Stiletto Coder

Sean loved the moment of transition. The precise moment when he hit 'compile' on the program, executing the code that turned him from Sean into Sienna. Sienna.exe. It wasn't the moment that the black thirty denier Wolford stockings slid onto freshly shaven legs. Not the moment the red wig went on. It wasn't even when the green satin blouse went on, perfume still clinging to the fabric from the last time it was worn. No, it was the moment the second high heel pump slid onto a stocking clad foot. Not the first one. The second. From then, "he" was "she". No longer was he Sean Gibson, IT Specialist for an international tech company. No, Sienna Gibbons, online crossdressing icon. There were lots of little differences. Sean liked craft beer, locally made if possible. Sienna liked single malt scotch, on ice or neat. Sean liked his four-wheel drive jeep, and Sienna liked the little Porsche coupe kept meticulously preserved in the garage.

Sienna took a final look at herself in the mirror. After finishing a longer than anticipated project at work, it was time for a little fun. The blouse was tucked into an olive-green pencil skirt that ended at a scandalous interpretation of mid-thigh. A thick black belt separated the two. Glasses give a quirky yet stylish air. Dangle earrings and a black choker necklace. Makeup, thickly applied after years of trial and error. A brand-new pair of nylons, running under the skirt with garters. Black satin gloves. She turned this way and that, admiring the way the five-inch heel lifted her ass in the skirt. Time for a few pics- maybe some near the car -- Sean had purchased it with bonus money a few years back. He almost never drove it. In fact, Sienna could barely remember him even taking it out for a spin. After some glamour shots on the hood and half hanging out the driver's seat, she clicked the garage door button. t opened to the deepening gloom of twilight, thickly wooded trees, and just the faintest trace of fall chill in the air. She felt the old electric thrill of going out as Sienna, the same thing she felt every time she did it. It seemed as though she could sense every nerve ending in her body, as she clutched the car into gear and surged out into the night, foot on the gas. She liked to get a little fishtail going on the gravel, even though it chewed up the road.

Her tentative plan was to drive a few miles down the road, to the local gas station/shopping mart, buy something, and get some pictures of her out in the world. Sienna's fans loved seeing her out in the world. She could just picture the expression on the cashier's face as she walked in, looking like a cross between a high-class hooker and a forty something realtor. After posting a few pics to her website and social media, she'd finish the evening with a strong drink or three, and a nice, slow, masturbation session. Sienna loved reading the emails and comments of her fans getting off on her pictures. She got off on them getting off on her.

The Porsche hugged the turns of the winding country road well. Rains the week before had made the gravel a bit sloppier than usual, and Sienna downshifted for the approaching turn. She stuck a stilettoed foot on the brake and was startled to find that there was no response. She hammered her foot on it again as the car picked up speed. "Fuck," she hissed under her breath. Too late, she pulled the emergency brake. In her panic, the car had accelerated, and she couldn't make the hairpin turn to the next downhill leg. The Porsche fish-tailed and slid off the road, to a slight ravine to the right. It struck a tree Sienna only had time to form one thought before it all went black. This is a hell of a way to come out of the closet.

Sienna slowly rose to consciousness in dim light. She gradually took stock of her body -- felt the Wolford's sheathing her legs. Still Sienna. Her head pounded fiercely. She let out a low moan and opened her eyes. The first thing Sienna's eyes focused on were shoes. Rows and rows of shoes. Paris Hilton levels of shoes. All kinds of women's fashionable shoes -- stilettos, mules, peep toes, platforms, slingbacks, and boots. She could smell the leather from her position in the bed across the room from the enormous walk-in closet, which stirred her into interest, despite her headache. The next thing she saw was a set of three different wigs, mounted on a table next to a vintage makeup desk.

There was a slight tap on the door, and she saw a man standing there, a mug of steaming something in his hand. "She wakes," he said. He was lean and lanky, with dark hair and stubble on his face. Flannel and jeans. She recognized him. Simon Fischetti, one of her neighbors from down the mountain.

"Wha..where am I? What happened?" She asked, still in Sienna voice, if a bit hoarse.

Simon set the mug down on the bedside table, along with a container of aspirin. "I heard the sound of your crash while I was out in the woods with my dog. I found you and got you out. Figured you didn't want an ambulance called while you were... in character. I'm an EMT, so I made sure you were OK."

Sienna realized her wig was still on, as were all her clothes. She saw her high heels sitting neatly on the wood floor next to the bed. "Th -- thank you, Simon. Is my car-"

"I sent for a wrecker. It's down at Jeorgi's over on County Road 6. They're trying to see if it's salvageable. You did quite a number on it."

She frowned, adjusted some hair out of her eyes. "The brakes failed."

"Hmmm. Interesting. You would be the second set of brake failures in the area in the last few weeks. Before I forget, make sure you go get cleared by a doc for concussion protocol."

She nodded. "Do you think someone cut my brakes?"

"It's possible. There's some weird stuff in the works on this mountain. That real estate developer guy, lives across the lake from you? Darby Charles?"

She had a flash of recollection. Sean had met him briefly a few months ago. "Yes, always throwing parties."

"I've been hearing some rumors. He may be trying to strong arm people to sell their properties to him. I've already been approached once."

"No one has contacted me yet. Well, I have gotten letters with offers, but no one in person."

Simon looked out the window. She saw he was wearing a pistol on his belt. "Just be careful, ok?"

She sat up, ignoring the pounding in her head, slid her high heels on. Sienna padded over to the closet, heels clicking on the floor. She could see Simon watching her from behind in the full-length mirror. She ran her hands over one of the shoe racks. "Yours?" she asked with a little grin, turning back to him.

His lips tightened, ever so slightly. "My late wife's. Vivian. She was a shoe fanatic, as you can see. She had cancer, at the end, so she had some wigs made up."

"I'm sorry, Simon."

"It's ok. Been a few years." He walked to the door. "I'll be downstairs. Just let me know when you're ready, I'll give you a lift home." He walked out, leaving her alone. Sienna freshened up a bit in the attached bathroom, then let him drive her home.

Later on, dressed in drab as Sean, he got ready to head to the hospital for a checkup, waiting for an Uber that took forever, out in the sticks. He looked Simon up on Instagram and Facebook and his mouth dropped open in surprise. Sienna bore a striking resemblance to Vivian. That must have been weird for him when he pulled Sienna from the wreck, he thought. He pushed the thoughts aside and headed out the door.

Thankfully, the ER doc cleared Sean of any head injuries, and he got a good night's sleep. The next day, he outsourced his work to Sienna and let her work while dressed. He had to be careful because she was a lot more outgoing and flirtier in emails, to both men and women. Sienna wore a darker brown wig, cut short at her neckline, a pinkish white dress shirt that her breast forms simply bulged out of, with a belted black pencil skirt. Black stockings, five-inch black heels with an ankle strap, and a double wrap of pearls completed her ensemble.

She had just come upstairs from her basement office to get some tea when she heard the front door open. Funny, I thought I locked that. She walked out from the kitchen and was surprised to find a short, thickly muscled man standing there. He wore a suit and was putting a set of lockpicks away. "Excuse, me, what are you doing here?"

The dark-haired man stared at her, taking no pains to hide that he was ogling her. His eyes swept up and down her body, and he let out a wolf-whistle. "Well, well, well, I was not expecting this. I thought Sean Gibson lived here alone."

She stiffened. "He does. He's not home right now. I'm his assistant, Sienna." She had left her phone downstairs, but she moved towards the wall mounted home phone she still kept.

The man tsked. "I don't think so, Sienna. We've only just met, wouldn't want to have to give you a spankin' already, darlin'." He slowly closed the distance towards her.

"What do you want?" She asked, backing up towards the stairs.

"You can call me Victor. I'm in the property business. I like yours. I'd like to make your boss an offer. In fact, I've sent him several very generous offers over the last several months. Offers that he has ignored. I have another offer for him here." Victor tossed an envelope onto a side table and stepped up to her. In heels Sienna was taller than him. "But now there's a price for not responding to my emails. It's rude."

He was in her space, and she could smell cheap body wash. She swallowed heavily. "What price?"

Before she could react, Victor pushed her up against the counter. "This price," and he mashed his mouth onto hers. Sienna struggled, but she was too weak to resist him. His mouth tasted like stale cigarettes and a touch of alcohol. She could feel that he was hard because he pressed his groin to the side of her skirt tightly. Thankfully she was well-gaffed in her panties, so she didn't think he could feel her own cock. He groped her breast forms, and she prayed they were adequate enough to fool him. Victor was like an animal, his tongue urgently pressing in and out of her mouth as his hands invaded her body. "Oh baby, I'm not leaving until you make me cum," he said as he stared her down. He put one of her hands on his groin. "Stroke it," he commanded. She pulled it away, shrinking back. He slapped her on the face, the shocking action stung, and her eyes watered a bit. "This can go ok for you, or it can go, not so ok. Your choice."

Slowly, slowly, as he locked eyes with her, she put her hand on his groin. Massaging his manhood through his pants. She watched as the pleasure in getting her to submit grew on his swarthy face. "Like this?" she asked.

Victor let out a low groan, his cock pulsing even through the material. "Oh yeah, you dirty girl. Take it out now." He kissed her again, and this time she kissed him back. As she did, she unzipped his pants. Although she'd played with dildos before--her fans loved it when she did, she'd never touched another man's penis. Victor's slid out and she grasped it in a hand, slowly moving up and down the shaft. She traced circles on the tip.

He was tightly wound, vibrating with desire. No doubt he was like many of her fans, yearning to shoot his load all over her, to penetrate her, defile her, use her for their pleasure. The thought sent a quiver of excitement through her, despite the danger of the situation. Sienna stroked slowly, and then began to pick up the pace. "Huh, huh, huh, huh," Victor groaned as she jerked and caressed his manhood. He bucked his hips to the rhythm of her strokes.

"Oh, you're so big, Victor," Sienna moaned into his ear, nibbling it gently. It was enough to push him off the edge.

"No, no, no," he groaned, and then let out a loud bellow as his cock began to pulse in her hand. Sienna directed it onto her floor as streams of hot semen pulsed out onto the wood. A little got on her hands as she milked him to the end of his orgasm. His stubbly face was buried in her wig, pressing her against the wall. After a while, he looked up at her, the slightest trace of embarrassment on his features. "Damn, we didn't even get to the part where you sucked me off. I guess you're just too friggin' hot, Sienna." He put himself away and walked toward the door. Victor turned and pointed a finger at her-- "you tell that boss of yours to read the offer and get back to me. I'd love to have to come back for another session." She nodded stiffly as Victor turned and walked out, back to his black escalade.

Once she was sure he was gone, she locked the door and collapsed to the floor, and the tears came. Tears for how violated she felt. Her house--Sean's house, had always been a safe haven, and now that feeling was gone. Tears for her first experience with a man being non-consensual. That was gone forever now, too. And finally, tears for how turned on she felt about the whole thing. She sniffed Victor's cum on her hand. Took a tentative lick of it. It tasted like some exotic fruit. Sienna found that she was completely hard, even in the gaffing. She massaged herself as she smelled Victor's seed. It wasn't hard to get off, remembering his intense desire for her to pleasure him as a woman. Here was a flesh and blood man, lusting for her as a woman. As she approached her own orgasm, thoughts of Simon came into her mind. Sienna climaxed in her panties, writhing on the floor, moaning, and thinking about Simon doing to her what Victor had just done. Crying and cumming. You're a fucking mess, Sienna.

A week passed. Sean and Sienna alternated. Simon texted here and there, checking in on her. Sienna tried to make sense of what had happened, both the threat to sell the mountain place, and how she'd felt being sexually assaulted by Victor. It was still such a confusing mixture of fear, trauma, and yet excitement and freedom. She told Simon one day when he came over to fix a part of the fence line that was keeling over. She had a few tears, but in the end she felt better to have shared it with someone. Simon's face had hardened, but he'd said little. Tonight, he was coming over for dinner, and the tiniest bit of a thrill came over Sienna as she considered what to wear, what to cook for him. She decided on a simple Italian dinner--pasta, bread, salad. And wine. Prodigious amounts of wine, of course.

She got most of the food ready and prepped before slipping off to dress. Sienna loved the anticipation -- she loved the heady experience of transforming into Sienna, and most of all, she adored the reaction she got from her fans when they commented on her attire and photo shoot choices. For Simon, she chose a white pussy bow blouse top, with a black belt and a burgundy pencil skirt. Sienna wore a dirty blond wig that was on the short side, her trademark glasses, a choker collar, and tan stockings. Naturally, black pumps to top it all off.

She was stirring the sauce, into her second glass of cabernet when she heard a knock on the solid wooden door. Sienna had been carrying pepper spray with her all around the house but set it down when she saw Simon walking up. He wore a pair of jeans and a corduroy sport coat over a nice button-down shirt. He had a bottle of whiskey in one hand, and a bag in the other. "Good evening," she said as she opened the door. The sky was dark, even in the late afternoon hour. It looked like rain was also on the menu for the night.

"Good evening yourself. This is for your collection," he smiled as he handed her the bottle.

"And what's that?" Nodding towards the bag.

"That's for later."

"Ooh, I love a little mystery." Dinner passed in a blur. They always seemed to be able to talk and connect on several levels. He made her laugh, and for a blissful hour she forgot about the events of the last week. They adjourned to the back deck, which Sienna had lit with tiki torches. With whiskey tumblers and nice, post-pasta buzzes, they looked out into the deepening gloom, and across the lake. Thunder boomed in the distance.

"Open it," said Simon, nudging the bag over with his foot. Heart pulsing, Sienna ripped off the tissue paper at the top to discover a shoe box. As she took the lid off, her eyes had just taken in the name on the side. Manolo Blahnik. Sienna squealed in delight as she held up a pair of five-inch stilettos to the air. They were white with black toe tips and back heels. She quickly put them on and stood up. "They even match my outfit!"

"They were Vivian's," Simon said quietly, watching her walk around and admire herself. "She would have liked you."

"Oh, Simon, they're gorgeous. I can't thank you enough. This really-" Her phone trilled on the table. Her work phone. "I'm very sorry, let me take this really quick in case it's my client in- "Even though she could see "unknown caller" she swiped to answer.

"Hello?" She answered sweetly. Over the last few months Sean had slowly worked Sienna in as his executive assistant slash trainee.

"Where's Sean Gibson?" Said the voice. Something about the tone made her afraid, and she put it on speaker phone so Simon could hear it. He leaned in, set his drink down.

"Sean is away at the moment -- this is Sienna, I'm handling his accounts while he is away."

"Sienna, huh. He didn't take his phone?"

She swallowed. "We're using call-forwarding for his work number."

The voice was silent for a few moments. "Has he looked at our offer?"

Sienna looked at Simon, who gave a tiny shake of his head. "He is still considering it."

"Huh. What is there to consider, Miss, Gibbons, is it? Did my associate not make it clear when he visited you?"

She swallowed. "Oh, he made things clear, alright."

"And did he not inform you that we would be back?"

Simon unbuttoned his sport coat, and she could see his pistol holstered there, as he got up and looked around.

"No, Mr. Fischetti, we're not out in the bushes. But we are watching. That was a touching moment, with the shoes, really it was. Kodak moment, as we used to say in the old days."

They both froze. Looked at each other. Sienna stood up, smoothed off her skirt and picked up the phone.

"Please sit back down, Ms. Gibbons." Next to her, her whiskey glass disintegrated as a rifle round lanced through it. A piece of glass struck Simon's cheek, leaving a tiny bloody mark. He made to draw his pistol but froze at the words that came next. "Let's keep this a pleasant discussion. You remain standing, Mr. Fischetti."

Sienna slowly sat back down, looking up at Simon in fear.

"What did you do to my associate, Victor?" The voice asked.

"I uh, I um, masturbated him."

"Quite right. He reports it was lovely. And what did he want you to do?"

"He, well, he, indicated that he wanted me to, um, give him, pleasure, orally."

"Suck his cock."

"Yes, um, that is another way of saying it."

"Say it."

Sienna swallowed. "He wanted me to suck his cock."

"You may regard this conversation as a virtual version of the one from the week prior. I'm sure you do many virtual meetings, working for Mr. Gibson. So, in lieu of one of my associates being personally present, Mr. Fischetti will have to stand in."

She looked up at him, eyes wide.

Simon's features hardened. "Listen, whoever you are- I won't let you-"

"But that's just it. You don't have a choice. We have two sniper rifles trained upon your little love nest there. In addition to some choice video equipment. If you make a move to leave the deck, there will be a little "hunting accident." These woods are filled with them, don't you think, what with the deer population exploding."

Silence. Simon looked down at her. He mouthed the words "I'll block the way", but she shook her head. She couldn't put him in danger like that, even if he wanted to.

"Well, Ms. Gibbons?"

"A- alright. Alright."

"Good. Now get on your fucking knees."

Sienna looked up at Simon and mouthed "sorry" as she sank down to the deck at his feet. She had an outdoor carpet, so it wasn't too bad, but Simon grabbed a pillow from a nearby chair and tossed it down. Simon stood there, glaring across the lake.