Matt's Story

#################### Part 1 ####################################

"Hello Matt dear."

Isabella slid into my car and kissed my cheek. She was one of my only regular rides who wanted to sit in the front seat.

I smiled "Hi Izzy. The mall again this week?"

She smiled that secret smile of hers and she gave my cock a squeeze through my pants.

Okay, changing room sex again.

################ Part 2 #######################################

Mrs. Isabella Ibenez-Marchand, Izzy to me, is the wife of one of the biggest commercial property developers in the southwest. And she had generational wealth inherited from one of the original Spanish Land Grant families in New Mexico. With homes in Taos, Scottsdale, Park City and an entire island somewhere in the South Pacific, she was my wealthiest client. In her late 50's she was obsessive about extending her youth. She worked out like an animal and, thanks to an unlimited budget for modern medical intervention and surgery, she had the body and skin of a woman in her late 20s. She had even had her vagina tightened.

As I discovered on my first ride with her, she had a thing for semi-public sex. The greater the risk of discovery, the hotter it made her.

Izzy had been referred to me by Lizzie Letterhammer. Our first ride started from her naturopath's office and was supposed to end at her home. I pulled into the parking lot of the Holistic Medical Center that had been set as where I was supposed to meet her. I kept the car running and the air conditioning going. It was 112 degrees in the Valley of the Sun that day.

At the designated time a woman who was about 5'3", 110 pounds max, came out of the darkly tinted doors. The tan on her long and toned legs and arms glowed in the blazing mid-afternoon Arizona sun and her long flowing dark brunette hair blew in the light summer breeze. She had on a frilly cream-colored summer sundress, her breasts unbound and bouncing lightly as she walked. Her well-turned calves were wrapped with thongs coming up from flat, roman style sandals. Her age was impossible to judge. Walking through the heat shimmer coming off the parking lot asphalt, she looked like some sort of goddess.

She walked up to the car. "Matt?"

"Hi ... ahh Mrs .... Mrs ..."

"Just call me Izzy dear. No need to be formal, we both know why we're here." Her slight Mexican accent was just detectable underneath some cultured schooling enunciation, probably Europe.

She opened the back door herself and got in. "Head towards my home if you would please dear but be ready to stop when I ask."

"Okay ... Izzy."

I never knew what to expect from a new ride. Some were into the whole coy thing, but really wanting to be seduced. Some were so nervous that I had to initiate intimacy. Some were flirtatious and wanted to keep things fun, light and breezy. Some wanted a taste of my highly empathetic side and shared a little too much of why she had engaged my services before getting down to business.

And then there were the ones like Izzy. I could tell right away she was the kind that just wanted paid for and uncomplicated sex, which is what I was selling.

Izzy rolled down the window, letting the hot Arizona breeze blow across her as she gazed out the window. Okay, not a conversationalist. Fine by me.

As we passed under the University Bridge over the road we were on she said "Here."

"Here??"

"Yes, find someplace to park. I'll decide from there." I looked back at her. Her dark brown eyes were wide and she had a small smile on her face. She looked at me, and those eyes were hungry.

I found a parking structure and pulled in. She was breathing a little heavy when she said "This is good. Find a corner, not next to any other car, but make sure there are some around. Make sure there is room on your side to open the door wide and it's visible."

Okay, I thought, this is interesting. The students at the university had left for summer so the structure wasn't full. I found a corner on the second level that was out of any direct sunlight. There were maybe half a dozen cars near, the closest one across on the row opposite the one I had pulled into and 6 spaces over.

As soon as I parked, I could hear her shifting around in the back seat. I turned and she had her hips up and was pulling off the tiniest G-string I had ever seen. Her vagina was shaved smooth, which was a little unusual for my clientele.

I had tried screwing rides in my car before. Although it evoked a lot of fond memories for both my ride and me, honestly given the average age of my clients it was never great for them. "Mrs. Marchand, I don't really think trying this in the car is the best ..."

"No." She said, her voice already a little husky with passion. "Just stay where you are. Open your door." It wasn't unusual for my rides to give me direction, after all they were paying me quite well for my services. I drew the line at disrespect or any attempt at humiliation and dropped those rides quickly, as Mrs. Andrea Vorkovsky had found out. But Izzy wasn't being rude or disrespectful. She just knew what she wanted and was letting me know.

I opened my door, swinging it out wide. She got out, came around to my side, knelt down by the car, grabbed my legs and swung them around so that they were out of the car. She started undoing my belt.

"Whoa .... Whoa ... hang on." I said. A public indecency rap and being a registered sex offender would kill my business forever.

She continued to fumble at my belt and was tugging at my pants, eventually yanking them and my briefs down below my knees. "I'll be quick. Do you think you can let up on your famous control and cum in my mouth fast?" My sexual endurance and ability to control my climax was well known amongst my rides and was typically one of the first things they mentioned when they recommended me to a friend. I was pretty sure there was a pool bet going to see who could break it.

"Ahhh, sure ... I guess soooOOOOO!"

Now I had gotten quite a bit of oral sex since I had entered into my line of work. Honestly, I wasn't entirely sure why. While I'm sure some women enjoy giving head, mostly what my rides were after was a good, long solid fucking with multiple orgasms. Not too many of them actively sought out getting me off into their mouth until I'd delivered what they were paying for.

Not so much with Izzy. She was putting so much suction on me she could have sucked my balls up through my cock. I've never used one of those penis pumps, but I had a feeling I was experiencing something similar. And she was making these short, sort of high-pitched humming sounds, which sent vibrations down my shaft, through my balls and straight into my hypothalamus. I don't think my cock had ever gotten that hard so fast. And there was something about how she said "... cum in my mouth fast ...", something I had never heard before, that had the launch sequence going already.

For her part, I could tell she was fingering herself frantically, apparently trying to get herself off as quickly as she was me. And it seemed like it was happening fast for her too. The little humming noises were starting to get higher pitched, little squeaks and squeals now. For my part my hips were starting to pump, and I was grabbing the handle above the door with both hands. That's when we heard voices.

Izzy immediately pushed her head down so that her lips were at the base of my cock and started swallowing. And then, so help me God and without so much as a by your leave, she stopped fingering herself, took one of her fingers that was well lubricated with her own juices and stuck it up my ass. She found my prostate ... and my Achilles Heel. My control, what little I had at that point, shattered. "Oh ... oh shit ... oh my god ...oh ... Jesus ....fuck ....". I think I actually spoke in tongues for a second. And then I spurted what felt like a gallon of cum into her mouth and down her throat. There was so much a little actually came out her nose which she had been breathing in through while moaning and shuddering with her own climax.

The oppressive heat of the parking structure and my unexpectedly quick orgasm had me dizzy and gasping for breath. But Izzy, she seemed as cool as a spa cucumber drink. She stood up, used one finger to scoop up the little bit of cum that had spurted out of her nose and put it in her mouth with a satisfied sigh. Then she straightened her dress and said, "Pull your pants up dear, those voices are getting closer."

################### Part 3 ##################################

I did take her home that afternoon. As we pulled through the automatic gate to their enormous ersatz Tudor-style mansion she said "Would you like to come in for a bit dear. My husband is out of town."

That afternoon I re-established by market bona fides by fucking her to six orgasms, each in a different position. The last one was bent over the arm of a heavily embroidered Tudor-style chair. After she stopped shaking, I pulled out my cock and started stroking myself with the intention of shooting a load onto her tanned ass, which some of my rides seem to enjoy. But as soon as she sensed what I was up to she spun around quickly, dropped to her knees and swallowed my cum again, this time without the ass play. When she was done, she sat back on her heels, wiping her mouth with the back of her hand.

"Sorry dear. I'm sure you understand. That chair and the embroidery on it is almost 500 years old." She stood up and kissed my chin. "Now I'm going to take a shower. Please help yourself to anything in the kitchen or behind the bar. I'll be down shortly." There was obviously no invitation for me to join her as she floated up the ornate sweeping wooden staircase to the mezzanine level above the living room where had been. She was humming softly to herself as she went through the double doors of the master suite and softly closed it behind her. I went to find the kitchen.

When she drifted into their large restaurant quality kitchen, I was eating a roast chicken sandwich on some really great and clearly homemade sourdough bread over the stainless-steel prep table.

"Oh good, you found something." She was dressed in a long gauzy cream-colored gown with a high collar and belled sleeves that was all but see through. It was belted with a gold embroidered sash and her feet were in matching gold embroidered slippers. Her long hair was pulled forward over one shoulder and caught with a similarly embroidered gold strip of cloth. She was agelessly breathtaking and looked like something out of Lord of the Rings.

She reached into the pocket of the gown and took out an envelope that was sealed with wax. She was really into this whole period thing. She slid the envelope across the table. It looked very thick.

"Sorry about the risky play earlier Matt. That's kind of my thing. I hope I didn't shock you too badly. There's something a little extra in there for you."

I picked up the envelope and hefted it in my hand. Holy crap. I didn't want to be rude, but I asked "Do you mind if I ..." I glanced at the envelope. She inclined her head gracefully and blinked slowly. I wiped my other crumb covered hand on my pants and used one finger to break the seal. There was easily $5,000 dollars in there.

"Izzy, this is too ...."

She interrupted me with a laugh. "Not at all dear! After all, I'll be collecting winnings that should be around $40,000 from all your other clients. You see, I won the bet."

God dammit, and on her first ride too. The other ladies were going to be pissed.

################ Part 4 ########################################

So that's how it began with Mrs. Isabella Ibenez-Marchand, and things hadn't changed much since. The day always started with sex in some semi-public place where she would race to get us both off before we were discovered, followed by a marathon session at her home because her husband was almost always out of town.

Today it was going to be in a changing room at a high-end clothing store, where we had been before. The risk of any discovery from the staff there was pretty minimal actually because Izzy spent a lot of money there and I am pretty sure they knew what was up when I discreetly slipped in at her invitation "Come in here and tell me how this looks dear."

I will say this, the dress looked great hanging on the door of the dressing room as Izzy, on her knees and in heels, lace bra and panties, bobbed her head, sucked me deep into her throat and found my prostate. I'm pretty sure the staff heard the thud of my head on the wall as I snapped it back and said "Oh ... holy ... fuck ..."

As far as I know and to this day, Izzy has never told another one of my rides the secret of breaking my control.