupid cock and balls. Let me elaborate on my voyeuristic adventures with Mrs. Smith. Although our windows were about 20 feet apart and I had a good view of the “action,” I wished I could have seen a lot more. I came up with a plan. Shortly after the nightly “shows” started getting longer, I pretended to be interested in bird watching (well, after a fashion that was a fact) and asked my mom for a nice pair of binoculars for Christmas. Luckily, she bought me a really nice set of zoom lenses, and now, not only could I get a better look at Mrs. Smith, but I could also see details I didn’t know about. I could now tell when Mrs. Smith’s nipples were getting hard, I could also see the little bumps on her nipples. When I zoomed in, one of her large breasts almost completely filled the field of view, as if she and I were in the room.
When I was spying on Mrs. Smith, I would masturbate with one hand and hold my binoculars with the other. It just doesn’t work. The view got really shaky (if you know what I mean) and when I started to cum I had to put them down so I could use my free hand to get some tissues to help control the flow of semen. Additionally, over the years I have developed the two-handed technique necessary to properly operate my big stick.
One day, as I was sitting there catching my breath after a massive orgasm, I found my answer. Mrs. Smith had just turned off the lights, and as I looked at the binoculars I had left on the bed, I saw a busbar underneath. It occurred to me that perhaps I could mount the binoculars on a tripod. I reached into the back of the closet and, sure enough, the tripod for my old camera was there. I immediately set it up and was very excited when I realized that my masturbation was taking a new turn. Now it was perhaps possible to watch Mrs. Smith clearly, steadily, and ruthlessly crush my throbbing body with her hands. Even more novel, I discovered that my plastic trash can could be placed between the legs of a tripod, and if I tilted it at the right angle, I could pump a large quantity of semen into it. Sure, it’s a little messy and I have to clean the bucket all the time, but hey, I don’t have to try to catch my big, sticky load with a useless paper towel. Overall, it was a lot better because when the head of my cock passed the wet end of the tissue, I was cumming all over the place, making it less messy. Have you ever tried to get a large amount of cum out of your carpet? It’s a lot better.
I’m excited to test the new arrangement. The next night I get down to business and start a new life. Mom has gone to bed. She’s a doctor at a research institute and starts work very early every day, so she always goes to bed early. With my ass bare, the tripod set up and the “cum bucket” in place, I slowly stroke my bad boy while I wait for Mrs. Smith to come into the bedroom and do her thing. When she finally turns on the light, I must have dripped about half a cup of glistening pre-cum into the bucket. Man, am I ready!
I was always a little worried that my mom would come into the room and find me masturbating. Even if she didn’t catch me red-handed (so to speak), there’s no mistaking the foul smell of a bucketful of semen. I used a lot of precum to lubricate my cock and make it nice and slippery, and as I did so, the smell got stronger.
While I was thinking all this, my thoughts were interrupted when Mrs. Smith went to the dressing table as usual and looked at herself in the mirror. As she took off her earrings, she tilted her head first to one side and then to the other. She had taken off her clothes somewhere and was now wearing a burgundy colored gown that looked like it was made of silk. This particular robe is one of my favorites (I have seen many of these over the years) because it is so short and the way it is tied around the waist leaves no doubt that Mrs. Smith is packing a world-class set robe.
I rarely see him change out of his street clothes and think he has to put his robe and laundry basket in the bathroom or something. Anyway, it’s nice that we can usually get straight to the point instead of wasting a lot of time taking off his clothes completely. (Although, I admit that sometimes I wish I could have seen him undress from the start.)
Thus, Mrs. Smith continued her nightly ritual. While she was still in her cloak, she would put her hands on her hips to check her figure and sway from side to side in a model-like pose. She would suck in her stomach (she had a small belly) and tighten the belt on her cloak for a minute to make her waist look as small as possible. Or maybe she did it to make her huge breasts look even bigger than they already were. I have no doubt that Mrs. Smith was proud of her large breasts, and I am sure she was very pleased with their size and shape. She held her silk-covered breasts in her hands, lifted them several times, still turned them from side to side while studying herself in the mirror. Then the moment I was waiting for came. She pulled back the hem of her cloak until it fell off her shoulders, then tilted her head back so that her long hair fell over her bare shoulders. Then her robe was lowered 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 tits together to create an even deeper cleavage. Man, I just want to bury my face inside her cleavage and bury myself in those soft mountains of breast flesh.
As she started to play with her cleavage, my cock got even harder. Man, it feels so good to have my cock stroked. Sometimes I used to worry that I would get addicted to masturbation. It feels so good! I could only imagine what it would feel like to have my cock between her big tits or in her mouth. I don’t know what it would feel like to get a blowjob or a wet pussy wrapped around my cock, but I’m sure if I ever got a real taste of sex I would be addicted to it forever.
In the theater of my mind, I could almost hear some raunchy striptease music in the background as I watched Mrs. Smith stroke my big cock up and down. She slowly began to take off her robe. It was still on her arms, but the front of it opened up and lowered enough to reveal her boobs. Well, most of her boobs were exposed. Her boobs were so big that the base of each huge boob must have been close to her stomach. When she sat down, I could only see most of her upper body through the window, but not the bottom of her boobs.
Then comes one of my favorite parts, where she undoes the belt on her robe and throws it over the back of the chair, leaving her nude from at least the waist up. Until she stood up, I couldn’t tell if she was wearing panties or nothing at all. There they are! Huge fucking cannon! Fuck me! I hope I never get used to the excitement I feel whenever those big babies come into view. Man, this woman has a set of major league funbags. She grabbed her left tit with both hands. She massaged it a little and then lifted it as high as she could. I love this part. She squeezed the entire nipple flesh and brought the big nipple to her lips. She swirled her tongue around the nipples and thanks to the high powered binoculars I could see the big nipples start to stand up. When it grew about half an inch she started to suck on it gently.
I wonder how many women can suck boobs as easily as Mrs. Smith. It reminds me of my mom. I was pretty sure Mom’s boobs were bigger than Mrs. Smith’s, and I wondered if Mom had ever given her boobs a tongue bath as I had seen. Before I knew it, I was stroking my cock faster and faster thinking about my Mom’s huge boobs. I scolded myself for a second or two, shook my head and snapped out of the daydream, then focused my attention on the live show that Mrs. Smith was putting on.
She “dropped” her left nipple and it fell down, shaking for a second before stopping. She picked it up and threw it away. She must have liked the way it felt when that soft flesh collapsed. Or maybe, like me, she just enjoyed watching that big ball bounce around.
Then, as was her nightly routine, she started the same treatment on her right breast. I love the part where she takes the nipple deep into her mouth. It seemed like she was sucking really hard tonight because her cheeks hollowed out while sucking. I let my imagination run wild, thinking about how her cheeks must have puckered up when she sucked my cock. What if she loved sucking cocks as much as she loved getting her tits sucked?
I knew the night’s “show” was coming to an end soon, so I really started stroking my thick cock. I felt that familiar feeling that signaled the cum was about to burst out of my balls and I was ready to shoot it in the bucket.
Not wanting to take my eyes off Mrs. Smith for a moment, I saw that she had put one hand under each of her huge breasts, held them in her hands as high as she could, and lifted them as high as she could. Her hands almost disappeared into the super-flexible breast flesh. She was now standing next to me and looking straight into the dressing table mirror. Now that she was standing, I quickly looked down and I could see the string of her thong going into the crevice of her ass.
My eyes returned to her huge tits and I saw her boobs bounce a few times before falling back down. She seemed to enjoy watching them jiggle as she squirmed. Now I really enjoy stroking my bad boy. I was about to cum and I tried to hold off until she got to my favorite part. It’s coming (so to speak). She grabbed both nipples and pulled gently at first, then harder. She pulled her nipples, causing her big tits to bounce up and down wildly on her chest. Then she pulled the nipples up and away from herself, severely deforming the nipples and turning them into pointy objects, each of which was bigger than a football. That’s it! My cock was so hard that I couldn’t bend it down to aim it at the barrel, so when I started to cum I had to bend over like a football hound and shoot the first stream of hot semen into the barrel. It snapped! Well, most of it went into the bucket. It hit the other side of the plastic bucket with a loud bang, I thought maybe my mom would hear it. Shit!
I poured a few more streams of thick semen into the bucket and looked through the binoculars again, hoping Mrs. Smith was still there. She was. And then…when I was eighteen, I nearly had a heart attack. As I zoomed in, Mrs. Smith turned toward me and lifted one large nipple so she could kiss that nipple, let it fall back onto her chest forcefully, and then did the same with the other nipple. This time, however, the suction between her nipples and her lips continued as she kissed, licked, and sucked her nipples, but then, she raised her head, and I suddenly realized that she was watching me with smiling eyes. The binoculars showed her just a few feet away, and I almost lost it when she looked directly at me. As I avoided her gaze, my cock shot several more thick ropes of cum against the wall. I don’t know why I ducked, but I did anyway. I think it’s a simple reflex of “getting caught.”
I didn’t know what to do, what to think or how to feel. I felt like a dirty little pervert for getting caught peeping, but at the same time, I felt strangely excited. All in all, I was pretty scared. What if Mrs. Smith told my mom that I was some kind of pond scum, a low-life perverted peeping kid? Shit!
I went to the bathroom, squeezed out the last few drops of semen from my cock and sat down comfortably. I wet a towel and went back to the bedroom to clean up all the semen that had leaked into the bucket, when I went crazy. I had to work in the dark because I didn’t want Mrs. Smith to see my light.
After cleaning the room as best I could, I went to bed and lay there, my mind racing. Does she really know I’m watching? Will she tell my mom if she finds out? Am I in deep trouble? How could I ever see her face again? What will my mother say and do if she finds out?
On the other hand, what if Mrs. Smith found out I was watching and liked that fact? What if she put on a show just for me? My cock started to thicken again and before I knew it, I was even more aroused than before. Shit! I couldn’t help myself and started to struggle again. In my mind, I imagined that Mrs. Smith wanted me to see her every night and know that I was stroking my bad boy while she was watching. I imagined her seeing my big cock and wanting it. In this daydream (could it be a nighttime daydream?) she picked up her huge tits and asked me to suck her nipples. Just as I was starting to imagine what it would feel like when she put her hand on my hard cock, I blew another load into the convenient bucket. I must have gone crazy! I grabbed some tissues, cleaned up as best I could and promptly went back to sleep.
