tagFirst TimeTomboy Ch. 02

Tomboy Ch. 02


Be sure to read "Tomboy" before starting this story. Things speed up more at the end of this chapter. 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 was in the basement listening to CDs when the doorbell sounded so his grandmother Bell had to answer the door.

"Yes, may I help you?"

"Err..hi...is Tom here?" Nancy asked as she pushed the short skirt down as low as it would go on her naked thighs.

"Who may I say is calling?" Bell asked. She wasn't bashful as her eyes moved down the tight halter top and down to the very short skirt.


"Wait here," she said sharply as she closed the door without bothering to show her in.

"TOM!" Bell yelled at the top of the basement stairs.

"Yes Grandma!" he yelled back. She was hard of hearing.

"There's a Karen at the door looking for you," she said.

"OK!" he yelled. Shit he looked at the mess in the basement room. "Tell her I'll be there in a few minutes." He grabbed his dirty underwear and tee shirt and pushed them under the sofa cushion.

Bell walked to the door and opened it. "He said to wait. How old are you?" she snapped at the young blonde girl.

"Eighteen ma'am," she answered. "I love your dress. It is so pretty."

"This ol'thing." Bell smiled. "It's a little long don't you think?" The older woman's eyes moved down to the ultra short skirt on Karen's thighs.

Karen knew the woman was judging her from her clothing. She wished now she had worn more conservative clothing. She was lost for a reply.

"Karen!" Tom said as he pushed around his Grandma. "Come in."

"Grandma we will be in my room," Tom yelled back at her. As they walked down the stairs Bell grabbed her grandson's arm.

"Can I talk to you a minute?"

"Sure," he said feeling the pain in her strong grip.

"That girl is a hussy," she whispered. "I can see it in her eyes."

Tom laughed. "Grandma she is not a hussy." He didn't even know what a hussy was.

"I'm not happy with you and her being alone downstairs."

Tom laughed and pulled his arm from her grasp. "If I need help I'll call for you." He turned and closed the door behind him.

"I don't think she likes me," Karen said sitting alone on the sofa.

"She doesn't have to like you. I do," he said as he sat next to her.

"You do?" she said smiling and moving closer to him. "I wasn't sure after you left my house so abruptly."

"I don't want to come between you and Jo," he said. His eyes noticed her hard nipples pressing out the front of her halter top.

"It's just a sister thing," she said. "Were cool with everything," she lied.

"I really like Jo and don't want to mess up our friendship. I was surprised when you said she was gay."

"Yeah I shouldn't have said that," Karen whispered. Her body turned until her lips were only a few inches from his. "She's not really gay."

Tom laughed. "Nice try."

"She's not." Her mouth pressed forward until their lips brushed.

"Yeah right," he said with his mouth barely touching hers.

They were so locked into each other they had not heard the door open or the footsteps.

"Would you kids like to have some cookies?" Bell asked as she stood with a plate of chocolate chip cookies.

Karen almost jumped off the sofa when she heard the woman. She was scared to death of her.

"Grandma, you should knock before you come into my room," he said upset.

"Why? Were you doing something you shouldn't be doing?"

"No ma'am," Karen said as she pushed her skirt down and moved away from Tom.


Jo took her time heading home from Tina's while thinking about the past few days. Normally her day started and ended with basketball but now all she could think of was Tom. She closed her eyes and could see him standing naked before her. She hopped the last few feet up to her door.

"Hi Mom!" she smiled.

"Why are you so happy?"

"I don't know," she lied. She grabbed a large celery stick in front of her mother and chomped down on it. "Where is Karen?"

"She said she was going to that new boy's house," Jo's mother said. "Why?" When she turned around the room was empty and Jo was gone.


"I thought she would never leave," Tom whispered as he moved closer to Karen. His hand dropped to her bare thigh and moved swiftly up to the hem on her skirt. She grabbed his arm.

"I'm afraid she will come back."

Tom smiled as he jumped up, ran up the stairs and locked the door. When he returned to the sofa he saw Karen lying on her back with her head on the small pillow. Her legs were squeezed tightly together.

"Getting sleepy?" he asked as he picked up her feet and placed them on his lap. As he lifted them he peeked under her legs and saw the black panties she had worn before.

"Yes," she giggled. "Why don't you wake me up?" Suddenly his fingers began to tickle her feet. "OH STOP!" She laughed as her body wiggled back and forth trying to get away from his fingers.

Tom laughed as well and was happily surprised to she her skirt now up over her panties. He stopped tickling and just stared at her exposed undies.

"Do you like them?" she giggled as she slowly opened her thighs causing the black silk to stretch across her blonde mound. Her fingers fished into the small pocket on her skirt and held up a small square-shaped shiny object.

Tom gulped when he saw the condom. He didn't have any more excuses. "Are you sure?"

"Yes I want you to be the first," she said as she raised her hips to allow her fingers to push her black panties under her hips. She tossed them aside and again offered him her virginity.

Tom slowly pushed down his shorts and fumbled in his boxers for his hard-on. Although he was a virgin he had put on rubbers before just to make sure he knew what to do when the opportunity arrived. The time was suddenly now.

Karen watched as he ripped open the condom and stretched it over the huge tip. Her pussy was dripping wet so she knew she was ready to finally become a woman. "Hurry," she said. He pushed the condom wrapper under the cushion and smiled.

Tom moved up between her legs and aimed the latex lance at her maidenhead. He pushed and heard her moan. He pulled away. "Are you OK?

"No wait let me get my breath," she said. The pain was overbearing because he was so big. She took ten big breaths and again lay back ready.

Tom moved slower this time and pushed gently against her hymen.


Grandma Bell looked at the clock and realized almost twenty minutes had passed since she was down in the basement. The apron hit the table before she walked to the door and found it locked. She smiled as she grabbed the tiny key. Before she opened the door the doorbell rang.

"Hi Jo," she said smiling. It was the tomboy girl who was there yesterday.

"Is my sister here?"

"Karen is YOUR sister?" Bell asked with a surprised look. "Yes she is downstairs with Tom."

"I need to get down there," Jo said looking nervous.

"I was just thinking the same thing," Bell said as she let Jo in. As soon as she unlocked the door Jo bolted down the stairs. She froze when she saw Tom's body poised to enter her hussy sister.

"STOP!" Jo cried out.

Karen and Tom both turned to see Jo standing at the base of the steps and Bell's feet slowly coming down the steps. "Shit," Tom said as he quickly jumped up and pulled up his shorts over his hard shaft. Karen moved up and looked for her panties but didn't have enough time to find them. She pulled down her skirt and sat back just as Bell's head looked under the basement ceiling.

"Jo arrived so I let her come down," Bell said smiling. "I wonder how that door got locked."

Both Tom and Karen's faces were bright red from the excitement of almost fucking and almost getting caught. "Tom can I see you a minute upstairs please?" Bell asked. She turned and walked up the stairs not waiting for an answer.

As soon as Tom walked away the sisters went at each other.

"You're such a whore," Jo said as she moved towards Karen.

"If you touch me I'll tell daddy," Karen said holding her hands up to protect her.

Jo held back her anger and picked up the balled up panties next to the sofa. "Maybe I'll show him these and let him know how easy they come off?"


"I'm ashamed of you," Bell said as they sat at the kitchen table. "I never thought I would ever say that to you."

"Grandma, I'm sorry," he said with his head looking down. "I don't know why I did it."

"Tom you have to be stronger and be aware of girls like her."

"I know."

"Do you want to tell her to leave or should I?"

"I will," Tom said.


"You know you don't have a chance with him," Karen said smiling at Jo as they waited for him to come back.

"If he wants you he can have you and I'll leave," Jo said trying her hardness not to pull her sister's hair out. She heard and saw Tom's footsteps coming down the stairs. Jo stood ready to leave.

"Tom, I'm sorry I'll leave," Jo said as she walked by him.

"No," he said grabbing her arm. "Karen has to go."

"What?" Karen asked. "You want me to go?"

"Yes," he said firmly.

"Well I've never...," she said as she grabbed her panties from Jo's hand.

Tom watched her walk up the stairs while taking aim at her bare buttocks under the short dress and glimpses of her damp pussy between her thighs. "And you won't with me," he said.

"I should leave too," Jo said feeling happy she had stopped them before he entered her but sad because he was probably mad at her for doing it.

"No please stay," he said. "I need a friend right now." He opened his arms and pulled her body into his.

"Careful your Grandma may come down," Jo giggled.

"She's not worried about you," he laughed.

That's the problem she thought. Somehow she needed to be someone Tom would make love to.

"You want to watch "Love and Basketball?" he asked as he moved over to the DVD and popped in the movie.

"Sure," Jo said smiling. "It's my favorite movie."


Tracy looked at the map and tried to drive through the dense city traffic at the same time. She wanted to surprise Tom and spend a couple of days with him until Clarkton High School started back But the biggest reason was that she had gotten intimate with another boy at the school dance last weekend and now had mixed feelings. She thought she loved Tom but after Saturday night she now was not sure.

"Hurry up!" she yelled at the stalled traffic in front of her.


Tom and Jo tossed a mini-basketball back and forth as they watched the movie.

"Your sister told me something interesting today," Tom said.

"I don't think I want to know," Jo responded.

"She told me you were not gay."

Jo caught the ball and just held it wondering now what she should say. "She did huh?" She tossed the ball back to him.

"That's all you have to say?"

"It's something I don't like talking about," Jo said. If she told him she was straight it would mean she had lied to him and she didn't know how he would take it.

"We're friends. I hope you can talk to me about such things."

"I've got to go to the bathroom. Be right back," she said.

As soon as the bathroom door closed Jo stood and put her back to it. She realized she had to tell him the truth. She hesitated as she thought of how she would say it.


Bell was dozing off in her favorite chair and was dreaming of Errol Flynn when the doorbell sounded again. "What now?" she said as she moved slowly to the door. Since her family moved in with her she had lost out on a lot of her naps.

"And who might you be?" Bell asked the cute young dark haired girl on her porch.

"I'm Tracy, Tom's girlfriend from Clarkton. I thought I would surprise him."

"Sure why not," Bell laughed. She didn't need to watch her soap opera today because she had a live one right now in her house. "He's in the basement so go on down."

"Can I use your bathroom first?" Tracy asked. She wanted to fix her hair and makeup.

"Sure," Bell said as she returned to her chair.

Tracy walked out of the bathroom and popped in a breath mint before she walked down the stairs.

Tom was lying on his back on the floor while tossing the ball up over his face when he heard someone coming down the stairs. "I'm being good Grandma," he laughed. He continued to watch the ball go up into the air when he saw legs walk up to his head. He saw thin bare legs who were definitely not his Grandma's and forgot about catching the ball. It landed on his face. His eyes moved up the smooth legs to the short skirt and then up under it to the black crotch of the panties. "Karen?" he said as he sat upright.

"No it's not Karen," Tracy said while not smiling. "Who is Karen?"

"TRACY!" Tom said totally shocked to see her there. "What are you doing here?"

"I thought I would surprise you," she said still not smiling. "Who is Karen?"

Tom was thinking of how to answer that when the bathroom door opened and Jo's face popped out.

"Tom I'm not gay," she said looking downward.

Tracy looked at the girl and back at Tom. "Is this Karen?"

"Who the fuck are you?" Jo asked as she glared at the cute stranger.

"Who the fuck are you?" Tracy glared back as they moved eye to eye.

"WAIT PLEASE," Tom yelled. "Tracy this is Jo. Jo this is Tracy."

Neither of them said a word as they stood wondering if they should just go at it.

"Tracy is my girlfriend from Clarkton," he said grabbing Jo's arm and pulling her away.

"Oh that Tracy," Jo said. She held out her hand.

Tracy still was upset for finding another girl in the basement and having Tom call her Karen and did not shake Jo's hand.

"Who is Karen?" She asked as she turned to look at him.

"She's one of the basketball players at the park," Jo lied quickly. "We all play hoops together and she was just here with us."

"Just basketball right?" Tracy asked.

"Sure....yes just basketball," Tom said as he hugged her into his body. He peeked over at Jo and winked. "Thank you," he mouthed without making a sound.

"I guess I'd better be going," Jo said as she watched their hands move over each other's back. "If you want to play some hoops let me know."

Tracy waited for the door to close before she placed her lips onto Tom's. Their tongues mingled for a couple of minutes before she broke away. "I've missed you so much," she said.

"Me too," he whispered back. Here he was again with a cute girl in his room with a chance to go all the way. But his Grandma was upstairs.

Tracy moved away from him and sat on the sofa. "So tell me what you've been doing since you got here."

Tom thought about having Karen jerk him off and Jo rubbing his penis with her elbow but said, "Not much really. Just been playing some basketball. How was the dance?" He sat down next to her.

"It was good," she said. "Jennie broke up with Matt."

"You're kidding," he said. "They've been going out longer that us. What happened?"

"They didn't want to be tied down when they went to college," she said.

Again the door opened upstairs and Bell came down carrying a tray of cookies. "I hope you want some of these," she said after sitting them on the small table in front of the sofa. "It's good to see you two being good," she commented as she walked back up the stairs.

"What did she mean by that?" Tracy asked as she bit into a delicious chocolate chip cookie.

"Who knows?" he said. "She's getting old."

"I HEARD THAT!" Bell yelled just before she closed the door.

"Do you think she will mind if I stay over tonight?" Tracy asked as she moved closer to him.

"I guess you can sleep on the sofa upstairs," he said smiling as her hand moved to his thigh.

"I was hoping to sleep down here with you," she whispered. Her fingers moved slowly up his thigh while stopping to give it a gently squeeze every three or four inches.

"That would be nice," he whispered. His hand moved over back and down to the top of her curvaceous ass. "But I don't think the family will approve."

"What can we do now?" her fingers moved over his large bulge.

"That, and this," he said as his fingers moved down to cup her smooth buttocks. He realized she was wearing a thong which was a first for her. "What's this?" His fingers pinched the thin strap moving down between her ass cheeks.

"Why don't you find out?" she giggled. She let go of his rod and stood in front of him. Tom's fingers trembled while moving up over her bare knees to her delicate thighs. The short skirt offered little resistance to his exploring fingers heading north under the thin material. He couldn't wait to see her womanly treasure as he pulled the vee shaped panties down over her hips and out from under her skirt. He noticed the crotch was damp but didn't say anything.

Tracy kicked her panties to the side and leaned over to pick up the front of her skirt. She knew he had not seen her vagina and smiled as she looked at his face as the material caressed her flesh as it moved upward.

Tom had only seen Karen's blonde bush and was not prepared for his girlfriend's neatly trimmed dark pubic mound. "God you are so beautiful." His hands moved with a purpose towards the target identified by the glistening moisture.

Tracy's knees were so weak she had to sit down next to him. She leaned back on the sofa as his fingers explored her slit. He rubbed her clit and she moaned. His mind remembered the feel of Karen's pussy as the fingertip moved downward to her virgin...suddenly his finger dipped into the opened hole waiting for him. He stopped.

"Tom I..." she said seeing his shock. "I should have told you first."

Tom moved his finger deeply inside of her feeling a hot pussy for the first time. Suddenly he pulled it out and sat back on the sofa. "Who was it?"

Tears fell from her eyes as she looked down not wanting to see his face. "It doesn't matter. I love only you."

"Fuck Tracy, I leave for two weeks and you fuck somebody." Tom quickly thought about how close he was to do the same thing that same morning. "At least tell me who it was."

"Don't be mad," she said pulling her skirt over her exposed bush.

"I've over mad," he said. "Just tell me who it was."

"It was Jack."

"My cousin Jack?"

"Yes, but it's not like you think."

"How can fucking my cousin not be like I think?"

"It wasn't like that," she said sobbing.

Tom took a breath and tried to calm down. "OK tell me the way it was."

"It was at the dance and I was all alone. Jack came over and we just talked for almost an hour mostly about you."

"Keep going."

"When the dance was over we went to the coffee shop and talked for another hour. That's when he told me how much he liked me but since we were going out he never pursued it. He had tears in his eyes so we left and drove around town for a while. We ended up at Eagles Point."

"He took you there and you didn't say anything?" Tom remembered it as the city's make out place.

"He said we were just going to talk some more. Since you left I've been so lonely and being with him made me feel better."

"Yeah a whole lot better," he quipped.

"When he first kissed me I was in shock and told him no. We talked some more and he kissed me again. I tried to resist but I was so lonely and........." she sobbed.

"Tell me the rest," Tom said. He wanted to know it all so when he beat the shit out of his first cousin he could remember everything.

"And...then we did it."

"You just did it? You just pulled up your skirt and down your panties and he stuck it in?"

"You make it sound so cheap. No it was not like that at all. We kissed for a long time and he touched my breasts and then under my dress. I touched him too."

Report Story

bySlickman© 0 comments/ 356179 views/ 81 favorites

Share the love

Report a Bug

3 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: