The Chauffeur…. Tina and Those Crazy Clients
Written by: PABLO DIABLO
As Tina and I left the office hand in hand, I smiled. I knew that I was in a much stronger position by taking care of Mr. & Mrs. Jaxson. They were wonderful people.
At this point, I was recapping, in my head, what has happened to me since I joined the Happy, Happee Limo Company:
• I’ve had sex with Sasha-my boss, Tina-her assistant, Paula-a colleague in the phone room, and Jill-the best driver in the company.
• I received a $2000 tip from Mr. Jaxson, just for doing what one is supposed to do to take care of a client.
• I’ve gotten a 100% pay increase due again to Mr. Jaxson, on the night of my very first day. My salary is now is a guaranteed minimum of $400,000/year plus tips and bonuses.
• I’m smitten with Tina.
• Sasha has used me for sex multiple times, at her discretion.
• Jill took me around to various top end Hotels/Resorts and introduced me to key women that I must keep in touch with to further my career.
• I’m now the ‘talk’ of the office.
• My antics have started a new club…. “The Fucked Unconscious Club”
Then, with a ‘ding’ the elevator opened to allow Tina and I to step on. We rode down in silence. My mind was way off in the distance. When the elevator doors opened, I was surprised that we arrived so quickly to our floor. We stepped off the elevator, Tina asked if I’m ok.
“Yes, actually I’m great! I have had an incredible two shifts working here.” I said, leaning in to kiss her.
“Wonderful, I want to hear it all.” Tina replied smiling the whole time.
We will, but not here. There are too many recordings and listening devices.
“How do you know that I’m not hiding a recording device?” Tina joked.
“Well, I guess I’ll just have to thoroughly search you.” I said smiling my cheesy smile.
“mmm, that sounds delicious!” Tina replied.
“Are you hungry? I’m starving, haven’t eaten since my second shift started.” I said without thinking.
“So, you did fuck Jill then.” Tina snapped back.
“Um, yes.” I said in an ‘I’m sorry’ tone.
The next few minutes, Tina railed on and on about how Jill gets all the sex she wants. Jill was such a slut. Jill was this and Jill was that…blah, blah, blah.
At some point, I just tuned her out. I wondered to myself, why is she so jealous about Jill? What the hell had Jill done to her?
“ARE YOU EVEN LISTENING TO ME??” Tina barked at me.
“No, not really.” That made her even more mad, if that was possible.
At the next intersection, I made a U-turn.
“What the hell are you doing?” She demanded
“Taking you back to the office. I’m not spending my two days off listening to a bunch of bitching and being miserable. Tina, I like you. I really do. But, maybe we are just not suited for each other. I’m sorry.” I replied.
The next few minutes, we drove in silence. I glanced over at Tina, she was caught up in mixed emotions. On one hand, she was so jealous of Jill. On the other hand, she thought, her and I would spend the next two days in bed together. I saw a small tear forming on the side of her eye closest to me.
“FUCK” I thought to myself.
I knew I had just hurt Tina. I put the dagger right through her heart. I didn’t mean to do that, it just came out. Guess once you’ve been burned on love, you tend to circle the wagons around your heart.
As I came upon an IHOP, I pulled in and parked my car. I got a very bewildered look from Tina.
“What are we doing here? I thought you were taking me back to the office and dumping me off.” She questioned.
“We’re going to eat. Have an adult discussion, which at the end of WE will decide which way this car will be headed when we leave the parking lot. Fair enough?” I replied as unemotional as possible.
“yes” Tina said sheepishly.
I got out of the car, walked around to her side, opened the door and waited for her.
As she got out, I leaned in and kissed her on the lips. Not overly passionately, but just to show that I’m still interested if we can work this out.
We went into the restaurant, which was nearly deserted. Only one other table with people. The other table was drunken college age kids having a raucous time. They were loud, but I didn’t care.
I asked for a table away from them. The hostess/night shift manager walked us to a booth away from the kids. She tossed the two menus down and said she’d be right back to take a drink order.
Tina slid in on one side of the booth and I slid in to the opposite side. I debated in my head about sliding in next to her but chose not to, not yet anyway.
I flipped my menu open. Looked over the listings and decided to just have breakfast.
“Any ideas what you would like? My treat.” I said as I looked into her tear-filled eyes.
My heart sank. I knew I wounded her. My head was a spinning top. Lots of emotions running through it simultaneously.
“Ok guys, what’ll you have?” The hostess/manager/now waitress asked smacking her gum.
“Well, I see a wedding ring, so I guess not you” I said, chuckling.
The waitress chuckled a bit, most likely at my stupid joke thinking it would help her tip.
“I’m sorry Ruth. That was a bad joke on my part. Don’t worry, the jokes are bad and get worse as time goes on. Tina, what would you like?” I said.
“Let me have a glass of orange juice, a water with no lemon, and the cobb salad with lite Italian dressing, please” Tina said still trying not to tear up
Then Ruth looked at me.
“I’ll have the man-breakfast, scrambled eggs, bacon, hash browns, pancakes with maple syrup, and a large glass of pineapple juice, if you have any, if not then apple juice with a large ice water also no lemon.” I directed to Ruth.
Ruth smiled, still smacking her gum and walked away.
I put my hands out on the table towards Tina, palms up. I was hoping she would reach out and put her hands in mine. But, alas, no.
“Tina, I do like you. I hope you know that. But, there is more to me than what you have seen so far. Can you understand that?” I asked quietly.
“I guess so. I thought we were going along so well, but then you went and fucked Jill.” Tina said with a tone of anger.
“Tina, we’re not married. We’re not even dating, in fact this IHOP would be our first date. I don’t know what happened between you and Jill for you to be so angry at me and upset with her. Which makes me wonder why is it ok for me to fuck Paula and have sex with Sasha at her whim? How do you find that ok, but not Jill? I’m lost here. Please explain.” I answered back as gently as I could.
There was a pregnant pause. Ruth arrived with our drinks and left again.
The silence was deafening. The college group got up, literally staggered to the cash register and began trying to put together enough money for the check.
“You’re about $20 short PLUS MY TIP.” Ruth barked
I told Tina to be still, that I would be right back.
I got up and went over to the register. The college group was digging in their purses, pockets, opening their wallets, looking everywhere for more money.
“Look, if you don’t have the money I’m going to have to call the Police.” Ruth barked at them again.
I walked up to the register and introduced myself. “Ruth, how much is their bill?”
“They’re about $20 short plus my tip” she replied icily
“Ruth, that’s not what I asked. How much is their total bill?” I asked again.
“Their check, ‘SIR’, is $67.50.” Ruth said dripping the words with a tone.
“Fine, I’ll take care of their check PLUS your tip. Good enough?” I answered her with a sarcastic tone of my own.
I reached in my pocket and pulled out one of the $100 bills I got from Mr. Jaxson.
The college kids were stunned. They all asked me for my name and where could they send the money to me.
I gave them a generic business card from the limo company. I wrote my name on the back, thinking to myself that I will never see them again. But, I smiled and gave the card to a nice young lady who seemed to be sober enough to drive the group safely home. They asked, while Ruth was finishing the transaction, if I owned the limo company.
“Nope, I’m just the chauffeur.” I replied smiling at them.
“No fuckin way” said one of the drunken college boys.
Ruth put my change down on the counter. $32.50. I picked up the ten, the two ones, and the two quarters and walked away. I left her the twenty for her tip. Coming from the restaurant industry most of my adult life, I knew Ruth had THE sucky shift and was being overworked by the company.
I walked back to the table where Tina and I were sitting. First thing I noticed was her smiling again. Well, that’s a step in the right direction, I thought to myself.
I sat down back on my side of the table.
“It’s nice to see you smile again. I was worried there for a few minutes.” I said to her.
Just then, Ruth showed up with our meal. She was so different now. She politely put our meals down on the table, offered ketchup, hot sauce, or more dressing for Tina’s salad. We declined them all, thanking her and she went back to one of the booths where she was rolling silverware.
We began eating. I looked at Tina wondering if I was going to have to carry this conversation on my own.
“Tina, you didn’t answer my questions. What gives. You bring Paula into the office for me to fuck, you bend over for me to fuck, hell, even Sasha keeps using me for her pounding and yet you are upset with Jill. I do not get it. Please explain it to me.” I inquired.
Tina began, stuttering a bit trying to hold back tears, “Sasha owns me. I am her personal servant/sex slave. Everything she wants from me she gets without question or objection. I brought Paula in because I just knew that you would enjoy her as much as I have…Jill, well Jill is another story completely.”
I sat there puzzled still. “So, explain to me how Sasha ‘owns’ you?”
“Well, that’s kind of a long story.” Tina replied sheepishly.
I looked around the restaurant. No one except Ruth and the short order cook behind the counter prepping something.
“We don’t have to be anywhere so keep going.” I suggested.
“Um, ok. Several years ago, I was in a horrible relationship with a guy. He was physically abusive, mentally abusive, and worse of all he had me have sex with all his friends, work buddies, and other random guys. I was raped repeatedly by his work buddies as he laid passed out from too much drinking. One night, that I really remember as if it was yesterday, they laughed and told me that I was going to ‘pull a train’. I ended up having hard painful sex with more than 15 guys that night, that I can remember. They whored me out. They called their buddies who showed up. They tied me to the bedposts, stripped me of my clothes. They had their way with me and it hurt a lot. This went on for an entire night. They put duct tape over my mouth to keep me from yelling for help. When my ‘boyfriend’ woke up, he saw me having rough sex with two guys that he didn’t even know, as his friends had all left. He went into a rage calling me everything he could think of. He beat me within an inch of my life. He beat me so badly that one of the guys that was fucking me called the police. When they showed up, he told them his side of the story and they arrested me. Here I was bleeding, battered, broken teeth, black eyes, dislocated shoulder and so much other stuff it pains me to just even think of that night.” Tina explained as tears rolled down her face like a river.
I was stunned. I didn’t know if I should even hear the rest, but I gently said, “Tina, if you want to stop here that’s ok. I understand.”
“No, no. I’m going to tell you how I got here. In jail, I met Jill. She heard my story and offered to take care of me and help me. That’s when I met Sasha. Jill and Sasha talked a bit. I couldn’t hear their conversation. Sasha posted my bail. They took me to the office. Cleaned me up. Called a doctor. Told me to lie down on one of the couches in Sasha’s office. I fell asleep. When I woke, there was a strange man with a black bag standing over me with a stethoscope listening to my heart and my breathing. Jill, Sasha, and the doctor all talked away from me. The next thing I knew Sasha had me give the doctor a blowjob as payment for making a ‘house call’. Jill took me home with her. She let me live with her for a couple of months. Sasha hired me as her personal assistant. She made me sign a contract just like you did, only mine had a clause stating that I was property of Sasha and Happy, Happee Limo company. Sasha explained to me that now she owned me. I was to do everything and anything she wanted, when she wanted, and how she wanted. I had no say in the matter. If I tried to quit, fight back, or run away she would find me and have me pull 10 trains a week. She called a big Italian guy into the office to prove to me that she could do it. He pulled out a huge cock, the biggest I had ever seen, even bigger than those guys in the porn videos. He grabbed my pants, pulled them down, and raped my ass. No lube, no gentleness, just hard sex that left me bleeding. All the while, Jill stood there and did nothing. There, you now know everything David. Are you going to take me back to the office now that you know my story?” Tina said with tears streaming down her face.
I handed her a napkin, so she could blow her nose.
“Tina, I’m so sorry. I had no idea. However, as heartless as this sounds, we need to discuss what happened in the car. Yes, I fucked Jill. However, she introduced me to lots of women at hotels that can help me financially. This would mean that I need .to ‘take care’ of them. Two of them wanted to try me out right then, but I took their card with their cell numbers on the back of every card promising that I’d get back with them soon.” I said.
At that point, I decided to move over to her side of the table. I put my arm around her and just held her. She leaned into me putting her head on my shoulder. We sat there in silence for about 20 minutes or so. I just kept holding her.
Tina looked up at me and asked softly, “David, may I come home with you?”
“Are you ready to go now?” I asked. She nodded her head yes. We got up out of the booth. I handed her a couple more napkins to wipe her eyes with and blow her nose. She crumpled them up and tossed them on her plate.
I picked up our check off the table. I kept my arm around her as we walked to the register. Ruth met us there. I put another $100 down to pay the check. Ruth asked if everything was ok. She cashed out our check and put the change back on the counter. I left her another $20 tip and walked over to the counter where the short order cook was working and called him over. I gave him a $20 also telling him we enjoyed the meal and thanking him for his hard work. He was stunned to say the least.
I went back to Tina, leaned in and kissed her and out we went back to my car.
We got in and headed to my place.
“Um, Tina, I do have a question about today.” I asked trying to be gentle.
“Ok, what’s your question?” she replied.
“I saw the dried cum on your panties. You said that you’d explain later. Well, its later.” I said matter of fact.
“Oh, that. I had forgotten about that. Sasha interviewed a couple of new guy drivers. She made each of them fuck me. They each came in just a couple of minutes. One of them squirted on my panties and Sasha didn’t want me to go clean myself up because I needed to be available to fuck the next interview in 10 minutes. I was embarrassed that you saw that.” Tina explained.
I pulled my car into my apartment parking lot. I leaned over, kissed her, and told her we were at my place.
I got out, went around and opened the door for her. Again, as she got out, I kissed her, this time much more passionately. Our tongues intertwined. We stood there for about 5 minutes or so just making out.
I saw my neighbor walking to his F-150. I knew it must be about 5 AM.
I broke our kiss taking Tina’s hand and headed for my apartment. Before we went inside, I warned her that my place is not that big. She giggled, telling me how sweet it was that I was concerned about the size of the apartment.
“I thought we were just staying in bed?” She playfully asked.
Doing my best Sasha impersonation, I said, “My Tina, please strip.”
That caught her off guard. Clearly, she didn’t find that funny at all. I apologized explaining that I was trying to mock Sasha. I saw a glimmer of a smile.
“David, please take me to bed. I’m tired of being her sex slave. I want to have my own life back. Can’t you see that?” She said with her eyes tearing up again.
“I’m sorry. That was cruel and non-thinking of me.” I apologized. With that, I scooped her up off her feet and carried her down the hall to the bedroom. I gently laid her down on my bed.
I kicked off my shoes and climbed on the bed with her. She just laid there obviously nervous.
“Do you want to do this or not. You seem nervous. Are you ok?” I asked being concerned.
“Yeah, I’m ok. I just gotta get Jill and you out of my head.” She replied.
“Ok, that’s it. What the heck is with you? Jill is just a driver. She may be Sasha’s favorite, but you told me that she helped you when you needed medical help and that you lived with her for a couple of months….so, I guess I don’t get it. Something’s missing to this story.” I said somewhat annoyed.
Tina’s eyes were welling up again, “David, please don’t be mad at me. You are right, there is a piece that I left out. You see Jill, the driver, right? Well, she was me before I worked there. SHE was Sasha’s assistant. When Sasha made me sign that contract she demoted Jill to driver and cut her salary by 75%. So, now, Jill works ten times harder just to make the money she was making before I came along. She blames me for everything going wrong in her life. She will tell you that I’m not to be trusted. That she helped me, and I stole her job. She hates me.”
“That’s not true. Not true at all. Jill was quick to point out that you and I are on everyone’s radar in the phone room. They all know, or think they know, about you and I. Jill gave me good advice for us to keep our personal feelings for each other OUT of the office. She said nothing but nice things about you. Not one time did she even make a backhanded remark about you. She likes you, I can see it. I think with all the crap you are put through from Sasha, she is breathing a sigh of relief knowing that it’s not her. She can’t tell you any of this for fear of the gossips in the office, like the twin trouble. Does any of this make sense?” I said.
“You’re just saying that to make me feel better.” Tina remarked.
“No, no I’m not.” I answered.
With that, Tina seemed to lighten up. I leaned over and kissed her. She started to take off her clothes. I just smiled and began taking my own clothes off.
When we were both finally naked, Tina sat up and wrapped her arms around me whispering in my ear, “Fuck me, gently please.”
Not needing to be told twice, I put my arms around her and knelt between her legs. She opened them willingly. She reached out and started pulling on my flaccid cock. It didn’t take but a few strokes for my manhood to be pointing at the ceiling.
I put two fingers in Tina’s mouth directing her to get them wet. When I thought they were wet enough, I moved them from her mouth to her pussy. I gently slipped both fingers inside of her. While they were in her, I used my thumb to gently rub her clit in small circles.
I used my other hand to finger her anus rosebud. Gently caressing it, but not trying to enter.
Tina began moaning. Her breathing became shallow and stuttered. I felt her wet, wanton pussy clamp around my fingers. Suddenly, my hand and fingers were soaking wet with lady cum.
I could see the glaze starting in her eyes.
I pulled my two fingers out and replaced them with my rock-hard cock. I gently pushed in just the head. Slowly, very slowly I pushed in a little more.
Another wave of orgasm rolled through her body.
I grasped both of her hips and gently slid my manhood all the way into her. When our pelvises met, she exploded with a gush of wetness. I slowly began to move in and out with my cock. I picked up my pace, but still being very gentle with her.
Her breathing became even more shallow. I saw her flexing her hands almost as if they had fallen asleep, but I knew better as wave after wave was rolling through her body.
“David, I’m cumming so hard” she said barely in a whisper. She was clearly not being able to communicate properly. I watched as her beautiful eyes literally were rolling to the back of her head as I continued to gently fuck her.
Then it happened. “DAVID, DAVID, OH MY GAWD, OH MY….MY……I’M CUMMMMMMMMMMMMMING. DAVID, I’M YOURS. DO WITH ME WHAT YOU WILL……OH GAWD, GAWD, GAWD…….” Tina exclaimed at the top of her raspy lungs.
Yet, I kept on my rhythmic in and out motion with my cock. I felt her weak legs wrap around my hips and her feet interlock on my ass.
As I watched this ebony beauty beneath me, I started to let my mind wander about how cruel Sasha could be and what could be done about it.
“David, where are you?” Tina asked.
“Oh, sorry, I was just enjoying the feeling of us.” Completely lying through my teeth, but not wanting to hurt her feelings any more than I already have.
“Come down here and kiss me, please.”
I leaned down to her and gently put my lips on hers. Gently, I parted my lips only to feel her lips part also and our tongues intertwining and doing the dance of love.
While our mouths were locked together, I kept up my gentle in and out motion.
I could feel her body continually tense, shake, and arch as wave after wave after wave convulsed over her.
Tina broke the kiss. “David, no one has been so kind and tender to me, ever. You are such a patient and wonderful lover. Your gentleness makes me feel so….so…. sexy. You have made me feel a whole different set of emotions ones that I believed were long dead. David, I know that I’m falling for you. Falling HARD. I hope saying that doesn’t scare you away.”
“No, it doesn’t scare me.” I said just looking into her heartfelt eyes.
I kept my fucking going, in and out. I was pushing my manhood as deep into her as I could, passing her cervix on each thrust into her.
I felt her wet delicious pussy begin to tighten around my cock. I picked up the pace, faster and faster I went. Her head was now writhing back and forth. She was gasping for air.
“OH, MY GAWD……. OH……OH……OH”
Then she went totally limp. Her breathing stopped. Her eyes were shut. I called out her name repeatedly, but nothing happened. Finally, I had to slap her to wake her.
‘Smack’ was the sound my palm made striking her cheek.
Tina took a huge gasp of air. She looked stunned almost as if she didn’t know where she was at.
“Tina, Tina, are you alright? Are you ok?” I said worried.
“Yeah, why?” She replied.
“Um, because you passed out again in the middle.” I said gently.
“Are you kidding? Please tell me that you’re kidding.” Tina said with a bit of apprehension.
I didn’t even reply. As she looked in my eyes, she knew. She knew that she once again had been ‘fucked unconscious’. I started the in and out motion again. Her pussy was still very wet. I could feel her ass as my balls were hitting her bum.
After a few strokes more, I started being a little harder with my fucking. Still being gentle, as she asked, but with a bit more force. In and out, in and out, deeper and harder than before. Her cervix was hitting my cock head. This was so pleasurable, not like the hard pounding that Sasha seemed to always want.
I noticed that the sun had come up as it was peeking through my curtains. This made me glance over at my alarm clock. ‘8:32 am’. What the hell? We’ve been going for 3+ hours?
Just at this point, my balls felt that twitch. Finally, I was passing the point of no return. I could feel the cum welling up in my balls, working its way up the shaft of my cock. I plunged as hard and as deep into Tina as I could. She knew what was about to happen. She purred in my ear. “Cum in me lover.”
With that simple statement, I came as hard as I could possibly cum. I shot 10 or more ropes of my man seed deep into her. My own eyes rolled to the back of my head. My body tensed all up. As it ended, Tina’s pussy kept milking my cock for every drop of cum.
It took all my energy to keep myself from just collapsing on her. I gently pulled my deflating cock out of her and rolled on to my side next to her.
We had sex every way we could think. Tina on top. Missionary position. Doggy style. I did her in the shower. I did her on my couch. I did her bent over the kitchen counter and I bent her over the kitchen table. We fucked on the living room carpet.
She squatted over my face and came multiple times while I ate her tasty pussy. We 69’d. I got a straight blowjob with her on her knees in front of me. Heck, one night she even blew me on the patio under the cover of darkness.
Wednesday evening came much too quickly. As we ate a light meal, sitting naked in my kitchen, we didn’t say a word. We both knew that the passion was there, but we now needed to put all that away because tomorrow we were heading back to work.
After we were done eating, I cleaned up the dishes and kitchen. I suggested that we take a long hot shower together before I was to take her home.
There was a sadness to our off days ending. I walked with her, holding her hand in mine, to the shower. I turned on the water. As I turned back around to ask her to get in, I was pushed back against the glass enclosure by Tina. She grabbed my face between her delicate hands and kissed me harder than ever before. This was not the gentle kiss of passion. This was a kiss of pure animal lust.
She released one side of my face only to grab my semi-erect cock pulling on it, making it hard rather quickly. She raised her leg up and put her foot on the vanity. I held my cock and stepped into her, placing my cock at her entrance. I pushed in as hard as I could. I buried my entire length inside of her. I leaned down and kissed her neck. I fondled her small pert boobs. All the while, I just kept fucking her. She let out a loud breathy moan.
I kept fucking her, faster and faster. We kept going like that for a while. She came multiple times splashing my cock with her love juice.
I knew I was close. I had cum so many times over the past two days that I was unsure I had much sperm left. I felt my balls tighten up and I sprayed what I had as deep inside of Tina as I could. She came hard too.
As our breathing returned to normal, we stepped in the shower together. I washed her, she washed me. We made love in the shower one more time. The water was turning cold, which signaled to us to get the heck out and dry off.
We were disappointed that our time together was over, for now. We dressed silently. I pulled out tomorrow’s suit making sure it was clean and pressed. Tina picked out a nice dress shirt and tie out of my closet. I put them all together and hung them on the large hook on the back of my bedroom door.
I put on a pair of jeans and a golf shirt with a little gator on it. I laced up my sneakers and helped Tina put her stuff back into her overnight bag.
We kissed one last time. I picked up my keys, my wallet, and her overnight bag to head out to the car.
We got in and headed to her house. When we arrived at the address, I saw Sasha’s car, but I didn’t say anything. However, in my head, does she LIVE with Sasha? If that’s the case, Sasha’s taking this much too far.
I kissed her as passionately as I could knowing that Sasha was probably watching.
I got out of the car, ran around to Tina’s side of the car, opened the door and grabbed her overnight bag. She stopped me, taking the overnight bag from my hands. She looked at the ground and sheepishly admitted that she had to live with Sasha. She asked me to just get back in my car and leave, otherwise it would create lots of punishment for her.
My heart sank. I didn’t know what to do. I complied. I kissed her and got back in my car, seeing a single tear roll down her cheek. I started the car but didn’t put it in drive until I saw that she was inside the house.
I drove back to my apartment. I couldn’t think of anything else but Tina and the horror of having to live with Sasha. When I got to my apartment, I sat in my car.
I kept debating to go back to Sasha’s and demand Tina. Yet, as bravado as that sounds, I knew it wouldn’t do Tina any good, only harm would come to her. I shut my car off and headed into my apartment for a long restless night.
About 8 am, I opened my eyes. I really didn’t sleep very well thinking about Tina. Our ‘fight’, her being ‘owned’ by Sasha, and her issues with Jill. Most of the night, I clock watched. 11pm, 12:03, 1:06, 1:59, 2:44, and on and on until I finally just passed out about 6am. I really didn’t come to any solutions. I felt exhausted, but Thursdays are supposed to be busier.
It dawned on me that I wasn’t sure what time my shift was scheduled. I decided to call the office.
“Happy, Happee Limo Company. This is Paula speaking. Is this for pickup or delivery?”
“Good Morning Paula! This is David, the new guy. Before I left on Monday night, I didn’t check the schedule to find out what time I’m due in today. Will you check for me, please?” I responded.
“Hold on just a second while I check the schedule…. Um, it says that you are scheduled in at 7pm and you are to ride with Jill again.” Paula told me.
“Wonderful, please let Sasha know I’ll be on time for my shift. Thanks Paula.” I thought to myself that I could set up for tonight and go back to bed for a few hours and hopefully get some sleep.
I doubled checked the suit that I had hanging on the big hook on the back of my bedroom door. Nothing missing. I looked at my shoes and belt, they’re just fine. I closed my room-darkening curtains, set my alarm for 4:45pm and headed back to bed.
I was so tired that I fell fast asleep in just a few minutes. I woke up exactly one minute before the alarm was set to go off. I rolled my eyes, turned the alarm off, and sat up in bed. Finally, I got some sleep. I did feel much better.
I decided that I needed to put at least half of the money from Mr. Jaxson in the safe.
“Don’t need to carry that much money driving.” I said to myself
I opened the safe and thought about how much I should carry. $200 + the change from the restaurant and put the other $1600 in the safe. That should be more than enough, I thought to myself. I also glanced at the calendar, noting that this coming Monday will be my first paycheck. Thank goodness I signed up for Direct Deposit. No need to go to the office unless scheduled.
I decided that I would eat on the road on the way to work. I got ready for work, making sure to masturbate before I finished my shower.
I put on my suit but left the coat on the hanger, so it would stay in pressed condition.
I grabbed my keys, my wallet, and cell phone. I left for work at 5:45, hoping I would miss some of the ‘go home’ traffic.
On my way to the office, I went through the drive thru at some local Greek restaurant ordering a Greek salad and a Gyro. I ate the Gyro in the car and left the salad in the bag for later.
I arrived at the office an hour before my shift. After putting on my suit coat, I checked the mirror making sure I looked ok. I grabbed the salad bag and headed inside.
I got off the elevator, took a deep breath and headed inside the office. Tina was the first to see me. She came over and gave me a ‘friendly’ hug. Nothing like the hugs I got from her before. I thought to myself “is she playing low-key like Jill suggested OR did something happen with Sasha after I left her?”
As she walked me to Sasha’s office, Tina reminded me that I was again riding with Jill, but tonight we will have a full-sized limo. I smiled and shrugged my shoulders noting that I had nothing to do with the car assignments.
Without knocking, Tina entered Sasha’s office and I followed behind her.
“Mr. David, on time. Nice to see that. Please sit down on one of the couches so we can discuss.” Sasha said in her eastern European accent.
I walked over to one of the couches and waited for her to join me.
“Mr. David, did we not speak about dating?” Sasha inquired.
“We did” I replied.
“Then whom authorized you to date My Tina?” She asked with a tone to her voice.
“No one did. However, you were clear that there is no restriction on sex. You ‘frown’ on dating but you even said yourself that you can’t stop it. I believe your words were something to the effect of dating only causes hard feelings.” I retorted.
I continued on saying, “Tina and I didn’t date. We had two glorious days of unbridled sex. Tina loved it. I loved it. We had a spectacular time.”
Sasha interjected, “My Tina says you went out to dinner. That sounds like a date to me.”
I rolled my eyes and laughed at her saying, “Well, you’re partially correct. We did stop for breakfast at IHOP before getting to my place. Hell, it was 2 in the morning and I was hungry. So, yes, we did eat but no, it was NOT a date.”
Sasha sat pensive before saying, “Ok, Mr. David. Please be careful as I’m watching you now.”
“Oh, like you weren’t already doing that.” I said dripping with sarcasm.
“You may go now. I’m sure Jill is waiting for you.” Was all that Sasha replied.
I got up from the couch, gave Tina a kiss (making sure that Sasha saw that) before heading out the castle doors.
Jill was heading towards Sasha’s office looking for me. I met her in the phone room and asked if we were ready to go. She said we were so, off we went to the 12th floor to get the limo for the night.
We walked in silence towards the limo. However, in the elevator I remembered I left my back pack in my car trunk. I poked a different button to get off at the floor to get my back pack from the car.
After getting the back pack, I headed up to the 12th floor and met Jill in the dark blue limo. She popped the trunk, I put in my back pack and joined her in the front.
She put the earpiece in and logged in with the dispatcher.
“We have a fairly full pick up list tonight. Our first pick up is at the airport, private jet area. We’re picking up some British rock n roll guy and taking him to the McCall. You’ll get to see Donna again. I’m sure she’ll be happy to see you.” Jill said with a smirk.
“Well, lets go pick up this rocker then.” I replied.
“He’s a client and I already know what special request he’ll have for me.” Jill said with a touch of disgust in her voice.
“Let me get the wording right. A ‘customer’ is just regular people. Whereas, a ‘client’ is someone who pays for extra services. Clients get priority treatment over customers. Am I getting the hang of this?” I asked rhetorically.
“Perfect. You’re catching on quickly.” Said Jill.
Jill continued, “So how was your two day ‘date’ with Tina?”
“Why does everyone think it was a date? It was just two spectacular days of unabashed sex.” I said, defending my position.
We arrived at the private jet side of the airport. The rock n roll guy’s plane was just finding a parking spot among other top end jets.
While we waited for his plane to park, Jill taught me about the 4 security cameras in the back of the car and how to watch what is going on in the back on the flip down screen.
When the plane came to a resting place, Jill jumped out and met the entertainer at the foot of the plane steps. I recognized him. He was quite aggressive with Jill. He grabbed her forcefully, kissing her on the lips and grabbing her ass simultaneously.
Jill, just let it happen without any resistance.
I got out of the limo and headed over to the plane to pick up his luggage and put it in the trunk.
“Blimey, who the hell are you bloke?” he said to me.
“Hello sir, I’m David. I’m new here and Jill is my trainer. Is there anything I can get you before we head to your hotel, the McCall?” I said as respectfully as possible.
“Bloke, you can stop and pick me up a couple of fags.”
“Pardon? You want what?” I replied as I had no idea what he was asking for. Did he mean a gay boy?
Jill piped up chuckling, “David, he means smokes, cigarettes. That’s what they call them in Great Brittan.”
“Oh, I apologize sir.”
“David, is it? Can you drive so Jill can sit in back with me and we can catch up.” Mr. rock n roll said.
“Um, sir that is up to my trainer. If she says its ok, then yes. But I may have not had enough training for her to turn the driving duties over to me.” I replied trying to give Jill a way out of whatever extra service she may have to perform.
“David, I think it will be ok since we are just going to the McCall. Just remember what I taught you before.” Jill said with a nervous tone.
Well, then, I’ll wait at the limo until your ready to head over to your hotel.
“Hey Chap, I’m ready now.”
I opened the limo door for Jill and him to climb inside the back. I went around to the driver’s seat. Immediately, he rolled up the private blackout windows. I turned on the security cameras. I flipped down the screen. When it came into focus, I saw that he had his pants already down to his ankles with Jill sucking his nearly erect very short cock. She was using only two fingers to hold it steady while she was trying to suck it.
I thought to myself, “Figures”.
I put the car in drive and headed towards the McCall. I remember that we had to stop for “a couple of fags” for the ‘artiste’. I switched on the intercom and used the interior phone and aske him what brand of smokes he wanted.
“At least two packs of Dunhill”
“Thank you, sir. When I pull the car over, I’ll jump out and get the smokes, so you and Jill can catch up. Then I’ll get you to the McCall. Is that acceptable?” still trying to be in a submissive and respective role.
“That’s fantastic.” He replied not knowing that I could see him and Jill.
Jill had moved from giving him a blowjob from his side to kneeling between his legs. I wondered what he tipped Jill for this extra?
I pulled the limo at the smoke shop two blocks from the McCall. I left the car running and got out to get the smokes. I inquired with the old crusty guy behind the counter how much Dunhill brand smokes cost.
“Ten bucks a box. You can get a carton for $95.” He said with a very raspy voice and a lit cigarette hanging out of his mouth.
“Ok, a carton then.” I said handing him one of the $100 bills I had with me.
I went back to the car, knocked on the door glass. The window opened just enough for the carton of smokes to be passed inside. Little did he know that I could hear Jill slurping and him moaning.
The window rolled back up and I got back in the driver’s seat and headed off to the McCall.
When we arrived, I didn’t see James, the valet boss at first but then he appeared.
I popped the trunk. I got out and waited by the back door until I heard a knocking on the window that it was ok to open the door.
Mr. Rock n Roll got out first. Jill followed him out of the limo. He leaned in and kissed her.
“Hey Bloke, how much do I owe you for Dunhill’s?” He asked.
“Why so cheap. When Jill gets them for me, they are $400.” He questioned.
“It was their last carton and I asked for two cartons and he lowered the price since he couldn’t sell me the two that I asked.” Once again lying through my teeth.
He took out three $100 bills and handed them over to me and squeezed Jill’s ass before heading inside the hotel.
Jill said she needed to see James and that I should go inside and see Donna.
I went inside and waited patiently as Donna was finishing with some other customers. She smiled when she saw me. I smiled back.
I looked through the automatic doors to see a valet get in the limo and pull it out of the portiere. I also saw Jill going around the corner with James.
I felt a pair of hands covering my eyes. “Guess who”
“Um, would it be the beautiful Donna?” I said jokingly.
“Why YES!” she said standing on her tip toes to kiss me.
“Can you take a small break?” I asked.
“Sure. Since you brought our last VIP we will only have regular customers the rest of the night. How long of a break do you need me to take?” she asked.
“Maybe 15-20 minutes. Jill and I have another client to pick up from the airport in about an hour.” I told her.
“Sure, come with me.” She said, taking my hand.
We went through an office to another office that had a door and window blinds.
When we got inside, she spun around and tried to kiss me. I leaned down and gave her a deep kiss.
I whispered in her ear, “Do you want to be fucked or have me eat you?”
“Well, I haven’t had oral in quite a while, but I’ve been working for a while, so I may not be too fresh down there.” She said hesitantly.
“Then oral sex it is” I said with a big grin on my face.
Her face just lit up with her smile. I sat her down in the office chair. I unbuttoned her pants and shimmied them down past her knees. I put my fingers inside her waistband and pulled her panties down also.
I dropped to my knees. I leaned into her wet womanhood. I took a deep inhale of her musky aroma.
“mmmm, smells delicious.” I said to her.
She parted her legs even wider for me.
I leaned even further forward and began my gentle assault on her wet and wanton pussy. I kissed around the outer lips. I licked her slit from top to bottom several times, hearing her moan. I used my tongue to flick across her clit. The first time I flicked it, she jumped. I slid first one, then two fingers inside of her. I gently thrust them in an out of her.
I heard her breathing begin to change. I thrust my tongue harder up and down her slit. I pulled my two fingers out and presented them to her to lick clean of her female cum juice. When they were sufficiently clean, I put them back into her adding an all important third finger. I kept pushing them in and out in a rhythm.
“Harder and faster” she requested.
Gladly I complied. I began pushing all three fingers into her as deep as I could get them. I removed my other hand off her clit and replaced it with my mouth. This made her really moan and move her hips into my face.
Faster and faster, harder and harder I thrust my fingers into her. I had my mouth sucking and nibbling hard on her nubby flower.
“Oh gawd, OH GAWD, I’M CUMMING. OH SHIT, I’M CUMMING. THIS FEELS SO FUCKING GOOD.”
I kept licking and sucking. I changed tactics. I began licking her clit, hard. All the while, sucking her love juice and swallowing it as fast as I could. My tongue was like a small dart on her clit. I felt the big orgasm beginning deep in her.
I looked in her eyes and saw them completely glazed over. With my two fingers going in an out of her at a rapid pace, I stopped. I replaced my fingers with my thumb and put one of my very wet fingers in her anal rosebud. This pushed her over the edge and she loudly said, “OH MY GAWD, FUCK, FUCK, FUCK, I’M CUMMING. GAWD, I’M CUMMING.”
Just then, there was a knock on the office door. I froze. I’m not sure Donna even heard the knock.
“Donna, David, its me, Jill. Let me in.”
I got up and unlocked the door.
“Holy crap Donna. You are so loud. I guess he’s a keeper then?” Jill said sarcastically.
“Oh yeah. I’ve been waiting for a GOOD male driver not the couple of pinky dicks you currently employ.
As the ladies were talking, I got up and wiped my face off with a paper towel. I pulled another couple off the roll and offered them to Donna. She used them to wipe the cum off her pussy. She stood up and wiped the soaked office chair seat.
I was still on my knees, when she pulled my head to hers where our lips met again. This time, she moaned into my mouth. She broke the kiss and whispered, “Next time I owe you.”
“That sounds nice, but I’m not done with you yet. Oh, I am for tonight, but not the next time we meet.” I said with a big smile on my face.
Donna fixed her clothes. Jill looked her over and they both inspected me before we left the office. Before we reached the front desk, Donna stopped and got back on her tip toes to kiss me and thank me.
Jill just stood there with a stupid smile on her face. As we got to the front doors, there waited the limo.
We both got in, Jill in the driver’s seat and me in the passenger side.
We checked in with dispatch and were told that two of our pickups were not going to make it due to severe weather. So, dispatch gave us an hour and a half to go have dinner.
I asked Jill to pick where we go for our 90 minutes. She said that she was truly hungry and wanted food, not just protein.
I smiled and told her to go where ever her little heart desires. She took us to Chili’s.
While we ate, I asked about her and Tina.
There was a pregnant pause again. “Oh” was all Jill said.
“Well then, tell me what happened?” I requested.
“It’s a long story.” She replied.
“Here’s what she believes, that it was your doing the reason she even got to work here. You recommended her to Sasha. Here’s where the train leaves the tracks. Once Sasha had her sign a contract with the company, Sasha demoted you taking away most of your pay. You’ve had to do things so much harder just to get back to where you were being paid before the demotion.” I explained.
“Well, that’s mostly true, but you’re leaving out a part.” She said
“Then tell me. Make me understand”
“When I got demoted and Tina took over my job. She knew that I was being demoted and yet she did nothing. Here, I helped her, and she stiffed me.” Jill said with a bit of anger in her voice.
“Wow, you both are angry with each other for the entirely wrong reasons. She blames you for not helping her when that big fat Italian guy raped her ass, leaving her bleeding. And you did nothing to help her except stand there and watch. Meanwhile, you’re angry at her for knowing that you were getting demoted and losing almost all your pay and she did nothing to help you. Am I right?” I asked.
“I guess.” Jill said in a submissive tone.
“You both are mad at the wrong person. It’s SASHA you should be mad at, not each other. Sasha sent the big Italian guy in to rape Tina and leave her bleeding and I’m just guessing you were not allowed to even move, or you would get the same treatment. Am I right?” I asked.
“Yes, how did you know?” Jill replied.
“Funny, that is exactly the position that Tina was put in when you got demoted and lost your pay. She was not allowed to interfere in any way or she would be hurt.” I added.
Jill sat there with a long pause thinking about what I had just said.
“David, I think you are absolutely correct. We are mad at the wrong person. You are a genius.” Jill exclaimed.
“What would you like for a reward?” Jill offered.
“Hold on, I’ll tell you in a moment.” I answered with Jill looking completely puzzled at me.
I dialed my cell phone. “Hey Hun, I have someone that you need to talk to. I’m going to hand the phone over.” I said into my phone.
I handed the phone to Jill. She looked at the caller ID, smiled at me and began talking to Tina.
“Hey there. Do you know that David is a wonderful person?” She started.
“He told me about how you were unable to do anything to help me when you found out that Sasha was demoting me an taking my pay away. Is that right?” Jill asked.
“Tina, I’m sorry about not helping you when you were getting raped by the fat Italian guy who left you bleeding. But, Sasha told me that if I even moved a muscle that I would get twice what you were getting. So, I had to just sit there and watch not being able to help. I’m so, so sorry.” Jill said with tears forming in her eyes.
‘Uh, uh, yes he is. I’ll give him a hug for you. He’s got a hug coming from me. He says that we should be mad at Sasha, not at each other. Do you agree?” Jill said into the phone.
I raised my wrist and tapped on it as if I had a watch on and we were out of time.
“Hun, I need to go. I’m so, so sorry. Maybe we both owe David our best.” Jill said, winking at me.
“Good bye dear.” And she hung up the phone.
I put money out to pay for our meal. The waitress came by and picked it up saying she would be right back with our change.
While she was gone with our money, Jill got up and came over to me and gave me a long deep passionate kiss. She whispered in my ear, “Darling, Tina and I will rock your world our next days off.”
I just smiled from ear to ear. I was proud of myself being able to put out this firestorm between Jill and Tina.
The waitress returned with my change. I handed her a $20 for a tip and we got up and left.
We got back in the limo. Jill checked us back in. Next, we were to pick up a state Senator and his trophy wife. Jill explained that usually she gets to satisfy them both but with me the time will be cut in half with us each getting about $5000 for a tip. When she’s by herself the tip is usually about $7500 but with both of us they’ll pay 5K each.
We drove quickly to the airport private jet area again. We pulled up to a Learjet. It was all white with no markings on it except the ID numbers.
I asked Jill what ‘special services’ the couple would need.
“Well, that depends on their ‘mood’. The wife, Darleen, likes big cocks. She has me use a 12” thick black dildo on her until she cums. She has never cum more than once, at least not with me. The Senator, he’s an odd bird. He likes a straight blowjob but only if I put something in his ass. The he really loves to watch his wife take it with the dildo. Once they are finished, there is no kissing. They fix their clothes and just leave, no goodbyes. We are basically “the help” and provide them with an extra service.” Jill explained.
“Um, ok. But how do you know that we will each get $5K? I asked.
“He’s told me many times that if I were to bring a second then we would each get the same amount.” She answered.
“Jill, that could mean we would each get $3500 not 5 grand.” I argued back.
“David, you got to trust me on this one. I know how to get the money out of him.”
“Well, you ARE my trainer. So, I leave everything in your capable hands.” I said in a flirtatious voice.
As we pulled up to the plane, we both got out of the limo and approached the stairs to the jet.
The Senator appeared first, followed by his wife.
Jill introduced me to the Senator, “Senator, this is David. He’s here to assist with your need’s tonight. Darleen, this is David. He will personally attend to your need’s tonight. He is my personal choice to cater to whatever you need him to do for you.”
I picked up their luggage and put it in the trunk.
Jill quietly chatted with the couple as they stood by the back door to get in the client area of the limo. I stood quietly next to the passenger door not sure what to do.
Jill leaned in and gave the Senator a peck on the cheek and another one on his wife’s cheek. She then signaled to me to get in the car.
She drove us to a parking garage that she usually used to take care of the couple since it was only three or four blocks away from their hotel “The Jonathan”.
“Ok, here’s the game plan. I will take care of the Senator and you will take care of his wife, Darleen. She likes it hard in the pussy and she’s ok with you cumming inside of her as she had her ‘factory’ removed years back. However, you can not finish before I finish with the Senator. He really wants to see someone fuck his wife. We will get in on the driver’s side of the back. We won’t get naked, but you will pull your pants down to your ankles for Darleen to have full access if she chooses to do anything other than fuck. DO NOT KISS HER, that only pisses off the Senator. If she kisses you keep it a friendly kiss, nothing passionate. If we do this right, they will pay us $15K together meaning $7500 each!” Jill instructed.
“Does he last a long time? I need to plan how fast or slow I need to go with Darleen if he takes a long time.” I said.
“No, he’s a quickie. I think he is more voyeur than participant.” She replied.
“Let’s go then.”
We got out of the limo and went to the back door of the limo. Jill got in first then me. The Senator already had his dick out and was stroking it. Darleen was massaging herself through her black panties with her skirt hiked up to her waist.
Jill immediately began sucking on the Senator. She licked the head of his old cock. She licked up and down the regular sized shaft. She played with his balls, gently touching him. Finally, she engulfed his whole cock into her mouth. You could hear the slurping sounds as she worked on his manhood. Her head began to bob up and down on his penis. She pulled all the way out only leaving the head inside of her wet mouth. She used her index finger to gently scrape with her fingernail up the shaft to her lips. She reached into his pants and plunged a couple of fingers up his rectum. That simple action made him cum. As his breathing slowed down, she pulled her hand out of his pants, removed her mouth from his cock, and used a tissue to wipe her mouth and spit his cum into the tissue.
He put his now flaccid cock back into his trousers and zipped up. Jill joined him on the seat readying herself to watch me take care of Darleen.
I reached over and began to remove her panties, but she stopped me.
“Just push them to the side. I don’t want to have to take off my shoes.” Darleen expressed.
I shrugged and told her that I would do whatever she requested. I unzipped my pants and shoved them down past my knees. I also slid my boxers down. I had to pull on my cock a couple of times to make sure that I was hard enough for her.
I grasped the base of my cock with one hand and pulled her panties to the side with the other. On my knees in front of her, I rubbed my now hard cock up and down her slit. I heard her moan. I kept rubbing it and spanked her clit with the bulbous head. She flinched. I pushed the head of my cock into her waiting hole. She gasped. I pushed it all the way in feeling her deep wide pussy. She was not tight at all. She was as loose as an old pair of sneakers even though she was this hot looking trophy wife. I began the in and out motion hard. I slammed my cock into her making my balls hit her ass. She was very wet. I kept up the pounding going harder and harder into her wanton pussy.
“That’s it baby, take it all. My gawd, you look so good with that hard cock pounding your sweet pussy.” The Senator said.
“Harder, harder please. Fuck me, Fuck me hard!” Darleen demanded.
I changed tactics on her by putting her feet over my shoulders, which allowed me to penetrate her even further. I started pounding her with the same furiousness that I use on Sasha’s pussy. I pounded harder and harder.
“C’mon David, fuck her. Fuck her like she wants you to.” Jill encouraged.
After several minutes, sweat was now forming on my forehead and my neck was all sweaty.
Then it happened……Darleen yelled at the top of her lungs, “Fuck me…. OH GAWD, I’M…I’M…CUMMING…. I’M CUMMING…. FUCK, FUCK, FUCK!”
The Senator exhaled. He smiled and gave Jill a white envelope which she folded up and put in her pants back pocket. True to Jill’s word, Darleen put herself back together not saying one word to me. Jill handed me a couple of tissues to wipe myself off with and pull my boxers and pants back up. Once my belt was buckled, we got out of the limo back and went back to the front seat. Jill started the car and we drove silently to “The Jonathan”. When we pulled in the valet opened the back door and the Senator and his wife stepped out. Another bellman took their luggage from the trunk. Jill started the car and we drove off.
We went a couple of blocks before Jill suggested that we get some water somewhere. We stopped at a quickie mart. However, before I went in she opened the envelope and counted the money. Inside, there was $7500 in cash and a personal check from Darleen, in the amount of $10,000. They put a small note inside also. The note read, “Jill. Thank you for your personal service. My wife appreciates what you did to take such special care of us. We look forward to seeing you and your trainee on our next visit. Thank you once again.” It was signed by the Senator.
“Well, how about that? He’s never ever said Thank you before. I’m going to have to bring you along next time they come to town.” Jill said smiling ear to ear.
I got out and went inside to get drinks for us.
Over the next 4 hours, we picked up several clients. A couple from a hi-tech firm from Silicon Valley who enjoyed fucking each other while Jill and I watched in silence. A CEO of a fortune 500 company who liked using street whores. A church pastor who wanted Jill to watch him masturbate. A pair of lesbians who wanted me to be their first cock in them since high school. And, finally a B-level movie actor who wanted to have me fuck him in the ass while he ate Jill out.
It was quite the crazy night.
Jill and I were plum tuckered out. However, we each made over $22,000. I sat in complete awe of our earnings. Oh, and of course, Jill had her ‘thank you’ note from the Senator, which she intended on framing and putting up in her home.
Jill called in to the dispatcher and took us off the clock. The dispatcher asked how much money we made. She replied that she made about $22K and David made zero as Sasha won’t let him get tips for his first 30 days. Dante, the dispatcher, rambled on about how unfair that was and how that rule needs to change. Just as I was about to say something, Jill put her finger to her lips signaling not to say anything.
She hung up with him and turned the phone off and put the earpiece into the center console for the next driver to easily find it.
“David, you fuck like a porn star. Are you sure I won’t find you in any porn videos?” Jill asked in a joking manner.
“Nope, I’m just the chauffeur.” I said with a huge smile on my face.
Thanks for reading this story. I look forward to reading your comments (good or bad) as I am always trying to enhance my writing for as many as possible to enjoy.
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