Meeting Miss Margaret

By TimsTails

Original link:

Tags: mature, older, younger, oral, voyeur

Added: 25 Dec 2012 Views: 14375 Avg Score: 4.88

Tim learns about, life, love and the lady next door.
Tim’s Tails

In the beginning ,,,,,,,

I can look back now and realize not only how fortunate and lucky I was as a child. Many of these memories bring more than a smile to my face. If you stick around long enough you will hear all of my tales.

I was raised in the house my mother was raised in in the western suburbs of Chicago in a simple Victorian home on a street of Victorian homes run by a Victorian woman. I am grateful I did not end up that way.

The home to the south of us housed the Parker clan. Mr. and Mrs. Parker had five daughters and one son, Terry, my best buddy. The house to the north was home to the Millers. They had no children as he was more interested in his high power banking job downtown. He retreated, sometimes with her, sometimes without to the Country Club.

Everyone in my town was white, and as I learned later my education was above average. There wasn’t a wide range of ethnic groups, and unless you went downtown on the bus, you never saw blacks. Most everyone dressed the same, spoke the same and ate the same. Religion was up to you.

There were three events my senior year in high school that changed my life. That is when the Miller’s moved in to the north, Terry had a lot to teach me, and my aunt Patty came to live with us. I will try not to mix them up, all at times it is difficult to explain one thing without referring to another.

Terry and I had developed a pretty serious system of peeking at his sisters and I would remember what I saw, go home, and jerk off like a mad man. We would sneak around to their back parch and could see into Karen’s room. She was the twenty-two and the oldest. We could also see into Janet’s room, she was nineteen, from there. Terry had rigged up a hole in his closet to watch Mary who was a year younger than us. Cathy was was way too young and we didn’t’ care about her. For some reason the best was his mom Nancy From that I could watch from our spare bedroom. If I can get some time there are plenty of stories are there. But I was tired of watching, I wanted to do it.

I went home and did my chores. You didn’t live at my house if you didn’t work. Mom came home from work and pretty soon dad appeared and dinner followed shortly. My homework got done but there was nothing to watch on one of the four channels on the TV so I just went to my room to read. I read a lot as a kid and enjoyed it. It was a fairly warm night and I laying there reading, and thinking what it would be like to have Nancy touch me. I got hard and slipped my throbbing cock out of my jeans and just started taking care of myself. I slipped into that special place and just did what I was so good at doing –jerking off. I shot a pretty good load and wiped it off on the bandanna I kept under the bed for just that purpose. I only hoped mom would never find it. As I finished and zipped up I heard a soft thud. I looked out my window and there was Mrs. Miller, fifteen feet away, opening her bedroom window. She saw me and waved. I waved back but wondered what she had seen. I was so used to watching Nancy from our spare bedroom I never thought someone could be watching me.

Going downstairs for awhile I made a mental note to look out my window that night to see what I could see. What if Mrs. Miller had been watching me? Did women watch guys and masturbate? Other than shoveling their snow and mowing their grass I had really never paid much attention to her or her husband. My dad made me work and I mowed a dozen or more lawns and shoveled twice as many driveways. I had to put all but ten percent of the money in the bank and show him the bank book to prove it. After I said good night I went into my room without turning on the light. No need to give myself away if there was something to see, just like I did watching Mrs. Parker, Terry’s mom.

Nobody closed their curtains on the second floor of our town. You could see lights all over. The Millers were no different, lights blazing from every window. Roland, Mr. Miller, was a real tightwad. No matter how well I mowed or shoveled, he never gave me a tip. I knew he was gone a lot and often came home after eight. They never had anyone over and the only time she left the house was to garden or go play golf at the country club. The worst part was they had been there a year and I didn’t even know her name.

My window was just a little bit higher and at a slight angle to Mrs. Miller’s bedroom. I could see everything but a corner of it. Tonight she was sitting in a chair reading. I kept dad’s binocular’s on my dresser for watching Mrs. Parker and could read the make and size, 36 b, of her bra. I got them and looked at Mrs. Miller only to find she was readying Lady’s Home Journal. Dorky pictures of dumb deserts. Wow this was wild. Then I noticed how sheer her nightgown was. These binoculars were awesome. I looked at her breasts, and she didn’t appear to have any, but her nipples had to be four inches wide. In all the Playboy’s I had looked at I had never seen anything like this. This was different.

She had her legs crossed so I couldn’t see her pussy, so I just decided to sit there and watch. Her hair was very short and very blonde, but when she got up I could tell that her pussy hair was not blonde. I never realized they had a bathroom right of their bedroom and I watched her walk over, lift up her nightgown and sit on the toilet. The binoculars were back in my hand in a heartbeat. So was my cock. I was fascinated by the view and when she wiped and exposed herself I was seeing more in a minute than my lifetime of Sear’s catalogs.

When she finished she leaned into the shower and turned it on. As she bent over I could see her ass spread and her pussy lips appear. After adjusting the water she stepped in, but unfortunately went out of view. I just kept jerking and shot a huge load. As she stepped out and grabbed a towel the binoculars went back into use. The view was good enough to see the soft cotton dabbing the water off. She stopped at her nipples, gently rubbing them after they were dry. She used the towel like sandpaper rubbing back and forth across them. Although her breasts did not seem to stick out that far, her nipples had to befour inches wide. As she pulled the towel across them they just got bigger and bigger and bigger. I was hard as a rock and jerking again.

When she was finally dry she walked back into the bedroom, and for some unknown reason pulled a candle out of the holder on her dresser. She opened a drawer and took out what appeared to be hand cream and moved back to her chair. As she sat down she put the towel on the chair then she licked her fingers and began rolling her nipples between them. I didn’t think they could get any bigger but they did. After what seemed an hour of doing that she hung her calves over the arms of the chair and opened the jar. She stuck her fingers in and got them covered in a creamy gel.

Her legs opened wider and her finger slowly moved up and down the crack between her thighs. If I didn’t know any better it looked like she had another set of lips down there. Each stroke she made forced her hips to roll a little and as she kept at it the lips down there got bigger and bigger. She stopped and put the left lip between her thumb and forefinger and began to tug on it. After she had made it twice the size it was before she did the same the right lip. She had what looked like a little button hid down in the folds of her lip. She would rub it as she pulled on her lips.

The next thing she did blew me away. She took the candle to her mouth and sucked on it with one hand and took two fingers from her other hand and began to slide them into her. The rhythm of the candle matched that of her fingers. I hardly noticed it but she started going faster and faster. She seemed to shudder, and then replaced her fingers with the candle. I guess the candle was maybe ten inches long. When she started it she only put a little of it in her but with each stroke she went deeper. She also went back to rubbing that button with her other hand.

Before I knew it she was putting almost the entire candle inside her. The hand she had been rubbing with her button with went back up to her nipple. Violently she pulled her nipple out, farther than I thought possible. In about twenty seconds she literally lifted herself out of the chair and spurted something from inside all over the towel she was sitting on.

She sat there for maybe a minute and then wiped herself off with the towel. She wiped the candle off as well, and then placed it back in the holder. The jar of whatever it was got put back in her drawer. She walked over and turned off the light. I had to jerk one more time. I don’t know how many times I jerked that day nor did I care. I wanted all I could get. I don’t care what happened with Michelle, I had much better at home.

I walked over and said hello.

“Hey young man, back from mowing a lawn?

“Yes mam.”

“Looks like you worked up a sweat.”

“You too”. I looked down and saw the sweat staining her tank top. I couldn’t understand how when she was in public she had tits and when I saw her naked she didn’t. “A shower will feel really good.”

“Sure will, but I am going to wait til 8:30 to take mine. I like to go up and sit in a chair in my bedroom and watch the sunset through my window before I clean up.”

My god she has seen me. I had trouble speaking. “Well I am not going to wait, I stink too bad.”

She laughed. “Don’t have too much fun tonight.”

God she really does know. I couldn’t get that thought out of my head when I walked through the kitchen, kissed mom, and headed upstairs. She knows. She knows I watch her. Then an even dark crossed my mind. She has watched me jerk off.

Even though I was scared I was hard thinking about seeing her. Then I had a different thought. Maybe she was telling me she had seen me jerk off. Maybe telling me she was going to shower at 8:30 so I would know what time to watch her? I flew through my homework and was up in my room by 8:15.

Sure enough there was Mrs. Miller, in her bedroom chair reading. Right at 8:30 she rose and slowly took off her clothes. One piece at a time just made my dick harder and harder. As she slowly stripped she kept looking out the window. I was convinced she knew I was watching. Instead of jerking off, I had a surprise for her.

She emerged from the shower and toweled herself off. Up go the binoculars. Tonight she walked over to her dresser, and while watching herself in the mirror she violently pinched her nipples. She pulled at them and tugged at them and after several minutes of this took hair clips and put them on her swollen nipples. Then she took her hair brush and smacked her ass a couple of times before pulling the jar out of her dresser and returning to her chair.

Carefully she placed a towel in her chair and .hung her knees over the arms. She took the handle of the brush and started running it up and down her slit. I could see her lips swell and start to glisten. With her other hand she began rubbing her button. The brush moved more quickly, only to stop to let her stick three fingers in her hold. She brought them up to her mouth and sucked on them while she rammed the entre handle of the brush in her. I thought she was going to jump out of her chair.

She just sat there as cum continued to leak out of her hole.

It was dark now so I went over and turned on my light. I wanted to see if she was watching me. Sure enough when I lay back down with my throbbing boner standing at attention she came over to her window. I went slowly and she watched every stroke. One of her hands disappeared and I can only guess she started touching herself. It was all I could do to slow down, but I knew she was loving it. I only hoped I could make her feel as good as she made me feel. When I could handle it no longer I just exploded. I thought I heard something from her side but I was too busy enjoying myself.

The next afternoon I got back from mowing, and sure enough she was working in the garden. Almost like instant replay. She saw me and said “Looks like you worked up another sweat.”

“You too. Looks like you will need another shower.”

“Yes but I have to go out with Roland tonight, so I will have to break my routine.”

She didn’t know how disappointed I was at that answer.

“I need a favor tomorrow,”


“Try to finish our lawn at about two, and make sure you have nothing to do afterwards. I need your help with something.

“I don’t mind starting early for you. Do you want me to bring Terry with me? Do you have stuff to move?

“No, No, No need for Terry, You can do this yourself.”

“OK. I will be done by then.”

She looked down at her watch. “Damn, look at the time. I have to run.”

“See you tomorrow” I said as I walked to the house. She ran into hers without seeing my longing look.

It took about an hour to do each lawn by the time you got there, you mowed, and then swept the walks. I did sixteen of these every week for a buck each. At thirty five cents a gallon in a good week I had no more than two bucks for gas. In the winter I shoveled about twenty sidewalks and drives, again for a buck each. Dad said once I saved ten thousand dollars for college I could do whatever I wanted with anything else I earned. Bad thing was I had to show him the bank book each week, I could only keep a dime for each buck I earned. But when it came for a car, I was going to have money for one.

The next morning I did three lawns before noon. It had gotten really hot, in the 80’s way above the seasonal temperature. I came home for lunch, did some chores for mom and started the Miller’s yard at 12:45. I did the usual bush trimming of their lilacs then mowed the front, side and back. It was easy to do their house, being next-door and not have to haul stuff around. While I was mowing the side yard Rolland came up with a suit bag hanging off his shoulder.

“I have to run to the club. When you get down my wife will pay you.”

Ok. He was never there when I mowed, and when he was he was so tight I never got a tip. Even if it was a dime, it was money he didn’t know I got.

When I finished I went up and knocked on the back door. Mrs. Miller came to the door, but instead of her usual shorts and polo uniform, she had a terrycloth robe.

“Come on in Tim.” I went in the door and sat at the kitchen table. “Do you want a pop on this hot day?”

“That would be great”. I often had a pop or lemonade or something.

When she handed me the soda, her robe opened just enough so I could see her naked tits. Not like outside where they seemed big, but like the binoculars where they were hardly there at all. They didn’t stick out at all, but the nipples were about three inches across.

I sat down and took a sip. She went into her purse and gave me six dollars.

“Are you paying me for the month? I am only supposed to get a dollar.”

“No hon, the extra five is a tip, but it comes with some strings attached. If you agree to what I want, every time you mow you will get a five dollar tip.”

“That’s like mowing five lawns.” Even better, dad wouldn’t know about this. “What are strings?”

“I knew you would be interested. First the money, and everything you do to earn it, is a secret. You can’t tell anyone else, Terry included, about what we do. No one. Is that a problem?"

“No, I would do just about anything for five bucks."

“Good, now come upstairs with me.” She led me upstairs to her bedroom. “The first thing we need to do is clean you up.” She started the shower and came out and took my shirt off. I couldn’t believe I was standing in the place where I had watched her. She dropped my shorts and tighty whiteys before taking off my shoes. I stood there as they say, naked as the eyes of a clown. She then proceeded to drop her robe right in front of me.

“What about Roland? What happens if he comes back?"

“There is a big function at the club tonight. He took his suit with him when he went to play golf. I have to meet him there at seven. Why do you think I told you to be done at two?”

“Just like telling me you took your shower at 8:30?”

“I know you have been watching me. I can see the reflection in the binoculars.”

“And I know you have been watching me. I saw you touch yourself looking at me the other night.”

“So get in the shower.” She led me over, got in, and put me in front of her. She dunked my head under the spray and started washing my hair. I had never had anybody do this, and I never realized how neat it was.

The soapy washcloth ran over my chest. She stopped at my nipple and played with it. As she did she moved her nipples against my back. Damn this was hot. As the washcloth reached my rock hard cock she wrapped it around it. She slid it slowly up and down, and my hips began to rock. The pace increased. I screamed and cum shot out like a canon.

She handed me the washcloth and turned around. I began washing her back, but I could see she was fingering herself as I did. When I got to her ass crack I got brave. I got it really soapy and started to push my finger in her back door. She squirmed and pushed and my whole finger popped in. She kept grinding her hand into her pussy and then she screamed. She shuddered and I thought I had hurt her.

“Are you OK?"

“I am way better than ok” she said as she turned around. She got down on her knees and sucked me hard again. She took all of me in her and sucked so hard. I was getting ready to cum again when the hot water ran out. The water went to ice cold and she screamed.

We jumped out of the tub and she dried me off. We both started to laugh. “That damn water heater always gives out at the wrong time.” She led me over to the bad and told me to lie down. She lay next to me and began running her fingers throughmy hair.

“This is so special Tim. We can have our own little world,, but you have to promise not to tell anyone.”

“OK” I murmured. What else was I going to say?

She leaned over and started kissing my neck. Then she stuck her tongue out and started licking me. I didn’t know what to do. It felt so good but seemed so weird. When she got to my right nipple she started flicking it with her tongue. I wanted to shriek but held it back. Then she held it between her teeth and pulled on it. God what a feeling.

As she was driving me nuts playing with my nipples she reached down and began stroking my shaft. It didn’t need any attention, it was rock hard already. She got up on her knees and hovered her pussy over my throbbing cock. I could feel something dripping on it, but we had toweled off after the shower. Then she just literally jabbed my cock into her with one thrust. Although I came immediately I didn’t get soft and she just kept riding me. She went slow, then fast then slow again. As her pussy worked my cock she pulled out on her tiny nipples. When she pulled on both of them at once she screamed and a flood came out of her pussy.

She just sat on me for a while as I got soft. I could fell a river of cum drip out of her, onto my balls. The sheet must be a mess.

“Tim, you are an awesome lover” she said looking down at me.

“uhm,,, shouldn’t we have used a condom? I mean I don’t want to get your pregnant?”

She started to laugh. “Honey, I am 57, there is no way that is going to happen.”

I lay there in shock? 57? I thought maybe she was in her forties.

She rolled off and began to lick me. She slobbered up every drop of cum and sucked on my balls for a long time. Then she looked at the clock.

“Hon, I hate to do this but I have to get ready.”

“That’s OK. “ I looked at her and thought how lucky I was. “Can I ask you a question?”

“Sure Tim, what is it.?”

“I don’t even know your first name, what is it”

She began to laugh. “You silly boy. It’s Margaret. But call me ‘Miss Margaret’ OK?”

“Yes Miss Margaret.”