The Agency Ch. 22

*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!

Keep in mind, this chapter will deal with the main character having sex with a man or men. Again, if you're not a fan, skip reading it. Sorry for the delay getting this story out, I actually got stuck for quite a while on it and just couldn't seem to move it forward. By the way, thank you for the Emails asking when this chapter would be out. I do respond to every email I get, if you didn't get one, it probably went to your spam folder or in your excitement (while typing one handed) you typed your email address incorrectly.

Michelle sat at the breakfast table, sipping coffee and eating a lightly buttered bagel, while running through the events of the past few hours of her life. It was probably going to take more than coffee for her to make sense of any of it, Michelle chuckled softly to herself while wondering if it would require some type of professional help. The biggest thing that happened was Brenda telling Michelle that she loved her, a feeling that Michelle wholeheartedly felt as well. The confusing part was, Michelle never pictured being a woman while falling in love with a woman. Maybe not 100% a woman, but womanly enough that Michelle had gotten more than a few nods and smirks from men and women alike as she made her way home in the late-night hours after leaving Brenda's place. Her hair tousled, a revealing dress and high heels certainly didn't convince anyone that Michelle was on her way to or from work, unless that work required her to wear a revealing outfit. So, not only had she told a woman she loved her, but then Michelle got to experience firsthand the walk of shame! Now, she was sitting in her kitchen wearing a flowing sundress, wedge sandals, a tiny floral print thong and some jewelry waiting for word that her ride to the airport had arrived. Michelle had gotten accustomed to wearing a bra, even before her breast augmentation, now that she wasn't wearing one she was even more self-conscious about her swaying breasts. The buzzer on the wall making noise jolted Michelle from her thoughts.

"Yes?" Michelle asked as she pressed the talk button.

"There's a car here for you Ms." Jack the doorman responded.

"I'll be right down!" Michelle responded.

Picking up her purse and the small bag for her trip, Michelle strode as confidently as she could to the elevator. Michelle could see her reflection in the door as she approached the elevator, the dress was complimentary of her figure, gathering just below her breasts and flaring out at her hips. The somewhat deep V-neck gave just enough of a hint of her cleavage without being too exposed, and the heels were the perfect height to show off her lower leg without making them too uncomfortable for a full day wearing them. Stepping into the elevator, Michelle felt as confident as she could. This was her first official date as an escort of The Agency, and while all the girls spoke highly of Bernard, she was still anxious about spending a three-day weekend with him.

"Good morning Ms.!" Jack called out as Michelle stepped off the elevator.

"Good morning, Jack!" Michelle responded as Jack rushed to meet her at the front door.

"Enjoy your day." Jack said as Michelle passed by.

"Thanks."

"Good morning," the driver said with a curt bow before opening the door to the car, "I'll take your bag Ms."

"Thank you." Michelle said, handing him the small bag before slipping into the back seat.

The driver had shown little reaction to the fact Michelle had only a small bag packed. Maybe he didn't know she was going away for an entire weekend, or maybe he did and knew enough not to question why she had so little with her. Truth be told, Michelle hadn't even bothered to look in the bag to see what was inside. All she needed to know was Bernard had selected what she was to wear during the weekend, and it was in that bag. The fact they were going to the Bahamas could explain why a lot of clothing wasn't needed. Michelle had checked the weather for the island of New Providence, it was going to be in the low 80's all weekend. Michelle's mind went back to Brenda, and their relationship as the driver navigated his way to the airport. The world outside raced past as Michelle tried to grapple with her feelings and how her relationship would work while she was contractually bound to Ms. Allison. Would Brenda understand she was being whisked away this weekend by an older man? Would she be disgusted by what took place at the photo studio earlier in the week? Or even whatever happened in Ms. Allison's office that week when she'd had her cage removed and been allowed to have sex with an unseen woman?

That was the other thing, Michelle had been far too distracted this week to think about who Ms. Allison had brought in to have sex with Michelle while she was blindfolded and bound. Whoever it was had certainly enjoyed herself, as Michelle could still imagine the feeling of her orgasm flowing over Michelle's empty balls and inner thighs. Michelle shook her head in disbelief, she'd had more sex in the past 5 days than she'd had in 5 years as her former self. It may not be anywhere close to what went through Michael's head while he fantasized about sex, but Michelle couldn't say she hadn't enjoyed herself. Shaking her head, Michelle had to stop thinking about her rather bountiful sex life and focus on today. Looking around, Michelle didn't recognize this part of the airport.

"I'm sorry," Michelle's voice was a bit uneasy as she spoke, "I thought we were going to the airport."

"We are Ms.," the driver replied, glancing back in the rear-view mirror, "you're not taking a commercial flight, we are going to the private side of the airport."

"Oh, okay." Michelle responded.

Private side of the airport? She asked herself. There's a private side to it? The driver pulled up to a security gate where he handed the security person whatever paperwork was required. This was all new to Michelle, she'd only flown twice before in her life and that was a family trip years ago. This plane certainly wasn't going to Disneyland!

The driver pulled up to a sleek looking private jet, with rows of windows and a small stairway that folded up as the door of the plane. As he got out of the car, Michelle could only stare and wonder how much something like this cost to rent or even own!

"If you have to ask, you can't afford it." Michelle whispered to herself just before the driver opened the door.

"This way Ms." He said, extending his hand.

"Thank you." Michelle replied, stepping out of the car.

"Have a good trip." The driver said as he walked off.

Standing rather dumbfounded for a moment, Michelle wasn't sure what she was supposed to do. That was, until a stewardess descended the stairs. She wore a white blouse, knee length blue dress, tan hose and blue heels. Signaling for Michelle to come to her, Michelle complied, figuring that getting on the plane was far better than standing next to it.

"Good morning!" The stewardess said with a perfect smile. "Right this way please." Ushering Michelle up the stairs, Michelle was amazed how much noise was cut out just by stepping onto the plane. "Right through there Ms." The stewardess said from behind her. "Your traveling companion will be here shortly."

"Thank you." Michelle replied, making her way to the elegant yet intimate cabin space.

"Would you like a mimosa?"

"Yes, please." Michelle replied, realizing the stewardess was also relieving her of the bag as well. "Thank you."

Michelle sat in one of the oversized leather chairs, carefully crossing her legs, as she waited for whatever was happening next. The stewardess returned a moment later with a champagne glass, handing it and a napkin to Michelle. She introduced herself as Janet and told Michelle not to hesitate to ask for anything else. Michelle silently wondered if Janet could make sense of her life to this point? After determining Janet probably couldn't, the stewardess was quickly exiting the plane. A moment later Bernard walked onto the plane. Michelle felt her stomach flip when he entered, even with his warm smile and kind eyes, her nervousness was taking over.

"Good morning, Michelle," Bernard said walking toward her, "you look stunning!"

"Thank you, Bernard." Michelle stood, deciding not to set her drink down and possibly drop it.

"You look amazing!" He said as he stepped to her and wrapped her arms around her.

Oddly enough, there was something almost reassuring about his hug. His arms were low around her waist, but she was also 6 inches taller than him without her heels on, yet his hands were not inappropriately placed. He held her hand high as she sat back into her chair again, she noticed his eyes leering around the V-neck of her dress and remembered that Bernard had been the one to fondle her breasts during her coming out party at Ms. Allison's home. Babette had even mentioned his enjoyment of breasts and blow jobs, which probably explained her lack of bra. Taking a long sip of her mimosa, Michelle crossed her legs and tried to relax. Bernard took the other seat nearby, as he did, Janet appeared with a champagne flute for him as well.

"Thank you, Janet." Bernard said while barely removing his eyes from Michelle. "Are we ready to get going?"

"Yes Sir," Janet replied, signaling Michelle if she needed a refill and getting a quick nod of approval, "the captain said we'll leave in about five minutes."

Janet refilled Michelle's drink, before going through her own preflight process. With Bernard and Michelle buckled into their comfy seats, Janet disappeared from view while Michelle made small talk and the plane taxied to the appropriate runway. Michelle, during that small span of time, found out that not only does Bernard own the plane but they would be staying at an exclusive resort he owns as well. When they reached the cruising altitude, Janet reappeared for refreshments again. Once she was out of view, Bernard produced a small red bag, handing it to Michelle.

"This is for you my dear." He said as he handed it to her.

"Oh Bernard," Michelle felt her face redden as she took it, "you didn't have to do this." Michelle pulled a jewelry box out of the bag, it was a rather upscale name she'd only seen in the Times, certainly not a store she ever thought to even enter on her own. "Oh my!" Michelle exclaimed as she opened the box. "This is gorgeous!"

"Nothing wears like a diamond." Bernard said with a warm smile. "Allow me."

Michelle's fingers trembled as she took the diamond anklet from the box and handed it to Bernard. She didn't dare ask how many diamonds were on it, or what it cost, but it looked and felt expensive. Instinctively, Michelle lifted her right foot so Bernard could put the anklet on her. She couldn't help but stare, it was the most expensive thing she'd ever owned and potentially the most expensive thing she'd ever held in her hands! Bernard clasped the anklet in place, letting his fingers slowly glide up Michelle's calf to her knee before lowering her foot. Michelle couldn't seem to keep her eyes off the anklet.

"I don't know how to thank you for this gift!" Michelle finally gushed.

"We have all weekend for that," Bernard replied, raising his glass to Michelle, "to a lovely weekend!"

"To a lovely weekend!" Michelle responded before sipping from her glass.

Michelle slowly shifted to her feet, taking the few steps over to his seat, then sitting as gracefully as she could in Bernard's lap. He seemed quite pleased to have Michelle's breasts so close to his face. "You won't let me fall," Michelle asked coyly, while leaning into his body, "will you?"

"Not a chance!" Bernard replied, letting his right-hand slip around Michelle's back until he was cupping her ass cheek while his other hand gripped her right thigh. "I could never let such a beautiful girl such as yourself get hurt."

"You are just too sweet!" Michelle responded with a deep blush.

Bernard's right hand slowly moved up Michelle's back, his thumb following the line of her spine. With the low back of the halter dress, it wasn't long before his hand touched her soft skin. Instinctively Michelle swept her long hair away from her neck with her right hand. Bernard's hand soon found the clasp behind her neck, with a quick flick of his fingers the front of her dress fell, exposing her from the bottom of her ribcage to her shoulders. Michelle fought the urge to cover herself.

"A very beautiful girl." Bernard said, his eyes transfixed on Michelle's exposed breasts.

"We will be landing in 15 minutes Sir." One of the flight staff called out from behind Michelle.

"You'd better buckle in." Bernard said reluctantly.

"Oh," Michelle made sure to sound disappointed in her reply, "I thought this was my seat for landing!"

"You are quite the minx, aren't you?" Bernard asked, his left hand gently touching Michelle's left breast.

"I'm glad you didn't say it like it was a bad thing!" Michelle giggled, then slowly moved to her feet. "Would you prefer I fix my dress after we land?"

"Oh would you!" Bernard replied like an excited child. "That would be wonderful!"

Michelle took her seat across from her weekend companion, buckling her seatbelt under the hanging top of her dress, then crossing her legs, making sure to tug the dress above her knee. Bernard was elated, adjusting himself in his seat. Michelle felt a bit awkward, she could see the legs of the flight attendant but not her face, so she was fairly sure she wasn't being ogled by anyone but Bernard. He seemed to truly enjoy a bit of the buffeting and moving the small plane did as it descended to land, each move of the plane causing Michelle's breasts to sway, bounce and jiggle. She could see he was getting quite excited about the entire thing. As the plane touched down, Michelle watched the legs of the flight attendant, and when she noticed they moved she quickly fixed her dress, much to Bernard's disappointment.

"Thank you," the flight attendant said as Bernard escorted Michelle out of the plane, "and enjoy your stay."

"Thanks!" Michelle had to giggle; this was her first trip on a plane ever. She was sure this wasn't how normal people traveled! Particularly the topless part. "Where are we going?" She asked as Bernard walked her away from the plane.

"There's a helicopter right over there," he pointed quickly, "that will take us the rest of the way."

"A helicopter?"

"Have you ever been in one, my dear?"

"That was my first time in a plane," Michelle blushed in response, "I've never been in a helicopter either!"

"Then you're in for a treat!" Bernard replied, waving to the copilot.

The copilot took Michelle's hand, while Bernard put his hand on her butt, as Michelle stepped up into the helicopter. With Bernard getting in behind her, and handing her a headset to put on, Michelle put hers on in time to hear the pilot welcoming them. As the helicopter started to rumble more, Bernard spoke to the pilot.

"Hey Mike," Bernard started, "can we take the long way, Michelle has never been in a helicopter before."

"Of course, Sir!" Mike enthusiastically replied.

Michelle found herself clutching Bernard's leg as the helicopter started to lift off, giving her the feeling she was leaving her stomach behind. The view of the airport opened up to the view of a small city before Mike turned bringing them to the coast. Michelle had never seen so many variations of the color blue in one place! It was awe inspiring as the blue was contrasted against white sand beaches and lush green areas. The flight had to be the most beautiful 15 minutes of Michelle's life.

"Where are we landing?" Michelle asked as the helicopter seemed to be heading toward a hotel and marina area. "He's going to miss the golf course if that's where he's aiming."

"We are landing on my yacht," Bernard replied reassuringly, "and don't worry, Mike knows what he's doing."

"Your yacht is big enough to land a helicopter?"

"In the right conditions, two!" Bernard chuckled in response. Michelle was going to respond, but the helicopter suddenly moved, making her stomach feel like it was now a third breast. "Don't worry my Dear," Bernard gripped her hand, "air pockets are a bit different in a helicopter, we'll be on the boat shortly." Michelle nodded, feeling like she was on a roller coaster more than flying at the moment. "Here we are!" Bernard said, removing his headset and hanging it up.

Michelle handed Bernard her handset, as he waited for the co pilot to open their door. Both gentlemen helped Michelle out of the helicopter, at which point she became almost dumbstruck by Bernard's yacht! The biggest house she'd ever seen belonged to the parents of a friend of hers in high school, it was a colonial with three floors, and it would be dwarfed by Bernard's yacht! Bernard eventually tugged her from where she was standing, through a set of glass doors before the helicopter took off. The living room area, where Bernard had just brought her, was bigger than the main area of her new condo! Michelle couldn't understand how something so large could float.

"If you go down that set of stairs," Bernard instructed, leading Michelle toward the stairs as he did, "follow them to the end of the hall, you'll find everything you need in the bathroom off that room."

"Okay." Michelle absentmindedly replied.

Walking down the stairs, Michelle followed the hallway to the door at the end of the hall, which led to the main bedroom. Like everything else, the bed and room were massive. She made her way to the bathroom, finding handwritten instructions and several items in numbered boxes. It was a pretty simple process. Step one went with box one, which contained two enema kits.

"At least I'll be clean." She said as she removed her sundress. "Inside and out!"

After flushing her insides, box two contained a black rubber plug and silicone lube. While not extraordinary, the base of the plug had a recessed hook. Reading through the instructions, Michelle made sure the hook was facing the correct way before inserting the plug. It wasn't overly large, so she managed to get it in place quite easily. The next box revealed the reason for the hook.

"This might be uncomfortable." She whispered to herself as she attached a silicone ring to the end of her plastic cage. "Now to find the hook."

Squatting slightly, Michelle tucked her caged appendage between her legs, holding it in place with her left hand while reaching behind her body to bring the loop to the hook. It took a couple attempts, but she eventually managed to get everything in place, and while it wasn't exactly comfortable having her boy parts held between her legs, it wasn't truly uncomfortable either, although sitting might take some practice. Michelle shifted her hips several times, trying to get things to settle into place before walking back to the counter for box 4.

"Is this it?" She asked herself holding up a pair of cute heels and a black thong. "I mean, this is everything?"

Stepping out of her heels, Michelle slid the snug fitting black thong up her legs. The thong was relatively simple, the only thing that made it stand out was the red anodized aluminum heart that held the material together just above her butt. She wondered if she'd have a small heart tan, which would definitely make for an interesting conversation with Brenda next week! Michelle stepped into the wooden heel with a canvas cross strap, then took a look at herself in the mirror. It was rather amazing how her body had transformed over these months working for Ms. Allison. At first Michelle could only pass the scrutiny of a quick look, but now her figure had more of an hourglass shape, her breasts were perky and beautiful and there was little indication she'd ever been anything or anyone but Michelle her entire life.