Sissy's First Trip Out

*This is my first story so please comment as much as possible to let me know what you think. Thank you!*

Kenny had always been obsessed with women's underwear. It all started out pretty innocently, well, as innocently as can be expected when masturbation is involved. He used to look through women's fashion catalogues and drool over the lingerie and bikini sections. But after a while this simply wasn't good enough. He wanted the real thing.

During his college years, he lived in an apartment with his two friends, Craig and Jane. Living in such close quarters gave Kenny the chance to steal some of Jane's underwear. He will never forget the first pair of panties he stole. They were white with pink trimmings and a Hello Kitty logo on the front. At first, he had just smelled them and jerked off, but it wasn't long before he was wearing them. Once he had gotten a taste for stealing panties, he couldn't stop. Every time he was invited to someone's house and the opportunity presented itself; he would be straight into the panty drawer. There was no doubt about it, he was a sneaky little pervert. Although Kenny had been doing this for years, surprisingly, he had never been caught. Of course, he wished he didn't have these urges, but they just wouldn't go away.

After graduation, Kenny moved into a new apartment and for the first time ever was living alone. Having the extra space and freedom was great, but this also meant that his panty obsession started to grow out of control. He no longer had to worry about anyone opening his mail, so he decided to order himself something special.

It was Sunday lunchtime, and Kenny was sitting at the kitchen table staring at a package that had just arrived. Inside was his first order from an online lingerie shop and he couldn't have been more excited. He grabbed a knife and opened the box. Everything was there: a pair of purple lace panties with a tiny bow on the front, a matching lace bra and a pair of thigh-high stockings. His cock was tingling just looking at them.

He raced to the bedroom and started stripping off. Kenny was 5' 7" and quite slim. He had been growing his light-brown hair out lately and at the moment it was about shoulder length. He had never been a hairy guy per se, but now that he was living alone, he shaved his entire body every other day. If you saw him on the street you wouldn't think he looked girly, but when he was naked, he had a feminine aura about him.

The lace panties felt amazing as they rubbed against his smoothly shaven cock and balls. He slid the stockings on, clipped the bra at the front of his chest and spun it around into place. His heart was pounding as he eyed himself in the mirror. He knew what he was doing was weird, but it felt amazing. Kenny had big plans, and he felt butterflies in his stomach just thinking about them.

Today he was going to go into town with his new lingerie on under his normal boy clothes. It would be the ultimate thrill for him and no-one would ever know. He didn't know exactly where he was going to go, but he planned to do some shopping. It didn't matter where he went really, because the important shopping had already been done.

After putting on the rest of his outfit, which was comprised of a pair of jeans, a plain black t-shirt and a black hoody, he headed out the door. He was pretty confident that no-one would notice his lingerie, although the outline of the bra was visible without the hoody. He pulled the zipper all the way up and kept walking. The feeling of the lace on his cock soon made him erect, so he had to tuck it up into the waistband to keep it from showing. It was only about 5" when fully erect, but he didn't want to take the chance.

Kenny checked the time on his phone, it was 17:38 already! He must have gotten carried away with himself prancing around in front of the mirror. Most of the stores on the high street closed at 18:00, so he would have to hurry. He peered through the windows, looking for somewhere that tickled his fancy. He stopped at a clothing store and decided it would do.

The store was almost entirely empty it seemed, as Kenny could only see one middle-aged woman perusing the merchandise rather uninterestedly. He walked between the aisles and pretended to be looking at some jeans. Suddenly he had a thrilling idea. What if he were to try something on? Then he could expose his lingerie in the changing room without anyone seeing. That would be so hot! He glanced around looking for staff members, but he couldn't see anyone. Kenny hadn't planned on pulling something so risky, but it would only take five minutes. The butterflies were going nuts in his stomach at this point. He took a deep breath, grabbed a pair of jeans and walked briskly towards the changing rooms.

The changing rooms in the store were not what he had expected. Instead of a wooden door, with a sliding lock, there was only a curtain to pull across the cubicle. There were three cubicles, each with three mirrors inside. Opposite the cubicles was a long wooden bench, presumably a waiting area for other shoppers. He thought about ditching the idea, but he had already come so far. "Fuck it," he thought and stepped into the cubicle.

He quickly unzipped his hoody and pulled off his t-shirt. He stood with his back to the wall and kept watch under the curtain, so he could see the feet of anyone approaching. He undid his jeans and slid them down. His cock was still fully erect and poking out of the top of his lace panties. He turned sideways to inspect himself in the mirror on the side wall. He thought his heart was going to burst out of his chest. Suddenly, he heard footsteps coming towards him and he saw a pair of high heels in the space beneath the curtain. His heart stopped.

"Anyone in here?" said Nadia in an English accent. Nadia had been living in the States for the past three years and had been working in the store for two. She liked her job apart from the fact she always had to do the late shift. This was the most undesirable shift, as it involved checking for any customers and then locking up. And there were always stragglers. Kenny was frozen stiff and unable to say anything. Nadia pulled open the curtain and her eyes widened in surprise.

"What the fuck are you doing?" said Nadia.

"I... er...," Kenny stammered. He had no idea what to say. Humiliation washed over him and his face turned bright red. Nadia was a beautiful woman. She had long, flowing, blonde hair and dazzling green eyes. Eyes that were currently looking Kenny up and down in disgust.

"Say something then, you freak!"

"I- I- I'm sorry," said Kenny. He was shaking.

Nadia sighed deeply. "I'm sick of dealing with dirty little perverts all the fucking time," Nadia said rolling her eyes. "Every day, some little freak is gawking at me or making pathetic attempts to hit on me, and this... this is just fucking gross!"

Kenny could understand why men would gawk at her. She had a body to die for. Her thick hips were being hugged by a tight black pencil skirt and her D-cup breasts were barely being contained by a thin white blouse. Even in a state of shock, his boner was going nowhere.

"But I guess you wouldn't hit on me, would you?" asked Nadia, "I mean you're clearly a faggot."

"I- I'm not gay!" Kenny blurted out.

"Really?" Nadia said, "because most straight guys wear fucking lingerie, do they?" She put extra emphasis on the word "lingerie" to make it sound fancy.

Kenny bent down to grab his boy clothes. There was no way he could explain his way out of this one, so he might as well just run.

Nadia's gaze followed him to the ground. "No! Don't you dare bitch!" She spread her arms out and grabbed both sides of the cubicle making sure there was nowhere for Kenny to go.

"I'm sorry, OK? I just want to go," said Kenny in a small voice. "I'll never come back, I promise."

"You're not going anywhere faggot. Do you really think I'm just going to let you pull this shit in my shop and get away with it?" said Nadia. She took a step back as she realised Kenny didn't have the guts to run. She looked him up and down and a smile spread across her full red lips. "Go on then sissy boy. Give me a twirl," said Nadia, making a twirling motion with her finger.

Kenny was taken off guard by this request. What was she playing at? Whatever her game was, he had no choice but to play along, besides, the idea of following Nadia's instructions seemed quite sexy. It would be just like one of those jerk-off instruction videos that were all over the porn sites. The ones where some dominating chick tells you just how hard and fast to jerk it. There's usually a countdown at the end followed by some insults.

Earlier in the day, Kenny had spent hours twirling and prancing around in front of the mirror, but now his motions were awkward and decidedly unsexy. Nadia giggled at his feeble attempts.

"Hmmm... this look is not quite working for you," said Nadia, "wait here a minute." She marched off leaving the curtain open.

Kenny hoped there was no-one else still in the store. He looked down at his slim body and noticed how fast his bra-covered chest was rising and falling. He had wanted a thrill but this was too much. He slid his hand over the front of his panties. His cock was still rock hard. In fact, he hadn't been this hard in months. Maybe he was a faggot after all. But he couldn't be, because Nadia was the one turning him on. What man wouldn't be hard with a goddess like her barking instructions at him.

"Here you are," Nadia said, throwing a balled-up piece of cloth at him. "This will be perfect."

Kenny unravelled the cloth and held it out in front of him. It was a white and yellow sundress with a floral design. It looked like it would fit, but it was going to be very short.

"What are you waiting for slut? Put it on."

Kenny stepped into the dress and slid it up over his shoulders. There was a small zip in the back that he couldn't quite reach on his own.

"Can you zip me up please?" Kenny asked.

Nadia stared at him with a look of contempt. "Step forward."

Kenny moved forward with one large step; he was now about a foot away from her. He couldn't bear to look into her piercing green eyes for longer than a few seconds. He was afraid he might fall into those emerald pools of seduction and never resurface.

Thwack! She brought her hand down hard on Kenny's face. His head spun to the side, and he let out a yelp.

"From now on you will address me as Mistress Nadia!" Nadia had seen her fair share of pornography so she knew just how to play the part.

Kenny brought his hand up to his face and held his stinging cheek. The slap was shocking, but what was more shocking was how much it hurt. Nadia was a lot stronger than she looked. She was only 5' 5" and, apart from her curvy hips and ample bosom, she was petit. She had slender arms and a waist so narrow you could almost cover the circumference with two hands.

"Yes, Mistress Nadia."

"That's more like it, sissy," said Nadia. "Turn around then."

"Yes, Mistress Nadia." Kenny spun around and she pulled up the zip on the back of his new sundress. Despite the hard slap, his boner was still going strong. The dress was short, but it covered his erection quite nicely. His smooth sissy ass, however, was peeking out from beneath the hem.

"Now, let's try that twirl again. And this time you better not disappoint me."

Motivated by his throbbing cheek, he twirled around in as girly a fashion as possible. This time he was much more convincing, he had had a lot of practice after all. He completed his twirl by curtsying and grabbing the bottom of his dress, lifting it slightly.

"Wow, you are such a good little faggot, aren't you?" Nadia clapped her hands together sarcastically.

Kenny was happy to have pleased her this time. A bell rang at the other end of the store, and Kenny heard the sound of the door opening. Nadia rushed off to see who it was. Kenny bent down and pulled his phone from his jeans pocket. He checked the time. It was 18:16. The store should be closed by now. He hoped that she had gone to tell whoever it was to beat it and lock the door.

After a few minutes he heard footsteps heading back towards his cubicle of shame. He heard voices. That's right, voices. Plural. Whoever had come into the store, she had not told them to beat it, she had invited them in. He closed his eyes tightly and wished he were back at home.

First around the corner was Nadia. She walked with an air of confidence, her hips swinging from side to side. Her full breasts bounced ever so slightly under her blouse. She was followed by a tall, dark-haired man in a shirt and tie.

"Here she is," Nadia said nodding her head in Kenny's direction.

"Fuck, you weren't wrong," the shirt and tie guy said, "I've seen it all now."

On closer inspection Kenny could tell that this guy was the security guard. Shirt, tie, black pants and black boots. He had a small laminated badge hanging from the front of his shirt pocket. SECURITY: DEAN.

"He says he's not gay," said Nadia. Her emerald eyes gleamed as she said this.

"Well, he's definitely not straight," laughed Dean.

Kenny just stood there; his hands clasped together in front of his waist. His shoulders were hunched forward as if he were trying to disappear inside himself. He was.

"Look at this, Dean." Nadia slapped his hands out of the way and lifted up the front of Kenny's dress. Only the tip of his erect cock was poking out above the waistband of his purple lace panties.

"What the fuck," Dean said. He winced and turned his head away in disgust. "I don't want to see that shit, Nadia."

"See, you're pathetic, revolting," Nadia said as she glared at him with contempt. "You're not a real man, are you faggot?"

"No," said Kenny.

A sharp burst of pain seared through Kenny as Nadia grabbed his balls and squeezed. He felt the pain travel up to the pit of his stomach and he let out a girlish squeal.

"No, what?" she demanded.

"No, Mistress Nadia."

"That's better." She released his aching balls and the front of his flowery summer dress flopped back into place. "What do you think we should do with him?"

"I can call the police if you want," Dean said shrugging his wide shoulders.

"Surely we can think of something better than that." Nadia stroked her chin in an exaggerated fashion to show she was thinking. "We could kick him out into the street like this and watch him squirm off."

"Suits me," said Dean.

"No, please!" said Kenny.

"Shut the fuck up, bitch!" Nadia shouted, "Get on your knees, now!"

His balls were still throbbing and he had a sick feeling in his stomach. He wasn't going to argue. He dropped to his knees in front of his new mistress.

"Why don't we show him what a real man does when a beautiful woman touches his cock," said Nadia. She turned to face Dean and grabbed hold of his crotch. Dean looked somewhat taken aback, but he didn't stop her. Who would? She kept caressing the front of his pants and soon his bulge started to grow.

After a few minutes of this, she removed her hand and started unbuttoning her blouse. Dean didn't take long to get over his surprise. He was eyeing her hungrily. One button. Two. Three. Pretty soon her blouse was off and she was working on undoing her bra. Dean continued to stroke the bulge in his pants as he enjoyed the show. Both Dean and Kenny stared in amazement as Nadia's big, milky-white tits burst out of her brassiere. They were heavenly. Dean placed one strong hand on her breast and started squeezing her nipple. She let out a moan and returned her hand to his groin.

"Make yourself useful and undo his belt," Nadia ordered.

"Yes, Mistress Nadia." Kenny shuffled forward on his knees and grabbed Dean's buckle.

"Woah, get the fuck off me!" Dean shouted, slapping Kenny's hand away.

"Calm down, babe," Nadia said seductively, "I know you've always wanted to fuck me. This is your chance." She took Dean's finger into her mouth and sucked on it gently.

"Fine," said Dean.

Kenny got back to work undoing Dean's belt. Nadia sucked Dean's finger. And Dean closed his eyes and breathed heavily.

It wasn't until Dean's black pants slid to the floor that Kenny realised just how big his cock was. He was wearing a pair of tight, white Calvin Klein's that left very little to the imagination. Dean's cock was only semi-erect, but it was easily 7" long, and thick. The thin white boxers were doing their best to conceal this magnificent cock, but they were failing miserably. And Kenny had a front row seat with his face just inches away from this monster.

"Now that's a real man's cock, sissy," Nadia said, noticing how Kenny couldn't take his eyes off Dean's growing member.

Kenny blushed and looked at the floor.

"There's no need to be shy, fag boy," said Nadia. She grabbed the back of Kenny's head and pushed his face into Dean's crotch. He could feel the warmth of Dean's cock against his face. "Get a good smell, bitch."

Dean opened his eyes and looked down at the strange sissy boy who had his face buried in the front of his boxers. "What the fuck," he said. Dean tried to pull his hips back to get away, but Nadia just pushed Kenny's head harder.

"Stop it Dean," said Nadia. "You do want to fuck me, right?"

"Of course," replied Dean.

"Well stop fucking around and get with the programme. Let me show this bitch what a real man is, and my pussy is yours, babe."

Dean didn't look impressed. He wasn't used to being told what to do by women, but he had fantasized about fucking Nadia since the day he met her. He nodded his head in agreement.

"Do you like the smell of his cock, sissy?" said Nadia releasing Kenny's head to allow him to speak.

Kenny took a deep breath as if he had been drowning. "Yes, Mistress Nadia." The musky scent of cock filled his nostrils, and he wondered how he'd let this happen.

"What a good little slut you are. Now get those boxers off and let's have a proper look."

Kenny knew what was coming. She was going to make him suck Dean's cock. He wasn't ready for something like this, but he knew he had no choice. Even if he could overpower Nadia, which he was unsure about after that slap, he would never be able to get past Dean. The guy was about a foot taller than him and ripped. He grabbed the waistband of the white Calvin Klein's and pulled them down. Dean's cock flopped out into Kenny's face and his jaw dropped. He instinctively made the same face all pornstars make when they see a cock. The oh-my-god-I-can't-believe-how-big-your-cock-is face. Dean's cock was now close to fully erect and was around 9" long, thick and throbbing.

"I knew you'd love it," said Nadia. She grabbed the back of Kenny's head again and rammed his face towards Dean's juicy member. Kenny's mouth was still open and was soon filled with hot cock.

The musky taste washed over Kenny's tongue, as Dean's cock slid past his lips and down his throat. He wasn't prepared for it to go so deep into his mouth, so he gagged. Nadia tilted his head back by pulling his hair. He gasped for air.

"How does it feel to finally taste a hard dick?" asked Nadia patronizingly. "I know you've always dreamed of sucking off a man."

Kenny said nothing and just knelt there panting. He was barely listening as he tried to make sense of the emotions running through his head. He felt like he was drowning in a whirlpool of shame, confusion and arousal. His own cock, which now felt microscopic after seeing Dean's, was still rock hard.

"Answer me, faggot!" demanded Nadia.

"It's feels... good," Kenny answered.

"Show me how much you love it."

Kenny turned his eyes back to the monster cock dangling in his face. He didn't even know how to suck a cock. What was he supposed to do?

"For fucks sake, it's not rocket science," said Nadia. "Grab the shaft and start stroking it."