Colon-Snake Convent

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'Do you want to become head acolyte? Maybe an envoy?'

'I'd love to travel, Master, so it'd be nice to be an envoy.'

'You'd want to leave my convent?'

'No, Master, I'd also be happy to—'

'There you go,' he said as the flexible dildo slipped further inside, eliciting a soft gasp from the girl. 'It has just entered your sigmoid colon; it should be easier from here.'

'It feels weird, Master.'

'Not painful, though?'

'Erm... no, Master,' she said as it crept ever deeper.

'That's fine then.'

Jessica trusted her master, and she tried her best to push aside the sudden anxiety that came with the revelation that he was pushing it deep into her intestine. Until now, she had assumed that the name of the ridiculous sex toy was merely a boastful exaggeration. The special, deep enema that Mr Cager had given her earlier that morning now made sense to her; she had thought it was just to ensure that she was extra clean for her special day.

She felt it burrow into her bowel, freely delving into the recesses of her body, impervious to the extraordinary nature of its incursion. It was an odd sensation -- neither pleasurable nor painful -- and as she got used to its intrusive presence, she began to experience a strange thrill. The thought of it reaching so deep into her belly awakened in her a kinky inclination that she was not previously aware of.

'Just one more bend to navigate,' he said as the obscene toy encountered more resistance, 'but it shouldn't need too much goading.'

Jessica felt it tug at her innards as it tackled the crook in her bowel, and she watched his hand twist and turn with intricate movements as he tried to coax it past the obstacle. She was slightly alarmed to see that there was still maybe twelve inches to go -- the base of the toy flopped about under his arm as he tried to feed the shaft deeper inside -- and she had to remind herself that her master would not harm her.

'Well done, Jessica,' he said. 'This is the last stretch; we've successfully accessed your descending colon!'

'Thank you, Master,' she said as the pressure eased and the snake continued its audacious journey.

She forced herself to adopt an unconcerned expression as it slowly tunnelled through her abdomen towards her rib cage. Her master rubbed her belly again, pressing firmly as though searching for something.

'Mr Cager,' he said with a satisfied smile, 'would you please release one of Jessica's arms?'

'Of course, sir.'

'This will be novel for you, Jessica,' said her master as she was freed from one of her bonds. 'Give me your hand.'

Obeying his command, she let him guide her hand -- small and girly next to his manly appendage -- to her abdomen and press it into her flesh. She realised with a start that she could feel the bulge of the object inside her.

'Could it poke my other organs?' she blurted, no longer caring if she appeared foolish. She didn't know much about human anatomy, but she knew there was important stuff inside her chest.

Her master laughed. 'An understandable concern. No, it won't exit your bowls.'

'But aren't there other organs there?' she insisted, feeling the bulge roll under her fingers.

'The tip may say hello to your stomach and spleen, but from within your intestine.'

Not entirely convinced, Jessica wanted to continue her questioning, but she felt the base of the absurd toy press against her bottom, completing its seemingly endless advance, and she fought the urge to take a deep sigh of relief. She felt the protrusion beneath her fingers stop just short of entering her rib cage.

'Well done, Jessica,' he said, grabbing a breast and giving it a congratulatory squeeze, 'you have passed with flying colours.' He turned to the supervisor. 'I'll give her a nine for that; she took the entire length without much fuss.'

'That'll put her in the top five on the board, sir,' replied Mr Cager. 'Shall I fetch her an acolyte uniform?'

'Yes, I think she's earned an early promotion.'

The supervisor nodded and left the room, and Jessica had to contain her elation while her master gently fucked her insides. Her jubilation was tempered by the knowledge that she would be despised by her novice peers who had been in the convent for months and even years. Indeed, even the acolytes would see her as a jumped-up inferior.

'You're allowed to be happy, Jessica,' said Master Radell, slipping a couple of digits into her wet cunt and causing her anus to tighten around the embedded snake.

'I am, Master,' she said with a grateful smile. 'Thank you so much!'

'You'll wear your new uniform well. I'll be showing you off to our members, so you'll quickly grow into your new rank.'

'I hope I make you proud, Master,' she said, watching the bump glide back and forth under her skin.

The supervisor returned and stood waiting with a neatly folded garment. Jessica caught his eye while her master's glistening fingers dipped in and out of her pussy, and she thought she detected a hint of frustration. He quickly looked away as though aware of his accidental communication.

'You can touch yourself if you want,' Master Radell suggested, taking her delicate hand and placing it on her moist sex.

'Oh, thank you, Master,' she said, a little hesitantly.

'Go ahead,' he said, squeezing her impaled bottom encouragingly.

Tentatively at first, she put her fingers to work, and she soon had them darting nimbly over her swollen clit, sliding smoothly in her juices and sending waves of pleasure coursing through her body. She watched attentively as the faint swell made its way up and down her belly, following the path of her descending colon, and the sheer deviance of it spurred her on in her quest for a second orgasm. Even the lecherous gaze of the supervisor was enough to feed her lust, and she was once again lost in a world of euphoric pleasure.

The snake reached as far into her body as it could as her master pushed its base firmly against her bottom, and the juices flooded from her pussy, spilling over the butt of the toy and soaking the chair afresh. She writhed in her remaining restraints, gripped by another turbulent frenzy of ecstasy; her anus grasped the dildo in a series of spasming contractions while her fingers continued frantically slipping around her throbbing bud and among her slick lips.

When she could no longer touch her insanely sensitive clit, she stopped abruptly, arching her back as the last of the fluids flowed forth to join the puddle she was now sitting in.

'It's always a joy to end with a high,' said Master Radell, fondly caressing her chest.

Jessica could only offer a drained smile. She had a feeling that she was going to have a great relationship with her master. She hoped that the other girls wouldn't be too jealous.

'Mr Cager,' he said, a hand still resting on her exposed chest, 'would you finish off? I'm going to be late for a meeting.'

'Of course, sir.'

Jessica thought the supervisor had a look of suppressed glee as her master rose from his chair and planted a kiss on her nipple and her forehead. She felt silly after instinctively angling her head to receive the kiss on her lips. Master Radell pretended he didn't notice, but Mr Cager's lips curled into a smirk as the other man left the room. She lay there regretting the embarrassing yet insignificant moment while she waited for the supervisor to release her bonds.

He went to her bound wrist and started to loosen the strap, but he paused and looked thoughtful. Making a decision, he took her free arm and positioned it to place it back in its restraint.

'Oh, aren't you supposed to release me, sir?'

'You don't mind if I just have a little moment to, uh...'

Jessica giggled as he tightened the strap. 'Of course you can, sir!'

'I'm so fucking horny after watching all that,' he said, pulling a lever on the side of her chair.

She gasped with surprise as she tilted backwards so that her bottom was higher than her head, and he toggled another control which caused the headrest to fall away, leaving her head and hair dangling.

'I had no idea this seat could do this,' she laughed, watching with an upside-down view as he unzipped his trousers and his stiff cock jumped out, almost slapping her face.

She opened her mouth, inviting him inside, and he slid his solid shaft right to the back of her throat, making her gag. She had taken him into her throat so many times in the last two weeks that the reflex no longer bothered her so much; she knew that she would not choke, and that she would not have to endure it for very long. The position of her head formed a straight passage into her throat, and he made the most of it, probing deeper than ever while she emitted wet, gargling noises.

Even while her body convulsed as she retched, she appreciated the aptness of his extended exploration of her gullet after what her master had just done to her. Indeed, the silicone snake was still hanging out of her bottom, and she imagined the two intrusions reaching right into her core and somehow meeting in the middle.

He gathered her breasts and pressed them together, kneading and palpating with increasing urgency, finding pleasure in the involuntary spasms which made her chest heave under his hands. It wasn't long before she felt the warmth of his seed as it spurted into her oesophagus. His enthusiastic thrusting ceased, and he pressed his pubis against her face, holding it there while his excited organ twitched and pulsated in the furthest reaches of the passage.

As the softening length slowly withdrew, Jessica's excitement grew; she was about to leave her master's office as an acolyte!

'Thank you, I needed that,' he said, letting his penis flip out of her mouth.

'That's alright, sir,' she said, smiling up at him through watery eyes. She took some deep breaths, enjoying the ease of a bodily function that she could usually take for granted.

He finally went about freeing her from her bondage, his demeanour brighter than it was earlier. She kept her legs open for him as he began the slow process of removing the super-long dildo. He didn't bother to reconfigure the chair, so her head remained dangling, and the extraction took place beyond her vision. She felt it pull at her innards as it retreated from her colon, snaking around the two bends with much greater ease than when it had entered. Her belly felt strangely empty when only her rectum was occupied, and she wondered when she might have her bowels filled again.

'That's a well-trained arse if ever I saw one,' said the supervisor, slipping a couple of fingers inside as soon as the head of the toy vacated her anus.

'Thank you, sir,' she replied, waiting for his rummaging digits to withdraw before closing her legs and sitting up.

Mr Cager helped her off the chair and onto her stilettos, and she felt a conspicuous dampness on the back of her skirt as it fell back over her thoroughly tested bottom.

'Let's get you out of this,' he said, sliding the novice jacket off her shoulders.

'I'm so excited,' she said, momentarily topless.

'As Master Radell says, you've earned it,' he said, tweaking an erect nipple before helping her into the acolyte jacket. He zipped it up for her and squeezed her breasts through the luxuriously silky fabric which barely covered them. 'You're officially an acolyte. Congratulations!'

'Thank you!' she said, struggling to contain her joy.

Releasing her soft chest, he opened the door and gestured her into the corridor. Girls who had moments earlier been her fellow novices regarded her with surprise and envy; they would now have to defer to her, but she certainly didn't feel that she could wear her new uniform with any degree of authority or arrogance, so she made a concerted effort to look humble as she made her way back to her room.

Seeing that her dormitory was empty, she sprang onto her bed and rummaged through her bedside cabinet. She retrieved her anal training dildo set and selected the largest one, which she had so far avoided using. She hurriedly smothered it in lube and lay back, spreading her legs. As she pushed it inside, she retreated into her head, reliving her incredible rite of passage from the beginning.


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DiaperboyMiDiaperboyMiover 1 year ago

Wow...awesome story!!!!!

Bailey_R_BrittonBailey_R_Brittonover 2 years agoAuthor

Thanks for the kind words, Popperotica!

I wish you great success in your writing.

popperoticapopperoticaover 2 years ago

Really enjoy your normalizing the most intimate and deviant acts and the enjoyment of willing participants rather than some supposed horror when sex gets beyond the prudish. Thanks. Please share some tips with a beginning writer!

AnonymousAnonymousabout 3 years ago

Not bad, but I amsorry you have to put up with this horrible formal format. High time the stories went back to the original style. Please pass that on to Literotica.

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