The Agency Ch. 04

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Michelle's training intensifies while Babette is away.
9.7k words
4.59
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Part 4 of the 24 part series

Updated 10/07/2023
Created 02/01/2021
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Ms_Allison
Ms_Allison
1,371 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!

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

In the morning, Michelle awoke, her panties soaked and caged member surging at its bonds. She woke up an extra hour early, changing into her selected workout clothing, then laying out her purple yoga mat. While she did feel incredibly odd, doing yoga in her cramped apartment, she had to admit Phoebe was quite good at her job. And incredibly flexible. At the end of the 50-minute workout, Michelle's butt muscles, hips and abdomen all ached.

"I'll have a nice round ass in no time with these workouts!" Michelle said downing her post workout drink.

As she'd done before, Michelle worked her way through the process to get ready for work. Although today, she'd decided to change up her pre-selected outfit. After exiting her shower, Michelle applied moisturizer and put on a short red satin robe. She loved the feel of the satin against her freshly shaved flesh.

"I think this will do nicely!" She said selecting a black satin and sheer rosette lace bustier and matching thong.

The thong was delicate, with a sheer black front panel inlaid with black roses and a rosette border along the top of the small panel. There was even a rose in the back of the thong that sat right at the top of Michelle's ass. The bustier matched, with the two front panels also consisting of black sheer lace and roses. The cups were sheer as well, with two large roses covering the nipples on Michelle's fake breasts. It was probably a bit over the top to wear to work, but Michelle didn't care.

"Time to give these a whirl!" Michelle said excitedly as she pulled a brand-new pair of back seamed stockings from her drawer.

They were long enough they came within an inch of her thong, with 4-inch lace tops to match the rest of her outfit. While it took some work to make sure her seams were straight, Michelle loved the feel of them. She then retreated to her bathroom to do her makeup and put on her wig. It took a bit of doing to find the perfect, deep red lip color to go with the look she had in mind. Eventually she found it, adding that and a bit of perfume before exiting the bathroom.

"Hmmm, which next?" She asked herself. "Oh, time to push yourself!"

Michelle walked to her closet selecting a pair of 4-inch heels that would fit perfectly with her dress. Yes, they were taller than her usual heel but the black and white "wingtip" look of them was what she wanted. Retrieving the silver plug, Michelle managed to find a nearly empty bottle of lube she'd bought a month ago when it had seemed like a frivolous expense. Tugging the thong aside, Michelle leaned over her bed, placing one knee on the mattress, to begin the process of inserting the plug.

"Relax." She told herself. "Deep breath, then let it out." The tip penetrated her rather easily until she tensed up. "Come on," she scolded herself, "you can do this!" It took three attempts to seat the plug properly, but she finally managed. "I wish I had a full-length mirror!"

Michelle felt incredibly sexy in her current state. Catching a glimpse of herself in the reflection in her bedroom window, Michelle saw her silhouette and knew she looked sexy too! Fixing her tiny thong, Michelle decided to wait on putting on her dress, instead she added a couple bracelets and went to the kitchen to make another cup of coffee and breakfast. She had almost twenty-five minutes before she needed to leave and wasn't in the mood to finish dressing yet. Instead, she enjoyed the freedom of just wearing her lingerie and heels for a while.

"It's about that time." Michelle huffed, slipping off her couch and retrieving her dress from the bedroom closet. "But this will be worth it!"

The dress had long sleeves and a hem that landed just below her knees. The white dress, with asymmetric black on either side, added shape to her masculine hips while making her waist seem smaller. Michelle not only loved the look but the satin lining which hugged her bare butt and caressed her midsection. She could feel it everywhere. Picking up her handbag, Michelle stepped out of her apartment and into the hall.

"Be careful now." She whispered to herself as she walked to the elevator.

The 4-inch heels forced Michelle to shorten her stride slightly, but it amazed her how much different the inch difference made not only physically but mentally. She could feel her butt was pushed out just a bit more and the heels added more definition to her lower legs. They even made her false breasts jiggle just a bit more. Stepping out of the building, Michelle paused for a moment to adjust to everything.

"Oh I caught him looking," Michelle giggled to herself, "and him." Turning to face the railing, Michelle kicked one foot up behind her as if she were adjusting the heel. "That worked!" She giggled louder as she watched a man walk into the light pole.

Walking down the steps, Michelle walked into the flow of the other pedestrians, feeling her hips move more with her new stride. Michelle easily made her way to the subway, her decadent lingerie seemed to make the vibrations filling her body far more enjoyable. She didn't even need to get off the train on the way to work like she'd had to do on the way home last night. Instead she embraced the slight numbness the massive vibrations had caused in her ass.

"Good morning Babette!" Michelle said proudly as she walked in.

"Good morning," Babette paused as she looked up, "well aren't you very Breakfast at Tiffany's looking today!" Michelle turned slowly, stopping to show off her seamed stockings. "Oh, you minx!" Babette's overjoyed response made Michelle proud of her appearance. "That is a fantastic outfit Sweetie!"

"Thank you!" Michelle gushed with pride. "You should see what's underneath!"

"How is your ass feeling this morning you slut!?!"

"It's not as bad as last night," Michelle replied blushing deeply at being called a slut, "and you said I'd always feel horny, so why not embrace it right?"

Settling behind the desk, Michelle assumed Babette's role while she oversaw. It gave Michelle a great sense of purpose and helped her focus on something other than how horny she was.

"And how are my girls doing this fine morning?" Ms. Allison asked as she entered the office.

"Great Ms. Allison!" Michelle proudly replied.

"Oh, look who's gotten out of her training heels!" Ms. Allison smirked. "Stand up and let me see you my sweet Michelle." Immediately standing and stepping to the side of the desk, Michelle turned slowly to show off her outfit. "Very nice, and your seams are so straight still!" Michelle beamed with pride at her compliment. "How have you managed with stairs in those?"

"I did okay on the few steps in front of my building Ms." Michelle responded confidently.

"You can get some more practice now," Allie smirked, "the Dr.'s office is two floors up and you have an appointment in ten minutes." Her smirk turned bigger as she watched the blood drain from Michelle's face. "Better get going."

"Yes, Ms. Allison." Michelle dutifully replied.

"Get going girlie!"

"Yes, Ms.!" Michelle walked to the office door as quickly as she could. "The stairs will be easier than the Dr. I think!" Michelle said to herself as she turned toward the stairway.

She was right, the stairs were relatively easy, it was a bit awkward stepping up on them with her heels on, but she managed okay. Stepping into the Dr's office, Michelle took a deep breath.

"Yes, can I help you?" The receptionist asked.

"Yes, um, I'm Mi," Michelle paused momentarily as she'd almost said her birth name, "Michelle Summers and I have an appointment."

"Okay, please have a seat, the Dr. will be with you shortly."

Michelle slowly sat, crossing her legs, and thumbing through a Cosmo magazine. She was glad the receptionist didn't ask which Dr.! Then it dawned on Michelle, who was the Dr.? Was it a he or she? Which would she want it to be? It was a no-win situation and embarrassing either way. Michelle was slightly lost in her thoughts when she heard a man's voice.

"Michelle Summers?" he said again.

"Yes, sorry." Michelle was the only patient in the waiting room so it was kind of silly for him to ask for her. Standing and smoothing out her dress, Michelle walked toward the male nurse. "I was just a bit lost in thought."

"It happens." His smile was warm and white against his tan skin. "Follow me please."

Even in a pair of scrubs, this guy was a stud! Michelle struggled to take her eyes off his well-toned body. He stopped, turning to guide her into a room only to catch Michelle checking out his ass.

"Right in here." He smirked as their eyes met.

Michelle sat, letting him take her hand as he took her blood pressure and other vitals. His touch was warm, almost loving. Even in her 4-inch heels he towered over Michelle, his hands dwarfed hers as well.

"The Doctor will be in shortly," his voice smooth like syrup in Michelle's ears, "please disrobe down to your panties and put on the gown on the exam table."

"Okay." Michelle felt her face blanch again! "Panties." She practically hissed as the door closed behind him. "Of all the days to wear this!"

Michelle removed her dress, hanging it up on the door before stepping out of her heels. It felt so silly to remove almost all the clothing she had painstakingly put on to perfection just a couple hours ago. On top of the gown was a small pair of pink socks with white rubber grippers on the bottom. Michelle pulled the robe on, tying the two knots in the back, before putting them on her feet. Sitting on the exam table, Michelle tried to relax but found that near impossible. Eventually there was a quick knock on the door.

"Come in." Michelle tentatively answered.

"Good morning Ms. Summers," said the middle-aged woman walking into the exam room followed closely by the male nurse, "I'm Dr. Jones but please just call me Nancy."

"Nice to meet you Nancy." Michelle replied, finding her eyes drifting back toward the male nurse for some reason.

Nancy gave Michelle a routine physical, checking her eyes, ears, listening to her lungs, having her lay on her back and pressing on her abdomen. The conversation was casual and relaxed, certainly more relaxed than Michelle was as her mind raced the entire time. Did Nancy know she wasn't born a girl? She must, right? Did her nurse know too? Surely Michelle wasn't the first patient that had come up to her office!

"Have you just recently started wearing heels?" Nancy asked as she took the small socks off Michelle's feet.

"Yes." Michelle smiled uncomfortably wondering how she could know.

"Make sure to stretch your calf muscles if you're going to wear them often," her voice was kind and certainly not judgemental, "or over time the muscles will shorten. I love your nail color by the way!"

"Thank you."

Michelle relaxed a bit as they talked about exercise and diet, with her proudly announcing she'd done yoga just this morning. As Nancy's hands moved to Michelle's knees, then further up, her tension grew again. Whether Nancy knew Michelle was a boy or not was about to be uncovered as her hands disappeared under the exam gown. Taking a deep breath, Michelle closed her eyes bracing herself for Nancy's unknown reaction. Without missing a beat, Nancy slid Michelle's thong out of the way to examine its contents. Michelle wasn't sure whether to be embarrassed or aroused!

"Make sure yourself lubricated if you're going to wear this every day," Nancy smiled warmly, "and from time to time forgo tight bottoms to keep yourself healthy, which may require you to go commando from time to time." Nancy gave Michelle a wink then continued, "Although I wouldn't suggest doing that at work."

"No, not at all." Michelle giggled.

"Okay, I'll need you to stand and bend over the table now." Nancy saw the panicked reaction on Michelle's face and gave her a warm smile. "Jeffrey, could you step out for a moment please?"

"Of course!" The male nurse dutifully replied before exiting the room.

"He's a good nurse, and would take your secret to the grave," Nancy said as she helped Michelle off the table, "but I also understand you're new at this."

"You could tell?"

"Oh Allie sends all her new girls up for their first check up with me," Nancy's voice was surprisingly soothing to Michelle, "I'm used to the reaction at this point." Michelle returned Nancy's smile and turned slowly to face the table. "He will need to come back in and take some blood though, I like to be thorough."

"Thank you," Michelle said as she leaned forward over the exam table, "should I pull my bottoms down?"

"They are adorable, but yes you should," Nancy replied as she moved the gown out of her way exposing more of Michelle's back, "I'd hate to ruin them." Michelle pushed the thong over her hips feeling it fall to her ankles. "Now, deep breath."

Feeling Nancy's hand on her back, then the base of the plug, Michelle exhaled deeply as Nancy removed it easily. Michelle didn't miss the feeling for long, as Nancy's gloved and lubed finger soon slid inside her. She fought the urge to moan.

"Stay right there for a moment," Nancy said as she extracted her finger, "it's far easier and less embarrassing to leave with this the same way you brought it in." Nancy quickly cleaned off the weighted stainless steel plug, before applying lube and reinserting it. "You can wipe up, then pull your panties back up."

Taking some soft paper towels from Nancy, Michelle did as she was told, then sat back on the exam table. Nancy spoke to her a bit about safety precautions with extended plug wear, and gave Michelle a prescription for an enema kit.

"It's not like you girls can claim that as a work expense after all."

Michelle wasn't sure how to take that, while she'd certainly considered anal play would that be a job requirement? That hadn't really been discussed, she knew Babette had a date a couple nights from now, what were the expectations? She would have to find a way to ask!

"Any questions at all?" Nancy asked.

"No, not really," Michelle had them but Nancy wasn't the person who could answer them, "thank you so much."

"I'll send Jeff back in just a minute," Nancy said as she walked to the exam room door, "when he's all set you can get dressed."

Michelle had to chuckle at the inference, crossing her legs and squeezing her sphincter around the plug, while she knew she wasn't gay there was something irresistible about the male nurse. She was lost in thought again as he entered and set a small brown paper bag on table. They made small talk while he got everything ready. As he approached her, Michelle wondered if she should move or uncross her legs or something.

"You're fine right where you are," Jeff reassured her as he stepped to her and straddled her lower legs, "this will just take a moment." Setting a vial on the exam table Jeff continued, "The Dr. gave me a couple samples for you to bring home."

"Oh, thank you." Michelle felt her hips practically wiggle on their own knowing what the samples meant.

Michelle was now over her initial embarrassment and uncomfortableness, started to feel sexy and a bit mischievous. As Jeff put the rubber band around Michelle's arm, she wrapped her right leg around his, letting the back of her foot glide up his leg a couple inches. Michelle couldn't believe it, she was overtly flirting with this guy! A guy! It felt so empowering!

"You're going to feel a slight prick." He said causing Michelle to giggle.

"Slight?" She asked while raising an eyebrow.

Jeff winked, then changed to the second vial. As he undid the band on her arm, he pressed his hips forward, pushing his crotch against her leg. Michelle felt him, his cock, against her leg! He was hard! She felt her ass tense again at the realization that she had been the one to excite him! A brief shudder ran through her body while he put a small Band-Aid on her arm.

"You're all set to get dressed now." Jeff gave Michelle a slow look up and down, as if he not only knew he could simply overpower her and take her right there, but that she more than likely wouldn't resist.

"Thanks." Michelle responded, slowly slipping off the exam table.

They paused for a moment, looking each other over, both feeling a sense of lust between them. Michelle squeezed her legs together while Jeff made no secret of adjusting the front of his scrubs. Finally the intercom interrupted them with Jeff being called to the front desk. Upon his exit Michelle had to sit for a moment and not only compose herself but come to terms with what she was thinking and feeling. There was no denying she'd been physically attracted to him, how could she not? He looked like a model! But she'd been sexually attracted to him as well. How far would she have let it go? Michelle shook her head, removing her gown and quickly getting dressed.

"Thankfully this is here," Michelle said, checking herself in the full-length mirror behind the door, "okay, seams are straight, time to go!" Stepping out of the exam room, Michelle walked toward the front desk, seeing Jeff leaning over to talk to the receptionist. His ass sticking out into the hallway, Michelle considered giving him a playful touch but decided against it. "Have a nice day!" She said as she walked past him making sure her hips swayed as she stepped.

"You too!" Jeff replied warmly.

Michelle quickly got back to reality as she tried to navigate walking downstairs in her heels. Coming up them had been far easier but by the second flight she got used to the awkward positioning of her foot. Back in the office, Babette was all smiles.

"Was Jeff there?" She blurted as soon as Michelle entered.

"Oh my God he is GORGEOUS!" Michelle responded feeling every bit the teenage girl.

"I heard he's quite well endowed as well." Babette replied.

"He didn't feel small," Michelle nervously, "when he pressed it against my leg."

"You slut!" Babette teased. "How did Nancy handle your backdoor exam?"

"I have to ask you about that," Michelle whispered, "she handled it fine but made a point about keeping cleaned out a business expense." Michelle tingled all over from the thought. "Are we expected to," she gulped then proceeded to ask, "you know."

"Get fucked in the ass?" Babette blurted. "Honestly, what happens or doesn't happen on a date is completely up to you," Babette replied seriously, "you'll know who it is beforehand as well as how they are and what they are into." Michelle felt a bit better but that didn't quite answer her question. "Your first date will be with a guy who's just into crossdressers, nothing too kinky to start off." Michelle eased into the seat behind the desk hanging on Babette's every word. "By then, that plug in your ass will be going in much easier."

"I'm sure." Michelle replied unsure if that was a good thing or not.

"Okay, I'm not supposed to tell you this," Babette leaned into Michelle and whispered, "but sooner or later you're going to get tied to that desk and it won't be a plug going in there." Both girls felt chills rush up their spines at that thought. "And you're going to absolutely love it!" Babette gushed, gripping Michelle's leg tightly. "I swear she had me begging for more in only a few minutes."

Michelle found it almost impossible to focus on work the remainder of the day. Her thoughts ranged from being afraid of her next call into the office to wishing it would happen sooner. It didn't come to that, instead, on her way out to door Ms. Allison asked about Michelle's appointment with the Dr.

On her way home, Michelle stopped by a local pharmacy to drop off her prescription. The pharmacist raised an eyebrow after reading, only to be winked at by Michelle. Confirming she could pick it up tomorrow, Michelle picked up a couple magazines before she headed home to relax. Walking into her building, she glided past Fred as he was changing a light bulb in the hallway. Standing in front of the elevator, Michelle could see him in the door's reflection staring at her as she waited.

Ms_Allison
Ms_Allison
1,371 Followers