The Squirting Limo Driver

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An older male passenger both teaches and learns a lesson.
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imhapless
imhapless
3,643 Followers

You probably like to fuck during the Christmas season, don't you? Christmas time is one of the horniest times of the year. People tend to be generous around Christmas time, both with their money and their bodies.

In college – especially since my school had a long winter break after finals, starting just before Christmas – I, Charlene, found out that a good way to make money for school over the Christmas Holidays when visiting my family was to work as a limo driver. It was also a good way to take my mind off the fact that I didn't have a "home town honey" and likely wouldn't be getting any cock for the Holidays. I had gotten a chauffer's license when I was 18. By the time of this story around Christmas, 2011, I had just turned 21 so I could even drive the limos with a bar in the back.

There was plenty of work to go around at the limo company I worked for, but that didn't mean we didn't compete for the jobs with the nicest people and the highest probability of tips. Just two days after Christmas a Fortune 500 company hired us to pick up two high powered male executives at Baltimore Washington International airport, and to drive them to a meeting in the mountains of Maryland, near Hagerstown, to close on the acquisition of a company that needed to be concluded in 2011. The client contact, Karen, dealt with us all the time and she gave us intelligence on both men.

Karen said that V. P. Kevin Simpson, single, of Denver was the personification of goodness. He treated everyone nicely, was never unreasonably demanding, always complimentary but never harassing, and known to be a good tipper.

On the other hand, Division Manager George Clarett of Los Angeles, married with three kids but always on the make, was the incarnation of evil. He was haughty, full of himself, deceitful, and a cheapskate even with the company's money.

Not surprisingly it was an understatement to say that Kevin and George didn't get along, and even though they were arriving within an hour of each other they were to be driven separately.

Six drivers wanted Simpson, no one wanted Clarett, so the dispatcher had us draw lots. I won and got Simpson. My friend Jason lost and got Clarett. The other four drivers got other jobs.

My chauffer's uniform was specifically designed to do a good job of hiding my big boobs and bubble ass. But it was hard to hide my face and hair, which I always received compliments on. The other drivers playfully accused me of getting the biggest tips because I was a good-looking female. I said it was because of my Les Mans driving abilities.

I arrived at BWI airport about 3:00 p.m., a half hour before Mr. Simpson was scheduled to arrive. I held up a professionally done sign that said "Mr. Simpson, XYZ, Inc." Jason was about fifteen feet away from me waiting for Mr. Clarett, whose plane had apparently been delayed, with a similar sign.

Right at the time I expected Mr. Simpson, a very handsome sharply dressed tall man, likely in his early 40s, stopped and looked at Jason and I. He put down his briefcase, seemed to rub his hands, and then approached me. With a friendly smile he said "I'm flattered that your company would send its most attractive driver to pick me up."

"Let's hope I don't attract traffic tickets, Mr. Simpson," I replied returning his friendly smile, and getting a laugh from him.

"Please, call me Kevin; and you are?"

"Charlene, but everyone calls me 'Share'."

"OK Share, are you ready to go?"

"If you are Mr. Simp..., I mean Kevin. How was the trip from Denver?"

"Surprisingly uneventful; no weather issues at all."

"Do you have any checked baggage, Kevin?"

"No, just this 'wheelie' carry on, and my briefcase."

"Can I take them for you?"

"If you don't mind you can negotiate the wheelie, but I'll keep the briefcase."

"Kevin" was one of the most personable people I had ever met, so we freely chatted while walking along. He insisted on walking with me to the limo lot rather than having me pick him up right in front of the airport, and by the time we reached the limo I felt like I had known him for a month. Once we got there he had a request indicating his unpretentiousness.

"Tell me Share, does your company have any policy against your clients riding in the front passenger's seat? I have no intention of doing any work as we ride along and I would much rather see the road."

"I'm not aware of any policy against that," I said reflectively as I put his wheelie and briefcase in the trunk, "though no one has ever asked before. But I aim to please, so if that is what you want, please go ahead. Let me get the door for you."

"Too late, Share," Kevin laughed as he opened the front passenger door, "I hope that doesn't get you fired."

"I won't tell if you won't," I chuckled in return.

The first hour of our drive we had one of the most fascinating conversations I have ever had. Like all 21 year old college juniors, I thought I was more worldly than I likely was, and I was very impressed that Kevin's topics of conversation were sophisticated. He didn't have the normal bullshit questions like "what's your major," "when do you go back to school," etc. But he quickly honed in on substantive topics of interest to me and seemed to actually listen to and respect my opinions.

Snow started once we got into the foothills of the mountains. The mountains in Maryland are not like the Rockies, but they can be treacherous, and they are rural. One road was closed by the State Police without a good explanation, so I tried a cellphone call back to the office to see if someone knew of a better alternative route than the limo GPS was giving me. No luck. Cellphone reception was bad in the mountains on the best of days, and with bad weather was now non-existent.

I was really glad to have the calming influence of someone from a snowy area of the country like Kevin. "You're doing just fine driving in this stuff; you could make it in Denver," he exclaimed a couple of times.

The roads started to get real bad; I spun out twice, and the second time my 270 degree spin-out on a small town street really freaked me! Kevin actually got out of the limo and with the help of two passersby pushed us out of a snow bank. When he returned to the limo he could tell I was shaken.

As he gave my arm a reassuring squeeze Kevin said "Don't stress out Share. My cellphone doesn't work here either, but let me see if I can find an old fashioned pay phone and call to see whether the meeting will go on early tomorrow morning as scheduled or if it will be delayed until late in the day. OK?"

On the verge of tears I simply nodded my head "Yes."

Kevin went into a drugstore, one of the few retail establishments in town, and came out a short time later.

"Boy, it's cold out there. Even for a guy from the Rockies. They say there's a phone at a motel just on the outskirts of town, only about a half mile up the road." Sensing my apprehension to start driving again he pretended to crack a whip and smilingly said "Mush."

Despite how tense I was I had to laugh a little. Going to school in Florida I wasn't used to driving in a snowstorm, but figured I could go half a mile, and trudged on. I visibly sighed as I pulled into the motel parking lot without further incident. Kevin found the pay phone, made a call, and then I saw him talk to the proprietor of the motel and believe he slipped him some cash.

"Well, my meeting is postponed until tomorrow at 5 p.m. Clarett wasn't able to get in yet and the roads are bad and getting worse. My counterparts at the company we are acquiring said it was best to stay here tonight. The motel has a couple of rooms for us."

I scanned the motel. It wasn't a flea bag, but I'm sure didn't have any of the amenities an executive like Kevin was used to. After a pause I said "Are you sure you don't want me to try and find something nicer?"

"No matter how good a driver you are, Share, with this rear wheel drive boat you're driving we're sure to spin out again. I'm OK with this place; it looks clean even if not fancy."

"If it's OK with you, it is with me," I replied.

We got our rooms – the last two in the establishment, mine the end unit, Kevin's next to mine. Then we almost immediately went into town to eat dinner. The only food service was in a bar. It had real rural décor and a simple menu, but the food was decent and the jukebox not too loud. We had a great chat and laughs during dinner, and several draft beers each. By the end of dinner I remember thinking "How is this guy not married? If I was on a date with this guy I'd fuck him unconscious."

After dinner we played some pool. After I won the first game, Kevin suggested "boilermaker pool," which I readily agreed to. Whoever lost drank a boilermaker. After I lost three games in a row I was tipsy enough that there was no way I could ever win again, so we called it a night and got back to the motel about 9:30 p.m. As we went to our rooms Kevin said "You're great company, Share, but I need to teach you how to handle hard rods and balls..." and after a pregnant pause, "that is to play pool."

Even though I was feeling no pain from the boilermakers, I got the joke and we both laughed. "If you run into any trouble just bang on my door," he said as we each entered our room.

When I got into my room I was anxious to take a shower. But it was freezing cold. I called the manager/owner. He came down to look and said the heat was busted and couldn't be fixed until the next day. I knew there were no other rooms, but I asked anyway to confirm it.

Shit. Now what do I do? I really wanted a shower, Kevin had been very nice, all the rooms had two beds in them, Kevin said to "bang on" his door if I ran into any trouble, and I didn't want to freeze. So I banged on his door.

Kevin said "coming, coming," and after 30 seconds or so answered the door with nothing but a towel on; he apparently had the same idea I did about a shower. He looked surprised to see me – and he looked REAL good in just the towel. He had great muscle tone, just the right amount of body hair, and broad shoulders. I almost chickened out because I thought for sure that in my tipsy condition I would make an ass out of myself by coming on to him, but a blast of cold air with some snow hit me in the back and he anxiously said "Come in, it's freezing."

I explained the problem to him. He was nonchalant about it. "There are two beds, and I have a bathrobe you can use. I'm not going to let you freeze."

"Thanks," was my only response.

I took his robe (it was a silk shorty), went into the bathroom, stripped and showered. I washed out my bra and panties because I didn't have any other clothes with me, so that they would be clean and could dry overnight, combed out my hair, put on the robe, and walked into the main room. Kevin was in bed with no shirt on, propping himself up with one arm reading a magazine. When I walked out of the bathroom his eyes got wide and he mumbled "Holy Shit."

His eyes were glued to me as I went to put my chauffer's uniform into a dresser drawer and asked if it was OK that I hung up my bra and panties in the bathroom to dry. As I walked between the beds – his eyes still looking like a frog's – and sat down on my bed he started to get up and said "Uh, well, maybe this isn't, you know, such a good idea, uh, afterwards, I mean after all. I'm sure I can stand the cold in your room."

When he stood up his erection was sticking through the fly of his boxers. I was high, fascinated by him, and horny, so I reached out and grabbed it. "I think your 'pool cue' wants to stay and give me a lesson," I said in as sultry a voice as I could summon, while staring into his eyes.

After about fifteen seconds of staring at me bug-eyed, with my hand on his cock and it getting stiffer and stiffer, he pulled his boxers off, climbed into bed with me, and had my robe off in an instant.

I didn't know if there would be any adverse work consequences, but at that point I didn't really give a rat's ass since I hadn't been laid in two weeks. We passionately embraced as we French-kissed. He was working on my ass with one hand, and a boob with the other, while I was digging my fingers into his back. After a few minutes of this, he went down on me.

He was a goddamn whirling dervish at my pussy. I swear he must have had three hands and two tongues for what he was doing to me. He seemed to like my shaved pussy with chevron-shaped landing strip – which he occasionally ran some fingers through – and I sure liked what he was doing to my clit and pussy lips. He attacked my clit from all different directions, one, then another, then with two hands and his tongue at the same time. By the time of my first climax my clit had grown into a miniature dick it was so full of blood.

As I was writhing around in the throws of a monster orgasm, he didn't let up for even a nanosecond. I begged him to let me recover, but he would have none of it, and by the time my first climax was finally subsiding, a second was building. I went through three orgasms before he finally let up.

After kissing me for a while after my third orgasm, he straddled my face with his crotch, and I latched onto his dick and balls. It was a real nice looking cock and his balls were low hanging. After playing with his dick with my hands, I shoved it into my mouth and started licking and sucking, hope to match the intensity he had shown in handling my pussy. At the same time I massaged and stroked his balls and ball sack with both hands.

I knew I was getting him close to cumming when he leaned over and asked "I want to fuck you; are you on birth control?" To be honest after I heard "I want to fuck you" I didn't care much about the rest, but I nodded my head as I continued to suck his dick and play with his testicles. After another few seconds he "pried" his dick out of my hungry mouth, flipped me over in an instant, and as I was lying with my belly on the mattress drove his cock into my sopping wet cunt.

He was like the fucking Energizer Bunny he was so active as he reciprocated, rotated, and twisted inside me while at the same time stroking the sides of one or both tits. God it felt soooo good! After bringing me to yet another climax, he lifted my ass off the bed while still impaling me, and started banging real hard. He held one hip with one hand, and shoved the thumb of the other hand – lubricated with my free-flowing pussy nectar – into my asshole.

It wasn't long before I was screaming in delight, he was grunting, and his thumb was twisting, as I hit an even higher level of exuberance while he blasted stream after stream of gooey joy juice into my cunt. We both probably stayed orgasmic for five minutes. That whole time he continued to slow pump in me, and I did my best to slow whack back.

He finally withdrew and lay next to me, face-to-face. We were both positively giddy.

"You're a real fucking machine, Kevin. I lost count of my orgasms."

"You're so plasma hot, Share, I'm surprised my dick didn't burn up inside you. That was as much fucking satisfaction as I have ever had!"

We continued complimenting each other, and other pillow talk, until he could see I was reviving a little bit. Then:

"Have you ever 'squirted,' Share?"

"Ha, ha. No, that's just a myth."

"Oh is it?"

"Yeah, I think."

"If I make you squirt will you suck my dick whenever and wherever I ask you to until you drop me off back at the airport?"

I knew there was no way he could, but I had nothing to lose. I'd suck his dick anytime for the asking anyway. So with a possum grin on my face I chuckled "Sure."

With that he stood up, got a bottle of oil out of his suitcase, lathered up his right hand, and as I lay on my back stuck the middle and ring fingers of his right hand into my cunt while pushing down gently on my abdomen with his left hand. Then he started vigorously moving his right hand up and down, increasing the pace slightly every few seconds. I closed my eyes, bunched up the sheets in my hands, and tried to relax.

I could not fucking believe how it felt! It was unique! While there was a small element of what for lack of a better word could be called "discomfort" there was also a large measure of stimulation and pleasure. Then, suddenly, a welling-up. It was almost like I had to pee – but I knew I didn't – and then, abruptly, a gusher. Kevin removed his hand – it was almost like it was fire-hosed out of my pussy – and liquid came spewing out. I opened my eyes and couldn't believe it – spurts of pure liquid going a good six inches into the air. Shit, I was "squirting!"

I heard Kevin saying "I'm getting photos of this" and saw his cellphone in his left hand. At that point in time I didn't give a shit about photos of me squirting but I yelled "None of my face," to which he replied "You got it." As unexpected as the squirting was the feeling that then started to overwhelm me. I started uncontrollable writhing, bucking, thrashing, and flopping, like a landed marlin. Kevin had to actually hold me down to keep me from flipping off the bed.

When I finally calmed down a good 3-4 minutes later, Kevin started laughing. "You need some water, girl?" he chortled as he got up and got me a bottle from the small frig in the room. I drank about half of it, oohing and aahing between gulps.

"Looks like I'm in line for a good cock sucking, aren't I?"

"Yeah, I didn't think it was possible, but you sure are."

I figured he needed me to give all my attention to sucking his cock after that display, so I sat him at the edge of the mattress, got out of bed, got on my knees in front of him, and shoved his ¾ hard pole into my mouth. While sucking like a sump pump I stroked the part of his cock out of my mouth with my right hand, and kneaded his balls with my left. As I was performing my task he was mumbling "shit yeah" under his breath, and rubbing my nipples at warp speed.

By the time he ejaculated into my mouth, I almost had had another orgasm from my titty stimulation – something I also hadn't thought possible before this night of revelations. I slurped down his man cream with alacrity, then gummed his testicles until he flopped back on the bed.

I crawled into bed next to him, with probably the best exhausted feeling of my life. But after a few minutes he was raring to go again. He wanted another squirting demonstration!

He laid me on my back, spread my legs, oiled up his fingers again, and once more stuck his middle and ring fingers of his right hand into my well-used cunt and started his energetic up and down movements. This time I didn't feel his left hand on my abdomen. My mind was so awash in endorphins all I could do was lay there with my eyes closed, moaning and jerking my ass up and down. I could feel another torrent of liquid expelling his hand from my pussy, and I started frantically flipping, twitching, and quivering, seemingly even more than the first time.

By the time I came down from my endorphin flood after the second squirting extravaganza, Kevin had lifted me off the soaked bed, dried me off with a towel, and placed me in the dry bed. He insisted I drink a bottle of water, then snuggled next to me under the covers.

I was essentially "out" for the rest of the night. But the Energizer Bunny wasn't. As I lay there almost comatose, he fucked me two more times before 10:30 a.m. when we finally dragged our asses out of bed. I squirmed in response to the rivulets of cum leaking out of my pussy all through breakfast – at the same bar we had dinner at – much to Kevin's amusement.

After breakfast we went back to our room and Kevin sucked and played with my tits for a good hour. Then he asked for another dick-sucking – which I was obligated to provide pursuant to our "squirting" deal – which he seemed to enjoy even though his balls ran out of ejaculate. By then the snow had stopped completely and the roads were basically clear, so we ate lunch, checked out of the motel, and got in the limo to drive to the meeting. It was slow going but we got there a good hour before it was to start.

imhapless
imhapless
3,643 Followers
12