The Accidental Hooker

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A silly prank backfires...
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CarrieQ
CarrieQ
159 Followers

In some ways, Ben was an ideal boyfriend. He didn't do commitment, which suited me just fine. I worked as a barmaid at a busy club and liked being free to go home with any hunk who happened to wander my way.

And seeing as he had a fiancee he was planning to marry some day, he was hardly in a position to complain. The truth was he just enjoyed a little spice now and then. Lots of men are like that; they marry someone homely and happy who loves kids, then look for action elsewhere.

Anyway, Ben's other half often worked nights, and that's when we'd hook up. He'd wait in the bar till I knocked off, then come back to my place for one of our steamy sessions.

It was really all just about sex..

We were like a couple of rabbits and could easily have fucked all night, except that Ben always had to get home in plenty of time for the little lady to come back from work and find him asleep in bed like a good little boy!

Once only, we had a session at his place, but it was a disaster. He spent the whole time worrying whether I'd lost an earring in the bedclothes, or how much of my hairspray was rubbing off on the pillow, and loads of other crap that turned his cock to jelly.

We'd only gone to his place cos it was my flatmate's turn to have a guy stay over. So next time we were stuck, Ben booked us into a cheap hotel instead.

It was in the seedier part of town, close to the red light district, and on the way there, we saw several hookers plying their trade.

"Know what would REALLY be fun?" Ben exclaimed.

"What?"

"If you got out and pretended to be a hooker! I'll cruise round the block then come back real slow, pretend to haggle a price, pick you up and take you to the hotel! How about it?"

"Alright!" I agreed. It sounded like a laugh. It was quite late and the streets were more or less deserted, so I couldn't see how any harm could come of it. And as I was dressed in a tight leopard print top with a short black skirt, seamed stockings and high-heeled stiletto sandals, I more or less looked the part!

So Ben pulled over, I slapped on a load more make-up, then got out of the car..

Only after he'd driven off did I realize how spooky the place was. Though it was eerily dark, the shadows seemed to shift a lot, and I kept hearing noises that only people can make, like a can being kicked or the distorted echo of a raucous chuckle.

I wasn't familiar with this part of town, and soon found I'd lost my bearings. I desperately wanted to get to somewhere a bit safer, but wasn't sure which way to walk. Also, much as I wanted to be elsewhere, I was scared to go too far in case Ben couldn't then find me.

To make matters worse, my steel-tipped stilettos echoed like little thunderclaps. So in the end, I decided the best thing was just to stand where Ben had dropped me and wait for him to come back.

"For fuck's sake hurry up!" I muttered nervously to myself.

At last, I heard a car trundling along..

The headlights didn't half dazzle me but the vehicle seemed familiar, and I was so sure it was Ben I stepped forward, putting on a brave smile so he wouldn't see how scared I was.

The car slowed down and, just as it pulled up level with me, I saw it wasn't Ben behind the wheel! I turned away, but it was too late, and the stranger wound down his window..

"How much?" he shouted.

"What do you mean?" I asked innocently.

"Don't fuck about, bitch!" he replied irritably. "How much are you charging tonight?"

"Oh, no!" I exclaimed, "I'm not.."

"Time-wasting slut!" he cursed, hurriedly accelerating away.

I was all alone once more, only now I felt twice as nervous. The minutes seemed to be ticking away with no sign of Ben, so I began to walk in what I could only hope would prove the right direction.

Another car slowed down behind me..

I looked back hopefully, but this one was the wrong shape to be Ben's, so I carried on walking.

"What you charging tonight, doll?" the driver shouted.

I ignored him and hurried on, but he deliberately kept pace..

"Hey, I'm talking to you!" he bawled.

"I'm not a hooker!" I hissed.

"Then what the fuck are you doing round here, you stupid cow?!" he retorted, before angrily speeding off in a cloud of burning rubber.

Quivering with a heady melange of fear and rage at Ben, I rushed towards the end of the road. I'd hoped to find somewhere I recognised, but wasn't in luck. All I found was a crossroads with every street more or less identical to the seedy one I was leaving.

I began to sob in despair, so much so that I hardly noticed another car pulling up..

"How much?" asked a voice.

"I'm not a.." I began.

"Wait a minute!" he interrupted, "I know you! You're that tranny barmaid from Gloria's place! What you doing all the way out here, luv? I wouldn't have thought this was your sort of thing.."

"I'm not a hooker!" I wailed.

"That's a shame!" he sighed, "Cos I'd have paid top dollar to go with the likes of you! Oh well, never mind! Goodnight, dear."

Saying which, he began to pull away..

"W-wait!" I cried, dashing up to his window. "Look, there's been a terrible mistake and I really need to get back home! Can't you please help me?"

"I'd like to," he mused, "honestly I would, but I'm lonely see, and I've come out for my one bit of fun of a week, rather than to work as a taxi driver!"

A sudden thought flashed through my mind..

"What if gave you the fun?" I asked, "Would you run me home afterwards?"

"Now that's more like it!" he said happily, "See, that's what I call initiative! Okay then, how much?"

"For what exactly?" I asked.

"Well, first I want you to give me some head, then I'll ride you bareback, cos I'm clean and I do believe you when you say you ain't no hooker. How much for all that, then?"

I hadn't a clue what to say as I hadn't the foggiest what hookers got paid, so I just plucked a nice round number out of the air..

"A hundred?" I suggested.

"Let's call it eighty," he haggled, "With another twenty knocked off for the taxi ride afterwards. So how about it, then?"

"Oh, okay!" I muttered and got in his car.

He must have been lonely, cos he soon proved something of a chatterbox..

After telling me he was driving to some wasteland not far away where we wouldn't be disturbed, he told me his name was Tony and that he'd been picking up hookers every weekend since his wife had gone off sex a few years ago.

"But if you're not a hooker, then how come you're out here, all tarted up like that?" he asked, so I told him all about Ben's sudden, stupid idea.

"Sure he hadn't just dreamt up an elaborate way of dumping you?" he asked.

"He's the one who's dumped!" I snapped, to which Tony just sniggered.

We pulled over onto a bumpy patch of wasteland. There was a full moon and not a cloud in the sky, so I could see Tony clear as day, and for the first time recognised him as a regular at the club.

He was a chubby, middle-aged guy with a perpetual smile on his big wide face and just a few strands of grey hair left on the top of his head.

The car was quite a large estate and, when he pushed the driver's seat back, there was plenty of room for me to kneel down under the steering-wheel.

Awkwardly, Tony unbuttoned his belt then unzipped his fly and pulled out his fat, throbbing manhood. He groaned as I teased the bulging cherry with the tips of a couple of manicured fingernails before popping it deftly into my mouth.

I blew a little, feeling Tony's every sinew tense as I slipped his quivering cock slowly down my throat. Then I began to work my lips up and down his juicy stem, blowing and slurping as I sucked at every last inch of stiff, pulsating flesh.

"Oh, Christ you're good!" he exclaimed, "I only wish you WERE a hooker!"

I could think of several appropriate replies to that backhanded compliment, but wasn't able to say much with my mouth full..

Instead, I just carried on pleasuring him, till the first drops of salty precum began to trickle slowly down my throat.

Abruptly, Tony withdrew his glistening ramrod from my mouth..

"We'll need to go outside now," he muttered.

After clambering out from below the steering-wheel, I followed Tony round to the back of the car, where he opened the liftgate. It was an incredibly clear night, and the surrounding buildings glowed like chalk in the moonlight.

"Don't worry," said Tony, reading my mind, "They're all empty office blocks, there ain't no one can see us down here!"

Saying which, he asked me to bend over the back bumper, so that my top half was inside the car but my legs were outside.

Obediently, I lifted my miniskirt and pulled my lacy pink panties down onto my thighs.

"Oh, yes!" Tony exclaimed greedily, his hand exploring my boy-bits indulgently before a well-oiled finger teased the rim of my tight little bumhole.

A moment later, and he was inside me..

He pumped fast and furiously, working his stiff, throbbing manhood up and down in a series of rapidly increasing thrusts that stretched my tender rim to tearing point.

Placing his large, cold hands upon my butt-cheeks, he squeezed me into his rhythm, forcing me to work my hips in synchrony with his fast-moving meat-rod, till I felt his throbbing cherry touching my furthest recesses, and squealed in harmony with his deep, low groans.

At last came the inevitable explosion..

Spurt after spurt of warm cream filled my aching bumhole, as Tony's groans turned gradually to whimpers and he stealthily withdrew his withering ramrod, his sated desire perhaps reawakening a cautious instinct.

We returned to the car, a broad smile further brightening Tony's always cheerful face.

"That was fucking fantastic!" he enthused, delving casually into his wallet and giving me the £60 we'd agreed. "I only wish you'd do this for me every week! How about it, eh?"

I shrugged ambiguously. "Just take me home please," I said.

Good as his word, Tony drove me across town, raving the whole while about what a great time he'd had, and how he'd love to do it all again. He even offered to pay double, but I refused to say anything more on the matter.

Outside my flat, I was surprised to see Ben parked up..

After saying goodbye to Tony, I strolled over to his car and tapped on his window. It startled him out of a nap and he woke with a jolt, banging his head in the process.

"What the fuck happened to you?" I hissed.

"S-sorry, babe!" he stammered. "You won't believe it, but I got pulled over by the cops for kerb crawling! I told them about our little game but they wouldn't believe it and took me down to the station. I was there over an hour, and when they finally let me go I drove round and round but couldn't see you anywhere! So where the fuck were you?"

"Having an interesting time!" I replied nonchalantly.

CarrieQ
CarrieQ
159 Followers
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ShortyMacShortyMacalmost 2 years ago

Careful Ben you will screw up a good thing if your not careful. I loved the story it was just enough kink to it to get my blood flowing. 😋 I’ve always had a thing for transgendered girls and some cross dressers too.

I’d give the story a solid 10 stars.

⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

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