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Chapter 1 - The Birth of a Peeping Tom

I grew up in the sprawling, upper middle class suburbs of NY. At the age of 14, I became more and more focused on two major subject - sports and sex. Sex seemed to be taking preference over sports. I spent many an afternoon and early evening playing in my backyard as well as around the neighborhood. Our neighborhood was filled with similar families to mine - 2 or 3 kids, a father who worked at a decent job and a mother, who spent much of her days shopping and hanging out with her particular set of friends. My mother was a card player. She played cards with her girlfriends 2 or 3 times a week.

Somewhere in my 14th year, I accidentally stumbled upon an activity which would, in a short time, become my passion - peeping into windows around the neighborhood. It happened quite by accident. I was out in my backyard one evening. The sun had set and I was just sort of hanging out, lost in my own thoughts. I looked over at my next door neighbor's house with no particular intention. I saw that their bedroom light was on and the shade was not fully drawn down. I thought to myself, "Hmmm. I wonder what I might see if I sneaked up to the window. Now let me say that this particular neighbor was not what you would call a beauty. In fact, she was downright ugly. She was fat and her face left much to be desired. If I were to fantasize about fucking someone, she would be the last one I would ever think about. But the opportunity was there, and when opportunity knocks, we must answer the call!

I slipped up undetected to the window and snuck a quick peek. She was in there! She was fully dressed, but just the idea of watching someone while they didn't know it was very intriguing to me. I watched for a few minutes. She went into the bathroom and I lost sight of her. I waited a couple of minutes and then I was rewarded for my patience. She came out of the bathroom and her tits were exposed. She was wearing a girdle and her fat rolls were hanging over the edge of her girdle. She did have huge tits, though. I stared at her with delight. She did a few things in the bedroom as I watched those big tits shake from side to side. I was enthralled. I didn't see much more of her that night, but the bug had bit me. If I could see this fat old bitch, why couldn't I peep at some of the many women in the neighborhood who I really wanted to see? I didn't realize just how easy it would be. I began to make plans for the following night.

Chapter 2 - The Quest Continues

I hate to admit it, but that night I went up to my room and jerked off thinking about that fat, ugly bitch next door. Yeah, she was ugly, but I had seen my first live tits and I was really turned on by it. I couldn't wait for darkness to fall the following evening. Now, my neighborhood was filled with nice homes. There must have been over a hundred in all. There were lots of windows to peek into. I wondered how many of them had slightly open shades, or blinds, or some way to get a peek at some good looking woman.

Finally, that next night came. My parents were pretty lenient with me and let me pretty much be on my own. It was summer and I usually stayed out until 9 or 10 o'clock, giving me a good hour or so to do some serious peeping. I took a walk around the block that night, with an eye towards a bedroom window with a light on. I found one. It was the G's house. Mrs. G was in her late 30's and she was pretty good looking. She was slim and always dressed nicely. She was pretty sexy. I slipped between houses, unnoticed. I crept up to the window. Sure enough, the blinds were only partially closed. As I later found out, many, many windows were like this. I suppose these people never even thought about someone peeping in their windows. Maybe, I thought, they did it on purpose. Maybe they WANTED some kid like me to get his rocks off sneaking peeks at their naked bodies.

I looked inside Mrs. G's bedroom. They were both in there, lying in bed. Mr. G was a fat, bald guy. I never really liked him and I wondered why she was with a jerk like him. He was lying there in his boxer shorts, his fat belly sticking out. She was wearing some kind of housecoat. It had slid up her legs. I could ALMOST make out her pussy, but it was more imagination than anything else. I made a decision to wait there to see if she would get undressed. There were some bushes around the side of the house and I felt I was pretty safe hiding out there. I'd sneak a peek every couple of minutes to see if she had gotten up. It must have been at least a half hour and I was getting ready to depart when she finally got up. She said something to him, I couldn't hear through the closed window, but I could see she wasn't real happy with him. She kept looking towards him, her lips moving as she started to take off her housedress. I watched with baited breath as she slipped it off to reveal a tanned, pretty body with her bra and panties on. Her back was to me as I watched her. Her hands slipped behind her and undid the bra as it fell limply to the floor. "Turn around! Turn around!" I silently pleaded to her. She slipped off her panties, still turned towards him. her ass was real nice. White as snow against the tanned body. She bent down to pick up her underwear and I could see her tits swaying as she did. They weren't as big as my fat neighbor's, but they were nice. Real nice! I watched and waited. She yelled something at him and then turned quickly and headed for the bathroom. It wasn't nearly enough time to take in all of the magnificence of that naked body. I did, however, get the briefest of glimpses of Mrs. G's fantastic cunt. I had never seen a real, live cunt before and hers was beautiful. I can still see it before me, even after all these years. She went into the bathroom and I could hear the door slam. I waited awhile to see of she was still naked when she came out, but to my dissatisfaction, she had on a nightgown. I had seen enough, though, to make my first night of peeping a successful one. O ver the course of the next two years, I would make many return visits to Mrs. G's window. On very few occasions was I disappointed. The worst was when I got to her window and the blinds were fully closed. Man, was I pissed off!

Chapter 3 - New Vistas

I began to make almost nightly forays around the neighborhood. It got so I was able to make a sort of schedule. I knew when someone would be getting undressed because those wonderful ladies kept to an almost regular schedule, at least during the week. Weekends were harder because they would go out many times and I would be left with nothing to see. I'd try and find a new woman every night if I could, though sometimes I would spend my entire time at one window, watching some pretty lady get undressed...or even more. I guess it was about the third week of my peeping that I got to see somebody fucking. That was an experience! Mr. and Mrs. "S". They were going at it pretty strong as I watched and jerked myself off at their window. He really fucked the shit out of her. I had never seen people fucking before and tried to take some lessons by watching them. Mostly, they were doing it doggy style. She had a real tight little ass and he fucked her silly.

I was building up my clientele slowly but surely. In the two years or so that I was doing this, I imagine that I saw 30-40 of my wonderful neighbors naked. The amazing thing was that I never got caught. never even came close to being caught. I attribute it to my great skill at being a peeping Tom. Maybe, though, I was just lucky. I couldn't get enough of this activity and found myself doing it more and more. I would get real pissed off if , for some reason, I couldn't get out to watch my "shows". I hated when it rained, although I even managed to make a few trips in the rain.

I thought I had seen it all in the course of that first year or so, but I was wrong. Every once in awhile, I would get a glimpse of something new and exciting. That first Summer turned to Fall. I turned 15. Soon, Winter had arrived.

Chapter 4 - The Best Tits I Ever Saw

Winter had it's good and bad points for me and my "occupation". First, I didn't get out nearly as much because of weather and school. On the plus side, though, was that it got dark much earlier, giving me more time to get around. I had lots of ground to cover.

Giving an award for the best tits I'd ever seen was easy. Her name was Francis W. Much of the neighborhood was friendly with one another, but Francis and her husband kept pretty much to themselves. They had two pretty daughters. One was my age, the other was in college. The closest I ever came to getting caught was at Mrs. W's house, and it was all my fault. I made regular stops there and I was usually afforded a pretty good view of her. She would leave her bathroom window slightly ajar while she did her thing in there. When she'd hop in the shower, she would be standing almost next to me and it got me so hot I could scream. One night, she went to take her usual shower and got into the stall. Her tits were absolutely perfect. They were average in size, but stood straight out and her nipples were a deep, dark brown and very large. When the water would hit them, they would harden and I swear that they stuck out almost an inch. If I could have sucked any tits in the world back then (or even now, for that matter) it would be hers without any question. Anyway, she started to lather up, her tits glistening. I couldn't help myself. I stood right up to the window and called out. "You've got beautiful tits!" Then I ran like hell! I'm not even sure if she even heard me. I was afraid to come back there for a long time after that, worried that they might be hip to me and be there waiting to nab me. God, that woman was beautiful.

My regular schedule consisted of having dinner, and then telling my mom that I was going out to play with my friends. "Be home before 11" Mom would tell me. She never minded, though, if I showed up later. In fact, I'm sure that most of the time she didn't even know if I was home or not. Anyway, I was making my rounds. It was a good night, that night. Usually, if I could peep in on 1 or 2 ladies, I would consider it a good night. This night, however, everything seemed to fall into place. It wasn't often that I would get to see something in every window I looked into.

I visited my old friend, Mrs. G first. There she was! She liked to prance around in her bra and panties alot. I think she was pretty impressed with her figure (why not?), and I constantly would catch her looking into her mirror, grabbing her tits, touching herself, enjoying herself. She really was hot and I wished that I could fuck her. I often fantasized about her. I would imagine me coming over for some lame reason and she would be there in her bra and panties. No one was home and she'd invite me in. I envisioned her coming on to me and telling me how much she wanted to see me naked. I'd undress and she'd get down on her knees and give me the best blow job. Then, she'd take off her undies and I would fuck her. Oooh! If only that could have happened!

Chapter 5 - Oh, Margaret!

It's funny how things work out. I got to see so many naked women in my travels, but the one that I most wanted to see, I never did....at least not on my peeping journeys. It wasn't for lack of trying, either. It's just that that damn window was never opened enough for me to see what was going on inside.

Her name was Margaret. Margaret T. She was my mother's best friend. She was blond and buxom and she had the prettiest face. She had always been so sweet to me and I had the biggest crush on her. She had a son my age and I became friends with him just so that I could be near her as often as possible. I must have tried a hundred times to spy on her with no success. I even snuck into her bedroom a couple of times when I was playing with Mark, her son, to open the shade just a crack. Then I would come by that same night, only to find that it had been closed. Mrs. T was my first fantasy. I'd be over there playing with Mark and she'd be walking around the house and I'd just be staring at her. She liked to wear those housecoats that were so popular back in the late '50's, early '60's. Lots of times she wouldn't be wearing a bra. She'd bend over to pick something up off the floor, and I'd get a quick peek at some tit.

It was with Mark that I had my first live sexual experience. We were up in his room playing one day when we were about 12. He suggested we take off our pants and see what our cocks looked like. I figured it would do no harm, so I did. He had a real little pecker and I think he got embarrassed when he saw mine. I had a big cock, even at the age of 12. I measured it once and it was almost 9 inches long when it was hard (which was most of the time!). He asked me if he could touch my cock and I said sure. He wanted me to do the same and both of us got a hard on. We started to jerk each other off and he came in an instant. I freaked when that cum came pouring out and he started shouting, "You made me cum! You made me cum!" I was embarrassed to say the least. A few weeks later, we were up in his room again and he wanted to suck my cock. I had no desire to suck his, but I let him do it. I got hard thinking about his gorgeous mother. He enjoyed sucking my dick and I enjoyed having an orgasm. What he didn't know was that orgasm was because I was fantasizing about his mother! I wasn't really into the homo thing and I discouraged him in the future. What I wanted was a way to get to his mother.

I even went so far as to sneak into her bathroom one day and go through her dirty clothes. I took a pair of soiled panties, a bra and a pair of pantyhose. They became my treasures. After a hard evening of peeping in windows, I would go up to my room, slip on her panties, bra and pantyhose and jerk off. Man, I had some great orgasms thinking about Mrs. T.

Chapter 6 - Kay Loves Jackie, Jackie Loves Kay

I turned 15 at the end of the Summer. I was still going pretty strong with my almost daily trips through the neighborhood, seeking out the naked bodies of my neighbors. It was funny, but I sometimes got a chance to peek into the window of girls my age or a little older, but I much preferred their mothers. I think this is where I got the "thing" for older women. It's still with me today. I've always enjoyed having sex with women older than me. My first fuck was with one and that just served to bury that desire deep within my psyche. It almost became run of the mill, until I would come across some new, exciting experience. I had a regular list of women who I would visit, but I was always on the prowl for new worlds to conquer. Mrs. Miller was one of those new worlds.

Mrs. Miller was a redhead, short in stature, with perky little tits. She was no knockout, but she had her moments. Her husband had been killed about 6 months earlier in a bad accident and she had a daughter who was in my class at school. I had never peeped into her window before and I decided it was time to take a shot. Her house was set back and easily accessible for a peeping Tom. There was alot of cover. The lights were on and as happened more often than not, there was a view through the shades right into her bedroom. I crept up quietly to the window and took my first look in. What a shock I got! Let me preface what I'm about to tell you by saying that the word around the neighborhood was that she was a little strange. Strange in what way, I wasn't quite sure, but strange nonetheless. Her daughter, Jackie, was pretty and she reached maturity alot earlier than most girls. In otherwords, she had a nice set of tits at an early age.

I peeked in and there was Mrs. Miller, walking around the room, putting some clothes away. She was naked as a Jaybird. I caught a glimpse of her pussy and it was as red as her head. I had never seen a red pussy before and I liked what I saw. I was really getting into her when I saw her turn towards the door. The window was open somewhat and I could hear her say, "Come on in, Jackie." It seemed kind of weird that she'd be totally naked and tell her daughter to just come in. Jackie walked in, wearing an oversized tee shirt and no pants. She had pretty nice legs, too. Jackie and her mom hugged each other, her mom running her hands through Jackie's long, black hair. I heard them both laugh and Mrs. Miller pointed to the bed and Jackie walked over and lay down on the bed while her mom continued to finish what she had begun before Jackie came in. I was enthralled. I watched and waited, not knowing what was going to happen. I just figured that Mrs. Miller liked to walk around naked and didn't care that her daughter could see her.

Mrs. Miller finished her work and walked over to Jackie, still lying there in the bed. She had her knees up and I could see that she had on a pair of panties beneath her tee shirt. They were talking to each other quietly and I could only make out a few words of their conversation. Then, Jackie took off her shirt. She had no bra on and her young tits were out in the open. Actually, her tits were bigger than her mom's. I couldn't believe what happened next. Jackie slid down to the edge of the bed while Mrs. Miller lay back, spreading her red haired cunt apart. Jackie pulled her hair back behind her head and began to eat out her mother! Man, was I getting turned on by that! Not only was I seeing two chicks going at it (which I had never seen before) but it was a mother and daughter to boot! Mrs. Miller was flailing around the bed as Jackie ate her pussy. She was moaning and yelping and I knew she was cumming hard when she started to scream. It was glorious. I guess this is what they meant by weird, I thought to myself.

Mrs. Miller pulled her daughter up her body after she came and Jackie lay right on top of her. They started to kiss each other. Watching two women kiss each other was more than I could bear and I came in my pants. I stayed, though, with my wet pants. I didn't want to miss a thing. Next thing you know, Mrs. Miller was reaching into the draw of her nighttable. She pulled out this pink thing. It took me a minute to realize what it was. It was a fucking dildo! There was this black strap attached to it and I watched her intently as she began to put it around her waist. She got up and fastened the belt around her. Goddamnit! She looked like she had a penis! She sat back down on the bed, next to Jackie. She lay down, spread her legs and that pink penis stood up like the Washington Monument between her legs. Jackie straddled her mom and, with her fingers between her legs, slipped that thing right up her wet cunt. Man, was I hot! Jackie started to bob up and down on that dildo, her tits flailing from side to side and up and down until her mom grabbed them and squeezed them tight. "I love you, baby! I love you baby1" She cried over and over as Jackie kept pumping away. Finally, she started to yelp and moan as she came. Boy, did she ever cum! She slipped the dildo from her cunt and lay down on top of her mother. Mrs. Miller wrapped her arms around her daughter and they kissed passionately. I felt as if I had just won the World Series in the seventh game by pitching a no hitter!

The two of them lay there for awhile and I thought they were finished, but they were far from done. Jackie strapped the same dildo around her and they switched. Her mom pumped away and was screaming when she came. Jackie sucked on her mom's tits as she came and then they repeated the same kissing and hugging scene again. I thought to myself, "Wow, I need to get some of that!" Jackie and I weren't very close friends, but I was a smart kid in school and she wasn't. I figured if I started to help her out with her schoolwork, maybe I could get some of that mother/daughter action. I made it a priority!

Chapter 7 - The Mother Fucker

Jackie already had a reputation around school as being kind of easy, if you know what I mean. No one claimed to have fucked her, but you know how stories and reputations get started. Of course, no one but me knew that she was fucking her mother! I started to talk to her a little bit more and you KNOW I was as friendly as I could be! I told her I'd help her with her homework if she wanted and she said okay. The first couple of times I went over there, nothing happened. Her mom was real nice to me and I thought about making a pass at her, but I didn't quite yet. The third time I went over, it was just the two of us. Her mom was out and we were alone. We did our work and we were watching TV when I slid up next to her. I put my arm around her and she didn't put me off so I figured I would try a little more. I reached over and it was if she was waiting for me to kiss her. She WAS easy! We kissed a little and I put my hand over her chest and started to feel her up. We were going pretty strong when we heard the keys in the door.

Her mom walked in and she knew right away what we were into, but she wasn't like most moms would be if they came in and found you feeling up her daughter. "Oh, hi kids. I'm not interrupting anything, am I?" She smiled, knowingly. "Jackie was cool, but I was a little flustered. "Your hair is all messed up, Michael." she pointed at my head. "Oh, ugh, must be the pillow on the couch." I felt like a moron saying that. She just walked into the bedroom, saying nothing about it. I told Jackie that I'd better get home. "See you tomorrow?" I looked at her. "Sure," she smiled back at me. I definitely got the feeling that she liked me. I liked her too. Of course it helped knowing that she liked to fuck her mother.

I was definitely looking forward to the next night. I figured for sure that I would finally break my maiden with Jackie. Wrong again! We had planned on me coming over around 7. I arrived promptly. I had showered and was quite proud of the way I looked. I even put on a little cologne I had for special occasions. I knocked on the door and waited for Jackie to answer. The door opened, but it was her mother who answered the door. The only reason I was a little disappointed was that I had hoped her mom wouldn't be home so that I could fuck Jackie. "Oh, Michael! Come on in." I walked into her large and pretty house and looked around. "Hi, Mrs. Miller. Where's Jackie?" "Oh, Michael, I'm so sorry. Jackie had to go over to her aunts house to baby-sit. It was kind of an emergency and she didn't get a chance to call you. I'm sorry." "Oh, that's all right, Mrs. Miller." "Michael, please don't call me Mrs. Miller. It sounds so formal. Just call me Kayl." "Ok, sure, uh, Carol." It felt a little strange calling her by her first name, but I did. "Well, I guess I'll see her tomorrow at school." I turned and began to walk to the door. "Wait, Michael. You don't have to leave because Jackie isn't here." My heart pounded, hearing that. "Why don't you come on in and we'll have a little talk." She reached her hand out to me and I took it willingly, excitedly and she lead me to the living room. I sat on the couch and she sat directly across from me in a large, comfortable looking chair. She crossed her legs and I saw much more leg than I was supposed to. Of course I had seen it all, though she didn't know it.

"Jackie seems to like you quite a bit, Michael."

"She does?" I smiled.

"Yes, she does. You know you are a very good looking young man. I'm proud of my daughter's taste." she smiled back at me, exposing just a little bit more leg. I tried not to let her see me look, but it was no use. "Would you like a drink?" She asked. "Okay. Do you have any coke?" She got up as I said coke and walked into the kitchen. I watched her tiny ass shimmer from side to side as she walked. She sure had a sexy walk! She came back with my coke and a drink for herself, which must have been alcohol. She sat down next to me on the couch and we began to talk about school and stuff. Just small talk. She had finished her drink and I could see she was already a little bit tipsy.

"Did you know my husband, Ron?" I could sense a tear welling up in her eye as she spoke. "Not really," I answered honestly. She went on to talk a little about him and by the time she had finished, she was sobbing. I felt uneasy. I wasn't quite sure what to say to her, but I really wanted to be of some assistance. Before I could come up with something, she did. "Oh, I'm sorry, Michael, I shouldn't burden you with this stuff. It's just that I've been so lonely since he's gone." She reached out and took my hands, laying them in my lap. She held them tightly. "You're so sweet to listen to me." She looked me in the eyes and I felt such empathy for her. "Thank you," she smiled and then she reached over to me and kissed me...on the lips! I was alittle stunned. I could smell the alcohol on her breath, but I could also smell the intoxicating scent of the perfume she had one.

She had deep, expressive green eyes. Her skin had a pinkish glow to it, although she had on makeup. Her red hair, which she had up in a bun-type style, glimmered with redness in the light of the lamp behind her. She wore a pretty, light blue dress with stockings beneath. She was a slight woman, maybe 5'4 and probably no more than 115 lbs. I assumed she was in her late 30's. I never asked her age.

She waited for a reaction. "Wow, Mrs., uh Kay!" was about all I could muster. I felt myself blowing this whole scene. She just laughed. "Michael, Michael," she grasped my hands in hers. "I'll bet you've never slept with a woman, have you?" Her head turned slightly to the side. She looked so pretty. I admitted that I hadn't. "That's okay," she said softly. "Everyone has to have a first time, don't they?" I nodded my head. She kissed me again. This time it was a more passionate kiss. Harder. Longer. Her eyes were closed as she kissed me. I peeked. "Michael?" she spoke softly as she lifted one of my hands to her chest. "Touch me." She placed my hand right over her tit. I started to rub across her breast. I could feel her nipple, hard and erotic. She tossed her head back as I massaged her tit. She moaned and sighed. "Oooh, that feels so good. Do you like that?" I was warming up to the situation, having gotten over the initial shock of her seducing me. From all that I had seen through all of those windows, I pretty much knew what to do and how to do it. I suppose my peeping was about to pay off.

This time, I kissed her. She took my lips smoothly and I felt her mouth open as we kissed. I felt her tongue against my lips and opened them. Her tongue slipped in and soon our two tongues were entangled and flitting back and forth over each other. I began to unbutton her dress, but she suddenly stopped me. She pushed me back. I was afraid she wanted to stop, but she just wanted us to go into the bedroom.

Without going into too much detail, suffice it to say that we fucked for about two hours. She went wild when she saw the size of my cock and she gave me the most wonderful blowjob. She insisted on swallowing every drop of cum I had. I fucked that lady like a madman and both of us had numerous orgasms. Her sweet red pussy was intoxicating and once I had tasted the juices within her, I became addicted to eating pussy. When we finished, we lay there naked, spent and totally satisfied. She told me that she had never been fucked like that before. Not even by her husband. I felt good. I felt great. I felt like a real man. I also was in love.

I suppose most guys fall in love the first woman they fuck, as long as it's a good experience. I was no different. All I could think about was Kay, Kay, Kay. She was smart enough to warn me. She told me not to fall in love with her because nothing could ever come of it. It didn't help, though, because I WAS in love with her.

 

Chapter 8 - Three is NOT a Crowd!

There was still the issue of Jackie to be resolved. When I got home, I thought about her and felt a little bit uptight about her. After all, how could I tell her that I was fucking her mother even though I knew that SHE was fucking her as well? The issue took care of itself the next night.

Jackie called me to apologize for having not been there the night before. I told her I understood about the emergency. Then she asked me a question that totally floored me. "Did you have fun with mom last night?" I wasn't sure what she meant. Did she know about us fucking or was she just asking if I had fun talking to her? I played dumb. "Michael, it's okay. Mom told me all about it. You see, mom and I have a very, uh, special relationship." She emphasized the word special. Of course I knew this, but she didn't know I did. Then she told me that she and her mom shared everything and would I like to come over tonight. She laughed when she said, "We'd like to share you, too!" Man, what did I do to deserve this? Did I die and go to heaven or what? I told her I'd be over as soon as I finished dinner.

I didn't eat much that night. I told my mom and dad that I was going over to Jackie's and that I might be late. We had a big test coming up and she needed a lot of help. No problem. I went upstairs and took a shower and got ready for what looked like the hottest night of my young life. It was. It was.