Toronto Tales - Cover

Toronto Tales

Copyright© 2010 by Julia Zenobia

Chapter 1

Erotica Sex Story: Chapter 1 - 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  

" ... 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."

"Bullshit."

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.

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