The Agency Ch. 15

*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!

Today marked the 3-month anniversary of Michelle's employment, she'd now spent one quarter of the year as Michelle. Her bank account was now fuller than it had ever been, there was actually a comma in her bank balance! Her breast augmentation and the following post-op visits had given her a natural looking full C cup, she even had extensions in her normal hair giving her more options on how to dress and do her hair. All of these things had been a slow process, and while she should have been happy about all these changes, her mind was elsewhere as she stepped into her seamless black thong. Tonight, was her "try-out" date with Mikey. Big Mikey to be exact.

The last time she'd seen Big Mikey, he'd been in the office lobby waiting to meet with Ms. Allison. Even with 4-inch heels on, Big Mikey was still taller than Michelle. He dwarfed her in every possible way. Mikey was also her key to moving out of Ms. Allison's front office and into Her stable. After Mikey reported to Ms. Allison how the date went, Michelle would then get to meet some of the clientele, from there she would start to go on dates. Michelle knew Ms. Amy would be one of her first, which she was really looking forward to, but there were other reasons. Babette's bank account made Michelle's look small, that, on top of jewelry and the cash she was getting, Babette would be financially secure for a long time in just a few more months. Michelle had never in her life been financially secure, the opportunity in front of her was a big part of her focus.

Michelle slowly pulled on a pair of black lace top stockings, which had rubber grippers on the inside to hold them in place. The stockings were long enough to almost reach her thong, which made it perfect for the dress she'd picked out. Taking the dress off the hanger, Michelle stepped into it, pulling it up her body enjoying the feeling of the satin dress against her flesh. The spaghetti straps sat on her shoulders, allowing the low-cut top to sit perfectly over her breasts. When she'd had the procedure done the Dr. had even shaved Michelle's Adam's apple minimizing it as well. This also allowed Michelle to be more daring in what she wore and how she presented herself, like this dress with its low cut back, which would certainly entice her date almost as much as her ample cleavage. Finally, Michelle stepped into the 5-inch heels she'd selected for the night. With her small clutch in hand, she waited for her date, not wanting to keep him waiting when he arrived. Michelle's stomach was fluttering, her entire body was a bundle of nerves not only because of the importance of doing well tonight, but also the fact this was her first-time having sex with a man.

"Oh geezus!" Michelle blurted and jumped as her phone buzzed with a text alert. "Calm down!" Michelle looked at the phone, gulped and uttered, "Show time!"

Michelle mindlessly straightened her dress, then grabbed her small purse and headed out, locking the condo door behind her. Babette was on a date herself, so she had the place to herself. Unfortunately, that also meant that if things went horribly wrong, she didn't have anyone to console her unless her date ended earlier than Michelle expected. It wasn't like she could call Brenda after all! They'd had a wonderful weekend at her friend's wedding, where Michelle had again shown her oral dexterity when it came to bringing Brenda to orgasm several times over. While Brenda had joked that Michelle wasn't allowed to kiss any guys at the reception, like she had during the bachelorette party, that was certainly going to be different tonight. According to Babette, Mikey was well endowed and seemingly insatiable. Walking past her doorman, who nodded politely while watching Michelle's breasts jiggle with each step, Michelle headed outside into the cool air of the city.

"Don't you look quite stunning?" Mikey said stepping away from the car and walking to meet Michelle on the sidewalk.

"Thank you," Michelle blushed, looking down slightly as she replied, "I do really love that tie with that suit." Close enough to touch now, Michelle placed her hand lightly on Mikey's chiseled chest brushing the tie with her fingertips.

"Thank you," Mikey replied before leaning in and kissing Michelle's cheek softly, "I hope you've been looking forward to this night just as much as I have."

"I have!" Michelle responded, realizing that even in her 5-inch heels she was still looking up to look him in the eyes!

"Let's go have some fun." He said turning and taking Michelle by the arm.

His hand dwarfed Michelle's arm as well, feeling like it was almost totally encircling her upper arm as he led her to the double-parked black car. The driver had appeared from nowhere and was now opening the door for her. He nodded politely as Michelle slid into the seat trying not to flash anyone. Slipping across the large seat, Michelle crossed her legs trying to at least look comfortable as Mikey joined her. With the car door shut, Mikey placed his hand on Michelle's right leg, giving it a soft squeeze.

"You know the place right Richard?" Mikey called out to the driver.

"Yes, Sir!" He replied.

"Great, I'll let you know when we're ready." Mikey said as he pressed a button on the door to raise the privacy divider between the front seat and the back. "As you probably know," he said as soon as the divider was all the way up, "I've been doing this for a while for your Boss." Michelle nodded. "This will be like any other date you'll go on during your employment where you are an escort," his voice was calm and comforting in a way yet still authoritative, "with the exception you don't get to choose if we have sex tonight."

"I understand." Michelle felt her stomach flip and sink at his words.

"We will have a conversation like it's a regular first date, my suggestion is to keep your background story mostly true," Mikey instructed while watching Michelle's reaction, "if you were a jock or a geek in school share that, just not the fact that you used the men's room of the school." Michelle looked confused by his words. "They know, but they don't want you to remind them in most cases," Mikey explained, "they're paying for a date with a girl and that's what they want."

"That makes sense." Michelle replied. "I guess."

"So, don't tell them you were a cheerleader, or make up a wild backstory," Mikey further explained, "because you may see them again 8 months later and not remember what you'd told them. Keep the conversation light but close to home."

"Thank you." Michelle felt amazingly reassured by his words.

Just as Mikey began lowering the divider the car slowed, pulling up to a well-lit entry way. The driver let him out, then Mikey leaned in to take Michelle's hand as she exited the car. She doubted her heard her thank him before he took her hand in his arm and led her inside. Mikey gave the Maitre'd a warm embrace before introducing her as his date. As Michelle followed the Maitre'd Mikey put his hand on her back, again she felt dwarfed as the heel of his palm touched her spine while his finger reached her side. His touch was warm and caring but reminded Michelle of his size.

"Very lovely to meet you Ms.!" The suave gentleman said lightly kissing her hand. "If you'll follow me, your table is ready."

Mikey held Michelle's hand lightly as she sat in the booth, and was certainly pulling out the gentlemanly charm as he ordered them a bottle of wine. Michelle had never experienced someone doting on her like this, it made her not only comfortable but filled her with a feeling of being wanted.

"So, tell me about yourself Michelle." Mikey said as he sat next to her again placing his hand on her thigh.

"Umm, well," Michelle wondered where to start, "I guess I've been with the Agency for three months as of this week, prior to that I was working in a call center, which was just a horrible job."

"What was horrible about it?" He asked with genuine interest.

"It was really a dead-end job, people just scream at you all day," Michelle replied earnestly, "but it was a paycheck and I didn't have to interact with people in person."

"I find it surprising that you sound like an introvert."

"Oh, but I am!" Michelle replied enjoying the conversation even though it was about her. "I have always been quiet and shy," Michelle said as the bottle was delivered to the table and the sommelier went through his process, "I wasn't popular, wasn't athletic, and wasn't one of the smart kids, so I just stayed in the background through high school and college."

"You look like this and remained in the background?" Mikey chuckled sliding his hand further up her leg.

"I was a very late bloomer." Michelle giggled unconsciously giving her breasts a squeeze together with her upper arms.

Dinner was an incredibly relaxing experience for Michelle, while it was odd that Mikey ordered her meal, it was the one she was going to choose anyway. It all seemed to increase her feeling of submissiveness and that she was "his". She found her need to please him increasing with each passing moment. When the meal was over, again Mikey was quickly to her side taking her hand as she slipped out of the booth. Michelle excused herself to use the ladies' room, it was one of the first times she hadn't questioned her decision to walk into a public restroom. She also wasn't surprised that the front of her sexy little thong was moist as well as she'd had difficulty not thinking about what was going to happen when they got back to his place.

"Ready to go?" He asked as she walked toward him.

"I am Sir!" Michelle eagerly responded.

As they waited for the car to pull up, Mikey stood behind Michelle, pressing his body into her back. She could feel him growing behind her, his crotch pressed into her lower back as he held her waist tightly. Pushing back into him, Michelle bit her bottom lip as his cock strained to reach her.

"I'm going to fuck your brains out soon." Mikey whispered in her ear.

"Yes, please!" Michelle's voice was dripping with need.

The driver came to the side of the car, opening the door and giving Michelle a wink as if even he knew what was next. Michelle settled into the seat, as Mikey got into the car and the driver shut the door. Her eyes grew wide as her gentlemanly date undid his pants, pushing them down to his knees.

"Well, it's not going to suck itself." Mikey looked at Michelle differently now, as if he were sizing up a race horse or something.

"Can you put the divider up?" Michelle asked just above a whisper.

Mikey leaned into her, touching the side of her face, and in a stern voice said, "Don't worry, he knows you're a slut. Now suck my cock."

Michelle trembled at the words and tone; the mood had shifted in the time it had taken the driver to get from the passenger side back door to his spot behind the steering wheel. Still, as Mikey's hand now guided her mouth to him, Michelle did not offer the slightest bit of resistance. There had been weeks of anticipation for this moment, she licked her lips just before taking the head of his large shaft into her mouth.

While she'd spent months practicing her oral skills, and even taken Babette's cage into her mouth multiple times, she couldn't prepare herself for the warmth of his cock in her mouth. She'd tasted plenty of Babette's precum at this point, but the warmth of her caged cock was never really transferred through the hard plastic. Mikey's hot cock now filled her mouth and eased toward the back of her throat. Michelle barely registered the fact he'd removed his hand from her head and was lightly stroking her back as she worked his cock with her mouth. Lifting her head, Michelle let it pop from her mouth before circling the head with her tongue and plunging downward again. Her left hand reached between his thighs, caressing and cradling his balls.

"All set Sir?" Michelle heard the driver ask.

"Yes, go ahead!" Mikey responded.

Michelle suddenly realized they hadn't even pulled away from the curb yet and were still in front of the restaurant. It didn't matter, her world was now directly in front of her face. Whatever went on around her didn't matter, she had zero interest outside of worshiping his beautiful cock. Even when Mikey and the driver talked back and forth about Michelle's skills and enthusiasm, it didn't matter to her. Mikey slid his left hand further down her body, tugging the back of her dress up until his hand reached her bare ass causing Michelle to moan loudly.

"This is for making me wait." Mikey said as he playfully gave her butt a whack. The spank, while nothing compared to punishments she'd received from Ms. Allison, sent a bolt of lightning through Michelle's body. "It seems someone enjoyed that, didn't you?" Michelle went to lift her head to answer but his hand on the back of her head prevented it. "Don't talk with your mouth full slut!" Mikey teased while giving Michelle's butt another spank.

Michelle suddenly found herself light headed with lust, she'd only read about women being in this particular situation and felt most of those stories were simply fantasy. How could they not be? Regardless, here she was in the back of a short version of a limo with a strange man's cock in her mouth while another watched and they both commented on her. Not just her oral abilities, which they both seemed pleased with, but her body and looks as well as how she reacted to being spanked. The word slut was getting thrown around like a badge of honor, and Michelle was striving to earn it. Mikey's finger now slid between her butt cheeks, causing Michelle's body to instinctively arch her back to bring her tight hole to his reach. This act elicited more comments from both Men.

"Looks like someone's ready to get fucked!" The driver chuckled.

"I'd say she is!" Mikey's pleasure was conveyed in his voice. "What about it slut?" He asked while still applying pressure to the back of her head. "Are you ready for me to fill your pussy with my cock?" Michelle groaned around his shaft wantonly. "I'll take that as a yes!" He laughed. "Soon enough."

Mikey started to lift his hips, meeting Michelle's mouth with each downward thrust with his own upward one. Michelle struggled to focus on breathing whenever his cock wasn't blocking her airway, but it wasn't as easy now as it had been with a dildo. Then Michelle was able to control the pace, now he was controlling everything. His finger teased and rubbed her ass, further adding to her dilemma. She'd also never given a bj in this position so there was the additional feeling of her breasts hanging and bumping against the seat as she moved up and down. Michelle tensed her legs, feeling a ripple of pleasure rolling through her body. Just after, Mikey's cock swelled in her mouth, his hand clamping tightly on the back of her head as he lifted his ass shoving his cock as deeply as he could into her mouth.

"Ohhhhh!" Mikey groaned loudly as the first fiery jets exploded from his body.

Michelle could feel him oozing down her throat, almost like drinking coffee when it's too hot and you can feel it burning all the way down, but far more enjoyable. Mikey released her head enough so the next globs of salty goodness filled her mouth. Michelle felt her stomach flutter as she swallowed, while milking and coaxing more from him with her left hand. She couldn't describe the feeling, or need, but she desperately wanted to taste more of him!

"Such a greedy little slut!" Mikey chuckled as Michelle continued to milk everything she could from his body. "Don't worry," he said releasing her head, "I'll make more."

As Michelle slowly sat up, she couldn't take her eyes off his now flaccid cock. Michelle physically felt disappointment as Mikey pulled up his pants and tucked his shirt back in. Looking up, she realized they were parked and the driver was again getting out of the car. With Mikey's clothing arranged as best they could be, he got out of the car, then turned to look for Michelle who slowly followed him. She suddenly felt like everyone knew exactly what they'd just done. His clothes were disheveled and her face was flush, hair was definitely a mess and her lipstick certainly a bit out of sorts. Anyone with half a brain would know she'd just sucked him off. There were a few people walking by, making Michelle feel incredibly self-conscious. It certainly didn't seem to bother Mikey as he took her hand in his arm leading her into the building. Michelle's heels felt like cannon shots each time she stepped on the marble floor.

"Good evening, Sir," the doorman said while eyeing up Michelle, "and Ms."

"Good evening, George!" Mikey replied with a grin.

Again, Michelle was convinced George knew why she was there as well as what she'd just done. Stepping into the elevator, Michelle was thrilled to be out of view of anyone, but only momentarily. The reflection in the elevator door did confirm her suspicion, her lipstick was a bit messed up as was her hair, she looked like a woman who'd just sucked a cock in the back of a car! Babette liked to refer to it as the "freshly fucked look" or FFL for short.

Mikey put his arm around Michelle's body, cupping and squeezing her breast through her thin dress as he stared at her in the reflection. His finger circled her rock-hard nipple as he pressed his crotch into her body again. Mikey's other hand moved down Michelle's side, over her hip then back up her leg to her ass, giving her a firm squeeze.

"You are quite stunning," he whispered in her ear, "Allie must be very pleased with your progress."

"Thank you." Michelle moaned, quickly getting over the brief moment of shame and wanting more.

As the elevator door opened Mikey took Michelle by the wrist leading her quickly down the hall to his doorway. Stopping there momentarily, he quickly opened the door, coiling both arms behind her as he walked her through the door. The door was still closing when the spaghetti straps of Michelle's dress fell to her elbows leaving her bare from the waist up. Mikey swept Michelle's hair over her right shoulder with one hand while pushing her dress past her hips until it fell free of her body pooling around her feet. His mouth quickly made its way to her neck while his hands freely roamed her body, occasionally pausing to tug and roll her nipples. The feeling was wildly erotic for Michelle who pressed her body back into his. Suddenly, he spun her quickly to face him. He seemed even bigger now, even more in control, as she stood there in her lingerie and heels.

"Undress me." He commanded.

"Yes, Sir."

Michelle felt an even greater level of helplessness as she stood there, with him holding her upper arms in his massive hands. Tentatively she moved her hands inside his jacket, letting her fingers touch his chiseled chest as she pushed it over his shoulders. Only then did he lower his arms, and release his grip on her, as the jacket slipped free. Michelle struggled slightly undoing his tie, but eventually unknotted it leaving it around his neck as she next tackled the buttons on his shirt. Mikey wore no undershirt, so each button revealed more of him to her. The anticipation was almost too much, but she wanted to take her time and enjoy the experience. Undoing the cuffs of his sleeves before untucking the shirt, Michelle's hands parted the front of the shirt, touching his chest. His pecs were large, his stomach flat, his shoulders broad and rounded with muscle. He was a specimen of masculinity in every sense and certainly the polar opposite to Michelle. His shirt soon joined his jacket on the floor.