Chapter 65: More old men

“Ok.” She said. She started to imagine where he would take her. Where would he like to fuck a schoolgirl? Maybe a secret playground? She chuckled as they turned onto a busy street. They pulled into a parking garage. He stopped the car and looked at her.

“We are meeting a friend. I have known him almost as long as Thomas and the guys. He’s a nice guy.” He said. Madison stared at him. She was not sure where this was going.

“I don’t understand.” She said.

“It will be like when Hank brought you to the house to meet us. But it will only be one guy and there won’t be any cameras.” He said.

“What do I have to do?” She said.

“Anything you want. You control this, right?” He said and she nodded.

“Yes.” She said. She felt herself getting nervous. What was she walking into? She looked at him and he was not smiling.

“You don’t have to do anything you don’t want to. You say the word and I take you home right now.” He said and she sighed.

She thought that might be a good idea and then she remembered Shelly’s eye and her anger spiked. She needed to give her the money. She could ask her daddy but what would that conversation be like? She got frustrated and angry last night just talking about not texting him. She looked at Anthony.

“He’s nice?” She said and he nodded.

“You can stop anytime you want. He will do whatever you say.” Anthony said. She looked down at her feet in the cute little socks.

“How much?” She said without looking up.

“$200, try to get that up front. He may give you more at the end.” He said and she nodded. That would give her $1400. She really wanted that laptop, but Shelly was more important.

“How long?” She said and looked up at him.

“An hour at the most but I will be surprised if he lasts more than 30 minutes with you unless you read him a story or something.” Anthony said and she chuckled.

“Ok.” She said. He smiled and opened the door. He walked around and opened her door. He held out his hand and she took it. They continued down the hall, and she thought about what she was doing. She knew the word, but she didn’t feel like that. It was the same as what she did with her men, they would just give her money now. Did that make it different? Would she feel different about Mr. Jones if he gave her $20 every time he fucked her butt? She didn’t think she would. She needed the money for Shelly anyway, so it was nice to get something for things she was already doing.

They walked into an elevator, and he hit the 9 button. An old lady got on and hit 11. The lady smiled at her as she stood there holding his hand. The doors opened on the 9^th floor, and they walked out. She looked back at the old lady.

“Precious.” The lady said softly.

Anthony led her down the hall and they stopped at room 923.

“What do I do?” Madison said.

“Just be yourself sweetie. You are irresistible.” He said. She took a deep breath and nodded, and he knocked. An older man answered the door. He had gray hair and glasses. He looked at her and smiled.

“Gary, how are you, you old buzzard?” Anthony said.

“Good, nice to hear from you.” Gary said and stared at her.

“Can we come in?” Anthony said. Gary shuffled back and held the door.

“Sorry.” Gary said and closed the door behind them.

Anthony walked over and sat on the chair near the small table. Madison stood next to him and put her hand on his arm for comfort. Gary sat on the edge of the bed. She saw him look up and down her body and then swallow. She looked at his pants and saw the beginning of excitement.

“So, Gary, this is Madison.” Anthony said. Gary looked like he was scared.

“Madison, Gary owns the car dealership at the edge of town and a couple of apartment buildings.” Anthony said.

“The big one with all the flags?” Madison said. Gary looked at her face when he heard her voice.

“Yep, that’s the one. Gary has a lot of money and nowhere to put it now that his kids are grown, and his wife is gone.” Anthony said.

“I’m sorry about your wife.” Madison said.

“Thank you, Madison. What grade are you in?” Gary said.

“I’m a freshman.” She said and he flinched.

“How old are you?” Gary said.

“14.” She said and he took a deep breath.

“Anthony, really?” Gary said.

“Gary, you pay women for sex, don’t start wrapping morals around that.” Anthony said.

“Why does this make me feel like a pervert?” Gary said.

“Because you are one. You have been one ever since I’ve known you, that’s why we’re friends and that’s why you’re here. If she had said 18, would you have been all good?” Anthony said.

“Well, sorta.” Gary said. Anthony looked at Madison.

“Say 18 sweetie.” Anthony said. Madison looked at Gary. She was starting to feel more comfortable, he looked harmless, and she thought he may be more scared than her.

“18.” Madison said and walked over to Gary.

She stood in front of him and pulled her shirt out of her skirt. She took his hands and placed them on her sides, under her shirt. He made a small sound as his fingers touched her soft skin. She looked at him and put her hands on the sides of his head. He looked a lot like Mr. Jones, and he had that same look in his eyes when his hands touched her skin. This was just another of her old men, she could do this.

“Are you good at kissing?” Madison said and he looked confused.

She moved forward and put her lips on his. She kissed him gently and then ran her tongue into his mouth just a little. She touched his and then pulled it back slowly, leaving her lips touching his for a few seconds and then moving back very slowly. She looked into his eyes, and he didn’t look scared anymore. He looked like all her men looked when they held her.

“Oh God.” Gary said softly. Anthony chuckled.

“Gary, when she is done with you, you may give her a car.” Anthony said. Gary looked over her shoulder at Anthony. Her mouth was very close to his ear.

“Would you be more comfortable if he left?” She whispered and he nodded.

“Anthony, you can go. I’ll be ok.” Madison said and stared into Gary’s eyes.

“Are you sure baby?” He said.

“Yes, but I’m keeping the car if that happens.” She said and Anthony laughed.

“Ok, I will be back in an hour or call me if he dies on you.” Anthony said. She kissed Gary lightly on the lips.

“Ok.” She said. She heard Anthony stand and then she heard the door open and close.

“You are so pretty.” He said and she smiled.

“You probably say that to all the girls.” She said.

“Yeah, but I realize I have never really meant it until now.” He said.

“You’re very sweet. I won’t need a car for a couple of years.” She said and he groaned.

“Try not to remind me.” He said and she smiled.

“Mr. Gary, I am here because I want to be here. I will never say anything to anyone other than you are a sweet man, and we had a great conversation.” She said and started to unbutton her shirt.

She watched his eyes as she popped each button. They got bigger when her bra came into view. It was just a white cotton bra, but it fit her well, her breasts bulged slightly out of the top. She finished with the buttons and let the shirt fall off her shoulders. He was staring at her breasts with his hands still on her sides. She pulled the red tie over her head and tossed it over her shoulder. She heard his breathing, and she rubbed his cheek. He looked at her and she knew he was hers to do as she pleased. She loved that feeling; he wanted her badly and she was in complete control.

“Mr. Gary, could you kiss me right here please.” She said and ran her finger across the tops of her breasts. She heard him suck in his breath and lean forward.

He kissed her breasts softly as she ran her hand though his gray hair. She let him kiss as long as he wanted, and he eventually pulled his head up. She kissed his lips softly.

“Thank you, that felt nice. Would you help?” She said and turned around.

She felt his fingers shaking as he slipped them under her strap and unhooked her bra. She put her hands over the cups and turned back around. She held her bra up for a few seconds and then let it drop slowly. His eyes bulged as her breasts came into view. She chuckled and he looked at her.

“You’re very cute.” She said. She remembered the first time Mr. Jones saw her breasts and he had the same expression.

“They are remarkable.” He said.

His hands were back on her sides, and she grabbed them and pulled them up and over her breasts. He grabbed them and just held them. She rubbed his cheek again.

“Your hands feel good.” She said and he looked up at her.

She smiled at him, and he squeezed gently. She gave him a little moan and he squeezed a little more. She pulled his head towards her chest, and he moved his hands slightly and kissed her nipple. She felt them stiffen and she held his head in place as he kissed and sucked on her sensitive nipples.

“Yes, just like that.” She whispered and he moved over and sucked on her other nipple.

She let him go again as long as he wanted. Her nipples were wet and tingly when he lifted his head finally. She kissed him again and let her tongue explore his mouth a little. His hands moved to her back, and he pulled her close. She put her arms around him and hugged him. She felt her breasts smash against his shirt. She broke the hug and looked into his eyes again.

“Are you having fun?” She said softly.

“Oh God yes.” He said and she giggled. She saw his eyes lock onto her breasts as they moved on her chest.

“Good, why don’t you do the next part.” She said and moved his hand to the button of her skirt.

He popped the button and pulled the zipper slowly down. Her skirt loosened and fell to her ankles. He gasped when her white cotton panties came into view. She understood now what Missy meant; her underwear today looked like a little girl’s underwear. That must be why Missy dressed her like this. She chuckled and wondered how much Missy knew. He was frozen as he stared at her panties.

She moved his hand to the waistband, and he slipped his finger inside. He pulled her panties down slowly and he stopped when they were on her thighs. Her pussy was perfectly smooth, she made sure of that this morning in the shower, she thought it was for Anthony, but this was just as good.

“Oh, sweet Jesus.” Gary said as he looked at the smooth teen pussy.

She remembered what Anthony said about his office being his church as she was bent over his desk, gagged with her arms tied behind her back. She looked at Gary’s eyes again, maybe this was her church, here with one of her old men. She pushed her panties down farther and they floated down to her ankles. She stepped out of them and picked up her foot and put it on the bed between his legs.

“Can you do my shoe?” She said. He unbuckled the strap and pulled her shoe slowly off her foot. He dropped the shoe and rubbed her small foot. He ran his fingers over the lace at the top of her little sock.

“On or off?” She said and he looked up.

“Oh on, please.” He said and she smiled.

She let him rub her foot for a little while and then she took it away and gave him the other one. He unbuckled that strap and started rubbing that one. She saw his excitement growing on his left leg and when he finally let go of her foot, she moved it onto his left leg and started rubbing his cock gently, wiggling her toes over it. He leaned back on his arms and groaned.

She reached down and opened his pants. She pulled down his zipper and then pulled her foot away and knelt between his legs. She yanked his pants down and pulled them down to his feet. She pulled his boxers down and then picked up his cock with her hands. He looked at her and she smiled as she kissed the head. She lapped up the small drop that leaked out and ran her tongue slowly around the top. He moaned and she sucked him into her mouth.

She kept her eyes on him as she moved up and down his shaft slowly. He was breathing hard, and she knew he would not last very long at all. She was right and he filled her mouth after only a couple of minutes. He groaned and laid back on the bed. She stayed on him until he was done and then sucked him clean. She stood up and crawled up on the bed and sat on his lap and looked down at him.

“Sorry about that.” He said and she looked at him with a strange face.

“Sorry about what?” She said.

“It’s been a while, and you are very good.” He said. She chuckled.

“Oh Mr. Gary, we are far from done.” She said.

“Baby, I am pretty much a one shot pony these days.” He said.

“That’s ok, I’m not.” She said and rubbed her wet pussy over his soft cock.

He groaned and she lowered her breast to his mouth. He licked and sucked as she slid back and forth over his cock. She kept it up until she felt herself heating up. She pulled her breast out of his mouth and looked at him.

“Mr. Gary, what else can you do with that mouth?” She said and he smiled.

“Come on up here and I’ll show you.” He said and she squealed.

She moved up his body and put her knees around his head. He grabbed her butt and pulled her down. His tongue licked up her warm pussy and she moaned. She grabbed the headboard and held her pussy just over his face. He squeezed her butt and lapped away. He was not nearly as good as Joshua or Katie, but he was very excited and that got her going. She moved her hips as she felt her orgasm climbing quickly. She wondered how thick these walls were as she felt her legs start to tremble. He sped up his tongue and then he licked all around her button.

“Yes, oh yes.” She said and he kept licking her button.

Her orgasm exploded and she squeezed the headboard and tried not to suffocate him. He pulled her down and she lost her balance and sat on his face. His tongue kept going and she kept cumming. She lifted her hips slightly and she heard him take a breath. He kept licking. She felt another surge of pleasure and she screamed. She bit her hand as another huge wave wracked her body. What was happening? He kept licking and her body was now trembling, and she couldn’t control it. He locked his arms under her and held her up as he licked her like a madman. She shivered and shook until she felt limp. He held her up and didn’t stop. She had never felt anything like this. She was hit with another surge of pleasure and the room started spinning. She tried to stay upright, and everything went dark.

Gary Wilson looked at the small girl quivering on the bed next to him. Her breasts were perfect, and he had trouble moving his eyes off them. Her body was tight and firm without an ounce of fat anywhere. He had never felt that before, surely not from the skanks he usually spent time with nowadays and even from his wife. He had loved her dearly, but she never felt like this little dynamo. He ran his fingers over the stiff pink nipples, and he heard her whimper. He smiled and lightly rubbed her tight belly. Even her bellybutton was cute. She opened her eyes and he looked at her.

“What happened?” She said softly.

“I love pussy and yours is exquisite.” He said and she smiled.

“You are amazing, that has never happened to me.” She said.

“You’re welcome.” He said and she chuckled.

“How much time do we have left?” She said and he looked at his watch.

“About 20 minutes.” He said.

“Good, that’s enough time.” She said and sat up.

“What do you have in mind?” He said. She grabbed his soft cock.

“You’re going to fuck me.” She said and he laughed.

“Baby, you’re going to need more than 20 minutes or some magic dust to do that.” He said.

“Did I forget to mention that I’m a witch?” She said and licked his cock.

She pushed him down on his back and started unbuttoning his shirt. She pulled it open, and he had gray chest hair. She ran her hands through it, and he smiled. She slid down his body and got on her knees between his legs. She picked up his cock again and kissed it. He looked at her.

“You close your eyes and think about how tight and warm my pussy will feel when you slide into it.” She said and licked his shaft.

He moaned and she went to work. She licked all over his shaft and then sucked him completely in her mouth. It went in easily and she felt it start to stiffen slightly as she held it in her mouth. She grabbed his balls and started to roll them in her fingers. He groaned and she knew she was on the right track. She slid his cock out of her mouth and licked slowly down the stiffening shaft to his balls. She kissed them and ran her tongue all over them. He groaned again and she felt his cock lurch in her hand. She sucked one of his balls in her mouth and held it as she ran her hand slowly up and down his shaft.

“Oh God.” He said and she popped his ball out of her mouth and kissed it before moving back up his shaft with her warm tongue. She was close, she felt his hardness and she sucked him back in her mouth, taking a couple of inches into her throat. She swallowed and he pushed his hips up off the bed. She moved off slowly, sucking as his cock left her mouth. She grabbed it and it was close enough. She scrambled up and dropped her pussy onto his cock. She settled on his lap, and he looked at her with big eyes. She felt his cock finish hardening inside her pussy and she wiggled her hips.

“I will be God damned.” He said and she giggled.

“I guess you’re a two-shot pony now. How would you like to do this?” She said and squirmed on his hard cock.

“Just like this, you are fucking beautiful, and I love looking at you.” He said and she smiled.

“As you wish, my lord.” She said and he laughed.

She moved up and down on him slowly and made sure she sat down after each stroke. His cock felt nice inside her. He was surely not Aaron or Joshua or even Frank, but it was nice, and it filled her well. He reached up and grabbed her breasts. That felt good as she moved up and down. His smile never left his face the entire time she moved on him. She stopped and looked at him.

“Thank you, Mr. Gary.” She said. He laughed.

“Well, this is a night of firsts.” He said and she giggled.

“Oh Jesus, that feels nice when you laugh.” He said and she giggled again.

She heard a knock on the door, and he groaned.

“Madison.” She heard Anthony’s voice through the door.

“Do you want me to send him away?” She said as she sat on his cock.

“Do you have to go with him?” He said.

“Yeah, kinda.” She said.

“Then let him in. He can watch all he wants if you stay right where you are.” He said and she giggled again. He groaned and she felt him push his hips up.

“You stay right here.” She said and he nodded.

She jumped up off him and scampered to the door. She opened it and then ran back and jumped back on his cock. She heard the door close, and Anthony laugh.

“I take it he’s not dead.” Anthony said and she looked back at him.

“Nope, we’ll be done in a little while.” She said and looked back at Gary.

“Now where were we?” She said and he grabbed her breasts.

She smiled and started moving up and down slowly. He was moaning a lot and squeezing her breasts. She leaned over more and started speeding up a little. She looked at his face and he was smiling. He really did look like Mr. Jones. She liked this, he loved touching her and she loved being touched. This was an old man with no repercussions. He didn’t have people like Mr. Jones. He wasn’t guilty like Aaron or Mr. Thomas. She bounced a few more times and she felt his body tremble. He groaned loudly and she slammed down onto him and pushed. His cock slid deeper, and she felt it throb inside her. She laid down on his chest and he wrapped his arms around her.

Anthony watched the end of their coupling, and he wondered if he would be able to get her away from Gary. She really was an interesting little girl. He remembered seeing her walk into Hank’s living room for the first time like a deer caught in the headlights. By the end of that session, she was handling them like tigers in a cage. He didn’t even think of it as a gangbang or an orgy, she sucked and fucked them and made it feel like a lovemaking session, just with five guys. Now, she looked like she might have made Gary fall in love with her. He never saw the man smile so much as he did the last few minutes. He had been angry or sad ever since his wife passed. He knew he used hookers a lot, but this was different. Madison provided a different level of service. He shook his head and looked at her cute little ass as she laid on the old man.

Madison sat up and kissed Gary one more time. He hugged her and they kissed deeply as his cock shrunk and fell out of her. She broke the kiss and sat up.

“I think I have to leave.” She said and he frowned.

“She has a daddy, Gary. You can’t adopt her.” Anthony said. Madison shivered when she heard that. Daddy would be very proud of her now. She was in a hotel room with a man she just met, and she sucked and fucked him for an hour. She felt her anger return but she tampered it down. She had to control her emotions. She smiled and lifted her body off him.

“Mr. Gary, do you want to help me get dressed?” Madison said as she stood next to the bed.

“I would love that.” He said and sat up.

“Do you think you could put some pants on first, so I don’t have to look at your junk?” Anthony said and Madison giggled.

“Hey buddy, this is my room, and you’re a guest. You can leave if you want, and I can take her home.” Gary said.

“You would keep her for a week.” Anthony said.

“At least.” Gary said and swung his legs over and pulled her between them. He put his hands on her tight little ass and kissed her nipples.

“That is not helping get my clothes on.” Madison said and he sucked her nipple and looked up.

“Sure, it is. I am getting these perfect little breasts ready for that bra.” He said and she giggled.

Madison broke out of his grip after a minute or so and picked up her bra. He put it on and only kissed her nipples a couple more times. She gave him her panties and he slid them up her legs. He rubbed her pussy for a minute before he slipped them over her hips. She picked up her shirt and skirt and he finished dressing her. She held out her shoe and gave him her foot. He rubbed her foot and then put on her shoe. He rubbed her other foot a little longer and then she stood up before him completely dressed. Anthony handed her the red tie and she put it on.

“I can’t decide if you are prettier naked or with clothes on.” Gary said and she hugged him.

“You’re a very sweet man, and I had a great time.” She whispered in his ear.

“You are an amazing girl. This was the most fun I have had in years. Can you hand me my pants?” He said.

She walked around the bed and picked up his pants and handed them to him. He pulled his wallet out of the pocket and opened it. He pulled out four bills and handed them to her. She looked at him.

“Two shots.” He said and she smiled. She hugged him again and tucked the bills into her bra.

“Goodbye, Mr. Gary. Maybe we can do this again?” She said.

“I sure fucking hope so.” He said.

“So, did you get a car sweetie?” Anthony said.

“Not yet.” She said and Anthony laughed.

She held Anthony’s hand as they walked out of the room. She looked back once more and saw Gary sitting on the bed with just his open shirt and staring at her with a smile on his face.

Madison snapped the seatbelt in place and looked at Anthony.

“How did it go?” He said.

“Really good, I was nervous at first, but it was like you said. I was in control, and it was nice. He is a sweet man.” She said.

“No, he’s not. He’s a prick just like me. You have the crazy ability to turn us into puppies.” He said and she chuckled.

“You said he was nice.” She said.

“Would you have gotten out of the car if I told you he was a prick?” He said.

“Probably not but what if he wasn’t nice to me?” She said.

“I know Gary and I know you. I wasn’t worried.” He said.

“Can we do this again tomorrow?” She said. She did the math in her head. She had $1600 now.

“Are you sure sweetheart?” He said and she nodded.

“Yes. I had fun.” She said.

Anthony put the car in gear and pulled out of the garage. They pulled into his garage 20 minutes later, and she was asleep. He looked at her for a second. She looked all of 14 as she slept against his door. She also just pulled $400 from her first client, and he was pretty sure Gary would want to see her as much as possible from now on. He shook his head and rubbed her arm.

“Wake up sleepyhead.” He said and she looked at him with half-closed eyes.

“I might need to take a shower to wake up.” She said.

“That would be ok. Can I watch?” He said.

“If you want.” She said sleepily.

He was joking but he was tempted. He knew if he did that, he would end up fucking her over the bathroom counter. She had done enough tonight; he would have to wait.

Madison took a shower and Missy brushed and dried her hair. She put on her shirt and jeans and her sneakers and grabbed her backpack. She thanked Missy and went downstairs. He was waiting in the kitchen. They left and she felt much better after her shower.

“Thank you for tonight.” She said.

“My pleasure baby.” He said.

“So, can we do it again tomorrow?” She said.

“I am pretty sure; I have a buddy coming into town tomorrow morning for meetings at the bank. How would you feel about dinner first?” He said.

“Ok. What do I wear?” She said.

“Just better underwear. We will dress you again from Nicole’s store.” He said and she chuckled.

“What would she think about you loaning out her clothes?” Madison said.

“She wouldn’t even notice if she was here.” He said.

“Will Herby be home tomorrow?” She said.

“Probably, I don’t think he has any meetings after school tomorrow.” He said.

“Do you think I could spend some time with him before we go out?” She said.

“Yeah, I think he would like that.” He said.

“Yeah, me too.” Madison said.

He dropped her off at her house and she took a deep breath. She felt better, let’s see if she could control her house a little better than yesterday. She looked at her phone and it was 6:25. Twenty-five minutes late, how much yelling would that get her? She walked through the door and the smell hit her. It was meatloaf. She loved meatloaf. Sam thought she was a lunatic, but she didn’t care. She walked into the kitchen and her dad was wearing an apron and pulling the meatloaf out of the oven. He put it on the counter and looked at her.

“Did you have fun?” He said. She wondered what he would say if she told him exactly how much fun she had.

“Yes, I did. I have a little bit of homework.” She said.

“Dinner’s ready, why don’t you wash up and we can eat. You can do your homework after.” He said.

She looked at him and he was smiling. She wanted to hug him so badly. What was wrong with her? He was her dad. She thought about the word that just crossed her mind. He was her dad but what she wanted was her daddy back. Her daddy would not be disappointed in her. She nodded and walked upstairs.

She brushed her teeth in case he got close. She didn’t smell like Gary anymore since she showered at Anthony’s house. She went into her bedroom and pulled the $400 dollars out of her bra and put it with the rest under her panties. She saw the white lace panties and she knew what she was wearing tomorrow.

Dinner was remarkably pleasant. He talked about his accounts and how Mr. Thompson was very happy with him. She was happy that he was doing good. The meatloaf was very good, and he made mashed potatoes which was almost a necessity with meatloaf. She ate a lot; she was really hungry.

“That was great.” She said and leaned back in her chair.

“I’m glad, I haven’t made it in a while.” He said.

“Save the rest, I love it leftover.” She said.

“Absolutely. How was school?” He said.

“Better, I was more focused in class.” She said.

“Good.” He said. Henry really wanted to talk about other things, but he was enjoying this so much he couldn’t bring himself to bring up any of them. He liked seeing her smile.

“So, tell me about Herby.” He said.

“He’s very sweet and he has a game he plays with two of his friends. It’s a fantasy game and he let me play. I’m a witch that can heal people. It’s really fun.” She said and he smiled. She sounded so much like she did before, maybe there was hope.

“That does sound like fun.” Henry said.

“Ok, I have to get my homework done.” She said.

“I’ll put up the leftovers.” He said.

“Do you want help?” She said.

“Nope, I got it. Get your things done and maybe we’ll have time for a movie.” He said.

She took off and he watched her climb the stairs. He was proud of himself, he made one of her favorite dinners and he didn’t upset her. This was a start, and he was hopeful. She seemed a little more like herself.

Madison walked into her room and pulled off her shirt. She chuckled at her plain white bra and how it was used to create even more excitement tonight. She pulled it off and rubbed her breasts. Gary really liked them, she shivered when she remembered how long he licked and sucked on them. She touched her nipple and sighed. What was it that made men crazy over these? She wondered how much they would grow. She rubbed on her belly and thought about her baby again. She hadn’t thought about her for a while. She smiled when she realized she thought of her as a girl. What if she had a boy? She wasn’t sure it would matter to her. She didn’t know enough about babies to know if there was anything different other than the obvious.