W is for Whore

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Debra works hard trying to save for a vacation.
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Many Feathers
Many Feathers
10,458 Followers

Debra stood in the darkened hallway surveying the smoke-filled bar. She'd just returned from the restroom checking her hair, makeup as well as ensuring that plenty of cleavage was showing. Not too much, but enough that she was sure her large breasts would receive more than ample attention, and hopefully appreciation. She never failed to draw attention to herself using her breasts as a lead-in. After all, she was a whore.

She smiled inwardly. Just a few more Johns and she would have managed to save up just enough to take that vacation she'd been so looking forward to. A chance to get away from her arduous and hectic life, a chance to relax, enjoy the sun and simply be herself.

She continued to survey the room. "There!" she said to herself now smiling. She spotted him at the far end of the bar. She had always had a thing for men in uniform, especially sailors. And this particular sailor was attractive even if he hadn't been wearing that uniform.

Debra wore her reddish-brown hair short, feathered, giving her a "just got out of bed," mussed up look that appeared sexy as hell and she knew it. She didn't dress slutty-looking either. Sensually yes. More like a high-priced two thousand a night 'call-girl' as opposed to an 'a-typical' streetwalker. And though her breasts were large, she considered her long legs as her best feature really, though everyone noticed her breasts first of course. But at nearly six feet, she wore her skirts short without being too short, showing off her legs to their best advantage.

Debra began walking towards the bar. Her timing couldn't have been any more perfect as someone had taken the bar-stool, leaving the only one open next to the sailor as she walked towards him. Taking it, she sat down ordering.

"Gin and tonic," she stated to the bartender not even bothering to look at the sailor, ignoring him for a moment as though he wasn't even there. She was smiling inwardly however, she knew without turning that his eyes were already glued to the deep 'V' of her black blouse, the lacy bra she was wearing barely supporting her breasts, hinting more than anything of what lay beneath.

She pulled a twenty from her purse placing it on the bar.

"Allow me."

"Thanks," Debra said, still not fully acknowledging his presence. She produced a cigarette and once again the sailor was Johnny on the spot, a tiny flame suddenly coming to life.

"Thanks again," she stated, this time turning slightly towards him though she cocked her head upwards allowing the smoke to blow away from his face. He was smiling, his eyes still very much focused on her tits.

Now came the hard part. It was time to let the guy know she wasn't just some gal that had stopped by from the office on her way home for a quick drink or two. She'd either be taking this sailor to bed shortly, or going for a walk. She allowed herself to glance over towards him more directly, now meeting his gaze as his eyes traveled upwards away from her tits back to her face. She smiled watching as he did.

"Don't get your hopes up," she told him without sounding haughty about it. But she noticed a slight frown come into his face. It was time to show her hand. "You couldn't afford me I'm sure," she added taking another drag on her cigarette turning away from him now so she couldn't see his added expression. "Would it be one of surprise? Shock? Or interest?" She waited, wondering.

"Oh?" Was all he said. At least he wasn't ready to throw in the towel quite yet. That was a good sign, so she turned back towards him, now crossing one of her long slender legs drawing his attention towards that as she shifted on her seat. She knew in doing so that she'd allowed him a very brief tantalizing peek at a good bit of her upper thighs while doing so. "You telling me you're a..."

"Whore," she finished for him. "Yeah, but not a cheap one either," she added now challenging him directly as she locked her eyes with his.

"I can see that," he said appreciatively, then lowering his voice as he spoke. "So...how much?"

"How much for what?" she responded. She had to be careful, even a guy in a Naval uniform could be undercover.

"For sex!" he said almost a little too loudly now. She laughed crushing her cigarette having also just polished off the rest of her drink.

"Depends on what you're looking for," she told him swinging herself around so that she appeared ready to leave.

"For a fuck!" he finally stated, no longer being the gentleman, which was always the way it was once they found out who they were dealing with. At least he'd whispered it this time.

"Two hundred for the hour, sixty for the room and yes, I already have one. After that we're on the clock and anything else we re-negotiate!"

He looked at her incredulously.

"Like I said, you can't afford me, thanks for the drink." Debra stood preparing to walk out the door.

"Wait!" he said swinging around joining her. Now it was her turn to be surprised. "Didn't say I can't afford it," he leered. "Just got in tonight, I have tons of money on me baby. Where too?"

She was relieved. "There's a motel just around the corner, room 147. Give me ten minutes, then meet me there," she told him and moved off before he could say or do anything else.

She noticed the thrown look from the bartender as she began to turn and walk away. Obviously he wasn't too happy at losing what had appeared to be a long-term drinking customer. She smiled, blowing him a kiss anyway.

#

The room was nice, certainly clean though small. She'd slept and fucked in nicer ones, but it was adequate for her purposes. And close to where she worked. So it saved time.

Debra hung her blouse as well as her skirt inside the small closet. She kept her brassier on, the "John" always got a charge out of removing it anyway, sort of like unwrapping a Christmas present. She always got a kick out of the smile's she got as the trick removed it. She wore no panties however, just matching black lace stockings and garters. It might have been 'old-fashioned' perhaps, but she never failed to get an additional look of appreciation and excitement whenever she wore them. Especially as she'd be lying on the bed, legs spread, already touching herself when he entered the room. That never failed to get things going quickly either.

She heard the knock, it was almost too soft. "Doors open," she spoke. Listening as the doorknob turned.

"Damn!" he said entering the room.

"You mind closing the door? Unless you want to pay extra for an audience," she advised him.

Sheepishly, he did so, stepping further on into the room, closing, and then locking it behind him. He reached in to the upper pocket of his Navy jumper producing a fairly large sized wad of bills.

"Lets get the preliminary's out of the way first shall we?" she began. "Show me your cock first, and it had better be hard, or we're not saying or doing anything more until it is."

Once again, he certainly 'looked' Navy, but she had to make sure that he still wasn't a cop. He walked over placing the cash on the top of the dresser, and then began undoing the front flap on his Navy bell-bottoms. Debra laughed.

"What's so funny?" he asked.

"Not laughing at you," she told him. "Was just wondering what the hell you do if you're really in a hurry," she asked. "With thirteen buttons to undo, I bet you really have to plan ahead whenever you've gotta take a piss right?"

"Actually...no," he said simply grinning at her. And then to her surprise, he pulled on the upper corner of the flap yanking it. It opened far quicker and far more easily than she could have ever possibly imagined.

"That's a neat trick," she admitted appreciatively.

"Yeah, works most of the time, though occasionally you can pop a button here or there. So don't usually do that every time," he informed her. More importantly however, Debra noticed his cock was nice and hard.

"So. What is it you want again?" she asked all business like, though she continued to lie there playing with herself as he watched, continuing to undress. In doing this, she knew she was raising his level of excitement, and more importantly about to make a bit more than was originally discussed, hopefully anyway.

"For the moment, I'm enjoying watching you," he told her.

"That one's on the house," she said grinning back at him. "For a few minutes anyway," she winked, but adding, "two hundred for the fuck."

She watched as he first counted out the money for the room, then for the fuck leaving the total in a separate pile on the dresser. He was naked now too, approaching the bed. She spun meeting him, presenting her back towards him. "You want to undo it? Or shall I?" she asked. His hands were already upon her undoing the clasp.

As expected, the moment her bra fell away from her breasts, his hands had replaced it. This was considered a 'free-bee', though she admitted she very much enjoyed having her tits fondled and caressed. Her nipples always had been super-sensitive anyway, and played with long enough, she had even climaxed by having them touched alone without doing anything else.

"How do you want me?" she asked after a time. She was aroused now herself, which always helped.

"How do you prefer it?" he asked ever the gentleman.

"Not about what I like," she countered. "You're the one paying for it, so you get to fuck me however you like it best."

He thought about it for only a moment or two. "How about, you straddling me?"

Debra smiled knowingly, already reaching over towards the nightstand tearing off one of the condoms from its package. Funny, but most of the time that was the request, her on top and in control, not that she minded, she didn't, it was far easier for her to have an orgasm that way too, and on top, she usually always did.

She popped the condom into her mouth, watching his delighted expression as she leaned over him. "Another free-bee as it were," she thought. But this was always a strange kind of treat too for one reason or another. She placed her mouth over the head of his prick, rolling the condom over his cock as she engulfed him. Once she'd done so, only then did she give him a quick, brief little suck or two, just one more additional special service, especially for someone in uniform.

"Damn, that felt good!" he acknowledged.

"You want more if it, that'll be extra," she advised. She saw his frown and felt bad for a moment. But she wasn't about to toss in any more free-bees for the time being anyway.

He said nothing more, so she straddled him, easing herself down. Having played with herself sufficiently before his arrival, she was wet, so she took him easily, her pussy slick with her juices. Even then, once she'd fully cunted him, she refrained from moving. They had plenty of time, the better part of an hour in fact. And whether or not he could come more than once in that time was up to him. If he was in a hurry and wanted to begin thrusting his cock inside her, well then it was after all his decision, and not hers to make. He seemed content to just lie there however, his prick embedded deeply within the confines of her pussy.

"Feels good!" he moaned pleasurably, taking her breasts within his hands as he began caressing them, touching, now teasing her nipples. Admittedly, she liked that, so she found herself in no real hurry, though she did flex her pussy muscles around him, teasing him that way, causing him to groan pleasurably. "Fuck! That's nice," he sighed.

Her nipples felt nice too. She liked the way he was rolling them between his fingers, slightly pinching each without causing pain, just on the edge of that, just how she liked it. Firm, but not too hard, little electrical like impulses running down from her breasts towards her clit, signaling it, causing it to spark with a sweet-feeling pleasure of its own.

At last he began moving in and out of her, slowly at first, then more firmly, urgently as the slickness of her pussy caressed him, exciting him further. "Oh baby!" he gasped as she began to stroke him harder now, impaling herself with nice full upward motions before crashing down upon his hard thick shaft.

"You like it huh?" she purred sensually, cunting him fully, now grinding against him in a circular motion with his prick embedded as deeply inside her as it was possible for it to be. "Like the way my pussy feels fucking your prick?" she asked once again, knowing full well that her dirty 'fuck-words' were having their desired affect on him.

"Oh fuck yes!" he hissed thrusting upwards even more deeply than he had been, causing Debra to catch her breath in turn as she felt the delicious sensation of his penis knocking at the door of her womb.

"Fuck me baby! Fuck me! Harder! Harder!" she cried out now in abandon, the pleasure her pussy now feeling edging her closer and closer towards her own real orgasm.

"Shit! Fuck! Suck! Cunt!" he cried out in single one-word sentences.

"Oh yeah baby, pinch my nipples, pull on them you bastard, come on, twist them you fuck!" she cried out as she felt the wetness beginning to form, pool, already threatening to explode even before he did. "You want to feel me squirt baby? Ever felt a woman squirting before? Want to feel my pussy bathing your big fat cock with lots and lots of pussy fucking juice?"

That did it for him. Debra heard his deep-throated groan of release, followed by the sudden lurch deep inside her as his prick exploded, showering the cavity of her now spasiming quim with his jisim.

Feeling his climax erupt, triggering her own, she relaxed allowing the liquid pleasures of her own sweet ecstasy to begin soaking his still thrusting prick, bathing his balls and ass with a mixture of her cream as well as his own as she sprayed him liberally with her essence.

# It had been a long hard week for her. Debra was looking forward to the evening. It was Friday and she was one step closer towards her goal. She stood on the corner briefly watching the traffic. Surprisingly it was light, both a good and a bad thing. Good that she'd be spotted easily, bad that it might be a while before someone actually stopped showing interest in her. And still she hadn't dressed like a real hard-core prostitute either. Though her skirt was certainly short, and the fact she wasn't wearing any panties, it wasn't that disconcernable that she wasn't unless she bent over slightly, which she would only do if asked to do so as a bit of a bargaining chip should it come down to that. She wasn't wearing as low-cut a blouse either, though wearing certainly a tight-fitting one around her full braless breasts. Her nipples stood hard, poking invitingly against the material of her knit blouse, invitation enough to anyone who might be interested. Looking up, she spotted a pair of headlights approach, the sudden veer over towards her as the car slowed. Debra smiled stepping away from the sidewalk into the street.

It was a sporty looking bright red Mustang convertible. Not too expensive, but expensive enough to tell her the guy had money. He pulled up next to her, almost pretending as though he had reason for doing so other than in speaking with her. Debra approached the car brazenly leaning against the passenger door looking in.

"Looking for some fun?" she questioned. He appeared nervous, glancing in his rearview mirror more than once as well as from side to side.

"Depends," he said simply looking all around him once again.

She figured this guy for a blowjob, so she started out with that. "How's a little head sound?" she asked, telling him what she was offering without being too obviously explicit. He knew what she was telling him of course.

"How much?"

"How about you showing me a nice hard cock before I say anything else," she told him.

"What if it isn't hard yet?" he tossed back.

"No problem, I'll wait," she said reaching up to thumb each of her still hard nipples, teasing them for him as she stood there. "Whenever..." she added smiling.

He looked about once again, a few cars passing them by, but none slowing or doing anything to cause him to be any more nervous than he already was. Finally he unzipped his pants producing a very nice hard erect cock. "How's this?" he asked.

"Nice," she replied. "What would you like me to do to it?"

"Suck it," he responded simply, adding, "How much?"

"One hundred if we stay in the car, that plus the cost of the room if you'd prefer to do that."

"Stay in the car," he told her. Debra opened the door slipping in to the passenger seat.

"There's a nice open parking lot at the grocery store around the corner from here," she explained. "A lot safer if we go there where you can keep an eye out for anyone," she instructed.

"Sounds good."

Debra had him pull into the place where most of the employees parked their cars. With two hours still to go before the store closed, the likelihood of any of the employee's coming out to go home now was remote. And most of the customers were too busy driving around trying to find closer parking places than this. It was reasonably safe, and backing in instead of pulling in forward, the 'John' would have an easier time being alert and aware of their surroundings.

She opened her purse producing a condom. "You have to use that? I'll pay extra to cum in your mouth," he told her.

Debra eyed him carefully, not that that was a for sure safe way to ascertain anything, truth was...it simply wasn't. But he did look professional, probably had a sweet sexy little wife waiting for him at home, though she probably didn't enjoy giving head, or as he'd asked...wouldn't allow the guy to come in her mouth either.

"That'll be another hundred," she told him. "And I won't swallow either," she informed him. He agreed.

She did like the way his cock looked. All nice and hard, the head of his prick purple and swollen just waiting to be sucked. So she did. Drawing him in-between her lips, just until she felt the ridge of his velvety little helmet, sucking just the tip as though it were an enormous nipple. His deep long moans assuring her that he was enjoying it.

"Keep your eyes opened," she warned him however. "Or you can suck yourself off," she added seriously.

Periodically looking up towards him to ensure that he did, Debra sucked, and then licked his prick like it was an ice-cream cone that was seriously melting. Though that was of course the farthest thing from actually happening. To her delight, he had also lifted the front of her knit top up and over her breasts, exposing them to his touch as his fingers toyed with her hard fat nipples as she continued sucking him, now moaning herself occasionally as her titty-pleasure continued to increase. Curiously she found as she leaned across him the way that she was, the corner edge of the seat was pressed against her pussy in a uniquely interesting way. With the additional stimulation of her breasts, slightly grinding herself as she sat sucking him, Debra realized with a little creative effort, she could actually climax this way.

"Hmm, tasty fucking prick!" she mouthed around his penis, tongue lapping at the head, tongue-fucking the tiny little eye-slit, slurping up the fat droplet of lubrication that her hand had managed to squeeze out. "You gonna cum hard for me baby?" She now asked. "You gonna squirt lots and lots of that creamy cock juice into my mouth for me? You wanna watch it dribble out of the corners of my mouth so you can see it do you?" she asked still sucking him.

"Oh fuck yes," he barely managed. "Oh fuck that feels good!" he added in a long drawn out moan of pure pleasure. Moments later he was filling her mouth with his cream, feeling her as she sucked it, draining him until there was simply too much for her to contain. Only then did she wickedly allow it to seep from her mouth, taking decadent pleasure as she soiled his pants as well as the nice leather seat he was sitting on.

Many Feathers
Many Feathers
10,458 Followers
12