Are You Tiffani Caine?
Reluctance/nonconsent Story

Are You Tiffani Caine?

by Senor_smut 18 min read 4.8 (4,900 views)
lesbian prostitution orgy sex toys exhibitionism group sex mf ff
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Author's Introduction:

This work in its entirety is dedicated to KF, whose life was brutally unfair and far too short. I will always remember you, always love you, and always miss you. Rest now, my brother. You've earned your peace.

Are You Tiffani Caine? Chapter 6

deals with non-consensual elements (blackmail, non-violent coercion), vaginal sex, anal sex, lesbianism, group sex (different combinations), explicit descriptions of meals, struggles with religious faith (Christianity), exhibitionism, and prostitution.

I welcome feedback, positive or negative. If you want a response, either leave a comment at the end of this story or email me at the address on my profile page.

All fictional characters that I made up in my head as fiction who engage in fictional sex are over 18 fictional years of fictional age fiction fiction fiction.

Up next:

That Damned Blessing, Chapter 6 and Epilogue

Are You Tiffani Caine? Chapter 6

By Senor Smut

Yet I swear I've seen my reflection somewhere so high above this wall

- Bob Dylan

Monday, September 19

It had been a wild day so far, and it was barely past noon. It was her departure day for her Dahlia trip to Portugal, where she was to be one of several sex toys for a billionaire named Manfred Bloch, and she'd been told to dress like what she was going to be for the next several days: an expensive prostitute. She already had a dress that allowed her to do that - the little lavender number that her other Dahlia client, Marku, had bought for her that she'd been too chicken to wear before. She'd managed to get the very short dress to stay down as far as it could by means of dress tape and hairspray, but it was impossible to wear a bra under the dress so her big ol' girls were bouncing free and bouncing wild, and her nipples were struggling to find a way through the fairly loose knit of the fabric. If that hadn't been enough, Jacey had taunted her into going commando for the flight, which meant that if she wasn't very careful she'd be flashing her lady bits to all and sundry.

Only she hadn't been careful. In the international lounge at the airport, she had very deliberately done a lengthy flash at an extremely hot guy, which had made her so wet as to become a problem. And so, fifteen minutes before her flight was due to be called, she was contemplating heading to the bathroom to put on the G-string she carried in her purse when the Caller rang.

"Are you Tiffani Caine?"

"That's me."

"This is Wilbur, and I must say you're actually sounding smug. What's up?"

"I'm sitting in an airport lounge in the shortest dress I've ever worn without a stitch of underwear on."

"It wasn't long ago that you'd have panicked at the thought, but here you are sounding happy about it."

"It's a lot more fun than I thought it would be. I could get hooked on this. It's so powerful!"

"In what way?"

"Well, for example, there's a middle-aged couple sitting across from me. The guy looks kind of wimpy and his wife looks like a real problem. I think she holds all the power in the relationship. But if I opened my legs at him, he'd stare at me - he wouldn't be able to help it. He'd stare until his wife noticed and then she'd give him all kinds of heck for it. I could cause a marital dispute and I wouldn't have to say a word. That's power."

"As a middle-aged man, I cannot deny the might of a perfect female form. Are you going to do it?"

"Gosh no!" she laughed. "That would be mean. I'm going to sit here with my legs crossed like a lady and wait for my flight. I don't want to be kicked off the plane before it even boards. Besides, he keeps looking at me out of the corner of his eye already."

"You should give him a little something."

"I am not going to flash him."

"No, but you could blow him a kiss or something."

She laughed. "Are you trying to instigate a divorce?"

"I can tell you're having a great time. Just give him a little something to remember you by. It doesn't have to be much."

"Gah, just...fine. Give me a bit." She had to wait until the woman was staring at her phone and the man was looking squarely at her; then she licked her upper lip in a lascivious fashion and gave him a wink. He turned red and his jaw gaped open -

And then she was back talking, not looking at him at all. "OK, that was

way

more fun than it should have been."

"What did you do?"

She told him, then added, "He's married. He's a married man with his wife right next to him and I deliberately gave him an erection. I am evil."

"And yet you don't sound upset."

"I'm not!" she giggled. "I didn't cause any harm. His wife never even noticed, and now he gets to have a nice fantasy about me. He'll probably be smiling for the rest of the day. Maybe he'll even have sex with his wife tonight, if she does that sort of thing."

"Cold, is she?"

"Loud and whiny and unpleasant, doesn't stop complaining even when she's not talking. Typical Karen."

"I think you wouldn't be having this much fun if you weren't looking forward to what's coming over the next few days."

"You're right. I stopped bitching about it and all of a sudden it seemed really fun. I'm having fun now, just sitting here waiting for the plane."

"You should join the Mile High Club, that would be even more fun."

She arched an eyebrow. "Is that an order?"

"No, it's a suggestion from one friend to another. You're on this trip to have lots of fun and lots of sex. You may as well start early."

"I don't know about that. I know Jacey wouldn't hesitate, but I'm not her. Yet."

"Yet?"

At that she sighed. "Yeah. The money I get from this is going to be great, but without a steady income it's going to be gone before I know it and I'll still be deep in the hole. The agency is starting to seem more and more like a viable prospect, especially because everyone keeps telling me to do it. Even Yvette."

"She mentioned that."

Sara considered for a moment, then said, "You know, Yvette said something to me. She said...well, she implied more than just stated, but she made it sound like she's been in my position - like the one getting the orders from you guys, not the one giving them. Even orders for..." She dropped into a whisper. "

Prostitution."

There was a pregnant pause before Wilbur said, "OK. Was there a question in there or are you just making an observation?"

"Is it true?"

"Any personal information you get about her will come directly from her. We don't talk about each other's pasts. She would never have told you that I used to be a counselor, for example. I wanted you to know so I told you; she wanted to tell you what she told you, so she did."

"OK. I guess I'll choose to believe her."

"Okey doke."

"So what do you think? About me with the agency?"

"I think it's up to you if you want to work there. I will tell you this, though: experience at the agency will be invaluable for many of the tasks we will give you. It will make you very skilled at sex, which will definitely come in handy - and anyone you're with in your personal life will reap the benefit. More than that, though, you could stand some hardening. You'll need to make coldly rational decisions in the future, and prostitution can help you build the emotional distance you'll need to succeed."

That was a hell of a lot to chew on, and she was quiet for a long time. "These things you're going to have me do will be dangerous?"

"Some of them."

"Criminal?"

"Many of them."

Of course, she knew that already - she just needed to be told. "I guess that kind of settles it."

"Don't sound so glum. Jacey is living her best life, isn't she?"

"You're not giving her stupid spy shit to do."

"Irrelevant. The tasks we set for you will be there regardless. Being a prostitute will just make it easier and safer for you to do them."

She sighed. "I don't really want to talk to you any more right now."

"I understand. Have a safe flight and a great week."

"Thanks." She hung up the phone and let herself slide into dark broodings; her mind didn't stay there long, though, because only a few minutes later, first class was called on her flight. She was still preoccupied during the boarding process, but when she got to her seat she was suddenly very focused. She had flown enough that it was no big deal for her, but this was her first time in first class...and it was

GOOD.

The seat easily occupied the space of three seats back in the hoi polloi section, and that was just width; the seat could turn into an actual flat bed, there was a shelf and place for her carry-on that would be in nobody's way, and nobody would be reclining their seat into her chest or kicking the back of her chair. Her seat was in the middle (there wouldn't be much to look at in a flight over the Atlantic anyway) and as the rest of the first-class passengers boarded it became apparent that she would have the whole row to herself. The whole row!

This was something she could get very, very used to - and Dahlia girls traveled like this every time they went overseas.

Damn it girl, stop thinking that way. It's not like I

want

to be a whore.

Speaking of being a whore, she texted Sam that she was on the plane. A couple minutes later came the reply:

Have a good flite! Text when you get to Amster.

First class FAs are nothing if not attentive, and barely had she settled in than the blanket she requested arrived. Planes are chilly when you're not packed in like hogs in a slaughterhouse, and the thin, short scrap of material that she was pretending was a dress had no thermal insulating properties whatsoever. Soon she was cuddled up under a snuggly blankie with a neck pillow, just as comfortable as she would have been in her own bed. Fifteen minutes after takeoff she had a cherry vodka sour in one hand and nice-sized bag of cashews in the other, watching a first-run movie and feeling very content for the long leg from Minneapolis to the Netherlands.

The contentment didn't last. An hour later she was worrying about her future again, wondering if she could handle everything the agency would throw at her - wondering if she wanted to handle it. Yvette and now Wilbur had told her it was a good idea given what they had in store, but they hadn't said she had to. She could take the harder road if she couldn't handle the easy one.

If only she could go back in time and stop herself and Adam from getting on that boat, her life would probably be so much less fraught now.

She was still brooding when it came time for the meal service. The airline meals she'd had before were anything but inspiring, but first class made all the difference. Here she was served delicious shrimp and grits, a zingy curry salad, and a decadent slice of cheesecake, all paired with a white wine that did fascinating things to her uneducated palate.

As good food so often did, the meal lifted her spirits considerably and she began thinking about Wilbur's suggestion to join the mile high club. It sounded fun and daring, and she was bored and horny. Besides, whether she joined the agency or not, she probably ought to get used to casual sex with strangers, given what the Callers might demand from her. There were a couple of people in the section she wouldn't have minded cramming into an airplane bathroom with, but she wasn't up to just asking her target. Maybe she could entice someone?

Hold on, Sara Moorhead wasn't the kind of person who would entice a complete stranger to have sex in a semi-public place where they were actually likely to be caught by people who would get very upset at her for doing it.

No, that's absurd. Keep your pussy in your panties, girl.

Only she wasn't wearing panties, and for the next week she wasn't Sara Moorhead. As far as anyone knew, her name was Tiffani Caine and she was a high-priced escort willing to have casual sex whenever and wherever. Holding onto Sara could only be problematic for the rest of the trip, at best making her act in ways that Tiffani wouldn't, and at worst pissing off her client badly enough that he refused to pay her the money she so desperately needed. She had to undergo a cognitive readjustment and get into character, and Tiffani Caine was definitely the sort of character who would drag a man into an airplane toilet for a quick fuck. Over the next half an hour the idea kept growing in her mind until it was making it hard to think, and making her cunt so hungry and wet that the only thing keeping others from noticing her smell was that she was covered to her armpits in a lovely, soft blanket.

This is insane. It's impossible.

But it wasn't, not for Tiffani, and Tiffani was who she was.

Her need finally made the decision. Taking her little clutch purse, she slid out of her seat and made her way toward the bathrooms, In the second row back from her target there was a man in a very nice suit; he wasn't particularly handsome, but he radiated in spades the distinguished-older-man vibes that really revved her up. She waited until she had barely passed his seat so he knew she'd give him a good angle...and dropped her purse. Slowly she bent over, letting her dress ride up her backside until both tantalizing pussy and pink asshole were visible. Her purse retrieved, she made her way to the bathroom, turned, and saw that her mark was giving her a huge smile. She winked and went inside, deliberately leaving the door unlocked.

And she waited. Then she peed. Then she waited some more.

Well, that was humiliating.

She exited the bathroom and headed back to her seat, only to see the man smiling at her and holding up his left hand, twirling his wedding ring with his thumb. Wryly he said, "If only."

She smiled back. He was a good man, being faithful to his spouse, and that mitigated the embarrassment...sort of. A little. She answered with a chuckled, "If only," and returned to her seat. Covering herself up with the blanket again, she tried to watch another movie. Her need didn't go away though - now that her mind was on sex, it wasn't getting off of it until she got off. Damn it.

The FAs made their rounds and she ordered a negroni. A few minutes later, drink in one hand and the other under the blanket, she let her thighs drift apart and slid her hand between them. Tiffani was going to get off one way or the other. Her pussy was juicy and steaming hot, her clit standing out proudly from its little shelter. She bit her lip to stifle a gasp as her fingers moved lower, wandering between her lips to gather the lubrication so readily available there, and then she moved her hand back up so she could find her button.

And to think that she'd deprived herself of masturbation for seven years! She must have been crazy to believe any religion that said you couldn't give yourself love. Now, those ludicrous inhibitions cast aside, she could lazily stroke her clit and revel in the sensations for as long as she wanted, or at least as long as she could hold out. She fantasized in explicit detail about the man she had tempted and how she wished he had followed her, how she wished he had shoved her against the sink, flipped her dress up to her mid-back, and fucked her deep and hard while telling her that this was where a dirty little fucktoy like her belonged, taking older men's cocks in a bathroom. Placidly sipping her drink and doing her best to keep quiet, she brought herself up to the very point of orgasm and then calmed herself down again and again, for almost fifty minutes. When she finally pushed herself over the edge and had a short, hard, intense orgasm, she turned her head and bit onto her neck pillow to keep from screaming aloud. She still had a dopey grin on her face ten minutes later when she slipped into sleep somewhere over the dark ocean.

Tuesday, September 20

She barely slept, because it was only half an hour later that the flight attendant awakened her. "Miss, we'll be descending into Amsterdam soon, so please secure your personal objects and put your tray table up."

"Oh sure, OK," Sara replied, having had exactly enough sleep to feel groggy and not one second more. She performed the needed tasks in a haze, then went to the bathroom; she didn't notice until she was in the bathroom that her dress tape had dislodged and her dress was up to the middle of her ass, meaning that anyone who had glanced at her as she moved has seen everything she had. Her initial reaction was a painful smash of embarrassment, but the sexiness of it soon swept that away - how hot would it have been if the whole section had seen her and now wanted to fuck her stupid? Tiffani would have been thrilled by the notion.

Damn, she wanted to masturbate again - but even more than that, she wanted a nice hard dick. Oh well, she was going to be seeing a lot of at least one cock over the next week. She could hold out until then.

Back in her seat, she contemplated her arousal as the plane landed at Schiphol. On the one hand, it was understandable: she hadn't been laid since Alissa had dumped her over a month before, and her naturally high sex drive needed sating; then too, she had just discovered the thrills of exhibitionism and how much that got her going. She was traveling for the specific purpose of fucking, and getting fucked by, several women and at least one man. Oh of course this was an adventure, an all-expenses-paid to the Algarve, and the impending week of hedonistic excess would naturally have her hyped.

Besides, Tiffani was a sex fiend.

As the plane was taxiing to the gate, she sent another text to Samantha to let her know she'd arrived in Holland. Although it was almost 11 at night back in Minneapolis, Sam replied instantly with a thumbs-up emoji.

She had three hours to kill here, and she would have been tempted to take a walk outside to get fresh air but it was raining like hell. Instead she headed for the bathroom to retape her dress, grabbed a black angus carpaccio from a restaurant called The Med. Then she stumbled to a lounge, set her phone alarm, and promptly passed out for almost two hours. Once awake, she went through the rigmarole of boarding her second flight and stumbled to the first class section without fully awakening, got a blanket, and fell asleep before the plane took off for the three-hour leg to Lisbon.

She awoke with forty minutes left in the flight, washed her face, redid her makeup, and felt wide awake when when the plane began its descent. She had a window seat this time and so had a gorgeous view of sun-dappled hillsides of red roofs as they came in for their landing. The moment the wheels touched down, she texted Sam that she was in Portugal.

She was met at disembarkation by a pair of unremarkable men in neat black suits, one of whom held a placard with her

nom de prostituΓ©e

, and she approached with a bright smile.

"O meu nome Γ© Tiffani Caine."

She thought her pronunciation was pretty good, but the man returned her smile and said in received pronunciation English, "A pleasure to meet you, Miss Caine. My name is Roger, and my companion is named Ambrosio. If you'll follow me to the baggage collection carousel, Ambrosio will take your bags to Mr. Bloch's aircraft, after which I will escort you to Mademoiselle Prudhomme."

"Mademoiselle Prudhomme?"

"Yes, I understand she is Mr. Bloch's personal assistant."

Sara tried to quiz Roger about Mr. Bloch, but it quickly developed that the two had never met and that Roger was simply a concierge for the airport. Once Ambrosio had taken her empty suitcases, Roger brought her to a rented meeting room in the terminal itself; they made small talk along the way, but Roger was not a particularly interesting person.

Once at the correct door, he knocked and the door was opened by an extremely put-together woman who had obviously had work done on her face; her age could have been anywhere from 35 to 50. She had long brown hair left free on top but with the back done up in a loose bun secured by a chocolate brown hair stick. Her facial features were quite attractive, but her forehead was extremely tall and her chin very short, so that it looked like all her features from eyebrows to mouth had somehow slid down; she was striking, though not in an altogether pleasant way.

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