The Business Trip

by Kristie Knight

Chapter 1

 

Young Michael Zorn was an up and coming professional for the Tress security firm on the outskirts of Atlanta, GA. The members of his firm routinely took travel opportunities to keep current on the latest techniques and equipment in the security game. Michael was married to Joan, but it was more a marriage of convenience than true love. Truth was, Michael loved to go on business as much as possible and get out of town. He had a secret; and was able to live some of his fantasies while away from the house. He always loved to wear silky lingerie under his business suits, slacks, etc.

Michael started years ago with just simple panties, but as his courage grew, he started wearing thigh-high stockings. The feel of the material against his legs drove him absolutely wild and he could have these feelings all day long during these boring seminars and classes. He always tried to make sure that the color of stockings matched the color of slacks. The problem was that these stockings didn't always stay up like they should.

His latest escapade began in late January down in Florida. He was told by his boss to get smart on this new fangled monitoring unit designed to not only film a specific area, but also to recognize faces and even voices. It even had a thumb-print scan for entry and exit – all the bells and whistles. Once he arrived at the hotel after a fairly short flight, he laid out his clothes for the first day's (Monday) seminar, including his new silk panties and black thigh-high stockings.

A few hours into the seminar, the stockings kept slipping down and he kept 'adjusting' them as discretely as possible. However, a rather attractive woman (Suzanne) in the classroom noticed this odd behavior so she began to watch him closely. Toward the end of the day, after numerous adjustments (which she saw), she came up to him during a break and began small talk and simple flirting. Then out of the blue she said: "Thigh-highs don't always stay put do they?"

Without thinking, Michael replied: "Why no, they can be a real…" he stopped mid sentence realizing what he was saying.

"It's OK honey. I've been watching you struggle with them all day. Meet me in my suite when we're done with class." She handed him her room card and wrote the number on back of it. His heart began to race. He had no idea what to expect.

At the end of the class, before he could get back to his room, she came up to him and said: "Let's go…now!" He had no choice but to follow. They got back to her room and she said: "OK dear, let's see 'em!"

"What!?"

"You heard me…let's see 'em – STRIP!"

He began to undress and got all the way down to just his panties and stockings. He tried to cover himself, but it was obviously too late for that.

"I thought so. I saw the outline of stockings while you were trying to pull them back up. See, the mistake you made is that you got them one size too big and you didn't shave your legs. The rubber elastic on the inside of the top lace doesn't stick to hair very well…plus, it's just not tight enough. Are your others the same size?"

"What others?"

"Don't fuck around with me little pansy, I know you have more and what's running through your mind. I'll spill your little secret if you're not honest with me. Get it!?"

"Yes ma'am…I've got it."

"Good. Now, let's start correcting your problems. Step 1, here's a new razor. Go shower and shave your legs."

"Are you crazy? I can't shave my legs…" -She cut him off mid sentence.

"Yes, you can…and you WILL my dear, otherwise I'll make sure your boss and your family knows all about you and what you do. You'll be fired and disgraced – but I'm sure it won't come to that…will it dear (as she lightly fondled his pantied crotch)? Now, get in there and shave!"

He went into the shower and took about 15 minutes to shave all the hair off his legs. He came out, dried off and showed her his work.

"Excellent…nice and smooth. Go put on your stockings like a good little slut. You'll notice that the elastic and soft inside rubber stick much better.

As he rolled the stockings up his leg…"Wow, you're right, they do seem to grip a bit better. Thanks!"

"Oh don't thank me yet…I have a couple more surprises for you. Here's the first one. No matter whether you're wearing thigh highs or just plain stockings, you should always were a garter belt – NEVER PANTY HOSE."

"Garter Belt!?!?! You've got to be…" She again cut him off mid sentence.

"Absolutely! You simply must. Trust me dear, you'll like it. Here, I'll help you put one on. Turn around."

He complied.

She helped him put on the jet-black garter belt and hooked the stockings to the straps. "See how nice and snug it fits you…plus ensures the stockings stay up high. This way the stocking tops won't show when you're wearing a short skirt. That's important. Now that you have them on, slip on your panties. Never put on the panties first. Oh, depending on the material of your slacks, you certainly don't want your new outfit to show through, so here's what you'll do." She handed him 2 pairs of long, silk 'knickers'…both back and white. "See it's basically a slip that has individual legs that will help hide what you're doing. Put them on dear. Don't they feel wonderful going over your shaved and stockinged legs!??!?!"

"Oh yes…yes ma'am they do. They feel wonderful!!!!"

"I can see that." She said as she noticed his cock hardening within his silky panties. She knelt down in front of him and began to caress his cock and balls thru the silky material. She ran her other hand over his stockinged legs which further excited his stiff dick.

"Oh my god, you feel so good…Oh, Oh, OH..."

She continued to tease his cock and ensured he stayed rock hard. She owned him at this moment. She then stood up, grabbed his ass…"Now, I want you to serve me honey." She hiked up her skirt revealing her garter belt and stockings…no panties. "Eat my wet pussy!" She forced him down between her legs.

He had no choice but to comply with her orders. He was very talented with his tongue and in short order brought her to 2 deep orgasms. She pushed him back down, dropped her skirt and went immediately into the bathroom to freshen up.

"But...but…but…where are you going? What about me?"

"I'll be out in a minute to take care of you dear – stay hard for me."

He continued to rub his cock through the silky panties while she stayed in the bathroom. She finally came out and he was still rock hard. She kissed him deeply, rubbed his cock and cooed accordingly. Once she had him about ready to explode, she moved around behind him and continued to fondle his cock thru the silk. He had his hands behind him fondling her pussy thru her silky panties. She then quietly reached into her bag behind her and pulled out something. He heard a clink and then felt something cold and steel on his wrists. Before he could move, she said: "There, my dear, now you are completely mine."

He then realized she had just secured a pair of handcuffs on his wrists! "What…what the hell is going on here!??!

"Oh nothing my pet, I just want you to realize who is in charge now." She then picked up a syringe and injected something into his ass. Within a minute he was passed out and on the bed fast asleep. Three hours later he awoke and still felt very groggy. His still stocking clad leg had a collar around it, attached to a small chain, which was attached to the bed post. He was also having trouble breathing. He slowly got out of bed and realized the chain attached to his leg was long enough to walk around the room a little, but not long enough to make it to the door or a window. The bed was so big and heavy that it would not move. It was also bolted to the wall and the floor.

He moved around the room a little, passed in front of a mirror and was shocked to see a woman looking back at him. He looked down and realized he now had on a skin tight corset with garter straps holding up the jet black stockings. He also had on black panties and his hair was now very long and fully styled. His face was made up, ears pierced and he wore 4 inch stiletto heels which were very uncomfortable and hard to walk in. The heels had ankle straps with small locks on them.

The feeling of constriction around his waist and the silk on his cock immediately made him rock hard. He began to rub his cock thru his panties and caress his silky soft stockinged legs. Before long, he was laying back on the bed masturbating furiously until he came violently all over the bed.

"Look at you lying there in your own cum, you little cock whore," Susanne said. "It was a nice performance though…I saw almost all of it and your eruption was quite impressive." Suzanne moved over to him and touched his softening cock, then locked a set of ankle restraints on Michael, and unlocked the chain attached to the bed. "Get up pansy and clean yourself up. Those new ankle chains will teach you to walk…along with the high heels that is – nice short steps."

Michael crawled out of bed into the bathroom and began to clean up. When he finished, he came out and Suzanne was holding a large knife. One hand was behind her back. "Come over here Michelle, I have something for you."

Too scared to argue or correct his mispronounced name, Michael minced over to her. Suzanne grabbed his panties and cut them off. She revealed another black pair of panties from behind her back. "Here's another pair for you – clean. The crotch snaps so you can put them on over your ankle restraints. Look how soft and silky they are…mmmmmmm…I just know your cock will love them…don't you."

"Yes, I'm sure it will too. Wait a minute. What have you done to me, you've turned me into a woman. I can't be a woman. I have to finish the conference and…"

Suzanne interrupted him, "Don't worry Michelle. You're still a man, well at least as much of one as you were before the clothes and make-up. You've got on a wig and the rest is just clothes…for now anyway. I just wanted you to see, and feel, what it was like. By your actions I just saw here on the bed and your current state of arousal, it pleases you…quite a bit…yes?"

"Oh yes, Suzanne. The feel of the silk and nylon and the garters and corset…oh, it drives me absolutely wild!!!!! I just love it."

"Good. It's late Michelle and you need your beauty sleep. I'm keeping you shackled to the bed for tonight and you'll wear what you have on…with one addition."

"What?"

"There's a long, red, silk nightgown in the drawer behind you. It has a medium slit up the side, but it absolutely gorgeous. Put it on, brush your teeth and I'll wake you in the morning. You have everything you need in the room."

"But what about the conference tomorrow? I can't go in there like this."

"Don't worry honey. We're taking this slow. You'll wear your normal clothes tomorrow…with some special things underneath of course."

"Oh goody, goody," Michael said as he hopped for joy.

"I thought you'd like that. Good night Michelle…I'll wake you bright and early."

"Good night Suzanne."

 

Chapter 2

5 am came very early and Suzanne awoke Michael with a light kiss and a rub on his still hard cock. "Wake up Michelle" she said as he stirred. "I've unlocked your ankles, so get undressed, shower and get ready for the day. I'll lay out your clothes while you're getting ready."

"Yes Suzanne."

Suzanne was already immaculately dressed in a sexy blue business suit and skirt that came a few inches above the knee. She laid out a boned corset with garter straps and black stockings while Michael was showering and getting ready. She also had one of his suits brought to the room.

When he finished in the shower, Suzanne instructed him to put on the corset first, then the stockings, then the silky black panties…and she also laid out a full length black slip with a long slit in the front and back. "I've decided not to let you wear the knickers today Michelle. The long slip will hide everything much better and give your whole body the caress of silk thru the day. You'll love it. And, since it has slit up the front and back, you can still wear your slacks. The garter straps on the corset will hold up the nylon stockings and the corset itself will shape you nicely…although it may be a bit tough to breathe until you get used to it. Now, hurry and get dressed or you'll be late. I'll see you in the conference room."

Suzanne arrived in the conference room and Michael rolled in just before it got started for the day. The feel of the silk (under his normal clothes) covering his whole body constantly sent shivers through him and his cock was like an elevator (up, down, up down…) all day long. About 11am, during one of the most boring parts of the day's speeches, he looked over and saw Suzanne staring at him…moving her highlighter pen in and out of her mouth like a small yellow dick. Michael was immediately hard again, but tried to keep his focus on the speech. It wasn't working.

The speaker ended around 11:15 and the entire group was released for lunch until 2pm due to a scheduling glitch. Suzanne came over to Michael and said: "Come on, we've got a lunch date."

The two left in her car. During the ride, his attention was focused on her long, sexy, stockinged legs coming out of that short, tight, blue skirt. His cock was hard all the way to the restaurant. They arrived and she remarked: "Better bring that down sailor or it'll be hard to walk to the door – ha ha!"

As they went in the main door to Chateau de Elegance, a very posh restaurant close to the conference site, Suzanne took over and soon they were both seated at a large, round table with a flowing floor-length tablecloth, candles and all the amenities a 5-star restaurant should have. "Why are just the two of us eating at such a large table Suzanne?"

"I have friends coming Michelle…to join us for a long, luxurious lunch. You will be the center of attention my dear."

Over the next several minutes, 4 other ladies showed up and introduced themselves and gave a big hug and kiss (on the lips!) to Suzanne. Michelle noticed that each lady was immaculate dressed in either a sculpted business suit or dress. And, each skirt had either a long slit up the side or middle showing off their legs exceptionally well. All of the women engaged in small talk and none of them made note that Michelle was a man with women's clothes on underneath. Each of them had a few drinks the mood lightened greatly as the meal went on. Shortly after noon, Suzanne began rubbing Michelle's leg getting him very excited. The touch of her hand rubbing his suit and consequently the nylon and silk underneath was giving him a raging hard on. He also noticed all the other women becoming very friendly toward each other…whispering in each other's ear and giggling, caressing each other, and so on.

Suzanne then told Michelle to look underneath the table and tell her what he saw. He leaned over to take a peak and noticed each woman fondling and caressing themselves and each other. Above the surface though, you'd never guess anything like that was happening. As Michelle came up, Suzanne whispered in his ear: "All the women are very, very discrete and would appreciate your 'special services'…if you know what I mean."

Michelle responded back: "Well, no…I guess I really don't know what you mean."

"Take another peak." Suzanne said.

Just as Michelle got low enough to see the action going on under the table, Suzanne pushed him down underneath and nudged him toward Roxanne, who was always one of the most amorous women. The next thing Michelle knew, a pair of hands had him by the ears and was pulling him toward the open legs of one of the women. Since her skirt was already slit high and short anyway, he could see her wet, glistening pussy directly ahead. The hands on the side of his head kept pulling on him until he was buried in her snatch. He began licking and kissing until her felt her shiver. He withdrew out from under her skirt and other pair of hands grabbed onto the side of his head and forced him into yet another yet, horny pussy. This action repeated itself until he wasn't exactly sure what direction he'd come from. After he serviced the last woman, she gently pulled him up from out from under the table. He apparently had just serviced Suzanne. She was very flush and had a wonderfully satisfied look on her face!

"That was wonderful Michelle!!!! Very gentle, but firm, soft and wet enough to make me cum. You'll do just fine…eh, ladies?" All the other women nodded and voice their agreement and pleasure.

It was now nearly 2 pm and he was starving. There were dirty plates scattered all over the table where the other women had just finished lunch. He had apparently 'eaten' all the other women while they ate a satisfying meal.

Suzanne said to all of them they needed to be going and everyone agreed that lunch was absolutely fabulous, but it was time to go. Michelle voiced her concern that she was still hungry and needed something (food) to eat.

"Nonsense;" remarked Suzanne. "You're a bit too heavy anyway and we need to slim you down to a respectable size so you'll fit everything. Plus the fact that's it's nearly 2 and we must get back to the conference anyway." On the way back, his eyes were still focused on Suzanne's long, stockinged legs and that short, tight blue skirt. He was hard again which made it difficult to walk back into the conference room.

The rest of the afternoon was torture as the thoughts of him under the table eating all those wet pussies ran thru Michelle's mind. That combined with the silk under his normal clothes kept his raging hard-on for the rest of the day.

After 3 more days of very similar activity – silk and satin under things, garters and stockings, lunches with the women around the table as the 'main course,' and Suzanne directing his every move; the conference was finally over and Michael went home – still in a bit of a daze. Now that the conference was over, Michael thought he was free and clear and would never run into Suzanne again. He could not have been more wrong.

 

Chapter 3

Two days after returning to work, his boss, Ron White called him into his office and informed him he's been transferred to the 'big' office further downtown. "It's a bit longer drive for you but with better growth opportunities. And you have been requested by-name by one of the executives so you should feel honored. You will also receive a slight pay increase and some fringe benefits, but the hours are quite a bit longer…so I'm told. You're supposed to report down there on Friday and see a Ms. Tress for further instructions. She's on the top floor…corner office in the back. Good luck!"

Michael had his marching orders so he cleared out his desk and said goodbye to his co-workers over the next few days. On Friday, he reported in to the main security office and went up to the 69^th floor. As soon as he exited the elevators, he saw the large "Tress Security, Executive Floor" sign directly ahead and the male receptionist behind the desk.

"Hi, I'm Michael Zorn and I am supposed to see Ms. Tress this morning…I was transferred from the…" The receptionist cut him off mid sentence. "Yes, we've been expecting you…please come this way and I'll show you to her office. She's at a showing right now, but will be in shortly."

"A showing?" Michael asked.

"Yes, a showing…she has them on occasion for selected employees."

The receptionist and Michael made it back to her office and he sat down in front of her desk and waited for Ms. Tress to arrive – he was nervous.

A few minutes later, he heard a very familiar voice: "Michael, it's good to see you again…welcome to the big office!" She closed the door behind him.

"Suzanne?!?!!?"

"Yes, it's me…but it's Ms. Tress here in the office! You will learn that quickly."

"You are Suzanne Tress – President of Tress Security Company!?

"President and CEO actually." Suzanne replied. I was soooo impressed with you at the conference that I just had to have you down here for my own personal enjoyment. The current receptionist is sort of, well, stupid to be honest and not very efficient…but, he's cute so I keep him around. I need someone who's proficient at security issues as well as attentive to MY needs – you're perfect for what I need here."

"Well, I'll certainly do my best here for you Suza…uh, Ms. Tress."

"So tell me Michael, or Michelle as we formerly knew you, are you wearing your special 'things' today?

"No ma'am, I didn't want to get distracted or have any problems with the new job and all."

"DON'T call me ma'am dear…it makes me sound like an old maid. I much prefer Ms. Tress – don't forget it! Understand Michelle?"

"Yes, Ms. Tress."

"Good. But from now on, you will take what I taught you at the conference and apply it here…and you know exactly what I'm talking about. Tomorrow, I want you in my office at 7:30 sharp and show me. Wear your favorites under your normal clothes and be prepared for my scrutiny. Now, get out of my office and talk to Pat about your new work space. She's down the hall on the right and knows you're coming. Don't give her any lip either."

Michael went and did as he was told and went to Pat's office. Pat was a larger woman, but still very beautiful and sophisticated none-the-less. She too had on a 'power-suit' which really accented her tiny waist and ample hips and thighs. She wasn't lacking in the chest area to be sure and her skirt of course showed plenty of leg with black stockings and 4" spiked heels. With the heels, she was easily over 6 feet tall and a commanding presence.

She took Michael down the hall further and showed him his new office – a bit small, but larger than his old office. Pat told him where the basic office supplies were and the computer was already on the table and running. As Michael passed her thru the doorway to his desk, she gave him a little pinch on the butt and grinned.

Michael looked around a bit and saw the sticker on the screen indicating his new login and password, so he began his day. The only thing different really about the new place were two small 4" rings about two feet apart and directly under the desk. There was a flat black glass plate in between them also. The rest of the day was quiet, but just before he was about to leave for the day, a reminder popped up on his screen: "Ensure to wear your proper clothes tomorrow."

The next day, Michael did as he was told and wore his silky underwear to include a bustier with garter straps and nylon thigh highs which he made sure he clipped into place. He also wore a long black slip with slits up the front and back so to hide the garter straps. Plus the silky feel of the nylon stockings against the slip felt incredible.

Around 7:30, he walked into Suzanne Tress's office and she was already there waiting for him. He began to sit down when Suzanne stopped him. "No, you won't have time to sit – just close the door behind you and strip down – DO IT!" Michael did as he was told and revealed his silky slip, underwear, bustier and stockings; and was sporting his usual hard on. Suzanne of course noticed this as she walked around him and evaluated her new employee. She caressed the material as she went and ended up standing behind Michael.

"That's very, very good dear. You look wonderful and obviously (as she ran her hand lightly over his pantied cock) feel the same way…don't you dear?"

"Yes, Ms. Tress, I do" Michael said as he trembled.

Suzanne then moved in front of him and lowered Michael's slip down to his knees. She began rubbing Michael's ever growing cock. "There's just one thing wrong with your outfit darling…your shoes."

"My shoes? What's wrong with my shoes Ms. Tress?"

"They're just plain ol' men's shoes with no style at all. I want you to go down…to the 'Lady's Boutique' and buy the pair of shoes that I have reserved for you. You'll love them dear – really you will. Make sure to wear them all the way back to work." She pulled Michael's panties down and revealed his cock and began to suck on it. But, just about the time Michael was ready to cum, Suzanne stopped, pulled his panties and slip back up and told him to get dressed and go get the shoes…and then come back to her to finish the 'job.'

"Oh God, please Ms. Tress, finish me…finish me off please…I need to cum…I need to cum!!!"

"I know you do dear…I know you do. That's why you must hurry back with your new shoes so I can finish…and so can you" she said with a wry smile. "Now go."

Michael finished getting dressed and wobbled out of Suzanne's office and down the road to the boutique as he was told. He walked up to the young lady behind the counter, mentioned his name and that he thought there was a pair of shoes waiting for him here.

The lady behind the counter said, "Oh you must be her new stu…uh, co-worker. And yes, I have the shoes she picked out for you right here."

As he opened the box, he noticed that they were black ladies shoes with a very short 1" sharp heel on them!

"There must be some mistake. These are women's shoes."

"I know hun. These are the ones she specifically picked out for you and you must walk back to the office in them. She apparently has a surprise waiting just for you when you return. Try them on…you'll like them a lot!"

Michael sat down and untied his normal shoes and began to put on the strappy shoes that Suzanne picked out for him. "Oh no, dear, you must take off your socks," said the saleswoman. Without missing a beat she slid her hand up Michael's slack and pulled off his socks revealing the sheer stockings he had on. "Very nice dear…very, very nice. These shoes will feel wonderful on your feet now."

As she put the shoes on him, Michael heard a distinct 'click.' "What are those rings on the inside of the shoe?"

"Oh that's just the latest style honey…a silver ring comes on most of the new style shoes – it's very, very popular."

"Well, OK" he said as she slipped the other shoe onto his foot and again her heard a distinct 'click.'

"There you go sweetie. Stand up and lets see how you look."

Michael stood up and was amazed how comfortable the shoes were and he actually was able to walk rather well with the low heel on there. And now that there was just a thin layer of nylon separating his foot from the air, it was nice and cool. "Oh that feels wonderful!!! I love them!"

"We knew you would dear…we just knew it. They've been paid for by Ms. Tress and she's expecting you back…uh, I'm sure."

"Yes, I need to get moving and get back there." Michael forgot all about his old shoes and left them in the store. Luckily his work was just a few blocks down the road so he was able to walk without difficulty all the way back and nobody seemed to notice the shoes especially since this slacks were fairly long and flared to begin with. As Michael entered the main office floor entrance he noticed that there were several men wearing these style shoes – he'd simply not noticed before. After all, how often do you really notice a man's shoes?

Once back in Suzanne's office, she again ordered him to strip. He did so without thought. "Oh those look much, much better darling…much more you to be sure!!!"

"Now, please Ms. Tress…you promised…I still need to cum!!!!"

"Very well dear, take a step forward closer to the desk." As Michael did that, Suzanne crawled under the desk and again, pulled his slip and panties down to reveal his ever growing cock. She began to suck on him again when she suddenly stopped and he heard two 'clicks.'

"What was that noise?" he said as Suzanne rose from under the desk (with Michael still having a raging hard-on). "And why did you stop…I still need to cum!!!!"

"Patience dear, patience. Do you remember how you went down on all those women in the restaurants last week? That's what I want you to do now…to me. Get under the desk – NOW!"

"But you promised Ms. Tress…you promised you'd let me cum."

"Oh stop your whining and get under the desk and lick my wet pussy!!!"

"No. Since you won't let me cum, I'm going to jack off til I cum myself."

As Michael began to jack himself off, Suzanne rushed around the desk behind Michael, forced both of his arms behind him, bent him over the table and locked a set of hand cuffs around his wrists. As she did this, it was now clearly evident those clicking noises he heard earlier and what the rings mounted in the floor were. His feet/shoes were now securely mounted to the floor and he could not move his feet more than just an inch or two.

"What's going on here? Why won't you let me cum…and why are my feet chained to the floor. Who are you and why are you doing this?" Michael said as he began to whimper like a little school girl.

"You didn't follow directions dear and all my men always follow directions. When you follow directions, life is much, much better and you get some of the things you want and you'll be very, very happy."

Still bent over the desk, he said: "Well, what is it you want me to do?"

"I told you dear, I want you under the desk and for you to eat my wet pussy UNTIL I CUM."

"Well, if I do, will you suck me 'til I cum…I still need to cum…badly Ms. Tress."

"I think we can probably make that happen!"

Suzanne let Michael up off of the desk and he bent down below as Suzanne sat down in her chair. She hiked up her silky skirt revealing no panties and a very wet pussy. She grabbed Michael's head by the ears and began to rub his face in her juices. He began to lick and lick as she carried on several phone conversations and typed on her computer like nothing was happening. Michael then heard: "Yes, he's under my desk right now sopping up my wet pussy juice with his mouth – he's very talented that way you know. His tongue…OH…OH…OH…oh, he's concentrating on my….OH, OOOOOH…clit now and I'm going to…to…OH, OH, OOOOH, OOOOOH, CUMMMMmmmmmmmmm…..YES!!!!!! Oh my God that felt soooooo good. I have to run now dear and clean up a bit. I'll talk to you later."

"That was very, very good Michelle…you haven't forgotten a thing from last week – which is part of the reason why I wanted you up here…or down here as the case may be…working for me! I'll be right back."

"But wait…you promised you'd let me cum if I ate your pussy…you promised…you promised!!!"

The pleas fell on deaf ears as Suzanne walked out of the office and locked the door. She returned a few minutes later only to stuff a pair of silky panties (which she used to mop up her pussy juice) in Michael's mouth. She then put tape around his mouth and head so he couldn't remove them and so his voice was severely muffled. She was now standing behind him:

"Now that you have the clothes, the shoes and the attitude of a simpering, helpless sissy, I'm going to continue your training my little Michelle," Suzanne said in an angry voice. She pulled down Michelle's slip and black panties and began massaging and inserting some liquid into his ass. She then began prodding Michael's anus with a small strap-on dildo. Michael began to scream, but the panties stuffed in his mouth and the tape muffled his pleas. Michael's head was still in Suzanne's chair and only his ass stuck out from beyond the desk. Once the dildo was inside Michael, Suzanne pumped very slowly while her right hand massaged and stroked his cock! Michael was experiencing more pain and pleasure at the same time than he'd ever thought possible. Suzanne kept fucking Michelle's asshole all the while stroking away on his hard cock until he came very violently. When he did, Suzanne pumped the dildo as far as it would go and squeezed it at the base shooting a warm cream deep into Michael's rectum…over and over while he too was still cumming.

Michael's pleas slowly stopped and his body went completely limp…as did his cock.

"There now little Michelle…wasn't that absolutely wonderful…to get fucked by this dildo and cum at the same time. Wasn't that just wonderful!!!!!!!! And here's the best part…see that little flat black piece of glass in the floor??? Smile, you're on candid camera!!! That's right honey, there are 4 tiny cameras under that glass capturing every possible angle. Everything is on film and we get to watch it until our heart's content!!"

All Michael could do was just moan a little because he just couldn't figure out how all this happened to him. Suzanne just laughed a little as she pulled the mild dildo out of his ass and left the office. She returned about 30 minutes later as pristine as ever. You'd have never known she was just wearing a strap-on dildo and fucking one of her new employees. "My dear little Michelle, now that you've experienced what it's like to be a woman in a man's world, I'm going to let you think about this experience overnight. Don't worry about the cum stains on the carpet. Our maid that comes thru here each night is very experienced and used to it…just don't interfere with him and he probably won't even notice you. Good night Michelle…and we'll see you bright and early in the morning!" With that, Suzanne, left the office and locked the door.

Michael was still too stunned to do anything…not that he could either. His feet were locked into women's heels and further linked to the floor. He was still wearing women's lingerie with both the slip and his panties down around his knees. He'd been fucked (literally) with a dildo by his boss, and the juices were still running down his legs…while cum still dripped from his limp cock. He was exhausted and fell asleep with his head still on her chair. He could still smell her 'perfume' coming from the seat of the chair.

 

Chapter 4

Around 8 pm and after all the other employees had gone home, Michael was still strapped to the floor, bent over on his knees, head resting on her chair and hands still cuffed behind his back. His ass had finally stopped stinging and was feeling a bit better. Just then he heard the door handle giggle and someone unlocked the door and walked in. He shook his body as much as possible back and forth and tried to yell for help, but all he heard was a young man snickering at his predicament. Michael being under the desk still and worn out, he could not see who was in the room. All he saw was a carpet sponge cleaning the carpets and finally a vacuum finishing the job. He heard more snickers and the office door closed again and he heard it lock. He was there for the night.

Michael was startled around 8 am when Suzanne sat down in the seat where his head was. Her legs straddled him and she draped her long flowing dress down over his head and it fell gently down his back. She reached under her dress and ripped Michaels tape off and removed her soiled panties still stuck deep in his mouth. Before he could get a word out, she grabbed the side of his head again and jammed his mouth in her wet pussy. "Eat it slut!"

Michael tried to stop himself, but her 'perfume,' physical strength, and his exhaustion made it impossible for him to resist her. She forced him to lick her for over 15 minutes and she came in spasms.

After this short session, she got up off the chair and lifted Michael's head with her hand and said: "See my little Michelle, this is just the start of your official welcome into our business. There will be much more to come if you cooperate; to include a sizable $5000 a year raise starting immediately. Interested????

"Oh yes Ms. Tress, I could really use an extra $5000. What do I have to do?"

"I'm glad you asked honey…I'm glad you asked. You've already began your eventual transformation into one of our full-time employees, but we have a long way to go. You must finish this week out satisfactorily – doing everything we say. If you do, then I'll make sure you receive that money. And it gets better…each week for the rest of the month, 3 more weeks to be exact, you'll receive a raise of the same amount until you have an additional $20000 per year raise. How does that sound?"

"Wow!!! $20,000!!!! That's incredible…and I just have to do what you say for the next month?"

"Yes."

"I suppose I can put up with just about anything for a month to get $20,000 extra a year! But, I'm still so horny Ms. Tress…I desperately need some relief."

"In that case, I'll be right back honey!"

Michael got very excited about possibly receiving some relief and really wanted to fuck one of the office skanks. He was hoping that's what Suzanne was arranging!

Suzanne walked back in the room and she brought another woman with her, although all Michael could see were her long legs considering he was still locked underneath the table, handcuffed, with his slip and panties still pulled down.

"Remember Michael, to get the money, you must cooperate with us and do what we say. This also includes no yelling or screaming or raising your voice. Each time you don't do what you're told, that subtracts $1000 from your total raise. Understand?"

"Yes Ms. Tress"

"Good. This will be part 2 of many of your initiation into the company. Mary is going to be sitting down in the chair now dear and you'll do exactly what she says." Mary sat down in the chair and she too was wearing a long dress which she slipped over the head of Michael. He really couldn't see anything but suddenly he felt something soft and rubbery against his lips.

"Take it inside your mouth dear and suck on it" Mary said to him.

At that point, Michael knew Mary was wearing a strap-on dildo similar to Suzanne's and he had no choice but to comply, especially if he wanted that big raise…so he started sucking as Mary began to fuck his mouth. "Make sure to make plenty of sucking sounds…and Oooooohs and Aaaaahhhhs while you suck it dear…that's better!" Suck it hard and fast and all the way down on the shaft dear. This one is just a training dildo so you shouldn't have any trouble getting it all down.

Michael couldn't believe this was just a training dildo – it felt like a baseball bat trying to be shoved down his throat, but he kept sucking it…deeper and deeper and made sure to made plenty of slurping, Oooooohhhs and Aaaaahhhs to make Mary happy.

A few minutes later, he felt the familiar feel of Suzanne lubing up his asshole and attempting to stick her dildo into his ass…again! He tried to squeal a bit, but the dildo in his mouth and the thought of losing his raise kept him from making hardly any noise…so he took it…again. Suzanne began fucking his ass again – this time quite a bit harder and faster than before. Michael whimpered in pain, but continued to suck on Mary's dildo.

"Work with me Michelle…work back on my cock as you suck to the end of Mary's. Oh yes, that's wonderful…work these cocks honey…work them…work them…work them." Suzanne then reached around Michael and began to stroke his member until he came.

"Now Mary!" Suzanne ordered. Mary squeezed the base of her dildo as did Suzanne, both shooting warm cream into Michael, at the same moment he was cumming. Mary filled up his mouth while Suzanne filled up his ass. All Michael could do was keep bucking back and forth while they all came together.

"Outstanding little Michelle…now that is how a good little slut sucks and gets fucked at the same time. You have done well this session and saved your raise…for now! Thank you for your time Mary…that'll be all today – take the rest of the day off and do some shopping – you've earned it."

"You have had enough training for a while little Michelle, so I'm going to unlock you. Go clean yourself up, put on some fresh clothes and then come back to see me. Make sure you have your pretty things on under there too!!!!"

Suzanne unlocked him and uncuffed his hands. Michael stood up slowly as he was now in great pain. He pulled up his panties, slip and slacks up and walked gingerly out of the office, to his car, and back home; where he showered and changed all his clothes. 2 hours later, he reported back to Suzanne for more instructions…and inspection.

He walked back in her office and closed the door behind him. "OK honey, let's take a look at you now. Go ahead, you know the drill…strip…let's see 'em." Suzanne said.

Michael began taking of his clothes revealing a scarlet red slip with slits up the front and back. When he dropped that, he showed her a very flattering red garter belt, red panties and black nylon stockings with the seam up the back.

"Gorgeous little Michelle…just gorgeous. But, I don't want you wearing just a garter belt yet. You're still too pudgy to work here so I want you to go out and buy plenty of bustiers and corsets. You can either wear just a bustier alone, or your garter belts with a corset. That way, your stomach will be kept in nice and tight…until you lose some weight."

Michael was exhausted and soon Suzanne let him get completely dressed and go back to his desk where a stack of work was waiting for him.

 

Chapter 5

Thursday, after a few more weeks of training, retaining his raise, and proving he was worthy of working for the company, he received an email to him, the other male secretaries, and several other male executives from the outlying departments in the city.

All the men walked into their large conference room and Michael, not knowing exactly what to do, followed the others in. Suzanne was sitting at the head of the table with two large females sitting beside her on both sides. The rest of the chairs around the room were occupied by other women who worked in the main office. The men began going up to her one at a time, kneeling down on one knee, kissing her hand, and then taking a spot behind her. Michael counted 26 men including him. They were all now standing behind Suzanne with all the other women looking at them. "All right ladies, there they are. Not the best looking crop we've had here, but they'll have to do I suppose." All the other women gave a polite applause. "The door is open behind you guys so hurry up and get ready. My girls are back there and ready to assist you. Don't give them any problems if you know what's good for you!"

The men began to file thru the back doors one by one and the ladies around the table began talking and generally relaxing. He was the last one to leave the room and as he did he noticed several men in strange clothes bringing in trays of food and drink, but he wasn't able to make out much more.

As he and the rest of the guys walked down this hidden hall, they finally came to a large room where there were bright lights, mirrors, make up tables and numerous outfits on hangers bordering each side. There were also several large females in the room directing where everyone should go. "ALL RIGHT SLUTS…WE'VE GOT A LOT TO DO AND A VERY SHORT TIME TO GET IT DONE – STRIP!" Loud dance music began to play and every man began taking his clothes off revealing garter belts, stockings, silky slips, bustiers and an assortment of sexy clothes underneath their suits. They all sat down at different stations around the room while the women who were back there began loading up their faces with make up, bright red lipstick, and wigs of all hair colors, sizes and shapes. Michael was then handed a long red silk evening gown with a slit up the side. It was gorgeous and felt wonderful as it draped over his skin. They then brought him red high heel shoes with several ankle straps that came half way up his calves.

The place was an absolute mad house though – sissies running back and forth in various and sundry levels of undress; women caring for their every need with hairspray, make up and clothes, clothes, clothes…everywhere. The woman helping Michael then jerked him by the arm and said, come on…you're on…and forced him thru this curtain where he saw a modeling runway, ultra bright lights, glitter, confetti, flashbulbs going off every 2 seconds and the music was pumping. He thought he could see Suzanne sitting in her same spot with the women who were in the conference room now lining the runway…yelling, cheering, eating and drinking and enjoying the 'show.' Michael didn't know exactly what to do, but walk down the runway in front of all the women cheering at him. He strutted the best he could in those heels, paused at the end of the runway like all the models he'd ever seen on TV and then walked back thru the curtain again.

The other men were also either walking down the runway or poised behind the curtain ready to show off their new outfits. As soon as Michael got back from the end of the runway, he was led backstage and immediately given a new garment to model. It was another red silk gown slightly shorter than the other, with a slit slightly higher up, but still absolutely beautiful…and sexy. Since the slit on this one was higher up, he did notice that his stocking tops and garter showed slightly, but decided to continue. He finished preparing, touched up his makeup and went to the curtain where again, he was ushered out onto the runway to model for the women in the audience. It was a parade of sissies…one after the other modeling for all the women executives there.

This went on for several more hours. He modeled women's business suits (always with short skirts), silk cocktail dresses, long, short and slutty negligees and probably 12 to 15 different outfits during all this – each one with different make up and underwear requirements; but it wasn't finished yet. After his last nightie (which required lots of makeup), he went back to the dressing table and was met by this very short black dress – very shimmery, short sleeved with white cuffs and a white lapel. He recognized it…it was a frilly French Maid's uniform, complete with white apron, black stockings, panties and bustier…and small white cap. The women assistants around the area helped him get dressed and giggled occasionally. Because of how the dress 'poofed' up, no one could see his raging hard on. The feel of the nylons encasing his legs and rubbing the dress material over the past few hours along with the high heels drove him crazy with lust…and all the women knew it. By the time he got to the main curtain to enter the runway, he could see all the other sissies also dressed in their uniforms too. The music was still pounding away and the curtain opened. Just as before, all the sissies went down the runway showing off their wares to the ladies in the audience. From what Michael could see, several of them were kissing each other, leaning back in their chairs masturbating, and still hooting and hollering at all the sissies on the runway. Some of them had also come on stage and were walking beside some of the sissies…some began putting their arms around their waists and rubbing the sissies too.

All of the sissies were now on stage and not allowed to go back thru the curtain to the dressing area. A large bell sound rang out and even more women came upon stage and stood next to or behind a sissy on stage. 2 women were standing around Michael. He saw a couple of the men (sissies) try to jump off stage and were immediately caught, subdued, and forced to the ground by the large women who were formerly back stage assisting them. Michael figured out that he better not try to run…but had no idea what the women were doing.

Two more bells rang out and all the sissies (including Michael) were forced down on their knees, their dresses pulled up, their panties pulled down and cream from tubes were inserted into their assholes. Most of the other sissies looked absolutely terrified as did Michael. One of the large women was standing directly in front of him and the other woman was in back and obviously inserted a large amount of some warm cream into his ass as well. He then noticed a large screen above the main curtain and saw a projector light up. It was him…on film…on the projector! They were showing the humiliating video of Suzanne and Mary virtually raping him…wantonly fucking and cumming inside of him as he was chained to the floor…helpless.

3 bells then rang out and the woman in front of him lifted her skirt revealing a large black strap on dildo and began forcing it into his mouth. Before he could object, the woman behind him inserted a large dildo into his ass and began pumping away. His mouth was now full of warm rubber dildo as was his ass. He did his best to look around and all the other sissies were being given the same basic treatment although some just had their asses filled and not their face. He could still hear the video of his office treatments, and could barely see it from the corner of his eyes. The woman in front of Michael held his ears and was face fucking him while the woman in back held his hips and was fucking him…over and over and over. He was helpless…no strength or will to stop this assault (even if he wanted to). This went on for what seemed like an eternity. The audience was now in a full roar… "Fuck the sissies…fuck the sissies…fuck the sissies!!!!!"

The woman in back began stroking Michael's dick and then he heard her say something. Just then, both his mouth and ass filled up with some warm salty fluid. Both women kept fucking him but the Amazon in front said: "Swallow it slut…swallow it all," as she rammed the dildo completely up to the hilt and to the back of Michael's throat. Michael's cock began to cum as the woman in back kept stroking it until exhausted. One by one, after they had finished with their sissies, most of the women left the stage and began walking out the main door…wiping the sweat from their brow, laughing, massaging their pussies under their skirts, finishing off their drinks, etc.

Once they were all done, Suzanne pointed to one of the women still remaining in the room, then she turned around and walked out the room as well. The woman that she motioned to said: "All right you sissy maids, you're already dressed for it, so get off your knees and clean this place up…NOW!!! One by one, all the sissy maids got to their feet, grabbed a mop, a broom, dust rag and so on and began cleaning up the bottles, plates, confetti, cum, cream and anything else in the room that needed it. For the next 4 hours, all they did was clean. It was now nearly 10 pm and Michael was exhausted and sore.

"You did very well little sissies…the room is now clean and you may go home. Get out and don't be late tomorrow morning!"

Friday morning came very, very early and he awoke, rolled out of bed and showered. He remembered it was "Dressy Friday." All the male sissies had to look their absolute best and show off their transforming bodies. Only skirts/dresses above the knee were allowed as were heels more than 4." Today was a shimmery blue satin dress, which made him instantly horny on sight. He was now thin enough (size 8) to wear just a garter belt and stockings. He made sure he had his C sized breast forms tucked into his shiny, satin blue bra too. The heels were also a beautiful blue with thin steel heel-points which made an ear-catching 'click' when he walked. The final touch was the silky, tight, blue panties, which did an excellent job of containing his prick.

He arrived at work, and joyfully clicked and bounced his way to his desk. He gave a very cheerful good morning to his boss Suzanne, sat down in his chair, rubbed this nylon-clad legs together to listen to the wonderful noise it made under the blue satin. His thoughts were only at the work before him, taking care of his boss's needs and of course of the next fashion show!

 

The End.

  

  

  

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