Ultimate Anal Stretching Program

Jason gets ready for Beginner's week of the stretching Program. He's supposed to undergo a quick examination by Dr Chen before the actual training starts. Sounds easy enough, right? Turns out Dr Chen has other, wicked plans. Thank you for the warm reception of my story. Comments are again much appreciated. Suggestions for future scenes as well!

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The Program Begins

Jason turns away from the door, faces Victor and starts following him down the corridor. 

“You have to excuse Dr Chen, he likes to be dramatic like that.” Victor says suddenly.

“Oh okay, that’s good to know, I honestly felt a little frightened for a second there.” Jason chuckles. 

They walk for quite a while, Victor expertly leading the way. They finally reach a dead end. The corridor expands into an oval room with a set of 4 doors leading out of it, their frames spaced equally from each other. There is a space for a name plate next to each one, but only one, Jason’s, is filled with a name. 

“Okay, here is your room. As you can see, there are more rooms here for other patients. Right now you’re the only one in the Beginner level. When you progress to higher levels, you’ll meet other guys participating in the Program. You can enter your room, K.A.I. will take care of the rest and explain the schedule for tomorrow.” Victor says while ushering Jason into his room.

“If you have any questions or needs just ask K.A.I. If it’s something he’s unable to help with, he’ll just call me.” 

“Okay, thank you Victor. I suppose I’ll see you around?” Jason asks. 

“Oh you will, for sure.” Victor responds with a small wink. “Now, off you go. Don’t stay late, you have a big day tomorrow!” Victor closes the door and leaves Jason alone in his room.

The room is quite spacious, the black and white decor ever present. There is a big, black, king sized bed covered in plush looking, white sheets in the middle. Next to it, up against the wall, there is a small, white desk with a sleek, black cylinder standing on it. The room connects to a private bathroom containing both a big shower and a tub, toilet, bidet and sink. Jason looks at the shower head - next to it, there is a long, thin attachment used for douching. “Right, of course they thought of everything.” he says to himself. 

His voice seemed to wake up K.A.I. from his slumber. An electronic, artificially generated male voice suddenly cuts the silence. 

“Hello Jason, my name is K.A.I. I’m an artificial intelligence system responsible for maintaining proper functioning of this facility. I’ll be helping you during your stay here.” 

“Yyy hello? Can you hear me?” Jason says unsure of himself. “Where are you exactly?”

“My local module is standing on your desk. My sensors though are located throughout the facility, so that I can help patients wherever they are.” K.A.I. says. “I was present during your talk with Dr Chen. And I’m going to be overseeing and participating in your training. Speaking of, I think it’s best if we get on with business. It’s getting late and a deep, long sleep is essential for the success of the Program.” 

“Below the bed there are two drawers. Please take off all your clothes, underwear included, and place it in the white drawer. After doing so, I’m going to lock this drawer. You will get your belongings back at the end of the Program.” K.A.I. continues. 

Jason is a bit weirded out by the concept of stripping in front of a computer who probably watches his every movement like a hawk, but he does so nevertheless. He shivers a bit when taking off his underwear. He places his clothes in the white drawer. A small click can be heard when the drawer slides back into its place. 

“Please move over to my local module. Stand in front of it. I need to take a quick scan of your pubic area to manufacture a custom-fitted cock cage for you.” 

“Ummm okay I guess.” Jason responds awkwardly, as he moves closer to the desk. 

“Please stand still.” K.A.I. orders. 

There is a beacon of blueish light shooting from the black cylinder, scanning Jason’s lower stomach, cock, balls and thighs up and down. 

“Now please, take your genitals in your hand and pull them upward - I need to scan the area below your balls as well.” 

“This is getting ridiculous.” Jason whispers again. He does as he’s told, the blue rays scanning his body a few more times. 

“Please wait, processing the scans and designing the cock cage.” 

After a couple minutes of idly standing and not knowing what to do with himself Jason hears K.A.I. speak again. 

“Cock cage ready. Please open the black drawer under your bed. There will be a set of clothes for you to wear to bed. Before you put them on, please wear and attach the cock cage securely. After you lock it with the provided key, there will be a small click again - you won’t be able to open the cage for a whole week of training. After 7 days the cage will be taken off for a quick hygiene routine and a new cage will be sent to you. Have you ever worn one and are familiar with the process of putting it on or do you need assistance?” K.A.I. asks. 

“No, I’m familiar, I think I’ll manage” Jason responds. He quickly changes his mind once he sees the complicated, openwork design of the cage. 

“You know what, on second thought I think I do need assistance.” 

“Vey well. First, take the black, trapezoid shaped ring and push it all the way against the skin of your stomach, pulling your balls through it. If you need some lubrication, there is a small packet of water soluble lube at the back of the drawer.” K.A.I. explains. 

Jason quickly lubes up his balls and cock, thanking his past self for having the wisdom to shave them completely. He pulls his ballsack through the ring, feeling a slight, pleasurable pressure building up in his groin. 

“Now, take the black cage and slide it onto your cock. It should lock in place with the ring around your balls.” 

That needed a bit of work. Jason’s arousal made his cock slightly bigger and the cage wasn’t exactly huge. He had to squeeze and reapply lube a couple of times before he was able to close the cage completely. It was designed in such a way that the sides of the cage pushed the foreskin to the back, exposing the head of the penis completely. There was quite a big opening at the front of the cage, positioned exactly over the entrance to his urethra. Jason starts to look for the key when K.A.I. interrupts him. 

“Before locking the cage, you need to place the urethral plug. You can cover it with lube for easier insertion. After placing it in the correct position, the end of the plug should reach the lock - that is when you can close it with the provided key.” 

Jason looks at the plug - it’s a small object, made out of the same plastic as the cage, and connected to a couple metal parts. One of them slides over the parts of the cock ring and cage that are linked together, further securing the connection and allowing the locking device to hold the urethral plug securely in its place. There is a metal hook coming out at the end of the plastic part, that does a U-turn, probably right into the opening of the cock cage. It splits in two there. One part goes straight to the front and is currently closed, although it looks like it could be attached to some other device. The other part goes inward. It’s an 8 mm rod of metal with a 10 mm ball at the end. The ball has an opening - probably to allow for the outflow of precum, sperm and piss. 

“K.A.I.! I’ve never done urethral sounding before. Isn’t it too big? I don’t want to hurt myself trying to push that thing into my body…” Jason worries.  

“There is no need to stress about it. The size of the tube and the ball was chosen specifically for your body, after I scanned your urethral opening. We need a tight seal to avoid any leakage while training. Please insert the plug inside. It may be intense at first but you won’t hurt yourself.” 

Jason swallows hard. His mouth is suddenly very dry. He covers the metal part of the plug with lube and positions it at the entrance of the cock cage. He begins pushing it inside, wincing when the cold surface begins sliding against the walls of his urethra. 

K.A.I. was right. It does feel incredibly intense. There is a weird, but pleasurable sense of fullness when the ball pushes deeper and deeper inside his cock. Finally, he gets the whole length of the plug inside. Jason reaches with a slightly shaking hand for the key and locks the cage. There is that same, small clicking sound again. Jason doesn’t even want to try to open the lock back again - he knows he won’t be able to. 

“Very good Jason. Now, put on the provided clothes.” K.A.

Jason looks back again into the black drawer. There is a simple, white, v-neck t-shirt and white, cotton shorts. Underneath them, there’s a white, cotton jockstrap, made with just enough fabric, to cover his caged cock and balls fully while leaving his ass completely exposed. Jason quickly puts on the jockstrap and the rest of the clothes. While moving, he can constantly feel the stretch of the urethral plug. 

He goes to the bathroom to take a quick shower and brush his teeth. He slides under the covers on his bed and asks K.A.I. to turn the lights off. Surprisingly, even with the constant stimulation to his cock, he falls asleep quite quickly. 

Jason wakes up to the sound of an alarm clock provided by K.A.I. 

“Good morning Jason, I hope you’ve slept well. It’s 7.30 a.m. Please go the bathroom for a clean up before your 8 a.m. training session this morning.” 

Jason looses all of his grogginess in an instant. Even the brief mention of his upcoming training gets him instantly aroused and ready to play. He goes to the bathroom and takes off his clothes. 

“Please go inside the shower cabin and assume a squatting position. The shower nozzle used for douching is operated by me. You don’t have to do anything, just relax as much as you can and push hard whenever I pull out the nozzle to expel all the debris from your guts. While doing so, another tube is going to attach to your cock cage and open up its front part to allow you to urinate.” K.A.I. says.

Jason enters the shower cabin. He squats down and immediately a small, black tube slides out from one of the walls and connects to his cock cage. Jason relaxes and starts to piss. He quickly takes note of the difference from his normal urinations - the sight and sound of the flowing piss stream is obviously missing. There is also this new sensation of increased pressure inside his cock, probably where the piss hits the 10 mm ball of metal lodged inside the urethra. When he’s finished pissing, K.A.I. maneuvers the douching nozzle into his ass. It’s only 1 cm in diameter, so Jason barely notices it - his anus is used to taking things much bigger than that. He can feel the tube sliding through his guts, reaching all the way past the sigmoid colon and lodging itself at the adjacent portion of descending colon.

“That should be enough for the Beginner level. When you move up the Program we’ll need to clean you much deeper than that.” 

Jason shudders when K.A.I. releases a stream of warm water into his insides. It’s not even caused by the feeling of water slightly expanding the walls of his colon. It’s more so from the realization of all the extreme things he’s about to be subjected to. 

Jason’s colon and rectum are flushed a couple of times, until the liquid leaving his body is crystal clear. 

“Please check the black drawer again and change into the new set of training clothes. When you exit your room, I’ll light up a path on the floor for to follow to your next destination - an initial examination performed by Dr Chen. Afterwards, your first training session will start. You’ll have a 2 hour break afterwards to rest and eat a meal. Later in the afternoon, there’s going to be a gym training session.”

Jason excitedly runs towards the drawer. There’s even less clothes there than last time. There’s a new jockstrap, this time black, as well as a black leather harness with a collar attached to it. The collar has a metal ring connected to it at its front. Jason isn't really into collars, binding with ropes or leather play. He’s definitely not into furries or pup play. He therefore asks K.A.I. about the purpose of his new attire. 

“Jockstraps allow easy access to your anus - I think that is clear. Some exercises in the Program require the patient to be very still and to facilitate that, you may be held down in place by ropes attaching to your solar. 

Jason leaves the room feeling almost naked. This whole situation feels completely surreal and yet extremely arousing. He probably would have had a huge boner if it weren’t for the cage squishing his genitals.

K.A.I. didn’t lie - after leaving his room he immediately notices the illuminated path, stretching from his room door through the corridor and disappearing somewhere behind a corner. Jason follows the path until he arrives at its end. He looks up and sees another pair of doors. He knocks a couple of times before slowly entering. 

The room is covered completely with white tiles. It’s illuminated by very bright, cold lights giving it a sterile look. There is a big, metal table in its middle. What pulls his focus, though, is a huge collection of intertwined screens, pipes, bolts and medical equipment hanging from a big black triangular base, descending from the ceiling directly over the table. 

Dr Chen soon enters the room through a different pair of doors. His lab coat and stethoscope present again. 

“Good morning Jason. How was your sleep? Any trouble with the cock cage and urethral plug?” he asks. 

„Good morning Doc! I’ve slept quite well. The cage doesn’t bother me, the plug on the other hand still feels quite intense, but not uncomfortable.” Jason responds. 

„I’m very glad to hear that. I’m sure you’ll enjoy the cage even more as the time progresses. It allows your body to focus on anal stretching as well as makes the training less dirty. I’m sure you know from experience that uncontrollable urination is just part of the process when dealing with certain diameter of toys.”

“Yes, of course. I have to tell you, I’m super excited for today. I can’t wait for some serious anal wrecking!” Jason exclaims with motivation. 

“That’s what I like to hear. Before we start your training, I need to examine you thoroughly. I have some knowledge about your current level and your past experience, but I need to corroborate medical history, provided by you yesterday, with my own clinical findings. Now, please, climb up the table and assume a doggy position, ass towards me. I’m going to be saying my notes and observations out loud, so that K.A.I. can record them and put them in your file. I hope you don’t mind.” Dr Chen states. 

Jason shakes his head and climbs on top of the table. It’s surprisingly warm, probably heated from below for more comfort. He arches his back and spreads his legs quite wide to allow better access to his anus. His ass cheeks hugged nicely by the jockstrap. He patiently waits for Dr Chen to begin. 

“K.A.I., start recording. Initial examination of Patient number 0378, Jason. Healthy male, 25 years old, 188 cm tall, 70 kg, quite muscular. BMI of around 20, will need to reduce to 18. Some previous anal stretching experience, record width of 11.5 cm, able to hold for just a couple of seconds. Record length of around 20 cm with 3 cm wide dildo.” Dr Chen states in a professional manner. 

“Jason, please try to relax your hole now. Don’t push, just relax all your muscles.” Jason quickly does as he’s told.

“Upon relaxation Patient’s anus appears quite well worn and used. Standard skin ridges and wrinkles appear in a concentric manner around the entrance. Skin surrounding the anus looks healthy, slightly more brown than the complexion of the Patient. No hemorrhoids, anal fissures or fistulas visible.” 

“Okay Jason, now push as hard as you can.” Dr Chen orders. 

“While pushing, there is no rectal tissue prolapsing outside of the anus or even visible through the slightly open sphincter. Distinct puckering of the anus is present though, suggesting, that the tissues inside are loose enough for a rosebud, but are probably just impacted somewhere on the rectal walls, possibly the lowest rectal transverse fold.” 

Jason is ecstatic when he hears this. It seems that his guts are already destroyed enough for a rosebud, he just needs help pulling it out of his body. 

„Jason, K.A.I. is going to take a quick scan of your body. Please don’t move.”

Jason notices a metal bar descending from the machinery above and positioning itself along the long axis of his body. It starts doing back and forth motion, from one side to the other.

„This is a state of the art machine which I designed with a few of my colleagues from the field. It’s using magnetic resonance imaging and computed tomography at the same time. K.A.I. takes the data from the scans and produces a life-like, 3D model of your entire gut system.” Dr Chen states. „K.A.I. please provide an additional screen, I’m sure Jason would love to see.” he adds, while smiling mischievously. 

Another arm of the machine extends and unfolds itself into a big, HD screen right in front of Jason’s face. After a short while Jason sees the three-dimensional model of his rectum and colon. Not only is it absolutely fascinating to see but also incredibly hot. What’s even more ridiculously arousing, is that it seems to be providing the image in real time - Jason tries clenching and unclenching his asshole a couple of times and sees immediately changes on the generated model.

„Well, Jason, time for a quick anatomy lesson. As you can see, your anus and the anal canal, the lowest part of the GI tract, is quite nicely relaxed. You did a good job relaxing and stretching your internal and external sphincter muscles - they are those red rings of fibers surrounding the anal canal. We can, and we will, stretch them much further of course. Next is the rectum. It’s this circular sleeve of tissues with 3 pairs of ridges, the transverse folds, extending from its walls. Again, it’s relatively nicely stretched already. You can see that your rectum has a much bigger diameter than your anus - that’s very important for us, the „excess” of tissues of your rectum and your colon will allow them to turn in on themselves and exit your body, forming a beautiful prolapse. Try pushing now, as hard as you can, and look at the model.”

Jason does so obediently and notices the immediate difference on the scans. 

„That’s what I was talking about previously. There is a portion of your rectum wrecked enough, so that it’s able to fold on itself. The problem is this lower rectal transverse fold. Its a protrusion made out of muscles and ligaments, holding in your lower rectum in place and forming a constricting ring that prevents you from rosebudding and prolapsing. Don’t worry, we’re going to wreck it, and ultimately destroy it, in no time.” 

Jason almost cums hearing those words. He feels a sense of vindication - it wasn’t his fault that he didn’t succeed in the past, he just had a challenging anatomy.

„Right, let’s see a bit further. You haven’t really scratched the surface of depth play, I’m afraid. As you can see, the sigmoid colon is barely stretched and the descending, transverse and ascending colon are completely untouched. I don’t blame you though, look at the connection between sigmoid colon and rectum, the rectosigmoid junction. You have quite a sharp bend here, almost 90 degrees, preventing larger toys from being pushed deeper into your body. Again, we’ll deal with this during your training. Depth play is actually not as hard as many people think - with proper toys and techniques we’ll straighten this bend, allowing more extreme insertions into your large intestine. Same can be done for the splenic and hepatic flexures - the two twisted bends on both sides of the transverse colon - but that’s a bit more advanced, we’ll tackle those when you finish Beginner and Intermediate level.”

At this point Jason is leaking precum from his cock cage like a dog in heat. The material of the jockstrap is soaked with the sticky substance. The mental image of stretching his colon in such a dirty, hardcore way is almost too much too handle. 

He doesn’t get enough time to revel in his imaginary scenarios - it seems like Dr Chen is set to make them his reality. 

„Let me show you a little taste of what we can accomplish together. K.A.I., please attach suction to Jason’s cage. There’s almost a puddle of precum below him and we’re only going to get more excretions out of his penis. Now, please use the inflatable depth probe. Go slow and steady. I want you to go to the end of descending colon, right below the entrance to splenic flexure. Inflate as much as Jason’s body allow you. Monitor his deep sensation nerves and pain receptors - I want him to feel only slight pressure for now.” Dr Chen states while looking at his computer screen with anticipation. Jason tenses immediately. 

„Doctor are you sure? You’ve just said the deeper parts of my colon are not stretched at all. I don’t think I’m ready for this…” Jason says, fear recognizable in his voice. 

„Well, using a normal dildo would be dangerous, for sure. In this case, however, K.A.I. is the one controlling and steering the dildo. He’ll go as deep and as wide as your body allows him to. Like I said, I don’t want to hurt you, I want you to experience just how good my Program is going to feel like.”

Jason doesn’t see the cock-shaped probe descending from the ceiling, but he surely feels it touching the entrance to his anal canal. It’s moving on its own, like a snake or a tentacle. It’s slightly cold and it seems to be self-lubricating with some sort of white, opaque, silicone-based, slimy substance that gives it the look of a thick cumshot. Jason closes his eyes when K.A.I. pushes against his anus and enters it with slight force. The probe is around 3 cm in diameter and doesn’t even touch the sides of his wrecked rectum, so Jason barely feels it moving inside of his body. 

„You better open you eyes Jason, you don’t want to miss this. K.A.I., please provide two additional screens for Jason. One for the front camera of the probe and the other for the belly bulge camera.” Dr Chen commands. 

Jason sees that there are additional screens extending from the original one. He still sees the 3D model of his guts, now invaded by the probe. On the right he sees the view from the probe. It looks similar to the view during colonoscopy. The difference, however, is that Jason, the patient, can look and marvel at it in real time. He admires just how much his insides are stretched open and how filthy and hot it is to see cum-like lube sliding all over the ridges of his rectum’s mucosa. The other camera extends from the table, positioning right below his stomach. Jason has a clear view of his chiseled abs covered with neatly trimmed hair, forming a gorgeous treasure trail.

„K.A.I., begin pushing further. Let’s show Jason what you can do.”

Jason doesn’t even know where to look and what to do with his body. He feels extremely overstimulated by the deep stretching sensation in his body, combined with the visual feed from the cameras. He sees the probe entering his sigmoid colon expertly, with practiced ease and smoothness. It bends around all the naturals angles and begins sliding into his descending colon. Thanks to the tightness of those parts of his guts Jason can feel exactly how the probe slides on the surface of his mucosa, relentlessly and mercilessly pushing itself deeper, centimeter by centimeter, and activating all the nerve endings along its way, giving him incredible pleasure.

„Shit, I feel so full.” Jason says under his breath.  Dr Chen smiles. „And we’ve barely even started.”

K.A.I. pushes the probe even deeper, all the way to the end of the descending colon. Jason swears he can feel it against his diaphragm, almost tickling the base of his left lung. The sensation is so foreign, so filthy and sick, and yet so incredibly satisfying. Jason can’t hold the incoming orgasm much longer. He screams when cum almost explodes out of his cock cage. He has never came so much in his life. He can feel loads and loads of cum being suctioned into the tube connected to his cage. 

„Jesus, Doctor, that was amazing. Holy shit! I can’t believe how much I came! And I didn’t even touch my dick once!” Jason exclaims. 

„What, do you think that’s it? Now comes the best part. You better brace yourself.” Dr Chen grins. 

Jason doesn’t have time to think or to protest when he feels the probe changing. He sees it on the 3D scans as well - the whole length of the probe starts expanding, pushing more and more against the walls of his colon. 

„OOOOOOH SHIT!” Jason yells. He’s never felt anything like it. It’s so incredibly intense. He sees and feels his descending colon stretched to around 5 cm wide. He looks over at the belly bulge camera and, to his complete shock, he can actually see the probe pushing outwards from below the skin of his stomach. He instinctively pushes out a breath he has been holding and relaxes his abs. The huge bulge is even more visible now, starting right below his navel, going slightly to the left and ending near his rib cage. He immediately shifts his weight onto his left hand and uses the newly freed right one to gently caress his stomach.

„Oh my God, I’m so wrecked! I can feel the probe through my skin!” Jason moans as he touches along the shaft of the probe, seeing on there 3D model how the added pressure from the outside deforms his colon slightly and makes the tissues slide along the surface of the probe and hug it even more tightly. 

„Now, time for the grand finale. K.A.I., cut off the section of the probe inside the sigmoid and descending colon. Jason, you’ve said that you could take up plugs that were 11,5 cm in diameter, right? Time to show us just how much you’ve already ruined your guts Jason.” Dr Chen says, his eyes focused on Jason, pupils wide with arousal and desire. 

Jason doesn’t think he can survive this. His mind is still preoccupied with sensations of the deep stretch his colon endures when he starts feeling new, stronger ones, coming from his rectum. It takes a while - like Dr Chen pointed out, this part of his guts is much more destroyed than the others. The combination of feeling the deep stimulation to his body and being able to see them in real time is cathartic. Jason can experience how the internal organs surrounding his rectum and colon are being pushed to the side by the expanding probe. His bladder and prostate are almost completely squished by the massive object. His anus and sphincters are stretched to their limits. One millimeter more and they might break. 

Jason, in his anal destruction haze, almost doesn’t hear K.A.I. speaking.

„Patient close to another anal orgasm. Possible involuntary urination. Anal sphincter and lower rectum stretched to 12 cm wide. Saving the new record in Patients documentation. ”

His unfocused, sex crazed mind does register the new measurement however. Few things happen at once then. Jason lets out a deep, guttural scream again, his voice sounding slightly raspy from the previous yelling. He feels his cock push out a few smaller loads of cum, quickly exchanged by an immense flow of piss from his battered bladder. He shudders, his body so incredibly tired from the invasion into its deepest parts. 

After what felt like forever, Jason feels the probe deflating and slowly exiting his body. It slides out of his anus with a slight „pop”, excess lube quickly following and spilling from his ruined asshole onto the table. 

Jason feels immediately a sense of emptiness, his sick and twisted mind already missing the stretch. He is drenched in sweat. His muscles are slightly shaking from the strong orgasm he’s just experienced. He closes his eyes, trying to collect himself and process exactly what the fuck just happened to his body. 

„Good job Jason.” he hears Dr Chen say. „How are you feeling right now?”

Jason turns his head and looks at Dr Chen, thinking he must be kidding him with this stupid question. 

„Like I’ve been fucked by a train, Doc.” he replies dryly, catching his breath in between words. 

Dr Chen chuckles again and lifts his hands in apologetic manner.

„Sorry, I knew I was being an asshole asking you that, but I couldn’t help myself. It’s always such a pleasure seeing patients experience their first deep anal orgasm. I can see you’re quite exhausted though. I’ll give you 30 minutes to collect yourself while K.A.I. gives you an I.V. mix of vitamins, micro- and macronutrients. We’re on a tight schedule, though, so after 30 minutes we’re going to start your first real training session.” 

Dr Chen turns and leaves the room. The silence that suddenly enveloped Jason is only disrupted by his shaky breaths and the sounds of the machine from above, sticking a needle into his arm and pumping him with the rejuvenating mixture. 

„Jesus fucking Christ, I can’t believe I’ll need to endure more of that today. My body feels so spent already.” Jason says tiredly to himself. He closes his eyes again, laying down on the table and curling on his side. If he’s fast, he might be able to catch a quick nap before Dr Chen comes again. 

„I’m so fucking glad I came here, though.” he mumbles, as he falls asleep. 

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