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
- 1
- 2
- 3
The next morning they walked back to the dorms and got ready for work. “So how was it?” Ryan asked Winnie. “What?” she replied. “You and Eric…. How was it?... Everyone saw you two walk off into the woods. We all know about his little camp. You’re not the first girl he’s brought out there…. So…. How was it?” he continued. Winnie mushed up her face…. I don’t know what you’re talking about. I have to go to work. “Hey look…. I’m just sayin…. Everyone knows. It’s no big deal. Eric brings girls out there all the time and he’s had his eye on you since you got here.” Ryan told her. Winnie turned around. “What do you mean?” she asked. “I mean…. He called dibs on you the moment he saw you. Told the rest of us guys to stay away.” He replied. “He called dibs?” she confirmed. “Yeah…. Well… You know. He wanted us to know that he was going after you.” Ryan admitted. “So he planned all this?” she asked now getting upset. “Look…. I’m just saying that he wanted you and he was going to get you…. I guess. I don’t know. I think you’re hot too… but he called dibs so I stayed away. Sorry if that bugs you. I just thought you should know.” Ryan replied. Winnie considered everything and went to work. When she saw Eric she didn’t say anything. “Hey beautiful. How are you?” Eric asked. “I’m fine.” She said without looking at him. Eric stared at her…. “Are you okay?” he asked. “Yeah…. I’m good.” She said looking over at him. Then she blew the whistle at some kids and that stopped the conversation.
Later after work Eric stopped her…. “Winnie, what’s wrong?” he asked. “You planned to take me out to the woods? You called ‘dibs’ on me? You told all the other guys to stay away from me?” she spoke… her anger seething out. “Well… It’s not like that. I just meant that…” he started. “That I’m some PRIZE for you to win???!!” she growled. “Okay wait…. Just hold on. Just because I saw you and liked you doesn’t mean that you’re a prize. I just …. I don’t know…. I wanted everyone to know that I liked you.” He offered. “You liked me? You hadn’t even met me yet? How could you like me without even talking to me. You just wanted to get me out to your little camp so you could…” she started to cry. “I can’t believe I let you do that to me. Oh my God…. I’m just another girl to you. I’m just another girl you slept with.” She cried. “Winnie wait. It’s not like that…. Please.” Eric called out but it was too late. Winnie was gone.
Winnie went to the girls dorm and ended up talking with the others and some of them admitted that they knew he was after her. Some of them had been to Eric’s little camp too. When they got down to talking Winnie admitted that it was her first time. Some of the girls felt bad for her but then one of them said… “Well wait. I’m mean it’s not like he’s bad in bed. I sure had a great time. How was it?” she asked. Winnie looked up and then cracked a smile. Then the girls laughed. “I thought it was special though. I really liked it… him. I don’t know.” she mused. “Well be thankful. My first time was with my boyfriend in high school and it was over way too fast. It took a few times before I even felt something. Eric is well…. he knows what he’s doing down there.” She confided. “Yeah… that’s what got me. He just knows exactly what buttons to push and the next thing you know your panties are on the floor.” Another girl offered. They all started to laugh. “Yeah…. I didn’t think it was going to happen like that but he just kept…. Pushing my buttons. I’d never done anything like that before…. So it was … well…. it was my first time… so I guess….” Winnie trailed off. “You got really lucky that you found a guy who was careful and took his time. Eric is not a bad guy… He’s just a player… and he usually gets what he wants.” The first girl advised.
Winnie went off and Ryan saw her and chased after her. “WINNIE!” he called out. She saw him and paused. “Hey…” she offered. “Hey…” he replied. “So listen. I didn’t mean to make Eric sound like a bad guy okay. It’s just… I don’t know. I guess I’m jealous. He always gets the pretty girls and I didn’t want you to get too hung up on him.” He confessed. “It’s okay. I thought about it and I’m not upset. I mean I’m still mad at him for treating me like a prize or whatever but well…. you know the rest.” She confessed. “Are you going to go see him again? Ryan asked. “I guess I should. He deserves the chance to explain… I didn’t really let him before.” She replied. “Well… he’d be pissed at me if he knew…. But I think you’re really beautiful and I don’t know…. I guess I’d like to go out with you too…. So if things don’t work out… maybe consider me?” he offered. “Yeah…. Maybe… I guess.” She replied.
Winnie went looking for Eric and she spotted him and stopped in her tracks. Eric was flirting with some girl who was a guest at the club. “Hey if you ever want to hang out… I have this cozy little spot out in the woods. It’s quiet and nobody will bother us.” He told her. “Sounds nice…. I might have to take you up on that.” She replied and smiled at him and off she went. Eric turned to see Winnie and he saw her face and knew it was over. Winnie turned right around and started to walk away fast. Eric ran after her. “Winnie…. Winnie wait… please.” He begged. “Why? Why should I wait? I was going to give you a chance to explain everything and I find you trying to pick up another girl… I mean after everything last night… You just couldn’t wait to bring another girl out there! You’re a pig!” She stormed off and went directly to Ryan.
“Wow…. What happened?” Ryan asked. “He was already trying to get another girl out there. Probably tonight for all I know. He’s a pig!” she growled. “Oh.” He replied. Ryan stood there not sure of what to say…. Winnie started to tear up. “Hey…. Okay don’t cry… please.” He asked. “I feel so stupid. I can’t believe I lost my virginity to that jerk.” She cried. “Oh wow… Okay wait…. Winnie look at me. Look at me.” He asked. She looked up and he wiped her tears away. “It’s a summer job. It’s a summer fling. It was going to end no matter what. He's going back to finish college and you’re going off to start. You’re going to meet lots of guys. And okay…. Maybe you shouldn’t have…. But he’s pretty good… you know…. at that stuff. All the girls here like him. They go out there all the time and come back really happy. You seemed happy when I saw you…. Right?” he asked. “Yeah…” she admitted. “Okay…. So most of the time… the first time is not good. Ask any girl and they’ll tell you. So you had a good time… for your first time…. And you were going to have to move on from him anyway…. Unless you were planning on following him to college and becoming Mrs. Head Lifeguard.” He teased. Winnie smirked and then let out a little laugh. “Okay I guess.” She agreed. “Alright… so let’s put that behind us and how about we get some food and you and me have a real date?” he asked. Winnie looked at him… Also handsome with blonde hair and blue eyes. “I guess so.” She said. “You guess so?.... Well there is a ringing endorsement.” He lamented. Winnie laughed and he laughed and he took her hand. “Come on…. You need to change.” He advised. “What why?” she asked. “I can get us in the restaurant but you can’t wear jeans okay.” He explained. “Oh… okay…. Let me get changed.” She agreed and Ryan replied. “I’m going to change too… I’ll meet you at your dorm in 30 minutes.” “Okay.” She replied.
Ryan showed up in slacks and a blazer… Winnie put on a cute dress that she brought just in case. “Wow…. You look great.” He said. “Thanks…. You look nice too.” Winnie replied. The pair took off and went to the restaurant. Ryan took care of everything. Winnie had a glass of wine with dinner. Nobody said anything. The pair chatted about school, Kevin and Winnie’s plans for after graduation. “I love art… That’s what I want to study.” Winnie told Ryan. “Interesting…. So are you an artist or you want to teach?” he asked. I’m not sure… but I love sculptures and paintings.” She said. “That’s wonderful Winnie. I’m happy for you.” He replied.
After dinner Ryan took Winnie on a moonlight stroll… They held hands and he led her back to his room in the hotel. “Where are we going?” she asked. “One of the perks of being the Front Desk Manager is I don’t sleep in the dorms. I have my own room…. With a view. I thought you might want to see it.” He answered. “Wow…. That’s great.” Winnie replied. The pair went into his room… It was lovely with a King size bed and nice furnishings. Ryan went to the sliding glass door and pulled the curtains back and opened the doors to his balcony. The view was beautiful and lit up by the moon. It was very romantic. Winnie following him out and was taken by the sight. “OH MY…. It’s…. It’s so beautiful up here.” She said. “Not as beautiful as you.” He replied softly in her ear. Winnie blushed and Ryan took her in his arms and kissed her deeply. Winnie felt that rush of excitement but she was nervous. She literally had sex with Eric the night before and she didn’t want to give Ryan the wrong idea… but he was a really good kisser.
After a few minutes of kissing Winnie tried to excuse herself. “I should really get going.” “No… please don’t go. I know what you’re thinking. You’re worried about what people might say or what I might think about it. Well don’t. I think you’re wonderful and special and I really want you to stay…. Besides…. Come and lay on this bed and tell me that you’d rather sleep on that dorm mattress….” He teased. Winnie couldn’t help it…. She grinned at that and followed him back into the room. Ryan plopped down on the bed and patted the spot next to him. Winnie sat and was surprised. “Woah…. Oh wow…. It’s so comfortable. This is better than my mattress at home!” she exclaimed. “Lay back.” Ryan offered. She did and just rolled around a bit savoring the mattress until Ryan rolled over on top of her and kissed her again. Winnie sighed in his mouth but he could tell she was still nervous so to break the ice Ryan started tickling her. “NOOHHAHAHAHAHAHAHAHAHAHA…. OH MY GOD…. STOOOOPPP… HAHAHAHAHAHA… PLEASE….. HAHAHAA.” She giggled. “Promise you’ll stay?” Ryan offered. “What?” Winnie replied. “HAHAHAHAHAHAHAHAHAHAHA….” Ryan immediately went back to tickling her and she howled with laughter. “Promise you’ll stay?” he offered again. Winnie caught her breath and smiled at him. “I want to but I don’t… I’m … I don’t think we should have sex okay?” “Okay.” He said agreeing with her immediately which put Winnie at ease. He looked down and her and kissed her fully again…. “We can make out some right?” She smiled at him and he knew it was okay. “I can’t sleep in my dress.” She said. “I have a t-shirt you can wear… and your underwear.” He replied as he got up and went to her feet. He slipped off her shoes and took her hand and stood her up and they kissed again. Then Ryan turned her around and kissed her neck and her ear and then she turned her head to kiss him again and he unzipped her dress. Ryan stroked her soft skin over her shoulders, down her back and even slipped his hands around the front of the dress to her tummy and caressed her as they kissed. Winnie wasn’t wearing a bra with this dress so Ryan thought about feeling her tits but decided to wait. Winnie held onto the dress so it didn’t fall to the floor and Ryan stepped over to the dresser and pulled out a country club t shirt. With her facing away he gently tugged the dress from her hands so it would fall to the ground. Winnie covered her breasts for a moment but Ryan wasn’t peeking, and he pulled the shirt carefully over her head and opened it so she could easily get her arms in and just like that Winnie was ready for bed. “The bathroom is right there and you can use my toothbrush.” Winnie padded off in her bare feet into the bathroom. She was loving this decision as it was so clean and fancy compared to what she had to share with the other girls. She brushed her teeth and checked her look. She wondered if she’d be able to resist sleeping with Ryan… she was already almost naked.
Ryan stripped off all his clothes except his underwear. Winnie came out and almost gasped as she saw this muscular hunk in nothing but his underwear. She didn’t fail to notice the bulge in his shorts. The handsome man took her in his arms and kissed her again and she melted. Her resolve was gone almost immediately. He could have stripped her right then and thrown her on the bed and ravished her and she wouldn’t have complained but Ryan was patient. He turned off the lights and such and got Winnie into bed and they started to make out. His hands slipped under her t shirt as they kissed and he stroked her tits and played with her nipples. Winnie didn’t even realize it but she wanted to feel his cock. As her hand touched it she could feel how big and hard it was. It felt hot just touching it a little and then she squeezed it and Ryan moaned and ran his hand right into her panties. (What has happened to me?) she thought as her decision not to have sex was flying right off the balcony.
Ryan massaged her clit like the experienced lover he was…. Winnie slipped her hand into his shorts and stroked his big cock. It was thicker than Eric’s and she stroked it and squeezed it and started thinking about what it was going to feel like and she didn’t even flinch when Ryan peeled off the t shirt and started sucking her nipples. His fingers danced over her clit and Winnie pumped and thrust against him until she came. “MMMMMMMMHHHHHHHMMMMMM” she moaned. Ryan slipped his fingers inside the teen and she purred and stroked his cock. Ryan could see that Winnie had changed her mind and he wasn’t going to question it. He stroked her pussy until she was panting and her nipples were hard and he slipped under the covers and peeled off her panties with no hesitation.
Ryan opened her thighs and Winnie moaned deeply when she felt his hot tongue plunge into her tight twat. (God I’m so turned on again…) she thought as her hands ran through the man’s soft hair as he licked and sucked her into and frenzy. Ryan also knew exactly what buttons to push and he pushed them very well making sweet Winnie gush and tremble with fantastic sensations. Ryan also found her G spot and combined with his tongue, her pretty pussy fluttered again and again as she moaned and groaned under the expert lashings of her master.
Finally it was time. Ryan mounted her and Winnie gazed up at the handsome stud as he opened her thighs and rubbed the head of his cock between her juicy lips. He pressed his thick cock into her tiny pussy. Winnie grunted but tried to relax. There was no pain…. Just the pressure and the feeling of being stuffed. But in the back of her mind…. She knew he was going to dominate her and she had already agreed that she would do whatever he said and swallow his cum. Her switch was on…. And Ryan felt her juices all over his cock and knew how wet and excited she was. She grunted as the last of his heavy hammer hit home. Ryan then leaned in and kissed her. Winnie purred in his mouth but he had to see her eyes so he lifted up and watched her expression as he pulled back and thrust into his prize. “UUUUHHHHHAAAAAAAAHHHHHH!!!” she cried. Oh it was Heavenly. She was so tight and hot and wet. Winnie’s eyes rolled back in her head and Ryan started to fuck her forcefully right away. He wanted to see how fast he could make her cum. Five minutes… Five minutes and Winnie was bucking and shuddering and he felt her pussy flutter. The man kept right on going and played with her nipples. He had her and now he knew she was his plaything.
Ryan fucked Winnie sideways and fingered her clit making her shriek into the pillows as he pounded on her. Each thrust hit her just right and Winnie was overwhelmed with lust. “GOD!!! YESSS!! PLEASE!!! YES!! YES UGH… UGH ….UGH GOD! .. OH MMM HHHMMM UGH UGH UGH….” Over and over she cried. The orgasms seemed to just roll through her in waves. Ryan would move her into another position and fuck her that way and she would cream. Then he’d move to another and she’d cream some more…. In the end Ryan put Winnie back on her back and put her ankles on his shoulders and gripped her tits and fucked Winnie deep, fast and hard making her yelp and throw her head from side to side until her orgasm crested and Ryan kept right at it. “Come on baby…. Cum again for me!” he urged as he could tell that Winnie was at his mercy. “UH UH UH UH UH UH UH UH AH AH AH AHHGAWD HUH UH UH UH UH MMM AHH… HAA.. YUH… HUH… MMM OH… OH… OHHHH…. GAWWWWWDDDDDDDD!” and her whole body shuddered as she came and gripped his neck bucking and thrusting. Finally he stopped and brought his cock right to her lips and Winnie moaned as she wrapped her lips around it like she’d been waiting for that all day. Ryan erupted a hot load he’d been saving for a couple days and it flooded Winnie’s mouth and she groaned in bliss as it slithered around before she swallowed it. Ryan laid back down next to her as the pair gasped and recovered. They kissed a little more and then both fell asleep.
- 1
- 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