Stiletto Assassin

Eric vaulted over the hood of the parked car, chased by gunfire. He leaned back against the car tire and pulled his hand off his side. It was slick with blood. The meeting was supposed to be a piece of cake- he made the handoff for the cash and was on his way out of the mall. He didn't count on getting double-crossed by his backup team. They'd ambushed him on the way out and Eric had taken a round in the arm. He turned and peeked up, lobbing a few rounds their way to slow them down a bit, then crawled down the line of cars. Around the corner of the building, he found a woman putting shopping bags in the trunk of her car. As she moved to get in the front seat car, he moved up on her. Her eyes flashed with surprise until she saw his gun, then went to fear.

"Please don't hurt me," she said. She was older, maybe late-fifties, but slim and well-put together. She had blonde hair and wore a skirt and heels, revealing toned legs.

"Eric grabbed her purse and quickly frisked her. "Get in," he ordered, and pushed her into the driver's seat. He noticed she had a wig on when he touched her head while pushing her into the car. Eric got a nice view of her ass he would have enjoyed more if he wasn't bleeding so badly. He got in the back seat and told her to turn the car on. Evelyn drove nervously out of the parking lot, and slowly took a few turns on the streets at his direction to ensure no one was following.

"Who are you?" He asked with a grimace, touching his side. The woman looked up, her blue eyes flashing in the rear-view mirror when she glanced at him. Eric watched her for a few long moments, the realization dawning on him.

"Are you a man?" He asked, the shock momentarily taking the place of the pain from his wound.

"Are you?" The man, or woman in the front seat answered haughtily.

"Me? I'm just trying to get through the days," Eric replied. "Give me your phone." She handed him the phone. Eric grunted as he reached forward to grab it from her.

"Are you hurt?" She asked.

"I'm fine. Go back to your place. I need to lay low for a few hours. If you do as I say, you won't be hurt." He was fading fast, knuckles white on the pistol as he concentrated on staying awake. Her home was on a nice, tree-lined drive on a slight rise, with long distances between houses. Money buys space and privacy. Evelyn punched the garage door opener. As she put the car in park and clicked the garage door shut, he felt a great weariness settle on his shoulders. His vision shrank to just immediately in front of him and he heard rather than saw the cross-dresser get out and come to the back seat door.

"I just need to rest a minute," Eric said, before closing his eyes.

When he woke, Eric noticed several things. One, he was in a bed. Two, he his clothes had been removed and his wound dressed. He was naked under the very high thread count sheets on the queen bed. Three, his gun sat on the nightstand. He sat up, wincing at the soreness in his side. Eric heard approaching footsteps, and the door opened.

It was the woman, or rather the crossdresser. New outfit, new wig. His mysterious host wore a dark blonde shoulder length wig, over a green sheath dress, flower prints down the side. Pantyhose and matching emerald high heel pumps completed the ensemble, along with some dangly earrings. Honestly, Eric's host wasn't a bad looking woman, even if it was just a masquerade.

"What, what's your name?" Eric croaked, as she set a tray bearing soup down on a nearby table.

"Evelyn," she answered. "My real name is Edwin, and as you correctly noticed, I am a biological man. But when I dress, I am Evelyn." She walked over and opened the curtains a bit more, revealing a large lake in the background.

"When you dress," Eric repeated, taking in her outfit. Her perfume, whatever it was, smelled lovely. Edwin, Evelyn, whomever he or she was, had a great ass and legs. Eric shook his head. He wasn't used to such thoughts about men. Still, it caused a bit of a flutter of something in his stomach. He didn't know what it was. Excitement, the unknown, the forbidden?

"Yes. My wife passed three years ago, and Evelyn started to come out more and more. Sometimes I take short day trips, like the one I was on when we, ah, encountered one another." Evelyn sat down on the bed next to him, leaning over and checking the bandage for any blood. She was heavily made up, with thick lipstick and eyeliner. Her thin, manicured fingers expertly swept over his wound. Her perfume was intoxicating. Eric found himself getting hard, under the sheets, through no conscious will of his own.

"Oh. What's this?" Evelyn said with surprised smile. Her hands had moved off his side, but when they encountered the hardness in his groin they paused. She made no move to take her hand off, but neither did she encourage his reaction. The two of them sat there, staring at each other. Eric's cock pulsed under the sheets. Evelyn moved her hands slowly, a light stroking, but she didn't remove them. "Is there an injury down here that I didn't notice?" She asked, staring at him. "Is there something down there that I should examine?"

Eric swallowed heavily but said nothing. Evelyn waited. Finally, he nodded. Her manicured hands crept under the sheets, slowly coming into contact with his cock. Eric made a little noise as her hand encircled it. She watched him intently, and then looked down at his cock. "Very nice," Evelyn remarked softly, as her hands moved up and down. Eric shut his eyes and leaned back, moving his hips to fuck her hand as she stroked him. One of Evelyn's hands circled his balls, caressing their shaven surface as the other hand traced circles on the head of his dick. It felt amazing. As the tempo of her stroking increased, he noticed her begin to migrate down to his ass with one hand. He was approaching climax when he felt her begin to massage his asshole. She fingered it, gently at first, but then deeper. Eric had never felt anything like that, so at first he nearly cried out and pulled her off him. But he wanted to come, so he gritted his teeth as she simultaneously jerked him and slid a finger into his ass. The pressure was uncomfortable at first, but something began to feel pleasurable as his orgasm built.

"Oh god, yes, yes, yes!" He cried as he came.

"There it is!" Evelyn exclaimed in delight, as hot jets of cum fountained into the air, coating her fingers with hot stickiness. To Eric, the orgasm seemed to go on forever. He'd never come so hard, so powerfully. Something about her fingering seemed to heighten the experience immensely. As his pleasure subsided, Eric sank down further into the sheets, looking up at Evelyn with a vague sort of guilt. She smiled broadly and broad her cum-coated hand up to her mouth, inhaling deeply, then licking just a dab.

She grabbed a towel from the nearby table and helped clean him up. Evelyn set the tray with the foot on his lap. "Get some rest sweetie," she said with a grin. "I'll check up on you in a few hours."

Over the next few days, Eric spent time on the internet researching the attack, and his former organization, with the use of Evelyn's computer. He no longer thought of her as Edwin, since from the moment she got out of bed she was Evelyn. And there was something that he couldn't understand that attracted him hypnotically to her. Many of the sexual encounters were similar to the first one, with him awkwardly showing her he was hard, and her either giving him a hand job or a blowjob, until he came in an eruption of pure bliss. Evelyn fingered his ass every time, and he grew to like it. Sometime she used a little butt plug device to heighten the pleasure.

His research unearthed some disturbing news. Apparently, he'd been identified as an international assassin, his name and face plastered all over open source media and law enforcement entities from the local mall cops all the way up to Interpol.

Eric told Evelyn about it one day, as his cock slowly deflated under her loving grasp.

"You know what you could do," Evelyn said, a mischievous twinkle in her eye as she cleaning his cock off with a hand towel.

"What?" He asked. The plug was still in his ass, and he felt like if he shifted around a bit, he could get hard again.

"You could masquerade as a woman. They'd never see you coming."

"What! No way. I could never pull it off."

"Are you sure? I can see you'd be a good-looking Gurl. Why don't we try, just once? No one has to see."

"Let me think about it."

Evelyn smiled and walked out of the room. She left the plug inside him. After she left, Eric thought about the idea. It made sense, in a twisted sort of way. He could even get close to the men who'd betrayed him without their knowing. He could get through their layers of security by posing as some woman they wanted to fuck. Assuming that he looked that good. Eric played with the butt plug and he felt himself get hard again. He thought about Evelyn's mouth on his cock as he stroked himself and ground his ass against the buttplug. It didn't take long until he came again, moaning with the pleasure. He felt a little guilty about messing with his ass, but it felt so good.

The next day, he told Evelyn that he wanted to try it, and they got to work. Three hours of shaving, exfoliating, manscaping, and outfit selection later, he was ready, or rather, she was ready.

"Come on out, Erica," Evelyn said, as she stood in the living room of her house, sipping a glass of white wine. She was dressed in a simple crimson cocktail dress and black heels, over tan pantyhose. Erica came out, slowly, tentatively.

"What do you think?" Erica said in the high-pitched, breathier voice they'd worked on during the preparatory session. She wore a black sheath dress that came to mid-thigh. Black pantyhose covered a set of legs that seems to go on forever. Erica had a brown wig that cascaded down onto her chest, and big hoop earrings in her ears. Finally, she wore a pair of five-inch, patent leather pumps.

"You look divine! But how do you feel?"

Erica walked up in front of her, looking in the mirror off of Evelyn's shoulder. "I feel," she began, stroking the front of her dress at her groin, "like I could have an orgasm at any minute. I feel like everything is heightened- all my senses and sensations. I have to cum, I need to cum," Erica said, as she took Evelyn's hand and pressed it onto her cock, which was gaffed behind black silk panties.

Evelyn smiled as she caressed Erica's cock through the material of the dress. "And you haven't even felt the desire of a man yet, sweetie. That's a drug that gets you high as a kite.

The next day

"I have a surprise for you, my dear," Evelyn said, standing up. "You have a date with my neighbor, a nice, eligible bachelor, a lawyer named Peter."

"What!" Exclaimed Erica. "I'm not ready for that yet!"

"Oh hush, you'll be fine," said Evelyn. "It's just a dinner. He'll pick you up at six."

Despite her nervousness and misgivings, Erica had to admit the date had gone well. Peter was a thirty-something man, slim and well-groomed, and their conversation had flowed as easily as the wine. Evelyn had been right--being the subject of a man's focused attention was indeed a heady drug. Peter steered his BMV up Evelyn's drive in the early evening darkness and put it in park.

Erica felt the next words on her lips, and her heart tripped with the excitement of the moment. "Would you like to come in?"

Peter eyed her sideways, across the shadows of his car interior. "Why, yes, actually, I would." They got out and walked across the driveway, and into the interior of Evelyn's house. There were a few lights on, but she must have retired for the evening. Erica made them a few drinks and they settled out on the screened in porch at the rear of the house. It overlooked a gorgeous view of the lake. The moon was coming up, and was reflected in the placid surface. The crickets chirped in their mysterious patterns.

Erica crossed her legs, conscious of Peter's proximity on the sofa. They both sipped their drinks in companionable silence.

"I've had a great time tonight, Erica," Peter said. "You are a beautiful and charming companion. I hope I get to see you again."

Erica blushed slightly. Without replying, she leaned over and kissed Peter gently on the mouth. It tasted of warm whiskey, like her own. Their tongues caressed, tentatively, then with a little more intensity. It felt strangely comforting to be in the arms of a man. They kissed for a long while, each growing more excited by the moment. Erica slid her hand to his groin. Erica could feel his erection through his pants. Heart pounding in her chest, she softly stroked Peter. She couldn't believe the effect that she was having on him. He groaned in her ear as her fingers traced the outlines of his cock. Could she do it? Why not, she thought, unzipping his fly as Peter's hands roamed over her body. Erica gently moved his hands away from her panties each time he tried to go there, but he squeezed her ass in a way that kind of turned her on.

"It's ok," he murmured. "I know."

"Know what?" Erica sat back, staring at him.

"Evelyn confided in me. I don't care what anatomy you have. I'm interested in you, Erica." He caressed her knee through the gauzy pantyhose gently as he stared at her. Swallowing, she reached over and grasped his cock, bringing it out into the shadowed room.

Peter leaned back, eyes closed in ecstasy, as Erica gently stroked him. It felt strange, touching another cock than her own, but not unpleasant. She slowly caressed his manhood, watching pleasure steal over his features in the moonlight.

"Oh God, Erica, that feels so good," Peter husked out in low tones. His body tensed. "Ahhh, ahhh, ahhhhh," he moaned as he came. Erica felt a surge of triumph when he climaxed, as if she'd passed some sort of test. They kissed for a few moments.

"Can I take care of you?" Peter asked, looking at her suggestively.

"No, no, that's ok." She smiled at him.

Peter cleaned up, a bit bashfully, and said goodbye, giving her a gentlemanly peck on the cheek as he left.

Erica put their glasses in the sink and walked upstairs. She found Evelyn sitting in the loft, reading. She wore a dark blue cocktail dress and black heels.

"Well? How did it go?" Evelyn asked, tapping the sofa next to her for Erica to sit. She did so, full of excitement.

"We kissed a lot, and I jerked him off!" She exclaimed triumphantly. "It wasn't at all as weird as I thought it would be. I'm so fucking horny right now I can't stand it.

"Well done, Erica. I think I know something that can help out with your problem. Come on." Evelyn led Erica by the hand to her bedroom. She turned and the two embraced. Erica was ready to go. "Now that you've experienced the affections of a man, I want you to try sucking cock, my dear," Evelyn said, as they kissed. She gently pulled Erica onto the bed, where the two collapsing into a writhing tangle of limbs. Stockinged legs pressed against one another as arms roamed, exploring. Evelyn hiked her dress up and pulled her cock out of the gaffing. Erica looked down when she saw it and felt a quiver of anticipation. It wasn't as big as Peter's, but she was curious. As Evelyn massaged Erica's cock through her skirt, she touched Evelyn's hardness tentatively. The older woman pushed Erica's head slowly down towards her mid-section, and she didn't resist.

"A cock. A cock to suck. My cock to suck," Erica said slowly, entranced by the sight of it. She caressed it and looked up at Evelyn, who nodded her head at her. Erica tongued the head tentatively. It tasted warm and hard, but not unpleasant. She put it in her mouth, and Evelyn immediately closed her eyes and moaned, putting a manicured hand on Erica's head, thrusting her cock deeper.

"That's it, that's it," Evelyn moaned, as Erica got into a sort of rhythm. After a few minutes, Evelyn pulled her off, and they changed positions so they could both suck each other. For Erica, the experience of being both dressed as a woman and having her cock sucked was exhilarating, and like nothing she'd ever experienced sexually as a man. They each caressed one another's stockinged legs and asses, deep-throating hard cocks in unison. First Evelyn, then Erica came, each spilling their seeds into ready mouths. Erica had never tasted cum, but was so horny that the experience fused into her own orgasm, seconds later. They both sucked and stroked one another for another few minutes, until they both began to soften.

"Holy Shit," Erica said, slowly slumping to the side and gazing across the bed at Evelyn, who bore an enormous smirk on her face.

"Good, huh?" She replied. "I love to please a man, but Gurl on Gurl is so hot."

Three Months Later

Erica stood beside the bed, tears streaming down her face. Their time together had been a blur- her abilities as a crossdresser had grown exponentially, while Evelyn's health had taken a turn for the worst. After several ER visits, doctor appointments, and finally, the dreaded hospice, the end was near. Erica cried silently, looking down on her friend, lover, and mentor. She'd pushed her budding relationship with Peter away to focus her attention on Evelyn. She squeezed Erica's hand now, eyes almost fully shut. Erica squeezed back.

"It's OK, darling, no one lives forever."

"But I just met you! There's so much more you have to teach me!" Erica got down onto her knees next to the bed.

"I'm grateful for the time that we did have together. I've written my memoirs- they're on the thumb drive on the desk there, along with some things you might need if you do decide to get payback against your old organization."

One Month Later

Hector pressed against Erica in the elevator, his touch filled with urgent need. The hotel elevator had a glass back that exposed their travel to the outside world. The mechanical box whirred its way silently upward, as rain drops hit the thick glass. "I'm gonna fuck you so hard, witch woman, you ain't gonna walk straight for a week," Hector said, grinding his groin into her side. He was short but well-built, with dark features. Erica had dubbed him short, dark, and handsome in her mind. She'd worked with him on some jobs in the past, so it was still a little strange to see him in this light, as a potential sexual liaison rather than an associate.

"Ooh, I like the sound of that," Erica cooed, while laughing inside. Is this how all men sound, she wondered idly. She wore a black dress made from some sort of satin-type material, a long brown wig, and black tights. A small dagger and black high heel pumps completely her "sexy witch" ensemble. It had certainly been a hit at the Halloween party. Finding Hector was relatively simple- Erica still had contact info for all the other personnel in her former organization, and they hadn't even taken the precaution of switching phones. I guess they figured I was dead, so why bother, she'd thought. When she tracked him to the airport hotel bar, it was easy to make herself seen, and then approached, by him. The elevator dinged for their floor and the amorous pair spilled out into the hallway, silent in the early morning hour. Hector gestured down the hall, so Erica could go first, and he could wrap a sloppy arm around her and cop a feel along the way. He had trouble getting his key in the door, so Erica helped him, and the two staggered into the suit.

"You're so fucking hot, baby, I been lookin' at you all night," Hector turned his attention to her fully, kissing her deeply by the enormous windows overlooking the downtown. Erica felt his need once more, his intense desire for her. It felt kind of alluring, she had to admit, the feeling of such focused wanting from a man. Evelyn was right, she thought ruefully, for what seemed like the hundredth time. Erica knew she would mourn properly after the mission was done. Hector's hands quested over her body, squeezing her ass through the satin fabric. She deftly kept his hands away from her own parts, and thus far Hector hadn't minded.