Chapter 57: Week of Prep Begins

Madison felt a shaking and opened her eyes. Jordan was smiling at her.

“Hey, kid, I have to go.” Jordan said and Madison blinked to get her bearings. She popped up and looked at Jordan who was naked and lying in her bed. Madison was still wearing her white stockings and heels.

“Jordan, I am so sorry I fell asleep.” Madison said and Jordan laughed.

“It’s fine, you were pretty wiped out and I love watching you sleep.” Jordan said and rubbed her cheek.

“That was quite a ravishing.” Madison said.

“Yeah, that was something, you seemed to like it.” Jordan said.

“You think? It knocked me out. Do you really have to go?” Madison said and Jordan frowned.

“Yeah, it’s 8:30, my dad is expecting me.” Jordan said.

“I am so sorry; I feel like I didn’t do anything. I feel bad.” Madison said.

“Didn’t do anything? You drove me out of my mind with these clothes and I don’t know if I have ever seen a more beautiful orgasm.” Jordan said.

“So, you liked my ravishing clothes?” Madison said and Jordan nodded.

“Very much.” Jordan said and Madison giggled.

“Ok, I guess I will have to owe you one.” Madison said and leaned over and kissed Jordan’s nipple.

“I will take that IOU.” Jordan said as she watched Madison lick and suck her nipple.

“You sure you don’t want to stay a little longer.” Madison said and ran her tongue over and around the small pink nub.

“Baby, I would love to stay here for a week, but I really have to go.” Jordan said and Madison pulled off her nipple.

“Ok, you might want to get dressed.” Madison said and Jordan laughed.

Jordan slid off the bed and picked up her panties. She slipped them on and reached for her bra. She found it and put it on. She pulled up her jeans and heard a giggle. She looked up to see a cute 14-yr old wearing only heels and white stockings and smiling. She was not sure she had seen anything so hot in her life.

“I just remembered you hopping around earlier trying to get your pants off.” Madison said and Jordan smiled.

“Yeah, that right there impacted my balance.” Jordan said and moved her arms in a circle in the air around Madison. Jordan heard that lovely giggle and slipped on her shirt.

Madison slipped off the bed and took Jordan’s hand. Jordan looked at the cute little body and sighed.

“You really make it hard to leave you.” Jordan said and Madison smiled.

“That’s the idea, right?” Madison said.

Jordan walked out of the room holding her hand. She went down the stairs, watching the little boobs bounce with each step.

“That is pretty.” Jordan said.

“So, you like watching me walk down stairs topless.” Madison said and Jordan nodded.

“Very much so.” Jordan said.

“Good to know.” Madison said and they stopped at the door.

Jordan put her arms around Madison and looked at her.

“You are something special.” Jordan said.

“Thank you, so are you.” Madison said.

Jordan moved her hands down to the firm little ass and then lifted Madison. Madison squealed and wrapped her legs around Jordan. Jordan kissed her and Madison grabbed her head and pulled her deeper into the kiss. Jordan squeezed the wonderful ass in her hands and wrestled with a little tongue. She pulled off the kiss and Madison gasped.

“You are like a drug; I can’t seem to get enough.” Jordan said.

“So, you’re addicted to me?” Madison said.

“Seems so.” Jordan said.

Jordan put her back on the ground and grabbed a cute breast.

“I will see you tomorrow, be ready to work. We only have 4 practices left. I don’t like to do much on the day before the meet. We may just talk.” Jordan said.

“And kiss?” Madison said and Jordan laughed.

“There may be some kissing.” Jordan said and Madison smiled.

“Aye aye captain, I will be ready.” Madison said and Jordan laughed at the little naked girl saluting her.

“Get some rest silly girl.” Jordan said and kissed her.

Madison watched Jordan walk to her car and Jordan turned and saw the cute little breasts one more time before she got into the car as Madison stood on the porch and waved. She looked around and hoped no one else saw, it was almost dark so that was good. She got into the car and drove away from her; she felt a little sad about that.

Madison walked slowly back up the stairs to her room and then slipped off her stockings. She thought for a second about keeping them on for Mr. Jones, but she thought maybe that was too much. She found some loose shorts and a t-shirt and slipped them on. She packed her bag with some clothes for school tomorrow. She grabbed her backpack, making sure her phone was in there, and walked downstairs. She locked the door and headed next door.

Barry heard the knock and opened the door. She was smiling and holding a bag with her backpack over her right shoulder. She was barefoot with her small shorts and shirt. He saw her nipple as the shirt was pulled tight by the backpack.

“Excuse me sir, do you have a room for the night. I don’t have any money, but I have other ways to pay you.” Madison said and lifted her shirt. He saw a little breast appear and he grabbed her and pulled her into the house.

“Madison, you have to be careful.” He said and she giggled.

“You are too nervous, it’s dark and my back was to the street, unless you have a neighbor in here or something.” She said and looked around.

“You are crazy.” He said and she smiled. She tossed her bag on the couch and her backpack on the floor. She pulled off her shirt and yanked down her shorts. He gasped as she turned around to face him.

“No, this is crazy. I have a new rule, no clothes in your house.” She said and he frowned.

“Madison, you don’t have to do that.” He said.

“Mr. Jones, I know. You didn’t make the rule. So, do you want me naked in your house or with clothes on?” She said and looked at him. He stared at those precious breasts, and he could not think straight.

“Um, naked, I guess.” He said and she giggled.

“You’re not sure?” She said and stepped closer to him, grabbing his hand and putting it on her breast.

“Um, no, I’m sure.” He said and she smiled.

She bent over and picked up her clothes and put them in her bag. He watched her little ass as she dug in her bag. She pulled out some yellow panties and a bra and dropped them on the couch. She pulled out a jean skirt and a green shirt. She dropped them on the couch and zipped up her bag. She opened another pocket and pulled out a brush and a small bag. She turned and looked at him. His eyes of course gravitated to her breasts.

“Mr. Jones, I am going to take a shower. I think you promised me some pizza. I am pretty hungry. I would also like you to brush my hair when I get back, will you do that?” Madison said and he nodded.

“I would love to; I will order the pizza.” He said.

“Cool, see you in a few minutes.” She said and he watched his young neighbor walk out of the room naked. He shook his head and wanted to pinch himself to make sure he was not dreaming.

Barry made the call for the pizza and then grabbed some paper plates and cups. He put them on the table, along with some napkins. He sat down and thought about what was happening. She was going to walk back in here naked most likely and she would probably want to have some sort of sex with him. She was 14 fucking years old. All he had to do was say no but he was not sure his mouth could make that word with her looking at him with that face. Alex said he was a puppet in front of her and he feared she was right. His old cock lurched in his pants, happy with his weakness. He sighed and put his head in his hands. At least at his age he wouldn’t have to worry about too many years in prison. He got up to get him some coffee to try and clear his head.

Barry sipped his coffee and then turned his head to see her walking over, her hair wet and hanging over her shoulders with a towel wrapped around her. He saw her cute feet and legs under the towel. His cock tingled again. She was holding her brush and smiling. She sat in the chair next to him.

“Mr. Jones, I broke the rule already, but I didn’t want to drip all over the furniture.” She said and he looked at her towel.

“I don’t know, I may have to punish you.” He said and she looked at him and then a smile formed on her cute face.

“Hm, maybe a spanking?” She said.

“I am thinking that may be appropriate.” He said.

“That sounds fair, but you have to use some lotion after you are done so my butt doesn’t hurt too much.” She said and smiled. He groaned and she giggled. She held out the brush and he stood up.

He started brushing the long hair and she sighed. He knew she loved this and he loved doing it. He ran his fingers through the soft hair as the brush ran through it. He was lost in a daze when he heard the knocking. He put down the brush and walked to the door. He opened it and an older man stood there with a pizza box. Mr. Jones took it and signed the paper. He noticed the man looking over his shoulder. He handed him the paper and the man smiled.

“You have a great evening sir.” The man said and smiled way too big.

He closed the door and took a deep breath. He carried the pizza to the table and set it down. She squealed and grabbed a plate. She looked at him and he looked worried.

“Mr. Jones, what is wrong?” She said and took a big bite of pizza.

“That man saw you.” He said.

“What man?” She said with a mouthful of pizza.

“The man that brought the pizza.” He said and she sighed.

“He saw me, so?” She said.

“Sitting at my table in just a towel.” He said.

“How did he know that?” She said.

“He saw you, Madison.” He said.

“Mr. Jones, he saw a girl with a towel wrapped around her bathing suit. She was probably your granddaughter or niece, and we were having pizza.” She said and took another bite.

“But, ok.” He said. She got up and walked over to him. She touched his arm.

“Mr. Jones, I understand. However, the only way anyone will find out what we do is if they see us or tape us. If anyone suspects anything and asks, I will say you have never touched me, end of story. So, no naked stuff in the front yard and no taping anything, ok?” Madison said and he sighed.

“I wish I could be as comfortable as you.” He said.

“Am I going to have to spank you after you spank me?” She said and he smiled.

“No, that would not be exciting.” He said and she giggled.

“Ok, fine. Enjoy your pizza and then we can have some fun.” She said and he took a bite of pizza.

He watched her and she was so freaking cute and so at ease with herself. He was very old, and she was very young, why was she so interested in doing stuff with him? He took a deep breath and tried to relax.

Madison finished her pizza and put her plate and cup in the trash. She stood next to him and put her hand on his shoulder. He looked at her and she kissed him gently on the lips.

“Mr. Jones, I don’t want to make you uncomfortable. Sam tells me all the time that I get carried away and make things weird. I don’t want to make this weird between us. I love you too much and it would break my heart.” She said and he nodded.

“But I think you are really cute, and I love doing these things with you. It makes me feel good and I love to see your face when we are doing them. I think it makes you feel good too. You could never hurt me because I love you and I want you to do this stuff with me.” She said and he nodded.

“So, here is what I am going to do. I am going to drop this towel and walk over to that couch. If doing this stuff makes you too uncomfortable then just walk over and cover me with the towel. I will understand, we will still drink chocolate and sit on your swing. But if you want to keep doing these things with me then walk over and start my spanking. Then we can keep exploring together and you can do anything to me you want. It will always be our little secret. Does that sound like a good plan?” She said and he nodded.

“Ok, you take your time.” She said.

She pulled her towel off and laid it over the back of the chair. She walked over and pulled something out of her bag. She got on her knees on the couch and put her head down into the cushion. He saw her young firm ass sticking up in the air and he sighed. He saw her close her eyes. She was waiting for his decision.

He sat at his kitchen table and looked at the young naked girl on his couch. He thought about his buddy in California and the conversations they had about her as they watched her on the cameras. He knew what his vote would be, but he didn’t watch her grow up next door and he was not friends with her father. He thought about the words she used, exploring and their little secret. What man would turn down that offer, a cute 14-yr old giving herself to him to explore things sexually with her. He was already most of the way there; she had sucked him, he had fucked her, and he had anal sex with her, and it was both of their first times. He chuckled when he thought about a 70-year-old virgin. He also thought about what would happen if anyone found out, Henry would be crushed, he would be in jail, and she would be very sad. Was all this potential fun worth the risk?

Madison wiggled her butt a little but kept her eyes closed. She was taking a chance; he was very nervous about the things they did. He might just put the towel on her and be happy with the talks. She would be sad; he was her favorite old man, and he was so good at the butt stuff. Who would she get to replace him. She chuckled when she thought about what Sam would say, “you don’t need a butt guy rock star”. Madison sighed when she thought about what she was doing, she was pretty sure everyone would think she was crazy. But they didn’t have these feelings running through them. Her pussy was dripping with the anticipation of his hand hitting her butt. She could not look at an old man and not feel a tingle between her legs. She loved this particular old man; she didn’t want to give herself to strangers. She thought about the talk with Katie, if she lost Mr. Jones what would she do? Something dangerous?

She heard the chair, and she knew he was standing. She heard his shoes on the floor. She prayed and hoped and stayed still. She tried to relax but she was so scared she was going to lose him. She thought about his worried face when he thought the pizza man saw her. She heard him stop, she wanted to open her eyes so badly and see if he was holding the towel, but she kept them closed. She could feel her skin aching for him. Please Mr. Jones, please, the words flowed through her young mind. She took a deep breath and then she felt the sting on her butt, and she yelped.

“You have been a bad girl.” She heard his voice and she smiled. She yelped again as she felt his hand hit her cheek.

“I am so sorry, Mr. Jones, I will be better.” She said and he spanked her again.

“You need to pay more attention to what you are doing.” He said and popped her again.

“I will, I will.” She said and tried not to cry out in pleasure. His hand hit her butt again and a moan escaped her lips.

“Are you enjoying this, my little scamp?” he said and she smiled. He spanked her again.

“Yes, sir, I am sorry for that as well.” She said and he laughed. She looked back and he was smiling.

“Sorry, that was funny.” He said and she giggled.

“Are you done?” She said.

“So, do you want me to be? Your butt is a little red.” He said.

“Yes, please, can you spread lotion on it?” She said and held out the bottle of lotion she had hidden. He groaned.

“You said you would, my butt is burning.” She whined and he took the lotion. She smiled.

She whimpered as he spread the lotion on her warm skin. It felt nice and she would not mind him doing that every day. He stopped and she looked back.

“Now put some inside.” She said and he looked at her butt.

He looked at the pink skin on her firm cheeks where he had spanked her and then he saw the little brown hole he had been in before. He took a deep breath and figured in for a penny, in for a pound. He squirted the lotion on her and slid his finger into the tight little hole. She whimpered and moved her hips. He moved his finger in gently and felt her grab his finger as she clenched. He pulled it out, squirted some more lotion and slid his finger back inside the warm tight opening. She moaned again.

“Mr. Jones, please.” Madison whimpered.

“Please what baby?” He said. He pushed his finger deep and moved it in and out slowly. She moved her hips and made a soft noise.

“Please put it in.” She said softly. He slid in his finger and reached for his pants. He popped the button and then unzipped; he was proud of himself that he did this with one hand as his pants fell to his ankles. He fished out his old cock and he was rock hard. He squirted some lotion on his shaft and spread it around. He slid his finger deeper into her tight ass.

“Are you ready baby?” He said and moved his cock over her cheek.

“Yes, please put it in.” She said softly.

He pulled his finger out slowly and she gasped. He put his cock on her small hole, and she wiggled her hips. He pushed and saw the head of his cock disappear into her ass. She whimpered and picked up her head. He pushed gently and more of his cock slipped into her warm teen ass. He watched as he moved completely inside her. She was moving her head and moving her hips. He put his hands on her hips and held himself deep inside her tight ass.

“God, that feels so good.” She whimpered.

He continued to be shocked that he was fucking his little princess in the ass. This was incredible and he was very happy with his decision. His cock felt amazing wrapped in the tight warmth, and he didn’t think anyone could come up with a punishment that would wipe the smile off his face. She grunted and threw her head in the air. He reached around and grabbed a small boob. She shivered and moaned.

“Mr. Jones, I love this, and I love you.” Madison said softly as he squeezed her boob and fucked her ass.

Madison’s head was spinning with pleasure. He felt so good inside her, she knew a larger one would probably hurt but his was just the right size for her. She pushed back against him and felt him go deeper. He was holding her breast and that added the extra flair to all of this. He was handling her body and she loved it. She felt him pull out and then push back in gently. He was a master at this, and she was a lucky girl.

Barry continued to convince himself that he was awake and not dead. His cock was in heaven as it moved in and out of the small hole. He looked at her ass and her small body and his cock got a little harder. Her breast was soft and firm in his hand and it gave him a little leverage. He squeezed it and then lifted her, pulling her body against his while he stayed buried in her tight ass. He moved his other hand up and held both of her breasts. He saw her turn her head and her eyes were unfocused. Her small, cute mouth was open slightly. He leaned over and kissed her. She moaned into his mouth as his tongue explored.

Madison felt his body against her back and then he grabbed her breasts. She was starting to vibrate a little with excitement. He rubbed her nipples and then he kissed her. She felt a surge of pleasure flow through her, and she felt a tremor. She reached down and touched her pussy. It was hot and wet, and she ran a finger over her button. Another tremor ran through her, and she pulled her finger back. She moved it around her button, teasing herself and bringing her pleasure higher. He was kissing her deeply, his tongue flying around her mouth. His hands were squeezing her breasts and pinching her nipples. His thing was hard and deep inside her body. She touched her button and pushed. She felt the massive wave of pleasure and she broke the kiss and screamed.

Barry heard her scream and felt her body start to shake. He held onto her boobs and pulled her back against him as she came hard. Her ass was squeezing his cock as her body shook and shivered. She was breathing hard with her mouth open. He held onto her little body and let her move through her orgasm. He had never felt anything like this before, it was magical. He was not sure he would ever be able to top this. She was slowing down her breathing and he felt her tremors getting a little farther apart. He kissed her cheek and she smiled.

“Are you ok?” He said softly and another shiver hit her, vibrating his cock.

“Yes, are you?” She said and looked at him.

“Baby, I have never been better. This is amazing.” He said and she smiled again.

“Good, but now you have to finish. You can let me go now.” She said and he let go of her breasts. She lowered her body and grabbed the back of the couch. She wiggled her hips and looked back at him.

“Mr. Jones, you can go ahead and fuck me now.” Madison said and his cock grew even bigger.

Barry grabbed her smooth hips and started a rhythm in her tight young ass. He knew this would not take long; he was surprised he hadn’t blown his wad yet. He held on and fucked her nice and slow, bottoming out on every stroke. He loved the feel of her butt cheeks as he moved against her. He was able to keep this up for a couple of minutes and he was sad about an orgasm for the first time in his life. He pushed deep into her and felt his juice flow into her bowels. He held her against him as his breathing slowed. She was not moving, just letting him drive and he considered just staying inside her as long as he could. He realized he was definitely dreaming about that and pulled out of her slowly. His cock seemed to want to stay as it moved out. He saw her hole stay open for a couple of seconds and then close quickly, a couple drops of his seed seeped out and ran down her thigh. The small hole looked pristine again as he moved back and collapsed on the couch.

Madison scrambled and sat on his lap, putting her head against his chest. She heard his heart, and it was remarkably slow and steady. She ran her hands over his shirt and then down his arm. She felt his thing under her, it was wet and soft. Her butt felt slippery and wonderful. She looked up at him and his eyes were closed.

“Mr. Jones, will you do that for me for my whole life?” She said softly and he groaned.

“Madison, I will do that for you as long as I can.” He said softly, not opening his eyes.

“Good, I really like it and you are amazing. Are you sure you have never done that before?” She said and he chuckled.

“I am very sure; that is not something you forget.” He said and she snickered.

“I guess we have to go to bed now, I have school tomorrow.” She said and sighed.

That comment slammed against his brain, school, yes, he just fucked a schoolgirl in the ass, a freshman at that. He was an evil man, but he was a very happy evil man. He moved his hands back over her small body, rubbing her smooth back and then grabbing that firm little ass. She giggled and he squeezed.

“I guess we should, are pajamas legal in the house?” He said.

“Nope, sorry, you have to hold me all night while I am naked.” She said.

“Shit, I was afraid of that. I will try my best.” He said and squeezed her butt again.

Barry walked out of the bathroom after brushing his teeth and sitting on his throne. He looked down at the cute little naked bundle in his bed and he smiled. Life was good. He moved around the other side and slipped under the covers. He moved closer and she scooted back until they were pressed together, his soft cock pushing against two soft cheeks. She pulled his arm over and placed it on her boob. He squeezed it gently.

“Good night, Mr. Jones.” She said softly.

“Good night, baby.” He said and held onto his cute little neighbor.

Barry dreamed about everything he had done with her lately. He saw her running around his house naked, laughing and giggling. The sounds were like music as he sat at his table and watched her dance, he loved the way her body moved. Her boobs moved slightly on her chest as her stiff nipples pointed at him. Her tight little ass didn’t shake at all as she jumped around in his living room. He took a sip of his hot chocolate, and she danced over and grabbed her own cup. She lifted it over her head and poured it over her pretty hair. He watched the chocolate move slowly over her small body. He saw her breasts with lines of chocolate running over them. He saw it flow over her belly and then move over her smooth pussy and down her legs.

“Mr. Jones, you will have to lick me all over to get me clean now.” She said and danced over to him.

He started licking her boobs, tasting the chocolate and the sweetness of her skin, it was a wonderful combination. He looked down and saw Roscoe jump on the chair and start licking her pussy. She giggled and lifted her leg, putting her foot on the chair to let Roscoe get closer. He saw his little dog start lapping away at her open pussy. He loved the look of that, and he licked across the small boob again. She took his cup from him and poured it over his lap. He looked down and saw he was naked, his cock now covered in chocolate.

“Oh no, Mr. Jones, now I need to clean you.” She said and then leaned over and sucked his cock deep into her mouth as his little dog worked hard between her legs.

He watched his cute neighbor suck and lick on his cock like a pro. His cock was clean now, but she didn’t stop, and he wasn’t complaining. Her little hand grabbed his balls and rolled them in her small fingers. She sucked him deeply and he felt her hair on his hips. She pulled slowly off his cock and looked at him. Her eyes were bright, and she was smiling with his cock against her lips. She was running her tongue slowly around his head and he wanted to take a picture of this. He reached down and touched her soft cheek.

“Good morning, Mr. Jones.” She said and he smiled. He shook his head and looked again, his cock slipped into her warm mouth and disappeared.

She reached up and grabbed his hand, intertwining her fingers with his. She squeezed and sucked his cock deep into her mouth. He lurched up and she pushed her face into his crotch. He felt his cock explode and he felt her swallow. She pulled back as he blasted more into her mouth, easily swallowing it as she went. She reached the end of his cock and then kissed it and looked at him.

“I am going to get dressed now, I have to go to school.” She said and he looked again.

“Madison, wait, what?” He said and she giggled.

“Did you have a nice dream?” She said and stood up next to his bed.

“Oh God, that really happened?” He said and looked around.

“Yes, it did. Was it good?” She said and he looked at her.

“Yes, baby, it was great.” He said and rubbed his hand over his face. She giggled and danced into the bathroom.

He sat up and moved his legs off the side of the bed. He saw his soft cock flop on his thigh, still wet with her saliva. He didn’t have any chocolate on him so that part was a dream. He groaned and stood up. His boxers were on the floor, and he grabbed them. He pulled on a robe and made his way to the kitchen. He needed coffee badly.

He heard her and looked up from his table to see her walk into the room naked. Her hair was in a ponytail with a green ribbon. Her clothes were still on the couch. She grabbed her panties and bent over to put them on. He saw her cute butt and her little pussy peek out between her thighs. Then he saw her panties cover her butt. She put on her bra and then grabbed her jean skirt. She pulled it up her legs, zipped it and snapped it. He realized then how short those skirts were, he saw it move over the panties but not very much. Were they always that short? She slipped on her shirt and walked over to him, her shirt open and flapping.

“Mr. Jones, sorry but I was in a hurry. Can you button my shirt for me?” She said and he nodded.

Barry started at the bottom and started buttoning. He made it to her belly and looked at the beautiful cleavage poking out over her bra. He kissed the tops of her breasts and she giggled.

“That is nice, I still love that.” She said and he smiled. He buttoned the rest, leaving the top two open. He could see some skin but no cleavage.

“Thank you.” She said and tucked in her shirt. She walked over to the couch and slipped on her sandals and grabbed her backpack. She walked back to him and stood next to him.

“Mr. Jones, I am going to school. I will see you this afternoon. I will want to sit on your swing a little and then have some hot chocolate. I will make you a deal, if this is on the table when I am here, I will know you want to have some more fun. If not, we will just drink chocolate and be silly.” She said and put the bottle of lotion on the table. He gasped and she giggled.

She kissed him gently on the lips and rubbed his cheek. She smiled and then skipped out of his house. He sat there and looked at that bottle of lotion and remembered her face down on the couch with her cute little ass in the air. He sighed and took a sip of coffee.

Madison walked to school and thought about Mr. Jones. He did not seem uncomfortable this morning when she practiced on him, but he probably thought it was a dream. He was wonderful last night on the couch. She felt a shiver run through her when she thought about that. She wanted to do that every day, but she didn’t want to assume he did. She did like the signal she set up, that would give him the option without it being awkward. She took a deep breath and crossed the street.