Position Switch

NO one in this story in a sexual situation is under eighteen; all situations are between those of legal age.

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I was a proverbial late bloomer. Even though my father, Jack Watson, was six three, and 240 pounds of muscle, and as tough as anyone around, I was a scrawny kid. It didn't help much in my early teenage years that my father said that he had been a late bloomer too because no one at the school that I went to cared, and I suffered in comparison to my next door neighbor.

Will Simpson was the kid next door. Although just a year older than I was, since he was big and muscular for his age and I was short and scrawny for mine, it looked like we were four or five years apart, not one. Looking back, I think that Will had - likely still has - some sort of mental problem or personality disorder because he fluctuated between treating me nicely and cruelly; I never could tell from day-to-day. If it wasn't a personality disorder or mental problem, maybe his mercurial actions could be explained by how weird that his family was.

Will had an older brother, Sam, who was the town teenage jerk. Sam obviously got it emulating Will's father, Mitch, who was the town's adult jerk. Fortunately Mitch travelled a lot so he wasn't around too much, and Sam seemed to always be out causing trouble, or in jail for various misdemeanors.

The only normal member of the Simpson family was Will's mother, Betty. Betty was nice to everyone, but seemed to take a special interest in me and if she was around would make every effort to mitigate the harm that Will inflicted upon me.

Betty also seemed much more intelligent and sophisticated than the other members of the family too, and since I didn't have the body or coordination for athletics as a teen, I made sure to study hard and get good grades in a wide variety of subjects. Betty was always interested in history, literature, civics as related to current events, and even science, so many times we had talks about all of those subjects. Since both of my parents worked, oftentimes I would go over to Will's/Betty's house after school. After a discussion about a subject of mutual interest she would usually send me away with a home-made bakery treat with a smile and "Thank you for coming over to talk with me, Jeremy; it was so enjoyable." When I got into my middle teens, I also did home improvement projects for Betty, which I was rewarded for with a big smile, a chaste hug, and another bakery treat.

Will got his good looks from Betty - she had a very pretty face. While I never really paid any attention to her body, there didn't seem to be anything remarkable about it. She wasn't skinny or fat, but beyond that you couldn't tell much because she always wore very conservative clothing, whether at home or out.

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I guess that it's human nature to remember the bad things more than the good ones; at least it was for me as related to Will's treatment of me. Will was the starting quarterback of the varsity High School football team as a sophomore, and I was a lowly freshman. At Will's urging I was manager (towel boy) for the team for one year but never again in view of the cruel tricks Will urged his teammates to pull on me, including taping my pants on me, putting analgesic balm under my armpits, and soldering my locker shut. These harsh behaviors were interspersed with just enough inclusive acts so that I didn't completely disassociate myself from Will, and there were some good times when I was just "one of the guys."

Being such a scrawny non-athletic teenager, I never really dated; I was too shy around girls - exactly the opposite position that Will was in. He was outgoing and dated - on and off again - by far the best looking and sweetest female in the school - Marcia Briggs.

Marcia was every teenage boy's wet dream. She looked like Kate Upton before anyone had ever heard of Kate Upton - I think that about sums it up. She was the Queen of everything in the school not just because she was beyond gorgeous, but because she was nice to everyone. Of course I worshipped her, but she was so far from being attainable that I never, ever even considered the possibility of acting upon my worship. I could barely get a greeting out, I was so awed by her, the times that she came over to Will's house when I was around.

One thing puzzled me about Marcia, however. I could never understand why she put up with Will's mercurial antics.

The most emotional pain that Will ever inflicted on me was when I was at my most vulnerable. At the beginning of my junior year I had just started to get a little self-confidence and decided that I finally needed to act on a crush that I had on Amy Williams, who was in a few of my classes. Amy was not someone who I considered unattainable, like the goddess Marcia, even if she was more desirable in every way than I was. Amy's looks were probably in the top half of girls in our school, though not even close to those of the girls that Will dated when he was off-again with Marcia. I made the mistake of telling Will about my crush on Amy.

It wasn't two weeks after I had stupidly told Will about my crush on Amy that I finally worked up the courage to ask Amy out. As I was talking - mostly stuttering - with her near her locker, Will barged right into our conversation and asked Amy out on a date that weekend. Of course she couldn't refuse the handsome quarterback, and I was left with a reddened face as they walked away from me, chatting like old friends and ignoring me. It wasn't a month after that before Will had fucked Amy and then proceeded to trash her reputation around the school. Poor Amy couldn't handle it and transferred to another school at semester break.

After the Amy episode I distanced myself from Will - I had to for self-preservation. Perhaps strangely, the only person that I told about it was Will's Mom, Betty, when she asked me point blank one day why I would always disappear when Will came around and never went anyplace with him anymore.

Betty was as distraught as I was, comforted me, and even shed a few tears with me. Then she told me something very surprising but uplifting: "Jeremy, while I love my husband and boys I know that they're self-centered jerks, and I apologize for that. Will doesn't deserve a good friend like you. You'll have it rough in your early years, but someday you'll be successful far beyond them and anyone else in our neighborhood. Your intelligence and kind, loving, disposition will eventually hold you in good stead. Don't ever change; don't ever become mean or cynical." Then she kissed me on the cheek and gave me a big hug.

That did more to buoy my spirits than any other single thing throughout my teenage years. After that, any problems that I had I felt more comfortable discussing with Betty than my own parents. Betty was always a good listener, often had good suggestions, and always made it clear that she was in my corner no matter what.

Things started to change for me physically at the beginning of the summer after my junior year in High School. I was seventeen. I first noticed it when things I always had trouble lifting before were now becoming much easier to handle. Then my shoes didn't fit; then my pants were too short; then the collar on my only dress shirt was way too tight; and if I had been a singer my voice would have deepened from tenor to baritone. By the end of the summer I was of average height and weight - no longer short and scrawny.

I continued to dramatically change throughout my senior year so that about two months before graduation I was six two, 210 pounds, with almost no fat. When I noticed my musculature starting to develop, for the first time I actually devoted time and effort into improving my body. While my lack of a sports background meant that I didn't try out for any team sports, my school had just started weight training and conditioning classes as an alternative to gym, so I took that course and became almost addicted to working out - easy to do when you see progress. While both my mother and father favorably commented on my drastically changed appearance the person who was most flattering was Betty. "Your body is now as fantastic as your mind and personality," she gushed several times, with a big smile on her face!

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It was about the time that my physical metamorphosis was almost complete that two tragedies occurred next door. Betty's oldest son Sam had committed a felony and had been sentenced to two years in jail; then about a month later her husband Mitch died in a vehicle collision in another state. Will could only make it home from college for the funeral and a few days afterwards - once again demonstrating how self-centered that he was. Betty had no other family in the immediate area. Therefore, just before my eighteenth birthday I became Betty's main confidant and support system.

"Confidant" and "emotional supporter" weren't jobs that Betty thrust upon me. I just always made myself available to her, including visiting her every day after school. She confessed that she could no longer afford the house that she was living in, and with no family nearby wanted to get it ready to go on the market.

The summer after I graduated High School, my life was looking up. I had changed physically into the person that I wanted to be, I was all set to go to a good state school on a three-quarters academic scholarship, and I had an easy, though unusually well-compensated, summer job.

A few days after I turned eighteen, my parents had the only party that they ever threw for me since I had turned eleven; a combined graduation and eighteenth birthday party. All of my relatives, a number of my friends - including several new ones since I had matured physically - and a few neighbors were invited. Of course, that included Betty. Will was not coming home for the summer but instead going to summer school so that he could keep eligible for football, and I had already promised Betty that I would help her get her house ready for sale so she didn't need his help for that.

I didn't open gifts during the party, but did the next day. Betty had told me that she wanted me to come over to her house a day or two after the party and she would give me a special gift. When I went over to her house after my summer job two days post-party she was bubbly when she greeted me. I remember thinking that I was really happy that she was coming out of her malaise after her husband died and older son was sent to jail, and probably for the first time looked on her as a woman rather than a mother-figure. Ever since her husband died she had dressed less conservatively, and she had insisted that I call her "Betty" rather than "Mrs. Simpson." By the time of my party I was comfortable doing that.

"Hi, Betty; is now a good time for me to come over? You've got me in suspense about what my supposedly 'special gift' is," I greeted her with a big smile on my face when she opened her front door. Then I instinctively, certainly not thinking about it, said "You look really nice in that dress."

"Thank you, Jeremy," Betty grinned back. "I do hope that you'll like your presents."

I noticed the plural of "presents" but it didn't register at that time.

Betty got me a glass of juice, and herself a glass of iced tea, and we sat down at her kitchen table. "Her is a card and your first present," she said after I took my first sip of juice, extending a small package and an envelope. "Present first," she continued.

I took off the wrapping paper and found an original hardcover of Stephen Vizinczey's book "In Praise of Older Women," signed by the author. I had heard of this book in literature class my sophomore year, but had never read it. Betty and I had discussed contemporary literature many times, but never this book. "How did you get it signed by the author?" I asked, making eye contact with Betty; I noticed that she was blushing.

"I have a friend who works for a big publishing house, and she was able to get an original edition of the book and through her channels get it signed by Mr. Vizinczey. I hope that it's an OK present?" she replied. She seemed to flush even more.

"I've heard of this book and I'm sure that I'll enjoy it," I replied with a grin; I noticed that she diverted her eyes.

"Uh,..., you should open the card now," she said in a low voice.

"OK," I replied, tearing open the envelope.

The outside of the card had a combined graduation, 18th birthday, printed message; probably hard to find, but certainly not bizarre, or even unusual. I wasn't really prepared for the hand written message inside, however. "Jeremy, you're my favorite non-family person on earth. There are no words to describe how much your companionship over the years has meant to me, or the tenderness that you have demonstrated in the last two very difficult months. I believe that I can best show you how grateful I am by making sure that you don't go to college a virgin. Love, Betty."

I gulped hard - then lifted up my head to look at Betty. She was crimson, but met my gaze with a resolute look on her face. Then she stood up and by pulling one string dropped her dress to the floor - it was the only article of clothing that she had on.

Like any normal eighteen-year-old I had seen lots of naked women on the Internet. Due to my shyness and lack of a real social life, however, I had never seen one live. I immediately noticed that her tits were much larger than I had assumed undoubtedly due to the conservative clothes that she normally wore. I was especially taken back by the size of her areola and the hardness of her nipples - both much more extreme than in my typical Internet perusal.

Her crotch was glistening and almost hairless - except for what I had been told in Internet articles was a "landing strip." Her labia looked much bigger and more inviting than I had seen on a screen, and there was no mistaking a musty type of odor - not something that comes through on a computer monitor. I was absolutely shocked by how "female" she was.

I'm sure that my eyes were as big as saucers as "Wow - Betty is really a sexy-looking woman" flashed through my brain.

I had no move - I was frozen. Fortunately, despite her obvious embarrassment Betty did have one. She slowly walked over to me, bent over, and gave me a slow kiss on the lips. Then while staring into my eyes she took one of my hands and raised it up to a nipple. She held my wrist and I instinctively lightly pinched and stroked her pencil-eraser sized and firmness appendage.

After a minute or so of that, she reached for my other hand and placed it on top of her snatch. I could feel the wetness seeping out of her crack. She moaned when my fingers came into contact with her outer labia.

After I rubbed the outside of her pussy for a couple of minutes, apparently Betty had established that I was not going to run away, so she slowly lowered her body until she was on her knees and started unzipping my fly. Although I certainly had felt tightness in my groin when I was touching Betty's equipment, only when her hands went to my crotch did I notice how significantly I had tented my pants - and how painful my cock was as a result. Betty took care of that in short order.

My belt was undone, my fly opened, my pants pulled down to my knees, and Betty's mouth was on my cock, in what seemed to be no elapse of time whatsoever. When her lips touched my rock hard dick I flinched, then sighed, as the best feeling that I had ever experienced washed over me like a rolling ocean wave. When my eyes were open I could tell that Betty was staring at me as her right hand held my cock, her mouth engulfed it, her tongue caressed it, and she fondled my balls with her left hand. All too quickly the glorious sensations ramped to a crescendo and I felt wad after wad of my cum spurting out of my penis into her pulsating mouth.

When the intensity of my orgasm had peaked, but a general sense of euphoria still remained, Betty gave my cock one last lick and then proceeded to completely remove my shoes, socks, and pants. Then she stood up, grabbed my hand, and said "Come with me to my bed; I knew that you'd be too quick for your first climax so I wanted to do it orally. Now I'd like to show you the pleasures of true intimacy."

At that point, my mind was off in space somewhere. I would have done anything that Betty told me to do. Although she never said a word, what she did tell me to do by her actions, soft hands, and looks, was to take off my shirt, and then lay down in bed with her while we kissed, she rubbed my balls, and I put my hands anywhere that I wanted to. After several minutes of this bliss, during which I came to enjoy both her wet hole and mammary glands more and more, she whispered in a silky smooth voice "I can feel that you've recharged. I'm going to mount you now."

I rolled onto my back, Betty straddled me, and gazing into my eyes with what had to be the most loving look that I had ever seen grabbed hold of my cock with her right hand, supported herself on my chest with her left, and lowered her slippery hole onto my cock. Every centimeter of penetration spiked my pleasure receptors; by the time that I was completely buried I felt even better than when she had sucked me dry.

Although at the time I had no idea what she was doing, in retrospect it was clear that Betty was pulsing her pc muscles as she slowly moved up and down. I quickly got the hint when she moved one of my hands into contact with one of her boobs, and I latched onto both of them as she rode me to euphoria. I'm quite sure that she had an orgasm which interrupted her bucking, and after she continued and I squirted into her love canal she had a second one. I felt a sustained exhilaration, a feeling incredibly beyond what I had ever experienced before. Betty collapsed on top of me and we lay together, with my key still in her lock, as a sense of well-being drifted over me.

When I got dressed and was ready to leave about an hour later, a still naked Betty - with a crimson crotch leaking some of my bodily fluids - gave me a passionate kiss good-bye. "Jeremy; would you like me to give you a key to my house. Until I move I'll always be available to you."

"I'd love that, Betty," I mumbled, then kissed her again. "This has been the best day of my life so far..."

She interrupted me with a wicked smile. "The best is yet to come."

And it was!

It was by far the best summer of my life. Betty and I didn't just have sex; we went to movies, plays, canoeing, and to the park, together, either in separate cars so as not to raise suspicions about our relationship, or under the pretext of doing something to help sell the house. My parents, involved in their own lives and that of my younger sisters, never questioned me. I'd visit Betty after work two or three days a week; we'd shower together and then fuck like minks. The days that I didn't come over after work I'd use the key that she'd given me and sneak into her house in the middle of the night, ravage my lover a couple of time, then return home not just satisfied but euphoric.

I don't think that there was one day that summer that Betty and I didn't have sex of one kind or another. It turned out that our mutual favorite was tit fucking. With her encouragement I tried it for the first time after we had been intimate about a week and I was changing from awkward to comfortable; and about a half hour after she had given me a blow job to relieve the tension in my balls. The sounds that she made and the looks on her face as I stroked my cock in the lubricated valley between her tits while she pushed them together drove me nuts. She actually orgasmed from my tit fucking alone, and when she came down from that shrieked "In my pussy, please, Jeremy!"

I instantly removed from cock from her valley and buried it in her soaking wet pussy in one thrust. It wasn't a dozen strokes later before I was cumming like a fucking volcano and she was writhing from a second orgasm within a couple of minutes.