tagMatureWish I May, Wish I Might

Wish I May, Wish I Might

bySoftly©

Arthur Lambert and Mark Wheeler had been classmates since the first grade. Both sons of university professors, they lived a block apart, adjacent to the university, in what is known as the hill section of the city. Besides excelling as students, they were excellent athletes. To the consternation of their parents, they were successful at the scheming and plotting necessary to pull off pranks that might have gotten them thrown in jail, if they were caught.

Like the time they "borrowed" a cow from the university farm. It made the local paper when the cow was discovered wandering next to the stage of the local movie theater. Only Mrs. Wheeler figured out who did it, when she found cow dung on Mark's shoes. "You better clean these before your father sees them," is all she said.

In early January of their freshman year of high school, Art made this observation to Mark. "You know, I think I have all this boy/girl thing figured out. You know, why the girls in our class don't pay any attention to us. I also have an idea as to how it will play out, too. And, my friend, I have something else that is really hot for us to work on."

"Really, old great Sahib, fill me in on your wondrous observations."

"Have you noticed what grade the guys are in that the best looking girls of our class are dating?"

"Huh?"

"Well, have you? I'll tell you. Every last one of the nice looking freshman girls are dating either a junior or senior guy."

"Hmm, now that you mention it, your right."

"The way that I have got this figured is that the attraction of the older guys is that they have cars, and move with the older crowd, who have the best parties."

"So, you've got it all figured out, Dude?"

"Sort of. Here is the plan. We keep a book listing each good looking girl in school, freshmen, sophomore, and junior. Each girl will have a page on which we will record the name of the guys that she dates. Also, who, and how long, she goes steady with one. Girls that we have an interest in, we try to sit near, when they go to the movies to try to determine just how intimate they are with each guy. Anything we learn about a girl goes into the book.

By their senior year, the guys that they are dating will have graduated, gone away to college."

"So what?"

"Don't you see? A girl who has been really getting it on with a steady guy will suddenly have no steady, or anyone for that matter, to take her to the dances or parties."

"Golly, what do you propose, Einstein?"

"Fuck you. Get serious. How many dates have you had in the last month? None, right?"

"You got me there. Go ahead with your words of wisdom."

"Okay. First, when we are sophomores, we ask out the dateless senior girls that went steady for a couple years. If they will date us, even if their only motive is to have a warm body to escort them to a party or dance, we will be with a girl who has done a lot of heavy petting, and is used to drinking with the older crowd.. Failing that, we try the junior girls in the same fix."

"Whoo, Imagine having a date with Ellen Austin?"

"Speaking of Ellen, her brother told me that her boyfriend, Troy Burton, has a full football scholarship at South Carolina, so next fall she will be available, with luck, for some kissy-facing."

"Sounds good. We will see how it works out. It is going to be a long year until then. What is the other hot project?"

"Have you ever taken a good look at Mrs. Bowerman, the lady who lives next door to me in the yellow house?"

"Not really, no."

"I know a secret about her. I heard my folks talking a couple nights ago. Mrs. Bowerman is a drunk. You know, an alcoholic. Dad was telling Mom that he heard that she made a fool of herself at a frat party that she and her husband were supposed to be the chaperones of. According to Dad, her husband took her home when he found her in a hallway with two guys, who were taking liberties with her."

"How does that help us?"

"I clean her yard. The other day when I was talking to her, just before ten AM, I could smell whiskey on her breath. She had a robe on. She did not notice that it was part way open. I could see most of her tits. Her husband, Mr. Bowerman, is the regional manager for an insurance company. He is away every other week. That is why they have me take care of the yard, as well as clean their pool. With my driver's license, I can offer to take her shopping, or wherever she needs to go."

"What the hell are you talking about? Why doesn't she drive herself?"

"I used to ask myself the same thing, until Mom and Dad mentioned it the other night. Mom, said to Dad, "Her drinking explains why she does not drive her car anymore. She must be afraid of being picked up for DWI." If that is the case, I could get in thick with her, if I drive her around. Let's go to my house. If she is sunning herself by the pool, there may be something to see. I can see over their fence from the attic window.

Peeking from the window, Art handed Mark a pair of binoculars, he had just been looking through. "You can see the side of her tits, plus some pussy hair."

"Just your average lady. Bleached blonde, with nice legs. How old is this babe?"

"How the hell would I know."

"Watch her often?"

"I check to see if she is out on the sunny hot days. Hey, notice the milk glass filled with her drink. If that is booze, it is a lot."

"It's booze. I can see the bottle, as well as a small ice chest, under her lounge."

During the rest of the school year, the boys carefully observed the girls in the school. In addition, they asked the other members of the football team, as well as the members of the basketball team leading questions about the girls that they knew or dated. One night in particular, they received a gold mine of information. The Friday night after the last football of the year, Jimmy Barnes held a keg party at his father's hunting camp. Everyone agreed that if they came, that they would spend the night so that no one would get caught driving drunk.

In fact, there were three kegs. Everyone chipped in twenty bucks for the beer, steaks, and chips. It was a great party. Only the football guys were there. At one time, there were seven guys pissing off the rear deck. Jimmy told them to piss off the deck so that the septic system would not overflow.

Anyway, Mark said in a loud voice, "How many of these cocks have been in a real live pussy?"

Of the seven, four turned to wave their cocks at Mark. Troy, Ellen's boy friend, could be heard slurring out his pronouncement, "See this pretty cockee righty here. This baby gets used a lot in a nice warm pussy, let me tell you. Hmm, hmm, hmm ,hmm."

Before the night was over, Art and Mark had identified twelve guys who claimed that they were doing it with their girlfriends. Like the good students that they were, the boys agreed that some of the guys might be exaggerating how far they could go with their girlfriends, but at least it gave them some girls to investigate.

The next two years were uneventful. Both boys dated upper-class girls, but neither had any success getting into any girl's pants. Mark took Ellen Austin to the New Years Eve ball. Everyone was invited to an after-ball breakfast at Dawn Simpson's house, just three doors from Ellen's house. No pussy for Mark that night.

Art was now a regular visitor at the Bowerman's house. At first, he drove Mrs. To the grocery on Wednesdays. He would push her cart for her, as well as unload the groceries onto her kitchen table so that she could put them away. He hit a home run, when he remarked that he wished that he knew how to dance better. Mrs. Bowerman, who now insisted that he call her Jenny, lit right up. "I love to dance. I would love to teach you."

"Oh, great. I feel like such a dunce at the dances now."

"Oh, Art. You are such a good guy. The girls will be all over you when you get older."

From then on, Jenny got more and more relaxed with Art. She let her hair down in more ways then one. She danced with him a couple nights a week, when her husband was out of town. At first, he could not smell whiskey on her breath. But soon, he noticed that the odor was strong. Her coordination, on those nights, would be off, as was her speech. He got bolder and bolder using his hands and legs to grope her, or run his legs between hers. When he did, he would notice that a slight smile came across her lips. He knew that she knew what he was doing. She thought that it was cute. Art was not sure of himself enough to try to go all the way with her, at least not yet.

Mark reminded Art several times that all his planning wasn't worth dip-shit. But then, one night in February of their senior year, their luck changed. Boy did it. It was a Saturday night. Art noticed that the Bowermans were throwing a big party. There were a at least twenty cars in the street. Art could see guys in suits, and ladies in long dresses pass, by the windows, all of which were open to allow the breeze to blow through the house. The Bowermans did not realize that Art could see over their fence, into most of the rooms, from his attic.

Art saw a man and a woman walk to the end of the pool which was out of sight of the rear porch. Shit, he thought, that guy just lowered the top of her gown to play with her tits. Art phoned Mark. "Me. Get over here right away. I will leave the front door open. Folks are out. Come up to the attic. Something to see. Hurry."

"On my way."

By the time that Mark got there, the couple had returned to the inside of the house. As Mark softly padded over to the window, Art said dejectedly, "All over. Want a coke?"

"Sure."

"Be right back. Keep your eyes on the pool area."

When Art returned, Mark hissed at him, "Wow, come look at this. Isn't that Mrs. Bowerman?"

Art took up a second pair of binoculars. "Sure as shit is. Never seen the guy before."

As they watched, the guy was running his hands all over her. He lit up what appeared to be a cigarette. Then they saw that both were sharing it in a way that they had seen pot shared. Finished, he backed her near the tool shed. Then he picked up a lounge mat. Thinking they would be hidden from view, he placed it on the cement deck behind the shed. Hidden from the house? Yes. From the boys? No. They watched her being finger fucked. Then both gasped as he lie on her, with his ass rising and falling. When they finished, Mrs. Bowerman used her panties to clean her pussy. She left them laying there, when she and the guy returned to the house.

"Give me five man. That was something," Mark remarked. Art sat back to sip on his "Coke."

Ten minutes later, Mark stiffened. "Oh shit, here we go again."

Mrs. Bowerman, with a different man, was in the bedroom near the front of the house. They did not bother to turn the light off, another moment of good fortune for the boys. "Be right back," Art tossed over his shoulder, as he ran out of the attic.

Art returned in time, with his camcorder, to record over ten minutes of hot fucking. When the guy finished, he got dressed. She lie back on the bed naked. Both boys enjoyed studying her.

Spring break came. A Monday morning, Art mowed the Bowerman's lawn. When he finished, Jenny offered him a glass of milk, plus some "Fig Newton" cookies, which he gladly accepted. Art could smell the booze on her breath across the room.

"Art, could you drive me over to Centerville Arbors, just past the Centerville dam. I want to buy some flowers to plant around the house."

"Love to. My folks have gone to Raleigh to visit my relatives. How about stopping at the deli on the way. After you buy your flowers, we could stop at Welder State Park. I know a neat place in the ledges over the lake to have a picnic."

Jenny was turning towards the sink as he said that. She stopped to turn back to look at him. Their eyes met. For all of six seconds she stared at him. Those six seconds, Art would remember all his life. It was the six seconds, he knew, when a full grown woman made the decision that she would allow him to have sex with her. "So, young man, do you think that it is proper for a married woman to picnic in a secluded place with a much younger single guy, like your self?"

Boldly, Art responded. He knew that she was playing with him. "It all depends on what the woman wants to do with the young man, and where does she want it to happen, don't you think?"

Jenny's eyes never left his. "And just what do you think a married woman might want to happen if she was with a young guy, such as yourself?"

Art stepped forward to where he could put his arms around Jenny. He kissed her on the lips. For a moment, she tried to push him away. He backed her to the wall. His body pressed against her. Her arms went around his neck. She returned his kiss. He backed her to the stairs. Jenny took his hand, leading him up the stairs, into a bedroom.

Both naked, standing by the bed, Art thought that he would cum, when his cock brushed against her naked body as they kissed again. Art knew nothing of foreplay. It made no difference. She was wet and ready for him, as he slid onto her.

She guided his eager, throbbing cock to her waiting cunt. As it slid into her, she tossed her head back, closed her eyes, and let out the long sigh of a woman who knew the pleasure a young cock would give an older woman. She had fantasized about having sex with Art. She had pictured, in her mind, him on her several times, one right after another.

On night, dreaming of being with him, she woke up with her finger in her pussy, humping away. If all went as she planned, she would have an in-house "Boy-toy" to fuck her every night that her husband was away. It was all working out. Art was an accepted fixture at her house. A fact accepted by both his parents and her husband.

Eyes closed, she was in ecstasy as Art's cock probed in and out of her place of pleasure. He come, with several groans. His eager hands grasped, fondled, her generous bosoms, as many men before him had done. Now hard, his cock was inserted again in her. This time, she felt the tingle of an orgasm building in her pussy, spreading to her spine. Then, "Yes, yes, yes, Oohhooo, Yessss, Ohhooooo."

After the second go, she took his head in her hands, as she gave him instructions. "You clean up in the bathroom down the hall. I'll shower in here. Drive me to Centerville. After I buy my flowers, we can stop at the deli, and then have a picnic. That will be fun."

Seeing the frown on his face, she added, "We can do some more of this, too."

Shopping done, they drove to the park. Settled on a blanket on a slab of rock thirty-feet above the water both enjoyed the lemonade, grinder, pickles, and potato salad lunch.

It was a warm, cloudless day, with the wind blowing at thirteen knots out of the southwest. A boat could be seen, over three miles away, trolling slowly, probably for walleyes. Jenny lie on her back, arms up under her head, with her eyes closed. Art was on his side looking at her. She had on a yellow sun dress. Her hair was up in a bun. Her sandals were off, laying to the side of the blanket. A pine fragrance came from a nearby strand.

Without opening her eyes, Jenny said, matter-of-factly. "Come over here. Rub me."

"Okay."

Lying next to Jenny, Art ran his right hand the length of her left arm, then across her midriff.

Jenny let out a soft chuckle. She took his hand off her. Standing, she said, "This is more of what you had in mind, isn't it." With that, she slipped her dress over her head, to stand over him, completely naked. Again on her back, she took his hand, placing it on her pussy. "Play with that for a while." She closed her eyes.

Art, sans clothes, lie next to her. His mind was going bonkers. He wanted to feel her tits, and finger fuck her, but he could not do both at the same time. So, he concentrated on his index finger which her was slowly probing her cunt with. For Jenny, enough was enough. She wanted cock.

Jenny lifted her spread legs in the air, while pulling him to her.. On her, he slid forward. She reached under her right leg to use her hand to guide his cock to her hair-covered, wet entrance. With one push forward, Art was in. Her arms held him tightly to her. As a woman would, she wanted him to savor it. She whispered in his ear, "Art, Honey, go very, very slow. Feel how nice your cock feels as it slips in and out of me. Do it real, real, slow."

She held him, She tutored him. She used her pussy to tease him. Yet when he stiffened, cock about to spurt, she became a slut-whore, who loudly demanded in his ear, "fuck me, push, fuck me."

She let him fuck her again that afternoon.

Art filled Mark in on all the details that evening. The conversation ended with him telling Mark, "I'm sure that she will fuck you too, if we set it up right."

She ask Art to drive her to the mall two days later. Art wondered how she would react to him. This meeting with a woman whom you had been intimate with was all new ground for Art. It somewhat amazed him that as far as he could tell, she treated him exactly as she had when she first started to teach him to dance. Friendly, warm, yet with no sexual overtone. That was, until, he had finished unloading her purchases, and she had finished putting them away.

She asked, "your folks back from Raleigh as yet?"

"No, not until next Wednesday."

Jenny walked to him. She placed a leg on each side of his, as she ran her pussy up and down his leg. She kissed him full on the lips. Her hand slid up and down his now hard shaft. She took him by the hand, as she walked up the stairs to the bedroom where he had fucked her before. There was nothing slow and easy this time. They both wanted hard sex. "Oh, Oh, Oh, Ooohhoooo, harder," she pleaded as her orgasm built in her. Together they exploded.

Art talked Jenny into driving up to her camp in the mountains. By now, Art knew exactly what she drank. He had fixed her a milk glass full before they left.. He filled a flask for her to sip on during the twenty minute drive.

Just before they had left, Art phoned Mark, while Jenny was taking a pee, to tell him that it was a "go."

Once at the cabin, Art lit the fire, as Jenny sat sipping on yet another drink, this one two-thirds alcohol. She blinked her eyes, as her head rolled from side to side, as he took off her clothes. "I'm a little drunkee, I am," she said, as her head bobbed up and down. "Just a little drunkee."

"Oh, but you are a sexy woman, Jenny."

"If your going to fucky, fucky me, you have to eat me first," she said with drunken, slurred, speech, as she opened her legs. The fingers of each hand now held her pussy lips apart, showing her red slash, protruding clitoris, pee hole, over her love canal.

Art lapped her pussy from the bottom to the top, not knowing just what he was supposed to do. It made no difference. After the tenth lick, she pulled him over her, while softly demanding, "put it in me Artie. Fuck me." His cock slid into her with ease. This fucking stuff is everything he thought that it would be. In and out he moved his cock until it expanded, then blew his load.

Jenny Bowerman lie on her back, eyes closed, drunk, expecting to be fuck some more. Art got off the bed., walked to the door, opening it to allow Mark to enter. Before he entered the bedroom, he shed his clothes. When Jenny opened her eyes, she beheld two naked boys, one with a hard on. She raised herself to her elbows, while shaking her head to try to clear the drunken fog. "It seems that your friend, Marky is here, isn't he? You boys planning on Jenny doing you both, huh? I'll just have to think about that." Her eyes closed and opened slowly twice.

Art looked at Mark, as he motioned with his right index finger by thrusting it forward and back in the air, indication that Mark should stick his finger in Jenny to finger-fuck her.

Her legs were a foot apart. She did not try to close them when Mark's finger found her cunt. As he ran it hard into and out of her, Jenny's eyes opened. She took a deep breath, closed her eyes, as her head rolled to the side. Art opened her legs further. Then, Art played with her breasts, as Mark explored her pussy with his finger. Finally, `Art simply said, "fuck her. Take your time. She isn't going anywhere. I'm going to get a "Coke."

Report Story

bySoftly© 3 comments/ 330095 views/ 4 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel