The Trouble with Roommates Ch. 02

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An accidental slip-up leads Nick to the next penalty.
1.8k words
4.4
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50

Part 2 of the 7 part series

Updated 10/30/2022
Created 02/16/2015
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KaylaG
KaylaG
205 Followers

As much as Nick hated to admit it, he was getting used to the feeling of his smooth skin. For the past month his roommate Brian had been making him shave twice a week as well as wear mascara and lip gloss that he was made to reapply whenever his lips lost their baby-pink sheen. He wasn't going to miss it, though, that was for sure. He'd been doing well with work recently and had not only been able to make every week's rent, he also almost had enough stashed away to square up with Brian. "Thank god" Nick thought to himself. Brian had really been taking this whole thing seriously. He checked on Nick's lips and mascara multiple times daily and ever since he had come home from work to find Nick without makeup he'd been making him send pictures at random times while he was at work. It was extremely humiliating, but Brian had him up against a wall. He either had to live with it or live on the streets, and that wasn't something he could do, so he kept himself shaved, kept his lips glossy, and saved money to buy his masculinity back.

Going out with his friends had been nerve-wracking. He skipped the pizza dinner, met them at the dim bar after dark, and wore a long-sleeve shirt to hide his shaved arms. He didn't think anyone had noticed anything, but his friend Owen had looked quizzically at him at one point and said "dude, there's something different about you... I just can't put my finger on it." Nick nervously laughed it off, but inside he was terrified someone would notice something. His worst scare of the night was when everyone clinked glasses for a cheers and he noticed the soft pink lip gloss mark on the rim of his glass. He quickly pulled his beer back and tried to subdue the nervous feeling in his stomach. "Nobody noticed" he thought. "If they had noticed, they'd have said something."

Since that night he'd turned his friends down for their weekly night out. He was looking forward to going out with them again this weekend once he was paid off. No lip gloss, no mascara, just himself the way he used to be (well, when the hair grew back). He spent his Friday humming to himself as he went about his daily cleaning and work, and couldn't even stop himself from smiling when he sent Brian the requested picture at lunch. He practically skipped to the plaza nearby to take out Brian's money and stopped in at the liquor store to buy himself a 6 pack of his favourite craft beer as a reward for doing so well. "I'm free!" he rejoiced, almost out loud.

That night he handed Brian the envelope of money and waited while he counted the bills. "It's all here, congratulations Nick. I didn't think you had it in you, I'm glad to see my plan worked this quickly." Despite this it seemed like Brian was a bit disappointed.

"Awesome!" Nick shouted. "If you need me, I am going to wash this stupid makeup off, take a long shower, and then drink some beer and start growing this hair back."

Brian laughed and shook his head. "Congrats again buddy, you did well. Hopefully this is a valuable lesson in how to handle your finances like an adult."

That night Nick was feeling great. He got out of the shower, toweled himself off, and looked at himself in the mirror. It almost felt weird seeing himself without the makeup now. Grabbing the makeup off the counter and shoving it in a drawer he muttered to himself "I won't be needing these anymore!" He went to the kitchen, opened one of his beers and went back to his room.

5 beers later Nick was feeling fantastic. Dancing to the kitchen, he grabbed the last beer and went back to his room, shutting his door behind him. He put the beer on his desk and went back to surfing the internet. Absorbed in his surfing, he lost track of time a bit and snapped out of it when he heard his cell phone ringing. He reached over to grab it and knocked his beer over. Frantically grabbing for the bottle as it tumbled end over end, he shouted out but couldn't stop it before it landed on top of his PC pouring beer right inside. It was too late, his PC sparked a few times and shut down completely. With a sinking feeling he opened it and desperately tried drying off the inside, but he knew it wouldn't work. Sighing in a defeated way he unplugged it and went to bed.

***

The next morning Nick took a morning bus to the store he had bought the PC at. The man behind the counter was very amused at his story and told him to wait while he assessed the damage. Nick impatiently waited while the repair man looked his PC over, and he soon came back. "Well, the good news is your hard drive is fine so you won't have lost any work. The bad news is the power supply, motherboard and memory are all fried, so you'll basically need a brand new machine. We've got some specials on right now, take a look and see if there's anything you like."

There was no way Nick could earn a living without his PC. There was no way Nick could afford to buy a new PC, he'd just given all his money to Brian. Unless...

Brian was at the table reading a book when Nick approached him that afternoon. Nick walked up and cleared his throat. "So, uh, Brian. My computer died last night, and I need a new one. Do you think maybe... I could borrow some money?" Brian looked up from his book and stared at Nick.

"I suppose that could happen. Yesterday you gave me this week's rent plus the 2 back weeks you owed. How much of that would you need back?"

Nick studied the floor and responded quietly. "Um... actually... all of it."

Brian didn't respond. Nick looked up and met his gaze. When he saw Nick was looking him in the eyes Brian flatly spoke. "I have it here. You know what to do."

Nick did know what to do.

***

An hour later Nick was once again clean shaven and had the familiar taste of lip gloss back on his lips. Shaving and putting the makeup on had felt like routine by now, but when he opened the box and saw the lingerie he was overcome by nerves. "I can't do this. I just can't. I'm a man, god damnit, and men don't wear frilly bras and panties." After a few minutes of struggling he got himself back under control. His options didn't seem too great. There was a soft violet pair that he immediately discounted as too girly of a colour. The shiny pink pair had small pearl white bows decorating it, and he definitely couldn't pick that pair. That left the black pair with white lace trim. He slowly slid them up his legs and noticed that the soft silky fabric felt fantastic cupping his hairless balls and shaft but he could feel the thong cut worming deeper each time he moved around. The bra was a bit trickier. It took him a few times before he figured out to clip it in front of him before spinning it around and putting his arms through the holes.

His reflection in the mirror was worrying. Before, his slim waist and hairless body had looked androgynous but he could still retain his masculinity. With the bra and panties on, however, at first glance you'd be hard pressed to tell him apart from a girl. His long blonde hair didn't help the illusion. To his shame, his cock barely stood out behind the panties, and his ass was what him and his buddies would've called a bubble butt. After putting his clothes back on over the lingerie he examined his shape closely. The panties weren't noticeable at all, but from the side he could see where the bra cups stuck out from his chest and he could see a faint outline of white lace through his shirt from the front. He took a few deep breaths, steadied himself, and went to find Brian.

Brian looked up when he entered the room. "I trust you've met the terms of the agreement?"

Nick couldn't make eye contact with Brian. "I have. As demanded."

"Take your clothes off. Let me inspect you."

Nick dropped his pants to his ankles and slowly took his t-shirt off. Brian stood up and circled him slowly, looking him up and down before pulling a chair over and sitting down in front of Nick. "Before you put your clothes back on, we need to go over some further rules."

"You didn't say anything about more rules!"

"I'm saying it now." Brian motioned toward the table where the envelope of cash was sitting. "If you want to borrow my money, you'll borrow it on my terms. Do you object?" Nick was silent. "Good. First, I prefer to lend money to people who treat me with respect. From now on you will address me as "sir" whenever you speak to me. If I tell you to do something, the response will be "yes, sir". Is that clear?"

Nick hesitated but gave in. "Yes. I mean... yes, sir."

"Second, the next penalty. If you fail to make your payment again, arrangements will be made with my friend Karen who runs a salon on this end of town. You'll have an appointment with her to have your hair cut and styled to my choice as well as a makeover with lessons, a manicure, and a pedicure. From that point forward while you are in my debt you will keep your hair styled and nails polished, along with a bare minimum of foundation, eye shadow, eye liner, mascara, and lipstick or gloss."

"No fucking way!" Nick shouted.

With a sudden movement Brian reached out and jerked Nick off his feet and over his lap. Nick tried to struggle but Brian's strong arms held him face down over his lap. Brian's hand gently massaged his butt for a couple seconds before he raised it and brought it down sharply. *SMACK* "You will never" *SMACK* Nick cried out at the sharp pain. "say no to me" *SMACK* Nick felt his legs helplessly kicking air as he squirmed under Brian's firm grip. "ever. Do you understand?" Nick hesitated. *SMACK*

"OK, OK! I won't say no! I won't!"

*SMACK* "That's not how I taught you to speak to me. Try it again."

"Ow! Yes, sir, I won't say no again sir!"

Brian's hold on Nick released and Nick pulled himself off and back to his feet. His ass was on fire and he couldn't stop himself from crying a little bit at the shame and pain. Brian looked sternly at him shaking. "That's better. I didn't want to have to do that, but you needed a strong lesson on who's in charge around here. Now put your clothes back on and go wash yourself up, your mascara is running."

KaylaG
KaylaG
205 Followers
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AnonymousAnonymousabout 2 years ago

Nick wouldnt have any of these issues if he never drank beer. Or like got a part time low wage job considering the rent is so low. Lmao

GrrrreatImaginationGrrrreatImaginationover 5 years ago
Brian has a...

marketable business model starting here. Specialized, small-batch financial assistance/training.

Nice writing, and a verrrry amusing storyline... except from Nick's point of view. ;-)

kamperman45kamperman45about 9 years ago
Keep it coming but longer chapters

Like the direction he is leading him into and the interplay that stated this time. Please, a little more detail and some longer chapters would be a plus. thanks.

AnonymousAnonymousabout 9 years ago
Great work!

Loving this story, please keep it coming :-)

hotnatasha1987hotnatasha1987about 9 years ago
nice but something missing

good one but something missing .. i dont like humiliation .. i prefer romance .. i am a pansexual girl .. and looking for a transgender girl for relation ... but i cant humiliate anyone .. can you bring some romance in between them ???? plz

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