Sissy - For Rent

"Good, good. Head back into your bedroom," he said casually, gesturing at the door, "strip and put that thong on, then come back out here and let me get a good look at you, sissy."

Brian blinked, looking from the thong in his hand and back to Tyler, almost as if his disgusting request hadn't quite sunk in. Surely, he hadn't just told him to wear a woman's underwear and present himself for inspection? Brian was petrified. He couldn't say no. He really couldn't. But he couldn't do this, it was too humiliating. "I...I can't do that."

Tyler sighed. "What happened to be obedience? Now. I'll give you one chance. You go back in there, you strip, you put them on and you get that big ass out here, or I fucking do it myself and then throw you out on the street in just those panties." Tyler's voice was stern and deep, and his threat didn't seem like an idle one. Brian's breathing was out of control. "Make your choice, but one way or another you're wearing those, either for me to see or for the world to see, faggot."

"No! Please, sir. I'll do it...I'll do it." Brian couldn't even begin to fathom the horror of the alternative and ran into his bedroom, tears leaking from his eyes. Trembling, he acquiesced to the perverted demand. Brian stripped all his clothing and stepped into Amber's dirty thong. He pulled the tiny material up his long, slender legs and let it nestle up against his micro-penis. He could feel the fabric quickly disappear between his two large ass cheeks as he pulled the waistband up his hips. Brian looked in the mirror and more tears rolled down his cheeks. He was practically indistinguishable from a woman.

The only give away was a very small bulge where his baby dick was hiding. Everything else was not only feminine but the pinnacle of the female form. Brian had always been self-conscious for this reason, he hated how delicate and womanly he looked. He'd always been bullied for his little AA cup tits, with their appealing rounded shape and big nipples. Now he was about to walk out in panties to be look at. He had no idea, no understanding of where this would stop. It had already escalated too quickly, and Brian felt significantly less safe by the second. For some reason, as he prepared himself to leave the room, his imagination was running rampant with the idea of Tyler's big black cock...that was the last thing he wanted to think about now, but it was unshakeable.

Taking a deep breath and wiping away the remaining tears, Brian opened the door and walked back into the room.

Brian nervously walked into the room, back towards the sofa where Tyler sat waiting, grinning. He crossed his arms across his chest to cover his shameful breasts, but in reality, all it managed was to develop alluring cleavage instead. Brian walked forwards and immediately his eyes glanced down at Tyler's crotch; his hand was still under the waistband of his shorts and Brian could see the massive outline of the pipe against his thigh. Tyler's jaw dropped as Brian timidly walked into the view. He was elegant and long, his soft pale skin contrasting with the black of the thong. He couldn't help but start laughing hysterically, how did this boy look this much like a tight young girl?

Brian stood in front of the man, eyes down and arms crossed. Tyler shook his head and laughed again. "What the fuck is your body, man? You were in a relationship with a hot slut and you still managed to have the best body haha." Brian's face was fully red, a deep beetroot colour. He knew right now Tyler was scanning him from head to toe. "Uncross those arms, lemme see those titties." Tears rolled down his flush cheeks and Brian lowered his arms. "Mmm, shit." He heard Tyler say quietly as his breasts came into view. He hated that his large, prominent nipples were hard, and he couldn't believe Tyler was clearly enjoying his body. "You've got better tits than plenty of women I've fucked." He added.

Brian looked up from the floor just long enough to see Tyler biting his lip and his hand moving vigorously under his shorts. He was masturbating to his body. Beneath the shame and self-loathing there was a small and unavoidable twinge of arousal. There was a deep burning desire in the old man's eyes.

"Turn around for me, I need to see that ripe ass." Tyler said. Brian did as he was told, as he always did, and revealed the fattest ass the black had ever seen. As he faced away, Brian heard the loud and pleasured groaning. "Unreal...you got the best ass I've ever seen."

Brian's tiny cock twitched at the compliment, and he blurted out a meek "Thank you, sir."

"Lemme get a better look. Get on this coffee table and get that ass up and face down, just like you did for your ex." Tyler demanded. Shaking with fear and a burgeoning and confusing arousal, he climbed onto the table and assumed the required position. "That's it, sissy. That's it right there." Tyler's breathing sounded more ragged and flustered. He was in love with this ass, it was perfect. He leaned back and slid his shorts down, unleashing his huge, black cock. He wrapped his large hand around it and began to openly stroke as Brian looked away, face pressed against the table.

He could hear the new sound of Tyler jerking properly now, spitting on his hand and lubing up his cock causing it to make sloppy noises as he pulled himself off. He kept him in that position for what felt like hours, each minute crawling along slowly as heard his landlord muttering under his breath.

After what felt like an eternity, Brian head Tyler stand up, groaning. "I'm gonna fucking blow all over your ass, slut." He cried out, tugging himself to completion. Brian didn't even have the time to mentally prepare before he felt ropes and ropes of hot thick liquid coat his lower back and fat ass. It was humiliating. He'd never felt smaller. Tyler laughed as he squeezed the last few drops from the end of his python all over Brian's ass. "All that for a week's rent."

Tyler pulled his shorts back up. "Here's your conditions for the rest of the week: you wear panties every day. And..." He heard Tyler pull something out and felt something light land on his back as Tyler thumbed out notes from a large roll of money and let them fall on Brian's cum covered back. "...buy yourself some slutty bras for those little titties too. Get yourself some food too." He walked over to the door. "You best follow my conditions, I'll be checking." Brian heard the door slam and he broke down, doggy style on the table still, covered in cum and money.

And just like that, it was over, for now. Brian rushed into the bathroom, removing his panties, and climbing into the shower. He felt dirty and he needed to be clean. He felt the cum under his fingers as he washed himself in the shower, there was just so much. He lathered himself up in soap and began to clean his body entirely. His chest felt so sensitive, and his nipples were swollen, they felt good to the touch. Forgetting himself, he began to squeeze and pull at them, relishing the sensation. He looked down to see his tiny cock was solid and couldn't help but use two fingers to jerk it.

He hadn't been this aroused in a long time and he hated it. Why had this turned him on so much deep down? Even his mind was betraying him, he tried picturing anything else, Amber, other women he'd been with...but the only thing he could picture vividly was Tyler on his couch stroking his big black cock. Brian had wanted to see it so badly, out of a morbid curiosity at first he thought...now, as he leaned with one hand against the shower wall and the other furiously pulling at his dick to the thought of black cock, he wasn't so sure it was just curiosity. With a loud but soft and effeminate moan, he shot his tiny load out in little spurts into the bathtub.

Conflicted further still, he stepped out of the shower and dried himself off. He looked at himself in the mirror as he did, at his feminine body, tracing his curves and features with his hands and the towel. Today was the first time a man has been enraptured with his body. Sure, people had made fun of him and bullied him for his body, but this was the first time he'd felt appreciated and desired. The encounter had been disgusting and cruel, no doubt, but Brian had always secretly enjoyed humiliation immensely.

He accidentally stepped on the thong as he went to leave the bathroom. He bent over and picked up the discarded and dirty underwear, feeling the soft lacy fabric in his fingers. He bent over and pulled them up his long, sexy legs until they fit perfect over his little clitty and ass. Then he walked out of the bathroom to collect his filthy money and do some shopping.

The package arrived quickly. Brian couldn't deny what felt like excitement when he opened the lingerie package. It felt weird spending the money Tyler had thrown at him, but he'd spent longer than expected browsing panties and bras, picking out what he thought would suit him best. After he'd submitted his order, he reflected on why it mattered, it was just for this sicko's amusement, right? Why did he spend the time admiring and picking what he thought was hot. And now it was here, and Brian was quick to slip into his underwear. It felt...right, the material was so soft against his delicate skin and the underwear was so pretty.

He'd managed to get the correct size bra too, he thought a little too proudly. It accentuated his breasts and cleavage more than he felt comfortable with, even with a loose t-shirt on it was clear he had more going on than a normal man should. It became too natural too quickly for him to wear the underwear each day. At first the fear of being caught without was what drove him, but after a few days it just felt normal and he enjoyed the softer feminine underwear against his body.

He fortunately didn't have many interactions with Tyler during this time. He'd see him when taking out the trash, the older man just stood and watched him move, eyeing him up blatantly and smiling. His demeanour towards Brian had shifted immensely. Gone was the cold and callous stares, replaced instead by a blatant, hungry lust...Brian had to admit it was an improvement and he was left flush and flustered after feeling his eyes all over him.

About five days later, Tyler stopped him in the hall of the apartment building. One large arm extended out to block his passage and the rest of Tyler's large body moved in the way. "Afternoon...think we best check if you're upholding your end of our deal." He said calmly, looking Brian up and down.

"I am, sir. I'm wearing what you asked." Brian responded, shy and avoidant of eye contact.

"Show me." He said, gesturing at Brian's t-shirt. He glanced around the hallway, it was empty for now but he still felt horrified at the prospect of revealing his little secret in a public place. But Tyler's size and proximity meant fear overrode the horror. Brian's trembling hands took hold of the bottom of his t-shirt, and he lifted the fabric up to reveal his little titties in a very nice red bra with black lace. Tyler nodded his head in appreciation, eyes pinned to the boy's chest. Tyler reached up slowly, Brian's heart thumping in anticipation. He gripped the bottom of Brian's t-shirt and brought it up to his face, "Open those sweet lips for me." He said and Brian immediately obeyed.

Tyler placed the t-shirt in between his lips and slipped a finger under his chin to gently close his mouth around it, holding the t-shirt in a raised position. "There we go...and now the shorts, gotta make sure you're following the whole deal, baby." More furtive glance let Brian know they were still alone...but in the middle of a hallway lined with over ten doors, that could change in a second. He wanted this embarrassment over as soon as possible, so holding the t-shirt up in his mouth, he pulled his shorts down to his knees. Tyler bit his lip and grunted in approval at the matching panties. It was evident to both of them that Brian was erect. With one big finger, Tyler made a circling motion at Brian. He knew what he wanted. Awkwardly, shorts still around his knees, Brian turned on the spot for him.

"I've watched that video a few times now and this ass looks so much better in real life." Tyler said, leaning in and whispering in Brian's ear. It was accompanied by the feeling of a large rough hand grabbing a handful of his ass, something that shocked him. He kneaded the flesh and gave it a short, sharp slap, setting both cheeks jiggling from the force and causing Brian to yelp. "Good to see you're taking our deal seriously. You can cover up now." He said calmly and Brian rushed to hide his matching panties and bra quickly. "Your rent is due again in two days...if you haven't got the money again, I'm sure we can work something mutually beneficial out again." The smirk on his face was broad. Brian had been unsuccessfully begging for money from anyone all week and hadn't heard back from any jobs, so he knew he'd have to take Tyler's offer again.

"I'm sorry, sir...I still don't have any money." He responded.

"That's OK...I'll get what I'm owed, gonna work you harder than last time though. Make sure you're wearing that set of bra and panties when I'm over on Sunday, you're looking fucking good for me." And he let Brian carry on.

Back in his apartment, Brian couldn't stop himself from touching himself. He'd leaked pre-cum into his panties, he'd never felt more objectified and desired. He blew his load inside his panties in seconds and orgasm was followed by a rush of guilt. He'd just been groped and humiliated...and this was his reaction? What was going on with him? He should've been immensely fearful for what Sunday held after Tyler's comments...but instead there lingered a subconscious and deep excitement.

Sunday came and Brian was ready. He'd shaved that morning, plucked his eyebrows more diligently than usual, he'd even put a subtle amount of Amber's leftover perfume on. And of course, he was wearing the matching set Tyler had appreciated so much. It was a hot day, so he hadn't even got dressed beyond the underwear. So when Tyler let himself in, he found Brian cleaning in just his underwear and his soft blonde hair up in a high ponytail.

"Shit, I didn't expect you to be this ready for me, haha." He laughed, walking in and sitting on the sofa in a way that signified he owned this place. "I reckon you like wearing that stuff." He said absently as he placed his feet on the coffee table. He patted the sofa next to him, "come on, sit down with me." It was a small sofa, so when he sat down next to the large black man, he felt incredibly small. Tyler placed a large, thick arm over the back of the sofa and imposed further on the small white boy. Brian could already see the fat lump in Tyler's shorts, the cock that had been plaguing his mind this whole week. He could feel himself salivating. "So, you got my money?"

"No...I'm sorry, sir. I've tried everything, but I still don't. Please don't kick me out, I'll do anything." Brian pleaded.

"Oh you'll do anything, will you? That's good..." He replied, his hand dropping and resting on the small shoulder of Brian, his black skin contrasting heavily against the pale white of Brian. "I got uses for a pretty little thing like you." He readjusted, spreading his heavy thighs and Brian could see his cock moving under the fabric. "But what I need is a good girl, not a good boy..." His rough hand began to massage his shoulder, fingers pressing in. "Now when I look at you, I see a good girl, ain't nothing even remotely male about. Not a single thing..." Brian had to do everything to control himself, he knew Tyler could feel him shaking. "So, I have no place for a good boy, but I could work something out with a good girl. So tell me, what are you?"

This was too much. Heart pounding, mouth dry, sweat beginning to bead. Every essence of masculinity was being stripped from Brian, every last drop. There was only one answer to the question, he knew it and Tyler knew it. Something in Brian was snapping, breaking...the words 'good girl' were loud in his head, they were something to obtain. Amber had called him it multiple times and he'd always detested it because of how small it made him feel. But now he was getting a taste for being small. He opened his lips and in his soft little voice, he said:

"I'm a good girl, sir."

"That's what I thought...your name is Brie from now on, is that clear?"

"Yes, sir." Brie responded meekly. Tyler's big hand squeezed Brie's shoulder tightly, the big man was looking down at her with a cocky grin.

"Perfect, perfect. I don't have room for a little white boy called Brian, but for a little white girl called Brie...I've got room." To Brie, this felt strangely reassuring. A few weeks ago, Brian would've despised this but now, with the offer of safety on the line and something awakening deep within, Brie was quietly content.

"Now for paying the rent this week, I got certain needs and..." With his other hand, Tyler reached over and took one of Brie's soft and tiny hands in his and guided it over. Brie watched as her dainty hand was placed directly onto the bulge on Tyler's thigh. Her heart exploded into life, it felt massive. Thick, wide, and the heat was emanating through the fabric. She couldn't believe it was happening. "... you'll be taking care of those certain needs for me." Tyler began moving her hand up and down the long shaft, Brie wasn't even going from tip to base yet it felt impossibly long, her eyes couldn't be torn from it. "I've seen you staring, baby girl, it's only natural. You want to see it, don't you?"

"..I, I do, sir." Her hand was now stroking up and down by itself.

"Tell me what you want, girl."

"I want to see your big black cock please, sir." Brie said through staggered breaths. She wasn't lying, it'd plagued her mind all week. It started as pure fascination but devolved into perverted obsession now.

Grinning at the affirmation of what he suspected, Tyler pulled his dirty wifebeater off, leaving him in just his shorts. Brie looked up at his large, imposing body. He was heavily overweight but so broad and powerful looking it made Brie swoon slightly, he was just all that much more masculine than her. He reached down and removed his shorts slowly. His massive black cock bounced out, free from captivity. Brie audibly gasped as it came into view. It was beautiful, far more perfect than she'd imagined in her fantasies. Long, perfectly formed, thick, circumcised. It must've easily been 10" long and as thick as Brie's wrist.

She sat there openly staring as Tyler leaned back to allow her to admire his full manhood. Even his big, heavy balls were spilling onto the sofa and resting on it. Brie felt her little clitty get harder than it ever had before, straining against the fabric of her panties.

"I knew you'd love big dick when I first saw you. Look at you, you can't take your eyes off me." He was chuckling and he was entirely correct. Brie's hand was resting on his thigh, painful inches away from Tyler's giant cock.

"Please...let me touch it, Mr. Green." Brie said, whiny and pleading.

"Shit, I walked in here expecting you'd need some hard convincing but that clearly isn't necessary. Go on, touch a real man's cock for once." Tyler couldn't believe his luck, she was already so submissive. With other tenants, it'd taken weeks and months of manipulation to get them to this level. He was going to enjoy his newest indentured slut, that was for sure.

Brie's intrepid hand shakily moved towards his monster cock. Her little white fingers curled and wrapped around the hard black meat in front of her. He was so thick she couldn't get all the way around. It felt so heavy and strong in her hand. A lump in her throat rose as she slowly and purposefully began to slid her hand up and down his impressive length, watching the skin move and feeling him throb.