In Racquel's Capable Hands - An Erotic Novellette

In Racquel's Capable Hands - An Erotic Novellette

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


From Jay Gaudette - As a business shark, keeping my life straight is a constant struggle. That's why I have to have a assistant to manage my business life...and my personal life as well. Racquel was the best. She could do it all, and then some. This is the story of how she became my personal assistant--my wingman--and how she rocked my world. In TWO parts.


From Jay Gaudette - As a business shark, keeping my life straight is a constant struggle. That's why I have to have a assistant to manage my business life...and my personal life as well. Racquel was the best. She could do it all, and then some. This is the story of how she became my personal assistant--my wingman--and how she rocked my world.
In TWO parts.

Chapter1 (v.1)

Author Chapter Note

From Jay Gaudette - As a business shark, keeping my life straight is a constant struggle. That's why I have to have a assistant to manage my business life...and my personal life as well. Racquel was the best. She could do it all, and then some. This is the story of how she became my personal assistant--my wingman--and how she rocked my world.

Chapter Content - ver.1

Submitted: June 08, 2015

Reads: 1276

A A A | A A A

Chapter Content - ver.1

Submitted: June 08, 2015



In Racquel’s Capable Hands
Part 1
Jay Gaudette’s Friends and Lovers
By Jay Gaudette
©2015 Jay Gaudette

This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

A note from Jay Gaudette

Hi. I hope you enjoy this great entry from my Friends and Lovers series of short stories. It’s a hot tale about my personal assistant, Racquel, and how she got and held onto the job of taking care of me, professionally and personally.

As a gesture of expressing your approval and appreciation, I hope you’ll consider leaving me a small tip via PayPal. Visit the link on my blog at jaygaudette dot blogspot dot com, and you will be directed to my tip jar.

Thanks in advance.

Now, enjoy In Racquel’s Capable Hands.


I meet many women in my travels. It doesn’t matter where I am—LA, Las Vegas, New York, London, Moscow, Tokyo, wherever—there is always an opportunity for me to enjoy some of the most beautiful women on the planet. That includes working professionals.

I enjoy booking a woman for an hour, an evening, or a night. Have a yen for Asian? No problem. Want some young tart? Check. More mature? Yes. Whatever your tastes, there is a professional courtesan who will gladly fill the bill. There are some skanks out there who are trouble, but you learn how to avoid them. However, for the most part, professionals don’t fuck with you when they fuck you. The vast majority of them are earnest babes who like what they’re doing and will gladly share their passions with you. I also like pros because they give you what you want. My tastes run the gamut from heavy kink to relaxing romantic sex, and it’s never a problem finding a woman who will take care of things the way I want them to be taken care of.

If I want a quick fuck, I generally am not too picky about age. Younger is fine. But if I want to go out in the evening for drinks or a party, I make arrangements with a woman closer to my age, a MILF or a mature woman. I guess I don’t want to look like I’m dating my niece. But I also find that older professional women tend to not watch the clock as much and, quite frankly, seem to be more appreciative of the attention. They put more of their body and soul into their services.

Interestingly, with all of the glamorous cities that I visit around the world, with all the variety of very high end escorts and courtesans available, my favorite pro is located in, of all places, Kansas City, Missouri. She’s a red-hot mature babe named Racquel.

She’s in her early to mid forties and is a very desirable woman. With a great body and a very pretty face, Racquel runs rings around many younger babes. However, the thing that sets her apart from the rest is her attitude. She is one of the most bubbly, affectionate, fun loving, and enjoyable women whom I have ever met. She’s smart too. Moreover, men, I’m here to tell you, her sex skills are unbelievable.

The Kansas City metro area, especially the Kansas side of the state line, has produced some very good commercial real estate investments for me, and I make it a point to inspect them every now and then. (I always try to mix business with pleasure during my travels. Thank you, IRS, for providing a way to write-off my sex tourism.) My favorite hotel in KC is The Ambassador, located in the middle of downtown. The suites, services, and staff are first rate, and they have a large bar in the lobby where the KC power set gather for drinks most evenings. I usually make some good contacts there.

I dropped an email to Racquel to let her know I was coming to town and that I wanted to hook up. But on that particular trip, I wanted to do something more interesting than the norm. I wanted to do a full-on role-play with her in an Oscar caliber leading actress role. I paypal-ed $3,000.000 to her for a twenty-four hour rendezvous, and I filled her in on the details of the role-play I had in mind. But as you’ll see, it went in an entirely different direction.


I arrived on Sunday evening and prepared myself for a busy week, at least the first several days, by ordering in a couple of young hotties for a quick two-girl party. They were quite the pair. The one girl, Liz, was a vivacious, blonde, prototypical, Midwestern girl, with an incredible body and a bubbly personality. The other was a demure brown-haired girl, Suzie, who seemed submissive to Liz and had a penchant for wanting big things shoved down her throat.

At the beginning, the blonde chick, Liz, excused herself to go to the bathroom. (That’s the standard set up where the money is left.) Suzie and I were alone in my suite’s living room. At first, she seemed hesitant, almost shy. While I sat on the couch, she approached me with a demeanor that said that she didn’t quite know what to do next. She nervously stood there and bit on of her fingernails.

“What’s the matter, doll?” I asked her.

“Nothing,” she said. “I’m fine. I just like my friend with me, that’s all.”

“You’re new at this, aren’t you?”

“This is only my second time,” she said timidly.

I told her, “If you’re really uncomfortable, you can sit on the side and watch.”

“No, no. It’s okay. I’m into it.” She tried to be enthusiastic.

I took her hand and pulled her to me. She sat on my lap, and I ran my hand up and down her body. Her breasts were small and firm, and her skin was smooth and fresh. She was like a freshly picked fruit; succulent and ready to be tasted.

I asked her, “What do you like to do the most?”

“I like to use my mouth. I like to blow things; dildos, bottles, cucumbers, anything.”

“What about dicks? You like sucking cock, don’t you?”

She giggled, “Well, yeah, sure. I love cock in my mouth. I love to give blowjobs.”

“You swallow?” I asked.

“Cum? Sure. I love it going down my throat.”

Liz came in and mock-scolded us. “Well, shit, you two; you starting without me? I’m here to fuck too, you know.”

I stood up and let the two of them strip me. Suzie, after she quickly took off her sundress, dropped to her knees and easily rammed my hard man-meat into her mouth and down her throat.

Liz laughed, and with a country twang said, “Damn, she loves dick in her mouth. She hardly has any kind of gag reflex at all, and she fucking can’t get enough of it. You want to see a real neat trick we do?”

“Sure, I’m game for anything,” I told her. I was too.

“Cool, baby.” Liz then grabbed Suzie’s hair and roughly yanked her head off my dick, kissed her on her lips, and said, “Get the toy, honey.” Suzie obediently crawled over to where her large purse was and pulled out an 18 inch long, rubbery, purple dildo. Liz then took it and ran it along Suzie’s eager mouth. She licked and moistened the monster dong with her lips and tongue. Liz giggled, “This is so cool. God, I love this part.”

With Suzie’s head in a headlock, Liz started the end of the dildo down the little girl’s throat. Deeper and deeper the purple monster slid down while Suzie gagged every now and then. Her eyes were big, and they watered while the dominant Liz tightly held onto submissive Suzie’s head.

Finally, down to the handle end, Liz grabbed it firmly and pulled it back out; almost all the way, just until the working end of the rubbery snake just came up into Suzie’s mouth…then she brutally forced it back down all the way. Suzie moaned loudly and gulped pathetically, but allowed herself to be brutalized. Liz pulled and pushed the big dong in and out time and time again until she and Suzie fell into a oddly comfortable rhythm. It was mesmerizing to watch. Liz, busty and rough, pummeled the monster cock-dildo down the throat of her little girlie slave, Suzie.

I sat on the couch and stroked my cock. Suzie saw me, reached up to me, pushed my hand away, and took over. Soon, her strokes of my cock matched the pummeling of the dildo down her throat.

Suzie then grabbed at Liz and broke the headlock. With surprising force, she slammed Liz onto her back and kissed her wildly. “I need a cock in me, Liz. I have to have a cock in me,” she wailed. She looked at me with mournful eyes, cried, and begged, “Please, sir, fuck me. I beg you, fuck me. I have to have it.”

It was time for me to take over. I grabbed Liz and threw her up on the couch. Suzie immediately dove her mouth in between Liz’s legs and ate her cunt ferociously. I then grabbed a rubber, put it on, and smashed into Suzie’s ready love-hole from behind. She grunted with every thrust. Liz pulled her legs out of the way as much as she could and grabbed onto Suzie’s head, forcing her mouth ever deeper into her gash. Finally, I felt that I was ready to explode. I grabbed Suzie’s hair and pulled her away from Liz’s muff. I turned her around, peeled the condom off, and smashed my rod into her mouth and all the way down her throat. She expertly sucked on my cock and eagerly swallowed every drop that I shot into her. Liz sat on the couch, encouraged us, and rubbed one out for herself.

It was a great way to start the week.


The first several days in Kansas City were filled with all the standard meetings and inspections that are part of the routine for that kind of trip. I was busy, and my schedule was jammed as I jumped from one appointment to another. It was normal.

There’s this idea that the kind of life I lead is easy street; a comfy cozy lifestyle. Nothing could be further from the truth. It’s nice, but when you’re a hustler like I am, when you land in a town, you’re on the go eighteen or so hours a day. It’s hard work.

 After my last meeting on Wednesday afternoon, I punched out of business mode, returned to the hotel, and headed to the bar. It was time for the best reason for going to KC, and I looked forward to it.

It was crowded with all sorts of business types: junior execs, presidents, middle-rung drones, and lots of hot women dressed in their best business suits. I think an attractive woman in a tailored business suit is an absolute turn-on, so I enjoyed the scenery. I sat down at the bar, ordered a drink, and waited for the fun to begin.

Oh, there is one thing about Racquel that is a bit of a drag; she’s always late. But being the smart guy that I am, I set things up for her to arrive at 4:30, which meant she was right on time at 5:30. Normal.

There was a noticeable hush in the room when she entered the lobby bar area. Racquel looked incredible, and many of the businessmen stopped mid-sentence to catch a good look at her. She wore a very nicely fitting dark blue suit with a subtle pinstripe. Her silk blouse had light ruffles, and its neckline plunged just enough to give only a slight peak of her cleavage. Add to that, her cum-fuck-me high heels made her silhouette tall and lean. She also received jealous glares from quite a few of the women there. You could almost hear them say, “Who the fuck is this bitch? She’s amazing.”

She found a seat at the other end of the bar from me. Almost immediately, several men there took a shot at her. They walked up and introduced themselves or tried some lame come-on line on her. She shot down every one of them with a gentle gesture or a few small words.

A slovenly looking and acting guy who sat next to me said, “Well, shut the door, would you? Hey, bud.”

“You mean me?” I asked.

“Yeah. You. Do you see that brunette over there?”

As if I hadn’t seen her yet, I looked over in Racquel’s direction. “You mean the one in the pinstripe?”

“Yeah, her. What the hell—are you blind? Wow.”

“I see her. Cute.”

“Cute? She’s a major smoke show.”

“I guess she is. Yeah.”

I don’t know why, but the idiot got a little pissy with me. “Are you blind? She’s incredible.”

I enjoyed fucking with that guy’s head. “You’ve seen one babe, you’ve seen them all.”

“You’re not from around here, are you?” he asked.


“Well, for KC, she’s exceptional. I mean, she’s way better looking than most of the women is this cow town.”

“That’s not a very nice thing to say. I’ve been around. KC has a lot of nice looking women.”

“Yeah, there are, I guess. But this isn’t Southern California, where awesome babes grow on trees. This is the border of Missouri and Kansas. Trust me—she’s the exception, not the rule.” He was about to make some other shitty remark about Midwestern women when he stopped cold and asked, “Wait a second. Where’d she go?”

We both then heard a woman’s voice from over our shoulders. “Hi. I’m so sorry, but I think I know you.” It was Racquel.

The surprised barstool jockey sat up and straightened his tie. Thinking that Racquel had spoken to him and he had hit the jackpot, he smoothed back what little hair he had left and bravely attempted a comeback. Sure as hell, he got all tongue tied and flustered. She then threw a get-lost-you-asshole glance at him that crushed his manhood. Embarrassed, he got up and left. Racquel then sat down in the newly available seat.

“I’m so sorry for disturbing you and your friend,” she said to me.

“No, no. He wasn’t a friend; just some guy. You said you thought you knew me.”

“I’m so rude. My name is Racquel; Racquel Daly. You’re Jay Gaudette, aren’t you?”

“Yes, that’s right. It’s a pleasure to meet you, Racquel.” We shook hands.

“The pleasure is all mine. I just knew it was you. This is so lame, but I’ve been studying you.”

“Really? What do you mean?” Her “studying” me was not part of my role-play outline I had sent to her, but I liked the angle.

“I know that you’re a major investment property player, and that kind of thing interests me greatly. It’s something that I would like to learn how to do better.”

“Better? You already have some real estate investments?” I guess it never occurred to me that she, a “professional woman”, might have aspirations in other areas.

Racquel answered, “Besides the house I live in, I own a small four unit apartment building on the south side of town, not too far from here.”

We talked numbers for a while, and she exhibited that she had a good grasp of the basics. However, it was also apparent that she was at her limit, both in her knowledge and skill set. I then revisited something she had said early on. “I’ve never been studied before. What else do you know about me?” I liked the direction the role-play took.

“Well, you started out with mostly small retail and rental residential property. You then moved to larger retail and commercial property; mostly office, but a few industrial parcels. You then made your biggest move—you bought up empty undeveloped parcels in Chicago, Dallas, and Phoenix, then leased them out to fast food franchise developers; well, all different kinds of franchises; oil change, gasoline convenience marts, things like that. Then you broke into government properties; mostly for agencies like the Social Security Administration and the Department of Defense. Your biggest play was with the United States Post Office.”

I was shocked. She really had done her homework on me and nailed what my trajectory had been to date. Impressive.

She continued, “But I do have a question. What triggered you getting out of lease-backs on post offices? I mean, your timing was perfect, but what made you decide to do that when you did?” Again, she showed that she had done some research. I held the leases on several hundred post office buildings, but dumped them about eight years ago.

“Pretty simple, really. I was sending out fewer and fewer communications via snail mail. More and more of it was email. I figured if I had been doing that, and I’m not a tech guru by any measure, so would a lot of other people. Electronic communication was the future. The Post Office was not. I knew that it was time to get out from underneath those leases before they became albatrosses around my neck.”

“And you made quite a profit,” she continued. “At least that’s what American Properties Magazine said.” The magazine did a short profile of those transactions and me. They didn’t release specific monetary details, but their inferences were spot on. I cleaned up.

“I was fortunate. My timing was good, but it doesn’t always happen like that.”

“Perhaps not all the time. However, from what I’ve learned about you, it happens way more often, and more profitably, then not. That excites me.” She lightly ran her fingertip along the base of her neckline. “That excites me a lot.”

“It’s all about money,” I said. It was at that point that I noticed that she had unbuttoned the top button of her blouse. I don’t know how I missed that small detail. I guess I had fallen into her role-play headfirst. I don’t know. She leaned into me more. The view was incredible, especially when she sneakily pulled the fabric open a little. What a tease!

She then said, “I love money, Mr. Gaudette. I’d do just about anything for more of it.” She licked her lips. “Mmm. Money makes the world go ‘round, doesn’t it?”

“It certainly can make things happen; lots of very interesting things.”

She then leaned back into her barstool, and displayed her long slender figure to me. It was as if she offered herself for my perusal. She continued. “How do you do it?”

“Do what?” I asked. Racquel had me on the ropes. She was twisting me around, but in a way that I enjoyed. It was fun.

“I mean, you’re a world traveler, a mover and shaker, a major player. You’re a shark, but not just any shark. You’re a great white shark looking for a kill. How do you manage all of your activities? How do you keep it all straight?”

I chuckled a little under my breath at that. Truthfully, it was very hard for me to keep all my obligations and very personal time straight. “It’s a little tough. But I am an app junkie, and that helps some. But my schedule does get screwed up occasionally.”

“You don’t have a wing man—a personal assistant—someone to help you?”

“I used to, but it didn’t work out. He didn’t really have what it takes.”

“Tell me about that. It seems to me that someone as important as you should have everything you need … or want.” Wow. Racquel dug in deep. What I had intended on being a simple “Hi, let’s fuck” thing had turned into something much, much more involved. I liked it.

I said, “A wingman, or wing-woman, has to be totally on top of everything. Absolutely no balls can be dropped, ever. And frankly, my last wingman fucked up a couple of times and it cost me some money. The last time that loss was in six figures.”

“Oh, that’s terrible,” she said. It was terrible. When that happened, I fired the guy on the spot and sent him home. Racquel continued, “That can’t happen. What does your wingman have to do?”

“The first thing is they have to take care of all my travel arrangements: airplanes, rental cars, limos, whatever. They then have to make sure that my hotel and resort stays are all lined up. I’m not an overly picky traveler, but I do have some standards. The hotels don’t always have to be five-star, but I won’t stay in a dump either. I would also like them to have some business acumen. They’d have to keep track of all my appointments and notes; make sure I have all my resources lined up and instantly available. I also want them to be able to see and hear what’s going on, and give me feedback.”

“How are you getting all that done now?”

“Well, for my air travel, I subscribe to a jet charter service. When I need to go somewhere, I call my account representative with them and she makes the arrangements. She’ll even arrange commercial air travel if that’s what called for.”

“How about your hotels?”

“Online. Just like everyone else.”

“Ground transportation?”

“The same.”

She followed a professional sales fact finding script perfectly. I’d like to say that I just went along with it as part of the role-play, but she had me engaged in the subject from a personal perspective.

I’m a highly trained and effective sales pro myself. I knew exactly what her next question was. She asked, “Jay, what would you change about that? Or how would you make it different and better?” Bingo. She nailed it. She had me.

“Well, Racquel, I really don’t like to fuck with any of it. I’d like to have someone who took care of all of that for me so I can concentrate on my business. Those kinds of details are distractions I don’t need.”

 “Jay, I understand, and others have felt the same way too. If I were to show you how that could happen; how your time and efforts could be maximized fully, you’d be interested in that, wouldn’t you?” Again, she nailed it.

Her phrasing was perfect. She asked the question in such a way that compelled me to answer it affirmatively, and truthfully. “Yes, Racquel. I’d be very interested.”

Now, if she had been trying to sell me only on her becoming my wingman, she would, at that point, have gone into a close. But she didn’t. She had something more heavy duty in mind.

She went for it. “Jay, role-play aside, I know a lot about you. I know all about your business success. But I also know a lot more about you. I know a lot about your more personal side.”

“Well, you should. We’ve partied together quite a few times,” I replied.

“You’re more than that, Jay. For instance, I know about how you spread not only your money around, but how you provide opportunities for others, the scholarships you sponsor, the job training you pay for, how you’ve given back to others. I know about how you provide for not only your family, but others as well. You’re a very kind and generous man. And you’re a very good man. You’re strong and successful. You’re a very important man, and you deserve the very best in life. Who takes care of you? Who takes care of what your needs are and makes sure that you are always relaxed and, well, happy?”

“Racquel, you know as well as anyone that I….”

“No, no, no. Not just great sex. That certainly is important, but you need more than that. You need support. Don’t you agree?”

Holy shit. That was a hell of a trial close.

“What do you have in mind, Racquel?”

She quietly said, “Jay, I admit that I get turned on by powerful, strong, successful and, to be frank, rich men, like you. And again, to be frank, this whole conversation has gotten me pretty wet and turned on. However, I want to approach you from a totally different angle. I think it’s terrible that you don’t have someone with you when you travel to make sure that not only Jay Gaudette, the businessman, is taken care of, but Jay Gaudette, the total man, as well. And I think that it’s not right that you, shall we say, have to outsource your release and pleasure. I think that you would benefit greatly if you kept it in-house.

Jay, you’ve always been straight with me, and you’ve always treated me with respect. I like you. I think that I can bring real value to your life by being your wingman, your personal assistant, your personal helper. You have a lot to do with your business and investments. You shouldn’t have to screw around with little bullshit details—all the little crap, like where your limo is or if your hotel is good enough for you. And you also need someone to interact with you who’s in your corner; someone who has your interests as their number one priority. I could do all that for you.”

At that point, my mind was totally turning around. This was supposed to be a fun fuck night. It turned into a job interview, and frankly, I liked what she had to say. Clumsily, I asked, “Do you have any college?”

“Bachelors in Financial Management from University of Missouri – Kansas City.”

“Racquel. Be real with me here. Really?”

“Mm hm. I’ll show you my diploma, if you want.”

I was totally intrigued by what Racquel proposed. It did sound terrific, but I was still hesitant. “I’m not sure, Racquel. I could use the help, but I’m just not sure, I mean you….”

“Jay, I understand that too. I’m not fooling.” She then opened her purse and handed me an envelope. I took a quick look in it. It was the amount, in cash, that I had paid her for the role-play. She then closed me. She stood up, pressed herself against me, and whispered in my ear. “Don’t you agree that having me as your wingman would improve not only your productivity, but make your life much better? You’d save time, hassle, and make more money. I can do all that for you, and more.” She then kissed me and said. “Call me with your decision.” And she left.

Holy crap. I was stunned.

After Racquel left, I ordered another drink and thought about everything that just happened. There I was, hoping to get my dipstick checked by my favorite escort, and then, boom, there I was on the receiving end of one of the best prospective employee interviews I’ve ever witnessed. And I seriously thought I should hire her to be my wingman.

There were a lot of pros and cons about it. On the plus side of the ledger was the fact that I did need some help keeping my hectic life in one piece. I mean, I managed on my own well enough, but to have someone take care of all the bullshit details was very appealing. I definitely could be more productive and less stressed out if someone helped me. And Racquel also presented herself very well. She looked great, apparently had a degree, and knew what the job entailed. At least I thought she knew. She was also damn positive and smooth about it. I believed her.

However, on the minus side was the fact that all I’ve ever known her as was as an escort, a whore, and one badass fuck. Man, she could suck the lead of a pencil. Did she really have the sophistication and savvy to be my assistant? I don’t want to sound derogatory and judgmental, but whores don’t usually rank high in the brains department.

Then, back on the plus side, there was the whole thing about her taking care of not only my professional needs but my personal needs as well. That sounded very attractive. And I wouldn’t have to dump my sex tourism lifestyle if she was onboard. If I wanted to fuck around when she’s out on the road with me, all I had to do was tell her to go back to her room and relax. Or maybe she could broker some action for me, and even join in. Hmmm.

Then there’s the whole thing about the money. She handed me an envelope with $3,000.00 in it; the money I paid her for the role-play and a 24-hour sleepover. She just gave it back to me. She had to be serious about wanting to be my wingman, or she wouldn’t have done that. That was some serious shit.


I invited Racquel back to my hotel the next afternoon to give her my decision. For the first time I could remember of all our dates, she was on time. When she entered my suite, she immediately went to the couch and sat down. I stood in front of her and imposed myself on her. She submitted to my dominance. I handed the envelope with the cash in it back to her and told her she could keep it. She looked at me with kind of a surprised look on her face.

I told her, “Racquel, if this is going to work we have to get some things very, very straight.”

“Yes, sir.”

“First and foremost, if all of that you said last night was all a bunch of bullshit, and I let you travel with me, and at any point you embarrass me…I swear, I’m not a violent man, but I’ll kill you. All a man has to bargain with, besides capital, is his reputation, and mine is impeccable. I routinely make deals in the tens of millions of dollars just on my handshake and my word. I will not put that at risk to any degree. Do you understand?”

“Yes, sir. I’ll be a credit and an asset to you.”

“And don’t you ever be late for anything I ever set up. That’s the quickest way to get your ass kicked as far away from me as I can kick it. Do you get it?”

“Yes, sir. I get it. Loud and clear. Never late. Never.”

“And I am the boss! What I say goes. You have to do whatever I tell you to do. Slip up even once, I’ll dump you like a bad habit wherever we are…and I go to some pretty unpleasant places.”

“Got it, sir. Yes, sir. I won’t let you down.”

I was very anxious and a bit angry about the arrangement. But there was something positive there. Amongst all of the possible potential risks about her being my wingman, I felt I could have some confidence about it. It was a gut play, but for some reason that was good enough.

“Mr. Gaudette, I want you to know that I’m very grateful for this opportunity. I know that everybody thinks that I’m just a whore. I want to do better than that. I can do better than that. I’ve just never known how. When I started looking at you more closely for the role-play, I felt that maybe you can show me how to get out of the pit that I’ve been in. When I was younger, I wanted to be like you—productive, successful—but I didn’t know how. Please, teach me. I’ll be a good student, and I’ll be the best wingman that you can have.” She then took out a folded piece of parchment paper out of her purse and handed it to me. It was her diploma. She told me the truth about that.

I asked her, “You have a stinking degree, for crying out loud. How did you get so sidetracked?”

“I made some really bad decisions when I got right out of college. There was this guy that I was really turned on about. Well … you probably know the story.”

“Were there any drugs?

“No, sir. No drugs. But there was swinging and shows. I got in deep very quickly, and I couldn’t ever seem to be able to find a way to get out of it.”

“If you want to get out of the sex business, why are you offering yourself to me like this?”

“Because I love sex. I mean, I really, truly, honest-to-god love it. There is nothing I like more than getting boned or giving a sloppy blowjob. I have a tight pussy that is ultra-sensitive, and I love the taste of cum. And I know that in this arrangement servicing you is part of the deal. I’ll be your slut. I’ll do anything for you. I know what I’m taking on.”

“Are you sure? One of the things I use women for is to take out my frustrations. I can be rough.”

“I know you can. I’m good with that.”

By that point, I was god dam worked-up about the whole thing. I reached out, grabbed her hair, and yanked her down onto her knees. I tilted her head back and ordered, “You will always call me either ‘Mr. Gaudette’ or ‘sir’. You will answer to me by your name or ‘slut’.

“Yes, sir, Mr. Gaudette.”

“Blow me, slut.”

“Yes, sir.”

She immediately undid and dropped my pants. And while she gobbled my cock into her mouth, I grabbed her head with both of my hands and pounded my rod down her throat as hard as I could.

“I want this from you anytime I want it, slut,” I grunted at her.

“(gulp) Yes, sir.”

“And I’m going to fuck you anytime I want.”

“(gulp) Yes, sir. Anytime, sir.”

“And you’re going to love it every time.”

“(gulp) Yes, sir. I love it, sir.”

“And you’ll offer yourself to me exclusively. No whoring behind my back. You’re exclusive.”

“(gulp) Yes, sir. Only you, sir.”

“And I’ll pay you ten grand a month, month to month.” I went overboard on that, but what the hell; I was really jazzed.

“(gulp) Thank you, sir. You won’t regret it. I’m worth every penny. I promise.”

When I came in her mouth, she sucked down all my jizz until I was dry.

While she wiped her mouth with the back of her hand, she gasped, “Was that good enough for you, sir? Did I prove that I’m serious about being your wingman and your personal slut?”

I threw her onto the floor and ordered, “Go home and get ready to travel. We leave for Palm Beach, Florida in the morning. We’ll be there for the weekend. Bring one business suit; the rest the time will be business casual. Be back here tomorrow at 10:00 am, sharp.”

“Yes, sir. Thank you, sir.”


Racquel arrived at my hotel suite on Friday morning at 9:59 am; right on time. So far, so good. She then picked up the phone on the nightstand and called the front desk to get a bell to come up to the room and get my luggage. On top of that, she had already talked to the hotel and had a taxi ready for us. Not bad at all.

A charter jet waited for us at the airport. We loaded up and took off.

Somewhere over southern Missouri, or maybe it was Tennessee, she said, “Sir, I’ve never been on a private jet before. This is cool. It’s beautiful and very comfortable; not like being crammed into a coach flight like a sardine in a can.” She was, obviously, excited about all of it, and her enthusiasm rubbed off on me too.

“It’s nice. You’ll get used to it. I don’t want to sound like a kid, but this kind of lifestyle, is, well, fun,” I said.

“Is this how you travel all the time?”

“Most of the time, yeah. It depends on where I’m traveling to and from. Sometimes I take a commercial airline, but only if first class is available. I don’t sit in coach, ever. I also like to drive. If a destination is close enough I’ll rent a car and make a roadie out of it. Look, there’s a lot of details about it all and probably too much to take in this quick. But you got off on the right foot by being on time. Having the taxi waiting was a plus. If this weekend works out, I’ll teach you all the ins and outs of how to manage my life. But for this trip, I primarily want to see how you think on your feet. I want to see if you’ll shine or freeze up.”

“Mr. Gaudette, what exactly is this trip all about?”

“We’re attending an investor junket. A company trying to get investors to bite into their investment scheme or idea sponsors a weekend party time. They get a bunch of us to fly to some locale, usually a high-end resort where they wine and dine us. At some point, they have to throw in some business-y kind of shit to be able to get the tax write-off, but for the most part, it’s a party. There’s lots of food, booze, usually some drugs, and almost always a bunch of women to keep the men attendees focused on whatever the promoters are promoting.”

“I’m familiar with the party aspect. Done some myself, but they weren’t investor functions; mostly sports and chest-pounding guy events, like the Super Bowl.”

“I usually skip these kinds of phony-baloney things, but I’m meeting up with a shark who is going to be there, mostly for the booze and babes. I caught wind of what his next play is going to be, and I want to be involved.

“What’s the shark’s name?”

“George Rambley. He’s from Atlanta, and he’s got himself entrenched in a niche that I like; automated warehouses for product distribution for online sellers. Rambley seems to know what he’s doing. There’s also a company in Charleston, South Carolina, called PalmerSC that is a player in the field. I’d like to get Rambley and them together.”

Racquel pulled a small fat notebook out of her briefcase and thumbed through the pages. “I don’t have anything on Rambley, but PalmerSC, especially a man named Bruce McCraey, is in here a couple of times.”

“Was he a client of yours?”

“No. But I had met him and got his business card…let’s see…twice before, at parties that I was hired to work. I tried to get him to party with me, but he declined. He said he finally met his perfect woman.”

“Do you keep records on all your clients?”

“Not particularly. If I think they’re influential, I keep loose tabs on them. You never know when you need some help or maybe some advice.”

“You looking for a sugar daddy?”

“Believe it or not, no. I do a lot of things, but not that. I know that sounds contradictory, especially with my line of work, but I’m pretty damn independent. That’s why I’ve never worked for an escort service or had a pimp. I’ll do it on my own, thank you very much; even it was being an escort.”

“You had a lot of info on me. What else do you know?”

Confident that she could speak freely, she said, “I know that you’re a good guy. You care about people, and you keep your eyes out for opportunities to give people a hand up. Your charity donations are impressive. Why do you give so much of your money away? I mean, it’s very admirable, but why?”

I had to laugh at myself about that. “Because, believe or not, I feel kind of guilty about it all. I’ve been very fortunate. I never married, so there aren’t any kids to blow it all on. You know the old saying; you can’t take it with you.”

She then asked me a question that floored me. “How do you reconcile that with your sex tourism?”

Wow. That hit close to home. I had to think about that for a moment. “I guess I’d say that, like you, I like sex a lot…a helluva lot. I have the resources, the time, and the opportunity to do what I want. I choose to fuck every beautiful woman I can get my hands on. I’m insatiable.”

Racquel looked at me very seriously and said, “So am I, sir. And maybe the best way to describe why I wanted to team up with you is to say that we can use each other. You need me to make your life easier. I need you to teach me how I can finally get myself straight. I don’t’ want to be a whore. I want to be successful and independent, like you. And the price I have to pay for that is to serve you as your wingman...and rock your fucking world as your slave.”

I was totally down with what she said. It was a good arrangement.

“One more thing, sir,” she said, “talking about this kind of shit makes me hornier than hell.”

“Well, do something about that, Racquel.”

“Yes, sir! My pleasure, sir!” She giggled and stood in front of me, lifted up her skirt, and revealed that she was commando. “Get your dick out, Mr. Gaudette … now!” I did, and she drove her wet muff down on top of it. “Fuck the shit out of me, sir. Make it hurt.”

She violently bounced up and down on my dick. Her tight pussy tugged on it, and she moaned loudly with every thrust. “You really are a fucking animal, sir. It hurts! I like it like this.” She pulled her blouse out of the skirt and lifted it up, then popped the front clasp on her bra open, and pulled my head on her tits. “Suck on ‘em, sir. Suck ‘em, bite them, kiss them. Flick your tongue on my nipples. That goddam drives me nuts.” The more I tongued her nipples, the wilder she got until she let loose with her own orgasm. Her moans were so loud that I was sure the pilots could hear her. Then, I felt her juices flow on my rod deep in her. “Oh my god, sir. That feels so fucking great!”

After she came from the tit-play, Racquel knelt down between my knees, stroked my cock, and said, “Sir, I’m going to do something that will, as I said, rock your world. You need to trust me on this, but I promise you will feel amazing. Keep your hands to your side…you might even want to grab onto the seat.” With that, she stroked my dick more deliberately and powerfully. “Now, sir, there’s a really good chance you’re going to pass out. What’s going to happen is that intense.” Her strokes were fast and strong. Her expert grip was with her entire hand rather than just a finger or two. I could feel the sensation of me wanting to cum getting stronger in me. Then, right before I came, she squeezed my dick hard to prevent the jizz from shooting out. Racquel then took her other hand, held it flat out, and lightly rubbed the head of my cock with the palm. Each time she circled the tip, my nerves exploded with an extreme orgasmic jolt. It was overpowering. I didn’t cum, but my balls exploded. Shockwaves dashed throughout my body. My mind was fried. I lost my vision and I think I actually did pass out for a minute, just like she said might happen. It was an amazing experience.

When I regained consciousness and opened my eyes, I saw her still kneeling between my legs sucking gently on my dick and emptying out my balls.

“Are you okay?” she asked.

“Yeah. I guess so. How long have I been out?”

“About ten minutes. I took it easy on you that time.”

“You took it easy on me? That was easy?” I exclaimed.

“Oh, I could have worked you much harder. You could have been out for hours.” She replied calmly. “And if I would have given it to you with both barrels, it actually would have caused your extremities to be paralyzed. It’s that extreme.”

“What the hell was that?”

“It’s called a lot of things, but I call it the Palm Swirl.”

“That was amazing. Why haven’t you ever done that to me before?”

“Sir, I don’t sell that for any price. It’s only for special people…like you.”

To be continued


If you’d like to show your appreciations for a job well done there are several things you can do. First, leave a comment about the story. Second, connect with me on social media (see below).Then, don’t forget to leave a tip.

About the Author

Jay Gaudette is an author of a variety of erotic genres. His novels include the Unconventional Affairs Trilogy; The Unconventional Affair, Tangier and Tough Cookie—epic sagas about the kind of love and life we all aspire to. Short stories include sequels based on the trilogy, Jay Gaudette’s Friends and Lovers series, and various other titles.

Connect with Jay (Visit my link section on my profile page.)






© Copyright 2018 Jay Gaudette. All rights reserved.


Add Your Comments:

Other Content by Jay Gaudette

More Great Reading

Popular Tags