tagFirst TimeTomboy Ch. 04

Tomboy Ch. 04


Be sure to read "Tomboy Chapters 1, 2 and 3" before starting this story. Do Tom and Jo get back together or does May move in? Everyone in the story is at least 18 years of age. Copies of this story may not be made for distribution, be publishing or copied to another webpage without explicit permission from the author.


Tom sat on a corner bench on a dark street corner after his talk with Jo. He fought back the tears and thought about calling her again but he knew she had already made up her mind and her basketball scholarship and grades were more important to her than he was. The thought entered his mind to go home and lock himself in the basement but he knew he would be too depressed. He put the cell phone in his pocket and headed down the street to Jack's Diner where the teams were celebrating.

"Hey Tom over here!" Calvin yelled at him from the back of the diner. Jack, the owner of the diner, was a big Central Catholic supporter and always had the teams over after the games. Most of the diner was empty except for the happy victors.

Tom staggered over trying not to look too sad about what had occurred with Jo. He saw Billie and Tina hugging in one of the booths and slid in before anyone else grabbed him. "Hi."

Tina had talked to Jo before she cut out and knew what happened. Billie also knew but neither of them had told anyone else. They wanted to hear it from Tom first. "Did you talk to Jo?" Tina asked.

"Yeah, I can't believe she feels I'm the cause of her bad game or grades."

"She is messed up right now being in love with you. She told me she hoped you can wait until the season is over and to give her another chance," Tina whispered.

Tom shook his head. Things had been so perfect. He had found someone he really loved and he enjoyed his success on the team. "God, it was just one game." He said as he leaned back and closed his eyes. He felt someone slide into the booth next to him.

"Nice game Tom," May whispered as she pushed her bare thigh against his leg. "I heard Jo is not coming here tonight."

"Get lost May," Tina glared at her larger team mate.

May thought about telling her to get lost but just smiled. "If you get lonely let me know." She stood and pushed down the short skirt before winking at him and walking away.

"We have a three day weekend coming up with no practices," Billie announced. "What are you going to do?"

"I think I'm going back to Clarkton," Tom said softly. "I have some loose ends to take care of."

"Tom, Jo loves you," Tina said hoping he would not go looking for someone else.

"If she really loved me she wouldn't be doing this to me," he said as he moved out of the booth.

An hour later only a few kids remained and the manager told everyone the diner was closing. Tom grabbed another Coke and headed down the street to his Grandparent's house. He did not notice the other person walking behind him nor did he hear her footsteps as she drew near.

"Tom," the voice behind him said. He turned suddenly hoping it was Jo but saw May instead.

"It's not a good time right now May," Tom said as he waited for her to catch up to him.

His body was rapidly betraying him as he thought of them on the bed at the party and her long legs opened ready for him to enter her.

"I heard about Jo," she smiled. "I just wanted to make sure you were alright."

"Not really," he answered. "How did you find out so fast?"

"There are not too many secrets at Central," she answered. "My house is just around the corner if you want to stop for a while."

"I don't think that's a good idea," he replied. He remembered what his Grandmother had said about girls who come on too fast.

She laughed. "I promise not to bite you."

Tom was hurting so much he did not want to be alone. He felt he could control himself around May and if things started getting out of hand he could leave. "OK but only for a few minutes."


Jo had tried to go to sleep but was too messed up as she thought about Tom. Maybe she had been too quick to stop their relationship until after the season. She quickly dressed and walked down towards the diner. Even if she wasn't going to go in at least she would be able to see him from the distance. When she arrived at the diner most everyone had gone but she could see his tall form towards the back room. "He's not having a good time," Jo thought.

She waited across the street behind a brick stairwell when she saw him come out. He walked slowly down the street towards his house.

"Maybe if they talked they could resolve some of her issues of him being in the stands and spending less time during school nights," she thought. As she moved up from the stair well she saw someone else come from behind the diner. It wasn't until the form moved under a large street light that she realized it was May. She tried to catch May before she got to Tom but couldn't and had to hang back as the two talked. Her worse fears suddenly came to be when they turned and walked down the street where May's house was.


"My mom and dad go to bed early so be quiet," May whispered as she led Tom to her bedroom which was on the first floor but towards the back of the home.

Tom realized May had done this many times before as she closed the door behind him and quickly cleaned up a few items of clothing. "Sit on the bed and I'll be right back," she grinned.

He felt like the fly waiting for the spider to return as he looked around her bedroom. Her closet was open and he could see a few silky blouses and dresses hanging on the rack. He knew this was a big mistake and stood to walk out the door when the bathroom door opened and May came walking out wearing only a beige teddy. At first he thought she was completely naked.

"God," he muttered. She giggled, walked in front of him, and pushed him back on her bed.

"Do you like?" she smiled as she did a slow 180 turn to show him her pink ass cheeks poorly hidden by the high rise teddy.

"May we can't do this," Tom said. His voice was saying one thing but his body said another.

"No strings attached," she smiled as she pinched the spaghetti straps on her shoulders and slowly pushed them down her arms. The beige silk moved like an apple peeling losing it's skin down her large mounds. "No one will know." Tom's eyes widened when the top of her pink nipples appeared and then the long hard tips.

"This is not a good idea," he whispered but again did not move. Suddenly both of her naked orbs popped out before his eyes.

She didn't respond as she continued to push the garment down over her flat stomach and small butterfly tattoo. "Do you like my butterfly?" she teased as her fingers gently brushed over the design that rested just above the top of her trimmed bush. "My butterfly likes to be kissed. Will you kiss it for me?" She moved her body forward until her knees pushed against his. Her fingers reached out and captured his head and pulled until his lips were only a few inches away.

His muscles were like putty and had no strength to resist. He closed his eye and pushed his mouth forward until they touched the soft flesh where her tattoo was. "No one will know," she repeated again as her own fingers pushed the teddy down past her dripping pussy to her ankles. She stepped out of the teddy and stood naked before him.

"Now you need to kiss my flower," she whispered. Her fingers gently pushed down his head until his lips moved over her thin sliver of pubic hair. As he moved lower his mouth automatically opened and his tongue licked at the top of her moist slit. She grabbed his hands and pulled them around behind her until they cupped her firm butt.

"No one will know," she smiled when the tip of his hot tongue flicked against her swollen clitoris.


Jo knew where May's bedroom was and hurried around the back of the house. She tried to peek in the small window but couldn't see around the curtains. She knew May was a slut and also knew Tom was weak after what she had done to him that day. Some how she needed to stop them. She wasn't sure where May's parent's bedroom was so she tossed small stones at all the windows on the second floor. At first she thought she was out of luck until a light suddenly came on. She ducked behind the garage cans.


Tom was in lala land as he sucked and licked May's experienced pussy. His fingers squeezed her ass as he felt her push him onto his back. He didn't resist as she quickly released his fly and pulled out his huge hard-on. He expected her to touch and explore him for a while and therefore was not ready as she quickly moved her hot hole over his shaft. As the tip pushed an inch inside her inner lips someone pounded on the door.

"May! Are you awake?" May' mother's voice rang out.

"Shit," she said. "Be quiet and I'll get rid of her," she whispered to Tom.

"Yes Mother," she yelled. She tried to lower her pussy down his shaft but Tom' hands on her waist prevented it.

"Someone is throwing rocks at the house!" her mother yelled.

"They will go away," May said totally pissed. "Go back to bed."

They both waited for a reply but got none. They heard her footsteps walking away. "She's gone so do it," May grinned as she pushed her juicy opening down almost an inch again before Tom lifted her up and off of him.

"What are you doing?" May asked totally exasperated.

"Something I should have done before," he said as he zipped up his shorts and moved to the door. "I promised my Grandma."

"WHAT?" May asked.

He smiled and slipped out into the hallway.

He did not see Jo hiding in the alley as he hurried down the street and back to his house. Grandma Bell was sleeping in the rocking chair near the door when he tried to slip in quietly. "I can hear you," she said.

"Hi Grandma," Tom said as he kissed her on her forehead.

"Did you have a nice night?" she asked. She stared into his eyes and could see something was bothering him.

"Not really," he said as he sat on the sofa across from her. "Jo and I kind of broke up."

Of all the girls Bell had met the only one she liked was Jo. "And you are just going to sit there and not do anything about it?

"There's nothing I can do," he said looking downward.

"I've seen the way she looks at you and the way you look at her so don't tell me there's nothing that can be done."

"She had a bad game tonight and said it was because I was in the stands distracting her. And she also failed an exam because we are spending too much time together during the week."

Bell shook her head. "Think about what you just said tonight and talk to me again in the morning. I'm going to bed."

Tom watched his elderly grandmother shuffle off slowly to her bedroom. He moved down the stairs and put on the DVD "Love and Basketball". As he brushed the fishy smell from his mouth and lips he looked in the mirror and smiled. "Thank you Grandma."


Jo didn't get much sleep that night still worrying about her relationship with Tom. She told her sister at the breakfast table what had happened just to keep her quiet and waited until she left for school before she picked up her cell phone to call Tom. She wanted to tell him one more time she loved him but couldn't be with him until after the season was over. As she walked out the front door to walk to school she took a big breath and pushed the send button. Suddenly she heard the ringing of a phone and looked down to see Tom sitting on her front steps. He looked at her name on his cell phone caller ID and smiled.

"Hi," he smiled as he pushed his answer button and turned to look at her.

"What are you doing here?" she asked into the phone.

"I had to see you," he answered with a grin. "I love you Jo and can't wait until the season is over."

She hung up her phone. "You have too," she said again almost in tears.

"Tell me you don't love me," Tom said as he stood to block her path down the steps.

"That's not fair," she said. "I'm letting down the team."

"I won't come to your games," he said smiling remembering what his Grandma had hinted at last night.

"But I'll still be thinking of you," she whispered.

"Jo, I hope you will be thinking of me anyway. All I'm asking is for you to try it once. I know you and know you don't like to lose," he smiled. "We can see each other on the weekends if this works."

Jo stopped and bit on her lower lip as she thought about what he had said. Then she remembered last night. "I saw you go into May's house last night. If you really loved me you wouldn't have done that."

"Jo I fucked up," he said. "I thought I could control my desires and was real lonely last night. If it wasn't for someone throwing rocks at her house I could have done something......" Then it hit him. She had saw them going into the house which meant it was Jo who threw the rocks. "Thanks," he said blushing.

"I did it for me not you," she said as she pushed him hard against his chest. "If you ever think about cheating on me again I'm going to use bigger rocks and my target won't be a house."

Tom smiled. "Does this mean we are still together?"

"Maybe if you carry my book bag to school I'll think about it," she grinned. She moved into his arms and gave him the hottest, wettest, and sexist kiss ever.


It was later that day during the girl's practice that Jo got even with May. A group of older boys from the baseball team had started pre-season practice and were sitting around waiting for the girls to finish their practice so they could have the gym. It was during the last defensive practice set that Jo waited until May's rear faced the boys on the bleachers when she grabbed hold of her shorts and panties and yanked downward. Before May could react her naked ass was mooning the whole baseball team upperclassmen.

Coach Meagan saw what Jo had done and thought about busting her but her star player had been having a rough time lately. Besides she figured May must have deserved it. She turned and left the gym before anyone saw her leave.

"JO!" May cried out as she tried to bend ladylike to pull up her panties and shorts. The problem was that if she bent with her ass to the boys they would see up under her legs at her pink slit. If she turned they would see her bush and pussy.

"What the hell," she grinned as she turned and slowly pulled up her panties and then her shorts. The whole team was standing and applauding.

"Shit," Jo said to herself. "She liked it."

Later as Jo stood under the warm shower she peeked out to see May walk into the shower room. She was ready to throw a punch at the taller girl but saw May smile and glanced down at Jo's nearly perfect body. "I can see what Tom sees in you," she said.

"You don't get it do you?" Jo laughed. "It's not the biggest tits or best blowjob. It's what's in here," she said pointing to the space between her breasts. "If you ever look at him again I'll kick your ass."

May tried to smile but couldn't. "He didn't do anything he didn't want to do."

"Just remember what I said," she said as she smacked May hard on her pink buttocks. The sound rang out into the locker room.

Tina and April were giggling when May walked out of the showers. They waited until she turned around before they saw Jo's hand print on her ass. "We didn't know you were into spanking," Tina laughed. May's face turned red and she started coming at the smaller girl until Jo stepped around the locker. Jo was small too but they all knew she could fisticuffs with the best of the boys. May turned and quickly got dressed.

"So everything is OK with Tom again?" Tina asked Jo as they walked to Jo's house.

Jo smiled and told her the whole story. "I guess we will see next week at the game. We will see each other only on the weekends."

Tina remembered what Tom had said about going to Clarkton. "Is he still going back to Clarkton this weekend?"

Jo stopped walking and looked at her. "He never told me he was going back there." Jo knew his old girlfriend Tracy would be waiting with open arms.

"He....," Tina hesitated. "He must have forgotten or maybe he changed his mind?"

Jo said goodbye to Tina and called Tom's cell phone. He had to be out of practice by now. He answered on the third ring. "Hi," he said out of breath.

"Did I interrupt anything?" Jo asked.

Tom realized she was referring to his heavy breathing. "No," he laughed. "I ran to the locker and had to fish out the phone. What's up?"

"Are you going to Clarkton this weekend?"

"I should have known Tina would have told her," he thought. "Yes but I was going to ask you to go with me."

"When were you going to ask me tomorrow morning before you left?"

"No, tonight when you come over to my house. We have the house all to ourselves. Even Grandma Bell will be gone."

Jo's pulse quickened. "Alone? Just the two of us?"

"That's OK isn't it?"

"Oh yeah, that's better than OK. What time?"

"My family is going out at 6:30PM so anytime after that."

Jo was waiting across the street at 6:20PM for the family to leave.


Tom told his family to leave and he would clean up the kitchen. It was getting late and he wanted them out of the house.

As soon as he heard their car leaving down the street the doorbell rang. He was wearing his Grandma' apron when he opened the door. "Are you a hussy?" he said in his best impression of his Grandma's voice. "That skirt is a little short isn't it?"

Jo laughed and pushed him into the door. She closed it behind her. "Why Grandma what big eyes you have," she giggled. She pushed on his nose. "What a big nose you have." Both were laughing as she picked up the apron and grabbed his forming bulge. "And, what a big THANG you have." Tom sucked in a big blast of air as she stroked his shaft. "Why Grandma," she giggled as she unzipped his pants and pulled out his hard-on. "Is this for little red riding hood?"

"Yes....dearie......." he gasped as she stroked him. He watched as she leaned forward and pretended to open her mouth over his huge crown. Suddenly she pulled back and ran down the hallway.

"Hey that's not playing fair!" He yelled as he ran to catch up to her. His hard prick bounced up and down with each step.

Jo ran down the hallway and into a small closet off of the kitchen. She heard him coming and moved back behind some long coats. His footsteps moved down the hallway and stopped by the closet door. She held her breath as she waited for the door to open. But, it didn't open and she heard him walk away. "Surely he saw me duck into the closet," she thought.

Jo remained in the closet for almost five minutes before she realize he was not looking for her. She moved out and peeked down the hallway. Nothing not even a sound. She left the door open and tip-toed into the kitchen. Still no Tom. A quick search of the first floor showed nothing either. She smiled as she moved down the squeaking stairs to his room in the basement. Again there was no Tom.

"OK enough is enough," she said softly as she climbed the stairs to the first floor and then the second floor. The first two bedrooms were empty but the third one had two candles lit and the bedspread turned down. She smiled as she entered.

"It took you long enough," Tom grinned when he saw her walk cautiously through the doorway. He moved from a small chair and walked up to her.

Jo giggled and looked at the bed. "Are you planning something?"

"Yes, and to make it interesting I'm challenging you to a game of HORSE."

Jo looked over his back at the small basketball goal mounted on the bathroom door. "And what are we betting?"

"First of all our clothing," he smiled as he unbuttoned the top button on her blouse. She smacked his hand away.

"And, second of all," she smiled.

"Whoever loses does what the other person asks."

Report Story

bySlickman© 0 comments/ 212487 views/ 59 favorites

Share the love

Report a Bug

5 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: