Stockings & Stalkings Pt. 02

Giselle stood on her tiptoes, raised up on her high-heels, leaning slightly forward her arms around him. She hesitantly returned his kisses, her dress rucked up around her waist, as Steve rubbed the delicate material of her dress against his body; caressing her tight pantied buttocks.

Steve's cock was now rubbing against the front of Giselle's panties; sending waves of pleasure through his body.

Steve guided his cock inside Giselle's panties so it nestled in the soft satin material. He guided her hand to his member encased in her panties.

She understood what he wanted and took the satin sheathed cock in her hand and softly squeezed it until she felt Steve buck against her; she ever so slowly began to masturbate him. She was surprised by the girth of his member and the by heat radiating from it as it pulsed in her hand. She masturbated him with long slow strokes, establishing a steady rhythm. Steve moved his groin back and forth in time with her strokes, fucking her hand.

After a few minutes of intense stimulation Steve slowly started to walk Giselle backwards until she felt the edge of the lounge against the back of her legs. He pushed her down so that she sat on the edge of the lounge her hand still stroking his enormous member.

Steve removed Giselle's fingers from around his cock and it stood out from his body, proudly erect, quivering inches from her eyes. Pulsing veins encircled the meaty shaft and a silvery thread of pre-cum oozed from the eye of his glossy purple knob down to her lap.

Giselle dreaded what was coming next but knew it was inevitable. Steve put out a hand and pulled Giselle's face towards his erection and thrust his hips forward until his glans touched her lipstick smeared lips. Giselle tentatively flicked out the tip of her tongue, breaking the string of pre-seminal fluid that hung from Steve's cock.

Giselle was repulsed but also inquisitive; what would it be like to put a penis in her mouth and suckle it? She had seen slutty TVs doing this activity online and she had always found it abhorrent; but was there something exciting and pleasurable about it? The girls in the videos she had seen seemed to like it. Giselle resigned herself to the task at hand.

Steve gasped as Giselle began to slowly lick his cock. She worked her tongue around the bulbous head until it glistened with her saliva and then she ran her tongue up and down the shaft concentrating on the delicate frenulum where the glans joined the shaft of his penis. Steve watched the attractive mature transvestite; her face somehow sexier with her smeared makeup, attend to his phallus with her tongue. He stood this for a minute or two but then became impatient and pushed his cock against her lips signalling his need.

Giselle understood and resignedly took a deep breath and opened her mouth as far as she could, and allowed Steve's hard penis to push over her lips and inside her warm moist mouth. She concentrated on her breathing as about six inches of the purple headed invader slid into her mouth and then she began to gag.

Steve eased himself out of her mouth a little until she had her gag reflex under control and then he began to leisurely fuck her face. Giselle submitted and stretched her lips around his shaft and slavered at his glands with her tongue; her aim now was to induce Steve's orgasm as soon as possible and get the ordeal over with.

Now that she had overcome her gag reflex it wasn't that difficult fellating Steve and deep inside herself she felt a little conceited that she was able to make this man so excited by her ministrations. She felt her own penis begin to stir in her panties. 'I'm not enjoying this!' she admonished herself.

Steve was close to coming but he didn't want to come just yet.

Steve pulled his cock from Giselle's mouth with audible plop and it wobbled menacingly in front of her eyes.

Steve moved onto the lounge behind Giselle and pulled her onto the lounge lengthwise, her dress still rucked up around her waist, and he admired the view: Giselle's buxom arse clad in the red satin, her legs encased in diaphanous fully-fashioned stockings and feet shod in the sexy black pumps. He stroked her buttocks through her panties.

Steve eased himself further up the lounge, pushing Giselle's knees apart so that he could position himself between her legs with his large cock resting on her panty-clad buttocks. He lifted the panty material away from her crotch and slid his cock inside so that it rested in the crease of her buttocks; the top of his penis covered by her satin panties. He slowly rocked back and forth, dry-humping her.

Giselle felt Steve's huge penis rubbing against her rear and realised that soon Steve would no longer be happy to dry-hump her and would try to penetrate her. The thought of that monstrous cock invading her virgin rear passage was horrifying and she made one last attempt to induce his orgasm. She pushed her backside out and began to pump back and forth in time with Steve's thrusts.

Giselle allowed her upper body to be forced down on the lounge so that she was kneeling on her hands and knees with Steve behind her dry-fucking her panty-clad derriere.

Giselle's movements were contributing to Steve's pleasure as he enjoyed the feel of her soft satin-encased buttocks pushing back and forth along the underside of his member but knew that he couldn't keep this up for much longer. He guessed correctly that Giselle was trying to get him to come before he could fuck her but he had other plans.

He quickly pulled his cock out from between her buttocks and spat into his hand and lubricated his phallus and then tore out the gusset of Giselle's panties and pulled the shredded satin away from her pale globes. He positioned the head of his penis against her puckering anal bud and pushed hard. His cock pushed at her puckered sphincter until his cock penetrated the tight fleshy ring and slid unencumbered deep inside her anal passage.

Despite the lubrication Giselle screamed as at first her sphincter and then the walls of her anus stretched to accommodate the pulsing phallus invading her back passage. When Steve had his cock buried inside Giselle he stopped pushing and rested, his hands gripping her wriggling hips as she tried to expel his invading member.

"Keep still honey; relax!" he ordered and slapped Giselle on the buttocks.

Through the searing pain Giselle knew Steve was right. The only way that she would be able to accommodate his member inside her without excruciating pain would be to force herself to relax her rectal muscles. She concentrated on doing just that.

Steve felt the vice like-grip of Giselle's sphincter slowly relax. He pulled his cock out of her passage until just his glans remained inside her and spit into his hand again and rubbed his saliva over his shaft and then slowly began to fuck her.

Giselle felt Steve withdraw and then slowly fill her again; this time the passage of his member eased by the lubrication provided by the saliva. Her back passage still burned and ached as Steve's cock invaded her but at least the pain was now tolerable.

Steve grasped the garter straps of her suspender belt and began to ride her like a rodeo rider, his cock slamming in and out of her tight anus.

Steve got into a steady rhythm pounding in and out of Giselle's back passage as she progressed through feelings of intense pain and numbness; until miraculously; she experienced a feeling of fullness that was not unpleasant, combined with small waves of pleasure emitting from a source just inside her anus.

Giselle had read enough about anal sex online to understand what was happening; Steve's penis was stimulating her prostrate gland, his shaft was also stimulating the sensitive nerves of her sphincter. She never dreamed that such feelings of pleasure could come from her back passage. She felt her own cock thicken in her satin panties.

Steve rode her, thrusting back and forth against her, enjoying himself and unaware that he was also unintentionally stimulating her. Her panty crotch rubbed back and forth across her penis and Giselle let out an animal groan from deep within her throat.

Steve slid his cock in and out of Giselle's soft sexy buttocks and Giselle rocked on her hands and knees in time with his thrusts. She couldn't believe this was happening. She was enjoying it; and her own cock pulsed inside her panties as rings of pleasure travelled out from her anus.

Giselle felt her panties tear apart as Steve pulled her buttocks back hard against his groin; he pushed forward with all his might forcing every last inch of cock deep inside her. Giselle pushed back against him as she felt stream after stream of hot semen fill her rectum.

Giselle's own orgasm rocked her and she ejaculated; flooding her panties with hot semen.

Giselle and Steve gasped and groaned in unison as he emptied himself inside the sexy transvestite he had impaled on his pulsing cock. Steve could feel Giselle's anal muscles spasm and her sphincter contract, milking him of his seed.

Eventually both of them began to descend from the pinnacle of their orgasms.

Steve pulled his cock from Giselle's anus with an audible plop. Semen ran in a rivulet from Giselle's anus down her thigh and soaked into her stocking tops. Steve wiped his cock on the remains of her ripped panties and then pushed Giselle facedown on the lounge as he dismounted.

Giselle felt depraved, face down on her own lounge, her derriere high in the air, semen leaking from her anal bud, running down her thigh and soaking into her stocking top; her tattered and semen-soaked panties bunched around her thighs. But she also felt sated. Giselle had not had any form of sex other than masturbation for a very long time and she was quite in awe of the gratification she had just experienced this despite the fact that she had been forced.

Steve reached down and pulled Giselle to her feet; she tottered on her heels, her dress still rucked up around her waist. Steve kissed her, gently this time, and pulled down and smoothed her dress.

"That was wonderful Giselle," he sighed, stroking her hair.

He kissed her again and then eased her away as he pulled up his underwear and buckled his trousers. He sat down and patted the space beside him and Giselle obediently sat. Steve kissed her again and then moved his fingers to her face gently wiping away her mascara-infused dried tears. He handed her a glass of wine and lit two cigarettes and offered one to her. When she took it he kissed her cheek.

"You are beautiful you know," he whispered.

"You are a pig you know," she whispered back, but Steve could see the twinkle in her eyes.

"You loved it," he grinned.

Giselle put her cigarette in the ashtray and suddenly slapped Steve across the cheek.

"That's for blackmailing me and forcing me to into depravity!" she snarled.

Steve looked positively shocked, his face stinging.

Giselle leaned into him and kissed him passionately; gently squeezing his deflating member through his pants.

"And that's for blackmailing me and forcing me to into depravity!" she giggled into his mouth.

Steve was even more stunned.

Giselle pushed him away, puffed her cigarette and stubbed it out. She drained her glass and stood.

"I'm going to get myself cleaned up, redo my makeup and change my outfit," she announced.

"Okay," Steve replied, still stunned at this turn of events.

"Then you are taking me to Sinsations for some dancing and drinks," Michele announced.

"If you are lucky I might follow you into the rest room sometime during the night to take care of the throbbing erection I will undoubtedly evoke when I rub against you while we dance," she smiled.

"And if you are really lucky at the end of the night I might let you come back here and shag my brains out!" Giselle beamed and spun oh her heels.

Steve reached out and slapped her buttocks as she sauntered off.

"Well I'll be fucked?" Steve articulated his amazement at the turn of events.

"Later! If you're lucky!" Giselle called as she closed the bedroom door behind her.

The End