Neil stood outside the hotel room fumbling with the door pass. He slid it through the slot, but the light turned red and he eared a loud “error” sound. He tried again and got the same result.
A pat on his backside brought him to attention. “Having trouble there sweetie? Here, let me help you,” his girlfriend leaned over his shoulder, one hand still firmly on his behind, the other reaching around to grab his hand. She pushed his hand to the slot and brought it down, brining an instant green light and grinding noise. “See? Not too hard sweetie. Now, bring the bags in.”
It was a brief moment, and one a passerby might have ignored. However, it filled his stomach with excitement. Everything from the possessive hand on him and the condescending way she had taken over, to the slight mocking change in the tone of her voice left him eager for more.
She walked in ahead of him, leaving the bags for him to carry. He took a moment to watch her tall, curved body strut in front of him and her long blond hair sway behind her. He picked up the bags and walked in after her.
They had spent extra to rent the suite, and it was worth every penny. He stood in a large living room with a couch and television, and a bar at the far end. He followed her past the door to a bathroom with a wide open tub, and into a bed room with a king sized bed. The walls were painted a deep gold and red, and prints of famous paintings were hung around it.
“Put the bags on the bed,” she said. Not said. “Commanded” was the right word, and he obeyed immediately.
“Now, lets see if you’ve been a good boy, shall we?” she said.
His heart jumped. “What do you mean?”
She walked up close to him, put a hand around his back, and pulled him so that his face was inches from hers. Her second hand reached down to his belt buckle. “I mean I didn’t get to check yet if you obeyed this mornings instructions, or if you’ll be getting a spanking.”
Neil gulped. “I uhh…”
“Mhmmm,” she said. She undid his buckled and reached a hand into his pants. He gasped as she grabbed him. She rubbed her hand back and forth, feeling the smooth, silken feeling of the panties he’d been ordered to wear.
She smiled. “Hmmmm. Good girl,” she pecked him on the lips.
This was a game they played often. They had found each other online, and his submissively tendencies played exactly into her dominants ones. At her instruction, he had had let his hair grown long, and even dieted so that his slight framed could perfectly fit into the dresses, skirts and corsets she gave him.
She stepped back and, without a seconds care for his permission, pulled his pants down to show his ruffled red panties. “And isn’t that a pretty sight?” she said. He blushed and looked at down, but the stiff front of his panties removed any chance for him to claim he didn’t enjoy it. She reached down and flicked it, causing him to gasp. “I think we’ll have to do something about that, however. We can’t have you gunking up your pretty panties.”
He looked at the clock. “But, we’re supposed to be going to dinner…” he said, but couldn’t contain his growing excitement.
She chuckled. “I know, but we do have to get ready first anyway. We’re not going in the clothes we flew here in, are we?”
He shook his head.
“Good. Strip. To your panties.”
If his state of mind had allowed for any disobedience, he might have questioned why he was stripping while she was still fully dressed. However, after only a few words from her he felt that independent part of his mind slow fade away as his submissive side took over. He stripped down. Somehow, with his underwear he felt even more naked then he would have been bare.
“Good girl, little Nelly.” He blushed at the name she used for him when they played. “Now, open that bag,” she pointed.
He walked to the bag she indicated and opened it. He stood back in shock, his hands going to the front of his face.
“I took the liberty of repacking one of your bags. Hope you don’t mind,” she said.
“But…” he struggled.
“Don’t worry, you’re other bag still has your ‘normal’ clothes in it, if you prefer. IF you prefer.”
The first thing he noticed when he opened the bag was the color pink. The second was the bright sheen of silk. It dawned on him that what he was looking at wasn’t what he had packed, but a small collection of the dresses and humiliating, feminine outfits she regularly dressed him in.
“Do you want to wear it?” she asked.
“We don’t have time,” he replied quickly.
“That’s now what I asked,” she said. She grabbed his hand and pulled it toward the dress. “Feel that silk? See the pretty colors? Don’t you want it on?”
“Think of how pretty you’ll look in that dress. Look at how good it well feel on your skin. Do you want that, or do you want your ugly boy clothes?”
The words sent images hurtling through his mind. Himself in now countless outfits, panties, skirts, bows… his made up face blushing in the mirror as he sashayed his skirt, then stumbled in his heels towards her on the bed, dressed in black leather, holding a rod…
“Isn’t this the perfect opportunity? Far from home, a city full of strangers. Not one will recognize you, and not one will remember the blushing girl in the pink dressed they passed, but I’m sure they all appreciate her pretty face. Don’t you want to look pretty for your mistress? Just a sweet little sissy for me?”
His stomach turned at the twisted, teasing tone of her voice. He had done it before. Walked around in skirts, praying no one recognized him. But those had been normal dresses, the kind a normal woman might wear. This… this was a costume, a sisified Lolita outfit people would stare at. He wished that didn’t make it all the more exciting. “Yes.”
She chuckled. She picked up the dress and a pair of long frilled stockings. She began rubbing them over his skin. The material was smooth and cold against him. She rubbed a hand through his hair, sending shivers down his spin. His mouth hung open. “Sorry, what did you say?”
“Yes!” he said louder.
“I want to wear the pretty dress.”
More images. The few times he went into public cross dressed. A few confused glances, others not even noticing, accepting him for how he dressed, as a shy, pretty girl…
“Please mistress. Please put me in the pretty dress. I don’t want to wear my boy clothes. Please mistress please mistress please mistress…”
his please became more and more desperate as his anticipation drew.
“Do you want to be my little sissy slave?”
“YES! Please make me your little sissy slave!” The humiliating words gasped out of his mouth. The entire world around him disappeared except for the sight of the comically feminine skirts and the feeling of her cruel hands rubbing and teasing him, and he wanted nothing more but to obey her, to humiliate himself for her pleasure.
“Good girl,” she said, and patted his bottom. “Now, on the bed.”
He would have asked why, but it didn’t occur to him to second guess. The fact he had no idea what she wanted or why she told him to lie down only added to the excitement of obeying her.
She reached into the bag and pulled something out. Like the rest of his clothes, it was pink and shone. Unlike it, it was square and crinkled with…