Tranny Encounters - Escort Fucked

I want to thank Wayne & Whordinarygirl for helping edit this piece. I hope that you enjoy reading it. As usual, please feel free to comment and vote on the story or write to me via email using the contact on my profile.

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Walking out into the parking lot, I wiped the sweat off my face as I headed to the car. Though it was spring time, the temperature seemed to be rising in Bluehaven fast. Atleast classes for the day were over and I could go home and relax in a nice bath. Just as I sat down in the car, my phone began to buzz.

"Hello, Simone," said a familiar female voice.

"Hello Cherrie," I replied.

"How are you today?" she asked, being polite.

"Good..." I responded.

"Are you free tonight?" asked Cherrie.

I bit my lip as I knew the question was coming. Money had been really tight. Ever since my parents had died it had been really difficult to hold down a steady job and do community college. A girl at college had introduced me to Cherrie who had the answers to my problems. Cherrie ran a very high class escort agency in Bluehaven. It was very hush-hush. Her clientele included some really big names ranging from big shot businessmen to high profile celebrities.

"Do you have a client for me?" I asked.

"Yes, it's a 3 hour appointment," she informed me.

"Who's the client?" I asked.

"Well, I don't know. The job is coming through a referral. Usually I would not agree to something like this, but the middle man is someone I know personally and a very old client. So I had to consider it."

"What does this client want?" I asked.

"I was told that this particular client wants someone young, between the age of 20-25, blonde, supple breasts and willing to do anything. So, naturally, I thought of you."

"Cherrie, I don't know. Have you even met this client?"

"No."

"Then how can I just go to client that even you haven't met and vetted."

"It pays more than what you would usually get for a full night."

"How much more?" I asked.

"Two thousand."

I was a bit shocked when I heard the figure. Usually most of the regulars I saw only wanted my company for a couple of hours and it wasn't half the price of what was being offered right now. This was over double and quite enticing.

"Simone?"

"Yes, Cherrie. I'm here," I replied.

"Well, are you interested or not?" she asked.

I silently sat in my seat, staring at the steering wheel, thinking if I should accept this offer.

"Simone, you need to answer me. Otherwise, I need to try to get a hold of one of the other girls."

"I'm still thinking..." I replied.

"Think faster, I need an answer before I hang up on this call," she said sounding a little annoyed.

The money was good. More than I had ever received for anything I had done.

"Simone!"

"Umm, sorry... uhh... yeah I'm free tonight," I replied.

"Good. So..." I cut her off.

"But... I have some conditions," I said, trying to sound a bit authoritative.

"And what are these conditions?" she asked sounding even more annoyed than before.

"No whips, no chains, no pain of any kind, no golden showers, no anal and absolutely no marks," I said. "The last client you booked me with wanted it all and it was not pleasant."

"Darling, in this business you cant keep conditions. The client pays you and you do what the client wants. End of story."

"Then I'm out," I said. I had heard the whole give the client what he wants speech before. While not every client was the same, there was an occasional one who didn't care and pretty much took what they wanted, leaving girls like me with bad experiences. And even though Cherrie said she would get another girl, I knew she didn't really have any options to go with. Most girls would never go out on something like this blind and she obviously didn't have any choice but to come to me.

There was silence on the line for a few moments. Maybe my bluff didn't work.

"Fine," she said, sighing into the phone.

"Okay. I'll do it then."

"You are to go to the Hotel Marquis. At the reception, ask if they have something for you. You will be handed an envelope with further instructions. Be there by 9pm and don't be late."

"Fine."

"Oh and another thing, the client has a request."

"Which is...."

"Dress classy."

"Don't I always?" I said, agitated.

"Classy doesn't always mean sexy. This client is apparently very particular and clear that you dress a bit conservative, but sexy."

"Okay, got it."

"Good, don't be late," she said before hanging up.

A little exasperated, I was glad the call had ended. Though I had nothing against Cherrie, she could be quite cold at times. She was very moody. On certain days, she would be like the best friend you never had. On others, she behaved like the ice queen.

Putting my phone back in my purse, I drove home. Fifteen minutes later, I took care of some college work before I made some dinner and left for my very secretive appointment for the night. Unfortunately, the college work kept me going through most of evening so I didn't time to prepare dinner at all. I only had time for a sandwich and a soda.

By 7:30, I got into the tub and took a nice warm bath with some scented oils. The day at college had been a bit rough, plus the heat did not help at all. I didn't want to meet a client smelling disgusting. After I was done, I decided not to use a lot of make and to keep things a little more simple. I never did usually use a lot of make-up, but tonight I decided that I didn't need to go all out to impress the client either.

After make-up and hair, I picked out a lace bra with matching panties, garters, and some black nylon stockings. I decided to go with a red dress that looked conservative enough to appease the client. Putting on a pair of black 4 inch pumps, I gave myself a once over before I decided to leave.

As I headed downstairs, I almost grabbed my keys but stopped. Maybe going out dressed to the nines to an elegant hotel in a shitty Honda Civic wasn't the best idea. I called a cab.

By 9pm, I was at the Hotel Marquis, heading toward the lobby. There was an older woman, probably mid-forties, standing behind the counter as I arrived at the desk.

"Do you have something for Simone Bradley?" I asked.

The woman looked in my direction and raised her eyebrow. She obviously knew why I was here.

"One moment please," she said, turning and walking away.

She returned a minute later with an envelope and handed it over to me.

"Thanks," I said and walking away from the desk.

Opening the envelope, I pulled out a key card and a note.

ROOM 704

Apart from the room number there was nothing else written on the piece of paper. Discarding the note and the envelope, I headed toward the elevator. Moments later, I stood outside Room 704 with the key card in my hand.

Taking a deep breath, I unlocked the door and let myself inside.

The room was mostly dark with just a couple of lights on. It looked as if no one was inside.

"Hello?" I called out nervously.

"Take off your dress," said a female voice.

Still nervous, I put my purse on the table and unzipped my dress, letting it fall on the floor.

"Did you agent give you the details for tonight?" asked the female voice.

I nodded, "Yes."

"And was it specified that you will be willing to do whatever the client asks of you, even if its unorthodox?" asked the female voice.

I nodded again. "Yes."

A light turned on next to the couch where a woman sat with her legs crossed. She had red hair, alabaster skin, and was wearing a white silk top and a black skirt. She looked very elegant, and with the look that she was giving me, she looked like the no nonsense type. Getting up she walked over and stood right in front of me. I noticed she had piercing green eyes as she looked me up and down.

"When does my client get here?" I asked.

Folding her hands, she gave me a sheepish grin. "I am the client."

This was definitely a first for me. Though I had been with a couple once, I had never been with a woman one on one.

Moving to a chair close by, she took a seat and crossed her legs, like a well-mannered woman would.

I stood there nervously as I didn't know what to expect.

"Take off your bra," she said, authoritatively.

Taking a deep breath, I began to unclasp my bra.

"Slowly," she ordered.

I unclasped my bra and slowly slid the straps down. Making eye contact with her, I dropped it on the floor. Running my hand on my breasts, I tried to cover them up.

"Don't do that," she said.

I immediately stopped and put my hands to my sides.

"Take your panties off; you can keep the garters and stockings on though."

Obeying once again, I pulled my panties down and dropped them on the floor next to my bra.

"Take off your shoes, I want you comfortable."

Slipping off my shoes, I stood in front of her, my hands a little fidgety as I felt like I was on display.

"Get on your knees in front of me."

Again, I did as I was told as I moved up next to her and got on my knees. She picked up a white box on the stand next to her and handed it to me.

"Open it and remove what's inside."

I opened the box and pulled out a white collar with a ring in the middle and a leash that could be attached to it.

"Let me help you with that," she cooed.

Handing the items to her, I lifted my hair as she put the collar around my neck and then attached the leash to it.

Leaning down, she gave me a soft, gentle kiss on the lips. "You're mine now."

Uncrossing her legs, she pulled her skirt up. As she did so, I noticed the garters, stockings, and the pair of silky black panties. The panties were covering a huge bulge. I gulped and looked up at her as she gave me a devilish grin.

"Take my panties off."

Doing as I was told, I pulled her panties off and a big cock sprang up from between her legs.

I gasped as her huge cock saluted me. It looked like it was close to 10 inches. I looked up at her even more nervous than before.

"Is this your first time with a woman with a cock?" she asked.

I nodded.

"Good! That's what I wanted," she said with a smile, pulling the leash toward her big meat stick. "Lick it."

I moved my hand up, grabbed her rock-hard shaft, and slowly began to lick it.

"Did I ask you to use your hands?" she growled.

"No... no..," I responded meekly.

"No what?" she asked menacingly.

"No, ma'am," I replied.

"Good," she said, her face lightening up a little.

Putting my arms to my sides, I began to lick her shaft from root to tip.

A moan escaped her lips as I licked the tip.

"You can take it inside your mouth," she whispered.

Slowly, without moving my hands, I took the head of her cock into my mouth. Lowering my head slowly, I tried to take in as much as I could. Due to the sheer size and girth of the thing, I was only able to take it midway and then slowly began to bob up and down on it.

"Good girl."

Pulling her cock out of my mouth, she grabbed my chin and gave me another soft kiss.

"My cock tastes good... doesn't it?"

"Mmhmm," I nodded.

"You want more?"

I nodded again.

"Then come suck on it some more," she said as she stood up.

She held her cock and gave it a few tugs before I took it back into my mouth. She grabbed my head and forced her cock further down my throat as she held on to the leash.

"Mmm, yeah, that's it. Suck on my dick."

I gave her cock a few licks and took it down and bobbed my head on it a few times and repeated these motions several times. Her moans and groans told me I was doing a pretty good job of blowing her.

"Look up at me when you do that," she grunted.

Making eye contact, I sucked the head back inside my mouth.

"Good girl. Keep sucking."

And I did.

Dropping the leash, she grabbed my head with both her hands and began to force fuck my face, pushing her cock deeper down my throat, causing me to gag. I held on to both her legs for support as she roughly fucked my mouth.

Holding me in place with three-fourths of her cock inside my mouth, she leaned down and spanked my ass. A few seconds later, she let me come up for air as she pulled it out. A sting of saliva connected my lips with her cock. Grabbing it, she began to slap my face.

"You like that? You like how I force fuck your face?"

I could only squeal in reply as she kept slapping me with her cock.

"Take more," she said, grabbing my hair and pushing her cock back into my mouth.

This went on for a few more minutes before she decided to pull out and let me catch my breath.

"Move into the bedroom, on your hands and knees."

Obeying her command, I got on my hands and knees as she led me to the bedroom.

"Get on the bed! On your hands and knees!" she ordered.

I moved into doggy position with my ass and pussy on display before her.

"Mmm, look at that pretty pink pussy," she said, rubbing my pussy.

I moaned as I felt her fingers rub my clit. A few seconds later, I felt a finger probe my pussy. She began to slowly move her finger in and out. I moaned in pleasure as she began to increase her speed. I felt my orgasm begin to rise.

"Ask for permission," she said, continuing to finger me.

"May I please cum," I squealed.

"You may," she replied and began to finger me faster.

Just seconds later, my orgasm hit as I felt my body begin to shake and quiver. As my orgasm died down, she removed her finger and flipped me over.

"What do you say?" she asked, pulling the leash.

"Thank you," I replied.

"Good girl."

Leaning down, she kissed me once again. This time a little more passionately. I was surprised at how soft her lips really were. Earlier I couldn't tell as she would just give me a peck on the lips and pull away. It didn't take long for me to being returning her kisses as we began to furiously make out.

"On your hands and knees again," she whispered silently as she broke the kiss.

Once in position, she aimed her cock at my pussy and slowly began to push in. I winced as she entered me deeper and deeper. I had never had a dick this big and thick before as I felt my pussy tightly grip her beast. Once down to the hilt, I buried my face into the mattress as she held me in place. After a few seconds, she began to push in and pull out.

"Push back on my cock," she commanded.

I did as I was told and began to bounce back and forth on her cock. She leaned down and grabbed the leash and began to pull on it as I fucked myself on her cock.

"You like that, slut?"

"Oohh yes."

"You like taking my big fat she-cock?"

" Oh yes, I love it!" I exclaimed.

"That's what I like to hear. Keep bouncing on that dick, slut."

A few bounces later, she pulled out. Grabbing my head, she pulled me off the bed and pushed me against the glass window of the bedroom.

Pulling my ass cheeks apart, she drove her mammoth beast right back inside my dripping wet pussy.

"That's it, slut. Scream for me. I want noise complaints. I want security to show up at the door so I can answer the door with your juices dripping off my big, thick cock!"

"FUCK FUCK FUCK!" I groaned as she drilled me hard and fast.

She pulled my right leg up and began to fuck me like there was no tomorrow as I leaned back a bit and grabbed on to her neck for dear life. Guessing that this position was a little uncomfortable, she put my leg back down as I arched my back. She grabbed on to my hips and kept pounding me.

"That's it! Take that dick!"

All it took was a few more strokes and my orgasm hit me again. This time my orgasm hit me even harder as I got pounded like a cheap whore.

"You didn't ask for permission!" she growled and began to spank my ass really hard as she pounded me. It hurt and stung like hell but I didn't care as I rode my orgasm in complete ecstasy. Just as I finished, she pulled her cock out of me and forced me to the floor.

Grabbing my hair she began to jerk off on my face. All it took was a few pumps and I felt rope after roper of cum hit my face. It felt warm, and it felt heavy as some of it flew into my hair, some hit my nose and my chin. Once she was done, she released my hair as I fell back against the bed.

As she pulled me up on my feet, I almost fell back as my legs felt like jelly. Once on my feet, she pulled me close to her and kissed me again.

"You can stay the night if you wish," she whispered.

"I can't."

"As you wish," she said, moving back.

She opened a drawer on the nightstand beside the bed and handed me an envelope.

"Take a shower before you leave," she ordered.

I complied.

Once I was done, I dressed up and caught a cab home. The entire ride back, I kept rethinking the whole night as my pussy began to leak again.

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