Diary of a High Price Escort Ch. 29

I had planned on a relaxing Sunday, but since my housewarming party turned into an all-out orgy, I had neglected to clean up my place before turning in Saturday night. So I slipped on sweatpants and a tight-fitting tank top and headed for the kitchen. After starting a pot of coffee, I collected all the dirty glasses and loaded my dishwasher. As I sipped my first cup of java, I thought about the previous night's events. Rhys and Liz were the only guests I had planned on fucking, since I wanted to complete my agreement with him to handle my real estate transaction on a discounted basis. I had to admit I got the better of the deal since, along with saving a lot of cash, I got to enjoy his rock-solid black cock and creamy thick load of cum. Liz was a bonus to that agreement.

My attorney, Laura, seemed to come out of her sexual shell somewhat, and her date, Alexis, proved to be an excellent fuck.

What surprised me most were my downstairs neighbors, the Starks. I knew beforehand that Richard wanted to stuff his hard cock in any opening I offered, but Rachel's apparent craving for a big black cock was something I hadn't expected. The way she took on Daddy's monster confirmed she'd jump at any chance to satisfy that craving. On top of that, her admission that she'd be interested in working for Daddy was an even bigger surprise.

Since Daddy had told me it was okay to give Rachel his number, I assumed he'd follow his usual routine of meeting with a prospective addition to Elegant Escorts staff for a verbal interview followed by a physical evaluation of her sexual talents.

I had finished my coffee and was straightening up the living room when my doorbell rang. 'Who could this be?' I thought as I headed down the stairs to my front door. I looked through the peek hole and found Rachel Stark on the opposite side. I opened the door and greeted her, "Morning, Rachel."

"I hope it's not too early," she said with a grin on her lips.

I stepped back a little as I answered, "Not at all; I was cleaning up the place. Would you like a cup of coffee?"

I followed her upstairs and into my kitchen. As I poured two cups, Rachel mentioned, "That was one hell of a party."

"I hadn't planned for it to go the way it did," I replied with a grin on my lips.

We sat at the island; Rachel turned her stool a little toward me as she said, "I should apologize. I guess my actions caused the change in plan."

I turned my head toward her, "We're all adults, and it seemed like everyone was okay with the entertainment."

She giggled, "Franklin was very entertaining."

I just smiled at her.

"Speaking of Franklin, I was hoping to get his number from you today," she said.

"He did tell me to give you his number," I replied as I opened the contacts list on my phone.

I watched as she entered his number into her phone and then began to save it as Franklin. "You should save his number as Daddy. That's his name on all contacts for Elegant Escorts.

She backtracked and saved his number under his alias.

"So, I understand you're interested in joining our little entertainment endeavor?" I asked.

"Yes, but only part-time. Dick plays golf faithfully every Wednesday and Sunday and always spends the evening in a poker game at the club." Rachel explained.

I knew she'd be able to set her availability to those two days, but I decided to let Daddy explain how that works once he completes his interview process.

"You mentioned last night that you wanted to add to your retirement income. How do you and Dick afford a club membership?" I asked.

Rachel grinned, "His winnings on the course and at cards cover the cost of the club, and we can enjoy the trappings of the country club life because of that fact."

"I see," I answered.

"I must admit that when Daddy suggested I consider coming to work for him, I was slightly surprised. Aren't all his girls much younger than me?" she asked.

"Yes, and to be honest, they're all younger than me," I said.

"I'm nearly sixty years old, and even though I can still hold my own sexually, how many of his clients would be interested in banging a woman my age," she asked.

"You'd be surprised. A lot of men enjoy the company of a more experienced woman." I explained.

"So, what can I expect to make working for Daddy?"

I smiled at her, "I'll let Daddy explain how that works, but judging from what I saw last night, you could expect to bring in more cash than Dick does gambling."

"So, how long should I wait before calling him to express my interest?" she asked.

"His interview process is rather lengthy, and he's normally free on Sunday, so I don't see any reason not to call him now," I replied with a grin.

Rachel pressed his contact number and, a few seconds later, said, "It's Rachel Stark."

She listened for a couple of seconds and then said, "I'd like to start the process of getting onboard with Elegant Escorts."

Daddy was apparently happy to start Rachel's induction into his growing stable of ladies. "Yes, I'm available this afternoon," she said.

"I'm sitting here with Angel, we were talking about the basics, but I have many questions."

She removed her phone from her ear and switched to speaker. "Angel, I'd like you to sit in on the interview. Can we get together in a couple of hours at your place?" Daddy said.

"Of course," I answered.

"Good. Can you fill Rachel in on the process? I'll be there around two." Daddy remarked.

"Not a problem. We'll see you a little later."

Daddy disconnected the call, and Rachel turned toward me, expecting me to explain how this whole thing works.

"So, he's going to question you about your sexual history, what kind of sex you enjoy most, and if there is anything you consider taboo." I started.

"That should be easy," she answered.

"He'll let you know how often he'll expect you to be tested for STD's and if that goes well, he may explain what you can expect to make."

"What about law enforcement?" she asked.

"Not a problem; most of the department's higher-ups are clients and many local politicians," I explained.

"After Daddy completes that part of the interview, he'll want you to demonstrate your sexual techniques," I added.

"So, I get to fuck him again?"

"Yes, but unlike last night when he let you do as you pleased, he'll test your limits fully," I remarked.

She giggled, "Judging from the size of his monster black cock that could be lots of fun."

"Trust me, I was sore for days after he interviewed me," I admitted.

She grinned, "Last night, when he was fucking me from behind, that beautiful cock stretched my cunt completely, and I loved how his cock head pushed against my cervix."

"Were you able to throat his whole cock?" I asked.

"The entire length, no, but I gave it my best effort," Rachel said.

I remembered when Daddy interviewed me and explained, "I didn't think I would be able to swallow all twelve inches, but he had me lay on my back with my head draped over the edge of the bed and proved me wrong. I can still recall how it felt surging deeper in my throat than any before and the sensation of his balls slapping my face as he throat fucked me."

"Did he ass fuck you?" she asked.

I smiled, "Yes, and it was the best anal sex of my life. The feeling of having his entire cock buried in my ass is something I'll remember always."

"So, you love fucking Daddy?" Rachel asked.

"Loved, Daddy doesn't fuck his employees, so I'd suggest you enjoy it today because it'll be the last time he fucks you."

"Do you think I should go downstairs and change into something sexier?" she asked.

"I wouldn't bother, don't look at this entire process as a seduction. He wants to test your sexual abilities and techniques. I'm sure he already knows how seductive you can be judging from his actions last night." I suggested.

"This is a little scary," Rachel remarked.

"Don't be scared, he wants to make sure you will be able to please his clients, and if you can handle his huge rock-hard black cock, you'll be able to satisfy every one of our clients.

She just grinned at me.

As the two o'clock hour approached, Rachel remarked, "I'm a little nervous."

"That's understandable; it's a big step. If you pass the test, you will be offered a job as a high-priced escort."

"Which is one step above being a hooker," she remarked.

"I had the same issues dealing with becoming nothing more than an expensive whore, but once you get past the first couple of appointments, you'll discover just how satisfying it is to provide men with something they don't or can't get anywhere else," I explained.

Two o'clock came and passed, and Rachel seemed to become even more anxious. "Maybe he decided not to meet with me," she remarked.

Daddy is always prompt, and I knew he'd have an explanation for his tardiness.

A few minutes later, there was a resounding knock on my door. I scurried downstairs and, without checking the peek hole, pulled it open. Daddy was standing there with a wide grin on his lips, but beside him, a younger-looking, thin blond guy was smiling even wider.

"Say hello to Marc," Daddy said.

I offered my hand to him, wondering what this second cock was about. "Nice to meet you, Marc," I said as I stepped back and to one side.

"Rachel is upstairs," I mentioned as we all started up the stairs.

I followed Daddy and Marc into the kitchen and found Rachel standing beside the stool she'd been sitting on for the last couple of hours.

Daddy crossed the room and hugged her tightly as he said, "I didn't expect to hear from you so soon."

She grinned, "I'm very interested in talking with you again, Daddy."

Marc was clearly undressing my mature neighbor in his mind as Daddy took Rachel's hand and walked her across the living room to the sofa. "Let's talk a little first. I apologize for being tardy, but I wanted Marc to join us this afternoon," he said.

Since I didn't expect to be involved in their conversation, I took Marc's hand and offered him a seat at the island. His youthful stare dropped to my cleavage, and I leaned toward him to permit him to check deeper between my big soft tits.

Daddy began with more of a statement than a question. "Last night, you proved beyond a shadow of a doubt that you enjoy sex, and since we'd never met before, I'll assume fucking anonymous men excites you.

Rachel grinned and replied, "Yes, especially men with big hard cocks."

Daddy smiled. "What excites you most about sex with a man you've never met?"

"The anticipation of undressing them, seeing their cock for the first time, and feeling it stiffen in my hand," she answered.

"And once you have a man fully erect?"

Rachel smiled, "I love taking a rock-hard cock in my mouth and seeing how deep it will reach toward my throat."

"So, you enjoy deepthroating a man's cock?" Daddy asked.

"Oh yes, very much so."

I could see that Marc was enjoying listening to them, which was confirmed by the growing bulge in his slacks.

Daddy sat back against the cushion and continued asking Rachel questions. "I understand you're interested in scheduling appointments a couple of days per week?"

"Yes, on the days Richard plays golf."

"Is he aware you're considering working for Elegant Escorts?"

"He's okay with it," she answered.

"Good, I'm sure your appointment calendar will be full," Daddy remarked.

Rachel just smiled at him.

Daddy continued, "We have a growing number of clients who are interested in a mother-son roleplay scenario. Many young men fantasize about fucking their mom or stepmother."

"Is that so?" Rachel replied.

"Yes, and I believe you'd be perfect for specializing in incest roleplay," Daddy remarked.

"I've done some roleplay before, but incest wasn't one of them. Normally I roleplay as a street whore." Rachel admitted.

"I've asked Marc to join us because his biggest fantasy is incest roleplay," Daddy explained.

"I want to watch you and him together, just to be sure you're the right lady for the job," he remarked.

I glanced at Marc, now understanding why he was included in the meeting, and judging from the sizable bulge in his slacks, he'd have more than enough to satisfy Rachel's love of big hard cock.

"Marc, switch places with me," Daddy said.

As he slid onto the stool beside me, Daddy said, "Angel and I will just observe; I'd like you two to adlib."

It was apparent that Daddy had given Marc some basic instructions about handling this roleplay because when he sat beside Rachel, he got a dejected look on his face and stared down at his lap.

Rachel picked up on this and immediately said, "Is something wrong, Marc?"

"Oh, it's nothing, mom," he replied.

"I can tell from your expression that you have something on your mind, son."

"I don't think you can help me," he answered.

"You know you can talk to me about anything, Marc," she said.

Marc was playing his role totally; he wrung his hands together and then glanced at Rachel's eyes. "It's my girlfriend; she broke up with me a couple of days ago."

"I'm sorry to hear that. Did she give you a reason?" Rachel replied.

Marc swallowed hard and then admitted, "I can't satisfy her."

"Sexually?" Rachel asked.

"Yes, she told me I give lousy head, I climax too quickly, and my cock isn't fat enough to fill her completely," Marc said.

Rachel glanced toward Daddy and me and then back at Marc as she said, "Mommy can help."

His flabbergasted look was as fake as they come, and when he answered, "Mommy, I could never fuck you."

"You don't think I'm sexy?" she asked.

"I think you're very sexy, but it's just not right to fuck your mother."

Rachel thought for a moment and then asked, "Did I help you with your schoolwork back in the day?"

"Yes,"

"Think of this as grown-up homework, Marc." She suggested.

"Okay."

"Do you want to touch me?" she asked.

"Yes."

Rachel lifted his hand to the neckline of her dress and pressed his palm against her naked flesh. Marc's eyes grew saucer-sized but remained frozen in place on her chest.

She looked at him and said, "Mommy can teach you to give fantastic head,"

He smiled.

She noticed the bulge in his slacks and moved one hand to stroke its length. "Cocks don't lie, and this one is screaming to fuck me."

"Are you going to suck it, mommy?"

"Do you want me to suck your big hard cock?"

"Oh yes."

"Mommy can train you to hold off on cumming for as long as you want. That way, you can satisfy your mom and any other girl you want to." She remarked.

Rachel stretched her dress open, exposing her big soft tits, and said, "Touch them gently,"

Marc's hands began lightly caressing the twin orbs of flesh, and as Rachel unzipped his slacks, he said, "Yes, Mommy, take my cock out and put it in your mouth."

His cock was fully erect and at least eight inches in length. It lacked the girth of most big cocks, but she smiled and remarked, "I wanna take it deep in my throat."

Rachel slipped off the sofa and knelt between his legs; using both hands, she yanked his pants and jockeys below his knees and then slowly stroked the entire length of his cock shaft while toying with his balls with one free hand.

Marc's fingers explored her chest, becoming more aggressive as the moments passed.

"I like how you play with Mommy's big soft tits," she said while stroking his rock-hard shaft.

She ran her flattened tongue over his balls, along his urethra, and then swirled it around his corona and glans. "Do you like how Mommy pleasures your big beautiful cock?"

"Oh yeah," he instantly replied.

As Rachel opened her lips and slurped his cock head inside her moist flesh Marc softly moaned.

I glanced at Daddy and smiled. He lifted my hand from my lap and placed it firmly against his loins. His cock, while not fully erect, felt very firm when I squeezed the shaft.

Rachel was now totally engrossed in her incestuous fantasy roleplay and began sucking Marc's rock-hard cock in earnest.

"Swallow it, Mommy," Marc pleaded, wanting to feel her warm moist throat surrounding his cock.

She was as talented a cock sucker as me, and in no time, his cock was impaling her throat, her slobbering wet mouth coating him completely.

"I wanna fuck your hot cunt, mommy," Marc exclaimed.

Rachel let his slippery cock slip from her mouth, stood up, and wiggled out of her dress. As she mounted his lap, she pulled her thong aside and pleaded with her lover. "Fuck Mommy hard and fast,"

Daddy's cock had swelled to nearly erect, and as he guided my hand up and down on his long thick shaft, he softly said, "Suck it, Angel."

I stood before him, undid his pants, and discovered he wasn't wearing underwear. As I knelt before his massive cock, I yanked his pants down his legs. His huge cum producing balls dangled over the edge of the stool, and as I stroked up the monstrous shaft, I licked my smooth lips.

Rachel had mounted Marc's cock and was slowly plunging and lifting to pleasure him completely.

"Your cunt is so tight," he said as they slowly fucked.

"Mommy loves how your cock fills her tight wet cunt," Rachel replied.

As I began licking his huge cock head, I knew that in the position I was there was no way I'd be able to throat Daddy's enormous cock, but I'd pleasure it as much as I could and plead for his savory reward.

While I lavished his cock head with my tongue and lips, Daddy concentrated on Rachel's cowgirl technique. She used her leg muscles to lift almost entirely off Marc's rock-hard cock and then slammed her loins down each time her flesh slapped against his lap. Each time she plunged, the flesh of her ass moved in a wave-like motion, and she loudly moaned when his cock head slammed into her mature wet cunt. Marc's fingers spread over her fleshy butt cheeks and forced her loins firmly down on his surging youthful cock.

Daddy glanced away and looked down into my eyes as he said, "Lick my balls."

As I dropped my mouth toward his scrotum, he wrapped his massive hand around the slippery head and began slowly pleasuring his cock, twisting his fingers around the corona and smooth glans. I slurped one giant testicle between my lips and used my tongue to lightly caress his cum producing ball.

While I concentrated on giving his scrotum and balls a slow sexy tongue bath, I heard Rachel deeply moan and then say, "You're gonna make mommy cum."

"Fuck her," Daddy said while returning his attention to the woman who'd become the next member of his Elegant Escorts harem of sexy ladies.

I didn't need to encourage Rachel, knowing that her climax had already started to build as Marc continued pounding her mature fat ass down on his throbbing rock-hard cock. Daddy grasped my head with both hands and yanked my mouth off his balls, and as I glanced up at his cock head, I noticed a stream of pre-cum oozing from the urethra and slowly running down the length of his massive twelve-inch cock shaft. I used my flattened tongue to capture his flow and licked up the rock-hard shaft until my lips surrounded the tip of his cock and a more forceful squirt of pre-cum coated my tongue.

"Suck the head," he demanded.

As I began sucking his cock head, I could now look toward Rachel and Marc as they continued climbing her orgasmic ladder.

"YES!" she repeatedly exclaimed as her climax slammed into her fully. Her hips shook violently back and forth while Marc held her firmly embedded on his big cock.

"Cum for me, mommy, cum all over my big hard cock," he exclaimed as Rachel rode him to the peak of pleasure.

"Oh god, oh my fucking god," she screamed as Marc's rock-hard cock transformed her into a quivering mass of sexually satisfied flesh. Marc's strong hands held her firmly, his cock head massaging her most sensitive deep spots.

As her orgasm diminished, she leaned forward, crushing her big soft tits against his body, and her mouth found his in a profoundly emotional kiss.