Loving the Crossdresser

Katie picked up the phone, distracted by the drama queen exit of her roommate, Alysson. "Hello?"

"Uh, hi, Kat?" came the nervous voice.

"Peter!" exclaimed Katie, thrilled to hear her friend's voice. That meant that he'd made the trip and was in town right now. "Where are you?"

"Well, if a blonde ice queen just stomped out of your room... I'm right outside."

Katie pulled open the door to her dorm room and there he was. She gave him a big hug, almost jumping into his arms.

"You made it you made it you made it!" she trilled. He held her in the air, smiling goofily at her exuberance. He kind of blushed as other girls in the dorm looked at them, but it was also part of what he loved about his friend, Kat.

A moment later she was dragging him and his duffelbag into the room.

"You made it!" she said again, her face filled with satisfaction and some amazement.

"Yea, it took some real favors and my parents don't really know where I've gone off to..."

"Peter, we're 19 and adults. It doesn't really matter what they think!"

"Well, I still live with them, so it isn't that different from last year."

The previous year had been a trial for Peter. His parents were quite strict and kept an eye on his activities fairly closely. He loved them, but it left him almost no time for privacy or things he enjoyed that had to be done in private.

This trip was a break from their control, their rules, and a chance to finally indulge himself in this... thing that he dreamed about and craved.

"Did you wear them?" asked Kat excitedly. Peter blushed but nodded. She waved him to show her and he hesitated.

Peter and Katie's relationship was one that he'd never had before and though he treasured it, he was always unsure of its boundaries. Sure, she was sexy cute and he loved her, he just couldn't tell if it was like a sister or something more.

"Don't be bashful already," she teased and he unbuckled his belt and lowered his pants enough for her to see the pink satin panties he was wearing, the panties she'd bought and sent to him.

"It's official," she concluded.

"What's official?" he asked cautiously as he buckled back up.

"Hailey has arrived!"

That made him blush hard but also grin. Even with his fears and caution, he knew that his friend was going to make this a great weekend.

-----

"Now remember, we're girlfriends," instructed Kat as she squeezed Peter's hand in her own. They were walking from her car toward a huge mecca of a suburban mall. "So you can tell me everything, what you like, what you don't. I'll see if something looks good on you and you'll do the same for me."

Peter swallowed hard but he was carried along by her confidence and his burning desire to experience the things she spoke of. He could feel the satin of his panties sliding a little inside his jeans, exciting him and just pleasing him.

The mall was not busy on this early Friday afternoon which gave Peter some feeling of privacy. Still there were dozens of people around and lots of girls. He couldn't even fathom what would happen if he were discovered by a guy but somehow being exposed for his fetish to a girl stranger was a thrilling dread to him.

"First things first," said Katie as she drew him into the Victoria's Secret store. Peter walked through a wall of perfume and lighting to emerge into a dreamworld, surrounded by women and lingerie. He trailed behind Katie, losing himself in the pinks and reds and baby blues of the chemises, panties, bras, and more. He stepped up to a satin bustier that dangled rumpled satin garters and looked at the price.

"Oh shit," he whispered. He couldn't afford any of this. Maybe one thong. Katie saw his reaction.

"Don't you worry about anything, Hailey," she said quietly. "I had kind of a windfall recently and money is no object for us today." She smiled at him and he returned it.

"Good, now obviously, this is the first thing you need to try on."

"Oh god, Kat, I can't do that!" he gasped, realizing that she really meant him to do it. She took his hands in hers.

"Hailey, I called ahead. I talked to the manager here and explained the situation. She was very gracious and told me that they have *girls* like you all the time. They just need to use a separate changing room for you away from the other customers."

Peter blanched at having been outed already to unknown women but he didn't pull away. He swallowed and pushed through his fears and caution.

"o.. okay," he said quietly.

"Good! Now let's get back to the fun!"

They picked the blue satin bustiers in two different sizes and Katie added a couple pink demibras and a garter belt. She led Peter to one of the many checkout desks and asked for Margeritte. In a flash, a stylish and beautiful woman stepped up, the ubiquitous ear-phone in her ear and they were led toward one corner of the store. She unlocked a wide door and stepped back for both of them to walk through.

"I'll be nearby if you need another size," she said and Peter blushed as he saw her talking to him. She shut the door.

They were in private, but there were gaps in the door at the bottom and the top. Peter could hear all the music and people just outside the actually very flimsy wood doors.

"Strip it, sister," giggled Katie. And then she proceeded to pull her own t-shirt off over her head. He stared at her in shock.

"Well, I wasn't just spending on you, silly!" she teased as she unsnapped her bra and dropped on the same chair as her t-shirt.

Now Peter's head was spinning and his panties were getting tight. She was beautiful and he couldn't tear his eyes from her breasts, no matter how he shouldn't stare. She put her hands over them and gave him a mock face of anger.

"I'll put them away if you can't behave, Hailey!" she threatened, ending it with a wink.

Peter got busy taking off his own shirts and when he looked over again, Kat had put on one of the pink demibras. She was shifting it around her chest, adjusting how it held her breasts. He could see her nipples through the sheer lace that made up the upper edge of the bras.

She handed him a bustier and he got back to focusing. His hands trembled a little holding the sexy lingerie, wondering the best way to put it on.

"You could pull it down over your head, or unsnap it all and I'll do you up." He open the long line of tiny hooks and then slipped his arms through the shoulder straps. Kat pulled it back against him and began to tighten it, hooking it back together. Peter looked down, kind of disappointed that the satiny cups were flaccid without gentle orbs of soft flesh to fill them.

"Wow, first try!" enthused Kat, looking past his shoulder at his image in the mirror. He looked up and was amazed. The bustier looked great on him, even without a chest. It shaped him just enough to give a hint of an hourglass figure, flare at the waist. He thrilled to it and felt himself warming in his panties.

"Ma'am?" called Kat through the door. After a moment, Margeritte returned. "We really need to see how stockings will look with this bustier. Can you bring us some?"

Three packages appeared over the door immediately. "I figured you would," replied the woman pleasantly.

"Off with your pants," commanded Kat as she undid the wrapping on the thigh high stocking package. Peter hesitated again.

"Hailey wouldn't hesitate in front of a girlfriend," encouraged Kat softly, seriously. He smiled and took off his jeans.

The effect of the panties and their current activities on his manhood was unmistakeable and now it was Kat's turn to blush and tear her eyes away. She had him sit on the chair, rolled up each stocking and showed him how to draw it up his leg to keep the seam straight in back. Then they did each garter as he stood so the stockings were pulled just tight enough.

"Wow," he said, seeing how the stockings took his visual transformation that much further. He turned as he stared in the mirror and even struck a pose or two, enhancing the feminine illusion.

"I think this really works for you," said Kat, almost as if she hadn't believed it until now. That thrilled Peter inside.

When they eventually walked out of VS, Peter had the bustier, the stockings, matching satin bikini panties, and a pink bra and panty set. The last item was in the little bag. The rest he was wearing under his shirt and jeans.

"It's incredible!" he whispered to Kat as they held hands and walked down the mallway. "The garters tugging the stockings, the pressure of the bustier holding me... I mean wow..." She squeezed his hand and gave him an encouraging grin.

"You really need shoes before we go further," mused Kat, looking around the mall.

"Shoes?" he said, not expecting that.

"Girlfriend, the right pair of heels makes everything else look SOOOO much better!"

With that she took him into one shoe store after another. They would politely decline assistance from the sales staff and Kat took care of Peter herself. He took off his sneakers and walked around with the black silk stockings covering his feet. She measured him and had him try a series of black, strappy heels. When they seemed to fit, she had him walk in them.

She'd only picked the low heels, two or three inches, so Peter actually got used to walking in them quickly. They stayed in their own deserted little corner until he picked the pair he'd fallen in love with. She boxed them up and added them to their collection of bags. They headed back down the mall.

"Next stop, a dress," she announced, making a sudden left turn into a store called JKR. Peter looked around eagerly and saw that it was a dress shop full of gowns for prom season. Beautiful, exquisitely feminine dresses, some that used petticoats to flare the skirts.

"Hi, is Sandra here?" asked Katie as she pulled Peter up to the counter in the center of the store. The girl there nodded and pressed an intercom. An older woman came out of the backroom, a tape measure hanging around her neck. She smiled as she came to the desk.

"Katie?" she asked and Kat nodded. "So this must be Hailey." Peter almost died. He felt like he would faint. He felt like he was blushing like a tomato but he was also grinning like a fool.

"Hi," he finally got out.

"Hi Hailey, I'm Sandra and I'm going to help you get fixed up." With that, she led Kat and Peter to the back of the store. The next room was like a large dressing room with a sewing machine station on one side, several mirrors, comfortable chairs and mirrors.

"We use this room for wedding gown fittings and for our special clients like you, Hailey," explained Sandra in a calm and welcoming tone. Peter swallowed realizing that they had served other boys, sorry men like himself, men that wanted to be women too, a little.

Katie plopped into one of the guest chairs and watched, smiling and thrilled that her friend Peter was getting such a perfect day. The conversation turned to colors and styles. They walked through the main room where Peter would just touch the dresses that he liked the most.

Then came trying on. Peter stripped to his new lingerie and put on his heels. Dress after dress came through the door and Peter stepped into each of them, letting Sandra slide them up into place and zippering or lacing them tight around his body.

They all felt like a dream, satin, silk, lace, taffeta, crinoline, in pink, white, black, and jewel tones of all colors.

He finally settled on a bright red dress that seemed to fit particularly well, matching the hourglass his bustier gave him, flaring at the hips and using a petticoat. It still needed full breasts to really make it pop, but that just wasn't Peter's reality, even if it made him just a little sad.

The dress was wrapped in a hanging bag and off they went again.

"Kat, I.. I don't know how to thank you," said Peter, stopping her in the middle of the walkway. "So much money, planning... this has been a very special gift." His mouth opened a little when he saw a tear run down katie's cheek.

She gave him a quick kiss on his lips and just led him onward. Peter was still very confused about what they were to each other. It certainly wasn't a typical relationship but it was obviously very special.

They left the mall with the packages and Katie drove them back to her dorm. Confirming that her roommate Alysson was still gone and scheduled to be at volleyball practice, she locked the dorm room door and announced, "Fashion show!"

Peter eagerly stripped down, slipped on his heels and let Katie help him into the petticoat and the dress. He straightened it on himself and just adored the image in the mirror.

"Sit here," said Katie, indicating one of the desk chairs. Peter swished over and sat down, careful to not harm the skirt of the dress. It was quite full and he felt wonderfully lost in it. It also hid his very eager erection from becoming a topic of conversation.

Katie brought up another chair in front of Peter and laid out her makeup kit. With care, she slowly applied each item, each layer to his face, ending with a sensual trip across his lips with a pale pink lipstick. She had him kiss a tissue and then let him see the mirror.

He was speechless. True, he was still a guy and anyone taking a minute to look at him would know it. But there was... just enough illusion there... maybe with a wig... all he knew is that he saw the girl inside himself. Now it was his turn to cry. Katie hugged him and the laughed as they cried together. He kept murmuring "Thank you" and she would reply, "I'm here for you, Hailey."