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Strap-On Enterprises Ch. 03

As the workday neared its end, I sat in my office planning for the rest of the week. Suddenly, Ms. Gere buzzed me. I put her on speakerphone:

"Yes, Ms. Gere?"

"What are you doing after work, Sam?"

"Uh, I, uh had no plans. Did you have something in mind, Ms. Gere?"

"Yes, Sam. I've got a new customer in town who I haven't met before. I always like to have an extra person with me when I meet a new client for the first time, and I'm hoping you can join me."

"Sure."

"Good. Meet me in the garage at 6pm and we'll go over together. She's at the Sheraton."

At 6PM, I waited in the garage for Ms. Gere. She appeared from the elevator and walked toward her car with a Halliburton briefcase. I approached her, and we walked to her car.

"So, Ms. Gere, may I ask who we are going to meet?"

"Yes, Sam. We are going to meet a potential new client. Her name is Alexandra, or I should say Mistress Alexandra. She has something I want, and we apparently have something she wants."

"What do we want, Ms. Gere?"

"I've heard through the grapevine, Sam, that Mistress Alexandra has an excellent selection of European riding crops. They are very rare and not commonly sold in the States. I'm thinking of doing a little bartering with her."

"So, this isn't a business deal?"

"Oh, it's a business deal. She seems to really be into strap-on, and when she sees what I've got for her, I'm sure she'll be a repeat customer."

We jumped into Ms. Gere's convertible Mercedes and headed downtown towards the Sheraton. Ms. Gere knew exactly where she was going; as we ascended in the elevator, she pressed 16.

"Room 1616, this should be it."

Ms. Gere knocked on the door. We could hear someone inside moving around. The door creaked slightly open.

"Yes?"

"Mistress Alexandra, it is Ms. Gere from Strap-On Enterprises."

"Who is he?"

"Oh, he's my employee."

"Tell him to go away."

"I'm sorry, Mistress. We are a package deal."

I had been to a mistress before and knew that the proper etiquette was not to question a Mistress' demands, but Ms. Gere was strictly business and had no time for games.

"Come in."

We walked in and the room was mammoth. It was a penthouse of sorts that overlooked the cityscape. The room had a wet bar, a hot tub, a magnificent king-sized bed, a sitting room, and an outdoor observatory deck.

Mistress Alexandra was a statuesque, beautiful woman with short blond hair. She had on a sheer white body stocking that left nothing to the imagination. Her curves were perfect, and she stood tall even when barefooted.

She led us to a table near the observatory deck where she had a briefcase of her own.

"If he is going to stay, I want him tied up," the Mistress said.

"Very well," replied Ms. Gere. "Come on, Sam. We need you in this chair."

"Strip," the Mistress commanded.

I took orders from Ms. Gere only, and I looked at her for approval. I did not know Mistress Alexandra, but I desperately wanted to please them both. Ms. Gere nodded for me to strip. As I took off my clothes, Mistress Alexandra circled around behind me.

"Very nice bitch ass, Ms. Gere. I'm sure you've trained him well."

"He is my best employee."

"Sit, worm!" the Mistress demanded.

I sat naked in the chair as Mistress Alexandra tied my hands and feet to the chair. Ms. Gere smiled at my helplessness. Mistress Alexandra tightened the last knot, and gave it a tug to make sure I was immobile.

"There... Now, let's get down to business."

I watched as Ms. Gere lined her Halliburton up next to Mistress Alexandra's briefcase. The two beautiful women had their backs turned to me. Through the Mistress' body stocking, I could see the outline of the crack of her ass. It was voluptuous. I could also see the black stripes of Ms. Gere's pantyhose vertically outlining her magnificent calves. My cock sprang to attention as I daydreamed of what these two might do to me. Or was I in their plans at all?

Mistress Alexandra opened her briefcase first.

Ms. Gere reached into her briefcase and held up a sleek leather riding crop. She held it up toward the window, and I could see that it was handcrafted black leather.

"Do you like it," Mistress Alexandra asked.

"Do I like it? I love it. I've never seen one so tightly put together. Ooooh... and I love the smell of leather on the lip. Where did you get this?"

"It is handmade by a dominatrix in the Netherlands. She does exquisite work. Try it out."

Ms. Gere smiled.

"I think I will."

She walked toward me and looked at my stiff cock. She lightly ran the crop up the length of my cock then, without warning, THWACK! She slapped the side of my cock with her riding crop. The welt on my penis turned red. Thwack! Thwack! Back and forth she hit my cock twice as I yelled with excitement and pain.

"Tell us how it feels, worm!" the Mistress demanded.

"It hurts, Mistress."

"Tell her, worm. She is your boss."

"Do you want more, Sam?" Ms. Gere queried.

"Just one more, please, Ms. Gere... just one more."

Ms. Gere raised the crop to her lips and kissed the lip of the crop. Then she came down with a quick blow to my cockhead. THWACK!

"Oh, Christ!" I screamed as my cock burned.

"This is very nice, Mistress Alexandra. Would you like to see what I've brought for you?"

"Absolutely."

The two women returned to the table, and Ms. Gere opened her briefcase. I watched as Mistress Alexandra's face smiled for the first time. She reached in and pulled out a flesh-colored dildo. She grasped it with both hands and held it up to her pelvis.

"Mmmmm, I love the power. Where's the harness?"

Ms. Gere reached into the briefcase and removed a red velvet sack. Reaching into the red velvet sack, she demonstrated that the sack also included a place to hold the dildo as well as storage for the harness. She handed it to Mistress Alexandra.

"This is perfect... Will you put it on me?"

"Of course," replied Ms. Gere.

Mistress Alexandra stepped into the harness as Ms. Gere hoisted it up around her waist. Mistress Alexandra placed the rubber cock into the harness, and Ms. Gere tightened the harness from behind. Ms. Gere stepped away and admired Mistress Alexandra.

"Oh, my God, that cock was made for you."

Mistress Alexandra retorted, "Yeah, it's nice and strong. I can fuck like an animal with this thing on."

"I'll bet. What do you think, Sam?"

"Yes, Ms. Gere. It looks fantastic on her."

Ms. Gere walked toward me and slapped my cock once again with the riding crop.

"Ow."

She turned away from me and said to Mistress Alexandra, "Well it seems we have a deal, but wouldn't you like to see how your new strap-on looks with a pair of lips on the other end?"

"As long as they're yours," the Mistress replied.

Mistress Alexandra walked toward Ms. Gere with her phallus hanging from her waist.

"Show me."

Ms. Gere bent over with her beautiful ass right in my face. She caressed her ass and teased me with it. Mistress Alexandra stood at Ms. Gere's face and guided her lips to her newfound cock. Ms. Gere began to suck the Mistress' flesh-colored cock while also unzipping her skirt. She stopped sucking Mistress Alexandra's cock only long enough to command me to lick her ass.

"Lick my ass, Sam. Lick my ass while I suck my mistress' cock."

In her high heels, Ms. Gere bent over and leaned back onto my face. Since she had her panty hose on, I couldn't get inside her, but I licked at her hole through the sexy sheer black stockings.

"Mmmm, hmm," she cooed as she sucked the Mistress' cock. "He's making my ass nice and moist for you, Mistress."

"Yeah, you like that, bitch? Do you like that worm eating your ass? Look at him trying to struggle through those stockings. He must really want to lick your ass bad."

"Yeah, he wants it really bad... but I want you to have it, Mistress."

"You want me to have it? You want me to fuck your ass?"

"Yes."

"Beg for it, bitch."

"Please take my ass, Mistress Alexandra."

"Rip her stockings with your teeth, worm!" Mistress Alexandra demanded.

I tugged and tugged at Ms. Gere's stockings, and I eventually got them to rip. I tugged on the stocking fabric with my teeth. I was preparing my boss' ass for her new Mistress.

"Get up," Mistress Alexandra demanded. "Lie back on that bed."

Ms. Gere walked over to the nearby bed as I could only sit and watch. Mistress Alexandra grabbed the riding crop from Ms. Gere and pushed her backwards onto the bed. She then reached her hand under Ms. Gere's ass and ripped the hose upwards, which left Ms. Gere's pussy exposed. Mistress Alexandra quickly thwacked Ms. Gere's clit with the riding crop.

"Oh, my god!"

"That's right! Who controls your pussy?"

THWACK

"Oh, no, oh, my God! You do, Mistress Alexandra. You do."

THWACK

Ms. Gere held her legs up in the air and spread them apart allowing Mistress Alexandra full reign of her most sacred area. Mistress Alexandra stood over Ms. Gere smiling.

"Do you like your new riding crop?"

"Yes!"

THWACK

A small tear formed in Ms. Gere's eye.

"Do you want me to stop?"

THWACK

"No..."

"No, what?"

THWACK

"Ahhhh, god! No, Mistress. Please don't stop."

"Good girl."

I sat in amazement while I watched these two gorgeous women going at it.

"Now, every time I strike your clit with your new riding crop, I want you to say my name... Understand?"

THWACK

"Yes."

"Apparently, you don't."

THWACK

"I said, every time I strike your clit with your new riding crop, I want you to say my name."

THWACK

"Mistress Alexandra."

THWACK

"Aaaoww, Mistress Alexandra."

THWACK

"Louder!"

"MISTRESS ALEXANDRA!"

THWACK, THWACK, THWACK

Ms. Gere had tears of joy and pain in her eyes. She winced with the multiple thwacks onto her precious bulb. She was really into this new woman controlling her, and I had no idea she was into such pain.

"Turn around, bitch."

Ms. Gere got on all fours on the big bed facing me. Mistress Alexandra saddled up behind Ms. Gere and ripped the remaining panty hose away from Ms. Gere's ass. She waited no time before she plunged her new strap-on cock into Ms. Gere's juicy, wet ass. Ms. Gere was so wet from my saliva and being turned on by Mistress Alexandra.

Mistress Alexandra squeezed Ms. Gere's ass cheeks as she entered her from behind.

"Look at your boss, now, worm. Do you like seeing your boss getting fucked?"

I didn't know how to answer. I was in shock.

"Tell your bitch to answer me," Mistress Alexandra proclaimed.

"Oh, oh, god, fuck... Answer her, Sam."

Ms. Gere was on all fours rocking back and forth viciously on Mistress Alexandra's cock. Mistress Alexandra pulled the hairpin from Ms. Gere's bunned hair. Her long blonde hair dropped into her face as she rocked back and forth on the Mistress' cock. Her make-up was beginning to run as beads of sweat formed on her face. She was getting totally fucked.

"What's my name, whore?"

"Mis... oh, god... Mistres..."

Mistress Alexandra thwacked her on her ass cheeks with the riding crop as she fucked her.

"What's my name, you fucking whore?"

"Mistress Alexandra!" Ms. Gere said boldly.

"That's right. I'm your mistress, now. Anytime I feel like having your ass, you will give it to me. Do you understand?"

"Yes, Mistress."

"Say it!"

"My ass is yours, Mistress... anytime you want it, oh, my god, it feels so good... please keep fucking me."

"Look at her, worm! I'm fucking your boss, now. I bet you'd like to fuck her."

"Yes, Mistress Alexandra."

"Oh, he speaks... well, too bad, worm. Her ass is mine, all mine!"

Ms. Gere continued to yell in ecstasy as Mistress Alexandra showed no mercy on her ass. Mistress Alexandra grabbed Ms. Gere's hair in her fist and pulled her hair backwards. Mistress Alexandra spanked Ms. Gere's ass hard on both sides.

"Yell for me."

"Please fuck me, Mistress!"

"Good girl. Do you want some cum?"

"Huh?"

"Have you ever drank your employee's cum?" the Mistress asked Ms. Gere.

"No," she said as she began fucking the cock without the Mistress' assistance.

I couldn't believe what I was hearing. I couldn't move, and I wanted to stroke my cock so badly. I could feel my cum burning inside. The slightest touch would have caused an explosion.

"Get down there and suck that man's cock! I want to see how a whore sucks a real cock."

Mistress Alexandra removed her strap-on cock from Ms. Gere, and Ms. Gere approached me and got on all fours in front of me. She bent down and began deep throating my cock.

"Don't cum in my mouth, Sam," Ms. Gere told me.

"Cum in her mouth, worm," retorted Mistress Alexandra.

"No, please, Sam."

Mistress Alexandra forced Ms. Gere's face onto my cock. She sucked with reckless abandon. I could feel the explosion about to happen.

"I'm sorry, Ms. Gere. I can't control it," I said.

Ms. Gere sucked faster.

"Yeah, suck his cock, whore... Are you enjoying getting sucked off by your boss, worm?"

I was trying so hard not to cum.

I felt a sharp sting across my face. Mistress Alexandra had slapped me.

"Answer me, worm."

"Yes."

"Yes, what?"

"I love being sucked off by my... oh, shit, I'm going to..."

The cum erupted into a white-hot geyser of sex. It was so much that Ms. Gere couldn't accept it all. I looked down at her and the cum dripped from her mouth as she still had my cock engulfed down her throat.

"There, now. You two are made for each other," Mistress Alexandra said.

Ms. Gere got up, and stormed off to the restroom ill tempered.

"What's wrong with her?" Mistress Alexandra asked me as she untied me.

"I don't think she wanted my cum, Mistress."

"Well, she'll just have to learn that she must do what I want."

As I put my clothes back on, Ms. Gere left the bathroom and picked up her riding crop. Then, she stormed out of the hotel room.

"I'll meet you in the car, Sam. Get dressed and come on."

Ms. Gere left the room, and as I zipped up my pants, Mistress Alexandra slipped me a piece of paper. It had her phone number on it, and said,

"You're mine, now, worm."

And in a weird way, I knew that she was right.
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