The Homeless Obsession Pt. 01

A trophy plaything for a wealthy Manhattan businessman takes an unexpected slip from life's pedestal when she finds herself underneath a homeless man -- but discovers it is just where she needs to be!

Racquel Darrian had grown tired of being an objectified fashion model -- it was such an empty existence. Something had to change, but what? Her uber-rich boyfriend, Craig, had put her up to the whole modeling thing and she had definitely excelled beyond even his lofty expectations. Her fit, tiny body, pretty face and her obedience in front of the camera made her an instant success, but there was a desire deep within her that she could not yet define, but she knew it would one day take over and she might finally feel complete.

Craig was a tall, handsome blonde Yale graduate with chiseled features and parents who lived in the Hamptons. He worked for a famous bank and intended to marry Racquel one day, once his dad had retired for good.

One morning, Racquel was alone up in Craig's penthouse suite 30 stories over Manhattan, peering through a high definition telescope at people down below all heading off to work. Racquel was dressed in a one-piece black and white striped dress with a skirt section that barely covered her ass. As per Craig's insistence, she was also wearing high-heels to show off her tanned, long legs. Although Racquel had a modeling job later in the afternoon, she could not but help spy on people on her free time - it had become her secret obsession that had made her late for modeling sessions several times already.

In a few situations, Racquel had caught girls getting dressed across the way in the facing condo and she had found it difficult to pull herself away from the free show. The previous Tuesday was pay dirt as she had the pleasure of spying on a fat, balding handyman screw a beautiful blonde dressed in lingerie and heels. Watching the man grimacing with pleasure amused Racquel at first, but she had ended up finger banging herself as she gripped the shaking telescope for balance -- it was one of her finest orgasms ever

For some twisted reason she had wished it was her underneath the old fella; whom she viewed as kinda gross and definitely not her type at all, but who had clearly given the pretty blonde a fuck to remember. Was she a hooker, or just girl dying for a random fuck? Racquel doubted she'd ever figure it out for sure, but had day dreamed about trading places with her every day since.

Tilting the telescope tube to street level, Racquel spotted some movement down one of the alleys. As she scanned around, she saw it was a typical New York setup with dumpsters, puddles, trash everywhere and a dirty mattress. As she zoomed in, she saw a filthy homeless man sitting on the edge of the mattress beating off to a dirty magazine.

She reckoned he was mid-fifties. He had messy hair, a grey beard and a beet gut. To her amusement she noticed he had a very thick, long penis. She then turned on the telescope recorder and began capturing video. Her breathing soon became shallow as she continued to check the action below. The noises around her then vanished and she found herself transfixed.

Racquel then flashed back to New Years at the Hampton's. Something had happened that night and she had never told a single person about it, but she knew then it was her desire for something so dirty and forbidden that she could not speak of it. And this man, 30 stories below, was somehow connected to such forbidden desires.

Thinking back to how that New Year's night had unfolded, she remembered the Lear Jet flight over with Craig followed by dinner at some restaurant that Craig had boasted had a six-month waiting list. They had eaten caviar in the limo and drank Champagne, but somehow the snootiness of how Craig had treated the staff on hand and the driver had both bored her and embarrassed her beyond words.

Like a mannequin, Craig had approval over what she wore in public and tonight he insisted she wear a white latex mini-skirt, white boots above the knee and a sexy white jacket with shoulder pads. He liked dressing her like the ultimate slut only he was allowed to touch.

Craig was already drunk as they arrived at their destination: a beachside mansion filled with the richest of rich, all seemingly donned in white casual wear. As the evening progressed, Craig continued to get more and more loaded with his old fraternity guys, all of whom thought she was a 'smoking hot babe' according to Craig. It felt like a victory for him that all his old chums wanted to screw his girl. Some men could get jealous over these kinds of head-games, but he lived for winding up his colleagues. For Racquel though, the evening was quickly becoming a dull and tiresome charade. She ended up sitting at the bar alone chatting with the very polite bartenders.

By 11PM Craig was nowhere to be seen. The event photographer then whispered to her that Craig had passed out on one of the deck chairs and pointed in the direction of the beach, assuming she'd just head right out there to be with her man. The assumption annoyed her. It was then that Racquel's life changed - forever. One of the bartender's, Henry, a middle-aged black man with grey flecks on his Afro and beard let down his polished act and started in with the smooth talk and long gazes. He had apparently sensed an opportunity and was not going to allow it to slip away.

Racquel knew what was happening between them and just let it escalate. He was being quite funny and they shared a few genuine laughs. Although she didn't consider him very attractive, his overconfidence intrigued her. Teasing him was fun and she hadn't had to do that for ages. It was obvious he fancied himself a cocksman of sorts, but she had certainly rebuffed a great many of those in her time so felt she could keep him in check if need be.

As the hour drew near, he looked at her as if he had a little plan he wanted to hatch. Checking both ways to see no one was spying on them, he waved her close and asked if she wouldn't like to take a tour out back to the kitchen.

She giggled and found herself nodding yes. He then pointed to a set of metal swinging doors leading to the kitchen and instructed her to meet him on the other side. She saw Henry wink at his other bartender, who knew what was up. Henry appeared through an archway and removed his apron, tossing it on a dish rack as he eyed Racquel, taking note for the first time that she was wearing a tiny mini-skirt and had incredible legs. In the huge, empty kitchen, her arms folded, Racquel appeared unsure of what was to happen next.

Henry approached her, and as she was about start in with small talk he placed his hands firmly on her waist pulling her to him. They kissed. It was all very sudden, but Racquel felt she was in the hands of a very confident, self-assured man and it excited her -- like he hadn't seen the trophy at all, but just some sleazy whore whom he intended to treat as the easiest lay at the party.

Is that what Henry really thought of her, Racquel wondered to herself? Did he have any idea WHO she was? For some reason it didn't bother her -- not like she thought it should anyway. Soon they were passionately French kissing as she stroked his neck and Afro with one hand and placed the other on his chest. She could feel his massive rod pressing up against her and she touched it with her long fingernails. She then found herself kissing him with more enthusiasm than she felt possible. It was the first time a black man had ever touched her and she knew right then it would not be the last.

At five minutes to midnight the noise outside the kitchen began to pick up. Henry then took Racquel's tiny hand and led her to the wine room, which was significantly darker inside. He lifted her up and planted her ass on a bench and hastily unbuckled his pants. Just like that, her panties were pushed to one side and Henry was on top sliding his giant wet cock inside of her. No condom.

She could not believe how fast it had happened. They were fucking. And it was incredible. She kissed him, unbuttoned his shirt and ran her hands all over his black body. She then imagined the shocked look on Craig's face if he found out and it made her even more aroused. Henry then began talking dirty to Racquel, whispering in her ear. She remembered him bragging he was going to shoot his black seed in her pussy.

And as anticipated, the clock struck midnight and he blasted a huge load inside of her. Wrapping her boots firmly around his waist, she then came as well. And at that moment didn't care if he had knocked her up. She just did not care. Henry had given her the best fuck of her life and as far as she was concerned all the cheering outside was for them

After the raucous celebrations had died down. Henry climbed off, zipped up his pants without eye contact mumbled something about her knowing which way is out and that he now had to close up the bar. She lay there stunned, legs open, watching her pussy hair glistening with the stranger's cum. Fucked and dumped.

She left out the backdoor and never saw Henry again. A few minutes later she was in the deck chair cuddled up in Craig's arms as if nothing had happened. On the flight back, Craig had obviously heard some gossip from the photographer about the smooth talker chatting up his gal and decided to bring it up. Looking her straight in the eyes he raised his finger and told her, "I don't want you talk'n to some nigger, you understand?"

Racquel smiled and nodded obediently, knowing she had a black man's seed inside of her and dried all over her pussy. It was then that she realized two things: her boyfriend was a chump and she had missed out sucking Henry's dick.

But what a fuck.

The fact that he had tossed her to the side as just another conquest did not bother her at all. One thing she knew for sure now was that she craved lowbrow excitement and she would never get that from Craig. She wanted to be a slut. Maybe even become a stripper at biker bar -- something. She had much to think about. No more fancy martinis, for this girl!

It was now a month later and she was certain Henry hadn't knocked her up. She was on the pill, but considering it was a stranger snaking her it had been a risk. Racquel decided she liked risks.

Like with the Henry thing, Racquel began to feel led by something dirty and impulsive that she just could not put her finger on. She desired another situation to arise, but something different. Later, at her modeling job, she sat off to the side checking out the video on her phone she had uploaded from the telescope.

During the afternoon she shared with her hair stylists and crew how she'd watched a hobo beating off from her balcony, but kept the video to herself. They all had a laugh and one of the gay boys wondered if she couldn't have ran down the 30 flights fast enough to help him out.

And although Racquel flashed them with her white teeth and winning smile in response, little did they know she was seriously considering paying the man a visit. How she was going to approach all this or what she even wanted from him was still unclear in her mind.

For sure, she wanted to help the man get back on his feet, but she also knew she wanted to ask him about his magazine. For some reason, she thought that might be a good opener. As the modeling shoot wrapped, her pussy that had been aching with memories of Henry banging her. She had never been used like that before, but she felt no animosity, as she knew in her heart a situation like that would happen again. Deep down, she just wanted to be a whore -- plain and simple. And the homeless man she had spied on was driving her like a magnet to that alley. He needed to free her somehow.

Back in her mini-skirt and heels, she put on her mink jacket, stepped out into the chilly evening and flagged down a cab. When she got upstairs to the suite, she grabbed a blanket and few drinks and snacks from the fridge and headed back downstairs. With her tiny clutch purse swung over her shoulder she noticed in the elevator mirrors that she pretty much looked like a call-girl. That was a look Craig preferred for her and she did indeed enjoy showing off her body more than she could ever readily admit. Craig was right about one thing: she looked fantastic dressed to kill.

As she stepped out of the turnstile glass doors, she spotted the alley and made her way across during a break in traffic. Looking around, she began slowly making her way down the concrete corridor past the dumpsters. The stench was terrible and it was now getting pretty dark. She thought about turning back, but noticed a glow from the side of one of the dumpsters and knew she had found her guy. There was a small tent with a light on inside. As she drew closer, she could see the tent was on top of part of the mattress she had seen from upstairs.

As Racquel carefully angled her way around to the front she could see the homeless man sitting at the entrance listening to his radio. She stood there for a second feeling stupid holding a blanket and food package. The old man checked out her legs and face and he immediately began to smile. She crouched down, perching on her heels and handed him the goods, explaining she had seen him from her apartment. She pointed to it way up high. Looking around, she then asked if he was alone. He nodded yes. She then handed him a can of cold beer. He thanked her and asked her name. They chatted for a few minutes and she occasionally caught him trying to peak up her skirt as she remained uncomfortably crouched down, afraid to kneel on the wet pavement.

After a lull in the conversation about his car manufacturing job laying him off the previous year, Racquel nervously asked if she might sit down on his mattress. Frank nodded yes, gesturing with his free hand. Doing so, Frank now had an excellent view of her legs and she didn't mind him one bit getting an eyeful. Using Henry's smooth talk and eye contact method, she began flirting with him and coyly asked if anyone else resided in the alley. Confused, he nodded no, and that is when Racquel took charge and began teasing him about his magazine collection.

Again pointing to her apartment, she told him how she had spied on him that morning beating off using her telescope. As he sheepishly laughed, she asked him to bring her his magazines. Reaching back into the tent, he grabbed a handful and placed them between himself and Racquel. Nudging closer, she raised her eyebrows in mock amusement and grabbed the heavily stained dirty magazines on her knees and began flicking through them. Mostly Hustler and Penthouse.

Having fun now, her eyes became large like saucers as she feigned shock as she flicked through a pictorial.

She asked him for one of the beers and edged in a little closer down the mattress as she pushed the dirty magazines behind her. As he handed it to her, she looked down and noticed the bulge in his filthy tweed pants. Pants that were pathetically tied up using a piece of rope!

She chugged a big sip of beer and blurted out: "You've got a really big penis. I saw it."

Although he was a bit shocked to hear those words, he found himself leaning back to show off what she was speaking of. Racquel stared at the bulge a moment and then found herself clumsily untying Frank's rope belt using her long red nails. He leaned back on his elbows realizing what was coming. She pulled down his pants and underwear past his thighs and shoved up his dirty, t-shirt, exposing both his huge dong and round, hairy belly.

Frank hastily switched off the radio.

Although she was aware of how badly he smelled, she was overcome with desire and just did not care. Staring at it in silence she knew she must have it in her mouth. Using one hand, she pushed him on his belly to lie flat on his back as the other hand grabbed his massive cock. She then closed her eyes and did the unthinkable. She sucked, licked and tongued a homeless man's penis.

The hair, grime and sweat she dutifully licked up off his head and swallowed it. Frank could not believe his luck! He looked down and watched Racquel kiss his head and run her tongue up and down his shaft as she tickled his balls with her glossy fingernails. She was wearing a gold necklace that was spooled in his pubic hair, but she was so consumed with licking him she didn't seem to notice. He then announced he wouldn't be able to hold out much longer. Breathlessly, she told him to come in her mouth. A few seconds later, he clutched the mattress with both his fists and let out a huge groan as he blasted inside of her.

Racquel sucked it all down, even seductively licking cum splatter, which was now soaking his belly and draining off onto the mattress. Racquel continued beating him off and squeezing his nuts till he was completely drained.

She gave him a huge smile as she gathered her things and began making her quick exit. Frank lay there in a heap, exhausted, his dick lying flat and wet on his stomach. In her crouching position again, Racquel opened her purse and pulled out two hundred dollar bills, placing them on the mattress.

She then thanked him. Taken aback, he looked down at the money and then up to her pretty face and stated,

"Anytime."

Racquel smiled, promising to return the next day.

As the elevator soared up to the 30th floor, she was feeling exhilarated by the previous hour. Racquel checked herself out within the mirrored enclosure, noticing the dried cum on her cheek and neck and a clump on her mink jacket. She then noticed her $1500 skirt Craig had purchased for her had dirt smudges on it from the mattress and the gold necklace he had purchased for some anniversary she couldn't recall had two grey pubic hairs hooked inside the loops. For some reason, it made her feel aroused as she flicked them off onto the carpet.

"What a slut," she thought to herself.

Aware it was past 7pm, she knew Craig would now be home. She also knew, albeit subconsciously, he might see another man's cum on her face and perhaps may even smell trash on her.

Craig had an early morning flight out, so she knew she would have more fun with Frank tomorrow although she wasn't quite sure how she was going to play this whole thing.

As she entered the suite, the couple exchanged pleasantries as he poured them both a drink. She gulped it down, smiled politely and headed for the shower. In their room, Racquel tossed the skirt in a dry clean hamper and placed the cum-stained mink on a hanger towards the back of her closet. As she stepped into the shower located in their spacious bathroom, she looked over at their massive circular tub positioned at the center of the bathroom. It looked more like a Jacuzzi, she thought. At that moment Racquel knew what her plans were for the next day: sneak Frank up to the apartment and bathe and spoil him all afternoon with kisses, cleaning and food.

Racquel cleaned herself off in the shower thinking about Frank's big, rough hands passing over her body. She found herself suddenly masturbating, but decided to save herself for the next day. Later in bed, Racquel was getting so turned dreaming about Frank's dirty, stubby fingers slipping inside her pussy that she slid on top of Craig and began kissing him. She then grabbed his small cock from inside his pajamas and slipped it inside her wet pussy.

Craig was pleasantly surprised and they fucked for several minutes before he came inside of her. He had that early morning flight out, so didn't put much into it.

Racquel slid off him and rolled over feeling somewhat disappointed. This was pretty much how sex had been before Henry had banged her, but since then it had just felt depressing and dull. Tomorrow she would get fucked properly.

When Craig left at 6am, Racquel had already been lying awake under the sheets waiting for an hour. When she finally heard him shut the front door, Racquel spent a few minutes cleaning up the apartment for her guest and then applied her best makeup, did her hair and put on some her most expensive, sexy lingerie followed by a black mini-skirt and white jacket. Racquel then put on a pair of above the knee black latex boots. Double and triple checking her face and body in the mirror she then ran a nice bubble bath.