The Agency Ch. 05

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!

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Thursday morning on the train ride in, Michelle was lost in thought. Perverted thought, but still, thought. The night before she'd practiced her oral skills well above the 20 minutes Ms. Allison wanted, this morning she'd done the same. Beyond that, she'd watched three of the video compilations that had been in the zip file to better understand how to give a great BJ, both physically but also visually. Mike had only gotten a couple in his life and he'd never understood what the fuss was about, but none of the women giving them had shown a fraction of the effort the girls in the videos had. She'd also taken the fatter plug out before bed, and reinserted it before her morning workout. It took a bit of time, as this one stretched her considerably more than the last, but she did manage. Now, her throat still tickling from the feeling of the dildo and her ass rhythmically buzzing with the movement of the train, Michelle's thoughts could move from little more than those to spots. Well, there was one other spot that was demanding attention, Michelle's balls ached badly!

"Oh shit!" She hissed to herself darting toward the train door. "This is my stop!"

Michelle had almost missed her stop because she was so distracted. Thankfully she'd chosen to wear a pair of 3 1/2" heels today instead of the 4" ones, she'd have certainly fallen if she tried to move that quickly in those. Walking up the stairs to the sidewalk, Michelle loved the feel of her dress rustling across her stocking clad legs. Being dressed truly made her happy! Her A-Line royal blue dress had a chiffon overlay which Michelle felt added a bit of elegance to it. She paired the dress with strappy silver heels, which coordinated nicely with her silver with white lace lingerie and nude stockings. She simply felt sexy, so it didn't matter that she was a bit overdressed for work. Carrying a small silver purse, Michelle entered the building.

"Well good morning," the gentleman waiting by the elevator said warmly, "Michelle right?"

"Yes," Michelle responded, really unsure of what to say, "good morning."

"Tom." The man replied. "I take it your cold is gone?"

"Oh, yeah," Michelle panicked for a moment then remember they'd run into each other the previous week, "I'm all better now thanks."

"You look fantastic."

"Thank you!" Michelle replied, feeling really good about herself.

It had been one thing for Fred to be "conveniently" out in the hall whenever Michelle left for work, he was a pervert, but Tom's compliment seemed totally genuine. Michelle even felt compelled to give him a polite wave as the elevator doors closed after she got off. Getting settled into the office, Michelle's phone beeped.

"There she is!" Michelle said, picking up her phone.

Babette had texted saying she would be in after 10 because the shoe store didn't open until then. Plus, she'd had a late night.

"Oh I can't wait to hear the juicy details!" Michelle said in response and out loud.

At 10:30 Babette walked through the door, wearing he black patent $500 heels which sported a 1-inch platform and spiked heel. She beamed as she entered and set down her bag.

"I have to go in to talk to Ms. Allison," Babette said, pulling Michelle out of her chair for a hug, "but after we'll go to lunch and I'll tell you all about my date!"

"I can't wait!" Michelle pulled Babette tightly to her as she responded. "Good luck!" Michelle said before softly pressing her lips to Babette's.

"Thanks!" Babette responded before heading off to Ms. Allison's office.

Michelle practically collapsed into her chair, she'd just kissed Babette! There was no hesitation, and Babette had kissed her back! She didn't know what to make of it, she'd never considered kissing a guy like that before. Then again, Babette wasn't exactly a "guy". Hugging her had felt so comfortable, so natural, the kiss just followed. She was closer to Babette than anyone she'd ever known before including her own family. Michelle shook her head remembering her friends advice not to get hung up on society's idea of what is right.

Babette eventually emerged from Ms. Allison's office, still beaming, and ready to share everything with her friend Michelle. "Let's go to that bistro next door!" Babette practically squealed, "If we go now we can get a seat by the window so I can show off my new shoes!" Practically pulling Michelle out of the office by her hand, Babette guided them to the elevator.

"Babette, I don't have my purse!" Michelle said, turning toward the office.

"You don't need it," Babette said as she tightened her grip on Michelle's hand, "your girlie made BANK last night!"

"Do tell." Michelle said as the elevator door opened.

Walking hand in hand into the elevator, they didn't release their touch until Babette held up her hand to show off her new tennis bracelet.

"Holy shit!" Michelle said, pulling Babette's arm closer. "Are those?"

"Canary yellow diamonds and emeralds in white gold!" Babette proudly responded.

"And what did you do to earn that?" Michelle asked, unable to lift her eyes from the expensive bracelet.

"At that point, not a thing!" Babette giggled as the elevator door opened. Finding a table in the bistro, with a window view, Babette finally got to tell Michelle all about her date. "He was cute, maybe 10 years older than me, but very fit." Babette smiled. "He picked me up in a limo, and gave me this on the way to dinner," Babette waved her wrist to make sure Michelle knew exactly what she meant, "then ordered a very expensive bottle of wine."

"Wow!" Michelle was floored, in one night this guy had spent more on Babette than Mike had spent on every girlfriend he ever had combined! "I can't believe he just gave you that and you didn't have to do anything!"

"It certainly gave me plenty of reasons to give him a blow job on the way to the theater!" Babette said, visibly excited by her own words.

"Slut!" Michelle teased.

"Oh I was later!" Babette replied with a wink. "He took me back to his place," Babette leaned in close as she whispered, "and fucked my brains out." Michelle felt the hair on her arm stand on end at her friend's words. "Honestly, I can still feel him back there."

"You mean sore?" Michelle asked quizzically

"No, not that," Babette replied, "but I can feel his cum and if I think about it and close my eyes, him filling me."

"Holy shit!" Michelle responded unsure of what else to say.

"At one point, I was on my knees on his bed," Babette closed her eyes momentarily before she continued, "black lingerie and heels, he's behind me on his knees ramming into me." Michelle held her breath for a moment as she listened intently.

"I look over at a mirror by the foot of the bed," Babette shuddered again, "it just looked so hot I practically came right there!"

"Did you?" Michelle blurted. "Did you cum?"

"Yes!" Babette practically squealed with delight. "Thankfully I caught it before I made a mess of his bed!"

"Oh my God!"

The swollen state of Michelle's balls was not helped with the conversation. She could feel herself leaking even more as she sat in the bistro and was sure her sexy little thong was soaked. They sat silently for a few minutes, both absorbing what Babette had just shared.

"What are you doing this weekend?" Babette finally asked.

"Nothing really," Michelle responded with a chuckle, "laundry, clean my crappy place, work on my bj skills. You know, the usual."

"Want to come over?" Babette asked. "I have a date Saturday night, but you can stay at my place while I'm out," she seemed to urge Michelle to say yes, "and I'm going apartment hunting on Sunday and I don't want to go alone."

"Sounds fun!" Michelle answered.

"Plus, you can work on your bj skills anywhere!" Babette teased a little louder than Michelle would have preferred.

Returning to the office after lunch, Michelle was called in to Ms. Allison's office while Babette remained at the front desk. While she knew it wouldn't help the ache in her thong, Michelle desperately hoped for a milking or more.

"Have a seat Sweetie." Ms. Allison said as Michelle entered.

"Thank you, Ms." Sitting with her back straight, Michelle crossed her legs, folding her hands in her lap.

"You seem to have adjusted to the bigger plug quite well."

"Yes, Ms.," Michelle blushed deeply wondering how she knew the fat plug was filling her ass, "it took a bit to get it in this morning, but I'm adapting to it."

"I'm sure Babette spent your lunch time talking about her date last night," Ms. Allison said, "and gave you all the details." Michelle smiled, feeling her face redden just a bit. "Just so you are aware, Babette was under no obligation last night to have sex with her date."

"I understand Ms." Michelle replied.

"Her date Saturday is a bit different, and there is a definite prearranged expectation." Ms. Allison leaned forward, expressing her sincerity and concern that Michelle understood what she was saying. "I will never put you in a position you are not prepared for and a willing participant."

"I trust you Ms. Allison." Michelle replied truly meaning the words she'd just spoken.

"That is very important to me," she continued, "all relationships of a sexual nature are built on trust, the more intense or unusual the relationship the more you rely on trust."

"Thank you Ms. Allison." Michelle responded. "May I ask a question Ms.?"

"Go right ahead."

"I don't know how to phrase it, but obviously Babette got paid quite well for last night." Michelle stumbled over her words knowing what she wanted to ask but unsure of how to do it.

"Yes she did," Ms. Allison responded, holding up her right hand, "she made just over a month's salary last night not including the tennis bracelet." Watching as Michelle's face blanched, Ms. Allison gave her a moment then continued. "The last two girls who recently retired left with over 1 million to their names." Michelle's jaw fell open momentarily. "Now, they earned every bit of that," Ms. Allison added, "but they also enjoyed earning it."

"Thank you, Ms. Allison." Michelle replied while adding in her head how many nights like last night she would need to make a million dollars.

"Now I bet you'd like to have a real orgasm wouldn't you?" The only thing that could take her mind off money was cumming.

"YES! Please Ms!" Michelle blurted almost jumping out of her chair.

"First take off that lovely dress," Ms. Allison instructed, "what you will learn is that orgasms during your training time are earned." Quickly complying, Michelle carefully stepped out of her dress not caring about the office windows but concerned she could rip the chiffon with her heels. "Now come around this side of the desk and kneel."

Complying quickly, Michelle knelt at the side of the desk. No sooner had she gotten into position then Ms. Allison turned her chair to face her newest employee. With her right leg crossed over her left, Ms. Allison slipped her right foot between Michelle's legs, pressing her foot directly against Michelle's thong. Adjusting her foot upward, the pointed toe of her high heel found the base of the plug which she pushed up slightly.

"Seems you've been excited today sissy." She chided.

"Sorry Ms.," mewled Michelle, "it's impossible not to get excited."

"Oh I know," Ms. Allison's voice dripped of cockiness, "when we are done today I'll help you make sure you don't ruin your dress."

"Thank you Ms."

"Pull your bottoms down just enough to expose your cage." Ms. instructed and Michelle immediately complied. "Now, I trust you watched a couple of those training videos last night," she said retrieving a key from her desk, "now it's time to see how much you learned." Dangling the key to the small padlock on her cock, Ms. Allison had Michelle's undivided attention. "First things first, put these on."

Michelle quickly took the two leather cuffs from Ms. Allison's hands, securing them to her wrists. The next two cuffs went on Michelle's ankles as precum began to pool on Ms. Allison's right foot and shoe.

"Now, before you get my foot any wetter," Ms. Allison said as she abruptly removed it, "let's get you in place." Standing, Ms. Allison turned Michelle to face her desk, then used leather straps in the shape of an X with D-rings on the ends to attach Michelle's cuffs thereby rendering her unable to stand or use her arms. "Here's how your reward will work," Ms. Allison said as she returned to her chair and undid the small padlock, "you're going to give this dildo a world class blow job, and as you do I'm going to play with your little boy parts here." Michelle nodded quickly until a realistic 7" shaft with a suction cup base was attached to the desk. "I will set a timer," she continued, then set the timer so it faced away from Michelle, "you have until it rings to orgasm!"

Ms. Allison left the cage in place, putting on a pair of latex gloves before continuing. She wanted Michelle to not only contemplate her position, but to make her wait. Michelle needed to understand she was not the one in charge of her orgasm. Gloves in place, Ms. Allison started the timer then removed the cage, watching Michelle's cock spring to life in an instant.

"The clock is running," she said as she leaned forward, "you'd better get to work!"

Michelle plunged her mouth downward on the shaft, feeling Ms. Allison's hand lightly grasp her throbbing member a moment later. Ms. Allison used Michelle's precum as lubricant, letting her index finger slip back and forth over the head while Michelle pushed her mouth further and further onto the shaft.

"Remember to breathe," Ms. Allison whispered softly in Michelle's ear, "when you need a break to catch your breath, use just your tongue on the shaft or balls."

Michelle plunged downward twice more before pulling back to let her tongue glide down the underside of the shaft. Returning to the tip, she circled it several more times before slowly taking it back into her mouth.

"That's it," Ms. Allison praised, "keep that tongue in contact and show that cock how much you love having it in your mouth." Michelle moaned softly in response, moving her head back and forth while slithering her tongue underneath the shaft.

"What a little blowjob slut you've become overnight," Ms. Allison teased while slowly stroking Michelle, "relax that throat just like you relaxed your ass to take that plug."

Ms. Allison's left hand glided over Michelle's ass, the fingers slipping between her cheeks, to find the base of the plug. Pressing on the plug base with two fingers, Ms. Allison moved her fingers in a clockwise motion watching Michelle react to the plug moving slightly inside her.

"That's it slutty sissy," her voice husky and sensual in Michelle's ear, "work that cock!"

Michelle's entire focus, her world had now become the realistic dildo she was worshiping. Everything Ms. Allison was doing, which was based on how well Michelle was servicing the dildo, reinforced that blowjobs equaled pleasure. Michelle moaned slightly when the hand moved away from her twittering shaft, then redoubled her efforts to earn its return. Working her mouth up and down the shaft as quickly as she could, Michelle groaned again feeling what felt like a condom slipping over her swollen head.

"Fuck that cock with your mouth my sissy blowjob slut!" She hissed in Michelle's ear, feeling the cock in her hands tremor. "It seems someone enjoys being called naughty names," Ms. Allison teased, "isn't that right my cock sucking sissy slut?"

Eyes fluttering, Michelle moaned, pulling back just enough to slather the dildo and balls with her tongue again. She'd gotten light headed and needed a moment to recover. It wouldn't last long because the stroking stopped again, she was so close, but the ground rules had been set without a word. Suck the cock and get stroked.

"Now focus," Ms. Allison's voice was kind and soft again, "focus on letting your throat open, focus on suppressing your reflex." Michelle did, slowly lowering her mouth onto the shaft before quickly pulling her lips back to the tip and slowly lowering again. Each time taking the shaft a bit deeper. "You don't get to cum until those balls touch your chin!"

Michelle kept from panicking, she could do this. The shaft was past the back of her tongue when she'd pulled back the last time, and she was so close to cumming. So close! Rolling her shoulders forward slightly, Michelle pressed forward again, the alignment of her mouth and throat now more accepting of the rigid shaft. She felt it! The big, bumpy latex balls pressing against her chin! She'd done it!

"There's a good slut!" Ms. Allison's praise filled Michelle's ears and soul. "Do it again!"

Lifting her mouth almost completely off the shaft, Michelle drove forward again, this time pressing and holding her chin against the latex balls. She repeated the process again and again, it seemed so easy now, plus, her orgasm was building.

Ms. Allison felt Michelle's body tense, it was only a matter of moments before she came. The next steps were all about timing. Slipping her hand from Michelle's ass, she continued to cheer her sissy on, making sure to use the terms that seemed to excite Michelle more and more. As Michelle's cock filled with cum, her head dove forward again.

"Hold it cock sucker!" Ms. Allison commanded while simultaneously gripping Michelle's shaft and holding her head in place with her other hand. "Hold it as long as you can!"

Michelle fought for air, unable to breathe with the shaft filling her throat, unsure of what she was supposed to hold, the shaft in her mouth or her cum in her cock! Tears streamed down her cheeks.

"Cum now!" She commanded.

Her entire body quaked as her aching cock finally erupted. Whether it was from lack of air, or the body shattering orgasm she'd just felt, Michelle's eyes fluttered. The hand on her head pulled her back, where Michelle finally gulped in air before being forced to wrap her lips around the shaft again.

"Nice and slow," Ms. Allison instructed, "you don't want to waste any." As she spoke she stroked and squeezed Michelle's shaft, filling the condom. "Guys love a sloppy blowjob, until the end," she continued as she slipped the condom from Michelle's rapidly waning shaft, "then they don't want you to lose a drop!"

Placing her the toe of her right foot directly under Michelle's shaft, Ms. Allison drained the condom on the dildo Michelle had been servicing. Hesitating for a moment, Michelle looked as her bodily fluid oozed down the sides of the dildo.

"The only way to be a cum slut, is to BE a cum slut!" Ms. Allison chided. "Waiting another six months before you get an orgasm like that again is the other option."

The choice was easy. Michelle had never experienced an orgasm as intense as the one she just had. Opening her mouth, Michelle slid her tongue along the bottom of the shaft, before enveloping it with her mouth. The salty taste filled her mouth while Ms. Allison's words filled her ears.

"Blowjob skills like that will make you a very popular girl in deed Michelle," she said praising her again while not moving far from the derogatory terms, "my clients love girls that can suck cock like a porn star!"

Ms. Allison knew the moments after an orgasm were important to maintaining control. Most men who enjoyed dressing up did so until they orgasmed, post orgasm they'd immediately change into their regular clothing ashamed at the fact they'd gotten off being dressed up. For her girls this wasn't an option, they had to not only remain dressed, but had to remain submissive and obedient. She couldn't have Michelle giving into her guilt.