The Devil You Know Ch. 02

Michele increased the tempo as she felt Brian's cock begin to throb. She could feel his orgasm approaching and she was a little trepidatious but she was considerably more curious about how this man's semen would taste. She removed a hand from his buttocks and placed her fingers around his scrotum and squeezed him; milking him of his seed.

Brian exploded in Michele's mouth; flooding it with hot semen. Michele fervently sucked and slathered at Brian's pulsating cock, swallowing his spend as it gushed forth into her mouth. Brian's knees buckled with the intensity of his climax and he placed his hands on the back Michele's and fucked her face enthusiastically; emptying himself into the pretty transvestite whore.

Michele realised that she too was close to climax; her cock was throbbing in her panties and aching for release but she didn't want to move her hands away from Brian's body. She was enjoying bringing this man to extremis with her lips, tongue and hands; it was exhilarating and powerfully erotic.

Michele swallowed the last of Brian's discharge and licked his cock clean as it slowly began to deflate. Brian reached down and pulled Michele to her feet and to her surprise he kissed her passionately with an open mouth. She tasted the remains of Brian's spend mingled with his saliva as he French-kissed her; wrapping her in his arms and muttering sweet sentiments into her mouth. Eventually his fervour ebbed and he broke the kiss; holding her in a warm embrace and gasping for breath.

"My God Michele; that was magnificent!" he whimpered into her ear; inhaling her perfume.

"Thank you darling; a girl like's to know she's appreciated," Michele giggled coquettishly.

She felt amazingly feminine and sexy. She was quite taken aback at how enthusiastically she had responded to Brian's advances. She was still peeved that he had blackmailed her and forced himself upon her, but if he hadn't done, she would never have experienced these wonderful feelings.

Brian led picked up his bathrobe and Michele excused herself and went into the bathroom to fix her makeup; her lippy definitely need some attention!

Brian called room service and ordered champagne and a plate of canapés and they arrived just as Michele re-entered the room.

"So; what are we on a date now? You told me you weren't going to take me to dinner but this is a little extravagant isn't it?" Michele said sarcastically.

"Behave Michele; after the beating you gave my credit card today you don't want to get too sassy," Brian replied, opening the champagne and pouring two glasses.

"But wasn't it worth it? Don't you like your sassy gal?" Michele laughed and pirouetted on her heels.

Brian reached out and pulled Michele across his knees.

"I'll teach you about sassy!" he laughed and playfully spanked her panty-covered buttocks.

Michele hardened slightly and Brian felt her stiff cock rub against his thighs. He reached under her and tugged playfully on her satin-sheathed member.

"Behave," he said and lifted her to her feet and pulled her down beside him on the bed.

He kissed her softly; one hand stroking her hair and the other exploring the welt of her stockings. Michele mischievously pushed him away.

"Time to eat, drink and be merry!" she said taking a glass of champagne in her hand.

They ate and drank; neither saying much; uncomfortable now with the situation in which they found themselves. After a while:

"Would you really have told my father and my colleagues about my crossdressing?" Michele asked, plaintively.

"I honestly don't know. All I know is that I became fascinated with you and I wanted you," Brian replied.

"To tell the truth; if you hadn't forced yourself on me, I would still be a transvestite virgin," Michele said.

"I would probably have never mustered the fortitude to arrange a meeting with another tranny; and I definitely would never have approached a man," she admitted.

"So; you like it?" Brian smiled at her and pulled her towards him.

They lay on the bed kissing and fondling each other; both becoming aroused again. Michele was still unsure where she wanted this relationship to go and she eventually pushed Brian away as his ardour began to intensify.

"I need to pee and fix my makeup again," Michele smiled and hopped off the bed and sauntered over to the bathroom.

Brian watched her ass sashay across the room and followed her long, silk-sheathed legs. Her red satin-sheathed buttocks peeked below the burgundy basque and her blonde hair draped down to her shoulders. The scent of her perfume remained on the bedclothes and Brian realised his cock was hardening again. He improved his erection until it was rock hard and then he jumped off the bed and followed her into the bathroom.

Michele was leaning over the vanity fixing her makeup when Brian came in and stood behind her. He put his hands around her waist and pushed his cock into the crevice of her panty-clad buttocks and began to hump.

Michele wriggled her buttocks trying to extricate his cock.

"Stop it you naughty boy," she giggled.

Brian did not stop; instead he pulled the gusset of Michele's panties aside and slid his cock into the crease of her soft creamy buttocks.

"Stop it!" Michele yelped; seriously now.

Michele had fucked herself many times with dildoes and vibrators but she didn't think she was ready yet for anal sex with Brian.

Brian had other plans.

He wrapt his arms around Michele's waist and pulled her back against him and his glans probed her sphincter. Michele screamed and wriggled but Brian was too strong. He held her with one arm and his free hand snaked out and grasped a little bottle of moisturiser from the vanity shelf.

"Please don't do this Brian," Michele begged.

Brian ignored her and flicked the cap off the bottle and squeezed the cold creamy liquid onto his cock and poured the remainder down Michele's ass-cleft. Michele struggled and stamped her feet when she felt the cool viscous fluid on her ass.

Brian pushed forward and the head of his glans entered Michele's puckered bud. Michele was shocked and she quit struggling as Brian slowly slid the full length of his penis inside her until his groin pushed against her soft round ass.

Michele's back passage felt uncomfortably full and for few seconds she felt excruciating pain but as the lubricated invader slid inside her anus she began to experience wonderful feelings of sexual excitement that no plastic dildo could bring forth.

"Ohhhh!!!" Michele groaned.

"Yessss!!!" Brian hissed.

His cock felt like it was being squeezed by a tube of warm pliant satin; Michele's anus was tight and velvety. Michele could feel Brian's cock slowly pulsing inside her; expanding and contracting the walls of her anus, his glans stimulated her prostate, radiating rings of intense pleasure.

"Take it slow!" Michele whispered and slowly began to rock back and forth on her heels.

Brian took hold of her waist and got into the rhythm; slowly fucking Michele's tight ass. Michele began to increase the tempo as her anus dilated and Brian's cock rubbed against her prostate; small spikes of delightful stimulation emanated from her sphincter which was tightly clamped around Brian's turgid shaft.

"Oh fuck me honey!" Michele moaned and began to push back against Brian as he jackhammered in and out of her tight passage.

Michele's cock became semi erect and she took one hand off the vanity to try to stroke herself but she couldn't maintain her balance because of the intensity of the fucking. Brian saw what she was trying to do and, with his shaft buried himself inside her hot tight anal cavity, he reached around and squeezed Michele's penis through her panties.

"Ohhh!!!" Michele moaned.

Brian fucked Michele and she fucked him back; both of them moaning and groaning with the intensity of their passion. Brian squeezed and stroked Michele's hardening 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 come!

Brian's cock throbbed and he pulled her back hard against him with his free hand burying himself deep in her bowels as he frantically squeezed her cock. He unloaded inside her; his cock pulsing and juddering as his scrotum contracted and forced steams of hot semen to spurt for his pulsating penis. Michele felt her back passage flood with Brian's sperm and this triggered her own orgasm.

A dark stain spread across the front of her panties and then a puddle of warm white semen formed on her panty-panel as her spend soaked through the diaphanous fabric. Brian reached inside her panties and smeared the hot come over her shaft and milked her of the last of her seed.

They remained locked together as they shuddered and gasped; their orgasms slowly subsiding. Brian slid his deflating member out of Michele's anus and roughly spun her around. He kissed her forcefully and she responded by hiking her ass up on to the vanity bench and wrapping her legs around him, pulling his body close to hers. Warm semen trickled from her anus and soaked into the rear of her panties; the front of her panties, already soaked with her own come, absorbed the few remaining dribbles of Brian's semen as it oozed from the eye of his cock.

Michele slid her stocking-sheathed legs up and down Brian's torso and pulled him harder against her; her fingernails raked his back as their lips crushed together and their tongues intertwined. Michele drummed her heels against Brian's hard buttocks and then pulled her face away from his; gasping for breath.

"We need to talk," Brian said.

They talked late into the night; stopping now and then to make love. By the time the sun crept across the room and woke them, it was late in the day.

Mike flew back home first-class seated next to Brian and they continued to talk and refine their plans for the future.

Two months later Mike Harris sat behind the desk in the office of the online publishing company he had set up with Brian. He had his feet on the desk and he was checking out the ample behind of Carolyn Jones who was bent over the bottom drawer of a filing cabinet. They had made Carolyn an offer that their previous employer couldn't match and she had joined the three-person company as a partner.

Mike allowed the leg of his pants to slide all the way up his calf revealing sheer taupe pantyhose. He wore pantyhose and panties under his male clothing all the time now and as soon as he got home he immediately transformed into Michele. He and Brian shared a house and on most nights they shared a bed.

Carolyn stood up and walked over and perched her shapely ass on the edge of his desk.

"Mike; I notice you make no secret of the fact that you wear nylons under your trousers. Is there something you want to tell me about?" she smiled.

"As a matter of fact............" Michele replied.

Later that evening Brian returned home. He preferred to arrive home after Michele so that she had time to transform. He let himself in and was surprised to find the house was dark. There was a sliver of light coming from the slightly-ajar bedroom door.

"Michele?" Brian called as he approached the door.

What he saw when he opened the door both astonished and excited him.

On their king-sized bed Michele was lying on her back dressed only in panties, bra, stockings and heels; her heavily made up face framed by a black bob was contorted in ecstasy. Kneeling between Michele's legs was Carolyn Jones dressed in a black bustiere, black seamed stockings and black high-heeled pumps. Her makeup was dishevelled and she was sweating profusely.

Carolyn was wearing a large strap-on dildo and was fucking Michele in the ass with enthusiasm; both of them were grunting and panting.

Michele turned her head and grinned at Brian.

"Are you going to get over here and join us; or just stare at us all night?" she smiled.

A few minutes latter, as Brian slid his cock inside Carolyn's buttery quim, he thought to himself how lucky he was to have two gorgeous women in his life.

When Brian's cock slid inside her, Carolyn didn't miss a stroke; she continued to enthusiastically fuck Michele in the ass as Brian began to enthusiastically fuck her sopping cunt.

The End