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by Bestest baby
Julia smiled to herself as she walked down the road towards her house. The normally carefree high school senior had an unusual sense of purpose in her stride that afternoon. Free of school until Monday and her parents away for the next week she had plenty of time to carry out the plan which she had been formulating for the last few weeks. The unsuspecting subject of that plan lay struggling upstairs in her bedroom, tied spread eagle to her bed by pantyhose and other lingerie. Tied into his mouth was a pair of panties worn for two days by Julia, into which she had released some of her pee before placing them, gusset down, on his tongue, and over his genital area was a disposable diaper. Beneath the diaper, which having been in place since julia left for school that morning was by now quite wet, was the object that was causing the captive man to struggle so much: a large vibrating plug, the one which he had bought for her as a “present for prom night” with the intention that it would finally get him some anal sex to brag about in the locker room. Julia had made sure to remind herself of the boasts he had made to his friends when she maked it into his virgin hole as a final act of humiliation before setting off to class. The battery had worn down over the course of the day, but the vibrations continued at a lower level, reminding him of his almost total subjugation. How different it was from the fantasy he had had of tying Julia down and having his way with her! He shook as he heard her coming up the stairs and wondered in frightened curiosity at the bag which she carried in her hand when she finally entered the room. She met his gaze evenly. No longer the sweet airhead of his imaginings, her face hardened to reveal the intelligence she had kept from him while she waited for the opportunity to realize her fantasy of having a male, a jock, completely at her mercy.
“Hi, Simon,” she said calmly as he stared up wide eyed at her. Despite all she had subjected him to so far he still thought her beautiful; her pert nose, the light hair, her smartly rounded thighs and breasts and her mouth which could smile so sweetly and innocently that he would never trust again. She noticed his looks and laughed. “You still can’t stop wanting me can you? You need to learn that the only penetration that’s going to happen around here anymore is the kind that you’re already getting used to. The only contact you can have with my pussy or my anus is the kind that I choose, and don’t think I want your cock anywhere near either of them. As a special treat if you behave well I might let you worship them with your face, but for now sucking on my juices will be as close as you get.”
Simon could only whimper in response to her cutting comments. The previous night he thought that they were finally going to have full penetrative sex. She had dropped hints about her parents being away and said that he should be prepared to spend the whole weekend here, which meant that he would certainly not be missed until Monday. He shuddered at the thought of being kept here until then at her mercy. All he could remember of the previous evening was taking a sip of his drink, sitting on the couch beside her and hoping that the alcohol he had been encouraging her to drink all night would soon have an effect and he could finally relieve his aching balls. The next thing he knew it was morning and he was lying in the bed which he had tried so hard to enter, tied down and with a salty tasting piece of cloth in his mouth. As he became more aware of his surroundings he could feel a strange sensation in his anus, and he saw Julia leaving the room. She must have just inserted it and the vibrations were dragging him out of his sleep. He felt something warm around his loins, and when he looked down he saw what seemed familiar from a distant part of his childhood…
“Simon!” Julia snapped him out of his panic-induced reverie with a shout. “I want you always to pay attention. You may have just earned yourself some punishment for drifting off like that. Now I am going to release you mouth. You must be very thirsty from the drugs and from not having any water today so I’m going to let you drink, but no moaning or crying or arguing, or I’ll head into the bathroom now and freshen these up with some fresh pee and put them straight back into your mouth and leave them there for a while! Understood?”
He nodded frantically and she loosened the cord holding the soiled underwear to his face. The panties slipped out of his sore mouth easily and lay around his neck, as she held a glass of water to his lips. When she had ensured he had drunk at least three glasses she retied the panties and sat back. “Now you’re rehydrated and more,” she said, glancing at his diaper and smiling what he would have previously thought of as her dainty smile “I’m going to tell you something about what you’re doing here.
I knew you had your filthy plans for me last night. Your supposedly “secret” conversations about what you wanted to do to me and how you wanted to do it, even the way you planned to record our time together and show it to your friends.” He started, and she smiled. “I went through your bag when you were ‘asleep.’ That video camera is going to come it quite handy in making sure that not only will you be my sissy slave this weekend, you will be mine every weekend from now on.” She giggles sweetly as he struggled against his bonds. “so you know what a sissy is do you?”, she said, stroking his diaper gently with her girlish pink fingernails, “a sissy is a boy who is dressed up and humiliated and made to please me. That’s the only definition that you’ll ever need. And you might be wondering about the diaper you’re wearing. I think that since the things you wanted to do to me with that prick of yours were so very naughty, I think you should have it kept in a diaper like the little bitch I’m going to make you into. I see you’ve already wet your diaper. That’s good, but you’ll do it many more times before I’m satisfied. But I will make a deal with you. If you progress sufficiently in you training and you are submitting to me in the way I need then I may allow you some freedom.”
Simon squirmed in his bonds. He could not believe his situation. His mouth abused and filled with the taste of the pussy he had once longed for edged with pee which his saliva lubricated and maked him to swallow, his cock encased in a diaper and soaked in his own piss, and his poor little rosebud held open and apart by the softy vibrating plug. Thinking about it made him struggle more, and Julia must have something in his eye as she looked at him and giggled.
“I hope you like how your little hole feels with that plug in it. Don’t worry, it’s there for a purpose.” The expression on his face told her that this remark had hit home. “Now I think it’s time we got on with your training.”
He lay back unable to move or speak as she picked up her bag and began laying out some items she had obviously purchased that day onto the table beside the bed. He almost cried when he saw that the bag contained more diapers, strong ropes and cuffs, and a large dildo attached to some sort of harness. She saw him looking at it in fear. “Don’t worry, Sissy Simon, you won’t feel this in your punishment hole until you’re ready. I don’t know if it’s good news or bad news for you to find out that that will be in a few weeks. For now, you’ll be accepting your new toy into a different opening.”
With that she removed that panty/pee gag from his mouth and replaced it with the dildo, which she strapped round his head. It protruded a fair way into his mouth, but the majority of it was outside. She busied herself attaching the cuffs to his wrists and ankles, and tied them to the opposite side of the bed to the limb they were attached to. He realized slowly that once she untied the pantyhose which now pinned and spread him on the bed she would only have to tighten those ropes to leave him lying face down instead of up, his bottom totally exposed to the punishment she had promised him.
“Before I turn you over, Sissy Simon, I think I need to demonstrate how useless you cock is to me. With a flourish the normally sexually reserved girl removed her panties with one hand and flung them across the room. She turned, facing his feet, and backed up towards his bound face. He was mesmerized and despite himself began to grow erect. She could see the bulge in his diapers and laughed before putting the dildo’s tip at the opening of her cave. She pushed it a little way in, and then in one go sat down all the way. He smell assaulted him, and his nose was pressed right up against her bottom hole. She wiggled it. “I do like being stimulated on my back hole,” she said, beginning to rise up again. As she settled into a gentle motion of up and down over the hapless Simon’s face she began to talk to him. “I don’t care that your little wee is getting hard, I have your face dildo for now; soon I’ll have your tongue to please me in both my holes.” she rubbed at the front of the diaper, and Simon realized that despite the torture going on in his rosebud, the laughter and humiliation he was receiving from Julia and the emasculating sensation of being diapered, he was as turned on by her as he had ever been. Looking at her diving labia being penetrated he began to raise and lower his head in an effort to match her strokes, and to massage her back hole with his nose. He was smelling her ass and being dominated down to the level of a sissy by her, but he could not help but enjoy it. Through the fog of her own sexual arousal, Julia noted with approval the change in his responses, he was already customizing himself to the role of a submissive. She could relax and enjoy herself now, but whether or not he held up to the next part of his training would be the real test of his psyche.
She began to bounce harder and higher on top of his by now bruised mouth, pleasuring herself by looking at his diapered and submissive state. As she came, she saw him humping at the soggy mass of the diaper, trying to match her strokes on his face. After she had come down and recovered from her cum, she slid off him. Her natural juices were running down the dildo into his mouth and onto his face, and he felt humiliated and desperate.
“I hope you enjoyed the view there, Sissy Simon, because that’s all your going to see of anything for a while,” and she abruptly untied his lingerie bonds and pulled tight the leather bondage equipment. He lay on his front, terrified by what might come next. She adjusted some straps and he felt that his ankles were clipped to a line at the bottom of the bed, allowing then to be held still at any angle. The purpose of this was revealed by her next command.
“Up,” she ordered and slapped his stomach. He lifted himself and felt her slide a pillow, then two more, under his belly. His feet were secured and his ankles crossed, leaving his knees bend wide and his bottom in the air. He could now feel the vibrator move into a 45degree angle to the floor and realized that not only was he in prime position for a spanking but that his hole was also available for whatever Julia wanted. As it happened, there was something that Julia wanted for his hole, but not what he expected.
She left the room, and came back with another bag. Behind the ever more frightened sissy she put on a pair of latex gloves and took out another diaper and a banana. She untaped his soggy used diaper and it fell to the floor.
“You might be expecting a spanking,” she said, “but I have other plans first. I have decided to lessen your punishment, although you may find it worse. I will give you the choice. Would you like a whipping now on your bare buttocks, or would you prefer to have that diaper up close to your face? You may answer me with the plug. I’ll hold it, and I want you to squeeze it with your bottom muscles once for a whipping and twice for having the pissy diaper up to your face.”
She moved close up behind him and grasped the plug with her latex covered hand. He knew he couldn’t face the pain, so he would have to swallow his pride and answer her in the way she wanted. He squeezed with all his might, but as he was mustering up his reserves for another squeeze she cried out- “Well Sissy, it seems you are made of stronger stuff. You’ll take the whipping will you? Good, because even though I was planning to take great pleasure in bringing you down and humiliating you for your disgusting thoughts, I liked to think that there was a real man in there to bring down!”
He knew what she was trying to make him do and he hated her for it, but he squeezed his anus again.
“Oh Sissy“, she said, “I was wrong about you. You are just a little sissy wimp who would rather have a pissy soiled diaper right under your nose for who knows how long than take a little beating. Well in a way I’m happier about what I’m going to do with you..”
She pulled the diaper away from his body, opened it to the dripping wet, cold side and lifted his head from the pillow. Before lowering him onto his smelly fate she removed the dildo gag. “I’m going to let you taste it too, sissy. You can try and keep it out all you like but some will get in there.” she laughed, and at that point Simon felt he might cry, but the surprise of Julia’s next move put a stop to his thoughts, as she pulling out the plug suddenly from his exposed bottom. She took out some gel and rubbed it on her fingers and then soothed his hot anus with the cool and slick substance, slipping one of her gloved fingers neatly inside. “Don’t get any ideas Sissy, this is not for your pleasure, this is part of your training. So far you have been passive only, but now you have the opportunity to demonstrate that you can be a good sissy and avoid further punishment by doing a little task with your bottom.” He heard her laugh as she said “you can even do it lying down!”
“What we are going to do, Sissy, is play a game.” She laid out a fresh diaper on the bed beneath him on the pillows which supported his midsection. “That’s to catch any pee that comes out, but I’m leaving your bottom open for our game. Turn your head to the side.” He pulled his face out from the soaked shame of his diaper and saw her holding a peeled banana and a tube of lube. “Open,” she commanded, and as he opened his abused mouth he felt her squirt the gel inside his mouth and then put the banana up against his lips. “If you hadn’t already guessed, Sissy, this is going in your tiny hole next, so you’d better suck it for me and get it nice a lubricated.” The banana was already going soft in the warmth and lubricated depth of Simon’s mouth as he desperately tries to please her. She noted with a flick of the eyes that he had already learned the basic lesson of submissive sissy behavior- that the first duty is to please Mistress. Once the banana was truly lubed up, she returned to his anus and explained the rules of the game over his shoulder.
“Sissy, you have wet your diaper today for me, but now I want you to submit further and learn what the total submission of messing your diaper means. I know that you might hold off from doing this, so I have devised a way of encouraging the right sort of attitude with this game. That plug should have gone some way towards relaxing your little hole today, and this is going to help you do it more. You’re going to receive this banana into your sissy pussy, and let it stay there. If you squeeze your little hole’s muscles just once, the banana will break in half and I’ll know you disobeyed me. If you push it out, I’ll punish you more, and if you can keep it there for half an hour I might let you have a little cum, on my terms of course. You’d like that wouldn’t you, sissy? Yes? Well you’d better get ready.”
Simon tried his best to relax as he felt the banana tip on his rosebud. It was wider than the plug, but he made a massive effort to relax his bottom and the fruit slipped in slowly. “Just to get us started, Sissy, I’m going to push it in to the tip, and you’re going to push it back out halfway, but no more.”
Simon felt her fingers on his bottom as she pushed it further in. “Okay, sissy, now!” she said and he pushed very gently back on the soft fruit. “Good, sissy, she said, just think of it as a natural to let it slide out from your anus, just let your control go, you’re not pushing it or even caring, it’s just hanging there as a reminder of your dirty mind and behavior.” The banana was now lodged exactly half in and half out. Julia’s eyes were bright with excitement as she revealed the final part of the plan to Simon.
“I hope you can keep it there sissy, since if you do break the rules of our little game and squeeze, the bit that goes into your hole will stay there and we’ll start again with another banana. So if you don’t want your hole to get too full then you’d better be careful.”
Knowing that he would struggle Julia settled back to watch his quivering bottom attempt to hold the fruit. Simon was finding it hard. Many years of toilet training as well as the effects of the day’s plug were screaming at him to clench his muscles or expel the intruder. It was a losing battle. Julia watched as the banana was neatly sawed in half by Simon’s bottom and one half dropped on to the diaper that lay beneath him. She began peeling another one almost immediately. “Oh, Sissy, I’m sorry, I forgot to tell you what happens to the other half of the banana, the one that has been all the way up inside your bottom and has now fallen out onto the diaper I put underneath you- you’re going to eat it!”
Julia watched Simon’s reactions carefully. If he baulked at this task, she would have to train him a lot harder than she had hoped. Simon felt low and humiliated, but he couldn’t deny that the stimulation his anus was receiving was erotic. He looked back to see that Julia had removed another item from the bag, a riding crop. Simon realized he was going to end up eating that banana whether he liked it or not, and wearily opened his mouth. Julia, although she didn’t let on, was ecstatic. He had finally understood her dominance. The next few bananas would go in nicely. But before that, she had to see to this one. She took the next fruit, together with the excreted piece, over to Simon’s face. His mouth was already open in supplication. She squirted more lube into his mouth and explained “Sissy, you will have the next one in while you swallow this one, to remind you where you need to succeed this time.” He sucked on and lubed the fresh banana, which she pulled out gently with her gloved fingers. The piece she lay on the soiled diaper in front of his lips. “Sissy, you must eat this piece in the way I command you to. You will suck the banana through your lips as I push this fresh one which has just left your mouth up into your anus, if you last long enough this time, Sissy, they might meet!”
She pushed and felt his anus open and accept the new intruder as at the other end his mouth accepted the soft and lubricated fruit, entering his body at both ends. He concentrated on swallowing the banana slowly to please her. At the same time she was pushing on the other end, and as his throat muscles contracted to accept the fruit, so did those at the other end, and the whole second banana was sucked up inside him.
“Oh dear, Sissy, you are greedy. Let’s hope you’re as keen for the next one,” said Julia, as without warning she pushed a third fruit up, up, and all the way inside his now uncomfortably full anus. She quickly taped up his diaper having achieved her aim- to humiliate her erstwhile jock boyfriend and fill him up with bulk which he would need to expel soon.
Simon only now realized her plan- to make him to mess into his diapers helplessly in front of her. If he only knew how much worse it would be.
She came back to the bed and fiddled with the restraints. Once she had completed what she was doing she pulled hard on the ropes and Simon felt himself turning over for the second time that evening. But this time as he lay on his back, the pillows were still underneath him, and as Julia pulled again, his legs were brought up over his head leaving his diapered crotch high in the air.
“Normally people can’t mess themselves upside down,” Julia said, “but thanks to our little game you shouldn’t have any trouble finding something to come out, should you?” Simon was horrified and humiliated by the prospect of pushing out bulk into his waiting diaper, but confused when Julia climbed onto the bed above him. He understood when she arranged her skirt over his face and settles down with her anus on his lips. Her scent was in his nostrils and despite himself he found himself getting hard, and Julia, sitting atop the humiliated sissy, could well see his excitement. “That’s right you dirty sissy, you filthy boy, you’re going to make two kinds of messes for me, aren’t you?” she lubed up her gloves some more and pulled the front of his diaper away to give access to his by now swollen member. She began to manipulate it gently at first, but then harder as he responded by licking and the penetrating her anus with his tongue, all the while hearing the humiliating comments of the dominant teen above him.
“Do you want to come, Sissy?” she cried as she rubbed him up and down, “if you do you know what I must see.” He did know, and despite himself began to push his anal muscles and felt his hole open. “Harder, Sissy,” Julia yelled, and soon about half a banana was out in the diaper. Julia reached over and rubbed the back of the diaper, smearing the banana all over it. He pushed harder and more came out, and as he was about to come, Julia suddenly pulled herself away from his face and sat behind his head, one hand still rubbing him, she pulled the ropes moving his legs higher and higher, and as the final banana was half in and half out he saw she meant for him to come on his own face, in a messy diaper, and not only that, but as he craned his neck upwards he saw the solitary eye of the video camera above, watching the whole scene. She followed his gaze. “That’s right Sissy you are going to come with your full diaper on, and come in your own face, on camera.”
Sissy Simon way by this time ready to do anything, he cried out for her to finish him, that he was a humiliated sissy bitch who loved to drink come, that he was a pissy shitty baby with no brain, and that he loved it. At the last moment she pinched his nose and as he opened his mouth she pushed with her other hand on his balls and he came into his own mouth. “Swallow, sissy” she ordered.
They lay for a moment, until Julia spoke. “Now is the time for that freedom, Sissy. Would you like to stay until Monday?”
Simon didn’t answer, but craned his neck upwards and planted a sweet kiss at the top of her pussy. She smiled, her task complete.
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