The Agency Ch. 08

Michelle descended the stairs to the office on pure autopilot. Mike had never been asked out by a woman, and could barely have gotten the attention of someone like Brenda on his own. Mike was a wingman at best, and a pretty shitty one at that! He was an introvert with little going for him. Michelle was the polar opposite of Mike, and it was apparently paying off for her! Walking into the office, Michelle barely had time to put her bag down before being paged to Ms. Allison's office. Quickly making her way down the hall, Michelle entered the office, dutifully removing her dress while servicing the dildo behind the door 10 times with her mouth.

"Multi-tasking I see!" Allie called out from behind her desk. "That's My girl!"

"Thank you Ms. Allison," Michelle replied after letting the dildo slip from her lips, "how are you this morning?"

"I'm very well," Allie replied motioning for Michelle to sit, "and how was your appointment today?"

"It went well Ms.," Michelle was slightly uneasy in her chair as she spoke, "the Dr. was pleased with the progress, but I have to tell you something odd that happened."

"Go ahead."

"The nurse, Brenda," Michelle's throat felt dry as she tried to get the words out, "well, she kind of, I guess, asked me out to dinner tonight."

"Really?" Allie was honestly surprised by this revelation.

"I hope that's not a problem Ms. Allison," Michelle hated the idea she'd have to text Brenda and tell her no, "I was shocked when she asked and just said yes without thinking. Please tell me You're not mad at me."

"Oh not at all muffin," Allie smiled warmly at Her nearly panicked employee, "tell Me exactly what she said."

Michelle started by describing the seemingly less that subtle flirting Brenda had done, the coffee date suggestions up to this morning and her comment about not looking better than her somewhere casual. Allie nodded and smiled while wondering what Brenda could be up to with Michelle? She'd known of Brenda for years, but only met her a couple times. Of course, Allie had sent over 20 girls to the office since Brenda's arrival, and she'd barely paid any of them any attention. What was it about Michelle? She had to admit, Michelle was quite passable as a girl and looked the part. Maybe it was that, or her sweet demeanor? Allie would have to investigate this eventually.

"I want you to go on the date," Allie finally said after a moment of silence, "it will be good for you."

"Really?" Michelle couldn't try to hide her shock at the response.

"Yes baby," Allie's tone was warm and caring, "you don't think My girls have friends that are girls outside of their jobs?" Michelle shook her head, feeling silly now for asking. "She obviously knows your limits when it comes to certain intimate moments," Allie continued, "but I want you to have fun, you should enjoy being a girl to it's fullest extent."

"Thank you, Ms." Michelle happily replied. A look of panic quickly returned to Michelle's face, "I don't know what I'm supposed to wear though. What counts as casual?"

"Oh I'm sure I can help you with that," Allie smiled, "while I think about your wardrobe why don't you come here and bend over the desk with your panties off." Immediately responding and reacting, Michelle's panties were off in a flash and delicately laid on the desk as she bent over, exposing her bare ass to the windows behind her. "You have a pair of Capri pants don't you?" Ms. Allison asked as She stood, revealing Her strapon.

"Yessss, Ms.," Michelle cooed at the sight of the thick phallus, "they're a dark tan color."

"Very nice," Ms. Allison said as She let Her fingers glide over Michelle's body while making Her way behind Her submissive, "those with those wedge sandals you bought a couple weeks ago."

Michelle's body trembled as she felt the lubed head of the shaft rubbing against her opening. It took far less concentration at this point for Michelle to relax, she'd become so used to being penetrated, her body seemed to ache for it now.

"I know the one's Ms.," Michelle moaned slightly as the head slowly penetrated her body, "the one's with the floral print and open toe."

"Yes sweetie, those," Ms. Allison looked proudly down at Her charge as She slid easily inside her ass, "and that adorable bohemian top with the white crochet at the bottom."

Michelle wanted to respond, instead she let out a long groan as the entire length of the shaft penetrated her body in one slow push. Typically, Ms. Allison gave Michelle time to adjust every few inches, but not this time. The feeling was odd yet still enjoyable making Michelle feel weak in the knees. She even felt her eyes flutter just before feeling Ms. Allison's hips pressing into her bare ass.

"Very nice sweetie," Ms. Allison said proudly, "you took that amazingly well."

"Thank you, Ms.!" Replied Michelle as she struggled to get her bearings about her. "This one feels, um, bigger."

"Maybe just a bit," Ms. Allison pulled back slowly, easing the pressure inside Michelle's body, "it's the biggest you've enjoyed to this point. What do you think?"

"Ohhhhhh," Michelle groaned again as Ms. Allison pressed forward, using Her weight to hold the phallus in place, "it's definitely rearranging organs to it will fit!"

"But you don't hate it do you?"

"Noooooo Ms.!" Michelle exclaimed as Ms. Allison pulled halfway out. "It's fucking amazing!"

"Good girl," Ms. Allison praised before thrusting into Michelle, "not everyone takes this one so well the first time."

"Thank you!" Michelle grunted as Ms. Allison began to fuck her in earnest. "Ohhhhhh fuck!" she groaned loudly.

Allie gripped Michelle's hips tightly, pulling Herself into Michelle's ass again and again. She hadn't been exaggerating when She'd praised Michelle, it was very rare that a girl took to this size cock the first time. Michelle was all but begging for more already. It was a very promising sign in Michelle's development.

"That's My slutty sissy," Ms. Allison exclaimed loudly, "tell Me what you want!"

"Oh please fuck me! Fuck me harder!" Michelle blurted as her body trembled. "You own me!"

"Would you like to know a secret baby girl?" Ms. Allison asked as She pulled Michelle up to an almost standing position without letting her escape the shaft. Seeing Michelle nod, Ms. Allison continued, "This is a model of your first dates actual cock. He makes sure you're ready for clients."

"Ohhhh gawd!" Michelle suddenly felt light headed as Ms. Allison thrust into her several more times, lifting her heels from the floor slightly.

Lowering Michelle's torso back to the desk, Allie carefully slid the shaft out of her body, leaving her hole gaping and sore. With Michelle's body slack against the desk, Allie retrieved a weighted plug, easily slipping it inside Michelle. Walking to the bathroom, Allie removed the harness, depositing it in the sink, before returning with a glass of water for Michelle. Setting the glass on the desk near Michelle's face, Allie sat at Her desk watching Her sissy slowly recover.

"Thank you, Ms." Michelle said before taking a sip of water. "Is he really that big?"

"Yes he is sweetie," Allie smirked before continuing, "but you're more than able to accommodate his size already." She paused momentarily as Michelle took another sip. "The biggest difference," She said turning back to Her computer, "is when he's done you'll have an ass full of his cum to enjoy too!"

Not surprisingly Michelle visibly shuddered at the thought. The feeling of a spasming cock was the one thing Allie could not prepare her for prior to her practice date. By that point though, Michelle would have progressed far enough in her training that she would not hesitate when presented a cock. She was already at the point that her mouth watered at the sight of a dildo, and was probably also feeling a twinge of want in her ass at the sight too. Having an employee freeze or worse yet, balk on a date was disastrous for everyone, as a result Allie took careful and calculated steps to ensure it never happened. For what Her clients were paying, Allie's girls had to be classy and smart when out and wanton sluts in private. Michelle was well on her way to fulfill those requirements.

"That would feel amazing." Michelle replied as she slowly raised herself from the desk. "May I go clean up Ms.?"

"Go right ahead." Allie replied feeling quite proud of Her newest girl.

Standing up in her 4" slingback heels took a bit of extra focus, still, Michelle managed to make her way to the bathroom. Michelle cleaned herself, then cleaned the toys Ms. Allison had left in the sink. Holding the dildo in her hand, Michelle found it hard to believe something that big had slid so easily inside her! She couldn't imagine what the man who had this stuffed into his pants could look like, but he obviously got a workout any time he needed to relieve himself!

"I could use two of these instead of pink dumbbells' in the morning!" Michelle giggled while feigning a curl motion. "Oh I am quite a sight," she said catching a glimpse of herself in the mirror, "thank goodness the essentials are always well stocked in here!"

Michelle's hair was slightly matted to her forehead, her lipstick was a bit smeared, and her eyes needed a touch up. All of which she could easily do without having to leave the bathroom. She had to admire herself a bit in the mirror as well, particularly the full length mirror on the door which was to her side. As she leaned forward, seemingly to touch up her mascara, Michelle arched her back and pulled back her shoulders before looking at the full length mirror. Standing like that, her cage hidden by her thigh, Michelle saw the reflection of a hot girl looking back at her and smiled proudly.

"Okay, back to work." She said shaking her head and refocusing on cleaning up. Michelle reentered the office to find Ms. Allison sitting on the side of Her desk, waving Michelle to her usual chair. "Where would you like these Ms.?"

"You can put the harness in the top drawer of the cabinet there," Allie smiled warmly as She spoke, "the dildo you can hold onto for now." Watching as Michelle complied, Allie continued, "Before you sit you can put those sexy panties back on as well."

"Yes, Ms.!" Michelle replied.

Placing the harness back into the cabinet, Michelle then retrieved her panties, using the table to brace herself as she stepped back into them. She was then left with the conundrum of what to do with the large phallus. Sitting in the chair, Michelle wasn't sure whether to hold it in her hand, or leave it lying on one of her legs. She didn't want to rest the bottom on one leg and hold it in her hand as it would look like she were fondling it rather than being respectful to her Boss. Finally, Michelle placed it across her leg and held it in place with one hand.

"How does your pussy feel sweetie?"

"A bit sore and tingly Ms.," Michelle blushed deeply at the question, "thank you."

"It's obvious you've taken your training to heart," Ms. Allison's voice conveyed Her pride in Michelle, "which obviously made this easier today." Michelle lowered her head, unsure of how to react to the compliment. "I would honestly say you are ahead of most of the girls I've hired to this point," Allie was truly proud of how well Michelle had taken to her role, "there's still a way to go, but, it's very positive." Allie smiled further as she noticed Michelle's fingers moving slowly over her new toy, nothing overtly sexual, but a slow loving touch. "Later tonight I will email you the outfit I want you to have on tomorrow."

"Yes, Ms." Michelle replied wondering why Ms. Allison would be directing specifically what she had on the following day.

"You can head back out to your desk now," Allie said returning to Her computer screen, "from what I understand you're going to lunch with Babette today?"

"Yes, Ms. Allison," Michelle replied as she got to her feet, "I hope that is okay."

"Very much so," Allie's smile was warm, "it was My hope the two of you would hit it off, it's easier when you have a mentor to help you through this process."

"She's been great Ms. Allison," Michelle replied genuinely, "I would be lost without her."

"Just keep in mind how she is with you when it's your turn to mentor your replacement."

"Yes, Ms.!" Michelle was excited at the idea of helping a new person become like her.

Worshiping the dildo hanging from the door with her mouth, Michelle then put her dress back on to return to her desk. As she walked down the short hallway, Michelle tried to figure out how to hide such a large phallus. She had a good size bag with her, but, it was across the entry way to the office.

"It sounded like someone met Little Mikey today!" Babette called out from one of the guest chairs.

"Little Mikey?" Michelle asked quickly moving her hands behind her back.

"Yes sweetie!" Babette teased, "You don't think I was on the receiving end of Little Mikey when I was in your position?" Michelle shook her head answering no. "He's quite a beast," Babette said as she approached her friend, "but Big Mikey is even better."

"Big Mikey?"

"The guy who sports the beast you've got hidden behind your back," Babette replied, "he's the sweetest man you'll ever meet, but you will not feel like one in his presence!"

Michelle chuckled to herself, she was wearing lingerie, perfume, makeup, heels, and a dress. How could she possibly feel like a man at this point? Her body was shaved and moisturized, her eyebrows shaped, she was getting breast injections. There was no way to feel manly. Even as Mike she barely felt "manly".

"Um, have you looked at me?" Michelle practically jeered, "How could I feel manly when this is how I look every day?"

"Oh it's possible to feel less manly!" Babette replied. "He's built like a god, and I'm not just talking about his cock!"

"Wow!" Michelle replied unconsciously squeezing the phallus behind her back. "Like action movie star built?"

"Yes! Exactly!" Babette slid forward, touching her chest to Michelle's before continuing, "But don't worry, he's so gentle you won't want him to ever stop!"

Both girls felt a rush up their spines at the thoughts. Babette, remembering her night with Big Mikey, and Michelle imagining it. Michelle realized she was clutching the dildo now with both hands.

"Okay, let me hide this thing and we can go to lunch," Michelle said stepping away from her friend, "I have so much to tell you!"

"Feel free to start now!"

"Well, I have a question first," Michelle said returning with just her pink wallet, "when do you close on your new place?"

On the way out of the building Michelle told Babette the story of her morning and telling Fred she was going to move out. Babette was not only thrilled Michelle was moving out of "that dump" but seemed very excited about her moving in. While Babette would still be in the apartment another month or more, her professional life was getting busier and she had more than a couple trips away planned already.

"So should I pay rent? Kick in towards rent and utilities? How do you want to work this?" Michelle asked as they walked down the street.

"Oh don't worry your pretty little head about that," Babette replied taking Michelle's arm in hers, "we can work something out!"

"That sounds rather ominous!" Michelle giggled.

"Rent is all set for the next two months," Babette replied, "most of the utilities are already included in the rent, and I'm not worried about food. Buy what you like!"

"Okay then." Michelle felt reassured and excited about her new living arrangement.

Turning into the restaurant, they only had to wait a minute for their booth to be ready. With their drinks ordered, sweet tea for Michelle, cosmopolitan for Babette, Michelle decided to go to the next topic.

"So what is the deal with you and nurse Brenda?" Michelle asked after a long sip of her sweet tea. "I get the feeling she's not a fan of yours."

"Probably not." Babette replied looking somewhat ashamed. "Okay, so before I became the gorgeous piece of ass you see before you," Babette said with a smile, "I worked on Wall Street."

Babette explained that she'd been a stock broker, and a very successful one at that, but gotten caught up in the market and over extended herself before things went south. Way south. Almost overnight Babette had lost everything, then she'd applied for a job at The Agency. Adjusting from being a big fish in a cut throat business to being a sweet, submissive girl wasn't exactly easy for her. In spite of the fact Babette was coming in for breast augmentation, she saw Breda as her former self would have viewed her, and it had gone horribly wrong.

"Well, you're going to be shocked to know this," Michelle said, wishing she was having a cosmo too, "but I'm going to dinner with her tonight."

"You're fucking kidding me!" Babette hissed. "How in the world did you pull that off?"

"Honestly, I didn't do a thing!" Michelle replied earnestly. "She's been hitting on me from the beginning!"

"What did Ms. A say?"

"She helped me figure out what to wear," Michelle replied, "and told me to have fun!"

"Well then, I hope you have fun too!" Babette replied, reaching across the table and squeezing Michelle's hand. "I mean that you know," she continued, "but how would that ever work out?"

"I don't even know!

"I hope your oral game is on point!" Babette chuckled.

"I've been working on it several times a day to the point my throat is sore." Michelle quipped.

"I don't think she has one of those silly," Babette chuckled a bit more, "I was talking the internal plumbing kind of oral skills."

"Oh, OH!" Michelle replied. "Well I doubt that would be a first date thing with her."

"If she was the one that suggested it," Babette smiled, leaning forward and squeezing Michelle's hand again, "then there will be more than one! Just don't be a jerk."

"That's pretty easy for me." Michelle giggled in response.

Lunch with Babette was relaxing and enjoyable, her soon to be roommate offered to create space for Michelle to bring her clothes and other essentials. Babette suggested burning the furniture in Michelle's apartment, and possibly the entire building, but Michelle said she'd simply donate it somewhere. Back in the office, the remainder of Michelle's work day flew by. While she somewhat wanted to be called back into the office again, she was thankful not to be bent over the desk just yet. Tomorrow though was another story.

Taking the train home, there was no sign of Fred upon Michelle's return. She was rather proud of herself, finally managing to overcome the incredible distraction of having a plugged ass on the subway. No doubt, she was still bordering on mind numbingly horny, but over her time working at The Agency she'd learned to live with it.

"Okay, where are those Capri pants?" Michelle asked herself as she walked through her apartment door and stepped out of her heels. "No wonder so many women on the train wear sneakers!" She said walking in her stocking feet to her bedroom.

Soon the dress was lying on the bed, quickly followed by the stockings and garter belt. Digging through the closet, Michelle found the Capri pants folded neatly on the shelf. She quickly stepped into them, pulling them into place as she walked to the bathroom.

"The things I do to look good," she grumped while stepping onto the side of her tub to try to see her reflection in the mirror, "oh that just won't do!"

The flat front of the Capri pants left little to the imagination when it came to Michelle's cage. Carefully stepping down from her perch, Michelle walked back to her bedroom while undoing her pants. Removing those, and the sexy bikinis she'd had on all day, Michelle retrieved a more sliming undergarment.

"It's not much to look at," Michelle said as she pulled up the nude, floral embossed bottoms, "but they'll keep you hidden!" With the bottoms almost in place, Michelle tucked her cage and balls inside before pulling them up. "Ohhh those are gonna hurt later," Michelle said with a deep exhale, "fuck, I should have taken that damn plug out first! Power thong is right!"