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  1. The Chauffeur......the Interview
  2. The Chauffeur......First Day/At the Office
  3. The Chauffeur...... First Day/ Jill
  4. The Chauffeur......Tina and Those Crazy Clients
  5. The Chauffeur.......Jill
  6. The Chauffeur.....The Plan
  7. The Chauffeur.....The Revolution, The Evolution
  8. The Chauffeur, Game On
  9. The Chauffeur....VEGAS BABY!
  10. The Chauffeur (#10)..Making it Great Again (part one)
  11. The Chair
  12. The Chauffeur(#11)..Making it Great Again (part two)
  13. The Chauffeur (#12), LA
  14. The Chauffeur (#13), The World Falls Apart
  15. The Chauffeur (#14) New Business, New Problems
  16. The Chauffeur (#15) Babies and a New Love
  17. The Chauffeur (#16) And So It Begins
  18. The Chauffeur (#17) The Fab Five
  19. The Chauffeur (#18) John
  20. The Chauffeur (#19) Diane and a Baby
  21. The Chauffeur (#20) The Return of Jill
  22. The Chauffeur (#21) Games.
  23. The Chauffeur (#22) Tampa and Dallas
  24. The Chauffeur (#23) The City of Angels
  25. The Chauffeur (#24) The Weekend (part 1)
  26. The Chauffeur (#25) The Weekend (part 2)
  27. The Chauffeur (#26) Bob
  28. The Chauffeur (#27) Getting Back to Work
  29. The Chauffeur (#28) Guns and Other Stuff
  30. The Chauffeur (#29) Selling the Horse Tracks
  31. The Chauffeur (#30) Red Door, Part One
  32. The Chauffeur (#31) Red Door, part 2
  33. The Chauffeur (#32) The Board of Directors
  34. The Chauffeur (#33) Thanksgiving
  35. The Chauffeur (#34) The Aftermath
  36. The Chauffeur (#35) Oh, the Tales We Weave
  37. The Chauffeur (#36) The FBI
  38. The Chauffeur (#37) Time For A Party
  39. The Chauffeur (#38) The Investigation Begins
  40. The Chauffeur (#39) Back to Business
  41. The Chauffeur (#40) The Trip
  42. The Chauffeur (#41) The Limo Companies
  43. The Chauffeur (#42) Extortion
  44. The Chauffeur (#43) Fighting Back
  45. The Chauffeur (#44) Seattle
  46. The Chauffeur (#45) John and Dallas
  47. The Chauffeur (#46) Shopping for Christmas
  48. The Chauffeur (#47) The Holidays
  49. The Chauffeur (#48) The Wedding
  50. The Chauffeur (#49) Christmas
  51. The Chauffeur (#50) New Year's Eve
  52. The Chauffeur (#51) Michael
  53. The Chauffeur (#52) Time to Reset

The Chauffeur...... First Day/ Jill

Categories Fiction, Anal, Blowjob, Consensual Sex


Published: 01 October 2018

  • Font:

The Chauffeur……First Day/Jill

Chapter 1

I picked up all the items for my back pack from the list. The back pack was stuffed full. I put it in the car, so I wouldn’t forget it.

I decided that I am hungry but needed a quick shower before I start dressing for the night shift. Once again, I felt nauseated. I took a slug of Pepto to help calm my stomach.

While I was in the shower, I decided to not masturbate. Not enough time, I thought to myself. I needed to dress, eat, and get over to the office by 6:30pm.

After the shower, I put on my navy-blue suit along with muted yellow long sleeve shirt. I had picked out a tie and handkerchief earlier but was now rethinking that choice. I decide that I was just overthinking something as simple as a tie. I put the tie on and grabbed my wallet and keys to head to work.

All the way to work, I wondered in my head about Jill. Former military-what branch? Plain spoken-to what extent? Most requested-why? I trusted Tina and to a certain extent, Sasha. Yet, I knew that Sasha was management and Tina was staff so ‘trust’ was like an egg, fragile yet sturdy.

I arrived at work. I was able to park on the first floor of the parking garage and was happy about that.

I debated on just going to the 12th floor to meet Jill or should I go to the office first? I opted for the office (quietly hoping to see Tina). Just the quick thought of Tina made my cock stir a bit.

I grabbed my back pack and headed to the elevator to ride up to the third floor for the crossover to the office building.

When I got to the crossover, I took a deep breath still trying to calm my nervous stomach.

“Well, here I go.” I thought to myself.

The security guy remembered me from a week ago. He congratulated me on getting the job. He didn’t even look in my back pack, which I found odd but none the less I got on the elevator.

At the 8th floor, I got off the elevator and headed over to the Happy, Happee Limo office doors. Again, no handwritten sign, so I just walked in.

Tina saw me first and sprinted across the phone room. When she got to me, she leapt into my chest and kissed me passionately. I dropped my back pack and put my arms around her and kissed her back intertwining my tongue with hers. I could feel her wonderful body pressing tightly against mine. My cock was at full mast with her in my arms. Gawd, she always smells so delicious.

“Is that hard-on for me?” Tina seductively asked.

“Absolutely!” I replied with a smile.

“No, its not. Its for Jill, isn’t it?” Tina asked with a pouty tone.

“Tina, how can it be for Jill? I haven’t even met her. I have no idea what she even looks like. So, stop worrying, it is because of you and for you if you choose.” I replied.

Tina let herself get down off me. She stood in front of me telling me that Sasha and Jill were waiting for me in Sasha’s office. My heart began to skip a beat. My head asking too many questions as I followed Tina and her beautiful body to the castle doors.

Tina knocked and walked right in to the office. I followed. I looked up to see Sasha sitting on the front edge of her desk chatting with a woman on one of her leather couches.

“Ah, Mr. David. I would like you to meet our best driver, Jill Morgan. Jill, this is our new employee Mr. David. I have a few things to go over with Mr. David, should take me about 10-15 minutes. Then he is all yours for the rest of the night. Sound good to you Jill?” Sasha asked.

“Yes Ma’am, sounds wonderful. David, I’ll be in the breakroom on my laptop when you’re finished with Sasha. Please come find me.” Jill said as she was walking out the office door.

I thought to myself “HOLY FUCK!” She is drop dead gorgeous. 5’9”/long black hair with straight bangs above her eyes/clearly an overly endowed chest 36EE minimum/flat stomach/tight ass/athletic legs/ and she smelled like roses as she walked by.

I felt self-conscious thinking about Jill in front of Tina. I looked over at Tina to see her chatting with Sasha about something. Tina finished her conversation with Sasha and walked by me, squeezing my ass as she went by.

“Mr. David, we have to do a couple of things before I turn you over to Jill. We need to make you an ID card and code it to our electronics. I need you to sign your contract. You left without signing it earlier today. But, the most important item is we need to discuss how to ‘service’ our preferred clients.” Sasha said to me.

“Well, let’s get started then.” I replied.

“Put your backpack on one of the couches and follow me to the computer room to make your ID badge. Oh, no, no, no. Stop. Let’s sign the contract first since you’re right here.” Sasha said.

I walked over to her desk where she handed me the contract. I looked it over, just making sure it was the same contract. Sasha handed me a Montblanc pen. I held the pen for a moment looking at it. I thought to myself that this pen probably cost more than half a million dollars.

I leaned down to the desk and signed my name. Sasha took the pen and signed her name. She buzzed her phone and asked Tina to step into the office.

She came right in. Sasha asked her to sign the contract as the ‘witness’. Tina took the pen, signed her name, kissed me, and welcomed me to the team. Then she left the office.

“Now, with that done. We can go make your ID badge. Follow me.” Sasha directed.

Sasha picked up the contract and headed for the castle doors. I followed and said nothing. When we stepped back into the main phone room, I realized that it was less than half full of young ladies on the phones. Clearly, not as buy as last Tuesday with I came in for my interview.

I followed Sasha to the computer room. She had me stand in a spot and the machine took my picture. We stood waiting for the machine to spit out my new ID. Sasha picked it up out of the tray, waived it over some sort of computer reader waiting for a green light to appear telling Sasha that my ID card was now coded properly for the specific places I would be allowed to enter.

Sasha clipped the ID card to an all-black lanyard and handed it to me.

“Place this around your neck until you leave the building. Then put it in your suit coat for safe keeping. If you lose this you need to notify me immediately, this way we can deactivate it so no one can breech our security. Do you understand Mr. David?” Sasha asked.

“Yes Ma’am. Since we need to talk about my service to our clients, should we talk as we walk back to your office or wait until we get there?” I inquired.

“We’ll wait until we’re back in my office.”


I followed her back to her office. She invited me to sit down on the leather couch that held my back pack. I sat after she sat down.

“Mr. David, let us talk about what you are willing to do and not do for our clients.” She said.

She asked me about how liberal my sexual appetite may be. She asked if I was straight, bi, or something else. (I said ‘bi’ but also explained that not since college have I done anything with a guy). She asked about whom I would not have sex. (Young children and animals). She asked what age, will I no longer be willing to pleasure a woman. (I told her that really depends on the woman). She inquired if I was willing to have sex with multiple women or even a couple. (Yes, and yes). She wanted to know if I had ever participated in a threesome, foursome, or an orgy. (Yes, to all three). Would I be willing to stay late or come in early, if a client asks for me (Yes). If I was offered a drug or alcohol no matter how little, would I partake (Not while I was working and certainly not if it would affect my ability to work). She ended the questions with would I have sex or pleasure a handicapped person (don’t know since I’ve never tried).

Sasha thanked me for my honesty. She buzzed for Tina and thanked me for my time and reminded me to take my back pack. Tina entered the office, took me by the hand, and lead me to go see Jill.

On the way to Jill, she pulled me into an unoccupied office.

“Did I hurt your feelings today when we were out in the hallway?” Tina asked sheepishly.

“Um, no. I understood what you meant. Was I a bit disappointed? Of course. Did I understand? Absolutely! Tina, you mean a lot to me. Your beauty, your charm, and your amazing smile make my heart flutter every time I see you. I know we’ve only known each other for two days, my interview and today. I don’t want to make anything difficult for you here. Nor, do I want to screw up what appears to be a great job working here.” I said with my heart in my eyes.

Tina smiled, kissed me passionately, and asked if I had been given a schedule yet.

“No, not yet” I replied.

“She said that she has already seen my schedule and ‘lucky us’ we both have the same days off Tuesday and Wednesday.” She said with excitement in her voice.

She went on to ask if we could get together on our off days, away from work, to see how well we click away from work. IF, that is ok with me.

“Absolutely!” I responded immediately.

“Great” She kissed me hard, intertwining our tongues.

I reached around her and grabbed her beautiful ass.

“Do we have enough time for a quickie?” I asked.

“No, not really. I’m supposed to be getting you over to Jill.” She said with a depressed tone.

We stopped hugging. I collected my back pack and off we went to meet Jill.

While we were walking to Jill, I had an idea.

“Hey, since we both have tomorrow off and Wednesday off maybe I could pick you up after work tonight?” I asked.

“Are you sure you want to do that? It might be late.” Tina replied.

“Tina, I will get to you no matter what time it is. Ok?”

“That would be wonderful.” She said excitedly.

“Where do you want me to pick you up, here at the office or do you want me to come to your house?” I asked, hoping she said the office.

“Right here at the office. I usually get off about 8 on Monday. I will go home and pack an overnight bag and be back before you get here.” Answering, still giggly.

She hugged me and kissed me again. She opened the door to the breakroom. Jill looked up from her computer, smiled and asked if my time with Sasha is over for the night. I told her it was.

Tina wished me well and excused herself, closing the door behind her.


“So, you’re the new cock in the hen house, I hear.” Jill said with an mischievous grin.

“Huh, what?” I was lost.

“Don’t worry about it. It was a bad joke.” Jill answered.

“Can we go somewhere private to chat a bit before our ride?” I asked.

“Sure. How private are you looking for big guy?” She said smirking.

“Anywhere we won’t be disturbed for a bit.” I replied as deadpan as possible.

“C’mon, follow me. I know where we should go.” Jill responded.

We walked out of the breakroom and down a short hall, around a corner, around another corner, down a long hallway to a lone office. Jill used her ID to unlock the electronic door, switched the light on and invited me in.

I sat down in a traditional office chair with Jill sitting in another one about 3 feet from me, facing me.

“Well? What do you want to talk about?” Jill asked.

“This job and you.” I replied surprising Jill.

I started by asking her what she had heard about me.

“Well, you apparently know how to please a woman. The gossip is that you’re packing a 9” cock. You made Sasha cum so much she had to beg you to stop fucking her, which by the way, has never happened before. You have fucked two girls, Tina and Paula, into unconsciousness. You are polite and a gentleman, which seems to make you the target for virtually every woman working here to want to have sex with you………Oh, and you have shown great affection towards Sasha’s assistant, Tina.” Jill said, smiling the whole time.

I smirked and shrugged my shoulders. I should have known that I was being too obvious about my feelings towards Tina. Now, everyone knows our business, or at least they think they do.

“What have you heard about me, David?” Jill asked.

“You are the number one most requested driver here. You are former military. You will make excess of $600K this year. You have been employed approximately 14 to 15 months. You are clearly Sasha’s favorite employee and you’re generally known for keeping your mouth shut. Am I close?” I said, kind of feeling like the cat who ate the mouse.

“Well, you don’t seem to know much about me sexually though.” Was her reply.

“So then tell me.” I replied in a smart-ass tone.

“I’d rather show you.” Jill said


We both stood up and wrapped our arms around each other, pressing our bodies together. Our lips met in a slow gentle kiss. She leaned in and cupped my face gently, all the while kissing me. She gently bit my bottom lip.

My hands began to roam over her body. She let go of my face and began unbuckling my belt. In one deft move, she unclasped my pants, unzipped me and had my pants around my ankles.

She knelt in front of me putting her fingers inside of my boxer shorts and pulled them down to lay on top of my pants. I’m sure I looked silly. Suit coat, long sleeve dress shirt, tie, socks and dress shoes.

She took a firm grasp of my cock. Licking the underside of the shaft started my cock to awaken. She swirled her tongue over and around the bulbous purple head. Her other hand started stroking my balls gently. After my cock finally sprang to full attention, Jill parted her lips and lowered her mouth over my entire cock in one move. She licked, sucked, and slurped my cock. I felt my cock go past her gag reflex of her mouth and into her throat. She swallowed my cock head without incident.

I gently caressed her head. It suddenly crossed my mind that I had not masturbated before coming to work and thus I may not be able to hold out very long. Jill had exquisite technique for giving a blowjob.

I decided to change tactics. I reached down and lifted her up by her arms, forcing her to abandon the blow job.

She looked quizzically at me, as if to say ‘what, I’m not doing it right’? I leaned in to kiss her again. I began unbuttoning her white dress shirt, unclipping her bow tie, and reaching inside of her shirt to put my hands on her amazing chest. I thought to myself that I have never had a woman who had such an endowed chest.

Thankfully, she had a front clasp bra on. I flicked the clasp and the boobs were unleashed. I bent my head down and began licking and sucking on her tits. While I was doing that, I slid her blouse and bra off her.

I spent a large amount of time licking her nipples and areolas. I heard a soft moan escape her mouth. Her hands were now massaging my hard manhood. I felt her rub the pre-cum drops up and down the shaft making me feel even more horny.

I moved back up to kissing her. She seemed to really respond by the kissing. I gently licked and kissed her neck, nibbled on her ear lobes, and gave her small little kisses across her forehead and nose, As I was kissing her, I felt her tense up and shudder.

I thought to myself, “did she just orgasm”? I had to know, so I leaned in and whispered in her ear, “Jill, did you just orgasm?”

“Oh yes, did you feel that?” she said looking into my eyes.

I kept kissing her. Softly at first, then a bit harder, till finally we were French kissing with force and passion.

Suddenly, there was a loud knock at the door. We froze. It was Sasha.

“Jill is Mr. David in there with you?” she queried.

“Ah, yeah. Why? Do you need him for something? We were having a private conversation.” Jill said, lying through her teeth.

I was rushing to put myself back together. I had my boxers up, my pants back up, my shirt tucked in when without warning the electronic lock clicked and the door flung open. There stood Sasha, smiling.

Jill hadn’t quite reconstructed herself. Her bra was back on and her blouse was on but only two buttons had been rebuttoned.

Sasha walked in and flipped the door closed behind her.

“Jill, dah-ling, you find Mr. David acceptable?” Sasha inquired.

“Well, actually we didn’t get very far.” Jill said matter of fact.

Sasha spoke up again, “Jill, you and I enjoy sex completely different. I prefer to be taken, like a conquest. I want my vagina driven home like the cock is a giant spike and my pussy is the board. You, on the other hand my dear, enjoy all that kissy, caressing crap. I never understood how anyone gets off on that.”

“Well Sasha, some people like the hard animal lust and some like the emotional lust…..I see you don’t understand…..let me try this way: We both like a sandwich, let’s say Peanut Butter & Jelly. You might like yours with crunchy peanut butter and grape jelly but, I might like smooth peanut butter and strawberry jelly. Both sandwiches are still PB&J just different. Make more sense now?” Jill asked.

“Well, Jill I came in here to include myself with you and Mr. David. I had an idea of getting fucked by him once more before you two get out on the road,” Sasha said with a grin.

“Well, how about he just fucks you, gets cleaned up and we head out with the limo to start the night.” Jill replied, with a bit of annoyance in her voice.

“That would be just fine Jill.”

“Mr. David, take off your clothes quickly and come to me and fuck me as you know how.” Sasha said with a gleam in her eyes.

I took off my coat, loosened my tie, took off my shirt, kicked off my shoes and socks, dropped my pants and stepped out of my boxer shorts. By the time I had done all that, Jill was fully dressed sitting in her original chair and Sasha was naked sitting on one of the leather couches.

Her hand was rubbing her already wet pussy. She beckoned me to come to her. I did as was requested.

My cock was again pointing up at the ceiling. Sasha was leaned back on the couch with her head resting on the arm of the furniture piece.

I grabbed my cock and thrust into her very wet womanhood. Yes, I remember this pussy from earlier today. As I thrust in and out of her hard, I could smell her musky scent. It smelled delicious but, I was more focused on pounding her, making her cum more than once but not cumming myself until after her 2 or 3 orgasms.

I turned my head to check on Jill, only to see her filing her fingernails with a facial expression of annoyance.

My brain was in overload. Jill was obviously mad. Sasha was obviously using her position of authority to get more sex from me.

I kept pounding away on her wanton pussy. I grabbed her clit roughly and pinched and twisted it, causing Sasha to yelp loudly. I heard her breathing become erratic. She was pinching her own nipples and pulling them/stretching them.

I reached up with my free hand to slap one of her nipples very hard. This caused Sasha to begin cursing in that Eastern European language. I also felt my cock and balls get very wet as she splashed my groin yet again.

I just kept banging her as hard and as deep as I could. I reached over, leaving her clit for a moment, to grasp her ankles and fold them back to be placed by her ears.

I heard Jill giggle softly. Yet, I kept pounding my cock hard into her.

Again, Sasha began that foreign gibberish with another splash of orgasm all over my mid-section. Yet, I kept hammering into her. I shifted a little bit so that I was now at more of a 10-degree angle pounding into her.

Again, she began yelling her foreign words and again, she splashed me with her warm, wet love juice.

“Mr. David, you may stop now. I think I have reached my limit.” Sasha said breathlessly.

Still, I kept pounding into her.

Jill piped up, “David, you need to hurry up now, so you have time to get cleaned up before we get on the road……David……. David, do you hear me?”

I slowed down and came to a stop. I withdrew my rock-hard cock, realizing that I still had not cum yet.

I just walked away from Sasha without saying a word. Jill pointed to a cabinet telling me there was cleanup towels in them.

I walked over to the cabinet, opened it and took out 4 towels. I walked back to where Sasha and I were coupled and handed Sasha two towels.

I began to clean myself off. Jill asked if I needed any help. I just shook my head no.

Sasha wiped herself down, tossed the towels on the floor, got dressed and left.

I finished cleaning myself up and got dressed. It was now that the items in the back pack made sense. I reached into my back pack, pulled out a small bottle of cologne, spritzed some on and told Jill I was all ready to go.


Jill and I walked silently to the limos parked on the 12th floor of the parking garage. I was amazed by the number, type, and color of limos they owned. I counted more than 50 vehicles. Long ones, super stretch, town car, Humvee, stretch SUV, as well as an open back super stretch with a hot tub in the open spot.

Jill walked over to one of the town cars. She popped the trunk. We both put our back packs on the far edges of the trunk. Hers’ on the driver side. Mine on the passenger side. She unlocked the doors and we got in. She started the car but, before she was able to put it into gear I reached over and turned the key off.

“Jill, I’m sorry.” I said.

“For what? You did nothing wrong.” Jill replied.

“Well, I FEEL like I did. You are clearly upset, and I feel as if I was the cause of that.” Looking directly at her as I spoke.

“It is HER! She knows how to push my buttons. She knows that I’m not going to quit. I’m a Marine dammit. Marine’s do not quit. We do not back down, and yet we’re prepared and willing to fight if need be.” Jill spoke clearly not annoyed, but angry.

“Well, I’m sorry anyways. I thought we were going along wonderfully before we got interrupted. Don’t you agree?” I said looking into her eyes still.

“David, after what I heard about your performance I was expecting the same thing with my pussy getting pounded. However, you read me correctly. I truly enjoy the soft, sensual, caressing, touching, and KISSING more so than the fucking. Don’t get me wrong, I like…no, I love being fucked but I prefer the emotional side more than the physical side of sex. Let me also give you a nickel’s worth of advice: Watch yourself. You have done something to Sasha that few, if any, have done before. You have given her multiple orgasms and have caused her to squirt. You, my friend, now have a target on your back. She is going to keep you under a microscope for a while. So, if the rumors are true about you and Tina, you need to keep it out of the office. Whatever is or is not going on with you two keep it completely professional at work. Got It?” Jill said in a plain tone.

She had given me a lot to think about now.

Jill restarted the car. Put on her ear piece to the mounted cell phone and dialed in that we were leaving the garage and will be available in about 5 minutes or so.

As we pulled out of the garage, Jill suggested we hit a Starbucks for a coffee. I agreed, even though I really don’t care for coffee. I figured that I’ll just get a bottle of water instead.

We sat in silence until we reached the coffee shop.

“Ok, this is going to be a very long night if you don’t start talking.” Jill advised.

“Well then, I’ll order 3 bottles of plain water, none of that fizzy stuff. Jill, how busy will we be tonight?” I asked.

“Hold on for a second.” Jill said at the same time the speaker asked for her order. She placed the drink order and told us to proceed to the window.

After we got our drinks, Jill answered my other question, “We should be dreadfully slow tonight. I would be surprised if we even make seven hundred dollars in fares tonight.”

“Um, if that is bad, what then is a good or even a great night?” I asked out of curiosity.

“Well, our average drive to ‘regular’ customers runs about 1200-1500 a night. However, that does not include the ‘clients’ who pay lots more for our personal touches.” Jill explained,

“Jill, I feel like I still owe you. We didn’t get to finish what we started in that back office. I would like to at least pay my debt.” I offered.

“Really? You think that you ‘owe’ me? No Hun, you don’t owe me. But, if you would like to finish what we started, then I’m in. However, you really got to stop thinking you owe people or feel like you need to be, submissive to Sasha. This place will tear you up if you don’t toughen up a bit. Remember what I’m sure Sasha has already said to you…….(mocking Sasha in an eastern European accent) {Mr. David, this is not making love. This is sex.}” Jill explained to me in a matter of fact tone.

She went on to tell me that when we log out for our lunch break, she knows a few nice hotels that will give us a room for up to three hours at no charge for us to get some shut-eye during a long shift. Of course, I found out that if you ‘service’ a manager or night manager every now and then will help things along too.


The first part of the night was dreadfully slow. We kept patrolling some of the upscale resort hotels with only one fare for a measly $200.

About 4 hours into our shift, Jill asks if we should take our lunch break.

“Um, sure, why not? I’m a bit hungry.” I said

“So, you don’t……” her voice trailed off.

“Oh, my gawd, I thought you were asking a real question about food. Of course, I want to finish what we started. Damn, I’m so stupid sometimes!” I said hoping she understood.

“GREAT!” she answered smiling now.

We drove about 3 blocks away to a very nice upscale resort known as the McCall. Built more than a hundred years ago but, updated into a top end resort hotel about 3 years ago.

“Hello Jill. Welcome to the McCall. Are you here for the night or just a short nap?” The valet asked.

“Just a nap James. We’ve been working since noon and won’t get off shift until about 4am. We are already bushed. Oh, by the way, this is David. He’s new and tonight is his first night.” Jill explained.

“David, sir, it’s a pleasure to meet you. I’m James, I run the valet service here at the McCall. If you’re first night is with Jill, then you are riding with the best!” James said, in a bit of a flirtatious tone directed at Jill.

“James, please don’t call me sir. David is fine.” I corrected him.

“Yes, sir. I’ll call you David, but please excuse me if I slip and call you sir. It is a habit from my training.” The valet said.

Jill popped the trunk and grabbed both of our back packs. She tossed mine to me and we went inside. Jill went straight to the front desk and a stunningly beautiful lady stood behind the check-in counter named Donna.

There was some small talk between Jill and Donna.

Donna handed over a plastic key and offered to have a bellman carry our bags to the room for us. She declined saying we only needed a couple of hours of sleep before getting back in the limo to finish our shift.

Donna came from around the counter and walked right over to me and introduced herself.

“Hello, welcome to the McCall. You must be Jill’s FNG. I’m Donna. Jill and I go way back to the days of being Marines.” She explained.

She then gave me a quick smooch on the cheek and went back behind the counter.

“C’mon, this way. She put us one floor below the Penthouse floor. Real nice suites. They’re barely used.” She explained as we waited for the elevator.

As we rode the elevator up, Jill explained that I should keep close tabs on Donna. She’s hardworking, dependable, keeps her mouth shut, and most of all….is fun in bed.

Yep, she shocked me.

“Tonight, we will visit some places and I will introduce you into some key women you need to take care of from time to time. These women are important to your financial success with this company. You see, if a client’s hotel plans crap out and you provide them alternate upscale accommodations, you could easily get a tip somewhere between 5 and 10 grand! This is the reason, it is very important you keep in close contact with those who I introduce you to tonight. Got it?” Jill explained.

“Absolutely! However, what is an FNG?”

Jill chuckled and said, “Fucking New Guy”

The bell rang for our floor.

“27th floor…. power tools, lingerie, and ME!” Jill said with a cheesy grin.

We left the elevator. I only saw 4 doors on this floor. ‘Nice’, I thought to myself.

We went to our left to door 27A-2. Jill inserted the key card and opened the door.

When I stepped inside, I was stunned. Never in my entire life had I seen such lavish luxury.

“Don’t get too excited, this is not the best that they have. This suite ‘only’ goes for $2500 a night. The penthouse floor above us, only has two suites to the floor and they each go for $15,000 a night” Jill told me seeing me flabbergasted.

Jill flipped the door closed behind us. Before I even had the opportunity to set my back pack down, Jill had her arms around me, kissing me passionately. I dropped my back pack where I stood. I put my arms around her and pulled her in tight. I could feel those wonderful breasts push against my chest.

As I was kissing her, I began unbuttoning her blouse. With some deftness, I got her blouse unbuttoned and pulled it off her working on her bra next.

Jill whispered in my ear, “I’ve thought about you all night.”

My cock was hard waiting for Jill. She knew it too. Her hand began tracing the outline of my manhood through my pants.

I kept kissing her, working my way from her lips to her neck. I licked from her collarbone back up to her ears. I nibbled on her earlobe once again. I worked my way around to the back of her neck, wrapping my arms around the front of her.

I kept kissing her neck. I let my hands gently caress her beautiful EE chest. I pinched her nipples all the while I was rubbing my hard cock in her ass crack. I was still wearing my trousers. Jill reached behind her and unbuckled my belt, unclasped my pants, unzipped me and pushed my pants and my boxers down.

I stopped playing with her wonderful chest for a moment to take her pants and undies off.

She took my hand and walked me over to this huge bank of windows. She hit the button and opened the drapes. The view was utterly beautiful. You could see across the city all the way to the water’s edge. I was stunned to say the least.

Jill, bent over at the waist, offering me her ass.

I asked, “Are you sure?” as I wanted to be sure she wanted ass sex and not to just do it ‘doggy style’.

Jill whispered back, “Yes my dear. Only a few select people have been allowed. Please take me, but be gentle at first until you’re all the way in.”

I was worried about what to use for lubrication. I stopped for just a moment and went over to my back pack where I reached inside and pulled out a small tube of lubricant. I hustled back to a waiting Jill.

She saw the lube and smiled. She was rubbing her delicious wanton pussy the few moments I was gone. I took those wet fingers and put them in my mouth and sucked them clean. She tasted wonderful.

I popped open the flip top cap. I squirted some on the crack of her beautifully shaped ass. Using my free hand, I rubbed it deep inside of her crack lubing up her anus rosebud before sliding my finger inside of her. She let out a gasp, since she was not expecting me to do that.

After a couple of moments, I put in another finger causing Jill to begin erratically breathe. Without any warning, I put in my two remaining fingers leaving only my thumb outside of her ass. I moved all 4 fingers in and out rhythmically. Jill reached her first orgasm. I could feel her whole body shake and spasm. The sphincter tightened around my fingers.

I squeezed more lube out on my cock and dropped the tube onto the floor. Using my now free hand, I rubbed the lube all over my steel hard cock.

Slowly I removed my fingers from her anus. I whispered in her ear that I was now going to begin fucking her.

“Oh yes, take me!” Jill breathlessly replied.

With my free hand that was just in her ass, I grabbed the base of my cock and gently pushed the head inside. I didn’t really need to be that gentle as her ass was in gape mode. I pushed my cock all the way inside until my balls were against her pussy.

I started slowly fucking her. I knew she would want me to be steady and not just ‘pound away’. I kept up the in and out motion.

I felt her body tense up, her breathing very erratic, and all at once I felt wetness on my shins. Oh, my goodness, this raving beauty just squirted! I kept fucking her ass.

Now, I was getting cockier by the minute. I began to pick up speed on her anal plundering. Breathlessly, Jill begged me to go deeper and harder into her.

I picked up speed and began hammering her ass with all that I could muster. In and out, in and out, over and over. My hips were in a blur going as hard and as fast as I was fucking her rear hole. Much to my surprise, I felt a new amount of pussy cum hitting my shins and feet.

“Oh, my holy gawd. David…. ahh…. ahh…. David…. you fuck my ass like no one else has ever.” Jill yelled while cumming yet again.

I leaned over her back. “Jill darling, I’m close” I whispered in her ear.

“I want you to cum in my ass. Please, please, please…cum inside my ass. Please David” She responded.


As we slowed down, her breathing became more regular. Her body more relaxed. It took all my remaining strength to not collapse on Jill’s back. My cock was now deflating, I stepped back withdrawing my cock from her ass.

I spun her around, stood her up, and kissed her hard. I whispered in her ear that we should probably shower and get dressed as we only have about 25 minutes left of our dinner break. I offered her to shower first. She accepted and grabbed her back pack, her clothes and shoes to head to the bathroom.

While she was in there, I messed up the bedding on two of the beds. That way, it would look like we did sleep.


I heard the shower turn off. I grabbed my back pack, my clothes, and left my shoes by the couch to put them on when I was dressed.

I heard Jill come out of the bathroom. She walked right up to me and planted a long passionate kiss. After our lips separated, I hurried into the bathroom for the fastest shower ever.

4 minutes to shower, not bad, I thought to myself. I opened the bathroom door and stepped out to dress. Jill was already dressed and waiting on me. I hurried through dressing, going out to the living room couch where I left my shoes and socks.

Once I finished and was ready, I asked Jill, “Anything we need to do before we leave?”

“Not really. Just make sure you have everything because the key card is single entrance only. Once the door closes behind us we are locked out.” She informed me.

I glanced around the room. Jill commended me for mussing up the beds to make it look legitimate that we slept. I pushed the button for the drapes to close and spotted the tube of lube on the ground by the windows. I picked it up and stuffed it in my back pack.

Jill and I took the elevator back down to the lobby. I offered to return the key card to Donna which Jill thought was a very good idea.

I went over to the counter. Chatted with Donna for a minute or two. I got her ‘business card’ complete with her personal cell phone written on the back. I smiled at her knowing that there were customers waiting to check-in behind me. I blew her a kiss from across the counter and headed out to the valet.

The limo was waiting at the front door. I saw Jill give James a light kiss and hand him some money. We both got in the limo, Jill put on the cell phone ear piece and checked in with the dispatcher.

“Oh, thank gawd you’re back. We’re in a bind. Mr. and Mrs. Paxton are landing in 15 minutes. Their usual driver, Denise had an accident tonight. Can you pick up the Paxtons?” the dispatcher asked in desperation.

“Sure, but you do remember I have David with me tonight.” Jill reminded.

“Sasha said that it doesn’t matter. They are long time clients and we can’t drop the ball on them. So, please get your gorgeous ass over to the private part of the airport. You won’t be able to miss their Gulfstream 7 jet. It’s painted purple. Pull up to their plane, aid them off the plane, if needed. Put their luggage in the trunk and take them to their hotel, the Pinetree.” Dante, the dispatcher said as if Jill had never taken clientele before.

“Dante, I’ve done this before, not with the Paxtons, but I know the drill. Oh, and by the way, you do know that have a town car not a limo?” Jill asked.

“Yes, Sasha told me you were scheduled to drive a town car tonight. Please just explain to them that their requested driver, Denise was in a serious accident tonight and that you and David were asked to step in. There will be no charge since they are not getting their requested driver, nor the proper car. They are usually reasonable people.” Dante said in a panic-like voice.

We had already left the McCall and were pulling into the airport entrance way to the private field for high-end aircraft when Dante hung up.

“Oh shit, I forgot to ask about Denise. They’ll want to know. I’ll just tell them that she was taken to the hospital and there is no word yet.” Jill said out loud clearly thinking the scenario through.

“Jill, may I handle this for you? You can easily step in if you don’t think that I’m handling the issue properly, please?” I asked.

“Um, I’m not sure. It’s your first night and all. But, you got to learn how to handle things like this at some point. So, I guess it would be alright. If you get in over your head, ask me and I’ll take over for you. Deal?” Jill said.

“Deal. Hey, there’s their plane. When we get to the plane, just pop the trunk and let me handle them.” I said smiling.

We pulled up to their plane before the aircraft door opened. I hoped out and stood waiting for the aircraft door to open.

When it opened the steps folded out, I stood at the bottom of the steps. Mrs. Paxton was the first to come out and head down the steps. She looked at me quizzically.

I put my arm out to offer her assistance with the steps introducing myself. “Hello Mrs. Paxton. I’m David. Your requested driver was in a serious accident a little bit ago. Jill and I were asked to make sure you and Mr. Paxton have a safe journey over to your hotel, the Pinetree.”

I was walking Mrs. Paxton over to the car, opening the door for her when Mr. Paxton appeared at the top of the Gulfstream’s steps.

Before he could even ask, his wife let him know that Denise was in a serious accident and the limo company sent them instead. Mr. Paxton seemed to relax knowing what happened to Denise.

I offered to get their luggage which the steward from the plane was lining up at the bottom of the stairs. I took one look at their luggage seeing it was the Rimowa brand luggage, which goes about $1500 per piece.

I loaded the luggage in the trunk. Got into the front with Jill and asked her to head to the Pinetree.

“Yes, sir.” Jill replied.

As we left the airport, I turned around and explained to the Paxtons that on behalf of the Happy, Happee limo company we will not be charging them for tonight because they are such preferred clients and we apologize that neither their preferred driver nor their requested limo showed up to transport them to the Pinetree.

Mr. Paxton spoke, “Is it David? Things happen. You have taken ownership of the issue and it was very responsible of you to show up to pick up my wife and I.”

Jill spoke up, “Mrs. Paxton is there anything you need? We are only about 5 minutes from the Pinetree.”

I thought to myself, ‘nice touch’.

“No, my dear. We just want to get to our hotel since we hit lots of turbulence on the flight over here. I’m ready for a long soak in a hot tub then bed, with my sexy hubby, of course” Mrs. Paxton said with a wink to Jill.

We pulled into the valet area, popped the trunk. I jumped out to open the doors for Mr. and Mrs. Paxton. The bellman was waiting for the Paxtons with a hotel cart and he began unloading their luggage from the limo.

Mr. Paxton waved me over and handed me three sets of folded up bills.

He said to me, “This one is for Denise. Please tell her from us, that we hope she is ok. Please call my secretary when there is word on her. The second one here is for your driver. She was pleasant, and it was a very nice touch of her asking my wife if she needed anything. And, David, this is for you. It was nice to see a manager take charge and take care of their clientele. I will be calling Sasha tomorrow and telling her what a wonderful manager you are.”

“Mr. Paxton, thank you, but it is more important that we keep our clients happy. You don’t need to make any fuss about me to Sasha. She knows me, since she is the one who hired me.” I answered.

“David, one more thing. If you EVER need a job, please call me. I can use a top-flight manager like you in my company.” Mr. Paxton said handing me his personal business card with his private number on the back.

“Mr. Paxton, I’m honored. Thank you. Please have a good night.” I replied.

As I turned around, I saw Jill standing outside the driver’s door with her mouth hanging open.

I went over to the car and got in. I asked if there had been any word about Denise. She told me that Denise was shaken up, but the limo is totaled. She said that Sasha would explain to us later.

I gave Jill the folded bills that Mr. Paxton gave me for her. She unfolded it and saw that there was, seven $100 bills. She asked about the other two folded money packets. I told her one was for Denise. I unfolded it and saw that there was, five $100 bills. Which made me curious about the packet he gave me as it seemed thicker. I unfolded it and Jill’s eyes got as big as saucers. I counted all the bills up and there was, a total of twenty $100 bills……he gave me a $2000 tip!

Jill laughed out loud, a real belly laugh.

“You need to put that money away and not tell Sasha about it. She thinks that no new driver should be getting tips for at least 30 days. Unless she asks you directly about it, then say nothing…not even to Tina.” Jill said smiling to me and giggling.

We spent the rest of the shift going to various top end hotels. Jill introduced me to Sara, Jackie, Dania, Susie, Marsha, and Eloise. Each one of them gave me a business card with their private cell numbers written on the back. Although, Susie and Eloise wanted to take try me out right then, Jill politely postponed the sex telling them that we had a customer to pick up.


As the shift wound down, Sasha called. Jill put her on speaker. “I just got off the phone with Mr. Paxton. He is requesting that I double Mr. David’s salary effective tonight or he will pull his business and terminate the contracts of his hotel chain with our company. If I fail to do that, he will recruit you to work for him and pay you FIVE times whatever I’m paying you. What the hell did you tell him to make him believe that you were a manager for us?”

“Nothing Sasha. I just spoke to him about why his requested driver, Denise, was not there and why we didn’t have the proper car for him and Mrs. Paxton. After a couple of minutes in the car, I turned around and told him that because he was such a valuable client that we would not be charging him for the journey to the Pinetree. He wants me to call his secretary tomorrow and update him about Denise. He even gave me $500 for Denise and told me to tell her that they want to hear from her when she is able to call them.” I explained.

“Well, you need to come straight to my office when you get back to the office.” Sasha said before she hung up.

Jill was now giggling again. “Time to get that cock wet FNG”

I laughed and off we went back to the office. When we parked the car in the ‘get ready’ area and got out, grabbed our back packs and headed for the elevator.

While we were waiting for the garage elevator, Jill leaned into me and gave me a nice wet kiss. She whispered in my ear, “You are amazing. My ass is available to you anytime you want it. We could have lots of fun. I haven’t had such a great night since I started working here. You are going to make a huge difference and if you ever leave many people will follow. Good night sweetie. I’m not going back into the office as my car is parked on the second floor.”

I went into the office and headed straight for Sasha’s office knowing what was going to happen next. I knocked and walked in not waiting for acknowledgement.

Once inside, it was Tina, Sasha, and me. I put the $500 for Denise on Sasha’s desk.

“Mr. David, you need to fuck my Tina and me.” Sasha directed.

I started taking off my clothes. My cock was beginning to stir seeing Tina.

Tina shed her clothes faster than any of us. But, I noticed that she had a small amount of dry cum in her panties. I looked at her quizzically. She whispered that she would tell me later.

Sasha directed me to let Tina blow me until I was hard at which time I was to come over to her and fuck her like the other times.

Tina smiled at me and winked when she got on her knees and took my nearly erect cock into her warm and wet mouth. I felt her tongue swirl around the bulbous head. She licked up and down the shaft. She took one of my balls into her mouth licking and sucking on it. While she had my balls in her mouth, she stroked my cock getting me fully hard. Seeing and feeling my hardness, she got up off her knees and gave me a smooch on the lips.

I whispered into her ear, “Don’t worry. I’m going to fuck Sasha hard like she wants it and then you and I can spend the next two days at my place not even get out of bed if that’s what you want.”

At that, I turned toward Sasha who was laying on one of her couches with her fingers stuffed into her wet pussy. She was finger fucking herself hard and fast so much so that you could hear the sloshing.

I smiled at her and went over to her. I grabbed both ankles and put them over my shoulders. I pushed my cock straight into her very wet love hole. I rammed it home hard right from the beginning. I used one hand to pinch and twist her clit hard, while my other hand began twisting her nipples.

I kept pounding in and out, over and over. I looked over at Tina, smiling at her. She had put her clothes back on and smiled back at me.

Harder and harder, faster and faster I kept fucking Sasha. Then the inevitable happened. She began to breathe unbalanced and stuttered. I knew she was close. I really pinched her clit with much more force, which put her over the edge. Once again, that eastern European language made its appearance. She was balling up her fists, holding her breath, and cursing in another language. When suddenly, she arched her back straining to stretch her body. I felt her feet kick me on the side of my head. Her whole body began to shake, violently.

Suddenly, her entire body went limp.

“Did she just pass out?” Tina asked, smiling her big beautiful smile.

“Um, I think so” I replied.

Tina jumped up and ran over to the couch. As hard as she could, she slapped Sasha hard across her cheek. Nothing happened.

I leaned down and slapped her myself. She made a huge gasp of air. Tina stood there smiling.

Tina said, “Sasha, welcome to the fucked unconscious club. You are member number 3!”

At that point, I uncoupled from Sasha heading over to the cabinet where she kept the cleanup towels. I grabbed 4. I stopped at the sink putting warm water on two of them.

I walked back over to Sasha who was still in a daze laying on the couch. I laid two towels on her stomach.

Tina took the other two towels and began cleaning me. After I was clean, she began drying me. I put my clothes back on and turned and walked out the door with Tina right behind me. We walked through the phone room. We saw the twins leave their desks to go assist Sasha.

As we waited for the elevator, Tina said to me, “WOW, that was impressive. I’m guessing you will be taking over now.”

“No. I’m just the chauffeur.” I said smiling to her. I leaned in kissed her and held her hand while we waited for the elevator.

I hope you enjoyed this chapter of the Chauffeur series. Please leave me a comment, good or bad, so I can continue to develop stories that everyone will enjoy……Thanks, Paul.

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The Chauffeur...... First Day/ Jill

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Comments (2)
countrycadillac — 02 October 2018 19:47
What else can I say other than WONDERFUL and of course PERFECT !! I shall forever read any and all of your future stories !! THANK YOU !!! COUNTRY CADILLAC
PABLO DIABLO02 October 2018 21:01
WOW! Thank you for your kind words. They mean a lot to me. Please do me a favor an read the Amy and Darleen series. The first and third story got really good marks but the middle one not so much. Maybe it was too much story and not enough sex, but I don't know. Please drop me a line and let me know what you think...…..Thanks, Paul.
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