The Agency Ch. 23

*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. I'm open for ideas of what happens with Michelle next, there are a number of characters out there she still needs to interact with, feel free to comment or email your ideas to me!

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Michelle woke up, feeling safe but for the moment wondering where she was, and who she was in bed with. It took a minute, but she soon remembered she was on Bernard's yacht. The man pressed into her back, who managed to be able to cup both of her breasts in his sleep, had to be her host. It took her a bit to extricate herself from his arms, but her bladder had needs that were not to be denied. Once out of the bed, Michelle tiptoed to the bathroom to take care of things. As she finished, Michelle stood and looked at herself in the mirror. It still made Michelle shake her head when she looked at her reflection from time to time. Instead of a struggling, well, whatever Mike had been, staring back at her, she saw a lovely woman wearing a nearly sheer black babydoll with red bows and a tiny pair of matching bottoms. Michelle turned off the light before returning to the bedroom, tucking herself next to her still sleeping host.

The second time she woke up, Michelle was thankful she didn't have to wonder where she was or who she was with a second time. However, why she had her hand wrapped around Bernard's shaft was a bit of a mystery. Had she put it there? Or had it been put there for her? Bernard was snoring slightly, but that certainly didn't mean he hadn't done it prior to falling back asleep. Either way, why move her hand? Michelle knew she would be doing much more than holding his cock soon enough. Michelle decided she felt a bit mischievous, deciding to slowly slide under the covers. Thankfully, Bernard had opted to sleep naked which made things easier for her.

"Well," Bernard cleared his throat as he felt Michelle's tongue on his shaft, "good morning to you!"

Michelle giggled to herself before lowering her mouth on Bernard's shaft. "Mom always said not to talk with your mouth full!" She said to herself. Working him slowly, as he preferred, Michelle enjoyed the warmth of her partner in her mouth and hands. While Bernard may not be her ideal dream of someone to be with, Michelle was happy with the fact he was such a warm and genuine person, which made it easier for her to settle into her role with him. She hoped she would be able to do that with each of her dates while employed. Michelle almost lost track of how she was working him and was somewhat surprised when Bernard finally exploded in her mouth.

"Oh you are quite magnificent with your mouth my Dear!" Bernard groaned softly as Michelle did her best to swallow his cum. "I don't mean to rush you," Bernard said as he lifted the covers, "but Chai will be here shortly."

"Chai?" Michelle asked. "I've only ever had coffee," Michelle continued as she made her way out from under the covers, "chai sounds interesting though."

"Oh, I think you'll enjoy Chai very much!' Bernard replied with a silly grin. There was a quick knock at the door to the cabin, "Come in Chai!" Bernard called out, looking over to see Michelle blush deeply.

"Good morning Mr. Bernie," the woman entering with a tray called out, "and good morning to you Ms."

Michelle found herself looking over Chai, feeling a mix of emotions and an unusual level of attraction. Chai's face was framed with short black hair that was swept behind her ears and held with a white ribbon and bow to match her white uniform. The uniform top fit so snugly, yet perfectly it had to be custom fit to her body as were her shorts. As Chai set the tray on a nearby table and poured two cups of coffee, Michelle's gaze was transfixed on her ass, the bottom of which peeked out ever so slightly from her shorts. Her perfectly toned legs were a soft caramel tone.

"Michelle darling," Bernard nudged Michelle who had been transfixed while staring at Chai, "Chai asked you a question."

"Cream and sugar Ms.?" Chai asked with an engaging smile.

"Oh, uh, yes please!" Michelle finally managed.

Chai brought the first cup to Bernard's side of the bed, Michelle couldn't help but watch her seemingly glide around the bed. Bernard thanked her as he took his mug, while Chai caught Michelle's eyes lingering around her cleavage. Michelle blushed again, and managed not to watch too intently as Chai returned to the tray to bring Michelle her coffee.

"Thank you, Chai." Michelle found herself staring into Chai's warm brown eyes.

"If I may Ms.," Chai said before touching the side of Michelle's mouth with her index finger, "just a little left over."

Michelle had to quickly bite her bottom lip and find something else to think about because her cage had suddenly become far too small. Chai dutifully served them bagels and some fresh fruit, only extending Michelle's discomfort, before she disappeared into the bathroom. It was then Michelle realized Chai had been the one setting her outfits on the vanity for her as well as the plug and other items. Chai obviously knew Michelle was not born a woman, but Michelle wondered if Chai had been or not? Bernard had a particular taste for transwomen after all, why wouldn't he have on here on his yacht? Then again, if he had one here, why would he bring Michelle, Babette and others here too? Maybe Chai was female? There wasn't a lot of room in her uniform shorts, but Michelle had spent the day in a rather tiny thong as well.

"You are all set for today Ms." Chai's soft voice had an almost musical quality to it.

"Thank you, Chai," Michelle finally managed to respond, feeling conversely awkward in light of Chai's elegance, "and thank you for everything you did for me yesterday as well."

"Of course. Ms.!" Chai gave them a slight bow before leaving the room.

Michelle silently sat in the bed sipping coffee and eating breakfast as she wondered how to ask Bernard the question burning in her brain. Chai was exotic and shapely, but was she all girl or was she a t-girl? Michelle was shocked she couldn't figure it out on her own. Obviously she knew who Babette was underneath everything, and the other girls of The Agency weren't out of place as women, but with Chai it was different. With each of the t-girls Michelle had met before, there was always some trace of identity that she could key in on and figure out they were born boys. There was none of that with Chai, but there was also nothing that led her to believe fully that Chai was a natural woman. What was almost as odd was how aroused Michelle had become with Chai around. Only now was the pressure in her cage finally letting up!

Their breakfast was casual conversation, where Michelle tried to figure out when and how to ask about Chai. Eventually, Michelle simply gave up on the idea and decided it could wait. Maybe she wouldn't see Chai again today and wouldn't have to worry about it anymore. Although, the idea of seeing her almost bursting out of her top was enough to make Michelle's cage stir again. Michelle made her way to the bathroom, where Chai had laid out a cute white thong with floral embossment and a jeweled chain attached to the waistband at both hips. Just as there was yesterday, there was an enema kit and plug with the hidden hook to hold Michelle's cage against her body. Michelle used the enema kit, then hopped into the shower to shave and prepare for her day.

After spending her day topless yesterday, walking through the yacht and onto the upper deck wearing just the moderately sized thong was easy enough. Michelle found her lounge chair, kicking off her low heels and rubbing lotion on her skin.

"This is a life a girl could get used to without a lot of effort!" Michelle giggled to herself. "I do wonder where my host is though?"

Michelle decided to settle into her lounge chair, it was Bernard's yacht and he would surely know where she was as well as his way around. The sun was hot but the breeze through Albany helped keep Michelle relatively cool, or at least comfortable. Above her Michelle could see a few helicopters pass by as well as one paraglider, which made her wonder who was checking her out from above?

"Excuse me Ms." Chai said from a distance. "Mr. Bernie is busy with a call," Chai stepped closer as she spoke, "he wanted me to ask if you wanted anything to drink? Or if you need lotion rubbed onto your back?"

"Oh, I don't know what to ask for first!" Michelle excitedly replied.

"Well Ms." Chai smiled sweetly, "among other things, I am Mr. Bernie's masseuse, so I would ask for the drink first."

"You have a wonderful point Chai," Michelle responded, tittering with excitement at the idea of getting a massage from her, "I'll have a drink first, your choice."

"Right away Ms." Chai eagerly responded before disappearing.

Michelle relaxed, feeling the warmth of the sun embracing her body. While the thong was a bit snug, particularly around her tucked parts, she loved the warm feeling on her breasts. Laying out topless had an air of naughtiness to it as well that she enjoyed. Certainly, it wasn't an issue here, but this wasn't something typical women did in America. Michelle giggled to herself, feeling wonderfully European. Her eyes opened as Chai returned, Michelle still found an incredible level of attraction to the slender woman. Although, still not completely sure of her gender, there was no denying her breasts had a lovely sway as she walked.

"Here you are Ms." Chai beamed with pride as she handed Michelle a red and yellow drink. "I hope you like rum."

"Oh Chai," Michelle's eyes opened wide after her first sip, "this is delicious!"

"Thank you, Ms.," Chai smiled at the compliment, "not too quick though, there are four kinds of rum in there!"

"I'll behave!" Michelle responded, taking another sip before setting the drink aside.

"Well," Chai had a particular gleam in her eye as she spoke, "behaving is another story Ms."

Michelle giggled at Chai's overt flirtation. Chai held Michelle's hand, helping her to her feet, before adjusting the towel and lowering the back of the lounge chair so Michelle could lay on her stomach. As Chai stood again, she was soon face to face with Michelle, the snug blouse covering Chai's chest brushed against Michelle's left breast as Chai turned. Michelle felt the tightness return to her cage as she could practically feel Chai's breath on her skin.

"I should lay down," Michelle whispered, her eyes locked on Chai's, "shouldn't I?"

"Yes, Ms.," Chai stepped back but only slightly, "I know you will enjoy my massage skills."

"I have no doubts about that!"

Michelle slowly moved herself into position, finding herself getting onto all fours before slowly lowering her body onto the lounge chair. She hoped that her deliberate movement gave Chai a view of her that would excite her as well. Even as she lay on her stomach, Michelle did her best to raise her ass, her second-best asset in her opinion. Chai moved Michelle's arms to her sides, Michelle could then hear Chai rubbing lotion between her hands before feeling them touch her shoulders. Michelle almost jumped at Chai's touch; she could feel her sphincter tighten around the plug as well as her cage strain to keep her in check.

"Just relax Ms.," Chai spoke softly, "you are very tense."

"That feels wonderful." Michelle cooed.

Chai slowly massaged her way down Michelle's left arm, then her right. She even took the time to massage both hands and wrists. As Chai's hands returned to Michelle's shoulders, she massaged the back of her neck into Michelle's hair line. Her touch was amazing, and Michelle was becoming more and more relaxed by the moment.

"If you don't mind Ms.," Chai said softly, "I need to straddle you, it will be easier."

"You can do whatever you want to me Chai!" Michelle immediately responded.

"Maybe later Ms.!" Chai giggled.

Michelle felt Chai moving, once in position Chai was sitting on the back of Michelle's upper thighs, her crotch rubbing against Michelle's ass. Feeling her in that position, with the plug inside her, it was almost as if the plug were Chai. A soft moan escaped Michelle's lips before she even realized it. The feeling of Chai's oil covered hands sliding up her back both relaxed and excited Michelle who began to wonder how big of a wet spot she was creating from all this sensory input. Chai's hands slowly massaged their way to Michelle's lower back, her thumbs working underneath the tiny waistband of Michelle's thong. Michelle wondered if she should offer to take it off? As she went to speak, Chai shifted again, her hands returning to Michelle's ass where she focused her efforts for the next few minutes.

Michelle found her mind racing, wondering if Chai had a tucked cock inside her snug shorts as well? She knew she would offer zero resistance if Chai decided to pull the plug in her ass and replace it with a cock. If anything, Michelle would gladly help! Michelle was actually disappointed as Chai moved to her thighs. While her touch was still heavenly, Michelle was getting desperate for some different attention. By the time Chai was massaging Michelle's feet, the swelling inside Michelle's cage subsided enough to be comfortable again.

"How do you feel Ms.?" Chai asked sweetly.

"Oh Chai," Michelle's voice sounded almost sleepy, "that was amazing!"

"When you are ready," Chai continued, "we can readjust your chair again and I'll massage your head and shoulders."

"Okay," Michelle replied, "I may not be ready to move for a bit though."

"Take your time."

Michelle wasn't tired, actually her mind was running a million miles a minute, but Chai had done such a great job massaging her that Michelle's limbs felt heavier than ever. She'd never experienced a massage before, but all her muscles felt like melted butter. Eventually she did manage to slowly turn over and was greeted by Chai's smiling face.

"Let's sit you up first," Chai reached forward with her hands as she spoke, "then I'll lift the back of the chair for you."

"Thank you." Michelle replied, slowly sitting up with Chai's help.

Chai moved the back of the lounge chair upward, locking it in place before lifting Michelle's hair as she sat back. Placing her arms on the rests of the lounge chair, Michelle slowly opened them, enjoying the expanse of luxury homes and yachts while the sound of the ocean and smell of sea salt filled the air. Chai's hands returned to Michelle's shoulders, slowly working their way up into her hair.

"A girl could get used to this." Michelle whispered.

"With any luck Mr. Bernie will have you back again!" Chair responded.

"That would be lovely," Michelle replied, "I'd show up just for another massage!"

Chai's hands returned to Michelle's shoulders, while she rubbed the front of Michelle's chest her hands remained away from Michelle's breasts. Much to Michelle's disappointment. Eventually, Chai stopped, moving around Michelle and standing off to the side. Looking her exotic figure over, Michelle still not 100% convinced Chai was a woman.

"I have other things to attend to Ms.," Chai smiled sweetly, "but I will be back out to check on you soon."

"Thank you." Michelle replied, smiling as well.

Michelle watched intently as Chai walked away, the rhythmic sway of her pert ass was mesmerizing. When Chai looked back, catching Michelle's stare, she gave Michelle a quick wink before bending forward slightly and sticking her butt out. Michelle puckered her lips, giving Chai a quick air kiss before she disappeared from sight. Sipping her rum and juice concoction, Michelle enjoyed the relaxation but eventually became a bit bored. Making her way inside, it was nice to get out of the sun for a bit. She was able to locate a small refrigerator behind the bar and cut up some fresh fruit, she knew there had to be some kind of crew for a yacht this big but there was no telling where anyone was due to the size! Michelle almost felt alone. At least she knew where Bernard's cabin was, and was able to make her way there to go to the bathroom. When Michelle returned to the lounge area Bernard was sitting on the couch.

"Ah, there you are!" Bernard had a smile on his face but there was underlying tension.

"Chai made me a drink," Michelle replied as she approached, "I had to relieve myself after." Michelle walked to Bernard, perching herself on his lap, which positioned her breasts directly in front of his face, eliciting an immediate smile. "Is everything okay?"

"Just a little market fluctuation," Bernard replied, "nothing to be too concerned about."

"I can gladly take your mind off things if you'd like." Michelle leaned into Bernard, brushing the side of his face with her breast.

"Who am I to say no to such a beautiful girl?" Bernard answered by cupping and squeezing Michelle's right breast with one hand and ass with the other.

"Flattery will get you everywhere!" Michelle replied, slipping her left hand between them to rub Bernard's crotch through his shorts.

Michelle began to wish she had the same amount of nerve endings in her breasts that real women had as she watched Bernard rub, squeeze, lick and kiss her breasts. Bernard guided Michelle so she was straddling his lap, he held one hand firmly on her ass while using the other and his mouth on her breasts. With a hand behind his head, Michelle braced herself with her free hand on the back of the couch. As she looked up she could see Chai standing where the lounge chair was, looking through the window, watching Michelle and Bernard. Chai's right hand was not visible, the angle of her arm led Michelle to believe it was between her legs, while Chai's left hand was groping her own breast. Michelle felt herself getting more excited as she watched Chai seemingly pleasure herself.

"My goodness my dear," Bernard whispered hoarsely, "you do know how to improve someone's mood!" Bernard slowly yet eagerly pushed Michelle, indicating he wanted her between his legs. Michelle somewhat reluctantly moved, losing sight of Chai as Bernard pushed his swimsuit down his legs. "But your mouth is such a wonderful treat." Bernard inhaled deeply as Michelle snaked her tongue around his balls and up his shaft, "I just can't deny myself that pleasure!"

Michelle took her time pleasuring Bernard, knowing that was what he enjoyed the most. She'd almost forgotten about Chai, until she looked up and saw her standing behind Bernard, her hand still fondling her breasts through her snug top while the other was now obscured by Bernard's head. Michelle redoubled her efforts, determined to give Bernard the most amazing blowjob he'd ever received while Chai watched. The next time Michelle looked up, Chai was no longer there. She felt disappointed for a moment, until she felt a body press into her back.

"It seems you've made a friend my dear!" Bernard groaned softly as Chai's arms wrapped around Michelle's body. Michelle moaned around Bernard's cock as Chai cupped and squeezed one of Michelle's breasts while her other hand freely roamed Michelle's body. "I suggest you not swallow everything," Bernard grunted, signaling he was getting close, "she's going to want you to share."

Michelle felt Bernard's cock swell in her mouth while Chai's hands clenched her tightly. Backing off his cock so just the tip remained inside her tightly sealed lips, Michelle feverishly stroked his shaft with her hand, massaging and rubbing his balls with the other one. She could feel the cum surging through the underside of his shaft before exploding into her mouth. Her mouth felt full, as she tried to milk the last of him out of his cock. Slowly letting his cock slip from her lips, Michelle leaned back, following Chai's hands moving her until they were facing. Chai's eyes burned with lust, her right hand slipping behind Michelle's neck, pulling their mouths together. Michelle and Chai got up on their knees, slamming their bodies together while Chai's tongue plunged into Michelle's mouth. Michelle grabbed Chai's ass with one hand, groping for her breast with another while Chai focused on simply holding Michelle as tightly to her as possible while they swapped Bernard's cum in their mouths. Michelle felt herself melting into Chai as they kissed.