First Time Tomboy

"No," she lied as she picked up the basketball and dribbled. He tried to steal it from her but her skills kept him away. She dribbled around him and laid the ball in. "Ya better get her off your mind before you play for the team," she laughed.

"What girlfriend?" he laughed as he did a cross over dribble leaving Jo in her tracks. His six foot three frame flew up over the rim for a two-handed dunk.

"Show off," Jo said while admiring his lean waist as the shirt moved upward.

When Tom returned to the house Tracy's car was gone.

"Where did she go?" Tom asked.

"She said she was going back to Clarkton," Bell said. She said to give you this. Bell reached into her apron to take something. She held out her hand and opened it.

Tom's mouth dropped when he saw it. In her hand was the condom package he had hid under the sofa cushion downstairs.

"Anything you want to tell me?" Bell asked.

"No," he said as he turned to walk downstairs.

Tom waited to give Tracy time to arrive at her home and called. Her mother answered and told him she came home but said she did not want to talk to anybody. She asked Tom what was going on but Tom avoided the answer. "You'll have to ask her that question." He hung up and fell asleep.

When the phone rang it was dark in the basement so he had a tough time finding it. "Hello," he managed to say still drowsy.

"Hi," Tracy said.

"Tracy, why did you leave?" he asked already knowing the answer.

"When I found the condom wrapper next to your underwear I freaked out but after driving home I realized we both had sex with other people so maybe we could forgive each other and start again."

Tom shook his head trying to get awake. "Tracy I didn't do it. I was about to do it when my Grandmother came downstairs."

"Karen?"

"Yes. But it doesn't matter if I did it or not because I was going to do it. I don't think things will work out with us after this." Tom heard her sniffle and waited for her reply.

"Promise me you will come home once before we go away to college," she said sadly.

"I promise," he said. He wanted to get back to Clarkton if nothing more than to beat the shit out of Jack.

"Before I hang up I want to know why that girl said what she did when she came out of the bathroom."

"Oh that was Jo," he laughed. "What did she say?"

"She said she was not gay. What did she mean by that?"

"She said that?" Tom asked. "Are you sure?"

"Well I was upset but some things you don't forget."

"Someone told me she was gay so I guess she wanted to set the record straight."

"Well I knew she wasn't gay just from the way she looked at you when she left us," Tracy said.

"Na, we are just friends," he laughed.

"Maybe you think so," Tracy said. "Call me next week."

"OK," Tom said before they hung up. They did not say they loved each other.

"Shit," Tom said a loud. Did Jo like him? "Na," he laughed.

Again the phone rang. It was Billie who invited him to a team party the following night at his house. Billie's parents were gone.

It was after breakfast the next morning when Karen was sitting on her bed and Jo knocked and entered. "Stay away from me or I'll scream," Karen said.

"Relax," Jo laughed. "I'm not mad. I was wondering if you would help me with something."

"Me help you?" Karen asked surprised. Normally Jo thought she was useless.

"Yes, would you show me how to put on makeup?"

Karen tried not to laugh but couldn't help it. "Ha, ha,...you're kidding right?"

Jo glared at her.

"OK sorry," Karen quickly said. "Come with me." She stood and walked to her dresser and turned on the makeup light. "Sit down."

For the next 45 minutes Karen showed Jo everything she needed to know about makeup. When she was finished Jo looked in the large mirror and gasped. She didn't recognize herself. "One last thing," Jo said. "Can I borrow one of your dresses?"

"Holy shit you are really in love," Karen laughed. "Sure." She walked to the closet and opened it up showing her tomboy sister a lineup of about 30 dresses. "Take your time trying them on."

"Thanks," Jo said smiling. Maybe her sister wasn't so bad after all.

"My underwear draw is over her in case you want to want to go all the way," Karen grinned. She again saw Jo's glare. "I mean 'all the way' getting dressed."

"Is there a party I don't know about?" Karen asked as Jo tried on about nine of her dresses.

"Billie's house for the basketball teams only." Jo pulled down a slinky black silk dress and smiled. The basketball players will shit when she walks in wearing this dress.

Tom waited as long as he could before leaving for the party. He couldn't wait to see Jo and to ask her about the "I'm not Gay" comment. He would also get to meet all of the basketball team members both girls and boys. When he arrived at Billie's house he was the second one to arrive. On the sofa was a tall but very cute girl whose name was May. They hit it off right away.

"I heard about you," May smiled. "A cute guy who can shoot."

"Thanks," he blushed. "What position do you play?"

"Any position you want me in," she laughed. Again he blushed. He was not used to the forwardness of these city girls.

Some more players arrived and Tom got to meet them. He was aware of Calvin's coldness right away because Calvin was the highest scorer on the team and had a chance to make all-city and possibly get a scholarship. Calvin also played Tom's best position which was the number two guard.

"You might get some time at the 3," Calvin said cocky. "Ellis is only six foot and has problems guarding the bigger small forwards."

Tom thought about telling him how he was going to take his position but decided to save it for another day. He met Ellis and realized he was about the biggest asshole he had ever met. The boy thought he was all-world in basketball and girls and probably wasn't in either. Tom was going to ask where he got his cheap cologne from but held back.

Tina arrived with another girl named Maggie who was one of the starters. She was pretty shy so Tom didn't get much of an impression of her. Jan was the last started who needed to lose about 50 pounds to look good. She said it was her playing weight to get rebounds. A half hour later most everyone was there and the booze and dancing had started when the door opened and Jo walked in.

"No fuckin way!" Tina yelled when she saw her best friend in a clinging black dress. "That can't be JO!"

Jo blushed and smiled as everyone stopped moving and just stared. She looked like her sister Karen in short hair but even better. "What's everyone staring at?" Jo cracked. "You never saw a girl before?"

"Yeah but we didn't know you were a girl." A guy named Allen joked.

Jo looked immediately to find Tom, who Billie said was coming, but she didn't see him. As she walked across the room Ellis grabbed her hand. "Care for a dance?" It was the first time Ellis and Jo had even talked.

"No thanks Chump," she said pushing him away. She moved up to Tina and whispered. "Where is he?"

"You came a few minutes too late," Tina whispered back. "He was dancing with May but I don't know where they are now."

"Shit," Jo whispered. "Help me find them."

As Jo passed the punch bowl she picked up a glass she knew had some booze in it and gulped it down. It was the first alcoholic drink she ever had. She smiled and picked up another one. If she was going to be intimate with Tom tonight she knew she needed some help.

Jo and Tina went opposite ways searching the first floor and met again at the base of the stairs. "Do you think they went upstairs?" Tina asked. Before she got an answer from Jo the sexy black dress moved up the long stairway.

Only one bedroom door was closed so Jo slowly cracked it and saw two figures lying together on the bed. "Tom?" she asked as she walked into the room.

May was the first to turn towards them. "Holy shit is that Jo?"

Jo could see May's blouse completely unbuttoned and the girl's pink bra on display. From under the girl's body popped up Tom's head and face. "Jo?" He looked at the silhouette figure in the doorway but could not see her face in the dim room. But he did see the shape suddenly turn and walk back out.

"Was that Jo?" he asked May who quickly turned and planted her lips back on his mouth. Tom went brain dead again as her soft warm body pressed down onto his own.

"Sorry Jo," Tina said as they walked back downstairs. "Men are bastards."

"Yeah," Jo said as she walked directly to the punch bowl again and downed three more glasses of spiked punch.

Ellis was standing in the corner staring at the girls to decide which one would be his conquest that night when he felt a presence next to him. He turned to see Jo smiling at him. "Don't hit me," he said jokingly.

"Hitting was not what I had in mind," Jo said giggling. The few drinks had quickly lowered her shyness around guys. "Didn't you want to dance with me?"

"Sure," he answered as he took her wonderful body into his arms and pulled her soft breasts to his chest. This would be his greatest conquest if he could fuck Jo Thompson. He would be famous in the gym shower room for years. His hands roamed slowly down her back expecting her to smash him in the face any minute.

Jo was messed up as they danced closer and closer together. She could see the other dancing couples touching each others asses and rubbing their legs between each other's thighs. Normally she would deck any boy who tried to do the same to her but Tom had fired up things inside of her she didn't know existed. She closed her eyes and pretended it was Tom's hands which were now cupping her round buttocks.

How many dances and drinks she had were lost in her drugged mind as she continued to melt her young virgin body to Ellis. She didn't stop him when his fingers snuck up between their bodies to caress her soft breast and to toy with the hard nipple. Nor did she mind when his lips found hers and his tongue danced with her own.

Tina tried to keep an eye on Jo and had lost her for a few minutes. She slowly walked around the dim lit room until she saw Ellis and Jo in the corner. She gasped when she saw the shoulder strap of her dress down her arm and her bra pushed down enough for her naked breast to be exposed and his lips on her nipple.

"Jo I need to talk to you," Tina said as she grabbed the drunken girl's arm and pulled.

"Hey leave us alone," Ellis said as he grabbed Tina's wrist and pulled her away from Jo.

"She's fucking drunk, Ellis. Leave her alone," Tina said forcefully. Ellis was at least a foot taller and a hundred pounds heavier.

"Tell her to go away," Ellis whispered to Jo who could barely open her eyes.

"Gggg.........ggoooo..." she grunted before her eyes closed again.

"See, she wants you to leave," he said as he pushed her back four feet.

"I'll be back," Tina said totally pissed. She needed some help and looked for Billie.

"He's over there," Jan said to Tina. Tina looked and saw him passed out on the sofa. She moved back to tell Ellis to leave Jo alone again and saw them missing. Shit. As she moved up the stairs she saw Ellis's back going into one of the bedrooms.

Tom's pants were undone and his hard shaft was pointing upward as May's hot pussy was about to engulf it. She had told him she was on birth control and to forget about a condom so he did. His mind was also fuzzy from the punch but he knew he was about to become a man any second. Flashes of Jo kept coming back and he suddenly imagined it was Jo's body on top of his. As her hot and damp pussy folds pushed against his tip the door suddenly opened. "Not again," he moaned as they stopped to see Tina standing there.

"Christ Tina leave us alone," May cried out just before Tina's hands pushed her off of his body. Tina stared down at the huge one-eyed monster sticking up at her. She suddenly snapped out of it.

"Tom you have to help Jo NOW!" Tina said not waiting for an answer. She grabbed his arm and pulled him off the bed until he landed on his ass on the floor.

"Fuck," he groaned as he stuffed his hard-on into his pants and followed Tina out the door. "I'll be right back," he said to a pissed off May.

"Jo is in there with Ellis. She is smashed and he is about to fuck her," Tina said with a panic look on her face.

"Damn, how do I get myself into these messes?" he said before he pushed open the door and saw a startled Ellis on the bed with his pants and boxers down around his knees. Jo's lifeless body was lying under him with her eye's closed, legs spread wide apart and her blonde pussy opened for his invasion.

"Get the fuck off of her," Tom yelled as he grabbed Ellis's arm and jerked him off the bed. He flung him around until the boy crashed against the door. OUCH!" Ellis cried out as he held his head. "I'm going to kill you," Ellis said as he tried to stand.

Tom stood back as Ellis tried to ram him but the pants, which had fallen down around his ankles, tripped him and he fell face forward again striking his head. This time he stayed down. Tina jumped on his back and started pounding her small fists against his back. Tom laughed and pulled her off. "I think he has had enough."

"Don't look," Tina said to Tom as she pulled Jo's sexy panties up the unconscious girl's legs and over her still virgin pussy. She pulled her dress down and turned to Tom. "You have to help me get her to my house."

"But," he started to say realizing that May's pussy was waiting for him in the other room. "Forget it," she said. His arms moved under Jo's body and he carried her while Tina led the way down the stairs.

"She better stay at my house because her parents will kill her if we take her home like this." Tom carried her to Tina's car and put her in the back seat.

"Come with me to help carry her inside," Tina said not asking if he wanted to or not.

Tom had given up on being with May and hoped he would have another chance. He kept peeking back at Jo's body in the black dress to make sure it was really her. God she looked good. "Won't your parents say something?" he asked Tina.

"They are gone for the weekend so the house is mine," Tina smiled as she thought of a way to get Jo and Tom together.

"Carry her up to my parent's room," Tina told Tom. She followed them and directed him to the right room. "Lay her on the bed."

Tom did and stared. "God she looks good."

"You know she is not gay right?" Tina asked.

"I just found out today."

"You also know she likes you a lot."

"Someone else told me that today but I didn't believe her," he replied.

"Help me get her dress off," Tina said as she moved to the bed.

"I...I...I don't think I should do that," he said nervously. She might get pissed if she finds out.

"I won't tell her and I'm sure you won't," Tina laughed as she pulled she dress straps off of her shoulders.

Tom hesitated until Tina turned and gave him a look. "Come on." He did.

"Lift her hips while I pull the dress off," Tina ordered. She smiled as he stared at Jo's filled lacy bra and matching panties. When she reached to release Jo's bra Tom said, "You are taking off her bra too?"

"She doesn't normally sleep in a bra," Tina grinned. The cups pulled off her pure creamy white orbs with light pink nipples.

"Tom...er.Tom...," Tina said laughing. He was mesmerized by her firm treasures. "Pick up her hips again." He did and stared at her flat stomach as the golden panties moved down over the trimmed corn silk mane.

"I'll be back with something to wear for her," Tina said smiling. She would make sure she took a few minutes for him to really appreciate her naked body.

"You are so beautiful," he whispered. He sat moving his eyes up her muscular but tender thighs covered with tiny blonde hairs. One of her legs was open just enough for him to see the pink folds of her thin pussy lips and the small rise of her clitoris resting at the top. He knew this was wrong seeing her like this but he remembered that she had seen him completely naked in his room. And she had lied to him about being gay.

"I'm glad you are not gay," he whispered. His eyes now moved north up and over her firm breasts. He wanted to touch them so bad but knew Tina would kill him if she came back and saw him doing it. Finally his eyes moved up to her cute face now covered with makeup. He realized he liked her better without the paint.

"Well what do you think?" Tina asked as she walked back into the room carrying a fresh pair of panties and a thin strap tee shirt.

"I still can't believe this is Jo," he said.

"I think you have brought Jo out of her shell. Help me," she said giving him the panties and shirt.

"You want me to dress her?"

"Sure why not?" Tina asked. She glanced down at the large bulge in his pants.

As Tina held up Jo's legs and hips Tom pushed the silky underwear slowly up her thighs until it covered her yellow forest. He savored the soft touch of her skin each time he accidentally touched her. Tina held Jo's body in a sitting position as he pulled the tight tee shirt down over her breasts. Again his fingers touched her softness.

While I call Jo's parents why don't you call yours to tell them you are sleeping over at Billie's house?

"I'm not planning on sleeping over at Billie's house," he laughed.

"I know," she laughed back at him. "You are sleeping over here." She turned and left the room.

"But..." he started to say before he realized she was gone. He picked up his cell phone and called his Grandmother's house.

He waited a few minutes and then saw Tina walk back into the bedroom wearing the same type things Jo had on. Panties and a tight thin strapped tee shirt. "Don't get any ideas," she laughed when she saw his eyes on her skimpy panties.

"Do you have any pajamas for me?" he asked with a smile.

"Nope I guess you will just have to wear your boxers." Tina pulled the covers down the king size bed under Jo's body and then up to cover her. "Are you getting under?" Tina giggled as she slid under the covers on the other side of Jo.

"She's going to be pissed in the morning," he said while removing his pants and shirt. He picked up the covers and held them high enough to see both girl's near naked bodies and he was not going to be able to do anything to them. Life sucked.

"Tell me all you know about Jo," Tom said to Tina in the dark room.

"When Jo was born her father wanted to have a boy. When Karen came out first he was disappointed and when they discovered there was another baby he again waited for a boy but discovered Jo was another girl."

"So Jo became his boy and Karen the girl," he said.

"Yes, Jo not only became the boy she was as good if not better in sports than most if not all the boys in the neighborhood. If she was taller she could play on the boy's team."

"Do you think she will get a scholarship?" he asked.

Tina laughed. "You don't know do you? Shit Jo has been offered a ship by UCONN, Notre Dame and Tennessee and that was as a junior."

"She didn't tell me," he said as his arm brushed against Jo's. "Does she have the grades?"

Again Tina laughed. "She's been accepted at Princeton and Yale."

"Is there anything she is not good at?" he laughed.

"Yes.......boys. She has tried her whole life to be a boy and suddenly she now wants to be a girl. I think tonight was the first coming out as a girl for her."

"I wish she would have gotten to the party a little earlier," he said.

"I'm sure she felt the same way when she saw you and May. May is the slut of the team by-the-way."

"I seem to have a magnet for those types of girls."

"OHHH!" Jo moaned as she turned her body to the side until her arm hooked over Tom's chest and her breast pushed into his arm.

"I think I should sleep somewhere else," he said feeling his prick expanding again.

Tina laughed. "Just keep it cool. Try to get some sleep because I think you might need it."

Tom closed his eyes and tried to forget the soft breast pushing into his body. He knew it was wrong but he couldn't help it as he slowly moved his hand up to the soft cushion until he touched her nipple. He smiled as he played with it until it was rock hard.

Jo thought she was dreaming about Tom again. It was the same dream she had for the past few days. She was lying in bed next to him as they touched and kissed. Her leg and arm was wrapped over his and his fingers touched her body. "Oh Tom," she moaned as her fingers found his grand salami and she stroked it.

Tina heard the moan and peeked over at Jo's body which was now wrapped over Tom's. Her fingers had found his long shaft and she was jerking him off. She had hoped her plan to get them in the same bed would work out and now it was. She was the best cupid in town.

Tom didn't know if she was awake or asleep as she rubbed up and down his shaft. Right then he didn't care as he moved his fingers over her stomach and down under her panties. He found her small hard clit and rubbed it at the same motion her fingers were touching his shaft. "Now Tom now!" she cried as she came.

Tina tried to go back asleep but couldn't because of what was going on next to her. She wished it was her hand jerking him off but it wasn't. She smiled as her fingers moved down over her quivering stomach and into her own panties. She found the little man in the boat and petted his head over and over again.

Tom woke up first and tried to remember if he had dreamed about them touching each other or if it was real. His head lay on the pillow just watching Jo's chest rising and falling as she slept.

Jo felt sick to her stomach as she opened her eyes. Through the haze was someone's face and eyes looking at her. She closed her eyes tightly and again opened them. "TOM! What are you doing in my bed?" she asked as she pulled the covers up to her chin. She quickly picked them up and peeked under to see if she was naked or not. She saw the tee shirt and panties. "DID WE....?"

Tom laughed. "No we didn't."

"Why are we in........." she realized she didn't know where she was or whose bed they were in. "Where are we?"

"You're in my parent's bed," Tina said smiling next to her.

"Oh God, I feel sick," Jo said as she pulled back the covers and jumped off the foot of the bed. She made it to the bathroom just in time.

"Are you OK?" Tina asked as she kneeled down next to Jo by the toilet.

"No, I'm not fucking OK. I hope someone tells me why I wake up in bed with Tom on one side and you on the other." Suddenly she threw up again.

"Do you remember anything from last night?" Tina asked.

"Last night. I remember wearing a dress and dancing with somebody and........" She spit out some chunky juices and continued. "Nope that's it. What is Tom doing here?"

"He carried you to my house because you passed out at Billie's." Tina said.

Jo slowly stood up, washed her face in the sink, and looked at herself in the mirror. "God I look like shit. I feel like shit too."

"Why don't you take a shower and then you will feel better?" Tina asked.

"Good idea," Jo said. "Tell Tom not to go. I need to tell him something."

"That you love him?" Tina giggled.

"Maybe," Jo giggled back. "Just don't let him leave."

She watched Tina close the door and turned on and adjusted the water. She quickly undressed and moved under the warm water. She smiled as she thought of Tom waiting for her in the large bed. Maybe this would be her chance to tell him how much she cared about him. Her soapy fingers moved over her hot stomach.

As she placed her face upward into the warm spray she heard the door open and then the shower door. "Tina leave me alone right now," she said.

"I'm not Tina," Tom's voice said behind her. "Do you care if I join you?"

Jo froze in excitement. He was in the shower with her and probably naked. "Sorry about getting sick," she said as she was a lost for words.

"I wasn't feeling too well myself," he whispered as he took the soap from her hand and lathered up his fingers. "Care if I wash your back?"

"No," she giggled. Her body was on fire as his fingertips gently moved over her tender shoulders and down under her shoulder blades.

"You looked beautiful in the dress last night," he whispered. The soapy hands moved up under her armpit and gently over her naked breasts. His hard shaft pushed up against her bare ass.

For the first time Jo felt like a female. "Tom I have to tell you something..." she said as she turned and faced him. She saw his smile and his eyes looking down at her naked front.

"I....ah...," she saw his mouth coming towards hers and tried to tell him she loved him but he was too fast. "I...Lo.." His kiss was a hot flame as their body's again pressed together. Their hands and fingers raced to explore areas never before touched by anyone but themselves. He pulled his lips from hers. "Tom I..." he smiled and put his finger on her lips. "I know....me too."

His fingers pulled her round ass towards his body until his shaft rested against her pubic mound. She opened her legs and guided his hard prick under her until she was almost sitting on it. It was now pressed hard against the length of her virgin slit.

"I've never..." she whispered in his ear as she nibbled on it.

"Me neither..." he whispered back.

"Do you wanta?" she asked now gasping to breath.

"Do you?" he panted as he pushed his prick into and out of her tight thighs.

"Here?" she asked as she felt the two of them slipping on the shower floor.

"No the bed..." he laughed as he pulled back and led her out of the shower and into the bedroom. They stood naked hand in hand looking at Tina who was reading a book on the bed. She glanced up and saw them standing dripping wet naked.

"I guess I should leave now huh?" she giggled as she stood and walked by him. She glanced down at his long shaft. "Jo you are a lucky girl."

"Call me Josephine," she giggled as she jumped on her back on the bed.

Tom walked over and looked down at her body. Finally he was going to get laid and it would be someone he really cared for. "What about protection?" he asked realizing he had not brought a condom.

"I just had my period," she giggled. "Can I get on top?"

"You want to be the boy again?" he laughed as he moved onto his back.

"No, I want to do it at my speed," she whispered as her legs opened and her hot dripping pussy pushed down on his shaft. "Plus I'm better One on One than the zone."

Jo grabbed a strong hold onto his shaft and rubbed it up and down her slit. She knew she had to take her time for it to fit because it was so big. Her fingers explored his length and cupped his sac of jewels. This was something she wanted to remember for a long time. Again she pressed down and felt her hymen give. "Just a little bit more" she thought. It was the first time she wished he was a little smaller.

"Are you OK?" Tom asked when he heard her moan deeply within.

"Yes," she giggled. She had always been a finisher and she was going to finish this. Suddenly it gave way and the tip of his shaft slid into her. "You're in," she giggled again even though it gave her some pain. She took a deep breath and lowered her hips another two inches.

"God you are so big," she moaned. His hips pushed up slightly until he pushed in another inch. "Wait," she groaned. "Let me do it."

The hot tunnel and the fact that his prick was finally in a girl's body was too much for Tom. He tried to hold back but the pleasure was too much. "Jo...oh God...I can't stop....IT!" He screamed as he shot his hot load deeply up into her. "OH SHIT!" he cried out as his body trembled and exploded.

Jo smiled and watched a guy climax. He looked so cute with his face all crunched up. She knew there was no chance for her to catch up to him so she slowly moved her pussy up and down the four or five inches he was inside of her. His hot juices were making it easier and easier for her. "Touch me," she moaned as she got closer and closer and felt him getting soft.

Tom knew where she meant and quickly found her hard clit. "Yes right there," she screamed. Although he was soft he was hard enough for her to keep fucking him. "Tom...OH GOD TOM..." she cried as she climaxed.

"I never knew it would be so good," Jo whispered in his ear as her spent body lay on his. His prick was still inside of her. "I'm sorry about lying to you about being gay," she said seriously.

"That's OK, because I'm glad it is not true," he laughed. Her hot pussy was stirring up some life in his shaft again.

Jo felt the expansion in her love canal and moved her head up to look into his eyes. "Why Tom I didn't know you cared."

Tom felt her pussy open wider and his shaft push in deeper than before. "Oh I care Jo, I care a lot," he moaned.

Jo's athleticism took over as she learned to pump her pussy up and down his shaft to give him the maximum pleasure. "Do you care about me more than my sister?" His shaft was sunk at least seven inches now.

"Yes," he groaned as her inner muscles milked his prick.

"Or Tracy?"

"Oh God yes," he grunted. He moved his lips up to capture her pink nip.

"Or May?"

"HELL YES! I LOVE YOU!" he screamed.

Tina smiled as she ate her Captain Crunch. "He loves you girl and it's all because of good ol' Tina," she said as she read the back of the box. With ten proofs of purchase labels she could get a Frisbee.​