Making Rent

Darren was roused from sleep by the shrill ring of his cell phone emanating from the bedside table. He sleepily groped around till he found it and swiped to answer. "Uh, hello," he mumbled groggily. He peered at his alarm clock and noted it was just after nine in the morning. Who even calls this early?

"Hello, this is Stephanie Miller," a pleasant voice greeted, "I'm looking for Darren Hyde. Are you he?"

"Yeah, um... what can I do for you?"

"Well, Mr. Hyde," Stephanie continued, "as you're no doubt aware, I manage your apartment complex and it's already the twelfth of the month, but I haven't received your rent yet. If you could get that to me as soon as possible that would be fantastic."

"Well," Darren began, "I, umm, I don't have it right now. I don't have all of it, I mean. I'm getting paid next week and as soon as I do I'll get it right to you."

"I'm afraid that's not acceptable, Darren. Are you available any time today? I'd like you to come to my office if you could, so we can discuss this matter."

"Yeah, I'm free," Darren answered. "When?"

"As soon as possible," the angelic voice replied.

"I just woke up so have to get ready. Is a half an hour from now OK?"

"That works, yes," Stephanie verified, "I'll put you down for 9:45, OK?"

"OK, I'll be there."

"Thank you, bye."

"Bye."

Not exactly the best way to start the morning, Darren thought. He was hoping he could get the rent sent in before anything like this happened, but that apparently wasn't to be. He dragged himself out of bed and wandered into the bathroom to shower. As he turned the water on and set the temperature just right he stopped to think about his landlady, Ms. Miller, as he usually called her, although considering their relative ages maybe that was silly. Darren finished college last year putting him at 23. If he had to guess he figured Stephanie to be maybe a year or two older. Not usually the age to already own a rental property, especially not a four story building so close to downtown, but Darren had heard she inherited it. Not a bad way to start life, aside from the obvious loss of a loved one, he thought.

Darren stepped into the shower and soaped up as he continued his musing. Picturing Stephanie in his mind he saw a slim woman, barely more than five feet tall, with moderate breasts, a cute butt and short dirty blonde hair that hung to about her chin. He definitely thought she was attractive, but at the moment that wasn't exactly what was on his mind. He was concerned about the rent situation, of course. He had most of it, but was a couple hundred or so short. He hoped maybe he could give her that today and the rest on payday. That would be the simplest solution. A surprising amount of time passed as he considered the situation so he was already rinsing off before stepping out of the shower and toweling down.

Darren made his way to the bedroom and once inside grabbed jeans and a T-shirt and threw them on. He didn't expect this to be a formal situation, after all. He stopped off at the kitchen, poured a bowl of cereal and wolfed it down. It was only a half past, but Darren always ran early rather than late. He figured that promptness could make a good impression for him when other things, being late with rent, for example, hurt that impression. Once he finished his breakfast he quickly rinsed the bowl then headed out the door.

He took the elevator to the ground floor and moments later entered the apartment complex's business office. There was a counter and a small work area behind it and Stephanie's personal office was off to the side. The shades were drawn on both the office's window and door. Darren took a seat and waited patiently for his landlady to come out. Just a few moments later the office door opened and Stephanie emerged. As soon as he saw her Darren knew he made the correct wardrobe choice. She was wearing a simple band tee and what appeared to be soft pink sweat shorts. The legs of her shorts weren't overly short, but neither were they long, leaving much of her toned and shapely legs exposed. Darren tried not to think about how alluring they were. He wanted to keep his mind on the business at hand.

"Ohh, you're early," Stephanie squeaked in surprise.

"Yeah, that's not a problem, is it?"

"No, of course not, please, come in."

Stephanie held the door as Darren walked past her, entering the office. He had a quick look around before taking a seat in the chair in front of her desk. Everything seemed the same since his last visit. Her desk was at one end of the room, knickknacks spread about and various personal items adorning the walls. There was a medium sized sofa along the wall opposite the door and houseplants took up just about the rest of the available floor space. It was a veritable jungle in there, but it made the place feel intimate and comfy. Stephanie closed the door before sliding behind her desk and taking a seat. She opened the folder in front of her and flipped through it before closing it and looking at Darren.

"Thank you for coming down on such short notice, Darren."

"No problem, Ms. Miller." Darren still chose to be formal with her.

"I've been going over your rental history and I'm a little concerned. I've overlooked your rent being late before, but it appears to happen nearly every month. Do you have an explanation for this?"

Darren considered his words before he spoke. "It's the job, Ms. Miller. I earn enough, but they only pay me every other week, so having the rent right when it's due is tough."

"That's understandable," she nodded, "and please, call me Stephanie. I get how hard budgeting can be, especially in this economy, but I can't keep letting you slide. It feels like I'm allowing you to take advantage of me."

"That was never my intent Ms.- err, Stephanie," Darren interrupted. "I swear."

"I believe you," Stephanie replied gently, "that does nothing to solve our little problem though."

"I can pay most of it now if you want," Darren offered.

"I was thinking we could work out another arrangement, if you're willing, that is."

"Umm, sure, what kind of arrangement?"

"Well, I could offer you a discount on your rent if you could take care of some things for me. That way it wouldn't be such a burden for you every month."

"Like odd jobs and stuff?" Darren inquired.

"No no, I have a handyman for anything I can't handle myself. I'm thinking of something more... unofficial."

"What exactly are you getting at?"

Stephanie looked Darren up and down before she answered. She found his lanky frame and mop of sandy hair enticing, as well as his cute face and the way his bottom lip quivered whenever he was unsure about something. "I'm just going to come out and say it, Darren. A woman has needs and I haven't been able to get them met lately. You're an attractive guy and you could use a little help, I thought we could kill two birds with one stone."

"I'm not sure I feel comfortable with that, Stephanie. It just seems... wrong."

"Don't be silly, Darren," Stephanie countered, "we're both adults. Just think of it as a transaction. And you'd really be helping me out, too."

"I dunno, I'll need to think about it, is that OK?"

"Take your time Darren," Stephanie stood as she spoke. Darren followed her cue, thinking their meeting was coming to a close. "There's just one thing you should know before agreeing."

"Yeah?"

Stephanie came around the desk and neared Darren before grabbing his wrist and pulling his hand towards her. "This," she said as she placed his hand on her left thigh where Darren could feel a decidedly unladylike swelling beneath her shorts.

Darren jerked his hand away in surprise. "Is that a-" the words hung in his throat

"Yeah Darren, it's a," Stephanie mimicked. "Is that going to be a problem for you?"

"Ohh Stephanie," Darren sighed, "You have absolutely no idea how much of a problem this isn't."

"Ohh, really," Stephanie probed, "do tell."

Darren's eyes were on Stephanie's shorts and the lump therein as he considered how to explain. "Well, [REDACTED] when I was finally given my own laptop I looked up lots of porn."

"Yeah, that sounds pretty typical," Stephanie observed.

"It was, at first," Darren continued, "but then one night while clicking through web sites all of a sudden I found myself at a site of girls... well, girls like you." Stephanie nodded. "When I saw it something just clicked in my brain. Like, I always felt like there was something missing when I was looking at porn and when I saw that site it was so obvious what it was. "

"Fascinating," Stephanie said as she casually reached into her shorts and pulled her cock out over the waistband. "Please, continue."

"Umm.. OK," Darren stammered as he took an eyeful of Stephanie's package, "uh... wh- where was I?"

"You saw a web page full of dickgirls and something clicked," Stephanie offered. She began slowly stroking her cock as Darren stared transfixed, his mouth watering.

"Ohh right, anyway I, umm, I didn't get any sleep that night, if you know what I mean."

"I don't follow," Stephanie grinned as she feigned ignorance. She really wanted to hear Darren say it.

"Well you know, I was too busy, you know..." Darren stumbled over his words, "fapping."

Stephanie burst out laughing. "Ohh I'm sorry Darren, that word just always cracks me up.

"Yeah, it's funny," Darren agreed as he continued ogling Stephanie's member. "Anyway, I remember the first shemale I ever masturbated to. She had blonde hair and wore pink lingerie. She was facing the camera sort of at an angle and had a hold of her cock right around the root and the rest of it just stuck out all bright and veiny. I can't tell you how many times I came to that pic, but it was a lot." Darren was surprised at the amount of detail he was pouring out to his landlady.

"Well, that was something else, Darren," Stephanie remarked. I suppose I still have to ask, although I'm guessing I know the answer. Are you up for my offer? Even if hearing your little back story makes me wonder if maybe you should be the one paying me."

"You've got to be kidding," Darren was taken aback a bit.

"Oh course I am," Stephanie laughed. "Relax buddy, keep your eye on the prize," she jiggled her hand, causing her erection to sway. "Sorry if I'm being too insistent."

"Ohh no, it's alright," Darren finally pulled his eyes off of Stephanie's beautiful cock and looked her in the eyes. "I accept your offer."

"Excellent. Would it be impatient of me to ask you to start right away?"

"Oh, I insist that I do."

"OK, well... just out of curiosity, what would you want to do, Darren?" Stephanie asked. She stopped stroking herself for a moment and touched an index finger to her pee hole before rubbing it all over the head, moistening it with her precum. Darren again found himself staring at her penis with lust.

"Whatever you want me to," he answered, licking his lips in anticipation as Stephanie continued painting her glans.

"Uh uh," she scolded, "I might not be the lady in pink, but you've got the closest thing to your fantasy standing in front of you ready to bust your dickgirl sex cherry. You're definitely going to remember this for the rest of your life, so we're doing what YOU want to do."

"Well, if you say so, Stephanie. I'd uh..." he faltered momentarily, "I'd really lick to suck it, if that's what you want."

"It's what you want, Darren," Stephanie purred, "so why don't you kneel down for me?"

Darren just nodded and lowered himself before the short woman with the impressive erection. As he did so Stephanie shucked her shorts and whipped off her shirt, flinging it towards the sofa on the other side of the office. She now stood before him wearing only her shoes and mismatched underwear. Her small breasts were held in what was actually a blue floral print bikini top. Farther south her panties encased her small rear and on the front side her testicles were still nestled within the bright red fabric. She was again gripping her cock, aiming at Darren, the head shiny and wet. He simply knelt there reverently, admiring Stephanie's package.

"Well," Stephanie asked after an uncomfortable amount of time passed.

"Sorry," Darren looked up at her, "I, ummm, I'm not really sure where to start."

"It's OK," Stephanie assured him, "Just do what feels right. Some people kiss 'em, some people stroke 'em. There's no wrong way to fondle a penis." She laughed at her painfully bad joke. Darren smiled. Then he found his nerve as he reached out, grasped Stephanie's womanhood and leaned in towards it. He held her shaft at an upwards angle and began kissing the underside of her glans. Stephanie let out a low moan of approval which encouraged Darren to continue. After laying a series of kisses all over the last inch or so of Stephanie's cock Darren sucked the head into his mouth. The sweet flavor of her precum invaded his senses, driving him wild. He loved how it tasted so he began painting her cockhead with his tongue in the hopes of persuading it to release more of the enticing liquid. Darren's tongue lashing had another effect as Stephanie groaned out her desire above him.

"Ohh fuck, baby," Stephanie moaned. Darren pulled away and looked up at her quizzically, which was the opposite of what she wanted. "No, I wanna be back inside that hot mouth of yours," Stephanie whined. Wanting nothing more than to please this little cock wielding goddess Darren sucked her crown back into his mouth along with another couple of inches. "Yesss, that's it, baby. Take all of me." His desire to please drove Darren forward, taking six inches of Stephanie's cockflesh before he hit a roadblock in the form of his gag reflex. Darren pulled off of her cock as he was wracked with an uncontrollable fit of coughing. Stephanie reached down and began gently rubbing his back till the coughing subsided.

"Are you alright," she asked, concern wrinkled her brow. Darren nodded at her, still not quite ready to speak. "Here," she grabbed his hand and pulled him to his feet.

"Damn," Darren swore, "I thought I was doing so well, too."

"You were, honey," Stephanie assured him before pulling him in for a kiss. It lasted for only a moment before she broke away and fell into a fit of laughter.

"What," Darren asked mystified.

"It's just funny," she teased, "you'd been sucking my dick for how long before we even kissed? That's not normally how it goes."

"Yeah, that is kinda funny," Darren laughed, "But I'm cool with that."

"Yeah, is it everything you'd hoped?"

"Totally!" Darren exclaimed, "well, it was till I gagged there."

"I got an idea," Stephanie said before heading behind her desk. She pulled her chair out and took a seat. "Maybe you just need a change of angle," she motioned to the floor between her legs.

"OK, but may I make a request?"

"Sure thing."

"Cool, could I um... could you..."

"Out with it, boy," Stephanie chuckled.

"I WANNA SEE YOUR BOOBS!" Darren blurted out, his face red with embarrassment.

Stephanie just burst out with laughter, but she dutifully reached behind her back as she did and pulled open the clasp of the bikini top, then she reached up and yanked the knot out of the halter before flinging the bikini top towards the sofa where her shirt was.

"They're not much, but," Stephanie said as she presented her small breasts, each one capped with a burgundy nipple. She wiggled them up and down alternately as she cupped them. Mesmerized by the way her humble breasts bounced Darren made his way to the other side of Stephanie's desk to join her.

"May I-"

YES! God, whatever you want, just do it," Stephanie laughed. "It's your party, quit asking."

Emboldened by the flippant way Stephanie invited him to do basically anything, Darren lurched forward and grabbed at her small tits, pulling, twisting and all around being less than gentle with them. As he played Stephanie pulled Darren closer. He wasn't exactly being nice to her poor little boobs, but Stephanie still enjoyed the closeness. Darren slipped down to kneeling between Stephanie's legs and captured one of her gumdrop like nipples in his mouth. He began to suck at it greedily as he teased and twisted the other. Stephanie let out a little squeal. Apparently her body was reacting to Darren's roughness differently than her mind had. As Darren began to nibble, then chew on Stephanie's nipple he felt her cock stir, poking him in the belly. He fully intended to take care of that gorgeous piece of meat later, but for the time being he was having fun with Stephanie's less impressive assets.

"Oh fuck, Darren," Stephanie groaned. "Maybe be a little more gentle?" The horny young man seemed not to hear her request as he bit down on her now sore nipple while he twisted the other and pulled at it forcefully. Stephanie cried out in pain and finally Darren pulled away. "Fuck, dude. A little bit was nice, but that really hurt! Look at my poor nip."

Darren shifted his gaze from Stephanie's face to the small breast he had just been gnawing at and was shocked to see several deep bite marks and a trickle of blood. "Ohh my god Stephanie, I am so sorry," Darren apologized profusely, "are you alright?"

"It's OK, I'm a big girl, I'll be fine, but don't you dare try anything like that on my girlcock, OK?" Darren nodded. "Speaking of..."

"I'm on it," Darren chirped excitedly before again grabbing at Stephanie's impressive erection and bringing his lips down over the head. He slurped at it noisily, running his tongue around it before he tried to take her farther into his mouth than before. Stephanie was right, he realized. This angle was much better for the act of fellatio. Before too long he had those same six inches in again, but this time is throat was a willing participant in the action. His confidence restored, Darren took Stephanie's womanhood deeper, throating the remainder till all nine inches of her cock were inside his hot, wet mouth and his nose was buried in the light tuft of pubic hair she kept carefully groomed just above the shaft.

"Ohh fuck Darren, you're a natural," Stephanie gushed as she reached down and stroked his cheek with one hand and his neck with the other, feeling her cockflesh lodged within his throat. The words were music to Darren's ears so he tried to see if he could top himself once more. Carefully he began pulling himself off of Stephanie's pole till her cock passed his windpipe. Able to breathe again Darren exhaled forcefully through his nose as he kept his lips locked around Stephanie's penis before drawing air in sharply. Lungs refreshed, Darren forced himself down upon the cock in his mouth and soon had his nose buried in Stephanie's pubes for the second time. He rested there for only a moment before pulling away to repeat the process. Darren quickly found a rhythm, taking Stephanie's pole to the hilt four or five times before refilling his lungs and going at it again. "Ohh my fucking god, Darren, this is incredible." Stephanie was downright amazed at this rookie cocksucker and the way he handled her formidable package. He'd been working away on her for five minutes or more without once pulling off. Stephanie was fast approaching orgasm with stimulation like this so she reached down between her legs and pushed insistently on Darren's shoulders. Darren desperately wanted to keep going, but felt Stephanie's pushing and after the nipple incident he had no interest in fucking up again so he pulled away, letting Stephanie's cock slip from his mouth with an audible pop.

"What? Did I do something wrong," Darren asked, both confusion and concern visible on his face.

"Not on your life, Darren. That might've been the best blowjob I've ever had, but, well, I'm almost ready to cum and I didn't want to choke you on it." Stephanie pushed her chair away from Darren and stood as she grabbed her cock and began to stroke it. "Darren, honey," she begged, "is it alright if I give you a facial? I think you'd look so cute covered in my cum.