The Case of the Extortive Escort Service

by Souvie

Caution: This Sex Story contains strong sexual content, including Fa/Fa, Mult, Coercion, Lesbian, Group Sex, Oral Sex, .

Desc: Sex Story: Blackmail is no laughing matter. Trudy Tolliver is once again assigned a dirty job, and it's got 'escort service' written all over it...

copyright 2000 and 2002

(A Trudy Tolliver Story)

This was originally posted back in 2000 under the title "Lovin' to Go." A couple areas have been changed and expanded, but for the most part, the plot (if you could call it that!) hasn't changed. And of course it has a brand new, much more appropo title. <g>

If you're not familiar with Trudy Tolliver, you can read about her first adventure, "The Case of the Masochistic Wrestlers" also at StoriesOnline.

I live for feedback.

It's "I write, you read," not "I give, you take." So please don't post this story anywhere without my permission.


"You need four parts sugar, six parts potassium nitrate, and a small container like a Coke bottle, but make sure to perforate it. Once you have all the ingredients-"

I stared at the small television as I walked into the break room. "What are we watching?"

"How to make a bomb," someone volunteered.

"It's a new daytime show. 'Sammy!' or something like that," Melissa said. I sat down at the table with her, my back to the TV set. Melissa worked in copy and we'd gone to the movies and lunch a couple times. She was okay in a sort of bland, vanilla kind of way.

"So what's new, Trudy?" she asked, offering me some of her grilled chicken salad.

"Nothing," I said, taking a bite. "I'm thinking about taking some of my vacation time."

"Where do you want to go?"

"I don't know, maybe someplace warm and exotic and far away from Mr. Peterson's damn bellowing."

Dirk stuck his head in the doorway. "Trudy, Peterson is yelling for you."

I smiled ruefully at Melissa and took one last bite. "Jamaica, I think. Yes, definitely Jamaica."


"You want to run that by me one more time," I said, trying to wrap my brain around what my boss had just told me.

"What part of English don't you understand, Tolliver?" Mr. Peterson asked, rummaging in his desk for a cigar. "You're going undercover as an escort."

"Escort as in escort service?"

"You know of another kind?" He gave up his search, and slammed the desk drawer in frustration. Everyone at the office knew that Mrs. Peterson was trying to get her husband to quit his cigars.

"Why me?"

"Because I just decided to make you this paper's new investigative reporter. You want it engraved in stone or something?"

"Okay, now why?" I settled back in my chair. I couldn't wait to hear his explanation.

"You may or may not know this already, but my sister is married to Councilman Voeks. Someone is blackmailing him. He wants--"

"Isn't that a problem for the cops?" I interrupted.

"Normally, yes, except for the highly sensitive nature of this whole thing. It's election year, and he's being bribed with porno pictures."

I whistled. "Got caught with his hand in the cookie jar, huh?"

He waved a hand in the air. "My sister swears that they're doctored. Either way, we need to find out who's behind it so that appropriate measures can be taken."

I interrupted again. "How can he not know who's blackmailing him?" If this Councilman Voeks was representative of our city government, we were surely on our way to Hell in a handbasket.

Peterson frowned. "The blackmail pictures and demand arrived unsigned by mail. He's supposed to deliver $30,000 by tomorrow at noon to an abandoned building downtown, or else the pictures will be sent to the local rag mags."

"Then how does he know this escort service is involved?"

"Shit, you're full of questions today, Tolliver! Because he goes through the escort service to get a date for society functions when my sister's out of town. He swears the company is legit -- never a hint of anyone coming on to him or propositioning him -- but something doesn't sound right to me. And that's where you come in."

He tossed some papers across the desk at me.

"What's this? I asked, picking them up and thumbing through.

"Your application for employment and some other forms you'll need. I've already placed the preliminary calls. Actually, I had Melissa place them for me. I need as much information as you can get me before 11am tomorrow."

I stopped flipping through the papers and pointed to one of them. "I never had a physical."

"It's required, I guess to make sure the employees are in good physical health. I had Dr. Rosetti fill out one for you."

"Dr. Rosetti from the county morgue?"

"He's a licensed doctor. It'll hold as long as no one goes checking his AMA license." His chair squeaked as he rolled it back and stood up. "Now shake your ass and get."


I stopped at my apartment to get a small bag of clothes together. According to my cover story I was Trudy Thicket, fresh off the bus from Kansas and in desperate need of a job and place to stay.

I was debating on whether or not to change out of my jeans when Remy stuck his head inside the door.

"Okay, you are home. The outer door was open so I just let myself in," he explained, leaning against the doorjamb.

"Yep, but not for long. Whatcha need, Remy?" I gathered my hair up in a ponytail.

Remy lived in the apartment below me, and was a private investigator. The epitome of "tall, dark and handsome," he was the subject of most of my late night erotic dreams. I'd never tell him that, though. We had a nice, simple, friendly relationship and I liked it that way. From all indications, he did, too. Sometimes fantasies are nicer when they never come true.

"I don't need anything."

Remy never just lets himself in. He looked about as nervous as a class jock at a high school reunion. I looked him dead in the eye and raised my eyebrows.

"Okay," he said, smiling sheepishly. "My apartment is being painted tomorrow and I wanted to know if I could crash here for the night?"

"What about Maria?" Maria was his current love du jour.

"She's got to go out of town, her mom's sick."

"Why don't you crash at her place then?"

"We haven't been dating that long. Plus she's shy and well, I don't exactly feel comfortable asking her."

I shrugged. "Okay then."

"There's just one more thing."

I sighed. There always was. "Which is?"

"I don't want her to know I stayed here. I don't think she'd get jealous, but like I said -"

"Yeah, yeah, you haven't been dating that long." I zipped up my overnight bag. "I won't be here tomorrow night anyway, so I don't see a problem. I'll give you the extra key now, and you can just lock up when you leave."

He grinned and hugged me. "Thanks, Trudy."

"No problem. Oh, while you're here, got any suggestions for subtly altering my appearance? I don't need anything drastic or permanent -- just something so that I wouldn't be easily recognized." My picture had been in the paper recently because of a big wrestling case, and I didn't want to take the chance that anyone at the escort service would recognize me.

"Hmmm. I've got that long black wig I wore last year when I was investigating a company for insurance fraud. You could wear that; it's not one of those super cheap ones where you can tell it's a wig. And you could touch your eyebrows up with mascara. That way it won't look like a dye job."

"Thanks, Remy, you're a lifesaver!" I kissed him on the cheek. I could have sworn he blushed. "You go downstairs and find that wig, and I'll just do the mascara touches and be down shortly."


Discriminating Delights was in a high-class business slash residential section of downtown. It was not what I'd been expecting. The office was in a renovated colonial style home, traces of old wrought iron fence posts framing the front entrance. The trim was done in a light pink color with a gazebo off to the side, a profusion of roses climbing up the trellis.

I walked up the brick path and through the large oak doors. A receptionist in a room off the foyer took my name and asked me to have a seat. I looked around, feeling like a hick on her first time to the big city. The understated elegance of the whole place had me wondering if I'd gotten the address right.

"Mrs. Coopersmith will see you now." The secretary's voice broke through my perusal of the room.

I shouldered my overnight bag, and walked through the door that the secretary had gestured to. An older woman was inside, sitting behind a large desk, and she smiled and stood as I entered. "Trudy, so nice to see you. Please, have a seat."

I sat in one of the plush chairs in front of her desk, and automatically handed her the sheaf of papers that Mr. Peterson had prepared for me.

She took the papers, and started rifling through them. She asked me some basic questions: Where was I from? How long had I lived in Dallas? Why did I want to be an escort?

I'd rehearsed what I would say on the drive over, so I answered her with confidence.

Mrs. Coopersmith put me at ease. With her upswept hair, chic suit and friendly demeanor, she reminded me of someone's well-to-do grandmother, not the owner of a successful escort service and potential blackmailer. I wondered what was wrong with her.

"Well, Trudy, all your paperwork is in order, and your physical checks out just fine. I'm willing to take you on a one week trial basis if you're still interested."

"Oh, I am!"

"Good." She looked at the top paper again. "I understand that you don't have any place to stay, is that right?"

"Yes, ma'am."

Her laugh was as clear as newly spun glass. "Please, just call me Constance. We're not that formal here at Discriminating Delights."

"Okay, Constance."

"Very good. Now, I'm writing down Cynthia's address. She's one of my most popular girls and she's got a spare room you can stay in until you get on your feet."

"Are you sure she won't mind?"

Constance handed me a piece of paper with an address on it. "She won't mind if she likes her job." She smiled and stuck out her hand. "Welcome to our family."


Cynthia lived in an upscale condo with an Olympic sized swimming pool directly behind it. I thought that if most of the escorts had similar places, I was in the wrong line of work.

A girl wearing workout clothes answered the door. "Hi, you must be Trudy. Constance called to let us know you were coming over. I'm Priscilla," she said, stepping aside to let me enter. From what I could see of the condo during Priscilla's quick tour, it was almost as nice as the company's office.

Priscilla led me upstairs to a room at the end of a long hallway. "This is your room. I'm right across the hall, Cynthia's roommate, more or less."

The room was huge. I could have fit my whole kitchen just in the closet alone.

While I put my clothes away, I kept glancing at Priscilla from the corner of my eye. She looked awfully familiar, but I couldn't quite place her. "Where is Cynthia?" I asked, placing my empty bag under the bed.

"It's her turn to do the grocery shopping. She should be back soon."

The phone started ringing and Priscilla reached across my bed to the phone on the night table to answer it.

The conversation was brief and she scribbled something down on a piece of paper. When she hung up she said, "That was Constance. You've got a date tonight. Mr. Adams will pick up you at 8pm, for the opera."

"Already?" Damn that was quick.

"Yes, it doesn't take long for her to 'initiate' you to the business." She laughed. "If you stay in this line of work, one thing you won't lack for is a date. Do you have something to wear?"

"For the opera? No."

"You're about Cynthia's size. I'm sure you can find something in her closet that's appropriate."

"I've got it!" I said, snapping my fingers and giving a Cheshire cat grin. "You're Priscilla 'Princess' Carver aren't you?"

Her face turned a pale white. "Oh, God." She sat down on the bed. "I knew someone was bound to recognize me."

"Your face was plastered in all the papers when your father threw that 21st birthday bash for you last year. It's not everyday the daughter of the premier oil baron of Texas turns 21."

"You're not going to tell my father what I do for a living, are you?" she asked in a quiet voice, looking up at me with worry in her eyes. "He thinks I'm modeling."

"I won't tell," I answered, sitting beside her and putting my arm around her shoulders. Call me crazy, but the cute little waif was already starting to grow on me. Maybe because she reminded me of the kid sister I'd never had.

"I need to tell you something before Cynthia gets home," Priscilla said in a low voice.

"Priscilla, get your bitch ass down here and help put up these groceries!" The front door slammed shut, and I could hear high-heels tapping across the tile floor.

"Too late," Priscilla said with resignation. "Coming!" she yelled back and left me sitting there on the bed.

I wondered what she'd been about to say.


Within the first five minutes of talking to Cynthia I'd come to the conclusion that she was a self-centered, stuck up little cunt. She'd informed me that if I was to be staying there, it was her way or the highway.

"Some of us girls do a little work on the side," she explained while she sifted through her closet, looking for something that would fit me. "You live here, you're going to do it, too. If not, I call Constance and your ass is back on the street."

"What do you mean by 'a little work'?" I already had a pretty good idea, but I wanted to hear her say it.

"You look pretty smart, Trudy, I'm sure you can figure out what I mean." Cynthia tossed me a black strapless gown, floor length -- a Versace, if I guessed right. It probably cost a month of my salary. "Ruin it and you'll pay me for it." She crossed to her dresser. It was only when she started to sort through her keys that I noticed one of the drawers had a lock on it. She unlocked it and took out a small wirebound book. "For the after hours stuff we all have code names. Yours will be... Trixie, I think." She wrote something down. "I've got an appointment with Sam tonight, about 1am or so. It's a two-person job so you'll come with me. That way I can watch you in action and know if you're going to give me any shit." She snapped the book closed and gave me a look that practically dared me to make trouble. "Any questions?"

Without a word, I turned around and walked back to my room. I flopped down on the bed and sighed. Remy, hunk extraordinaire and star of many of my wildest fantasies, was spending the night in my apartment, and I was stuck being an escort for some stranger. Life wasn't fair.


Mr. Adams turned out to be a kindly old gentleman, a retired lawyer who was so polite to me, you'd have thought we were related. He took me to see Phantom of the Opera and I had one of the best times I'd had in a long while. He told me all about his son who'd taken over the firm and just opened a branch office in Ft. Worth, how his wife had died recently of cancer, and how his granddaughter had just been accepted to Vassar.

He dropped me off back at Cynthia's condo and gave me a chaste kiss on the cheek. With a smile and a wave, he climbed back into the limo.

I had less than 30 minutes until the "1am or so" that Cynthia had mentioned earlier. I went up to my room to change clothes. She hadn't said what to wear, so I grabbed one of the few outfits I'd brought: denim mini-skirt, blue western-style shirt and some low sandals. I went to walk back downstairs when I noticed that Priscilla's light was still on. I tapped quietly on the door and then opened it. She was laying on the bed, dressed in a frilly nightgown, an open book on the bed in front of her.

"How was your date?"

"Surprisingly, I had a great time."

She smiled. "Good. I'm sorry I didn't have time to warn you about Cynthia earlier."

"It's okay," I said. "Are you in her little book?"

There is more of this story...

For the rest of this story you need a Registration + Premier Membership
If you’re already registered, then please Log In or Register

Story tagged with:
Fa/Fa / Mult / Coercion / Lesbian / Group Sex / Oral Sex /