Taylor Gets To Know Andrea Better

This is more backstory about Andrea and her slave girl Taylor, both transwomen, who appear in the Mistress Barbara series.

Taylor kissed Brad goodbye on the sidewalk in front of their building as he was about to climb into the cab that would take him to LaGuardia.

"I'll be back in about two weeks, baby."

"I'm going to miss you so much."

"I'll miss you too, but you have the number for my burner if you need anything. If I can't answer, leave a text or voicemail and I'll call back as soon as I can. I'll call you every night when you get home."

"I love you."

"I love you too. Now get going or you'll be late for work."

They kissed once more before he slid into the cab and pulled the door closed with a final crunch. She stood watching as the cab pulled away. As it turned at the corner onto the avenue, she gave one final wave and turned away, then trudged sadly up the street.

When she arrived at the entrance to Andrea's place, she paused for a moment to check her reflection in the window before entering with a bright, manufactured smile.

Bridget was standing at the checkout desk fussing with some paperwork.

"Hi Bridget."

"Andrea wants to see you, back in her office."

Taylor tossed her a questioning look.

"Back through the kitchen to the right."

"Okay, thanks."

Taylor waved at Suzi when she passed the bar and made her way through the kitchen until she came to a door in the rear right corner past the large commercial refrigerator. She opened the door and entered Andrea's simple office for the first time.

Andrea was seated behind a medium size, weathered walnut desk speaking on the phone. When she looked up at Taylor's entrance, she raised a finger signaling her to wait while she concluded her call.

"Right, I'll expect to see you tomorrow then. Very good."

She hung up and turned her attention to Taylor.

"Bridget tells me you did fine on your first night. How are you liking it here?"

"Very much, Ma'am. It's nicer than my last job."

"Where was that?"

"The diner at a truck stop. Nicer guests here for sure."

Andrea scoffed, "I try to keep the joint classy. Glad you approve."

"I really appreciate the job."

"I like congenial, pretty waitresses, and you seem to fit the bill, plus I like Brad and his recommendation was a bonus. How'd you met him?"

Taylor blushed, "We kind of picked each other up in the street."

"Cruising?"

"Not exactly. It was my first day in the city and I was wandering. We passed on the sidewalk and smiled at each other. One thing led to another. He invited me to lunch, and we hit it off."

The wry smile and nod Andrea responded with illustrated her confirmation of her assumption.

Taylor giggled awkwardly, "I guess it was cruising in a way, although I wasn't looking for action, he's just so handsome."

"And charming."

"Yes."

"Well, Bridget has signed off on you, and we need a waitress, so if you would like to join our little family here consider yourself on staff."

"Thank you, Ma'am I would like that very much."

Andrea nodded solemnly at her and gestured toward a closet door.

"There are unis in there, find your size and get to work."

"Unis?"

"Nothing elaborate, white tops and black skirts with stockings. Within reason you may pick your own shoes that go with the rest, heels of course."

Taylor remained seated nodding agreeably.

"Well, get to it."

Taylor popped up eagerly, opened the closet to reveal about a dozen short black skirts and simple white shirts.

"Stockings are in the top drawer, undies in the next two down."

"Where should I change?"

"Right here, sweetie. Don't be shy, it's just us girls," Andrea punctuated that with a wink.

Taylor held various items in front of herself, gauging sizes while Andrea shuffled some papers on her desk.

"Can't I just wear my own undies?"

Andrea rose from her desk to step over beside Taylor and put an arm around her.

"Don't be shy, sweetie. I understand you're used to your own techniques and if you'd like to continue with the familiar techniques, but trust me, I totally understand."

With that Andrea opened her own wine-colored wraparound skirt to expose her delicate cream lace panties.

"Can't tell, can you?"

"No, Ma'am."

"Tomorrow, we'll take you to the little shop I favor. Angelique runs the place, and she'll fix you up."

Andrea carefully lowered her undies and freed her cock for Taylor to appreciate how the arrangement worked.

"Oh my. That's so elegant. Your cock is lovely, Ma'am."

"I'm glad you like it. Let's see what we have to work with."

Taylor reached toward Taylor and slipped her hand between the girl's legs. Taylor backed away shyly.

"None of that, Brad tells me your large, let me see if Angelique will be able to fit you properly."

Taylor blushed as Andrea reached for the waistband of her pink panties, but let her slip them down revealing the massive cock that was taped down between her legs.

"That looks terribly uncomfortable. Let your clitty free."

Taylor hesitantly complied and released her giant cock which was beginning to thicken. Andrea couldn't resist and reached for the stiffening organ.

"Wow, you are a very big girl."

Taylor nodded sheepishly, blushing but appreciating the attention as Andrea stroked her. Andrea stared at the blossoming erection with a leer.

"You like me touching you?"

"Yes, Ma'am. It feels good"

"Touch me."

Taylor reached out to touch Andrea's generous cock that sprang quickly to life in her hand. It was large, although nowhere need as impressive as Taylor's.

"Was Brad able to handle you?"

"It took a while to prepare him, but yes and it was extraordinary. You and he...?"

"Just once. It was awkward. He couldn't really handle me, but if he could take this you must have been very patient and gentle."

"I wanted him to like it, so I was very gentle, and we spent quite a while working him up to it. I love him so much, all I thought about was making it pleasurable for him so it would be something he wanted again."

"He's a really nice guy. Do you mind that he was with me?"

"No, Ma'am."

They remained silent for a moment. Taylor still held Andrea's stiff cock and began gently stroking it. Her own cock joined in rising to the occasion. Andrea took it in her hand and encouraged Taylor to her full substantial length and girth.

"Your cock is amazing, the biggest I've ever seen, let alone touched."

"I wish it weren't. Brad is the first guy who's ever been able to enjoy it."

"Have you ever been with a cis woman?"

Taylor blushed and cast her eyes downward.

"Yes, Ma'am. Twice. I guess I'm bi. They both enjoyed my size."

"I imagine they did. Pussies stretch more easily."

Taylor's stroking of Andrea's rock-hard cock had drawn a trickle of precum that slid down her glans. Taylor smoothed it into her skin with slow circles of her thumb.

"Ma'am, may I suck you?"

"What do you want to suck, slut?"

"Mmm, your beautiful cock, Ma'am, may I please suck your cock?"

"You may."

Taylor dropped to her knees and brought Andrea's glans to her lips. She kissed the plum shaped knob delicately to savor the salty pre cum. She teased the tip of her tongue into the slit, seeking more of the delicious nectar, before giving in to her wanton hunger and plunging her mouth down on Andrea's throbbing meat.

Andrea pressed on the back of Taylor's head and plunged into her voracious mouth forcefully, driving herself into the girl's throat. At first Taylor gagged and had to pull back from the assault, but she quickly recovered and forced her head back down to accept all of Andrea's swollen cock. deep into her throat.

Andrea took that as license and began to thrust rhythmically, skull fucking Taylor freely. Taylor relaxed and accepted the forceful near rape of her mouth and throat. She cupped Andrea's large balls and worked them in rhythm with the piston strokes of the big cock.

"Yeah baby, just like that, take all of Mama's big dick."

Taylor grabbed hold of Andrea's firm buttock and pulled urging her to fuck her with abandon. Soon she felt coiling muscles and the balls in her hand draw up.

"Cuuuummming."

With a series of intense strokes deep into Taylor's throat Adrea emptied her balls in a flood of hot tangy cum that eventually began oozing from her mouth and sheeting down her chin and onto her throat. Andrea pulled out to shoot the last spurts onto the girl's face and tits.

Taylor grinned up at Andrea with more cum flowing over her lower lip, scooped a fingerful to her mouth and sucked it provocatively from her finger.

"Thank you, Ma'am."

"That was lovely, you're very skilled."

"Thanks, it was my pleasure."

"Go clean yourself up and get to work, customers await."

"Yes, Ma'am."

Taylor grabbed up her uniform and scurried for the bathroom.

When she emerged from the bathroom wearing her new clothes Andrea was seated at her desk going through some paperwork.

"Is this okay, Ma'am?"

Andrea looked up and nodded.

"Those fit well enough for tonight. We'll get them altered a bit tomorrow. Go shake that pretty ass and make us some money. Come see me at closing."

The boss returned to work and Taylor flashed her a smile before hurrying out the door.

It was a busy night. Taylor was tired when the last customers finally left. That meant she could finally do what she had been thinking about all night, return to Andrea's office. The taste of cum had left her mouth hours before but the memory of the massive load she swallowed and been coated with remained.

Knock, Knock.

"Ma'am, it's Taylor, you wanted to see me?"

"Come in."

As she entered, Andrea rose from her desk and came to take her in her arms and give her a big, passionate kiss. Their tongues came together, and Andrea grabbed Taylor's ass, pulling them together. Their cocks began to rise immediately. They each reached for the other, working through fabric as quickly as possible to grab the hardening girl cocks as they seemed to be intent upon devouring each other's faces.

When that first burst of passion began to ebb, albeit slightly, they shared a deep breath and a sigh.

"Taylor, what is your situation with Brad? Is he keeping you?"

"I guess so, Ma'am. He's gotten us an apartment and says he'll be here once or twice a month. It's all so new, I'm not sure what to expect."

"How do you feel about him."

"I think I'm falling in love with him."

Andrea nodded and stared into her eyes.

"I really like you."

"I like you too, Ma'am."

"Are you exclusive with him?"

"The subject hasn't really come up."

"Have you gotten kinky together?"

"No, Ma'am."

"Have you ever with anyone?"

"There were a couple of regular drivers that came to the truck stop. One of them liked me to spank him and another who liked to use a flogger on me."

"Did they know you were trans?"

"The one who liked to flog me did, and other one probably did."

"Did you enjoy that?"

"It was kind of fun."

"I'm a Domme, you know what that means don't you?"

"Yes, Ma'am. You're sadistic, right?"

"Yes, I am."

"Do you want to hurt me?"

"Yes. I want to do all sorts of wicked, profane things with you."

"I see."

"Taylor, if I have my way, and I always do, you will be mine."

That left Taylor speechless.

"What will you do to me?"

"Telling would ruin the surprise. And we wouldn't want that, would we?

"I guess not, Ma'am."

Andrea grabbed Taylor's balls forcefully and squeezed. Taylor yelped.

"These will belong to me."

She pulled down until Taylor dropped to her knees. She leaned forward to nuzzle the bulge under her boss' skirt.

"You like sucking cock."

"I really liked sucking yours before."

"That's good, you'll get to do it often."

"I feel funny, cheating on Brad so soon."

"You'll be coming home with me tonight."

"I will?"

The look Andrea threw Taylor's way left no doubt as to her veracity and she bent down to administer an even stronger squeeze, evoking a choked scream.

She leaned close and kissed her. Taylor tried to respond despite the pain Andrea was administering to her aching balls.

"Yes. You will."

Half an hour later Andrea unlocked her apartment door to let Taylor enter. Taylor walked in, a nervous expression coloring her lovely face. Andrea pointed toward a door.

"Bedroom's there. lay your clothes on the dresser."

Taylor gnawed her lower lip and hesitated.

"It wasn't a suggestion."

Taylor nodded, walked awkwardly to the door, opened it and entered the room. Andrea followed her. Taylor undressed slowly, unsure of making the commitment. Andrea followed her into the room carrying a riding crop which she slapped threateningly into her palm.

"Naked, slut. You know you want this."

"I love Brad, Ma'am. This feels wrong."

Belying her words, she removed her bra to reveal her lovely tits and receive a harsh lash from the crop.

"Oww."

"Panties too, I will have my slave naked for me."

Taylor's eyes protested as her hands pulled down her panties to reveal her traitorous stiffening cock. As soon as it sprang free the crop bit into the glans eliciting a howl.

"Grab your ankles."

Taylor responded slowly and her reticence was rewarded with a series of crop strokes to her shoulders and back until she was folded over gripping her ankles. With her body offered obscenely. Andrea began beating her thighs and ass harshly. Leaving bright red stripes. Taylor whimpered pitifully, inflaming Andrea who delivered several strokes up between her legs that made her shriek and collapse to the floor in tears.

"Get up, slut."

Taylor's hands came together protecting her cock and balls from the crop.

"Uncover that cock, slut."

Taylor reluctantly moved her hands away from her junk and stared fearfully at Andrea who laid the popper against her glans and lifted her cock with it. Taylor trembled, expecting that the teasing gesture was soon to change into a vicious slash from the cruel implement. Andrea continued to tease the terrified girl's delicate flesh.

.

"Please don't hurt me anymore, Ma'am."

"I bet you can beg better than that."

"Please, Ma'am, let me serve you. I'll be so good. You can use me any way you want."

"Maybe what I want is to hurt you."

Taylor cast her eyes at the floor, hunched her shoulders protectively, and shuddered.

"Brad is gentle and loving with you, isn't he?"

"Yes, Ma'am," Taylor mumbled.

"Do you ever wish he'd be dominant and just take you hard and fast, use you like the slut you are?"

"I like the way he treats me, Ma'am."

Andrea teased her cock more, lifting it and pushing it side to side, then provocatively gave her balls a series of teasing prods. Taylor shuddered at each contact.

"You can leave anytime you'd like."

"Thank you, Ma'am."

"Or if you want sex with me..."

Andrea's tone made the words into an invitation, that she punctuated by stroking Taylor's cheek gently with the popper.

Taylor nodded silently as her eyes filled with tears.

"Is that a yes, slut?"

Taylor shuddered, but nodded again, sheepishly.

"Say it."

"I want you, Ma'am, very much."

Her cock beginning to stiffen in steps confirmed her words.

Andrea brought the popper back to stroke Taylor's glans, letting the leather fold over as she pressed softly. Taylor dropped to her knees and bent forward to kiss Andrea's rock-hard cock.

"Good girl, get me nice and wet."

Taylor followed her directions immediately, taking Andrea's substantial meat deep in her mouth, slobbering gratefully on it so saliva ran down in rivulets onto her scrotum.

"That's enough, hands and knees on the bed."

Taylor hurried to comply, rising and hurrying to present herself on the bed. She raised her ass, offering her puckered hole blatantly. She looked back at Andrea over her shoulder and smiled invitingly.

"Please fuck me, Ma'am. I need your gorgeous cock inside me."

"You think my cock is gorgeous?"

"Yes, Ma'am, it's beautiful. I love sucking it and I can't wait to feel it deep inside me. I want you to fill me with your delicious cum."

"Lovely."

Andrea removed her dress to reveal her spectacular body, from her exquisite 36 C breasts, down her toned tummy, to her hard seven-inch cock, dripping precum.

She climbed onto the bed settled on her knees behind Taylor, pressed her cock down to bring her crown in position at Taylor's starfish. She let a glob of spit drop onto her purple knob and pressed into the tight opening. Taylor moaned and arched her back to draw more of Andrea's thick shaft into her rectum. Encouraged by the eager response Andrea drove deeper into Taylor's hole, then reached around to grab her huge cock.

They quickly found a rhythm and Andrea began fucking her with abandon, deep into her, relentlessly plunging with hard, fast strokes. Taylor mixed whimpers with moans as the pain and pleasure from the brutal fucking transported her into a blissful passion zone. Andrea's hand working her cock and the insistent pressure on her prostate was bringing her closer to orgasm with each forceful penetration.

"Oh my god, fuck your slut Ma'am, fuck me hard, I'm cumming."

Andrea dug her nails into Taylor's cock, making her scream.

"Wait your turn, slut. Mama cums first."

Taylor gasped at the cock pain interrupting her release. Andrea continued fucking her harder until after a few more powerful thrusts, she shot a series of cum rockets deep inside Taylor's bowels.

"Oh god yes fill your slut with cum, make me yours."

"You are mine, bitch. I own your ass now, don't I?"

"Yes, Ma'am."

"Shall I let you cum now."

"Please Ma'am, I need to cum so bad."

"Ask nicer."

"Please, Ma'am. Please let your nasty little slut cum for you. I need to so badly."

Andrea slipped her gradually softening cock from Taylor's distended opening and pulled her around and forced her own to bring her mouth to her cock.

"Suck me clean, bitch. Do a real good job and maybe I'll let you cum."

Taylor quickly took the funky cock, fresh from her ass, into her mouth and began sucking it aggressively, cupping Anrea's balls as she sucked her deep into her throat.

"Mmm, baby really wants to cum. Clean that funky cock, slut. Get all my cum and any of your nastiness off it."

Taylor increased her work with tongue and lips, carefully cleaning every inch of her cock, swallowing her own spit mixed with Andrea's salty, bitter semen and the funk of her rectum.

"Enough. On your back."

Taylor released Andrea's cock and rolled over onto her back. Her rigid monster cock stood up at an angle twitching and begging for attention. Andrea teased the length of her shaft with delicate fingertips.

"You may touch yourself."

Taylor's visage clouded into a near pout.

"I am about to let you cum, you didn't think I'd do it for you, did you?"

"I..."

"I want to watch you masturbate, slut. Show me how you do yourself."

"Yes, Ma'am."

Taylor slowly took her cock in her right hand and her balls in her left and began to fondle her balls as she stroked her cock.

"What are you thinking about?"

"I'm remembering how wonderful it felt when you were fucking me, with your big cock pressing on my prostate as you stroked my cock."

"You liked that, didn't you?"

"Very much, Ma'am."

"Better than when Brad fucks you?"

"Yes, Ma'am, your cock is bigger."

"You need something in your ass."

"It helps, Ma'am."

"Raise your knees, but don't stop."

When Taylor raised her knees Andrea brought the crop up between her legs, placed the handle in her crack, found her anus and pressed it inside her. Taylor groaned at the intrusion and rolled her hips to assist the penetration.

Her breathing accelerated and deepened. She worked her cock more intently and fondled her balls more aggressively.

"When you're close ask for permission to cum."