Married Whore Fetish

I'm not a normal guy for many reasons. The first two are good -- at least I think that they are. I have lots of money, more than I can spend in one lifetime; and I have a big dick. The others are not so good -- at least to most people. I'm commitment adverse, I'm often pompous, I'm not very charitable given my wealth, and I have what I have been told by professionals is an unusual (they call it perverted) fetish. My fetish: I don't get excited during sex unless it is with a married woman that I am paying for the sex.

To satisfy my predilection I particularly like mature married woman who more than likely have never cheated on their husbands. I'm not real fussy about how beautiful they are, but they at least have to be a six on a ten point scale. I do have a particular type, but they are few and far between, so as long as the woman is at least a six, is married, and will take money for sex, I'm as happy as a pig in poop.

Unfortunately finding the right women is not the easiest thing in the world and I have been slapped or had a drink thrown in my face many times. I don't hold it against the woman if she does that, but of course I don't like it. Therefore I have developed a scenario that provides the least possibility that I'll be on the receiving end of a slap or a drink in my face.

*********

One reason that I have lots of money is because I'm CEO of two different very profitable companies and am a hands-on manager. Therefore for most critical contract negotiations with customers, clients, or suppliers, I like to consummate the final deals myself. This necessitates a fair amount of travel but since I have no family at home and like to see different places and can afford luxury suites in hotels I actually quite enjoy the travel.

During one week that turned out to be remarkable I travelled to XYZ Corp.'s international headquarters in the Chicago area. I had done business with XYZ for several years and I wanted to conclude a contract with XYZ that would bring in many millions of dollars for one of my companies. I was staying in a luxury suite at the Waldorf-Astoria hotel, one of the most expensive hotels in the Chicago area, Room 1812 (which also happens to be the name of my favorite piece of Tchaikovsky music).

On the same floor as the president's office of XYZ was a new secretary, or at least one that I had never seen before. She turned my head because she looked like my type. She was about five feet ten inches tall in what I assumed were two inch heels, brunette, about forty, with a sleek body and a pleasant if not beautiful face. She didn't dress very well and had kind of a perpetual pouty face. Maybe pouty isn't the right word; perhaps "almost glum," but not quite, is more accurate. Anyway, even with her less than stellar attire and normal facial expression to my tastes she looked like a nine on a ten point scale.

She had a tiny engagement ring and a silver wedding band on her left ring finger. I not-too-subtly found out that her name is Mrs. Eleanor Morton. For some reason I have always liked the name Eleanor, maybe because that was the name of my favorite, now deceased, aunt.

Even though Eleanor was not the secretary for XYZ's president I did find occasion to interact with her the first two days at the office, including politely entreating her to make copies of some documents for me, and to get me a particular coffee-based concoction from the café in the building next door and rewarding her by paying for her lunch.

About 4 o'clock the second day that I was there I asked her if at 5 p. m. she could meet me for a drink at a high class bar one street over called Casey's.

"I'm married," she said with raised eyebrow, "and I'll miss my train."

"This is a business discussion, not a pickup, and I'll pay for a limousine to take you right to your doorstep. It will likely not take more than one drink's time -- 20 minutes," I countered.

"You'll pay for a limo? Leaving at 5:30?" she inquired again with raised eyebrow.

"For sure," I replied. I gave her a business card for the limousine service that I used and told her to call them and when they answered to hand the phone to me. She did. When I got the phone I said "Reggie Portofino here. Can you provide a pickup of Mrs. Eleanor Morton in front of Casey's bar at 5:30 p. m. today and charge it to my account. I'd prefer Bruce or Cheryl as the driver, but anyone will do. (Pause) Thank you I'll tell her."

I handed the phone back to Eleanor and with a smile said "Cheryl will be your driver in a dark blue Mercedes S-Class sedan."

She actually smiled and said "I'll meet you at Casey's a few minutes after 5 Mr. Portofino."

I smiled back.

I actually timed my exit to walk with Eleanor from XYZ to Casey's. I got us a remote booth and flagged down a waitress even before we sat down and ordered a Martini for me and a glass of Chablis for Eleanor.

Since we had exchanged pleasantries on the way over I got down to business, only interrupted when the waitress ultimately delivered our drinks.

"Eleanor if I give you $100, no strings attached, will you agree to listen without reaction to a business proposal?"

"That's an odd question Mr. Portofino."

"Please call me Reggie; if you feel you must call me Mr. Portofino in your office I understand, but I'm no better than you are and I'd really prefer Reggie outside of the office."

"OK; that's an odd question Reggie."

"Perhaps, but what have you got to lose? Certainly you can keep your composure in a business discussion for fifteen minutes, can't you? That's all that I ask Eleanor, the $100 paid in advance," I continued as I removed a Ben Franklin from my fat money clip.

At that point the drinks arrived, we thanked the waitress, and Eleanor took a sip. Her face now had a wan smile, not a pout, and I was re-scoring her face from a 9 to a 9.5. "OK," she finally said, taking the $100 bill from my hand and putting it in her purse.

"I first have to somewhat explain myself -- again, keep your composure. I have a predilection for paying beautiful married women for sex. As you should already know you are definitely in that category. I am very respectful, don't do exceptionally kinky things, am never in any way violent, I love to eat pussy and otherwise please my lover, and pay in advance. If you would be so kind as to accept my invitation for two hours of sex tomorrow night from say 5:15 to 7:15 I would again see to having a limo take you home."

At least she didn't slap me or throw a drink in my face, but she didn't look pleased either. After a long delay where we both stared into each other's eyes she said "So you think that I'm a whore?"

"Absolutely not; I'm simply asking you to satisfy my penchant. If I could satisfy it without paying a married woman money, I would -- but part of my 'fetish' if you could call it that -- is that I need to pay."

"You're a good-looking fit man, why do you have to pay for sex?"

"Again I don't have to pay -- I just get much more pleasure from the experience when I do. I don't know why, I just know that it's true."

"Have you seen a shrink about it?"

I'm not normally interrogated by possible conquests, but this woman intrigued me and I had no problem answering her questions -- up to a point -- so I did answer. "Yes, I have; actually three different ones. They all had different takes; the one from Harvard said it was because of my mother, the one from Yale because of other females in my family, and the one from Northwestern because of a coach I had in High School. Just before I cursed him out for being a fraud the Harvard guy told me "You can overcome your fetish if presented with a better alternative." They all were just spitting out mumbo-jumbo as far as I'm concerned. I don't really care that I am the way that I am, and I do get enormous pleasure out of it and believe that I provide pleasure too in addition to real money."

"How old are you?"

"Thirty eight."

"I'm forty one, you know."

"No I didn't know but I don't care. Age is just a number. You fit my tastes so I honestly don't care if you're 21 or 61."

"Do you expect romance?"

"Hell no; I only expect mutually-rewarding physical pleasure."

"How do I know that you'll be discreet?"

I took a document out of my inner suit coat pocket. I handed to her. "This is a contract whereby we both agree that we will not tell anyone, unless forced to by a court of law having jurisdiction, about what we do in a meeting we have -- in the blank spot we fill in tomorrow's date. If I violate I pay you $50,000. If you violate you pay me $2,000."

She was silent again so I continued. "I also can provide you with an STD-clear certificate so that we both can get maximum pleasure out of it." I reached into my inner suitcoat pocket again and pulled out a lab test from five days ago and handed to her. She seemed to be interested in the lab report because she took a few minutes to look it over before she handed it back to me.

"If I were interested, how much would you pay, and what would you do for me if I let you fuck my pussy?" she countered again with that wan smile.

"I'd pay $500 for two hours. If you wanted I'd eat your pussy to orgasm and lick your ass before I fucked you, and -- again if you wanted -- I'd stick a vibrator up your ass while I fucked you."

"How big is your cock?"

"When erect approximately 7.6 inches in length and 6.2 inches in girth."

"Liar," she chuckled. If she was chuckling I was getting somewhere.

"Tell you what, you can measure it and if it's more than a quarter inch less for either length or girth I'll double what I pay you."

"So if you're lying you'll pay $1,000 for two hours instead of $500?"

"That's right."

Eleanor looked at her watch, bolted down her drink, and said "Can I text you tonight?"

"Sure," I smiled. "Here's the number of my burner cell -- which I will recycle in two days, but works great now," I said as I wrote my phone number down on a cocktail napkin.

"You're an interesting guy, Reggie," she said with a smile as she shinnied out of the booth and walked toward the exit, wiggling her ass. I looked at my watch; 5:28 and 32 seconds.

I took the last sip of my drink and then noticed that my cock was tenting my pants. "Shit," I mumbled to myself, "I hope that she agrees that was the most stimulating conversation I've had in years."

*********

Just before I was going to shower and then go to bed that night I got a text on my burner phone. "How much for the whole night?"

I had some little blue pills with me; was this really happening? "$1,000" I typed back.

Not two minutes later the next test from Eleanor said "$1500. 3000 if you're a liar; deal?"

I counted my little blue pills; I had brought a bunch and could safely only use two, but two I would. "Deal," I texted back followed by a smiling emoji, it followed by "Sign contract tomorrow, delete texts."

"Good, deleted," came back thirty second later.

I was so charged up that I almost couldn't resist beating my meat that night, but I finally convinced myself that I needed to rest up for tomorrow night and kept my hands away from my cock and I actually got a good nights' sleep with visions of pussy and tits dancing in my head.

*********

I concluded my contract with XYZ and had all of the papers signed and a $1,500,000 advance in my corporate account by 3 p. m. the next day. I was not getting a flight back that afternoon only because of my deal with Eleanor. Neither of us treated the other differently during the work day, but I did notice that she was dressed more nicely than the other days. Pretending to be talking about having her make photocopies of a document I handed her two copies of our secrecy contract that I had already signed. She signed, gave one to me and kept one. I surreptitiously passed her an envelope that had $750 in it, a note that said "The rest tomorrow morning," and a keycard for Room 1812 at the Waldorf. I then went to my hotel room to take a nap and get ready for Eleanor's arrival.

Eleanor arrived at 5:12 -- not that I was anxious and keeping track of the time -- carrying her purse and a small valise. She used her key card to enter. She put her purse and valise on the first piece of furniture she encountered then she walked up to me, put her arms around my neck, and asked "Do whores kiss on the lips?"

"You need to," I grinned and then smashed my lips into hers.

"Would you like a drink?" I graciously asked.

"No, I'd like to get down to business and after some activity maybe order room service," she grinned as she kissed me again. When she broke her kiss she said "Let's shower together."

We slowly disrobed each other. When we were both naked and my cock was standing proud she said "Hold on a second." She walked to her purse, opened it, and came back into the area right outside the bathroom carrying a seamstress' tape measure.

Without saying anything she got down on her knees and measured my flagpole. She measured both the length and girth twice. "You were right you bastard; length only a tenth of an inch less than you said, shockingly girth a tenth of an inch more. According to the Internet that puts you in the 98th percentile for both length and girth. You're really going to have to loosen me up to fit that weapon in my poor little cooch," she snickered.

I liked it that Eleanor didn't slap my hands no matter where they roamed in the shower, even though she fake complained about my fingers when they touched, or went inside, certain parts. She did seem to have a snug cooch. It might take me awhile to bury my pole in her cooch but what fun that would be.

When we dried off, pulled back the comforter and top sheet, and lay on the bottom silk sheet. With a wicked grin she said "I'll take two oral orgasms, no ass licking, and then my pussy fucked with a vibrator up my ass if it will fit with your cock filling my cooch."

"Yes Ma'am" was my reply. Then I got to work.

Why pay a whore and then give her pleasure rather than the other way around one might ask. The answer: I love to eat pussy, as long as it's clean and hasn't been just fucked.

I was very pleased with Eleanor's body. Her thighs were muscular and creamy, her ass was firm, her tits probably a C cup and East-West (I love East-West tits) with hard protruding nipples. Her crotch was not completely hairless but primarily so. She had a snug pussy for a woman her size, and a prominent clit. Plus she tasted like almonds -- I like almonds.

I was also pleased the Eleanor was very multi-orgasmic and quick on the trigger. Just my tongue alone wiggling in her pussy while my fingers spread her labia apart resulted in a quick first orgasm. After she came down from that I fingered her cooch for a while and then sucked her clit into my mouth. Her reaction was what I supposed it would be if she had been shocked by a 120 Volt line. She stiffened, she screamed, she pulled my hair, and her entire core shivered.

I was grinning like a Cheshire Cat by the time that she came down from her second orgasm. When she regained complete awareness she looked me in the eye and cackled "Smug bastard. Now let's see if you can fit your monster hog in my poor delicate little kitty," as she got on her hands and knees on the bed.

I put my dick head at her vaginal vestibule and started slowly pushing in. She was really tight, but lubricated enough from her two orally-induced orgasms to allow penetration. She moaned, and I groaned, both of us in pleasure, as I penetrated her centimeter by centimeter. Despite the fact that she was about 5 feet 8 inches tall and 130 pounds she was the tightest woman I had ever been with.

Once I was about halfway in she started swearing. "Stick that freakishly large cock in my pussy, you bastard; oh sit that feels good and hurts at the same time; come on you wimp, get with it!" were some of the many things that she yelled, groaned, and mumbled during penetration. I had never had a woman talk like this before, and it was really turning me on. When she groaned "Is your fucking thing useless you fucking pervet, bury it!" I obliged.

I could tell that Eleanor had a little bit of pain when I buried myself balls deep, but that apparently quickly dissipated because she started simultaneously pulsing her pc muscles and banging back and forth. I soon got with the rhythm and did my own type of banging, my balls slapping against her firm ass cheeks. She came twice in rapid succession, each time clamping down on my cock. It was then that I thought about the vibrator.

I reached over to the nightstand for the vibrator and even though it was thin it was not going into her ass -- she was filled with my cock. After I failed in a third attempt to insert it Eleanor screamed "Forget the fucking vibrator; it isn't going to fit. Just fuck me you perverted asshole."

After only six quick strokes I was unloading a tsunami of cum into her anxious pussy. She screamed in orgasm a couple of times and then went limp. After my last salvo of cum I slowed down dramatically but still leisurely reciprocated into her. Her only signs of life were low pleasure moans and an occasional set of spasms as we were hit by asynchronous aftershocks.

I don't know how long it was before it was clear that she was cognizant again, but it was a very gratifyingly long time. "Get that fucking weapon out of my pussy, bastard, I need to collapse," she said in an amusing tone.

I withdrew but was surprised that my cock was still three-quarters hard. Normally I go completely soft after as intense of an orgasm as I just experienced.

We collapsed next to each other face-to-face. After a few minutes of silence she stared into my eyes and said "Am I a good whore?"

"You have to ask after that?" I chuckled. "Actually, though, you're not a good whore -- you're a fantastic whore."

"I'm going to be your best ever by tomorrow at 9 a. m.," she chuckled, and then shinnied down and started sucking my cock. Her mouth had the suction power of a vacuum pump and I was hard again in minutes. Then she pushed me on my back and mounted me.

Despite the fact that I had just pasted the hell out of her it was slow going as she wiggled her pussy over my upright appendage. Once she was buried she rode me like I was a rented mule while I mauled her flopping tits. She came twice before I unloaded all of the buildup of seminal fluid in my testicles in two prolonged powerful ejaculations. She screamed as her pussy clamped on my cock, and then her chest fell onto mine. It was by far the best second fuck I had ever had.

Eventually -- again after surviving a few aftershocks -- we separated and she lay next to me. "That was fun," she cackled.

"You think?" I laughed.

"So am I on the way toward being your best whore ever?" she inquired with a look hard to decipher.

"So far," I laughed.

"I'm hungry and whores can't live by cock alone perv. Why don't you order me some red meat by room service then we can shower together while waiting for our meal."

Wow she was a cheeky bitch -- but I loved it. I ordered us each a steak with all the trimmings, a bottle of red wine, some coffee, but no dessert. Then we showered together again where again she never slapped my hands as I mauled her tits, pinched her ass, and inserted a couple of fingers into her pussy.

After our shower I got into a robe to answer the door in the living room part of my suite when room service arrived. Showing how absolutely diabolical she is Eleanor waited in the bedroom until she saw that the room service employee was a male, then walked out of the bedroom naked, smiled, and said "Whoops," but made no effort to cover up. His eyes were as big as baseballs and he couldn't tear them away from her. As he exited I wondered what was the better tip for him, the $30 I added to the room service bill, or seeing Eleanor naked.

The rest of the evening only added to my confirmation that this was the best night of my life from the sex standpoint. Eleanor was all of playful, sexy, warm, charming, lascivious, and above all HOT!