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May December Lessons In Love

May December Lessons In Love

by slimlong9
20 min read
4.66 (9000 views)
adultfiction

May/December - Lessons In Love

A wealthy, longtime, acquaintance had recently divorced. One evening I ran into her at a local coffee shop and struck up a conversation. She revealed that she was nervous about getting into the dating scene. It had been almost 25 years since she had dated anyone other than her ex-husband. Her two daughters were now in college and she had a huge home, that was soon to be empty. She said that she did not know where to start and that she really needed to fill the void with a companion.

I asked her if she had any preferences in men. To which she replied, "I just want to have fun with no strings attached."

To that I offered to write a story about one way that she could solve her dilemma. She gave me her e-mail address and I began writing.

This is that story. It was written over a months' time with each part sent separately when it was completed. For this first publication I gathered the parts together.

As a new contributor to this site, I'd appreciate any thoughts or constructive recommendations you have about it.

Whoever heard of an 18-year-old having a gut-wrenching orgasm they would remember over 40 years later? I have, that is who.

She was what my dad called a "country clubber". Her house was located along the golf course. It was big and fancy with a bluegrass yard, manicured shrubs and a huge, elevated patio that looked over the backyard and into the water hazard on the sixth hole. She had two college age daughters, two Cadillacs and an executive husband that never seemed to see me when I was there.

The summer of my graduation from high school, she hired me to do her yardening... or at least that is what I thought. The job was simple. Every Saturday morning when I reported for work, she gave me instructions then left to do her shopping and other chores. My jobs were trimming, weeding, painting fence and such. She would always return around noon to feed me lunch. The afternoons were then spent mowing. I pushed the Lawnboy to trim along the fence and shrubs. She rode her Snapper.

Although she had a nice body and a pretty face, for her age.... Those two college girls of hers really caught my attention. I tried all sorts of things to get a peek at them. Their cars were parked in the circle drive, out front. Most days, between 9 and 10 o-clock, one of them would come prancing out the front door and walk up to the road to get the mail. Soon after, they went shopping or someplace else with their friends. At any rate, I always managed to do the front yard chores at about that time.

One Saturday morning, three other gorgeous coeds arrived at about 10 o-clock. I was trimming the wisteria when they pulled up. They piled out of their convertible amid giggles and laughter. Each carried a beach bag and wore short shorts and a tank top. I almost trimmed my thumb. They walked right in front of me and went inside through the front door without even looking my way. That got my curiosity and my prick UP!

The next half hour was maddening as I struggled with figuring out what they were up to. I stayed around the front. I set to trimming shrubs and digging dandelions in view of the front door. Were they going down to the country club to go swimming? Would they be leaving soon or would it be afternoon before they re-appeared? I didn't have much more to do out front and the backyard list wasn't getting any shorter. Then I heard them.

Their girl talk drifted over from the back yard. When I walked around there, I saw them on the patio. Five college girls in bikinis more than beat my expectations. I had to think fast. Ah, yes, the Weedeater. I hauled the cords out to the sidewalk at the bottom of the patio steps, laid them there and went back for the Weedeater. There was a latticed privacy screen to hide the garden shed and trash toter from the patio. It was perfect for peeking at the girls without being seen. I stepped inside and turned to look. There they were.... pulling out lounge chairs. spreading out towels and setting up the radio. I drank it all in from my seclusion. I never realized how many times girls had to pick their bikinis out of their butts or reach down their bras and make adjustments. But, those were some of the sights I catalogued in my young mind. Then they laid down to tan.

The patio was elevated enough that I couldn't see them well from my vantage spot any more. So, I folded my hard prick out of the way, grabbed the Weedeater and headed toward the cords. It took some time to spread all the cords so, I caught glimpses of their gorgeous butts as they lay there, face down, on their loungers. They hadn't paid any attention to me so far and I was a little nervous at the thought of disturbing them. But, the only plug-in was on the patio and they were blocking my path to it. Steeling up my courage and once again adjusting my boner, I stepped up on the top step and cleared my throat. That got their attention immediately. All five looked at once.

Amid their giggling and stares, I don't remember what I said, but somehow the youngest daughter got my message and plugged the cord in. Her hand touched my finger as she grabbed the end of the cord from me. I tried not to stare as she walked away from me, toward the receptacle. The other girls had already looked away, so I was able to secretly watch her bikini-clad butt. Too short a time elapsed as she walked away, bent over and plugged it in.

Back to work. I started trimming along the sidewalk and worked my way away from the patio. As I did, it became increasingly difficult to see what was going on up there. The grass close to the patio was trimmed immaculately. The further away that I got, the less attention the grass got. Finally, I finished and laid the weed eater down. I needed to trim the front, but I wasn't about to start that as-long-as the show was out back. I grabbed the pruning shears and started trimming the bushes around the house. The view was fantastic as I worked my way around the circular patio. The girls chatted and paid no attention to me. One especially, caught my attention. She was laying on her back with her leg bent and knee up. I could see a hint of pubic hair peeking out at me. Her top had ridden up and a good deal of one breast was showing below the cup. I spent at least a half-hour on this 10-minute task.

Just as I finished, my boss drove up in front. When I heard the car door close, I knew I was running behind. I asked the girls to unplug the cord. In a frenzy, I drug the Weedeater around front and started trimming. By the time she unloaded her groceries and fixed lunch, I was almost done. She met me at the shed just as I was putting the cords away. My heart leapt, when she told me that lunch was on the patio. I wasn't sure that I could eat with that many gorgeous girls laying around in bikinis. But alas, I didn't have to worry. By the time I washed up in the bathroom off the garage, they had already gone back inside. I ate my lunch alone with my thoughts.

After lunch, she came out and we started mowing. I always liked the way she looked. Her busts were full and firm. Her legs toned and tanned. She liked to wear short button-up blouses, which tied above her midriff. She either went braless or wore a thin bra. Tight white tennis shorts completed her outfit. She had a pretty face, but her butt was definitely her best feature. It was clear where the two daughters got theirs from.

We mowed all afternoon. It was hot and humid. I was wet with sweat and so was she. I noticed on one occasion that her nipples were peeking through the sweat soaked material of her bright yellow blouse. The girls had left while I was eating lunch, so it was just her and me. A lot of possibilities ran through my juvenile mind.

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When we finished, she paid me and said, "I'll see you next Saturday."

I said I would be unavailable for our regular Saturday yardening. It was my older sister's wedding and the venue was a couple of hours drive upstate. I had been fretting about this conversation for a couple of reasons. There was of course the Job Security issue. But, more immediately, I'd miss my opportunity to "perve" on her daughters. She smiled and said that she understood how important a family wedding was. In the end, we decided on doing the yard on Thursday.

May/December (pt. 2)

Thursday, she was gone when I got there. I set about my job doing the standard trimming and weeding. All the time, I was grousing about how her daughters weren't there to feed my prurient interests. About 11 o-clock, she returned. A few minutes later a delivery truck brought her new Snapper riding mower. I helped the guy unload it and load the old one. It was bigger and a bit fancier than her old one. He showed her how to start it and do basic maintenance. She got on and started to mow before the guy even left. This mower was wider and mowed a lot faster than her old one. I almost had to run with the push mower to keep trim-mowing ahead of her.

We never broke for lunch. I figured that she was so excited about getting a new mower, she just forgot. So, I just kept working. The pace of work, coupled with only five days since the last yardening, meant that we were finished by 2 o-clock. She shut the mower off outside the garage and went in to get us a drink. Meanwhile I cleaned the grass out from under the mower deck.

As we drank the lemonade, I couldn't help notice that she was staring at me. I averted my eyes to the yard and remarked how nice the new mower worked. She said, "Yes, it does and so do you."

I blushed.

She took my empty glass and disappeared inside. I put the mowers and tools away and went inside the mudroom to use the guest bathroom. When I came out of the door, I met her head-on. She asked me if I would mind coming inside to move some furniture. I told her I was too dirty and sweaty to walk across her carpeting. She looked down at my grass covered legs and pointed behind me at the shower. I started to object, because I didn't have any clothes but remembered that I had a t-shirt and cutoffs in my pickup. I'd have to go raw dog without my underwear but, I told her, "OK." She nodded and said she would be back down after she also showered.

It didn't take long and I was dressed and sitting on the patio when she came out. She asked me to come in and help her move a chest. As I followed her to her bedroom, I couldn't help but notice her butt. It was exceptionally fine in the tight cut-off white denim shorts she had put on. Once there, I grabbed one handle, she grabbed the other. As she bent over, her cleavage showed. She paid no attention. But, I did. Her deeply tanned breasts poured over the top of her low-cut cotton blouse. Her deep cleavage showed that she wasn't wearing a bra. A hint of her areolas showed above the neckline.

To this point in my life, my real-life experiences with breasts were confined to glimpses of my older sisters A-cup tits and the few times that my prudish ex-girlfriend had let me cop a quick feel at the drive-in theatre or in the dark front seat of my pickup. At 18, going on 19, I believed that I was the oldest virgin on planet Earth!

I was frozen, mesmerized by her ample breasts, when she looked up, smiled and asked me how the wedding went. I stuttered and stammered as I told her it was great.

She then asked me to lift the end of the bed so she could reposition the rug. As I lifted it, she bent over and flashed her breasts at me again. This time, she looked up, stared me straight in my eyes and asked me, "Do you like them?

May/December (pt. 3)

That caught me by surprise. The bed slipped from my hands and dropped the few inches onto the rug. I didn't know whether to try to deny that I was looking or tell her the truth. She recognized my quandary and answered for me. One restraining button unfastened, a quick tug on the tied shirt tails and her blouse fell open. I was standing there looking at the fully developed breasts of a woman old enough to be my mother and it had me speechless. They were perfect. They didn't sag. The tan line came just above her areolas. They were huge. Bigger than a silver dollar but smaller than a Coke can. Their dark brown shade contrasted mightily against the milky white globes within her tan lines. They held two nipples that were about the size of my little fingertip and hard as erasers. My cock became a chubby.

She walked over and sat me down on the chest. I watched as she slipped the blouse off and began rubbing her titties with both hands. She then pinched the nipples and locked eyes on me to see what I would do. My hands rose, on their own, to touch them. Her hands uncupped and laid them in my shaking hands. They felt marvelous. So firm, so soft, so smooth and the areolas were textured with numerous bumps and freckles. None of my few, previous sights, or touches could hold a candle to this. My chubby became a woody on an instant!

She stepped closer and I leaned forward. I just had to nurse! My lips went straight for the first nipple. As my lips pulled it in, the primal experience from being a breast-fed baby tool over. The urge to suck closed out awareness of all surroundings. The nipple was absolutely succulent.

It was a good while before I realized there were two of them and one was being unused. So, I repositioned my hands. My needy tongue and lips then moved to the neglected nipple.

I was enthralled with sucking the nipples but the urge to lick the areolas took over. They felt and tasted wonderful as I slathered them both with my tongue. I was salivating like a puppy looking at a Milkbone. Her chest was heaving as her breath deepened. My woody was now solid oak and sawing against the raw teeth of my zipper.

With all the visual, tactile and lust clouded sensations, I almost didn't notice her bending down.... I just adjusted my position to accommodate her. Then I felt her hand rub my crotch. The first touch felt like a casual brush, but the second time was clearly intentional. She swayed her chest back and forth to direct each breast to my mouth and continued running her hand up and down my blue steel hardened pole through my shorts.

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We continued this heavy petting for a few minutes more. Then, she stood up.

I watched in awe as she pulled me to my feet and reached to unbutton my shorts. Without unzipping the fly, she slipped my shorts down. I almost came when the relief from pressure and chewing zipper teeth hit my throbbing dick. I remember thinking, "This can't be real.... Don't blink or you'll wake up."

She grabbed it with her hand and led me to the bed. When I sat down, she stepped back. Her shorts slipped down her hips in one smooth motion, leaving only her panties to block my view. Her thin yellow panties were almost shear from the wetness in her crotch. I couldn't move.... My conscious mind was registering its first glimpse of what I would someday learn to call, 'a perfect cameltoe'!

She aroused me from my stupor when she pushed me back on the bed, bent over and wet the head of my prick with her tongue. I couldn't take it anymore.and shot off like a rocket.

She wasn't prepared for it and blinked just in time to keep it out of her eye. But, she recovered quickly. Her head dropped down and she sucked the last couple of pulses down her throat. Her mouth and tongue felt unbelievable. I could feel my still stiff prick throb every time my blood pulsed through it. The view of her lips as they encircled the tip of my prick was a total turn on. The stringy cum dripping off her head was HOTT!

Even so, I was shocked. The circumstances had totally overtaken me. The prior brushes I had with my prudish ex-girlfriend had left me unsatisfied. Her two attempts at blow jobs were more hand jobs than mouth. They were also, quick and delivered in cramped, uncomfortable places. To this point in my life, I preferred masturbation to actual sex.

She raised her eyes and met mine. They weren't wide eyed in disgust, like my ex-girlfriend's had been. Rather, they were sort of squinted in, what I have now come to realize as, lusty concentration. The swelling never got a chance to recede.

As she peered at me, it slipped out of her lips. As my eyes met hers, she asked, "Is this your first time?'

I felt my face and neck flush, then stammered out, "YYYeeesss".

The embarrassment of admission was short lived as she nodded and sultrily whispered, "I'll teach you."

Before I could fully process what she said, I felt her hands come up my body in a breaststroke like motion as she reached for my chest. Once there, she started rubbing my nipples. I didn't even know I liked that, but she did. A little attention there had them so sensitive that they almost hurt.

She continued the lesson by bringing her ample chest up to my still hard dick. She rubbed her nipples back and forth and up and down along it. Because she was looking down at my dick, I couldn't see what was going on. But, her nipples were so hard, I could feel when they made contact.

Soon, she looked up at me. I watched as her hands left my chest and pushed her ample titties together making a cradle. With that, she stroked my member up and down slowly, making sure I felt every inch of each stroke. As I looked down to watch the tip poke in and out of her cleavage, her head dropped. I felt the tip of it go into her sucking mouth on every down stroke she made and pop out with a sucking sound on every up. The stirring in my loins started again.

She seemed to sense it was coming and raised up. "Not yet", she said as she wrapped her fingers around the base and squeezed hard. We lay there like that for a few seconds as she watched my eyes to make sure the impulse had passed. When she saw that it had, she let go.

My swimming head thought it heard her say, "Have you ever given a girl a blow job?" I must have been daydreaming. There was no way this prim, proper lady had said anything that nasty to me. Then she repeated, "Have you?"

I muttered "Nnno."

She said, "Time for your next lesson. Let me teach you how. Just follow along and I'll tell you what to do." She crawled up the bed until she was right next to my head. Patting the bed in front of her she said, "Sit right here."

As I sat up, she rolled over on her back with her head toward the headboard. Her breasts settled on either side of her chest with their hard nipples poking skyward. Her stout brown legs and tan lines framed her silky yellow panties. She had them slightly spread and I was taken aback by the creased mound between them. This was yet another new view for me, So, I stared her up and down for all it was worth.

She started her lesson with. "A lady likes you to start soft and slow. Go harder or faster only when I tell you to. But, first, help me take these off." She raised her butt off the bed and held the waistband of her panties with her fingertips. I resisted the impulse to rip them off her and tried my best to work them down with care. It was like watching a rising sun. At first there was the hint of sun rays as her little triangle of dark blonde pubic hair started to appear above the receding panty horizon. Next in view was a stretch of pink sky as the soft skin below came into view. Then the sun rose. Slowly it showed its head. A remarkable sight as (what I later learned was) her clitoris peeked out. Thus, followed a revelation of the full heavenly orb as her somewhat darker outer labia and cleft emerged. It was the most glorious sunrise I had ever seen! Even now, I love to get up early and watch the sun rise. It is such an impactful fleeting moment, filled with beauty and anticipation of what is to come.

I worked them off her legs and laid them beside me on the bed. She settled her rear back on the bed and said, "Watch closely." While her hands moved down and completely covered her crotch, her knees came up. Her legs spread and her hamstrings became taut. She removed one hand and rubbed her inner thighs. "A lady likes it when you start by kissing her here. Then you move up." She stroked her thighs slowly and purposely, showing me that you start away and end near.

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