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."
