Chapter Three – Compromise
Michelle called Linda the next day and she came around to Michelle’s place and Michelle told her all about the previous evening except for having to give Frankie a blowjob.
“You ain’t telling me everything are you?” Linda teased.
“I don’t know what you mean,” Michelle blushed.
“You telling me Frankie ‘The Stallion’ Caputo had you all alone in that private booth and didn’t do any more than kiss you?” Linda beamed.
“Well he felt me up too,” Michelle’s cheeks reddened further.
“Bullshit! What else did he do?” Linda squeezed Michelle’s fingers and looked inquiringly into her eyes.
“Well I might have blown him a little bit,” Michelle grinned nervously.
“Oh my god sister! You sucked your first cock!” Linda broke down into a giggling shambling mess.
Michelle glowed a bright crimson and then broke down too and they both lay on the rug laughing uncontrollably. When they finally got their wits together they sat up on the lounge and Linda took Michelle’s hands in hers.
“Seriously. Was it ok? Are you alright?” her affection for Michelle evident on her face.
“It was strange at first but I actually found it empowering not degrading. I have to tell you a secret Linda. I really like being Michelle. I mean I really like it. I don’t feel like Mitchell anymore; he’s a distant memory. I feel so feminine; I mean like all the time. Am I a total faggot?” Michelle had tears in her eyes.
“Oh honey; I don’t think of you as Mitchell anymore either. You’re my girlfriend Michelle,” Linda brushed away Michelle’s tears and kissed her on the side of the mouth.
“You need to be careful with this guy Michelle; he’s dangerous. I know you gotta milk him for information but please don’t put yourself at any more risk than you have to babe,” Linda stroked Michelle’s hair.
Michelle felt so safe and secure when she snuggled up to Linda. Linda was so attractive and her full breasts pressed against Michelle; she breathed in Linda’s perfume and sighed.
Michelle looked into Linda’s eyes and softly kissed her. Linda kissed her back; chastely, just lips on lips.
Linda stroked Michelle’s forehead, flicking her fringe out of her eyes.
“I love you as a friend Michelle; but I find you really sexy too,” Linda cuddled Michelle.
“I love you too as friend. But I still think you’re hot,” Michelle giggled.
They kissed for a long minute and at some stage they both realised that if the kiss continued it would no longer be a chaste, friendly kiss. They both felt their hunger stirring. Just before the point of no return, Michelle broke the kiss.
She looked searchingly into Linda’s eyes and saw the same questioning gaze.
Michelle lowered her face to Linda’s and kissed her passionately; sliding her tongue into Linda’s willing mouth. She tasted like lipstick and cigarettes.
Linda had had a couple of lesbian encounters in her formative years and that’s when she discovered that she was bisexual and of course she and Michelle had already had sex at Linda’s place. But that time it was hurried and the fucking was hectic and not altogether satisfying. This time Linda intended to enjoy Michelle to the fullest.
Michelle’s kisses were soft and sensual; the need restrained. There was no necessity to rush and they explored each other’s mouths with their tongues and caressed each other, taking their time.
They were both identically dressed in miniskirts and satin blouses and Linda pressed her bosom against Michelle’s through her white satin blouse.
Michelle bought her hand up to Linda’s bosom and stroked her breasts though the silky material. Linda gasped in her mouth and Michelle felt Linda’s nipples harden through her blouse and bra. She undid a button and snaked her hand inside Linda’s blouse and found her ample breasts cupped in a lace bra, warm, soft and inviting.
Linda reciprocated and slid her hand inside Michelle’s blouse. She found Michelle’s breastforms and ripped them out their cups and dropped them on the floor. This left Michelle’s meagre bosom encased in a satin and lace brassiere; Michelle’s small breasts were smooth and her nipples hard.
“I want to feel your skin honey; not those plastic tits,” Linda whispered into Michelle’s ear.
Michelle nodded and pulled Linda closer.
They kissed and caressed each other, slowly unbuttoning each other’s blouses and then discarding the garments so that they were both dressed only in skirt and bra. They pressed their warm flesh against each other’s bodies and gasped with lust.
Next to go were their brassieres; dropped on the floor. Linda’s ample bosom pressed against Michelle’s meagre breasts and they pulled each other close and opened their mouths wider as they kissed and flicked their tongues together. This was so gentle and so feminine.
Linda led Michelle over to the ratty sofa and instinctively Linda lay down with Michelle astride her. She raised her head and suckled Michelle’s small breast and Michelle gasped with pleasure. Michelle held Linda’s face to her breast and then lowered her face to Linda and lifted her face from her breast so she could kiss her.
They kissed for a long time; Michelle pushing her groin into Linda’s and Linda pushed back. Michelle engulfed Linda’s aureole, flicking her tongue across the hard nipples. Linda held her there and gasped.
They tenderly attended to each other’s breasts and alternatively and passionately kissed each other. They were in no hurry although their sexual arousal was building.
Linda slid her hand under Michelle’s skirt and was not surprised to find that she was wearing pantyhose to help hold her penis in place. She played with Michelle’s thighs until her groans goaded her to seek what Michelle kept in her panties.
Linda thrust her hand inside the waistband of Michelle’s pantyhose, Michelle was wearing her satin panties over the top of her nylons to help gaff her penis and Linda struggled for a little until she found Michelle’s penis tucked between her legs. She gently freed it and Michelle’s erect penis fell into her palm.
She squeezed the turgid organ; already erect and leaking.
Michelle gasped and slid her hand under Linda’s skirt and gently scraped her fingernails across the tender flesh of Linda’s pantyhose encased thighs and then grazed the front of her nylon panties and felt Linda shudder.
Linda’s panties were soaked and Michelle put a finger inside them and explored Linda’s labia and found her clitoral hood. Linda wailed with delight and her heels rattled on the couch.
“Oh god that is lovely!” Linda sobbed with wantonness.
Linda squeezed Michelle’s penis through the layers of panty and pantyhose but she wanted to feel the hard flesh in her hand again. She released Michelle’s tumescent member from the silken trap and softly grasped it.
Michelle lay between Linda’s legs and kissed and fondled her as Linda reciprocated.
Intuitively Michelle knew it was time and she eased the gusset of Linda’s panties aside, used her fingernail to tear a hole in her pantyhose, and slid her engorged member into Linda’s slick channel. They took their time tenderly kissing and caressing each other as they slowly fucked. Linda rising to meet Michelle’s thrusts and Michelle grinding her pubis into Linda’s crotch to ensure she stimulated her clitoris.
When they orgasmed it wasn’t frantic. There was no frenetic thrusting of penis in vagina. Instead, as they sensed their orgasms approaching, Michelle pushed herself deep inside Linda and ground against her, ensuring clitoral stimulation. Linda raised her legs and pulled Michelle’s body hard against hers and rose up and scoured her sopping sex against Michelle; her vaginal sheath pulsed, milking Michelle of her ejaculate.
The two former prostitutes, now lovers, caressed, kissed, fondled, and canoodled; exacting every scintilla of pleasure from their union.
Michelle lay still with her head on Linda’s shoulder, nuzzling her neck and Linda cradled her head in the afterglow of their lovemaking.
“Did I tell you that Frankie stuffed a wad of cash in my handbag for me to go shopping?” Michelle broke the mood.
Michelle stood up and smoothed her skirt and slipped into her blouse but left it unbuttoned as she searched for her bag.
“Look,” she held out the money for Linda to see.
Linda was sitting up; getting dressed and she looked over at the chunk of cash Michelle was holding.
“Jeez girl you must give great blowjobs,” Linda teased and ducked under a high heel that Michelle flung at her.
“He said it wasn’t payment for sex; that I was to buy some nice clothes so he can take me out again tonight,” Michelle moued.
“Ok honey let’s go shopping!” Linda proclaimed.
“Hey. Frankie didn’t say anything about sharing with my girlfriend,” Michelle taunted.
“Well you at least owe me for the pantyhose you ripped when you fucked me,” Linda chuckled and ducked under a second high heel.
The two women hit Macy’s and Bloomingdale’s, buying Michelle a nice evening gown, high heels and costume jewellery to go with it and a pile of lingerie. They also bought her some nice daywear as Michelle’s small wardrobe currently consisted mostly of skanky streetwalker clothes.
Michelle generously spent some money on Linda too and the girls splurged and got a taxi home. They broke out the Jack Daniel’s and had drinks while they opened and inspected their wares. Michelle’s table, lounge, and floor was soon festooned with wrapping paper and packaging as the girls amused themselves, handling and trying their purchases.
After a couple of drinks and considerable amusement Linda finally broke the mood.
“I gotta go babe. I gotta meet the Feebs and update them. Let them know that you met with Frankie last night and that you are meeting him again tonight,” Linda said.
After seeing Linda out the door Michelle suddenly realised that no matter how much Linda loved her as a friend, she really was on her own.
Michelle began to prepare for the forthcoming evening. She reluctantly cleansed herself inside, hoping that she wouldn’t have to engage in any activity where said cleansing was essential. She was happy to kiss, cuddle, engage in foreplay and even fellate her newfound beau but the thought of anal sex was repellent.
She carefully applied her makeup and brushed her hair. She applied a fresh coat of nailpolish and had a drink and a cigarette while it dried. She tucked and gaffed herself and carefully stepped into a pair of luxurious fully-fashioned nylon stockings that she had bought on a whim. They felt wonderful and clipped them to a waist-cinching garter belt and then pulled up a pair of full-cut translucent black full-cut panties to smooth everything out so that she could slip into the red satin sheath-dress she had bought for tonight.
The dress was backless and split on one side all the way to the top of her thigh. Michelle had decided to forego her breastforms and just wore a red satin plunge bra that had slightly padded cups. With the bra she didn’t look quite so flat-chested, and besides, the ‘waif look’ was currently the rage. Anyway, her long legs sheathed in those diaphanous black stockings were going to draw attention away from her chest.
She slipped on a pair of red high-heeled pumps and accessorised with sliver costume jewellery. Michelle had been wearing earrings with her civilian attire as a detective in the drug squad so she already had both ears pierced. This allowed her to wear diamante-encrusted drop earrings that accentuated her neck and bare shoulders. They matched the necklace she wore which emphasised her meagre décolletage.
A liberal spray of perfume followed by packing the essentials into a small silver clutch purse and she was ready to go.
Only one thing.
Frankie had said he’d pick her up at eight and they would have dinner together and he would explain to her what it means to be one of his girls.
Surely he didn’t expect her to walk down to her Hunts Point street corner and wait for him there? Not dressed like this!
The answer came with a knock on the door.
Michelle opened it to find Salvatore dressed in a tuxedo with a smile affixed to his large tanned face. He was an imposing sight; six foot six inches of muscle.
“You look absolutely gorgeous honey. Frankie’s gonna go nuts when he sees you,” Salvatore beamed, he stuck his head in the apartment briefly and looked around inquisitively.
He assisted Michelle down the rickety dingy staircase, offering her his arm and steadying her when her heels rocked, then he escorted her to the limo and opened the door for her. Michelle noticed that he more than glanced at her long legs and stocking-tops when she slid into the back seat.
When she arrived at Delmonico’s Restaurant in Frankie’s limousine he was waiting for her at the curb and opened the door for her. She smiled when she alighted from the limo and her dress split open to reveal her long legs all the way up to her thigh. Frankie couldn’t help but stare.
Salvatore came around and whispered into his boss’s ear; Michelle would have liked to have known what was being said.
“Michelle. Delighted to see you again; I apologise that I couldn’t come and pick you up myself but I had to attend to some business,” Frankie offered Michelle his hand as she stepped onto the pavement.
He kissed her fingers and handed her a white rose.
“How thoughtful Frankie,” Michelle smiled and crooked her arm through his.
As they entered the restaurant all the heads turned.
“They're all looking at you because you are so beautiful,” Frankie said graciously.
“Or because you are so handsome,” Michelle squeezed his hand.
“Or maybe because I am a; what do you call it? A femminielli?” Michelle challenged.
“No! You look more feminine than any of the women here and even if anyone here suspected, they would know better than to say anything disparaging,” Frankie’s ire had risen.
“I’m sorry; I didn’t mean to upset you,” Michelle sounded genuinely concerned.
“You could never upset me while you look you do; you are the most gorgeous creature I have had the pleasure to meet,” Frankie patted her hand, still resting in the crook of his arm.
Michelle was impressed with the splendour of Delmonico’s and she looked around in awe. It was the swankiest place she had ever been in.
Frankie pulled back her seat and pushed it in behind her when she sat. He dismissed the drink waiter with an order and gallantly flicked her napkin and placed in her lap.
“I have taken the liberty of ordering us both a martini,” Frankie reached across the table and gently took her hand.
The drinks arrived and Michelle was delighted with it once she took a sip. She was feeling frisky and decided to tease Frankie and she licked the olive seductively on the cocktail skewer and then crushed it between her teeth.
Frankie gulped and waved to the waiter and ordered dinner for them both and the accompanying wines.
Over the entrée Frankie and Michelle engaged in repartee.
“Did Salvatore tell you where I live? Was that what he whispered in your ear when I arrived?” Michelle asked; a little embarrassed.
“You told me that you know who I am so you should not be surprised that I made some enquires about you; your background and so on. You came to New York from Nebraska and you are living full time as a woman; of this I approve. You are an elegant, beautiful and vivacious young lady,” he said, chewing on his linguini.
“But you are supporting yourself as a prostitute and of this I don’t approve. I told you last night that as far as I am concerned you are finished on the streets,” he broke off a piece of crusty bread and mopped up some sauce.
“So how do I support myself Frankie? I’m not going to be a kept woman. That is nothing more than another form of prostitution,” Michelle made a spirited reply.
She was pushing herself into dangerous territory but if she let Frankie hole her up in some apartment so he could come around and have sex with her whenever he felt like it she would achieve nothing. She needed to see who Frankie met with and to listen to what they talked about in order to get the information she needed to be released from this undercover task that had been forced on her.
“Well it’s like this. I don’t have a problem with prostitution per se, to me it is a victimless crime from which I make a lot of money,” Frankie smiled.
‘You should see some of the drug addicted, beaten up and preyed upon streetwalkers down at Hunts Point if you think prostitution is victimless,’ Michelle thought but kept her opinion to herself.
“As well as my nightclub, I also run a high-class relaxation establishment, a house of assignation, a bagnio,” his smile was wolfish.
“A brothel, a cathouse, a whorehouse,” Michelle replied a little tersely.
“Shall we compromise and call it a bordello. That word is not quite so harsh,” Frankie grinned.
“So are you offering me a job? Leave the corner and set up in your premises,” Michelle raised her brow.
Frankie blushed and for the first time showed her some annoyance.
“No! It’s not like that! I told you I don’t want you doing that anymore,” he sounded irritated.
“Look I’ve seen your place from the outside and Salvatore tells me that the place is…well excuse me…it’s a dump.”
It was Michelle’s turn to blush and show her ire.
Frankie patted the back of her hand soothingly.
“Well I would like to offer you a job and with it, a better standard of accommodation,” Frankie continued.
Michelle was about to interject but Frankie held up his hand.
“My current Madame, the lady who runs my establishment, has quit and none of the other women I employ are suitable.”
“You would have your own apartment above the establishment. It’s a nice place and has a separate access. What do think?” Frankie looked pleased with himself.
“You want me to be a brothel-keeper?” Michelle was incredulous.
“Hey you get a nice apartment; you get a well-paid job, you work for me so you’re as safe as you’re ever going to be. And…you no longer have to perform sexual services for a living,” Frankie sounded convincing; at least to himself.
“But I don’t know about that side of the business,” Michelle countered.
She was conflicted. If she took Frankie up on his offer she would undoubtedly get close to him, his businesses and hopefully his business partners. But it meant she would effectively become his kept woman.
“Look. Let’s finish our meal and I’ll take you to look the place over before you make up your mind ok?” Frankie countered.
Michelle nodded and drank some wine; her head spinning with apprehension, and she had to admit; a little anticipation.
“Let’s discuss other things, you are delightful conversationalist as well as a stunning young lady,” Frankie turned on the charm.
And they did. Frankie turned out to be a man of the world and quite the philanthropist, despite the fact that he was an organised crime kingpin.
Salvatore drove Frankie and Michelle through the boroughs of New York back towards Hunts Point. It turned out that Frankie’s bordello was not far from the street corner where Michelle had pretended to ply her trade.
During the ride they cuddled in the back of the limousine, the dark glass partition providing them with privacy. Frankie was delighted that Michelle was wearing stockings instead of pantyhose and he slipped his hand inside the spilt of her gown and helped himself to her thighs.
Michelle was happy to kiss him and she responded to his ministrations, stroking his hard member through his trousers. She was tempted to unzip him and fellate him in the car, hoping that it would preclude him wanting to fuck her.
Frankie allowed Michelle to take out and stroke his huge phallus but when she went to lower herself down to it he held her back.
“Let’s not sweetheart. Let’s wait until we get to your new abode where we can get comfortable,” he said and kissed her.
The car pulled up outside of a rather dilapidated three-story brownstone building; the curtains gave off a soft glow, the first floor curtains were red, which made Michelle smile. There were large glass double doors attended to by besuited, large doorman who nodded to his boss and Frankie nodded back.
“It looks a lot better on the inside. The façade is designed to keep the place incognito for those who don’t need to know,” Frankie grinned and touched the side of his nose.
“We will use the private entrance,” Frankie took out a key and led Michelle to a doorway at the side of the building.
He opened the door for her and let her take the lead.
“We’re on the third floor. The bordello is on the ground floor, I keep an office on the second, and the apartment takes up all of the third,” Frankie explained.
Frankie couldn’t help but play with Michelle’s satin-clad buttocks as climbed the stairway ahead of him. Michelle giggled. She had to admit that she was flattered.
The apartment looked to be spacious and tastefully decorated but Michelle could do no more than get through the door before Frankie pinned her against the wall and began to kiss he passionately.
Michelle managed to break the kiss and held him out at arm’s length,
“Frankie I really want to have a good look around before I make up my mind. Can we just do that without any hank panky?” Michelle beseeched him.
Frankie took her hands in his and kissed her cheek.
“Of course we can amore mio. I will behave like a gentleman I assure you,” Frankie smiled.
Michelle was more than a little surprised that Frankie had used the term ‘my love’. He had called her sweetheart and other terms of endearment but ‘amore mio’ seemed a little excessive.
Frankie led Michelle around the apartment extolling its virtues as he did. It had a small kitchenette, a large lounge room and even larger bedroom with a well-appointed ensuite bathroom and walk-in robe. It made her own grubby apartment seem paltry and demeaning.
“Check out the bedroom and amenities sweetheart and I’ll bring us a glass of wine,” Frankie kissed her cheek and left for the kitchen.
He returned with two glasses of red wine to find Michelle sitting on the huge king sized bed that had been made up with satin sheets and comforter. She was bouncing on it, testing the springs.
Frankie put down the wine and came over to her.
“It’s great bed Michelle. Here lie back on it,” he eased her back on the bed and stood back looking at her.
“Good you look good in that dress; I’d like to kiss your toes and then follow the seams of your stockings with my tongue,” he said to Michelle who was prone on the bed with her dress split open showing off her legs.
“Behave Frankie; you promised you would,” she chided him.
“But you’re just so sexy; I want to do things to you,” he smiled.
“Nice things,” he winked.
“Once I’ve licked your legs I’d like to rub my cazzo along them too, and maybe on your cute bottom,” he grinned wickedly.
Michelle felt fear creeping up on her. She knew that Frankie would soon want to do more that just talk about sex; he would want her body. She weighed her options but there weren’t many. Deep inside herself Michelle knew that eventually she was going to have to submit to Frankie; she just wanted to delay it as long as possible.
But what if he forced himself on her? She could try and fight him off; but he was a lot stronger than she.
Or she could capitulate. Just for tonight she could encourage him and let him hump her legs and ass which he seemed keen to do; worse case scenario she could even fellate him again. Turns out giving Frankie a little head wasn’t as bad as she’d imagined; she actually felt empowered when she did it last time. This seemed the safest option. Play along but at all costs but prevent him from fucking her.
Michelle sat up on the bed and Frankie handed her, her wine and took his own glass. They clinked glasses and drank.
“What other sort of things?” she looked over the rim of her wineglass.
The room was dark; lit only by the bedside table lamp.
Frankie looked at Michelle intently; Michelle had shifted position and now sat on the bed with her legs curled under her; the red satin evening gown clung to her body. The split was open and her long legs clad in the slinky nylons, seemed to shimmer in the lamplight and he was sure he could just make out the dark bands of the welts. He loved that Michelle was wearing stockings and he gazed at the dark seams and the reinforced fully-fashioned heels of her nylons as Michelle seductively dangled one of her high-heels from the toes of her right foot.
She was teasing him!
He looked into her heavily made-up eyes; then at her rouged cheeks and red-lipsticked lips, her jewellery glittered at her earlobes, wrists and decolletage. His eyes found hers again and he drew in a breath and inhaled her perfume.
“You know what sort of things. The sort of things I told that I want to do to you,” Frankie’s breathing was heavy.
He began to undress. He took off his jacket and kicked off his shoes and pulled off his sox. His bow tie went the way of his sox.
Frankie was now barefoot, dressed only in tuxedo trousers and a pressed white cotton shirt, which he had opened to the waist. His chest was exposed and the beginnings of an erection began to tent the fabric at his groin.
“We agreed there would be no hanky panky but it looks like you’re going to renege on the deal so I propose another deal,” Michelle said, she swung the high-heel from her toes.
Frankie was mesmerised by the shoe rocking back and forth; dangling from her dark-nylon clad toes.
“Deal?” he lifted his brows.
“You can play with my legs and my bottom as requested; I might even suck your, what did you call it? cazzo, if you behave yourself.”
“But no fucking. We save that special milestone in our relationship for a celebration” she glared at him intently.
“You mean I can dry hump your legs and you’ll suck my dick but I can’t fuck you,” Frankie grinned lasciviously.
“If you must put it so lewdly yes. And I keep my clothes on. All of them!” Michele replied, grinning cheekily at him.
Frankie seemed to consider Michelle’s proposition. Of course he could just take her if he wanted; but he didn’t want their relationship to be that way. He was genuinely infatuated with the pretty travisto.
“Agreed,” Frankie answered; his voice thick with lust.
Michelle let her dangling high heel drop to the floor and pointed her toe directly at Frankie. Her red-varnished toenails just perceptible through the gauzy black nylon.
“So what were you saying about kissing my toes and then following the seams of my stockings with your tongue?” Michelle wriggled her toes at him.
Frankie eagerly stretched Michelle’s legs out straight and pulled off her remaining high-heel. Michelle wriggled her toes again in anticipation of what was to come.
She really liked the feeling of power she held over this man as he worshipped her feet. His hands held her silken-clad ankles firmly and she could feel his hot breath on her feet through her nylon stockings. Then she felt his tongue begin to explore her toes. He ran it under the toes of both of her feet and then he licked each of her toes individually. She felt her cock hardening, tucked away in the crevice of her buttocks, held in place by the gaff.
Frankie tasted the silky material of her nylons, a scintilla of sweat, and a little of her perfume as he sucked her toes. He explored the ridge under her toes and then examined the whole of each foot with his tongue. The then put the toes of each foot into his mouth, alternating from left to right and sucked and slathered her feet. His cock was rock hard and he was tempted to reach for it but he had a better idea. Michelle had her eyes closed and was breathing quite heavily. The sensuous tactility of this man worshiping her feet was surprisingly erotic and she was extremely aroused.
Frankie removed Michelle’s feet from his mouth and lowered them towards his groin. Michelle lay back on the bed filled with expectation and lust. She was going to enjoy giving Frankie a footjob. Once again she felt empowered by her hold over him.
Michelle leaned forward a little and the split in her gown opened wide exposing her stocking-tops and the crotch of her full-cut panties. She lowered a stocking encased foot into Frankie's lap and watched him begin to squirm and moan.
"Oh Michelle!" Frankie moaned.
Michelle's dark reinforced nylon toes rubbed against Frankie's hard penis through his pants. Frankie lifted Michelle's other nylon encased foot and rubbed it all over his face. Michelle enjoyed listening to his muffled moans.
Michelle rubbed one of her feet against his erection while Frankie worshiped the other foot pressing it firmly over his nose and mouth; inhaling her foot odour and licking at her nylon imprisoned toes. He reached down and stroked the stocking foot that was pressing on his hard cock. He continued to moan; licking and sucking on Michelle's gossamer-glad toes, sliding his other hand farther up and down Michelle's long, sleek stockinged-encased legs.
"Take it out," Michelle whispered seductively.
Frankie fumbled at his lap; unbuttoned his fly and released his engorged penis. Michelle worked her stocking foot all around his huge rampant member. She worked her toes on the underside of his shaft, just below his glans. After a few strokes from Michelle's toes Frankie was squirming and groaning. A filament of pre-ejaculate oozed from the tip of his penis and adhered to Michelle's foot; the translucent globule glistened on her dark reinforced nyloned toe. Frankie ran his hands up and down Michelle’s stocking-sheathed leg from the tips of her toes to the tops of her hose. He moaned with pleasure as Michelle massaged his phallus with her silken foot.
Michelle pulled her other foot away from Frankie's face and dropped it into his lap. She placed each of her feet together and arched her soles, trapping Frankie's engorged manhood between them. She moved her feet back and forth masturbating Frankie's cock with her nylon-sheathed feet.
Frankie's cock was swollen, the glans bright red and almost ready to ejaculate onto Michelle's feet. Pre-seminal fluid was flowing freely from the eye of his penis, and the sensation of the wet slick nylon sliding up and down his shaft was exquisite. Michelle's toes became soaked with Frankie's pre-seminal fluid.
Frankie looked down at his lap again and watched as Michelle's shapely feet slid up and down his straining penis, milking him with her diaphanous encased appendages. The nylon over her toes glistened with pre-ejaculate and Frankie ran his hands up and down Michelle's legs all the way up her thighs to the dark welts and garter straps. He bucked back and forth fucking Michelle's feet and he could sense his orgasm approaching. He firmly grabbed her ankles and pulled her feet from his cock.
“Hey! I was enjoying that!” Michelle whined.
“That’s not the way I wanna come darling,” Frankie smiled up at her.
He stood up and dropped his pants and ripped off his shirt so he stood naked before her. His penis was rampant and throbbing. He fell on her and Michelle giggled as he began to hug and kiss her.
Michelle opened her mouth and met Frankie’s tongue with her own; she crushed his lips with hers whilst at the same time raising her legs and wrapping them around his flanks. She could sense that Frankie loved the feel of her nylons against his bare skin and her plan was to get him to ejaculate against her legs or her body; worst case scenario she would fellate him. To be honest she was enjoying every minute of their passionate embraces. Her cock was hard; trying to break free of the gaff. As long as Frankie didn’t try to fuck her, Michelle was confident that her plan would work and she could maybe take a little pleasure herself whilst Frankie took what he wanted from her.
Frankie’s cock was rubbing on Michelle’s thighs; he enjoyed the different sensations as his cock shifted from her sheer nylons to the cool firm flesh of her upper legs. His cock touched one of her garter clips and he winced as the cold metal snap nipped the flesh of his penis. He didn’t mind actually because the mild pain held back his orgasm. He was close to coming but didn’t want to just yet.
He extricated himself from Michelle’s embrace; but much to her dismay she found that Frankie had other plans as he mounted her again. She willingly opened her legs to accommodate him; even helping him ruck up her dress so he had unfettered access to her legs. He kissed her and his cock brushed against her stocking welt leaving a silvery trail of pre-cum on the silky dark nylon. Michelle felt Frankie adjust himself then she felt his hot cock on the front panel of her full cut satin panties; it was hard and throbbing and she became concerned about what he might try next.
“Oh Frankie you can rub on my panties but remember our agreement; no penetration!” she warned him.
She raised her hips and ground her belly against him. The feel of his hard member pressing against her flesh with only the flimsy layer of panty material between their bodies was extremely arousing. She kissed him deeply, driving her tongue deep into his mouth, wriggled her hips and wrapped her legs around him once more. She wanted to bring him to release. To feel his hot seed splash on her thighs or her belly.
Frankie slid his cock under the leg opening of her panties and his cock came into contact with her warm flesh. Michelle panicked and tried to push him off her but Frankie hung on and probed at her groin with his hard manhood. She drummed her heels on his back and pushed at his shoulders to try to dismount him.
“No Frankie! No! You promised!” she shrieked.
It was too late; Frankie’s cock was buried in her groin.
“Stop! Stop! Stop” Michelle cried, but Frankie was committed.
“Shh. Shh. Shh, Michelle it’s ok honey,” he whispered in her ear.
He stroked her hair and then kissed her eyelids, her cheeks and her mouth with extreme tenderness.
Michelle reluctantly realised she might have to give up her virginity tonight. As far as Frankie was concerned Michele had been fucking guys for money for nearly ten years; there was no reason for her to turn him down.
Michelle set her resolve and stopped struggling and lay still letting Frankie kiss and embrace her. It felt comforting, exciting, and terrifying all at the same time. She looked in his eyes.
“Please be gentle?” she whispered.
They kissed and fondled each other and Michelle felt Frankie begin to rub his erection on the front of her panties again and she began to respond to his attentions; she was very aroused herself. His hands stroked her stockinged legs rubbing them from knee to stocking-top and then his fingers stroked her bare thighs.
“Mmm, that’s nice,” Michelle purred.
Frankie slid his hand along the front of her panties and then he slipped his fingers inside the waistband. Michelle began to struggle again.
“Shh, it’s ok; just let me do this, trust me you’ll like it,” Frankie kissed her ear.
Michelle felt more than a little trepidation as Frankie’s hand slid inside her panties. His fingers found her penis, semi-erect, taped under her groin. She struggled a little but Frankie held her still and gently extricated her cock from the gaff, dropping the disused tape on the bed. He positioned her member along her stomach and pulled her panties back up over it and lay down on her. His erection pressed against hers through the satin panty material. He began to rub his cock against hers and he kissed her deeply.
Michelle had never felt anything so exciting in her life. She had at times masturbated with panties or stockings covering her penis but the feelings could not compare to the sensation of having a hard member rubbing her own with the layer of panty material between them. She could feel Frankie’s cock pulse and throb as it massaged her own quivering shaft.
She lifted her legs and wrapped them around Frankie’s body; locking her heels behind his back.
“I like this Frankie! Please make me come!” she whimpered and ground herself against his hard, hot cock.
Michelle was close to orgasm and she hoped Frankie was too. She wanted to feel his hot seed flood her panties and coat her cock with his semen as she too erupted.
Frankie adjusted his position slightly and pushed his cock into the crevice of her panty-clad buttocks and began to hump her there. It felt nice but not as nice as his cock rubbing on her cock.
“Put it back please honey,” she whispered in his ear and kissed him passionately whilst she wriggled her buttocks trying to extricate his cock.
"Stop it you naughty boy," she giggled.
Frankie did not stop; instead he pulled the gusset of Michelle's panties aside and slid his cock into the crease of her soft creamy buttocks.
"Stop it!" Michelle yelped; seriously now.
Frankie ignored her and his glans probed her sphincter. Michelle screamed and wriggled but Frankie was too strong. He held her down with one hand whilst he used the other to guide his penis into Michelle’s anus.
“Please don’t Frankie; I don’t want this I’m not ready for this,” Michelle pleaded.
“It’s ok Michelle. I know my cock is big and the first time I put to you it will hurt a little but then it will be wonderful. It will be just like your first time,” he smiled down at her.
Frankie did not know that this would actually be Michelle’s first time and that she did not want to be sodomised.
Frankie reached out to the bedside table and opened the drawer. He kept a tube of KY jelly in there and he squeezed a dollop of viscous lubricant and spread it thickly over Michelle’s sphincter and his long thick shaft; all the while Michelle wriggled and struggled underneath him. He used his body weight to hold her down.
“Stop! Stop! Don’t! Don’t!” she screamed.
But they were alone in Frankie’s apartment and there was no one to hear her pleas; besides she knew her deflowerment was inevitable. She just didn’t want it to be tonight; or any night.
The glans of Frankie’s penis pierced her sphincter. The lubricant eased the entry of Frankie’s cock past her tight bud but the pain was still incredible. Michelle moaned and bucked but Frankie would not remove his phallus from inside her, he only had his glans inside her and he didn’t try to push any more of himself inside her but he still held her down.
“Oh that hurts!” Michelle whimpered.
“Shhh Honey; relax and it will be ok,” Frankie whispered, trying to sooth her.
“Please take it out!” Michelle moaned.
Michelle was feeling a constant deep burning sensation combined with spasmodic twinges of intense pain shooting from her sphincter. She whimpered and wriggled, trying to expel the offending intruder from her back passage but Frankie held on.
“Michelle! Listen to me!” he hissed; and she stopped struggling and listened to him.
“Look honey, the worst is over I promise, if you lie still and let me; I can make this experience special for you. Or you can keep struggling and I’m going to fuck you anyway but then it’s going to hurt.”
Michelle realised that she had no real choice and besides she would do anything to stop the excruciating pain that was coming from her sphincter. She sighed and lay still; her anus pierced by Frankie’s penis but she was smart enough to know that fighting was only going to make the pain worse. She tried to relax her sphincter but her instinct was to try to push against the object invading her anus; not to accept it.
“That’s it honey,” said Frankie as he felt Michelle’s sphincter spasm as she tried to relax it.
“It will be ok I promise.”
Michelle was quietly sobbing but at the same time she forced her inner muscles to relax. Amazingly the twinges of intense pain began to subside; she still felt the burning sensation around the entrance to her anus but it was tolerable. Frankie took another globule of KY jelly and applied it to his shaft.
“Ok honey; keep relaxed, I really don’t want to hurt you,” Frankie soothed.
Millimetre by millimetre Frankie slowly pushed himself inside Michelle; he took his time and whenever Michelle flinched he stopped and soothed her as his shaft slowly disappeared inside Michelle’s rectum. Michelle felt full and intensely uncomfortable, the urge to expel Frankie’s penis was immense and she had to physically prevent her internal muscles from contracting.
After ten minutes Frankie had about half of his girth buried inside Michelle’s anus he raised her legs so that they rested over his shoulders. He looked down at her pretty face and smiled.
“It’s ok Michelle; you’re doing fine.”
Michelle’s only response was a silent tear. She had stopped sobbing and now and only mewed softly, but now that she had learned to relax her sphincter she really didn’t feel any pain. Even the burning sensation had subsided; she just felt full.
Frankie continued to press slowly forward cooing and encouraging Michelle to stay calm and relax her anal muscles. When he had about three-quarters of his shaft inside her, he sensed her internal flesh respond and she gasped. He knew what it was; it was not pain. His glans had found her prostate gland. Her reaction was pleasure not pain.
Frankie knew better than to rush things; he took his time pushing the remaining few inches of his shaft inside Michelle until eventually he was buried inside her with his scrotum resting snugly against her loins. He wriggled his penis inside her to stimulate her prostate and he kissed her. Michelle began to respond and she kissed him back.
“Mmm, that feels good Frankie. The pain has stopped and it feels quite nice,” she smiled up at him.
“I told you it would hurt but only for a little while. Just stay relaxed and it will get better,” Frankie lowered his face to hers and kissed her again.
He stroked her silken-hosed legs and she rubbed then against his body because she knew he liked it.
She felt Frankie’s glans rub against an area inside her that suddenly caused waves of intense pleasure to course through her body. As his penis stimulated her prostate, rings of pleasure ran up and down her; her sphincter responded and slackened and began to emit its own tingling ripples. Michelle gasped.
When Frankie lowered his mouth to hers she kissed him back, deeply, passionately. She drove her tongue into his mouth and lifted her buttocks up off the bed and pushed herself up against him; she moved her legs so they were around his waist; she locked her ankles together and held him against her. She felt totally feminine lying here underneath this man; wantonly giving herself to him.
They fucked slowly but passionately taking their time; Frankie easing his penis in and out Michelle’s anus with long slow thrusts as she raised herself up to meet him. There was no fervent thrashing or pounding; just firm, slow deep thrusts provided the maximum stimulation for both of them. They said little to each other, the fucking was accompanied by one long passionate kiss.
"Oh fuck me honey!" Michelle moaned and began to push back against Frankie as he slid in and out of her tight passage.
Michelle's cock became fully erect. Frankie’s reached down and squeezed her through her panties.
"Oh jeez!" Michelle moaned.
Frankie fucked Michelle and she fucked him back; both of them moaning and groaning with the intensity of their passion. He squeezed and stroked Michelle's hard penis and the stimulation she felt from having her cock massaged through her satin panties amplified the rings of pleasure that radiated from her anus. She was going to orgasm.
Frankie's cock throbbed too as he frantically squeezed Michelle’s cock through her panties. He ejaculted deep inside her; his cock pulsing and juddering as his scrotum contracted ejecting steams of hot semen. Michelle felt her back passage flood with Frankie’s sperm and this triggered her own orgasm.
Michelle felt him orgasm; his cock was fully embedded in her, his scrotum tickling her buttocks when he shuddered and wriggled his member inside her as it pulsed and throbbed. He was kissing her passionately, their tongues entwined, lips mashed, their teeth occasionally cracking against each other with the intensity of the kiss.
Michelle moaned as her own orgasm shook her body and she felt her penis begin to pulse and expel her issue. Frankie slid a hand between their bodies and milked her as she ejaculated, hot semen soaked into her panties.
Michelle slid her stocking-sheathed legs up and down Frankie's torso and pulled him harder against her; her fingernails raked his back as their lips crushed together and their tongues intertwined. Michelle drummed her heels against Frankie's hard buttocks.
Frankie lay on top of her, supporting his weight on his elbows as they both slowly came down from their orgasms. He placed little soft kisses on her lips and kissed her on the eyelids and stroked her hair. Michelle felt feminine and fully sated. She felt like she knew what it was like to be a woman who had just been made love to, and her lover was contentedly happy to remain in her arms.
"I’ll take the job and the apartment," Michelle said sometime later and smiled up at her new lover.
To be continued.
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