The Agency Ch. 21

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After her wild day, Michelle goes out with Brenda.
8.8k words
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Part 21 of the 24 part series

Updated 10/07/2023
Created 02/01/2021
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Ms_Allison
Ms_Allison
1,374 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!

Keep in mind, this chapter will deal with the main character having sex with a man or men. Again, if you're not a fan, skip reading it. Sorry for the delay getting this story out, life has gotten busy.

Michelle awoke slowly, feeling Babette's body still pressed into her back and her left hand resting between Michelle's breasts. As she slowly started to move, she felt the soreness in her shoulders as well as her backside. Both were expected, and semi welcome reminders of her photoshoot the day prior. Michelle pulled on a long red satin robe before plodding out to the kitchen for coffee. Per her usual routine, she looked at her phone for any signs of Brenda. Almost as if it were perfectly timed, a text message arrived.

"Morning coffee?" Brenda texted.

"YES!" Michelle replied excitedly.

"At the coffee shop, say 8ish?"

"Sounds great!" Michelle replied looking at the time.

Quickly making herself a cup of coffee, Michelle hustled her way back to the bathroom to start getting ready. She had time, but she didn't want to keep Brenda waiting, and if they both arrived earlier than 8, all the better! Michelle quickly showered, shampooed and shaved before heading back to the bedroom where Babette was nowhere to be seen. Picking out a soft green sheer with floral embroidered lingerie set, Michelle started to dress.

"Where are you off to so quickly this morning?" Babette asked as she reentered the bedroom.

"I'm meeting Brenda for coffee." Michelle couldn't help but smile as she pulled up the side string thong.

"So, are you going to ask the naughty nurse how she's been spending time with Ms. Allison?"

"I don't even know how I would start that conversation," Michelle replied as she clasped her front close bra, "and what would I do if she didn't answer or said she couldn't answer?"

"What would you do if she did answer?" Babette pried as she took a seat on the edge of the bed.

"And what if she can't answer," Michelle replied as she slid on one of her tan lace top stockings, "and then told Ms. Allison I was being nosey?"

"Hmmmm," Babette paused, taking a sip of her coffee, "there are worse things than getting a spanking from Ms. Allison!"

"Okay, you have a point," Michelle replied finishing with her lingerie before going to select a dress to wear, "but, I'd rather not upset either of them."

"Chicken!" Babette teased.

Michelle selected a dress slightly darker green than her lingerie, with a complimentary pair of 4-inch heels to go with it. Stepping back out of the massive walk in closet, Michelle added some jewelry and a cute watch as well as some dangling earrings to complete her look. Taking one look over herself in the full-length mirror, Michelle felt she at least looked ready to take on the day.

"Don't you have packing to do?" She asked Babette, who was still sipping her coffee while sitting on the bed in a rather flimsy nightie. "You are moving in a couple days aren't you?"

"Are you that eager to get rid of me?" Babette walked over to Michelle, adjusting her necklace and the collar of her dress slightly. "You've barely mastered dressing yourself at this point," Babette said as she gave Michelle a quick but firm hug, "I'm not sure you're ready to live on your own as a girl!"

"It's going to be odd when I come home Sunday night," Michelle said as she hugged Babette tightly, "and you're not here."

"Oh, that's right," Babette backed away slightly, looking Michelle in the eyes, "you have a trip with Bernard this weekend! Lucky you!"

"I"m a bit anxious about it to tell you the truth," Michelle responded hugging Babette again, "I have no idea what to expect."

"You'll be fine," Babette said reassuringly before letting Michelle go, "he's an absolute sweetheart who will spend most of the time ogling and touching your boobs interspersed with the occasional BJ."

"Okay." Michelle blushed at the realization that Bernard would be her 4th cock this week!

"Go have fun with your naughty nurse!" Babette said, giving Michelle a kiss on the cheek. "I've got yoga to do!"

"Have fun!" Michelle replied, grabbing her purse and heading out.

Michelle made her way through her morning commute without so much as a second thought. It seemed years ago that she'd been near panic trying to step onto the subway train with heels on! Or even making her way down the sidewalk without tripping had seemed unimaginable at one point. Now she barely gave any of that a second thought. Walking into the coffee shop, Michelle smiled and waved at the young girl behind the counter. By the time she got to the register her cup was ready to go, with little more than a quickly drawn heart on the side.

"Just one?" Michelle asked quizzically.

"Your date is already here." Replied the girl with a warm smile. Michelle looked around the coffee shop, not seeing Brenda's typical ponytail and scrubs, then looked back at the girl at the counter. "The navy blue sweater by the window," she instructed, "I like her new look."

"Thanks." Michelle replied walking toward the woman who was reportedly Brenda. "Good morning." She said as she approached.

"There you are!" Brenda quickly stood throwing her arms around Michelle. "I feel like I haven't seen you in forever!"

"I didn't even recognize you!" Michelle replied before taking a seat, "I mean, you look amazing," Michelle looked over Brenda again, "are you still working in the Dr's office?"

"Oh, you're so sweet," Brenda replied, placing her hand on Michelle's thigh, "I am still there, but I've had so much fun the past few days, your Boss is amazing you know!"

Michelle swallowed hard as Brenda brought up Ms. Allison first. The fact was, Brenda spending time with Ms. Allison had definitely made changes with Brenda. Her usual ponytail was replaced with a French braid, and she surely used a curling iron on the front of her hair. Michelle couldn't remember if Brenda had bangs before, but if she didn't she certainly did now! Brenda also had makeup on, at best she wore mascara, but now she had blush, foundation and lipstick as well as having done her eyes a bit more than usual. Everytime Michelle had seen Brenda on work days she had on scrubs and sneakers, now she was wearing dress pants, a luxuriously soft sweater and heels!

"Are you wearing heels?" Michelle almost gasped at the realization Brenda was far more dressed up than usual.

"Cute aren't they?" Brenda asked as she extended her foot to show off the 3-inch heel. "I still don't know how you wear those," Brenda said nodding toward Michelle's heels, "but these aren't too bad!"

"All I can say is wow!" Michelle responded dumbfounded.

"Guess what?" Brenda said leaning in closer and not waiting for a response. "My lingerie even matches the rest of my outfit!" Michelle stared blankly, only shaking her head after Brenda pulled the V-neck of her top aside enough to show off the strap of her navy blue demi bra. "What do you think?"

"I, I'm, well," Michelle struggled to form a sentence, "you look fucking amazing." Michelle blushed, realizing she'd blurted that a bit louder than necessary. "I mean you look great."

"I think I liked your first answer better," Brenda chuckled, "how about dinner tonight?"

"That sounds fun," Michelle replied, "you can tell me all about your week."

"And you can tell me all about yours!" Brenda responded watching for Michelle's reaction intently.

Brenda could tell Michelle was confused by her dressier appearance, and obviously holding back in the conversation as well. She wondered if Michelle had any idea that she'd been in the office with Allie two days before while Michelle had been blindfolded? The entire time in Allie's office, with Michelle helpless and bound, had been an incredible experience for Brenda and beyond eye opening. Even now she felt herself wiggling slightly in her seat at the thought. No, there was no way Michelle could know it was her, she'd been far too distracted as Allie showed Brenda the ropes. How Allie could control herself like she did was beyond Brenda's comprehension, but her new Friend did a lot of things different than she was used to, like caging Michelle's cock. Brenda understood it made Michelle more obedient, but Brenda had certainly enjoyed Michelle uncaged the other day.

"What are you thinking about?" Michelle interrupted Brenda's day dreaming.

"Oh, nothing terribly important," Brenda replied, hoping her face wasn't as flush as it felt, "part of the reason I'm dressed up is I have to look for a new place to live, so I need to look a bit more professional than scrubs."

"I can see that." Michelle responded.

They chatted idly for a few more minutes before walking to their building. The elevator being a bit crowded gave them the excuse to walk up the stairs together. Making their way past Michelle's floor, Brenda lingered behind momentarily.

"What does my sweet girl have on today?" She asked playfully while lifting the back of Michelle's dress. "Such sexy undies!" Brenda giggled.

"I knew you'd lift my dress," Michelle replied, "so I wanted to look my best!"

"Well your ass and legs are stunning as always!" Brenda giggled, giving Michelle's butt a firm spank. "That's a fun sound," Brenda laughed while giving Michelle's other butt cheek a spank as well, "maybe I can do that more tonight after our date!"

"Maybe." Michelle felt her excitement growing rapidly as she tried to focus on continuing up the stairs without falling.

As they reached the landing for Brenda's floor, Michelle felt her head spinning as Brenda quickly backed Michelle into the corner behind the fire door. Brenda's hands still under Michelle's skirt, her manicured fingers digging into Michelle's butt, Brenda pressed Michelle into the corner with her body, pausing to look Michelle in the eyes. Michelle felt like prey as Brenda's eyes met hers, just as she went to speak Brenda pressed her lips to Michelle's, quickly pushing her tongue into Michelle's mouth. With one of her arms pinned by Brenda's grasp, Michelle wrapped the other around Brenda's body, but it was quite evident who was in charge. Michelle became even more aroused, whimpering softly as Brenda's body pressed firmly against her own.

"Oh God!" Michelle panted as Brenda broke their kiss. "You're going to make focusing on work very difficult today!"

"Think so?" Brenda deftly pulled her right hand free, letting the backs of her fingernails slowly glide their way up the side of Michelle's body before sweeping Michelle's hair off her neck. "Would that be a bad thing?" Brenda whispered in Michelle's ear before lightly licking MIchelle's neck.

"Ohhhhhh!" Michelle's body trembled with excitement as Brenda kissed and nibbled her neck.

"Did you like that?" Brenda smirked as she leaned back, knowing full well Michelle was completely aroused. "No need to answer," Brenda continued, while letting her left hand slip around Michelle's hip until her hand was cupping the front of Michelle's panties, "I can just check myself right?" Michelle nodded, feeling her knees buckle as Brenda lightly massaged her crotch. "Seems you're a bit damp," Brenda said as her fingers slid over Michelle's swollen balls, "I hope you don't stain your dress!"

"I'm, I'm sure it'll be fine." Michelle responded, closing her eyes and savoring Brenda's touch.

"Okay, I guess I'll have to trust you on that." Brenda replied, watching Michelle's reaction to her touch intently. "Maybe we can meet up for lunch too," Brenda said softly, "what do you think?"

"I'd love that a lot!" Michelle responded eagerly.

"Sounds like a plan!" Brenda said abruptly releasing Michelle and stepping back, quickly severing physical contact with her. "Don't forget to fix yourself before you go to the office," Brenda said with a wink, "I wouldn't want anyone to question what you've been doing in the stairwell!"

"Yes," Michelle stopped short of calling her Ms., "I will."

Brenda backed up just enough to allow Michelle room to readjust her dress. As Michelle turned to leave, Brenda gave Michelle's ass another firm squeeze before walking through the doorway to her floor. Michelle felt the need to steady herself as she descended the stairs. What had come over Brenda? Obviously, spending time with Ms. Allison had her dressing up a bit more, but the apartment hunting made sense for it too. Had chumming around with Ms. Allison also made her more assertive? Michelle's mind raced with questions as she entered the office, setting her purse aside, then ducking into the lady's room to double check her lipstick.

"Good morning Michelle," Ms. Allison said gleefully as Michelle stepped back into the office, "how was your day yesterday?"

"It was quite the adventure Ms.," Michelle replied, unsure of what details to go into, "they were very nice as well."

"I am sure they were," Ms. Allison motioned for Michelle to take a seat at the reception desk, "I've been using them for a few years now, they take great photos and seem to enjoy the extra perks of the job." Michelle blushed, feeling the familiar tingle in her backside as Ms. Allison took a seat on the edge of the desk. "Did you see Brenda this morning?"

"Yes, I did Ms.," Michelle replied quickly, "she looked quite lovely, I've never seen her with that much makeup on."

"She is a very attractive woman, and doesn't really need anything to highlight that," Ms. Allison said while looking Michelle over, "I think she just got used to downplaying her femininity and needed a nudge back to it."

"That does make sense Ms. Allison." Michelle replied meekly.

"I am sure you can help her with that as well," Allie continued, "as you're certainly not one to downplay your femininity."

"True." Michelle blushed in response.

"That green does look lovely on you today Michelle." Ms. Allison smiled warmly, enjoying Michelle's reaction to Her comments. "I'll let you get to work," Ms. Allison said as She slowly slipped off Michelle's desk, "we may have a new applicant coming in next week to replace you."

"That will be nice!" Michelle replied, excited to give up her office job.

"And I am sure, after I build your profile on the site and upload yesterday's pictures," Ms. Allison said as She started to walk to Her office, "you'll have a very busy social calendar soon."

Michelle trembled slightly and blushed at the idea more people would see her pictures. It wasn't just that people would see them, Mistress Tina, Bernard, and everyone else she'd met at her coming out party would soon be looking her over. Michelle could feel her face burning red, remembering some of the poses, positions and actions she was captured in during the course of the day. It was scary, yet arousing to know they would look at her with lust in their eyes.

The morning passed quite slowly for Michelle, suddenly her phone beeped. She assumed it would be Brenda about their lunch date, instead it was Babette, who as usual started the conversation by calling Michelle a slut.

"Pics are up on the site!" Babette texted.

Michelle didn't even respond, quickly moving her mouse she brought up the private site where the girl's had profiles, her face blanching as she saw her profile picture. It was a nice picture, like a professional headshot, but Michelle knew there was far more behind it. Finally mustering the courage, Michelle clicked on her profile. The description was fairly mundane at first, name, age, measurements, height and weight. Unlike a normal dating profile, Michelle's interests were not her personal interests but sexual ones! It was almost terrifying to think unknown people could read this and know every kink or sexual act Michelle enjoyed. It certainly removed the mystery to it!

"Scroll to the very bottom," Babette texted, "the number of visitors gets tracked."

Quickly scrolling past the folders of pictures, Michelle saw the number was already up to 10. She was almost pleased with herself, considering the site just went up today, 10 was a good start in Michelle's mind. Scrolling back up, Michelle started at the tamer picture folders. It was hard for her to believe that the pictures she was seeing were actually her own, or, more accurately, were pictures of her! Michelle hadn't noticed how shapely her legs had become, how round her bottom was now, and of course how amazing her breasts were.

"I'm hotter than Cynthia will ever be!" She said proudly to herself. "Stuck up bitch!"

"I hope that wasn't meant for me!" Brenda said as she walked into the office.

"Oh!" Michelle's eyes got wide, her face white as Brenda approached. "No, that wasn't for you," Michelle was obviously panicked as she tried to close the browser window, "I was just looking at, um."

It was too late, Brenda was standing next to her already and looking at the screen. Thankfully, it was still one of the tamer looking pictures of her, although it was still a bit risque to share with Brenda. Or so Michelle thought. In the picture Michelle was wearing a snug fitting gown with a hefty slit up her left leg and a strapless top that gave her chest a bit of a lift. To show off the legs slit, Michelle's left leg was cocked outward slightly as she stood putting more of her weight on her right foot.

"Well my girl certainly carries herself quite well," Brenda said rather proudly, "you look sexy as hell!"

"Thank you!" Michelle blushed deeply, hoping Brenda wouldn't ask to see more pictures.

"Do me a favor," Brenda said leaning forward so her mouth was closer to Michelle's ear, "download that picture and send it to me." Brenda's voice was soft, stern and breathy causing the hair on the back of Michelle's neck to stand on end. "I want to make your stunning look my phone's background!"

"Okay!" Michelle replied, quickly right clicking the photo. "I can do that!"

"You're so good to me!" Brenda said, standing slowly while letting her hand slowly trail up Michelle's left arm. "Ready for lunch?"

"Sure!" Michelle replied, relieved Brenda's interest in the picture she'd seen lapsed so quickly, hit send on the message for Brenda's new background.

"Let's go," Brenda smiled while extending her hand to Michelle, "but don't forget your purse!"

"Oh, I can't do that." Michelle replied somewhat flustered.

As they approached the outer door to the office Brenda stepped ahead and held it for Michelle. Once through the door, Brenda took Michelle's arm in hers, walking them to the elevator. As they stood at the elevator door, the muted brass door reflected their images. Michelle was somewhat dumbstruck by what she saw, feeling almost more effeminate than usual. Brenda's French braid made her hair look shorter, while not masculine it was certainly not as done up as Michelle's hair. Brenda's sweater, dress pants and wider stance was also a stark contrast to Michelle, who had crossed one foot in front of the other while they waited. Michelle's dress and heels showed off her legs, the large purse hung from her other shoulder, while her hand hung loosely from Brenda's arm. A quick glance and someone could certainly mistake them for a regular, male and female, couple. The exception to that was the obvious male was female and the very obvious female had been a male. The little voice reappeared for the first time in forever in Michelle's mind asking "what are you doing?" Michelle shook her head quickly to quell it.

"Everything okay Sweetie?" Brenda asked.

"Yeah," Michelle replied as the elevator doors opened, "I'm good."

A gentleman in the elevator held the door with his arm, while smirking at Brenda and Michelle as they entered. Obviously, Michelle surmised, he knew who the girl was in this relationship too. What she hadn't noticed was the smirk on Brenda's face as the dynamic was not lost on her either. It was a carefully crafted dynamic based on Allie and Brenda's time together. As the elevator doors closed Brenda's phone made a noise. Pulling it from her pocket, Brenda opened her messages, retrieving the picture of Michelle in the dress.

Ms_Allison
Ms_Allison
1,374 Followers