Escort

Chapter 2

The dinner was coming to its end and everyone was saying their goodbyes.

Boring, it was. I spent most of the afternoon pretending to care about conversations between Tom and his friends or sitting at a table and people-watching. I'd occasionally go through my phone and search through clothing websites. Throwing things into my cart is a hobby.

I held Tom's hand in mine as he spoke. And I'd grin and nod when they would do the same to me.

"You have a good evening, Mr. Hathaway." said some man named Bill Ryn.
"You as well." Tom replied and pulled us towards the exit.

"Um..." he began.
We made it to the vehicle we were chauffeured in.
"Yes?" I responded.
"Can...When we get back, can you..."
"Do you deserve it?" I asked and felt the car pull off.
"I think so..."
"Hm. What do you want? Use your words."
"I...want to be inside..."
"Yea?"
"Please..."
"Please, who?"
"Please, mistress..."
"I'll think about it on the way there."
"Okay." he agreed. "Can I hold your hand?"
I looked at his hand as it pulled at the leather seat. He was eager.
I held my hand out.
He happily took it.

____________________________________

Tom sat on his knees in front of me. Only in his black underwear with a leash around his throat that I held loosely in my hand. I kept his wrists cuffed together just for the hell of it. He was the only one that had changed. I still wore my dress and heels, my leg poking out of the split.

"You look pathetic." I insulted as he stared at me with large eyes, hoping for something to relieve his sexual frustrations.

"Please..."
"How much longer are you going to beg me to do something with that needy dick of yours? Aren't you tired?"
He whined.
"You know how I feel about whining."
He nodded.
"So then...you also know what that means, right?" I got up and began walking to the closet.
"I'm sorry..." he stated.
"Oh, it's too late for apologies, sweetheart. You tried to rush mommy and you know that's not okay."

I grabbed my favorite toy and a black blindfold.

"Strip for me, okay?" I called from the closet.
I could hear the chains from his leash and handcuffs as he stood up and began moving.

I walked back out and saw him sitting back on his knees with his shorts folded to the side.

I snickered. "See. Sometimes you can be such a good boy."

He picked his head up and looked at me. Noticing the toy in my head.

"Please...not that one..." he begged. "I'll do better, I promise..."

It was a vibrating cock ring. Doesn't sound too terrible until it's around you and forcing you to cum eight times in a row.

"It's either this or the catheter while I thrust inside. Choose." I commanded.
He was silent.
"That's what I thought."

I walked over to him and crouched down.

After attaching it, I tied his blindfold over his eyes, and turned the ring on.

I could tell he was nervous.

"You won't touch it, right?"
He nodded.
"Words, baby." I instructed.
"I won't touch it. I promise."
"There's my good boy. Where's he been all evening? Stay there and be very still or else we're going to have a problem. I want you to stay in this exact position. If you move, we'll bring out Charlie."

Charlie was the name of my favorite whip. He gets things done.
I use those tears to flavor my morning coffee.

"And you don't want that, do you?" I asked.
"No, ma'am."
"That's right, baby. What a smart boy." I bent over to kiss his head.

I watched him shiver as I started walking out of the room.

I closed the door quietly then headed to the kitchen.

I looked at my phone while I walked over to the bar of the hotel.

I grabbed a wine glass and looked through the options. I decided on a red and poured it in.

My phone began to ring.

"Hello?" I answered as I closed the bottle and took my glass.
"Leilani?" By the use of that name, I knew who it was.

I rarely save a contact. I know them by whichever name they call me.

"This is she..." I responded.
"It's Tony."
"Hi, Tony..." I smiled as I sipped my wine. "How can I help you?"
"How much longer will you be here?"
"It's actually my last night before I ship back home tomorrow afternoon. Why?"
"Are you leaving with Tom?"
"No, he's going elsewhere for a business conference."
"I want to pick you up tomorrow at around 3pm." he stated.
"Mm...And why do you want to do that?" I wondered and sipped my wine again.
"I want to discuss business."
"What's your last name, Tony?" I asked him.
"Claiborne."
"Well, Tony Claiborne, my flight leaves at 4:30, so what are we going to do about that?"
"I don't plan on having you leave." he responded.
"Will you be paying for my hotel?"
"You'll sleep at my home." he offered.
"That sounds suspicious, Tony."
"Leilani, I'm 54 and live alone besides the occasional maid that stops by to clean. What could I possibly do?"
"Hm."

I did usually have a taser and pepper spray on hand in case the men forgot their place anyway. I had yet to use them...I wonder if I come off as intimidating or something.

"Alright, Tony." I agreed. "I'll see you at 3 tomorrow."
"Perfect. Have a good night."
"You as well."
We hung up and I took the final sip from my glass.

I looked at the closed bedroom door.

I placed the wine glass onto the counter and walked back to the room.

When I opened it, I saw Tom laying on the floor, shaking, and covered in his own excitement. He whimpered softly as his fingers tried gripping at the chain of his handcuffs.
I watched as he came again.

"N-No more...please..." he begged.
"Aww but look at how cute you are. Weren't you begging me to cum earlier? Isn't this what you wanted?"
He was still shaking as his breathing hitched beyond his control.
"Poor thing. Let me help you." I offered.