Mistress Barbara Pt. 22

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Mistress leads a road trip to the city.
4.9k words
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Part 23 of the 37 part series

Updated 03/02/2024
Created 08/15/2021
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After breakfast we adjourned to enjoy the beautiful day by the pool. We were alone for a bit and swam, splashed, and generally frolicked like kids in the water. Then we lay out on lounge chairs soaking up some natural vitamin D.

Eventually the others joined us looking bedraggled. Chloe and I exchanged a smile at their obvious state of post coital exhaustion. Miss Lucy and Alexandra pitched a blanket and lay on it together.

Mistress approached Chloe and me.

"Did your Master take charge of you again, fuckbunny?"

"Oh yes, Mistress, he did." Chloe grinned at me, and then at her.

"I think we should all rest a bit, but this afternoon we'll be taking a road trip into the City. You should get squeaky clean and put on presentable clothes in about an hour or so."

"Yes, Mistress. Squeaky clean, eh?"

"Be ready for anything."

"Inside and out?"

"Yes, fucktoy." Her expression spoke of any possibilities to come.

After enemas for both and a douche for Chloe we lathered each other slowly, enjoying a steamy shower and the opportunity to caress, kiss, and fondle.

"What do you think she's planning?"

"The look in her eyes sparkled with mischief."

Our mutual expectation of Mistress' wicked implication hung voluptuously in the steamy shower. Chloe's hands gently took hold of my cock and balls. She cradled Mistress' balls lovingly and stroked Mistresss' rapidly hardening cock to full staff, then dropped to her knees, looked up at me and asked huskily, "May I, Master?"

I petted her wet hair and drew her toward me in a silent response.

As she sheathed Mistresss' cock smoothly, letting her tongue caress the underside while the glans slid along her palate. When I came to the top of her throat I pushed fully into her. Her hands cupped by ass, pulling me as deep as possible into her hot hungry mouth. I love the way she swallowed me and began working her wonderful tongue. I felt an orgasm building rapidly. She fluttered her tongue against the glans while sucking simultaneously. Her skills never ceased to amaze me and the rapidity with which she had learned exactly how to please me best was dazzling.

As I thrust into her mouth, clenching my hip flexors and locking my knees she reached two fingers into my ass and deftly found my sphincter at the perfect moment to accentuate my first explosive shot of cum escaping down her throat. Then she pulled back slightly to take the next two spurts in her mouth. Finally she pulled back to take the last spasm on her face and rubbed Mistress' cock against her lips and cheeks.

I reached down to grab her under her arms and lifted her up so we could kiss. Our tongues met immediately stirring the cum she had conserved into a froth. We kissed and caressed each other as the shower pelted us.

Dressed in comfortable, presentable clothes we wandered out into the living area to find the others waiting.

Alexandra jumped up from the sofa and her pretty flowered sundress lifted enough to flash a brief glimpse of her magnificent unencumbered cock waving like a cheerleader's pom pom.

"Roadtrip."

Mistress laughed at her own exuberance and led us to the car.

"Slaves in back."

We piled in with Chloe straddling the hump. Mistress and Miss Lucy sat in front. Traffic wasn't heavy and we made it in good time. We sang along to a couple of songs. Chloe, a rose among thorns, took advantage of her position and stroked our thorns. She timed her work so she could take the results of her work in her pretty mouth sequentially.

"You sluts are insatiable." Miss Lucy snarked.

Miraculously Mistress found a parking space just up the block from Miss Lisa's tattoo parlor. My heart leapt anticipating the reason for this visit. Thoughts of how I would like to mark Chloe had been teasing my imagination ever since her collaring.

When Mistress knocked on the door despite the closed sign, the door quickly opened to reveal Miss Lisa. She wore a black leather biker vest revealing her amazing sleeve tats. It was open to show off the panorama that that spanned her chest.

"You brought the whole crew."

She and Mistress embraced. Then she and Miss Lucy did as well.

"Lucy, it's been a minute, how are you, gorgeous?"

"Life is great now that Barbara and I are back."

"I never understood why you weren't for so long."

"It was my fault, but it's all cool now." Mistress took Miss Lucy's hand and they smiled warmly at each other.

"So what can I do for you tonight, Barbara? Is your slave's marking doing well? It's Erik, isn't it?"

"Yes, Miss Lisa."

"Let's take a look, whip that thing out."

I obeyed instantly and she leaned down, took Mistress' cock in hand and inspected her handiwork.

"That looks like it's weathering well, do you want it touched up, Barb?"

"Let's save that for another time, we have two other victims for your needle though."

"Oh, good."

Miss Lucy gave Alexandra a gentle shove forward.

"This is my slave Alexandra. I would like her marked like the way you marked Erik for Barbara. Lift your dress, slut."

When Alexandra raised the hem of her dress to reveal her huge cock Lisa gasped.

"Damn, Luce. That is about the biggest cock I've ever seen. And on such a pretty girl."

"She is a beauty and what a lovely lagniappe."

"I'll say. You want her marked like Erik?"

"I think a nice fancy script L would be pretty, don't you?"

"Mmm, what color?"

"Bright red I think. Possibly with edge shading, you're the artist. I'll leave her cock in your hands."

"Lovely. Come here sweetie." And Miss Lisa led her to a pair of chairs near the needles and ink. Alexandra raised her dress and Lisa took her cock in hand. She cleaned the glans thoroughly and made a sketch to guide her work, looked to Miss Lucy who gave her a nod of approval, and bent back to her task.

"Let's go down to my store and leave Lisa to it. We need to get some new toys." She leaned over and whispered something in Alexandra's ear.

We walked the few blocks to Miss Lucy's giddy with excitement from being in the city together and contemplating the adventures to come. When Lucy let us into her wonderful toy store it was like Christmas morning for pervs.

I picked out a pair of toe cuffs, an inflatable plug, a cock gag, and consulted with Miss Lucy regarding items for Chloe's clit training. I dragged my sweet slave along while Lucy showed me an electric suction pump and we tried attachments for size, eventually settling on two. While we were sizing the choices for clit torment and growth, Mistress joined and asked, "I want a penis tube for fucktoy and it might be fun to get one for Alexandra, see how big that baby can get."

"Great idea. We can try for the Guinness book with hers."

We all laughed at that one and shared a hug. Miss Lucy brought out a box with a giant penis tube that would work with the electric pump system. Then she found a smaller one, motioned to me and I dropped my pants so she could slip Mistress cock into it and we decided it was probably the right size. Mistress grabbed her cock and said, "I can't wait to try that on you, fucktoy."

"It will be fun to see how big you can make me."

"Indeed." She gave her cock a hard squeeze.

Miss Lucy gave Mistress a seductive look as she added a huge double dong to the pile. It was like Alexandra squared, back to back.

They each took one end in hand and leaned together for a deep kiss.

Mistress selected a wicked looking crop, a small single tale, and a humbler with electrical leads and a TENS UNIT that made me shudder.

Several tubes of lube and various other stocking stuffers filled out the pile.

Shopping done, we walked back to Lisa's carrying bags decorated with heart shaped handcuffs. A couple of passersby smiled at us knowingly along the way.

Lisa was just adding the last shadow flourish to Alexandra's swollen glans when we returned. Unsurprisingly her work was lovely. Alexandra's face reflected the pain she was feeling.

Lisa daubed up the last blood from the shadowing, applied the dressing and swiveled her chair to face us, "Who's next?"

Chloe stepped toward her, "Hi, I'm Chloe. I hope I'm not wrong, but I think Master would like you to mark me for him." She turned to look my way nervously.

"You're right, fuckbunny. Miss Lisa, I would love you to mark my slave."

I turned to glance at Mistress who grinned broadly and nodded affirmation.

"She called him Master, am I marking her for him then?"

"He owns her."

"You've always marched to your own drummer, Barb, but this is different even for you."

"Make it special."

"How would you like it, Master Erik."

Miss Lisa's wry grin was wicked, no, make that Machiavellian.

"I think a fancy Gothic E, black with red highlights. Centered on her pelvis right above that wonderful clit."

She sat Chloe down, had her remove her skirt and stopped, stunned when she got a good look at her subject's clit.

"Oh my God, will you look at the clitoris on this woman. It's as amazing as the other one's cock."

Chloe beamed proudly.

"You don't do anything small in your family do you guys? Mind if I touch it?"

"Please do." My pride in Chloe was based on many things, but that magic clit was a showstopper.

Lisa took my clit in her fingertips, squeezed it, rolled it, and pulled it. Chloe responded almost instantly to the attention, arching to offer my clit eagerly to Lisa.

"Holy shit, she's practically dripping already. Is she allowed to cum?"

"Would you like to cum, fuckbunny"?

"Oh yes, Master, may I cum, please."

"Yes, baby you may cum. It's up to Miss Lisa though. If you'd like to make her cum, feel free."

Miss Lisa leaned forward, took my clit in her mouth and began working it avidly. Chloe moaned and clutched Miss Lisa's head to her. It only took about a minute for her to began spasming and squirting into Miss Lisa's voracious mouth.

"Master, shouldn't I return the favor?"

"Would you enjoy that, Miss Lisa?"

"Hell yeah."

"Fuckbunny, you definitely should reciprocate."

"Thank you, Master."

Chloe fell to her knees before Miss Lisa, helped her pull her jeans down and eagerly dove face first into her hairy bush. Miss Lisa shifted her position to accommodate Chloe's efforts and immediately voiced her approval of the attention she was receiving.

She caressed Chloe's head with one hand and manipulated her own ringed nipples with the other. She moaned and her breathing became deeper and quicker. Chloe adjusted her position a bit and slid her hands under Miss Lisa's ass to increase the intensity of her worship.

Miss Lisa gasped at the shift and began emitting an escalating groan that finished with an ecstatic scream as she came, bucking and thrashing into Chloe's face.

"That was as wonderful as your Master was when I inked him. He taught you all his tricks."

"He did." Chloe smiled smugly as she licked pussy juice from her lips and settled back on her haunches. Miss Lisa lounged back in her chair, sighing contentedly.

"Damn, Barb, that's some pair you have there."

Mistress smiled proudly and hummed, "Mmmm."

"Hell, if you throw in Lucy's Secretariat what more could you two want."

"It's a helluva family unit," Miss Lucy chimed in."

"Hey, take a look at Chloe's tatt."

She helped her up into the other chair and adjusted a light to highlight her artistry.

The Gothic G, black with red highlights was impeccable and she'd added an adorably sexy spread legged rabbit next to it. Between the rabbit's spread legs a pink clit jutted provocatively.

All of us gushed at her work and Chloe beamed proudly. Miss Lisa went over the directions for tending to the fresh tatts and gave us a bag filled with all the necessary materials.

Hugs all around as we prepared to leave. Miss Lisa grabbed me by the crotch and said, "I look forward to touching up that cock before too long, fucktoy."

"Come visit us soon. You can attend to that and take advantage of the amenities of the house," Barbara said as she hugged her friend goodbye.

"Definitely."

We piled into the car, letting Chloe have a window seat and room to arrange herself carefully. I took the hump so Alexandra could protect her sore cock too. I wasn't alone in my surprise when Mistress found a parking spot around the corner from Miss Gloria's.

"I'll just be a minute."

She jumped out of the car and headed around the corner.

Miss Lucy remained stoical when we quizzed her about what was up. I assumed she knew and was keeping Mistress counsel.

It turned out that my services were going to be required. Mistress drove us up Avenue of the America's (Sixth Avenue to most locals) and into the garage beneath the New York Hilton.

We went upstairs to our suite and Mistress explained that I had a trick in the next door suite with a a married couple who liked to share boys. She reassured me that they weren't into inflicting pain but would probably use me quite thoroughly.

"Get going, fucktoy. Make me proud."

I took the fifteen step journey to the next door and knocked. The door opened quickly to reveal a tall, handsome man in his early 30s wearing a hotel robe that hung open revealing a toned body. His cock was large, although hardly in Alexandra's league.

He escorted me in, shut the door behind me, and led me to a bedroom. Lounging on the bed I found an absolutely gorgeous woman. She had an amazing bikini model figure, long wavy brown hair fanned out around her head on the pillow, and flashing blue eyes. Her tits were large, firm and highlighted by sculpted conical aereolae and pencil eraser nipples. Her abs formed a subtle six pack. I hoped she would have me worship the magnificent shaved pussy that beckoned me as if it had a voice.

"Oooh, he's pretty."

"Gloria always comes through."

"Get those clothes off, let's see what you've got."

I undressed, folded my clothes and lay them on top of a dresser that fronted a mirror. I could see them watching as I did it and was happy to see the desire in their eyes as they inspected me.

He followed me and caressed my ass with one hand while reaching around to cup Mistress' balls with the other. That hand slid up and stroked Mistress' stiffening cock. I was fully erect quickly.

He turned me around and pushed me toward the king size bed.

"Nice cock for you, baby."

"Perfect size. Do you like worshipping pussy, cutie pie."

"Yes, ma'am I love it."

"Show me."

He slapped my butt and I scrambled onto the bed between her beautiful, lithely muscled legs. I skip kissed her thighs on my way to her exquisite folds, then teased them with my tongue, gradually separating them to expose her sweet glistening hole and shimmering pearl.

Her bouquet was citrus mixed with ocean breeze, intoxicating and beautiful. My head spun with desire for this magnificent woman. As my tongue dipped deeper into her hot, pink opening the flavor overwhelmed me. The ocean and citrus compounded with the rich notes of woman, butter and caviar blended in a scrumptious, complex melange. She opened herself to encourage my exploration of her succulent sex, moaning happily.

My reverie was interrupted when I felt his hand caressing my ass, one finger slipped into my crack and the tip tickled Mistress' puckered opening.

"My turn, do you like sucking cock, too?"

"Yes, sir."

"Do you mind, Grace?"

I shot her a questioning look since it seemed like she was really the one in charge.

"That's okay, let Rory join the party, we've got all night, pretty boy."

She gently pushed my head away and turned me toward Rory. I moved down to take his junk in hand cupping his balls and guiding his half hard cock to my lips. I kissed his glans, then teased it with my tongue dipping the tip into his slit as I caressed his lime sized balls.

When I took his full length into my throat then slowly slid back to hold only his glans and flutter my tongue on the spongy tip, he moaned happily, and clasped my head. He was rigid now and I took him back into my throat while I rolled his balls in my fingers. I could peek at Grace's beautiful face as she leaned close to get a better view of the action.

While I sucked her husband she fondled me, working Mistress' balls and cock alternately. The next time I slipped back up his thick eight incher she pulled my head back and kissed me deeply.

I felt his hand in my crack and realized he was lubing me as she pulled my face back to her glorious gash. He got behind me and as I dove in with my eager mouth and resumed the delightful duty of devouring Grace's delicious pussy I felt his plum sized glans beginning to stretch my puckered hole. I cried out slightly as it popped inside which made her moan with pleasure. I focused on suckling her pearl and teasing it with my tongue, which kept my mind off the painful invasion of my rectum..

"Oh Gracie, he's nice and tight."

"He has the mouth of an angel."

He quickly picked up the pace, pounding me deep and fast. With each stroke he prodded and stroked my prostate with his thick glans. When I moaned into her she responded like call and answer blues. we quickly established a perfect rhythm that drove each of us toward nirvana.

She surprised me with a machine gun series of quick spasms, part of a complex orgasm accompanied by a crescendo of ecstatic cries that built to a musical closing note with a shuddering vibrato. She drove her pussy forcefully against my face and flooded my mouth with her nectar.

She shook and quivered before finally pulling away to roll her husband off me. His softening cock slipped out of my ass and she surprised me by taking his cock in her mouth. She sucked him clean greedily, then shocked me more when she brought her mouth to my ass and began sucking his cum from me. He stroked her hair as she dined on my anus. It felt wonderful needless to say.

She rolled over and twerked her glorious, muscular ass at me.

"Your turn. Worship my ass, baby."

How could I resist? It's not like I don't enjoy what she was requesting, and hers was arguably the most beautiful ass I had ever seen. I spread her open and leaned in to tease her lovely puckered rosebud. The aroma was actually sort of floral blending with the expected hint of muskiness. Her rosebud was beautiful and quite delicious. I was in heaven devouring Grace's perfect opening. Rory moved up and they made out while I tongue fucked her anal passage. She took his cock in hand and worked him up to a full erection. He reached for my cock and found it ready for action then smeared a generous glob of lube onto me.

"He's ready too, baby."

She climbed on top of him and sheathed the big cock that had just fucked me into her delicious pussy. The lube left me in no doubt about what was expected of me and I slowly slipped my rock hard pole into her delicious ass.

Rory and I quickly fell into a steady rhythm. He thrust in as I pulled back and vice versa. This drove Grace into a frenzy almost immediately and we strove to hold our orgasms at bay as we gave her at least four spectacular ones. She cried out at each peak and whispered hoarsely, into Rory's ear to fuck her hard.

I flashed back to the bridal shower, when Alexandra and I had sandwiched several of the guests like that. I was definitely becoming a fan of this action.

When Rory's pace increased I could feel him fire off stream after stream into his wife's cunt and i let myself follow suit, shooting what felt like a massive stream into her rectum.

"Thanks, beautiful there's cash on the dresser." I took her cue immediately, grabbed my clothes and the cash on my way to the door. I caught a brief glimpse of them kissing contentedly in the mirror before I peered into the hallway, stepped out naked and hurried next door.

I was about to knock when the door opened and Chloe reached out to yank me inside and shut the door behind us.

"That sounded like a helluva party, fucktoy."

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