Stiletto Equestrian

"Come on, baby, take it out," Steve whispered. Begged. Begged for release.

Rachel slowly dragged the zipper of his jeans down. Took a deep breath. Reached a hand into his pants. It didn't take much, and his cock flopped out.

Steve groaned at her soft touch. He bucked his hips slightly, and Rachel instinctively made an "O" with her fingers. His cock slid up and down inside it. With effort, Steve seemed to master himself. "OK, Rachel, put it in your mouth."

At the sound of such an ardently expressed wish, she found herself yearning to please him. She leaned over and kept her eyes on Steve's as her face came level with his manhood, fixing a stray wisp of wig hair that blocked her view. Rachel was submitting, and yet firmly in control. She was the architect of his pleasure--in charge of the pace and timing of his satisfaction. Rachel took him in her mouth and watched him lean back, close his eyes in total pleasure. Steve groaned as she pulled his cock deep into her mouth and began to suck.

He put a hand on the back of her wig as he met her downward motion with hip thrusts into her mouth.

Fucking her mouth. A man was fucking her mouth.

"That's it, Rachel, you gorgeous woman. You're so hot. Suck my cock."

She turned her full attention to the task at hand, warming to it. Steve's dick was hard and hot, and Rachel found that she wanted to do a good job of sucking him off. If she was going to do it, she might as well be world class. She tried to do what woman had down to Ray hundreds of times in the past, and it seemed to work, from the ragged state of Steve's breathing. Rachel herself was hard as well, and her cock rubbed against satin panties in a gorgeous friction.

Steve leaned over as she sucked, caressed her ass and legs. He ran his hand over her tights, under her skirt. Rachel felt a little uncomfortable about, but she kept going, her head moving in a rhythm while one of her hands stroked and jerked him. Steve's fingers found her asshole and began to massage it gently. Strange at first, but after a minute or two it felt ok. Then he inserted a finger into her ass. Then two. It was a sort of pressure she'd never felt before, but after she got over the initial discomfort, it actually began to feel good. Rachel had heard of prostrate stimulation- in fact, one of Ray's former lovers had tried it until he'd stopped her. Now, she found herself bending to Steve's will as he fingered her asshole. In and out. Rachel bucked her hips back, into his probing digits.

Rachel was approaching an orgasm as her tongue caressed his manhood, and she fondled herself with one hand. She could sense Steve getting close. She looked up at him, lost in the throes of pleasure. Pleasure that she was giving him. Steve thoroughly was convinced that she was a woman- or at least enough to go with the masquerade long enough to get his rocks off.

"You like sucking my dick, Rachel?" He panted

With a mischievous grin, she simply nodded in response.

"Oh god, you're so fucking hot. I'm gonna cum," he murmured as he pushed her head deeper. She felt him spasm, then a warm spurt of cum invaded her warm mouth. Rachel had never tasted it before. Not unpleasant. At the same time, Rachel felt her own orgasm grow-- the combination of sucking Steve, touching herself, and his fingers stimulating her prostrate gave her an earth-shattering climax of the kind she'd never experienced before in her life. Rachel moaned with complete pleasure as she swallowed his seed, squirming her ass to get his fingers even deeper. After what seemed like an eternity, the orgasm subsided, and she slowed her sucking. Steve slid his fingers out and squeezed her pert ass as his manhood began to deflate. Rachel sat up, and adjusted herself into a semi-presentable position, feeling completely awkward. Her panties were thoroughly soaked in her own semen. She cleaned up a little cum remaining on her cheek with a finger. Licked it. Steve zipped himself and sat back in the seat, sighing contentedly as he looked at her with a grin.

"That was amazing, Rachel," Steve said at last. "That might have been the best orgasm I've even had in my life."

Rachel nodded. "I've never felt anything remotely that powerful." She watched the jockeys, heading back to the stables in the darkening twilight. "Am I really that passable?"

Steve laughed. "Rachel, I'm getting hard again just thinking about you. You're completely passable. How do you feel, mentally?"

"It feels.... Interesting. This is so new for me, I don't know what to expect. I've spent the last five years seducing women, so it's a bit strange to be on the other end of that. But I thoroughly enjoyed it, without a doubt."

Steve started the truck and backed out. "Well, I think Rachel is going to do just fine."

Present Day

Rachel left the photo shoot, checking her phone as she walked out of the building onto the crowded downtown street. As she walked, a bearded man in a finely tailored suit detached from the bus stop and melded his path to hers. Rachel was used to dealing with horse-racing fans accosting her for autographs and pictures.

"Ms. Sims. Good afternoon. I apologize for the interruption, but it's urgent that I speak to you about a private matter." The man looked to be in his early fifties, and his eyes sparkled as he held out a business card to her. It read:

Henry Winston

Elegant Solutions, LTD

"What is it, Mr. Winston?" Rachel asked, looking closer at the man. Well-built. Lean.

"Please, call me Harry. I would prefer to discuss it in a more private setting, my dear Ms. Sims, or is it Mr. Sims? I think it would be better for all parties." He cocked his head to the side and looked at her directly. "Wouldn't you agree?"

Rachel swallowed hard. Fuck. She'd been worried about this since a few months after sucking Steve off, when she began her now legendary winning streak on the horse racing circuit. Someone was bound to find out. "When?" she husked out.

"I would be delighted if you could join me in my suite at the Plaza hotel downtown tonight, say around 8pm?"

Rachel nodded stiffly. "OK."

"The Emperor Level. Until then." And Harry seemed to melt and vanish as the crowd closed around him.

Emperor Level? Rachel walked off towards her SUV. Amidst the fear of the unknown she felt something else. Was that excitement?

Rachel had to stop at the front desk to get a key card for the elevator. She rode it up alone. The card gave special access to the level normally off limits to most of the hotel guests. The walls of the elevator were mirrored, so she checked herself out. Rachel's black dress fell off her body in a flattering manner, and the giant necklace plunged right into her cleavage line. The five-inch black high heel pumps elevated her calves and made her legs irresistible for ninety-nine out of one hundred men. And the last one probably wasn't worth it anyway. Her dark wig cascaded down her back and framed her cute nose and chin.

After what seemed like an eternity, the car whirred to a halt. On the Emperor Level, the doors opened right into the suite, apparently. Rachel walked out cautiously, stilettos echoing on the hard wood as she did. Cavernous main room, gaudily decorated, with paintings, furniture, and refreshments everywhere she could see. A bottle of champagne chilling in a nearby ice bucket, and a note to pour herself a drink. Rachel took a seat near a gas fireplace, crossed her legs and took a sip of the champagne. Not bad--she'd had the vintage before after winning a major derby that year.

After a few minutes, Henry walked out, dressed in a tuxedo. "Good evening Miss Sims. Thank you for taking the time to meet with me, under these unusual circumstances."

Rachel glared at him haughtily. "It's not like I had much choice, Mr. Winston. What's the meaning of this?"

"The meaning, Ms. Sims, is that your nation needs you. You were turned into a quite passable woman by Dr. Kelly Keener, correct?"

Rachel slowly nodded her head yes. "Well, I like to think so. And several thousand masturbating fans of horse racing, who send me pictures of their dicks every month." She left out just how hot it made her feel, how much she adored the intensity of desire her fans had for her.

Henry poured himself a flute of champagne and walked over to the window, looking out at the deepening dusk of the city. "There's a need for humans with a rather "flexible" gender identity to help protect this world. To punish the unjust and the corrupt." He turned to face her, looking her over from stiletto tip to wig top. "I am offering you a job. It will entail getting to know some rather rich and powerful men and women. Some here at home, and some abroad."

Rachel took a sip of her drink. "And if I refuse?"

"If you say yes, you'll be compensated well for your work, and you'll still be able to compete in horse races."

"Again, if I refuse?"

"Let's not go down that road, shall we, Ms. Sims?"

Rachel looked at Henry. He was an older man. Full head of thick gray hair. He actually smelled good to her, some sort of faintly sage aftershave. And he looked good in that tuxedo. Henry's eyes sparkled. "I've got dinner reservations in the steakhouse on the second floor of the hotel- it would be an honor if you could join me?"

Rachel paused to consider. She still hadn't said yes to his proposal, and she didn't know if she wanted to. "I can do dinner," she admitted. Henry offered his arm, and they walked over to the elevator.

Three hours later they were back in the elevator, heading back to Henry's suite. Rachel's heart was beating triple time with excitement. Dinner had been amazing. Henry was funny, handsome, and knew how to make her feel attractive and desired. At one point he touched her stockinged leg gently to make a point, and she felt her heart quicken. He must have felt the chemistry as well, because he invited her for dessert and a nightcap.

The pair eyed each other hungrily in the elevator car, and Rachel struck first. She leaned close and kissed him lightly on the mouth. "Dinner was amazing. I can't wait to see what's for dessert."

Henry paused for a moment, blinking away the surprise, and then he grabbed her around the waist. She loved the feeling of his strong arms around her. "You're going to like dessert, Rachel, I promise." He kissed her deeply, and she moaned as their tongues entwined and fought one another for dominance. His erection pushed into her own, and she gyrated slightly so they rubbed even harder. The doors opened and they poured into the suite, articles of clothing flying off with the speed and urgency of new lovers. Soon Rachel was standing before Henry, clad only in silk panties, a bra, and her black pumps. Henry was completely naked. His manhood completely shorn of hair, standing at rigid attention in the soft light. A gas fire burned in the fireplace and served as the only lighting.

"Get on your knees, Rachel." Henry said with such complete confidence that Rachel had no choice but to comply. And it felt so good. It felt right. As her knees sank to the plush carpet in front of the fireplace she felt the thrill of excitement that only submitting to a dominant man can bring. Henry stroked himself, staring at her with a predatory intensity. "Have you pleasured a man before, Rachel?"

She smiled coyly, hypnotized by the length of his manhood. "Just once."

"But have you been fucked by a man?"

She shook her head lightly as she reached for him. Rachel grasped and gave a few strokes, watching him closely. He leaned in and grabbed a fistful of her wig, pulling her closer, so his cock was laying flush with her mouth. His trembling desire came through his iron grip on her head. "I have to have you, Rachel." She opened her mouth, and with her tongue licked up and down the sides of his manhood. Henry slapped it on her lips and shoved it into her mouth, unable to restrain himself. He grabbed the other side of her head and moved his cock in and out of her mouth as she drank in his lustful expression. Henry's breathing grew ragged, and she began to fondle herself. Lost in the art of pleasuring this man, stroking and sucking him, watching how she brought him closer and closer to orgasm.

Finally, Henry pulled her to her feet. She tottered on her heels for a moment, but then regained her balance with his help. He led her to the bedroom door and wrapped his arms around her, kissing her deeply. Without another word Henry spun her around and slid her panties off. He nestled his cock in the cleft of her ass cheeks. Rachel pushed back against the hot steel she felt there, gyrating on his shaft. Slowly, slowly, Henry inserted eight inches of rock-hard manhood into her ass. The pain was extraordinary, and she bit her lip and moaned. With one callused hand Henry grabbed her jaw and pulled her face back until he was looking into her eyes from behind her.

"You're mine now," he said as he thrust into her. "Say it."

"I'm yours," she replied, losing herself in the pleasure of his thrusts. It went on and on, until a fiery pleasure grew to unbearable proportions.

With a groan, Henry climaxed, spurting hotness inside of her. She came seconds after, in a wave of bliss that seemed to last for ages.

With a murmur of disappointment, he slipped out of her. "That was quite the performance, Ms. Sams. I expect great things from you."

She laughed. "It's not like I have a choice. Will I see you again?"

"Soon."