Trying It On

Wednesday Nika called Billy and said, "We need an escape." So Thursday afternoon, they were in her convertible heading to her family's place on the lake for a long weekend. Nika had decided its was time for Billy's coming out party.

They'd been best friends since childhood. The two were close in an opposites attract kind of way. Nika Umbertide was extroverted, assertive, impulsive and adventurous. Her parents were professionals and well off. In contrast, Billy was introverted, sensitive, bookish and thoughtful. He came from a blue collar family.

What they shared were bright and curious minds. From the start, they complemented and challenged each other. Billy was thin and wiry, while Nika was a competitive swimmer with a tall, sleek, yet muscular build.

They'd helped each other grow and explore as they'd navigated school and the tumult of their teen years. The friendship had been good for both. Nika was protective of Bill. Nonetheless, she pushed him outside of his reticence to expose him to things he'd never try on his own. For his part, Billy's sharp wit and observant sense of humor kept her in stitches and checked her ego. They became mature and worldly due to their bond and shared experiences.

As sophomores in college, Nika was a driven business major with bold entrepreneurial plans. Billy leaned toward literature and communication. Although at different schools, they kept close friends and confidantes. A deep mutual trust guided an inherent concern for the well being of the other.

At Nika's initiation, they had engaged in sex. They agreed it was educational. To satisfy physical needs, rather than a romantic connection. A means to explore, learn and have fun with a trusted partner. There was still some of that, but, now it was an occasional friends-with-benefits kind of thing. Nika had frequent sex in and out of a number of relationships. Billy, with a reserved personality, was less active, but he wasn't celibate. He had connected with a few girls, sometimes as a result of Nika's prodding.

This August afternoon was another of many times they'd spent at the lake cottage. The sanctuary was a source of fun memories and a favorite location for both. Hidden in the trees, the cozy cabin was a short walk to the water.

After the two hour drive, the pair unpacked the food they'd picked up in town. They dumped luggage in the rustic, but well-appointed retreat. Billy commented on the number of suitcases Nika insisted she 'needed' for a weekend.

Usually, Nika favored casual clothes of the t-shirt and cutoffs variety. Today, she wore a particularly feminine outfit. She'd come straight from her summer job and was still wearing a high-waisted, pale purple jumper skirt. The thin cotton covered a flowered, short-sleeved and lacy blouse. Standing on the deck, the light material moved in the breeze along with her short black hair.

Next to her, Billy leaned with his back to the railing and sipped a Coke. He wore a more relaxed outfit of a black, polo jersey; khaki pants; and Teva sandals. He'd let his blond hair grow long for the summer.

Stretching her back to remove the kinks from the ride, she tapped the toe of her espadrille on the deck. She said, "Let's walk to the lake before we unpack. I want to wade in and cool off."

"Sounds good. You wanna change first?"

"Nah."

It was a five minute stroll down a narrow path to the small, private beach.

Settling onto the dock, they soaked in the relaxing warmth of the late afternoon sun. The isolated setting was bucolic and wild.

Gazing into the distance Nika said, "We should go to the Cosplay Convention next month."

Although aware of the concept, Billy wasn't familiar with the details. Stretched on his back and without opening his eyes, he asked, "A what?"

"They're a lot of fun. It's like a fantasy or comic book event. Everyone dresses up. Some go as a movie or anime or science fiction character. People are seriously into it. It's a great excuse to have fun dressing up in wonderful costumes. You watch movies and intense parties. I've been to a couple. There's one near school in late September."

Rolling on his side, Billy asked, "You mean like a giant costume party?"

"Kinda", Nika answered. "Only more elaborate and structured. A little escapist and kinky."

Typically shy, Billy said, "I'm not sure I'd enjoy that. I'm not into acting."

"Don't be silly. You create characters in the stories you write. This is a twist on that." Nika eyed him appraisingly. "Besides, it would be good for you. Open you up to new experiences. That's what college is supposed to be about. Trying new things and learning new perspectives."

"I'm already learning all sorts of new stuff at school."

Nika pressed on. "You're learning new subjects and facts. But, life's a lot more than that. You're thinking about being a writer. A writer has to get inside and understand all sorts of different people. Cosplay let's you do that. It's a chance to be creative and let your imagination run wild. People inhabit a new character." She paused to watch the sunbeams dapple the water. She continued, "If you give yourself over to it, you can see the world through another set of eyes. It's very liberating. You can experiment and learn stuff about yourself, and others, that you never expected."

Billy was skeptical. But, Nika had unlocked many stimulating experiences for him. "Like what?"

"I went as Captain America. I felt bold and confident and heroic. My roommate wore a revealing and sexy medieval princess costume. It drove the nerds nuts."

Now she had his attention. He opened his eyes and looked over to see if she was joking. "How come I never heard about you doing this?"

Nika answered, "You don't known everything about me."

She had a mischievous expression. Billy knew that meant she was excited about something. This might be worth exploring. Turning onto his stomach, he said, "Tell me more."

Sitting on edge of the dock with her shoes off, Nika swirled her toes in the glass clear water. She explained more about Cosplay. Describe elaborate outfits people made, the presentations with actors, and the after-hour parties. In passing, she mentioned the popularity of crossdressing at Cosplay. As he lolled in the sun, the general concept sounded intriguing, but he was only half-focused.

"Let's swim. Save ourselves from taking a shower."

Billy said, "I don't want to walk back and get our suits."

"Who said anything about bathing suits?" Nika stood and pulled her dress over her head. She unbuttoned her flowered blouse.

Torn, Billy watched as she disrobed.

"Last one in does the dishes."

With that challenge, Billy kicked off his sandals, but Nika had a large head start. She dropped her blouse on top of the dress, and pulled at her watch. With quick moves, she released her pink bra and shimmied out of her shiny, red, french cut panties.

The sight of her pale bottom and the tan line on her sculpted behind, gave him a rush. Even given their sexual history, he was flustered by his friend's casual nudity.

Nika flashed him a taunting smile, gave her behind a shake and dove in. Following her lead, Billy finished ripping off his clothes and joined her.

The water had the right amount of chill to be exhilarating. They swam for about 20 minutes, splashing and laughing. When they began to cool, they climbed back onto the dock. The air was warm compared to the water and there was enough sun to dry their bodies. They laid on the wood and lolled in the forest scenery.

Billy heard Nika stir next to him, but stayed prone in a comfortable daze. When he finally opened his eyes, he was surprised to see Nika dressing in his clothes. She had on his underwear and was reaching for his pants. Confused, he stammered, "What... what are you doing?"

"It's time for dinner. I'm getting dressed." she casually replied.

Sitting up, Billy said, "I can see that. But why are you wearing my clothes?"

As she finished buckling his belt, she said, "We're going to practice for the Cosplay Convention. I told you crossdressing is a big part of it. Weren't you listening?"

"Yah, I heard you. But, I didn't agree to anything. What am I supposed to wear? I can't go nude."

With a smile, Nika nodded toward her pile of clothes.

Billy eyed the feminine outfit with alarm. "No, no, no. I'm not wearing your clothes."

"Like you said, you can't go nude. It's no big deal. I'm wearing your clothes."

With a flash of annoyance, he said, "That's different. Come on, Nik, give me my clothes."

Instead, she slipped on his sandals and said, "Don't be a pussy. This will be a new experience. That's what growing is all about."

"I'm not comfortable doing this."

Her face warmed in sincere friendship, "Admit it, there are a lot of things I had to push you to do. And, they turned out great."

He stood with a sullen expression. He was increasingly aware of his nudity.

Nika pressed on, "You've talked about being a writer. Think of this as a chance to understand and write about women. You'll be more realistic."

The argument had enough resonance with him that it curbed his negative emotions a bit. Nika had a knack for keeping him off-guard with persuasive points. She'd often overcome his initial reluctance to try new things with compelling arguments.

This was different and radical. He stopped to think about it, rather than follow his initial negative reaction. Nika was determined. Knowing he couldn't wrestle the clothes off his stronger friend, he tried to bargain. "I'll think about it for the Cosplay Convention. But, not now. What if someone sees me?"

She looked around and spread her arms. "There's no one here but us. That's why we could skinny dip. It's just me, and I'm your best friend. Don't you trust me?"

Billy was on the defensive.

Nika pressed her advantage, "You're the one who is always saying 'there's no time like the present'." Crossing her arms in feigned annoyance, she continued, "You could have been dressed and to the cabin by now."

Knowing Nika, it was pointless to continue to argue. He could refuse and say "No" without further explanation. Or, walk to the cabin naked. On some level he was unwilling to do that. It's not how they operated. Nika wouldn't call him a 'chicken', but she'd be disappointed in him. They always tried to avoid disappointing each other. It was part of their bond.

He did trust her. However, he was naturally tentative and the surprise proposal had him uneasy.

She added, "It's just clothes. These days anything goes. Most stuff is asexual anyway."

"It's not 'just clothes'. Maybe girls can wear anything. But a dress is very definitely feminine." It was true, but, it sounded whiny even to his ears.

"Come on, try it. Where's the harm? I'm looking at you naked. What's the difference with seeing you in a dress?

Billy knew there was a big difference. But, she said it so matter-of-factly. Still, his spinning mind couldn't marshal a logical response on the spot. Plus, he didn't want it to seem it was something he couldn't handle. She was right. it was just clothes. And, only until they got to the cabin. And, there was no one around.

She kept dressing in his clothes. He didn't want to seem close-minded, but this was a stretch for him.

Faced with the prospect of wearing her clothes, Billy looked at the pile. With closer examination, they appeared especially effeminate. The red panties were shiny with bows and delicate trim. The pink bra had a scalloped edge and lace cutouts. The flowery blouse was a pastel pink with puffed sleeves and frill adornments. The purple jumper had a curvy shape and the length only reached above the knee. Studying it, Billy realized it was one of the more girly outfits Nika had ever worn. He was piqued at his lack of choices and the position she had put him in.

Nika had stopped talking and had turned to face the lake as she played with her hair.

In the end, his body decided. Her intellectual arguments had some merit. But, he was reacting on a more physical level. Focusing on her clothes had stimulated his sexual imagination. It made him think of sex, and women, and their lingerie, and sex. He was getting addled and aroused.

It was compounded by seeing Nika, braless, in his shirt. With her hands over her head, her breasts pushed out and her nipples were visible. It was strange he found this exciting because she'd just been naked. However, that had been a romp between friends. Now that she was clothed, it was somehow different, and stimulating.

The whole thing was mystifying. Which was true for many things sexual for Billy. But, he knew the longer he stood there nude and looking at her attractive body, the more aroused he would become. The one thing he didn't want was for her to see him get hard.

He blurted out, "OK. But just to the cabin."

Over her shoulder, she said, "Of course. Great". Nika spoke like it was the most normal thing in the world. Women notice everything and she saw his nascent arousal. Nika knew him well. In some ways, better than he knew himself.

She didn't give him a chance to reconsider. With an energized gleam in her eyes, she said, "This will be fun." She wanted to start neutrally, so she handed him the low socks, "Start with these".

It was hard to object to socks. After all, they were just socks. They were a pale pink. Unlike his normal socks, these were short, dainty and barely covered his feet. They had a small cotton ball at the back. Each said, 'girl', but not so much that he could legitimately object. He pulled them on.

Billy couldn't see, but Nika smiled at this success. She knew each little victory would make the next easier. Now, for the hardest part.

Picking up the lacy hi-cut hipsters, she casually said, "Now slip on these briefs." She had been careful to use an asexual term and not call them panties.

Nonetheless, Billy recoiled. "Why? The dress will cover me up."

She pressed on with a tone that said it was obvious, "Because, you can't go commando. It will mess up the look. And you wear underwear everyday. Besides the idea is to get into the part. If we're going to experiment for Cosplay, we can't go halfway.". Nika knelt and lifted his foot. "Besides, it's only a piece of clothing." She said it in a level voice that made it seem completely ordinary.

She knew better. Panties were so much more than another piece of clothing. More than almost anything else, panties were the epitome of femininity. Especially, a pair as frilly and girly as these. That's why she had carefully selected them. On a woman, they were... cute... sexy... erotic. On a man,... she wasn't sure, but she knew if he put them on, it was a milestone. It could warp his perception and alter his self image. At the least, it could arouse him. Or, make him more susceptible to all sorts of suggestions. She knew that if she could get through this barrier, anything was possible. It was like breaking a horse. Her heart raced. She half expected that he would stop her.

He stiffened. Neither moved for a second. Then Nika started to pull them up. Billy didn't stop her.

When she reached his thighs, he pushed her hands away. "I've got it." He gripped the panties and brought them up the rest of the way. Billy snapped the panties into place with a wiggle.

Nika beamed and thought, 'Success'. It reinforced her beliefs about her close friend that had made her decide on this experiment. She felt an inner satisfaction.

Billy had to pause a moment. He was overcome by an unexpected tide of physical sensations and emotional feelings. He unthinkingly smoothed the underwear into place across his bottom. They were so completely different than his baggy cotton briefs. These were physically light, but tight. Silky and caressing. Looking down at the unusual sight, they were visually stimulating. He felt a disorienting jolt surge through his body. He flushed at the reaction.

Nika noticed Billy's cock start to grow and stretch the fabric. She didn't want him to get embarrassed and undermine the progress. "Here, let me help." She reached forward and into the panties. Nika grabbed his penis and pushed it down. "Tuck it between your legs. It will be more comfortable. We don't want it bulging your dress."

Billy gasped. Nika's assertive move broke his reverie. He was too stunned to stop her and it was over before he could speak. He was overwhelmed by everything. Standing outside... her grabbing his penis... wearing sexy red panties... his body, and mind, thrilling to novel sensations. Especially provocative was these were panties had nestled against Nika's vagina. He felt vulnerable. Speechless. Docile.

He stole an embarrassed look at his body and saw a mound in the panties, rather than the usual bulge. He reacted as if seeing a woman in such exotically attractive underwear. His penis pulsed but was held in place by the panties. It couldn't grow as it normally would. It added to the strangeness. He felt he was not himself.

Nika took advantage of his haze and pressed on. She lifted the bra and slipped it over his arms. With his mind spinning in a panty induced haze, Billy hardly noticed. He thought to object then swallowed and remained silent. He realized that once he had acquiesced to the panties, he had crossed a threshold. Protesting the bra would be pointless.

Adjusting the straps of the brassiere, Nika kept up a patter to normalize the situation. "This will be fine. You want it snug, but not binding. Does it pinch anywhere?"

The practical question distracted him and brought Billy somewhat back to reality. Twisting his shoulders, he mumbled, "No, I don't think so."

She placed a reassuring hand on his shoulder. "If it does, let me know. It's easy to fix."

Nika reached for the blouse. As she pulled it over his head, Billy inhaled the lingering scent of Nika's floral perfume. It added to his sensual overload and adhered to his skin. Down the front from the Peter Pan collar, there were ruffles paralleling the buttons. These feminine clothes were inextricably associated with women. Now, his mind grappled with the fact they were becoming linked to him.

He was almost eager to put on the dress to conceal his arousal. Billy stepped into the pastel jumper dress and pulled it up. It had suspender type straps and a high bib in the front that had come below and accented Nika's breasts. After pulling the straps over his shoulders, he smoothed the fabric. The movement was instictive. All the sexy pieces worked together to excite his skin. It continued the maelstrom in his head.

He couldn't fully close the zipper. When Nika spun him to zip up the back, the light purple material fluttered like a flower in a breeze. He'd watched girls twirl to raise their skirts. It had always riveted him. Now that he was the flower, he felt as spellbound by the visual flow. The impact was enhanced by the delicate material caressing his legs.

Nika finished zipping the dress. It snugged tight and the outfit encased his body. Trapped. It was a strange combination. Tight around his chest, stomach and hips. Simultaneously loose, bouncy and vulnerably open below the waist.

The hem hit above his knees. In reality, it was about the same length as shorts he wore. But, he felt much more exposed. Billy was dramatically aware there was nothing to conceal his underwear. His position reversed those times he'd tried to glimpse an upskirt flash of some girl's panties. He flushed and placed his hands on the dress to keep it in place. A surge shot through his tucked penis.

Each piece of clothing had been a first for Billy. The panties were a psychologically weighted step, because they were so dainty, enticingly soft and forbiddenly feminine. The others added to the shifting scales of his self-image. They brought with them freighted sexual meaning. Donning the dress wrapped it all up. Because it completed the package and was so uniquely female. Although different, men and women both wore underwear, and shirts and socks. Only women wore dresses. The totality wasn't simply a fabric outfit. If the clothes make the person, Billy was a different person dressed as a woman.