Alex's Humiliations

Webster picked up the pace pulling his cock almost all the way out and then long-dicking it back into Alex's throat. Alex held onto the edges of the desk and grabbed short breaths between strokes.

Without warning Webster pushed his cock deep into Alex's throat and shot his load of cum. Alex swallowed and swallowed but the position that he was made it difficult for him to swallow the load. Webster stayed buried deep in Alex's mouth until his cock stopped pulsing then pulled his cock out. Strings of saliva and cum stretched between the cock and Alex's mouth and has run down the sides of his head.

"Clean up time." Webster laughed.

Alex lifted himself off the desk and knelt down and started licking Webster's cock. He was again humiliated and sickened and just wanted to get out of there. After about 10 minutes Webster pulled back and started to get dressed.

"Get out of here."

Alex got up and headed for the door.

"By the way" Webster said, stopping Alex before he opened the door. "Meet me at the airport tomorrow at 2:00. And another thing, shave before you get there."

"What?"

Webster leered back at Alex.

"I want you to shave. Shave everything below your neck. Arms, legs, balls, arm pits. Everything."

"What for???" Alex did not like where this was headed and felt that he had been humiliated enough. "Haven't you had enough fun?"

"Look, cocksucker, I own you now. I have enough to get you fired and your hacking stunt is probably enough to send you to jail. But maybe you'd like that, wouldn't you? You'd have a cock in your mouth all day long in there. You'd make someone a real nice bitch. Just do as I say and stop asking questions."

Alex felt he was trapped. Webster was the kind of guy who would crush him if he got in his way. He needed this job and certainly did not want to go to jail. He didn't know what Webster had in mind, but it didn't matter. He turned and walked out of the office.

He was Webster's bitch now.

Chapter 3

Alex stood in the shower with a can of shave cream and a razor. Webster's request, no, command, was puzzling. It made no sense. It had to be one more thing that Alex had to do to humiliate himself. He figured Webster would check to see whether he had actually shaved and then mock Alex for the entire trip. Again, he did not have much choice in the matter and got down to business.

Alex shaved his arms, underarms, legs and started on his balls. He was afraid that he would cut himself and they would find him in the bathtub where he bled to death. Smoothly shaved but dead nevertheless. As he shaved his balls, the touch of the razor started his cock to twitch. Soon he had a raging hardon.

That was fine… all the easier to shave his cock. He ran the razor up and down his cock until his pubic hair was nothing but a memory but his cock was still standing tall. He squirted more lather on his cock and started stroking it slowly. His thoughts went back to that afternoon when Webster's cock was raping his throat and, strangely, it excited him. He was not gay he kept telling himself, but the thought of Webster's balls and cock in his mouth got him hornier. His hand moved up and down his cock faster and faster just as Webster's cock had slid in and out of his mouth. What was he thinking??? Why did it have this kind of affect on him???

In minutes Alex felt his load rise up his cock and shoot on the shower wall. His cock pulsed and pulsed as he milked every drop of cum out of it. It was an intense orgasm and puzzled him why his thought of being used by Webster triggered such a response. Maybe it was pent up frustration. Maybe it was a normal reaction to the kind of sexual acts he had performed on Webster. Whatever the reason, it did not matter. He realized that he had forgotten to shave his ass. He grabbed the shave cream and razor and proceeded to finish his humiliating chore.

When he stepped out of the mirror he looked at himself in the full-length mirror on the door. As a swimmer in high school he had shaved his legs and had never had a lot of chest hair, but could not remember not having pubic hair. His balls and cock looked naked hanging just there. "Fine" he said aloud. "You got what you wanted, Webster. But this is nothing that I can't live with. You can have your laugh but it will grow back." He wrapped the towel around his waist and headed for the bedroom where he packed a small overnight bag for the trip.

By the time Alex got to the got to the gate, the passengers had already started to board. With any luck, Webster would miss the flight and give Alex a few hours without him. He started into the plane and proceeded through first-class when he saw Webster sitting there. Typical of Webster, he had booked himself into first class while Alex was sitting in steerage. Webster looked up from his newspaper, saw Alex in the aisle and with a not-so-subtle voice addressed him.

"Alex, nice and smooth, are you?" Webster just laughed and went back to reading his paper.

Alex reddened. He knew what Webster meant. Maybe everyone who heard him knew also. More than likely they thought Webster was referring to the flight. Hopefully they thought Webster was referring to the flight. It didn't matter. Alex had sucked Webster's cock, been face-fucked and deep-throated by him and swallowed his load. How much more humiliated could he get?

He sank into his seat. 41E. Webster couldn't even get him an aisle or window seat. Just add it to the scorecard. Webster 100, Alex zero. He closed his eyes and hoped he could just sleep through the flight, but his mind kept reliving events in Webster's office the day before. Again, despite Alex's revulsion at sucking another man's cock and swallowing his cum, Alex's own cock started to respond. He tried to push the thoughts out of his mind, put he couldn't. Alex could feel every thrust of Webster's cock and taste every drop of his cum. In desperation, Alex grabbed a magazine and opened it up trying to not only concentrate on something else but to hide his building erection. It didn't help and for the entire flight Alex could not get the scenes from replaying in his head.

After touchdown, Alex made his way through the plane and caught up with Webster in the gate area.

"We need to go down to the baggage area to pick up a bag." Webster said without looking at Alex.

"Pick up a bag?" Alex thought to himself. It was a one-nighter and Webster was already carrying an overnight bag. What did he need to pack? How many changes of clothes does this guy go through in a day? It did not matter. Alex fell in line behind Webster and headed off to the baggage area.

After retrieving a fairly large suitcase, they caught a taxi and headed for Georgia Enterprises. They would spend the day there taking care of business and it was a relief for Alex. He spent most of his time with other IT geeks and little with Webster.

"He seems like a nice boss," they told him. "Yeah, right" Alex thought to himself. "If you only knew."

At the end of their day, they headed their hotel. It was 6:00 and Alex was starved. He was hoping that Webster would have something to do that night and Alex could grab dinner and have a pleasant evening in his own room without Webster's company. The break would be nice.

The cab pulled into the hotel parking lot and they climbed out and headed for the lobby. It was a decent-looking hotel, not the Ritz, but probably a good business traveler type of place. They walked up to the registration desk and Webster pulled out his wallet.

"Reservation for Atlas Engineering." he said as he handed his credit card to the clerk.

"Yes sir. We have a two-room suite available as you requested." the clerk replied.

"Two-room suite?" Alex thought to himself. "I have to share a two-room suite with him?" This was not good. These set ups usually mean someone sleeps on the foldout couch and someone gets the bed. And he knew who was going to get the couch. Just one more point for Webster he thought.

The registration process completed they headed up to the seventh floor and to their suite. Like all business type of hotels, this one had an Internet connection and the first thing Webster did was set up his laptop check his email. After a couple of minutes Webster headed for the bedroom turning back to Alex as he walked.

"We're going out to eat shortly. We'll get ready in a few minutes."

"I can hardly wait," mumbled Alex. He heard Webster moving around the bedroom and heard him open the clasps on the suitcases. If Webster were true to form, he would probably have too much to drink tonight, come back upstairs and fall asleep. That would afford Alex with some time to himself. Maybe Alex could shave Webster while he was drunk. Maybe…

"Get in here."

Alex snapped back to reality. He headed for the bedroom and found Webster with an array of clothes spread out on the bed.

"This is what you are wearing tonight." he said, looking at Alex and waiting for a reaction. Alex walked over to the bed and looked at the clothes, a black waist-length leather jacket, white blouse, black leather mini-skirt, thigh-high black boots and women's underwear.

"WHAT THE HELL IS THIS?" Alex shouted. "IS THIS SOME KIND OF JOKE?"

Webster walked over to Alex and stood close enough that Alex could feel his body heat.

"Listen, cocksucker, you are going to do what I say and you aren't going to complain and you certainly aren't going to shout at me. Understood?"

"Mr.Webster, this is going too far." Alex pleaded. "I sucked your cock twice. You made me swallow your cum. I've never done that to anyone. Haven't you had enough?"

"No, I'm just getting started. Now unless you want to be an unemployed convict when you get home, I suggest that you strip." Webster ordered.

Alex lowered his head. He had gotten himself in deep now. In hindsight he probably should have walked out of the first meeting with Webster but he didn't. And by fooling around with Webster's PC, he just sealed his fate. No, he was in deep now and just hoped that this final humiliation would satisfy Webster.

"Can I at least have some privacy?"

"No, you're going to need a little help." smirked Webster.

Alex unbuttoned his shirt, pulled it off and threw it on the bed. Next came his shoes, socks and eventually he slid his pants and boxers down to his ankles and kicked them off. Webster reached into the suitcase and pulled out a roll of duct tape.

"This is to keep things in place." he chuckled. He pulled off three strips about 18 inches long and walked over to Alex.

"Spread your legs." he ordered. Alex did as he was ordered and Webster stuck the strips of tape to him just below his navel. "Turn around and bend over."

With Alex's back to him, Webster fumbled around the suitcase again. Alex heard a squirting sound and suddenly he felt something cold against his asshole. Without a word, Webster pushed a small butt plug that he had lubed into Alex's ass.

"W… WHAT ARE YOU DOING?" Alex cried and tried to straighten up, but Webster just pushed his head back down.

"Just making sure I have your cooperation tonight."

Webster reached between Alex's legs and grabbed the ends of the tape and pulled them between the legs and back up taping Alex's cock and balls tight to his body and sealing in the butt plug. "We don't want them getting in the way, do we?" he smirked. "Get up."

Alex stood up and faced Webster. His cock and balls were taped so tightly to his body that it appeared he didn't have any. And he could feel the butt plug, as small as it may have been it felt huge in his asshole.

"See this?" Webster said, holding up a small device like a car door opener. "This sends a signal to that thing up your ass. When it does it will give you a shock. I can control the intensity from 'light' to 'extra crispy'. This is 'light'.

With that Webster pushed a button on the control and a stinging pain shot into Alex's groin. It did not knock him over but it made him wince.

"Do you want to try the next level?"

Alex was convinced by the 'light' setting that he did not need another demonstration. "No." was all he could muster.

"Good. As long as you don't step out of line I won't need to use this. And I won't warn you. If you give me grief or a hard time, I'm pressing the button and you can get what's coming. Just hope you don't piss me off enough to use the 'extra crispy' setting. Now get dressed."

Webster turned, walked out of the room shutting the door behind him Alex looked at the clothes on the bed. He started with the underwear which included fake tits in the bra. It was his first time dealing with women's undergarments and after 15 minutes Webster was pounding on the door telling him to hurry up. A few minutes later he opened the door and walked out of the bedroom for inspection.

Not bad Webster thought. Alex's short hair was covered by a wig of straight black hair. With the pseudo-spike collar around his neck, Alex looked like a cross between a punk chick and a biker girl. He stood wavering in the boots that had spike heels.

"Better get used to those boots." Webster chuckled. "You're wearing them all night."

Webster walked behind Alex and checked him out from the rear. His hands wandered over Alex's shoulders, down his back and over his ass. Alex just stood there. There was nothing he could do.

From behind Webster put his hands on Alex's hips and pulled him close so that Alex's ass ground into his groin. He reached around, grabbed Alex by his "breasts" and fondled him. He bent down and kissed Alex on the neck and then moved up to his ear.

"We're going to have some fun tonight, right?" he said as he nibbled on Alex's ear. "Let's go."

They headed for the door, went down the elevator and out the front door of the hotel. At a quick glance, one would think they were hooker and her john. Maybe that's exactly what Webster wanted Alex thought. "Parade me around like a whore."

They climbed into a taxi and Webster gave the driver the name and address of a restaurant. In about 20 minutes they arrived and Alex looked out the window. He could guess why Webster chose this particular restaurant. It was in an area of town that Alex guessed to be the "gay" area. He saw couples ranging from regular-looking guys holding hands to two women engaged in a lip-lock so tight one was certain to pass out. Webster open the door and got out, then turned and offered his hand to Alex to help him out of the taxi.

Once out, Webster offered Alex an arm and they strolled into the restaurant arm-in-arm like a couple of newly-weds. They were seated immediately and Webster ordered a bottle of wine.

"I hope you like the wine. It should help you loosen up."

Alex figured there wasn't enough wine in the whole restaurant to get him loose. With a little luck he could get himself hammered and would be unable to participate in Webster's little play. The first glass went down quick and Webster refilled it just as quickly.

"Don't go overboard." He cautioned Alex and lifted the remote control out of his pocket. Alex was in the process and downing the second glass and thought better of it and put the glass on the table. "That's better," he said and he put his hand on Alex's.

He then took Alex's hand and placed it on his thigh where Alex felt Webster's cock in his pant leg. Webster moved Alex's hand up and down the length of his cock and then let Alex do it himself. Alex looked up and saw the waiter approaching and started to move his hand, Alex grabbed it.

"Don't stop." he commanded.

Alex's hand returned to stoking Webster's cock as the waiter came over to the table. Alex did not look up knowing that the waiter could see everything. While he was taking their order, he could not help but notice Alex giving a hand-job under the table. The waiter looked at Webster, gave him a knowing nod and turned and headed for the kitchen.

"That's fine for now." Webster said removing Alex's hand. "We can continue that later."

They sat quietly sipping their wine until the waiter returned with dinner. After serving, the waiter turned to Webster and asked, "Is there anything else sir?"

"No, we're fine thanks." replied Webster.

"Then sir," the waiter said looking at Alex, "you ENJOY your dinner."

Alex was not in much of a mood to eat. Besides, food would just dull the effects of the wine and he wanted so badly to be oblivious. If Webster was limiting the wine, Alex could limit the food.

"Not hungry?" Webster said as he stuffed more food into his mouth.

"Not really" replied Alex. But he was and eventually his hunger won out. He was disappointed since he would probably be coherent for the rest of the evening.

The rest of the dinner was uneventful. Webster did not get the rest of the hand-job from Alex which disappointed Alex. At a minimum he had hoped to satisfy Webster without having to suck on his cock again. Better yet, it would have been nice to see Webster cum and leave the restaurant with a big wet stain on his pants. But neither was going to happen. Webster paid the bill, left a big tip for the waiter (on Atlas Engineering, of course) and as they left the waiter nodded to Webster.

"Enjoy the rest of your evening, sir." He said as he winked to Webster.

"I intend to," replied Webster.

"Fuck you," muttered Alex.

Webster reached into his pocket and in a split second Alex stiffened and almost toppled off his spike heels.

"Behave yourself" Webster said with a scowl. "Don't make me do that again. The next time will be worse."

"Sorry, I won't" said Alex. He almost sounded subservient, like a trained dog or something. Was he finally beaten? Was he Webster's bitch? Maybe he should concentrate on self-preservation and not worry about that right now.

They headed for the nearest taxi and climbed in. Alex was uncomfortable. As if wearing the butt plug wasn't uncomfortable enough, getting shocked left his ass burning and he almost felt that he was going to lose control over his bladder. He had that tingling sensation associated with having to take a wicked piss, but knew it was the result of the shock. Or at least he hoped it was.

Webster had instructed the driver to take them to the Michael's Club, a high-class strip club (if there can be such a thing as a high-class strip club) and as they drove along Webster rested his hand on Alex's thigh and stoked it. Alex was perplexed. Webster's hand felt nice running up and down his thigh but he kept saying to himself that he wasn't gay. But his cock, straining against the tape, told him that something else was happening. He was aroused but didn't want to admit it. Had it not been for the tape, his cock would be standing at attention. He wished he could pull it out and jack off to release the pent-up feelings. But instead, he had to sit there holding it in.

He was grateful when the cab pulled up to Michael's and Webster reached for his wallet. Once inside, he would try to position himself in a way that he wouldn't have to stroke Webster, and Webster would leave him alone. Once again, they strode arm-in-arm into the club and were seated in a small booth-like area. But the booth was not ideal for keeping away from Webster and they ended up almost in each other's lap. Webster ordered wine for Alex and shooters for himself. A good sign Alex thought. Webster was headed for a good night's sleep.

They watched the girls on stage do their thing and Alex could tell that Webster's cock was hard. His would have been also except for the tape. He considered asking Webster to take it off, but he knew that wouldn't happen. Instead, he drank his wine hoping that the alcohol would deaden the effects that the dancing girls were having on him.

After about 15 minutes, the doorman approached them and sat next to Webster. He was a big man, maybe 6'6" and 280 pounds. He looked like a football player, or a bouncer.

"Sir, we don't allow that type in here," he said to Webster.