Pillow Talk Ch. 03

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.

Michelle screamed.

"No!"

"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.