Lucy's Revenge Ch. 04

"Oops! Looks like we forgot lubrication. Guess you'll just have to give it head while we watch you to get it lubricated."

They couldn't expect me to do this! Whoever "they" are. It could be one or more persons, men and/or women. I had no way of knowing but was too embarrassed to suck on the dildo.

"Start giving head or you're fired!"

I couldn't and I wouldn't suck on the dildo while unknown people were watching. It was too humiliating.

"You have 10 seconds Cynthia or you're fired."

I opened my mouth wide to accommodate the head of the dildo and started giving head.

"Very good slut! You keep giving head till we tell you to stop."

"Make sure you're always looking at the Webcam with your eyes open so we can enjoy your humiliation that much more. But occasionally look at your monitor for new instructions."

The humiliation of it! Here I was a senior manager in my company sitting at my desk giving head to a black dildo that I was going to be putting up my ass soon. My pants and panties were down around my ankles. And some unknown techies were watching me on the Webcam.

I kept looking at the Webcam as I sucked and licked the dildo. I was hoping they'd have mercy on me and tell me to stop giving head soon but at the same time worried they'd still make me put it up my ass.

After what seemed like five minutes a new IM popped up.

"I think that big black cock is wet enough. Stand up, turn around and kneel on your chair so your ass is up in the air facing us and work the dildo up your ass"

They were actually going to make me do it! I knelt down, reached behind me with one hand and pulled my cheeks apart giving them a good view. Then I reached behind with my other hand and pressed the head of the dildo against my asshole.

It was decision time. I could either stop now and be fired or work the dildo up my ass and they'd own me.

I guess I truly am a slut because I worked the dildo all the way up my ass.

When I had it all the way in (and by the way it hurt like hell because it was so long and thick with only my saliva for a lubricant) I stood up and turned around. What bothered me most was my cock was trying to get hard. Why was that happening?

Thank God for the chastity device or the techies would have seen me get hard and who knows where that would have led!

"Very good Cynthia. Now pull up your panties but remove your pants and put them in the drawer that the dildo was in. We'll tell you when you can put them back on."

I quickly typed "But what if someone comes in my office?"

"We'd recommend you not standing up to shake hands."

"But my admin comes in my office throughout the day for various reasons. What am I supposed to do when she does?"

"We'd recommend you not stand up to shake hands."

This was getting frustrating. As soon as I turned off the Webcam my pants were going back on.

The techies must have been reading my mind because the next IM popped up.

"A couple of things you should know Cynthia. First the Webcam is hard wired without an off button. We can watch you all day every day if we choose. You'll never know when we'll be watching so you better do as instructed or you're fired."

"Secondly, the Webcam is a newer model with "automatic face tracking". Which means the camera will automatically follow you as you move about in you office always keeping you in the video."

"Pretty slick huh? Check it out on the internet if you have any doubts. But don't let us catch you visiting any porn sites!"

I had no idea if these techies were even in the same building as me but I could swear I heard them laughing at me.

I sat at my desk and tried to work but couldn't. The thought of sitting there just wearing my panties and possibly being caught was turning me on. And I hate to admit it but the large dildo up my ass was making me squirm because it felt so good. In fact I caught myself rocking back and forth on the dildo several times trying for more stimulation.

I just hope the techies weren't watching me because my face would have given away how much I was enjoying this. I was totally turned-on and my cock was as hard as the chastity device allowed me to get. I needed to masturbate so fucking bad. God I hated Lucy for getting me in this situation.

I admit I'm a crossdresser and an exhibitionist when I'm dressed in women's clothes. But I'm not gay and don't like sucking cocks or taking them up my ass even though I had done plenty of both the previous week.

My admin Gayle did come in my office several times that day and each time I scooted closer to my desk so she couldn't see I was only wearing panties.

Let me tell you about Gayle. She's a few years younger than me and is married with one son. She's got a good body and perfect breasts. At least that what she tells me but has refused to show them to me to prove it even though I once offered her $200 just for a look.

We have a great relationship with plenty of harmless flirting with sexual innuendos. I don't fit into her category of "Doable Dads" and I wouldn't consider screwing up my marriage to fuck her. We're both happily married and just have fun teasing each other at work. It's a special friendship developed over a number of years working together.

I missed lunch because I couldn't leave my office in just panties and really needed to go to the bathroom. I wanted to ask permission but couldn't address an IM to "Techie who is blackmailing me" so I sat there on that large dildo and squirmed all day.

Around 3:00 I finally received an IM telling me I could put my pants back on but the dildo was to remain up my ass. It also said there would be a dildo check sometime before I went home and it had better be where it was supposed to be.

I quickly put on my pants and practically ran to the bathroom because I needed to pee so badly. Wouldn't you know it, both stalls were occupied and I couldn't pee standing up with the chastity device on my cock.

Finally a stall was free and I went in and relieved myself. But the relief I really needed wasn't to be. My cock was locked up tight and I couldn't masturbate. Hell, at this point I didn't care who knew or saw. I was so fucking horny I would have jerked-off in the lobby of our office regardless of who was watching.

True to their word, at 4:45 I received an IM that just said "Dildo check"

I knew what was expected so I stood up, turned around so my ass was facing the Webcam and lowered my pants and panties to my ankles. I bent over and spread my cheeks so they could see the base of the dildo that was still up my ass.

Can you even imagine doing anything so humiliating?

"You can remove the dildo and put it back in your desk."

After I pulled up my pants and sat back down another IM popped up.

"You're a player Cynthia. This will work well as long as you do what we say. And we say tomorrow you either wear high heels to work or you bring them in your briefcase to wear after you get to work."

That didn't take long to decide. I wasn't wearing heels to work so they'd be in my briefcase.

Again they were reading my mind "But if you don't wear heels to work you will wear long fake fingernails. Have fun deciding the lesser of two evils."

"Either way, your choice will be on display in your office tomorrow or you're fired!"

What a choice! I decided heels couldn't be hidden but fingernails could if I kept my hands in my pockets all day.

The next day I got up extra early and did a complete body shave then dressed in matching red bra, thong and garterbelt. I put on suntan stockings and hooked them to my garterbelt. I hoped if anyone looked and saw I wasn't wearing socks they'd just think the stockings were my natural color and wouldn't recognize them for what they were.

I glued on bright red fingernails (I didn't have a more subtle color) then put on a red polo shirt and tan slacks. Damn I hoped the red polo shirt hid the slight padding in my bra and the straps didn't show through.

I got to work early like always and at that hour was able to avoid anyone I knew. I got to my desk shaking from what I was wearing. The garterbelt and thong didn't bother me. But stockings without socks did. I looked in my mirror before I left home that morning and didn't think my bra showed through my shirt but didn't know for sure. I knew my long red fingernails nails were safe as long as my hands stayed in my pockets.

I turned on my computer and almost immediately an IM popped up.

"Let's see if you followed orders. Take off your shirt, pants and shoes and put them in your desk drawer."

I quickly typed "But my office door is open and anyone can see me."

"Then close it Cynthia"

Before I could even stand up - "Because you aren't grasping what we want as quickly as we want it. Perhaps this will kick start your brain."

"Before you close your office door, take off your pants, shirt and shoes and put them in the bottom left hand drawer of your desk and close it tight. You'll put on your heels then walk slowly to your office door giving anyone who happens to walk by a chance to see you before you close it."

I had no choice so I did as ordered. I stripped down to my lingerie and put my male clothes in my desk drawer. As soon as I closed it tight I heard the unfamiliar click of a lock. I'd never locked my desk before and immediately tried to pull open the drawer with my clothes in it.

It was locked tight and here I was stuck in my office wearing a garterbelt, stockings, thong, bra and heels.

I practically ran to my office door and shut it and I didn't give a damn if they said "slowly". I would have paid big bucks right about now if the company allowed us put locks on our doors.

When I got back to my desk I was in a total panic. I quickly responded to the IM – "What now? I can't sit here in lingerie all day or I might be caught and fired!"

"Well we don't want you fired or our fun will end. Tell you what, you sit there looking nice and sexy and we'll figure something out."

Right then Gayle, my admin, opened my office door and walked in. She took one look at me in my lingerie and said "Oh my God!"

I knew I was going to be fired as soon as she reported me. But to my utmost surprise she closed my office door behind her and approached me.

She said "I was told I would encounter a slut in red lingerie today and I was to let that slut eat me till I came. I had no idea it would be you. I thought I was going to be forced into a lesbian encounter."

It hit me. Gayle was caught like me and was now a player. I had no idea what Gayle's indiscretion was, but I wish I did for taking advantage of her in the future.

She continued with a very red face "I can't believe I'm going to have to show you my pussy and let you eat me. How embarrassing!"

I didn't care. I'd lusted after Gayle's tits for years and now I was going to have to suffer by only eating her pussy. Poor, poor me. My tongue was hard just thinking about it and couldn't wait.

Gayle said "After you give me an orgasm, I'm supposed to reciprocate. I know I've joked about it over the past few years but I guess you are going to find out today just how great a cocksucker I am."

Obviously Gayle didn't know my cock was locked in a chastity device. This wasn't fair!

Gayle took off her pants and her sexy little g-string and sat down on the edge of my chair facing the Webcam. She slowly parted her thighs and kept spreading them till her knees were far apart and I had a perfect view of her shaved pussy.

I thought Gayle must be really getting into this as her pussy lips were parted and I could see she was already wet.

"Well, what are you waiting for? Get on your knees and eat me."

I didn't need to be told twice. I ate Gayle till she begged me to stop. Which by the way wasn't till after she had three orgasms.

She gave me a shy smile and told me it was my turn. I figured a picture was worth a thousand words so I stood up and pulled down my thong panties and showed her the chastity device on my cock.

She didn't say a word. She just reached down between my legs and started to gently play with my balls. I was going nuts with desire but any orgasm was denied.

She finally whispered "Too bad. I'd really like to have blown you as thanks for what you did for me." She let go of my balls, got dressed and left my office.

I really hated Lucy! I know none of this was her doing – it was the techies. But it fit in perfectly with Lucy's plan of keeping me horny as hell with a case of blue balls till she decided to remove the chastity device.

But what now? I'm in my office only wearing lingerie and there's no lock on the door. Anyone could walk in at anytime and there was no place to hide!

Gayle came back in my office a few times that day and each time I thought I was going to have a heart attack. The second time she was almost laughing at me when she asked "Are you going to get dressed or are you going to stay that way for your 2:00 meeting?"

Oh shit! I forgot about the meeting in my office that afternoon. In thirty minutes four other managers would be walking into my office for a meeting! What was I going to do?

I told Gayle my clothes were locked in my desk and I didn't have the key. I asked if she would please help me but she declined stating the techies might fire her if she helped me.

An IM popped up "Ask Gayle to stay in you office till 2:00."

I typed "Why?"

"Just do it! But do not let her know we're giving you orders or you're fired."

I said "Gayle please stay till the meeting starts."

"But why?"

Another IM "Tell her you have something to show her?"

Stupid me should have known the Webcam had a microphone. How else would we be able use them for business calls?

"Gayle there's something I've wanted to show you. Hold on for a minute while I reply to this e-mail then I'll show you."

Techies' IM "Time for you to work your dildo up your ass while Gayle watches."

"No fucking way" was my typed response.

IM "You now have only twenty five minutes till your meeting starts. As soon as the dildo is all the way up your ass we'll tell you where the key to your locked drawer is. You do want to get dressed don't you?"

I wrote "Of course I do! But there's got to be some other way!"

The techies' IM didn't even dignify my protest with a response. Instead the message back to me was "Since we forgot to leave you lubricant again, you'll just have to show Gayle what a great cocksucker you are. Unless of course you want to work it up your ass dry. OUCH!"

Another IM "Times a wasting. And remember if Gayle even suspects you're doing this because we told you to vs. on your own – you're fired. If Gayle leaves your office before the dildo is up your ass - you're fired. Let the show begin!"

I didn't know what to say or do. I couldn't pull a dildo out of my desk drawer and suck then fuck it while my admin watched! On the other hand, I needed my clothes in twenty minutes or else.

Like the blathering idiot I was at that moment I said "Gayle, I'm so fucking horny I'll do anything to get off. But with this chastity device on I can't stroke myself. My thought is if I can massage my prostate I can cum – at least that's what I've heard."

And with that I pulled the big black dildo out of an unlocked drawer in my desk.

"I don't have any lubricant so I'm going to lick this dildo then work it up my ass and try to cum. I want you to watch because it will turn me on that much more and I'll have a better chance of cumming. Please stay and watch me."

I cannot believe I said that to Gayle. I was waiting for her to run from my office screaming. But instead she sat down in a chair across from my desk. She smiled and said "This should be fun to watch. I just wish I had my video camera. Get to it slut, you only have fifteen minutes."

What was worse than telling Gayle what I was about to do was doing it! But I had no options if I wanted my clothes back. I took off my thong panties and quickly gave the dildo head to get it as wet as possible. I put its base on my chair so I could work it up my ass by sitting down on it.

Gayle didn't allow me to. She said "You asked me to watch and I can't see anything that way. Get on your hands and knees with you butt facing me and let me watch you work that dildo up your ass."

I was running out of time so I didn't argue with Gayle. I did as she wanted and was thankful she couldn't see the humiliation in my eyes as I worked the dildo up my ass.

By the time it was all the way up my ass the meeting was about to start. Gayle was still laughing at my slutty behavior when she stood up and told me she'd stall the meeting participants as long as possible but didn't think that would be more than a few minutes. Then she left my office.

How would I ever be able to face Gayle again??

I quickly stood up and looked at my computer's monitor. There was an IM telling where the key to my desk drawer was and that I was to keep the dildo up my ass until told otherwise.

I quickly got dressed with my lingerie under my work clothes and greeted the meeting participants as they entered my office. Thank God Gayle stalled them for a few minutes.

The four of them pulled up chairs and sat in front of my desk while I sat behind it. My heart was still racing and the dildo felt huge up my ass.

Techies' IM "Having fun Cynthia? We want you to rock back and forth on your dildo like you did yesterday. We want to see that same look of lust we saw yesterday."

How could I rock back and forth on a dildo while four people were sitting across from me? It would feel so good and I'd get so horny. I knew I wouldn't be able to control my facial expressions. So I sat there not moving.

"We looked at your calendar in Outlook and know your meeting is supposed to last another 45 minutes. Start moving your ass on that dildo and don't stop till your meeting is over or you're fired."

I started rocking back and forth and hoped it wasn't too obvious. The dildo was pressing against the right parts up my ass and I was getting turned-on. Without the chastity device I would have had a raging hard-on.

My face was getting flushed with excitement when another IM popped up.

"We think we can see your bra under your top. Yep, those are padded cups and bra straps on your shoulders."

I looked down to see but couldn't be sure if my bra was visible or not.

"Don't be bashful. Lean back in your chair, put you hands behind your head and stick your chest out. We want everyone to know you're wearing a bra. Do it now!"

I did as ordered and everyone looked at my chest. I didn't know if they could tell I was wearing a bra or just suspected it, but what difference did it really make?

"Keep working that dildo in your ass." was the next IM.

I did. Damn I was horny and I no longer cared who was watching. I rocked back and forth on the dildo hoping I could get myself to cum but no such luck. All I got was four people staring at me wondering what the hell was wrong with me.

The meeting finally ended and as the four participants left Gayle entered my office. She walked right up to me and kissed me full on the lips. Wow! I never expected that.

She said "You are so fucking hot. Take off your male clothes and I'll let you eat me again."

How could I say no? I quickly striped to my lingerie and anticipated licking her pussy again. She told me to close my eyes and reach out my hands and she'd let me play with her perfect tits but only if I kept my eyes closed.

I closed my eyes and reached out for her boobs and that's when she put the handcuffs on me. Granted they were in front of me vs. behind my back but I was still helpless. I looked at Gayle with pleading eyes and asked why?

"I'm sorry boss. But the techies ordered me to do this or I'd loose my job." And then she gathered up my male clothes and walked out of my office. She left me there wearing just a bra, thong, garterbelt and stockings. I guess I could put on my heels but why?