A Boo of Letters

Kathryn Sellers watched the computer monitor intently. Her stomach tingled as the thrill of what she had accomplished washed over her. Sitting in the corner of her home office, Kathryn shifted in her black, faux-leather desk chair. She felt a slight pull on her bare thighs as they separated from the cheap material. It occurred to Kathryn that she had been sweating, a realization she found disconcerting since she prided herself on her self-composure.

Kathryn exulted as she watched Alex Gentry, a 45-year-old partner in an architectural firm, leaving his office. Kathryn had spent the last six months of her life working toward this moment. Her plans, for both Alex and herself, had just taken a colossal leap forward. Kathryn had watched Alex read the letter in the leather-bound journal, all while nervously biting her lower lip, not knowing with certainty how Alex would respond. She knew from her work that the human mind is not always predictable, so she had watched, waiting, filled with trepidation.

Now that Alex had left his office, Kathryn leaned forward in the chair, her long, slender fingers deftly working the keyboard. She looked up and the monitor began replaying the recorded video from Alex's office. It showed Alex facing her camera, just minutes ago, with a look of complete resignation on his handsome face. As he dropped his pants and boxers, Kathryn could not help but laugh, seeing again the shriveled stump of his cock, which appeared half-withdrawn into his body. "Too perfect," she thought to herself.

As the screen showed Alex pulling on the white lace panties, she paused the video. Frozen in time, Alex stood there, the panties hugging his hips. In preparation for this moment, Kathryn had spent months thoroughly researching the life and times of one Alex Gentry. Cameras had been surreptitiously planted throughout his apartment and office. She had found nothing to indicate that he was a secret crossdresser, or that he had any particular affinity for women's clothing. Yet, here Alex stood, in his sexy panties, just as Kathryn's alter ego, Miss Becca, had commanded.

Kathryn knew much regarding the psychology of middle-aged males, particularly men like Alex. Straight American males had been nurtured in a society where women's clothing was designed to appeal to their prurient interests. Panties, stockings, low-cut bras, high-heels, and skirts of a certain hemline were designed to activate a male hormonal reaction. Kathryn believed that it was precisely the male physical and mental reaction to feminine clothing that generated the paradox of societal rejection of male crossdressing. After all, it can be terribly confusing for a man, who thinks of himself as straight, to want to fuck another man simply because he is wearing nothing but a pair of silky panties and thigh-high stockings.

Kathryn never bought into the idea of the completely straight man, of course, believing that virtually all men fall somewhere in the middle between gay and straight, even if they are unable to acknowledge or accept this truth. And it was this knowledge, founded in extensive personal experience and reading, that caused her to land upon this path for Alex. She had forced Alex to take the first step, and many more steps lay in front of him. For now, Kathryn felt deep satisfaction that her months of work appeared to be paying dividends.

Kathryn had not been surprised by Alex's decision to wear the panties. She was, however, surprised by her own reaction. Kathryn looked at the clock on the wall; 9:35 p.m., she noted. She still had twenty-five minutes before Bruce was scheduled to arrive. Kathryn turned in the chair and looked to a second monitor to her right. This monitor contained a live feed of a room down the hall, what used to be the master bedroom of her home but which she had converted several years ago into the room in which she worked with clients. The camera in the master bedroom aimed at a corner, where one of her clients lay in a fetal position, trapped in small cage.

Kathryn was a 38-year-old, twice-divorced woman. Her first husband had been her high school sweetheart, nothing but a boy who became an abusive drunk. Kathryn had once been a meek, sweet girl, and she had loved this boy. At first, he made her feel like a princess; he was handsome and athletic, and he doted on her. He had given Kathryn her first orgasm when she was 17, a memory she still cherished, only because it was an orgasm that came from a real physical and emotional connection with another person, an experience she had never been able to replicate. But within two years, as the glory days of his high school years faded into memories, her husband became embittered, and began directing his frustrations into a cycle of drunkenness and abuse. Kathryn barely escaped this marriage intact, when she was 22, and only after she had mustered the courage to run.

This escape left Kathryn with nothing but the clothes on her back, a jar of change, and a beat-up Civic. Despite the obstacles, Kathryn somehow managed to survive the ordeal of the next few years. She worked around the clock at odd jobs, as a waitress, a maid, anything to pay the bills and feed herself. Then, she met an older, single man in a restaurant, and the promise of an easier life led her into a loveless, second marriage. This marriage lasted 6 years. The only good thing to come from it was Kathryn had been able to go to college, earning a degree in psychology. After divorcing this man, Kathryn swore she would never allow herself to depend on anyone again. At 31, she set upon a path of self-reliance and empowerment.

Now, for the first time in her life, Kathryn felt truly empowered. She had forced a successful, handsome, semi-wealthy man to do her bidding. While she had been doing this for years, it was in a different capacity, part of her side business as Mistress Kate. None of it was real, however. Her work with Alex, however, was very real. It was control; it was power. And, the black thong panties Kathryn was wearing were drenched. She could not remember ever being turned on like this.

Kathryn was half-dressed for her 10:00 appointment. Her make-up was done, and her long, wavy auburn hair was pulled up, only a few stray locks falling out to frame her delicate face. She wore a black corset, the tops of her 36D breasts spilling out. Kathryn's thin knee-length wool skirt was bunched half-way up her thighs, pushed up as she had leaned into the computer screen.

Kathryn turned back to the frozen screen shot of Alex and reached for her mouse. She zoomed into the front panel of Alex's panties and marveled at how flat it looked. She noted the hair of his legs poking out the edges, a not so appealing contrast to the white lace of the panties. Kathryn briefly thought to herself how much better he would look without the hair, and then zoomed in so she could see only the panties themselves, with just the tiniest of bulges pressing against the satin fabric.

Kathryn pulled her right hand from the mouse and placed it on her knee, brushing her thigh with her fingertips, slowly caressing her leg, until her hand made it to the edge of her own panties. She slipped a finger under them, touching herself for the first time. An electric bolt flashed through her body as her index finger slipped down her moist, hairless mound, through and into the folds of her pussy. Kathryn drew her finger up, reveling in the heat pouring off herself, and as she reached her clit, the lightest touch of her finger sparked a shudder.

Kathryn circled her clit, her body reacting to every brush of her finger, and her mind turned back to Alex. Alex had a beautiful cock. 6 inches, cut, smooth, perfectly-proportioned, and when fully engorged, ram-rod straight. A cock made for sucking. A cock made for filling a hot cunt. A cock made for any number of things. "Fuck," Kathryn moaned softly to herself.

She reluctantly pulled her hand away and stood to reach behind one of her monitors, quickly grabbing a six-inch, pink, silicone dildo. She sat again, pushing her skirt to her waist, and quickly drawing her panties down to her knees. Kathryn lifted her bare right foot to the edge of the desk, her left foot planted on the floor, shifting her hips for better access. Bringing the dildo to her mound with her left hand, she probed, and then, in one fluid motion, she pushed the dildo all the way inside her waiting pussy. Kathryn gasped as the toy filled her. Her pussy was remarkably tight for a 38-year-old woman; it had not been used much in recent years.

Kathryn held the dildo firmly with her left hand, and returned her right index finger to her clit. Her mind turned back to Alex. She imagined Alex sitting in her chair, wearing nothing but his new panties. But now his cock was hard, the perfectly-formed head and three inches of shaft reaching out of the panties, pressed hard against his stomach. She imagined herself in front of Alex, standing, looking down with pleasure on him, admiring that cock of his, incredibly aroused at the thought of him wearing the panties she had given him. Alex, looking deep into her eyes, a crooked grin on his face, as he slips his thumbs under the lace waistband, pulling the panties out and over his cock and balls. Now his entire manhood is waiting for her, imploring her to impale herself on it. She imagines moving forward, slipping one leg and then the next through the gaps in the back of the chair, balancing herself with her hands on Alex's shoulders, her throbbing pussy positioned just over his waiting cock. Then, Kathryn releases her body, letting Alex's entire shaft fill her in one glorious movement.

In the present, Kathryn's body explodes as an orgasmic wave rushes through her, her pussy contracting on the pink dildo, her juices washing over it, spilling down its silicone shaft. Kathryn screams, "Oh God, Alex, Alex," as she continues to furiously rub her clit. The wave of the orgasm tears through her, and then, seconds later, another one arrives, moving the length of her body, reaching her brain, the pleasure sensors temporarily overloaded. As the second wave subsides, Kathryn realizes she could keep going, that the pleasure might never stop, but she briefly looks at the clock, and realizes she must stop. She withdraws the dildo, sets it aside, and pulls her up still wet panties.

"Jesus, get a grip Kat," she thinks to herself. She moves to the far wall of the office, where a rack of clothing and shoes sits. Kathryn unzips her skirt, and exchanges it for a smaller mini-skirt, this one made of black leather, just barely long enough to cover her panties. She grabs a second pair of black thong panties, putting them on after removing and throwing the dripping pair in a hamper. Kathryn sits at a vanity next to the clothing rack, and slowly pulls on a pair of sheer black hold-up stockings, after which she slips into and zips her four-inch black stiletto boots. She examines herself in a full-length mirror, straightening her clothes, adjusting her corset, tucking her hair in. Despite her best efforts, however, Kathryn cannot entirely stop thinking of what just happened, the first multiple orgasm of her life.

Kathryn looks at the clock, 9:55 p.m. now, and returns to her computer desk. She examines the live feed from the master bedroom, while she takes deep breaths in an effort to refocus her mind to the work at hand. Waiting for her down the hall is one of her regular clients, a 57-year-old banker with a penchant for masochism. When the banker is in her house, she refers to him only as "Shit-Head." Shit-Head had arrived around 7:00 a.m., and Kathryn, or Mistress Kate as she was known to her clients, had begun her work with him.

Shit-Head was nude in the cage, except for the black leather mask over his head. Hidden under the mask was a ball gag to keep him quiet. His hands were tied together and to the bars of the cage with a strong plastic tie. The banker's ass was striped with welts from the caning Kathryn had given him that morning. Sticking out of his ass was a medium-size black dildo, about 8 inches long, but only about 4 inches of it had been inserted after his caning. Shit-Head appeared to have fallen into a fitful sleep.

Shit-Head was a disgusting blob of a man, probably over 300 pounds, with hair in all the wrong places. Kathryn did not find it difficult playing the sadist with Shit-Head because she found him repulsive, but he paid well. And she never judged a man or woman based upon their kinks, so if this is what he wanted, and he paid, Mistress Kate was happy to oblige. Kathryn had a special treat for Shit-Head tonight before she released him back to his boring life, something she knew he would both hate and love at the same time.

Shortly after 10:00 p.m., the doorbell to Kathryn's house rang. She went to the door, and standing outside was Bruce, a hulk of a man, 6 foot 4 inches tall, and packed with 230 pounds of muscle. Kathryn worked with Bruce regularly, and she smiled as she invited him inside and gave him a hug. "Hi, Bruce, how is the family?" Kathryn inquired. "They're great, Kat, it's good to see you," Bruce replied, as he handed Kathryn a piece of paper. Kathryn looked over the paper containing Bruce's most recent STD test results, which she folded and stuffed into her corset. She then handed Bruce an envelope with $400 in cash. Kathryn said, "Well, let's go see Shit-Head."

Kathryn opened the master bedroom door loudly, slamming it against the outside wall. The banker jolted awake in his cage, a muffled grunt coming from under the mask. She quickly walked to the cage and yanked it open while Bruce stood outside the door in the hallway. She grabbed a pair of wire cutters and freed Shit-Head's hands, as she ordered him to "get the fuck out." The banker crawled out of the cage, moving slowly, obviously stiff and in some pain from his beating.

When he had extricated his entire mass, Kathryn planted the sharp heel of her boot in his ass and ordered him to crawl forward. When he had made it to the table on the far side of the room, Kathryn exclaimed, "I have a real surprise for you tonight, Shit-Head, so get your fat ass up." He slowly stood, and Kathryn pushed his hairy upper back, hard, so that the front side of him fell onto the table, his feet planted on the floor. Kathryn moved to the opposite side of the table, and roughly grabbed the banker's arms, locking his wrists into a rack at the end of the table. Now, he was bent over, prone, unable to move his upper body, with half a dildo sticking out of his ass, and Kathryn summoned Bruce.

Bruce walked to the front of the table so the banker could see him. Bruce was wearing only black leather pants, a black leather vest, and motorcycle boots. His pectoral muscles rippled under the vest, his stomach a washboard. The banker's eyes widened when he saw him for the first time. There was fear in them. Kathryn lowered her head to the banker's right ear, and whispered, "Shit-Head, this is Bruce. You are the most disgusting piece of shit I have ever seen, but despite that, Bruce is here to fuck you until your eyes pop out of your skull. What do you think about that?" The banker responded by thrashing about on the table in a futile attempt to get his hands free, all while grunting unintelligibly under the mask. As he continued thrashing, Kathryn moved behind him, holding a cane, and gave the banker three quick lashes on his ass, a result of which the muffled grunting turned into muffled screaming and more angry welts rose up on his ass. Kathryn moved back to the banker's ear, whispering, "Now shut the fuck up Shit-Head and stop moving or you are getting ten more." The banker immediately silenced his grunting and stilled his body.

Bruce gave Shit-Head a wicked smile and moved his hands to the buttons on his pants. Slowly, Bruce undid one button after another as the banker watched. Then, Bruce pulled out his cock, and Kathryn was momentarily frightened as the banker's eyes, which had previously been the size of saucers, closed and his body slumped. It looked like he had passed out. But, then he stirred and re-opened his eyes, and Kathryn breathed a sigh of relief.

Bruce's flaccid cock was at least 6 inches. It was thick and covered in veins. His huge balls, the size of racket balls, hung below. Bruce, never saying a word, grabbed the shaft with his right hand and began stroking it. The 6 inches of flaccid meat quickly grew into 10 inches of thick, crooked cock. No doubt, Bruce's cock was one of the ugliest dicks Kathryn had ever seen. Kathryn moved into the banker's ear again, "Are you ready for Bruce to split you open?" The banker grunted furiously, but he kept his body still. "No, well, let's get you ready anyway," Kathryn continued. She moved behind the banker, while Bruce continued stroking his cock in front of him.

It was bad for business to hurt clients in ways they had not asked for, but Kathryn knew of the banker's fantasy to be forcibly fucked. She needed to prepare him for Bruce though, so she removed the half-inserted dildo, threw it to the side, and lubed a clean, slightly larger dildo. She slowly inserted the dildo into his ass, feeling the resistance of his inner sphincter. She stroked him with it a few times, warming him up, and when she could sense his body accepting it, Kathryn pushed it all the way in. The banker's muffled cry shot out, the pain hitting him, but Kathryn continued pumping him, fucking him with the dildo for a few minutes until the banker adjusted to it. Then, she pulled it out, and motioned for Bruce.

Bruce stood behind the banker, who was thrashing again, resisting. Bruce grabbed his hips with his strong hands to settle him. He then lined up the head of his cock with the banker's well-used asshole, and pushed the tip in. When it was firmly in place, Bruce powered his entire shaft into the banker's ass in one hard thrust, bottoming out, his sizeable balls hitting Shit-Head's meaty thighs. The banker's muffled screams were even louder than when he had been caned. Bruce did not stop. With his hands on the banker's hips, he repeatedly pulled his 10 hard inches back to the tip, and pounded back in, building a rhythm, fucking the banker mercilessly.

Kathryn was at the banker's ear, her voice rising over his muffled screams, "Yes Shit-Head, you are getting fucked good now, aren't you? This is what you wanted wasn't it? You are such a dumb fuck, such a pathetic little worm. God, you look so disgusting, getting fucked by this big, strong man. You don't deserve it, do you, Shit-Head? You don't deserve to have his seed inside you, do you, Shit-Head?" The banker just screamed into his gag.

As Bruce continued pounding him, the banker's screams faded. They morphed into soft, stifled moans. The banker was now pushing back into Bruce's pounding cock, wanting it even deeper inside him. Finally, Bruce erupted inside the banker, pumping a full load into him. Before he was spent, Bruce pulled out, shooting two more ropes of hot cum onto the banker's back. Kathryn could see that Shit-Head had shot an enormous load of his own, apparently by rubbing his little cock against the table in tandem with Bruce's long strokes. The banker's semen spilled out from the edges of his fat belly.

Bruce cleaned himself up and left, giving Kathryn a small hug in the hallway, thanking her for the business. Kathryn returned to the room and unlocked the banker's hands. The banker was clearly spent and exhausted, but Kathryn spoke to him in a firm voice: "Get your fat ass up and get dressed. Don't you dare clean any of Bruce's seed off your body before you get dressed. You don't deserve any of it, so you should treasure it a little longer. Next time, I might have him put it down your throat so none of it goes to waste. And you better clean up your own mess off that table, Shit-Head. If I see one drop of your filthy mess later, I am going to open up your back with the cane next time. Now, get cleaned up and get the fuck out. You have 5 minutes."