Where it happened: on her bed
Mrs. Jennison was the mother of two girls I went to school with, and one of my mom’s best friends. The Jennisons lived about four houses down, on the opposite side of the road, and I was always over there playing when I was a kid. April, the oldest daughter, was the babysitter of her sister, Heather, my brother and I, when we were younger, and we would spend many a summer day playing in their pool. Mrs. Jennison, was almost like mom-away-from-home. Heather was a year older than me, so we were in school together, and April was four years older.
As the years went on, and I started to approach puberty, I began to look at April, Heather, and Mrs Jennison, as well as every other woman who crossed my path, in a very different way. I slowly realized that Jennison was a beautiful woman, a bit on the
plump side with full arms and big tits, nice big legs and broad wiggly rear end. She had a very breathy way of speaking that was subtle, and unintentionally sexy. Her natural friendliness was just fuel on a fire that was slowly getting started.
Looking back to that time of my life, I don’t feel that I was different than any other boys my age. Hormones permeated everything I did. One of the things I would do at night, to help me fall asleep, is close my eyes and picture having a sexual encounter with any woman I knew… aunt (by marriage), my neighbor, my teacher, etc. Mrs. Jennison, unbeknownst to her, was often a star in my little dream plays. I hadn’t yet discovered masturbating, and wouldn’t until my third year of college, so I would just drift off to sleep with sugar plums dancing in my head. In my mind, I could create any situation I chose, and act the puppeteer so that Madam X would do what I want, when I want. If only life could be as ideal as dreams. Although I was bold in my mind, in reality, I didn’t have the balls to try the things I fantasized about. The opportunity would have to present itself in such a way that there was no question as to the outcome. But, as I said before, hormones permeated everything I did, and sometimes it could override logic and modesty. Such was the case with Mrs. Jennison.
By the time I was 15, and finishing up my freshman year of high school, I had a whole new set of friends and didn’t spend much time over at the Jennisons. I would occasionally see Heather in the halls, or April in passing in the neighborhood. The only times I would see Mrs Jennison is when her and her husband would go out with my parents, or if I needed to drop something off for my mom. In each case, Mrs Jennison was always very friendly without being teasing. I was sure she never shared my overactive imagination, at least I never had that feeling.
I ran into Heather in the hallway on the last day of classes and she invited me over for a swim after school. Seems a bunch of kids on the block were heading over to celebrate the beginning of a new summer, and for me the end of freshman year. I got home about 2:30 and still had an hour and half to kill before heading down the road. I threw my notebooks down on my bedroom floor, to be saved for a bonfire at a undetermined time in the near future, and got something to eat. I took my pooch for a walk, and still had about a half hour to kill so I decided to go over a little bit early. If nothing else, I figured I’d bullshit with Heather until everyone else showed up.
When I got to their house, I went around back to see if anyone was around. The Jennisons had a second story deck that opened up from their kitchen and dining room, so I started up the deck stairs. I heard some music playing on a portable radio and figured it was coming from an open kitchen window, or sliding glass door. When I got to the top, my first observation was that some woman was lying topless on a blanket. She didn’t hear me over the music, and her somewhat sleepy daze. April had been away at college, and Robin had blond hair, so within milliseconds my brain registered Mrs Jennison. Before she knew I was there, I was able to just stop and stare at a pair of beautifully 36 D cups in all their glory. My dad’s Playboys and Amanda Jenkins 13 year old nibblets were about the only real experience I had, so to see a set in real life was the chance that every 14 year old boy dreams about. Mrs Jennison had April when she was about April’s age, and was looking better than any 40 year old women I knew in person. She didn’t flaunt herself in any snobby way. She was very down-to-Earth, almost oblivious to the effect she could have on the male species, which is what made her even more attractive.
By this time, in a hormonal fog, I had walked closer to Mrs Jennison, and the vibration of my feet must have woke her up because she suddenly jumped and grabbed a towel. She was embarrassed and asked how long I’d been there.
“Only a couple seconds,” I stuttered.
“You scared me. I thought you were a stranger. Heather isn’t home yet, but I thought I’d catch a little sun before she is. Come on in and I’ll fix you some lemonade while you wait.”
She held the towel over her chest as we walked inside. She told me to help myself to the lemonade and that she would be right out. She came out in the same bikini bottom with a half shirt on and we just talked until Heather and the gang came around. We swam and played pool volleyball from 4:30 until about 8:00, at which time everyone who could still feel their fingertips grabbed a towel and headed home for dinner. Mrs Jennison continued to lie out in the sun until it was getting dark, although covered on all vital areas, and I continued to catch a peak out of the corner of my eye every 10 or 15 seconds. I noticed, in between glances, that I was not the only one with involuntary glances. All the guys were nonchalantly looking in her direction in between volleyball serves. Don’t get me wrong, Heather looked like a younger version of Mrs Jennison, but Mrs Jennison was a woman. Every 14 year old male fantasy is to be with an older woman. At last, I headed home as the sun set on a new summer.
I got a job that summer mowing lawns in the neighborhood. It was hot, and sweaty, but it paid for gas and CD money. The Jennisons were on my list of houses to mow, and I always hoped I would run in to Mrs Jennison on the deck again. I never did. But somewhere in the haze of August, I ran into Mrs Jennison under different circumstances.
Mrs Jennison’s husband, Dan, was a Vice President in one of the local banks. His professional success allowed Mrs Jennison to stay at home and take care of the girls and the house. My normal routine was to find Mrs Jennison after I was done mowing, and she would pay me. Sometimes she would be cleaning in some far off corner of the house and she wouldn’t hear me, so she told me that if she was home, but didn’t answer to come on in. I knocked about three times, but didn’t hear an answer. I knew she was home because her car was in the driveway, so I opened the door and walked in. I called to her, but there was no answer. I could hear the shower running and the radio playing in her bedroom, and decided that she hadn’t even known I was mowing today.
There comes a time in every young man’s life when he has to decide how big a set of balls he really has. Not literally, figuratively. Is he going to be a follower, or a leader? Is he going to talk the talk, or walk like John Wayne? This was the time that hormones overrode common sense. I slowly walked up the stairs, trying not to make too much noise and scare her, at least that’s what I told myself. I was actually trying to minimize the sound of rushing blood in my ears from a heart that felt like it was going to explode from nervousness. I was trying to listen for anyone else who might be coming home to find me sneaking into my neighbors bedroom. The sweat began to pour, but I remained focused. I finally reached the bedroom door, and by now I had the intensity of Tom Cruise in Mission Impossible.
I entered the bedroom and headed towards the bathroom door. I could see and feel the steam coming from the shower as I slowly approached. From where I was standing, I could see Mrs Jennison’s outline in the glass mosaic shower door. Although distorted, I could make up enough of an outline to figure where all the pieces fit. She turned slightly, and I could see a little brown patch where her pubic region should be. She appeared to be soaping her tits, which was when I noticed my shorts pointing to true north. Seeing a real woman naked can do to the penis what steel girders can do for a building. My dick felt so hard it was painful. So painful in fact that it brought me to a moment of clarity. If I just barge in there, she’ll freak out. So, on to plan two, which was really no plan at all. I slowly walked back to the bedroom door and knocked on the door frame.
“Mrs Jennison….I just finished mowing your lawn and came in to see if you were around. I knocked at the front door, but I guess you didn’t hear me, so I came in.”
As I began to speak, she jumped as if the voice came from the shower nozzle itself. Within seconds she realized what was going on and continued soaping up.
“Oh, OK, Shawn, I’ll be out in a minute. Just make yourself comfortable.”
Sure will, I thought to myself as I just stood in the doorway and waited. When she was all done, she grabbed a towel and proceeded to wipe down behind the glass shower door. She wrapped the towel around her chest and stepped out. She looked like a drowned rat, but in some ways, it made her look vulnerable. I found it very sexy. She grabbed another towel on her way in to the bedroom and started to dry her hair. She didn’t seem to mind that I was there, and I wasn’t going to excuse myself without a fight. She started to ask me questions about my summer so far, how my parents were, etc. and we made small talk while she dried her hair.
She finished with her hair and grabbed some lotion for her legs. As she did this, the subject changed to the dangers of sunbathing and how good lotion can help keep you from getting dry, wrinkly skin. She put some lotion in her hands, rubbed them together and started to rub some on her legs. The conversation went back to my plans for the future as she began to rub up her legs and thighs. She was so concentrated on putting the lotion on that she didn’t notice me watching her as her hands went higher and higher up the towel. I was still standing in the doorway, and my view was from her side so I couldn’t see anything graphic, but my thoughts were racing a mile a minute from the unintentional teasing.
When she finished with her legs, she put some on her arms. She asked if I would mind rubbing some on her back, since no one else was home to help her.
“Oh my God,” I thought, “I’m gonna die. I’m gonna die right here, with a boner.” Up to this point I’d had my shirt pulled down over the front of my shorts, so I don’t think she noticed the effect she had on me.
She lied down on the bed and pulled the towel down so as to reveal her statuesque back. I put some lotion on my hands, which was tough because they were shaking like an 80 year old Alzheimer patient, and placed my hands on her shoulder blades. I touched her like I was touching an angel in Heaven. With an awe and respect that would befit the loveliest goddess on the highest pedestal, I slowly began to move my hands. It was electric. As I began to follow the contours of her back, my senses became heightened and I could feel every inch of her skin…..every nerve aware. When I got to the small of her back, I rubbed down under her towel a little, to test the waters. She didn’t seem to notice as she was talking about how April did in school her freshman year in college. I turned my body so that I was now sitting on the bed, to her side facing in the direction of her feet. I began to motion down her low back and fan out over the top of her ass. With each stroke I went lower and lower. I asked her if she wanted me to put some lotion on the back of her legs, and she said “sure”. She then went back to talking about how she thought the Giants would do this year, and how Dave Brown, the quarterback, was a wuss.
I rubbed some lotion in my hands and went back to work. I stroked down the middle of the back of each thigh and then back up the sides. With each stroke up towards her ass, I moved a little closer and closer to her inner thigh.
“…And can you believe how much money they’ve already spent….” she said, as I got off the bed and positioned myself around to the foot of the bed.
“Uh-huh” I said as I put more lotion in my hands and began the stroke again. I moved the towel up so I could get to her upper thighs and as I did, I saw it. My first real view of a pussy. It was beautiful. I could just make out the outline of her thin inner lips between a nest of chestnut brown pubic hair. I swallowed hard, blinked my eyes and kept rubbing. Mrs Jennison didn’t seem to notice that I was rubbing closer and closer on her inner thigh as well as higher and higher.
“How’s this feel?” I asked, in a sneaky attempt to draw her attention away from my wandering hands.
“Feels good Shawn…it’s almost putting me to sleep”. As she said this, she shifted slightly, opening up her legs a little bit more. I started to concentrate on just her inner thigh now, stroking gently up and down, and in little circles. She was starting to get very relaxed and finally stopped talking. Her thighs felt soft and silky as I placed my hands between her thighs. I felt Mrs Jennisons thighs clamp and press against my hands as she crossed her legs.
When she opened her legs I got my first scent of a woman. It was strong, but sweet. Whether she said anything or not, I could tell that I was having an effect on her. I moved my hands back up to her thighs but started to stroke up under the towel and on to her ass. I could hear her moan, and I wasn’t sure whether it was from sexual excitement or just pleasant relaxation. Either way, I didn’t care. Since Mrs Jennison had not protested or said anything, I decided to proceed. I took a deep breath and moved the towel to one side.
What kept me from ripping off my clothes and diving between her ass cheeks is beyond me. It’s times like these that you have to believe in a higher being. She was gorgeous, she was naked, and she was quiet. With each stroke of her ass cheek, I would press a harder and harder. This opened up her up a little more each time and I thought I would explode as I watched her asshole appear and disappear between her soft mounds. I began to move back towards her thigh, destined to take the chance and touch her pussy. I got some more lotion on my hands and began to work her inner thigh again. With each stroke I moved closer and closer until I could just feel pubic hair and the warmth of her pussy. I accidentally brushed up against the wetness between her pussy lips and I heard her whisper a quiet moan. The moment I touched it she parted her big thighs a couple
of inches more to let me get at it easier.
Then, I did it. I gently touched between her lips and stuck my finger in. I looked at her to see if she was going to jump up and swat me upside the head but she clung to the bed sheets with both hands and moaned. I began to slide my finger in and out. I could see how wet it was and hot she was. Each thrust became easier and easier as I slide two fingers in now. With my other hand, I began to massage her ass again. I was too young and inexperienced to know anything about a clit, so unfortunately for her, that wasn’t going to happen, but she didn’t seem to mind. I stopped fingering her. It was so perfect. I began to wet my fingers in her pussy as she began to grind a little bit.
With Bruce Springsteen sullenly singing about being on fire, I’d had enough, I wanted to jump in and take the plunge. With her legs spread, I could smell her everywhere and I was getting to the point where just a light breeze would send my shooting to the moon. With her still lying face down on the bed, I got between her legs and began to rubbing her pussy. I was totally inexperienced and just winging it, but I was like a kid in a candy store.
As I became more confident, I stayed around her pussy more and more. Unintentionally, but much to her liking, I would accidentally brush against her clit and when I did, she would take a deep breath in and exhale in a passionate moan. I began to concentrate more and more on the area that seemed to cause the most pleasure. She quickly grabbed two pillow and placed them under hips so that I now had a better vantage point. The more she moaned, the faster I went, until her breathing was very rapid. With her face buried into the mattress, her body began to spasm. It was hard to keep doing what I was doing, but I held on for that championship ride. Then it happened, I came. It felt wonderful and disappointing at the same time. I was concentrating so hard on her that I didn’t even really get to enjoy it, but I felt the warm sticky fluid run down the inside of my shorts as my penis bounced and twitched to the rhythm of its own beat.
After about 30 seconds, my penis began to settle down and return to sanity. I stopped doing what I was doing to her. My hands moved up to her shoulders and I slowly rolled her over. I looked down, Mrs Jennison lied there silently her head slightly tilted back, her eyes closed. She looked so beautiful and relaxed. I took a deep sight and placed my other hand on her breasts. I slowly moved my hands in a gentle circular motion, rubbing and caressing her breasts. Mrs Jennison’s breasts felt so soft and smooth and warm under my hand. Within a few seconds I was again standing at attention. It’s only now, as I reflect back on that dawning of a new era, that I can truly appreciate the teenage libido and it’s ability to recover quicker than a flash of lightning. The pressure in my shorts was unbearable, my penis was now very hard. I unbuttoned my shirt and slipped it off and took off my shorts, my hard penis popped out and stood straight out. Then I edged closer to Mrs Jennison and gently pressed my body against hers. My hand moved over her vagina and started to caress her lips backwards and forwards. I was slowly and carefully moving my hand all over her smooth belly, over her buxom naked hips, up and down her velvety thighs, returning to her cunt again and again to play in the thick silken hair, carefully rubbing the swollen lips, petting the crack, easing my fingers into the wet warm hole. She was lubricating and the juices were beginning to coat the lips of her pussy, making them glisten. I guess I must have spent too much time inhaling the intoxicating aroma, which emanated from that hot slit between her legs, I was in a trance, just staring at the most beautiful, most enticing sight that I had ever seen.
Finally, she couldn’t stand it any longer, and turned toward me, her arms slipping around my neck, her plump leg draped across my hip. She was offering me her pussy! I put my arms around her and tightened my grip and pulled her close. Her face was close to mine and her fresh clean breath sort of puffing into my nostrils as she panted in her eagerness. I could feel Mrs Jennison’s breasts press up against my chest, her stomach rubbing against mine. My legs moved between hers and parted them, my warm penis pressed up against her public hair. I let out a small groan of pleasure as I felt her fingers gently running back and forth over the shaft of my penis. Although I was just an inexperienced kid, my body knew just what to do. My arms wrapped around her shoulders and I positioned my penis at the entrance of her vagina. I slid forward and inserted my penis into Mrs Jennison and let out a grunt of delight as I penetrated her lovely pussy.
A little gasp of pleasure came from Mrs Jennison and she was pushing hard against me, impaling herself to the root on my cock. “God! She fits my pecker as tight as a glove!” I was thinking as I felt the hot, wet, velvety softness of her sheath
welcome me to her depths. Oh, what a FEELING! She was warm, wet and tight. I had fantasized about Mrs. Jennison at nights, but nothing had prepared me for this. I had no idea that my teenage body was capable of the sensations that it was experiencing then. I tightened my hold around Mrs Jennison’s shoulders and we were locked there for what seemed an eternity. Then I slowly started to thrust my penis backwards and forwards into hers, my chest rubbing against her breasts. I could feel the pressure building in my penis and started to thrust even faster. She put her arms back around my back, her heel pulling at my thigh. She was so hot and wet that I had to fight back the urge to cum immediately. Her open mouth was suddenly crushing mine, our tongues fluttering against each other, wriggling together as we passionately moved to and fro. I felt a sensation that I had never felt before in my life. We kissed for what must have seemed like a minute, then I broke off and gasped for breath. My God, we were fucking! I was already struggling to keep from shooting off. My thoughts began to wander back to that one summer when I walked in on my grandmother in the bathroom, then I wondered briefly what Dan would think if he knew what I was doing to his loving spouse. It seemed to help for a second or two, but her bumping and grinding was not giving me much room to hold back.
Mrs Jennison moaned as I began to pump her harder and harder which seemed to help slow the feeling, and I could see that she was about to come. Her foot was pulling harder than ever at my hips, her arms having tightened around my neck, her face now hiding in the side of my neck. It hit me like a sledgehammer! She was coming, this woman was coming! This time I went for broke and she exploded in wave of orgasmic spasm. She was really climaxing, and I could feel it! I never knew that a guy could feel a woman climaxing, but I damn sure felt Mrs Jennison’s that day. It was the way her vagina was pulsating around my cock. It had been pulsating throughout our fuck, but as she was climaxing I could plainly feel the tight walls gently squeezing and relaxing rhythmically along the length of my shaft. My head began to swell and I knew that there was no holding back this one. Then all of sudden I saw stars. I felt the slow spasm of orgasm as I began to pump her pussy harder and deeper. The deeper I pushed the harder she pulled me close. The feeling of cumming in her pussy was like nothing I could ever describe on paper. I just remember shooting and shooting as wave upon wave of ecstasy overcame me. My cock was jumpimg and jerking in her, shooting into her warm receptive belly. Just as erotic as the physical act was the control I had over this woman. Here I was, 15 years old, bedding this 40 year old woman. This is one memory that I would relive over and over in many a pre-slumber fantasy. I groaned loudly as I felt the heat transfer from my penis into Mrs Jennison’s vagina.until I collapsed on top of her. I lied there for few minutes, still inside her, placing kisses on her face. Her breathing had returned to normal again. I then moved to lay down beside her.
We laid there for several minutes, kissing and fondling one another. She was gently squeezing and stroking my cock and I was alternately playing with her nipples and letting my hand slide down her body to rub her pussy. From time to time, I sucked one of her tits into my mouth. It didn’t take long for her tender manipulations to turn my cock as rigid as an iron bar. I mounted her again. This time, I entered her more slowly than before and was even able to remain still and keep my prick buried up to the balls for a short time. To my surprise, I was able to last longer this time, I guess it was because I had just shot my wad such a short time before. She pumped her hips up to meet my every inward plunge. I maintained the long, slow stroking for several minutes, reveling in the sensation which her grasping vaginal muscles produced. It was as if her pussy was sucking my cock. It soon became necessary to increase the speed of my thrusting, both her passion and mine demanded it. I built speed slowly and Mrs Jennison matched my tempo, perfectly. When we had reached a fairly brisk pace Mrs Jennison began moaning. As her climax approached her moans became louder and louder. Soon she was panting, ÃƒÂ´Oh God! Yessss, yesss unnnnggggh, unnnnngggggh!ÃƒÂ¶ When she came she wrapped her legs more tightly around my butts, hugged me close and kissed me. I slowed to the long, slow, deep strokes, as her orgasm hit, it triggered me and I pumped another load of the thick, gooey jizm into her!
Finally, it was over and she sat up against the headboard on the bed. She said she wanted to talk to me about what had happened. “Look, Shawn, I never intended this to happen, and we can both get in a lot of trouble for this. You need to promise me you will never tell anyone about this.” At that moment, I would have promised her my soul. I agreed, and it wasn’t until my freshman year in college that I actually broke that promise. She couldn’t expect a boy to keep his first sexual experience a secret forever. She stood up and left the room to get a pair of Dan’s shorts for me to wear home. I lied back on the bed, still in shock. Did this just happen? Did I just fuck my 40 year old neighbor? I wanted this moment to last forever, but was quickly brought back to reality when she returned with a pair of worn out jeans shorts. She asked me how I was doing and again reminded me that this was our secret. She confessed that she would never have ever thought of doing this before, but she felt kind of sexy having a secret. She new she had taken my virginity, and that was something that gave her a sense of power and control.
I got dressed and as I was leaving she stopped me…
“Shawn, I forgot to pay you for the lawn. There’s money on the kitchen table if you want to grab it on your way out.” The perfect end to the perfect day. On my way home I could still smell her on my hands. In some ways I didn’t want to shower again for awhile, just so I could savor the biggest day of my life. I eventually did shower, and well, let’s just say that the Jennison’s had the nicest lawn on the block that summer.