Toronto Tales
Chapter 1

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,

Desc: Erotica Sex Story: Chapter 1 - Craig's hot sister-in-law has more to offer than most women, as he soon learns.

" ... and so that's why I can't join you on the cruise, Craig. Sorry, but it's just too big an opportunity to pass up."

Craig could not summon the necessary energy to reply to his girlfriend's email, and instead hit the delete key. The chance for Michelle to assist her firm's senior partner in a difficult trial was far more alluring than a week's cruise in the Caribbean, even though the trip had been planned months in advance. But now it was all ruined. Craig flipped open his cell. His sister's partner answered.

"Bad news, Nicole. Michelle can't come." A shocked gasp, and then Craig gave the details.

"She can't come? Sounds to me more like she won't come," Nickie said. "She knows how much that trip meant to you. To all of us. Your sister will be disappointed, too."

"Only because she knows I won't be all that happy. Amanda doesn't care for Michelle all that much."

"And do you blame her? This isn't the first time Michelle has let you down."

"I understand why Michelle, couldn't come," said Craig. "It's true that I don't have to work for a living, but Michelle does, and she can't afford to give up a real career opportunity."

"She wouldn't have to work either, if you'd just ask her to marry you."

"You're happily married, so you wish it on everyone," said Craig. "And maybe one day I'll be as happy as you and Amanda are. But I've only known Michelle six months."

"So what are you going to do?"

"Well, I'm not going to ask her to marry me just to get her to go on the cruise."

"Silly. You know that's not what I meant. I hope you're still going."

"Yeah, I suppose so. After all, Michelle's going to be out of town. I could go with her, I suppose, but she'll be really busy on the trial she's doing, and won't have time for me. So I might as well go on the cruise. But who should I give Michelle's ticket to? It would be a shame for it to go to waste."

"Do you really want suggestions?"

Craig did need suggestions. Not yet thirty, he was already absurdly rich from his career as an investment banker. For five years he'd worked as hard as a man could work, and the hours he'd put in, along with the tens of millions he'd made, had separated him from all his old friends. Sick of the Wall Street routine, he'd quit, leaving New York for good and returning to Canada. At first he'd been exhilarated by his freedom, but of late, he'd felt lost. His characteristic verve had been dormant for some time.

"Who do you have in mind?"

"How about my sister? Louisa's great company, and I know we'll all have a good time."

"Suits me fine. Ask her, and let me know. It's really short notice, and if she can't come, I have no idea who we can ask." It was Friday, and they were to fly out of Toronto the next day for Florida, where they'd meet the cruise ship.

Craig got along just fine with his sister-in-law. Unlike so many woman, Louisa was underwhelmed by Craig's money. He'd learned to detest the glint he saw in women's eyes when he met them, the naked avarice that could render the most beautiful woman's face unattractive. But Louisa, like Nicole, was well-off, a handsome inheritance rendering them both if not financially independent, at least free from having to save for retirement.

Craig met Louisa for the first time a few weeks before Nickie and Amanda got hitched the previous year. He'd dropped by near the tail end of a wedding shower at his sister's place.

"Like what you see?" asked Amanda, who'd followed him into the kitchen when he went for a beer.

"Am I that obvious?"

"Your eyes were practically eating her alive. When you come out with your beer, try not to drool over her. You should know, by the way, that Louisa used to be known as 'Louis'. But her name's Louisa now."


Amanda laughed.

"Suit yourself. Just thought you should know." Amanda gave him a peck on the cheek, opened a bottle of wine and headed back to her living room while Craig looked for a bottle opener. He opened several kitchen drawers, his mind unable to focus on the search. 'Louis?' No way. Not a chance. Amanda, his senior by two years, had always enjoyed messing with his head when they were growing up, and took particular delight on raining on his parade. She'd seen his reaction to the beautiful Louisa, and had obviously decided to toy with him. But maybe not, thought Craig. What did he know about such things, anyway? For all he knew, he'd met shemales before without ever realizing it. He started going through the drawers again, trying to focus on finding a bottle opener instead of the image of Louisa's tall, shapely form, flowing black hair, and the gorgeous green eyes, the sexy alto voice he'd heard when they'd been introduced, the way the girl moved when she'd risen to shake his hand, the touch of her skin, the perfume she was wearing -

"Looking for something?"

Craig turned and stared. There was a long pause.

"You were exhibiting the classic signs of searching behaviour, I'm sure," said Louisa, her eyes laughing. "You were rooting through a drawer, turning things over."

Craig began to speak, but stammered, his face reddening.

"Let me guess. You're holding a beer in your hand, and maybe — just maybe — you were looking for something to open it with." She stepped closer, and took the beer from his hand. In her heels, she was his height, a woman that belonged on a runway instead of the kitchen of a downtown Toronto condo.

"Maybe I can help," she said, opening the bottle with an easy turn of her hand. "It's a twist-off. Most beers are now, you know." She took a swig, and passed the bottle back to him.

"Thanks," she said, smiling. Craig noted the perfection of her teeth.

"For what?"

"For liking me. I like to be looked at."

"You must get looked at a lot."

"I never get tired of it. By the way, it's true, what your sister told you."

"Should she have told me?"

"I asked her to. You're going to be my brother-in-law in a month."
"You're the most beautiful sister-in-law a guy could have."

Louisa leaned forward, and her lips brushed on his. And then she was gone, leaving a confused Craig in the kitchen.

Since then, Craig had met Louisa a number of times, and they always got along fine. There had been no repeats of the raw sexuality Louisa had exhibited in their first meeting. But maybe that was because Louisa often had a date with her; she never lacked for companionship. Craig knew that if Louisa came on the cruise with them, she'd be good company. But they probably wouldn't see much of her: without a doubt, she'd be surrounded by eager men within seconds of boarding the ship.

"I have no idea how this happened," said the steward to Craig and his party shortly after they boarded the ship at Miami, directing some men to take the party's bags to their cabins. "Somehow when you called ahead to say that one of your group was not coming and another was to be here in her place, there was an error in how this was recorded on our system. We still have two cabins booked for your group, but only one of them is meant for two, with a king-sized bed. The other's small, intended for only one person, when of course a cabin for two was what was required. I'll do my best to fix this, and I'll come speak to you at dinner." The steward mumbled more apologies, and then left hastily. He was lucky at least in that the victims were all Canadian, and thus unlikely to make a fuss.

A few hours later at dinner the steward was true to his word. But wisely, he waited until Craig and the three ladies were well into their third bottle of wine before approaching the table.

"I'm sorry," he said. "It is most lamentable, but there is nothing to be done. We have only the same two cabins, one with the king-sized bed, and the other a single. I was hoping that we would have some no-shows. There is always a couple or two who don't make it, for some reason. Always, always. Except this cruise. We have a full ship, and there is nothing to be done."

"Then there's nothing to be done," said Craig, sipping his wine. "Thanks for doing your best." The steward shuffled off, glad he had escaped so lightly.

"But what are we going to do?" said Louisa.

"That's easy enough," said her sister. "You may have notice that Nickie and I are vertically challenged." Nickie laughed drunkenly, almost dropping her wine. "It's true," continued Amanda. "Although I realized it only the other day. I'm only a few inches over five feet. And Nickie, how tall are you?"

"Five feet. Exactly five feet. And anyone who says less is a liar."

"I thought as much. You're even shorter than I am. I think we can manage in a single bed just fine, don't you?"

"I think we've managed just fine in small spaces before. A couch up at that cottage. The back seat of your car. And once, after leaving that restaurant on Queen, when -"

"Hush, inebriated one. You made your point. And mine. So it's obvious who should get the big cabin with the king-sized bed," said Amanda, turning to her sister. "You and Craig can have it."

"Fine with me," said Craig. "But Louisa — would you be uncomfortable with that?"

"No problem. Depending on whether I hook up with anyone I meet, maybe I won't be in the cabin too much at night."

But not the first night. Louisa was tired, and so was Craig, and after a short stop in the ship's casino where Louisa lost at the roulette wheel and Craig won at poker, they headed to their cabin.

"I've never been on a cruise before," said Craig. "Often it's hard to believe we're on a ship. The dinner was great, and the casino was beautiful inside. It's like we're in a hotel," he observed as they headed down to a corridor to their room, stopping in front of it. Louisa pulled out the plastic key from her purse, and ran it through the scanner. The door unlocked, and Craig opened it, allowing Louisa to step in first.

"Such a gentleman, you are," she said as she entered the room. "Let me get my night things. I'll get changed in the bathroom. You can get into your pyjamas. I won't be long." Louisa opened her suitcase, and pulled out her night clothes and a small bag. A moment later the door to the bathroom closed behind her.

Craig wondered what he should wear to bed as he looked through his suitcase. His preference in his own place was to sleep nude. The night before their departure, they'd all discussed sleeping arrangements, and the plan had been for Craig to share a cabin with his sister. He wished he's brought a set of pyjamas, but he would have to make do with a pair of boxer shorts and a t-shirt. He hung up the clothes he was wearing, and looked for his toothbrush. Finding these, he looked for the switch to control the lights on the side of the bed. He flicked switches here and there. The door to the bathroom opened just as he tried another switch, turning the lights off in the cabin but for the bathroom light

"Nice boxers."

He turned. Louisa was in the door to the bathroom, turning to close it behind her and wearing a white nightdress, oversized and appropriately modest. But Louisa had not reckoned on the effect cause by the backlighting from the bathroom, and her perfect figure was displayed through the sheerness of her clothing, under which she wore only a pair of panties. Craig took in everything at a glance, including the perfection of her breasts. He averted his eyes.

"What side of the bed do you want?"

"You first," said Louisa, and Craig slid under the sheets, eager to hide from Louisa the physical response this glimpse of her body caused in him. But he could not hid his reaction from himself, and he settled his head onto his pillow, his back towards Louisa's side of the bed.

"The bed's a little small for a king sized, don't you think," said Louisa, her mouth only a few inches from Craig's ear, her voice soft, low and so sexy that the man could not will away his nascent erection, his organ instead swelling to complete hardness in seconds.

"I suppose so," he mumbled. He was grateful when she took the cue to not try to engage him in conversation, and not long thereafter, he heard the sound of her breathing, deep and regular. A few minutes later he too was asleep.

When Craig awoke, he was at first confused, unable to place himself in his surroundings. Then in an instant all the events of the previous day rushed to him at once: the flight, switching planes, boarding again, another flight, the trip to the port, boarding the ship. The confusion over the cabins, sharing a room with Louisa, his hard-on just before bed.

His hard-on.

The hard-on was back, and with a vengeance. And as the cobwebs of sleep cleared a bit, Craig realized why. In the night he had turned towards Louisa, and she away from him. He was nestled against her in the classic spoon position, his groin thrust against the woman's posterior. No wonder he was hard. Louisa had a perfect ass. He noticed as much when he'd first met her. Athletic, firm, perfectly shaped, and, as his cock now knew, soft. Very soft, and the cleft between the cheeks perfectly shaped. Louisa moved a bit in her sleep, and his manhood was now encased in female flesh. Craig moved away slowly, and then turned on his back. His organ, reluctantly freed from Louisa's shapely confines, felt the cool air, for Craig's cock had in its hardness escaped from his boxers. Craig didn't bother to tuck it in, afraid that his movements might be detected by Louisa. He noticed that he was missing his t-shirt. It was warm in the cabin, and he must have taken it off in the night without realizing it. Craig's eyes searched for and found the t-shirt, a pool only slightly less dark than the darkness of the cover on top of which it lay.

At one level, he felt no desire for Louisa. That the girl was one of the most beautiful women he'd ever laid eyes on was true beyond a doubt. But Craig's taste's, so far as he was aware, did not run to shemales. He'd never had a desire to date one, or to make love to a girl who, like him, possessed a own cock. Yet he had responded to her. Of course he had responded. Of course he was hard, he told himself. How could he not be. He remembered the fleeting glimpse of Louisa's body just before bed, the slim female figure, the dark hair descending in waves down her back, the side view of a round, ample breast capped by a dark, alluring nipple. He could not banish the image, which apparently had been seared onto his retina.

He felt his cock twitch, and wondered how he would fall asleep again. He turned his head towards the bedside clock to read the time: 2:53 A.M. He turned back, and saw that the head of his penis glowed faintly, bathed in the red light from the clock and demanding attention. He turned very slowly to his left, and looked down at Louisa. He could barely see her face, but so far as he could tell, the girl was fast asleep.

Craig knew that he would not be sleeping any more that night, not until he had an orgasm. But to get out of bed, to cross the floor to the bathroom, would make noise. And opening the bathroom door in the dark would make even more. And what then? To quietly pleasure himself in the dark, and then slip back to bed, hoping that Louisa had heard nothing when surely she must hear something in the stillness of the cabin? Or even worse, to run the water for an unnaturally long time to cover up the sound of his solitary activity? No, that would practically be an advertisement of what he was doing.

Craig thought, and thought again. He raised himself gently, and took another look at the clock. 3:42 A.M. Damn. This really wouldn't do. He would be awake all night. In desperation, he moved his right hand to his cock, and with two fingers only gently began to pleasure himself. He could not afford the amount of movement necessary to quickly achieve relief, and it was a few minutes before he felt his orgasm rising within him. But then something else was rising as well. Louisa's breathing changed, and he sensed that she was about to turn over. He ceased his movements, and then her face was next to his, her faint breath tickling his ear.

Damn, he said to himself again, and resigned himself to a long, sleepless night. And now his excitement was heightened when Louisa in her sleep extended an arm across his chest. He inhaled the scent of her perfume, and sighed.

"Poor thing," whispered Louisa, her hand slipping downwards, her cool fingers encasing his throbbing organ. She began to jack him off with quick motions, her technique perfect. "This is what you need, isn't it?"

"Yes!" cried Craig, cumming instantly. That part of his mind still capable of thought was amazed to feel his cum hit his cheek, and the next blast, his neck. Three more jets landed on his chest, and then deposits landed on his abdomen, a small pool of cum gathering in his belly-button. And still Louisa's hand moved, for she had not stopped when his orgasm started, but had increased her speed and his pleasure with her attentions. Only when the sperm ceased to fly from Craig did Louisa slow, but she did not stop, instead gently milking the last of the cum from his penis, stopping only when the raging hard-on finally began to soften, the head of his cock concealed by Louisa's fingers, and her fingers by a coating of cum, solid evidence of the pleasure he'd received and that it was her hand that had given it to him.

Craig lay still as Louisa picked up his t-shirt, using it to wipe his torso.

"I'll be right back," she said.

He watched as Louisa rose, headed to the bathroom, and returned. He felt the wet warmness of a hand cloth on him as she cleansed his neck, his chest, his stomach, and lastly, his manhood. Her task finished, Louisa returned the facecloth to the bathroom, and joined Craig in bed once more.

"Do you think you'll be able to sleep now?"

Craig turned to her, Louisa's beautiful face clearly visible in the light from the bathroom. He laughed softly.

"I hope so."

"Oops. Missed a spot," said Louisa, noticing the translucent cum shining on Craig's face.

"Don't get up," said Craig.

"I won't," said Louisa. She held Craig's face, turning the cum-stained side towards her. She kissed Craig's cheek, and then gently tongued him clean. Craig felt himself returning to tumescence, and was uncomfortable. But Louisa came to his rescue.

"I'm going out for a while. I'll try not to wake you when I get back." Louisa dressed easily in the dark, and after a visit to the bathroom to check her hair, left the cabin.

Emilio, the ship's assistant steward looked at the clock: 4:20 A.M., and his shift would soon be over. And he would finish that shift richer by an unexpected $100, a donation from the beautiful Canadian guest to allow a staff member to leave early if he requested it. Puzzled, he had pocketed the cash without hesitation, and not long afterwards, young Juan had approached him, his face betraying his trepidation and expectation of a refusal when he claimed he was not feeling well, and asked to be excused from the rest of his shift. Emilio ruled the night shift with absolute authority, and everyone under him knew better than to attempt to take any liberties. Juan was amazed when Emilio granted his request with a nod. Emlio watched with amusement the allegedly ill Juan departed the casino at a run, only a minute after the Canadian guest had left. Why the tall, unspeakably beautiful woman would take to her bed a short, wiry young man made no sense to Emilio. There was no understanding why some men were attractive to women.

Emilio was wrong in his conclusion that the woman was taking Juan to her cabin. Rather, it was Juan taking Louisa to an unused area below deck where he knew there was no risk of interruption. His jacket was rolled up beneath his head as a pillow as he lay sprawled on the deck, his pants off, his dick hard as rock, and the woman's head bobbing up and down.

"That's good," he moaned. "That's great. Yeah keep sucking my cock..."

Louisa refused to give in to her mounting annoyance at the young man's instruction, and kept her temper when she felt his hands on her head, holding her still as he fucked her mouth. He was under the mistaken impression that he was in charge. Time to disabuse the young fellow.

"Just how old are you anyways?" Louisa asked, holding Juan's hard cock in place with her hand as she came up for air.

"Twenty-two," lied the man, who was not yet out of his teens.

"Anyone ever done this to you before?" Juan felt something nudge at his rectum, and then gasped at the deliciousness, the unbelievably exquisite sensation of a smooth, long feminine finger snaking up his ass and heading unerringly for his prostate. But he lacked the vocabulary to express all this.

"Fuck no fuck that's good oh fuck!"

"You like my finger up your ass? Or do you want me to stop?" asked Louisa, finger fucking Juan as her mouth took him in once more, but this time to the very root.

"Don't stop oh fuck no don't whatever you do don't-"

But Louisa did stop. Her mouth let go Juan's cock, and she admired the hard slapping sound it made as it landed on the young man's abdomen. She licked and kissed her way up Juan's torso, nipping and licking at his nipples and drawing fresh gasps. And then her mouth was on his, their lips locked and their tongues intertwined. Juan felt the woman's hand caress his ass, and then her hand was at his entrance once more.

"You want me inside you again?"

Juan answered her by swivelling his ass, willing her finger to enter him once more. He felt the woman's right hand touch his face.

"Open your eyes, and spread your legs."

Juan did as he was told, and looked into Louisa's face, unbelieving that a woman so beautiful had chosen him. His legs splayed and his heart racing, he felt the woman's finger at his entrance once more. Her lips released his, and she asked him,

"My finger again, or would you like something bigger, like my thumb, or two fingers?"

One finger had been great, thought Juan. Surely more was better.

"More please pleassssssse" he hissed. Louisa silenced him by lowering her mouth to his, and herself onto him. She wrapped his legs around her waist, Juan rendered biddable by the sexual ecstasy that possessed him, greater than anything he had hitherto experienced. He felt Louisa at his entrance once more.

"Relax," she said. "Open yourself for me."

Juan did so, and felt the thumb at his entrance. Or more than a thumb. Two fingers at least. His muscles clamped around the invading flesh, and then at Louisa's command, he forced himself open again. And then again. Pain, pleasure, pain, and then the incredible joy of penetration, his hips bucking, thrusting upwards insistently to take all of what Louisa gave him. No sooner had he commenced a rhythm than the rhythm changed. Instead of Juan thrusting at Louisa's hand, it was Louisa thrusting at him, and he lay passively on the deck, splayed beneath her as as she penetrated him over and over again. When her lips left his, the small room they occupied was filled with his moans, and hers.

"Fuck that's good yeah fuck that's good keep doing it!"

"Do you like me fucking you?"
"Yeah keep fucking me like you are I like it so good like that!" Their hands joined and Louisa picked up her tempo, slamming into the boy and enjoying his moans of pleasure.

Their hands stayed grasped together, joining them as they fucked. Their hands! thought Juan. He turned to his right, and saw his hand holding hers. He turned to his left, and saw his other hand in hers. And yet he felt the penetration into his core, the pounding.

"What? How? What are you doing?"

"I'm fucking you."

"With what?"

"My cock. And you're tighter than hell. You've never been fucked before, I'm sure."

"Get off me!" said Juan, struggling to break the woman's grip. In fact Juan was far stronger than Louisa, and could easily have bested her in a fair wrestling match. He was thin and wiry, but much stronger than he looked. But the wrestling match was anything but fair. Louisa was a good six inches taller than he, and now she had his arms pinned to the deck with her elbows. Juan could not plant his hands or feet anywhere to gain a purchase, no matter how hard he tried. He fought, but not for long. It was so much easier to surrender. He gave in to the beautiful face above his. He abandoned himself to the green eyes that smiled down on him. He was defeated by the sight of the woman's hair tumbling down, and what little will to resist that remained was conquered by the cock piercing him, massaging his prostate with each entrance and withdrawal, satisfying a need he had never known existed.

Louisa lifted her elbows, and knew she had judged Juan perfectly as she felt his hands grasp her ass, pulling her into him deeper and more insistently. Louisa raised the boy, his ass off the deck now as she pistoned her cock into him.

"Put your hands on the deck to hold yourself up," she commanded, and Juan obeyed, wanting nothing but to do what he was told. No longer having to hold the boy up, Louisa took his cock in her hand, and in seconds Juan was returned to full hardness. He came at the same time as Louisa, she filling a rubber with her cum, he spraying his in fountains and with greater force than he had thought possible. Finally Louisa stopped fucking him, and pulled her softening cock from his ass. Juan was breathing heavily, his chest shiny with sweat and his cum.

"Can we do this again?" he asked.

"I'll find out right now," said Louisa, gathering up some of the boy's cum on her fingers, and holding them up to his mouth. Juan opened wide, and took her fingers, soaked with his cum, into his mouth, and sucked greedily.

"Good," she said. "We'll do this again. But we'll start with something different. Next time, you'll suck my cock, swallow my cum and make me hard once more. Then I'll fuck you, and for longer. I'll fuck you until your ass is so sore you won't sit for a week."
"Whatever you say," said Juan.

Leaving the boy naked and motionless on the steel deck, Louisa returned to her cabin, and had a quick shower. She slipped under the sheets, and noted with satisfaction that Craig was fast asleep. Now she would be able to sleep, too.

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