Diary of a High Price Escort Ch. 22

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Angel meets a client's dad, then does a freelance john.
15.4k words
4.81
11.2k
8

Part 22 of the 29 part series

Updated 06/12/2023
Created 10/01/2010
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It turned out that I could have enticed Rhys to come inside to continue what was an extremely erotic sexual encounter because when I dialed up Silk, she explained that Daddy had scheduled her for an appointment tonight and that she'd have to take a rain check on our plans to go shopping and enjoy dinner together.

I'd have the rest of the day to catch up on my laundry and housework, but first I logged into my email account and found a new message from Daddy. I clicked on the email and read, "Angel; I have received a request for an appointment from Jonathan Westfield, you may recall that name since he arranged for you to meet his son James a little while ago. He was obviously impressed with the service you provided James and would like to spend Friday afternoon with you. Since your schedule with EE is clear for tomorrow afternoon, I took the liberty of confirming with Jonathan. As before, he'd like to meet you in the lounge at the Grand Hilton for cocktails about one o'clock tomorrow and has requested you dress in business casual attire. Jonathan is a long-time client and judging from the reports I've received from other employees I'm certain you will enjoy his company. Let me know if there is anything that might keep you from taking this appointment. Daddy."

I sat back in my chair and recalled Jonathan Westfield as being a middle-aged gentleman with an air of sophistication about him, his perfectly styled salt and pepper hair, clean-shaven face and sexy white smile holding my attention as we discussed his son's needs last Thursday afternoon. I remember thinking that I'd be very interested if he scheduled an appointment through EE to meet me and smiled knowing that request came so quickly. I suspected his body would match his handsome facial features and if his sexual prowess came close to that of his young son, I was certain it would be an extremely enjoyable afternoon for both of us.

I leaned forward and clicked reply typing, "Daddy I'm pleasantly surprised that Jonathan has requested an appointment so soon after I met with his son and will be happy to handle his appointment. Angel." I thought about asking Daddy how Silk was doing since it appeared her calendar was quickly filling with appointments but decided not to address that in an email. I clicked on send to confirm the appointment for Friday.

While I had my email account open, I sent a request to my attorney Laura asking her how the negotiations with Barry's lawyer were going, then sent an email to Rhys Collins thanking him for his initial efforts to find me a new home. I also told him that I was looking forward to future showings and made sure to mention I'd be happy to meet with him and his friend if he was still interested. The idea of having an interracial threesome intrigued me and I hoped Rhys got the message.

After having a light dinner alone, I spent the remainder of my Thursday catching up on laundry and cleaning around the house turning in a little after ten.

I opened my eyes Friday morning to the flat light of a cloudy day, peering out my bedroom window to find a light rain falling. It was a good thing that I'd be parking in the Grand Hilton's underground garage and would avoid having my hair and clothes become damp. As I showered, I thought about Jonathan Westfield and what I might do to enhance his experience. Since I would be dressed in business casual attire, I decided that I'd excuse myself after we were alone in the hotel room and change into something more seductive. After drying and curling my long blonde locks I pulled them back into a ponytail, I love the look of having my hair pulled tight along my scalp with tight curls beyond the band holding the ponytail. I went ultra-conservative with my make-up only applying the slightest hint of eye shadow and a coat of clear lip gloss. Since Jonathan had asked that I dress in business casual I decided on a pair of fashion, navy-blue slacks and matching blazer with a pale blue, cotton blouse that featured ruffles to hide the buttons. Jonathan and I were meeting in the lounge so I assumed we'd share a drink and talk some before moving to his room. I saw this time together in a public setting as an opportunity to begin my seduction of this middle-aged gentleman and decided that I would not wear a bra under my blouse. I could unbutton my blazer and allow him to see the points of my nipples through the cotton fabric of my blouse.

In the months since I started with Elegant Escorts, I've added to my collection of sensuous lingerie to wear when seducing a client. For Jonathan, I chose a red satin garter and matching bra with a seriously deep plunge between the cups that allow my big soft tits to ooze over the tops. To further enhance my visual appeal, I chose a pair of red fishnet stockings and as one final sensual accent, I included a very thin red satin choker. I carefully folded these items and placed them in a shoulder bag and then added the make-up items I'd need to change my appearance from ultra-conservative to seductively sexy. Having everything I needed to complete my seduction I began dressing for our public meeting. I slipped on the red satin thong that matched my garter and bra set, then the pale blue, cotton blouse. As I buttoned the blouse, I was happy to see that my nipples poked seductively at the soft fabric. I was certain that they would be more pronounced once Mr. Westfield's attention was drawn to my first little tease. Slipping into the navy-blue slacks, I carefully smoothed the tails of the blouse down around my waist and hips, the outline of my big, firm tits showed perfectly, accented by the nubs of my nipples at their center. "Very sexy," I thought as I reached for and slid into the blazer, buttoning it closed to conceal my lovely tits. The bottoms of my slacks rested perfectly on the black four-inch stilettos that finished off my outfit. With my bag slung over one shoulder I headed for the garage and as I backed out, I realized that this time I would be the one arriving late.

The light rain that had been falling all morning was now more like a steady downpour and traffic moved slowly as I made the drive across town to the Grand Hilton. The same valet parking attendant that had promised to take good care of my Benz greeted me with a big smile as I stepped out of the car. "Nice to see you again Miss," he said as he handed me the parking ticket.

I returned his smile and replied, "Gonna treat my ride extra special?"

"Absolutely, will you be staying the night?" He asked.

"Ya never know," I answered wondering if that possibility might become a reality.

As I rode the elevator up to the lobby level, I unbuttoned my blazer gave my nipples a quick tweak to ensure that when I unveiled my braless tits to Jonathan, he'd be sure to notice the twin peaks of pleasure I had to offer.

The lounge was nearly empty when I entered, allowing me to instantly spotting the handsome Mr. Westfield sitting at the bar. I approached him just as he glanced at his wristwatch.

"I'm late," I mentioned as he looked up toward me.

Jonathan smiled and replied, "Payback for last week."

I turned the bar stool a little toward him and as I slipped onto the seat next to him, I replied, "Traffic was moving kinda slowly in the rain."

Seeing me join Jonathan, the bartender approached and asked, "What'll you have," while keeping his eyes focused on my face.

"The lady will have a red wine spritzer," Jonathan offered remembering my choice from a week ago.

I had already crossed my legs and as the bartender moved away, I moved my leg to let my sexy stiletto touch the back of his leg. Jonathan was dressed in a gray pinstripe, three-piece-suit, his vest buttoned tightly over his clearly muscular form. I leaned toward him and placed one hand on his thigh the muscle contracted under my delicate touch. I looked into his eyes and said, "I was so pleased when I got the email that you wanted to see me."

Jonathan smiled while he waited for the bartender to place my drink on a coaster in front of me. His hand moved to mine as I gave his thigh a firmer squeeze and said, "I was quite impressed with you when we met last week."

"Did James mention anything to you about our time together?" I asked as I lifted my hand and moved both to my thigh.

His hand slipped off mine and as he returned the gentle caress of my leg, he leaned very close to my ear and whispered, "James tells me you claim to be the best cock sucker on the planet."

With his hand softly caressing my thigh through my slacks, I took a sip of my drink, then leaned back a little and unbuttoned my blazer as I replied, "That's true, but I have a lot of other talents."

His wide smile confirmed that he was looking forward to exploring each and every one of my sexual talents. I figured this was as good a time as any to show off my talent for teasing a man and slowly pulled my blazer aside letting him see my erect nipples poking at the pale blue, cotton fabric of my blouse. I smiled at him and remarked, "I love the art of seduction."

Jonathan's eyes dropped to my chest and for a brief moment, I thought he was going to slide his hands up to touch my big, soft tits and erect nipples right there in the lounge. Instead, he just smiled and said, "I can see already that you're quite the tease and I love it."

I grinned and shook my shoulders a little causing my big tits to jiggle beneath the fabric of my blouse. He had no idea of the kind of teasing I had in store for him once we were along.

"What else did James tell you about me?" I asked after taking a healthy gulp of my red wine spritzer and after placing the nearly empty glass back on the coaster.

Jonathan paused for a moment, I assumed he was thinking about how much of the details of the afternoon I'd spent coupled in passion with his young son, then replied, "Let's just say that James has an entirely new outlook on how to treat a lovely woman."

I smiled widely, proud in the knowledge that the sensual lessons I'd given him a week earlier had the desired effect.

The bartender returned and asked, "Would you like another round?"

I glanced at Jonathan and barely moved my head from side to side letting him know that I was more than anxious to be alone with him in our room.

"We're good," he replied as he handed his credit card to the bartender.

I slide off the bar stool, buttoned my blazer to again conceal the nubs that were now totally erect and waited for Jonathan to sign the credit card slip.

"I can't wait to get you alone," Jonathan said as he offered me his arm.

I just smiled and hooked my arm into his as we walked toward the exit of the lounge.

As we waited for the elevator, Jonathan glanced at me and said, "You know Angel I've been thinking about you for the last week."

"I hope your fantasies will be fulfilled," I replied as I gave him a sexy wink and a wide smile.

The doors glided open and I stepped into the elevator ahead of him, but before I could turn around to face him, I felt Jonathan's hands on my hips, then sliding forward to unbutton my blazer again. I felt his loins pressing against my ass as he slid his hands up to gently cup both full breasts, lifting them ever so slightly. I arched my back and tilted my head back as his fingertips found the erect nubs of my nipples.

"Hmmmm..." I moaned as he pinched my sensitive nipples through the cotton fabric protecting them.

His lips were next to my ear and after kissing me softly there he whispered, "You are so god damn sexy."

I wanted to turn and kiss him fully on the mouth but his hands and those oh so talented fingertips kept me frozen in place. I moaned again as my nipples began to tingle wanting more than anything to feel his caresses skin to skin. I could feel the moisture begin to flow inside my loins and as the elevator doors opened, I said, "You've got me so wet already Jonathan."

He released his sensuous grasp on my chest and slid his hands down to my hips again, with a twisting motion he turned me to face him. I glanced down at his loins, the outline of his erection clearly showing through his slacks. As I looked up into his eyes, he clutched my hand and placed it against the bulge saying, "You can feel what you've done to me."

For a brief moment, I used my hand to size up Jonathan Westfield. Through two layers of fabric, his cock felt massive, not only long but equally wide in girth. As I released his cock I remarked, "That's quite a package."

Jonathan just smiled and again offered his arm to me as we exited the elevator which had reached our floor. I kept up with his stride as he seemed to walk down the hall with a sense of urgency. The tiny light on the lock changed from red to green and with one swift motion, Jonathan pushed the door open. I stepped through the open door knowing that from this point forth I would no longer be inhibited by the ruse of a business casual meeting.

I placed my purse on the luggage stand across from the bathroom door, then took a couple of steps into the open area of the room which featured a king size bed and a seating area with two comfortable looking chairs beside the bank of windows. Turning to face him I watched as Jonathan slipped out of his suit jacket, then took the time to carefully place it on a hanger above the luggage stand. He walked slowly toward me his wide-eyed lustful stare fixed on my face. I knew that if I held my ground, he would be removing my blazer and most likely unbuttoning my blouse so he could feel the smooth flesh of my big, firm tits uncovered from the pale blue, cotton fabric that before this escaped his touch.

"Let's have a look at..." Jonathan began to say but I interrupted him as I turned around and quickly stepped toward the windows. "I just love having sex in broad daylight," I said as I began opening the heavy drapes covering the windows.

Jonathan was having none of that, and as the flat light of the gloomy afternoon flooded the room, he again approached me from behind. His hands moved to lapels of my blazer and as he lifted the garment from my shoulders he said, "Let's see if they are as lovely in broad daylight as they were earlier in the elevator."

He slipped my blazer off my shoulders and as he placed it over the arm of one chair, I turned to face him moving my fingers up to slowly undo the buttons hidden by the ruffles running down the front of my blouse. His eyes followed my digits as one by one the buttons came open, with each one I spread the fabric slowly revealing the smooth flesh that had been covered before. As my fingertip released the fourth, I pulled the material wider giving Jonathan his first view of both lush orbs of pleasure, the sensuous smooth cleavage between and just a hint of areola. As he stared at my chest, he commented, "Absolutely lovely."

I smiled at him as I released the garment allowing it to slide in covering some of what had just been exposed to his lustful stare. "I want you to take a seat," I said.

His somewhat confused expression didn't surprise me, but as he sat down, he said, "Are you going to do a sexy striptease for me?"

As I moved behind where he was seated, Jonathan's eyes followed, his head tilted back so he could keep eye contact with me. I smiled and leaned down kissing him ever so gently on the mouth, then moved my lips to his ear and said, "I actually have a sexy seduction planned."

"I like that even more," he remarked as I placed my hands on his shoulders.

My fingers slid down along the edge of his tight-fitting vest feeling what I knew would be rock-hard pecs until they reached the top button as slowly as I had unbuttoned my blouse moments earlier, I now started opening each one of the buttons holding the garment tightly around his body. My fingertips detected equally defined abs as they traveled down toward the waistband of his slacks.

Jonathan moaned as I leaned over, fully pressing my tits against his shoulder so I could reach the thick, rock-hard bulge tenting his slacks. I placed my hand flat against the head, then curled my fingers to run them along the length of his shaft. He moaned again this time a deeper, lusty moan. Through the layers of fabric covering his manhood, I could only estimate its length and girth. I knew that before I could release it from the fabric prison holding it so I could study its nuances, I'd have to excuse myself and change into my red satin lingerie.

I removed my hand from his loins, straightened up and walked around in front, then sat down on the edge of the bed. Before I could speak Jonathan asked, "Is something wrong, Angel?"

"Oh my gosh no," I instantly replied.

He looked a little confused until I explained, "You see Jonathan, your request that I dress in business casual attire to meet you really doesn't fit my personality."

"But you looked wonderful, and still do," he answered.

I smiled at him, then said, "Thank you, but I prefer to dress for sex so to speak,"

He grinned widely at me, then said, "I'll keep that in mind for the next time."

"Why wait for the next time, give me ten minutes and I'll show you what I'm talking about," I answered as I stood up from the bed.

"Oh my!" he exclaimed as I walked toward the bathroom grabbing my purse just before making a turn and disappearing from his view.

I tried to change into my red satin lingerie set as quickly as possible, change to bright red lip gloss and finally stretched the red satin choker around my neck. I love the way my big, soft tits look when the flesh kind of oozes out over the top of my cups and gives the appearance that my bra size is a cup too small.

Jonathan was apparently quite anxious to see exactly how I dressed for sex because before I was completely finished, I heard him ask, "Are you okay in there?"

I cracked the door open a tad and answered, "Oh yes I'm more than okay, don't start without me."

I heard him giggle as I opened the door fully and stepped from the bathroom.

"HOLY SHIT!" he exclaimed seeing me for the first time dressed like a slutty whore. His eyes got a big as saucers as he took in the image of how I dress for sex.

"You like?" I asked as I dropped to my knees.

"Very much," he replied.

I reached up and released my hair letting it fall haphazardly around my face, then leaned forward and dipped my head shaking my hair out even more. Looking up at him, I smiled seductively knowing that the image being burned into his memory was that of a sultry seductress, a middle-aged cougar about to pounce on her prey and as I slowly crawled toward him his eyes grew more lustful and his smile widened.

Jonathan had crossed his legs while he waited for me to change but as I approached his chair, he uncrossed them his totally erect cock now tenting his slacks and stretched off to one side. I straightened up between his thighs and placed my forearms across his legs.

"So, tell me, do you like the business-like Angel or the sultry cougar Angel better?" I asked hopefully already knowing the answer.

His reply surprised me some, "I love them both, but this one makes my cock pulsate."

I licked my shiny red lips as I placed one hand on the tented bulge in his slacks, then said, "I've been imagining what this looks like since I first touched it in the elevator."

He grinned at me as his fingers undid his belt buckle which I of course took as permission to satisfy my imagination.

My deft fingers made short work of the clasp holding his slacks tightly to his waist and after pulling the fabric open as far as possible, I hooked a couple of fingers under the elastic waistband of his jockeys and slid my free hand inside capturing his rock-hard cock with my fingers. It felt fiery hot, a combination of the blood coursing through the veins and having been imprisoned in such an erect state for so long beneath his clothes. His glorious cock head came into view as I liberated it from its cotton prison; to describe it as glorious was an understatement. It was most likely the widest, mushroom shaped cock head I'd ever seen, with a corona that stood a full half inch from the shaft just below. I could only imagine what it would feel like inside me. I looked up at him and smiled, knowing this cock head would stretch my throat, caress my G-spot and, if he wanted, spread my sphincter wider than any cock had ever hoped too.