Adult-FanFiction.org : Television / Streaming

The Wonder Years - Country Club Cutie	By : Tricky_Dick Category: -Misc TV Shows > Het - Male/Female Views: 107 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own The Wonder Years, nor do I make any money from this completely fictional story. I don't know Danica McKellar or anyone else in the Wonder Years cast.

Chapter List
- 2
- 3
They were jarred away by the alarm clock. Winnie got up and went to the bathroom. She quickly got dressed and went to leave but not before Ryan got a goodbye kiss. “I’ll see you later.” He said. Winnie smiled at him. “You were perfect.” She said. Ryan was overwhelmed and watched her scurry back to the dorms to shower and change before any noticed. Of course it didn’t matter. People saw them walking to dinner. They knew she didn’t come home and a couple people saw her doing the walk of shame. When she showed up at the pool Eric was cold to her. Winnie said virtually nothing. They just did their jobs.
All of a sudden, “Gwendolyn Cooper please report to the main office. Gwendolyn Cooper, please report to the main office.” Over the loudspeaker. Winnie looked at Eric. “Am I in trouble?” she asked. Eric shook his head. “I don’t know. I’ll cover for you…. Go and see what’s up.” He said. Winnie was scared. She was really worried that somehow she was in trouble.
At the main office the secretary buzzed the Country Club Manager that “Gwendolyn Cooper is here to see you sir.” “Excellent…. Send her in.” came the man’s voice. Winnie nervously entered the office. A man with dark hair and hazel eyes stood up and greeted the teen. “Gwendolyn… well I guess everyone calls you Winnie right?” he said. “Yes sir.” She said. “I am Richard Morris and I’m the manager of this country club.” He said. He extended his hand and Winnie shook it gently. “Am I in trouble?” Winnie quietly asked. “Absolutely not… quite the opposite.” The man said. “Please sit down.” Winnie sat in this big comfy chair and Richard moved next to her in the other chair so he could sit close to her. “Winnie… You’re very popular here at the club. Your escapades have not gone unnoticed. Your boyfriend shows up and you get him a job. He caught you kissing another guy and apparently you broke up with him?” he offered. Winnie was shocked. “How…. How do you know about that?” she exclaimed. “Winnie there is nothing that goes on in my club that I don’t know about…. Like Eric’s little campsite in the woods and what he does there with co-workers and sometimes guests.” He continued. Winnie’s eyes went wide with shock. “And apparently you visited with him out there…. Correct?” he asked. Winnie throat went dry and she nodded. “And everything that happened was completely consensual?” he asked. Winnie nodded, “Yes sir.” “And then something happened and you broke things off with him.” He continued. “Uh…. Yes… well it’s complicated.” Winnie offered still stunned to find out that the club manager was aware of her personal affairs. “I understand you had dinner with my Front Desk Manager Ryan last night.” He again offered. Winnie swallowed again and nodded. “And you spent the night in his room.” He continued. Winnie started to panic and her lip started to quiver. She was about to cry. “Winnie…. You’re not in trouble. Everything is fine.” He said. Winnie looked around and down and then finally back up at him. The man just smiled at her. “I’m assuming that your evening was well spent?” he asked. Winne’s heart was pounding… she nodded again. “Excellent…. Then allow me to get down to the point.
Richard scooted right up to Winnie so that their knees with nearly touching. “I’d like to offer you a promotion.” He stated. Winnie stared at him for a moment. “I’d like you to consider becoming my personal assistant. You would work here in the main office and run errands around the property for me conveying messages to different departments. I might ask you to run an errand or answer a phone. You can cover Denise’s desk out front when she goes to lunch. It’s more money but most importantly it has a very special perk. There is an additional $100 a week bonus.” He offered. Winnie’s eyes got big and she smiled. “$100 dollars a week?” she asked. “And that’s on top of your salary as my assistant.” He finished. Richard leaned in close and placed his hand on Winnie’s thigh and looked into her eyes. “As my personal assistant you’ll be spending quality time with me.” He stated as his hand slid up her thigh moving closer and closer to her crotch. Winnie felt his hand but didn’t stop him immediately. “I believe you’re exactly the girl I’m looking for… fun, adventurous, beautiful and sexy.” And as he finished his hand touched her suit. Winnie looked down at his hand and Richard moved right next to her and put his arm around her pulling her to him and whispering in her ear. “You’ll make over $2000 by the end of this summer….” He caressed her pussy and Winnie squirmed a bit and Richard started to rub her clit…. “Think about what you could do with all the money.” He said as he fingers worked the sweet teen’s clit. Winnie put her hand onto his hand almost as if to stop him…. But he continued to massage her love button. Richard leaned down and kissed her neck pulling her tighter as he heard Winnie moan from his efforts. He started planting little kisses on her neck, ear and cheek. Winnie sighed lustfully as her legs parted and she scooted forward to give him better access to her pussy. Then she put her arms around him as her legs started to tremble. “I think you’ll enjoy this much more than babysitting a bunch of screaming brats at the pool…. Right Winnie?” Winnie was hot and about to cum. She gripped his shoulder and tucked her head against him. Richard focused his energy on her nub and Winnie moaned into her shoulder, “MMMMMMMMMMMMMMM”, shuddered and came. As she was panting Richard lifted her chin and kissed her. Winnie melted… He was a good kisser too. Richard slipped his fingers under the edge of her suit and slipped them inside her. Richard continued to kiss the teen and finger her and Winnie began to groan. “Yes…. That’s my sweet, sweet baby.” He whispered in her ear.
Richard continued to kiss Winnie as he fingered her until she came again and then he stood up and took her hand. The man led her around to his side of the desk and placed her on top of it laying her back to the desk. He sat in his chair and casually moved her bathing suit to the side and began to lick Winnie’s pussy. “OOOHHMMMMMMM” she moaned and then covered her face. Richard lapped away at the sweet little teen. Doing this in broad daylight on her boss’s desk…. It was so dirty and depraved and yet Winnie was absolutely sizzling with excitement and lust. She kept her mouth covered as she came….. and again when Richard fingered her G spot. Winnie couldn’t believe what was happening but she also realized in that moment that she liked it. Winnie pumped her hips and clutched at Richard’s head as her pussy fluttered and she came….. “UUUUUUUUUUHHHHHHHHHUUUHHHHHHHH….”. Winnie lay there on Richard’s desk, her body trembling as the man stopped and sat up. “Ms. Winnie…. I don’t really want to stop the fun but there is work to be done. I need your answer.” He stated. Winnie sat up with a huge smile and replied, “Yes…. I’ll take the job.” “Excellent and to seal our agreement I’ll need an oral presentation.” He said with a knowing smirk. Winnie was confused for a moment but then realized that he wanted her to suck his cock. She grinned at him and he back at her and she slipped off the desk and onto her knees. Winnie looked up at this handsome man and started unbuckling his belt and slacks. Winnie’s heart nearly stopped when she saw how big Richard’s cock was. It had to be ten inches long and thick. In spite of her shock, she managed to get the head into her mouth and start sucking. Richard pumped his hips, and the teen sucked with all her might. Winnie mewed, moaned and groaned as Richard started to fuck her face… Faster and faster they thrust against each other as Richard’s cock kept banging the back of her throat. Winnie gurgled and groaned lustfully as Richard panted and thrust. Then he gripped her head for the final few thrusts…. “YEEESSSSS MY SWEET BABY!! YEESSSSSS!!!”, and his cock twitched and sprayed a fat load of cum into her waiting mouth. Winnie sighed and cooed as the juice filled her mouth. There was a lot of it but it tasted great… This was the third different guy who’s cum she’d swallowed in three days. She realized that she liked the taste… and also it felt kind of gratifying to make the man cum after all the licking and sucking he had done. Winnie stood up and Richard took her in his arms and they kissed again. Winnie’s heart pounded as the man caressed her and savored her lips.
Richard took her to a closet and offered her a temporary uniform. “You can change into this, but as my assistant you’ll be wearing a dress on a daily basis. I’ll take you shopping for some nice things to wear. Also you won’t be sleeping in the dorms anymore. I’ll have much better accommodations for my personal assistant.” Richard stopped her for a moment as she was changing. “Winnie. Discretion is vital. AND I want to make it perfectly clear that our relationship will be completely private and exclusive. There will be no fraternizing with ANY guests or staff, especially Eric and Ryan. Is that clear?” he advised. Winnie nodded. “Yes sir. I understand.” She replied. “As far as anyone is concerned, I’ll be training you in Hotel Management… It’s very valuable and marketable skill Winnie…. Actually… I believe it will be more appropriate to call you Gwendolyn during business hours. I can call you Winnie in private…. But I think it’s important to use your full name in a professional setting.” He advised. Winnie realized that this wasn’t just some offer for sex… It was going to be a real job. “If any of the staff ask why you’re being promoted you may tell them that your father requested that I teach you a marketable skill. You can say that he and I are old college buddies. They will believe that.” He instructed her. “Yes sir.
Winnie left the main office in the new uniform and collected her belongings from the dorms. Nobody was around to question her and she never went back to the pool. Winnie was given a desk down the hall from Richard’s office and close enough to Denise’s desk where she could call out to Winnie if she needed anything. Richard then took Winnie under his wing and started explaining elements of hotel management. He was really going to teach her and she was excited to learn.
After work, Richard had Winnie collect her suitcase and he said, “Follow me.” Which she did. He approached his car and took the bag from her. “Where are we going?” she asked. “I can’t have you stay at the hotel. Your position doesn’t warrant a room like Ryan’s. I don’t want my sugar sleeping in the dorms…. So you’ll come and stay with me. If anyone asks your father has arranged a room in a house nearby and I’ve agreed to drive you to and from work.” He explained. Winnie was intrigued by how well crafted Richard’s story was. It’s possible that people would figure out that they are having sex, but unless someone saw something there would be absolutely no proof. And to all outward appearances it looked completely professional. “Oh…. I don’t think I need to tell you that there can be ZERO displays of affection towards each other. Everything here at the hotel must appear strictly professional. At home we can be as bad as we want to…. And if we decide to make out in my office…. Well that’s okay too…. But we can’t be too obvious about it…. Understand?” he advised. “Yes sir.” She agreed and with that he opened the door for her and Winnie got in.
Richard drove her to his home. It was a lovely house and Richard led Winnie back to the master bedroom and let her put her things away. He rejoined her in the bedroom and playfully tackled her onto the bed. “AAAAHHHHHH” she squealed and they landed together! “GOTCHA!” he growled as he gently bit her on the neck. Richard sucked on her neck for a moment and then he stared into her beautiful brown eyes and kissed her.
Richard finally had his prize at home in private and on his bed. He was going to take his time with this sweet little teen. Winnie was very turned on. She thought back to how he licked her pussy and what his cum tasted like and how big his cock was and she was ready to feel it. In the back of her mind she wondered how less than 72 hours before she was a virgin and now she’s all excited about having sex. Crazy…. She thought to herself. Richard gently undressed his little teenaged fuck toy…. Unbuttoning her blouse and unhooking her bra and sucking and nibbling on her tits… spending quality time on her nipples and mixing in kisses as he continued to strip her. Her skirt came off next and he could see her little cotton panties were wet. He stroked her supple legs and gave her thighs kisses and little licks towards her heavenly juncture…. Teasing the sweet girl and making her squirm with desire. Winnie ran her fingers through his hair and he got her hotter and hotter until he couldn’t wait anymore. He slipped off her panties and gazed at the sexy seventeen year old pussy. Richard licked his lips and went for it. “UUUUGGGGHHHYYEEEAASSSS” Winnie moaned. It was even better than on his desk…. She was so turned on…. Richard licked away at her sweet cunt savoring her sexy juices and enjoying her wiggles and pumps as he took her higher and higher until her thighs came together in a shuddering climax. “MMMMM….. MMMM….UHHHHUUUHHH….. UHHHUUUUHHH…. OOOHHHGAWD…. OHHHHGGAAAWDDD!...... OOOOHHHHGGGGGAAAWWWDDDYEEEEAAASSSHHH!!” She cried as her toes curled and she creamed.
Richard was just getting started. Now he put three fingers into her tight honeypot and stretched her out. “AAAAHHHHHHHHYEEEEEAAAAHHHH” she moaned. He continued to paint her hard little clitty with his tongue alternating licking on it and sucking and nibbling on it as Winnie writhed and bucked against his fingers. As soon as she came again Richard started to rub her G spot which made Winnie arch and squeal. “EHHHHHHHHHHHHHAAAAAHH”….. “Yeah come on sugar….. come hard for me!” he commanded and Winnie was happy to comply. Her hips bucked wildly as her pussy fluttered and clenched around his rapidly working fingers. She moaned and groaned and popped as juice oozed out of her sweet, sweet teen pussy. Richard licked up some of it but intended to use her sexy juice for a better purpose… sexy lube.
He was hard as a rock now, having popped in her mouth earlier today so he was ready for the best fuck of her life and possibly his too. Richard mounted his tender teen and Winnie looked up at him with her very happy and flushed face…. She was excited and ready to feel that cock in her. Richard spit on the head for extra lube and pushed into her. “UUUGGGHHHH” she groaned. (Oh GOD it feels so good) Winnie thought with just a couple of inches in her. “UUUUUMMMMPPPHH” she grunted as Richard pushed more in. “AAAAHHHHHHUUUUUHHHHH” she sighed as he was now deep in her pussy and it was already clenching him. “UUUUGGGGHHHHHHHMMMMMM” she moaned as the man bottomed out in her tiny little pussy. All ten inches of his thick cock buried in her tight teen pussy….. trembling and clenching at him as she became accustomed to it.
Winnie gasped….. “HHHHHHUUUUUHHHHHHHHH” as Richard pulled back and thrust it into her. “OOOHHHHGAAAWWDDDD” she cried as he started to fuck her. It was amazing. “SO DEEEEP!” she cried. “Yeah… my sweet baby…… you like my big hard cock don’t you?” he praised. “YYYYEEEEEAAAAAASSSSUUUHHHH” she moaned in luscious response. Winnie was already addicted to his cock and was going to cum. Her little hips popped up with a feverish pace as Richard began to thump her tight cunt. “UGH…. UGH… UHHUHH…. UHHHUUUHH….. OH GAWD…. OH YES…. OH YES…. YES…. YESSS…. YEAAAASSSSHHHHHH!” she cried is lustful bliss as her cunt spasmed around his thrusting shaft.
Richard turned the teen over and drove it in from behind. “OOOHHHHGGGGAAAWD!” she gushed as he was owning her tight little body. The man held her firm and pounded on her cunt as Winnie squealed and cried into the pillows. He marveled at how loud she was knowing she could make all the noise she wanted because the pillows muffled it…. But he had to hear her lose it for himself…. So he pulled her up by her shoulder and started rub her clit as he thumped her cunt. “UGH UGH UGH AHH AHH AHHH YAWW YEAWW YEAAWWW!” she cried over and over. “You like that baby…. You like to get fucked hard?!” he called into her ears. “YEEEAAAAAHHHHSSSIIRRRR!!” she moaned. THAT was a huge turn on when she called him Sir. “I want to hear you say it…. Winnie….. I want to hear you say Fuck Me hard. Say Fuck Me hard with your big cock Sir.” He ordered. Then he went back to fingering her clit. “UUUUHHHHHGGAAWWDDD…. YES PLEASE SIR…. PLEASE FUCK ME…. FUCK ME HARD WITH YOUR BIG FUCKING COCK!!” she screamed. Winnie was on fire….. her pussy was like liquid hot metal and Richard couldn’t hold out any longer…. He was already wildly pleased with this first fuck so he pulled out of her tight little pussy and laid Winnie down. He stuck the head in her mouth and the babe sucked on it hard and fast…. But Richard had other ideas. He pulled out and jerked it shooting streams of hot cum all over Winnie’s beautiful face. She gasped as it splattered over her cheeks and eyes and finally Richard put the head back in her mouth for her to clean him off. Richard rubbed his shaft over her face pushing cum into her mouth and Winnie happily cleaned it all off. Another first for her in this three day span…. Her first facial. Winnie was completely smitten. She looked up at the man and was absolutely under his spell.
- 2
- 3
You need to be logged in to leave a review for this story.You need to be logged in to leave a review for this story.
Report Story

The Wonder Years - Country Club Cutie