Sweet 16 Party

Sweet 16 Party
by RogerGirl

  Carlos and Tyrese were playing basketball with some of their friends after class one afternoon.  They were both gifted athletes and were on several of their school's sports teams.  Living on the island that the Kaplan family had set up for people to live or vacation openly as crossdressers without having to worry about judgement from society, many students played multiple sports.  While the amount of kids had grown as more people settle on the island and had families, there were still fewer students than most schools.  Because of this guys and girls would often play on teams together.  While no one was forced to crossdress, many of the students enjoyed crossdressing from time to time like their parents.  While not everyone crossdressed, the students who didn't left those who did alone and treated them as whatever gender they presented themselves on any given day.  Some male students would play baseball as a guy and star in school plays as a girl, while some female students would cheer on the cheerleading squad as a girl and play on the basketball team as a guy.  

  After their game, a group of girls came over to talk to the group.  They handed each of them an invitation to Jacqueline's Sweet 16 party.  Carlos had long had a crush on Jacqueline, but got very shy around girls.  Every time he was around her he would clam up and get very nervous.  The only time he was able to talk to her was when she played on the basketball team as Jake.  They would even hang out after school sometimes and Carlos was able to talk to Jake and joke around with him like he did with any other guy on the team.  Carlos glanced at Tyrese who was smiling nervously at Jacqueline's sister Michelle.  Like Carlos, Tyrese was very shy around Michelle, but was able to hang out with her when she was Mitch.  As Mitch, Michelle also played on the basketball team with Carlos and Tyrese.  The girls finished handing out the invitations and walked off to hand some to another group.  

  Carlos and Tyrese said goodbye to their friends and grabbed their stuff to head home.  They lived across from each other in one of the condo complexes that had been built on the island.  They went up to Carlos' family's condo and went inside.  His mom, Alejandra, was still at work, but his dad, Reggie, had gotten home early to transform himself into Regina.  While they didn't crossdress regularly, Carlos' parents often planned date nights where they would go out as Regina and Alejandro.  

"Hey son," Reggie said coming into the living room to greet him, "Hey Tyrese.  Can you help me zip my dress up?"

"Hi dad," Carlos said as he helped his dad zip up his dress, "We got invited to Jacqueline's Sweet 16 party today.  Are we doing anything this Saturday?"

"No, we don't have anything planned," Reggie said as he put on his 5" heels, "Isn't that the girl you have a crush on?"

"Yeah," Carlos answered quietly as he read the invitation, "Oh, it says it's a crossdress party.  Can you help us find outfits to wear?"

"Sure," Reggie said in his Regina voice, "tomorrow night we can go check out the shops."

"Thanks dad," Carlos said as his mom walked in the door.

"Oh, who's this beautiful lady?" Alejandra said looking at Regina, "I better go get ready."

  Alejandra said hello to Carlos and Tyrese then went to the bedroom to transform herself into Alejandro.  She returned a while later wearing a suit.  

"Dinner is in the fridge," Regina said as Alejandro put his arm out for her, "We should be back around 11.  If you need anything just call the restaurant."

  Tyrese went to the kitchen to grab a soda while Carlos watched his parents leave the building.  While his dad was an average guy as Reggie, with normal male interests, when he became Regina he became a different person.  Carlos began to think about this and came to a realization.

"Hey man," he said to Tyrese, "this party is the perfect place for us to get over our difficulty of asking out Jacqueline and Michelle.  When we're girls and they're guys we'll be much more confident in talking to them.  Remember how easily we hang out with each other when we're all girl or all guys?"

"Yeah, you're right," Tyrese said, "we better look good for the party."   

  The next day, Carlos and Tyrese went with their parents to shop for outfits for the party.  Neither of them nor their parents were crossdressed today, but living on the island they were comfortable shopping for female clothing as guys.  They went into one of the shops and asked for some help picking out dresses for the party.  The salesgirl, Dominique, was very helpful and showed them each a variety of dresses and heels.  Dominique was a guy named Dominic, who was a friend of theirs from school.  He and his girlfriend Eva were both going to the party and they decided to become Dominique and Evan a few days before since they didn't crossdress as often as some of the others going to the party.  Dominic didn't normally work at the dress shop, but Eva had asked her boss to let him take her place for the week.  Dominique gave each of them some sample breast forms so they could see how the dresses looked with the female figures they'd have the night of the party.  

"You look good in that one," Tyrese's dad, Adrian, said when Tyrese came out of the dressing room.

"Yes," Tyrese's mom, Jenna, said bringing over a pair of heels, "These shoes would go perfectly with that dress."

  Tyrese tried on the heels and agreed with his mom.  He enjoyed showing off his legs when he was Tyra, and this dress and heels showed off his legs very well.  He went back to the dressing room to take off the dress and returned wearing his regular guy clothes.  His parents paid for the dress and heels and a few other items to go with the outfit.  Meanwhile, Carlos had also found a dress and heels he liked and his parents had found him some accessories to wear with the outfit.  They paid for everything and thanked Dominique for her help and told her they'd see her at the party.  They took everything home and went out to dinner with their families.  At the restaurant, Jacqueline and Michelle smiled and said hello to them as they left with their mom and dad.  Tyrese and Carlos waved nervously, but couldn't say anything.

"Those girls are very cute," Alejandra said, "Why didn't you say anything to them?"

"I don't know," Carlos said embarrassedly, "We can talk to them when we're all guys and when we're all girls, but when we're our normal selves we just clam up.  Hopefully we can do better at the party."

  For the next few days things went on pretty much as normal.  They would all see each other at basketball practice as guys, then later at cheerleading practice as girls.  As guys, Jacqueline and Michelle would act like average high school guys.  They'd go out and eat lots of pizza and burgers, watch sports and action movies, and joke around with the rest of their teammates.  Similarly, when Carlos and Tyrese were girls they would go to sleepovers, shop for clothes with the other girls on the squad, and watch reality shows and romantic comedies.  When they were in the alternate identities, they thought of themselves as real guys or girls and were able to act casually around others, even in the locker rooms.  When they passed each other in the halls, however, Carlos and Tyrese would continue to clam up.  

  Finally, the night of the party had arrived.  Tyrese and Carlos spent the day transforming themselves into their female alter egos, Tyra and Carmen.  When they were ready, they posed for some pictures for their parents, then left for the party.  They went to the hotel across the way and went to the main hall where the party was being held.  They were greeted at the door by their parents who complimented them on their outfits.  Both girls were wearing short dresses and heels that showed off their long legs.  They thanked them for the compliments and took their gifts over to the gift table.  After putting their gifts down, they looked around for Jake and Mitch.  They saw a lot of their friends there dancing, eating, or just hanging out.  Dominique was dancing with Evan on the dance floor and she waved to them.  While Dominic and Eva rarely crossdressed, they enjoyed making the most of their switched identities whenever they did.  There were also some first time crossdressers who had dressed for the first time for the party.  While most of them looked a little uncomfortable dressed as they were, some of them found they enjoyed their new male or female identities and would definitely dress again after the party.  Unable to locate Jake and Mitch, Carmen pulled Tyra onto the dance floor to dance.  They had fun dancing like two teenage girls and even danced with some other guys and girls at the party.  

  Eventually, they spotted Jake and Mitch walking around and they went over to them to wish Jake a happy birthday.  They ran over and hugged Jake and gave him a kiss on the cheek.  Jake and Mitch told them they both looked beautiful and the girls thanked them.  Feeling more confident since they were dressed as girls and they didn't have crushes on Jake and Mitch, the girls pulled the brothers onto the dance floor and danced with them.  They continued dancing until it was time to eat.  Jake and Mitch escorted the girls to their table and they each pulled a chair out for the girls.  The waiters served the dinner and everyone began to eat.  Carmen and Tyra were having a good time with Jake and Mitch and knew tonight was their chance to ask them out.  After dinner, there was a few games and cake was served.  The gifts would be opened at home since it was easier to carry things home in boxes than as loose items and since most of the gifts were female clothing, but Jake thanked everyone for the gifts.  

  After the party, Jake and Mitch asked Carmen and Tyra to stick around after the party.  The girls sat down while the brothers said goodbye to their guests.  After everyone had left, Jake and Mitch escorted the girls back to their condos.  As they walked, the boys created some distance between themselves so they could talk to their girls in private.  Jake was holding Carmen's hand as they walked down the path.  

"Did you have fun tonight?"  Jake asked.

"Yes," she replied, "it was a nice party."

"Thanks," Jake continued, "I had a good time hanging out with you in different circumstances, not as all girls or all boys.  I've liked you for a long time and was looking forward to spending time together.  I hadn't originally planned to have a crossdress party, but every time I said hi to you when we were out of drag you would get all shy.  Tonight though you seemed pretty comfortable as my date, but I hope you feel the same way when we're Carlos and Jacqueline."

"I think I can," Carmen said, "I've liked you for a long time, but I was afraid you didn't like me the same way.  I didn't want to make things awkward between us by asking you out."

"Awkward?" Jake said laughing, "We've showered together after cheer and basketball practice and stayed over at each other's houses.  Even though we were all girls or boys at the time, I don't think there is anything that could make things awkward between us."

"Yeah," Carmen said laughing, "I guess you're right.  Well, here it goes.  Would you like to see a movie this weekend?"

"Yes," Jake said, "I'd like that very much.  Although hopefully I'll get to be the girl this time.  As much as I like being Jake, I don't know how comfortable I'd be making out with girl.  Although, if I were really a guy, dating the captain of the cheerleading squad would be nice."

"Sure," Carmen said, "I don't know how I'd feel making out with a guy either."

  They laughed and suddenly Jake stopped and gave Carmen a soft kiss on the lips.  Carmen was a bit surprised, but returned the kiss.  They broke the kiss and stared each other in silence.  

"What was that?" Carmen asked.

"Just wanted to get my birthday kiss," Jake said as they resumed walking.

"Well, am I a good kisser?" Carmen asked, "That was actually my first kiss."

"Actually," Jake said, "it wasn't too bad.  I'd still rather be the girl, but you have soft lips.  Oh, and that was my first kiss too."

"I was kind of hoping my first kiss would be with a girl," Carmen said a little disappointed, "but the kiss was OK."

"Don't worry," Jake said, "that was just Jake and Carmen's first kiss.  Carlos and Jacqueline will have to wait until next weekend to have theirs."