Jennifer shifted in her seat as she picked at her spaghetti, even though it had no effect on the plug lodged deeply in her rectum. As soon as Jennifer had pulled herself together and gone to her room that day, the finger that had been exploring her rear orifice had pulled itself out, leaving Jen free to scrunch her starfish closed and prevent any subsequent entry. But she could only stall the inevitable, and as Jen felt something oily and slick grease she knew she was fighting a losing battle. Still, she didn't want to give her thief the satisfaction of an easy win, and so she kept her port tightly shut. She tightened her anus even more when she felt it get picked up, then deposited onto some sort of metallic surface.
Soon enough, she felt a silicone tip press against her entrance. You're going to be pushing for a while, thought Jen as she steeled herself. But that's exactly what happened, as the plug besieging her puckered gate was pushed at an unwavering, insistent intensity for hours. She had done her homework, had a short conversation with her parents when they had arrived home, and had dinner in her room, the entire time struggling against an extremely patient force ready to invade her backside at any moment. Finally approaching the end of the day and knowing she'd never fall asleep with how much effort she was putting into the defense, she had surrendered, and reluctantly invited the plug in. Immediately, she felt her rectum engulf the silicone bulb as what seemed as wide as an cucumber embedded itself in her bowels, and soon afterwards she was picked up off of the metal surface and deposited onto a layer of cloth. Jennifer's eyes had teared up in the knowledge that her sphincter would only be able to close again after the plug was pulled out, and she began to sob quietly on that first night as she felt a weight begin to press on the plug and mash it even more tightly against her rosebud.
----------------------------------------------------------------------------------
Nick had expected Jen to deny him entry again when he pulled her rectum off his finger as he walked into his modest house. He had an idea for how to begin training her for anal, but he needed to finish setting it up before his father came home. Going into his room, he got two items; a sized anal plug set that he had planned to introduce to a future girlfriend one day, and an empty pringles can. After opening the can and removing the smallest plug from the packaging (still much thicker than his finger at 1.2 inches in diameter), he smeared Jen's anus with coconut oil, which takes a long time to dry. He then placed it on the bottom of the pringles can, followed by the plug, whose circular base was wide enough to prevent it from pointing anywhere but straight down into Jen's pucker.
Now, what can I use to weigh it down? Ah, the obvious choice. The final part of Nick's ad-hoc contraption was completed when he got a 8-pound weight from the small rack he had in his room (Nick had a skinny physique due to being a late bloomer, but he still exercised regularly) and put it on top of the plug. The weight was just narrow enough to fit in the can if it was completely vertical, and cleared the can by about 2 inches when combined with the length of the plug. Satisfied with his setup, he left the can on his dresser and let gravity do the work.
Nick had just finished playing video games for the night when the moment he had been waiting for arrived. As he got ready for bed, he saw the weight budge, then slowly drop into the can. Removing the weight and picking up the plug base, his pants became tight as he beheld the proof of Jennifer's surrender to him. The plug now looked like it was just a circular plate of silicone with a smaller circle of skin in the middle, but Nick knew that that circle was stuffed with the other 4 inches of the plug, and the thought that it would remain so regardless of which side of the plate he left it on delighted him for some reason. In another spark of pseudo-sadistic creativity, he placed the plate between his two mattresses before lying down, enjoying the subtle feeling of it as he rolled over it as his tossing and turning ensured Jen wouldn't get one millimeter of reprieve from her anal penetration.
-------------------------------------------------------------------
And so it had continued. Nick, not wanting to risk losing Jennifer's anus, began leaving it at home between the mattresses during the day, and over the days steadily increased the size of her gape with increasingly-girthy plugs and his contraption which gently forced the insertion. As for Jen, her life was not getting any easier. Throughout the day, while talking on the bus, passing notes in class, doing cheer routines, or making out with Brad (who she had lied to saying that she always left it at home), she was constantly reminded of her anal domination by the thick plugs in her behind. She suspected her anus wasn’t even on school grounds as she hadn’t felt any significant amount of time outside of the same-feeling metal or cloth surface, and with no clues as to who had taken it that first day she had no idea whether she would ever see her own asshole again. Checking in the her mirror every day, she masochistically watched the evidence of her continuing training as she spread the globes of her round rear end, the blank patch of skin corresponding to her distant hole progressively widened into a small “O” between her cheeks.
Because Jen no longer pooped, a fact Nick became aware of when his attempt to give her her first enema had never returned out of the hole he had squeezed it up, there was no reason to ever remove her plug except to install a larger one into her anxious pucker. This sometimes took a while for Nick as the thinness depth-wise of Jennifer’s detached part meant that it was difficult to get a good grip on the sides of her sphincter, and today was no exception. “I know you love it up your ass Jen, but I’ve got to pull it out now!” Nick said to her to her tightly-grasping ring with a smirk. On Jen’s side, this unintentional conditioning meant that she began to get anxious whenever her rectum was emptied of its silicone, glass, or metal intruders, even though she despised them every moment they were in.
By 2 months in, she had stopped fighting the exhausting, untiring force pushing each new plug into her weeks ago, softly sighing with pursed lips as she accepted a new guest through her back door while she ate dinner with her parents. It was an extra layer of humiliation, especially the time she had been forced to open her hole for a new toy as she gave Brad a long kiss goodnite after a date. It wasn’t until a second later that she realized with shock that this next guest was in fact a cock.