The Trouble with Roommates Ch. 03

The Trouble with Roommates Ch. 03

Big Dicks

Nick had never been so humiliated in his life. His mascara was running down his eyes from where he’d been crying, making him a pitiful sight. The bright red mark on his ass stung when he touched it. To his shame, he could make out a clear white handprint right in the center. Frustrated and embarrassed at how easily Brian had done this to him he took his time washing his face and briefly considered skipping his makeup before he decided risking being over Brian’s knee again wasn’t worth it. If Brian wanted him to wear the lingerie and makeup he’d do it, just until he got the money together again.

When he got back to his bedroom the envelope of cash was laying on his desk. “At least I can get my PC back up and running” he thought as he grabbed it. He bundled himself up in thick jeans and a heavy sweater to disguise the telltale signs of the bra and panties and headed to the computer store.

The guy at the store was friendly. “Got the cash now? OK, we’ll get her running again. It’s Saturday now, we’re closed Sunday and we’ve got a lineup of jobs, so come back in Thursday, we’ll have it ready for you.”

“Thursday?” Nick’s mind raced with panic. He owed another week’s rent on Friday. There was no way he could earn enough money to pay a whole new payment on Friday after only having his computer for a day. “Are you sure you can’t have it any earlier? It’s really important to me…”

The man wouldn’t budge. Nick left in a huff, trying to think of ways he could raise the money. He stormed back to his room and slammed the door angrily. His bum was too sore to sit down and he couldn’t keep his attention on video games, so he went to sleep in frustration.


The next week was terrible for Nick. The thong cut panties constantly rode up reminding him of his predicament, and every time he was near a mirror he noticed the obvious outline of his bra through his shirt. To top it off, Brian was constantly “reminding” him of things to clean and Nick had to answer any questions with “yes, sir”! Thursday couldn’t come fast enough, and when it did Nick went to finally pick up his PC from the store as soon as it opened. He practically ran home to start it up and see if he could finish enough work to get some money before the next day. His inbox was filled with disappointment. “Nick, you haven’t returned my mail for almost a week!” one email shouted. “I can’t work with someone who doesn’t even respond to me. Consider our agreement over.” He assessed the damage. Overall he’d lost 4 of his clients and was left with only large scale jobs. They would pay great, but there was nothing that he could finish in 1 day, possibly not even in 1 week. “I can’t deal with another week of calling him ‘Sir’ “, Nick frantically thought “and if I don’t get that money by tomorrow I’m going to be worse off!”


Nick sat in Brian’s passenger seat fuming. It was Saturday morning, and they were on their way to Nick’s salon day. Exhaustion had caught up with him Friday morning after he worked through the night trying to complete a job, and when Brian had found him Friday evening he hadn’t made a dime. So, here he was. “You know, you are going to be treated like a princess today. Karen makes her living pampering women, if you could relax you might enjoy yourself. From what I’m told it’s very pleasant. You don’t want me to hear that you’ve been uncooperative.”

“Sir, I don’t want to be treated like a princess! I’m a man!”

Brian chuckled. “Nick, you’re wearing lingerie, you’re totally hairless, and you’re even wearing makeup. Now is not the time to pretend you’re some macho man.”

The rest of Betturkey the ride was spent in silence with Nick ashamed, frightened, and angry. He couldn’t believe Brian was doing this to him. He couldn’t believe Brian was ENJOYING doing this to him. When he’d confessed he didn’t have this week’s rent last night Brian hadn’t even been upset, just smiled and told him to be ready for a 10AM appointment. It was almost worse than the stern warnings he’d gotten previously, Brian almost seemed excited for Nick to fail.

The salon was busy when they arrived. Nick felt paralyzed when he saw the crowd of ladies inside, but Brian went around, opened his door and held out his hand. “Miss?” Nick shot him a glare but took his hand and followed him inside. Brian led him straight to the front counter where a petite teenager waited. “Good morning. We have an appointment for Nick for the full treatment with Karen.”

“She’s in the back. Just a moment sir.”

The girl returned a moment later followed by a breathtaking young woman in a form-fitting red dress. “Brian! Great to see you as always. And this is Nick? I’m told you are here for the Princess treatment? What a treat! We usually only do that for groups for special occasions like bachelorette parties, but Brian’s such a great friend I cleared my schedule. Not everyone gets a chance like this, you should thank him!”

The room had gone quiet. Nick could feel every eye in the place on him. Some of the women were murmuring to each other while they stared at him, giggling to themselves. Nick felt himself turn beet red as he looked over at Brian. “Thank you, sir.” he reluctantly said.

Brian was beaming. “Only the best for my princess. I’ll be back in 4 hours. You and Karen have fun!”

Karen led the blushing boy to a chair in front of a sink at the back of the salon. He sat as requested and she started brushing his long blonde hair back. “You’re lucky to have such gorgeous hair, Nick! It’ll look just amazing when we finish. I love your lip gloss too, it suits you so well. Did you pick it yourself?”

“Uh, no miss, Brian got it for me.”

Karen smiled. “He’s so thoughtful. He really has a great sense for what will bring out the best in people. Lay your head back please.”

The warm water was soothing and the exhausted Nick felt himself getting more and more relaxed as Karen massaged his head and washed his hair. When she finished she wrapped his hair in a baby pink towel and pointed to it in a mirror. “Princess” was written in sparkly red letters along the edge of the towel. “Don’t you love it?! You can take it home with you, it’s part of the package. Unfortunately we have to clean Brian’s gloss off your lips, but it’ll be worth it. Let’s move up front now and get the real fun started.”

To Nick’s dismay Karen led him to a chair right beside the front window within full view of the street. He was instructed to lean his head back and close his eyes, and Karen called 2 girls over to help. He felt one remove his shoes and start massaging his feet in a tub of warm water, while the other girl did the same to his hands. As much as he hated to think it, he was enjoying himself. The massages were incredibly relaxing and he found himself easily conversing with Karen as she cut his hair. The massages were replaced by the girls trimming and shaping his nails and separating his toes with small pieces of foam before they began to apply polish. He tried to look but Karen gently pulled his head back upright. “You can see when we’re all done. Until then, no peeking!”

The girls gave him 3 coats of polish on his fingers and toes Betturkey Giriş as Karen finished cutting his hair. “Now for the main event.” Karen opened a large case on a nearby table. Inside was the largest collection of makeup Nick had ever seen. Karen walked him through application step by step as she did his face, teaching him how to use foundation, blush, powder, eye shadow, eye liner (“I’m using liquid for right now, but I’ll send you home with a soft pencil that you can smudge to get a really smoldering bedroom look” Karen winked at him), mascara, and lip liner followed by lipstick (“You’re lucky to have such pouty lips! Brian will adore them, just wait”). Nick didn’t enjoy the makeup, but he HATED when she spent almost 5 minutes plucking his eyebrows. Whenever he moved his face he felt the makeup on his skin and he could feel and taste the waxy feeling lipstick coating his lips.

Finally two girls carried over a large mirror covered with a sheet and placed it in front of Nick. “Are you ready?” Karen asked him. She walked over and ripped off the sheet.

Nick’s heart stopped. There was no mistaking the woman in front of him for a boy. His golden hair fell in loose curls around his face. His eyes were rimmed in a thin black line that flicked off the edge of his eye in a small wing. Shimmering violet eyeshadow surrounded it, making his blue eyes seem intense and alluring. His eyebrows were shaped in a delicate arch and even he had to admit pouty was the perfect word for his soft pink lips, made up into a perfect cupids bow. He gasped and brought his hand over his mouth where he saw his nails, shaded violet to match his eyes and covered in a glossy finish.

“I knew you’d love it!” Karen gushed. “Brian’s paid for one of every kind of makeup we used today, so you can just follow my instructions to recreate this look! I’ve also included some other shadows and lipsticks as well as some pencil liner, so you’ve got no excuse to not experiment” she teased. Nick nodded mutely. “Here he is now. I’ll let you have your first impression” Karen spun around and was off.

Brian slowly walked over to Nick. “Wow. You look even more stunning than I imagined. Your hair fits you perfectly. Shall we go?” Brian called for Karen. “I hope he didn’t give you any trouble?”

“He was a darling Brian. Although the way he looks right now I’d say he’s trying to get into some trouble…” Karen winked at Nick. “Here you are, as requested.” She handed Nick an open box filled with a stash of makeup and the pink Princess towel. “Come back anytime Nick, a friend of Brian’s is a friend of ours.”

Brian held the car door open for Nick and got in the driver side. He pulled the car out of the parking lot and it was a few blocks before he said anything. “I’m glad you went through with that, I was afraid I’d have to punish you more. Karen’s a good friend of mine and it means a lot to me that you didn’t give her a hard time.”

“You may be wondering why I haven’t told you the next penalty yet. To tell you the truth I wanted to see how today went before I decided what I should do. You’ll find out soon enough, but for now we have something to discuss. To put it bluntly, the name Nick is no longer fitting. You are no more a Nick now than you are a David or a Tom. When you are in my debt, your name will be Nicole. Do you like that name, Nicole?”

Nick looked down at the floor of the car. “No sir, I don’t like it.”

Brian reached over and flipped down the mirror on the back of the sun visor. “Take a good look at yourself. Do you look like a Nick or a Nicole?”

The woman in the mirror looked Betturkey Güncel Giriş deeply back at him. The pink lips moved and he heard a voice say “Nicole, sir.”

“That’s good. I agree.”

The ride continued in silence until Nick noticed Brian take a right turn. “Sir, your house was left there.”

“Nicole, we’re not going home. If you fail to make your rent payment again, I will replace your wardrobe with entirely clothing of my choice. We will spend the afternoon buying that clothing.”

Nick started panicking. “Sir, I can’t go shopping! Not like this!”

Brian smirked. “I was hoping you’d say that. You would stand out, the way you are currently. Those jeans, that t-shirt and those shoes are hopelessly at odds with the rest of your look and people will wonder why that girl is dressed like a boy. Some may even notice that you’re not a girl at all.” Nicole waited nervously for him to continue. “I’m willing to purchase you a more suitable outfit for shopping, we can find it at the first store and you can wear it out. All you have to do is ask me.”

Nick felt himself burning with embarrassment. “How did it come to this?” he thought. It felt so sudden, like he’d never had a chance to really stop it. “Sir… would you please buy me an outfit for shopping?”

“I would be glad to, my dear.”


The mall was packed. Brian led Nick by the hand to the change rooms at the back of a large department store. “Wait here, Nicole. I’ll bring you something more suitable.”

Nick spent the time until Brian returned silently stewing at the predicament he was in. When Brian got back he handed 2 packages through the door. “Put these on and hand me your clothes.” Nick opened the first package, feeling the soft fabric and unfolding it into a yellow sun dress. The next package was a pair of white sandals with a small heel that buckled around the ankle. Nick pulled the dress over his head and watched in the mirror as the fabric fell loosely around his slender body. The hemline was mid-thigh, and the dress moved and caught the air as he moved around. He slipped the sandals on and was surprised to find the low heel was actually fairly natural to walk on. His violet toes accented the white of the shoes below the dress.

He opened the door and felt vulnerable and exposed when Brian hungrily looked him up and down. “Can we please just go? I feel like everyone’s watching me.”

Brian smiled at her. “They are, Nicole. You’re a very pretty girl, you deserve to be watched. Shall we?” He put his arm around Nick’s waist and led him out into the mall.

By the time the pair left the mall Nick was exhausted. Brian had dragged him in and out of store after store, making him try on more clothes than he ever had in his life. Brian even forced him into a lingerie store, where he not only purchased more pairs of panties and bras for Nick to wear daily, but also bought a garter belt with sheer black stockings and worst of all a corset that he delighted in having the sales girl fit on Nick. The sales girl made flirty conversation as she laced Nick up tightly. “Is this a present for you? Or maybe it’s really a present for him…” cocking her head toward Brian. She gave Nick a knowing look and he blushed. “Ah, as I suspected. Well, I’m sure he’ll love it.”

Nick mentally tallied up what Nick had bought. 6 pairs of panties, 6 bras, 1 garter with stockings, 1 corset, 8 dresses, 6 skirts, 7 blouses, 4 pairs of shoes from the white sandals to a pair of deadly looking stiletto heels (Nick would’ve thought of them as “fuck-me shoes” if he had have seen anyone else wearing them), and finally a bikini. He’d been tallying what Brian was spending and by the time they left he’d spent well over what Nick owed him. “That bastard” Nick thought to himself. A sinking feeling in his stomach told him Brian had bigger plans in mind than just rent money.

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