Sinderella

Despite the fact that I had resolved to do this, I was nervous sitting at the bar at the very upscale hotel only ten miles from my house early evening on a Friday. I checked once again the envelope containing $500 in cash in my sport jacket pocket, like it might have flown away since the last sip that I had taken of my Scotch and soda. My right foot nervously tapped the footrest on the bar stool.

"Are you Jack?" a lilting voice to my right rear asked.

"Yes," I blurted out as I turned, recognizing the made-up name that I had given myself in my communications with "Sinderella" when I made arrangements for this meet. "You must be 'Sin,'" I replied using the shortened form of her trade name as I gently shook her hand. Except for the fact that her obvious blond wig wasn't perfectly perched on her head, and that she had a little too much makeup on, she looked as sexy and I thought that she would. Per my request, so as not to make it obvious that we were concluding a business deal for sex, I asked her to wear jeans and a not-too-revealing casual top. Her idea of "not-too-revealing" was different than mine, however, since her ample cleavage was clearly on display. Also, the jeans looked painted on rather than worn they were so tight - but they got the desired reaction as my cock immediately stiffened.

"Did you valet park?" I asked, just to break the ice.

"Just like you said to," she replied with a wicked smile.

"What would you like to drink?" I asked.

"Just club soda or seltzer - I'm working," she shot back with an even more devilish smile.

"So, you've decided to accept my proposal?"

"Not yet - but I'm working nevertheless. Don't you have something for me for showing up?"

Sin was cautious in her email dealings with me. She said that she normally didn't meet her prospective sex partner at a hotel bar, but I partially convinced her that she had nothing to fear at an upscale bar like this, where the drinks were a minimum of $20. The deal I had made with her was that I'd give her $100 just for showing up to evaluate the situation and $500 more for two hours if she agreed to "take me on."

I surreptitiously slipped her a Benjamin, she quickly confirmed that it was a C-note, then she slithered it into her clutch.

"You look really good in that outfit," I said, hoping that I wasn't drooling.

"I know," she chuckled. "So tell me about yourself, Jack."

"I'm just an average fairly well-to-do businessman in the city. I've got a wife of six years, I play tennis or racquetball two or three times a week, and go to the health club another two times every six or seven days. My life if fairly routine; almost boring."

"So, you're looking for a little 'spice?'" she inquired again flashing her evil grin.

"You could say that," I chortled.

"Wifey not keeping you satisfied?"

"She's OK; just a little conservative. I need something uninhibited; when I saw your profile I thought that you were just the right person to provide some spice."

"I'm more cayenne pepper than cinnamon, Jack; are you sure that you can handle it?"

"I'd love to find out," I responded with a big shit-eating grin on my face. "So tell me about yourself; do you like your profession?"

"You bet; however, a girl who does what I do has to be careful. There are a lot of perverts out there, which is why I screen all my clients. Since you wouldn't give me your real name to check you out, I had to have this meet in a public upscale place."

"Do I pass the non-perv test?"

"Too early to tell. You're nice looking and I can see by the significant bulge in your pants that unless you carry a pickle around in your pocket I'd probably enjoy fucking you. But looks can be deceiving."

I proceeded to sip my grossly expensive Scotch and soda while she nursed her $15 seltzer water as we talked about many things, some with sexual overtones, others without. She had a good grasp of current affairs - and I don't mean the sexual kind - and a very sultry manner. I could feel my cock getting stiffer and stiffer.

After about forty minutes of chit-chat she lightly put her hand on mine. "Did you bring the test results with you?"

"I sure did," I replied, covertly handing her a sheet of paper with a lab's name at the top that said that I was free of all STDs. "And you?"

She slyly handed me a similar sheet, which I looked at just enough to see the "99% probability of no STDs possible to test for," at the bottom.

"Are you ready to close the deal?" I expectantly probed.

"Do you have payment?" she shot back.

I removed the opaque envelope sealed with a classic string and buttons closure and handed it to her. First looking around to see that no one was paying attention, she unwound the string and peeked inside. She inserted her right hand, obviously spreading the bills out to count them. "There's only five hundred," she mumbled under her breath.

"I thought that was your rate for two hours," I mumbled back.

"Not without a condom and when I had the expense of getting the STD testing done. I need $200 more."

Since my cock was straining at my zipper - something she clearly noticed - she knew that she had me, and I knew it too. I didn't want to do anything to spook her because I badly needed her cayenne pepper approach to sex, so I clandestinely removed another $200 from my money clip and slipped it to her.

"Plus valet parking is twenty bucks and I had five bucks worth of gas getting here," she said with a sly smile while holding her hand open under the bar so that no one could see it.

"Shit, you better be worth it," I grumbled as I removed a five and a twenty from my now almost completely depleted money clip and slipped it to her open palm.

"You have NO worry about that," she snickered as she stroked the hand with the $25 in it over my crotch, almost causing a spontaneous ejaculation.

After she inserted the additional $225 into the envelope, and added the $100 from her clutch to it, per our agreement she took the envelope to the front desk. In a voice and with body language that had the young male hotel desk clerk slobbering said "Could you please hold this for me for a few hours. I don't trust the safe in my room. I just need a claim check after you put it in the hotel safe."

"Uh, certainly, ma'am," the clerk stuttered, unable to take his eyes off Sin's cleavage. He got out a claim check, taped one half onto the envelope, and gave her the other half.

"Thanks soooo much," she gushed as she slid her hand over his as she retrieved the claim check causing the clerk's eyes to almost pop out of his head.

When I was sure no one was looking and we were in a secluded part of the lobby, I gave her a key card. "Room 414; I'll be up in five minutes."

"I'll be ready she grinned," taking the key card from me much like she took the claim check from the poor clerk.

I couldn't wait the full five minutes. "Shit, no one will catch on," I convinced myself as I went up the elevator only two minutes after she did. When I opened up the door the covers had already been pulled down and Sin's shoes were sitting off to the side. She gave me a big smile, sashayed over to me, removed my sport jacket and hung it up, took off my tie and placed it on the dresser, and then turned on the music channel on the TV, found what she was looking for, and started a strip tease.

Holy shit was she sensual! My dick was the hardest that it had ever been. When she approached me with her jiggling big tits and shaved pussy with prominent lips I was afraid that I was going to cum in my pants. She apparently sensed that as she undid my belt while murmuring "Normally I'd suck you for a while but you look like you're about to blow and since I rarely get cum in my pussy - usually condoms - I don't want you to waste one."

When she pulled me down on top of her on the bed I still had my shirt on, although mercifully my cock was now completely free. "No foreplay necessary, stud," she whispered into my ear, "just fuck the shit out of me."

I didn't need any more encouragement. I couldn't believe how wet her pussy was when I shoved my cock into it - tight but well-lubricated. As I started banging away she wrapped her sculptured thighs around me and pulsated her pussy muscles. When after only two minutes I spurted a huge load into her anxious pussy she screamed and then seemed to go almost comatose. I was so overwhelmed by the intensity of my ejaculation and her pulsating pussy muscles that I was close to comatose myself as I lay on her, careful not to crush her, with my cock still firmly planted in her cunt.

I really don't know how long it was before we both became fully aware again. When I rolled off of her my dick was still three quarters hard, and a string of cum and pussy excretions followed my cock out of her amazing cunt. She giggled, I chortled. "I didn't know that call girls had orgasms," I said staring into her sparkling azure eyes.

"Well this one sure did," she chuckled. "I'm not a good enough actress to fake something that intense. I have no idea why, but that was one of the best fucks of my career."

I smiled at that. Then I lifted her legs up in the air and put a pillow under her ass.

"What are you doing?" she asked with a look of puzzlement.

"I want to see my cum leaking out of your pussy while I stroke your lips and finger your asshole."

"I don't do anal," was her sharp reply as I held her legs up.

"My cock wants your pussy, not your pucker hole," I laughed. "I just want a little finger play - you'll like it."

She was a little apprehensive but I could tell that she liked me lightly pinching her labia and probing her brown hole with a finger or two. After about ten minutes she said "While that feels good, enough of that stud. Lick my clit to get me ready for round two.

I was a little apprehensive. "I don't eat my wife after I fuck her," I weakly replied.

"First of all, I'm not your wife. Second of all, I said lick my clit not suck the cum out of my pussy. Just leave the cum there - I like the feel of it - but I want my clit stimulated!"

I did as told. She had a very sensitive clit and obviously enjoyed my tongue action on it. She also enjoyed my hands squeezing her ample tits while I licked. After a few minutes she shuddered and moaned "Lay on your back."

I again did as told. She straddled me and sucked my cock to maximum hardness in no time flat, then held it as she impaled herself on me reverse cowgirl, groaning loudly as the last few centimeters buried themselves in her snug channel. She then proceeded to vigorously move every way imaginable as she supported herself with one hand on my thigh, and massaged my balls with the other hand.

I was enjoying things too much, and sitting up was too difficult, for me to reach and latch onto her fabulous tits, so I squeezed her ass with one hand and fingered her pucker hole with the other. She was doing such a good job of acting on my cock, and I was so excited by her activity and manipulating her delicious ass, that I blew another monster load in short order, probably the shortest time between two major ejaculations in my life. I swear that she had another orgasm too because no one outside of a stage can act that well!

When she finally raised her abused, dripping, cunt off of my flagpole, I again put her on her back, raised her legs, and started playing with her labia and pucker hole. I couldn't believe it when the alarm went off.

"You set the alarm?" I asked, quite incredulous.

"Hell yeah - as fun as you are, stud - and by the way I really do like your cock, it fits me perfectly - I am a good businesswoman. But that is just the hour-and-a-half alarm. We have time for a shower together."

Well at least I felt better about that.

In the shower we kissed and groped each other more than cleaned. I'd love a shot - maybe in the future - at fucking her fantastic tits. She insisted that I leave her crotch alone, however. "I like the feel of your cum in me. I don't get that when using a condom like I require 95% of the time," she whispered while fondling my balls.

After our shower, Sinderella immediately got dressed in her lace panties and bra and skin tight jeans and sexy top, gave me a passionate kiss, and was out the door almost exactly two hours after she had entered. Her last words "Did you get your money's worth, Jack?"

"Hell yes," I mumbled as I gave a tit and ass cheek one last squeeze.

I was wiped out, so without getting dressed I lay on the bed - careful to avoid some spots that were still wet whether from sweat, pussy juice, or cum - and took about a forty five minute nap with pleasant memories swirling through my brain the entire time.

After my nap, I got dressed and drove home, expecting a bad reaction from my wife Cindy. I wasn't wrong.

As I walked in from the garage, I had to duck to avoid a flying object - fortunately an empty thin-walled plastic water bottle, so it didn't do any damage when it hit the wall near my head.

"You fucking bastard, you were out whoring, weren't you?" Cindy screamed.

"Eight hundred and twenty bucks is hardly the cost of a whore," I chuckled to myself, but presented an outwardly serious façade and replied "Where did you get that idea. I told you that I'd be late. I had a business meeting."

"Bullshit, Tom. I called your office and they said that you left promptly at five and no one knew of any 'business' meeting. You were whoring, weren't you?"

"I'm telling you, Cindy, that I had a business meeting. The people in my office don't know everything that I do. Now come on; why would I go whoring when I have a beautiful wife like you?"

Actually, Cindy is a beautiful woman; but now a seemingly angry-as-a-hornet one.

"Don't give me that shit, Tom. You haven't been worth a damn in bed recently and I'm sure that you're getting pussy on the side. Since no one but me would ever let you fuck them without a payment of some kind that means that you must have been whoring."

"Now come on Cindy," I said approaching her with open arms and trying to defuse the situation, "don't insult me like that. I've always treated you with respect; and you have no grounds for your accusations."

When I tried to hug her, she pushed me away, and started belittling me some more, calling me "dickless" and a number of other choice names. Finally I decided that it was time to show her who was "dickless," and with my confidence buoyed by how pleased Sinderella seemed to have been with my performance, I grabbed Cindy and carried her to our bedroom. She was kicking and screaming the entire way, but I'm much bigger and stronger than she is so I got there without being the recipient of too much damage.

As I threw her down on the bed I held onto her dress, ripping the entire fucking thing off of her. As she kicked and screamed I ripped off her lace panties and turned her face down on the bed and unclasped her bra, freeing her ample tits.

"Get the fuck away from me, fucktard," she yelled as she kicked. I knew that I'd have a few bruises the next day but I was on a mission. I kept a pair of fur-lined handcuffs, which I had not yet had the chance to use, in the night table. While fending Cindy off with one hand I got them out of the top drawer, and then held her wrists together.

"Ouch, you're hurting me," she cried out.

"Then stop flipping around like a landed marlin and resign yourself to getting fucked."

That comment didn't help much, but I did overpower her and got the cuffs on her, threaded through our sturdy metal headboard. She was on her knees on the bed facing the headboard to which she was cuffed and swearing like a sailor. I casually removed my clothes on the side of the bed so that she could see me doing it and the major hard-on that I was sprouting.

"Don't you dare get that little impotent cock anywhere near my sweet pussy," she bellowed several times.

I slapped her ass and using the old platitude from Victorian England when married women were counseled on how to do their unpleasant martial duty of succumbing to their husband's sexual advances, I chuckled "Cindy darling, just close your eyes and think of England."

That didn't get a laugh, just more swear words.

I was finally able to hold her ass still enough to shove my dick into her. Despite her protestations, she was as wet as I ever remember. I bent over her back, grabbed her abundant tits, and lightly pinched her nipples as I pounded her as hard as I ever had. It was only a couple of minutes when her swearing stopped and she started pounding back into me and moaning in a low voice. Then she even started pulsating her pussy. I thought that she was having a heart attack she spasmed so much when I grunted loudly as I ejaculated my third massive load of the evening, and after a banshee scream she went limp.

I really, really, really felt good as endorphins flooded my brain while I lay on her limp sweaty back as she emitted random groans herself. There was a loud "pop" when I finally pulled my deflating cock out of her drenched pussy. I undid the handcuffs, turned her on her back, and just like I did with Sinderella elevated her legs, put a pillow under her ass, and played with her labia and pucker hole.

* * * * *

After about ten minutes Cindy regained clarity. A big smile crossed her face. "I love you so much, Tom," she gushed with a few tears in her eyes.

I gently guided her legs back onto the mattress and cuddled up to her nose-to-nose. "I love you too, Cindy, with all my heart!" I sincerely replied.

"Then honestly tell me," she giggled. "Did you enjoy me more as Sinderella or the wronged, aggressive, pissed-off wife?"

"God, you were so fantastic in both roles that you missed your calling. You should have been an actress. All I can say is that tonight I had the three best sexual experiences of my life with a cayenne pepper call girl as beautiful as my wife, and my wife as hot and sexy as a cayenne pepper call girl."

"Do you think that Dr. Bradford knows what the hell she's talking about? Will this role-playing when I'm at my most fertile period result in a pregnancy? We've been trying so hard for so long..." Cindy got out before tears started flowing.

"Damn right it's going to work," I smiled as I wiped away some tears. "That was the most sperm I've ever spewed out in my life, and we raised your legs up for ten minutes after each time, just like Dr. Bradford said, to give my little swimmers the best chance."

"I have a good feeling about it," she giggled as she wiped away the remnants of her tears.

"By the way, I need some of that money back to buy stuff with tomorrow," I grinned.

"Are you saying that I wasn't worth $820?" she snickered.

"Hell no, you were worth a hundred times that. I simply need to buy some stuff with cash tomorrow, and I gave it all to you."

After a pause for dramatic effect and with a diabolical grin and a chuckle she continued "Well, let's see how good you eat me right now, and if you get it up a fourth time tonight I might give you a couple of hundred back."

I tickled her, then sucked on her clit, and for the first time in my life got it up a fourth time in one twenty four hour period.

As we fell asleep in each other's arms I was absolutely giddy with the thought "we have another few days while Cindy's in her most fertile period, and I intend to keep my cock buried in her pussy that entire time."

* * * * *

Three and a half weeks later Cindy found out that she was pregnant. She insisted that we celebrate with another role-play. I acted as a cop who pulled her over in the park for drunken driving, and fucked her twice in the back seat of the car (once her pussy, once her tits) as my payment for not writing her up. It was almost as awesome as the prostitute-angry housewife scenario!