Sport Model

JL Williams

Part 2

 

Kevin and Tommy whistled at the girls and amid the laughter Tommy whispered to Bobbi that she looked terrific. Soon enough they were at the school and buying their admission tickets to the dance. Gina, Jeri, Kevin and Tommy dispersed into the crowd leaving Bobbi alone as she walked into the dance. She hoped that Jeff was there, but she didn't want to look like she was desperate in looking for him. She didn't need to worry. Jeff was waiting near the entrance. He looked so handsome in his khaki shorts and short sleeve blue shirt….and the huge smile that was meant for only Bobbi.

Bobbi smiled back and Jeff took her in his arms and kissed her. She just naturally opened her mouth to accept his tongue. She just as naturally wrapped her arms around his neck. When they broke the kiss, Jeff looked down at Bobbi and said, "I am so glad to see you. I missed you!"

Jeff escorted Bobbi into the cafeteria and they held hands while they talked. Bobbi didn't know why but she was excited to be with Jeff. She didn't know if it was Jeff or the excitement of being dressed and with a boy, but she knew she was turned on and hyper. She wanted to jump on this boy and have sex. She knew she shouldn't, but her teenage hormones were in maximum overdrive.

She asked Jeff "Is your car nearby? Can we take a walk?"

Jeff said that his car was in the lot, and he'd love to go for a walk. With that, he took her hand and they headed out into the parking lot. They passed all the smokers who were huddled outside the door, and through the rows of cars in the parking lot. Jeff's car was parked in the second from last row in the lot. He pressed the key to unlock the door as they neared the car. He moved swiftly to open the front door, but Bobbi motioned to the back seat, the seat where they wouldn't be encumbered by the bucket seats in the front.

Jeff switched to the rear door, and let Bobbi into the car. He then sprinted around to the other side and hopped into the car. Once Jeff hit the seat, Bobbi was on him. Kissing him and running her hands through his hair. Jeff quickly caught up in the emotional frenzy that Bobbi had brought about. He was kissing Bobbi back; he was caressing Bobbi's legs and working his way up under her short dress. Bobbi spread her legs to give him better access.

There was a flash in Bobbi's mind. This was wrong, this was irrational. This was gay. She fought those thoughts off. She felt Jeff's hand reach inside her panties and free her penis. She knew she had to reciprocate. She unzipped his pants and freed his penis as well. They both stopped for a moment as they realized they were about to do. Their inexperience suddenly loomed large.

Finally, Jeff said, "Bobbi, I love you. Let me take care of you. Let me kiss you down there."

Bobbi countered with the same plea. "Jeff, I want to take care of you. There isn't enough room back here for us to sixty-nine. Slide around; I want to take you in my mouth."

Jeff nodded dumbly. He repositioned his body and Bobbi went down on her boy friend. She sucked him within an inch of his life. She caressed and kissed and loved his dick. Jeff moaned and squirmed; he pushed his hips up and within a couple of minutes he exploded into Bobbi's mouth. She did it. She sucked him off. She felt pride in being able to do it and to hear Jeff babbling about how wonderful she was. She continued to suck until she completely drained him. Finally, Jeff said, "Bobbi that was wonderful. I love you so much. You have to let me take care of you now."

Jeff didn't wait for an answer. He gently pulled Bobbi up and laid her back in the seat and went down on his girl friend. Bobbi caressed his head and cooed and sighed as Jeff brought her to an explosive orgasm of her own. She pulled him off of her and they kissed, soft sensuous cummy kisses. They savored the tastes of these kisses wordlessly. They were both sated for the moment. They were both content to be in each other's arms. They found they were breathing in unison and even sighed contentedly in unison. Jeff broke the spell by gently turning to Bobbi and saying, "Bobbi, I have something for you."

Jeff slid forward in the seat and went into the glove box. He took out an oblong box and handed it to Bobbi. Bobbi looked at him with questioning eyes. She wanted to say something, but only smiled shyly. She slid the ribbon off of the box and opened it. Inside was an ankle bracelet. It was gold and delicate. There was a heart attached to the thin gold chain, and engraved on the heart was "To Bobbi, all my love Jeff"

Jeff said, "I didn't know if I was going to give this to you tonight, but now I am so sure I love you Bobbi."

Bobbi kissed him passionately and held him tight. Despite his best efforts Bobbi was crying. Bobbi felt so feminine and so loved at that moment, but in the way back recesses of her mind she felt like a fraud, and she felt like no matter how much she liked this she shouldn't be doing this.

When Bobbi finally composed herself, she let go of Jeff and he immediately moved to put the ankle bracelet on Bobbi. She moved her leg up so he could have easy access to her leg. Jeff snapped the bracelet on her and smiled broadly. Bobbi smiled too; she loved the look, and was already wondering if she could wear it more than occasionally.

Bobbi, said, "We should head back into the dance, and I must look a mess. I have to fix my makeup." Jeff agreed, and they walked arm and arm into the gym.

Bobbi made a bee line into the ladies room and made her best attempt to recreate the look she started with earlier that evening. When she was satisfied she headed back out to find Jeff.

The rest of the night was spent dancing, laughing and making out like teenagers in love during the slow songs. Jeff wanted Bobbi to go with him to his friend's house after the dance, but Bobbi just couldn't she needed to go with Gina and Jeri….especially if her mom were to call. Bobbi promised to call Jeff the next afternoon. The dance ended a little before midnight, but it was almost twelve thirty before Bobbi got into Tommy's car for the ride to Gina's house. Gina and Jeri were giggling and teasing Bobbi about her boyfriend. Bobbi sat between them silent, but blushing furiously.

Tommy dropped off the three girls at Gina's house, and told Bobbi that he'd pick her up at ten in the morning. The girls piled into the house and ran up to Gina's room. In short order they were in short satin baby doll pajamas. Gina and Jeri were in bed kissing and groping each other. Bobbi came out of the bathroom and hesitated as he saw the girls going at it on the bed. Jeri looked over and motioned for Bobbi to join them. She did, but something was missing. The excitement, the passion, the wantonness was simply not there.

Gina sensed it first, and asked "Bobbi what's wrong? Are you okay?"

Bobbi started to say yes, but before she got the word out she started to cry. Gina took Bobbi into her arms and held her close. Jeri joined the two of them and they huddled on the bed and comforted Bobbi. Soon Bobbi composed herself and thanked the girls for being there for her. She said, "I don't think that I will be too much fun tonight, and I don't want to ruin your fun. Is there somewhere I can sleep?"

Gina said, "Don't be silly. We want you to be with us. We're not all about sex. We haven't known you for a long time, but we think of you as a friend. Please sit right here and tell us what's bothering you."

Bobbi took a deep breath and said, "I don't know what to think. Tonight I felt so sexy and wonderful. I loved the dress, the shoes, everything. Then when I saw Jeff I never felt so feminine and so much like a woman. I talked him into going out to his car…which wasn't very hard to do…and we made out and then I sucked him off and he did the same to me. I loved it. I felt proud to take care of my boyfriend. Then he gave me this beautiful ankle bracelet." Bobbie pulled her leg up and showed the girls the bracelet. She smiled broadly as she saw the delicate gold chain on her slim ankle and her painted toe nails.

Bobbi continued, "Then when we were in the car and I was in his arms, I suddenly realized…I am not a girl. I am a man, I am in the back seat of another man's car in a dress, and I just gave him a blow job. I cried then, and I am crying now. I am ashamed, but I don't want to stop dressing like this. I shouldn't be doing this, but I want to so badly to be with Jeff. I don't know what to do."

Gina kissed Bobbi on the cheek, and said, "Bobbi you are going through what every one of us has gone through. I did it, Jeri still does it. We all are faced with coming to grips with the fact that our wiring isn't what the world considers normal. What you have to know is that it is normal for you to want to dress, that it is normal for you to want wear makeup and that it is normal for you to want to be with Jeff or me or Jeri. Why are we like we are? I don't know, but if we let the constrictions of society make us behave like 'they' want us to, well we'll wind up in the loony bin. We need to be who we are. No guilt, no second guessing and no compromising who you are."

Bobbi nodded and hugged Gina. The three girls never really got wild, but they bonded and became wonderful friends as they talked, cried and hugged each other all night long. Morning came and Bobbi began the transformation into Bobby. He left the ankle bracelet on, sure that his socks covered it. He said his goodbyes to the girls as Tommy honked for him in the driveway.

Bobby and Tommy talked all the way home, at least Tommy did. He had a great night and never even noticed that Bobby was merely answering politely. Tommy pulled into his driveway and said, "Bobby, I will call you later."

Bobby entered he kitchen and saw his mom having a cup of coffee while she was reading the Sunday paper. She looked up and smiled. Bobby returned the smile and they talked about their Saturday nights. Bobby for all appearances seemed happy and cheerful, but his mom sensed something wrong. She felt he was forcing his smile and how happy he was. She wanted to ask him, but thought she'd wait until dinner time

Bobby went up to his room and tossed his clothes…even though they hadn't been worn very much into the hamper. He went to his computer and checked his emails. There were two that weren't junk. The first was from Jeff:

Bobbi thanks again for such a wonderful night. I can't wait to see you again,

I will call you tonight if it is okay. Please let me know. I really have to ask

you something. Love, Jeff

The second message was from Gina:

Bobbi, I hope that you are okay. I know this is very new to you and you have

gotten swept up into this whole scene. Usually it is a much more gradual process. Please call me or email me if I can be of any help. Your good friend, Gina

Bobby smiled at Gina's note. If nothing else, he would stay friends with Jeri and especially Gina. Despite her wild side she was bright and insightful. Bobby emailed her back a brief thank you and said that he would call her, because he did need to talk some more about this matter.

Bobby then turned his attention to returning Jeff's email. Part of him wanted Jeff to come over that night and come up to his room and have wild passionate sex. Part of him wanted to write to Jeff that they couldn't see each other again. What he wrote was:

Jeff, I will be tied up with my mom tonight. How about if I call you later this week? I had a great time last night too. I can't wait to talk to you. Love, Bobbi.

Those two lines took almost forty minutes to write. Bobby thought he should err on the side of being "Bobbi" and nice rather than being "Bobby" and curt. He hoped this would do for now.

Bobby knew he had to get his running in, so after he sent the emails he changed into his running stuff (leaving the bracelet on) and headed back downstairs. He told his mom he'd be back in an hour. Bobby ran his six mile speed run without really knowing where he was or how fast he was running. It was his mind that was really "running". What was he doing? Why was he doing it? Should he stop? Could he stop? He didn't know any of the answers. The only thing he really knew was he was being overwhelmed with questions.

Bobby ended his run a block from his house, as usual, and was walking home when Mike drove up alongside him. "Bobby, where have you been man, guys are asking about you?"

Bobby replied, "I've been around, it seemed more like people were avoiding me since the fight with Paul Taylor."

Mike laughed and said, "You might be right, but didn't you hear? Taylor got in a car accident last night. He was in a car with three other football players….all drunk, and they missed the turn at Route 19. Nobody died, but they are all pretty banged up. I heard Paul busted up one of his legs, and might even lose it."

Bobby was stunned. He didn't like Paul, but he certainly didn't ever wish him ill. He and Mike talked for a while about "stuff" and then Mike said he was on his way to Cindy's house. Mike said he'd call Bobby if he heard more about the accident.

Bobby walked into the house and told his mom what Mike had told him. She said, "See why I worry about you all the time?"

"Mom, you know I don't drink. And I would never get in a car with someone who had been drinking. Don't worry," Bobby said.

"But those boys could have hit someone who wasn't drinking as easy as anything," she added. Jean, then put her arm around her son and added, "I am your mom, and it is my job to worry. And speaking of worry, you seem very distracted lately. You want to tell me why? I am a good listener."

Bobby almost blurted his secret out. But instead he replied, "Aw mom, I am just thinking about school, and cross country and college and you know…."

Jean, nodded, but she still thought there was more to it.

Bobby headed up to shower and to check his emails. The only worth while message was from Jeff. Jeff wondered if Bobby was okay. Bobby emailed back that he was fine, but everything was moving so fast that he needed another day to take stock of the whole situation. Bobby reiterated that he really liked/loved Jeff, but he needed another day before he talked to him.

That day stretched into two and then three. Bobby threw himself into his "guy" things. His running became furious. He caddied everyday and hung around to try and get out twice each day. He avoided Tommy all week. He even took off the ankle bracelet and placed it carefully in the back of his sock drawer. Jeff emailed him again, but Bobby didn't respond. He managed to get all the way to Friday without masturbating while thinking of Jeff, Jeri or Gina. He focused on the cute girls in his class. But Friday was different. He wanted to dress again, and he wanted to wrap his arms around Jeff. That morning in the shower that is what he thought about as he took care of his morning wood.

Bobby put the ankle bracelet back on, and emailed Jeff before he left to caddy. He said that he'd call Jeff that night.

Bobby did call Jeff that night, and they had a great call. Unknowingly Bobby had gotten horny enough to suppress his guilt. Jeff was excited to talk to Bobby, because he wanted to invite Bobby homecoming. Jeff explained how no one would know who Bobby was, and how Bobby had done so well at the club, why not? It would be great fun and a chance for Bobby to get dressed up.

Bobby was totally taken aback. On one hand he was thrilled. On the other he was scared to death. Bobby said, "Jeff I am honored that you asked me, and I do want to be your date for homecoming. But there are some logistics that need to be worked out. I am saying yes, but I need to figure out how to get out of the house, what to wear, this is more complicated than a regular date!"

Jeff said that he understood, but the offer stood, and he wasn't going to the dance with anyone but Bobbi.

Bobbi was touched by Jeff's statement, and he vowed to do everything he could to make this happen.

Things kind of quieted down after that. Bobby was busy with cross country and caddying. He didn't try and avoid Tommy, but their schedules didn't match up. They were reduced to waving at each other when they would see each other in their respective driveways.

The Sunday before school was to start Tommy came over to see Bobby. He asked if Bobby was avoiding him for any reason. Bobby honestly said, "Tommy I have been so busy with running and caddying that I haven't done anything else. Of course I'm not avoiding you. In fact I know that you have been talking to Jack and Bill and their friends and you are going to be involved with the gay student group at school…Bill runs cross country too."

Mike smiled, "yeah, they are great guys, but I still miss my friends in the city…especially one friend, if you know what I mean."

Bobby smiled too, "I have been emailing Gina and Jeri. They are the best. Gina keeps asking when we're going to be back in the city. I don't know. I have cross country every week now through mid-November. Plus…." He started to say the homecoming dance with Jeff, but caught himself.

"Plus what? Come on, what? You were going to say something about Jeff, weren't you?"

Bobby 'fessed up, "Yes, he asked me to his homecoming, but I don't know how I am going to do that. I really would like to go with him, but I am scared I might see someone I know…or who would know me and I don't know how I'd get out of the house unless my mom was gone all day."

"There has to be a way for you to do this. It is too cool not to do it. Maybe I can help. When is there homecoming? Maybe I can get my mom to go out with your mom," Jeff offered.

"No, No, Jeff, you are a good friend, but please, I need to work on this myself for a while. If I need your help, I will let you know."

Tommy let it go, but he knew he'd let Jeri and Gina know, and he would do what he could to make sure Bobby went to the homecoming dance with Jeff.

They finished off their conversation with Tommy offering to drive Bobby to school in the morning. His mom would be happy to do it. Bobby would get a ride home from Mike since football and cross country ended about the same time. Bobby readily agreed since it would be a big help to his mom.

On his way out of Bobby's room Tommy turned and asked how Jeff was. Bobby simply showed Tommy his right ankle where under his sock was the bracelet Jeff had given him. They both smiled, that said it all.

School started and folks seemed to settle into their usual routine. It looked like the fall sports teams would be more than just good. The football team jumped out to a 2 and 0 start even without the four defensive players hurt in the car crash. Mike told Bobby that the accident might have made the team better. The cross country team was 3 and 0, and Bobby had won two races outright and finished second in the third. Classes even seemed to be fine. The only thing looming on the horizon was Jeff's homecoming.

It was three weeks before the dance and Bobby was still stalling Jeff. Jeff said that if Bobby couldn't go to the homecoming, what about a movie…anything. He said he was desperate to see Bobby. Bobby for his part was stewing over what to do. On that Saturday things were about to happen.

Bobby had a cross country meet against the neighboring high school. His mom said she was going to visit his sister Grace, and wouldn't be home until late. Bobby said no problem, he'd be home around two o'clock and he had school work to do. His mom hugged him and said, "I am so lucky to have such great kids."

The cross country meet was a mess. It poured rain all morning and despite slipping and sliding over the three mile course Bobby came in first, and the team won as well. As he predicted he was home at two o'clock. His mom left a note on the kitchen counter saying she left around one thirty and that she left money for a pizza. She suggested that Bobby ask Tommy over later.

Bobby read the note and disregarded it immediately. He hadn't been able to dress in over a month, and he was determined to try on some of Grace's dresses to see if any of them would fit him….just on the outside chance he could go to homecoming.

He bounded up the stairs and dug out his stash of undergarments and makeup. He laid them out on his sister's bed and then went to the bathroom and took a long luxurious bath. He shaved what little hair was on his legs, arms and chest. He decided to blow dry his hair, which by now was long enough to put a pony tail in Bobby's mind but it was more like a little stub of hair. Nevertheless he loved that it was getting longer. Once dry Bobby fixed it in the most feminine look he could muster. He went into his mom's room and found nail polish. He did his fingers and toes. After waiting for his nails to dry, he went to his sister's closet and found her fancy dresses. He knew it was too cliché to wear black, and he wore black on their last date…that thought made him smile. So he hunted around until he found a royal blue dress that might fit. It went down to just above his knees, had a scoop neck, short sleeves and the back was cut very low. He laid it out on the bed and put on his undergarments. Nude stockings were what he figured, or no stockings at all…he didn't know what was right; he'd have to email Gina. But for now it would be okay. He slipped into the dress and it fit remarkably well, and Bobby liked the fact that he wouldn't need a bra since the cups were in the dress.

Bobby found the matching shoes that Grace wore with this dress and crammed his feet into them. They were tight but not painfully tight. He admired his legs in the mirror and smiled at the ever present ankle bracelet. He added a choker and earrings from his limited accumulation of jewelry and augmented the look by taking things from Grace's jewelry box. He knew he should have put his make up on before he got dressed, but he didn't want to get undressed. So he put on some light blush, eye shadow and lipstick. He was so intent with getting the look right and thinking about doing this for a date with Jeff, that he was totally oblivious to everything else around him.

He never even heard the car pull up in the drive way. He never heard the front door open. He didn't hear the footsteps on the stairs or in the hall way. All he heard was his mother say, "Bobby?"

He almost fainted. His brain shut down. He opened his mouth, but nothing came out. He thought he was going to cry, but he was so panic stricken that he couldn't even do that. He just sat completely frozen at the makeup table dressed to the nines.

Jean didn't know what to think at first, but when she saw the look of abject horror on Bobby's face, she knew what she had to do. She walked over and sat next to him at the makeup table and put her arm around her son. She kissed him lightly on the cheek and said, "You look beautiful. I want you to tell me all about this, but first let me see how you look standing up."

Despite his proficiency at wearing high heels Bobby wobbled around the room. He was so shaky that he almost couldn't walk at all. He turned and faced his mom. She was smiling up at him. She didn't look upset or angry. She looked like she was seeing her daughter for the first time. His psyche went from fear to joy so fast that he completely broke down. He started crying uncontrollably. Jean went to him and led him to the bed and sat him down.

Jean said, "Bobby, I love you and I want to know what you are doing. I am not judging you and before you start saying this is the first time you've ever done this, or you will never do this again, don't. Now when you get yourself composed, we can talk about this. I want to know everything."

It took Bobby a while to get himself together, but he did, and he looked at his mom with new admiration. She was handling this so great. He started telling her his secret from the very beginning. As he told of his secret stash and dressing while she was at work, Jean reached out and took her son's hands and held them in hers. She loved him so much and she could see the anguish in his eyes as she continuously lifted his chin so he wouldn't tell his story with downcast eyes.

It took Bobby forty five minutes to get to the part where he met Tommy and went to the dance in the city. When he got to this point in his life he stopped. Up to this point his dressing had been innocent enough. Now he was going into uncharted territory. He knew that he had to tell her, but he would do some editing.

Jean listened as Bobbi told her about getting caught by Tommy and how they went to the two dances. He told her about Gina and Jeri, but left out the orgy! He finally told her why he was dressed as he was. He told her about Jeff and the invitation to the homecoming dance, again he told the story without the sex part.

When Bobby finished he looked at his mom with questioning eyes. Jean hugged him again. She said, "Bobby, I love you and I can see that this is a very big part of you. Let's do this. Why don't you get out of the dress and hose and come down stairs. We can have a cup of tea and discuss this further." With that Jean went and took one of Grace's loveliest dressing gowns and handed it to Bobby. "Wear this, it will look great on you," she said.

Jean went to her room and exhaled. She was so shocked. She took a deep breath and changed into a robe herself. She wanted to be sure and not scare him. She wanted him to be open with her and she wanted to be totally informed on what he was doing.

Bobby shakily took off the dress and hose. He removed the earrings but not the choker or his ankle bracelet from Jeff. He rummaged around in Grace's closet for a pair of nice looking slippers, but finding none, he went down to the kitchen barefoot. As he walked into the kitchen he saw his mom had micro-waved two cups of tea. She handed him one and led him to the living room. They each sat on the sofa. Jean knew it was her turn to talk. She had to ask some hard questions.

She went for the jugular, "Bobby, do you want to go to the dance with Jeff?"

Bobby quietly, and almost girlishly said, "Yes, mom, I do."

Jean then asked, "Bobby do you like boys?"

"I don't know mom. When I am wearing jeans I don't like boys, but when I am dressed as a girl, I know I like Jeff. Mom, I am so sorry…."

Jean cut him off, "Bobby, there is nothing to be sorry about. This is you and you are a wonderful person. This is who you are, and if you want to go to the dance, then you will go. But you aren't going to jam yourself into your sister's old dress. We will get you your own properly fitting dress…and shoes."

Bobby protested that it would cost too much, and that he wouldn't wear it enough to justify that cost, then he added, "Mom, I can't try on dresses in public!"

Jean laughed and said, "You make a beautiful young lady. I think I am going to like her. In fact, since the weather is going to be bad tomorrow and you won't be able to caddy, we are going to go shopping…we can go to the Beaufort Mall. That's far enough away where you won't see anyone you know. Bobby, now let me see you nails."

They talked for more than an hour. Jean admired Bobby's nails and gushed over his ankle bracelet. She critiqued his makeup and even asked if he wanted his ears pierced. He initially gasped and said no, but admitted that if he could he would. Finally it was time for bed. As Bobby went to his room his mom stopped him and handed him one of his sister's short night gowns.

Jean kissed him goodnight, and said, "I can't wait to go shopping with you tomorrow. I loved you, now get some sleep. We have a big day tomorrow!"

Bobby practically floated to his room. He removed his make up, but left his fingers and toes painted. He slipped on the soft nightgown, and before he went to bed went to his computer. He had to tell Jeff that he officially accepted his offer of going to homecoming, and that he was going to shop for a dress tomorrow with his mother.

Bobby looked at what he typed before he sent it. He couldn't believe it. His love for his mom took on a new level. He hit send, and went to bed. He tried to sleep without masturbating, but the thought of shopping, going to the dance and the sensuality of the nightgown made it impossible. Bobby thought of dancing and more with Jeff and soon he was cumming into the tissue he had brought into bed, 'just in case'.

The flash of lightning and the crash of thunder awakened Bobby at eight thirty Sunday morning. Bobbi leapt out of bed. He was ready to go shopping with his mother. After a quick stop in the bathroom, he checked his emails. Sure enough there was a message from Jeff:

Bobbi, I am so glad that we are going to the dance! Wow, your mom knows. How did that go? Please call me!! I love you, Jeff.

Bobby replied that he'd call Jeff that night and that his mom was being wonderful about the whole thing.

Bobby logged off as his mom walked in his clothes for the day. She had a rose colored sleeveless dress, a padded bra, and three inch strappy sandals. Bobby looked at the outfit and smiled. He thanked his mom and said he'd be down as soon as he was dressed.

Jean said, "Bobby just put your robe on and come down for breakfast. We aren't leaving right away."

After a quick breakfast Bobby raced back upstairs. He showered, shaved, did the best he could with his makeup…he was shaking with excitement. He then donned his panties, painfully tucking his manhood 'down and under' and the bra. He strapped on his shoes and slipped into the dress. He wanted to add a choker, but couldn't decide if that would be too much, so he would bring that down and ask his mom. He did take a bracelet and watch from his stash and added them. He checked himself out in the mirror. He was, except for his hair, very pleased.

Bobby slowly walked down the stairs and into the living room. There his mom was sitting waiting for him. She smiled broadly as she saw her son. He did look very cute. His hair would need a little work before they left, but otherwise he did a great job. Jean didn't know why she was so at ease with this. As she thought about it the night before she realized that Bobby had always been a gentle child. Even though he was active in sports he never seemed overly competitive. She also deep down felt this brought them closer together, and she loved him and wanted him as close as possible.

Jean took him by the hand and had him sit on one of the kitchen chairs. First she gave him a pair of clip on hoop earrings and two rings. She did some work on his hair, and then declared it was time to go. She made sure he had an umbrella, and as they were walking out the door said, "Aren't you forgetting something?" Bobby gave her a dumb look, and Jean handed him a purse. Bobby dropped his wallet and the choker into the wallet and thanked his mom once again.

Bobby and Jean talked all the way to the mall. Jean asked Bobby what kind of dress he was interested in, and Bobby just started babbling. Jean knew it was his nervousness, but she was also impressed with how much he actually knew about women's fashion.

They arrived at the mall at a little after noon. Bobby was really nervous, but he was determined to do this. But he really didn't have to do too much. Once they walked into the mall Jean walked them around for a while, and made sure that Bobby was comfortable as Bobbi. Then she steered him into the first of half a dozen stores that catered to teenaged girls. They tried on multiple styles and colors. They appeared to all the world to be a mother and daughter combo on a Sunday shopping trip. By four o'clock they had selected "the" dress. They had bought new undergarments, shoes, night gowns and casual apparel. Jean had totally forgotten that Bobby wasn't Bobbi.

They were heading out to the car with their purchases when they passed an ear piercing stand. Jean stopped and looked at Bobby. She asked him with wordlessly if he wanted to get his ears pierced. He silently responded with a no. He wasn't ready just yet.

On the way home they stopped for dinner, and talked about their day. Bobby kept trying to thank his mom over and over, but she stopped him every time. She simply said that she loved him and wanted him to be happy. Right now she was just enjoying seeing him be so happy, happier than she had ever seen him.

Upon their arrival home Bobby did a complete fashion show for his mom. He tried everything on once again and modeled everything. Finally, his mom suggested that he put his clothes away. He had school the next day and she suspected homework as well.

Bobby went up to his room. He donned the new baby doll pajamas and did his homework. For the first time in his life he smiled as he did his calculus. Even this dreaded subject could not make him feel bad. This was one of the greatest days of his life.

School seemed to be happening at hyper speed. Cross country was more than half over and Bobby was receiving calls from division one schools regarding scholarships. He was winding down caddying. He only had a couple of Sundays left, but his cross country reputation was earning him greater tips. Seems like the members knew more about him and wanted to take care of the jock from the poor background….Bobby was so embarrassed by that article.

He kept his friendship with Mike and the rest of his buddies at school, but seemed somewhat distant to them When he was with them he was his usual self, but he had so much going on they cut him some slack. He spent as much time with Tommy as he could, but Tommy had really gotten into the gay scene at school and had made some great friends. He was even dating a guy from school, although his mom didn't know.

Jean became Bobby's best confidant. She gently prodded him, just about every day, about what he was doing, where his head was, and what was going on with Jeff. Bobbi confessed his confusion almost daily. Unbeknownst to Bobby Jean was consulting professionals, and using their advice to try and keep the lines of communication open while continuing to learn more from Bobby.

Bobby and Jeff saw each other only once during the two weeks preceding homecoming. Bobby ran against Jeff's high school the week before the dance. Jeff went to watch, as did Bobby's mom. The most awkward thing Bobby ever did was to introduce them before the race. He dreaded leaving them alone while he ran, but he had no choice. When he returned he found them elated for his victory, and discovered they had become fast friends.

Jean suggested that Bobby go home after the meet with her and not on the team bus. Bobby readily accepted and as they approached the car he saw Jeff waiting there. Jean said, "I invited Jeff to go to lunch with us, he seems like such a nice boy. I hope you don't mind."

How could Bobby mind? How could he even fathom this? Jeff seemed okay with it, and the three of them headed off for lunch. Within minutes of sitting they were talking about the dance. Bobby was very hesitant at first, but the enthusiasm of Jean and Jeff got him caught up in the conversation. Jean drove Jeff back to his car at the park. Jeff and Bobby awkwardly said goodbye, and promised to talk later.

Jean talked all the way home about how she liked Jeff. When she told Bobby to make sure Jeff came early the next Saturday so she could take pictures, Bobby couldn't believe it. This was getting too weird. His mom was being too good about this. He decided to ask her about it….but procrastinated all week.

Saturday morning and the high school cross country sectionals. Bobby was totally wired for the meet. He had the wonderful combination confidence and nervousness that he wanted. When the gun signaled the start of the "cavalry charge" at the start of the race Bobby was immediately in front of the pack. He felt comfortable and loose as he began the three mile course. No one really challenged him, his focus started to drift to the dance that night, but he forced himself to think only of the run. He won easily and the team finished first as well. Next week would be the regionals and that would be more difficult. Once the race was over his mind shifted completely to the dance. The school bus couldn't get him back to school soon enough. He hoped that his mom would be there waiting when the bus got there. He wanted to get the dirt and the sweat off and begin his transformation to Bobbi.

True to her word, Jean was in the parking lot when the bus arrived. Bobby bounded out of the bus and waved "see 'ya" to his teammates and ran to the car where his mom was waiting for him.

Bobby leapt into the car and started jabbering about the cross country meet and how well he did, and then how he needed to get ready for the dance. He was so hyper that he was jumping all over the place while jabbering to his mom. Finally Jean said, "Bobby, calm down. We have over five hours to get you ready for the dance. Plus I have surprise for you at home. So slow down and tell me about the race while we go home."

So he did just that. He told her that they won and that they would be going to the regionals next week and that coach was very pleased with the whole team's performance. He finished his story as they pulled into the driveway. There was a strange car parked in front of the house, but Bobby didn't notice it.

Walking into the house Bobby started to get hyper for the second time this Saturday. Only this time he was nervous and not confident. Suddenly he was afraid of this whole idea. He was about so say something to his mom as they entered the house. But he was cut short when his mom introduced him to Sherrie.

"Bobby, this is my good friend from the hospital, Sherrie, she's here to help with your makeover. She is a beautician and knows about your secret. Now run upstairs and get cleaned up. Then get back down here….we have a lot to do." Bobby started up the stairs, and his mom added, "I put a robe out for you, just wear that!"

Bobby's brain was now in complete overdrive. Good Grief! His mom had told someone. Now everyone would know that he was a freak. But what could he do? He couldn't back out on Jeff now. He'd have to go with the flow and then throw all this stuff away and end everything tomorrow.

Once he entered his room he took a deep a breath and steadied himself. He headed into the shower and saw the note his mom had left on the mirror to use the Nair she left on the counter. She also added, "calm down, I love you! Don't worry about Sherrie; she's a lot like you!" He looked up into the mirror in disbelief. Maybe this would be okay. He smiled and started an unconscious transformation.

He read the directions and applied it generously all over his body. He waited the allotted time and jumped into the shower. Bobby carefully washed and then shaved what little beard he had…three times. He dried himself off and donned the silky bathrobe his mom had left for him, and padded barefoot downstairs.

Sherrie and Jean had set the kitchen up to resemble a salon. There was a hairdryer in the corner and nail "stuff" on the table. Cosmetics filled the balance of the table. Bobby was speechless. Sherrie and Jean just smiled and had Bobby sit down opposite the nail paraphernalia.

Sherrie went to work. She started on his hands, filing and buffing and then polishing his nails a glorious shade of pink. Sherrie then started on his toes. She repeated the process while she talked to Bobbi about her life. She told him how she was a lot like him…or her. How in high school she did all the same things he did, but without the kindness of her parents. She told him about how her father had thrown her out of the house at 17, and how she lived on the streets for two years. As she finished his toes she finished her story; and how through the kindness of some people at the hospital helped her get her life turned around.

Bobbi pulled his gaze from the loveliness of his feet to look at his mom. He wanted to thank her, but couldn't he saw her crying from Sherrie's story. When he saw her crying, he started, and then Sherrie joined them.

Sherrie got her composure first, and said, "thank goodness we did the nails first and not make up! We'd have to start over!" Bobbi and his mom laughed and dried their eyes.

Sherrie then started on Bobbi's hair. Jean and Sherrie decided on a sophisticated upsweep, and hoped that they'd have enough hair to do it right. It took a while but Sherrie was finally done, and even though Bobbi couldn't see the result, his mom's smile made him think it must look good.

Now on to the make-up; Bobbi was talking to Sherrie like she was an old friend. Bobbi was filling her in on his journeys outside as "Bobbi" and how much fun "she" had. Bobby was now Bobbi. Jean sat in the corner and marveled at the mental transformation as much as the physical one. Sherrie brushed some powder on Bobbi and then gently took her chin and moved Bobbi's face from side to side. Sherrie smiled, looked over to Jean, and said, "She's beautiful don't you think?"

Jean stood up and took Bobbi's hands. She gently pulled Bobbi to her feet. Jean smiled and said, "Sherrie you did a magical job. She is truly beautiful"

Bobbi wanted to see how he looked, but both women said not until she was fully dressed. Jean escorted Bobbi back upstairs and into his/her room.

Jean sent Bobbi into her room to get into her under garments. Bobbi quickly donned her panties then stood around for a moment before realizing that panties were the some of her undergarments. They had decided her tanned legs wouldn't need stockings and her bra was build into the dress. Bobbi painfully tucked herself "down and under" and called her mom.

Jean came into Bobbi's room smiling. She was so glad to see Bobbi happy. Jean took the strapless royal blue dress from its hanger and helped Bobbi into it. Jean carefully zipped it up the back and helped her beautiful son adjust the bust line. She then helped Bobbi with earrings, bracelets and a surprise. She handed him a beautiful choker. It had a ribbon that matched the dress perfectly and had a single pearl drop (that matched the earrings) in the center. Bobbi hugged his mom and fought back tears. (S)he was so happy at that moment. The preparation had taken his mind completely off the dance. It was if the act of getting ready was the event.

Now it was time to let Bobbi see the final result. Jean watched as Bobbi slipped into the beautiful three inch royal blue pumps and she led him to the full length mirror. There wee no words that Bobbi could use. His hand flew up to his mouth. He felt weak in the knees. Jean held Bobbi as he regained his composure. He was just babbling thank yous to her. Jean kissed him on the cheek, and said, "You're welcome. I love you."

Neither Jean nor Bobbi heard the doorbell. But Sherrie did, and she called upstairs that Jeff had arrived. Jean told Bobbi to wait upstairs; Bobbi needed to make an entrance. Jean hurried downstairs and Bobbi listened as she complimented him on how handsome he looked, and how Bobbi would be down in a few minutes.

Bobbi wanted to go down now. His guy persona informed him that he was ready, he should go downstairs. He paced in his room, alternating between being nervous about the whole night and then looking in the mirror in total disbelief at how beautiful he looked. Finally, he heard his mom call out, "Bobbi, are you ready?"

Bobbi steeled himself and responded, "Yes mom, I am on my way."

He carefully walked from his room to the stairway and slowly descended the stairs. When Bobbi came into the view of Jean, Sherrie and Jeff he heard Jeff gasp. Bobbi instinctively smiled. She then saw him. He was very handsome. He looked great in his suit. Bobbi walked down the stairs and Jeff had the audacity to kiss her right there in front of his mother. Bobbi was shocked, but not shocked enough to not return the kiss.

Jean "harrumphed" them, and when they broke their embrace, she said "time for some pictures."

Jeff suddenly remembered the corsage….he presented a white box to Bobbi. Bobbi opened it and found a beautiful wristlet of white tea roses. She slipped it on her left wrist and she and re mom oohed and aahed appropriately. Jean went to the kitchen and produced a boutonnière from the refrigerator for Jeff. Bobbi tried to pin it on with absolutely no success. Jean stepped in and expertly affixed a matching tea rose to Jeff's lapel.

 

Once properly "flowered" Jean positioned the couple near the fireplace and took a dozen pictures. Some were of the couple and she took pictures of each of them. Finally, when she hesitated for a moment, Bobbi declared that they had to go.

Jeff thanked Jean and asked for copies of the pictures, and they headed for his car. Ever the gentleman he opened the front door and the car door for her. They then headed out for the dance. Jeff turned the corner and pulled over to the curb. He looked at Bobbi, and said, "Bobbi, you are absolutely beautiful. I never dreamed you would be this amazing. You are going to be the prettiest girl at the dance." He then leaned over and kissed her passionately. Bobbi returned the kiss and it took all of their will power to break it off. Bobbi almost suggested skipping the dance, but knew that wouldn't be a good idea.

Twenty-five minutes later they pulled into the school parking lot. Jeff helped Bobbi out of the car and they walked, arm in arm, from the lot to the gym.

Bobbi was very confident of her look, but was still a little nervous about being there. She really didn't know anyone form this school except for some cross country runners, a couple of basketball players, and three or four guys on the baseball team. Once she did that count in her head, she thought that was a lot of people! Well it was too late now, and she confidently walked with Jeff into the gym. He immediately started introducing her to all of his friends. Bobbi tried her best to remember all their names, but was failing miserably. She smiled and nodded at all of them.

It wasn't too long before the DJ started playing and Jeff took her out to the dance floor. They were out there for half a dozen fast songs, and then there was the traditional "we're going to slow things down for a moment" statement by the DJ. Jeff took Bobbi into his arms and Bobbi looked up into his eyes. She smiled and said, "I am so glad to be here with you. This is so much fun." She then put her head on his shoulder and sighed.

Jeff pulled her tighter into him, and gently stroked her back. He quietly said he was proud to have her as his date, and he was even more convinced she was the prettiest girl at the dance. Bobbi looked up at Jeff and felt loved and protected. She felt warm and wonderful all at the same time.

The song ended and they kissed. Bobbi felt her melt into his arms. When they broke their embrace, Jeff said, "I love you."

Bobbi, felt completely at ease replying, "I love you too Jeff."

They danced and talked to Jeff's friends for a couple of hours. Finally, Jeff whispered, "do you want to get out of here?"

Bobbi asked where would they go?

Jeff said his folks were not home. They could go there, and it was only a couple of minutes away.

Bobbi leaned over and kissed Jeff on the cheek and said, "Let's go handsome!"

Less than ten minutes later Jeff opened the door to his folks house, and let Bobbi in ahead of him. Once he walked in to the hallway, he spun Bobbi around and kissed her again. Bobbi was all over him as well. The two teens were both totally aroused. Jeff said, "Let's go to my room."

Bobbi said, "Catch me if you can!" She took off up the stairs with Jeff in hot pursuit. She turned left at the top of the stairs and Jeff called out, "Wrong way! I am at the end of the hall….the other way!"

Bobbi tried to turn quickly turn, but couldn't do it. She fell. Jeff reached down and helped her up. They were both laughing uncontrollably. He then lifted Bobbi up and carried her to his room. When they got there he gently laid her on the bed. She held her arms out to him, and soon he was in her embrace. They kissed and fondled each other until Bobbi finally said, "Let's get out of some of these clothes."

Jeff got off the bed and started to take off his shirt. Bobbi jumped up off the bed and said, "Here, let me do that." She undressed him completely, then sensuously kissed his chest and massaged his butt. Jeff then reached behind Bobbi and slowly unzipped her dress. In seconds she was only wearing her choker. Jeff kissed her softly on the neck and moved down her throat, and gently kissed and sucked her nipples. Bobbi was going crazy with desire. Their dicks were touching and making each of them more and more aroused. They each knew that they had better access to each other if they were horizontal and soon enough they were back on the bed. Each one was trying to do something wonderful for the other one.

Jeff finally took control. He whispered to Bobbi that he was going down on her and wouldn't take no for an answer. Bobbi wanted to "69" but Jeff insisted on taking care of his girl friend.

Bobbi was moaning loudly and massaging Jeff's hair as he bobbed up and down on her. She couldn't last any longer. "Oh Jeff, I'm cumming..Oh darling you feel so wonderful. I can't wait.!!"

She filled Jeff's eagerly sucking mouth with her hot cream. She sank back into the bed while she pulled Jeff up to her mouth. She hungrily kissed him. She tasted her own cum and tried to suck it all off of his tongue. She was in love. She wanted to show her lover how much.

Bobbi said, "Oh Jeff I love you so much. I want you in me. I want you to make love to me as a woman. Do you have any lubricant? I can't wait baby, I want to feel your cum inside me and I want you to love me."

Jeff didn't say a word, he reached over to the nightstand and took out a tube of KY Jelly. Bobbi smiled to herself and thought, "I love this guy, he was ready for this all night."

Jeff started to lube Bobbi's love hole while she lubed his penis. She laid back on the bed spread her legs and placed them on his shoulders. Bobbi was gasping for air when Jeff leaned down and kissed her. As he did he slowly started to penetrate her. Bobbi was nervous and afraid, but wanted him to make love to her. She relaxed as best she could and kissed him back. She felt the tip of his penis start to enter her. She kissed him harder as he slowly moved back and forth inching his way into her.

Jeff looked at her and when Bobbi saw the look on his face, the total expression of love, she knew it was worth any pain she experienced. Bobbi and Jeff were now rocking together in unison. Bobbi slowed them down, she wanted this to last for both of them.

 

She looked up at Jeff and smiled. She wanted to feel him in her for a long time. It really was feeling good. She wanted Jeff to enjoy this too. They spent the next twenty minutes whispering sweet nothings to each other. Then Jeff started to speed up. He was going to cum. Bobbi started to buck faster too. She pulled him on to her and cried out, "Jeff I love you!" Jeff merely grunted and came with a force he never experienced in all his young life. He started to roll off of her, but she held him fast. She didn't want him out of her yet. She caressed the back of his head, and scratched his back. She felt his breathing become normal again. She hugged him again, and this time he slid off of her. Bobbi curled up in Jeff's arms and snuggled close to him. She felt like a woman. She had taken care of her man. He had taken care of her. For better or for worse they were a couple now. She felt Bobby trying to get into her brain. She wouldn't let him. She buried her head in his shoulder and massaged his penis.

Bobbi didn't want this to end, but she knew she would have to go home. Jeff was starting to get frisky again, but she knew she'd have go home. She tried twice to get him to stop, and when that didn't work she eagerly joined him in another sexual romp. They were soon in the classic 69 position. It didn't take long for either of them to cum again. They luxuriated in the afterglow for a while and then Bobbi got up and into her dress. While in the bathroom she surveyed the wreckage of her makeup and hair. She redid her makeup as best she could, but her hair was beyond repair. She undid it, and pulled it into a pony tail. Jeff got dressed as well. They walked down to leave holding hands and staring lovingly at each other. Neither wanted to go, but they new they had to.

As Jeff drove them back to Bobbi's he asked Bobbi where she was going to go to school next year. He said he was asking because maybe they could go to the same school. Bobbi replied, "I don't know yet Jeff. I need a scholarship, and I am hoping to get one for either cross-country or baseball. I should be hearing soon, and you know that I will let you know about every offer. Have you made any decisions?"

Jeff mentioned two big state schools and a private East Coast school, but added he wasn't enamored with any of them.

Soon enough they were parked in front of Bobbi's house. Jeff took Bobbi in his arms and said, "Bobbi thank you, this has been the most wonderful evening of my life. I really do love you."

Bobbi, simply kissed him, and said, "I love you too. Thank you! This has been a spectacular night. I don't know how we are going to top this."

Jeff said, "I don't know, but it will really be fun trying."

The two teens laughed and Jeff bounded around he car and let Bobbi out. He held her hand as they walked to the front door. They kissed again, and promised to call each other in the morning. Jeff didn't want to leave and Bobbi didn't want him to. They kissed again and promised to call each other in the morning again, and then again. Finally Jeff laughed and said he did have to get home. Bobbi opened the door and waved good bye to him. She watched at the doorway as he drove away.

Bobbi closed the door and leaned up against it with her eyes closed and smiled. It had been a wonderful night. She opened her eyes and saw her mom standing there with the a huge smile on her face.

"So….how was it?" Jean said.

"Oh mom it was great. We had a wonderful time. The dance was great. Jeff has lots of wonderful friends. The DJ was cool. I had a wonderful time." Bobbi said.

Jean then asked, "well what else did you do?"

"Mooooommmmm…." Bobbi said, "I can't tell you that."

"Why don't you get undressed and put on a robe and come down stairs, let's have a cup of tea, and let's do talk about it. Don't worry, I just want to share in your happiness." Jean said.

Bobbi took off her heels and bounded up the stairs. She took off her dress and carefully hung it up. She then combed her hair and reset her ponytail, she left her makeup on because she wasn't ready to go back to Bobby with a "y" yet. She put on her pajamas and her robe. She glanced down at her painted toenails and smiled. What a great day this had been. She still felt beautiful, and she still had the warm afterglow of being loved.

Bobbi headed downstairs with some trepidation, but she knew this was a conversation that was long overdue. Jean had been way to tolerant of this whole thing and Bobbi figured it was time that his mom reeled him in, at least somewhat.

Jean was sitting at the kitchen table with two cups of tea. Bobbi sat opposite her and smiled at his mom. He thanked her for the tea and took a sip, then said, "What's up mom?"

Jean looked at her son; with his soft feminine features made all the more feminine by make up and long hair, and smiled back. She sighed and said, "What are we to make of all this Bobby? Where do you see this going? I don't want to make this hard on you tonight, but I want you to at least be thinking about it."

"Mom, I don't know. Earlier today, when I was going to take my shower I vowed to tell Jeff that this whole thing was over and I was going to throw away all my girl things Sunday morning. Then I had such a wonderful time tonight as "Bobbi" I know that won't happen, and I certainly didn't tell Jeff this was over," Bobbi replied, "In fact if anything I like dressing even more than I did when I left the house for the dance. Mom, what's wrong with me? I like being a guy, I love cross country, basketball and baseball. I don't want to be a girl, but tonight I told a boy I loved him"

Bobbi started crying as he finished that sentence. Jean came around and took him in her arms. She held him. She was surprised at how hard he was crying. She couldn't see his face, he hid it from her. Finally, Jean said, "Bobby, you don't have anything wrong with you. You are a wonderful person. I don't know why you like to do this either. But we can look for the answers together. I hope you'll agree to see a doctor who can help explain this for us. She's a great lady. She'll help us together. What do you say?"

Between sobs, Bobbi said, "See there is something wrong. Why else would you want me to see a 'shrink'? I'll do it, but we can't let anyone know…not anyone."

Jean promised no one would know. Then after some lightweight banter about the dance (Jean chickened out about asking what Bobbi and Jeff had done sexually) they both headed off to bed.

Bobbi took off his makeup but still left his nails painted. He still wasn't ready to be Bobby. He took a Kleenex to bed with him. He knew would be thinking of Jeff before he went to sleep, and that meant one more ejaculation before sleep.

 

To be continued

  

  

  

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