Chapter Text
"Penny.." Florian whined quietly to her. The sound of the vibrations from the large buttplug filled the air in the room. "Why did I agree to this?" He mumbled out. The freedom to talk was about all that she had left him agency for, his arms were bound tightly behind his back, the ropes digging into his wrists as he struggled to free them. Penny looked him over while he was moaning, his dick straining against the cage holding him limp looked painful, but she didn't care.
"You told me yourself that you were a bottom. Bottoms don't get to choose how or when they get to come. Or even if they do at all." She turned her head to look at him completely, planning on adding more to his struggles soon. "You DID agree to wear the chastity cage for me too, and I DID warn you what would happen." She reminded him.
"B-but.." Florian cut himself off quickly as he saw his girlfriend's smug smile, that was never a good sign for him. However much he whined and complained about his lack of orgasms, Florian didn't actually hate this, he loved the teasing and the torment. His eyes widened as he saw Penny approaching him with a cloth blindfold in her hand, which she quickly tied around his head with minimal effort, only lifting his head enough to tie it off behind.
No matter how much you whine and beg, I have no intention of letting you out of that cage anytime soon. Penny thought to herself as she reaches into her drawer in the nightstand and pulls out a roll of tape, tearing herself off several strips, which she attaches to the corner of her nightstand temporarily.
"Open wide, say Ahhhh," Penny said after she finished tearing some of the tape off, scooping up a white pair of her used and dirty panties off of the ground from her laundry pile in the corner. Glancing the undergarments over she can see the slight discoloration of stains leftover from her own orgasms. Before Florian could process the order she shoved them in his mouth and all he could feel is the tape covering his mouth as she secured the dirty undergarments in his mouth with it. "I'm done with your talking, I'm just going to be playing with my toy now." Florian begins to struggle anew as he tries to spit her underwear out, but multiple pieces of tape made sure that they're secure in his mouth and not going anywhere. "Those are one of the pairs I've been wearing while I touch myself, I wanted to make sure you had something flavorful for your teasing today." Penny leans in and whispers in his ear. Florian's struggles continued on more and more, becoming more frantic now that she shoved those in his mouth. "Those must taste delicious, enjoy them because they aren't coming out anytime soon."
Florian can only hear the rattle of the keys around Penny's neck as she moves off of her bed, he has no clue where she is going or what she's doing. Knowing the keys to his freedom were always so close, but were never obtainable for him, while being visible to others hanging from that chain she wore was driving him mad. "I thought these keys of mine might be lonely, so I bought something for you." Well, more like ordered online.. Penny thought to herself. "Lift your head up Florian." Her tone was flat as she gave him the order. At least he's already quick to obey, no questions asked. She continued on in her own head as she moved back over to the drawer in her nightstand to pull out the leather collar and lock.
Florian, still unable to see anything feels a slight bump and hears a jingle as something lands on his bare chest. He continues trying to push Penny's underwear out of his mouth, but can't. The taste of her and the constant vibrating of the buttplug is starting to make him want her even more. He feels something light begin to wrap around his neck as he's lost in his own thoughts, the feeling quickly snapping him back to reality. Before he even knows what's happening, Florian hears the click of the lock as it closes, securing the leather collar around his neck at the same time his girlfriend starts speaking. "You're my newest veevee.." She purrs in his ear, "I'm going to train you good and proper, just like any good pokemon deserves. I even bought you your own veevee costume to match that new collar of yours, and it doesn't leave anything to the imagination."
After glancing over to her closet where his costume was hidden, Penny looked her boyfriend up and down. Her gaze lingered longer than it should have on the black leather collar locked around his neck and the metal chastity cage locked around his member. After a moment Penny began to undress herself, starting with her hoodie and ending with her skirt, shorts, and patterned gray tights. She stood before him in nothing but her undergarments, not that he could see her. "You need more, you aren't needy enough yet." She said loud enough for him to hear her as she slowly pulled her panties down and let them fall to the ground, lifting them to her hand with her ankle before making her way over to Florian again. "Lift your head up again," Penny commanded, voice still flat and even. When Florian lifted his head up, Penny slid the freshly worn pair of panties onto his head. "These were on me for uhhh.. a few days. I needed them to be soaked with my essence for you." Penny said. while speaking she slid the panties down and hooked the elastic underneath his chin, putting the crotch area of her underwear right into his nose, forcing him to breath her smell in. This should help drive him crazy, Penny thought to herself.
Pulling out her rotom phone, Penny snapped a few pictures of Florian as he lay bound and gagged on her bed. Florian heard the click of the phone camera, after a few seconds it dawned on him what the sound was, he started to struggle against the ropes more while moaning into the gag, every breath inhaled making him want more and more. "I'm going to save these," Penny said nonchalantly, "I want these available whenever I want to see them. And if you don't behave.. maybe I'll send them to our friends." Penny said after a slight pause. As she was speaking, Penny laid down on top of her boyfriend, resting her entrance right up against Florian's locked cage, rubbing herself lightly on the metal cage, enough for him to feel it but not enough to be uncomfortable for herself. Just enough to work herself up a bit and get Florian all hot and bothered. With her phone still in her hand, Penny looked him up and down. Florian was panting and moaning into the gag, louder now than before. After a few clicks on her phone, the vibration level of the buttplug was turned down. Just enough to be even more teasing.
Florian felt the buttplug's vibrations weaken slightly which meant that he still felt it, but it made him want more, this lower setting wasn't enough. He could feel his girlfriend rubbing herself against his cage, hearing her moan quietly as she pleasured herself. Florian'smind was racing while she kept going, he was having trouble keeping coherent thoughts. Unable to see, unable to speak, and unable to move much meant Florian was having trouble. The longer they went, the more he wanted to come. Penny had put the cage on him about two months ago, taking it off to let him orgasm once after the first week of it being on. Penny hadn't teased him or antyhing during that week, she just didn't do anything sexual with him really, the two of them would just kiss ocassionally. Penny just let the cage start doing it's job and kept him wanting. After the first week Florian was begging her to uncage him. She had agreed, but told him that the cage only came off while he was tied up. This was fine for Florian when he first agreed, but he had assumed that the cage coming off meant that Penny would let him orgasm.
Florian was very VERY wrong with that assumption, Penny had tied him up and taken the cage off but stopped short of his orgasm every time. Florian wasn't sure how she knew, but Penny got awful good at figuring out when he was close and stopped just in time for him to get nothing. Florian learned very quickly after that first week that Penny liked uncaging him and letting him get hard so that she could line his member up and push down onto it, letting Florian fuck her but not letting Florian come. Her favorite activity lately seemed to be playing with him when he was tied down, but not letting him orgasm. She was getting very very good at teasing and edging him though. She kept him on the edge for hours at a time. In this haze of pleasure, he vividly remembered her mentioning that he had an eevee costume now, he wondered how long she had been thinking of that. While she was pleasuring herself on the cage preventing him from any pleasure at all from her slit, he found it harder and harder to think. The smell of her from her panties covering his face was starting to get to him. His dick kept trying to get hard, but the metal cage prevented that, just like it prevented him from touching himself.
Through his haze of pleasure, the deep breaths he was now taking bringing more and more of her essence into him, he heard Penny again. "I didn't fully understand you, but I think I know what you said. You asked me if you can fuck me right?" Florian nodded eagerly, hoping that she would let him. "I think I will, but we'd need to get you ready for that." Florian thought he misheard at first, but as he heard the keys jingling as Penny got up, he realized that she was going to let him! After a minute or so, he started second guessing himself, she hadn't unlocked him yet, despite his member straining so much against the cage. After about another minute, Florian guessed, he heard Penny again. "Stand up. I can't put this on you while you're laying down." Florian was unsure what she meant, but he tried to stand up. After alot of help form his girlfriend, he managed to stand up. He was unsure what she planned to do, but she did say he could fuck her. While he was lost in thought, he thought he felt a belt tighten around his waist, and before he could process that feeling, he felt another strap run between his legs and separate around his member, attaching to the front piece.
"There, the strap-on is on. Lay down and we can begin." Florian was floored, she had attached a strap-on so that he could fuck her, but refused to uncage him and let him use his own parts. It took a few seconds for him to process and realize that he was not going to feel anything, and he would in fact be fucking his girlfriend just like he asked. She was making him use a strap-on to get her off, while forcing him to remain caged and feel nothing. After laying down for about a minute, florian felt her weight on top of him again as she settled herself onto the strap-on. "I have plans for you, my precious new veevee." Her tone of voice had shifted, no longer just playful. "I'm going to train you good and proper. you'll be able to come on command, without experiencing an orgasm." She stressed that last part and made sure he processed it before speaking again, "and I'm going to clicker train you, just like the good veevee I know you'll be."
Up and down, on and off. Florian could feel his girlfriend pushing herself onto and off of the strap-on, imagining that she's pushing it deep into herself. A small moan escapes him, muffled by the cloth in his mouth making it nothing more than a whisper. "Oh are you turned on right now?" He heard her ask him, a laugh escaping her mouth as she continues to tease and mock him. Eventually, after some time of feeling her on top of him he gives in and starts thrusting with the strap on, hoping that pleasing her would get her to remove the cage quicker. While he's thrusting, he can imagine her sitting up, pushing the strap-on even deeper into herself as she continues in rhythm with his thrusting. After what feels like hours, he feels Penny pull herself off of the strap-on. He may be caged, but even he can feel her fluids as they coat the entire dildo, hear her move and pull herself off of it. The smell of sex in the air makes Florian want her even more. "We aren't done yet. Stay quiet while I do this and maybe there will be something for you too." This command makes Florian's mind race, what would she give him? Would she really take the cage off and reward him if he stays quiet? She lifts the panties covering his face up, uncovering the tape on his mouth. With no hesitation, Penny pulls the tape off and removes her now wet panties from his mouth.
Penny glances at the wet panties in her hand and tosses them on the ground, opting to grab another pair, equally as used, crusty, and in her opinion, flavorful for him, and cleans herself up with them, rubbing her fluids all over her new pair in her hands. "A new tasty treat for my wonderful boyfriend and soon to be new veevee," Penny says, her tone teasing still. As she speaks this she shoves this new pair in his mouth and reattaches the tape over it. "Besides, it's time for you to see your new outfit! I hope you like it!" Penny says, removing the top part of the underwear followed by the blindfold, only to put her panties fully back over his face again, making him look at her through the leg holes while the elastic keeps it on his face. Penny stands up now that he can see again, the keys on her chain around her neck rattling as she moves. Looking at that, Florian notices a new key there, and realizes with a growing dread that Penny probably has not intention of removing the collar either. Holding up the 'clothing' she must have been talking about earlier, the veevee costume as Penny had told him he noticed that it covers literally nothing. The top was a glorified bra disguised as a crop top with a fluffy collar to match the fluffy fur around eevee's neck. It looks like the neck fluff eevees have, but it won't cover any part of my collar. and the bottoms aren't any better.. They left literaly nothing to the imagination. They were basically panties, but with a small hole in the back and extra fabric in the front, for what he could only assume was space for his cage. She intends to keep me caged while I wear this.. Florian thought dejectedly, the deeper realization that Penny does, in fact have no intentions of removing his chastity cage for the forseeable future.
"The hole in the back is for the tail. It's also a buttplug, and yes it vibrates too. If you're lucky and once you're better trained, we can show our friends how good of a veevee you can be! Besides, this is just the start of everything. I have several skirts picked out for you too, not for the veevee costume, but for wear with your school uniform. They match our uniforms perfectly. They're in a bag with your new socks, bras, and panties. They're your new clothing. We can go shopping for proper weekend clothing this weekend or after we finish up classes on Friday. I hope you're as excited as I am!" Penny said smugly, "After all, this is exactly what your chastity cage is for. The collar shows everyone else that you belong to me and only me. You're going to wear this later for me, I need to take my new veevee for a walk and show her off to everyone." I also need to use that new harness I bought, the one for your arms and legs, Penny thought to herself. We'll go to the park and give you a good and proper walk.
After a few moments of silence from his girlfriend, he heard her moving around and felt her removing the strap-on from his waist. Unable to see, all Florian can do is wait. Wait and see what she has planned for him. He hears the snap snap of the rotom phone taking more pictures while he hears more movement, but he can't tell what she's doing, only hearing the opening and closing of a drawer. What? What's she doing? What could she- Florian's train of thought is cut off as he feels Penny pull him by his collar, urging him to stand up and repositioning him so that he's bent over at the waist leaning forward on Penny's bed. Florian had long given up trying to spit her used panties out, the tape was doing a good job of keeping them in his mouth. The sour and sweet taste of her fluids in his mouth was keeping him excited, his member still pressing against the metal of the cage that kept him soft and unable to properly masturbate. How long does she plan on keeping this cage locked on me..? Florian pondered while waiting for whatever his girlfriend planned to do.
"If you move or try to stand up I'm going to punish you and it'll be worst. Best you stay bent over," She said confidently as Florian felt her hands on his ass moving closer to the plug. After a few tantalizing and teasing moments Penny gripped the flared base of the buttplug and yanked it out, eliciting a loud yelp from Florian only partially muffled by his gag. He instinctively tried to stand up, but Penny put her hands on his back and pushed him back down, none too gently. She was getting somewhat forceful with him now and it kind of turned him on more.
"This is your last warning, I told you not to stand up. Don't do it again!" Penny hissed into his ear, "Do it again and you won't like the results."
Florian tried to apologize but all he could say were incoherent sounds through his gag, which were cut short as Florian felt Penny's hand with some sort of cold lubricant on it. He let out a small yelp of surprise as she rubbed it all over his ass, including using two of her fingers to spread it into his ass. Without warning he felt the head of the strap-on push against his ass and with one quick thrust Penny pushed it in, deeper than he expected. Florian let out another yelp, this one louder than the previous one, as Penny kept thrusting. In and out the strap-on went, deeper and deeper it pushed. Florian starting moaning more and louder as he felt a heat rising inside him and a good feeling as the strap-on kept pushing in. On and on this continued as Florian lost track of the time again, no longer thinking about anything besides the pleasure and warmth he was feeling from being fucked this way. After a few more thrusts Florian moaned louder than the past few and he subconsciously tried to stand up again as he felt Penny's hands forcefully push him back down again.
"Alright, I gave you a final warning." Penny said, Florian winced as he heard the iciness in her voice. He heard more movement and another drawer open and close, "If you stand up during this punishment I'm going to tie you down more and your punishment will be worst."
He tried to mumble an apology to her, but the gag did well stopping him.
"I'm going to beat some obedience into you and hopefully you learn to listen properly." Florian didn't have time to process the words, he heard a whistling sound of something then a loud THWACK as pain blossomed on his ass. Penny had gotten a belt out of her drawer. She waited a few seconds longer and aimed a second strike. THWACK, wait a few seconds for the pain to bloom more THWACK. On and on she went, pausing for a few seconds between each hit. The pain in his backside worstening as each strike hit home. Florian lost count around 40, his backside felt inflamed and badly bruised. After one final THWACK of the belt, Penny let up and Florian heard her toss the belt to the side as he let out a tearful sob. His ass hurt, it hurt a whole lot. A pulsing pain that didn't let up. Florian let out several more sobs, tears were escaping unbidden, caught by the blindfold over his eyes. He felt the strap-on push against his ass again, pushing in deeper and deeper as Penny continued where she had left off. The pain from his beating mixed with the pleasure of the fucking and Florian realized that if this kept up, he was going to orgasm. Penny stopped thrusting as she saw him getting closer and closer to the edge, nearing orgasm from the pegging. Florian let out a small moan of dissatisfaction as he realized she still didn't intend to let him orgasm.
"We're done now I think, we need to get ready to head out and go get something for dinner. I know we started playing like this mid morning, but it's almost dinner time now, and we need to clean up." Penny said as she helped him stand up. "Are you okay? Can you stand up Florian?"
As she was asking him these questions, Penny was removing her underwear from his face and mouth, taking him into an embrace as she did. "You did so well!" She told him as she undid the restraints slowly, massaging his arms and legs gently as she went. Florian was speechless, her taking care of him afterwards is always something he looks forward to. He likes it when she gently touches him and makes sure everything is well with him. After the restraints are removed the two of them laid there together in her bed. He did notice that she still didn't remove his chastity cage or collar, just like she hadn't removed his cage in the past. It seems like she really does plan on keeping this cage on for quite some time. I hope we didn't disturb anyone in a nearby dorm, we weren't really quiet today..
"Come along, we need to shower and clean up," Penny said gently as she got up and began scooping up the toys that they had used. Seeing Florian not getting up, Penny gently tugged on the ring on the front of his collar, encouraging him to stand up so they could prepare to head out. When she tugged on his collar like that, he felt a fluttering in his chest. He perused over this new feeling as she led him to her bathroom in her dorm room and turned on the hot water for the two of them.