Introspection

"I just... Don't think I could bring myself to do it."

"Why not? It's just dressing up for fun, no one's gonna think you're gay or anything. Besides, if they did who cares? As long as you're confident in your sexuality then it doesn't matter what others think."

Jimmy didn't like that response, but truly he was the least confident in his sexuality. He didn't respond and was staring off in thought.

She walked over to him and grabbed his shoulder, "You are confident in your sexuality right?" Her expression was soft and understanding.

He once again didn't know what to say and instead looked her in the eyes.

"Is there something you want to tell me?" She said softly, holding his arm as if to suggest she was supporting him.

Looking at her, he knew he was safe to tell her. Besides, she was his closest friend now and the only reason he had any friends at all. He didn't want to lie to her, "Yeah, I guess so."

She pulled him away from the kitchen saying, "Okay. But tell me in your room."

So he showed her to his room and they sat down on his bed. She looked around, obviously expecting telltale signs that he might be gay or something and a little let down not to see them, "What is it?" She asked.

"Well... It's weird, and hard to explain. But that's exactly why this whole thing seems so uneasy to me... In a way, it hits too close to home."

She only cocked her head in confusion, "What do you mean?"

"Well... In all honesty, I don't think I can say I'm at all straight anymore. But I don't really consider myself gay. It's more like... I don't now, I prefer to be the girl?" He said hesitantly and unsure.

"Like... You think you're trans-gender?"

"Maybe? But not really... I enjoy being a boy outside of it. It's just like... Well here let me show you." He said as he pulled out his phone.

He scrolled down to the earliest photos he took of himself as a girl, knowing that the newer ones would be too lewd to show her, and handed her the phone. She looked at the photos and was a little shocked, "These... Are you?"

"Is it that obvious?" He asked, sheepishly.

"Well... Yeah, but not bad. There's a lot of giveaways and rookie mistakes you make with things like makeup, but honestly you're kinda hot. With more experience you'd be passable." She handed him back his phone and looked back at him with a grin, "So what then, you're some kind of cross dresser?"

Knowing that she was starting to get it, he decided to push the line a little more, "Technically what I am is a sissy."

"Sissy? Let me look that up..." She said grabbing for her phone, but Jimmy stopped her.

"I'd rather you didn't. Know that you're close with cross dresser." And she nodded understandingly.

"So I don't get why you don't want to do it then. It's your thing already, shouldn't you be super excited?"

"Yeah but... I've never done it in public."

"So what? Are you afraid of being exposed as one? Is this sorta like coming out of the closet for you?"

"I... I guess..."

"Well you shouldn't be. Like I said, you'd make one hot girl. And listen, I can do your makeup, clothes, hair, everything. I promise you, the guys won't know you're one of them. All they'll see is one hot girl at a Halloween party."

"I don't know..."

"Pleeeeeeeeeaaase? For me..." She gave him her biggest puppy dog eyes.

"Oh my god, fine! You're too good at that face." He laughed and she laughed with him.

"Now, since I already know you have girls clothes show me your stash!" She said excitedly.

Jimmy showed her his clothes, shoes, wigs, everything but the sex objects for the rest of the day before Alex came home. Caitlin went home, and Jimmy ate dinner like usual. The rest of the night was normal as ever, but with violent butterflies in Jimmy's stomach. The next day of school was pretty regular too, just everyone was a buzz talking about the party. Caitlin explained that she would come with him home after school to get him dressed and ready. They'd leave before Alex got hom to save Jimmy the trouble, then go to the party. And as the final bell rang, Jimmy's heart was pounding through his chest.

They made their way back to Jimmy's house and got to work. Jimmy studied Caitlin as she worked, and soon realized that he had been in the minor leagues. She brought twice as much makeup as he owned, a nicer wig twice the price and quality of his, and a costume wrapped in a box so he couldn't see what it was. She started by asking him to quickly shower and shave everything. After that, he moisturized again, and put on a pair of panties. He was extremely embarrassed to only be wearing panties when she walked in with her makeup, but she insisted that it was fine.

"You're basically one of my girl friends, remember? We don't care if we see each other nearly naked." Is how she justified it.

He sat down and followed commands in embarrassed diligence as she did his makeup. It took about twice as long as when he usually did it, but there was obvious reason. She skipped no details, and used product after product, half of which Jimmy didn't even know what they were. But finally, she spun him back around and let him see himself in the mirror. Jenny had never looked so hot. Her face in the mirror was a sexy woman ready to go to the club, without an ounce of male anywhere. Somehow through makeup, Caitlin was able to hide even Jimmy's facial features that defined him as a man. She didn't even have time to enjoy the view before Caitlin began the next steps.

Caitlin pulled a satin corset around Jenny's waist and instructed her to suck in her breath. It was painfully tight before she breathed out again. And while Jenny sat in stiff pain from it's tight clutches, Caitlin pulled out two small fake breasts and a bra. She cupped the fleshy busts to Jenny's chest and pulled the bra around them. Suddenly, Jenny had almost an hourglass figure with a real bust to speak of. Caitlin then rolled some white stockings up Jenny's legs and a white garter belt around her hips. Caitlin then stuck the wig over Jenny's head, and it was a long mid-back sandy blonde wig with some vicious curls all down the length of it. Jenny finally got to look at herself for more than a moment while Caitlin went to get the next piece.

Caitlin came back in with the box and an excited look on her face. "Are you ready to see what you'll be going as?" She said.

"Sure?"

Caitlin opened the box and pulled out a slutty nurse costume. Jenny's heart both sunk and beat ten times faster at how hot and revealing the costume was. Caitlin began to take it out of the packaging and laying it out over the counter. First came the main dress, a white uniform that started around her bust connected only by thin spaghetti straps and went only down to her mid-thigh. Then were the long white gloves that came up to her elbows. Next, the white cliche nurse hat that sat on top of her head like a small tiara. And finally, something that Caitlin had added on her own accord, a pair of three inch white pumps. In total, Jenny was smoking hot. She got to sit and take photos of herself while Caitlin quickly got ready. It amazed Jenny how fast Caitlin could do it to herself rather than on someone else. In a little over half the time Caitlin stepped out as a sexy police officer and they took a few photos together.

That's when they got back in the car and drove off to one of their friends house. By an hour before the party, all of their girl friends were at the house and all were dressed as slutty whatevers. Jenny wasn't even the only sexy nurse. All of the girls were amazed and adored how cute Jenny was. They all get their story straight about her, her name was Jenny and she was a girl from a different school that they knew through old summer camps. They all took some group photos before gathering their things and heading out. The party was just out of town in a big property owned by some rich boy. They all parked and walked up to the party together, and they could see the entire party watching them come up in awe. Jenny was still trying desperately to control her panic with all those eyes on her.

They entered the party and began about the regular party routine. They all started together, and vowed to take a shot as a group. They gathered around the table with their shot glasses, counted down from three, then took the shots in unison while most took selfies or videos of them together. After that, the group began to split apart while they got dragged away by other people. Jenny stuck with Caitlin and their other friend Natalie. The three stuck together and moved all over the party talking to various people to introduce Jenny. Most boys seemed so nice to her, and they were all eager to meet her. After that first shot, they began filling solo cups with mixed drinks. After three of those, Jenny switched to regular beers. She was beginning to feel extremely tipsy by the later half of the night.

Jenny and the other two were all in a happy place as they bounced around and talked. Jenny was slow to notice it in her current state, but she soon realized that the guys were hitting on them. And some would even try party jokes and pranks to get them more drunk. But Jenny couldn't mind, she was having too much fun. And she couldn't tell if it was the alcohol, or the clothes, or the attention that was giving her such a high, but everything hit her soft spot. Everything was good, everything intoxicating, and every word she heard made her blush with sissy joy. She struggled to keep her boner hidden through her dress for most of the night. Coming up around midnight and the party was still buzzing. Most people had reached their high and were doing the craziest things they would do. Some jumped into the pool half naked, while others got on the roof. Jenny, Caitlin, and Natalie were out on the grass in the back yard sitting around a fire pit with three other boys when they did the first thing that Jenny would consider crazy. All three boys were attractive jock type, and Jenny saw that her two friends were really interested in them already. They were playing some stupid game that the boys had obviously made up on the spot.

The game was simple, truth or dare but between the genders. At the start of it, they had agreed to keep it non-sexual, but that didn't last long. Jenny had to kiss both other girls, had to slap each others asses, and had to let one of the other girls ride on her back like a horse. But they got back at the guys by making them kiss, by pouring a drink over each others heads, and by jumping in the pool with their clothes on. But as the boys were walking back from the pool, they were whispering to each other. They got back, and asked the girls a truth: How much they liked dick.

The girls were angry because they didn't want to answer, and had asked to keep it non sexual. But the guys insisted. Natalie said about an eight out of ten. Caitlin said nine. And in her drunk stupor, Jenny wanted to one-up them and said ten. The guys whooped and hollered at her answer, and a few jokes were made, but the girls then whispered to each other and came up with a response. They dared one of the guys to go pants a random girl by the pool. The guys were obviously uncomfortable, but the boy on the right got dumped with the dare. He snuck up behind a slender blonde girl and did the deed. While they all laughed at them, the girl spun around and slapped him so hard he fell once more into the pool. He swam back up to her, explained it was for a dare, and she slapped him once more.

But as he came back and sat down, the guys were all grinning, and Jenny was getting the feeling that this was all part of their plan. The guy in the middle said, "Well if you guys are okay with it being sexual and are gonna make it about dropping clothes, then we dare you to flash us your tits really quickly."

The girls got angry and screamed at them, but they stood their ground. When it became obvious that there was no convincing them otherwise, and that they had planned this already, the girls looked at each other reluctantly. After nodding, they all quickly grabbed their tops and bras and yanked them down quickly for a few seconds before pushing them back up. Jenny did it a little quicker to avoid them noticing that they're fakes. But the guys seemed extremely happy with it, and the girls were done with playing the game. And so they just sat around and talked. First, one of the guys left. Then, Natalie left. Then, a few people came over and took both Caitlin and one of the boys, leaving just Jenny and the last boy.

His name was Kyle, and he was a tall, well built, dark haired, tan guy. He was dressed as a fire fighter, and his brown eyes glowed in the light of the fire. Jenny had been trying to deny the fact that she found him attractive, but the more they talked the more she found herself lost in her own sissy desires. They were talking with each other for a while before the guy made his move. He stood up and made a remark that it wasn't warm enough in the fire. He walked over and sat down next to Jenny, putting his arm around her. Despite her quickly beating heart, her sissy instincts made her lean in and rest her head on his shoulder. They kept talking, but in a quieter whisper now. Their conversation grew slow and stilted before she looked up and into his eyes. They leaned in, and he began to kiss her.

It started out as an innocent kiss, but quickly divulged into a drunk french kiss with their hands exploring each other. She turned her body to face his, spreading her legs around his waist. He grabbed her butt with both hands and pulled her close. His hands stayed on her ass while hers were pressing her face into hers. Their sloppy kiss made the sounds of love as their tongues explored each others mouths. Jenny's mind was lost in a foggy haze of lust. She knew it was wrong, knew it was stupid, but wanted it all the more. All the thoughts of her sissy fetish flushed her mind, the pictures she took, comments online, and videos she watched. In that moment there, she was living her dream. But just as she began to feel his hands slip up her dress onto her skin, they heard Caitlin behind them.

"Jenny? Sorry to break you two up, but I need you for a sec..." Caitlin said with her trademark sadistic smile.

The two jerked away from each other in surprise, Jenny red with embarrassment while Kyle sat grinning, obviously pleased with himself. She apologized and stood up to walk off with Caitlin. They walked back into the house and through the kitchen. Caitlin lead Jenny past everyone and into the back hallway. Caitlin opened the door to the bathroom and dragged Jenny in, shutting and locking the door behind them.

"What was that?" Caitlin asked with glee, holding Jenny's shoulders and leaning in as their chests touched.

"I-I-I... I don't know. Something came over me and I just..."

"No no no, it's okay cutie. Really, it's better than okay."

"How much did you see?" Jenny asked timidly.

"Enough. I was standing there for a moment or two."

"Oh..."

"No but Jenny, listen to me. I saw you with him happier than I think I'd ever seen you. You were so into it. This whole night you've been really into it, and happier than you are as a boy."

"Yeah well I've also been drinking so-"

"Oh don't pull that crap on me, Jenny. You obviously love being one of us girls. Admit it."

"W-well... I..."

"Admit it Jenny!" Caitlin whispered as she leaned in closer to Jenny's burning red face.

"I... Yeah. I do love it."

Caitlin leaned in and began to kiss Jenny. It was another hot kiss, but this one less sloppy. Whereas Jenny's kiss with Kyle was hot and messy like a raging fire of passion, Caitlin was kissing her soft and smooth with complete composure like a slow burn. Their mouths slowly opened as their tongues began to dance. Jenny couldn't help herself from getting an erection. She had one while kissing Kyle, and here it was again. But now Caitlin was rubbing against it, and she could obviously feel it. Caitlin pulled away and looked down with a Cheshire grin. Caitlin slowly crouched down, rubbing her hands down Jenny's body as she moved. Jenny moaned quietly as Caitlin positioned herself in front of Jenny's crotch and began rubbing her bulge.

"Looks like my girlfriend is excited to be kissing me..." Caitlin said as she began to move Jenny's dress up and tug at Jenny's panties, "Looks like you are a sissy. You like being a girl, but you're a girl with a fun little surprise."

Caitlin pulled away Jenny's panties, and Jenny's seven inch cock sprung free into Caitlin's face, "Oh! It's not so little! My my, you're a girl's dream!" She sad as she began to rub it, and looking up at Jenny, "A perfect girl friend who could fuck me or be fucked with me. I love it."

Jenny had to stifle her moans by clasping her hand over her mouth as Caitlin placed her lips on the tip of Jenny's cock. Caitlin began to show off her skills as she took Jenny's entire length down in seconds. Jenny bit her tongue as Caitlin began to bob up and down with precise speed. Within a few minutes, Jenny was feeling herself ready to blow. Caitlin was holding Jenny's smooth thighs as she dove down and back on Jenny's cock. Jenny began to stammer, warning Caitlin that it was coming. Caitlin slowed down, working the entire shaft with smooth long strokes. Jenny began to tense up, and Caitlin pulled back and placed her lips on the head as she rubbed the shaft with her hands. And Jenny came into Caitlin's waiting mouth.

After the few ropes of come filled Caitlin's mouth, she closed her mouth and began to stand up. Caitlin never broke eye contact with Jenny until they were face to face once more. Caitlin leaned in, and began to kiss Jenny once more. Jenny got a warm surprise as her own come began to fill her own mouth. Their tongues danced with each other once more, and the kiss was sloppier as they traded the warm liquid between their mouths. Jenny had never tasted come, and though at first it was bitter and uncomfortable, the warm and thick liquid began to grow on her. It's bitter taste began to turn sweet in a way, and she was enjoying it in a way she had never enjoyed anything before. Finally, Caitlin pulled back one more time and clearly swallowed her share of the come. Jenny followed her lead, closed her mouth, and swallowed. She felt the viscous liquid crawl down her throat, and it sent shivers all down her spine.

"How'd you like that?" Caitlin asked.

"I loved it." Jenny responded out of breath.

"Perfect. Now we're not done, I have so much more to show you. Follow me."

Caitlin unlocked the door and began to lead Jenny out of the bathroom. They walked back through the party and past the kitchen. Jenny noticed Kyle getting another beer from the fridge. He looked at her and smiled, and she smiled back. Caitlin kept pulling Jenny through the party, around the corner, and up the stairs. The music was softer upstairs, with the beat thumping through the walls. There were fewer people up there, but Caitlin then lead Jenny to these two boys standing by a door talking. When the boys saw them, they smiled and stepped back to open space for the two girls.

"Hey guys, this is Jenny. The girl I was telling you about."

"Hi, I'm mark." One said, "Hi, I'm James." The other added.

"Hi, I'm Jenny, nice to meet you." Jenny smiled.

The four began to talk a little bit. Jenny could see that they were obviously eyeing her up and down, but Jenny didn't mind anymore. They talked for about ten minutes before Caitlin began to lean closer to Jenny. Caitlin reached down and began to hold Jenny's butt. When Jenny could see that the boys were also noticing this, Caitlin spoke up.

"So, are you boys still down? Think you can handle us?" She said as she squeezed Jenny's butt.

"Oh, please. If you two want it that bad we're always down." James said.