Megan's Summer Education Ch. 04

"Well you seem like a sweet man," Megan said. "I bet you're a great daddy." She used the word "daddy" on purpose, understanding the double meaning. She bit her lip for effect. She felt so naughty.

"Your boyfriend is a lucky guy," Tom said.

"Oh, I don't have a boyfriend," Megan said. "We broke up a few months ago. Both going our separate ways, you know. Plus, he was kind of immature."

"High school boys can be that way," Tom said.

"Well, he was a little older than that," Megan said. She left it hanging there. No details, but floating him the idea that she liked older men.

"I see," Tom said. "Well, I'm sure he's regretting letting you get away."

"Thank you for saying that. You're very sweet."

"And you're very patient," he smiled. "You came over here asking for a simple ride and I've had you talking for 15 minutes. Let's get you that ride and you can get back to your, um..."

"My grandads," Megan said. "I usually call them both daddy though. It's easier. A girl can never have too many daddies, I guess."

"I suppose that's true," Tom was even cooler than she expected. He had to catch on to her flirting, but he didn't really show it. He seemed bemused. He was enjoying this, yes, but his expectations were muted. He was aware that this was all mostly a game. He was just happy for the entertainment. She liked that vibe she was getting from him.

He finished his beer and they walked side by side to the ticket booth. He bought them each a ride ticket and they headed to the Tilt-A-Whirl. A few men gave him the head nod, like, "Way to go" or "How did you score that?" A few women his age scowled at him. Megan did her best not to notice. She was focused on Tom and playing her role of sugar baby on the prowl for a sugar daddy. She needed to continue to flirt and make sure he knew she understood that his generosity deserved to be reciprocated. On impulse, she took his arm, holding him as they walked. He didn't pull away nor did he seem phased by the eyes upon them.

As they waited in line for the ride, for the first time he hinted at a little payback for his generosity.

"You know, one of the things I always liked about this ride is how that car kind of wraps around you so you're sort of enclosed," he said. "People aren't staring at you. You're just spinning and sliding and your body is kind of out of control."

"Yeah," Megan latched on to the opportunity. "You're kind of bumping into each other and your hands are flying around."

"You never know where they might land," Tom laughed.

"That's why it's good to have a ride partner who doesn't mind," Megan said suggestively. "They can land anywhere they want."

"Hands do have a mind of their own sometimes," Tom said. For the first time he really looked her up and down, as if plotting exactly where he was going to put his hands.

"Looks like yours are thinking already," Megan teased.

"Possibly," Tom said. "Right now they have a bit of a dirty mind, I'm afraid."

"Nothing to be afraid of," Megan said. "The Tilt-A-Whirl is a judgement free ride. And I'm a judgement free girl."

The previous ride ended and it was their turn to get on. Megan sat down first, then Tom sat next to her, putting his arm around her neck. "Cozy in here," he said. "Hope you don't mind."

"Of course not, sir," Megan said. To emphasize the point, she arched her back as if trying to get comfortable, purposely pressing her breast into his hand. He didn't move it away.

"Guess you can't wear a bra with a dress like this, huh?" he said as they waited for the other riders to get into their cars.

"No," Megan said. "Sure can't. Luckily it's not too cold tonight or I would be putting on a bit of a show."

"Trust me, you already are," he said. "But in a good way. A very good way."

As the ride slowly started moving, he slid his hand inside her dress, cupping her breast. He didn't ask if it was OK. He knew it was. In response, she giggled and put her hand between his legs. He was getting hard.

"Hmm," she said. "That could be an issue when we get off this ride."

"Nah," he said. "No one sees me when we're walking together. They only see you."

The ride went faster and their car, true to the name of the ride, started spinning and twirling. He did the same to her nipple. They moved so fast they weren't concerned what people could and couldn't see. Certainly some might notice something, but by the time they really looked, the car was spinning again and moving away to the other side of the ride.

Knowing that the ride would be over far too soon, Tom reluctantly moved his hand from her firm breast and pleasingly rigid nipple. He only had a few minutes to reach between her tan thighs and touch her pussy. He wasn't about to miss that opportunity.

She moved her arm out of the way, holding her arms up like she was on a roller coaster while his hand went between her soft thighs and under her dress. He deftly moved his fingers, pushing aside her g-string, touching her bare mound and moist slit. He could only imagine how tight this hard-bodied teen would feel riding up and down on him. He knew he would jerk off later that night, envisioning that very moment.

The ride ended and he took her hand, helping her out of the car. They walked hand-in-hand back through the carnival, neither caring what anyone thought. It had only been a few minutes, but Megan really liked him and was proud of her first choice.

"I know this is just a brief moment," he said. "But I want you to know that I appreciate that you never asked what I do for a living or tried to find out how much money I had. You really are drawn to older men, aren't you? I mean, you're not just looking for a sugar daddy."

"That's true," Megan said. "I have always been drawn to older men. I don't really care about looks or money or age. I just like maturity. You treat me like a woman, not a toy. I like that."

They took out their phones and exchanged numbers. Megan then stood and let him take a couple of pictures of her -- nothing sexual, just standing there, giving him a smile. He walked her back over to Mick and Harry. He introduced himself and shook their hands.

"You have a wonderful granddaughter," he said, winking at them to let them know he knew she wasn't their granddaughter. "I just wanted to let you know that she was extremely polite and mature and respectful."

"Thank you," Mick said. "We are very proud of her."

"As you should be," Tom said. "Out of respect for you both, I wanted to let you know that Megan and I exchanged numbers. I will not pester her nor make any unwanted advances. But I am a real estate agent and would be happy to be of assistance to any of you if you ever need it. Even if you already have an agent, I'm happy to offer any advice. No charge."

"That's very kind of you," Harry said, accepting Tom's card. "We were talking the other day about possibly selling our house and moving as needed to stay close to Megan."

"I can certainly understand why you would want to do that," Tom said. "And I would be happy to help you if you decide to do that."

Tom accepted a kiss on the cheek from Megan and turned away, just as his son and his friends approached, asking for more money to play more games.

Megan sat back down with Mick and Harry, smiling. "That was fun!" she said. "He was so nice!"

"Looks like you aced that one," Harry said. "Good choice. You really thought that through."

"By the way, how's the butt plug feeling?" Mick asked.

"You know, I still feel it but it doesn't bother me anymore," Megan said. "It's just kind of there. I guess that's good, right?"

"Yes, that's good," Mick nodded. "So, ready for round two?"

"Yes, sir," Megan said. "I just hope I find someone as nice as Tom. Does it matter which thing I ask for?"

"No," Harry said. "You can complete the remaining assignments in whatever order you choose. I would remind you that the Ferris wheel is a longer ride with some privacy. You will probably get stopped at the top. So choose wisely."

"I wish I had chosen Tom for that one," Megan said. "Hopefully I can find someone else just as sweet."

"We'll see if you had good judgement the first time or if it was just beginner's luck," Mick said.

Megan looked around the beer tent and stage again. Plenty of men there, but most were in a large group or there with family or girlfriends. She looked at the bingo tent. There she saw a man sitting by himself. She watched him for a few minutes. He was smiling and chatting with the people running the game, but he seemed to be alone.

He looked older than Tom, maybe early 50s. He was black and had a stocky build and looked to be pretty short. He seemed to be having a lot of fun. Megan liked his laugh, which was audible above the ambient noise, and smile.

"Him?" she nodded towards the man. Again, she explained her reasoning and the guys agreed.

"I'm kind of hungry," Megan said. "I thought I might ask him for a snack."

"Go for it," Mick said. "We'll be right here."

Megan walked over to the bingo tent, keeping her eyes on the man, trying to decide how to approach hm. She had never really approached even guys her age before. Now here she was trying to figure out how approach men old enough to be her dad or grandfather. They wouldn't expect that she was trying to pick them up, so she had to be pretty forward. But she didn't want to be so forward that they mistook her for a prostitute or gold-digger or as part of some sort of prank. Plus, she had to be protective of herself, reading them to make sure she would be safe with them. It was very challenging. She trusted her instincts, ability to read body language and ability to be very polite and engaging. Her experience as a cheerleader helped her see the value of being cute and perky. Some found it annoying, true, but very few were put off by it. Most of all, she wanted to be as genuine as possible in hopes of him reciprocating.

"Excuse me, sir," Megan said, approaching him hesitantly. The man looked at her, his eyes quickly going up and down her body. Not leering, but he certainly noticed. "I was wondering, um, could you teach me how to play bingo? I've never played and you seem to know what you're doing."

"Don't know how to play bingo?" the man asked skeptically. Megan knew it was a pretty thin opening, but it was all she could think of. So much for being genuine.

"I know," she said. "I mean, I played it as a kid but I don't really know how you get the cards and how much it costs and all that."

"I see," the man said. "Well sit down here if you want and I can show you while I play."

"Thank you," Megan said, sitting next to him so she could see his cards. He was playing three at once.

"Your parents know you dress like that?" he asked.

"They are out of town," Megan said. "What they don't know won't hurt them, right? Besides, I'm 18. I can wear what I want."

"True enough," he said. "Name's Bud. You are?"

"Megan," she said, shaking his hand. "Very nice to meet, sir."

"You didn't really come over here to play bingo, did you?"

"No sir," Megan frowned. "I'm sorry. I just, well, you have a great smile and it seemed like you were having so much fun, I wanted to meet you."

"And..."

"And I wanted to see if maybe you wanted to share a funnel cake with me."

He looked at her skeptically. "You don't have any money, do you?"

"No, sir," Megan said. "But I'm not asking for your money. I mean, yes, I suppose you would have to buy the funnel cake. But I don't need money. I would just like the company. I promise, that's it."

"You got a thing for black men, older men or what?" he said laughing.

"I have a thing for men," Megan laughed. "Mostly older, I guess. Just real men, you know. I don't suppose you like 18 year old former cheerleaders in tight little dresses, either, do you?"

"Hell no," he laughed out loud. "What kind of man would be attracted to someone like that?"

They both laughed and he said, "All right, let me play another round and then we'll go find some good fried carnival food. I'm not looking for any trouble from your dad or a jealous boyfriend or anything, so we'll keep it casual and just get to know each other. I'm still trying to figure you out."

"I understand, sir," Megan said. "I know it's weird for me to approach you like this, but I promise there's no trick, no angry dad or boyfriend or anything like that. I won't bring you any trouble."

He played the last game, winning $20 which he said would pay for their treat.

"Thank you," Megan said. "I want you to know that I'm not a gold-digger. I'm not looking for handouts or trying to con anyone. I just, well, it turns me on to flirt with older men."

"That's a dangerous game," Bud said. "You realize sometimes flirting can be interpreted as an invitation for something more, right?"

"I know," Megan said. "That's why I'm careful. I watched you. I saw how you interacted with people and how you smiled. I thought you would be fun to flirt with but, well, safe, too."

"What do I get out of this then?" Bud said. "I know you're not going to go home with me and let me pull that little dress off you."

"No, sir," Megan said. "I can't do that. But I will do something for you. What do you want?"

Bud stopped and faced her. "You really want to know what I want? All right. Well, my wife is home tonight. She's home every night. We've been married for 26 years. I love her to death. But she had a stroke a few years ago. She needs constant care and, well, she can no longer care for my needs. I'm not complaining, but I do have to make time for myself. I'm not proud of it, but it's true."

"Of course you do," Megan said, her voice filled with genuine compassion. "You poor thing. Maybe we can find a quiet place and I can jerk you off?"

"Nah, little girl," Bud said. "I'm not asking for that. That's just trouble waiting to happen. But what I would like is a little show. A video that I can, uh, use later when I'm alone. A video for my eyes only."

"Uh, sure," Megan said. "What did you have in mind?"

"You're hungry, right?" he smiled.

"Yes, sir," Megan said.

"You know how to eat and make it look sexy?"

Megan smiled. "Yes, I sure do. Maybe buy a corndog and a funnel cake with lots of that white powdered sugar and whipped cream on it?"

"I like that," Bud said. "I'll get the food. You find a place where we can have a little privacy but with enough light to make a good video."

"Yes, sir," Megan said. She was smiling as she looked for a good place. This was going to be fun too. She felt much less like a slut knowing that she was doing something nice to help this poor, sweet man.

She looked around and saw a small building with a sign that indicated it housed arts and crafts exhibits. But exhibitors were gone and the building closed for the night. There were plenty of people walking by it, but no one approaching it or the three small round picnic tables sitting under a security light next to the building. Anyone looking over would be able to see them as they walked by, but there was no real reason for anyone to approach them. It was too open to have sex or anything like that, but not too open to make a little sexy video.

She went back and joined Bud in line, helping him carry two corn dogs, fries and a funnel cake and two drinks back to the table.

"Perfect," he said. "Before we start, let's just do a little test to make sure the video and audio and lighting and everything is OK."

"Sure," Megan said. She was feeling comfortable now, creative, having fun. She stood up next to the table and looked at his phone as he recorded. "Hello Bud. I'm very happy to make this video for such a sweet man. I wish I could do more for you, but I hope this helps fulfill your needs for a long time to come. My name is Megan, I'm 18 and I'm, well, as you can see how I'm dressed, I'm not a very good girl. But I am very good at being very, very bad. Just watch."

"That was pretty hot," Bud said, stopping the recording. Megan looked over his shoulder as he played it back. It was a little grainy from the lighting, but overall the quality was quite good. "That will work for sure. So, look, I'll ask you some questions and give you some direction and you just do your thing. OK?"

"Yes, sir," Megan said. "Direct me. Tell me how to turn you on."

"Damn, there are days I wish I didn't love my wife," Bud chuckled. "This is one of them."

"I know you don't mean that," Megan giggled. "But I'm flattered. I'm so impressed by your devotion to her. You shouldn't feel guilty about this at all. Every time you jerk off watching this, just remember that you're a good man and that I'm doing this because I respect you and want you to be happy."

"You're not what you look like at all, are you?" Bud said as they sat and ate some fries before starting the video.

"What do you mean?" Megan said. "I mean, I know I look like a little slut dressed like this."

"Exactly," Bud said. "Like your IQ matches your dress size. But this is new to you, isn't it?"

"Yes, sir," Megan said. She proceeded to tell him about her athletic career, good grades and solid family life. "I have been very fortunate. I know I should embrace the opportunities I have, but, well, I just needed to try being different. I need to know what I want to do with my life, not what everyone thinks I should do."

"Yep, you have to figure out who you are," Bud said. "That's the only way to be happy. I can see that you really like doing things for other people. You're a giver. And I thank you for giving me a gift tonight."

"You're very welcome," Megan said. "Thank you for understanding and not judging me."

"Not a thing about you I don't like," Bud said. "Now, about the video, you don't mind talking a little dirty and stuff like that do you? I mean, it's all just pretend."

"Not at all," Megan smiled. "Only I don't have to pretend to be turned on by you."

"Fuck, you're just natural-born hot. You know just what to say and how to say it," Bud said. "All right, let's do this."

Bud held up his phone and started the video, "So Megan," he began, "do you like sucking cock?"

"Of course I do," Megan said. Her answer was straightforward, honest. Not some fake tease. "And I'm pretty good at it."

"How did you get good at it?"

"Practice, of course," Megan said. "And not just with cocks. I'm not a total slut! I practice with popsicles, blow pops, suckers, dildos, oh, and corn dogs!" She held the corn dog up by her face.

"Why don't you show us a little of your technique?"

'Well, the main thing about being a good cocksucker is you have to want to do it," Megan said. "Sometimes I think I enjoy it more than the guy does. Or at least as much. There's just something about having a big hard cock to play with and tease and worship."

"Worship?"

"Oh yes, in that moment, I'm a slave to cock and balls, a humble servant unworthy of the mighty cock and nutrient-giving cum. I pay my respects and homage to the mighty cock. I stroke it with my hands, kiss it and rub it all over my face." As she said these things, she acted them out with the corn dog. "But I am not worthy, so I punish myself for being so selfish, so lusty." She slapped herself in the face with the corndog, hitting both cheeks.

"I stuff it in my naughty little mouth and stretch myself to make sure I do the job right -- all lips and cum, no teeth." She put the corn dog in her mouth and stuffed it inside her cheek and jabbing it back and forth, showing the corn dog pushing her cheek in and out.

"I know I don't deserve it, but I'm starving for it, so I put it in my mouth, just the tip at first, showing as much restraint as I can." She demonstrated for a few seconds, kissing and sucking on the corn dog. Then she pulled it out and continued talking. She put the corn dog down and picked up a clump of the funnel cake. "I'm so hungry for it though and I know what I really want comes from the balls. So I lick and suck on them too, showing my respect and begging them to share with me." She licked the powdered sugar off the funnel cake and stuffed the full piece in her mouth. After she ate it she said. "I put both balls in my mouth at the same time just like that and give them tongue bath. I make them churn and ache with pleasure, so full they are desperate to be drained."