Lucy's Revenge Ch. 05

Story Info
Cynthia's continuing humiliation up to the bachelor party.
8.8k words
4.54
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Part 5 of the 6 part series

Updated 10/27/2022
Created 07/20/2006
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Cynthia_D
Cynthia_D
606 Followers

The techies had fun at my expense for the rest of the week and for the most part I was enjoying it. Everyday I was ordered to wear a different set of lingerie under my male clothes to work. Then at some point each day I was ordered to remove my male clothes and give them to my Admin Gayle who would lock them up in her desk till the techies sent her an IM telling her to give them back. I admit it was humiliating to strip down to women's lingerie while Gayle watched, but since she seemed to accept my crossdressing it turned me on that I had a willing audience.

I also knew Gayle went along with this because she was being blackmailed by the techies just like me. But I also believe, based on the wicked smile on her face, that she got a kick out of watching me humiliate myself by stripping down to my lingerie in front of her everyday.

The one change the techies did make came that Wednesday morning in an IM -

"Just want to let you know you will be receiving orders from Gayle as well as from us. We're betting Gayle will find additional ways to add a little more humiliation to your life and we're all in favor of it. We've instructed her to let her imagination run wild and order you to do anything she can think of as long as it exposes you to others in lingerie and embarrasses the hell out of you."

The IM continued "You're to treat every order from Gayle as if it came from us and immediately comply or else you'll be fired. She's already shared a couple of her ideas with us and just we know you'll love them. She has a very sick mind you lucky slut." Even though I know it's impossible, I swear could almost hear the techies laughing.

Gayle came into my office that morning at 10:30 and told me to strip. I was wearing pink that day – garterbelt, thong, bra and beige stockings. I was embarrassed as I took off my male clothes and handed them to Gayle. My face turned bright red when Gayle eyed me up and down then started laughing while she told me how feminine I looked and told me to put on the heels I brought to work in my briefcase.

Gayle walked out of my office with my clothes and as she reached my door she turned and said "I'm going to leave your door open and you are not allowed to close it. In fact, from now on I will decide when your door is to be open or closed. And trust me it will be open for a good portion of each day when you're stripped down to your lingerie."

She continued "If you ever close the door without my permission I will call for an immediate staff meeting in your office. I'm sure you don't want me to do that do you? How many staff do you think will show up and walk in your office and see you nice and pretty in your lingerie? 10, 20, 30?"

I quickly sat behind my desk scared to death someone would enter my office and catch me sitting there in just a sexy bra, thong, garterbelt, stockings and heels. If this happened HR would be paying me a visit and I would lose my job!

At lunchtime Gayle came into my office and closed the door. I breathed a sigh of relief with the door being shut but at the same time became concerned with Gayle's evil grin. She told me to stand up and step away from my desk, turn my back to her then put my hands behind my back.

I did as she ordered. After all what choice did I have with the techies watching and listening? She walked up to me and I felt the cold hard steel of a pair of handcuffs being put on me.

I was going to ask what she was doing when she said "Don't say a word and do everything I say and you'll enjoy today's lunch." And with that she tied a blindfold over my eyes completely blocking my vision.

Almost immediately my office door opened and I heard the footsteps of more than one person enter my office. What could I do? The answer was nothing. I stood where I was praying whoever it was, was also being blackmailed by the techies and security wouldn't be soon escorting me out of my office.

I heard some feminine giggles that gave me some relief there were no screams and footsteps running from my office. But it also hit home that here I was a senior manager in my company standing in front of unknown women wearing only women's pink lingerie. I could feel my face turn a very bright red.

Gayle's words were of no comfort to me "Cynthia, in your office are a few secretaries that I've told how submissive you are and how you're paying me to dominate you. About how you like to dress in lingerie everyday and then like to strip for me to get yourself excited. I've told them how you beg me to take your male clothes and lock them in a drawer and not give them back till I decide to not when you want them. It's just one more example of how you like to be dominated."

"I hope you don't mind but I just couldn't resist sharing your fantasy of being caught wearing only lingerie by a group of secretaries and how they make you into the office slut. It's the role reversal fantasy you keep asking me to make happen with the secretaries being in charge of you and how you're willing to do anything they want to keep your job. Not surprising a few of these women doubted what I was telling them so I had no choice but to prove it by letting them come here today and see you in your lingerie."

Gayle continued but now talking to the women in my office. "Doesn't he just look so feminine in his pink bra and thong? And when is the last time any of you wore a garterbelt and stockings? Only sluts like Cynthia wear them these days. If one of you is willing to pull down his thong you'll see how he keeps his pubes shaved into a nice landing strip."

I was so humiliated! What in the hell was Gayle talking about? I was dressed like I was because I was being blackmailed, not because I wanted to. And I had no fantasies of being caught or being the office slut.

My thoughts were cut off by Gayle's next comments "Cynthia, I've also told everyone here what a good pussy eater you and they should experience it themselves. I want you to kneel in front of your desk and you're going to satisfy the pussy of every secretary that wants you to. Of course you won't know who you're eating but they will know you and those that choose not to be eaten will just get to enjoy watching you in your sexy lingerie.

"I imagine you'll be the talk of the office because you know how a woman likes to gossip and this is just too good to keep to themselves. In fact, I want each of these women to share how they've seen you dress with all their friends. I want everyone to know what a slut you are and hopefully take part in your future humiliations."

Oh shit, how embarrassing. Gayle had me over a barrel with the techies watching and listening. I know I shouldn't have thought this way but the thought of eating pussy popped in my head and turned me on. My cock got as hard as the chastity device allowed. How I hated Lucy! If I were to know whose pussy I was going to lick then it might put me on a more level playing field. Or at least I thought it would since they might be embarrassed that I got to see their pussy. But it wasn't to be, the blindfold prevented that. I ate three different women to orgasm that lunchtime but had no idea who they were and who else was watching.

Gayle waited till all the secretaries left my office before removing the blindfold and handcuffs. She laughed at me as she left my office leaving the door wide open reminding me I wasn't to close it. As embarrassed as I was, all I could think about was how turned on I got eating those secretaries and how my blue balls were back with a vengeance. I was beginning to hate Gayle as much as Lucy. And thinking of Lucy, I wondered if she was ever going to remove the chastity device and allow me to cum or was I doomed to have blue balls forever?

Thursday turned out to be stretching my ass and abuse my nipples day. The techies had sent me an IM late Wednesday telling me to wear matching open tip bra and crotchless panties Thursday.

I didn't own an open tip bra but knowing better than to disobey the techies I went to the mall on my way home and stopped at Frederick's of Hollywood to purchase one. Normally I buy my feminine clothes online and no one knows it's a man buying them. But with the overnight timeline the techies gave me I was going to have to buy in person and face a store clerk.

Fortunately Frederick's had the bra I needed to buy but of course it wasn't on display so I had to ask the clerk if they had one. She stared hard at my chest then smiled at me before saying yes they had them and asking "Is this bra for you or someone else?"

I wanted to die of embarrassment. I realized I was still wearing my pink bra under my shirt and she must be able to see the outline. I had to wear the bra under my shirt when I left work or the techies would have had me fired. But by now I was so used to wearing a bra all day long I didn't even think to remove it in the parking lot before entering the mall. How stupid was I?

I was ready to say for my girlfriend when several thoughts hit me at the same time. A girlfriend with a 40DD chest is unlikely, the clerk already knows I'm wearing a bra and the thought of making her day so she could tell everyone she knew that she helped a crossdresser convinced me to say it was for me.

She giggled and got the bra and held it up for me asking if I wanted to try it on before buying it. The thought of making her day left in a second to be replaced by humiliation. I barely squeaked out no I didn't want to try it on but would she please find a matching pair of crotchless panties to go with it. By now the other customers in the store were listening to our conversation and staring at me. She now laughed out loud as she told me to follow her so she could find matching panties for me to wear. After she got the matching panties she held them up and asked if I was sure these were what I wanted to wear.

When we got to the cash register the clerk (enjoying my humiliation) said in a voice loud enough that everyone in the store could hear "OK, I've written down bra and panty size in our special book so the next time you're in here shopping for your risqué lingerie I won't need to measure you. Shall I put down your real name or do you have a fem name you'd rather I use?"

She looked at me like she really expected me to answer her question. Was she nuts? Then I realized all the other customers in the store had stopped shopping and were staring at me. They also were waiting for my answer.

This much was clear; the clerk had my credit card and wasn't going to finish the transaction till I answered her. It was bad enough she knew my real name but I didn't want it going down in any "special book" for anyone else to know.

I whispered "Cynthia" so no else would hear.

Again in a voice loud enough everyone could hear she said "OK I'll put you in the book as Cynthia. By the way, that's a very pretty name."

She started writing in the book then looked up at me smiling and said "I just noticed we have a couple of other crossdressers named Cynthia in the book. I better write down your real name also so there won't be any confusing you with another feminine man on your next shopping trip."

She was having way too much fun humiliating me in front of the other customers. Their reactions ranged from snickers to outright laughter. I refused to turn around and look at them so they could see my red face. I just looked at the clerk with pleading eyes hoping she would hurry up with the transaction. When she finally handed me my credit card and purchase, I got the hell out of the store as fast as I could knowing I'd never set foot in there again.

When I arrived at work on Thursday there was a package on my desk with a note telling me not to open it till I was told to. At noon Gayle came into my office, shut the door and sat down in a chair opposite my desk without saying a word. Almost immediately an IM popped up on my computer which convinced me she was here because the techies told her to and I knew this did not bode well for me.

The IM said "Open the package slut and let's play!"

I slowly open the package afraid of what was in there. It contained a black box labeled "KLYSTRA'S Improved Dilators", a pair of Japanese clover nipple clamps and assorted weights. I had no idea what the dilator box contained but I knew about the nipple clamps. They were ingenious in that the more you pulled them or as I was guessing was going to happen, the more weight attached to them the harder they clamped down on a nipple.

"Open the box" was the next IM.

I opened it and saw it contained five black hard plastic dildos. They weren't very long but each one was progressively fatter in diameter. The second thickest was bigger than anything I wanted up my ass and I couldn't even imagine my asshole being able to stretch enough to accommodate the thickest one. But somehow I had a feeling that is what the techies had planned for me.

"Strip and give Gayle your clothes. And we had better be seeing you in an open tipped bra and crotchless panties or else."

I did as instructed and Gayle walked out of my office with my clothes to lock them up so I wouldn't have access to them. Gayle was walking back into my office when the next IM popped up.

"Stand up; spread your legs then bend over so Gayle can work a dilator up your ass."

I had no options so I bent over and Gayle took the smallest dilator out of the box, and held it up to my lips. I knew this was the only lubricant I was going to get so I opened my mouth and proceeded to lick the dilator getting it as wet as I could.

As humiliating as that was it was nothing compared to when she walked behind me and worked it into my ass. Fortunately it wasn't very thick so it didn't hurt too much. When it was all the way in she told me to stand up straight and put my hands behind my back.

I knew she was going to handcuff my hands and she didn't disappoint me. She had me sit in my chair then took a long black leather belt and wrapped it around my waist and the chair. She cinched it tight and buckled it behind the back of my chair. I was stuck in my chair with a dilator up my ass. With my hands cuffed behind my back there was no way I could reach the buckle to free myself.

Gayle spun my chair around so I was facing her and she started playing with my nipples. She pinched, pulled and twisted them. She wasn't causing any real pain; in fact it actually was turning me on. Then she abruptly stopped and put on the nipple clamps. These hurt! But not as much as when she added some weights to each clamp.

She turned my chair back around so I was facing my computer monitor then she left my office. Thankfully she closed the door on her way out.

IM "Every hour Gayle is going to replace the dilator that's up your ass with the next size larger. She's also going to add more weight to your nipple clamps each time."

I did the simple math. Five dilators equals five hours. Oh shit! All I could think of was how much my nipples already hurt and to add more weight? And the two largest dilators were going to give my poor asshole a real stretching. I was not looking forward to the remainder of the afternoon.

"With your hands cuffed you can't really work so Gayle has cleared your calendar. We'd hate for you to be bored so we'll play some movies for you. Hope you enjoy."

And with that a porno started playing on my computer screen. It was a threesome consisting of a hot blonde woman and two muscle bound guys. Only it wasn't the normal threesome. As one guy went down on the woman the second guy started sucking the first guy's cock. Eventually the first guy pulled his hard cock out the other guy's mouth and started to fuck the woman. Once he had his cock buried in the woman's pussy the second guy buried his enormous cock up the first guy's ass. The fucking took some coordination but they managed to get a good rhythm going till everyone exploded in orgasm.

I don't know why but movie got me horny and the hour flew by. Gayle came back in office to exchange the dilator and add more weight to the nipple clamps. She first took the next size dilator and put in my mouth so I could try to lubricate it. While I held it in my mouth by sucking on it she undid the belt so I could stand up but didn't take off the handcuffs. She took off the nipple clamps which hurt much more than when she had put them on earlier. The blood came back into my nipples and they throbbed with pain.

Next she bent me over and pulled out the first dilator and immediately grabbed the second one from my mouth and worked it up my ass. This one was thick enough to hurt. She sat me back down and strapped me back to my chair.

With an evil grin she started playing with my nipples but pulling, pinching and twisting them much harder than she had previously. I couldn't help myself and let out a moan because of the pain. She stopped playing but put the nipple clamps back on. This hurt worse than what she had been doing and that's when she added more weights to the clamps.

She left my office and the second movie started. This movie was a compilation of blowjobs. The problem was they were all given by one man who looked very similar to me! There wasn't a woman in the entire movie. But there were a lot of cum shots in his mouth. He proved them by opening his mouth to show the camera it was full of cum. If a man did pull out and came on his face he was sure to lick up as much as he could.

Before I knew it Gayle was back and followed her previous routine. The next porno was ass fuckings – as in the same guy getting his ass fucked time and time again by different men.

I wondered what sublime message the techies were trying to send me. Whatever it was I wanted no part of it.

The fourth and second largest dilator really stretched my poor asshole and my nipples were in agony. I couldn't help myself and cried out in pain. I begged Gayle to take off the nipple clamps and remove the dilator. I was actually crying when Gayle walked out of my office.

Gayle walked back in my office within two minutes but not to give me relief. She put a penis gag in my mouth and strapped it tightly around my head. "No one likes a whiner so this should keep you from complaining. But let's test it to make sure. Shall we?" And with that she grabbed the weights hanging from the nipple clamps and started pulling. When she had my nipples stretched as far as she could get them without ripping my nipples off she twisted the clamps. I saw stars it hurt so bad but no sound came out. I was effectively gagged.

Before the next porno started an IM popped up on my computer.

"You're doing good Cynthia. Only one more but much thicker dilator to go before the day's over." This didn't make me feel any better.

"We almost forgot to tell you, we're letting Gayle leave early today to get her nails done. I wonder who we can get to put that last dilator up your ass? Well don't worry we have an hour and I'm sure we'll find someone!"

Oh my God what was I going to do? I struggled against my bonds to escape but to no avail. I had to sit here for an hour panicked about who was going to walk into my office and find me like this. Would they release me or take advantage of me?

Then the porno started. It was of me sucking cocks and being butt fucked! It was like a "best of" with a lot of different scenes playing in an endless loop! Where did the techies get these different videos to splice together?

At 4:00 in walked Dan from the mailroom. I'd talked with him a few times in the past and knew he wasn't the smartest man in the building but was probably the most muscular and he was openly gay!

An IM flashed on my screen that said "Play along or you're fired" In my restrained state and penis gag in my mouth, I didn't have much choice.

Dan said "I received your e-mail and I must admit what you want is very kinky but I'm willing to try anything once. Also, I didn't know you were gay. I guess when the time is right it's time to come out of the closet. I'll do my best."

Cynthia_D
Cynthia_D
606 Followers