“ Would you like to see the sights, or go on a picnic, or something?” he asked as he felt his cheeks flush red. He couldn’t believe he was saying this to this young girl.
“ Or something…?” she joked with him coyly. “ Sure, why not. I’ll meet you across the street a couple of minutes after twelve.”
“ See you then,” he said in amazement, and drove off.
Harold, or Harry to his friends, was a pretty normal middle-aged guy living in a small town in Nebraska. He had a family, a regular job at City Hall that didn’t bring him into the public’s eye, and a pretty wife named Diane that he’d been faithful to for the last twenty-one years of his life.
Harry never gave any thought to the idea of a mid-life crisis, yet he had recently bought a used little convertible and found his eye was straying to young women more frequently than it used to. Even then, when Diane and he got together with their neighbors and shared a bucket of margaritas on a Saturday night, they might kid around about a mid-life crisis, but really none of them even knew what a mid-life crisis was supposed to look like and couldn’t be bothered to look it up. It was worth joking about, but not taking seriously, until last Sunday that is.
Saturday night, Harry and Diane had stayed up with their neighbors, Trish and Dave, drinking margaritas a little later than usual. Toward the end of the evening when the margaritas were running low, Harry had brought out a twelve year old bottle of single malt whiskey and he and Dave had downed a stiff three fingers worth, not once, but twice, so when Sunday morning rolled around, Harry was in pretty bad shape. He woke up early with hot, red eyes and an acid gut that gave his whole being a smoky, burned electrical tinge. Stumbling into his clothes from the night before, he pulled a baseball hat on, put on his sunglasses, and trudged out to his convertible. He put the top down even though it was a little too brisk yet, and slowly drove off to buy the usual latte for Diane and black coffee with one sugar for himself.
Driving across the small country town, he wasn’t thinking much… just feeling sort of guilty about how much he had drunk and whether Diane was going to give him grief when he got home. Making the usual promises to himself to stop drinking so much, he pulled into the parking lot of the farm store where his regular coffee shop was located. One cool thing about driving a little sports car he thought to himself as he sped by signs for John Deere and Round Up, is the coffee girl has to lean way over to hand him the coffee, thus adding a beautiful shot of her cleavage to go with his order. Perfect! He wondered who it would be today as he pulled up under the window.
He was pleasantly surprised when a new girl came to the window. It was always hard to tell how tall a girl was when they were in the window above him, but this one seemed pretty short, albeit unbelievably striking. She was thin and paler than he usually cared for, but she had this amazing straw-like, fly away blonde hair that was almost white. She was wearing a tight dark blue tank top that was concealing what appeared to be beautifully full, yet small, melon like breasts. As they exchanged the usual pleasantries of good morning, his glance took in her shoulders and noticed there were no spaghetti straps from a bra. He immediately got a hard on and he scootched down in his seat a little to conceal himself.
After ordering the latte and black coffee, he hungrily watched her as she worked the machine. Fortunately, the ledge of the window was low enough that he could see she was wearing tight cut-off shorts that hugged a high, firm ass. He found himself wondering if she was wearing panties, since she didn’t seem to be wearing a bra, as he worked his wallet out of his pocket and noticed he had a few more twenties than he thought.
“So are you new here?” he asked, trying unsuccessfully to think of something interesting to say.
“Do you mean am I new to town, or new to the job? The answer to both would be, yes,” she replied as she put the caps on the coffee. “ I just moved here to go to school about a week ago, and today is only my second day on the job. I hope it picks up a little though. I was hoping this one job would be enough so I wouldn’t have to work two jobs, but I’m not too sure it’s going to work out. Do you want a carrier for the coffee?”
“No thanks,” Harry said and added, “ Well I hope it works out for you,” and held up a twenty for her. As she leaned over to exchange the coffee for the money, her long blonde hair fell over her shoulders, but with a gentle shake that rocked her cleavage and made the bulge in Harry’s pants even harder, she swung it over her shoulder. Harry’s hands brushed against her slim, long fingers as he took the coffee and an electrical tingle ran straight to his crotch.
“That’ll be six dollars,” she said as she straightened and made change in the drawer for him.
Thinking fast, Harry scanned the parking lot and pulled another twenty from his wallet. “ So the coffee business is a little slow, is it?” he asked with a hint of concern in his voice.
“Yeah,” she replied as she turned to him and stood for a minute to converse with him. “ As I said, I was hoping I would make enough in tips, but it’s not going too well so far.”
“ I have an idea,” said Harry. “ If you’ll lift your shirt and give me a quick peek I’ll let you keep the change and add another twenty,” he said with a smile and surprising calm as held up the twenty for her to see. Ready to speed off and hope he never saw her again if she didn’t go for it, he mentally kicked himself for just asking her that. What a fool he was!
Yet, to his astonishment, she quickly scanned the parking lot and seeing no one, said furtively, “ Okay,” and pulled up the front of her tee with both hands. Her breasts bobbed free and were glorious! They were perfectly round, full little orbs and tipped by the daintiest of dusky pink nipples standing proudly to attention in the cool morning air.
Harry moaned, “ Oh my god, you’re beautiful,” and she quickly slipped her shirt back down over her breasts. He handed her the twenty and the two of them held each other’s gaze in a strange air of part embarrassment, and part secret shared, that was tantalizing. “ Thank you,” Harry said quietly and putting the car in gear, continued with, “You have made my day!”
Blushing, she replied, “You’re welcome!” and, “Come again!” with a big smile.
The smiled at each other and Harry sped off, angels singing in his head as the sun shone down! “What a great day it is!” he thought as he sped home to where he hoped Diane was still in bed so he could ravage her.
Harry usually didn’t go to the coffee shack during the week, but this week he did. Unfortunately, the girl wasn’t there and his hopes flagged. Maybe she had been forced to get a different job after all.
Come Saturday though, there she was again, only this time there was a line of cars already in place when Harry pulled up. When it was Harry’s turn, they gave each other a big, knowing smile, and Harry asked how the job was turning out. She said it was getting better, and that unfortunately, today it didn’t appear he was going to be able to get his “desert” as she put it. He smiled at the entendre and holding up a twenty for a tip, brazenly asked when she got off work. Pausing for a minute to look at him, she replied hesitantly before replying twelve, noon.
“ Would you like to see the sights, or go on a picnic, or something?” he asked as he felt his cheeks flush red. He couldn’t believe he was saying this to this young girl.
“ Or something…?” she joked with him coyly. “ Sure, why not. I’ll meet you across the street a couple of minutes after twelve.”
“ See you then,” he said in amazement, and drove off.
“What the hell was he doing?” he thought as he slowly drove home. He was a happily married man who had just asked out a young college aged girl… and been accepted! He didn’t know whether to jump and down, shouting in joy, or hang his head in shame and go crawling to his wife to ask for forgiveness. It was killing him!
When he got home, Diane told him she was going to be out for the afternoon with her friends and if he wouldn’t mind, would he sort through his clothes so she could take his old ones to the donation store. Harry mumbled yes, of course, have fun, say hello for me, etc., as he walked around the house in a sort of detached daze.
A picnic he had said… what did that mean? A drive in the country and lunch? Where was he going to go, and what was he going to do for lunch? He mulled these problems over as he stood in his closet and absent-mindedly sorted through clothes, tossing those he didn’t want in a pile on the floor.
At ten, he took a shower and dressed in shorts, a tropical print shirt, and flip-flops. Combing what was left of his gray hair, he practiced sucking in his gut in front of the mirror.
At eleven, Diane was picked up by one of her friends. As soon as she left, Harry ran to the linen closet upstairs and ***********ed a large, soft blanket and a couple of old down pillows. Throwing those in the car, he put the top down and set off to do some shopping before he picked the girl up. He went to the next town over, hoping he wouldn’t run into anyone he knew, and went shopping at their local market first, buying things that seemed appropriate for a picnic. He bought sandwiches, fruit, and a bottle of wine.
Then he walked to the drug store next door. After furtively walking up and down the aisles, he found the condoms and picked out some ribbed ones that were lubricated. He noticed next to the condoms different jellies and creams so he picked a small “picnic” sized tube of a jellied lubricant. Trying to act like he did it all the time and it was no big deal, he sauntered up to the check out counter and laid the items before the young girl working there. Fortunately, she didn’t give it a second thought as she rang it up and made change for him. They must train them to not be surprised at what people buy he thought as he left the store. With sweaty palms, he was finally off to go pick up the girl.
Driving back to his town, he stopped and put the top up on his car. He didn’t want to run the risk of someone seeing her in his car. Then he stopped at the ATM and took out three hundred, just in case. With what he had in his wallet, that gave him a little over four hundred. Better prepared for anything than not, he thought.
Pulling up to the farm store, he saw her waiting across the parking lot, on the other side of the street as she had said. She was wearing another tank top, red this time, and what looked like the same cut off shorts. Like him, she was wearing flip-flops, and also like him she seemed a little nervous as she was chewing one of her nails while she looked up and down the street.
Harry drove through the parking lot, pulled across the street and stopped in front of her. Without getting out of the car, he leaned across and opened the door for her with a smile and said, “I’m glad you decided to make it. I was a little worried you wouldn’t.”
Sliding into the car, she replied with a grin, “I wouldn’t want to disappoint my biggest tipper!” and with that, she quickly flashed him! Laughing, she settled back in her seat and put on her seatbelt. “So, where are we off to?” she asked. “I haven’t had a chance to explore much, so this should be fun.”
Still reeling from seeing her pert boobs so suddenly and trying to control his hard on, thank god he had worn a loose shirt and shorts, Harry replied, “I thought I’d show you the country side and we could stop for a picnic. How’s that sound?”
“Sounds good to me, I’m starving,” she said.
Harry sped straight out of town, cautiously avoiding anyone he might know as he kept up a steady banter of questions for the girl. As it turned out she had just turned eighteen the month before and this was the first time she was away from home. She didn’t have a boyfriend at the moment, but she had had a pretty serious one for quite a while it sounded like. Her family was not particularly well off so this wasn’t the first job she’d had, and, her name was Penny.
Once out of town, Harry pulled over and put the top down. Back on the road, he indirectly drove to a secluded field of tall grass on the side of a hill that overlooked the town. Pulling off the road and driving down the fire trail of tall grass, he was so excited he hoped he wouldn’t have a heart attack!
Finally stopping, they both got out of the car. “Oh, this is beautiful,” Penny said. “Thank you for bringing me out here.”
“I like it, too,” Harry replied as he got the supplies and the blanket and pillows from the car. God he was lame at making idle chit-chat with her.
“Pillows?” she asked with a raised eyebrow as she helped him spread the blanket.
Giving her a cheesy smile, Harry quipped, “Doesn’t everyone take pillows with them when they go on a picnic?” and put the food on the blanket.
Standing beside the blanket, watching Harry nervously arrange the food, Penny said, “Listen Harry, we need to get something straight. You’re a nice guy and all, but if anything happens here, it’s going to cost you,” and with that, she pulled her shirt over her head and off and laid down on the blanket, settling one of the pillows under her head. “I’ve been thinking about it on the way up here, and twenty was good for you to look at them, but it’ll be forty if you want to touch, and two hundred if you want to go all the way. What do you say?” she asked as she looked at him and blocked the sun from her eyes with her arm.
With his cock raising his shorts like a tent-pole, Harry said, “Of course, I understand,” and pulled his wallet out of his shorts. Counting out two hundred, he said, “Put me down for all the way.”
Taking the money from him and putting it in her pocket, she said, “This is going to be a good relationship, Harry,” and she peeled off her shorts revealing pink panties. Sitting up and peeling those off, she then laid back and asked in a matter of fact tone, “What do you want me to do?”
Momentarily unable to speak as the blood rushed to his head, Harry took in her magnificent body laying on the blanket. Her firm, round breasts with their pointy little nipples… her flat, tone stomach. The soft patch of fuzz on her mound that was so light in color it was almost invisible. Her firm thighs and long slim legs… it was all like a miracle to Harry and it took him a moment before he said, “Don’t do anything,” and unbuttoned his shirt. Standing up, he undid his shorts, freeing his rigid pole.
Harry had always been a little proud of his cock. It measured a solid nine inches and was a good four inches or so around. Diane had always said it was the biggest she’d ever seen, but that didn’t mean much as she hadn’t been with too many men before they met.
Penny, on the other hand, said, “Oh my god Harry, you’re huge!” and that meant all the world to Harry. Still standing over her, he stroked his cock slowly while looking down on her and then in one motion he took his shirt off and knelt beside her.
He slid his left hand down her flat stomach and into the fuzz of her mound, while with his right he lightly felt the cool, firm roundness of her breasts. Kneading them a little, he bent over and lightly tickled her nipples with his tongue while his other hand slid between her now opened thighs and ran lightly up and down the moist folds of her lips. With one finger he spread her lips and slid in her tight hole, in and out, slowly.
“Mmm… you feel so good,” he sighed as he worked her faster between her legs. “I have to have you, I can’t wait,” and sitting up, he reached into his shorts and pulled out a condom.
“Oh Harry, you’ve thought of everything, haven’t you?” she said as she watched him roll the condom down his shaft.
When Harry crawled over and knelt between her thighs, she raised her hips to meet him. Guiding his cock between her legs, he first parted the folds of her swollen, wet lips with the head of his cock, then he slowly pushed into her tight, hot hole. “Yes!” she moaned as she rocked her head back and strained to meet the slow penetration of his massive cock. Slowly he slid in her until half way in, he held her by her slim hips and with two quick in and out thrusts, sank all the way in her until he could feel his head pushing against the wall of her womb while his balls ground tightly against the clenched cheeks of her buttocks.
“Oh my god, Penny,” he moaned as he held her hips tight against his grinding, stirring cock. “You feel so fucking good! I don’t know how much longer I can go…” he added as he lowered her hips to the blanket and started to pump her vigorously. Straining, he watched her tits jiggle and bounce as he jerked into her. Sliding her lithe young body slowly up the blanket with his thrusts until her long white hair tangled in the grass, he continued pounding between her legs, faster and faster until with a groan, he laid his sweaty body on her firm coolness. Squeezing her to him by her shoulders, he continued with quick, rabbit like thrusts. Suddenly arching though, while still straining to grind as deep into her young body as he could, he gasped, and came in her. Shuddering, he pumped her hard, once, twice, then again, slamming his hips into her as his seed drained him, leaving him tired and sweaty. Spent, he laid on her, momentarily burying her under his weight.
Rolling off her he covered his eyes with his forearm and said, “Penny, you’re a goddess.”
Sitting up, Penny replied, “You’re not too bad yourself, Harry, but that was pretty quick,” and she reached over him for a handful of grapes. Laying back down, she plopped them one at a time into her mouth. “We’ll have to work on that in the future.” Turning his head to watch her, Harry was a little embarrassed to feel himself becoming aroused again.
“Listen Penny,” he said, still watching her, “since this seems to be a pay as you go relationship, which is great by the way, I want to ask a favor of you…”
“Sure, what is it?” she asked as she continued to look at the sky and eat grapes.
“Can I do it to you in the… the… you know… Greek style? My wife has never let me do it that way with her and I’ve always wondered what, if anything, I’m missing.”
Penny paused a moment, and turning to look at Harry said, “Sure Harry, but you’ll have to be gentle. Oh, and it’ll cost you three hundred, not two.”
“I can do that Penny, but I only have about another two fifty on me, is that okay?”
“That’ll work. Now I’ve never done it this way either, so what do you want me to do?”
Feeling himself at full, raging hard on status, Harry stripped off the used condom and said, “Well why don’t you lie on your stomach. I brought some lubricant and we can go from there. Here,” he said rolling up one of the pillows and sliding it under her hips so now her slim, hard buttocks were held in the air, “let’s try this.”
“Try that oil, would you Harry? As I said, this is new for me too and I don’t want to get hurt,” Penny said as she reached under her with one hand to play with her clit a little. “Oh, and I don’t think I’m going to get pregnant doing it this way so don’t use the condom would you? I think those rib things might wind up hurting a little.”
Going through his shorts again, Harry pulled out the little tube of jelly and squirted some in his palm. Stroking it onto his rock hard, throbbing cock with one hand, with the other he liberally squirted it over her tightly puckered pink little hole. Letting himself go, he worked the jelly into her buttocks by massaging one with each of his hands. Continuing the massaging motion, he worked his thumbs toward her hole and with a rubbing motion, pressed one of his thumbs against her until she relaxed enough and his thumb momentarily slid in.
“Oh… Harry,” Penny moaned as she stopped playing with herself and reached out to grab a fistful of grass with each of her hands, “just go ahead and do it!”
Paying heed to her command, Harry stopped fingering her ass and sidling forward on his knees so his thighs were spreading hers outward, Harry positioned himself above her. Holding himself steady with one hand, he propped himself up with his other and lowered his hips until the head of his fat cock was lined up and pressing against her tight little hole. Pressing down into her, her hole wouldn’t give as he pushed her hips down, until with an almost audible pop and a gasp from Penny, her hole stretched open under the force of his pressure and in slipped the head of his cock.
The tensed pressure of her lips around him was fantastic! Slowly, he pushed deeper inside her incredibly tight hole as she groaned and then bit the blanket to keep from calling out. Clenching the grass until her hands were white from pressure, her whole body was rock hard rigid as Harry continued to push his cock deeper in her ass.
Finally, putting all his weight into driving his cock deep, with a final thrust he pushed her down into the rolled pillow, his hips flattening her buttocks as he buried his shaft balls deep in her. Grinding, stirring his cock inside her, he paused, and pulling out enough to adjust his legs, straddled her between his thighs. Settled, he dropped back into her like a rock, bringing a short, stifled grunt from her before he began to pump away at her ass. Using his legs, he thrust his full nine inches into her only to pull out so his head was visibly stretching her hole back up, then down again he would plunge, fucking her deep into the pillow. Working up a sweat as his hips rhythmically slapped into her ass cheeks, he put his hands on her shoulders to get a better angle for his thrusting cock. Leaning into her, he pressed her slight frame down into the blanket as he drove furiously at her ass, shaking her with each slam home.
From a distance, all that could be heard were the grunts of Harry and the slap, slap, slap of his fucking her ass.
This went on for some time until tiring, Harry went down on his knees and releasing the pressure on her back with one hand, wrapped her hair around his fist and used her hair like a bridle to pull her back into his wildly bucking, ravaging hips. Gasping with each thrust, Penny started to moan and groan, and finally, between the strokes of his plunging of his cock in her ass, she gasped in syllables “Har..ry..stop..it’s..too..much!..please!”
Ignoring her for a moment, Harry, drove only harder, whispering to her as the sweat rolled off him, “I’m almost there!” Releasing her hair, he grabbed her by the hips and started to slam furiously into her. There was no rhythm or gentlemanliness about him as rode her hard, tearing into her, pressing her hard into the grassy field one moment, only to suddenly rear up as he shook her frame with his powerful thrusts the next. He was truly lost in the savagery of the moment as he used her like a doll, her hair flailing from side to side, her breasts snapping up and down, until with one final jerk, driving her young body skyward like a sacrifice, he pulled her tight against him and pumped his seed down his grinding, throbbing cock, deep inside her ass. Pumping again and again, his cum spewed into her until finally spent, Harry relaxed and they both fell to the blanket. Harry pulled out and kissing her on the shoulder, rolled onto his back on the blanket.
“Oh my god Harry,” Penny said as she too rolled on her back, “that was incredible. I never thought a girl could enjoy doing it that way, but it was amazing.
I’m so glad I met you. If we meet and do this once or twice a month, I won’t have to work at another job.”
“I loved it too, Penny, but I don’t know if I’m going to be able to afford it. I just work for the city and I don’t think I’ll be able to spend so much without my wife noticing. I know for a fact I won’t.”
“Oh, that’s too bad Harry. You have any friends you can introduce me too?” she asked with a smile.