To be perfectly clear I'm not naive and I know how lucky I am to have navigated the potential pitfalls of the escort lifestyle. I was never arrested, never abused and most importantly I never got pregnant or infected with some disease.
At the end of the day I'm 23 and partially retired. I have apartments in multiple cities and a little beach front villa here in Ibiza, Spain. Why 'partially retired'? Well, when the CEO of some Fortune 500 company wants to meet you in Paris for a weekend so you can fuck him in the ass with a strap-on and is willing to pay you 50 thousand dollars it's really hard to refuse. I can afford to select who I want to entertain and who I don't. Nowadays it's about what's in it for me. So when someone wants to give me 50K and a weekend in Paris' elite establishments, who am I to say no?
It started the summer before my Junior year in High School. My foster family finally let me get a job at a soft serve ice cream shop at the beach near where we lived. It paid minimum wage and whatever tips you got which was none. About the only bonus to working at the soft serve was that you got free uniforms. No matter how hard you tried to stay clean by the end of the night you were covered with a nasty sticky coating of ice cream. So being able to change out of a uniform and have a laundry service wash them for you was pretty nice.
The normal routine was whatever crew closed the store would grab some beers and go for a walk on the beach. It was common to go swimming in our underwear or even skinny dip to cool off. On a few occasions someone would bring some pot and a few people would smoke. It was mostly innocent and just a way to pass the time. Most of the employees got along pretty well and even the manager was nice. Maybe it was because he was 18 and still one of us, a teenager.
With a little over a month left before school started I did my first trick. Don't get me wrong, I wasn't looking for customers. I didn't even know what an escort was.
It was my manager. Like I said he was 18 years old, one of us and semi-cute. He was also our main contact for getting some beer. My manager and I were working the “closing” shift on a pretty slow night.
“You want to walk on the beach tonight?” I asked.
“Why so you can mooch more beer? You never fucking pay for anything.”
He was right. I didn’t. Not because I didn’t want to but because my foster parents made me give them half of what I earned and then deposit the rest. They didn’t want me to spend any of my money. “You have to save it for college,” was the mantra I heard every week.
“Forget the beer. Let’s just go for a walk.”
“After working here all fucking day I would rather forget this place instead of the beer.”
When 11:00pm finally rolled around we shut off the outside lights and closed the windows. We did our normal closing tasks and when we were done I went into the office to change. I undressed down to my bra and panties and took a quick sink bath. If we weren't going to the beach I at least wanted to get the dried layer of ice cream off my arms. When my boss walked in I was already done wash and was standing in front of the small office fan with my arms spread to the sides in an attempt to cool off.
“Damn girl! You should put something on or I might not be able to control myself,” my boss said as he walked in.
“Yeah, right. You see more than this at the window every day.” I said referring to the constant parade of bikini clad girls that came to the store.
“Here. Have a beer.”
“No. I can’t pay you.”
“How about this. I’ve already seen your sexy little body. What do you say you give me a kiss? Just a little one on the cheek and we call it even.”
“Yeah, I'm sure all you want is a kiss.” I said sarcastically pursing my lips.
“Even better. Take off your bra and panties and I’ll give you 20 bucks. That’s 20 bucks just to let me look at you’re your little titties.”
“I knew it. There’s always something with you. Would you like me to do a little dance too?”
“I'm serious. I can already see half of it anyway. Just slip them off and let me have a look.”
“No. I’m nasty right now.” I said not knowing why I added the last part. Sure I was nasty but why not just ‘No’ and end it. Instead I left it as an opportunity.
“Let’s run over and take a quick swim. I can use to clean up too.”
“Okay, let’s do it but that doesn’t mean I’m showing you anything.”
My boss opened a beer and took a long drink. “Here, finish it.”
We did a dash from the store, across the street to the beach, into the ocean and back in five minutes.
We were back in the office drying off when my boss said, “You should really take the 20 bucks. Your bra and panties are soaked and I can see everything.”
“Give me a beer.”
“How you going to pay for it?”
“From the 20 bucks you’re about to give me.” I said and slipped my wet panties to the floor. My bra quickly followed.
"Wow," My boss picked up a beer and walk over to me. “What would it cost if I wanted to touch you?”
I took the beer and took a long nervous swig. “I don’t think you could afford it.” I said defiantly as I stood there naked
My boss slowly walked around me looking up and down. He stopped in front of me and sat down on the desk.
“What if I wanted something else?”
“You still couldn’t afford me.”
“How about 20 bucks for a blowjob?” my boss asked.
“That’s all? You want me to blow you for 20 bucks? Hah. Not even close.”
“Oh! So there is a number. What about 25?”
It was a game. Well, maybe it was for me because I thought it was just a joke. My boss had seen me naked before so that wasn't a big deal but as much I was playing he was serious and kept throwing out numbers.
I slipped one of my fingers into my mouth and slowly pulled it out. "I told you. You can't afford this."
“Nothing less than a 100.” I said with a teasing laugh.
“Okay. 100 bucks it is. But you swallow.”
My heart stopped and a surge of anxiety slammed into every fiber of my consciousness. What the fuck had I just done? I never thought he would pay 100 dollars for a blowjob. I didn't think anyone would pay that.
I tried to think of a way out of this situation. “No, it's a 100 bucks for the blowjob but if you want me to swallow that’s an extra 50.” I had a moment of hope. He would never agree to that. I silently let out a breath.
“Deal. I’ll even throw in a beer.”
I was in a complete state of shock. I was outside my body watching myself negotiate a price to give a blowjob. I could hear the words and see myself standing naked in front of my boss but I was powerless to stop it.
I had given blowjobs before but only to guys I had dated so it was different. I was dating those guys. They were boyfriends and I liked them. It was what boyfriends and girlfriends did. You know, kissing, foreplay, sex, all that stuff. I started to try and rationalize the situation. It was 150 bucks, no, 170 bucks for what? A five minute blowjob? He was cute and in pretty good shape.
My boss broke my trance by standing and pushing his shorts down to the floor. His hardening cock swung out into the space between us. He then flopped down in the lone chair in the room.
“What are you doing?” I asked.
“What’s it look like? Sitting down and getting comfortable. I'm gonna enjoy this.”
“What about my money? 170 bucks.”
“170? We agreed on 100 for a blowjob and 50 to swallow.”
“And 20 for me to get naked.”
“Damn. You’re fucking expensive."
“Yeah but look at this." I said holding my arms up in the air and showing a smile that contained absolutely no confidence. "I'm worth every penny.”
Like I said I had given blowjobs before but I’m not sure they were any good. Every guy will tell you that you give great head when you have their dick in your mouth.
My boss stepped over to the safe and worked the dial. When he opened the door he grabbed a thick wad of twenties and quickly peeled of nine of them.
“Here. There’s an extra 10. Consider it a tip."
There was no making out or feeling each other up. My boss just went back to the chair and sat down with his legs spread. His cock was already semi hard and was laying on his stomach.
“Come on. Let’s see what a 150 dollar blowjob is like.”
I stood there looking at his cock. The tip was swollen and the urethra was thick. At least he wasn’t huge. That would make it a little easier.
“What’s the matter? Cat got your tongue? Well he better fucking move because I paid for that mouth and I can’t wait to feel it wrapped around my cock.”
I swallowed hard and moved forward. I still had a chance to stop. I didn’t have to do it.
“I promise it won’t bite. Kneel down.”
I did as I was told and knelt down between his legs. I slipped my hands up his thighs until my hand touched his now hard cock.
With his cock in my hand I started to kiss his balls. Then I followed with little flicks of my tongue and ended by sucking each ball gently into my mouth. I could taste the saltwater from the ocean on his skin. From there I started to lick up the shaft I stopped when his cock tip was right near my lips and looked at my boss. He was staring down at me as I planted soft kisses on the underside of the tip and right on the tip.
“Good girl. Nice and slow.”
I let my mouth get nice and wet with saliva before I swirled my tongue around the tip. I spread a thin coating of saliva around the salty tip before slipping my tongue into the opening.
“Take it in your mouth.”
Finally, I took the tip into my mouth and worked my lips up and down. I took a little more in my mouth and I stopped at the rip and pulled my lips over it repeatedly. I started to suck and release on the tip before starting to take him into my mouth. His thick shaft was warm against my lips. He cock was pressing against my tongue and spreading my mouth open as I took more and more of him. I kept taking him until I felt his pubic hair against my nose.
“Oh fuck yeah. You’re a good little cock sucker aren’t you?”
After a few minutes of continuously taking his entire cock into my mouth he started to moan so I slowed down. I didn’t want him to cum too quickly. For 150 dollars I might as well give him his money’s worth.
After a few minutes of slow soft sucking he calmed down but it was time. I started to slowly slide my hand up and down his shaft in unison with my mouth. I kept my mouth on his cock the entire time and started to suck harder each time he was in my mouth. His legs started to tense and he started to thrust up into my mouth. I squeezed his shaft and pulled my hand down toward his balls and held him tight. I could feel his cum starting to pulse against my hand and spill into my mouth.
“ooohhhh, Holy Fuck.”
I kept my lips tight around his shaft and looked up into his eyes. He kept cumming. He grabbed his cock shaft and quickly jerked it causing a bit more cum to squirt into my mouth.
I squeezed my lips tight to his shaft and slipped his cock out of my mouth. No cum spilt out. I looked into his eyes and swallowed. I didn’t allow myself to make any bad facial expressions as I did it and I even gave him a little smile when it was gone. I finished by taking him back into my mouth and sucked him until he was flaccid.
“Well, what do you think?” I asked while biting my bottom lip.
“Holy fuck. Where’d you learn to do that?”
“I’m self-taught. I’m glad you liked it. Anytime you want to try it again just let me know.”
“What’s it going to cost me to get into that pussy of yours?
“How much money do you have?” I said with a smile.
It didn’t last any longer than ten or fifteen minutes. I had been paid to give blowjob. No matter how I tried to spin it I was just paid to suck some guys cock. I just turned a “trick”. It was just a blowjob but it was a trick just the same. I couldn't help but think how I had just worked 5 hours making $7.25 an hour for a whopping $36.25 working as an Ice Cream Clerk but I spent 10 minutes on my knees and I made $150. That would be $900 dollars an hour. Not bad for an hours work.
I took the last sip of my beer while I finished dressing.
“Can you work the closing shift tomorrow?” my boss asked.
"It would be just the two of us."
“Yeah, I think I can be here.”
I had my first official customer and he wanted a repeat performance.
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