Sent Away Ch. 04

Story Info
The Sissy's humiliation increases.
1.7k words
4.4
10.5k
11

Part 4 of the 11 part series

Updated 06/11/2023
Created 03/10/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

This is the fourth chapter of a multi-chapter story of a young man being turned into a crossdressing sissy slut.

While I licked clean the cum stains from the couch and floor my mother and Harry drank and discussed my 'future'. My mother was slurring her words and befuddled as Harry regaled her with his ideas on curing her son of his deviant sexual urges, maybe even making a man out of me. "Well you see Bonnie," Harry mused, "I intend to show the boi first hand how terrible it is to be a Sissy in a man's world."

"Oooo," my mother sighed cluelessly while casting Harry a bemused look of adoration, "are you sure it's not too much trouble."

"Not too much trouble at all babe," Harry assured her, "I feel it's my duty and a real privilege to help you and the boi out." While my drunk mother nodded her head blankly, Harry caught my eye and winked. I felt my body shudder in response.

Smiling wanly my drunk mother slurred, "He is so lucky to have you honey."

"Yes, he sure is," Harry murmured quietly before snapping, "crawl over here boi."

My mothers dull eyes watched me with contempt as I complied and crawled to the spot before them with my caged cock swaying heavily between my thighs. "Kneel," Harry demanded tersely and gingerly I did, keeping my head bowed focusing on the floor. Slowly one of Harry's feet edged towards me. Above me Harry's disembodied voice commanded, "Kiss my boot boi."

Hesitantly and hating myself I lent forward to carefully peck Harry's proffered boot. Over my mothers snort of derision Harry pronounced, "Again." And I did. When I made to pull away Harry growled, "don't stop." And while my mother tittered with amusement I felt my body flush hotly with shame but I kept my lips glued to Harry's boot.

"You see babe," Harry crowed, "you have to teach a Sissy its place." I could hear my mothers chuckling agreement and cringed when Harry's voice announced, "Lick it." At first I couldn't believe it but when Harry flicked his foot into my lips I swallowed resignedly began licking his big black boot.

On the couch I could hear Harry making out with my mother and straining to look, I watched Harry's hand slip up beneath the hem of her dress. While I licked Harry's boot he frigged my mother and her moans of passion soon filled the room. She was too drunk to care that her lover was caressing her lustfully in front of her grovelling sissy son.

While my spirit withered with humiliation Harry skillfully manipulated my mother until she was horny and panting like a bitch in heat. She seemed oblivious to me on the floor as Harry slipped her panties down her legs and dropped them casually on my head. I could smell my mothers sex and feel the hot wetness of her panties. Shamefully I kept licking obediently at Harry's boot until he abruptly pulled it away.

Stunned, I froze until Harry's hoarse voice growled, "Look up here boi." Timidly I obeyed as mother's panties slipped from my head to fall into my lap. Distracted, I was stunned at the sight of my mother's bushy womanhood. She had her feet on the couch with her legs spread wide open exposing herself fully. Harry's hand cupped my mother's mound possessively with his fingers buried deep in her pussy. He pumped them absently into her as he smirked at me ogling my mother's wet cunt.

My mother either didn't care or was too overcome with her own base needs to worry about her own son seeing her exposed and fondled. With her head buried in Harry's shoulder she mewed quietly as her body twitched beneath Harry's skilled fingers. While he fiddled with my mothers pussy Harry asked, "What are you boi?"

Staring dumbfounded at his hand and my mother's hairy twat I mumbled dejectedly, "I'm a Sissy."

The hand in my mothers cunt lashed out, slapping me viciously across the face knocking me to the floor. Shocked by the harsh unexpected slap I lay there as my mother's squawk of distress turned into cruel laughter. "Kneel," Harry cursed and meekly I complied as my mother pulled Harry's hand suggestively back between her legs.

Absent mindedly Harry went back to caressing my mother's pussy while I knelt before him, with the left side of my face burning red with his hand print. In a casual tone Harry started lecturing me, "Boi you are a Sissy." Sadly sniffing back a tear I nodded yes and Harry continued, "As a Sissy you have got to know your place. And a Sissy is inferior to all men." And again I nodded while Harry's hand brought my mother to a noisy orgasm. While my mother squealed her pleasure Harry ignored her and his words crushed me, "For a Sissy it is always 'Yes Sir,' 'No Sir,' 'Three Bags Full Sir.' Do you understand Sissy?"

Sniffling some more and trying not to cry I whined forlornly, "Yes, Sir."

"Good Sissy," Harry snickered like he was talking to a wayward puppy and I flinched when he reached out to ruffle my hair good naturedly chuckling, "Yeah that's a good Sissy."

The hand ruffling my hair had just been fondling my mother's pussy when she had cum and as Harry gently stroked my cheek with it I could smell her scent. Using a slick finger to lift my chin so that I was staring into his glittering eyes Harry murmured playfully, "Now why don't be a very good Sissy now and try on your mommies panties for us."

I dared to give him a 'you can't be serious' look only to suffer another vicious slap that knocked me over leaving my face burning and my ears ringing. Not needing two I squirmed awkwardly on the floor struggling to pull on my mother's panties. They were a lace edged pair of white nylon briefs that were sheer enough that I could make out the metal cage about my cock and balls. I could feel the very damp crotch of her panties as I carefully resumed my position kneeling before the two of them.

"Oh Bonnie," Harry crowed looking me over, "now doesn't your Sissy boi here look cute in your panties."

Drunk and sex dazed my mother's slurred response dripped with the contempt she held for me, "Little fucking pervert." Then seething with anger she stomped her feet back onto the floor and leaning forward slapped me snarling, "Buy your own fuckin' panties you filthy little fucker!"

Though not as hard as Harry's, my mother's slap stung in a much more humiliating fashion. While I burned with shame and humiliation Harry chortled in the background, "I'll take your Sissy son panty shopping tomorrow Bonnie."

My mother glared at me, cleared her throat then scornfully spat in my hair. As her spit dribbled down my shocked forehead Harry laughed and my mother rose unsteadily. After making a fumbling attempt to straighten her clothing she stormed off. Harry just grinned his evil smile and chuckled to himself.

Sniffing forlornly, I hesitantly spread my knees apart when Harry pressed his spit slick boot against them. Cringing with fear I kept spreading my thighs until the toe of Harry's boot rested beneath my panty covered caged cock. Simpering with distress I raised my eyes slowly when he murmured quietly, "Sissy." Harry's eyes were so cold and vacant that I gasped with real fear.

My body began trembling as I stared into Harry's implacable eyes captivated while he drawled scornfully, "Hump my boot Sissy." Terrified and uncertain I slowly began rubbing my pantied crotch and caged cock back and forth over Harry's large black boot. While I rubbed Harry began tapping the toe of his boot into my crotch and balls. He did so slowly and softly at first causing my cock to swell uncomfortably in its cage but as I continued to hump his boot Harry picked up the tempo while increasing the force.

Soon I was grunting with every forceful tap while Harry bounced me up and down on his boot. It wasn't long before my grunts changed from distress to arousal. My cock was trying to become ever more painfully erect in its cage but Harry's toe pushing into my groin was all I could focus on. As the tempo and force increased I had to reach out and grasp Harry's leg to keep from toppling over. Harry was relentless and as I rode his boot I threw back my head howling wantonly as I came.

Stars, flashes, fireworks, the orgasm was so intense that I lost my senses falling against Harry's leg and holding on tight. I became vaguely aware that Harry's toe was still massaging my groin as his hand gently stroked my hair. My body shivered and trembled unconsciously as I clung to Harry's leg. After what seemed like forever Harry's stroking hand grasped a handful of my hair and pulled my head up. My body was limp and my vision was blurry as Harry smirked down at me.

Effortlessly the large man rose dragging me off his leg. Holding my swaying body by my hair Harry muttered, "Clean up your mess Sissy." On the toe of his boot I could see the wet cum that had seeped through my mothers panties. When Harry released my hair I slumped to the floor at his feet. When he nudged me with his boot I needed no further encouragement and promptly started licking away at the cum slick toe.

While I licked Harry's boot clean my mother returned with more drinks for them. Snuggling up to her man my mother slurred, "You've wasted enough time on this little prick for one day Honey." When Harry didn't respond she continued shrilly, "Let the little pervert do something useful while we fuck."

I heard Harry laugh but didn't dare stop licking his boot. My mother though, had had enough and using her foot pushed my face away from Harry's boot snearing, "Fuck off and go clean the kitchen you useless little shit." While I cringed on the floor she pushed past me dragging Harry towards the couch with her.

It wasn't long before I could hear them making out passionately and when I finally looked up my mother was pawing at Harry brazenly. Noticing that I was still in the room she stopped suddenly and threw half finished drink at me while screeching with fury, "Go clean the fucking kitchen already!"

Startled and hurt I scurried shamefully away on my hands and knees to do as I was told.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
sissyjolie4usissyjolie4uabout 2 years ago

This is becoming more and more interesting, can't wait for the next chapter.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Sissy's New Daddy Billie is forced to be a sub-sissy.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
Feminized by BBC Friend Ch. 01 My BBC friend slowly feminize me.in Transgender & Crossdressers
Blackmailed by Mr. B A student is blackmailed and used by an older man.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
More Stories