Sport Model

by JL Williams

 

Bobby carefully placed the gym bag in the rear of his closet. He double-checked the lock on the Nike bag, and as he piled boxes around his stash he sighed. It seemed like he never got to dress very much anymore. His mom finally got enough seniority at the hospital to work days. He should've been happy to see her, and have dinner with her….but it took away his time to dress. Bobby turned off the light in his closet and headed downstairs to start dinner in his own drab clothes.

Bobby wondered about his fate as he started dinner. He was 5'6" and 120 pounds. He was popular at school. Despite his size he was a three-sport athlete. He had finished eighth in the state cross-country finals last year as a junior. He was picking up his running now this summer…hence the spaghetti dinner. Even though he was short, he would be the starting point guard this year on the basketball team, and it was going to be a very good team. His first love, after dressing, was baseball. He would be starting again this spring at shortstop. Not bad for a runt he thought. His grades were good too—a solid B+ average. He didn't hold out much hope for a division one scholarship, but five division three schools were putting together excellent grant in aid packages and had contacted him. He wanted to go away to school, but if worse came to worse, he could do like his sister Grace, and go to the local junior college before going to State.

Dinner was ready when Bobby's mom, Jean, arrived. She looked great in her nurse's uniform, but she was tired. She had been a single mom since Bobby was two and Grace was five. Her husband just didn't come home from work that fateful day. He had some gambling debts, and foul play was always suspected, but never proven. She worked to raise her kids and was proud of her success…. and theirs.

She kissed Bobby on the cheek and thanked him for making dinner. She poured herself a glass of wine, sat down and started asking him about his day. Bobby said that he had gotten out early at the golf course and was done caddying by 2:00, he came home and shot hoops and "stuff"…the thought of what he secretly meant by "stuff" made his cock twitch. Bobby's mom worked in the emergency room at the area trauma center hospital, so she always had great stories. They talked about their days until dinner was over. Jean, Bobby's mom, insisted on cleaning the kitchen after dinner. She asked if he was going out. He said no he had to get up early; there was a tournament at the golf club the next day and Mike Williams was picking him up at seven in the morning. Jean said she worried about him not going out more, but he said he was busy enough. They were both in bed and asleep by ten o'clock that night.

Friday morning dawned clear and warm for a July day in the Midwest; but Bobby was up before that. He got in six miles before six AM. This Friday would be a perfect day for golf. After his run Bobby was feeling great. He took a hot shower, ate some breakfast and bounded out of the house to the sound of the horn of Mike's car. They had been friends long enough to be comfortable to just listen to the radio on the short ride to the club.

The caddy master liked Bobby; and he knew that Bobby needed the money, and that he was dependable and always polite. The caddy master gave Bobby a good loop, one that would give Bobby a great tip whether he won the three day tournament or not. Bobby and Mike wound up in the same foursome that was great for Bobby, which meant he wouldn't have to wait around for a ride home, or worse have to walk, if Mike left early. The idea of getting a car was one that Bobby knew was out of the question.

After their round Bobby and Mike cleaned the members' clubs, and headed off for home. Mike dropped Bobby off in front of his house. Bobby begged off going out with everyone that night, using having to get up early and get his Saturday long run in before caddying as a pretext. Actually his mom was going into the city to go out with some old high school friends and wouldn't be home 'til late. He could dress tonight!

When Mike pulled up in front of Bobby's house there was all kinds of activity going on next door. There was a moving van and a couple of unfamiliar cars. Bobby remembered that the Simon house had sold, but he didn't know that today was move-in day. He told Mike that hopefully there would be beautiful triplets moving in next door. Mike laughed, and said they'd have to be really beautiful to look better than Cindy. Mike had dated Cindy for two years and Bobby thought that Mike was right. She was drop dead beautiful. Before Bobby could get his gear out of the car, Mike had called Cindy. Mike yelled that the cheerleaders were back from camp, and Cindy would be able to fix Bobby up tonight. Bobby thanked Mike for that but he really needed to sleep and run in the morning. Bobby knew that Mike would be hanging with the football team tonight. Despite Bobby's jock status, the football players, at least the core Neanderthal group, tried to bully him. However, Bobby had enough friends on the team to keep them at bay, but he always felt uneasy around the Paul Taylor group.

Bobby walked over towards the movers. He spotted a woman in her early forties directing the movers, and went over to introduce himself. She was his new neighbor Rita Wilson. She seemed very nice, and was impressed that a teenager would introduce himself. She called out two names. Bounding out of the house was Pete Wilson. Bobby recognized him. He was the starting quarterback at State two years ago, and destined to be a number one pick in the NFL draft until he trashed his knee in the Cotton bowl.

Pete said hi to Bobby and turned to his mom and said they were just about done. He added a nice to meet you kid, turned and with only a slight limp bounded back into the house. Pete passed someone who looked to be Bobby's age. He came out of the house at a snail's pace. He had body language that screamed, "Let me be anywhere but here!" Rita called to him, "Tommy don't dawdle, there is someone here I want you to meet."

Tommy was almost six feet tall and very handsome. He would have looked even better if he hadn't been scowling. His mom introduced them to each other, and they discovered they were the same age. Bobby immediately knew why Tommy was scowling, Bobby thought about how horrible it would be to transfer schools in high school, let alone your senior year. Bobby tried to be friendly, and even offered to fill Tommy in on school, but Tommy would have none of it. He mumbled something about it being nice to meet Bobby and wandered back into the house.

Rita tried to apologize for Tommy, but Bobby said not to worry. He understood. He said he wouldn't want to switch schools in his senior year either. Rita thanked Tommy, and asked where his parents were. He explained about his household, and said he was sure his mom would stop by tomorrow. With that, he headed home…to dress….but by the time he got home; he was paranoid about his new neighbors coming over. He wasn't sure what he should do. He puttered around the house for a while, and then as soon as it was dark he couldn't resist the siren call of his bedroom.

He donned his favorite panties, nylons and garter belt, but kept them hidden under a pair of jeans until almost nine o'clock. Bobby then put on his sister's prom dress, a strapless slinky number in shocking pink. Bobby crammed his feet into the matching shoes, and applied a little make up. He did what he could with his hair, but it never looked like he wanted it to look. Bobby waltzed around his sister's room secure in knowing the doors to the house were locked and the shades and curtains in his sister's room were drawn. Bobby imagined he was dancing with a handsome man, one who would take him in his arms and take his breath away with hot steamy kisses. One who would late take him to bed and make sweet sensuous love to him. When it came time for the love making in Bobby's fantasy he carefully hung up his sister's dress, and donned one of her satiny baby doll pajamas. Bobby lay down on her bed and masturbated as he thought of this faceless lover taking him, and Bobby taking him into "her". As always once he came stripped off the clothes, put every thing carefully away, and removed the makeup.

Saturday morning dawned as a repeat of Friday. Bobby had run twelve miles by the time Mike was scheduled to pick him up. Mike was right on time and they headed to the country club for the second day of the tournament. Once again Mike and Bobby finished at about the same time, so Bobby got a ride home. Mike said a bunch of the kids were going to Katie White's house that night for a party. Did Bobby want to go? Since Bobby knew his mom would be home, and there was no chance of dressing, he said sure. Mike said that the party would start at about 8:00 and he'd meet Bobby there. Bobby bounded out of the car and as he looked up he saw him mom talking to their new neighbor.

Jean and Rita were laughing and getting along like old friends. Bobby walked up and they greeted him warmly. Bobby's mom was pleased because he had been so polite and outgoing yesterday. Jean and Rita asked him about the golf tournament, and he said it was fine; his "loop" had a chance to win some serious money, which would transfer into a good tip for him. Jean asked what he was going to do that night. He told her about the party at Katie's house. Jean said they would be eating with Rita and her family, and maybe Tommy would be interested in going to the party and meeting some of his soon to be classmates. Bobby absently said fine, and headed into the house to clean up. After seeing Tommy yesterday, he was sure he wouldn't go.

Dinner was terrific. Mrs. Wilson was a great cook. Pete was a lot of fun and he seemed interested in Bobby's athletic ability. Only Tommy was quiet. Sullen really, he ate quietly and looked at Bobby like he was a dangerous intruder into his home. Jean suggested that Tommy go to the party with Bobby, and Tommy flatly refused. He excused himself from the table and went to his room. Mrs. Watson tried to make excuses for her son, but Pete cut her off. He said that Tommy was being a brat and that he'd go up and take care of the "little shit". Out of nowhere, Bobby said, "Pete if you don't mind, maybe I can help. Let me go up and talk to Tom." Both mothers were impressed, and Rita Wilson thanked him profusely.

Bobby wandered up to Tommy's room; it was the only one with the door closed. He knocked, and called Tommy's name. "Go away!" Was the response to the knock. Bobby ignored this and brazenly entered. Bobby saw Tommy laying face down on the bed. He appeared to be crying. Bobby walked over to the chair by the desk and quietly asked why he was taking this move so hard.

Tommy said that Bobby wouldn't understand. Has Bobby asked the question again, he was given the same answer. Finally, after an awkward silence, Tommy shot up and blurted out that he was gay. He said that his mother and brother brought him out to this God forsaken suburb to get him away from his friends in the city and to make him straight by making him live in this "white bread" environment.

Bobby sat there stunned. He couldn't believe it. His mind was racing. Finally he said you know it won't work. You are what you are. In fact there is a school sponsored GLBT group. I know the president and would be happy to introduce you to him.

Now it was Tommy's turn to be shocked. He was totally surprised by Bobby's reaction. He thanked Bobby for the offer, but he felt he needed more time by himself before meeting new people.

Bobby said that he just wanted the time to feel sorry for himself. The president and his boyfriend would be at the party tonight. Tommy should go, and if he really didn't like the party they could leave. Tommy reluctantly gave in, and agreed to go. Bobby said he would pick Tommy up at 8:15, no sense being too early. He said just wear shorts and a golf shirt.

When Bobby told the women that Tommy was going Mrs. Wilson hugged Bobby so tight she almost squeezed all the air out of his lungs.

As Tommy and Bobby walked to the party, Tommy did all the talking. He explained how his dad, now divorced from his mom, couldn't understand why he wasn't like his brother. His brother called him an embarrassment. His mom tried to understand, but she couldn't. So she decided that moving to the suburbs would "cure" him. Bobby listened, and silently empathized with him.

The party was in full swing when they arrived. Katie's house had a huge back yard and her folks had put a temporary dance floor in the middle of the lawn. Her folks were at the entry point of the yard, and Bobby introduced Tommy as a new kid in the school to them, and then brought him around to his friends, both the boys and the girls. Finally, they happened on Jack Moore and Bill Jackson. Bobby introduced Tommy to them and added that Tommy only came to the party to meet them. Jack and Bill got the idea, and Bobby left them to talk.

Bobby found Mike who was talking to three of Bobby's running mates on the cross-country team. As the night wore on, he danced, talked to a bunch of other folks and kept an eye on Tommy. Tommy seemed to be smiling and animated as he talked to Jack and Bill. Bobby smiled. He was glad to have introduced them. But his smile faded as he saw Paul Taylor and four of his football buddies half stumble into the party. Bobby looked desperately for Katie's parents, but they must have gone into the house. The Neanderthals headed straight for Paul and Jack, and Tommy. Bobby instinctively headed to the confrontation. He could hear "faggots" as he neared them. Tommy stepped up to confront Taylor, but Bobby cut in front of him. He told the middle line backer who towered over him by at least nine inches, to leave these guys alone and as a matter of fact if they were smart they would leave the party period.

Paul Taylor leaned down into Bobby's face and sneered. Well look who we have here the runt jock he said through his beer breath. Are these faggots your friends? Bobby sneered back that they were and they were better friends and better people than him and the knuckle dragging jerks he was with. Paul stepped back to hit Bobby, but Katie's dad called and demanded to know what was going on there. Bobby looked toward Mr. Green. Paul didn't stop; he caught Bobby on the side of the head, and knocked him out with one punch.

When Bobby came to, he found the party over. Tommy was sitting with him along with Mike, Cindy and the Greens. Bobby found out that the cops had come and had taken Paul Taylor and his buddies to the police station. Mr. Green had called Bobby's mom and she was on her way to get him.

On the way home Tommy thanked Bobby over and over, but also said that he could take care of himself. Bobby said it was his responsibility since he invited Tommy. Jean wanted to know what started the fight, and Bobby said that Paul Taylor was drunk and wanted to pick a fight with the new kid.

Bobby insisted on caddying the final day of the tournament, and was waiting for Mike at 7:00 Sunday morning. Luckily Sunday was an off day for running 'cause Bobby still had quite a headache. Mike cruised up to the curb right on time. He whistled softly as he saw the shiner and bruise on the left side of Bobby's face. Bobby asked him not to make him laugh 'cause he had a headache, and his face really did hurt.

The day went by with a minimal amount of comment, and Bobby's loop came in third. Good enough for a lot of money, money that Bobby would give to his mom for his college fund.

On the way home Mike was on his cell phone the whole ride. Evidently Paul Taylor had acted up at the police station. He was still in the holding cell, and it looked like he was in jeopardy of being kicked out of school. The rest of his friends were released and looking for Bobby. Mike looked over to his friend and suggested that he go on vacation for about six years. Paul's friends were bad, but once Paul was out of police custody he would really be looking for Bobby…to do some permanent harm. Bobby was nervous, but he tried not to show it. He said Paul got in a lucky punch, and next time the outcome would be different. He knew he didn't believe it, but he had to put on a brave front.

Mike dropped Bobby off and waved good-by. Mike liked Bobby a lot, but he made the mental note to put some distance between himself and his friend for a while…his physical well being would depend on that. When Bobby entered the house he found his mom on the telephone. She motioned for him to sit down. When she hung up she said that she was talking to the police, they wanted him to press charges. Bobby said no. He said that it would make things worse. It was just a high school fight, and it should end there. Besides, he knew this went to court Tommy would get dragged into it, and he didn't want that. Jean, asked him to reconsider. Then she changed the subject. She asked how he did caddying, and he gave her the money to deposit. She then suggested he go to bed, and get some rest. He agreed.

The next few weeks were actually uneventful. Paul heard that Bobby was not going to press charges, and while he boasted that it was because Bobby was afraid of him, he also stayed away from Bobby. Not because he was that smart, but because the football coach threatened him with the beating of his life if he did anything else stupid this summer.

Bobby noticed that Mike was becoming scarce, and he wound up spending time talking to Tommy. It turned out that Tommy was bright, funny and very interesting. He regaled Bobby with tales of the big city, and Bobby said they needed to make a road trip. Tommy agreed, and said if Bobby didn't mind, his mom would feel much better letting him go to the city if Bobby went with him. That was on a Sunday night, and the plan was to head into the city Saturday night, if Tommy could get the car.

Monday the golf course was closed and Bobby's mom was at the hospital. It was a cold and rainy day that was all right in Bobby's mind 'cause he was going to spend most of the day dressed. After running in the morning, and having breakfast, it was time to transform. He took his time. He took a bubble bath, and then he shaved what little hair he had on his legs and arms. The rest of his body was hairless already. He took out his Nike bag, unlocked it and decided that since this was the first time he was dressing without the shiner from Paul, we was going to go all the way. He took out the nail polish, which he rarely used, and did his toe and finger nails in soft pink. Once they dried he put on his garter belt and nude hose. He then donned a black bra and inserted the two breast forms he had bought through the mail. He put on a robe that his sister had left behind and went into the bathroom to put on his make up. Forty minutes later he emerged. Bobby was happy with the work he had done. The lipstick matched his nails, and he felt like he had done his best work on his eyes…ever. He had combed his hair into what he called his Lorrie Morgan look. He added the clip-on earrings from his stash and the choker; he had a passion for chokers. He then went to his sister's room. He knew exactly what he wanted to wear. He went right for her black dress. He had to tuck his erection down before he put it on. He loved the dress. It fit him, and he always felt sexy in it. He put on the three inch black patent leather shoes and turned to look into the mirror.

Bobby sighed, he loved dressing, and it was so relaxing. His plan was to spend the next few hours dressed, for now in the sexy black dress, and later in the scanty baby doll pajamas, and while dressed in them, he would masturbate. Then reluctantly he would remove his make up and nail polish, and return to being "the runt jock". He frowned as he thought how that comment from Paul had stuck with him. Bobby decided to head downstairs and get something to drink. He walked down the stairs with the confidence of someone who has done it in high heels many times. When he hit the landing the front door burst open, and Tommy entered, without knocking and his coat over his head to keep the rain off of him. When he pulled the coat down he saw Bobby, frozen in terror.

Bobby couldn't move. Tommy couldn't either. Finally Tommy said, "Bobby you are beautiful. Don't worry, I love the look." Then he smiled. Bobby couldn't believe it, but he started to cry. Tommy moved to his new friend, and put his arm around him, and walked him to the living room, and gently sat him down on the couch. Tommy positioned himself across from Bobby and sat on the footstool. He handed Bobby his handkerchief and reiterated how pretty he looked.

It took Bobby a while to compose himself, and he finally thanked his neighbor for being so understanding. Tommy laughed, and told him that everyone had their little secrets. Some, like the two of them are a little more out of the ordinary. Then Tommy peppered him with questions. How long had he been doing this, was he gay, had he gone out of the house dressed, did anyone else know, and on and on. Bobby quietly answered all the questions. He said he'd been doing it for a long time; he was no different from the rest of the cross-dressing community…at least what he knew from the internet, he had never gone out of the house, and he didn't think he was gay.

Bobby finally felt okay with Tommy, and Tommy told Bobby not to worry, he wouldn't hit on him. He explained that he was a "bottom" and that he and Bobby would probably wind up fighting for the same man. That got a laugh from Bobby. They wound up spending the rest of the morning talking and laughing. Bobby even fixed lunch for the two of them. Finally Bobby said he had to change, and clean up. Tommy said he'd come by after dinner he had a great idea for Saturday night. Bobby, kissed him on the cheek and held Tommy's hands, and gave him the most heart-felt thank you he had ever said to anyone. Bobby quickly went upstairs, masturbated and transformed himself back into a boy.

Bobby finished preparing dinner as his mom entered the house. She kissed him on the forehead, and after putting her coat away joined him for dinner. She asked about his day, and he honestly told her that he and Tommy spent a lot of time talking. He also mentioned that Tommy asked if he could go into the city Saturday night. Jean said she worried about driving so far. Bobby persisted, and Jean finally relented. She said if Tommy could get the car, she would let him go. Bobby thanked her and they cleaned the table together. Bobby offered to wash the dishes, but Tommy rang the bell before his mom could say anything. She said, "You've done enough, go!"

Tommy was flush with excitement. He couldn't wait to tell Bobby his plan. They went up to Bobby's room, and he laid out their Saturday. First, they would leave at one o'clock. Tommy had talked to two of his friends in town who were teenaged cross dressers, and they would help Bobby with his transformation. Then that night there was a dance sponsored by the local teen adjunct of GBLT in the city. They could go to that and have a great time.

Bobby was too shocked to answer. First this was the most animated he had seen Tommy. Second, Tommy was talking about Bobby going out in public dressed as a girl!! He couldn't do that, could he? Suddenly, Bobby felt himself getting caught up in Tommy's enthusiasm for this plan. Bobby opened his mouth to say "no" he couldn't possibly do this, when the word "yes" came out of his mouth. Tommy was so pleased he hugged Bobby. He said this would be so great. He said he couldn't wait for Saturday to come.

Bobby could wait. He was scared and was going to tell Tommy he couldn't do it. But as the week rolled on Tommy kept his excitement level to the point Bobby couldn't tell him no. On Friday, Tommy told Bobby he didn't need to bring anything. He told him that Gina and Jeri were very excited to meet him and to work some magic on him. He also told Bobby that the dance that night would be fun; it was the first dance in quite a while so it should be well attended. Bobby nodded dumbly. He was trapped, and while he was sure this would be a bad idea, deep inside him he was excited. He finally asked if he shouldn't bring make up or shoes, or something. Tommy said no the girls were going to have everything.

Saturday dawned gray and rainy. This made it easy for Bobby to skip caddying. He was up early for his long run, which gave him a lot of time to think. He couldn't do this and he would tell Tommy that he'd go to the city and the dance, but dressing was out of the question. Still, when he got home even though he couldn't take a bath, he scrubbed and shaved everything he could in the shower. He came downstairs to see his mom finishing her coffee. She looked up and smiled. She said since Bobby was going to be gone all day, she was going to see Grace at school. She said she was going to stay over at Grace's apartment, and she'd be home by noon or one o'clock Sunday afternoon. Bobby tried to hide his glee. This meant he didn't have to worry about getting home early. Jean said she was ready to go, and at noon she pulled out of the driveway.

Bobby was outside by five to one. He couldn't help but bring some "stuff" (he wasn't going to dress, but just in case he changed his mind). He had earrings, his ever-present choker, a pair of panties, nylons and a garter belt. Tommy backed the Wilson's car out of the garage. Rita Wilson came out and told Bobby how glad she was that he had made friends with Tommy. She felt so good that Bobby was going into the city with him. Bobby felt his stomach churn. He was embarrassed and felt like a fraud. He wasn't helping Tommy, he was abetting his condition; but Bobby also knew there was no "cure" for Tommy or for him for that matter. Bobby mumbled a "no problem", and climbed into the car.

Tommy saw the change in Bobby's demeanor and asked what was wrong. Bobby told him about what his mom said and Tommy replied, "Bobby, this is a great adventure for you. I am so excited to be doing this. This is partial payback for your kindness to me. Promise me you'll just have fun…no guilt allowed." Bobby promised.

At 2:20 Saturday afternoon Tommy rang the doorbell at his friend Gina's house. Bobby thought he'd faint. They heard "they're here!" squeals before the door opened. The door flung open and there stood Gina. She was a knock out. She grabbed Tommy and hugged him. Then she looked at Bobby, and exclaimed, "She's cuter than you said!" Bobby blushed furiously and tried to say something, but no words came to him. Gina took him by the arm and practically dragged him into the house. Inside the house was Jeri, a statuesque beauty who after hugging Tommy welcomed Bobby as excitedly as Gina.

Once inside the house the two girls motioned for the boys to sit. They told Tommy that he was free to go after he took them to the store. Tommy knew that already, this afternoon had been meticulously planned. The girls then explained to Bobby that they were in reality both boys. Jeri was like Bobby his folks didn't know, and he only dressed on the weekends with Gina. Gina on the other hand lived here with her mother who knew, completely understood and as Bobby would later discover actually encouraged her. They also explained that Gina's father, who was divorced from Gina's mom, was spectacularly wealthy and had no idea what Gina spent every month on her credit card, so they were going to transform Bobby….their treat!!

Bobby protested, but the three of them wouldn't hear of it. They finally dragged Bobby upstairs and got him into a pair of girl's shorts, a tank top and sandals. They put some rudimentary make up on him and said, "We're off to see the wizard!"

Ten minutes later they were in a small ladies boutique at the entrance to the mall. Gina and Jeri knew the saleslady and introduced "Bobbi". The next thing he knew he was in a dressing room with her being measured. Bobbi was torn between excitement and complete fear with side trips to who knew where. Maggie, the sales lady, did her best to calm Bobbi, he found himself actually shaking. Gina and Jeri were at another store making decisions on Bobbi's outfit for the dance.

Maggie wrote down the measurements. She then had Bobbi sit at the manicure table. Gina and Jeri had left instructions for the color—red. They figured Bobbi could be subtle later; this was a coming out party. Maggie struggled with Bobbi's trembling hands, but finished her job. She then did his toenails in the same bright color. Bobbie was practically transfixed by the sight of his digits. He moved as if in a trance as Maggie moved him to the chair where she would do his hair. It was a little long for a boy, but too short to do much with, but Maggie did her best to give him a feminine look. She then worked on his make up. She knew the "girls" would make her work a little more dramatic later, but Bobbie would look great in the mall.

Maggie finished as the girls erupted back into the store. They were so excited to be doing this; they were unable to control themselves. They burst into the back room, and immediately started gushing over Maggie's work. After being critically reviewed by Gina and Jeri, Bobbi was finally allowed to look at Maggie's work. He couldn't believe it. He really looked like a teenage girl. He couldn't take his eyes from the mirror nor could he stop smiling. Jeri stepped forward to put some clip-on earrings on Bobbi; Gina paid and extravagantly tipped Maggie.

Now it was time to head into the mall. The girls grabbed their new girl friend and pulled her out of the boutique into the crush of the mall. Bobbi was afraid at first but walking between Gina and Jeri he gained confidence with every step. The girls took him from store to store. Armed with the right measurements Bobbi soon had a several sets of bras and panties. He had four dresses and several skirts and tops. The most fun was the shoe store. The shoe salesman was a teenage boy and while Bobbi was reasonably well behaved, and Jeri was okay, Gina tormented the young man unmercifully. Gina kept leaning forward showing off the fact that she was not wearing a bra, and sitting in a very unlady like position while he was putting shoes on her. In all the girls bought fourteen pairs of shoes. Bobbi couldn't believe she now had four pair of her very own shoes….even if she would have to leave them at Gina's.

While Gina once again paid, Jeri called Tommy to pick them up. The girls carted their treasures through the mall, Gina flirting shamelessly with the few teenage boys who crossed their path. Tommy was waiting for them when they exited. He had a boy in the front seat with him. The girls knew him, and with the exception of Bobbi everyone kissed everyone else. Tommy introduced him to Bobbi, his name was Kevin, and he was obviously Tommy's boyfriend. The girls piled their purchases into the trunk, and then all three piled into the back seat. Bobbi was wedged into the middle of the back seat. He was smiling. Jeri had his arm around him, and whispered in Bobbi's ear that if he thought buying things was fun, wait until they started trying things on.

Bobbi had no chance in keeping up with the multiple conversations in car. Gina was so excited to have a new toy in Bobbi; Jeri wanted to talk about their purchases; Kevin was asking the girls about the dance that night. Tommy and Bobbi or was it Bobby, he/she was losing his/her grip. Once again the girls were dropped off, and Tommy promised to be back at 8:00 to pick them up. That left them just over two hours to get ready.

The next hour was a blur to Bobbi. Gina and Jeri had him in and out of all the outfits they bought and all the possible combinations of them as well. Finally, without much input from Bobbi they settled on a red low rider mini skirt and a pink colored cami top that boldly showed off her navel; and for shoes…three inch sandals. Jeri handed her a small red shoulder purse to accent the look. Bobbi protested that the outfit was too skimpy, but Gina laughed and said Bobbi should wait until (s)he saw the finished product. With that they girls hustled him into the bathroom and began the magical transformation. They even added a red choker to accentuate the look. By the time they were finished with Bobbi and themselves…Jeri was in a slinky metallic electric blue minidress and Gina was wearing a white tube top and a green mini skirt…it was 8:00. Gina and Jeri took Bobbi with their hands over her eyes to the full-length mirror and said what do you think?

Bobbi was completely prepared to say that he couldn't go out dressed like this. That is until he saw himself in the mirror. When the girls removed their hands he almost fainted. He was astounded. He couldn't believe what the girls had done. He actually got tears in his eyes. He hugged the girls and was gushing thank you after thank you when the doorbell rang. It was Tommy and Kevin.

Jeri ran down to let the two boys in to the house. She made them wait in the foyer until Bobbi would come down the stairs. Gina came first and announced the coming of Bobbi, "her greatest creation". Gina and Jeri made trumpet sounds and Bobbi came out of the bedroom and down the stairs. Kevin whistled loudly and Tommy burst into applause. Tommy couldn't believe his next-door neighbor looked so wonderful. Bobbi tried to look serious but he couldn't stop smiling. He hugged Tommy and thanked him for bringing him to the city.

The five teens piled into Tommy's car and headed to the dance. It was being held in a church gym not far from Gina's house. Tommy parked the car in the lot and they headed in, the boys first and then the three girls. Gina, Jeri and Bobbi made quite an entrance. They turned every head in the place, even the chaperones.

Gina and Jeri were in charge and introduced Bobbi to everyone they knew, which Bobbi surmised was everyone. Meanwhile Tommy was busy seeing all his friends and Kevin was sticking close to his side. The DJ started playing some songs the kids could dance to and Gina pulled Bobbi on to the dance floor. Bobbi always considered himself an okay dancer…for a guy, but now in three-inch heels and a mini skirt he never felt so self-conscious in his life. But the longer he was out there the less and less self-conscious he felt. Soon Bobbi had forgotten everything but that he was having a wonderful time.

Finally, the DJ played a slow song and Bobbi and the girls were heading off the dance floor, but Tommy stopped Bobbi, and asked her to dance. Before Bobbi could say no, Tommy had her in his arms. Bobbi smiled up at him and saw Tommy smiling down at him. Tommy said that he was happy Bobbi was having fun and this was just the first of many weekends they could spend in the city like this. Tommy also said that the plan for tonight was for Tommy to stay at Kevin's house, and that Bobbi could stay with Gina and Jeri. Tommy would pick Bobbi up at nine o'clock Sunday morning. That was fine with Bobbi, but he asked if staying over was okay with Tommy's mom? Tommy said his mom was okay with it since it would be late and that Bobby was there with him. Tommy hugged Bobbi and kissed him on the cheek. Then walked Bobbi, like the true gentleman Tommy was, back to the girls.

Bobbi danced with a group of girls for at least an hour. Some of the girls were cross dressers and some were lesbians but they had one thing in common, they were all having a great time. When the DJ played slow songs the lesbians and the boys danced together. Bobbi's mind was like a sponge. He prayed that he would remember every bit of this night. At about ten-thirty the DJ played another slow song and Bobbi was heading off the dance floor when he was gently tapped on the shoulder.

"Excuse me, would you like to dance?" Bobbi turned and saw a six-foot tall very nervous young man desperately hoping Bobbi would say yes. In an instant Bobbi remembered what it was like for her; rather him, to ask a girl to dance and he/she smiled and said, "I'd love to".

Bobbi put her hand out and he tentatively took it. He led her to the dance floor and gingerly took her hand, put his arm softly around her waist and they started to dance. Before she could ask his name, Bobbi noticed he was a very good dancer. She looked up to see his smiling face and, smiling back at him, Bobbi asked his name.

He stumbled around for a second, and then said, "Jeff". Bobbi smiled again and asked if that was his real name. Jeff looked shocked, but he said it was. Bobbi couldn't believe how in control she was. Here she was the first time dressed in public, and had this nice looking boy as nervous as anyone she'd ever seen. She said, before he could ask, "My name is Bobbi, and it's my real name too."

Jeff said he was going to be a senior at a high school not too far from Bobbi's. Bobbi knew a lot of kids from there…cross-country runners, basketball and baseball players, but he was reticent to ask Jeff if he knew them. Bobbi merely said he was going to be a senior as well. When the music stopped, Jeff asked Bobbi if he wanted to get a Coke. Bobbi again said sure and they headed to the refreshment area.

Compared to the gym this part of the church was almost too quiet. Jeff grabbed two cups of diet coke and brought them to the table that Bobbi had selected. After a couple of minutes of silence, Bobbi asked Jeff if he attended many of these dances. Jeff said no, this was his first event. He added that he was really nervous about coming, but his mom suggested that he attend. He then asked Bobbi, if she was a regular. Bobbi said no, this was her first as well, and she came with a neighbor, her mom didn't know.

Pretty soon the two teens were talking and laughing about all matters of things. First and most important to Bobbi, was Jeff asking Bobbi about cross-dressing. Bobbi was glad Jeff knew that, but was secretly disappointed he knew she was a guy (she really lost track of what he was saying when she thought about the intermixing of pronouns). It turned out that Jeff was very involved in theater and student council. No one at his school knew he was gay. He had been battling his emotions for years. Finally he went to his mom, and she got him some help. His mom had family in the city and he was staying there tonight. Bobbi told him how he was involved in sports and he had been battling his cross-dressing since puberty. He then added that he didn't have the courage to tell his mom. Then he added that he was having a great time tonight.

Jeff asked Bobbi if she'd like to dance again. Bobbi nodded and smiled. Jeff took her hand and led her back to the gym in time for another slow dance. Jeff took Bobbi into his arms with exponentially more confidence. He held her tighter and moved with more confidence. Bobbi first reaction to this new found confidence in Jeff to be a little scary, but soon she relaxed and let him lead. Jeff moved gracefully and Bobbi found herself with her head on his shoulder. She caught herself and as she tried to move she felt Jeff's hand gently caress the back of her head. She laid her head back on his shoulder and felt a kind of dreamy existence take her over. She felt totally lost in the moment. This was the real life version of her fantasies while dressed at home. She closed her eyes and without thinking put her arms around Jeff's neck. He reciprocated by putting his arms around her. Jeff softly stroked her hair, and as he did pulled her even closer to him. Bobbie was suddenly very aware that Jeff was sporting a hard-on. T heir dancing slowed to mere swaying to the music. Bobbi dreamily looked up to see an equally enamored Jeff. When their eyes met he kissed her.

Bobbi was stunned. She started to protest, but that only opened her mouth. The next thing she knew Jeff's tongue shot was in there! She was all set to pull her head away; this was too gay, when she found herself massaging his tongue with hers. Jeff cradled her in his arms and Bobbi moaned. His brain/her brain, Bobbi's brain had come close to short-circuiting. She had to stop this but she was totally aroused. She wanted to take this further, but knew, or thought she knew, she shouldn't. Bobbi broke off the kiss, but she didn't back away from Jeff. Instead she buried her head in his shoulder and held him even tighter.

When the song ended she looked up into Jeff's eyes, god they were a pretty blue, and said, "Oh my God Jeff, we need to talk." With that she grabbed his hand and pulled him back into the refreshment area. Bobbi found an empty table and sat down. Jeff looked nervous, but Bobbi took his hand and said, "Jeff, I really like you, and I really liked that kiss. But this is moving a little fast for me. I am really confused right now." Then she started to cry. Bobby never cried. But here she was crying. Jeff came over to her side of the table and put his arm around her. He started to say he was sorry for kissing her, but she put her finger on his lips. She said she was glad he did, but she was so confused right now.

Jeff held Bobbi for a while, and then Bobbi looked up and kissed Jeff. No tongue this time, but a kiss that held both passion and thanks. She then took Jeff's hand again and they reentered the gym and danced some more. During a break Jeff asked Bobbi for her telephone number and email address. She gladly gave them to him and asked that he call her next week. Jeff promised he would.

Soon it was last dance, and once again it was a slow song. Jeff and Bobbi held each other tight. Jeff stroked Bobbi's neck and hair as she did the same to him. When the song ended, they looked into each other's eyes and once again kissed, this time Bobbi opened her mouth out of desire not shock.

Jeff walked her over to Gina and Jeri; they were smiling broadly as the two teens approached. Bobbi introduced Jeff, and just that fast they were saying goodbye. Bobbi got into the back of Tommy's car with Gina and Jeri. She wasn't prepared to talk, but Gina was peppering her with questions. The girls had seen Bobbi and Jeff kiss. They also had seen them holding hands in the cafeteria. For some reason Bobbi felt okay telling Gina and Jeri, but she didn't want to talk about it in front of Tommy and Kevin. Bobbi softly said she'd fill them in at Gina's. The girls understood, and shifted their attention to Tommy and Kevin. The boys said they had a blast, and as they pulled up in front of Gina's, Tommy said he'd pick Bobbi up at 9:00 am.

 

The three girls piled out of the car and into Gina's house and straight up to her bedroom. Gina and Jeri started to undress while Bobbi stood there with a dumb look on her face. Finally, Jeri said it was bedtime and she needed to get out of her clothes, makeup and into her nightie. Bobbi nodded and reluctantly took off her clothes. The girls gave her a lesson on makeup removal. Soon Bobbi was sitting on the floor in a royal blue baby doll pajama set. She still felt wonderful, but knew her time for dressing, at least for now, was coming to an end.

The three girls sat and talked for hours. Bobbi never felt so at ease in her life. She told them about how Jeff was such a nice guy; how surprised she was when he kissed her; and to the squeals of delight of Gina and Jeri how wonderful it was. She also told them that she gave Jeff her telephone number. She said she needed help, and wanted to know what she should do. Gina and Jeri were good about relating their stories about first kisses and first boyfriends and even first sexual experiences. Bobbi sat transfixed. He knew all about what they were talking about but only in the abstract. These two girls had done everything!

Bobbi thanked them for their help, and while he tried to stifle it, he yawned. Gina jumped up and said it was time for bed. The girls got up and Gina insisted to Bobbi that they all sleep in her bed. Soon enough Bobbi knew why.

Once in bed Gina and Jeri attacked Bobbi. They had the pajamas off in a shot. While Jeri was working from the bottom, sucking Bobbi's toes and nipping his instep; Gina was kissing Bobbi passionately. Bobbi tried to resist for a minute but soon caught up in the body worship the girls were lavishing on his body. He was squirming and moaning. He never felt so wonderful in his life. Gina moved down on Bobbi and was now sucking on his nipples. Jeri had moved to the back of his knees. Bobbi was totally at their mercy. He did make a half-hearted effort to try and do something for the girls but they would have none of it. Gina told her to simply enjoy it, and so she did. The two girls met at Bobbi's dick. They took turns licking and sucking. Bobbi gasped when one of them put two fingers in her butt. It felt foreign at first but wonderful within seconds.

Speaking of seconds within seconds of the dual assault on his manhood he came. It was the most intense and fulfilling orgasm of his life. He felt like he had cum all the liquid in his body. The girls didn't miss a drop. They sucked him until he couldn't take it any more. Then they slithered up him and both gave him tonguey and cummy kisses. At that moment Bobbi loved them both. He hugged them and pulled them close to him. The girls then turned their attention to each other and preceded to sixty-nine each other until they came. Then the three sleepy girls all entwined in each other's arms fell into blissful sleep.

Gina's alarm went off at 8:00 am. Bobbi knew he had to get up but the girls wouldn't let him go until he got a good morning blowjob from Jeri. While she was busy with Bobbi's dick Gina was making out with Bobbi. Bobbi wanted to do something for her. He reached down into her panties and started to stroke her dick. Gina moved closer so Bobbi could take care of her, but Bobbi had made a momentous decision, he wanted to please Gina like she pleased him. So he took both hands and pulled the cute blonde up onto his chest. Gina looked down at him and asked if he was ready for this. He nodded his head and pulled her forward. Bobbi opened his mouth and Gina was in him. Bobbi sucked for all he was worth. He was worried that he wasn't doing it right. Gina sensed it, and as she caressed him soothingly told him he was doing great. Suddenly Gina grabbed Bobbi's head and said, "Oh baby, I'm going to cum, do you want to take me in your mouth?" Bobbi nodded and experienced his first taste of fresh cum.

Moments later, while Gina's dick was still being massaged in Bobbi's mouth he came in Jeri's mouth. Bobbi was once again overcome with emotion. As the girls repositioned themselves on either side of Bobbi, he fought back tears. He was so happy. He wanted to quit school and live here with Gina and Jeri. He wanted to find Jeff and have him hold him while they danced. The last thing he wanted to do was to get dressed in his Bobby clothes and go home. But that is just what he had to do. He kissed both girls and got out of bed and headed for the shower. He turned to see Gina going down on Jeri. My god, he thought those girls were insatiable

Bobbi emerged from the bathroom as Bobby. He was really sad. He thanked the girls again and again. Gina said there was another dance in two weeks. She said all of his stuff would be here waiting for him when he came back. Then she added except for one outfit. Bobby looked at her quizzically. Jeri handed her a bag, she said that there was an outfit in there for Bobbi to wear next weekend when she went out with Jeff. Bobby started to protest, but the girls just laughed and said, we have a bet….we are sure you'll be going out next weekend. Bobbi started to protest again, but he heard Tommy's horn blow out front.

The girls walked outside to see Tommy. They thanked him for giving them Bobbi for the night. Tommy smiled broadly as Bobby blushed. In unison, they said see you in two weeks. To waves and wistfulness Tommy backed out of the driveway and headed towards the suburbs.

The two boys rode in silence for a while, and then Bobby started to thank Tommy for a wonderful weekend. Tommy stopped him and said that he had a great weekend too, and if it wasn't for Bobby he couldn't have gone to the city. Bobby asked about the dance in two weeks, would Tommy be going? Could they both go? Tommy said he had planned on it, and he smiled as he added, I guess you had a good time. Bobby quietly said he had a great time.

The boys pulled into Watson's driveway a little before 11:00 am. Mrs. Watson came out to meet them along with Tommy's brother Pete. Mrs. Watson wanted to know how they were and what they did. Tommy had a complete story already made up. He talked about dinner and the movie and the friends and where they stayed (one of Tommy's straight friends as Bobby found out later). Pete was smiling as was Mrs. Watson. They felt like Bobby was being a good influence on Tommy. Bobby thanked Tommy for driving and said he looked forward to going into the city as nonchalantly as he could. He also thanked Mrs. Watson for letting them go. He said it was fun and hoped they could do it again.

Bobby headed to his house; he noticed his mom wasn't home yet. Once inside he ran up the stairs to his room to see what the girls had packed for him. He smiled. They had put the "little black dress" in the bag with sheer black nylons, a garter belt, black bikini panties, a wispy black bra that he didn't remember getting, breast forms, three inch black pumps and a beautiful black choker that he knew he hadn't bought. Bobby carefully carried the dress into his sister's room and hung it up among her things. He took the undergarments, shoes and choker and carefully hid them with his other stash.

Bobby headed back to his room to check his email. Like every teen he felt he'd been out of touch for way too long…22 hours. He logged on and heard the familiar sound of "you've got mail". He scrolled down to see if there was anything good and halfway down the list was an email from Jeff. Bobby clicked on the email.

 

Bobbi, thank you so much for such a great time last night. I can't begin to tell you how wonderful you made my first dance. I really hope you'll be at the next dance, but I don't want to wait that long to see you again.

What is our chance of getting together this weekend? I would love to take you out Friday or Saturday. We could go out for dinner and dancing or dinner and a movie. Please email me and let me know if I can call you at home and we can work out the details. Thanks, Jeff

 

Bobby didn't know what to do. On one hand he was scared to death. He couldn't start dating a guy. But the Bobbi part of him was so flattered. Jeff had gotten in touch with him right away. Bobbi must have made a great impression. While Bobby was thinking over what to do his fingers were responding.

Jeff, I had a great time too. Here's my number, please call so we can decide what to do. I am not sure which night will work best for me, but I should know by late Monday. Bobbi

Bobby hit send before he knew what he was doing. Oh God, I kind of said I'd go out with him and signed it Bobbi. Bobby knew he was playing games with himself. He wanted to go out with Jeff, and now he had to get his mom's schedule for next week. He needed her to be out one night so he could dress and go out with Jeff.

Bobby's mom got home around three o'clock. She was surprised to see Bobby asleep in front of the television. He wasn't much of a TV watcher, but she figured he had a good time with Tommy and was tired. She turned off the television and let her son sleep. She woke him at 5:30 to let him know that dinner was ready. Once he was awake she peppered him with questions about the night in the city. Bobby found himself to be a good liar. He was animated as he described events that never happened. Tommy had drilled him on the car ride home, they wanted to be sure they had their stories straight, just in case their mothers decided to compare notes, and Tommy was sure his mom would want to verify his story.

Finally Bobby grilled his mom on her trip. She told him about how well Grace is doing in school, that she may have a boy friend, but Grace wouldn't tell her too much about him. Bobby asked, as nonchalantly as possible what his mother's schedule would be the following week. She said that she'd be working days Monday through Friday, and she would be off for the weekend. Bobby tried to hide his disappointment. This meant no date this weekend. Then his mom added that she would be going into the city with two of her nurse friends. She laughed and said she'd be doing "a Bobby" leaving Saturday and coming home Sunday morning. They both laughed.

Bobby was excited and scared. He rebooted his computer and with hands that were shaking so violently he could barely type sent another message to Jeff.

 

Jeff, Saturday works for me. You can pick me up at my house, but you'll have to pull into the garage since it would look odd for Bobbi to be leaving my house. Let me know what time! I can't wait to see you again. Bobbi

 

About five minutes after Bobby sent the message, Jeff called him. They talked for a while but the conversation was stilted and awkward. Bobby had a hard time talking to Jeff about a "date". Bobby could sense the same in Jeff. Nevertheless they worked out the details and each was committed to going.

Bobby tried not to think about the date during the week. He did his running and caddying as usual. The only times he thought about it was with Tommy on Wednesday night. Tommy was excited for him, and admitted to being a little jealous that Bobby was going out while he was sitting home. Bobby suggested he call Bill and Jack and see what they were up to this weekend. Tommy said he'd think about it. Gina and Jeri had sent emails with suggestions and some very outlandish ideas. Plus, Bobby did get a couple of emails from Jeff during the week and they were clever and funny. They really helped Bobby from chickening out of the date.

Finally Saturday rolled around. Bobby was up earlier than normal to run and to caddy and luckily got an early loop. This meant he'd be home in plenty of time to get ready. Mike was in his loop and offered Bobby a ride home. As they headed to Bobby's house Mike let Bobby know that Paul Taylor was still seething at Bobby and was waiting to get him. Mike added that he'd never seen Paul so angry and focused on anything. Bobby thanked him for the information as he got out of Mike's car. Mike pulled away and Bobby thought how Mike had stopped asking him if he wanted to go to any parties. Paul really had a major influence on the social goings on in the high school. Bobby shook his head and as he started for the house he saw the garage door go up.

Bobby's mom was leaving for her trip into the city. She leaned out the window of her car and kissed Bobby. She told him to have fun and then added that he should behave. They waved to each other as she rolled down the driveway and out onto the street.

Bobby tried to look nonchalant as he went into the house, but he was smiling in spite of himself. The first thing he did was lock all the doors and first floor windows. He didn't want another surprise while dressing. Then he bounded up the stairs to begin his transformation. He had his schedule plotted carefully in his mind. He started the bath first, carefully adding scented oils to the running water. While the tub filled he took out his razor, and got his makeup from his sister's room. Bobby applied the shaving gel to his legs, and turned off the water. He luxuriated in the tub, and when he was done he carefully cleaned it. He didn't want to have the hair in the tub. Once he was satisfied with the results, he dashed into his sister's room to begin dressing for his first date. He was tempted to do something about the hard on that kept bouncing up and down in the tub, but he wanted to stay as excited about this as he could. It would have to wait. Bobby moved to his sister's vanity table to apply nail polish and make-up.

He was going with the black dress, so his undergarments would be black as well. He tucked his penis "down and under"..it was a painful process that took a while. He put on the garter belt and carefully slid the sheer nylons up his smooth legs. Bobby was becoming Bobbi in not just body but mind. She smiled as she thought about dancing with Jeff again. Once she had the nylons on and straightened, she slipped on the black lace bikini panties.

Bobbi then went to work on her hair. She didn't want to wear a wig, so she played around with it for almost an hour before she was happy with it. She always called it her Lorrie Morgan look, but she had let her hair grow out more than usual this summer, it was now kind of betwixt and between in length. Finally she moved to her makeup. She made her eyes a little more dramatic than the mixer in the city, and she made sure her lipstick matched her nails. She was now totally Bobbi and she really wanted to impress Jeff.

Jeff was to pick her up at 7:00, and it was now ten to seven. Bobbi stepped into the black dress. It was strapless and very form fitting. He inserted the breast forms into the dress and zipped it up. He finally stepped into the almost 4 inch heels. Finally she added the choker. She never felt dressed without one. She figured if he was going out somewhere nice he was going to go all the way. Bobbi admired herself in the mirror. She picked up her purse, added the necessary cosmetics and her id. She carefully walked down stairs and hoped that Jeff would be on time. At two minutes to seven Jeff called and said he was one minute away. Bobbi asked him to pull into the garage, she was ready to go.

Jeff pulled into the driveway in a new Chrysler 300. He jumped out of the car as Bobbi came from the house to the garage. Jeff was about to open the door for Bobbi when he saw Bobbi. Jeff stopped dead in his tracks and his mouth fell open. Jeff couldn't believe the vision in from of him. He smiled and tried to regain his composure, Bobbi smiled and said "hi". She walked to the car and without any plan to do it kissed him right on the lips. Jeff recouped enough to kiss her back. Bobbi opened her mouth and naughtily sucked his tongue. After a minute she broke off the kiss. She looked up into his blue eyes and asked where they were going.

Jeff said that if she kissed him like that again they weren't going anywhere; he would carry her into the house and make love to her all night long. He then said there was a dance at his parent's club for the high school seniors and college kids, a kind of end of summer bash, and they were going there. Now it was Bobbi's turn to be stunned. He tried to say I can't do that when Jeff put his arms around her and said, "Don't worry about it, you pass wonderfully and no one will ever know."

Jeff was so convincing that before she knew it, Bobbi was in the car heading to the country club dance. Jeff filled Bobbi in on what he had to know to pull this off. Jeff then added that he didn't want to stay too long and he didn't want to spend any time with anyone other than Bobbi.

Twenty minutes later Jeff gave the car to the valet and went around helping Bobbi out of the passenger seat. Jeff took her hand and led her into the club. There were about seventy couples, most of them older than she and Jeff. They entered the dining room and Jeff picked up the table assignment and whisked Bobbi to their assigned seats.

Bobbi found herself sitting with four other couples. They were all college students and seemed to be okay. The girls professed amazement that Bobbi was still in high school. Bobbi noticed one girl try to subtly keep her date from staring at Bobbi. Jeff was a great date, he kept Bobbi in conversations and he was very funny. It turned out that Jeff's family was very very wealthy. He was right at home in this environment. Soon dinner arrived and after dinner the band started. Since it was such a fancy place the music tended to be less hip and much slower. This played right into Bobbi and Jeff's desires. They staked out a corner of the dance floor and hung on to one another during every slow song. The time flew by. During the fast songs they talked about school, about college for next year, about their families and Jeff and Bobbi found themselves becoming friends. Then it was back to the dance floor for another slow song. Bobbi had her arms around Jeff's neck and her head on his chest. She felt so feminine. She loved this feeling and she didn't want it to end.

Jeff was smiling. He had a beautiful woman in his arms…and more than one of his friends had told him so; but she was more than that, she met the extra requirement that he needed, she was really a guy.

Jeff and Bobbi were pretty antisocial after dinner and at a little after ten Jeff suggested that they leave. Bobbi agreed. She said she needed to use the ladies room. She smiled as she entered what had once been forbidden territory, she never even hesitated. She was Bobbi tonight, and she knew that when they got back to her house, she wanted to ask him in.

She met two of the girls at from dinner table, and they talked for a few minutes. The girls were all gushy over Bobbi and how wonderful she looked. Bobbi thanked them and said she hoped to see them again soon. She, like the other girls, fixed her lipstick, and exited.

Jeff had gotten the car by the time Bobbi exited the bathroom. He helped her into the awaiting car, and they headed back to Bobbi's house. On the way they talked about nothing and everything. The time passed, and as they pulled into Bobbi's driveway she pulled out the garage door opener and they cruised into the garage.

Jeff put the car in park and turned off the engine. Bobbi turned to him and asked if he'd like to come in. Jeff smiled broadly and said "absolutely".

Bobbi led him into the family room and asked if wanted anything to drink. She went into the kitchen and retrieved two diet cokes. She returned to the family room and sat onto the couch next to Jeff. Jeff took Bobbi into his arms and stared deeply into her eyes. He gently caressed her face, and then leaned forward and kissed her. Bobbi slowly lay back on the couch and sighed as Jeff explored her mouth with his tongue. The two teens kissed passionately for several minutes. Bobbi felt Jeff shift and he was now lying on top of her. Jeff ran his left hand down Bobbi's leg and started to caress her thigh through her nylons.

Bobbi moaned softly as they continued to kiss. Jeff was looking to move their making out to the next level. He tried to reposition Bobbi so he could unzip her dress, or at least get his hand under Bobbi's dress. Bobbi knew this was a huge step, but she wanted more too. She wanted to be treated like a woman and she was more than willing to let Jeff be the one to treat her that way. She gently pushed Jeff up and broke their kiss. She smiled at the horny teenaged boy and motioned for him to let her get up. She stood over Jeff and slowly and she hoped seductively unzipped her dress and let it fall to the floor. She stood now in here heels, stockings, panties and bra. Jeff reached out and slowly slid her panties down to her ankles. Bobbi couldn't keep her hard-on hidden any more. Her dick sprang out in front of Jeff's face. Jeff gently kissed it, and then stood up and removed his clothes. He moved in to kiss Bobbi and their dicks rubbed against each other as they slowly and sensuously ground into each other's pelvis.

Jeff asked Bobbi where his bedroom was. Bobbi hoarsely said upstairs. Suddenly Bobbi was swept off of his feet and carried up the stairs. Bobbi was doing his best to give Jeff a hickey as he climbed the stairs. Without taking her lips off of Jeff Bobbi pointed to the left and they entered Bobbi's room. Jeff gently laid Bobbi on the bed. Each teenager was caressing and stroking the other. Bobbi was never so happy. Jeff had Bobbi's bra off and was now sucking on his nipples. Jeff worked his way down and was now kissing Bobbi's dick. Bobbi didn't know what to do, he didn't want this to end, but she knew she was going to cum. She warned Jeff, and he responded by speeding up. Bobbi came in torrents. She cried out, she wasn't sure what she said but it might have been, "Jeff I love you!"

Jeff sucked until Bobbi couldn't take it any more. She gently pulled him off of her and cradled his head in her hands. She kissed him softly and as his tongue reentered her mouth she tasted her own cum. She moaned with utter happiness. She opened her eyes and looked into Jeff's eyes and suddenly started to cry uncontrollably. Jeff asked what was wrong, but she couldn't talk for a good two minutes. Finally she managed to say that she was never so happy in her whole life. Jeff hugged her tightly and caressed her back.

After a few minutes Jeff said he had to get home. Bobbi said she couldn't let him go yet. She had to do something for him. Jeff said he didn't expect Bobbi to do what he did, but if she would stroke his dick 'til he came that would be wonderful. Bobbi pushed Jeff back onto the bed and started kissing him. She took his dick in her hand and slowly started to massage the boy's manhood. Jeff started to squirm and Bobbi picked up speed. It didn't take long for Jeff to be shooting his load into Bobbi's hand. Now it was Bobbi's turn to hug Jeff.

After a few minutes two teens knew that Jeff had to go home. They headed downstairs and Bobbi put the dress back on and watched as Jeff put his suit back on. They kissed again and Bobbi walked Jeff out to the garage. She opened the door for him and watched as he drove off into the night.

Bobbi hugged herself as she walked back into the family room. She picked up the diet cokes; neither was drunk, and put them in the kitchen. She straightened out the sofa and took his bra and panties upstairs. Bobbi never felt as sad as when he took off his clothes to go to bed. Before long Bobbi was Bobby. He had removed his makeup and nail polish; she had washed out his cum stained nylons and hid all of her clothes. In just his boxer shorts Bobby sat at his computer to send Jeff an email. Jeff had beaten him to the punch. Jeff's note said simply,

 

Bobbi, thank you for the best night of my life. I can't wait to have you

in my arms (and more!!) again. I love you, Jeff

 

Bobby's hands shook as he got ready to reply. He wasn't sure what was going to be typed. He was on automatic pilot.

 

Jeff, I had a wonderful time too. This night has really complicated my life.

I want to be in your arms more than you can ever imagine. I love you too.

Bobbi XOXOXO

 

Bobby even sent the email in pink…..and he didn't care, he never felt so feminine and confused in his life. Bobby took one more look around to be sure the house looked okay and went to bed.

Bobby awoke early Sunday morning to the sound of thunder. He peaked out of his bedroom window to see rain coming down in sheets. It was his off day from running, and he was happy not to have to caddy today. He didn't know what he wanted to do, but caddying was not on the list. He crawled back into bed and thought about Jeff and how he loved having Jeff kiss him and especially how he was carried up to his room. Then he thought about resting his head on Jeff's shoulder while dancing. Then he came in his hand. Bobby hardly knew he was touching himself. He took his hand from his groin and studied his cum. He impulsively licked it from his palm. It tasted okay. He knew that if he saw Jeff again, he would want to do more than just masturbate him. If Jeff tasted like this, he could do it.

Bobby drifted back to sleep and it was almost 11 o'clock when his mom got home. The noise from the garage door opener awakened Bobby. He slipped out of bed and into some sweats and sleepily went down to see his mom.

Jean at the sink making some coffee when Bobby came into the kitchen. She turned around and smiled at her son. She chided him for being such a slug-dog and sleeping so late (but she secretly was glad, she worried about how much he ran and how early he got up every day. She thought on such a rainy day it was great that he slept in.)

Jean said that she had invited the Watson's over for dinner and that they would be over around six o'clock. Bobby said that would be great and what could he do to help. Jean said she'd need him to go to the store for her and pick up a few things. They then lapsed into small talk about what each did the night before. Bobby felt terrible lying to him mom. He never did that before, and now he was beginning to get too good at it. He suddenly felt like he should tell her what was going on in his life, but just as suddenly he thought better of it. He didn't know what to do.

Jean sensed that something was bothering her son. She asked if there was something he wanted to tell her. He said no, he was fine. Maybe he was just getting jittery about school starting, being a senior and all, and the cross country season right around the corner. Jean thought that it made sense and told him to just relax and enjoy his senior year. That was the end of it, for now. Bobby wasn't sure what to do, he needed someone to talk to, maybe Tommy.

Bobby helped his mom get the dinner ready, and as he worked on the salad he started to daydream about making dinner for Jeff. His mom poked him and said "earth to Bobby, earth to Bobby. Where are you?" She jolted Bobby back to the present. She asked him again what he was thinking about. He was at a loss to tell her, and simply said the teenage mantra, "nothing." Jean didn't press him, but clearly wondered what was preoccupying her son.

All three Watson's showed up for dinner. Mrs. Watson brought wine. They had a great time and since Bobby and Tommy weren't going anywhere they were allowed to have some wine as well. As usual Tommy didn't say much when his brother was there, and Pete took over the conversation, regaling them with his football stories and his current tribulations trying to be a good employee at the insurance agency he now worked at. Pete wasn't dwelling in the past, and he wasn't bitter about his injury. He had a great sense of humor and had everyone laughing at his story about how his boss didn't even know that he had ever played football.

After dinner Pete headed back home to watch a baseball game, and the two moms shooed Tommy and Bobby out of the kitchen as they cleaned up. The two teens headed up to Bobby's room ostensibly to play video games. Once safely in Bobby's room, Tommy asked Bobby about his date. Bobby said it was wonderful and that Jeff was really a great guy. He then described the club and the college kids at the table. Tommy pressed for more details, but Bobby said a "lady never tells". Their talk then turned to the dance in the city this coming Saturday. They both really wanted to go, but Bobby wasn't sure what his mom's plans were yet. They decided to just say they were staying at a friend of Tommy's…he suggested a Jerry Wilson. Bobby asked who that was, and Tommy said, it was Jeri of Gina and Jeri. They both laughed and thought that would be a great cover.

Monday marked the first official day of cross country practice. Bobby's schedule changed from morning pre-dawn runs to now running late afternoon. Bobby planned to caddy earlier, but the caddy master knowing his situation and his opportunity with the state tournament gave Bobby a job in the bag room. It meant regular hours, regular pay and the ability to be at practice on time. Bobby should have been totally happy, but he was as jittery and preoccupied as he could be. When he ran he would be distracted by the upcoming dance in the city, by the fact that he was meeting Jeff there, that Gina and Jeri had called and wanted to do another make over, that he hated to lie to his mother. The same thoughts haunted him at night in bed and when he was alone in the bag room at the country club. Twice that week he was tempted to tell his mother, and twice he stopped himself.

He did talk to Tommy who told him to just go with the flow and tried to convince him that the lies he told his mother were for her own good. He cited his own existence as proof that honesty wasn't always the best policy. Bobby let Tommy convince him…for now.

Saturday was soon upon them and the two boys headed into town at one o'clock same as two weeks ago. Tommy dropped Bobby off at Gina's, this time not even bothering to get out of the car. Bobby was once again swept into the house by the girls. Gina had already decided on Bobbi's outfit for the night so there was no need for a trip to the mall. What they did do was start with manicures and pedicures. The girls, now including Bobbi, were in Gina's room dressed in babydoll pajamas while they did each other's fingers and toes. Jeri and Gina wanted to know all about Bobbi's date with Jeff. She told them a little, but not all. Gina, easily frustrated and over sexed, suddenly had Bobbi's penis in her mouth and Jeri was asking if Bobbi did this to Jeff, or if Jeff did this to Bobbi. When Bobbi blushed furiously at this Jeri gleefully cried out and started kissing Bobbi. The three girls were quickly naked and moved to Gina's bed. Bobbi took Jeri's cock into her mouth and quickly brought her to a cummy orgasm while someone did the same to her.

After all three girls had been serviced Gina said there was no time for lying around, they had to get ready for the dance. It was decided that they would get Bobbi ready first. Gina had selected a short cranberry halter top dress for Bobbi to wear. Gina and Jeri had Bobbi dressed in a minute….there wasn't much to put on. She had the sleeveless dress on, and tied around her neck. She had the built in bra stuffed and a pair of wispy panties holding her penis tucked in. Bobbi slipped on the three inch matching sandals and she was dressed.

While she waited patiently for the other two girls to get dressed Bobbi applied the lotion Gina had given her to her legs. The lotion made them look sleek and sexy. Gina as always was hotter than a two dollar pistol. She was wearing a skirt that wasn't much more than a belt. She had a halter top and that was it. Jeri was more subdued but still dressed to the nines. She had a red vinyl minidress and four inch stiletto heels. Now it was time for makeup. The girls did Bobbi first and once her makeup was on they did her hair. Gina said that she was so glad that Bobbi hadn't cut her hair. Bobbi spent the time Gina and Jeri were getting ready admiring himself in the mirror. It was all he could do to not masturbate at his image in the mirror. The other two girls were finishing up when Tommy called saying he was two blocks away. The three hot girls were giggling and laughing as they piled out of Gina's house and into Tommy's car.

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.

 

…………….to be continued.

  

  

  

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