In Praise of Older Women

never happened to me when growing up. Would have loved for a much older woman teaching me all about pleasing a woman.
 
Example 5. Jeanie Our Next-door Neighbour

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Our next door neighbour Jeanie lived in that same house on Willow Street since before I was born. She was mom’s emergency, go-to Lady. Mom would call Jeanie when she had to work late. If one of us kids got sick we spent the day at Jeanie’s house. When both mom and Jeanie were home thay religiously spent from 10 to 11 in the morning at our kitchen table drinking coffee and talking each other’s ears off. As mom’s greatest confidant she knew things like when Didi and Ida got their periods. And mom knew when Robert, Jeanie’s husband had an affair. They shared the stuff and meaning of each other’s lives.

Jeanie always dressed more formally than mom, skirts and blouses or summer dresses, that kind of thing. Mom was a sweatpants and sweatshirt kind of gal, so I naturally looked Jeanie up and down...up her skirt and down her blouse. I know she noticed and would give me arousing flashes whenever no one was watching. She would smile wickedly when I beatled off to the bathroom to toss one off. It became our own personal show and tell sport. It was thrilling to know that an older woman enjoyed exciting me and knowing that she made me masturbate constantly. One autumn morning just after I turned eighteen Jeanie popped through our front door. “Yoohoo! Anybody home? Hello…”

I of course was enjoying my alone time by wacking off on my bed. “Just a sec Jeanie,” I called out from my room. I slipped on my jeans and a t-shirt and scampered out to greet her. My cock was still rampant and a wet spot of precum stained a growing circle on my jeans, highlighting where my cock head was trapped sideways in my pants. Jeanie made no pretense at ignoring my stiff dick. She stared directly at it. “I see the truncheon is in play today.” My mom and her had discussed my cock, its size and how concerned mom was that I was going to masturbate myself into the luny bin. “God,” Didi had once remarked in front of mom and Jeanie. “I wish he’d just yank on his prick right out here in the open and free up the bathroom for the rest of us.” Jeanie was party to all that and more concerning my cock and my appetite. If something was on mom’s mind, she blurted it out to Jeanie.

Today, Jeanie smiled knowingly at my blatant display and approached me across the room. Something was different. I had known her all my life and sensed the shift. My instincts registered sex. “Just how many times a day do you masturbate Tommy? Your mom says you are always at yourself.”

“Well a few, well more than a few times, a lot actually. Like now that I’m alone today, I’ll jerk off, then grab a snack and get right back at it. All day long really.” I was laying it on because I hoped to encourage the palpable sexual tension. I aspired to some nasty sex with an older woman; a woman that I had fantasy fucked in every posible position and scenario.

“You know what Tommy “ she purred moving so close beside me that her right tit pressed into my arm and her tummy lay against my thigh. “I’d like to see you do it.”

“Jeanie?”

“I’d like to see you play with your cock and make it cum. It’s a bit of a thing with me. Something happened to me years and years ago with my older brother that keeps stirring within me, making me ache to recreate the image over and over and over.” she pressed herself against me more urgently.

“What happened Jeanie?”

“Let’s discuss that another time Thomas. I know that your mom will be out the entire day and I, well, I hope that you will…ACCOMODATE me… accomodate me till she gets home.” The palm of her left hand began to slide back and forth across my prick from my balls to the head.

“I would...I mean I will Jeanie...I will accommodate you all day long.”

“Promise. Promise Thomas that you will do whatever I say. I masturbate alot too and this is what I masturbate about. And, the boy in my mind is always you or my brother Ben. Promise me Thomas.”

“I promise Jeanie. I promise.”

“Okay Thomas you have to take off all your clothes. Strip naked.” I quickly flipped off my t-shirt but slowed before pulling down my jeans.”Aren’t you going to get undressed as well I asked.”

“Don’t ask questions Thomas or I’m out of here...I want you naked.” Down came my jeans and she took me by the hand and led me to the couch.” Sit and spread your legs and arms behind you so that I can see everything.” I did so and my prick stood up like a Hindi snake, greedily waving about for attention. She then nestled up beside me. She wore a tight black skirt and placed a leg over my knee. Her left arm she lay over the back of the couch. “Just watch Tommy, You promised to let me do whatever I like. That is a crucial part of my daydream.”

She smiled and bent my cock down till it touched the seat of the couch then she let go and it ‘boinged’ back up like a Jack-in-the-box. “Lovely, a stiff, young cock naked and at my control.
So do you want to fuck me with is Thomas? Stick me with this spear of yours?”

“Oh yes, Jeanie… so, so, much…”

“Good, my pussy is so wet for your cock Tommy.”

“You can’t touch it. Let me do everything.” She pushed the skin as far down as she could so that it felt like it was going to tear away from the head. “Does that hurt Tommy? Good. So when your cock looks like it’s going to cum, I can jam it down like that and the pain will stop you shooting your load.. What about this.” she yanked up pulling my skin up and over the head even my balls rose up high to about mid cock. I yelped and she smiled. “ See, I can pump your beautiful cock as quickly and as strong as I like. Then when I see you raise your ass off the couch or tighten your stomach muscles and start puffing like a steam engine. I can just push down hard, hard, hard to stop you. Watch.”

She began to really jerk me off fast and hard, just like I like it. I felt the cum boiling in my nuts. My hips rolled hungrily. Then, she slammed the skin of my prick down hard so that her fist pounded into my balls and the skin threatened to rip away from my cock head.

“Aaah,” I screamed and she held my prick stretched like that until I settled down. Then she started again jerking me off again, bringing me up the mountain once more. When she saw me about to blow, this time she yanked so hard on my cock that she pulled my ass high off the seat and my balls flattened out and rode up the underside of my shaft.

“That’s what I lust for Thomas, a horny young cock that wants to cum again and again, that can never get enough. I take you up and bring you back down...over and over...teasing...torturing until you are about to explode… then stopping it again….Mmmmm” After five or six of her trips up the mountain I began to beg.

“Oh, Please Jeanie… let me cum this time...I’ve gotta cum...Please.”

“Well, maybe. You see...That’s the thing...You don’t know which time I’ll let you cum. I’ll be watching you through it all… watching you and loving it...Then there’s a big surprise at the end. Jeanie, molested my cock in this fashion for a good hour...though it seemed like a day. Then she finally hammered my prick long and hard to an earthquaking orgasm. The trick of course was that when she did let me cum she continued pumping. Ironically, I now begged for her to stop. I writhed, twisted, yelled and squealed but she pumped away. I damn near passed out before she stopped stroking me. “My brother taught me to do that and I love it… every stage of it. Next time we get together you can do anything you want to my naked body...We’ll take turns. But, every other time I get to live out my ultimate fantasy with your beautiful truncheon.”

We then watched some TV. I was still naked and she toyed with my flaccid cock; rolling it, gently pinching it, petting, stretching it as we watched the show. Sooner than I would have predicted my cock began to stiffen. Jeanie giggled and sat up. She started once again to jerk me off. Then, slam, she stopped me and we did a full repeat of her cock edging game…complete with my begging her not to stop then pleading with her to quit.

Some of my exploits with Jeanie were epic from that day forward….


I dream of Jeanie!!
 
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