Teaching Humiliation Ch. 01

Teaching Humiliation I

Brian Davis had finally earned his first teaching position at Grey Coast University. He was young, yet determined to make his mark on the university and to have an impact on the students. Although the current hiring climate had made it hard to find teaching jobs in his state Brian found himself one of the more lucky jobless teachers when a female friend, Paige Reynolds who worked at Grey Coast, gave him a heads-up on a job opening. She even went as far as putting in good word for him with the head of the history department (which was Brian's field) all but ensuring that he got the job. Paige was the department secretary and carried enormous sway with the department head, James O'Halloran, who had always had a thing for her.

Brian arrived in the relatively small college-town only a week before the first day due to his late hiring and found it to have very few options for living arrangements. Once again he lucked out when Paige informed him that her apartment had plenty of room and even had a spare bedroom that he could have as long as he agreed to pay half the rent. He leaped at the opportunity in part because it was the only option, but also due to the fact that it was a chance to live with Paige who was a beauty that he used to have crush on when they were younger.

Brian woke up feeling pretty good his first morning in the apartment. He entered the bathroom, which he of course shared with Paige, and looked at himself in the mirror. He was decent looking guy. A slim frame and average face kept him from being 10/10 but by no means was he ugly. Brian wondered to himself if it were ever possible for Paige to see him as any more than a friend. He knew she was way out of league in regards to looks. Her perfect long black hair, gentle and wonderfully feminine face, and knockout body was all that any man could ask for.

A knock came on the bathroom door. Brian realized he had probably been standing there in thought for quite a while.

"Yes?" he called out.

"You almost done in there? I have to get ready too you know?" came Paige's playful reply.

Brian splashed some water on his face before responding, "Yeah I'll be right out".

He quickly brushed his teeth and exited the bathroom to allow Paige to begin her daily bathroom preparations. As he passed her, Paige told Brian that they could head over to the school together since they worked in the same department. He agreed and they carried on getting ready.

When they were both finally prepared to leave Paige drove them over to the university. It was a boring day for Brian. Since classes had yet to begin he spent his time meeting the other members of the staff, such as the head of the department Mr. O'Halloran, devising lessons, and sitting in on university faculty meetings. Before long the workday was over and Paige drove them back to the department. After getting into more comfortable clothes the two began preparing dinner and discussing what they had been up to the past few years, as they had yet to have time to talk at length. Once dinner was prepared they sat down in the living room. Paige asked Brian how his first day was and he told her about the boring meetings. She didn't respond for a moment, but then her face lit up as if a bright idea had come to her.

"I have an idea that could liven up both our workdays! Mine are no better when there are no students," she said.

"What do you have in mind?" asked a highly interested Brian.

"Myself and a friend who used to work at the college with me used to play a game where we each give the other a task to complete at work each day."

"Ok...," Brian was confused as to how that would liven up his day, "how exactly does this work?"

"It's not necessarily super-exciting but it does add an element of surprise to the day depending on what the task is. My friend and I usually picked pretty lame tasks, but sometimes they got pretty risqué."

Paige leaned in which Brian recognized as the body language for someone who was about to tell a secret.

"One time she had masturbate in Mr. O'Halloran's office."

"Holy shit that's what I call risky!" said Brian letting out a surprised laugh.

"Now of course we could always start off tame or if you don't want to do it I will just drop it."

"No, no I'll give it try."

"Great!" Paige let out giggle and leapt over to hug Brian which he enjoyed quite a lot, "Let's think over what we'll make the other do and tell each other in the morning. And to make sure one of us doesn't back out the first one to decline a task has to pay full rent for three months."

Brian thought for a second. He didn't suspect Paige would make him do anything too bad, so he figured there would be no harm in agreeing. "Sounds good to me."

Brian got up from his chair and entered the bathroom to use the toilet before heading to bed. After a few steps in his foot slipped on something on the ground and he fell backwards. He had barely enough time to catch himself on the counter saving himself from a hard fall, but he still knocked off several items from the edge of the counter causing quite a commotion. He heard Paige rush to the door when she called out.

"Are you ok in there?"

"Yeah, I just slipped on something. You can come in."

As Paige opened the door Brian bent over to pick up the cause of the near fall. The culprit was a pink pair of lace panties. Paige snatched them from his hand.

"Those seem to be to blame for my close call."

"Oh my! I must have accidentally dropped them when I changed earlier. I am so sorry."

"No worries, no harm done."

Paige eyed the panties for a moment then looked back at Brian.

"You know what, though? This gives me a good idea for your task tomorrow. I want you to wear these panties all day tomorrow!"

Brian's mouth gaped open. "You're kidding right? I cant do that!"

"Oh come on, no one will know. And its just for a day. You don't wanna have to pay full rent based off the first task?"

Brian sighed. Wearing them wouldn't really hurt him as long as no one saw them, which would be unlikely. "Fine, I'll wear them."

"Great! Then here you go," Paige said handing him the panties, "and don't do anything funny with them."

She left laughing to herself and Brian continued with getting prepared for bed. He had a long day ahead of him in the morning.

When he awoke the next day Paige reminded him that he still needed to give her a task. He stated that he couldn't think of anything. Paige told him that if it helped he could choose simple task for her to do all week then he wouldnt have to think of one every day if he was having troubles. He thought about it in the shower, but still couldn't really think of one that matched severity of what he had to do. So he gave her the lame task of having to wear one article of clothing all week. It could be of her choosing as long as it wasn't shoes. After some deliberation she chose to wear the same socks for the week as it would be the least obvious. The pair she chose were a black pair of knee high socks. She told herself she as long as she wore dress pants then no one would notice, so other than how gross they would get it wouldn't be too bad.

As Brian pulled out the clothes he would wear that day he instinctively pulled out pair of boxers, but quickly put them back when he remembered that he would be wearing the panties instead. He grabbed the lacey garment and stared at them for a moment before begrudgingly sliding them on. He had to admit that the feel gave him a brief rush, but he would hardly call them comfortable. In fact, the very thought of wearing them made him uncomfortable. Brian pushed the thoughts aside and finished dressing in his regular work clothing.

As he entered the living room he saw Paige running about. He wasn't really sure what the problem was until he looked at his watch and saw the time. They were 20 minutes later than usual!

"Brian, are you ready?! We need to leave now before we are late!" Paige stated hurriedly.

Before he knew it they were off and Paige was racing the car down the street. At the college they rush inside and barely made it in time. Other than the rushed morning the day went on as normal. That was, until lunchtime...

Around noon Brian was sitting in his office starting to eat a sandwich he got from the faculty lounge when Paige walked in. She was her usually radiant self, wearing a tight-fitting pantsuit.

"Well, Brian, in our rush this morning I forgot to check if you were wearing your panties," she said plainly.

Brian's eyes grew as he choked on his food due to surprise.

"Can you keep your voice down?" he coughed through his full mouth, "yes I'm wearing them."

Paige stood in front of him hands on her hips.

"What?" as asked.

"I don't believe you. Prove it."

"Here? Now? I cant do that!" he responded.

"There's no one else in the office and it will only take a second. Now stand up and show me. Unless of course you are lying?" she said questioningly.

"I am wearing them I swear! Ugh, fine I'll show you."

Brian rushed over to the door and closed it. He then closed the blinds on the small window looking into the room. He faced Paige, who still stood waiting, and unbuckled his belt. He lowered his pants a bit showing the top of the panties.

"Come on, drop 'em. You gotta let me see the whole thing."

Brian dropped his pants which fell to ankles. He now stood with the panties in full view of Paige. His embarrassment was off the charts. Paige, however, was ecstatic that he had followed through. Her happiness made him feel a bit better, but only a bit.

"Now do a turn, so I can see the back."

Brian turned slowly. As he came back around he was stunned by the sudden flash of Paige's phone camera.

"Oh come on! You gotta delete that!" he said as quickly snatched up his pants.

"No way! I want it to remember the moment. Besides, no one else is going to see it. I promise I'll keep your panty wearing secret. And to prove that I followed through as well I'll show you this."

Paige slid up one of her pant legs showing the knee length black socks she'd be wearing all week.

"Now we both know the other followed through."

With that Paige left his office. Brian slumped into his chair hardly able to comprehend what just happened. Brian sighed and carried on with his work. All was normal for the rest of the day and evening.

Brian awoke the next morning with relief that his embarrassing task from the previous day was over. He completed his morning bathroom routine and ate some breakfast. He was returning to his room to get dressed when Paige popped in front of him.

"I got your task for today!" she beamed.

"Hooray..." he responded sarcastically.

"It's like yesterday except I want you to wear a bra with the panties."

"What!? No way! I will be with O'Halloran most of the day. I cant wear lingerie again."

"Oh come on. He wont know what's under your clothes and besides you don't wanna be the first to break and have to pay up."

"Ugh, fine."

Paige smiled and tossed him a bra and panty set she had in her hand. Brian once again slipped on the panties, this time followed by the bra, before putting on his regular work clothes. At work he worked with O'Halloran for a large portion over the day and sat uncomfortably. While the clothes didn't actually bother him, the thought of O'Halloran discovering secret did. He made it through with little to no problems and the day went smoothly. He hoped that after two days of wearing lingerie Paige had her fun and would give him some other task for the next day, Friday. Somehow, he knew he would get no such reprieve.

Much to Brian's dismay Paige had him once again don lingerie, but this time she included stockings and a garter-belt. Luckily, the day was spent mostly in his office and he never had to risk someone seeing his stockings under his trouser legs. When they returned home Brian was relieved to have made it to the weekend without any real significant embarrassment, but the evening was to be very, very different.

Brian was in the midst of getting undressed and putting on some more comfortable clothing when Paige entered his room. He almost fell over trying to cover himself up as he was only in his lingerie at that point.

"Hey, don't you know how to knock?!" he asked indignantly.

"Calm down, I just wanted to see your lingerie again before you took it off. Now give me one last turn."

Brian figured she had already seen him in lingerie a couple times and that at this point there was no point in fighting, so he slowly did his turn as Paige gleefully cooed. He finished his turn and saw Paige's eyes grow as if an idea came to her head.

"I just had a great idea! If you promise to do what I ask for the next 30 minutes I promise I won't have you wear women's clothing for your task next week."

Brian eagerly accepted without thinking about it even though he probably should have. Paige disappeared for a moment and then reappeared holding some clothing and two small bags.

"Since I won't be able to see dress up again I want to take this opportunity to see how you would look fully dressed!" she said.

"You got to be kidding me!"

"Nope. You agreed to follow my orders and besides, it gets you out dressing up next week."

Not believing what he had gotten himself into he once again just went along with what Paige wanted. She first filled his bra with some pantyhose to give him some cleavage and then slipped a tight corset around his midsection. It was tightened far more than Brian wished or thought possible. A black cocktail type dress was place on him next. It was followed by a blonde wig put on his head. The wig looked incredibly realistic and Paige explained that it was from a Halloween costume a couple years prior. She slid some 5 inch heels onto his feet.

Now that the outfit was complete she led him to a chair and spent 20 minutes applying makeup. This included thick mascara, blue eye shadow, concealer, foundation, blush, and several coats of bright red lipstick. She brought him to the full length mirror and Brian was absolutely dumbstruck by his feminine appearance. Paige had actually turned him into a girl!

"My own family wouldn't recognize me!" Brian exclaimed.

"I know, you look so good!"

"I guess you had your fun so I'll just get undressed now."

Before any further conversation could occur a knock came to the front door and was opened shortly after.

"Paige? Brian? Its James. Paige you told me to just walk in when you invited me over and I have dinner with me."

Brian was shocked and didn't know what to do.

"You invited O'Halloran over!?" Brian whispered hurriedly.

"I totally forgot!"

"What are we gonna do? Im dressed as a girl and my boss is about to walk in!"

James' footsteps neared the room.

"Just go along with what I say."

James entered the room and looked a little surprised.

"Oh, hello ladies. I was expecting Brian to be here."

Paige stepped forward.

"Brian is visiting family this weekend and this is a friend of mine from out of town. She's staying in Brian's room tonight...Brittany this is James O'Halloran from work."

James walked over and took Brian's hand.

"Nice to meet you Brittany," he said.

"You as well," Brian said as quietly and softly as he could.

There was an awkward silence for a while.

James finally spoke, "well let's eat! I set it out on the table."

They all exited the room and sat around the table small talking and eating. After the meal was done Paige's phone rang. She answered and spoke to other person for a moment.

"Im sorry guys, its my mom. She needs help with something on the computer. I have to walk her through something, so I'll be in my room for a bit, so just hang out for a while."

Brian, whose nerves were already though the roof from being disguised as a girl in front of James, pleaded with his eyes for her not to go, but Paige didn't notice or didn't care.

"So Brittany, I must confess that I wasn't really surprised to see you here," said James.

Brian was very confused as he didn't see how it was possible for James to know there would be another girl here with Paige, or what he thought was a girl.

"What do you mean?" responded Brian in his best recreation of a feminine voice he had been using throughout dinner.

James leaned in and whispered, "Paige told me you'd be here when she invited me to dinner. She said her single friend from out of town would be staying over and that I should come meet you, but act surprised. She also said you're kind of a slut, but don't like to admit it."

Brian was flabbergasted. Paige had set him up! James was here under the impression that he'd be meeting with a single lady who put out. Brian shifted nervously in his seat not really knowing what to do. James slid closer and put his arm around Brian.

"Paige will be gone for a while, so we have time to...you know.." whispered James as he place Brian's hand on his crotch. Brian could feel James' swollen cock through his slacks. It was enormous! And still growing! He sat there frozen in shock. His mind was a blur as he let James rub his hand more vigorously on his crotch. Brian was in such a state of disbelief that he didn't resist when James slowly pushed him down to his knees and unbuckled his pants revealing his 10 inch penis. Brian's mouth instinctively opened in astonishment which James took as an invitation to slide in his cock. At least as far he could. At first James did most of the work thrusting his big sweaty cock in and out of Brian's mouth. Soon though James' hands grabbed Brian's head and began bobbing it on his shaft. Brian again offered no resistance as he had no clue what he should do in the impossible situation he found himself in. After a while James began to grunt and pound his face harder. Brian knew he was about to take his first load of cum.

Out of the corner of his eye Brian spotted Paige walking in. He went to pull his head back but James kept him attached to his close-to-orgasm cock.

"Hold on James, I don't know if she is ready to take a load as big as yours just yet," said Paige.

"What do you mean? I thought you said she was a slut," came James' reply albeit through his grunts.

"I may have exaggerated a bit. Just pull out I have an idea."

James listened and removed his pulsing cock from Brian's mouth. Paige stepped behind Brian, grabbing his hands, and locked them in a pair of fuzzy handcuffs. She then bent over and removed one her black knee high socks she had been waring all week and slid it over James' penis. She began stroking his cock with the sock and in a minute James blasted the sock soaking it with cum. Brian could see the massive load through the sock and gagged a bit from the smell. Without another moment to think he saw Paige remove the cum filled sock and in a swift move shove it into his mouth. A ball gag was then quickly latched to his face pushing it further in and holding it in place. Paige must have brought it with her from her room.

Brian stayed on his knees as he began to sense the taste. The sock was truly filled with cum and he almost instantly felt it coating his mouth. Along with the strong flavor of James semen he could taste Paige's sweat that was almost as strong. She had obviously done more than just wear them the last few days. It was as if she had just ran a marathon they were so vile. He looked up at his tormentors who looked back at him.

"What now?" asked James.

"I think I can have some fun with her now and give you some time to refuel," responded Paige with devilish grin.

Brian's night was far from over.