Shemale Street Hooker
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“Thank God they don’t know!” she thought with a blush. What they didn’t know was that they were ogling a pair of crotchless pantyhose, with a tiny little pair of panties over them. And that for a few hundred dollars, any one of them could be fucking her. She leaned over to kiss Robbie and Alicia good-bye, careful to keep the back of her flared skirt in a respectable position.
“Where are you going today, mom?” Alicia asked. “You smell really nice!”
“The agency called last night,” Lori replied truthfully. “They’ve got a job for me downtown today.” The family thought she worked for an office temp agency - not an escort agency that catered to men with expensive, and often unusual, tastes in women.
“Are you going to work in somebody’s office again?” Alicia continued.
“Yes, I am, sweetie!” Lori lied to her little daughter, as a knot formed in her stomach. She had a rendezvous scheduled with a man named George Smithson at a posh downtown hotel at 10:00. She thought that it probably was his real name - it was a very expensive, very discrete agency, and they were meeting at a hotel that would almost certainly demand a credit card.
Back in her car, she discarded the conservative jacket concealing the very sexy white satin blouse that crossed over her beautiful, perfectly shaped breasts. Richard always said that you really couldn’t tell how big her boobs were until you saw them naked. What Richard didn’t know was just how many men knew exactly how big her boobs were. She drove leisurely downtown, knowing that she would be there well ahead of her appointment. There was a food court under an office building that was connected to the hotel, so Lori joined the throngs of office workers getting their morning coffees, and sat down at a table to enjoy hers, before she had to take off her clothes and offer herself to George - whoever he turned out to be.
The agency didn’t have too many women who only worked in the daytime, but they did have a surprising number of clients who wanted to indulge their peccadilloes during business hours. Lori was the agency’s daytime “specialty” girl. She had very few limits. Once she discovered that she could make a lot more money by doing things the other girls wouldn’t, she swallowed whatever pride she had left, and told the agency she’d do just about anything that didn’t leave visible marks on her body. George had made it clear to the agency that he wanted a woman’s ass, so Lori got the call. Lori knew she wasn’t the only girl at the agency who would take it up the ass, but it was something that not all the escorts would do.
The Follis family had debts. Unpleasant debts. Richard, for all his knowledge of finance and money management, had placed a few very large, very stupid bets - using money borrowed from somebody his bookie recommended. They were well behind on their mortgage payments to Richard’s bank, but that was just how it was going to have to be if Richard wanted to keep his legs intact. What an enforcer might do to him would be doubly painful if his own office ever found out what he’d done. Lori was determined not to lose the house. She was already humiliated by the whole situation, so picking up the phone to call the escort agency - the most “exclusive” one she could find in the underground newspapers - to ask for a job turned out not to be completely impossible, as she would have thought. But it was extremely difficult. Richard, the idiot, seemed to want to buy the story that she could make thousands of dollars as a temp. Lately, she had been careful to keep him out of her personal finances, which didn’t surprise him at all based on his recent track record. The sooner she could pay off the debt, the sooner she could stop working as a prostitute. Guys like George just sped things up.
With a final glance at her watch, she picked up her purse and walked, much more sexily this time, into the lobby of the hotel. She picked up the house phone, and asked for Mr. Smithson’s room. The lobby connected her.
“Hello?”
“Hello, George. My name is Lori. The agency sent me over to visit you this morning,” she purred into the phone. A man two phones away glanced up quickly, then turned away. He might have heard what she said, or he might just have heard the sexy murmur. Either way, she blushed.
“Hi! I’m in room 2215. Come on up, Lori.”
After a short elevator trip, Lori found herself knocking on the door of room 2215. She saw the peephole darken for a second, then the door opened. George, as it happened, was a late forties, tall man, quite bald on top, grey on the sides, but not at all bad looking. He wore a hotel bathrobe.
He invited her inside, and kissed her cheek. “You’re very pretty,” he said. “You know I asked for something special, right?”
“I do,” Lori said, putting on a sexy smirk. “Sounds like fun.” She turned around so that her cute ass faced him. “You like?” She asked, looking into his eyes over her shoulder. George took the opportunity to put his hand on her bottom.
He caressed it gently, and murmured, “Oh, yes.” His other hand slid up Lori’s side, and tentatively slid under her arm where the fingertips tickled the outside edge of her tit, through her bra. “The money’s over there,” he continued, nodding at a small pile of hundreds on the desk.
Lori gave George a small peck on the cheek, and walked out of his hands and into the money. Safely stashing the fee in her purse, she removed a couple of condoms from it before returning to George.
Taking her cue from the fact that George hadn’t dressed to meet her, Lori said. “I’ll bet you’d like to get out of that housecoat first, and then we can take our time getting me out of my clothes. Do you like my little ensemble?” She turned slowly, giving George a chance to drink in her beauty. The mid-thigh, flared, pleated skirt was black, which contrasted nicely with the white, sheer, low-cut satin blouse, through which her black push-up bra was clearly visible. The nylons were very sheer, and just dark enough to be obvious. They were calculated to make any man want to slide his hands up under her skirt, whether he knew she was a prostitute or not.
“Oh, yeah, baby. You’re so fucking sexy! So ass-fucking sexy!” he laughed as he took her back into his arms. So he wants to talk dirty, Lori noted. “You like fucking young ladies up the asshole, do you?” She whispered in his ear. She undid the housecoat and slipped it off his shoulders. His erection greeted her immediately. She’d seen bigger cocks in a professional capacity, which was important to consider when she thought about where it was going. At least it wasn’t some monster penis that would make her anus hurt for days. George kissed her on the lips, making it obvious that he wanted to slip her the tongue. Lori obliged, opening her mouth to let it in, even though she thought this part of the job was worse than many of the kinkier acts that she took money to perform. George now had one arm behind her back , pulling her close, while the hand on the end of his other arm fondled her breast firmly. Their tongues mingled, and Lori took his penis into her hand. It was straight and firm. She caressed it gently, slowly, careful not to cause an accident.
George’s hand slid down Lori’s back, across her firm ass, where it lingered for a moment, then down to her pantyhose. On its way back up, his hand slid under her skirt, rising until it found the edge of the cutaway section under her cheek. His cock surged in her hand. “Crotchless pantyhose! Oh, yes! Fuck, they turn me on.” He groped her ass, then her thigh, then her ass again. And his tongue slid back into her mouth.
“Let me take your top off,” George stated. He found the single button on the inside of the top, under her right breast, undid it, and pulled the top out of her skirt. She helped him slide it off her shoulders, and stood before him in her skirt and sexy black bra.
“Pull up the skirt - slowly,” he commanded. Lori did what was asked of her, and when the skirt was just below her crotch - when the cutaway edge was barely visible - she pirouetted slowly, exposing her ass cheeks for a split second. George moved towards her, caressed her shoulders for a moment, then reached down her back to unclasp her bra.
“It opens from the front,” Lori giggled as she reached up to undo it. George slapped her hand away, firmly but gently, and undid it himself. He slid his hands under the open sides, and brushed the cups off her tits as he took each one in his hands. Then he sat on the edge of the bed in front of her.
“Beautiful. Fucking gorgeous tits,” he commented. Her pink nipples stood at attention after his ministrations. Then his attention became riveted onto her left hand. “You’re married?” he asked incredulously. Damn! She’d forgotten to slip her rings into her purse. She nodded uncomfortably. “Does your husband know you do this?”
“Yes,” she lied quickly. Best not to give him any ideas of blackmail.
He searched her eyes. “Kids?”
She started to shake her head, but realized that her face had given her away, and looking at her shoes said quietly, “Yes.”
“So this is what - a hobby? Bored housewife breaks up the day with a little sodomy and fellatio between the laundry and the vacuuming?”
Lori was blushing furiously by now. “Something like that,” she muttered. “Look, I don’t want to talk about my kids, okay?” She had crossed her arms in front of her breasts.
“Sure, sure, I’m sorry,” George said gently. “But you have to know, this is an even bigger turn-on for me!” He pulled her arms away from her luscious boobs.
“Wh-what do you mean?” Lori asked shyly.
“Well, I mean, I’m going to go around the world with some guy’s pretty little wife, while her kids are - at school?” he guessed. Lori nodded, blushing anew, and wondering what this guy’s definition of “around the world” was. “Okay, we won’t talk about it, but you did ask,” he added. And he finished quietly, as a statement of fact, with “Your husband doesn’t know.”
His cock was literally twitching as he contemplated the situation that he had fallen into. Lori decided it was time to get down to work. The sooner she was out of here the better - but she knew she’d better please this guy. She couldn’t afford bad reports back to the agency. Too much depended on her getting a lot of money in a short time.
A condom was mandatory for intercourse, but she didn’t mind a little oral sex without one. Lori knelt in front of George and cupped his balls in one hand. With the other she stroked the shaft. She kissed the tip of his penis, then licked it a few times to lubricate it. She looked up at his face, and purred, “I’m going to suck your beautiful fucking cock. Make it good and hard for my tight little asshole.” Her head bobbed down over the shaft, and she began the work of blowing him. She had become very good at cocksucking in the few months she had been selling herself. She knew how to keep him far enough from the edge that there was no danger of getting a mouthful, but excited enough that he knew he was getting a wonderful blowjob. Her lips, her tongue, her hands, all worked in concert. George moaned, then chuckled, “I’ll bet there’s a condom on it the next time it’s in your mouth.” Without breaking the rhythm, Lori looked up at him and scrunched up her forehead, with a questioning “Hnnh?” from her throat.
“Oh! Hmmm... I guess this would be a good time to tell you exactly what I want. You’ll suck me for a while - this is fucking marvelous - then I’ll strip off your skirt and panties, and fuck your pussy. I want those gorgeous pantyhose on the whole time.” Lori continued to fellate him slowly. “Then you’ll get on your hands and knees on the bed, tits down and ass up, and I’ll stick it back in your pussy for a bit. I’ll be working on your asshole with my fingers, to open it up. When you’re ready, I’ll pull out of your cunt and stick it up your ass. I assume the condom is for the fucking parts, correct?” Lori grunted a “yes” from her pretty, busy mouth.
“Okay, then I’ll fuck your ass until I’m getting close. When I tell you, you’ll whip around and suck me off, with the condom on, until I come in your mouth. Okay?”
Lori stopped sucking very suddenly. She stared up at George, wide-eyed. “You want me to suck your cock after it’s been up my ass? You must be kidding!” .
George took her head in his hands and stared back at her. “I was told that you would go around the world. Mouth, pussy, ass and mouth. When you go around the world, you end up where you started off, okay? Look, they told me you’ll do just about anything. That’s what I’m paying you for.” They held the stare for a long while, in silence. Lori thought about the money in her purse. Finally, she asked, “Can I take the condom off so you can really come in my mouth?”, thinking that would be the lesser of evils.
George shook his head with a tight smile. “No, that would defeat the purpose, wouldn’t it?”
Lori was silent again. George still cupped her face. “All right,” she said. “They just didn’t tell ME I was supposed to do that.”
George spoke to her kindly now. “All right, then. What do you say we get you out of the skirt now?” Lori rose to her feet in front of him, correctly assuming that he would want to continue undressing her himself. He found the clasp on the waistband of her skirt and undid it quickly. Soon it was at her feet, and George drank in the sight of her in nothing but skimpy black panties, crotchless pantyhose and sexy heels.
“Do you always wear your panties over your pantyhose?” George queried.
“When they’re crotchless, and when I’m... working, yes,” she replied. “Men like to see me in these things,” she continued, running her hands lightly across the nylon. “It’s a lot easier to take off your panties if you don’t have to take off and put back on your pantyhose and shoes, too.”
“Right, off with them, then!” George pulled her panties down to her feet, feeling her legs through her nylons all the way down. Her neatly trimmed pussy quickly captured his attention. His hands slid back up her long legs, then darted between the shapely limbs when his fingers left the nylon and found bare flesh at the very top of her milky thighs. He worked his middle finger into her pussy, then a couple more when she parted her legs for him.
“Fuck me,” she invited in her sexiest whisper. “Shove your cock up my pussy... you’re making me so fucking horny!”
George took Lori in his arms, then threw her gently onto the bed. He fell onto her, aiming his mouth for hers, and kissed her deeply once more. Lori worked an arm free, and reached for a condom.
“I know a really fun way to put on a condom,” she said with a sly grin. She took it out of the wrapper and put it in her mouth. George nodded his approval, and rolled onto his back, erection sticking straight up. Lori positioned herself over him, one knee on either side of his head, facing his loins, then leaned over to give her mouth access to his penis. George wasted no time in getting his hands onto her legs, caressing the nylon and the flesh she presented to him. One hand slid up to her breasts, tweaking her nipples firmly. With her tongue and her wet lips, Lori rolled the condom down the length of his shaft. He kneaded her breasts, her thighs and her bottom while she bobbed her pretty head up and down his cock. She focused on his groans, little noises, the rhythm of his gentle thrusting, and the pulsing of the veins in his hard penis, so that she could tell when to ease up on her sucking and prevent him from coming during the preliminary blowjob. George’s mouth had found Lori’s naked pussy - or rather, Lori had lowered her naked pussy onto George’s mouth - where he snaked his tongue up and down the slit, from the tasty little hard clit at its top, to the sloppy, hot, wet hole at the bottom. It was clear to George that Lori’s cunt was ready to be stuffed.
“I want to fuck you now,” George mumbled into Lori’s pussy. “Lie down!”
Lori pulled her mouth off his cock with a loud slurp. She swung her nyloned leg over his face and knelt on the bed while George moved to give her room to lie down. She took her place with her head on the pillow, then drew her knees up to her chest and spread her legs wide open. Her hot pussy glistened, open and available in front of him, framed beautifully by her crotchless pantyhose and sexy black heels. George climbed eagerly on top of her. Reaching around under her right leg, she found his cock and guided it into her waiting quim. George lowered his weight onto her chest, and began to pump into her slowly. He pressed his lips against hers, spearing his tongue into her mouth and thrashing it about wildly. She responded dutifully, but convincingly. George found a rhythm that was not at all unpleasant for Lori. If this sex session had been for her pleasure as well as his, she would have asked him to stay at it until she came - but this was his time. She was being well paid to do what he wanted, and she was under no illusions about that. And so, inevitably, George stopped fucking her before her time, and ordered her onto her hands and knees. It was time to get down to business.
George moved into position behind his whore and slammed back into her with one hard thrust. He pumped a bit harder this time. While one hand fondled the globes of her lovely round bottom, the other slid up her back, around her side and clutched her swinging breast. He pinched her nipple hard, drawing a sharp gasp as she threw her head back. He did it again, then stretched his arm underneath her and did it to the nipple on the other big, beautiful tit. And again. And back to the first erect nipple. Lori tensed each time, but decided he was still within the bounds of the services he had purchased.
The last time George took a tight grip on her nipple, he didn’t release it. Lori swung her head around and look perplexedly at him. The discomfort was evident in her expression. Her eyes suddenly grew wide as she felt a finger plunge into her asshole. George slid it in and out, just as his cock slid in and out of her cunt. He released her breast and jammed his finger as far up her ass as he could. He began to make circles with his wrist, which stretched her anus a little at a time. He continued to fuck her pussy. His finger slid back to the edge of her asshole, then two fingers plunged in. He pumped her pussy some more. Then three fingers plunged into her ass. She cried out. He fucked her, he opened her asshole wider. He slurped out of her cunt, withdrew his digits from her ass, then pressed the head of his cock against her yielding rectum. With four or five short thrusts, he was inside. Then he stopped moving completely. She gasped, then whimpered. The sensation of the hot cock in her asshole overwhelmed her completely; it was a sharp, unrelenting pain that never lessened, no matter how many men she let in there. George wriggled around, rather than thrust, inside her. To Lori, it felt as if she had to empty her bowels. He explored her body with his hands, his tongue, wherever he could reach. Her tits, her legs, her ass, her back, her stomach, her pussy all got fondled by his hands. Her neck, her ears, her back, her arms got licked and kissed. He took his own sweet time. She knew he wanted her mouth, and obligingly turned her face towards him. He plunged his tongue into her mouth, and said, “Soon!” He began to rock his hips slowly, a shade farther each time, until he was fucking her asshole. In and out of her tight anus his prick slid, each thrust as disconcerting as the last. He fucked faster. His balls slapped against her cunt.
“Okay, now! I’m ready!” he moaned, and after one hard, deep thrust, pulled right of her asshole, and began jerking himself. Lori swung around, grateful that the painful intrusion was over, and opened her mouth, before she could think too long about what she was about to do. George eagerly jammed his cock between her waiting lips. Shit. She could taste her own shit. She wanted to be sick. But she clamped her lips onto it anyway, and proceeded to give him the best blowjob she was capable of. She bobbed her head as fast as she could, pressing her lips against the dick that had just left her asshole as tightly as she could, trying to make him cum as quickly as she could. George took the back of her head in both hands, and pulled it deeper down his shaft. He took over the rhythm of her motion, thrusting his hips into her face. When she thought she was just about to gag, his cum filled the end of the condom. He cried out, and thrust again. And again, until he was spent and fell back onto the bed.
Lori was drained. She just wanted to get out of there as soon as she possibly could. But George lazily reached up and cupped her breast with his hand, kneading it gently, slowly and lightly. Lori was an experienced enough hooker to know that pulling away now would leave a bad impression - the last thing he would remember was that this was a business transaction after all. Not at all good for her reputation or for repeat business. Instead, she subtly sped things along by saying, “Here, let me look after that,” as she carefully peeled the soggy condom off his now-limp penis. Holding it up between forefinger and thumb, she had the perfect excuse to leave the bed. After disposing of it, she fished her lipstick and brush from her purse and sat in front of the mirror. The trick now, she knew, was to keep doing sexy things while she prepared to leave. Like fixing her lipstick and pulling her brush through her raven hair while she was still topless. Like asking him to toss her panties over to her. Like excusing herself use the facilities before she dressed (leaving the door open, of course), then coming back into the room before slipping into her panties, and reaching languorously across his naked body to retrieve her bra, affording him one more feel of her tits, before sitting on the bed beside him to put it on, which gave him the opportunity to caress her nylon-clad legs as her bare breasts disappeared from his view. She stood in front of him as she donned her silky blouse, legs slightly apart, and he didn’t waste his last chance to experience her crotchless pantyhose. She couldn’t help but notice that his cock was beginning to stir again. She pulled on her black skirt.
“Lori,” George began tentatively, “is there any chance we could... I could talk you into giving me another... um, quick blowjob before you leave?” He saw her hesitation, and named a generous price quickly. She nodded, too hastily, she admonished herself. The trick is to make it seem to the client like the money’s not important.
She began to remove her skirt again, but George said “No, no! Please don’t undress!” A clean condom emerged from her purse. She knelt on the bed between his legs and took his half-erect prick in her hands. Stroking it gently, she leaned over and ran her tongue across his balls and onto the shaft. Then she took the shaft in her mouth and sucked it until it was hard, which didn’t take too long at all. She could taste his cum. There was a ring of fresh lipstick at the top of his naked penis where her lips had first made contact. The condom disappeared into her mouth, the reappeared seconds later over his cock.
Lori sucked hard and fast. Once again, George’s hands began to roam over her body, but they stayed outside her clothes. Within a few minutes he had spurted again, and he groaned in delight. She quickly removed the condom, reapplied her lipstick, and bade him farewell. At the door, they pecked each other on the lips as George handed her the extra bills. “Thanks. You were great,” he told her. “I fulfilled a fantasy today. Not too many girls would do that, you know.” Lori knew. She felt herself reddening.
Lori’s job was done. She went straight back to her car, painfully aware that she ran the risk of being late for retrieving her kids from school for lunch. Her bottom was still sore on the drive back. And she was pretty sure that she was not imagining the taste that lingered in her mouth.
At school, her children waited for her. She was only seconds behind the bell, and the schoolyard bustled with parents and kids. Little Alicia pursed her lips for a kiss when she saw her mommy, but Lori had to turn her own head to the side to make her daughter kiss her cheek. A tear appeared at the corner of her eye. She couldn’t kiss her own children because she hadn’t washed the shit out of her mouth after taking money to let some stranger fuck her ass then come in her mouth!
Back at home, she rushed to the bathroom, where she scrubbed her teeth and gargled with strong mouthwash. Then she went into her bedroom to get out of her sophisticated hooker costume. When Lori had removed her skirt and blouse, the door opened and Alicia walked in, eying her mother in her sexy underwear.
I know why you wear those funny pantyhose, mom!” she declared. Lori’s stomach knotted in an instant. “So you can pee easier!” Alicia finished.
“That’s right, dear,” Lori lied. But please don’t mention it to dad, she added to herself. -->
Geraldine
- 09.04.2021
- 25
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