Stiletto Deceptions

I can't believe I'm doing this. Alex pushed through the doors into the mall department store, leaving the chilled fall air behind. The words of instructor Haskins rang in his ears from the morning's final meeting. Before the man released Alex and his peers to begin their insertion to the training area.

"It's a simple setup. The exercise will commence when you leave this building. Check the signal site and make your way to the rendezvous at the city center hotel. There will be ample surveillance all over you. If you're caught," the man paused, and stared stonily into all twenty of their faces. "Don't get caught. You won't like it."

Alex used the mirrors above the escalators to check behind as he ascended to the second floor. So far, nothing, but he knew that wouldn't last long. He glimpsed at least two cars worth of surveillance as he walked in from the parking lot, and he knew they would soon send agents into the store after him. Not much time. The store was nearly empty in the late morning hour--Alex spotted a few housewives and a retiree or two idly browsing, but that was it. He approached a woman in her fifties with a name tag in the women's section. Alex took a deep breath and handed her a receipt, glancing behind more than once.

The woman smiled, lingering on his hand just a fraction of a second longer than needed. "Please, come with me." She winked and led him deeper into the store.

Still no sign of pursuit. She took him to a lonely checkout counter on the far end of the woman's section. "Here you go, hon. Let me know if you need help with anything." The woman parked a suitcase and two shopping bags in front of him.

Alex murmured his thanks and took the bags. After a final gaze around, he headed to a changing room and locked himself inside, exhaling raggedly. He stared into his reflection in the mirror. Did he really want to do this? Was there any other way? Of course there was. But this was his only plan for infiltrating the city undetected. With one final look in the mirror, Alex began strip his clothes off. He'd always been a little on the skinny side, but months of yoga had toned his body down to a lithe figure. Last night, he'd shaved every inch of his body, and he had to admit it felt great.

From the shopping bag in the dressing room, he pulled out a makeup bag and gave his face a light coating of foundation, rouge, lipstick, and mascara. He sprayed a hint of perfume into the air and leaned into it. Then he began to dress. First, silk panties and a matching bra, with a bit of a padding. Then the thick, nude pantyhose, and a black skirt that came down nearly to his knees. A gauzy gray blouse top went next, with intricate lace patterns. Earrings, and a pearl necklace. The raven black wig took a moment to adjust properly in the mirror. Finally, he slid his stockinged feet into high heel pumps, letting out an involuntary sigh of pleasure.

"Hey there, Lexie," the woman in the mirror said, a hint of a twinkle in her eye. The experience of presenting as a woman was always electric. Sheer legs, sheathed in nylon, elevated in four-inch stilettos. Lexie closed her eyes and exhaled a few times to calm her fluttering heart. Then she opened them and nodded firmly at the reflection. Time to work. She opened the suitcase, found a Coach purse inside, and loaded it with cash and items from her old clothes. Lexie stripped the tags and stickers off the other items in the suitcase--a few other choice outfits. One final touch up of the makeup and she was ready.

The lady who walked out of the dressing room appeared to be late thirties, office professional. She strode past the red-haired woman, busy helping another customer. The woman looked at Lexie and slightly nodded her head. Lexie winked and continued towards the escalator. A man in a business suit marched briskly toward her, and her heart skipped a beat. He glanced at her quickly and continued his purposeful walk into the store. Lexie noted the small earbud and the wire extending from his ear into his shirt collar. On the way out, she noticed several more members of the surveillance team, but thankfully they paid her little attention.

The signal site was in a bookstore in the middle of the mall. Just a sales rep stopping to get something to read on the way to the airport. Pharmaceutical sales, she decided. They always looked sexy. Lexie got a coffee and checked out the exact location-- a message board near the bathrooms. She noted no fewer than three static surveillance positions, covering the board from all angles.

The best cover is nonchalance. Coffee in hand, she walked toward the women's room, heart pounding. After lingering for a minute in the stall, Lexie came out with a piece of paper--a sales flyer for a Peloton bike that didn't exist. At the board, she quickly memorized the phone number for a massage parlor--the signal, then moved to attach her flyer. With the coffee, it was difficult to do with one hand, and she flinched when a man approached.

"Here, let me help, miss," he said with a smile. She recognized him as one of her instructors, but the man gave no indication he knew it was Alex.

She offered him a demure smile. Although she'd been practicing her voice, she preferred to use it as little as possible. "Thanks."

His eyes swept up and down her appreciatively. "My pleasure."

As she walked off, she felt his eyes upon her. To her utter shock, no one moved in to intercept her. Holy shit, he was checking me out. No time to process. Keep moving. The far end of the mall held an entrance for the metro, and she moved that way, sighting a few of her classmates moving with a nervous energy. Lexie watched one of them, Mike, get stopped by a pair of men in collared shirts and khakis, who hustled him towards the parking garage. She was in luck- a train was ready to board when she arrived. Lexie purchased a ticket at the kiosk and boarded. She crossed her legs and opened a discarded newspaper she found on the seat. She felt the men in the train compartment ogle her, and she dangled a heel idly without so much as a glance toward them. The attention felt exhilarating, like the high from some illicit drug.

She got out after four stops and walked a block before hailing a cab, just to ensure she was clean of pursuit. The front desk at the hotel informed her she still had an hour before her room would be ready, so she left her suitcase and went into the bar to get a late lunch and a drink. She needed one after that experience.

Lexie sat at the bar and picked at her salad, sipping a glass of chardonnay. To her left, she spotted a man in a corner booth, a trio of empty beer glasses on the table. He returned her stare. Instructor Bellos, one of the exercise controllers. Their stare deepened. Five seconds. She felt a quiver in her stomach, a firing of something, a lurching sense of shifting. She smiled and looked away. A plan began to form in her mind. Did she have the courage to enact it? In the mirror above the bar, she watched Bellos stand up, and walk over.

An hour of small talk, drinks, and laughter later, and they were in the elevator. Bellos pawed at her chest, kissing her sloppily, and took a hefty pinch of her ass. Lexie's heart raced--had she made a huge mistake? Rather than be repulsed, she was intrigued. Attention from men was one thing, but focused, lusty desire was another entirely. It was a heady concoction. She held off his advances long enough for the elevator door to open. Bellos led her unsteadily towards his room, sliding the key into the lock with such difficulty that Lexie thought she would have to do it. The combination of alcohol and what she'd slipped into his drink was finally working its magic on his stocky physique. Finally, Bellos figured the door out and staggered inside. She followed with trepidation, looking around carefully. She had just set her purse down when he was on her again, kissing her and pressing his erection into her skirt. Bellos took her hand and guided it down to his groin. She felt him through the denim material, and her adrenaline surged--she was touching another man's cock!

"Oh, baby, that's it," Bellos grated into her ear. Lexie inhaled raggedly. Could she do it? He unzipped his zipper, and his manhood flopped out. Bellos guided her hand to it, muttering and groaning. Lexie slowly explored the hardness and the heat of his shaft. So different from touching her own. Bellos bucked his hips toward her, begging her to stroke it. Lexie reveled in the power she had over this man--she could control of pace of his pleasure.

"I want to fuck you so hard," Bellos said, cupping her ass and stroking the pantyhose under her skirt.

"It's my time, baby," she murmured. "Not today." She traced a pattern on the head of his dick with her fingers and felt precum soak her thumb. Wow, she was really doing it for him.

He cursed softly, and Lexie steered him down onto the bed, sliding a silken thigh over his leg. The precum had lubricated her hand a bit and eased her stroking of his shaft. She increased the pace, and she felt Bellos tense up.

"Oh god, oh god, oh god, jerk me baby, yeahhhhh." With a roar he came, his seed shooting into the air. Bellos lay on the bed like a beached whale, panting heavily. Lexie noticed he had broken out in a flop sweat. Suddenly he lurched up, eyes wide, and stumbled to the bathroom, slamming the door behind him. She heard the sound of heaving and retching, the visine finally catching up with him.

Quickly, Lexie looked around the room. On the table, she found a folder labeled "Exercise Scenarios" and she snapped a picture of a few documents. On a whim, she grabbed the key to Bellos's room from the table before slinking out before he came out of the bathroom.

Downstairs, the front desk clerk informed her that her room was finally ready. Lexie took her suitcase and went to her room, bolting the door with a relieved click after leaving the "do not disturb" sign outside on the handle.

She dropped her stuff and stood in front of the mirror, looking at herself. Lexie had always dressed up in the privacy of her own apartment, but this was the first time she'd actually interacted with people in the world, and it was both exciting and overwhelming. She massaged her cock through her skirt. It had basically been hard for the last three hours, running on adrenaline and the thrill of her womanly masquerade and the seduction of Bellos. Her balls ached.

Lexie slipped out of the skirt and blouse but left the heels, pantyhose, and bra on. She grabbed a towel from the bathroom and lay on the bed. Lexie closed her eyes. Stroking herself, she realized it wasn't as bad as she thought it was going to be. She actually kind of liked it, she realized with a lurching, quickening pulse of her heart. Lexie imagined sucking Bellos, on her knees in front of him. The thought of both being so submissive and so powerful was a huge turn-on. She imagined putting his cock in her mouth as she massaged hers, reveling in the silky feel of both the bra and the pantyhose.

Now Lexie saw Bellos turn her over on the bed and inserting himself into her. She thought about Bellos hammering her ass from behind with his cock, taking what he wanted while being consumed with desire for her. Lexie put her legs in the air so she could admire them- the sheer, gauzy hose and the stiletto pumps reaching skyward. With a moan of complete ecstasy, she climaxed, putting the towel on her cock so she didn't soil any of her undergarments. The stress of the day caught up to her, and she felt waves of exhaustion sweep over her. Lexie nodded off, completely satisfied.

Later, she changed out of her clothes, and back into Alex. It was a little sad, but he knew that Lexie would be back soon- his secret weapon had already come in handy once on the operation. Kevin, a teammate, was supposed to have the room next door, but Alex had heard no activity there. He ordered room service and hunkered down. He checked the pictures and made notes. Finally, around midnight, noises next door. Alex crept over and tapped a code on the adjoining door lightly. A pause, then the answered tap series came back. Alex unlocked the door on his side.

"Got caught. That did indeed suck," Kevin reported. He was tall and leanly muscled. "Three hours of interrogation. But, I picked up the technical equipment from the dead drop. What about you?"

"I managed. But I got something else." Alex showed him the pictures.

"How the hell did you pull this off?" Kevin asked, sipping a beer. "We literally just got here today. Are you running a source already?"

Alex took a deep breath and explained what he'd done. He watched the look of shock slowly morph into confusion, and perhaps a touch of curiosity at the end.

"You know, all the people in this exercise are dudes," Kevin said. "We can turn this crossdressing thing into an advantage."

The next day, they planned to go look at one of the targets locations, posing as a couple. Kevin wore a hat and eyeglasses, and Alex went as Lexie.

When she came into his room before they left, Kevin whistled softly. "Damn, Lexie, no one's going to look at me--they'll be too busy staring at you."

She smiled, red shading her cheeks as she did a little twirl. Black sheath dress with a chunky belt, black stockings, and high heel leather boots.

When they saw some of the instructors milling around near the target location, Kevin pulled her close, caressing the side of her face lovingly. "We're just another happy couple, out for an evening stroll," he murmured, staring into her eyes.

Even with her high heeled boots, she was still shorter than him. Her pulse quickened at his touch, and she pulled him closer. She stared at his lips, biting her own. The instructors moved off, and Kevin stepped back.

Lexie felt a pang of something. Regret? Sadness?

Kevin looked at her. "That was close. We'll have to be more careful."

"Yes. Careful."

They walked hand in hand toward the taxi stand.

"So," he began, "do you like being Lexie?"

She swallowed, feeling the flutters in her midsection. "Umm, well, to be honest, I do like it. She's my alter ego."

He looked at her, then out in the distance. "And so, are you, are you like interested in dudes when you are Lexie?"

She stopped at a water fountain, found a coin in her purse. "I don't know. It's complicated. I'm not gay exactly, but when I'm dressed like this I just feel like--"

"Like a different person," Kevin finished, flipping a coin of his own into the fountain.

"What'd you wish for?" She asked playfully after flipping her own in.

"I'll never tell," he responded with a smile as they kept walking.

"You know," Lexie began, "I kept a key to Bellos's room. Technically, the hotel is supposed to be a safe zone for operational activities, but all's fair in love and war, as they say. I could go back and bug it with our gear."

"No way," Kevin said, staring into her eyes. "Too dangerous. No telling what he would do to you if you got caught."

Lexie stared back, taking one of his hands in hers. "It's worth it. We can have a nice dinner afterward."

"We can have a nice dinner anyway, without the risk."

"Kevin. I have to do it." She saw the hurt in his eyes.

"Fine."

He insisted on riding up to the instructor level in the elevator. "Be careful in there," Kevin whispered in her ear as he planted the touch of a kiss on her cheek. She felt a heady mix of excitement and fear as she walked out of the elevator.

Lexie knocked on the door to the suite. Deep breath to calm her surging heart rate. She wore a gold and brown patterned silk blouse top, a black skirt, black stockings, and five-inch black high heel pumps. Lexie had a necklace adorned with white stones, big dangly hoop earrings, and heavy makeup. Looking around quickly, Lexie inserted the key and entered. Empty. She quickly spread the bugs around and was in the midst of taking more pictures of the exercise scenario when she heard the chirp of the door lock. Fuck.

The door opened, revealing Bellos. He looked her up and down swiftly. "I was wondering if I was going to ever see you again."

"I wanted to give you another chance," she said simply, staring back at him. She tried to calm her raging pulse and clamp down on the panic surging through her.

Bellos wore a pair of faded jeans and a button-down shirt. His hair was slicked back and his blue eyes looked her up and down hungrily. Like a predator sizing up his prey.

She steeled herself and walked forward, heels clicking on the hard floor. "Like what you see?"

He nodded slightly. "Why are you really here? Did one of the students hire you?" In a flash, Bellos closed the distance to her, pressing her up against the wall. He stared intently into her eyes, and she saw raw fury. But also, something else. Desire.

"Students? What do you mean?"

"You know what I mean." His face was inches from her.

Lexie shook her head. "I'm in Sales."

He stared into her eyes. The moment lengthened, and she tried to will her story to be true. True enough for him to buy it. After what seemed like an eternity. He grunted. Suddenly, he kissed her, sliding his tongue into her mouth.

She was so shocked that she didn't pull back, and a moment later she found herself kissing him back, just thankful that he seemed to believe her story. Bellos stroked her wig and pressed his body into hers. He felt tightly coiled. Tense. It felt good to be wanted. Wanted like a woman. She couldn't decide if she was scared or attracted. It was somehow both at once. Bellos moved his hands down the back of her blouse top. Lexie slid a hand down the front of his shirt, and down to his groin, lightly rasping the material with her nails. She felt the hardness there, waiting. Waiting for her.

Bellos groaned into her ear. "That's it. Touch it, touch it." He pulled her to her feet, close to him. Bellos slapped her ass and grabbed a handful of it, sliding his fingers under her panties. "I don't like surprises. You're gonna pay for it."

He put his hands on her shoulders and guided her slowly but firmly to her knees on the carpet. He unzipped his pants and Lexie found herself staring at eight inches of hard cock, standing rigidly at attention. For her. Slowly, slowly, she reached up a hand and grabbed it tentatively, prompting a sharp exhale from Bellos. The touch of his hot manhood with her bare hands sent a thrill of the forbidden through her. She stared up and watched the yearning flicker across his features, consume him like a fire in a dry forest.

Bellos cupped the side of her face with an iron grip. "Put it in your mouth," he husked out in an imposing voice.

Lexie swallowed and opened her lips, taking him inside. It wasn't much different than dildos she had sucked in the past, except that she could feel every pulse and twitch of it as she sucked.

"That's it, that's it, you dirty girl," he said, moving his dick in and out of her mouth. He held onto her shoulders and the back of her head, fucking her face. She gagged on the thickness of his cock, but Bellos kept going. Lexie shook her head no, but he wouldn't stop. He was a rampaging bull, a tornado that wouldn't let up until he was satisfied. Soft tears fell from her eyes and went unnoticed as he drove his manhood in and out of her mouth.

"That's it," he said, panting. "You're my bitch now. How does it feel, bitch?"

Lexie moaned in between gasping for air. This went on for another minute or two, and mercifully Bellos lost control. With both hands on her head, he bucked his hips and launched a jet of hot cum into her mouth. She did her best to swallow it, in survival mode. Lexie was surprised at how well she handled it, licking his dick clean in a few moments. She looked up over his deflating cock, a trail of semen dripping down her chin, at a look of pure contentment on his face.

Without another word, Bellos walked over into the bathroom, and she heard the shower kick on. Lexie, for her part, was a mess, and he tossed her a wet towel to clean up. He shut the door. She quickly made herself semi-presentable, then grabbed several items out of her purse. After listening at the door to ensure he was really in the shower, Lexie positioned the bugging devices around the room. She scrawled the number of the throwaway phone on a piece of paper and left it on his bedside. Quietly, she made her way out of the suite, taking the stairs rather than the elevator.