The Trouble with Roommates Ch. 04

Nick spent the next week trying to keep his mind off his closet full of women's clothes. Brian was getting more controlling as the money owed kept increasing, and now he was texting "Nicole" at random times during the day demanding a selfie to see if his makeup was done or to make sure he was wearing a bra and panties at all times.

Unfortunately for Nick he'd barely been able to get any work done over the past week. His daily makeup and hair routine took him close to an hour before it passed Brian's strict inspection, and by the time he was dressed and had cleaned the house it felt like half the day had passed. When Friday rolled around and the fact he'd be short again sunk in he tried to enjoy the last of his time in male clothes before he sunk into the inevitable.

Brian was again pleased to hear he couldn't make his payment. Saturday morning he woke Nick up bright and early and told him to go shower and get ready. By the time Nick had his hair and makeup done and returned to his room wearing his daily lingerie, Brian had ransacked his room and put all his male clothing into a large locking chest. Making a show of snapping the lock shut and pocketing the key, he turned to Nick. "Nicole, I'll leave this chest in the basement. If I find out you've tried to sneak something out of it you will be severely punished, and I don't want to do that to you. I don't think you want that either, but maybe you do..." he gently stroked Nick's pantied ass. Nick shuddered. The worst part about the week since his makeover had been how touchy Brian had gotten with him. Nick could barely walk by in the hallway without Brian pulling him closer by the waist, rubbing his ass or worse, giving him playful spanks as he walked around. It was all Nick could do not to be sick, but he was forced to smile and say "thank you, sir" when Brian complimented his appearance. Now that he was going to be dressed as a woman full time, he knew it wouldn't stop.

"Since it's your first day, I'll let you pick your outfit. Make it sexy for me. All the shoes you own now are high heels, that wasn't a mistake. Between noon and midnight you must be wearing heels at all times, and you will be punished if I catch you barefoot. I'll be waiting in the living room for you."

Finally Nick was alone. He took a few minutes to himself before opening his closet, now entirely dresses, skirts, blouses and lingerie, and fingering through his options. He finally settled on a dress that he hoped wouldn't draw too much attention, a forest green A-line halter dress that came to just below his knees. A pair of black suede booties with a 2" heel complimented the dress well, and he walked across the room a few times getting used to the feeling of walking in them. The heels caused his hips to sway as he walked and forced him to take shorter steps, and he noticed his walk was automatically more feminine. He took a deep breath and went out to meet Brian trying to ignore the click, click, click of his heels on the floor as he walked.

Brian whistled a low whistle when he walked in. "You are a vision of desire, Nicole." He walked over and circled Nick slowly, running his finger around his waist, along his bum, and down his thigh before stopping in front of him. Nick shivered at the light touch and Brian chuckled. "You seem nervous, Nicole. There's no reason to be nervous. You look like the kind of girl who is used to being wanted." He stepped forward and wrapped his hands around Nick's waist. "I spent a lot of money on these pretty clothes for my pretty girl. Show me how grateful you are, give me a kiss."

Nick wished he was somewhere else, anywhere else but here with Nick's strong arms around him. He knew he couldn't kiss him, but he didn't dare refuse. He was paralyzed with indecision. Brian saw the expression on his face and moved in and down, kissing Nick's neck gently as a hand moved lower and started caressing his ass. An involuntary moan escaped Nick's lips when Brian gently bit his earlobe. "I'll ask once more" Nick felt Brian's hot breath as he spoke quietly in his ear. "Give me a kiss."

A wave of nervousness, shame, and arousal swept over Nick, making his knees go weak. His legs gave out but as he fell he felt Brian's strong arms holding him up. His arms reached up and around Brian's neck, and he felt himself moving in for a kiss. "I can't be doing this" he thought. His lips grazed Brian's. "This is wrong" he felt Brian gently bite his bottom lip and breathed hard. "I'm a man!" Their tongues met, and his mind went blank as he sunk into the kiss.

Nick lost track of how long their kiss was. When he regained his senses he was still in Brian's embrace and could feel his hand stroking his ass through the dress. He turned bright crimson. "That wasn't... I mean, I didn't want to... I mean..."

"Shhhh" Brian placed a finger over Nick's trembling lips. "You did want to, whether you admit it or not. I wanted to, too. And like it or not, you enjoyed it." That part was true. Nick had kissed his fair share of girls, but he had never had a kiss like that, that had left him powerless and that he had felt deep down inside himself.

Brian stepped back. "Nicole, I don't demand much of you. I do, however, expect you to treat me with some affection, and that includes a kiss when I get home from work, among other times. You're my girl, and I'm your man, so it's part of our arrangement. Speaking of our arrangement, next Friday when you fail to pay rent you will be given a choice of penalties. You will either have your ears pierced 3 times in each ear, or you will have your ears pierced once and have your belly button pierced. I can't decide which I like more, so you can pick for yourself. You're dismissed, I'll be in here if you need me."

"T-thank you sir" Nick stammered before leaving the room shakily.

The rest of the day was a blur. All he could think about while he was trying to work was Brian's lips, the way he'd submitted to Brian's strength, how powerless he had felt in Brian's arms. All he could think about was how right it had felt. His dreams were no escape.

***

As usual, Brian hadn't been kidding. Monday afternoon a text message from him arrived. "Nicole, I'll be home in 15 minutes. I want my pretty girl to meet me at the door." The same Tuesday, Wednesday, and Thursday. On Thursday evening when Nick returned to his room he was surprised to find an email from one of his old buddies.

"Nick, bro! It's been forever! I know you've been dodging our calls, probably busy with your work or whatever, but tomorrow we're taking you out for beers if we have to take you kicking and screaming. We'll pick you up at 8 at your place. Can't say no, dude!"

Nick swallowed hard. His buddies weren't the type to joke around like that, if they said they'd be here no matter what they'd be here. He knew Brian would let them in, he had been teasing him about why he hadn't been out drinking in a while ("Nicole, why haven't I seen your friends lately? You look great these days, you should want to show it off!"). He was going to have to ask for a day off.

The best way to get Brian to agree to something like this was to butter him up. Nick knew he didn't have too much of a chance but he had to risk it and he had to make the best impression possible to do so. A shower was followed by a careful makeup session and a quick couple coats of nail polish. All the tricks Karen had taught him came to play. When he was satisfied he went through his closet until he found something he hadn't had the nerve to wear yet. It was a short red dress that was contoured to fit his body perfectly, giving him the illusion of curves. The bottom hugged his thighs and only barely covered his butt and would've undoubtedly showed panty lines if he wasn't wearing a thong. The dress came up to a halter top, tying in a bow behind his neck. He knew he had no choice but to wear the fuck-me shoes with a dress like this. He spent a few laps around the room getting used to the high spike heels and calming his stomach. Finally he knew he couldn't delay any longer.

Brian was watching TV when Nick strode in. He'd used silver eyeshadows and a smudged soft eyeliner to give himself eyes that radiated desire. His lips were done up in a bright cherry red and he stuck the bottom lip out slightly to give himself a poutier look. Brian looked over and switched off the TV. He slowly looked Nick up and down. Nick gave him a spin without being asked, showing off his shapely butt.

Brian spoke slowly. "Nicole. What's the occasion?"

Nick struggled to find his voice. "I have a favour to ask of you, sir"

"Oh? What is it?"

Nick swallowed. It was now or never. "Can I please go out with my friends as Nick instead of Nicole tomorrow?"

Brian contemplated it for a long moment. Just when Nick thought he wasn't going to respond, he spoke. "That is a lot to ask, Nicole. We've worked very hard to try and ensure you're up to date on rent. One night off could undo a lot of effort."

"Please, sir. I'll be back in lingerie as soon as I get home, I promise. I wouldn't let you down." Nick hated playing this submissive role to Brian, but he'd been forced into a corner where he saw no other option.

"Yes, I believe you would be, I think we both know that's your place. I need something more, though. I want you to prove to me that you belong to me. Do you have any ideas of how you could do that?"

Nick could barely speak. He had hoped Brian would simply let him go with some flattery, but it was obvious now that wasn't the case. "What... what kind of thing, sir?"

"Oh, Nicole, you're a very pretty and very creative girl. Can't you come up with any ideas to show that you belong to me, that you're my pretty girl?" Brian leaned back in his seat and opened his legs slightly wider. "I'm afraid if you can't come up with anything I won't be able to let you go out as Nick tomorrow. A pity."

The floor felt hard on Nick's knees as he slowly lowered himself to kneel in front of the chair. A voice in his head was screaming at him to stop but he pushed it back and tried to focus on happy thoughts. His bright red fingertips moved forward and slowly unzipped Brian's jeans. The bulge he felt underneath told him he had made the right choice. He slipped his fingers in through the fly and pulled Brian's cock out. Nick's eyes went wide when it popped out, thick and long and getting harder. Other than his own, Nick had never felt a cock before, and he simply stared at it for a moment.

"Kiss it" Brian commanded him. Nick looked into Brian's eyes and realized what a sight he must be, a gorgeous blonde in a red dress on her knees looking up seductively before she takes the cock in her mouth. His heart was about to pound out of his rib cage as he slowly leaned forward and touched his lips to the head of Brian's dick. "That's it, Nicole. You can do it." A firm hand grabbed the back of Nick's head and pushed down gently, guiding the cock through his lips and into his mouth. His nose was filled with a musky smell. He gingerly moved his tongue around the shaft in his mouth and heard Brian groan. The hand let him back up briefly before pushing him down again, this time further down Brian's swelling cock. He continued to lick and suck as much as possible, focusing on breathing while Brian moved his head up and down. "Good girl, Nicole. You're my good girl." Nick couldn't believe how thick Brian's cock was. It was all he could do to keep his mouth open enough to take it, and when his head was pushed fully down his nose was still a couple inches away from touching Brian's body.

Once Brian got into a rhythm Nick started to notice more details. He noticed his cherry red fingernails wrapped around the base of Brian's cock, matching a lipstick stain he'd left. He noticed his blonde hair bouncing as he bobbed up and down. He noticed Brian's groans as Nick's tongue worked around his shaft. He began to lose himself in the moment and felt his mind shift as he began to associate with Nicole and startled himself by letting out a low moan. Brian was no longer moving her head up and down, she was bobbing and sucking all on her own. The experience was intoxicating. Nicole began to notice she could make Brian groan by gently massaging his balls, or working her tongue around the head, or taking as much of his thick cock in her mouth as she could fit and sucking deeply.

Nicole was so caught up in pleasuring Brian she barely noticed when he put both hands on the back of her head and held her down. Nick came to and frantically started begging but all that came out was a muffled "mmm! Mmmm!"

The cock twitched and exploded, splattering in his mouth and down his throat. Brian's hands continued to hold Nick's head down and he had no choice but to swallow. "That's it, swallow it, that's a good girl." Brian released his grip and Nick fell backwards, the cock sliding out of his mouth with a pop. He felt something run out of the corner of his mouth and absent mindedly licked it up, tasting more of Brian's salty jizz. He looked up to see Brian smirking at him. "This is the start of a wonderful relationship, Nicole. You can go out as Nick tomorrow. After tonight, I have no doubt that you know you belong to me."