Trying It On

His cheeks reddened with the thought. He told himself it was playacting. Practice for a possible silly Cosplay. Only for a short walk to the cabin. To please Nika. Evidence he had an open and adventurous mind.

All those clicked in the logical portion of his brain. Yet, his churning emotions were dealing with a range of new, scary, stimulating feelings.

Watching while Billy absorbed it all, Nika was elated with the outcome. She was only somewhat surprised he had acquiesced so quickly. She didn't mention it aloud to keep from scaring him off. However, her friend did have the body type for this feminine attire. He was, of course, flat chested. That could be remedied with a little padding. Still, it didn't detract from how the outfit clung to and accented his slender figure.

Nika brushed some of his longish hair forward into bangs. "You look great," she said in a cheery voice.

"I feel ridiculous."

To keep him amenable, she returned to the concept of Cosplay. "No,. I've seen guys at conventions who didn't look as convincing as you. And, they worked at it."

Billy wasn't sure this was as complimentary as Nika intended. The implication was he was already so feminine it didn't take much to complete the transformation.

Sensing renewed reluctance, Nika moved them along. If she kept him occupied, he'd have less opportunity to argue. "Time to go." She handed him her shoes with slight heels. His feet fit. They were pink to match the blouse. On Nika, they had looked like a stylish complement to her outfit. On him, they were subtlety different. More girlish.

To complete the swap, Nike moved a sparkly ring from her finger to his. They exchange sunglasses. Nika put on his black, mirrored. wrap-around pair. Nika's glasses had large gradient lens' in heart shapes. She removed her beaded necklace and snapped it around Billy's neck. "There. Now we're ready."

They left the dock. He was a little unsteady in the unfamiliar shoes. A nervous knot tightened in his stomach as they moved to the path. Billy was conscious of the swishing skirt. He was careful to keep his knees close together to avoid any possibility of exposure. He knew it was ridiculous. The only one there was Nika. And they'd been swimming naked. A panty flash should be meaningless. But, his mind had the womanly thought that it would be indecent. He was surprised he seemed to be operating on a feminine wavelength.

Walking up the trail, he felt self-conscious and nervously noticed every little thing. The disconcerting breeze up his legs, the tug of the bra on his chest; the erotic massage of the silky panties on his penis with every step. His eyes darted on alert for anyone to appear.

Noticing his tension, Nika softly touched his shoulder, "Relax. There is no one around." To distract him, Nika said, "You know, at the Cosplay Convention, you'll need a different name."

"What? Why?"

"It's part of the act. To play a different person. Billy won't do."

"Why not?" As he struggled not to trip in the unfamiliar shoes, he was only partly listening.

She steadied him with a firm grip on his upper arm. When he glanced at her, she raised her eyebrows and nodded at his female outfit.

"Oh... right." He sighed.

"It's best to keep it simple," she continued. "And, something only a girl would be named. Not something ambiguous like Dana, Blake or Taylor. How about Fawn or Kitty?"

Billy scowled.

"We don't have to decide for the convention right now. Let's pick one for the weekend." She brightened. "You like the outdoors. Think about a flower. Maybe Rose or Daisy."

He shook his head. Nika thought she was losing him. Then, he said distractedly, "I'd prefer Lily."

Nika was thrilled and couldn't keep the high pitched excitement from her voice. "Of course. That's perfect. I love it. Nice to meet you, Lily.' She gave him a big hug. She was certain he was relaxing and more accepting of the switch. It was a big step to pick his own fem name. She pressed her advantage, "Now, think of yourself as Lily. Become Lily."

To let that work on his subconscious, she distracted him. In an intentionally deep voice, she said, "And, you can call me Mac."

"Mac? Why not Nick?"

She waved at the male clothes she was wearing. "I feel like a Mac in these. Nick is the same as Nika. Besides, Mac makes me feel stronger."

If that's what 'Mac' did for her, then, 'Lily' re-enforced the shifting perspective that had him on the slippery slope to becoming like a girl. On one level, he supposed it was good. If in fact he was to 'play' a girl, best to act and think like one. On another, it was unsettling. Lily wasn't certain how much was 'acting', and how much was genuine feelings. He put those thoughts away for later contemplation. For now, it was easiest to suppress the doubts and immerse himself in the 'part'. He plunged in. Lily shook her head to clear her mind and told herself to enjoy it and learn. She walked with a lighter step and a sway.

Lily's 'role' was to play the stereotypical feminine counterpart to Mac's macho bearing and demeanor. Billy had never had an excessively masculine appearance. His body was lean. He only needed to shave a couple of times a week. The blond hair on his arms and legs was downy. It was easy to shed manly traits when wearing a dress and his skin sending constant reminders of having on a bra and delicate panties.

As they walked and chatted, Lily toyed with the fabric. Her eyes looked down to watch the bounce and swing of the hem. It was a random and hypnotic flow of material that was eye-catching and fetching. He'd ogled many girls walking in their pretty sundresses. This perspective was new. As enthralling, but for entirely fresh reasons. Instead of someone observing a girl, this was part of him. Either by subconscious adoption of gender roles or intent, Lily's moves were different. More delicate. Smaller steps. Softer voice. Hair was brushed from her face with the tip of fingers, rather than a rough hand across the head.

Mac noticed, but didn't comment on the subtle changes. She wanted this experiment to be relaxed, comfortable.

Whether Mac had been serious or making it up to convince her friend, she'd been right. Lily was beginning to get insights into a woman's view of the world. She was attentive to beautiful sights, gentle touches, light smells, the fluid movement of her body. Like many new adventures, it was eye-opening and intriguing.

Lily's curiosity tuned to the details and sensations. The light and breezy cotton dress that caressed her thighs. The ruffly sleeves of the blouse were more stylish than a boy's rough and boxy shirt. In many aspects these were little changes, but the cumulative effect was enormous. As fingers played with the beads on the necklace, Lily relished the air on exposed flesh. She had a sense of discovery of hidden desires.

To extend the walk, Mac turned down a path along the shore. She wanted her new 'girlfriend' immersed in the female persona for as long as possible.

Lily paused, "Why are you going that way? This is the trail to the cabin."

Mac took Lily's hand and urged her to follow. "It's such a gorgeous evening, let's see the view from the Point. It's only a bit longer."

At the rock overlook, they stood holding hands and took in the scene. The setting sun transformed the sky and clouds into shades of purple, orange and pink. Sunbeams sparkled on the water like dancing jewels.

In a soft voice, Mac said, "You're a good sport to do this." She wanted Lily at ease in her new skin. Then, with sincerity, "And, you look very pretty in that cute outfit, Lily. It suits you." She finished with a squeeze of their hands and gave a light kiss on Lily's cheek.

A flash went through Lily at the unexpected compliment. A short time before, she had rebelled at the clothes swap. Now, for reasons she couldn't understand, those thoughts waned. Lily looked into her friend's eyes to see if Mac was making fun of her. She saw warmth and caring. Her mind buzzed with tenderness and affection. She was less self-conscious.

Mac leaned in to touch foreheads, "Let's go back to the cabin."

Lily moved beside Mac in a docile and dreamy state.

Walking hand-in-hand on the road, they were almost to the cottage. They heard a car approaching. Lily panicked. Looking around, she said, "We have to hide in the woods. People can't see me like this."

As she turned to leave the road, Mac grabbed her wrist and held her in place, "Don't be silly. There's poison ivy in there. Act natural."

Lily stammered, "But... but... this isn't normal."

Mac took charge and pulled her close, "No one will be able to tell." Wrapping Lily in strong arms, Mac gave her a passionate kiss to hide her face.

The car slowed, then passed. They saw a couple of young lovers enjoying the evening, and each other.

Lost in the embrace and adrenalin, Lily barely noticed the car. Her lips were afire. She went weak in the knees. Her head was light and her heart raced. And, there was an erotic stirring in her loins. Different than anything before. Magnified by the girly dress and the tight, but delicate bra. And, especially the lacy panties massaging her excited flesh with every movement.

She'd kissed before. And, liked it. This was different! Unfathomable.

Mac guided them home. Leaning against his shoulder, Lily felt safe. At the cabin, Mac whispered, "That wasn't so bad. Kinda fun. I'm so proud of you, Lily."

Lily welcomed a sense of accomplishment from doing something brand new and scary. It mixed with relief they were at the haven. Her nerves at being outside from the fear of being caught decreased. Here, it was the two of them. Familiar and loving intimates. Their clothes and roles were reversed. But, their souls were still compatible and trusting.

When they entered, Mac pressed their bodies together against the door and kissed her. This one was shorter, but as pleasant. Tilting his head, Mac kissed her ear and whispered breathily, "This is so hot. You've got me all worked up, Lily."

Still 'Lily'. Not merely a name for Cosplay. But, as a real person. A stimulated and stimulating person. The Billy part of his brain struggled a little. Who was he? Why did he have such a fantastic rush at this feminine expression of himself?

As their bodies moved, skin flamed and ignited desire. Rationality and doubts were swept away by erotic cravings. Billy receded and Lily blossomed. She didn't want the intoxication to end. In a weak voice, she said, "I want you, too."

It was the consent Mac needed. He took her by the hand to the bedroom. "That's my girl."

Lily followed in a blissful daze. Relaxed. Willing. Billy gave himself over to this new character. Not half-hearted. For the next few hours, she'd be Lily. Like Mac said, 'What's the possible harm?'

Mac tingled at her friend's acceptance of the transformation. As she had suspected, there was a different spirit beneath the surface. A Lily wanting to explore, express and bloom. Mac was an excited guide to this metamorphosis. And, roiling with a new exhilaration herself. Their intimacy had always been special: caring, eager, satisfying. This was unfamiliar territory. She'd nudged her friend to try an unested path. Now, she saw Lily in a new light. All the same positive characteristics that bound them. But, in a changed package, manifesting softer mannerisms and revealing attractive qualities.

In her boudoir, Mac turned on the low light next to the bed. She moved Lily against the wall and said, "Wait here." She rummaged in her pocketbook and set several items on the bureau. "Let me freshen a few things."

She tilted Lily's face up and deftly applied a thick coat of bright red lipstick. With a brush, she styled Lily's swim-tangled hair into a cuter look.

While she did this, Lily gazed trustingly into Mac's deep blue eyes. Lost in the warmth of the delicious moment.

"Close your eyes." Mac spritzed her neck with a floral perfume.

Lily was immersed in a bouquet of femininity. She inhaled and felt a magical buzz.

Mac moved her before the mirror. Lily opened her eyes and gasped. She was disoriented by the reflection. She saw a winsome young woman. There were subdued hints of Billy. Those were overwhelmed by the alluring image of a girl. Undeniably female. Not just the clothes, everything.

Over her shoulder, Mac said, "You look adorable."

Lily brought a hand to her face. She continued to absorb this new reality.

Next to her ear, Mac whispered, "You like?"

A smile emerged and widened on her face. "I like." Lily startled Mac by turning, embracing her friend and giving her an appreciative, sloppy kiss, "Thank you."

Mac pulled her into a hug. Lily relaxed into the protective arms. Mac initiated another kiss. Longer. Lascivious.

Mac slid a hand down Lily's back. It made her more conscious of the fabric, the bra. The hand rested on the small of Lily's back and began a gentle movement. She liked it.

Lily moved with the stroking and pressed forward against her taller friend. She felt attractive, desirable, pursued. The cuddling continued with feathery kisses to explore their lips. She'd tasted a woman's lipstick before. Now, the sensation was magnified. Her lips were slick, alive, sensitive, succulent. Mac switched and kissed her eyes and neck.

Lily was becoming more charged with every moment. The contact. The enchanting smell of perfume. The sensual clothing moving seductively against her flesh. Her mind swam in a sea of pleasure. Her excitement advanced to arousal.

Mac squeezed her behind. Lily started. In a husky whisper, he said, "Should we move to the bed, my pretty?"

They were usually equals in their lovemaking. Now Nika... Mac... was taking the lead. The thought brought Lily back to a moment of clarity. A whiff of doubt surfaced. The evening had moved from trepidation, to discovery, to physical enjoyment. She wanted to continue. But, what would that mean? Would it cross a threshold from heterosexual sex to... something... unconventional? It seemed a significant gateway that could alter everything.

Mac sensed the hesitation. "Lily?"

She dropped her head to Mac's shoulder. Through a constricted throat, she croaked "I'm not sure."

Mac didn't want to press her lover beyond what she wanted. Mac was spontaneous and decisive. She knew her friend was deliberate and had to think things through. Mac remained silent to let Lily process. Her fingers moved across clothes and flesh with a gossamer touch. Their cheeks brushed.

Lily struggled to make sense of swirling emotions. It was like she had entered a labyrinth. Twists and turns led down murky corridors to an unknown destination. Totally disoriented without an idea how to leave or proceed.

Mac said, "You're safe here. I've got you."

Lily treasured her BFF's support and encouragement. Spurred on by her friend's confidence, Lily calmed and felt her strength grow.

Mac gave a warm look of encouragement. "It's OK. You can decide whatever you want." She held their bodies together and moved them in a slow dance.

"Does it feel good, sister?"

"Oh my, yes." Lily breathed without hesitation.

"Do you want to feel good?" Mac asked.

Lily closed her eyes as a soft sigh escaped, "Yes, yes."

Mac kissed her ear, "It's a fantasy. You can be anyone you want to be, at any time. Open up and experience it. Then, ponder at your leisure."

The advice sounded wise. Perhaps, it gave her the permission to do what she subliminally wanted. Luxuriating in the warmth and closeness, Lily murmured, "It feels right." No coherent thoughts came to her. And,....she was okay with that. There was more to life than rationality. Sometime you have to follow your heart. Her emerging soul decided the only choice was to continue and hope the path would lead to a happy place.

Flicking her tongue in Lily's sensitive ear, Mac continued, "I'm here for you, my friend. Do you want me to help you decide."

Lily relaxed a bit and nodded her head.

"Who has on a dress?"

Lily hesitated. "I do."

Massaging a hand down Lily's side, Mac continued, "And do you like the feel of that pretty dress on your soft skin?

"Yahhhh," she exhaled.

Mac kicked off the sandals. Relishing the wonderful sensations flooding her mind, Lily followed her lead.

"Who wears dresses to tease with their sexy bodies?"

Lily blushed.

Mac repeated, softly. "Who wears a dress?"

Lily looked into Mac's eyes and saw kindness. She whispered. "Girls do."

Mac rewarded her with a light kiss. She moved them to sit on the bed. "And who wears delicious lipstick that makes your mouth irresistible?"

The kiss created an electric buzz. In Mac's strong embrace, Lily lost more tension. "Girls wear lipstick." She melted back into the delight. Her concerns began to recede.

"That's right, sweetheart." Mac nuzzled Lily's neck and inhaled as their bodies squirmed in close contact. "And, who wears flowery perfume that is driving me crazy?"

Lily giggled at the question, "Women." Mac nibbled her ear. It made her body quiver.

Mac breathed a barely audible, "Who?"

Lily released and dove into the pleasurable pool of complete immersion into her new self. "Lily put it on to seduce you."

"Yes you did you naughty girl. And, it's working." She gave her another kiss. Not soft and tentative. This one was passionate and wanting.

Lily swooned. She lost any sense of being anyone but, Lily. Relishing the nuzzling, she returned Mac's moves. Stroking arms, kissing forehead. Now the frilly clothes were more than light and feminine. Feathering her skin, they were sultry and sensual. In her soul and every cell, she wanted the kissing and the touching to continue.

It was Lily that pulled them down to the mattress. Their tongues danced and bodies twined. Heat rose. They shifted from tentative preliminaries to thoughtless carnal engagement. Reflection disappeared and universal desires governed. As Mac explored her body through the delicate clothes, Lily felt sparks in places she never had as a man.

Mac moved a hand to her belly. Hesitated, then inched upward. He copped a feel of the chest covered by the satiny bra. "You are such a beautiful person."

Lily moaned and burned with lust. She combed her fingers through Mac's glossy hair. She kissed with abandon and thrust her hips forward. The ravenous twinkle in Mac's dark eyes filled her with delight.

Continuing to massage Lily's excited nipples, he moved his other hand to her leg. He seductively said, "You have the most lovely and creamy skin."

Lily stiffened from the rousing caress. Her fingers unbuttoned Mac's shirt and squeezed his breast. It caused his eyes to flutter. She could feel the nipples grow and harden in response. He thrust his groin into hers.

Mac's hand climbed the sensitive skin of her inner thigh.

Squirming, her breathing deepened. "Oh, my."

His fingers reached and toyed with the trim of the leg opening.

Lily's passion bubbled. She tugged at Mac's shirt and pulled it over his head. The firm breasts glowed in front of her. She dove in with hands and mouth. Fingers massaged, lips sucked, tongue flicked.

"Ahhhh!" Mac gasped as her ecstasy climbed. "THAT... feels... wonderful." Her head flung back. Her eyes were unfocussed slits. Hands pulled desperately at the jumper. "Take it off!"

Lily paused her breast assault long enough to sit up and help remove the dress. Her disheveled hair flew in a halo. Her entire body was alive. Everything was delight and soaring. Except her groin. Her genitals were trapped and fighting for release. Lily reached into her panties and freed it from the constraining material. It was small in size but sprung up like a rocket launch. The organ was as hard as it had ever been. Still in the panties, but now liberated for direct and sensitive contact.

Mac discarded the khakis and briefs. He almost drooled seeing the panties. They were one of his favorite pairs. Often a choice on a 'fuck me' night. Seeing the red flag of lingerie on her bed partner was a visual treat. "I love your hot, girly panties. But, I REALLY love your stiff clit."