Mother, May I part I

"Sorry, Mrs. K, er, ah, I was looking for Joe."

She was my best friend's mother and I came across her tanning, stomach down with the her two piece top straps undone. Their yard was surrounded by a seven foot tall wooden fence. I always came around the back and knocked on Joe's bedroom window.

"No need to be so shy, Jack. I used to change your diapers."

And she had, being my mom's best friend since moving to our little cul-de-sac heaven, three split-level ranch homes, the architectural embodiment of the sixties. Her house was the western most, mine was the eastern most, and the Rippington's sat in-between.

"Is Joe home?" I looked up and around, anywhere but down in her direction. She was a second generation Italian beauty with olive skin and a stout fleshy body. I felt my face turning flush as I tried to bury thoughts of her naked. If she only knew how many times I had masturbated to her squat, lithe vision.

"So you only like me when I make spinach ravioli?" She craned her head up from her chaise lounge, careful to ensure her untied top stayed put and put her glasses on.

" You know I love your cooking, Mrs. K." I have spent a lifetime trying to find an Italian restaurant to match the culinary magnificence of her spinach ravioli. She made everything from scratch, part of the last generation of stay-at-home moms, and my teen-aged cock longed to find its way home between her fecund thighs.

"Maybe you could help me make the sauce and pasta one of these days before you run off to college."

"Gee, Mrs. K, I don't know, sounds like something my s****r should do."

"What, a boy can't cook? Take a look at can of Chef Boyardee? Does he look like girl?"

"Come on, Mrs. K, you know what I mean." She loved to challenge me and Joe. I'd call it thinking outside of the box, but that phrase makes me puke.

"Joe went to the hardware store."

"Geez I forget, the rocket..." I slapped my hand over my mouth.

"What?" She lifted her body up in a jolt, forgetting to hold onto her top. I stood with my eyes wide open staring at her D-cup, fresh Italian breasts. Joe had made a solemn pledge to abandon his pursuit of crafting rockets, the last flight going terribly wrong from the start. We made the mistake of launching from the middle of our cul-de-sac street. The rocket took off on a low, sideways trajectory directly into and through the Rippington's front window.

"We weren't going to launch it anywhere close."

"It's just that Sylvia can be such a b-i-t-c-h." She started to cry. Sylvia being Mrs. Rippington, a little piece of Hades rooted in our cul-de-sac Shangri-La. It was a time when bad words were still spelled, not said. She seemed to have been unaware that she was now sitting up topless. I thought about turning around and running away, but it was the first time I had seen a grown woman's nipples in the flesh. They were a beautiful union of pink and brown and erect. I sensed that the cause of her crying was something other than Mrs. Rippington being a b-i-t-c-h.

"I swear on a stack of bibles that I'll talk Joe out of it." I could feel my cock getting bone hard and thick.

"It's more than that." She sobbed. I didn't know what else to do, so I took off my t-shirt and offered it to her to wipe the tears away.

"Oh, Jack, you're such a sweet young man." She took it and dabbed her cheeks."Sit down." She patted the empty space on her lounge and I did. I was left in cut-offs and sneakers without socks.

"What else, Mrs. K?" I wanted to know. I mean, she was like a mother to me. She put one arm around me and the side of her breast nuzzled into my chest.

"It's Herman," she whispered. Her husband, an ebullient man, always with a story to tell, or a recommendation for a book to read, or the latest theory on where UFO's really came from. He was a salesman and on the road more often than not. "He's having an affair." I was old enough to know what those words meant, but not old enough to know how to render solace for them.

"Gosh, Mrs. K, that's um, er, bad."

"Look at me, sweetie. Do you think I'm fat?" She turned her body to me, her breasts literally took my breath away, I couldn't imagine wanting anything else in a woman, ever, and can't to this day.

"You're beautiful, Mrs. K, I mean, I, well, you know, I, ah..." I couldn't believe that I was sitting with my best friend's half naked mom.

"You what?" She looked at me with tear-swollen brown eyes.

"I, um, think about you and play with myself, you know?"

"Oh my sweet Jacky boy." She smiled. I smiled to see her feeling better. "Show me how you do it, Jack" Her smile gone, she looked into my eyes at the same time as her hands fumbled with the top button of my cut-offs.

"Don't you think that would be a sin?" I was sweating, besides the fact that Joe might walk through gate to see his mother reaching for my tool.

"Do you think this is a sin, Jack?" She took my hand and placed it over her naked breast, I cupped it feeling so many things, but sin was not one of them.

"No, I think it is the most beautiful breast that I have ever seen." I pushed my jean shorts down and then my jockeys. My gaunt prick stood rigid and gleamed with pre-cum.

"Oh my, Jacky boy, you have done a lot of growing since I changed your diapers, but to tell you the truth, even then your little cock would always be hard for me."

"Really?" I squeaked although my voice had changed long before that day.

"Would you like some help?" She knelt down before I could answer and took my fledgling cock in her mouth.

"Oh my god, Mrs. K, that feels so good." I watched her head bob up and down, my shaft feeling the liquid pressure of her tongue and her lips. She angled her face up, her glasses still on, my dear Mrs. K, and slurped the raging purple mushroom head.

"Why Jacky boy, I think you like this more than my spinach ravioli." She managed to talk and suck at the same time. I just shook my head, unable to articulate one single thought, my cock lost in her mouth, her tongue, her brown eyes, my mother's best friend.

"Mrs. K, I am going to explode." I was matching orgasm to rocketry, not knowing the simple action verb of cum.

"MMMM." She hummed and just as I was ready to let go, she took my cock out and let it spray over her full pendulous breasts.

"Oh my god, Mrs. K, I am so sorry." I didn't know what else to say. I felt as if I had spat at her.

"Sorry for what, dear." She said as she played with my sperm and rubbed it into her skin as if it were more lotion.

"Joe's going to be back soon."

"So?" She said.

"Well shouldn't we get dressed?" I reached for my jockeys.

"Oh Jack, you've so much to learn." Just then Joe came into the yard. "Look who's here," she said.

Joe held a bag behind his back, but didn't change his expression. Joe was a genius of sorts and seeing his best friend naked next to his topless mom didn't seem to register in his ethereal mind as anything odd. He didn't say a word until he turned four when he began speaking in simple complete sentences. The doctors had thought he was autistic, but I think he was waiting until he could articulate complete thoughts.

"You've been a naughty young man, Joey." His mother wagged her finger at him. "Another rocket I hear." She looked over at me as she spoke.

"Sorry." Joe pulled the bag from behind his back. "I've got all the parts for a miniature launch tower, like Project Apollo."

I stood there naked except for my sneakers. Mrs. K had my jockeys in one hand and indicated that Joe turn over the bag of parts to her.

"If you want your precious parts back, you're going to have play the game."

"Geez, mom, really?" Joe started taking off his clothes like he knew what was coming.

"A game?" I said.

"Mother may I, with a real mother." Mrs. K positively beamed.

"Like scissor steps and stuff like that?" I was totally confused.

"Don't be such a moron." Joe said.

"You're the douche bag who put the rocket through the riptard's window, not me."

"Now boys, behave yourselves. You simply have to ask what steps that you could take with me." She propped up the chaise lounge and sat down like Cleopatra and looked as good as Liz Taylor in her bountiful days."And Jacky take off your shoes, you look so silly with them on."

Now Joe had indicated to me a few times that his mother was different from other moms and I had noticed how she kissed him good-bye or touched him over the years, and, besides building rockets, we had been jacking-off together regularly to a quality stash of porn that we had discovered in the Rippington's garbage while scavenging for parts. I'll be honest, we enjoyed stroking each other's cocks, and slapping them together in little sword fights. That was the real purpose of my visit that day, I was hoping for a nice little jack session. But the thing is, we never really talked about what we did, we just did it.

"You start, Joey, Jack will learn as we go along."

"Mother may I take off your bottoms?"

"No you may not, but you may rub your cute prick against my right nipple." Joe's cock was a little longer than mine, but not quite as thick. He did as he was told, getting stiff by the third circle he traced over her nipple.

"Your turn, Jacky."

"Mother may I take off your bottoms?" I figured she'd say no again and that I'd get to cop a feel, either way my dick was hard again.

"Yes you may, but you must do it with your mouth." She put her feet up on the edge of the chaise. I gulped and Joe pushed me forward.

"It's best if you work all around the edges pulling a little bit each time." He said. I supposed he had done it before or had quickly figured out the amount of f***e and torque needed to overcome the weight of his mother's round ass.
I knelt down and did as he said, nibbling at bits of fabric, inhaling the scent of tanning lotion, ass, quim, and skin. My tongue falling against her trim pubic mound and getting a hair or two in my mouth. Mrs. K was more than cooperative, lifting her butt and urging me on. Once I had pulled it down past her hips, it was an easy trip across thighs, legs, and back over her feet.

"Well done, Jacky boy."

"But,how do you win?" I said. It was a game after all.

"It's esoteric." Joe jumped in.

"Geez Joe, I don't have my dictionary handy!"

"Darling, it's not who wins or loses, it's how you play the game." With that Mrs. K reached up and took my face in her hands and pushed me down to her pussy. "Mother says eat me!"

"Hey,it was my turn."

"Mother makes the rules, come close so I can give you my special kiss." Joe strutted by me and placed his long, thin tool in his mom's open mouth as I discovered the juicy taste of her wet, puffy core.

"Lick my clitoris gently." She spread her lips and guided my mouth to her pert little bud peeking out. "Now faster," she urged with Joe's dick in her mouth, pushing her hips into my face and swiveling to the rhythm established by my tongue. If only Mrs. Rippington could see the three of us, I thought. A thought that was weirdly timed to the side gate's open and shut clack.

"Oh Sophia!" Sophia was Mrs. K's unspeakable first name, unspeakable for me that is.

"Hi, Mrs. Rippington." Joe said it as if he were passing her on the way to the mail box, instead of standing there naked with his pecker in his mother's mouth... to be continued

92% (31/3)
Categories: First TimeMatureTaboo
Posted by jackevermore
2 years ago    Views: 3,381
Comments (11)
Reply for:
Reply text
Please login or register to post comments.
4 months ago
dont go away with the thought that mother stories are all fantasies small fur,
this is a story that just could be true but I do know of cases of reality, belive me.
well done jack evermore! good start
1 year ago
Man you hit a weak spot in me with this story. This type of story is my FAVORITE!
1 year ago
Man that is a weak spot for me. Stories like this are my FAVORITE!
1 year ago
Mother fantasies are just that - fantasies. But the goal of a good fantasy is to make it as real as possible. Mother, May I uses two layers of role playing to bring me into this story. I could have been there.
2 years ago
finish the story I need to cummmm
2 years ago
part 2 please!
2 years ago
very good
2 years ago
more please
2 years ago
next part please?
2 years ago
More ~ pls
2 years ago
great start will there me more?