Sky Diving

Jim woke to a loud noise. Helicopter blades slicing through the air. He slowly opened his eyes, and found himself looking into a man's face.

"Goor morning ma'am!" The man said in a deep voice.

"I, wait… 'ma'am'? Why did you call me- my voice. Its…. girlish. Why is it girlish!" Jim quickly sat up and screamed a girlish scream. He had a beautiful model body. Flawless skin combined with perfect curves. He had massive Double D breasts and a shaved vagina. And he was naked.

"Your lady friend was very specific ma'am. She said that you had been cheating on her, and she wanted to teach you a lesson," the scruffy man said. Jim saw that he was wearing a red plaid shirt with the sleeves rolled up.

"So she turned me into a woman?!"

"A damn fine lookin' woman if I do say so myself. She had you flown up here in this here helicopter to go skydivin'."

"Skydiving?" Jim repeated, his mouth hanging open?

"Yes ma'am."

"Why am I naked?" Jim asked abruptly.

"Another request by your lady friend. She wanted you to be humiliated."

"But I can't skydive naked!… Can I?…"

"Sure you can ma'am. It'll be chilly, but you can. Don't fret though, your friend wasn't that cruel. She had some clothes packed for ya. Although it wasn't a full set…." his voice trailed off as he got the bag from the front of the helicopter, where the pilot was checking various navigation instruments.

"Over the drop zone in five!" He called.

"Hear that ma'am? Not much time to get you ready."

Jim unzipped the duffel bag. The first thing he pulled out was a pair of silky white panties.

"Ma'am, we don't got much time," the man said. Observing Jim's hesitation. "You really should put those on."

Jim realized it was in his best interest. He slipped on the silky garments. They hugged his private areas in ways his boxers never did. He looked back inside the bag and pulled out a pair of extravagant white heels.

"Ma'am, we got about three minutes before you're free fallin'. Quick, put on your shoes. It'll make for a betta' landin'."

The man grabbed a backpack from a hook on the side of the plane and handed it to Jim.

"Take this," he said, and then went to grab helmet.

Jim slipped the backpack on. The heels weren't very comfortable. And they weren't even that high.

The man put the helmet on Jim's head and stuffed his long curly blonde hair inside.

"Don't want your hair wippin' around and gettin' in your face," he said smiling. "See that handle?" He pointed at the strap on the bag. "Pull that to deploy the chute when you're ready. But don't take too long, or you won't have time to decelerate enough before you reach the ground."

He opened the door of the helicopter. Jim stood there on the edge, wearing nothing put heels, panties, a backpack and a helmet. Things were happening so quickly. He could feel the cold wind touch his naked body. His nipples started to harden.

"Well ma'am its time to drop. But I can't let an opportunity like this pass me by, so…"

"An opportunity like what?" Jim started to ask. But he didn't have time. The man turned him around so they were facing each other, and kissed him on the lips. The man put one hand on Jim's large ass, and held onto a handrail of the chopper with the other. Then, with one last squeeze of Jim's soft behind, the man let go, and let Jim fall.

The helicopter was shrinking into the sky. He was falling backwards, his back towards the ground. How close was he? He had to turn himself around quickly. He shifted his body around and faced the Earth. It was far, but how soon would he get there? He didn't want to wait too long. But pulling the chute too early would mean going much much slower, and he wanted this to be over with as soon as possible. It was freezing. The bone-chilling wind was all around his naked body. At one point he thought he might lose one of the heels, but looking back, it was snug around his foot still.

He decided to pull the chute. One quick tug of the string, and the chute exploded from his backpack. Suddenly, he was jerked upward, and he again thought he was going to lose the heels. He started to gently float down. The worst of it was over. Although he wasn't sure what was going to happen when he landed. Hitch a ride maybe?

The ground eventually started to come closer, and he found himself preparing for a hard landing. Both heels touched the ground at the same time, and he tried to roll as best he could to divert the momentum sideways. The hit still shook him a little though. He could see a road to his left, a few cars passing by then and there.

He removed the helmet and slowly made his way over to the highway. Each step with the heels proved a little difficult. He eventually made it to the side of the road and realized he was naked except for his panties and heels. He stuck out his thumb and waited.

After about a minute, someone in a large van slowed down. The woman pulled up next to Jim and rolled down the window.

"Um… you need a ride?" She had short brown hair in a pixie cut, dazzling blue eyes, and full lips. She was very pretty.

"Yes is that ok?" Jim asked nervously.

"How come you don't have any clothes?"

"Its a long story. This is all I've got," he said, gesturing to his panties and heels.

"Sure. I can give you a ride. And I can probably help with… well that," she said, gesturing to Jim's naked body.

She opened the car door and grabbed Jim's hand in hers. She had soft skin. His new friend brought him to the back of the van, where she opened the double doors in dramatic fashion. Inside were clothing racks all down the sides.

"You… you have spare clothes!" Jim said excitedly.

"I rent out costumes and clothing to different acting firms and drama departments. Lots of choices."

"Do you have any male clothes?" Jim said quickly. "They just feel better on my skin."

"Boy clothes? With a body like that? Honey I don't think so."

Jim was about to protest, but found it best not to argue with someone who was giving him clothing and transportation.

"So the trick is," she said, ruffling through the clothing racks. "To find something cute. But it has to fit that body of yours. And I don't want anyone to miss it. So something low profile. Aha! Perfect!"

She held up a pink sundress to Jim.

"What do you think?" she asked.

Jim didn't know what to say. He had to make himself sound girly. "Its adorable! Thank you!" he said, taking the dress.

"Here, let me help you put it on."

The kind woman held Jim's long curly blonde hair back for him as he slipped into the dress.

"It goes great with those heels!"

"Thank you for this!" Jim said, giving the girl a hug. The stranger hugged back, letting her arms fall a little lower than Jim was expecting.

"Well, do you want to hit the road?" she asked.

"Yes please," Jim replied, happy to finally be wearing something. As they climbed into the car Jim turned the conversation towards her. "Whats your name?" he asked.

"Roxanne," she said. Roxanne, Jim thought. What a pretty name. And her cute hair and pouty lips sure got his attention. "Whats your name?" she asked.

His name? He hadn't thought about that. He couldn't say it was Jim. His mind immediately went to his girlfriend's name. Or maybe ex-girlfriend at this point. "My friends call me Tiffany."

"May I call you Tiffany?" Roxanne said playfully.

Jim giggled. "Yes, you definitely can call me Tiffany."

As they started to drive, Roxanne asked again, "So why were you stranded out there with no clothes?"

"Long story short," Jim took a deep breath, "my girlfriend dumped me."

"Oh." Roxanne said. "You know, I swing that way too." She turned and smiled at Jim, who hadn't realized he made himself sound like a lesbian. Couldn't go back on it now, he thought.

"Oh you do?" Jim tried to sound interested.

"Ya. Ever since I was fourteen. Boys were always mean and ugly. But girls are nice, and pretty, and they're more fun to be with. How about you? When did you realize you were gay?"

"Oh, about the same time." Jim was making stuff up on the fly. "A girl kissed me on a dare and it just felt right. Been a lesbian ever since."

"But your girlfriend dumped you huh?"

"Ya. And left me stranded."

"Well, her loss. She'd be lucky to have a girl like you."

"Thanks," Jim said with a genuine smile. "Do you have a girlfriend?"

Roxanne blushed a little. "Nope. Not yet at least." She winked at Jim, who felt his stomach turn over happily. Roxanne took one hand off the steering wheel and interlaced her fingers with Jim's. "Your hands are warm," she said.

"Yours are too," Jim smiled.

They continued to drive and make playful small talk until it got dark, and they needed to stop somewhere for the night.

"Do you want to stop at a motel?" Roxanne asked.

"Sure, if you want to."

"A two bed room is going to be expensive."

"We don't have to get separate beds," Jim said quickly. "I mean…. if you don't mind the both of us…" his voice trailed off.

"No I don't mind!" Roxanne said perkily. "It'll be cheaper. Thanks," she said with a smile.

"You don't have to say thank you. You're giving me so much. The ride, the motel room, this dress," he said, looking down at his gown.

They parked in the almost empty parking lot and walked inside together. Roxanne placed her suitcase down at the front desk and began to check in. Jim looked around the lobby. It was pretty motel. Paintings and mirrors on every well-lit wall.

"Ok Tiffany," Roxanne said, walking over to him. "You take my bag up to room 312, I have to get some more stuff out of the van." She handed Jim a key card and walked back outside. He found himself watching her body as she moved.

He went into the elevator and pressed the third floor button, raising a perfectly trimmed eyebrow at the choice of elevator music the motel had chosen. After finding his way through the different hallways, he found room 312, inserted his key card, and opened the door. Roxanne made it up to the room with another suitcase a short time later.

"Whats that?" Jim asked her.

"Some stuff for you," she said, opening the suitcase on the double bed. "I got you a nightie for tonight, a fresh pair of panties for tomorrow, and a new dress too."

Jim didn't know what to say. "You're so nice. How can I repay you?"

"Put it on!" She said eagerly, placing a hand on Jim's waist. "I want to see how it looks on that body."

Jim giggled like a little girl. "Ok! One sec!" He went into the bathroom and took off the high heels he had been forced into. The dress was a little more difficult, but he eventually got out of it. The nightie was pink and lacy, and kind of small too. Roxanne clearly wanted to see Jim as much as possible. He slipped it over his head and his long blonde curly hair, and let it fall down his body. He adjust the top and found it to be quite comfortable. The breast line was tipped with white lace, and it only came down to his upper thighs, almost exposing his white panties.

He walked back out into the bedroom in just his underwear and nightie to find Roxanne already in bed. She was wearing black lace panties and a matching bra. She gestured to Jim to come closer with her delicate fingernails. Jim slowly walked towards the bed, excited for what was about to happen. He slipped both legs under the covers, lied down, and turned to Roxanne. She immediately took hold of the situation. She wrapped one leg over Jim's waist, and used her other thigh to put pressure on his vagina. She slipped one hand up his nightie and played with his nipples, and held his soft cheeks with her other. Roxanne kissed him passionately, using her warm and wet tongue to fill Jim's mouth to prevent him from speaking.

"Of Tiffany…" she said, moaning. Your body is so warm.

"Roxanne.... you're so.... forceful. I love it," he whispered. He played with her boobs as well, and tickled the inside of her vagina a little. They played for a good portion of the night, and slept in late into the morning.

Jim awoke to a room filled with sunlight. The curtains had been spread wide. For a moment he heard the shower running, but then heard it shut off. A minute later, Roxanne walked out of the bathroom, tying the knot on the cotton white bathrobe the motel provided in the closet.

"You're finally awake," she said, walking over to Jim. "Wanna hop in the shower?" she asked, placing her warm hand on his soft tummy. "Don't worry," she added, "I'll be waiting for you when you get out."

With that, Jim smiled and got inside the shower. The water was still warm, and it felt good to finally be clean. He stepped out of the shower onto the cold tile floor when he was done, realizing he didn't have anything to put on.

"Is there another one of those bathrobes in the closet Roxanne? Jim called out to her, shivering.

"No." Roxanne stepped inside the bathroom with Jim and locked the door. "Just the one. But I don't mind sharing." Roxanne kissed Jim on the lips as she untied her robe. She opened it up and wrapped it around Jim's back while it was still on her. She then tied the knot behind Jim, tightly. The two of them were both inside the same bathrobe together. Their hot, wet bodies pressed up against each other. They kissed some more until Roxanne asked, "So, you wanna hit the road?"

Jim looked at her with a raised eyebrow. "No. I don't." And kissed his new girlfriend again.