Story Details

Dorothy, The 40 Year Old Next Door

Loverboy69 on Short Sex Stories

Dorothy was the beginning of my love for mature women. Dorothy was divorced and lived with her mom in the duplex next door. Dorothy was everything I came to love in a woman - dark haired, sexy, flouncy, a little chubby, but just ever so much, a wide butt and baby bearing hips and nice average sized breasts.



When I was a teenager Mom had the woman next door keep an eye on me. I was 15 and 16 at the time, but Mom still wanted Mrs. M to keep an eye on me and check in to make sure I got home from school okay while she worked. Mrs. M would feed me dinner if mom had to work late and I was a guest in Mr's M's house on a regular basis. She was a nutty old woman., She had a mini poodle that she carried everywhere she went. She never changed out of her bedclothes and drank 6.5 ounce Cokes in the bottle as if they were her personal elixir of life. She even taught me to play Canasta.



Dorothy moved in with her mom at some point and I remember being excited at seeing her everyday. She worked nights for the phone company so she was usually home during the days. Once, the unexpected happened.



One afternoon I was at Mrs. M's house eating those horrible fudge brownies she always made and drinking one of the Cokes in the little glass bottle. For some reason the Myna birds upstairs started squawking and Mrs. M asked me to go check on them. I ran upstairs, made sure all was well with her feathered friends, and went back down the steps. As I reached the landing I turned and looked back up the stairs. I heard a noise behind me and looked back to see what I'd heard. Wow, was I in for a treat.



There stood Dorothy, naked - totally, completely and absolutely. She had been in the bathroom at the top of the stairs and she'd heard me bound up and then down the stairs. She emerged from the bath before bathing to get a fresh towel. As I turned and looked up the steps Dorothy was just opening the linen closet door. Dorothy saw me and smiled, then she winked at me, smiled even bigger and turned to go back into the bathroom. I damn near fainted.



I had been having sex since I was 13, but never with a woman. Always with girls my own age. Somewhat nubile, occasionally a full breasted one, but usually the average 15 or 16 year old girl. Cute and fun, but not yet women. They were not yet curvy and full like Dorothy. I was completely smitten. I hung around til Dorothy emerged, dressed and came down to go to work for the evening. I could hardly look at her due to embarrassment, mostly for the thoughts I was having, but for her part, she was having none of it.



She knew my little mind was racing and she eased my issues with her kindness. She smiled at me and walked over and hugged me - the first time ever - before she went to work. She walked out and looked back and smiled at me and she was off.



My Mom came home soon afterward and I went home and excused myself to take a shower, or to be honest, to beat my meat. I came three times in about 5 minutes in the shower. By the time I came down and hung out with mom for awhile I was beat. Drained, as it were. Soon I went to bed and dreamed of Dorothy.



Luckily for me, she lived in the duplex next door - not the one attached to my own dwelling. Our homes were separated by a double-wide driveway. Her house was a mirror image of my own floor plan, so across the driveway from my bedroom window was Dorothy's bedroom. I began leaving my blinds open so I could spy on Dorothy if she was ever home in the evenings, or in the day for that matter. Soon I noticed she too left her blinds open - not up mind you, but the slats were opened, so in the dark I could see directly into her room, and she mine. But it wasn't a night that the first "mutual admiration" incident manifest.



Late one afternoon about 4 or 5 days after the linen closet incident Dorothy was in her room. I was in mine. I was lying on the bed stuffing a bowl with various things of illegal smoking natures. I looked over at Dorothy's room and I could see her shadow moving. I opened my blinds a little more and sat staring until my eyes adjusted to the darkness of her room. From the position of the Sun her room was back lit from the other back facing window in her bedroom and lo and behold, she was watching me too.



She was wearing a garter, stockings (this was in the very early 1970's so some women still did not wear the dreaded panty hose) and a bra. She did not have on panties. She walked around her room in that state for some time. Within minutes I was stroking myself to beat the band, and she knew it too. Occasionally she glanced out her window to make sure she still had my attention, then she began to fondle herself. Soon her bra was on the floor and she was naked but for the garter and stockings. After a moment or two they disappeared as well and there she was naked before me again.



At first she never looked directly at me, but she really put on a show for me. I started getting dizzy with lust. Ya know that feeling in the pit of your belly? I had it in spades! She remained standing, leaning back against a wall, and rubbed her breasts, tweaked her nipples and slid her hand down to her crotch. Soon she became more brazen and I joined right in.



As a young guy I was scared to be too overt. What if I misconstrued all that had taken place? What if I threw open my blinds and stood at the window proudly stroking the 7 inches of my full hard on? Would she call the cops and report me as a sexual deviant? I was scared, cautious, and horny as hell. But in a few moments it became too obvious for even my fearful young butt to ignore.



I think I finally lost it when she took her hand from her crotch and licked her fingertips. She looked up directly at me when she did it. Our eyes made contact and that was it for me. I ran to the window, all 6 feet from where I stood, and fumbled as I threw open my blinds. Her tongue licked her dry lips ever so sexily and she looked at me. Her eyes pierced me and I started cumming all over the window panes, and sill. She saw that and seemed to get fueled by it. She opened her eyes very wide, Her nipples exploded off her chest and swelled up so that the aureole became tiny and covered with little goose bumps. She stared at me. Her mouth hung agape, a look of wanton lust and sluttiness in her eyes as she brought herself off.



What got me the most was that she never took her eyes off me once she made eye contact with me. Her already naturally full lips became swollen and her upper chest blushed red. Then she opened her eyes so wide I thought they would drop from their sockets as she orgasmed. God that turned me on. I was still rubbing my hard on and delivered another load for her to see. I began to use my left hand to rub my nipples and she liked it.



After what seemed like hours that passed in mere seconds, it was over. She slowly and rather demurely ended our event by approaching the window, at which I was still glued, and slowly turning the blind slats closed. She looked at me the whole time. Her smile was warm, loving and understanding. And to totally hook me, she winked at me again as she warmly smiled.



I will be glad to tell more chapters of this story if any reader is interested. Love feedback. Thanks.

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