Haley for Hire Pt. 02

Story Info
Haley takes on 8 guys and expands her repertoire!!
3.2k words
4.66
13.7k
17

Part 2 of the 4 part series

Updated 12/02/2023
Created 06/09/2023
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While I valued my alone time, the good thing about being a 'looker' is there's never been a shortage of interested parties when I need one. Men look and can't look away, their imaginations likely going wild.

It must really be a struggle, especially when they're with their wives, to lock in on my goods and have to do what I understand to be creative staring. It is apparently an actual skill.

They might be thinking, 'Man, I'd like to fuck that girl over there' and then go about staring...but not staring. A customer told me once that it involved taking a brief mental snapshot, savoring the picture, and then looking again, This is all going on surreptitiously while carrying on a conversation with the wife/girlfriend, "Do you think this looks good on me?".

FYI, there's only one answer to that question.

If you're a girl like me, you love clothes because being purposefully dressed accentuates the positive. Just like the black tights have an effect on every drooling hang dog, I love attractive fashion and have the closet to prove it.

So, naturally, I spend a lot of time in clothing stores. And so do horny men taking mental snapshots of me. Some end up as customers, some wish I was their girlfriend, some have the strength to resist.

Once, I was shopping at a high end boutique which had numerous women followed around by their reluctant but dutiful partners. Most men highly value what I refer to as the 'guy waiting around' chairs or sofa. It's the first thing they look for and it's agony when they're occupied.

These are a treasure trove of high visibility and potential income for a working girl.

In this example, I lingered around their sight line and held things up to me and occasionally dropped something that I'd have to immodestly bend over to retrieve in an extremely short skirt. I noticed they either watched or ran over to pick the item up for me.

The watchers hoped for a possible panty fringe sighting but the helper was aiming higher.

"Here, let me get that," he said sweetly.

"Oh thank you. I almost need a man to follow me around."

"Well that shouldn't be a problem for you. If my girlfriend wasn't in the changing room I'd be glad to apply for the position."

Then I opened the innuendo door very wide and said cheekily, "There are a lot of positions to choose from. Would that be your favorite?"

Caught slightly off guard he changed the subject, "You'd look beautiful in that dress."

"Do you think so?"

"I do, of course you'd look beautiful in anything."

"Well aren't you the flatterer." I smiled that smile that grabbed him by the balls.

He looked around to see if his girlfriend came out and then wrote something on the back of his business card, "Take this and call me if the mood strikes." After they left the store I looked at it, "Lunch, and...?"

His name was Brad and I texted him the next day. "Thought I'd take you up on your kind lunch offer though I'd be remiss not to mention the $300 fee for the 'and' part. Still interested?"

He texted me back quickly, 'I paused for a long moment at the 'fee' but then remembered how gorgeous you were. Basically, my cock is taking you to lunch.' I laughed when I read it. He texted the time and place. I wore a yellow, off the shoulder, empire waist dress and I'd be lying if I said I looked anything other than fabulous.

We met at the restaurant and he kissed me on the cheek. We had a great conversation over the meal, sometimes even touching on my career choice, and then he mused that for such a wonderful lunch date it was somewhat unreal that I was a call girl.

"Such are the mysteries of life," I said.

"I suppose it takes the pressure off desperately trying to get you into bed."

I teased him, "Oh! I didn't know you had that on your mind. So you wanted to get me loose on wine and then fuck me?"

We walked to his office downtown, very close to where we'd had lunch and he kept a spare room for just the occasion. I couldn't guess how many women he might have had there but now he had me.

I explained that I eventually had to get home to walk Sasha but he said, "For the money I'll take my time. We'll finish when my cock is done with you. Strip, Haley, and let me see what I fantasized about last night."

I gave him a show that any seasoned stripper would have been proud of and initially he was tender with me but soon that gave way to a desire for dominance. Pulling me to my knees he never stopped talking, revealing his every thought about me. "You're so beautiful it will be a treat to take you like a sex doll." He forced his cock down my throat and gently patted my cheeks. He occasionally released his hold so I could get a breathe and then resume face fucking me.

"I still can't understand how a girl like you became a hooker. You could have any man you wanted."

Still gasping for a breath, "That's the point. I like fucking them but I don't want one of my own."

"Lie face down on the bed, legs slightly apart," he instructed me.

I felt the cold of the lubricant on my anus and prepared for the initial discomfort of the entry. He was taking advantage of his purchase. This definitely wasn't the girlfriend approach.

"I love a good ass fuck, don't you?"

He straddled me and eased the head of his cock into my hole. "Ohhhhh...ahhhhhhh"

"Nice and tight," as he found a comfortable rhythm.

He went deeper and with more energy and I felt that good feeling build in my belly. He slapped my ass and the feeling grew. "Fuck me, Brad...harder."

"You are a horny bitch, aren't you?"

"Oh fuck, ya, I love your cock in me," and then the surge of pleasure poured out everywhere and I was in heaven. He kept banging my ass for awhile and then withdrew and had me go cowgirl on him.

"I like you riding me so I can see that pretty face of yours." He reached up and took a couple handfuls of my delicious tits while I bounced my bottom on his boner. In no time at all I orgasmed again.

When he came close to climax I dismounted and dropped to my knees and he unloaded on my face, his jizz dripping from my chin.

"Pretty as a picture," he said, admiring his artwork.

***

When I got home Sasha was all over me, probably picking up the strong scent of sex. "Okay, girl, we're going out. Just let me wash my face." After reapplying my makeup I checked my messages.

'Hey, Haley, saw your classified and I want what you're selling. Text me back.'

'Haley - Not sure this is a real picture but if it is I just gotta fuck you. I've got the cash.'

'Hey, hottie! I've already jerked off to your ad-pic. All that's left is to hit that in person. When? where? Cash not a problem.'

One of the things I struggled with at the beginning was what to charge. I had nothing to really go by but a stripper friend told me she gets $300 an hour back in the VIP room and that's for nothing more than a bump and grind and not the slightest chance of actual sex. So I used it as my starting point even though I knew I was worth more.

Making one last mirror check I snapped the leash on Sasha and off we went to dress up the neighborhood.

It was a beautiful day and, freshly fucked, I had that confident, satisfied glow. I passed plenty of guys that gave me the furtive glance then the look back. One guy made quick eye contact and then turned around and walked backwards a few steps to check me out. My hips worked a little harder when that happened.

Then there's the dog attentive guy, "What a cute dog!" (bends down to pet Sasha) "Aren't you, girl? Aren't you a beauty?" (followed by) "What kind of dog is this?" (and) "I love dogs."

He got what he was shooting for and that's a conversation. It's what I dubbed, 'The dog dance to get in my pants.'

I tried to never blurt out that I was an escort but instead insert enough innuendo so that it was impossible not to figure it out.

A few times the flirting escalated to looking for a safe place to fuck me or quick blowjob but cash was a usual stumbling block because a lot of men didn't routinely carry cash anymore and I didn't take credit cards.

Even so, those times that we hooked up on the fly (at a discount) were places like on a front hood in a carport, in a bathroom stall in the park restroom and behind a grocery store loading ramp (got discovered by a very happy truck driver).

Even though I don't do it very often, having sex in a public place is very exciting. The risk heightens the senses. Very fun.

So as Sasha and I merrily made our rounds I always expected the unexpected. This day, walking down a side street, an SUV pulled alongside us. "Haley!!" he shouted out from the driver's seat, "Haley!"

Oh no, it was the fast food restaurant manager I had filed far away in my memory bank as 'And then that happened.'

"Oh, hi...ah..." I realized I never knew his name.

"Russ," he said. "I was your manager."

"How are you?" I said not really caring about the answer.

"Great, but we sure miss you at the restaurant."

I bet you do, employee fucker, "Well tell everybody hello for me," and I started to walk away.

"Hey, wait! (oh shit) Can I talk to you a second?"

I reluctantly leaned back into the window. "Got an appointment to get to," I lied.

"Just take a minute, c'mon get in."

I got in but left the door open to Sasha, "What's up, Russ?"

"Ya, well I couldn't find a number for you but anyway I'm having a group of guys coming over for a fraternity reunion Saturday night and I wanted to ask you if maybe you'd be the entertainment. It just came to me that you'd keep it from being boring."

"Entertainment?"

"Ahh, you know...entertain the guys at the party.

"You mean fuck the guys at the party?"

"Ya, you know, like individual or, you know, in a group? Something like that? I was going to hire a stripper but then I saw you and, you know..."

"Russ, for god's sake spit it out, you want me to come to your house and gangbang your party friends from college."

"Ya, that's it."

"But why me?"

"You know why. Look, I'm willing to pay you well for your time and, um, skills."

"What makes you think I'd prostitute myself like that? You think I'm a cheap hooker?" I toyed with him because I didn't like him.

"No, no, no! I just thought, you know, you blew that guy in the parking lot and then my office...I just thought you might need the money."

I just looked at him a while longer until he was uncertain and uncomfortable. Then I got down to business.

"How many guys and how long?"

"Eight including me for two hours."

"One thousand."

"I was hoping for a little less."

"Well we all have to be disappointed with something. Yes or no?"

"Yes, for sure, yes, I'm still remembering you in my office."

"What's your cell number?"

He told me and I texted him back. "There, now you have my number. I gotta go. Text me the details and I want cash up front." I hopped out of the SUV and headed home with Sasha. I'd had enough adventure for one day and, besides, I had to get back home to schedule the guys looking for appointments.

***

Saturday morning came and all I could think was I'm going to fuck my asshole ex-boss and seven of his probably asshole frat brat friends. You shouldn't have to start off the day with that thought but it jumped in my head the first moment of consciousness. But a job was a job.

The only plus was that I had cum with his dick in my pussy. Come to think of it I was more pissed off that I'd orgasmed with a man I didn't even like but that only cemented in my mind that I'd made the perfect career choice.

Russ wanted me there at 9pm, after the boys had a drink or two. His idea was to explain to the group libido that they were in for a fun evening with a surprise guest.

When I walked in the room wearing a short black skirt, sheer black top, see thru to a white bra and very high heels every head turned as if on the same swivel.

As a playful homage to my former boss I wore my hair in a ponytail, coming through a visor we wore at the fast food restaurant. I heard a cacophony of comments such as:

"Of, fuck me," "Holy shit," "Hotter than fuck," and other such things. I knew we were all on the same page. Russ handed me an envelope which I deposited in ny handbag and then he introduced me to the boys as one of the "best managerial decisions" he ever made while stroking the bulge in his pants.

Everyone knew what was coming.

There was polite laughter at his joke but eyes were only on me. Their ravenous attention made me wet and when I walked through the room their hands reached out, feeling my ass and the inside of my thighs.

Turning to face them I posed and said, "Hi, I'm Haley, place your order when ready!"

As soon as one man got up and started to unzip my skirt it was on.

They groped me seemingly everywhere and their overwhelming touch had me already on the verge of cumming. Clothes were discarded everywhere until everyone was naked and jerking their cocks.

This is a good time to note that it was early in my career and I'd never been gangbanged. Furthermore, I had never participated in group sex with the exception of a night of strip poker when I was about 19 and at the end all we had were four uncomfortable friends.

But this was not that...far from that. This was animalistic. Pure frat house fun. The only things they left on were my heels and the visor.

Circling me they played grab-ass and slapped my buttocks like men enjoy doing. They fondled my tits and kissed me, an occasional finger fuck.

I closed my eyes and surrendered to them, lost in a sea of touch.

From everywhere they presented their cocks and I sucked them as efficiently as I could. Their hands everywhere caused the first of many orgasms. My body spasmed.

Russ had arranged a long padded bench in the middle of the living room and they began to jostle for position in order to be the next to fuck me or have me suck their dicks.

At first they were lined up for a missionary fuck but it wasn't long before they had me on all fours. Never taking a break, as soon as one cock pulled out another took its place, while the rest went about keeping their hard-on so they'd be ready.

It was a carousel of cocks.

I saw him out of the corner of my eye. He was big, tall and burly. I was surprised I hadn't noticed him earlier but he approached my backside like he was stalking something. His cock hung straight out like a curtain rod, no assistance necessary. He kneeled on one leg and drove his weapon deep into my wet receptacle.

The bench sagged and rattled like it might break. Each time he pushed it knocked the wind out of me. Then he grabbed my ponytail and used it for even better leverage. He was a fucking beast.

Russ leaned over my ear, "I need you over more often."

"You can't afford me."

"I'll take out a loan."

Then he shoved his dick in my mouth. "There we go, baby doll. Suck me off while Geraldo does his thing!"

Geraldo's big hands wrapped around my waist and rammed me senseless until I came again. Then, with the roar of a bear, he lost his load in my pussy and when he stood up to let the next guy in I could feel his cum running down my inner thigh.

A guy mounted me, Jimmy, who while fucking the daylights out of me, leaned over to ask if I'd go out with him. I had read about the Madonna/Whore Complex, where a man wants to adore a woman and then fuck her like a whore. This was that.

This is where my cuteness kept stepping in because my admirers couldn't quite see past my looks to honestly see me. Instead, they saw an idealized version who happened to be a good fuck.

When I said no, he fucked me hard enough to knock my teeth out.

During a break in the fuck frenzy, "to give Haley's pussy a breather," announced Russ, men came up to me with their business cards to either hire me for a party or some one on one action. I cashed in on most of those.

I stayed another half hour getting fucked holding on to the kitchen counter until Russ suggested going bukkake on my face. Geraldo picked me up and laid me on the bench and the men, surrounding me jerking off, collectively shot their spunk all over my face and tits.

And it was over.

Russ let me shower before I left. Of course, not without watching me from the door.

After the goodbyes he walked me to my car, "Let me take you to dinner, okay?"

"Burgers and fries?" I joked.

"No, a proper meal. Okay?"

"Sorry, Russ, but I don't date. Thanks for the gig but I'm not interested."

"You say that now but I'll eventually grow on you."

"If that happens I'll get an antibiotic," I said laughing, "See ya!" and drove off.

At home, Sasha welcomed the returning warrior with lots of kisses mixed with some bladder urgency. After that was accomplished I sat down and answered all my requests for some pussy time. When it was done I'd nicely filled out the calendar month with 5 more outcalls and 2 incalls. Outcalls, I went to them and incalls came to me.

The classified website I used let me post multiple photos of my rockin' bod and particulars about measurements and things I was into. I confidently added, 'gangbang'.

As I had just finished answering I got another ad request:

'I've never stepped out of my comfort zone but one look at you and...'

Fuck me, baby?

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AnnalovesitAnnalovesit10 months ago

I like Haley, I think there is a lot more to cum from her!

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