Broken on My Break

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
TopSeeker
TopSeeker
196 Followers

I lifted my head and that ebony beauty's smile nearly took in her ears, "Don't worry about me just yet little boy. I won't feed you until after you've sprayed that smooth little body of yours with your own sissy cum!" I dropped my gaze back to my Scarlet haired rapist.

Her hands were already working lube over her weapon. "Stare into my eyes slut, you aren't broken let alone broken in yet." her smirk deepened, "By the time we are done your ass will be destroyed and loose enough we could slip into you dry any time we choose to... which will be often." She dried her hands on a nearby towel and then forced my knees further back. I felt horror and disbelief as the tip of her dick touched my already spread ass crack. When I felt the heat of her cock cover my hole and then some. I began to cry silently. Her tits jiggled as a shiver passed through her. "Here comes my favorite part."

Slowly the pressure on my anus built. An intense burning sensation began and I felt the skin turn inward. Charity's deep voice interceded "Bear down little boy, it will help" I did so and felt the ring relax only slightly, but it was enough. The slick head started to spread my most private of places open. Bit by bit that monstrous meat was beginning to enter me. Veronica wiggled back and forth, whimpering in anticipation and frustration.

My vision exploded in lights from the pain as just the head popped on and the ring snapped shut just behind it. She leaned over and moaned as her tongue dominated my quivering mouth. Sweat already coated my chest, from her or me I didn't know. I already felt like a massive ball had been shoved up my ass and I knew it was just the head and head probably another 11 or 12 inches to go. Soon she was whimpering like a puppy as she humped me. Still my ring was so tight that the little increase in thickness wouldn't allow any progress. She ceased the sloppy kiss and watched my eyes. I grimaced and bore down again. With another little heave my asshole slipped over the ridge and she started to slide in deeper. My breath soon became shortened. I was so full I could believe it.

A zing of sensation electrified my cock and balls, I gasped. "Oh there it is!" the little she devil exclaimed. Whatever it was she hit, she was now angling her dick to meet it directly. Never had I experienced this much pleasure, especially with my ass aching more than anything had hurt before now. She kept at it until I lost my balance even just laying beneath her. Giggles filled my ears and just as the previous pain faded away a new deeper pain filled my bowels. More of my breath was lost. My check stung as I was sharply reminded to stare into her eyes. I took a moment too long and my already constricted testicles were squeezed. Shaking and dizzy I stared right into the green abyss of her eyes. Another shove and my bowels started to move of their own accord, attempting to accommodate the invading behemoth.

She started slow and short, exhaling with each inward stroke. Every movement reducing the pain, producing another long jolt of pleasure, and yet another deeper pain. Her strokes lengthened. The shaft began making the sphincter feel incredible along with the prostate massage. An inadvertent groan escaped my lips. Something shifted in her eyes as her brow furrowed and her hips and member became more demanding.

Pain mixed with pleasure flared as her cock finally bottomed out. She whimpered and huffed, "Time to get inside the colon whore..." My intestines were stirred as she rotated the log first one way and then the other. Soon she was sliding deeper past a new burst of pain in my gut. Her abs felt as though they were made of steel, as her pelvic bone crushed my nuts against me. My mouth fell open and a squeak came out. "Such a good little slut, not long now until you are mine totally..." She ground in a wide circle at full depth. I couldn't get a breath in as my innards were stirred.

"I know that look, ready or not here she goes!" I had almost forgotten about the African here holding my head. With a long slow pull out Veronica lay flat on me, breath right on my nose as she stared into my soul. My prostate was vibrating with pleasure and my hole sang with joy. SLAM! I screamed, not completely in pain. My entire field of vision was green eyes, My body filled with the intense sensation of being fucked. My skin was on fire and incredibly sensitive. The softness and warmth of her skin against mine covering my body and feeling tits with rock hard nipples digging into my chest, it was all so was erotic.

This feeling was incredible, I never knew such forbidden pleasure could exist. She repeated the motion again. The slow withdraw and then crushing blow, flattening my constricted balls with her iron hard abs. Again and again the sequence repeated, each time faster and with a feminine grunt. Soon I was wobbling and shaking both from the sensory overload and the repeated flows of the crotch against my ass. The feeling of her formidable balls slapping against my ass was erotic in a way I had never known.

I tried to scream as my body was wracked with mind numbing sensations but no sound could exit my throat. My hole was heating up from the fast friction as she continued to use full strokes. I could feel an orgasm crash against some wall and my legs began to shake uncontrollably. The pressure in my balls suddenly released without warning. I could register only the explosion and release like a massive balloon popped, yes it didn't cease and continued as long as I was being hammered and my balls continually crushed. I felt the war wetness of tit flesh leave my chest and stream after stream of hot goo splash my chest and face. She let out a long moan, "There is our little toy, I love feeling a brand new fuckhole squeezing my cock over and over like this."

My red haired mistress never stopped pummeling my body. Her teeth were grit and nostrils flared as she worked. She sat up, her thrusts getting even deeper than I had though possible, open mouthed squeaks being emitted at the end of each thrust.

A sharp yank ripped my gaze from her. I was now looking down the barrel of a biological WMD, dark as midnight and pulsing. Even in my haze of pleasure I saw the clear drip fall from its tip. My mouth was already open in a silent scream when suddenly instead of just seeing it I could taste it. In a single thrust my throat felt like it had been torn open. Charity wasn't quite as long as Veronica but it was a damn close thing. What she was, was thicker. Her testicles were tighter and it felt like soft marbles slamming into my eye sockets as she too began to ravage my body with full strokes. Quickly increasing in tempo to match my other mistress. After a bit even my throat rape started to feel good, like a long sexually charged throat massage from the inside.

I have no idea how long they carried on like that, using my body like it was some frenzied lifeline. I could barely make out the sounds of sloppy kissing, moans and whimpers above me. A hand crushed my nuts in a vice grip as both cocks slammed deep and just began to grind as hard as they could. Hot lava filled my intestines flooding my core with heat I could feel it, both traveling deep and leaking along the entire length, spraying out my stuffed hole. While all I knew now, was I had to swallow what seemed to be a pint of cum from the pulsing meat lodged in my throat. After some circular grinding on both ends, the pleasure sticks withdrew reluctantly. The chocolate treat stopping just long enough for me to try and get more sustenance straight from the tap...

"So little boy, how do you feel now?" Higher pitched, that was Mistress Veronica.

My blacked out vision faded back in, the sight of the big black cock filed me with a desire for more. All I knew was more, no other thought could fill my head and my brain felt like mush. I lifted my abused fuckhole from the mattress and humped at empty air, looking for something to fill it as I open mouth whimpered at the treat just out of reach.

Deep laughter echoed and that obsidian source of sustenance and pleasure wagged in front of me, "I think that was our answer sis, but lets switch this time. I want to take our new toy on his hands and knees.

The details were a blur for me. The only thing on my mind was being complete again. Once free I spotted the pale pillar between its owners legs at the head of the bed and scrambled on all fours for it. Once I had reach it I slammed it all the way down of my own volition, not caring that I was still gagging. A pair of small hands grabbed my hips and a sharp pain shot through my butt when my fuckhole was re-stretched out, with threatening growls behind me. The angle was almost straight down though. A direct slam into my prostate on each down-stroke. My own moans produced moans from Mistress Veronica as Mistress Charity began to abuse my prostate, growling at me as she did so. I felt complete again. Every single nerve in my ass was electrified and exploded in pleasure as my new purpose sawed in and out of me. I tried my best to work for another meal from the meat in my throat. It must not have been good enough because Mistress Veronica soon grabbed my head and was fucking my face harder and faster than I could have moved on my own. I lost track of time again and came to as the I heard the Irish woman's voice cry out.

"OH FUCK! Here we go again, TASTE THE WHOLE LOAD YOU SLUT!" and my head was then held so that just the cockhead filled my mouth. I closed my mouth around it and sucked as hard as I could, screaming and moaning on it as my newly christened fuckhole continued to be abused. The force behind each cumshot was incredible. I swallowed as fast as I could, letting very little escape. The assault on my ass slowed enough for me to clean Veronica's cock off before she moved. Suddenly my ass was being slammed deep and harder than I had felt thus far, each stroke accompanied by a rough feminine grunt. I couldn't control it. I stayed on my knees but my chest dropped to the mattress, eyes rolled back in my head, and I began to continually scream. The hand that crushed my balls was the last straw and I started cumming, my ass convulsing through the entire orgasm. Three more massive impacts deep inside my ass and then my bowels were overflowing with my Mistress's gooey gift. The pressure on the nuts released and I collapsed forward. A flood of warm cum poured out of my now gaping hole, covering my balls.

As my consciousness faded I heard my new owners talking.

"We should probably let him rest a little bit."

"Just for a little bit. Then we wash him up and do it all over again!"

"I'm going to love waking up to shooting an orgasm down this toys throat all week..."..."

TopSeeker
TopSeeker
196 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
28 Comments
AnonymousAnonymous12 months ago

Alsome I so looking for .y first time so very much

Sassybutterfly99Sassybutterfly99over 1 year ago

Was going great until he stared liking it 😢

AnonymousAnonymousover 1 year ago

You know I been straight for 59 years of my life and I trying to sever my mistresses but I been trying to stay straight but I think it's going to end in December I read this make me want it so bad please make more of this stories

AnonymousAnonymousover 1 year ago

Well I hope you finish the story with the hottest part which is when they cut his throat with the scalpel and watch him choke to death as he bleeds out. Now that is sexy!

AnonymousAnonymousover 2 years ago

You deliberately ignored the disclaimer at the beginning and the tags just to insult people? Come on now

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Turned Out A male college student gets used by a dickgirl classmate.in Sci-Fi & Fantasy
Brutal Shemale Lovers Pt. 01 Jake gets more than he bargained for from Tanya and Sarah.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
More Stories