Taylor Begins her New Job

This is another chapter in the backstory of Taylor from the Mistress Barbara series.

It would be best enjoyed with some knowledge of those stories and the preceding chapter wherein Taylor arrives in Greenwich Village and meets Brad who introduces her to Andrea, the transwoman who will become her Mistress.

Taylor checked her appearance in the mirror for the fourth time. She'd been ready for an hour and realized that her neuroses were running rampant, but she really wanted to make the proper impression on Andrea. Brad assured her that Andrea liked her and all she needed was to do her job well, but she got the job because of his recommendation, and she wanted to make him proud. Andrea's lovely club was nothing like slinging hash at the truck stop and she knew she needed to be at her best for the different class of customers.

The alarm on her phone went off, signaling that her time for agonizing self-indulgence was over. She grabbed the lovely Hermes bag Brad had given her to commemorate her first day at the club and swept through the door.

Every day in the Village had been a marvelous adventure so far, she loved it. All the cool people, hell, she even got a kick out of the tourists. She paused just outside the entrance to Andrea's Place, took a deep breath, and got into her work headspace.

"You the new girl?"

A severe looking woman with a short, mannish haircut stared directly at her from behind the small desk just inside the door.

"Yes, I'm Taylor."

"Bridget, I'm the manager. Andrea told me to get you started."

"Nice to meet you, Bridget."

Bridget handed Taylor a check pad and led her to the kitchen. At the double doors she stopped and looked inquiringly at her.

"You've done this before?"

"Yes, Ma'am. Right hand door."

"Very good."

Bridget breezed through the right door and Taylor followed her. She introduced her to the chef and sous chef, Dani and April.

"You hang your food orders here. Keep the master copy for yourself to use when they order more drinks or dessert."

Bridget continued showing Taylor around, introduced her to Suzi who was tending bar, and assigned her four tables.

"We usually start to get busy pretty soon. You understand the system, right?"

"Yep, I think so."

"If you have any questions now's the time."

"Do I need to write a drinks check for Suzi?"

"Just tell her what you need. Make sure it's on your master check though."

"Of course, thanks, Bridget."

"You'll be fine, kid."

Bridget bustled back up to the desk and Taylor checked her tables to verify no one had sat down. She wandered over to the bar where she introduced herself to Suzi who gave her a club soda.

She took one sip of her drink before she noticed a couple sitting down at one of her tables, and so her busy evening began. It was very different from busy at the truck stop, but the system at Andrea's was more complicated and she'd found herself needing to redo paperwork several times.

When all was said and done Bridget walked up to her, patted her on the arm, and told her she'd done okay. It wasn't a glowing commendation, but the smile accompanying it was the warmest feeling she had gotten from her since they'd met.

She returned to her empty apartment and poured a glass of wine before settling on the comfy couch that arrived earlier before she left for work. Yet another example of Brad's amazing generosity. She wished he hadn't had a business meeting so she could feel his comforting arms envelope her in love. The worst part was that this meeting would conclude his reason for being in New York, and he'd be heading back to Cincinnati the next day.

The thought of being without him for weeks was terrifying. She'd come to depend upon him and his seemingly boundless love for her. She loved the sex, but his support was the greatest gift he gave her.

She took her shoes off and began massaging her aching feet. That, accompanied by several sips of wine were beginning to make her feel human when she heard Brad's key turning the lock. He entered smiling and hurried to her side.

"Let me do that for you."

He reached for her feet and began massaging.

"Oh, that's wonderful, thank you. How was your meeting?"

"It was great, the partnership is going forward."

"That's great."

"How was your first night at work?"

"It was fine, everyone was nice, and I made fifty bucks in cash tips."

"Did Andrea welcome you?"

"She wasn't there, Bridget, the manager I guess, showed me the ropes."

"Do you like working there."

"So far so good."

He let his hands work their way up her legs gradually, massaging her stiffness away as he went. She lay back, luxuriating in his attention. When his hands began working on her thighs she moaned and arched her back and raised her hips. Brad got the message immediately and reached up to take her stiffening cock in one hand and caress her balls in the other. She was rock hard in seconds and reached down to stroke the backs of his hand and wrists encouraging him.

He lifted her skirt and leaned over to nuzzle her and transferred her cock from his hands to his mouth. Her massive cock strained his mouth as it always did, forcing him to open his jaw fully to accept even her glans in his mouth. He swirled his tongue around it and began stroking the shaft with his fingers while caressing her balls with his other hand.

He shifted his position to better accept more of her massive organ. He sheathed her aggressively, sucking and working her with his tongue as he opened his throat to take her deep. He was improving his ability to take her all the way with practice. Of course, this delighted her. She beamed lovingly, looking down on her beloved man as he pleasured her.

She felt her balls draw up and knew an amazing orgasm was approaching.

"I'm cumming, baby."

He redoubled his effort, sucking intently and working her balls, letting his fingertips stroke her internal shaft to milk her in a way he knew she adored. That drove her over the edge, and she began firing a series of cum jets into his hungry mouth.

Brad held as much of her cum in his mouth as he could until she pulled him up to kiss him for a snowball. They kissed furiously, devouring each other's mouths as her hands slid down to free him from his pants.

His rock-hard cock sprang free, and she stroked it as they continued to kiss each other. She broke the kiss, panting, and gasped, "Please fuck me, baby," then slid down to take him in her mouth for a moment, before rolling over to offer her ass.

"I'll get lube."

"You're wet enough already."

He picked her up in his arms and carried her to the bedroom where he lay her gently on the bed. He quickly removed his pants, grabbed the lube from the nightstand. He began slathering his cock with the slick goo, squirted a bit more on Taylor's offered hole, then brought his glans to bear and pressed into her with one firm thrust. She pushed back, eager to fill herself with his raging meat, and they immediately fell into a perfect rhythm.

He pounded her relentlessly as she pushed back, greedy for the hard fucking he was giving her. He reached around to stroke her cock.

"I can't wait for you to fuck me like this, baby."

"Soon."

Taylor worked her muscles to tighten herself when he drew back, milking him. He rocked his hips on the in strokes trying to maximize contact against her prostate.

"Fuck me hard, I want you to fill me up, baby."

Brad worked her cock as he thrust as fully as possible, driving his cock deep inside her. She slipped her hand between them to give him extra friction. She could tell from his breathing and muscles flexing that he was getting close.

"Flood me."

Brad's cock pulsed as he began an intense orgasm. He shuddered and cried out pumping his seed into Taylor's rectum while she came into his hand milking her cock. They melted together, their passion spent, and love enveloping them.

Brad awakened the next morning to the savory aromas of a sumptuous breakfast Taylor was preparing in the kitchen. She knew she was overdoing it, but she needed to demonstrate how grateful she was for all he had done for her and how much she loved him. When she finished assembling his plate, she placed it on a bed tray and proudly carried it to the bedroom.

"Wakey wakey, pancakes, eggs, and bakey."

Brad rolled over, knuckled his eyes, and smiled happily.

"Good morning, baby. Wow, look at that. You want me to get fat?"

"I just want to spoil you. God knows you deserve it."

He started to reach up to embrace her. but she forestalled him by setting the tray across his lap.

"Don't let your breakfast get cold, I worked hard to get it just right."

They shared a smile and she sat next to him on the edge of the bed. She beamed at him as he tucked into the pancakes first, eating them with gusto."

"Mmm. these are great. Thank you, my love."

"What did I do to deserve you?"

"That's a long list."

"Aww," she awkwardly reached over the tray to kiss him.

"Now eat up, we need to save time for a going away suck. You don't want to leave me horny, do you?"

He shoveled his breakfast down greedily and handed the tray to Taylor. She set it on the floor and jumped into bed with him, threw her arms around him, and showered him with kisses. They went from kissing to caressing which quickly progressed to a ravenous sixty-nine.

Once they finished attending to each other's needs they settled in to loving chit chat about his business meeting and her job. Then he broke the news he'd been saving.

"I'm not leaving tonight."

"What," Taylor was clearly delighted.

"I changed my flight 'til tomorrow."

"Oh my God."

She kissed him giddily.

"Are you working tonight?"

"Not until tomorrow."

"That's perfect. We get to spend all day together."

"And all night."

"Shall we stay in or go out?"

"When will you be back?"

"About six weeks I think, although I might be able to arrange a reason to come a bit sooner. We'll see what comes out of the new agreement we made yesterday."

"That would rock, I'll miss you so much."

"Me too, but let's just enjoy today."

"And tonight."

"I really want you to fuck me tonight. I can't get it out of my mind."

She stroked his cheek and kissed him gently took a handful of his balls and reached to the nightstand for the larger plug.

"Then we'd better see how you do with this."

Brad rolled onto his stomach arched his back and spread his legs. Taylor spread lube in his crack, focusing on getting plenty inside him. Then she coated the plug liberally and brought its tip to his offered anus.

"Remember to push out, that will help."

Brad did as instructed and Taylor guided the plug into his straining hole. It began to slide in and went easily until the flared portion approached. He cried out when the fattest part began to stretch him wide.

"Try to relax, I'll stop pushing for a minute."

Brad shifted, trying to improve his angle for her. Taylor stroked his lower back and buttocks as she murmured quiet encouragement.

"You're doing great, baby, push out when you're ready for more, no rush."

He nodded quietly. Followed her instruction and felt the plug shift deeper by a tiny bit. When she added gentle pressure the flange finally passed his ring and quickly popped inside. It felt huge, filling him completely.

"Oh my God, it's in."

"How does it feel, baby."

"So good, I'm so proud to take it. Will you fuck me tonight?"

"You really want that, don't you?"

"Desperately. I want you to take me, make me yours."

"Then we'll belong to each other."

"Yes."

"Does it hurt?"

"A bit of ache, but as soon as it popped all the way in pleasure soared and pain ebbed. I love being so full."

Taylor rolled him over and immediately dove down, taking his stiff cock in her mouth, his balls in one hand, and slipped the other behind him to grab the base of the plug.

He groaned at the three-way stimulation and writhed under her hands and mouth. She took him deep into her throat, teasing with her tongue and humming. She fondled his balls, working them in her fingers, and teasing his shaft internally. Her grip on the plug base allowed her to rotate it gently and stimulate his prostate intently.

She loved the response he was giving her, whimpering, needy, and clutching her head while he arched his back to thrust deep into her throat. She rotated the plug base like a video game joystick driving him wild, coupled with her hand fondling his balls, and her throat clutching his thrusting cock he exploded.

He shot what felt like quarts of cum. The first ropes went down her throat, but she backed off enough to take the rest in her mouth, continuing to suck strongly as she drained the last oozing of his pungent spunk.

He reached down to grab her head and pull her face toward him so they could kiss passionately. They shared the cum that filled her mouth and he reached to find her hard cock pressing against his belly. He wrapped his fingers around her massive organ and drew on her thickness insistently.

He broke away from the kiss and forced himself down to swallow her cock. It spurted multiple streams of cum almost immediately. This time she pulled him up to share her tangy ejaculate.

"So, tonight?"

"Yes, my darling. I will fuck your lovely ass tonight."

"Thank you. I can't wait."

They hugged one another fiercely. Settling in to gentle fondling and stroking they idled away leisurely minutes before adjourning to the shower. They teased each other in the shower, allowed their hard cocks to playfully fence with each other and happily made out.

They eventually dried off and dressed casually before going out so Brad could show her some touristy adventures. They went for a round trip sail on the Staten Island Ferry, explored South Street Seaport, ate cannoli in Little Italy, and visited the Stonewall Inn where they had a beer to toast the heroes of the famous 1969 riot.

When they got back to their love nest Taylor took charge, preparing for his anticipated deflowering. She poured two glasses of wine and set them out on the coffee table, sat down and patted the spot next to her. He joined her and she raised her glass in a toast.

"To us."

"To us."

They took a sip, and she leaned in for a kiss. She began unbuttoning his shirt and soon they were in a shared rush to peel each other's clothes off. Once they were freed, they reached for each other's hardening cocks.

"Ready?"

"I've been ready since we met."

She led him to the bedroom and helped him adopt the position she wanted him in, bridged across a pillow under his hips to present his butt provocatively. When she trailed her fingers along his crack he raised himself to meet her, making her fingertips graze his puckered man pussy. He groaned and strained to increase the contact. She laughed and smacked his buttock.

"Patience."

She bent down, pried his buttocks apart with her thumbs, leaned in to lave his entire crack with her tongue, then focused on his opening. Her tongue made tiny circles around the crinkly, brown flesh before plunging inside, tongue fucking his funky hole. He pressed toward her ravenous mouth, straining to maximize the wonderful sensation.

Taylor plucked the lube container from the nightstand and began applying a generous dollop to his offered hole. She worked it inside him with two fingers. He moaned when she completely filled him with three copiously lubed fingers.

"Oh my God, that's incredible."

"That's just the appetizer."

"Then bring on the entrée."

She slowly withdrew her fingers stroked his buttocks and positioned herself on her knees between Brad's legs, pushed her massive helmet down against his opening and pressed gradually.

"Remember, push like you're trying to shit."

Brad grunted as he pushed. Taylor's huge cock popped past his sphincter. He howled. She scowled.

"Oh, baby, I'm sorry."

"No, keep going. Fuck me. I want you all the way inside me."

"Sure?"

"Positive. I want you to fill me with your cum. Fuck me, baby."

She grabbed his hips and pressed all the way deep into his rectum, then began a gentle rhythmic pumping most of the way out, followed by a smooth reinsertion, gradually increasing her pace. She made a point of maximizing pressure on his prostate. Her right hand slipped around his hip to find his cock. That helped him find his own rhythm melding with hers.

They fucked slowly, savoring the sensations, the closeness, and the soft passion. The pain ebbed as the pleasure grew for Brad. Taylor's gentle yet insistent stroking was bringing them both growing delight and incipient tingles of orgasms building in their loins.

"I'm cumming."

"Me too."

When Taylor felt Brad's cock twitching as he began ejaculating in her hand she thrust hard enough into him to practically lift him off the bed as she began her own almost coincidental orgasmic emission, shooting a series of thick spurts into his rectum.

They cried their joy out together in gleeful harmony.