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June 11, 2007

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Filed under: mature ladies, mature vs young, sexy older women — Kamo @ 1:47 pm

When I was growing up in south Florida in the ’50s, I lived a privileged life. My family wasn’t really wealthy, but we were more than comfortable. We lived in a large, lovely home on a golf course. We were members of the exclusive country club in our area and traveled in all the right circles. From the time I was sixteen, I had my own car and was a member of the “in” clubs at my high school. I wanted for nothing, nothing that is except an exciting sex life.

I was good looking, best described as “cute”, but I wasn’t the school stud. As a sophomore in high school, I was 5′ 7″ tall and weighed a hulking 135 lbs. It wasn’t until my junior and senior years that I experienced a growth spurt which resulted in my attaining the lofty height of 5′ 10″. Nor was I the school jock. I was athletic, but my size mitigated against football stardom. I did play on the junior varsity team for awhile, but in a scrimmage against the varsity, I made the serious, and almost fatal, mistake of attempting to tackle the varsity fullback who weighed about sixteen tons. At least, that’s what it felt like when he flattened me like a steamroller. After my recovery from unconsciousness, a fractured jaw and several broken teeth, I joined the golf team and had a very successful high school athletic career as an orthopedically sound, if not champion, golfer.

My sex life, like that of most teenagers in the ’50s, was woefully inadequate. I had plenty of dates and my fair share of girlfriends. I even got laid once by one of the girls on the “Easy” list. It was a quick, exciting, wet, sloppy, frantic and not altogether fulfilling experience. The rest of my sexual experiences with members of the feminine gender generally consisted of furtive groping in the back seats of darkened automobiles. I remember many fondled breasts, wet fingers, blue balls and cold showers. Other than that, my sexual satisfaction was provided by “Mother Palm and Her Five Lovely Daughters”. I definitely was not an accomplished lover, that is, until after my experiences with Evelyn!

My mother was the quintessential southern belle socialite. She was a member of the UDC (United Daughters of the Confederacy), the DAR (Daughters of the American Revolution), the local women’s club, the Diggers (the exclusive garden club which my Dad dubbed the “Hoers”), and the local Baptist church. She volunteered at all sorts of things. In addition, she played golf, tennis, and bridge regularly. Her golf, tennis, bridge, church, and garden club “buddies”, collectively known as the “girls”, were always underfoot at our house. I was always having to run the gauntlet of ladies’ embarrassing comments about how much I had grown, how handsome I had become, how I must be a lady killer, etc., etc., ad infinitum, ad nauseum. However, Evelyn was the one “buddy” who didn’t make that kind of comment. I loved her for that alone.

Evelyn was unique to my mother’s circle of friends. She was employed at a paying job. She was the executive secretary to the one and only true billionaire in our area. She had been employed by Mr. D for many years. He was a widower and had no immediate family. Evelyn became his family, and he treated her as his daughter rather than as his secretary. Evelyn had never been married and lived in a private wing at his mansion. She shared most of his servants but had her own personal maid. She drove a baby blue Lincoln Mark II purchased for her by Mr. D. It was said that she had acquired so many shares of stock in Mr. D’s companies over the years that she was a millionaire in her own right. At any rate she was accepted in the highest circles of society.

There were some whispers, of course, that the relationship between Mr. D and Evelyn had been intimate at one time. However, since she was in her early forties, and he was in his eighties and the most powerful man around, the whispers remained just that–whispers. Although there were many male suitors seeking her favors, Evelyn never dated. At the opera, the ballet, and other functions Evelyn was either escorted by Mr. D or attended alone. I suspect that this was one of Mr. D’s rules.

At this point I should mention that Evelyn was also very beautiful. She was tall and shapely with a trim figure. Even in her forties, her full breasts were carried high on her chest, and her round derriere had not yet begun to spread. Her medium length auburn hair was perfectly coiffed with never a hair out of place. Her clothing and jewelry were tasteful, conservative and obviously expensive. In sum, she always looked as if she had just stepped out of a fashion magazine. She was perfection personified.

Even when she played tennis, she was too cool to believe. In her tennis whites, she was a dream. Her long, tanned legs propelled her effortlessly across the court to the ball, and her short, efficient strokes rifled it back across the net. Even in the south Florida heat and humidity, she never seemed to sweat. What is that old saw? “Ladies never sweat; they perspire.” I don’t know that Evelyn perspired, even when she played tennis. Every now and then she would dab at her forehead with one of her wristbands, but only occasionally, as if it were an aberration. And her ice-blue eyes were just as cool as she was. By now it must be obvious that I had a heavy-duty crush on Evelyn, and I have to admit that I entertained numerous erotic fantasies about her. Remember “Mother Palm”?

Evelyn was always warm and friendly to me, never patronizing. She seemed genuinely interested in me and the mundane events of my life. I have always been a voracious reader, and my mother evidently told Evelyn that, in addition to my schoolwork, I read two or three books per week and all the magazines in the house, including the monthly issues of National Geographic. One day Evelyn called the house and asked for me. When I picked up the phone, she asked me if I would like to have a complete leather-bound set of National Geographics from the first issue date to the present. She said that Mr. D had two sets, was willing to part with one, and that she had already cleared it with my mother. Of course I was ecstatic and jumped at the offer. We made arrangements for me to meet her at the mansion on the following Saturday to pick up the books.

Saturday dawned bright, hot, and muggy. I dressed in an old Lacoste “alligator” shirt, a pair of shorts, and my trusty old Weejun loafers. I was excited for two reasons. First, I was eager to get the books. Second, and of equal importance, I was practically salivating at the chance to spend some time alone with Evelyn.

When I arrived at the mansion and was greeted by the butler and then Evelyn, I was stunned. She was wearing the shortest short-shorts that I had ever seen on a feminine body. In addition, her breasts were only semi-encased in a bandana-halter-type-thing that defied description. I mean, those beautiful mounds and their nipples were practically right out there in the open air! I just stopped dumbstruck and stared at her entire body.

I was very suave! My mouth dropped open like that of a cretin, and I probably would have started to drool if I had been left to my own devices. Fortunately, Evelyn laughed–a full throated, musical laugh that brought me to my embarrassed senses.

“Obviously, you like my outfit,” she giggled.

As I regained some of my composure, I replied very articulately, “Mmmm, Uhhhh, Gurgle, Gurgle, Mmmm, Yeaaahh!” mixed together with some other gibberish.

Evelyn giggled again, grabbed me by the arm, and said, “C’mon we’ve got work to do.”

She propelled me into her kitchen, and I was painfully aware of her physical presence next to me. Her right breast was burning a hole in my left arm as she calmly asked me if I would like a Coke before we started. Somehow I sputtered out a “yes”. I was so addled that I probably would have taken a cup of hemlock had she offered it to me. I also become painfully aware that I was developing a growing erection. Thankfully, my shirt wasn’t tucked into my shorts and was covering the rising embarrassment. The thought did occur to me that I was making a complete ass of myself.

Evelyn offered me a chair at the kitchen table and brought me a Coke. She took a seat on a bar stool at the counter opposite me, hooked her feet into the rungs of the stool and casually spread her legs. The view was sensational but hardly conducive to clear thinking. I could see the ultra-tight crotch of her shorts pressing against the full lips of her sex, and when she spoke to me she would lean over to the point where her breasts were on the verge of tumbling out. The fact that they didn’t was some sort of an engineering miracle.

I actually felt dizzy and at first had no idea what she was saying to me. Then I became aware that she was asking me about school, the golf team, my girlfriends and my social life. I really don’t know how I responded to her questions, but I must have carried on some semblance of a conversation, probably in words of one syllable. I’m sure that my eyes were the size of saucers, but she acted as if everything were normal. Then she steered the conversation around to herself and asked me if I found her attractive. Naturally, I fell all over myself telling her how beautiful and attractive she was. I was a fumbling, fawning idiot!

She then became very quiet, got a pensive look on her face and said that we better get to work. I choked down my drink and painfully followed her gorgeous ass into the library. My hard-on just wouldn’t go away, and I decided that it was going to be a permanent condition as long as I was around Evelyn.

The library was enormous and had one of those ladders on rollers attached to a track for easy access to all the books. Evelyn pulled it around to the area where the Geographics were located and pointed to them on shelves well over our heads. She volunteered to climb the ladder and hand the volumes to me while I also steadied the ladder. As she climbed I found myself face-to-cheeks with her beautiful derriere. She seemed to wiggle it a lot, and the ladder wasn’t that stable. I was ready to faint with desire but was afraid she was going to fall.

Evelyn looked down at me and said, “Perhaps if you held my legs the ladder wouldn’t shake so much.”

I panicked and responded, “Oh no. The ladder would be much more unstable that way!”

I’ll never forget the exasperated look that Evelyn gave me. She climbed down the ladder, turned around and stood with hands on hips facing me. She reached around my neck with her left hand, cupped the back of my head and placed her right hand gently on my chest. She leaned forward and said in the most sensual voice imaginable, “Sweet Boy. How am I going to seduce you if you won’t cooperate?” She then cut off any response by taking my face into both of her hands and planting the hottest, wettest kiss in creation upon my lips. Her tongue probed deeply into my mouth searching for mine. I was momentarily paralyzed, but only momentarily. Reacting instinctively, I kissed her back hard. For what seemed like an eternity, our tongues dueled, and the only sound heard was the smacking and slurping of our mouths.

Evelyn then stepped back and began pulling my shirt over my head saying, “I need to get rid of this so I can see your young body and that thing in your shorts that you’ve been trying to hide since you arrived.” Once my torso was naked, she reached for my shorts and unbuttoned and unzipped them. As they fell about my ankles, she pulled my briefs down also. I numbly stepped out of the garments pooled on the floor and kicked off my loafers. I stood there naked and erect under her steady gaze. I was no longer embarrassed. I was just burning with lust!

“Yes! That’s more like it,” was all she said. She leaned over and kissed and gently nibbled each of my nipples. Then she dropped to her knees in front of me, reached for my cock with one hand, grabbed my ass with the other and pulled me to her. I had pre-cum all over the head of my prick and was on the precipice of an orgasm. She leaned over again, gave my cock one quick lick on its head and took my erection into her mouth. I exploded instantaneously, and my cock pumped copious amounts of cum into her sucking orifice. She swallowed my entire load and smiled up at me angelically.

I began to apologize profusely for my hair-trigger indiscretion, but she shushed me at once. She looked up and chuckled, “That’s the glory of youth! You’ll be ready for me again in a few minutes, and you’ll be more in control the next time.”

“The next time?” I gasped. “You mean there’s going to be a next time?”

“Of course, you silly boy! We’ve got the entire day ahead of us. Now, let’s adjourn to my bedroom where we can be more comfortable.” She handed me my clothing and shoes, arose, took me by the hand and led me upstairs to her bedroom. On the way, she asked me if she were my first woman. I told her about my one experience with the “easy” girl and said that she would be my first real woman. She laughed and said, “Good! I’ve lots to show you.”

In the middle of her huge bedroom was the largest four poster bed that I’ve ever seen. It was draped in colored fabrics and sheer silks and reminded me of the stories I read of Arabian harems in “A Thousand And One Nights”. It was too erotic for words, and I was totally turned on. My cock was already standing at attention again. As we stood by the side of the bed, Evelyn fondled my hardness and my balls.

She asked, “Do you want to watch me undress or would you rather do it yourself?” I opted for the latter, and after a good bit of fumbling around with my ten thumbs, she stood nude in all her glory right there in front of me. Her breasts were exceedingly full, and her large dark pink nipples were standing out proud and hard. She had trimmed her pussy hair to a small triangle, and my eyes were drawn to it like a magnet. I could see that she was wet. Hers was the first pussy that I really had a chance to visually examine in detail, and I was ready to die right then and there.

She then crawled onto the bed and beckoned me to join her. As I crept in beside her, she said, “Now I’m going to teach you how to make love to a woman.” We kissed passionately, and she placed one of my hands on her breast. “That’s it. Caress my breast. Fondle it gently and tease the nipple with your fingers. Pull on it but not too hard.”

She led me through the all the steps necessary for competent breast loving– the fondling, the kissing, the suckling and the nibbling. I was in heaven. She then showed me how to really turn a woman on by touching, caressing , licking and love-biting all of the various erogenous areas of a woman’s body.

I clumsily pawed her pussy with my hand, but she slowed me down and taught me how to properly finger and tease her pussy and clitoris. Apparently, I was a quick study, because she began to make whimpering sounds as I finger fucked her. “Mmmmmmm,” she moaned as I stirred the honey between her legs. “Oh yes!” she cried as I inserted two, then three, and then four fingers into her.

After awhile she stopped me and pushed my head down between her legs saying, “Oral sex is where the men are separated from the boys, my love. If you can please a woman orally, she’ll do anything for you. Come pleasure me, darling!”

As I was pushed down her taut body, I was at first overwhelmed by the musky odor of her sex. However, that passed quickly because I was so turned on that I would have done anything to please her. When I was ensconced between her legs and looking at her juicy pussy, she began to coach me, and I followed her every instruction.

“Blow softly on my pussy. Yes, that’s it. Oh, that’s making me crazy! Now, take the tip of your tongue and lightly circle the outside of my pussy lips. Oh yes! Tease me! Again! Now, flatten your tongue, and gently lick my pussy from bottom to top. Ohhhhhhhh! Again! Again! Don’t stick it in yet! Keep on licking. Yes; yes; yes! Now, sharpen your tongue and stick it in me. Fuck me with your hard tongue. That’s it! In and out. Fuck me with your tongue! Tease my clit! Now, suck it. Suck it. Suck it! Eat me darling! Oh, Sweetheart, you are on your own! ”

She was moaning and crying almost incoherently by now, and I felt like the king of the world. I had the power over Evelyn, and I never wanted to stop worshiping her. I licked and teased, and suckled and probed, and kissed and nibbled until she was wailing nonstop. Finally, after what seemed liked hours but must have been only a few minutes, she screamed, “I’m commmiiiinnnngggg!”

Her thighs seized my head in a death grip, and she came like freight train. “Stop! Stop!” she pleaded, but I didn’t, and she continued coming again and again. I suckled and drank her enthusiastically until she again begged me to stop. I finally paused , and we then collapsed together. I couldn’t help but notice that Evelyn and I were drenched with sweat, not perspiration, but good old fashioned sweat! The ice queen had melted.

“That was heavenly,” she murmured and began to cuddle me. I cuddled back for awhile, but she began to doze off.

I jabbed her in the ribs with a finger and said, “Don’t you dare fall asleep on me yet, Ma’am. Like John Paul Jones, I have not yet begun to fuck!” She giggled sleepily. I laughed and began to nuzzle her breasts. Nuzzling became kissing, which in turn gave way to suckling. I reached down between her legs and began to gently finger her and tease her clit. She began to whimper again, and reached for my little captain who was more than ready for battle. Her tiny hand on my throbbing cock felt so good that I began to moan as well.

Evelyn laughed again and said, “We sound like a couple of cows mooing. And by the way, don’t call me Ma’am, you young squirt!” She chuckled again as she squeezed my cock more forcefully.

“Yes Ma’am. I mean, no Ma’am. I mean, yes Your Ladyship! And before this day is over, I do intend to squirt–in you!”

We both laughed heartily. The love play was wonderful, but that little hand of hers on my cock and mine on her pussy had begun to heat things up. The laughing became cooing, and there was no longer time for word play. The words became moans, and the squishing sound of my fingers sawing in and out of her pussy filled the room.

She tore her mouth from mine and cried, “Fuck me. Fuck me right now!”

As I climbed between Evelyn’s legs, she reached down, took my cock in her hand and began rubbing the head against her pussy lips. I was on fire and tried to push it into her. “Wait a minute,” she said and continued to rub my cock up and down against her dampness. Gradually, she inserted it little by little past her hungry lips. I couldn’t stand it anymore, so I impaled her with one final thrust. She held me tight and urged, “Be still.” Then, as I strained to remain motionless, she began to squeeze and massage my cock with her vaginal muscles. I couldn’t help it. I started to move, slowly at first and then with more intensity and speed.

She began coaxing me again. “That’s it, honey. Fuck me! Fuck me! Slowly! Slowly! There; there; there! Oh Yes!” Now we were moving in concert faster and faster. “That’s it baby! Faster! Harder! Fuck Meeeeeeeeeeeeeeeee Babyyyyeeeeee!”

I couldn’t hold back any longer. I shouted, “Here I come!” and fired my hot cum deep inside her pulsating pussy, spurting again and again.

“Aaaaahhhh!” she screamed as her raging climax followed almost immediately. She wailed and shouted and clutched and bit. Her legs wrapped around me so tightly that I couldn’t breathe for a few moments, but they loosened their hold soon after we released our mutual passion. We lay coupled together until my cock wilted and gradually slipped out of her. Evelyn mewled her disappointment at my withdrawal, and we cuddled together until we both began to nod off.
Just before we drifted into sleep, Evelyn said, “You learn quickly. I give you a B+.” That remark earned her a slap on the fanny and a kiss to make it better. I was intensely cocky and proud of myself. I slept like a baby.

Later I called home and told my mother that Evelyn had a number of chores that I was going to help her with and that I would be home after dinner. We made love several more times that day and evening and many more times during the ensuing days and months. We fucked and sucked in more ways and in more positions than I could have imagined. For almost a year, Evelyn schooled me in the fine arts of love and sex, and I explored every nook and cranny of her lovely body. Later, she said that I not only matriculated in her college of love but graduated magna cum laude. I responded that I graduated magna cum cum!

About a year after Evelyn and I first made love, Mr. D died. He left much of his estate to charity but also provided well for Evelyn. The mansion and its furniture and furnishings, a large chunk of stock, and several million dollars were bequeathed to her. In addition, she was made the lifetime income beneficiary of a monstrous trust. During the administration of the estate, Evelyn fell in love with the attorney who was handling it and the trust. She married the man, sold the mansion and moved to New York as a dutiful wife. We corresponded for awhile, then exchanged cards at holidays, and ultimately lost touch. We both were living busy lives.

Because of Evelyn, I became an accomplished, patient and sensitive lover. Because of her, I learned many of the nuances of sex. Hopefully, I’m still learning. Over the course of many years, I have made love to many women. If I pleased them, Evelyn was at least partially responsible. Many times, as I lay between a woman’s legs after having turned her inside out with my tongue, hands and cock, I silently and fervently thought, “Thank you, Evelyn!”

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