The Agency Ch. 08

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Michelle has an intense training session and date w/ Brenda.
9.5k words
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Part 8 of the 24 part series

Updated 10/07/2023
Created 02/01/2021
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Ms_Allison
Ms_Allison
1,372 Followers

*Author's notes: This is a work of fiction, hopefully that is not a word you struggle with. It is a story of fictional, consenting adults who enjoy power exchange, lingerie, heels and the like. It's in the transgender/crossdressing category for a reason, if that scares you please back away slowly. For the rest of you, please enjoy!

~~~~~~~~~~~~~~~~~~

Tuesday was almost as big a blur for Michelle as Monday had been. She was thankful she'd chosen an easily removable dress, as Ms. Allison called her into Her office no less than five times. With each entry to Ms. Allison's office, Michelle removed her dress, hanging it on the back door quickly followed by her servicing the dildo hanging above her dress, then awaiting instructions from her Boss. Each trip to the office was different, two involved normal conversation between Boss and employee, the second of which happened over lunch. Another trip into the office had Michelle squatting deeply to deep throat another dildo, while on another occasion Michelle willingly bent over the desk while begging to be fucked. On the final trip into the office, Michelle lovingly serviced Ms. Allison's strapon, relishing in the compliments of how she'd improved her blowjob abilities. While Michelle expected to be "too tired" to play at home, after all she'd worked a dildo down her throat no less than twelve times that day, a call from Babette quickly changed that.

"Hi sweetie!" Michelle answered cheerfully.

"Hello there," Babette's voice was warm and inviting, "what are you wearing?"

"Nothing fun." Michelle responded.

"Well, I have pictures to share," Babette teased, "but you may need to have something fun on to view them!"

"Are they on the website yet?" Michelle could feel her excitement building quickly.

"Nope!" Babette giggled. "I'm giving you a sneak peek, but you can't be under-dressed for this!"

"Oh, you are quite full of yourself tonight, aren't you?" Michelle quipped.

"Deservedly so," Babette chuckled louder, "I did spend a couple hours with a horse tail butt plug up my ass to make these happen you know!"

"What!?!" Michelle almost dropped her phone in response. "You didn't!"

"There are more," Babette teased, "call me back when you're ready to see them!"

"Oh, that bitch!" Michelle rolled her eyes as she looked at the now disconnected call. "Fine, I'll play her game," Michelle grumped, "but she won't see what I have on, all I need to do is tell her what I supposedly have on!" Michelle's phone beeped. "Fucking bitch!" Michelle blurted upon seeing the text from Babette. "Pics needed, no cheating!"

Rushing off to her closet, Michelle quickly dug through to find something Babette would deem acceptable. Selecting a pair of black opaque thigh highs, with chiffon ruffles and white bows, Michelle stepped into her highest pair of black patent heels as well. She then pulled on a black teddy with white lace and ruffles which made it appear like a maid uniform. The teddy came with a ruffled choker and wristlets, which Michelle put on as well. Applying a dark red lipstick, Michelle placed her phone against her nightstand, propping it up so she could see most of herself on the screen. Everything but her shoes could be seen.

"This will take some creativity!" She said to herself. Rushing to hit the button and get back into position, Michelle lifted her foot, kicking it behind her, to bring it into frame. Unhappy with that one, Michelle attempted three more before settling on a picture to send Babette. "That should do it!"

A moment later Michelle's phone rang again. "Nice ass!" Babette gleefully exclaimed. "Pull up your tablet and I'll send you the file!"

"Okay, you got it!" Michelle responded sitting on her dilapidated couch and pulling up her tablet. "I'm ready."

"While it downloads, you'll have to tell me about work today!"

"You know, the usual," Michelle giggled, "fucking, sucking and in general being my Boss' plaything!"

"Soooo, the typical work day then huh?" Babette laughed loudly.

"Yeah, pretty much." Laughed Michelle. "Okay, the file is open, where do I start?"

"Just click on the first one," Babette gleefully said, "and we can go from there."

"Well look at you!" Michelle's legs squeezed together as she looked at Babette's picture. "That's a cute outfit." They slowly looked through pictures together, as they went along pictures got more and more risqué.

"Holy crap!" Michelle blurted. "There's my little pony!"

"Ha, ha," Babette replied, "very funny."

Babette was covered head to toe in hot pink latex, with a strange looking pair of white knee-high boots made to look like hooves and a pink tail that almost reached the floor. The outfit was topped off with a white corset, arm binders and bridle. Michelle was scared but also incredibly turned on by the sight.

"Go to the next grouping!" Babette instructed, obviously excited to share these with her friend.

"Holy shit!" Michelle gasped. "I mean, holy shit!"

"I know, right?"

Babette was in a flesh toned latex catsuit, with one glaring difference to all the others. The catsuit came complete with a bright red sheath that covered her definitely erect cock and balls. The face had large cat-like eyes as well. A following picture showed Babette's erection tucked away.

"What was worse," Michelle teased, "getting your cage off or having to put it back on?"

"Definitely putting it back on!" Babette replied. "It definitely wasn't easy."

"Oh, and they don't stop there!" Michelle felt herself getting even more excited as she started slowly scrolling through bondage pictures. "Was the photographer a guy?"

"It was."

"How long did he have you all tied up and helpless like that?"

"Only until I ached!" Babette chuckled a bit sheepishly as she answered.

"What did you do!?!" Michelle demanded.

"I may have given the photographer," Babette paused momentarily, "a bit of a tip when we were done!"

"Wait, you gave him one?" Michelle could barely contain herself, laughing through the rest of her thought. "Or he gave you one?"

"Keep scrolling slut!" Babette replied.

"Ohhhhhh that's more than the tip he's giving you!" Michelle clicked quickly, feeling her cage choking her cock. "And he had a friend!?!" Babette was moved through several positions, all while wearing cuffs and rarely in a position to defend herself and even more rarely without at least one cock inside her. "Wow! I mean just wow!"

Setting the tablet aside, Michelle was now sitting in the most unladylike way, stroking her sore balls with one hand while scrolling back through the pictures with the other. Her hips were moving slowly in time with her hand, she was practically humping herself while watching her friend in action.

"Guess what?" Babette teased. "Those two will be your photographers as well!" Michelle gulped at the thought realizing suddenly that her mouth was watering. "Lunch tomorrow?"

"Sounds good to me." Michelle replied.

"Don't forget to dress up for Brenda tomorrow," Babette teased further, "and enjoy your dreams tonight!"

"No kidding! Dick dreams!" Michelle chuckled unable to take her eyes from the picture of Babette.

A chill shot up Michelle's spine as she pictured herself in Babette's position. She was on her knees wearing elegant white lingerie with red accents, a satin bustier, wide lace top stockings and a long curly deep brown wig. Behind her a well build stud had one hand tightly gripping her hip while the other held her shoulder, his crotch pressed into her ass, obviously buried deep inside her. In front of her was another muscular stud, a sharp contrast to the build of Babette. One hand on the top of her head, fingers wrapped around the back holding her head in place, while his soon to be empty balls rested against her chin. Babette's throat bulged slightly to accommodate the shaft inside her.

"Dear God," Michelle huffed, "I need to get fucked like this!"

Her face blanched at her words, but they were accurate. A couple months ago getting fucked meant something completely different in that apartment. In reality it was only life that had been fucking Michael, now Michelle wanted what Babette had, or to be summoned into Ms. Allison's office. Her body yearned to be slutty, ached for it. Her ability to say no was quickly diminishing. Michelle hustled to her bedroom, grabbing the two dildos along the way. She quickly found herself in her new favorite sexual position, pinned between two large dildos on her knees in the door frame, all the while imaging she was Babette between those two studs. Michelle remained there until her urge was sated enough for sleep. Stepping out of her heels, she simply climbed into bed still dressed as she'd been almost two hours ago.

Michelle's alarm clock went off earlier the following morning, waking slowly, she felt a bit sore. "That damned Babette," Michelle grumped while tugging the crotch of her teddy downward a bit, "getting me all horny before bed." The slight headache was nothing compared to the two aches she felt as she sat up. "I blame the two of you again!" Michelle said looking at the two dildos still lewdly hanging from the door frame. "Fuckers!"

Chuckling, Michelle slid off her stockings and removed the teddy before plodding past the dildos and into the bathroom. Emerging a few minutes later in a pair of black yoga pants with sheer cut outs and a matching sports bra, Michelle set up her yoga mat in her small living area while her coffee brewed. While Michael had never enjoyed any kind of workout, Michelle had started to really love them. She could see the subtle changes in her body that a proper diet and active lifestyle brought about. Her butt was more shapely, her stomach flatter and toned, and her legs more shapely and defined. Michelle may not have been much to look at when she was a guy, but she was becoming a hot girl! The positive results pushed her to work harder as well. Michelle made her way back to the bathroom, carrying her morning coffee with her and delicately balancing it on the tiny vanity.

"I have to ask Babette when I can move in over lunch!" She said to herself as she stepped into the shower.

The morning regimen had been a slight nuisance at first. Shaving, exfoliating, moisturizing, then the makeup had seemed to be just too much. Michael could stumble out of his apartment 30 minutes after waking up freshly showered with a full stomach, for Michelle it was more like an hour not including her workout. But, Michael was happy in thrift store jeans and a t-shirt he'd had since freshman year in college. Michelle stepped out of the shower, padding herself dry before rubbing cocoanut body butter over her skin. She loved the smell of it, and after all this time using it her skin was now incredibly soft.

"If yesterday was any indication," Michelle said to herself as she walked to her closet, "I'm going to need to go with a dress and just deal with taking it off for Brenda this morning."

Michele's eyes lit up as she looked through her closet. She immediately picked the perfect dress for the day, and knew exactly what lingerie to pair with it! Grabbing a dark gray satin and black lace ensemble with black stockings, Michelle started to get dressed. The dark gray satin panels were strategically placed in the middle of the high cut panties and bottoms of both bra cups, while lace adorned the rest. All three had small bows in the middle, the lace and bows looked elegantly feminine bringing a smile to Michelle's face. She added her favorite perfume, and adjusted her wig before putting on the belted black dress. For safety sake, Michelle placed a small pin in the somewhat plunging neckline of the dress. It would stay there at least for her commute as her cleavage was not passable under close inspection. The dress fit perfectly, moving just enough with her while remaining snug enough to show off her hard fought figure. Stepping into a pair of black sling back heels, Michelle made her way to the door knowing Fred would approve of her outfit this morning.

"Good morning." A rather dull female voice said from behind Michelle in the hallway.

"Good morning Cindy." Michelle's voice was far perkier than the sandy haired blonde from down the hall.

"You look nice this morning," Cindy's voice had a hint of envy as she was certainly not dressed to Michelle's level this morning, "any word from your ex?"

"Oh, Mike?" Michelle smirked, "Not since he moved to warmer climates no," Michelle relished in the fact that the woman who'd shunned Mike was now asking about him, "although he did invite me down to visit."

"Where is he again?" Cindy's envy grew exponentially.

"He bought an island owned by that guy," Michelle couldn't believe how catty she was being, but she couldn't help herself, "the one that has his own airline. You know, big house on a small, private island."

"Oh," Cindy replied flatly, "sounds nice."

Cindy was normally more cheery than she was acting, although not when Mike was around. She'd always treated him with disdain or simply ignored him. Michelle was rarely this heartless, but felt more justified considering Cindy wouldn't be giving Mike the time of day or asking about him if he hadn't "won the lottery".

"I may head down next month," Michelle continued as the elevator door opened, "just to see what I can do about getting rid of my tan lines." Holding the door for Cindy, Michelle stepped into the small elevator remembering the time Cindy had elected to wait for the next one rather than ride with Mike. "White sands and crystal clear blue water sound good right about now."

"I can imagine." As the elevator door opened, Cindy uttered, "Shit, I'm in no mood for him."

"I've got you covered." Michelle said confidently stepping off the elevator walking directly toward Fred. "Good morning Fred!" Michelle felt a rush of power as she approached the building manager, who was only in the hallway to check her out on her way to work. "I've got great news," Michelle didn't wait for him to respond and kept going, "I'm moving out at the end of the month, please let the land lord know."

"What?" Fred blurted.

"You heard me," Michelle adjusted her path slightly, taking Cindy by the arm and heading to the door, "if they care to ask why so suddenly, tell them it's because some creepy asshole sits in the hallway every morning waiting to leer at us on our way out!"

"Holy shit," Cindy's shock was evident in her voice, "what did you ever see in that dolt Mike?"

"If you must know," Michelle turned to stare Cindy in the eyes as she spoke, "have you ever orgasmed so much or so hard your stomach muscles cramped?" The way Cindy's jaw fell open the answer didn't need to be said. "Yeah, and that was only part of it!" Feeling an even greater rush, Michelle leaned forward lightly pressing her lips to Cindy's. "Have a great day!"

Michelle never turned back to see if Cindy even moved from her spot. She wanted to relish the looks of shock from both her and Fred! On top of everything else, she'd have to talk to Babette about moving in soon. Michelle giggled at how easy leaving that place would be, everything that she hadn't gotten since starting at the Agency would go into the dumpster! That was mostly the furniture as it was, which would make moving incredibly easy. Before she knew it, Michelle was entering the Dr.'s office with coffee in hand a full 25 minutes before her appointment.

"Good morning!" Brenda called out from behind the desk.

"Good morning to you!" Michelle replied with a big smile.

"Someone is in a great mood this morning," Brenda said as she opened the office door allowing Michelle inside, "what have you got going on?"

"I don't even know where to start!" Michelle tittered in response.

Walking into the exam room, Michelle pulled up a seat on the table while Brenda sat on the stool. Over coffee Michelle told Brenda the details of her morning, as well as the back stories on both Cindy and Fred. Brenda intently listened, showing surprise and support for Michelle. It was odd how comfortable Michelle felt with Brenda, sharing these details seemed far too easy. The time seemed to fly past as the Dr. was soon heard entering the office.

"Oh shit, look at the time!" Brenda was slightly panicked as she quickly stood. "I need you to get into the robe quickly!" Grabbing the robe from behind the door, Michelle stood remembering to first undo the small pin hiding her cleavage. "Let me help you with that." Brenda stepped very close to Michelle, deftly undoing the belt in front of Michelle's dress. "I was so enthralled in your morning I lost track of time!" Looking up, their eyes met momentarily. "No time for that!" Brenda said pulling the belt free.

"Time for what?" Michelle's head was spinning again. Was she flirting with her?

"Never mind," Brenda said as Michelle slid the dress off, "for as much as you look like a girl you still think like a boy!" Brenda leaned in close, her hand quickly sliding around Michelle's torso as she unclasped Michelle's bra. "Hurry up, he's almost here."

"Sorry." Michelle replied letting the bra fall off her arms and quickly pulling on the robe.

The two of them felt like kids who'd just gotten caught doing something wrong by their parent. Thankfully the Dr. seemed oblivious to it, but Michelle couldn't stop thinking about Brenda's comment. What did she mean that Michelle though like a boy? She had to be flirting with Michelle! But what could she ever see in a cross dressing submissive that she didn't see in Babette? Michelle's head spun trying to understand it. Sitting with the robe bunched around her waist, Michelle finally came back to reality as the Dr. began the next round of saline injections. She could feel her skin stretch somewhat, not an uncomfortable amount, but still her small breasts were definitely getting larger.

"And I'll see you again on Friday." The Dr. said before getting up and walking out of the room.

"I'm sorry," Michelle said as Brenda approached with the cream, "I just don't understand why or even if you're interested in me."

"You do realize I've been flirting with you since the beginning right?" Brenda said making eye contact with Michelle, conveying her sincerity, "Like really flirting with you."

"I just don't get why though," Michelle replied, "I mean, look at me."

"Do you think I don't know?"

"That's it," Brenda responded warmly, "I do know, I just find you to be special." Michelle blushed deeply, it was the first true compliment she'd received from a woman. "There's just something about you."

"My fashion sense?" Michelle giggled in response.

"Oh you definitely have that going for you!" Brenda replied. "And your taste in lingerie is amazing!" Michelle blushed at the compliment. "I just find myself attracted to you," Brenda admitted, "and while I can't put my finger on why, it's undeniable."

"I don't know what to say," Michelle felt tears welling in her eyes, "other than thank you."

"Say you'll go to dinner with me tonight!" Brenda exclaimed.

"Okay." Michelle responded quickly then immediately questioned it.

"Here's my number," Brenda said as she pulled a yellow post-it note from her scrub pocket, "text me and we can figure out where and when."

"I will." Michelle replied looking at the phone number with awe.

"Put that away before the Dr. sees," Brenda whispered somewhat sharply, "let the cream dry and then you can get dressed again."

"Okay, thanks." Michelle responded while wondering where to put the post-it. "I'll text as soon as I get downstairs."

"I'll reply as soon as I can," Brenda responded as she walked to the exam room door, "somewhere casual so you don't look better than me though, okay?"

"Okay." Michelle replied feeling her face burning brightly. "I have a date," she said to herself as she stepped into the hallway, "with a girl!" Michelle's tone was pure disbelief. "As a girl!" Now it turned to confusion. "What the fuck am I getting myself into here?"

Ms_Allison
Ms_Allison
1,372 Followers