The Agency Ch. 19

Story Info
A trip to the office with Ms. Allison and someone else...
6.8k words
4.83
14.1k
22

Part 19 of the 24 part series

Updated 10/07/2023
Created 02/01/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
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!

When Melissa awoke in the morning the first thing she did was check her phone, there was still no message from Brenda. She climbed out of bed, walking into the living room to see if Babette may be there. As Michelle stepped into the main living area, Babette was nowhere in sight.

"I swear this is more torturous than a corset!" Michelle hissed, walking to the kitchen to make coffee.

Michelle had showered and dressed by the time Babette walked back in, openly and brazenly doing the walk of shame. Babette's dress was definitely not something anyone wore first thing in the morning, the blue sequins and short hem made more for a cocktail hour than morning coffee run.

"I'd ask how your night was," Michelle giggled while pouring Babette a coffee, "but it's kinda written all over you!"

"It was a good time," Babette replied with a smile, "how was your day with Anna?"

"It was okay, but I have a question," Michelle's voice dropped to a whisper, "does Ms. Allison employ real women too?"

"Real women?"

"Yeah, like women who don't have their manhood locked up under their cocktail dress silly!"

"I've never known Her to since I've been here," Babette replied, "but I've only been here five or so months before you." Babette sipped her coffee before continuing, "Why would you ask that though?"

"I was supposed to go to lunch with Brenda yesterday," Michelle replied, "but I went to see Anna, and Brenda went to lunch with Ms. Allison. Then last night they went out together again! I'm losing my mind."

"Relax Sweetie!" Babette said, pulling Michelle in for a hug. "I'm sure there's nothing to worry about," Babette's voice and hug were reassuring, "I don't know any of the other girls that were born girls if that helps."

"Yeah, it does a bit." Michelle replied. "But I still haven't heard from her either," Michelle said as she stepped back from Babette, "and that's not like her."

"Well," Babette started as she walked to the living room, "maybe she's tied up in the dungeon and can't call you because she has a ball gag in her mouth?"

"Oh come on!"

"Standing there in a pair of heels, perspiration all over her sensuous body, a deep purple waist cincher holding up long black stockings," Babette's voice was syrupy smooth emphasizing the sultriness of the picture she was painting, "arms lifted high overhead with big black cuffs and the remnants of the candle wax that had been dripped ever so slowly on her nipples."

"Jesus Babette!" Michelle snapped. "That's not an image I need in my head right now!"

"Why not? It's the image I have in mine!" Babette teased.

"You are no help at all!" Michelle tersely replied, the sound of her phone beeping caught her attention though. "Oh there she is!" Michelle said as she looked at the notification on her phone. "Well, she's not tied up in the dungeon," Michelle replied somewhat relieved, "but she's not feeling well and isn't coming in today."

"Sure," Babette sipped on her coffee, "gotta let the whip marks heal."

"You are incorrigible!" Michelle replied with an eye roll.

"Yeah, but you love me that way!"

"Yes I do," Michelle responded, walking up to her roommate, "I'll miss these conversations when you move out."

"And I'll miss you too," Babette replied, "sleeping with you is the only time I get to be the bigger spoon!"

"You are too much!" Michelle said, "I have to go to work," she said, giving Babette a soft kiss on the lips, "one of us still earns her living inside of an office instead of on her back!"

"Oh I was definitely on my front," Babette teased, "and my knees, and all fours, and a few other positions!"

"You're such a slut!" Michelle giggled, giving Babette's but a light spank.

"And you want to be one too!"

"I'm just hoping my girlfriend doesn't end up having the same thoughts!" Michelle replied before heading out.

For the first time since commuting to work, Michelle didn't pay attention to those around her. Usually she revelled in the attention, enjoyed the so-called "man glare", or the envious looks of real women. Instead, today Michelle was locked in her own thoughts, and the thoughts Babette had so cruelly put there. Could Brenda really stand in heels or allow herself to be gagged? Michelle shook her head; these weren't the questions she needed to ask herself. What she really needed to do was focus and try to make it through her work day without blurting questions to Ms. Allison about Brenda.

Entering the building, Michelle took the elevator to her floor, still lost in thought. It wasn't a surprise, Michelle had deep feelings for Brenda and was moderately sure she felt the same way. While Michelle didn't feel like she'd been tricked into taking her current job, she was concerned Brenda wouldn't be so aware of what was happening. It was truthfully a baseless thought, but still, Ms. Allison was quite cunning in finding out about people. Certainly, Brenda was doing far better financially then Michael had been, so she could resist better than he, but then again Ms. Allison was a master chess player.

"Well good morning, Michelle!" Ms. Allison's voice startled the distracted girl.

"OH! Good morning Ms. Allison!" Michelle responded almost dropping her purse as she looked at her Boss. "I wasn't expecting you in so early."

Ms. Allison was perched on Michelle's desk, leg's crossed, the long black skirt She had on pulled up over Her knee showing of the kidskin thigh high boots the loose-fitting dress typically covered. Moving Her legs slowly, Allie smirked as Michelle's eyes followed Her leather clad legs. Michelle's fetish for heels and love of legs were her Achille's heel.

"How was your visit with Anna yesterday?" Allie asked as Michelle attempted to settle in for her morning.

"She was quite nice," Michelle replied sincerely, "I enjoyed my time with her."

"I understand you got some wonderful outfits as well," Allie said as She slipped off the desk walking slowly toward Michelle, "I am sure you'll look amazing in them!" Michelle blushed unable to hide her excitement at the outfits. "Do you know what tomorrow is?"

"Yes," Michelle gulped, "my photo session."

"And are you looking forward to that as well" Allie asked.

"Yes, I am Ms." Michelle blushed even deeper.

Ms. Allison slowly walked up to Michelle, lightly touching the side of her face, "And if you think paying Anna for her services were fun," She said lowering her hand slowly, letting it glide over Michelle's neck and breast, "you're really going to enjoy paying them for their services." Michelle felt her body shudder at Her words. "they're stamina is out of this world!"

Allie enjoyed the reaction she was seeing from Michelle. The hair on her arms was standing on end and She could see Michelle's blouse moving from the rapid beating of her heart. Even Michelle's breath was a bit quicker than usual. Allie leaned in, pressing Her chest to Michelle's, feeling her employee tremble even more.

"Why don't you follow Me to My office baby girl." She instructed before abruptly moving past the still shuddering Michelle.

Following Ms. Allison down the hallway, Michelle felt the sudden tingling throughout her panties. While she'd never considered herself kinky before coming to The Agency, she certainly embraced the kinkier side of her employment. Even now she could feel her mouth watering, her asshole loosening and tingling and her caged member raging and leaking inside. Whatever was about to happen, she was much more than a willing participant in the events.

"Don't bother disrobing," Ms. Allison said as She led Michelle into the office, "in the bathroom there is everything you need for today."

"Yes, Ms." Michelle replied hearing the slight shudder of excitement in her voice while her stomach flipped.

"Don't rush, you have an hour."

"Thank you, Ms. Allison." Michelle felt her left ankle buckle briefly as she walked through the door to the small hallway leading to the bathroom.

The full bath just outside Ms. Allison's office had a long vanity on which a number of items sat. A hand written note stated Michelle needed to start from the left side and end on the right. The first item in a red bag was an enema kit. Michelle felt the hair on the back of her neck stand on end. Her trembling fingers undid her blouse, which she hung neatly behind the door. Removing her dress and stepping out of her heels, Michelle started to remove her lingerie. Picking up the enema kit, Michelle walked stark naked to the toilet. While the process was quick, Michelle still found it odd that she got excited over the rush of fluid entering her body.

"Okay," Michelle said unsteadily to herself, "let's see what we have!"

Opening the first box, Michelle held up the first article of clothing, looking at them quizzically. Finding a small tag, she was able to figure out which part was the back. Stepping into the panties, Michelle pulled them upward feeling the red lace slide over her skin. The lace panels in the front and back were connected by two small elastic straps which framed her cage like red lace curtains.

"Crotchless panties?" Michelle asked herself as she looked at them in the mirror.

Michelle pulled on the next item, which was a matching red lace bralette with small shelves which made up the cup leaving ninety percent of her breasts exposed. Next came a pair of red lace stockings and matching elbow length gloves. Michelle put her hair up in a ponytail, held in place with a red scrunchie. By the time Michelle looked at the next box a line of precum dangled from her cage to the floor.

"Ohhhhh!" Michelle moaned at the sight of the red strap cuffs and heart shaped padlocks.

There were four red leather cuffs with silver buckles, the cuffs were roughly an inch wide and thin. With a cuff locked on each ankle and wrist, Michelle found another one with a heart shape in the front and a dangling ring that she put around her neck. The last box contained a pair of red patent heels with a 1/2 inch platform and chromed spiked heels which Michelle slowly slipped on.

"I almost have to stand with my knees bent in these." Michelle said as she tentatively pulled her fingers from the counter top. "Okay, time's almost up."

Michelle walked out of the bathroom, slowly opening the door to Ms. Allison's office, feeling more exposed than she'd ever been before. It was odd, she was clothed, yet her clothing covered next to nothing. As she stepped she could not only feel her breasts sway but also her cage.

"Well don't you look like a little slut!" Allie teased as Michelle stepped into the office. "A little slut with an adorable blush!"

"Thank you, Ms. Allison."

Michelle was directed to the corner of the office where a wheeled pedestal with a red padded top was placed. As many times as she'd been in Ms. Allison's office, Michelle had never gotten used to the fact that both exterior walls were nothing but windows.

"Go ahead and kneel on the pad," Allie directed and motioned, "knees nice and spread too."

Allie locked Michelle's ankles to the base by the attached D-rings, then clipped her wrists together, pulling another strap to the base and cinching it tightly. The strap holding Michelle's wrists would keep her arched back slightly, but would help hold her upper body in place. Walking slowly back to Michelle's front, Allie enjoyed what She was seeing. Michelle had created a small pool of precum in the short time she'd been on the platform, her mouth was also slightly agape as she practically panted with excitement. The entire plan for this day was to make sure Michelle left as horny and frustrated as possible, well, that was part of the plan.

"Just two more items to put on you now," Allie smirked holding up a large red satin blindfold, "just in case there was any question as to what you truly are."

"Yes, Ms.!" Michelle tittered with excitement as Ms. Allison held the red blindfold up showing the silver embroidered word on the front. "I am a slut."

Allie placed the large blindfold over Michelle's eyes, the bottom extended beyond her cheeks and the sides past her temples, Michelle's world had just turned to darkness. Michelle could feel a pair of earbuds being placed in each ear, suddenly hear ears were filled with white noise. She could hear Ms. Allison talking but Her voice was muffled and indistinguishable. Ms. Allison all of a sudden sounded as if She were talking while Her mouth was covered by Her hands.

"Can you hear Me baby girl?" Allie asked just above a normal conversational tone. Leaning forward, Allie asked again, "How about now? Can you hear Me?"

There was no reaction from Michelle at all. Allie knew that if Michelle had heard Her at all, Michelle would have answered. Michelle was far enough in her training; she would not be able to mislead her Boss. Plus, any time Michelle was in a situation like this, bound and vulnerable, her dependence on Allie increased exponentially. Allie undid the lock at the top of Michelle's cage, then carefully but quickly removed the two pieces. By the time She set them on Her desk, Michelle's hardon raged, protruding vulgarly from her body. Allie smirked, then turned to the hallway Michelle had just left. Walking past the bathroom Michelle had changed in, Allie knocked on the second door lightly before opening it.

"Are you ready for this?" Allie asked in the most reassuring voice She could.

"I think so," the woman replied, "I feel a bit odd about all of this though." The woman's voice cracked with nervousness as she spoke. "I mean, this outfit is definitely not me!"

"I for one think you look fantastic," Allie replied calmly, "and she will have no idea what you look like unless you want to share it."

"And she will be okay through all of this? She won't get hurt?"

"No, she won't get hurt," Allie smiled easily while reaching for the woman's hand, "and she's a very willing participant!"

"Okay, let's go before I chicken out!"

"You will be fine," Allie replied leading her to the hallway, "and Michelle will absolutely love the idea of you becoming Ms. Brenda."

Unseen to Michelle, when Ms. Allison led the soon to be christened Ms. Brenda entered the office, they were both mostly clad in black leather. Ms. Allison had shed Her long skirt, blouse and jacket revealing a strapless leather bustier, leather boycut bottoms and the thigh high leather boots Michelle had seen already. Brenda had on a pair of 3 1/2 inch black kidskin heels, a black leather miniskirt, black hose and a black leather halter top style bustier. Brenda inhaled deeply at the site of Michelle, unconsciously squeezing her legs at the site of her friend bound and excited.

"Maybe it was a bad idea not to wear panties today." Brenda whispered.

"She is quite a sight isn't she?" Allie giggled.

"You promise she cannot hear me right?"

"MICHELLE!" Allie called out. "Brenda's here to learn how to be a dominant!" There was no reaction from Michelle while Brenda blushed deeply. "If you're not okay with that, make some kind of movement or say any word at all!"

"Okay, okay!" Brenda tugged at Allie's arm. "I get it! She can't hear us."

Brenda walked slowly toward the bound Michelle. After meeting Michelle, and becoming attracted to her, Brenda had started to do a lot of online research not only about The Agency, but Allie as well. All this had come to light the night Brenda had logged into the personality assessment. Just as Michelle had done, yesterday while Michelle was with Anna, Brenda had gone through the other quiz. Over lunch, Allie had explained a lot of the goings on with Brenda. Obviously, not all of them, but the highlights to include Her own role in all of this. For the past month or more, Brenda had been watching D/s videos focusing on Dommes and femme submissives. Before their first meeting, which had happened before their lunch, Allie had mentioned doing this exact thing with Michelle. While scared and nervous about it, Brenda eventually agreed. While most of the employees that Allie had sent upstairs to see the plastic surgeon, until she'd seen Michelle, she'd considered them all men trying to be women. It had been impossible for Brenda to see Michelle as a man from the very beginning, regardless of what had been tucked into her panties. The thought had been what had immediately attracted Brenda to her. Now, seeing her bound, blinded and exposed, Brenda could feel the heat growing inside her very short skirt.

"What do you think?" Allie asked as Brenda slowly walked around Michelle.

"You're sure she can't hear us?" Brenda asked.

"Just watch." Allie said as She walked to the opposite side of Her charge from Brenda. "This should convince you." Allie said as She leaned downward until her mouth was barely three inches from Michelle's. "Baby girl," Allie said in Her normal voice, "your girlfriend is here to learn how to treat you like the slutty submissive sissy you are!"

"Jesus!" Brenda blanched yet pressed her hand against the front of her skirt while squeezing her legs tight enough to lift her left foot from the floor.

"Exciting, isn't it?" Allie smiled warmly, obviously pleased by Brenda's reaction.

"Yes!" Brenda blurted, shaking her had and lowering her foot while trying to recover her composure.

"Now, the idea is to excite her to the point she almost cums," Allie said walking back to Her desk, "but not allow her to cum."

"Okay." Brenda replied unable to lift her gaze from Michelle.

"First, we will let her know that there are two of us here," Allie said handing Brenda a long feather, "rub those over her nipples for a bit."

"Okay." Brenda replied then asked, "Um, how?"

"Think of how you'd enjoy feeling those against you own breasts," Allie replied as she put on a pair of latex gloves, "and do that to her. Plus, she will let you know what she likes."

Running her index finger over the edge of the feather, Brenda enjoyed the smooth plume, knowing exactly how she'd enjoy it. Putting her hand close to Michelle's left breast, Brenda slowly drew the feather over her rapidly hardening nipple like a bow on a violin.

"Ohhhhhhh!" Michelle moaned and tensed, straining at her bonds.

"She seems to like that," Allie said confidently, "try doing that on both at the same time."

Brenda did as Allie had suggested, watching Michelle's cock twitch and dribble more precum. After doing that across the top and bottoms of both nipples, singularly and together, Brenda twisted the feather between her finger and thumb to lightly beat Michelle's nipples with the edge. Michelle groaned louder, trying to escape the feeling while also trying to get more.

"Okay, now do that to her crotch," Allie instructed, "you've rubbed estrogen on her nipples enough for her to recognize your touch, we don't want her knowing who else is here."

"Particularly if it's me!" Brenda giggled.

"Although it'll make for interesting dinner conversation later this week!" Allie laughed.

"No kidding!" Brenda replied while drawing the width of the feather across the underside of Michelle's aching cock.

As Brenda went to glide it back over Michelle's cock again, Allie stepped behind Michelle, leaned forward and began to rub both breasts with estrogen cream.

"Oh my God!" Michelle blurted as she soon discovered whatever was going on required three hands.

The hands on her breasts were firm, tugging and rolling her nipples. The scent of the estrogen cream filled her nose, but it was the feather sliding over the underside of her crotch that had her puzzled. Although, thoughts requiring much focus required far more brain power than she could muster at the moment. The conflicting feelings, the sensitivity of her hard nipples and raging cock, filled Michelle's brain. In another minute, it didn't matter to Michelle how many hands were on her, she just wanted to enjoy their touch and hopefully orgasm!

Ms_Allison
Ms_Allison
1,374 Followers
12