The Agency Ch. 20

*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, life has gotten busy.

Michelle stood uneasily, the heels she had on were the highest she'd ever worn, the black patent material shining brightly seemingly further away than her feet belonged. Dave, the photographer's helper, held a very full looking petticoat on the floor in front of her for her to attempt to step into. Adding to her lack of stability, or general uneasiness, Dave had also just laced her into a black satin corset with cups that thrust her breasts upward much like the way Victorian women were shown in movies. Michelle rested her hand on the wall, tentatively lifting a foot to step into the very small hole her body would fill soon.

"There you go!" Dave said encouragingly. "Now the other one."

"Okay." Michelle answered sounding as shaky as her balance.

With her second foot in the hole, Dave slowly slid the petticoat up Michelle's legs. The black back seamed stockings she wore were made of real silk, sending ripples through her body as the soft material gradually made its way upward. The stockings were also long enough they almost reached the small pair of white bikinis she had on, which featured small white ruffles across her bottom.

"While I attach this," Dave said holding the petticoat up with one hand, "you can put these gloves on."

Michelle took the satin looking white gloves, figuring out which one went on which hand, then slowly pulled the first one on while Dave buttoned the corset behind her back. She then felt him add a small choker to her neck as well. The outfit she was ending up in was a far departure from how she arrived! Babette had suggested comfort, so for one of the very first times Michelle left their condo in yoga pants and sneakers! It felt liberating not having to wear heels, even wedges, as she made her way to the limo. Dennis was obviously disappointed by her oversized sweatshirt, but his pleasure would be the least of her worries today. Dave and Eric had seemed nice enough when she arrived, Eric even handed Michelle a mimosa to help her relax. She'd never had one before, and as Dave helped her dress Michelle was occasionally sipping on her second one. At least they were being served in champagne flutes and not pint glasses!

"Luckily this goes over your head," Dave said as he approached again, "we just have to be careful with your hair."

"Well, that's a plus," Michelle giggled slightly, "because I can't see my feet anymore!"

"I'll make sure you're all set," Dave replied warmly, "please lean forward just a bit and put your arms out like you're going off a diving board." Michelle complied, feeling her breasts surging forward in the small cups as she leaned forward. "There we go," Dave said, "now stand up slowly and let me guide your arms into the sleeves."

Michelle did as she was told, letting Dave guide her arms into position. The bright white petticoat was now covered with shiny black satin with a white ruffled edge. She felt Dave zip up her back, realizing quickly that the zipper couldn't have been much more than 6 inches long based on how bare her back felt. A quick flash of white, and soon a white satin apron with white lace edging appeared. Dave, who had also fixed Michelle's hair into a sweeping up do, did something else with her hair before declaring her done. The short sleeves of the dress started off Michelle's shoulders and ended just above her elbows only a couple inches above the white gloves.

"Okay, you are ready," Dave said looking Michelle over again, "and look amazing!"

"If you say so," Michelle replied, "but what do I do with my hands right now? It's not like I can put my arms at my sides."

"Here, give me your hands." Dave said putting his hands out.

Dave put Michelle's hands on the small apron, her fingers barely touching. As he led her out, Michelle took smaller steps, uncomfortable at the fact she couldn't see the floor in front of her as well as the height of the heels making her uneasy. With each short step, Michelle felt the petticoat rub her skin as well as her breasts jiggle. It was oddly arousing.

"WOW! Eric exclaimed as Michelle approached. "Dave, lip gloss!"

"Oh, sorry!"

As Michelle was waved toward an oversized red leather chair, Dave disappeared from view. The canvas backdrop behind the chair made it look like a library, with shelves and shelves of books. Next to the chair was an oval end table with a small green glass and brass lamp. It looked like a place Sherlock Holmes would sit to read his paper.

"Okay, Michelle look at me please." Dave said as he returned.

With her head held so she could look at Dave, Michelle could only see occasional flashes of the color he was applying to her lips. It was definitely a bright color of red he was putting on, which also felt heavy on her lips.

"Okay then, let's get started!" Eric said with a big grin.

He directed her through several poses, hands on her knees leaning forward made it feel like her boobs were about to hit the camera. She stood on one foot, with her hands on the back of the chair for what seemed like an hour before she could take a break. Michelle also quickly realized that the length of the dress and petticoat meant her ruffled panty covered ass flashed slightly each time she bent forward. It became more apparent when Dave had to adjust a somewhat rolled stocking top just below her ass before Eric was happy with the picture. When it came time for a quick break, a straw had been inserted into the champagne flute of mimosa for her.

"Okay, now a few with the feather duster." Eric said as he worked on the camera without looking up.

"Here you go." Dave said sticking out the feather duster's handle to her.

"Really?" Michelle somewhat protested after seeing the veiny dildo handle jutting out toward her.

Dave could only shrug, and looked quite relieved when Michelle took it into her hands. She was directed to simply wander around the small set, dust, and lean as needed while Eric moved all about her snapping away. As things progressed, Eric had Dave pull down one of the elasticized shoulders, revealing Michelle's corset. By now her nipples were just becoming visible against the black satin. With the zipper undone behind her, Michelle had to keep one hand pretending to keep the dress from falling off, while clumsily pretending to cover herself. Much to Michelle's delight, the dress was eventually removed. She was even thankful when Eric directed her to kneel, as she was finally able to take the pressure off her feet. It was short lived as Michelle was on her knees leaning over the front of the chair sticking her ass out to the camera.

"That's perfect!" Eric exclaimed, "Just like that! And now bring up the duster."

Dave untied the corset, and now Michelle played the game of pretending to hold that up after the petticoat was finally removed. A flash of her breasts her and here and there, and Eric finally decided he had enough pictures. Michelle couldn't believe how many he took, it had to be over one thousand.

"Okay Michelle," Eric said as he handed the camera to Dave, "why don't you take a look." Pointing to a large screen just off the side of the canvas backdrop, Michelle turned her attention to it. "I think you're going to look far more amazing than you think!"

Pictures started to slowly start scrolling through the large screen, Michelle barely recognized herself, she certainly didn't look like she'd spent the majority of the last two decades living as Michael! She was stunning! The shortness of the dress and height of the heels made her legs look even longer than they were, her butt was nicely rounded as it peeked out from under the petticoat, and then there was her chest. Michelle had seen herself in the outfit in the mirror, but the pictures were far better. She was down right sexy!

"Ready for another look?" Eric asked with a grin.

"Sure!" Michelle excitedly replied.

The next outfit Michelle tried was a snug fitting and short pinstripe skirt, a double-breasted jacket over a semi sheer white blouse, purple and black lingerie, stockings and heels. The backdrop this time was an office setting with a padded swivel chair. As before, the pictures started out tame enough, Michelle simply sitting there with her legs crossed looking secretarial. Eventually, the snug skirt rode up further and further. The jacket came off, as did the blouse all while the poses got more and more provocative. Michelle got more and more excited with each passing wardrobe change. After the secretary, the next two outfits were mostly lingerie. Michelle seemed to be spending more time wearing less and less and it all seemed to stay on for shorter periods of time. The end result was always the same, Michelle barely recognized the sexy woman in the photos as herself. The woman looked more like a professional model.

"I can't get over how great you make me look in these!" Michelle blurted as she continued to look at herself.

"You have a magnificent butt!" Dave said looking at Michelle's ass instead of the pictures.

"Ready to step things up a bit?" Eric asked adjusting his crotch as he stood.

Michelle realized both men were looking her over. She hadn't realized that as she'd been looking over the photos the hand holding her bra up had fallen away. Michelle was now standing there in a small thong, heels and stockings. Looking down, Michelle could see a line of precum leaking from her soaked thong.

"Let's go for it!" Michelle replied, feeling a chill run up her spine.

"Dave, you know the outfit I want next." Eric replied getting his cameras ready.

"Yes, I do!" Dave replied eagerly, "This way Michelle."

Michelle felt almost light headed as she followed Dave to the changing area. What could they mean about stepping up the outfit? Her last outfit had consisted of a pushup bra, thong, stockings and heels. The outfit before that had been a soft pink fly-away baby doll made of mostly sheer material, a tiny pair of bikinis and short heels with some kind of feathers on the front that tickled Michele's toes.

"Why don't you put your hair up in a ponytail," Dave instructed, "high up on the back of your head please." Doing so, Michelle realized that lifting her arms presented her bare chest which Dave was struggling to look away from. "Uh, yeah" Dave said slowly, "just like that."

Michelle didn't know why she did what she did next, maybe it was the fact that she'd been feeling sexy all day? Maybe she was because she was so horny? Maybe it was the impressive bulge in Dave's pants that caused her to do it. Whatever the reason, Michelle slowly wiggled her shoulders, smirking as Dave's eyes followed her swaying boobs.

"What next?" Michelle asked as she lowered her arms, hooking her thumbs in the thin waistband of her thong. "Do I need these for the next outfit?"

"Uh, no you don't," Dave replied finally pulling his eyes from Michelle's chest and looking her up and down, "you won't need anything you have on right now."

"Okay!" Michelle sounded almost bubbly as she stepped out of her heels and turned her back to him. "I hope you don't leave me naked for too long Dave." Michelle said slowly bending forward while pushing her thong to her ankles. A slight groan escaped Dave's mouth, at which point Michelle looked over her shoulder at him. "Everything okay?"

"Yeah, I'm good." Dave said clearing his throat. "Here, these are for you."

"Okay!" Michelle replied taking an interesting pair of stockings from Dave's hand and sitting down.

Michelle removed her stockings, slowly rolling one of the black "wet look" stockings in her hands as Dave left the changing area. The material felt and clung to Michelle's legs like lycra but looked almost like polished latex. At the top of the stocking was a strap with a small silver roller buckle and d-ring. Putting both stockings on, Michelle sat awkwardly waiting for Dave's return. When he finally did, Dave walked in holding what looked like a web of tangled leather straps.

"So, you're going to have to put your feet into these holes," Dave said as he knelt in front of Michelle, "great, then I'll slide it up and you can stand." Michelle did as she was told, and was soon standing almost face to face with him. "Arms through her please." Dave pulled the item up over her shoulders, then stepped behind Michelle to close the back.

"Well, this doesn't leave much to the imagination, does it?" Michelle asked as she looked at her reflection.

The most covered part of her body was the panel covering her cage. The rest of it was a series of one-inch-wide leather straps, that crisscrossed her body meeting every few inches where they were linked together by metal rings. There was a metal ring between her breasts, above them, and on either side which framed her breasts in leather straps but left them exposed. As Michelle was admiring herself in the mirror, Dave put a wide leather collar on Michelle's neck which had three small d-rings on the front.

"This is definitely a different look." Michelle said as long black gloves that matched her stockings slid up her arms. "Is there more to it?"

"The shoes are right over there." Dave said pointing toward a rather large looking shoe box.

Michelle's hands shook as she lifted the lid to the box. Inside was a pair of lace up boots with the tallest heel Michelle had ever seen! The boot stood on a solid black platform. Taking the first one out, Michelle looked at Dave, who simply nodded. Sliding the boot on, Michelle pulled it place then picked up the other one.

"I'll tie it for you," Dave said as he approached, "it'll be tough to do with your gloves on."

"Thank you." Michelle replied putting on the other boot. "Um, how tall are these?"

"It's a 7-inch heel," Dave responded, "and just under a 3-inch platform."

"Geezus, these are tall!" Michelle said turning her foot outward to look at the stiletto spike. "I hope I don't fall!"

"You'll be okay," Dave smiled warmly at her, "you're almost ready."

"Almost?"

"Yup!" Dave winked then placed a thick leather cuff over the boot just above Michelle's ankle. "We have a few of these to put on you." Dave secured the cuff with a small brass padlock.

"Is the lock for show?" Michelle asked hesitantly.

"Oh no," he answered putting the next one on her other ankle, "they are all very real, there's already one behind your neck holding your collar on you."

Reaching behind her neck, Michelle could feel the padlock just below her hairline. Padlocks were added to the straps on her stockings and gloves as well as both wrists. Dave extended his hand, helping Michelle to her feet. For the first time she was now looking Dave eye to eye.

"Let's go get your pictures taken." Dave said as he led Michelle to the studio.

"Well look at you!" Eric said as Michelle approached.

Michelle was taking shorter steps because of the heels, as a result she felt her boobs jiggle with each step. The canvas that held the backdrop was now flat black, the normal furniture was also replaced with a padded sawhorse wrapped in leather.

"Well then let's get started." Eric said with a smile.

Eric started taking pictures, first of Michelle standing around or posing near the saw horse. Michelle was handed a crop, she held against her lips, breasts and face as directed. At his direction she squeezed the crop between her breasts holding the tip to her mouth. The poses became more sexually charged, at which point Michelle was bent over the sawhorse and heard the distinct metallic clink of her ankles being secured to the base. Subtly, Michelle tested the restraint, quickly discovering she could only move her foot a couple inches. Feeling herself getting more excited, Michelle focused on the camera and Eric's direction, posing with her hands above her head provocatively straddling the sawhorse.

"Okay now," Eric looked pleased and horny as he watched Michelle move, "lean forward and put your forearms in those spots."

Doing so, Michelle felt vulnerable and sexy as Eric clipped the locks securing her wrists. She realized that Eric had been the one to secure her wrists, and began wondering what happened to Dave? Michelle saw Eric in front of her, then felt a hand on her ass. The firm hand started at the bottom of her ass, where it met her thigh, slowly glided upward as the fingers lightly grazed her sensitive hole.

"Ohhhh!" Michelle moaned at the touch, her back arching presenting her ass and extending Eric's touch on her hole while Eric took pictures of them. "There you are." Michelle cooed and moaned louder as Eric slowly slid the length of his middle finger over her now loosening hole.

Michelle's hips started to move forward and back in time with Eric's fingers, her mouth open as she panted. Her body lurched as Eric gave her taught butt a light slap, causing both men to chuckle. Michelle's body was on fire, she could feel the heat rushing to her face. All day she'd felt so sexy, on top of it so undressed around two fully clothed men. Both well over 6 feet tall, not overly muscular, but certainly more muscular than Michelle could ever hope to be. She'd felt beyond feminine in their presence. Now, she was tied up, vulnerable and beyond horny.

"So, Michelle," Eric smirked still snapping away with the camera, "we are going to have some fun, then we are really going to have some fun. Sound good?"

"Yes!" Michelle panted as Dave continued to tease her ass. "But what kind of fun comes first?" Michelle felt the familiar warmth of lube being poured between her butt cheeks. "Ohhhh, that kind of fun!" Pressing her sternum against the sawhorse, Michelle felt the first digit penetrate her body. "I love that kinda fun!"

"If you're really good," Dave whispered in Michelle's ear, "we'll let you cum too."

The words sent a ripple through Michelle's body while Dave's finger continued to slide into her body. Michelle no longer saw Eric in front of her with the camera, the other sensations assaulting her body and overpowering her mind were all she could handle. His finger unmoving, Michelle desperately tried to rock back and forth on the sawhorse, struggling against the cuffs to feel the fucking she so desperately needed.

"It seems someone's horny huh?" Michelle couldn't even tell which one of them said it.

"I need you to fuck me!" She squealed. "Please!"

"Oh, we will," one of them teased, "you're going to leave her as full of cum as you can stand!" Michelle groaned again, her frustration only increasing. "This will help."

In front of Michelle was one of their cocks. It was thick, hard, and had a small bead of precum exiting the slit. Michelle's eyes and mouth opened wide as it neared. As soon as it was close enough, Michelle thrust her tongue forward, taking one quick lick up the front and savoring the precum. He held the head just close enough for Michelle to lavish it with her tongue. It didn't matter, Michelle was going to do everything she could to get the rest of the hard cock in her mouth. Drool seeped down her upper lip, but eventually the head slipped into her mouth. Michelle moaned around it, sealing her bright red lips around the shaft. She felt a hand grasp the ponytail, causing her eyes to roll back as she braced herself for more.

"Are you ready for more?" One of them asked.

Michelle answered with a long moan and a flick of her tongue over the cock hovering in front of her mouth. She was rewarded with the cock being slowly fed into her mouth. It went past the back of her mouth and glided into her throat until his shaved body bumped against her nose. Michelle started to feel light headed as she was deprived of oxygen until the cock was removed from her throat. Gasping deeply around the head of the cock still in her mouth, Michelle wanted more, as she exhaled through her nose Michelle sucked on the head swirling her tongue around it.