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My Fantasy Becomes Reality

Category: Mature
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My story is one that started out as a fantasy and wound up being a reality. I am a middle-aged man living in a south suburb of Chicago, actually in Indiana. My fantasy turned reality centers around a beautiful mature schoolteacher in the early fifties age bracket. She happens to be a wonderful woman who knows exactly what she wants.

Her name is Jan and she is without a doubt, the most sexiest, passionate mature woman that I have ever met. When I met Jan for the first time was at the hospital, she was visiting a mutual acquaintance of ours.

Jan introduced herself and I learned later that she was a high school English teacher. In fact as we began talking, she tutored my cousin at one time in English and still remains friends with one of my aunts.

Jan was married, but she was a very lonely woman and filled her leisure hours by helping other people. So as time went by, I began to see her more often because she had volunteered to assist homebound elderly people that have been recently discharged from the local hospital. She was so kind and compassionate that aside from her physical attributes, I really started to take an interest in her.

Jan had a lot of nervous energy and she channeled that into her random acts of kindness and chores that she performed for other people.

For example, I was visiting my elderly father and I was surprised to see Jan there mowing his yard. I told her that she was working too hard and she replied that she liked to remain active in her time away from school and try to stay in good physical shape. I told her that she looked almost perfect to me.

Jan seemed a bit embarrassed that I said that and she said thanks for noticing. She said her husband was a career educator too and he was hardly ever home anymore. I could not help but notice how attractive she was, even with no makeup on and regular clothes. When I was younger and in high school, I often fantasized what it would be like to have sex with my female teachers.

I found myself staring at her chest, as her blouse was all sweaty and clinging to her. She had several buttons unfastened and quite a bit of cleavage was exposed. Jan was moderately endowed and I could not help but look. Jan caught my leering expression and to my delight, she just smiled slightly and asked if I was married. I replied that I was divorced and currently not seeing anyone.


At this point in the conversation, I was definitely interested in her and I decided to offer a cold beverage and allow her to take a break and get to know her better. She accepted and when I returned with the cold beverages, I noticed something different about her. I thought for a moment, then I realized that while I was gone, a few more buttons on her blouse were unfastened and I could see the lacy edges of her brassiere.

Furthermore, I got the impression that she might even be interested in me, because her nipples were almost poking through her bra and I surely would have noticed that earlier. Jan seemed to not mind my ogling as I handed her a beverage. I was starting to become aroused myself, just thinking about my fantasy and a schoolteacher.

Jan continued to ask subtle questions about my personal life and I gladly answered them. Even though I was having a difficult time concentrating because she kept slowly pumping her leg back and forth and crossing and uncrossing her legs. She wearing shorts and they were not really short, but they were a little baggy and I swear she was not wearing any panties. In fact on one occasion, I thought I saw a wisp of her pubic hair peeking out from the leg of her shorts.

The more often she moved her legs, the higher her shorts rode up her legs and exposed some very firm white thighs. Just then, I had a naughty thought about how I could help her burn up some of that nervous energy.

The longer we talked, the hornier I became, and just thinking about how we could make my fantasy come true.

I believe that Jan knew I was not interested in conversation any longer, because she suggested that she wanted to pull some weeds from the flowerbed before she finished. So she asked me if I could assist her and of course I said yes. I held the lawn bag while she pulled the weeds and at one point, she bent way over pretending to pull a stubborn weed and lingered there long enough for me to fully admire her beautiful ass. Oh was she a tease, I almost groped her right there.

Jan’s legs were completely tanned, all the way to her ass and they were so firm and tight. Not really skinny, but muscular and quite firm.

She definitely took care of her body and since her shorts were of a Very light color could tell that she was wearing dark color bikini panties.

As Jan continued to bend over in front of me, I was just mesmerized by her lovely ass and the more she bent over, the view of her sexy ass was even more enhanced.


I am certain that Jan knew that my eyes were glued to her sensuous ass, because she would turn and smile and slowly bend over again a wiggle that sweet package ever so slightly. When she finished this little task, she turned around and smirked wickedly and looked me in the eye at first, then averted her stare to the ever-growing bulge in my pants. Jan stared momentarily and then looked up at me and licked her lips.

I definitely did not need any more encouragement than that, so I asked her fi she would be interested in going out for an early dinner with me when she finished her good deeds for today. It did not take her long to agree and I was certainly delighted. Jan then bent over again to pick up her gardening tools and this time I was facing her and her tits were practically falling out of her blouse now and I could see her nipples clearly.

Jan suggested that instead of going out for dinner that she would make dinner for me if I didn’t mind. I immediately accepted and inquired about her husband and she said that he was out of town on business.

My mind went numb now just thinking of the possibilities that existed for me to make my fantasy come true. Jan asked me if I could help her put her

Gardening equipment in her car and I said sure. As I stood behind her, handing her the equipment, she backed right into me and I had a raging hard on. She reached quickly behind her and discretely gripped my cock and gasped.

I apologized for being so forward, but I told her that she was really beginning to turn me on. In fact, I said I was horny as hell and we needed to do something about this. Jan said she was looking forward to a little fun.

She made me promise that this would be our little secret and to meet her at her house in one hour.

So I raced home, showered and changed clothes and picked up bottle of wine and sped to her house. When she answered the door, she looked like a million bucks. She had just showered, put her hair up and applied her makeup and smelled heavenly. She asked if I was hungry and I looked her up and down and said I could eat you right now. Jan said she had never been told that before. I told her that she looked absolutely ravishing.

I noticed that Jan did not seem to have much clothing on under her robe and I was dying to see just exactly she did have on. I offered her the wine that I had brought and she poured tow glasses for us and offered me a seat in her living room. As we sat down, Jan’s robe parted slightly and I got a peek of what appeared to be bright red garters possibly pink panties and they accented her black nylons marvelously.


As Jan and I sat and chatted while drinking our wine, she confided in me that she was not much of a drinker, in fact the wine was making her a bit light headed. Of course, being the gentleman that I was I offered her to rest her head on my shoulder and she did. Jan then put her arms around my waist and said that she and her husband had not done this in years. I said shame on him; a lovely woman like you needs to be treated with tender loving care.

She told me that she liked the sound of that.

I felt emboldened now to make my move and I let her hair down and brushed it over her shoulder and turned her face towards me and kissed her.

She offered no resistance, so I gently placed my hand behind her neck and firmly kissed her on the lips now and her willing mouth opened to accept me. Within moments, we were both moaning in ecstasy and my hands were roaming her body freely. I cupped her breasts and she sighed and then she grabbed my belt and unfastened my pants.

I was amazed at the grace and skill that Jan demonstrated in undressing me while I was frantically French kissing her. She had my bare cock in her fist pumping and pulling like she would lose it if she ever let it go. She commented on how wide I was and I said that makes up for length and she said baby this is fine.

As I continued kissing her neck, and shoulders, I slowly managed to open her robe and she was wearing the sexiest lingerie that I have ever seen and she smelled so intoxicating. I was ready to do her bidding, anything she wanted. I was totally smitten with her charm and sexiness. I could not help myself, I lowered my mouth to her breasts and started sucking and groping them through the thin satin material of her negligee.

This obviously pleased Jan because she promptly removed the top half of her sexy ensemble. This allowed me full access to her fantastic breasts and soft erect and puffy nipples. Jan said that her nipples always were a bit sensitive and she loved to have them sucked. I told her that her wish was my command and I immediately went to work sucking and teasing her nipples.

Jan was thrilled, she was making a low purring sound in her throat and I was sucking like a starving baby. Without warning, she grabbed me by my ears and pulled me tightly into her sensuous bosom and whispered oh lover, that feels so fantastic, please do not stop. As Jan was writhing and holding tightly to my head, I managed to take my free hand and explore her treasure between her legs.


What I found was a wet, gushy surprise, Jan was sopping wet and I almost was able to wiggle my entire hand under her panties and into her pussy. As I brushed my fingers across her clitoris, she squealed with delight and started trembling and she exclaimed oh my god I am cumming already!

Jan was really a gusher when she came, and while she was gyrating and shrieking I was able to use my thumb to stimulate her clitoris and prolong her euphoria.

Jan eventually calmed down and she kissed me hard on the lips and said that was a first for her to have an orgasm from just foreplay. I was quite proud of the fact that she was so pleased. I extolled her virtues as well, being the sexiest mature woman that I had ever met. With that, Jan got down on her knees and proceeded to give me the best blowjob that I have had in quite a long time. She certainly had the energy of a much younger woman and I loved it.

Jan sucked so hard, I thought she might just inhale my cock, balls and all. After experiencing this fantastic head, I was ready to release in not time at all. I waned Jan and she just murmured HmmmHmmmm and I let loose with what seemed like a flood and she sucked every last drop. Even I was surprised, when she was finished I was still semi-erect. She was pleased that she had this effect on me and she suggested that we move into the bedroom.

Her bedroom was fantastic, she had a huge bed and fragrant candles were glowing everywhere. I took her by the hand and gently laid her back on the bed with her legs overhanging.

I gently rubbed the arches of her tiny feet and then I kissed her beautifully manicured and painted toes one at a time. Jan was smiling contentedly as I methodically kissed my way to her upper thighs. When I arrived at her beautiful bush, I casually removed her panties, garters and nylons. When I had removed the last bit of her sexy attire, I placed her ankles on my shoulders.

Jan was pleading with me in a low husky voice to fuck her now, instead, I started licking and kissing her juicy pussy. She was wetter now than before and writhing all over the bed and moaning. With her ankles dangling over my shoulders, I was able to grab her hips and grip tightly enough to keep her from wiggling away while I devoured her pussy. She was into it now, instead of trying to hold her legs apart, she pulled my hair to force my down on her even harder as she was screaming how wonderful that felt.


Jan was so turned on that she wrapped her ankles tightly around me and she managed to lift her ass of the bed to hump my face like a cowboy riding a bull. She was definitely a wild woman when excited and by the look of total ecstasy on her face, she was enjoying every lick. This mild mannered schoolteacher was a nymphomaniac in disguise. I loved the way she reacted when presented with a challenging position.

When she finally had another orgasm, I was gasping for breath as well and she was almost delirious with pleasure. She released my hair and just kept kissing my face and biting my lips. When she collapsed onto the soaking wet bed, she told me she could never repeat that again. Jan gasped that she was totally exhausted and thanked me for the best oral sex she has ever had in her life.

Jan was lying on her back panting when I grabbed her by her ass cheeks and pulled her to me and without warning, I drove myself deep into her womb and she instinctively wrapped her legs around my hips and held on for dear life. I fucked her like a horny Neanderthal and she kissed me passionately and scratched at my back as she had smaller multiple orgasms.

We fucked like young rabbits for quite some time until I spewed my load deep into her belly and we both collapsed onto the bed in

Each other’s arms.

As we lay there happily satisfied, I was feeling horny again and I started kissing her belly and tits. Jan was starting to become aroused again too and I gently rolled her over on her side and playfully explored her ass with my hands. At first, she seemed a bit apprehensive about what I was doing, and then she was pushing her ass towards me and sighing with anticipation.

Suddenly, Jan rolled over and reached into a drawer on her nightstand and retrieved what appeared to be a brand new tube of KY lubricant. She just winked at me and smiled and I said oh baby you are very resourceful.

Jan laughed and said it was meant for her toys, but this is far better and more enjoyable. I wasted no time in applying liberal amounts of lube to Jan’s delicate rosebud. In fact, she said that she had never had anal sex before.

I assured her that I would be very gentle and if she wanted to stop, to just tell me so. Jan kissed me full on the mouth again and then she lay down on her stomach and slightly raised her hips. I placed several pillows under her abdomen and then I went to work massaging her anus with the lube.

At first, her rosebud puckered very tightly to resist the intrusion of my fingers. However, it was not long at all before she was grinding that sexy ass against my fist.


Jan was extremely horny again and while I was pumping four fingers in and out of her butt, I was massaging her clit with my free hand. She was swiveling her hips tremendously now and pleading with me to take her.

So without any forewarning, I pullled her hips towards me and guided my cock into the tightest ass on earth. I could not believe how her muscles instantly started contacting and expanding around my cock.

She was a fantastic sex partner and I am surely grateful for her allowing me to be the first to pleasure her in this manner. I was pumping as gently as possible and she was grinding down on my cock feverishly. I rose to the occasion and pulled almost out and began repeatedly pumping her ass ferociously. She suddenly squealed in a high pitched voice for me to pound her harder because she was on the verge of another orgasm.

I felt my tension building rapidly as well, so I reached under her and grasped her vaginal lips between my fingers and rubbed them and she howled fiercely Ohhhhh lover, Ohhhhhhhh baby I am coming now!

Almost simultaneously I filled her gorgeous ass with my sperm. In fact, it was running down her cheeks and she was quivering tremendously. I held her tightly by her hips until she relaxed and I fell to the bed beside her face to face and we kissed softly.

Jan told me that was the greatest experience of her entire life and I told her that she made it the greatest sex ever. This fantastic woman has the stamina of an eighteen-year-old girl. I asked Jan if she thought she could introduce her husband to her newly acquired techniques and she replied absolutely not. Those are reserved for her and I. Then she asked me if we could become steady lovers and meet discreetly as often as possible for repeat performances.

I replied to Jan that there was no way another woman could ever satisfy me after this night. Of course we finally went our separate ways, but not after many hours of unbridled raucous sex. Furthermore, I confessed to Jan that my ultimate fantasy was to have sex with one of my high school teachers. Although, she was not one of my teachers, she certainly was the best sex partner I have ever had. Therefore in my opinion my fantasy was fulfilled in a big way. Jan kissed me lovingly and said so was her fantasy.

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