Toronto Tales - Cover

Toronto Tales

Copyright© 2010 by Julia Zenobia

Chapter 3

Erotica Sex Story: Chapter 3 - Craig's hot sister-in-law has more to offer than most women, as he soon learns.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Fa/ft   Teenagers   Consensual   Reluctant   Coercion   Lesbian   Heterosexual   TransGender   Shemale   Cuckold  

Louisa lay back in a deck chair. The heat of the day was tempered by the breeze wafting over the deck, the shade of the semi-covered deck area, and the Pina Colada at hand. Louisa loved hot weather, but not sun. She was not one for tanning, her skin as pale as could be. Craig lay in a chair beside her, sipping a beer while reading. The area was crowded, but most guests preferred the sun, and had moved their chairs out of the shade, leaving Craig and Louisa to a little section by themselves.

Louisa spared Craig a surreptitious glance, taking in his long, lanky form. He was in good shape from regular gym visits, but not bulky. She couldn't tell if he had a six pack; the towel across his midriff prevented her from discovering that. His knees were raised to support the book in his hands. Louisa noticed that Craig was still at the beginning of chapter 27 of whatever he was reading, the same place he'd been when he put the book down to get her a drink twenty minutes earlier. She put a hand on his, and turned towards him.

"You're not exactly a fast reader, are you?" she asked, amused at the blush this question induced.

"I guess I'm having trouble concentrating." Craig, ending the pretence of reading closed the book and put it his side.

"I think I know why," said Louise. She raised herself, and did a quick look around to see if they were being observed. Shen she lay back down, and moved her hand, hearing Craig gasp as the tips of her fingers whispered over his rock-hard cock under the towel. "You're still thinking about last night. And so that means you're thinking about tonight, as well. Right?"

"I haven't thought about anything else since I got up this morning," Craig admitted.

"Like I said at breakfast, last night was gratis. No need for you to reciprocate. And I know you won't be able to sleep tonight if you're in the same condition. So why aren't you trying to pick up someone? You're young, you're rich, you're funny: there must be some girl on board you could charm into bed."

"You're starting to sound like my sister," said Craig. "Amanda was always trying to set me up."

"So maybe you should let her do just that. Go to the casino tonight with her and my sister. They'll have you hooked up in no time." There was a long pause. Craig took a sip of his beer, and then said,

"I'm wondering whether she's hooked me up already."

Now it was Louisa's turn to blush. She stared down at her magazine in confusion.

"Now who's pretending to read," said Craig, taking the magazine from her. She looked at him, reading the sincerity in his eyes.

"Craig, you're a nice guy, and I like you. A lot. But you don't know me at all. You don't know what you're getting into."

"Then tell me. I'm all ears."

Louisa paused, wondering whether to trust him. But he was family, after all, and she wouldn't be telling him anything that her sister and Craig's sister didn't already know.

"You know I'm transgendered. I don't need to tell you about that. But there's other things about me, and if you knew them, I don't think you'd be interested."

"Now you've really piqued my interest," said Craig, turning towards her, their faces close so that Louisa could speak in a low voice and yet be heard.

"I'm anything but monogamous. It would be difficult for me to be with one guy, forever. It's not because I have to be unfaithful, at least, not quite. But it's this. I need one man, and one man only, to be the dominant male in my life. The man that I can look up to. At the same time, I have a need to dominate others. By definition, that means I can't dominate the dominant man in my life. So I have to have other people that are submissive to me." She paused, not sure if Craig understood.

"Are you talking about being top or bottom?" he asked.

"In crude terms, yes, but there's more to it than that. But you can use "top" and "bottom" for starters. Yes, the man I look up to, would be a man I could never fuck. It just wouldn't turn me on. But I do need to fuck someone, now and again, and so I have to hook up with people like Juan the busboy. Now and again. It's just a basic need I have, that someone like you could never satisfy."

"That must create issues for you in your relationships. How do you keep the two halves of your relationship life separate? How do you prevent the dominant man in your life from bumping into the subs that you have on the side?"

"I'll tell you," said Louisa, deciding to trust him, "but you have to swear to tell no one. I mean it!"

"Pinky swear," said Craig, and the two interlocked their fingers. Then Louisa began to speak.


Louisa, although independently wealthy, still needed to work, if for no other reason, than to avoid excessively drawing down on income generated by the trust fund her father had set up for her prior to his death. She had been not quite thirteen when her father had died, and she still had vivid memories of him. While he'd accepted her transgender status, Louisa was quite sure that he would not have approved her spending six years in University earning a master's degree in Psychology, only to waste it working as head of security at the Eaton's Centre. Nor would he approve of how she got the job (seducing the property manager's rep at the centre, sodomizing him while he was in pink cuffs, videotaping the encounter, and then persuading him to give her the job in exchange for her discretion and a nice salary). She'd had the position for almost two years now, and loved it. The fringe benefits were the only reason she'd sought out the job. A few weeks earlier provided a perfect example.

"What have we got here?" said Louisa, rising from behind her desk as a guard brought in a pair of teens, the boy downcast, the girl in tears, the guard holding each of them by an arm.

"Couple of shoplifters," said the guard.

"Leave them with me. I'll have a talk with them, before we call their parents." The girl cried even more upon hearing this. Louisa stepped over to the door, and locked it behind the departing security guard. Louisa pointed at the boy. "You! Sit down over there. Now." The boy jumped to do as he was told, sitting in the chair across from Louisa's desk. Louisa then turned to the girl, and rather more gently, directed her into the interview room, a small room connected to Louisa's office. The two rooms shared a wall, and most of that wall consisted of a one-way mirror. The interview room was sparsely furnished, containing only a table, a chair, a couch, a cabinet and a mounted video camera to record interviews with in-custody suspects. The girl walked into the interview room, and Louisa closed the door, leaving the girl alone in the sound-proofed room. The girl could hear nothing from outside, but microphones in the interview room passed on the slightest sound to those outside. Louisa watched as the girl looked about the room, and then turned towards the glass. The girl observed her own reflection in the mirror, realizing now that she was being observed, and that she could not look upon those who were observing her. She sat in one of the chairs, and her tears began anew, her sobs easily audible. The girl's face was almost hidden by the long, blonde hair that reached almost to the girl's waist.

Leaving the girl to stew in solitude for the moment, Louisa sat behind her desk, staring at the young man across from her. Seventeen, maybe eighteen. A few inches shorter than her, skinny, well-dressed. Very well dressed.

"Turn out your pockets," she commanded, watching as the boy placed his wallet, car keys and cell phone onto the desk. She picked up the car keys, observing the BMW logo on the key chain. She looked at the boy curiously.

"It was a birthday gift from my dad," the boy mumbled. Louisa raised herself, and reached across her desk, grabbing the boy and pushing his head onto the cold metal surface.

"So why the fuck do you need to shoplift in my mall?" she whispered in his ear. "Why? Why is it that more often than not, the thieves my guards bring to me have plenty of money to buy things? Punks like you, or rich businessmen, or bored housewives: the same crap, over and over again. I'm getting sick of it."

"I'm sorry! I'll never do it again," the boy said. He would have said more, but Louisa ground his head into the desk.

"I'm sorry!" she repeated, mocking him. "And I suppose you were also going to tell me that 'it was my first time', and that 'you don't know how it happened', and other crap like everyone else says?"

The boy was silent now, for Louisa had taken the words out of his mouth. Louisa let go of his hair, and reached for his cell phone. "What's the password?" she asked, turning on the phone. The boy raised himself in alarm.

"Did I say you could take your head off my desk?" Louisa asked, her voice a low hiss. The boy placed his head back on the desk. Louisa repeated her question, and receiving an answer, unlocked the boy's phone. She went straight to the photos. She selected a few of them and a couple of videos as well, and then emailed them to her herself.

"Do her parents know you're fucking her?" Louisa asked.

"You looked at my photos!" the boy complained, but keeping his head on the desk as ordered.

"Yes, and I emailed them to myself as well. But I see you're not good at answering questions. Let's see what I can do to fix that," said Louisa, pulling a set of cuffs from her desk drawer. The boy lifted his head off the desk and started to stand, but Louisa was too fast for him. In a trice the boy found himself back in his chair with this hands cuffed behind his back. Louisa leaned back against the door to her office, staring at the boy, he staring back at her.

The boy took in Louisa for the first time since arriving. In other circumstances, he would have liked what he saw. The mean guard woman was hot as hell, long, black hair, sea-green eyes, and a body that sought to burst out of the tight blouse and skirt that barely confined it. But he looked for a little too long.

"You little shit," said Louisa, "how dare you even look at me?" The boy dropped his eyes, and then his head. "Too late," said Louisa, "I'll give you something to look at, all right," she added, as she moved his chair so that it was now facing the window looking in on the interview room. Louisa opened the door to the interview room to join the girl inside, and firmly closed the sound-proofed door behind her, leaving the boy behind, cuffed and unable to escape, but able to look through the glass into the interview room.

The girl turned in alarm as Louisa closed the door, and started to speak.

"Just sit. It's going to be ok, but I need you just to sit down, and listen," said Louisa, not unkindly. The girl immediately did as she was told, taking a seat on the couch. Louisa was glad that the girl seemed biddle. She pulled up the room's only chair and sat opposite the teen, and began to ask questions. The girl's name, date of birth (barely sixteen), address (Rosedale, Louisa noted to her annoyance: a rich shoplifter just like her boyfriend). The girl began to calm as she answered questions, eased by Louisa's gentle manner. When told to, she emptied her pockets without protest, and surrendered her phone and password as well.

"I'm going to take a more detailed statement from you now," said Louisa, "and I'm going to videotape it, ok?"

"Does it have to be on video? Really? Suppose it gets out there, somehow? My parents might see it!"

"It's only for security purposes," said Louisa. "It's really for my protection rather than yours. But I'll tell you what I can do. If you like, I can let you wear something over your face, so that anyone seeing the video won't be able to tell it's you. Do you want that?" The girl nodded, glad that she was being listened to. Louisa got up, and opened a drawer in the cabinet. She stepped behind the girl, and gently wrapped and then tied a pale blue silk blindfold behind the girl's head. Louisa thought the blindfold contrasted very nicely with the girl's flowing blond hair.

"I can't see!" said the girl.

"Of course not," said Louisa. "Would you rather I took it off for the on-camera interview?" The girl shook her head in the negative. Louisa turned on the camera. "Now that we're recording, let's go through some of those same questions," said Louisa, looking through the photo albums on the girl's phone.

"Caroline Appolonova," said the girl when asked to repeat her name.

"Russian?" asked Louisa, smiling as she found selfies of the girl posing semi-nude in front of a mirror.

"Yup."

"You're in a lot of trouble, you know," said Louisa in fluent Russian. "Maybe I can help you." Louisa was amused to see the girl's mouth open in shock.

"I don't speak it very well," she replied in the same language, "but I understand it ok, if you speak slowly."

"English is better, then," said Louisa. "Is this the first time you've been arrested?"

"Yes," said Caroline, her lips trembling slightly as she spoke.

"So tell me why. Why were you shoplifting? You, obviously from a good family, no shortage of money at home. Why would you come to my mall to steal? That's what I need to know, before I decide what to do with you." Louisa sat patiently as the girl began to speak. The story was the usual nonsense, the girl claiming that she hadn't wanted to steal, that it was all her boyfriend's idea, and that he'd insisted, claiming it was just a joke, really, and that they'd never get in trouble. Louisa listened only with half an ear, her attention mainly on another photo album on Caroline's phone. Here the teen was fully nude, and with nude girlfriends as well. Some of the photos showed the girls comparing breast sizes, with Caroline the clear winner. Louisa emailed these photos to herself as the girl prattled on. Then she started going through the girl's purse.

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