Stiletto Equestrian

She is slim and petite. Rachel wears a ghost white dress which ends scandalously at mid-thigh, revealing much whilst somehow leaving even more to the imagination. She stands, hand on her hips in the corner of a room as the photographer takes dozens of shots in various positions. Her auburn hair hangs straight down, framing a narrow nose and a set of slightly imperfect teeth. Azure eyes glare directly into the camera, challengingly. An enormous, jeweled necklace covers her breasts, and a set of matching hoop earrings adorn her ears. Her legs are clad in tan stockings. A pair of black five-inch patent leather pumps lightly reflect the studio spotlights into the lens.

The man behind the camera whistled softly. "Looking great, Rachel. All done."

Rachel brushed a piece of nonexistent lint off her thighs. How had it come to this? Balder Cup Champion. Jockey of the Year. Celebrity Endorsements. Hundreds of men yearning to get into her skirt. It had been a wild year, and it was still just August. She thought back to the beginning.

Eleven Months Ago

Ray stood before the judge, bleary-eyed and squinting as the morning sun invaded through the windows. The old guy droned on and on, and Ray tried his best to pay attention. Or at least seem it. The party the night before was still fresh in his mind, muddling his thoughts with a nagging headache.

--"Given the complexity of your situation, as well as the gravity of the circumstances, I take this decision very seriously. Unfortunately, this act cannot stand without consequences. Beginning tomorrow, I am instituting a twenty-year ban from both competing in and participating in the horseracing industry. Ray Sims will go nowhere near a horse--not to compete, or even to work on horseracing teams. Is that clear?"

Ray nodded stiffly, his lips tight with anger. The judge banged his gavel on the table, and the Ray winced at sharp and final sounding boom. Outside the courtroom, his lawyer explained the situation in greater detail. After calling the man every foul word he could conjure up, Ray stalked off, catching an Uber to his favorite dive bar, Post Time, down by the Tracks. He figured he couldn't be in there the next day, so he might as well indulge. The place was deserted in the late morning hour, but Ray knew the owner, who set him up with a tall beer in his favorite corner booth. When the door creaked open, he stewed on his third drink. A sixty-something woman walked in, way overdressed for the place. She wore a gray and black polka-dot sheath dress, with a long black leather coat. Peep toe high heels clicked on the scarred wood floor as she noticed Ray and walked over. Slid into the booth next to him without asking for an invitation. The woman's perfume washed over, the scent calling to mind some distant, primal memory. To his great surprise, Ray's cock immediately sprang to attention, rubbing against his jeans and clamoring to be let out. This woman was old enough to be one of his mother's friends- hell, she could BE one of her friends.

"Good morning, Mr. Sims," she began, gesturing to the bartender for a cup of coffee. She wore a wedding ring, Ray noticed, along with a big silver necklace and a matching bracelet. "Tough break today. Shame a jockey of your skill will be denied such a promising career. What are you planning to do?"

Ray decided to just go with it. Although he wanted solitude, the presence of the woman was comforting, and put him at ease. "I can appeal, but my lawyers don't see much chance of overturning the ruling. Betting on your own races is frowned upon." He took a swig of beer as the woman's coffee arrived. "How do you know about it?"

She smiled at the bartender and thanked him before fixing her gaze on him once more. "Oh, I have my sources. Let's just say a benefactor of yours got in touch with me. What if I told you there was a way that you could still race professionally?" The woman slid a card across the table with a manicured hand, lingering just a moment longer than necessary to touch his finger. Ray's cock twitched. She seemed to be slowly moving towards him in the booth. He was sure that the woman was several feet away when she sat down, but now, out of some bizarre, unconscious magnetism, they both seemed to have scooted closer. He could see the stocking tops on her thighs, and they looked gorgeous. Ray tore his eyes away from her shapely legs and looked at the card.

Dr. Kelly Keener

Private Practice Psychologist

I can help you become who you want to be

kelly@shrinksinstilletos.com

"I could race again?" Ray looked over at her, her words finally catching up and sinking into his brain. "How?"

"There's a way," Kelly said. "But there's a price, and you must be willing to pay it."

"I'll do anything," Ray blurted out, turning towards her. His legs came into contact with hers, and his hardon pulsed.

"Hmmmm. Let me see something first. Do you know anything about hypnotherapy?"

"Not really, I've just seen people do funny things on stage and stuff."

"Well, not everyone is susceptible to hypnotic suggestion. Let me see where you are on the spectrum. Stare at my necklace. Don't look at anything else as I talk to you."

Ray looked down at Kelly's necklace. It appeared to be a high-quality metal and made up of intricate, interlocking hoops of various sizes. They bent and flexed in her ample cleavage, reflecting the afternoon light as she moved.

"I want you to relax." The sound of Kelly's voice was calming and soothing. "I want you to think of a place where you feel completely safe in your mind and imagine yourself there now."

Ray imagined his parent's horse barn. His father was a well to do lawyer, and he set up a small apartment inside where Ray could live and be close to the horses.

"--And now you're awake," Kelly said. Ray looked around and then down at his pants, face reddening. He realized that he had ejaculated in his pants during the hypnosis.

"That's normal for one of my sessions, don't worry about it," Kelly smiled sweetly. "The 'point' is, you are an excellent candidate for my methods."

The word choice made him even more embarrassed. "How is getting hypnotized going to get me racing professionally again?" Ray asked, adjusting his now flaccid penis in cum-soaked jeans. He put a napkin over them for some semblance of modesty.

"It will. Promise," Kelly said. She got up from the table and left a five-dollar bill for the coffee. Kelly put a manicured hand on his, stroking the top of his hand softly. "Call me, Rachel."

He looked at her funny. "My name is Ray."

"Right," Kelly nodded. "Call me if you want to ride again."

She walked off from the table, leaving Ray to stare at her shapely ass, heels clicking, out the door. He felt himself beginning to get hard again.

That night, Ray did his best to research Kelly, figure out what her background was. Her website said that she was a psychologist to many high-profile celebrities, CEOs, and politicians. Powerful people. He couldn't find out much about the company she worked for, though.

Ray had always been the ladies' man--he'd cultivated a bad boy image during the three years he competed on the pro circuit. Even the amateur league before that had its share of female spectators more than willing to go home with a hot young jockey. Ray had an entire spare closet filled with items that various women had left at his place over the years. After seeing the pictures of Dr. Keener on the internet and being reminded of the earlier meeting with her, he felt inexplicably drawn to it. Ray began to root through the contents, his pulse racing with a strange excitement. He found several pairs of high heels, a few sundresses, even pantyhose. As he did, one part of him watched the situation with a bit of detached curiosity.

Moving purposefully now, he found his last year's Halloween costume--a rock star, pulled out the long wig that came with it. Ray brought it all into the bathroom and dropped it on the floor. He looked at himself in the mirror as he stripped his clothes off. Ray was a small man, like most jockeys, with little body fat. He kept his chest already shaven, along with his manhood. His cock was at full attention as he pulled open the drawer beneath his sink. There, more female products abandoned by his various guests lay. Ray had no idea what he was doing, but he pulled up a few videos online, and just like that, he was in business.

He painted on a few lines of eyeliner and added a more touches here and there before pursing his lips and looking at himself in the mirror. Ray's cock was at full attention, and he stroked it idly as he turned to the clothing. He slid on the tan pantyhose first, careful not to create a run with a hangnail, as the video recommended. Tucked his rock-hard cock in best as he could. Next, a black patterned sundress and a thick black belt. Ray clasped on a necklace and a bracelet before adding the rock star wig. In the back of his mind, he wondered why he was doing what he was doing, but that was far away. What mattered was exploring this new idea in front of him.

Finally, he stared down at his choices of shoes. There was a pair of platform sandals, some strappy peep toes, and finally classic black high heel pumps. He remembered very clearly the woman they belonged to- Veronica Miller, a high-powered lawyer from the city. Damn, she was a tall woman. Ray thought back to the night she stayed- her astride him on the bed, him fucking her from behind on his balcony, and finally Veronica on her knees, taking him in her mouth. His seed erupting all over her face. Ray slid his feet into the pumps. Surprisingly, they fit fairly well. Tiny footed jockey, he thought with a smile as he tried walking in the five-inch heels. They boomed as they hit the tiled floor, then went silent when he walked into the carpeted bedroom. He kept walking, until he got out in the living room. All of Ray's senses were afire. His heart pounded in his chest. He saw the world with new eyes. Almost without thinking, his mannerisms became more feminine, little gestures with his hands and the way he walked. He set up his phone and put the timer on, made a few poses. Ray took a set of photos this way and stopped to take a look. He was shocked to see what he found. He looked passable as a woman!

Rachel, he thought to himself as he flipped through the pictures. He was Rachel! He sat on the sofa and pulled up some porn on his laptop. Rachel was transfixed by the sight of the woman in the scene giving a blowjob to the man. She wore business attire, while the man was completely naked. Rachel watched the woman, hypnotized by the loving attention that she showed the hard cock. She felt the inexplicable urge to try it herself, to have something in her mouth. Walking swiftly to the kitchen, she pulled a carrot from the fridge and quickly skinned it, hands almost shaking. Rachel brought it back to the living room and hit play again. As she watched the scene, she put the carrot in front of her face and imagined it was a cock. Slowly, tentatively, she put it in her mouth and began to suck, while stroking herself through the skirt and gauzy pantyhose. Ray sat on the couch and arched back, heels pressing in the carpet as he stared mesmerized by the sight of the woman on the screen getting face-fucked by a well-built man. It didn't take long before she felt the orgasm building. Rachel grabbed her shaft through the pantyhose and came with a level of force and intensity she had never felt before. Waves of bliss crashed over as she writhed and caressed himself, the carrot held deep in her mouth. Finally, she slumped to the couch and lay there, utterly spent.

Now the questions and the guilt began to come in earnest. What the hell happened? What had possessed Ray to do such a wild and out of character thing? Dr. Keener. It had to be her, and whatever voodoo magic she had worked during the session.

Rachel showered and washed the clothing, sliding into bed naked. Back to Ray. He slept long and deep, head was filled with images he only vaguely recollected when he awoke.

The next day, he called Dr. Keener's office and made an appointment with her assistant to meet up. He strode into the office before anyone could stop him, bursting in just as Kelly finished a phone call. She looked at him with an inquisitive expression as he took the phone and ended the call. Dr. Keener wore a black blouse and skirt combo, with black pantyhose and heels. She gazed at the pictures on Ray's phone, sliding the screen left and right. Slowly, she nodded.

"The treatment is proceeding faster than I expected. You seem to be very susceptible to hypnotic suggestion."

"Treatment? Suggestion? I was dressed as a fucking woman!" Ray blurted.

"Mr. Sims, let me ask you something. Do you think you can ever compete in professional racing, say, as a man in a disguise?" Kelly put her feet up on the desk, giving him a great view of her legs as she leaned back in the chair.

Ray frowned. "No. Too many people know me. They would see right through the disguise."

"Well, what if she were to enter the pro racing circuit?" Kelly gestured at the phone with a manicured hand. "Could "Rachel" pass without being discovered as your secret identity?"

Ray looked at the picture again. He didn't even believe it was him, much less someone else. "She probably could," he allowed.

"And you did tell me that, more than anything, you want to compete again, did you not?"

"But... As a woman?"

"Let me ask you something? How did it feel?"

Ray swallowed. "It felt...exciting. New. Sexy."

Dr. Keener leaned forward. "Did you masturbate?"

Ray slowly nodded. "It was amazing. Hot."

"You haven't seen anything yet, sweetie," she replied. "If you do decide to go this route, that was just the tip of the iceberg.

"Can we, um, do another session? Just to see?" he asked, a bit sheepishly.

"Of course, Rachel- I mean Ray," Kelly said with that Cheshire cat smile. "Please, sit on the sofa there and get comfortable."

"-And now you're coming out of it, coming back. Just sit there and relax until you get your bearings." Kelly got up with a cup of coffee and walked off.

Again, Ray felt the wetness in his pants that signaled that he'd cum. This time, however, he had wadded a washcloth in his groin, so it wasn't quite so bad. He leaned back and watched the back of Dr. Keener's shapely legs and ass as she refilled her cup and poured him one. "Do you have any cigarettes?" he called out jokingly.

She smiled at him from across the room. "I think we made some progress today."

"So, how does this thing work?" Ray asked as she handed him the cup.

"The successive sessions build on one another, creating the space in your mind for another persona to emerge- one you can shift into on command to assume the female--or male in the case of my woman clients."

"So, I'll be able to create a new identity as Rachel, and actually go out in the world?" Ray sipped the coffee. Already he was excited at the prospect.

"Yes, and what helps you is that you're quite good-looking as a woman. Not every man has the looks or the body type to successfully pass, but you are a rare case."

"OK.... When can I see you again? I want to get this thing done soon so I can start riding again."

Kelly crossed her legs. "It's best not to rush these things. We can plan for another session in a week or so, after letting this one sink in a bit."

"Are there any goals that I should be shooting toward?" Ray asked.

"Just let things, arise, on their own," Kelly said cryptically.

Ray left the session and hurried home. There were a bundle of packages waiting for him on the front steps of his apartment. He brought them inside one by one and took a long shower, washing and shaving his entire body. He finished with some scented lotion from the girlfriend drawer and then poured a whiskey on the rocks.

Then he turned his attention to the boxes. Ray had dropped some serious cash, and he hoped that the investment would be worth it. He laid out four woman's outfits, stockings, tights, pantyhose, and several new pairs of high heels and wigs. Already his cock was quivering in anticipation. Before he started, he watched several more videos on female impersonation online--how to walk, mannerisms, and finally voice and speech.

He tried on the first outfit and walked around the apartment. Ray practiced a feminine voice and mannerisms in the various mirrors around his place. The afternoon went on, and the whiskeys multiplied.

"Rachel, I'm Rachel now," she murmured into the mirror. She had been working on her cover story for a little bit now.

Her phone chirped, and when she checked it she saw it was from Dr. Keener.

It just read: Ready for a challenge?

Rachel typed back: Bring it on.

The response was almost instantaneous: Goldenrod Hotel bar, downtown 6pm. Tall, dark, and handsome. Blue shirt. He will assess the state of your transformation.

Rachel's heart began to beat overtime at the thought of interacting with a man.

Walking through the hotel lobby as Rachel was terrifying. At every step, she was afraid to be outed as a fraud. She wore a black jacket over a light blouse top, a dark skirt, and black tights. Black pumps, and a coach purse completed her look. She had to admit, the admiring glances she was receiving were exciting.

Steve was waiting in the bar- tall, dark, and handsome, as described. He was another psychologist and described himself as "an old friend of Kelly's, from the beginning." Whatever that meant. They had a drink together before Steve suggested a drive.

Without really being conscious of it, Rachel had fallen into her feminine persona, finding herself answering Steve's questions, and even flirting with him. Rachel found that she liked the way he took the lead in several instances, holding the door for her and acting the perfect gentleman.

They talked as he drove, and Steve's hand found its way to her knee. The touch of his hand sent a thrill of excitement through every corner of her body. Steve traced little concentric circles on the gauzy material on her knee. Rachel realized they were heading towards the racetrack.

After another few minutes of driving, Steve pulled his truck into a dirt patch overlooking the practice track. Dusk was falling, and many of the jockeys were riding their prize steeds back to the stable. Rachel felt the magnetic intensity of Steve's stare as he looked over. She felt drawn to him in a way she'd never felt before. Ray had never been pursued; he'd always done the pursuing. "Rachel, you are a gorgeous woman. Did you see the way all the men looked at you at the bar?"

She nodded her head yes slowly as he took his hand off her knee. Rachel found that she wanted it back. That she missed the touch when it was gone.

"I want to try something Rachel, I want to check how far the sessions have progressed." Steve's glance stirred something deep inside her, seemed to unlock some frozen part.

Rachel slowed nodded. "Okay."

"I want you," he began, with a gaze that seemed to cut into the heart of her, "to suck my cock, Rachel."

She felt her stomach lurch. Heart pounded triple time at the thought. Could she? Rachel glanced at his groin. In the twilight, she could see the hardness of his manhood, straining at the stitching of his jeans to get out. To get at her. He was hard for her! Sucking a carrot was one thing, but a man's cock was another thing entirely. And Steve was so commanding. The commanding tone demanded to be obeyed. Demanded her to submit.

Steve spread his legs slightly in the driver's seat and leaned back. "But only if you want."

For a brief moment, Rachel thought refusing, running away. She realized she didn't want to run away. She was actually curious. And there was something about Steve's desire, something magnetic, something so attractive to her. Timidly, she reached over to his lap. Rachel set the palm of her hand down on his pants, feeling the tightly bound heat under the denim material. She watched Steve's face, saw the ecstasy and desire reflected. Rachel slowly slid her hand up and down, caressing his hardness, pulse racing.