The Bet

I knew one day my mouth would get me in trouble. I've done well enough so far, helping found and grow a technology start up, where I am now CEO. Last year, we sold $10,000,000 worth of our product, enough to hire some aggressive sales people. For the last fiscal year, I set the goal of $30,000,000. I thought it was a stretch -- few companies grow that quickly. Ellie, one of the new sales directors said she was certain we'd sell $100,000,000. I said I'd go to work naked if we did that.

Going in to the last month of the fiscal year, things looked good, we were at just over $25,000,000. I thought we'd hit our goal, but I had no idea of what was in store. Ellie had been working on a contract for the federal government. Those things take years, but they could mean a lot of money for the company.

On the last day of the quarter, I was gobsmacked -- Ellie brought in a federal contract for $80,000,000. As she was telling me this, she smiled, and said she was looking forward to seeing me at work the next day. I thought she was thinking of her commission check -- around $8,000,000 into her bank account (once the feds paid us.) That kind of pay day make one happy with their work.

The next day, Rosie, my executive assistant, was grinning when I came in. She told me my first meeting was already in my office, waiting for me. I looked at my calendar before going in, and I saw Ellie was scheduled for several meetings on my calendar, including the first meeting of the morning.

"So, Bert, why are you dressed today?" Ellie said as I walked through the door. I was confused, I didn't immediately remember my comment, but then it dawns on me.

"You know i was speaking metaphorically."

"I'm sorry, but I didn't hear it that way. You said you'd come to work naked -- and I thought you were a man of you word."

"Oh, come on, Ellie. You know I can't work naked."

Ellie pulled out some papers from a gym bag she was carrying. "I think you can. And if you don't, I have resignation letters from the bulk of your sales staff.

"Oh, and the Federal deal does away. Your choice -- work naked, or explain to the board why you let three quarters of your company's revenue go up in smoke."

Ellie had me over the proverbial barrel. For a 40 year-old, I am in reasonably good shape -- I hit the gym every morning at 4AM before heading in to the office. I don't have the body of an athlete, but I think I look OK. So, I started to take off my suit -- figuring I'd let Ellie have her laugh and get dressed again before the next meeting. I was down to my boxers, and hesitated.

"All of them, Bert. Take it all off, or you lose your sales team." I was turning red as I hooked my thumbs under the waistband and started to lower my boxers.

At this point, I should note that Ellie is quite the looker. She's not yet 30, but advanced to sales director at her previous company before joining us. She has an MBA from a well known business school in Florida, where she also did her undergraduate degree while being a member of their dance squad. I don't think there was an ounce of fat on her -- well, except where it should be. She's got a 34D chest. And today, she was dressed casually -- skin tight jeans and a loose blouse that definitely highlighted a cleavage that distracted many a client. I've wondered how much Ellie uses her appearance to make sales.

But now, I was the target of that charm. I was responding to her looks as I dropped my shorts. Ellie had a look of glee -- as she quickly grabbed my clothes and shoved them in her gym bag. Then she called out to Rosie if she could come in the room.

Trying to maintain my control was difficult. Rosie, though not a dancer, was quite attractive, too. She has a nearly perfect hourglass figure with firm breasts and ass. I could feel the blood leaving my head... Rosie walked in, and giggled. She had what looked like an o-ring in her hand, and she walked boldly up to me, and grabbed my cock.

That was too much -- I quickly grew to full size and Rosie started to give me a hand job. But when I was getting close, she stopped, and snapped the o-ring around the base of my cock. It stung for a moment, and Ellie then said, "I wanted to make sure we could see what you're offering the ladies! That's a cock ring -- you can't lose your erection now even if you tried."

While Rosie was getting me worked up, Ellie had put a lock on her gym bag. She then handed the key to Rosie, and Rosie left my office. "Don't think about getting dressed, Bert. You said you'd work naked, so you'll get your clothes back at the end of the day." Ellie then left the office, as Rosie returned with a length of leather. She wrapped it around my cock and balls and pulled on it like a leash. "I'm going to take you to your next meeting -- the it is a meeting of the women's working group."

I blushed -- this was a meeting with ten women to discuss the working issues they face. I was going to be naked when I talked with them. Rosie led me into the room, and it was clear the women knew I would be naked. Ellie was at the head of the table, and told everyone that it was about time I learned what it was like to be a woman in the working world. She then invited Rosie to sit in the one empty chair,and told me to fix coffee for everyone. Rosie undid her leash on me. I had my hands full as I went to fill cups with coffee and serve them to the women. As I'd lean over the table they'd pinch my ass, or give my cock a squeeze. By the time I finished serving everyone, i was drooling pre-cum. As I was giving Mai Lin her cup, some of the pre-cum dripped onto her dress.

"How dare you dribble on my dress? Do you know how much dry cleaning costs? I'll have to change." Ellie immediately joined in, "That is no way to treat a lady, is it Brett?"

"No, maam," I answered -- the humiliation of being naked bringing out my submissive side.

"I think you should be punished. What do the rest of you think?" Ellie called for a vote... All the women agreed, I should be spanked.

Mai Lin had left to change, the women decided she should be the first to spank me. While she was changing, Ellie got creative -- she had me lie on my back and tied down my arms. Then the women grabbed my legs, pulling them up over my head leaving my ass exposed, along with my cok and balls.

When Mai Lin returned, she was wearing a mini-skirt and a halter top, and knee high black leather boots. "It was what I was going to wear when I went out after work, now I have to wear it all day." Her halter top barely covered her 32B chest; it was clear to me she was not wearing a bra, either. She decided first to tease me a bit... Leaning over me and letting her long black hair caress my bound body -- and also giving her the opportunity to get even more upset as she got my pre-cum in her hair after dragging it over my cock. "How many strokes should he get?"

Ellie responded, "three each, and you go twice. That should be thirty six."

Thirty six didn't seem like so much, how bad could that really be? I was to find out when Carole said, "I've got my sorority paddle back in my office. Let's all use it!"

It didn't seem so bad at first... Sure, it stung, but it wasn't so bad until Jackie came up. Jackie must have played baseball at some point, she's an athletic woman to begin with, but she really got her strength into her swing; she hit harder than I thought anyone could. That left my backside sore, as the remaining women took their turns. My the time Mai Lin was finishing her second trio, running a feather on my ass would have hurt. Meanwhile, my cock was as hard as ever, unable to go down, and the puddle it formed on my belly was large.

When done, they first let my legs down, and lying down on my beaten ass hurt. Then they released my arms and let me off the table. I started to try to clean up my belly... and my hands were held behind my back by Jackie, as Mai Lin said, "Let it dry there." Someone found some wrist cuffs, and cuffed my arms behind my back.

The women went back to talking about work issues, but every now and then for the rest of the meeting one of the women would idly fondle my cock or rub my ass. The meeting lasted 90 minutes, and when it was done, Rosie put the leash back on me and took me back to my office. There, she sat me down in my chair (ouch!) and cuffed my arms behind the back of my chair.

Ellie had her second meeting of the day with me -- trapped in my chair. She came around and coo-ed. "You've been taking this well." She reached down, and rolled the cock ring off my cock. If anything, that made me even harder, as she started to rub me. She poured a little lubricant on the head of my cock, and in less than a minute, I was exploding into her hand. She was good about collecting all of my cum, I thought... Until she brought her hand up to my mouth, and said, "Lick my hand clean." I shuddered -- and she gave me a choice, "Eat your own cum, or I'll smear it on your face. Do you want to go to lunch with cum dripping off your face?" The she added, "It's no big deal -- women eat cum all the time. It's time you learn what it is like."

Gingerly, I stuck my tongue into the pool of cum in her hand. There had to be a couple ounces -- I had been teased for so long, my orgasm had been epic. She then forced her hand to my mouth, and just said, "Eat. Now."

I licked. It was salty, and tasted a little pasty. I didn't like the flavor, but I had no choice, as I lapped away at her hand, eventually licking it clean.

"That's a good CEO. I heard that your original lunch meeting canceled, so I arrange for you to meet some students from my business school at the office buffet. But you won't need to wear the cock ring any more.

"Let's see who we have for lunch!"

At least Ellie allowed me to clean up, before I went to the company cafeteria. I got a bunch of strange looks, but no one questions the CEO. At the far end of the cafeteria were a bunch of tables pushed together, and some students. As I walked over, Carole stood up and beckoned me. Carole is a strikingly beautiful woman, nearly six feet tall, with blonde hair and a perfect 34C chest. She looks like a Viking goddess, as she summoned me over to her group. "These are the freshmen and sophomores studying business nearby I figured it was time that they learn the old adage, 'Those who wish to lead must first learn to serve.' so you're going to serve us lunch."

When I was close enough, I met a group of about 20 students. Several of them snickered at seeing me without my clothes, and I think I heard one of the boy whisper to the girl next to him, "Mine's bigger, isn't it?"

Our cafeteria serves lunch as a buffet, and Carole told me I had to fetch everybody some lunch. I quickly saw the items available (salad, spaghetti, garlic bread, and an option of a meat sauce or meatless sauce.) and had to take everyone's order. At most, I could carry maybe four plates of food, so I ended up going back and forth to the buffer and the table. And even when I thought I was finished, I was given orders for more drinks. Standing and serving so much hot food made me perspire. I kept getting orders, and ended up going back and forth, my cock bouncing freely, to the amusement of the visiting girls.

It was bad enough being sized up by the boys in the class, but some of the girls were gleeful. There was one blonde -- I forget her name -- who kept having me go back and forth to fetch things for her. When I wasn't running food, she'd stare at my cock. Seeing her stare would make my cock twitch and dance. Occasionally, she'd say something to the girl next to her, and point at me... When I'd come over to her call, she would pinch and twist my nipples, and laugh.

Most of the students acted as if there was nothing odd about having a naked man serving them food.

After an hour of this, the students had to leave. I thought I'd finally get a chance to sit down and eat something, but Ellie came back, and told me it was time to find out how well I knew my employees. It was a rather cryptic comment, but she smiled, and led me to our board room.

"While you were enjoying lunch, I did a little shopping."

I complained that I hardly enjoyed lunch, and didn't get the chance to eat anything for myself. "But I let you have that snack before... Do you want more?" was all that Ellie could say. I was hungrier for something more substantial, even a slice of the garlic bread would have been nice.

"Don't you want to know what I bought?" continued Ellie. "She held up what looked like a miniature whip. "It's called a quirt. It is used for a special kind of flogging," and with that she struck my cock with the quirt. It felt like my cock was on fire. "We'll see if I need to use it. Lie down on your back on the table."

I did what she told me to do,, and she first grabbed my ankles, spreading my legs apart and tying me down on the table. Then she did the same with my wrists, leaving me spread eagle. At that, she put a blindfold over my eyes.

"This game is called 'How well do you know your employees?' Four women have agreed to ride your face for as long as it takes them to reach an orgasm, so you better be ready to use your tongue. Then, you have to say who it was whom you just pleasured.

"If you get all four correct, you avoid the quirt. But for every one you get wrong, the woman will be allowed to take a swat at your cock and balls with the quirt -- as many swats as you've gotten wrong so far.

"If you want to avoid this," as Ellie took another swat at my balls with the little whip, "then you had better know who is on your face.

"Are you ready? The first woman is." And with that, I heard some rustling of clothes, and then I was faced with the scent of a woman. She started by rubbing herself on my nose, but apparently, I didn't act fast enough, as I felt a hand grab and squeeze my balls. It was Ellie, as she just said, "you had better get your tongue in gear."

I stuck out my tongue and met moisture. So I started licking. The woman ground down on my face -- she felt heavy. But the pubic hard I found seemed soft. Damn, there isn't much to go on! I kept licking, as if my life depended on it. After a while, I got to hear a moan. It was low pitched -- which of the women who work for me would have a low pitched moan? She kept grinding, and I was soon met with her muscles clenching as she orgasmed. There was a sigh. She got off my face, and Ellie asked, "So who was that?"

I had no idea. I took a guess, "Was it Marian?" Marian is the oldest woman in the company, she works as supervisor of the test team, and to be honest, she could lose a little weight -- but when you're in your sixties, it probably doesn't matter as much. But instead of it being Marian, all I heard was a chuckle, then the burning sensation as I was struck on the cock and balls with the quirt. Then Ellie called for the next woman.

This woman was lighter -- and as I licked, I could not find any pubic hair. But light as she was, it was difficult for me to get any response from her. I was licking, and licking, when I got a squirt of something in my mouth. At that point, she got up. My jaw was already tired, as Ellie asked me to identify the second woman. Again, I had no clue, and took a guess. "I think it was Mai Lin." That was met by two quick slaps with the quirt. It felt like my skin was being flayed.

The third woman came in, and she orgasmed almost before I could stick out my tongue. Ellie told her, "That wasn't enough time, was it? You should bring her to more orgasms before you have to guess. Get busy with that tongue!"

So I did my work with my tongue reaching into the clefts of her pussy. I gave her at least two more orgasms before she was through, and with each she stifled a scream. "I know that's Carole" I said, even before Ellie could ask. As an answer -- I got three more stinging blows across my poor genitals.

It clearly must have been doing some damage, as I heard Ellie tut a bit, and it felt like she put something cold and slippery on my cock -- and started to rub. Oh my, she isn't, is she? I got hard as a rock again, and she let go.

"Ready for the fourth? We're going to do something to keep you focused this time, I think you were not paying as much attention as you should." I felt her put a couple straps on my cock, and the fourth woman got on my face.

As I started to lick, I suddenly felt something buzz in my cock -- Ellie had attached some electrical device to my cock and was giving me shocks. It didn't have the effect she wanted - it was hard for me to pay attention to the pussy wrapped around my face, instead of licking, I'd exhale with pain every time the shock ran through me. As a result, it took longer to get this woman to orgasm, but when she did, it was a large one. I thought she was going to squeeze my head of with her thighs.

"Very good, Brett," said Ellie, as she took the apparatus off my cock, "She hadn't reached orgasm with her lover in several months." Was that a clue? Who has been having trouble with their partner? I know Rosie hasn't been on a date in a while, but it didn't feel like what I imagined Rosie would feel like. Still, it was as good a guess as any.

"Was it Rosie?"

"That's oh for four, Brett." I steeled myself for what was coming -- whomever it was gave me two quick strokes across my balls, then two more lashed directly on my cock. With the third lash, I let out a cry of pain. My center of pleasure was nothing but a morass of agony. "Don't be such a baby, Brett, it is almost over. Just one more meeting."

I knew that -- it was the meeting I dreaded the most. Every Friday, we have a company meeting. All 80 employees gather in the cafeteria to hear the state of the business. I would get to give the company the news of the sales, while standing naked in front of them.

"There's one thing I need to do before the meeting, though." I heard the sound of some aerosol and felt something smeared all around my crotch. I then felt a razor against my skin. "I'm going to shave off your pubes." I felt her run the razor all over. It felt colder -- it is amazing how much warmth that little bit of hair can provide.

"One last thing," she said, as she then slapped something cold on where she shaved me. It went from cold to burning hot in a moment -- she was using some after shave on that very sensitive skin!

And with that, she took off my blindfold. She was the only person left in the room. I asked her, "So, who were the four?"

"You'll never know. Let's get to the meeting." And with that Ellie cuffed my hands behind my back, "We don't want you hiding anything, do we?" and led me to the cafeteria.

The rest of the company had gathered -- I guess everyone knew what had been going on all day, so they were waiting eagerly. I stood in front of them, and gave them the news of year's sales. I wanted the meeting over quickly, so I could end the day and get dressed and go home.

Instead, when I finished, Mai Lin came up to the front of the company, and said, "We've arranged for a photographer, anyone here can have their picture taken with the CEO!"

Oh my, how much longer can this go on? Different employees came up to have their picture taken -- some taking other liberties, such as holding my cock or having me kneel. Mai Lin insisted that I lick her boots in the picture, and Ana put some binder clips on my nipples, which hurt like hell! And then when she took them off, they hurt even worse. Carole wanted a picture of her beating my ass with her sorority paddle, so she got get another wallop on me.

In the end, there was one person left, Robert, a new hire. He asked if he could have his picture taken with me sucking his cock. I didn't want to do that, but Mai Lin said I would -- so I got on my knees as Robert undid his trousers and pulled out a rather large cock. He then grabbed my head and pulled me to him, and I put his cock in my mouth and started to suck. Snap snap the photographer took pictures as Robert got close before exploding in my mouth. They held my mouth closed and forced me to swallow -- some dribbled out the corners of my mouth -- as Robert commented, "You know, there isn't any anatomical different between the inside of a boy's mouth and a girl's mouth."