Sugar Brother

With three of her brother's fingers penetrating her and his tongue on her clit, Tess was in heaven. She leaned back on one elbow while lifting her other hand up to her chest to play with her extremely sensitive, and extremely swollen nipples. As she did so, the blonde glanced over at the window of David's office. It took up the whole wall of his office and she was sure that anyone from neighboring buildings who happened to look toward them would be able to see everything that was going on. The thought only turned her on more.

She imagined David leading her over to the window and pressing her up against it as he bent her over and finally gave her his cock. She could easily picture her big breasts pressed against the window, her lips open as she moaned, her brother standing behind her, his hands on her hips as he pounded away at her already sopping cunt, dozens of people in the next skyscraper watching the show.

Her nasty daydream was interrupted by movement from her brother. He was standing up, and for a moment, Tess was sure that he was about to guide his dick inside of her and begin fucking her right there on the desk. She bit her lip in anticipation, but instead of shoving his throbbing cock inside of her, David shoved it back into his pants and zipped up. The teenager's anticipation quickly turned to frustration until she heard the word 'surprise'.

"I love surprises," Tess responded as she slid off of David's desk and began to dress. It'd better be a fucking good surprise though, cause I was just about to cum, she thought to herself as she slipped back into her clothes and tried her best not to look like she'd just been getting the best head of her life. After a last check of her makeup and brush of her hair, the teen declared herself ready to go.

They walked out of David's office, a bit more disheveled than professional decorum usually calls for, but nobody else was left in the office on that Friday afternoon. David used his key card to swipe the elevator to bring them back down to the street level. David and Tess walked through the revolving door and hit the downtown street.

"I'm leaving the car here," David told her, "because it's in walking distance, trust me you'll like it."

As they walked down the street they passed several skyscrapers with the ground level floor windows giving them peaks at expensive jewelry and fine clothes. One of the stores was a block away from the building with David's new condo and had lingerie displayed in the ground floor window. David stopped and pulled his teen sister by the wrist and pointed at the lingerie.

"Maybe tomorrow we can come back here," David pointed down the street at all the stores, "I can buy you some nice things, make you pop at some of those modeling auditions."

They headed to the building with the doorman and Tess and David were let in. They got to the elevator and went up to the 22nd floor of the 30 story building. The hallway only had three doors, and they walked to the door marked 22B. David knocked on the door and a pleasant realtor with graying hair and conservative blouse and skirt answered.

"Ah David," the woman said, "come in."

David and Tess walked into the furnished loft. The back wall was mostly floor to ceiling windows showing off the entire view of the downtown skyline. Smart furniture mixing wood and stainless steel was set up through the entire loft.

"The furniture was delivered earlier today, smart choices," the realtor said and then looked at Tess, "and who is this?"

"This is Tess," David said quickly, "now where are the papers?"

"Right here on the counter," she said, "escrow has already paid and if you sign this we close, and this loft is officially yours."

David walked over to the counter and signed. He shook the hand of the realtor who handed him the keys and she said goodbye leaving a business card on the counter and shutting the door behind her. David walked over to Tess who was looking out at the city and slipped his arm around her waist.

"This place, in the heart of the city, all mine," he said, "but that's not the surprise. Since this place is downtown, within walking distance of all of the agencies and big ad agencies...I want you to move in here with me. What do you say?"

David looked at his sister waiting for her answer.

Tess was all giggles and smiles as she and David paused in front of the store window to admire the sexy lingerie. The busty teen was still flush with the excitement of having her brother go down on her in his office, and the thought of modeling expensive lingerie for him, and having him rip it off of her only heightened her excitement to another level.

She wanted him, even thought she knew she shouldn't, and as they moved on, she found herself wondering if this surprise place that David was taking her to would be private enough for her to finish what they had started in his office.

The moment they stepped into the luxurious loft apartment, Tess was in heaven. It was perfect, from the furnishings to the paint, from the layout to the unbelievable view of the city that she found herself entranced by. As David discussed business with the realtor, the blonde stood in front of the massive window and marveled that David was actually purchasing such an amazing space.

"It's beautiful," she murmured as she felt her brother move up behind her and slip his arm around her waist.

"Since this place is downtown, within walking distance of all of the agencies and big ad agencies...I want you to move in here with me. What do you say?"

Tess spun around in David's arms, her body pressed against his chest, her face lit up with wonder, "Are you fucking serious? Hell yes, I'll live here." Without hesitation, the teen lifted herself up and kissed her brother enthusiastically. She'd never wanted him as much as she did at that moment.

"I've got something for you too," the blonde said as she stepped back until her back was pressed against the window. With her eyes locked on David's eyes, Tess slowly began to undress herself. A button, a soft shake of her hips and the rustle of clothes and a moment later she was standing completely naked in front of her brother, her clothes puddled on the floor beneath her.

Without a word, the teen turned her back to her brother. She placed her hands on the window and bent over, exposing her pussy to him, letting him see her arousal, wanting to feel him inside of her at last...

David let the question hang. He wasn't sure if Tess would agree to it. He thought he was gaining progress with her, making it work more like a mutual desire relationship and less like the quid pro quo mechanism they had set up during the weekend they bought the car. However, asking her to move in with him was the way to test that theory.

"Are you fucking serious? Hell yes, I'll live here."

David breathed a little sigh of relief. He was excited at the prospect of having Tess available for his sexual release on a 24/7 basis, but was now wondering what the limit to it was, and how would their new dynamic work. He even thought of the fact he had yet to even have her pussy yet. He had yet to put himself inside of her, and they were already setting up a cohabitation.

He was a little lost in his thoughts but came to to see Tess undressing. Before David knew it, his teenage sister was completely naked with her ands pressed against his new windows, bending over for him.

With some quick rustling sounds and the thud of his belt buckle hitting the hardwood floor, David was naked. He slowly sauntered over to Tess and licked his palm and slapped her hard across the ass. The smack echoed throughout the cavernous loft.

He positioned his cock at her entrance, and slowly pushed the tip in.

"I'm still amazed at how tight you are," David said confidently as he continued to push his rock hard dick into his sister's cunt, "your pussy must be magic."

His cock went deeper and deeper, but slowly. Then David started to pick up the pace going in and out a bit faster, he was still holding back a little bit, but planned to be balls deep in his sister within a short amount of time.

As he fucked faster, David moved one hand from Tess's hips to one of her huge tits jiggling in front of the window. He grabbed it as his huge cocked assaulted her pussy. He rolled her erect nipple between his thumb and forefinger as he moved in and out, going just a little bit deeper each time.

He looked down at his nubile sister's perfectly tight ass and became mesmerized by a distinct feature. David couldn't take his eyes off of Tess's asshole. It was like it was beckoning him. Her silken cunt was pulling at his cock like some sort of flesh magnet and knew he couldn't hold out for much longer, because of the way Tess denied him over the last week, but wanted to make the most out of their first fuck.

David took his hand away from her tit and licked his thumb. Her body smelled like vanilla and he picked up the scent on his thumb. He put his hand on her ass, and rubbed her hole with his thumb. Then, as he finally put his full length deep inside Tess, he buried the tip of his thumb into her incredibly tight pucker.

Tess smiled when David commented on her 'magic pussy', but the smile quickly disappeared as she felt him slowly begin to penetrate her, his thick, hard cock pushing into her, opening her up. Her entire body was alive in those moments as her brother took her for the first time, as if the excitement of the moment had left her with a heightened awareness of her body; her palms, pressed firmly against the window were cold; her hair hung down across her shoulders, tickling her bare skin; her toes curled against the soft, thick rug that she stood on; her small, rough nipples, swollen and hard, ached wickedly at every touch of David's hands; her thighs quivered slightly beneath her; and her pussy seemed to hum and pulse around the head and shaft of his manhood.

Oh Fuck! Tess thought as she felt David begin to rub her asshole. Her head dropped low between her shoulders as she surrendered to the sheer pleasure of the moment. His cock was so big and so deep inside her it was hard not to think of anything else and yet, the gentle rubbing of his finger between her cheeks was so soothing and so maddening...then without warning he pushed his thumb into her forbidden hole.

"Oh fuck, David!" the teen cried out as her head jerked up and she moaned unabashedly. The thought of having anything inserted into her ass had always secretly intrigued Tess, and at the same time, frightened her and the thought of being filled in both her holes at the same time had never even occurred to her. It was utterly amazing, so much so, that the blonde found herself pushing back against her brother's cock and thumb wanting him to fuck her faster.

"Fuck me, David, fuck me, please..." it was a stupid thing to say to someone who was already buried deep inside of you and doing exactly what she was suggesting and yet, it was what she wanted. More, harder, deeper, faster.

After David stuck his thumb inside of his teenaged sister's asshole, she perked her head up and let out a more animalistic moan. He wished he could have captured it on video and replayed it. He only wish he could have saw her face. Not only was she the most beautiful girl he had ever seen, but he guessed when he buried his thumb in her forbidden hole that her eyes probably widened with absolute shock.

"Oh fuck, David!"

He loved the fact he could elicit such a response from the glamorous sister who up until a week ago never would have imagined he could do such a thing. He continued to probe her tight little hole with his thumb as he drove himself into her more welcoming opening. He wanted to be in control of her, make her come under his terms, but make her come harder than she ever had before.

"Fuck me, David, fuck me, please..."

At that, David took his free hand and wrapped some of Tess's lustrous blonde locks around his hand and started to pull her hair a bit. His thumb still in her ass and his cock pounding her tight little pussy, David felt like a god as he looked out the windows over the city.

"I'm fucking you, sis. I'm fucking this fucking amazing pussy," he said honestly as he gave her hair a bit of a tug. "You like fucking your brother, Tess? You like that your brother has his thumb in your tight puckered butthole?"

As Tess stared out at the cityscape in front of her, she felt something she'd never felt before, a sense of surrender, to David, to the moment, to the pleasure that was coursing through her body. Until that moment, sex and sexuality had always been about one thing for Tess, getting what she wanted, whether that was a modeling job, or a new gucci handbag or an orgasm. The blonde had always prided herself on being in control, not only of her own desires, but of the men she was with. She could get whatever she wanted and always without going a step further than she was willing to go.

Until now.

This time she wasn't in control, she wasn't trying to get anything from her brother. That may have been how their sexual relationship had begun, true, but this was so far beyond that now. This was surrender, this was freedom and liberation and disregard for the consequences. This was lust and desire and just flat out getting fucked.

This was amazing.

The blonde teen was brought back to reality by a hard tug on her hair as David began to thrust into her even harder.

"You like fucking your brother, Tess?" she heard him ask.

"I love it, David...I love being your whore..." she answered as she continued to thrust her hips back, meeting the forward thrusts of his hips, forcing his engorged manhood deep into her, pounding into her, his balls slapping against her loudly as her moans grew more intense.

David could sense himself reaching the edge. He wanted their first time together to do enough to get Tess on his side, to make sure that she didn't look at him and think about him like an odd job for a little extra cash, but to actually want to be with him. He knew he would at least have to make his sister come if he wanted her to want something beyond a mere sugar daddy/sugar baby type of arrangement. He wanted a situation no different than an executive and a trophy wife...except for the fact David and Tess just happened to be brother and sister.

The older brother could tell he was getting cooperation out of his teenage sister, because her hips were responding. Not only did David pick up the subtle cues that she was into their fuck session by the way she responded to the thumb. The moans could have been faked, but at least it would be a sign of trying. However, when David started driving into her faster, with more intensity, she started bucking her hips back towards him. Hungrily she tried to get more of his cock into her. Her pussy was responding to, and David was finding it more onerous to move out of Tess's tropical vacuum of a vagina.

"I love it, David...I love being your whore..."

David had to refocus himself, to keep himself from exploding at that very moment inside of his sister's pussy which had been pummeled thoroughly by his dick by that moment. He wasn't certain if she had given herself over to the moment, to him, or was just teasing, but it gave him the confidence he needed.

He knew he was about to come, and didn't care that it would be inside of her. She knew what she was doing when she stripped naked in front of that window and pressed her hands against it. She invited him to do whatever he wanted.

David let go of her hair and reached for her chin. He grabbed her face and twisted it back so she could see him as he craned his neck. He moved his to her ear. His breath hot on her ear while he fucked her furiously. His balls smacking against her ass echoed off the window, hardwood floors, and high ceilings. His hand moved from her chin to under her arm and mauled one of her tits, rubbing her nipple.

"Come with me," he said. "Come with me."

He moved his lips from her ear to her mouth and did what she didn't let him do at his old place the weekend before. He kissed her hard as he rubbed her tit. His cock reached its bursting point and buried his thumb past the knuckle in her ass as he freed his mind and unloaded his balls inside of her teenage pink.

Tess couldn't have said what it was that finally sent her over the edge into a blissful, mind numbing orgasm but when it hit her it hit her hard. Maybe it was the way her brother urged her to come with him, or maybe it was those last couple of hard thrusts from his cock, or the way he pushed his thumb just a bit deeper into her ass, or maybe it was simply the feel of him erupting inside of her, filling her with cum. Whatever it was, the orgasm was more intense than any she could remember, so intense that her knees actually buckled at one point.

She managed to catch herself, her hands pressing tighter against the window, giving her just enough time to recover her legs. The blonde stayed there bent over for an eternity, just enjoying the afterglow of her climax, enjoying the feel of David's partially spent cock inside of her, the feel of his cum inside of her, his naked body against hers, their breathing in unison.

David's cock gave its last gasp inside his sister's clenching sex. She had milked it for every drop of cum that his balls had in reserve. It really was no surprise that he expended a huge load of it inside of her. She had drained him pretty good the previous weekend, but during the week, David couldn't bring himself to masturbate, his hand just didn't do justice to his teen sister's mouth, and he discovered moments earlier, her pussy.

He pulled his softening member from her tight pink and swore he heard something close to a popping sound while he did it. It increased the size of the grin on his face. He was thinking about all of the ways he'd get familiar with her body over the coming days and weeks, sharing that loft. He looked down at her vagina and saw his white man batter drip from it and created a sticky white trail on her thigh, physical evidence of the size of his load he dropped inside of his own sister.

Once his cock subsided, David pulled his slacks back up and like that was fully clothed again.

"So, Tess, why don't you go take a shower, get cleaned up," he said as more of must-do than less of a suggestion. "Then I'm going to take the hottest woman in the city out for an expensive dinner at the best restaurant in town. How does that sound?"

Even after David pulled out, Tess remained in position for a long moment, bent over, her hands pressed against the floor length window, her brother's cum running down her inner thighs, her head hung down between her shoulders as she breathed deep, her breasts jiggling. She felt David back away and heard him pulling his pants back up.

"So, Tess, why don't you go take a shower, get cleaned up," the teen heard her brother say. "Then I'm going to take the hottest woman in the city out for an expensive dinner at the best restaurant in town. How does that sound?"

The blonde finally straightened up and turned around, pressing her back against the window as she smiled at David, and smiled at the thought of dozens, maybe hundreds of strangers watching her at that moment. Strangers who just watched her get fucked hard by her own brother.

"That sounds amazing," she responded, pushing herself off the window, leaving a smear of David's cum behind as she stepped past him and toward the bathroom, pausing just long enough to kiss him lightly on the cheek, her breasts pressing firmly against his body.

Tess could barely stop from grinning the whole time she was in the bathroom and the shower. Her pussy still ached from the fucking that David had just given her, and she couldn't remember ever being so happy.

David watched the busty nubile blonde sway her naked ass as she walked to the bathroom to shower. The animal in him, his id, wanted to follow his aspiring model of a sister and fuck her silly in the shower, but the cold, calculating young executive wanted to take her out and flaunt the fact he was with a beautiful woman... who just happened to be his teen sister.

He looked at the little white smear she left on the window. David searched the cabinets and cupboards for cleaning supplies. As with a new place, most everything was bare. However, he did come across a cupboard with some cleaning supplies most likely employed by the realtor. He grabbed the Windex and walked to the stain caused by brother and sister fluids mixed together and stopped. He put the bottle down and thought how fun it would be to have the maid clean fuck stains a couple of days a week.

David then remembered that he told the movers to move a gift box he had left on his old dining room table. He walked over to the living room closet and opened the door. Sure enough, a white department store box was there. Inside was a slinky red designer dress that David bought during the week. It was in Tess's size, or at least the size she claimed to be on her promo shots. He placed the box on the bed outside of the bathroom and expected her to see it when she came out.

While she showered, David walked down to the garage and pulled suitcases full of clothes out of his trunk and brought them back up to the new loft. He sat on the couch waiting for his sister/fuck buddy to come out.

When Tess emerged from the bedroom several minutes later she was wearing the slinky little dress that her brother had left next to the bathroom door, and a smile from ear to ear. "I love it," she said, running her hands down over her hips to smooth the dress.

The teenager had arranged her long, blonde hair in a thick, loose braid that hung down in front of her right shoulder, the soft hair tickling her breast which was partially exposed by the strapless dress. Luckily the three inch heels she'd been wearing complimented the dress well.

"I think it fits perfect, don't you?" Tess asked David as she walked around to stand in front of him and give him a look at her dress as she slowly spun in place.

When Tess walked into the luxurious living room wearing the dress David had bought for her, the older brother could do nothing but drink in the sight. She was the epitome of glamour and sex appeal. The braid hanging over her shoulder complemented the attire perfectly, and finally David could picture the teenager on the cover of high fashion magazines, to become the envy and object of desire for women and men across the globe, and she was his...at least for the time being.

"I think it fits perfect, don't you?" Tess asked David as she walked around to stand in front of him and give him a look at her dress as she slowly spun in place.

David put his thumb and forefinger underneath his chin and squinted his eyes. He was looking critically at the girl as she spun in front of him. He moved around a bit and made some quizzical noises. He finally walked over to his sister and put his arm around her waist and pulled her tight to him.

"It fits like a glove," he said as he pushed her braid aside to smell her neck and kiss it softly. "Now, let's go turn some heads."

With that the two walked down to the front door and jumped into a black towncar that brought them to the restaurant.