Harold and Wendy

This is my first short story, any feedback would be welcomed. I'm planning on writing more so let me know how to improve. Hope you enjoy.

*****

Harold Thompson has woken up promptly at 8 o'clock every morning for the last six months and sees nothing but an empty side of the bed where his wife used to sleep. Her name was Deanna. He thinks about her every day how she'd always smile as he woke up and tells him good morning. Now there are no more good mornings for Harold.

At age 56, Harold was never as physically active as he was before. He spends most of his time inside keeping himself busy by doing puzzles, crafting model airplanes, or watching T.V.. He only goes outside only when needed and has yet to find any other reason to have a life again.

Harold has always been described as more or less fit especially for his age. He and Deanna would always go out for a walk everyday in order to keep healthy. However after six months of doing pretty much nothing, Harold noticed he was getting a little pudgy around the midsection. Even though he had no one to walk with he decided it was time to get up and start moving again.

Eventually he decided to go for a walk around the neighborhood. In the beginning he would walk for a few blocks and come back home. After a few days he would go further and further until he reached a mile. He would also walk faster each time until he eventually started doing a light jog. He started to enjoy himself and knew Deanna wanted Harold to enjoy himself as well.

One day when Harold was going out for a jog, he noticed there was someone moving in across the street. He thought nothing of it and was about to go for his run when all of a sudden he noticed a beautiful young woman coming outside of the house. She was a brunette, average height, fit body but on the slender side, and she had the most gorgeous green eyes Harold had ever seen. He couldn't help but stare, even though he was old, he was still a man. The brunette went to the moving truck and went to help the movers bring in boxes, she then turned and noticed Harold. She waved and smiled at him. Harold instinctively waved and smiled back and couldn't help but feel a little bit shy. He then snapped out of it and went on his way.

Throughout his jog he couldn't stop thinking about her but at the same time he felt a little bit guilty thinking it was wrong to be having these thoughts about a much younger woman especially after his wife passed away. Thoughts about holding and kissing the woman ran through his mind making him feel hot and bothered. He hadn't thought about a woman like that in years, and he and Deanna hadn't been sexual with each other even longer than that. He tried to push it out of his mind, for he knew it wasn't right and he also knew a woman like that wouldn't even be interested in a man as old as he was. However, he thought to himself, why not just be friendly and welcome her to the neighborhood.

When he got back home he washed himself up and put on a fresh clean outfit. He told himself he just wanted to make a good first impression but subconsciously he wanted to look good for her. When the movers left he walked over to her house and knocked on the door nervously. She answered and Harold couldn't help but feel a little flustered when he saw what she was wearing: a fit white t-shirt and short jean shorts which didn't leave much to the imagination, Harold thought she was even more beautiful up close.

"Hello, can I help you?" she asked.

"H-Hi. My name is Harold Thompson." Harold stuttered. "I live across the street and noticed you just moved in and I just wanted to welcome you to the neighborhood."

"Oh that's so sweet, thank you, I remember I saw you earlier. My name is Wendy." she said.

"Wendy, like from Peter Pan?" he asked.

"Yeah, exactly. My parents were big Disney fans." Wendy said embarrassingly.

"My wife and I used to go to Disneyland all the time when we were younger." Harold remembered.

"That's nice. What's your wife's name?" Wendy asked.

"Her name was Deanna. She actually just passed away a few months ago." he said a bit saddened.

"Oh I'm so sorry to hear that. It must've been difficult." Wendy said as she touched his arm.

"Yes it's been fairly hard and a bit lonely but I'm getting through it." he said. "Well if you need anything at all just let me know I'm right across the street. If you need help with fixing anything I'm pretty good with my hands."

"Thank you, I'll be sure to let you know." she said.

"Okay, I guess I'll see you later, Wendy." Harold said with a little glee.

"Bye, Harold." she said with a cute smile. Harold blushed and walked back to his house with a little vigor in his step. He knew nothing would come of it but it didn't hurt to have a cute neighbor girl to talk to every now and then.

A few days had passed and Harold went about his daily routine secretly hoping that one of these days Wendy would come knocking at his door. He didn't care if it was to have a nice chat or to help her fix her toilet, he was just longing for that interaction with another woman. Luckily for him, that day had come as he heard a knock at his door. He went and answered it faster than he had ever did before. He opened the door and she was standing there in a tight purple tank top and fit yoga pants which accentuated her curves nicely.

"Hi, Harold!" Wendy said. "I noticed you liked going for jogs and was wondering if I could join you." Harold was surprised and excited realizing this could be a great chance to get to know her better.

"Sure, Wendy!" Harold said eagerly. "Let me just change first and we could go."

"Yeah no problem." she said. After Harold changed they both started their jog. Wendy figured Harold wouldn't be able to run as fast so she kept the pace slow. They talked while they jogged and Harold never felt more comfortable with another woman apart from Deanna. They talked about what each other did for a living and what they liked to do in their spare time, which eventually led Harold to ask if she was single or not.

"No I'm not seeing anybody at the moment." Wendy said. "I guess most of the guys I meet have always been a bit immature and I guess I'm just looking for someone who's more relaxed and easygoing."

"Well, I'm sure you'll find somebody". Harold said. "You're still young. How old are you actually, if you don't mind me asking?"

"I'm 25. Although my friends tell me I act more like a 30 something year old." she laughed.

"Yes you do seem more mature. I guess an older man would be more your type." he said slyly.

"Yeah, probably." she smiled. They talked all the way back home both sweaty and tired. Harold felt like he was making progress with her but still never really thought they could be involved romantically. Older men seemed to be right for her but she could never be interested in a wrinkly old man like himself, he thought.

"Hey could I ask you a favor?" Wendy asked

"Sure. What is it?" he asked.

"My shower is kind of on the fritz at the moment, would it be alright if I used yours?" she asked embarrassingly.

"Um, yeah th-that's fine." Harold stuttered. "Come on in." Harold immediately imagined her naked fit body in his shower but then tried to keep those images at bay knowing it was inappropriate. He showed her up to his bathroom and said for her to take as much time as she needed. Harold went back downstairs and heard the water running. He couldn't take his mind off of her knowing she was up there naked running her hands across her supple young skin. He tried to keep himself from getting aroused but it was so difficult he almost thought about jerking off but decided against it.

After a while he heard the water turn off and tried to act natural by turning on the T.V. He could hear her coming down the steps and knew she would have to go soon which saddened him a little bit. However when he turned around to say his goodbye he saw something that almost gave him a heart attack. There she was completely naked in his living room.

"Wendy? What are you doing?" Harold said perplexed. She walked toward him.

"Come on now, Harold. You said yourself an older man would be more my type." Wendy said seductively. She walked closer to him, grabbed his hands, and put them on her curvy hips. "Don't you like what you see?"

"I do, very much so. I just never thought a beautiful girl like yourself would be interested in an old man like me." Harold said nervously.

"Well that's not true. I think you are so handsome and kind and nurturing. Nothing like the other men I've been with." she said, right before she planted a soft kiss on his lips. "I want you, Harold. Don't you want me?"

"Oh, you have know idea." he sighed. She smiled and gently pushed him down on the couch. Wendy straddled her tight naked body on top of him, her pussy right on top of old crotch. She kissed him passionately and he kissed back, at first not knowing what to do since it's been so long for him but he got back into the rhythm of things. He kissed her neck and moved down her chest to her nice C cup sized breasts and sucked on her nipples.

"Oh my, that feels so good." she moaned. He continued to suck her tits and moved back to making out. Suddenly she stopped. "You've probably hadn't a blowjob in long time huh?"

"Long time? I don't think Deanna ever did that for me." Harold said excitedly knowing what was coming. She moved herself down to the floor and unbuttoned his pants. She released his 5 inch member which was hard and throbbing. "Sorry, it's not that big."

"Don't worry about it, it's big enough." she said as she stroked it. She teased it with her tongue licking the tip before putting it all in her young warm mouth. He moaned. She sucked it like a pro, going up and down with her head and occasionally licking his wrinkly ball sack while jerking him off. Her tongue felt so good on his hard cock, he felt like he was in heaven. Harold never had a blowjob before and couldn't hold himself any longer.

"Oh my God, I'm gonna cum!" he exclaimed. He burst into her mouth while moaning. Wendy held it in her mouth and swallowed.

"Mmm, yummy." She said. "Now that I've done you, I think it's time you return the favor. Have you ever eaten pussy before sweetie?" Harold shook his head, he was still calming down after exploding in her mouth. "That's okay. Let me teach you." They replaced positions, her on the couch now and him on the floor. Wendy gently placed his head in between her legs. "All you have to do is pretend like it's a french kiss." Harold immediately kissed that young wet pussy like he was starving for it. She moaned at his touch. Her juices flowed through his mouth as he kissed and licked her pussy lips.

"Go ahead and stick a finger in me, baby." she said. Not knowing how to do it properly, Harold slowly and gently placed his finger deep in her cooch. Wendy licked her lips and caressed her perky breasts. Harold noticed and grabbed her left boob twisting the nipple all the while fingering her pussy and licking her clit faster and faster. "Oh yes just like that don't stop! Oh you're gonna make me cum!" Harold's hand was getting tired but he kept going until she came and let out the cutest moan Harold's ever heard. "Baby you've still got it. Can you get it up again? I want you to fuck me." Harold's dick hadn't seen any action in years.

"Of course I could get it up." he thought to himself. His dick got hard immediately and couldn't wait to go deep inside her. "Do you mind if we do it doggystyle? That's my favorite." he asked.

"Anything you want, sweetie." she said. Harold flipped her around and got a nice look at her sweet tight ass. Without thinking about it he gave it a good smack. "Ooh damn, you're pretty rough for an old timer."

"You're about to see this old timer has still got some juice left in him." Harold whispered in her ear. He rubbed her pussy a bit from behind and then eased his cock into her. He started slow feeling how warm and tight it was as Wendy bucked her ass back into it. Since he came earlier he knew he could last longer and so continued at a steady pace of fucking her as she moaned. Harold then yanked her hair playfully. "You like that, Wendy? You're pussy is so tight, I love it!" He continued faster wanting to make her scream and cry out in ecstasy.

"Make me cum again, baby! Make me cum again!" she screamed. Harold's jogging helped him trained his endurance and he kept pushing himself harder than ever before, giving her as much pleasure as he possibly could. His cock thrust into her harder and harder until she came again much to his delight. His cock wasn't done yet, he needed to cum again too.

"Suck me off, honey. You gotta finish me off." Harold said. Wendy sucked his throbbing cock harder than before. She jacked him off so hard it felt like a workout but she loved every minute of it until he came on her face again.

"Look at you, such a stud. That was amazing." Wendy said while licking the cum off her face. They then sat there on the couch completely exhausted and wanted nothing to do but cuddle in each other's arms. Harold told her one last thing before nodding off.

"Wendy, for the love of God, never grow up."