Do What the Nice Man Says Honey

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was over quickly.

"Come on luv; give it a bit of a suck before I fuck you," Andrew laughed almost manically.

Despite his younger age and handsomeness, Andrew was a brute compared to Donald.

Alex was on her knees with her pretty blue eyes looking up into Andrew's handsome but merciless face. He put his hand on her jaw and forced her mouth open. He grinned as his long slim cock slid over her lips, her lipstick leaving a red smear on the smooth translucent flesh.

Alex had heard Andrew say the words 'before I fuck you' and knew what she had to do. She looked up into Andrew's cruel eyes with her own wide big blue eyes that were full of fear. Alex guessed that Andrew would get off on this. She tentatively suckled his cock, using her lips on the shaft, slipping her tongue under the glans, licking his fraenulum.

Andrew gasped and entwined his fingers in her blonde locks and began to fuck her face. Once Alex learned to breathe in and out through her nose the task became simple. All she had to do was suck on Andrew's appendage. It was long but not thick and she could easily accommodate him in her mouth.

Within minutes Alex had become an accomplished fellatrix. She suckled his bloated phallus, stopping frequently to pop it out of her mouth and kiss and caress it and then when she felt him become insistent she slipped him back into her mouth and went back to work with her lips and tongue. She slathered her tongue around the underside of his glans, swallowing the sweet nectar of his precum and worked her lips up and down the shaft.

She used one hand to lightly caress his scrotum, alternatively tickling it with her fingertips and then slightly scratching it with her fingernails. Her other hand snaked up his body and tweaked a nipple.

The desired result took quite a while to be realised because as soon as Andrew felt he was about to climax he would rip his cock from Alex's mouth, drag her to her feet and kiss her and fondle her and begin the process all over again. If Alex was honest with herself she would admit that she was beginning to enjoy being treated a little roughly and enjoying the ongoing tension of bringing Andrew close to release and then backing off.

In fact she began to do just that without further encouragement. She sucked his bloated organ, swallowing the bitter-sweet pre-ejaculate and then she immediately stopped when she felt it begin to pulse prior to extremis. Then she would leap to her feet and press her body against him like wanton whore, kissing him with her lipstick-smeared mouth, her fingers raking his flesh, her stockinged leg snaked around him, grinding her pubis into his.

Then she would drop to her knees and start sucking him all over again.

Andrew moaned and groaned and whined and whinnied until he couldn't take it any longer. This slattern's mouth was driving him insane.

He clamped one hand either side of her face and fucked Alex's mouth until his scrotum roiled and his cock exploded.

Alex tried to swallow all of the musky issue as it spewed from his cock but she couldn't and a runnel of creamy white spunk ran down her chin. Alex looked down at her pretty face: her eyes filled with trepidation and shock, her pretty mouth stained with smeared lipstick, her eye makeup smudged, eyeliner and mascara running down her cheeks as tears filled her eyes.

Andrew ripped his cock from Alex's mouth and spattered that last of his issue on her face. Clumps of hot semen splattered across her cheeks onto her eyelashes. A second smattering of his essence spurted onto her lips and her chin. A third rope of scalding sperm fell onto her platinum locks, a string of semen dangled from her fringe like an accusatory stalactite. Her face was a mask of ruined makeup and spattered semen. Despite the mess she was still beautiful to look at.

Andrew's breathing was deep and erratic. It was one of the most forceful orgasms he had ever experienced. His only regret was that he hadn't fucked her.

He guessed that it might have been her plan all along: suck him to climax so that he wouldn't fuck her. Well he was definitely going to fuck her the next time he came to 32 Clifton Road and that would be soon. The gorgeous young tranny was eminently fuckable!

Andrew wiped his cock on Alex's face, comingling his semen with her makeup; a last act of defiance and punishment.

Alex fell to the floor and hugged herself. She felt sorry for herself but also disgusted with herself. Despite her feigned indignation she was sporting an erection. Her cock was pressing against her flimsy nylon knickers and it was rampant. Although she felt used and debased she also felt powerful and in control. She had made Andrew act the way she wanted him to act; to become angry and impatient and fuck her mouth and surrender his seed so that he was spent and unable to fuck her.

Alex lay silently on the floor until Andrew left the room then she leapt to her feet and scampered to the bathroom on tottering high heels. She looked at her face in the mirror: still pretty but her makeup smeared and ruined and comingled with Andrew's drying semen. She looked disgusting. She looked like a slattern. But she desperately wanted to take her penis out of her knickers and stroke it furiously while she looked at herself but she resisted the urge.

Instead she washed the semen off her face and wiped it out of her hair and went back to her room and redid her makeup: heavy and slutty just like it was before and she coiffed and sprayed her hair.

"You must have done a really good job on Andrew. He's booked you for an hour next Friday and he left you a generous tip," Julie chuckled and handed Alex another scotch and coke; this time it was a double.

"It was awful! It was debasing and disgusting," Alex whined.

"If there was any way to stop this I would," Alex huffed.

"Methinks the lady doth protest too much," Julie chuckled.

"What am I to do mother? Where am I to go? Who am I going to tell?" Alex snapped at Julie and gulped at her drink.

"Oh don't be so dramatic. It's only sex! You've only got one punter left to go and you're finished for the night. You will have earned more in one night than I earn in a fortnight so stop your whinging," Julie snapped.

They both smoked in silence and Julie helped Alex properly adjust her clothing and fix her makeup. For a few seconds it felt to Alex like they were mother and daughter. They had both just finished their second cigarette and third scotch and coke when the doorbell rang and the ritual continued.

Dennis was in his early thirties, handsome, virile and eager.

He eyed Alex up and down and smiled at her.

"You are the most beautiful thing that I have ever seen," Dennis whispered as he began to undress.

Alex was over it by now. Two men had used her for their pleasure and she had submitted to both but she felt guilty about it after. She lay on the bed and watched Dennis undress. He turned towards her and he looked even more handsome naked. Dennis's limbs were muscled, his pectoral muscles well-defined and his stomach flat as a washboard. His cock was long and thick and swung from side to side, semi-erect already as he approached the bed.

"What do you want to do?" Alex just wanted to get it over with.

"I want to fuck you of course," Dennis smiled down at her and he reached out and stroked her blonde hair.

Alex shuddered. Dennis's cock was inches from her eyes and the very thought or that monstrous thing going anywhere near her anus made her baulk.

"Let's do something else," Alex reached out and took Dennis's massive cock in her hand began to stroke it.

It was sleek and warm, the veins defined and pulsing, the pink glans exposed and glistening with dewy pre-ejaculate. Alex felt the appendage grow in her hand as she caressed it. It seemed to throb with tantric energy. She felt both terrified and powerful and also a little ashamed.

The thought of having to suckle this monster cock or even worse, allowing it to enter her was terrifying but the power she held over this man was thrilling. Dennis was mewing and groaning; encouraging Alex to stroke his phallus; almost begging her.

"Oh yes honey, oh that is so wonderful, please don't stop, yes... that's it... right there... oh my god!" Dennis moaned; his knees trembling as Alex caressed his cock.

She cupped his large scrotum and gently squeezed and stroked it whilst the fingers of her other hand featherlightly ran up down Dennis's engorged penis, her fingernails gently scouring the velvety flesh, the pad of a finger circling his fraenulum. His cock was rock hard a runnel or clear pre-ejaculate hung from the glans in a silver thread.

It was this that made Alex feel powerful. She could feel her own cock awakening inside her knickers.

And this is what also made Alex feel ashamed.

Alex had only been with two men and already she was behaving like a slattern but even worse she was enjoying the power of it; the sexual energy, the need that the men had for her; their lust for her; their craving. She was scared that it might become addictive.

The bedsprings creaked as Dennis climbed onto it and lay down beside her. Her hand was still on his cock, stroking and caressing the sleek appendage and when Dennis put his lips on hers she kneaded it a little quicker and squeezed it a little harder. She willingly opened her mouth and her tongue met Dennis's and they intertwined as Dennis pulled her close and pressed her body to his.

They kissed languidly; their passion bubbling away just below the surface. Dennis stroked her hair and told her that she was beautiful and sexy and delightful, between bouts of kissing. His hands began to explore her body, stroking her stocking-tops, softly caressing her bottom, circling her nipples on her flat chest.

His handsome face began a journey. His mouth suckled her earlobes and he nipped them gently, he softly kissed her neck and the hollows of her shoulders, down her décolletage to her tiny breasts. She hadn't padded her breasts exactly for this reason; although she didn't have any real heft to her breasts she did have very sensitive nipples and Dennis's lips and teeth found them.

He peeled down the top of her basque and his mouth fell on her little breasts, his lips sucking on the tiny teats, his teeth nipping her nipples gently. Her nipples hardened and she growled deep down in her throat. At the same time Dennis's fingers squeezed her plump buttocks a little harder and it felt heavenly.

Alex's cock had sprung free of the confines of her perineum and tented the front of her knickers and when Dennis's hand drifted across her stocking-sheathed thighs and brushed the engorged organ she shuddered. It was the first time a man had ever touched her there and she liked it.

She gripped Dennis's cock even harder and began to stroke it vigorously. She wanted him to climax quickly, not because he was hurting her but because she was enjoying it and she felt that she shouldn't.

"Please don't," Alex tried to push Dennis's hand away from her groin.

This only made Dennis more insistent and he caressed her throbbing organ through her knickers and put his mouth on hers. Alex shuddered with the ecstasy of it. The taste of Dennis's mouth, his lips crushing hers, his tongue exploring her mouth, her nipples still burning from where Dennis had lapped and nipped at them, her thighs tingling from the ghost of his caresses and her cock radiating circlets of intense pleasure as Alex stroked it.

Alex rolled over on her back like a slattern and opened her legs so that Dennis could climb on her; his cock pressing against hers, the silky gossamer of her knickers intensifying their pleasure. They kissed fervidly, her heart beating faster, her breathing ragged. She locked her legs around him and pulled him tight, her lips crushing his, their tongues deep in each other's mouth.

The circlets of pleasure radiating from her crotch intensified as Dennis ground his cock against her, rubbing it, pressing it, humping her. Dennis could feel Alex's cock, fully engorged inside her silky-soft knickers. He liked the feel of it pressing on his organ; the slippery knicker-fabric enhancing the sensation.

Alex was no longer reticent and Dennis decided it was time to strike while the iron was hot.

He'd spied the lube of lubricant on the bedside table and his fingers scrambled for it, clumsily unscrewing the cap with one hand. He squeezed a dollop of the viscous gel onto his hand and smiled at his ingenuity. Alex had no idea what he doing.

She first became aware of it when Dennis slipped a hand inside her knickers and pushed the viscous gel between her buttocks, onto her puckered sphincter. The gel was slippery and cold and shouldn't be there and Alex began to panic.

She unhooked her legs from around Dennis's body and beat her hands on his chest, trying to drive him off her but Dennis just persisted and eased the gusset of knickers aside and pushed his cock into the crevice between her buttocks.

"Stop! Don't!" Alex screamed.

"Ready?" Dennis smiled down at her as if he hadn't heard a word she'd said.

He covered her mouth with his to stifle her screams as he slowly impaled her on his enormous, engorged phallus.

Alex felt like she was being ripped open by a red hot poker. Her sphincter stretched until Dennis's glands were able to pierce it and then the full length of his shaft slowly distended her virgin anus. Dennis pushed until it was fully inside her and his scrotum bounced on her perineum.

The pain was unimaginable. It almost felt like he was tearing her apart. But at least Dennis stopped when his penis was fully inside her and Alex's screams became gentle sobs

"I'm sorry; I didn't know this was your first time. You're a brass; I thought you'd had hundreds of cocks up you," Dennis whispered trying not to orgasm because Alex's anus was gripping his cock like a tight sheath.

"I'm not a brass!" Alex was able to whisper indignantly through the pain.

She realised how phoney this sounded. Hadn't she just had sex with two men for money?

"Well I wasn't but I am now," Alex pouted.

She realised how silly this sounded coming from a transvestite lying on her back wearing full makeup, dressed in a sexy basque, fully-fashioned stockings, slinky knickers and high heels, with a man lying between her legs with his cock buried up to the hilt inside her.

"I suppose you are. But you are still beautiful and adorable," Dennis kissed the tip of her nose.

"This coming from a man who has his cock stuck up my arse," Alex whined.

It was then that she realised that the pain had gone away. Not only had it gone away, something wonderfully decadent had replaced it. A deep perception of delectability was radiating from her prostate and as Dennis's cock continued to press on it the feeling intensified into a sphere of sexual bliss. Her stretched sphincter was no longer aching; it was emitting little sparklets on intense pleasure. Her anus felt full and bloated but in a good way. She was accommodating Dennis's engorged phallus quite comfortably now.

"Well come on then. Do what you said you were going to do. Fuck me," Alex said sulkily and looked up at Dennis with a challenging grimace on her face.

Just hearing her say 'fuck me' was enough to send Dennis over the top.

He gripped Alex by the shoulders and thrust once, twice three times and then he ejaculated deep in her bowel.

Alex grimaced and grunted each time Dennis's cock thrust in and out of tight channel. As he did so his hard belly pressed on her engorged cock, still trapped inside her knickers. It was heaven.

She felt Dennis ejaculate deep inside her. His cock shuddered and she could feel his scalding semen filling her anus. His whole body shook with a paroxysm of pleasure and his mouth fell on hers and he kissed her passionately as he voided his essence inside her.

Instinctively Alex wrapped her diaphanous-sheer-stocking-clad legs around him, her high heels raked his flesh as they drummed on his muscled black. Her nails tore at his skin and she raised her hips to grind against him as she filled her knickers with her issue. Her sphincter palpitated and clung to the shaft of Dennis's cock as he rammed it in and out of her tight channel, the spongy mass of her anus clutched his throbbing cock, milking him of his seed and his glans spewed forth the viscous profusion of his semen and pressed on Alex's prostate, intensifying her orgasm into a mind-blowing blissful explosion of pleasure.

The two lovers clutched at each other, reluctant to relinquish the satiety that they felt in each other's arms.

Alex's big blue eyes gazed up at Dennis's handsome face.

"Do that again," she whispered and she pulled him close, her ankles locked behind his back as he wriggled her body under him.

Dennis smiled down at her and kissed her and then he granted her wish and he did it to her all over again. This time it was slower and more loving, each of them extracting every scintilla of pleasure from the other.

When Dennis was sated and could no longer perform and Alex's anus was numb, but in a wonderfully decadent way, they said their goodbyes. Alex escorted Dennis to the landing at the top of the staircase and kissed him farewell with a long lingering kiss.

Julie stood at the bottom of the staircase and smiled up at them.

Dennis paid Julie the agreed stipend and added a generous tip and told Julie that he would be back soon to see Alex. Julie closed the door to 32 Clifton Road and looked up at Alex who leaning on the newel post smoking a cigarette and drinking the remaining dregs of her scotch and coke.

"I'll take four gentleman callers tomorrow night mother. Bring me up a fresh drink please," Alex smiled smugly at her mother then turned away.

The End

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
18 Comments
juliemay808juliemay8086 months ago

Oh what a wonderful story takes me back to the 80s where being a girl was a lot harder but so pleasurable and the joys of the first time with a man Absolutely love this great writing

richgo50richgo506 months ago

Excellent story. Well developed. Liked Mom and son quite a bit. Personally I wanted to read about mom sucking Alex off, but that is just my perversion. Even though you knew where the story was going, it was so expertly written that I wish there were four more pages to read.

BrendaNWBrendaNW7 months ago

Hot and sexy story .. you got me wet and horny 😘

7Locks7Locks7 months ago

Excellent writing, as usual. You write the sex scenes so well. I also enjoy your clothing descriptions.

AnonymousAnonymous7 months ago

I loved it 😍

Show More
Share this Story

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
More Stories