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“Wait a sec, the school has a guidance counselor?”
Issei seemed surprised at this news as he stood up in the middle of class. The PA system had informed him that he was meant to head to their office later in the day, once this period had finished up. It brought attention to him, with every student and the teacher looking at him with a blank expression.
“Issei, take your seat,” groaned the teacher, “we don’t have time for your moronic outbursts.”
“Hey, hang on!” Issei said. “Nobody’s answering my question. We have a guidance counselor? Since when?!”
“Since always, you dumbass!” said Aika Kiryuu, pushing down on the top of Issei’s scalp. “Now sit back down and let the rest of us focus on the schoolwork!”
For the remainder of the class, Issei couldn’t help but wonder what a guidance counselor would want with him. That, and the pain from Kiryuu’s force was still there.
When the bell rang, Asia got out of her seat, chasing after Issei as he powerwalked his way into the hallway. “Issei, is everything okay? You’re not in any trouble, are you?”
“That’s what I’m about to find out,” he replied, exhaling as he looked at the ceiling in thought. “I don’t get it. I don’t really do that much to get in trouble, do I?”
“Well I do know that your friends tend to get you in a lot of perverted trouble,” Asia replied, tapping her finger against her chin.
“Uh, about that…” Issei said with a nervous smile.
“I mean it isn’t your fault that you found them spying on the girls’ kendo team, right?”
“Asia, actually-”
“Or the other time they were ogling the swim team in the locker room…”
“Asia-”
“Oh! What about that time you were trying to protect Rias from them being in the ORC’s shower room?”
“Okay, THAT one wasn’t my fault…” Issei responded after multiple interruptions. Still, he thought about how long that behavior among him and his friends had been going on for, and how they had never received any sort of punishment for doing such things. Okay, they got walloped by the girls for their perverted nature, but he felt that was enough of a lesson for them to learn. Even if they kept repeating their actions…
“Hey, Asia, do you know where the counselor’s office is?” he finally asked the blonde pawn.
“Oh, sure! Anything for you, Issei!” Asia giggled. “Do you need me to come with you for support?”
“Nah, but thanks, I think I should be able to handle this on my own.” Issei followed behind the religious devil, watching out for her while she guided him to his destination. Once they were there, Issei thanked her for her assistance and made his way inside.
“Good luck, Issei!” Asia said as he went in. “Hopefully you aren’t in any kind of trouble!”
“Yeah, that makes two of us,” he mumbled, shutting the door behind him. Once he took a few steps in, Issei was met with quite the sight; his eyes widened as he spotted a huge rump in his face, one draped in a sleek and silky red dress. Sucking on his lip, the young pawn soaked in the ass, committing its shape to memory while he kept ogling at it.
The owner of the ass stood upright, pivoting around to see the eager expression in the perverted devil’s eyes. “My my,” said the woman, her lips curling in at the sight of his short physique. “So you’re the infamous Issei, hm? A pleasure to meet you.”
“Uh, yeah, same! And you’re...the student counselor, right?” Issei asked, looking her up and down. He could see that she was a very tall yet curvaceous woman, with dark skin and black hair. She had her bangs dyed with a bit of red, matching up with what was in her dress. “You dress pretty provocative for someone at the school,” he said, taking note of the boobs and the way they were spilling out of her cleavage.
“I get that a lot,” she laughed, “nothing to worry about. Let’s have a seat, please. And take a little something to enjoy yourself.”
Sitting before her desk, Issei took note of the small pile of sweets in a basket, with some sodas collected together on the other corner of the desk. He wasn’t feeling particularly thirsty, but he supposed having a little drink to keep his gut occupied before lunch couldn’t do him much harm. He opened up a can as the woman looked over some paperwork, the wait to hear what he was here for making him anxious. “So uh...miss…?”
“Call me Sylvia, sweetie,” she replied.
“Sylvia, okay. That’s cool. So what am I here for, again?”
“Isn’t it obvious? You’ve been quite the naughty boy on the campus,” Sylvia said, pressing her finger against his nose in a teasing manner. “Wanting to kiss the girls and make them cry, what a poor boy you could be…”
“Whoooa whoa whoa!” Issei shouted, crossing his arms before the counselor. “I’ve never kissed any of the girls here. Except maybe Rias, but-”
“But you were still ever so close to trying anything to get to them,” Sylvia continued. “I have plenty of documents on hand illustrating that you have been caught on multiple occasions being a world-class pervert.”
“But the girls beat me and my buds up afterwards!” argued Issei. “Don’t you think that’s punishment enough?!”
“Maybe the last counselor had thought that to be the case,” Sylvia said after a short hum, “but not me. I take such complaints about this behavior quite seriously.” As she said that, she leaned over the desk, letting her breasts rest atop the desk, which Issei’s eyes caught. He couldn’t help but notice just how big they were as they sat atop the surface, with the counselor even flexing her muscles a bit to make them jiggle. She knew what she was doing, illustrating a point, and the young man took the bait without problem.
“Wha-N-Now hold on!” Issei shouted, his face turning red as he felt caught. “You’re looking pretty scantily clad for someone being a pervert yourself!”
“I’m an adult,” Sylvia said seductively, “I can do what I want because I don’t worry who gazes at my appearance; all eyes are valid.”
“I feel like we’re talking about two completely different things…”
“Nonsense. Now, given how many of these incidents have you as a recurring foil, there’s going to be quite a bit of detention that you’re going to have to serve. Unless.”
“Unless what?” asked Issei, folding his arms as he cocked an eyebrow at her.
“Unless you let me fuck you.” The counselor sucked on her lower lip, humming with pleasure as she gave the young man a seductive stare. Issei blinked repeatedly, staring blankly at Sylvia as he tried to fully process the sentence, as well as the request.
“I’m sorry,” he responded, “you want me to fuck you?”
Sylvia shook her head, “No no, you didn’t hear me right, Issei. I will forgive your past behavior, so long as you not only promise so stop being a pervert, but also let me fuck you. As in, I get to fuck your ass.”
Issei’s sphincter clenched up at the mention of that, his lips thinning out at the horror that filled his mind. The implication was clear, and he couldn’t think of a way that he could turn it around on the guidance counselor. “But...wait, that doesn’t sound right!” Issei argued. “Like that’s some weird student-teacher relationship stuff, right? Ain’t that against the school’s rules?!”
Seeing through his avoidance to be pegged by her, Sylvia stood up, reminding Issei quickly as to how much taller she was compared to him. She bent over him to let her breasts hang over his head, almost letting them dangle out of her dress. “Rules aren’t exactly something I like to follow,” she explained, “I like to make my own when it comes to keeping my students nice and safe. And the school seems to let me have that freedom, given they believe my way to be the right way.”
“Okay, but what if we don’t-” Issei found himself interrupted by Sylvia planting her lips onto his, an unwanted moment in his life. For a brief moment, Issei understood what it was like to be on the other side of such perverted actions, and yet he was slowly enjoying the kiss of a woman who was not only older, but taller than him as well.
While remaining in his seat, Issei reached out for Sylvia’s tits, pushing the dress out of the way so that he could play with her darkened nipples. With so much softness attached to her chest, the perverted devil could knead away without end, taking enjoyment out of how much there was to play with. His hands rubbed and massaged against her mounds, wishing that he didn’t have to stop. He was growing more ignorant of the counselor’s kiss, how her saliva seemed to run its way down her throat. Her tongue tussled with the young man’s, who was slowly growing relaxed the more they made out.
Sylvia soon squatted before Issei, making it just a little harder to grope her breasts. That wouldn’t be too much of a problem for the Breast Dragon Emperor, as he could at least lean into her, moving forward enough to grab at her ass. He felt the shape and squishy nature of her behind, his fingers rubbing through her dress all the while. He might not have been able to feel the skin of her rear like her boobs, but he still felt fascinated by the shape of it.
While they were occupied with each other’s mouths, Sylvia started to undo Issei’s pants, which filled his mind with more perverted thoughts. It was nigh on impossible for the young devil to let his hormones remain in place, especially since the tanned counselor looked to egg him on in such fashion. Perhaps she thought that the idea would be for him to use this as an outlet to let off steam, please him with her assets until he was all hormoned out, or something.
The counselor helped get Issei’s pants off, soon helping the young man off his seat. Once she pulled away from his lips and licked the saliva off hers, she began to purr while batting her seductive eyes at him. “Now, Issei, I want you to turn around,” she requested. “Don’t worry, nothing too dangerous is going to happen. For now.”
Issei gulped, doing as he was told by the counselor. He kneeled on the seat, letting his bare ass stick out. “Okay, whatever you say…” Issei replied, a bit nervous as he felt the wind against his exposed backside. His hole puckered at the tanned woman, who seemed to drink in his tight behind with her eyes. As the sphincter clenched in, she thought the whole thing was adorable, seeing the virgin nature of the student and the inexperience he had. She could just go in dry, but there wasn’t too much fun with that for a rookie.
Instead, Sylvia brought her lips onto Issei’s pucker, her tongue pushing up against it. The young man yelped, feeling the warmth of her tongue go against his posterior. He shivered, his legs squeezing together while his dick found itself in the middle of his thighs. The rod pumped against them, veins full of blood as his staff started flowing with blood to get him erect. But that wasn’t where the tanned counselor’s attention was, instead fixating on his rear end and the delectable taste it provided her
“Mmmm, your ass is so tasty, Issei…” Sylvia moaned.
“Really? Because I wouldn’t associate the butt with tastyyyyy!” Issei tensed up, his ass pushing into Sylvia. She had flicked away at his posterior in an attempt to squeeze her tongue inside his rectum, though why she would want to puncture that was beyond him. He huffed and heaved at the sensation, which was too much for him to withstand, until he was able to come down from the sudden high that brought. His cock had started throbbing wildly as a result of the anal lashing, something different from what he thought it would feel like.
It was just that he never felt himself being on the receiving hand of such a treat.
As she realized Issei was getting hard from her anal rimming, she squeezed her hands between his thighs and brushed them apart, leaving his dick hanging in the air. While her mouth remained fixated on his rectum, she used her hands to tug away at his shaft, hearing him groan and huff while having to endure the pleasure that all of this brought to him. It was strange and unusual, not at all what he thought sex would be about. He seemed to think it was more durable for a woman to have her ass played with rather than his own.
But the stroking that Sylvia brought to his dick was incredibly great, how she had her hands straightened out, both palms rubbing on the sides of his shaft. She ran them down from the base to the glans, with the crown being ignored for the most part. That was where the blood had been storing itself to ensure it was fully stiffened up. “Holy shit…” Issei groaned, resting his head on the back of his chair. “I never thought something like this could feel so good!”
“That’s right, slut,” Sylvia said, admiring the amount of drool she left behind on his rump, “you just keep on enjoying yourself.”
“Slut?” asked a confused Issei. “Wait, I’m not a sluuuuuut!” Issei’s eyes widened, his grip on the chair tightening as the counselor punched her tongue through the anus, letting it slip inside of his tight hiole. It was the most intense thing ever, as though he felt something placed inside of him, like...a penis? But no, that was just Sylvia’s tongue, right?
Whatever the case, her hands were still stroking at his shaft, though squeezing it tightly to get him to shoot his wad faster. “So this is what sex is like…” Issei groaned.
Sylvia ignored him, working hard to get him off. She could feel the veins pumping against her palms, which told her just how close he was to letting out a climax. There was just one more thing she was certain would let him release at last. Removing her hands, she used one of them to squeeze in on his nut sack, causing him to tighten up and, at long last shoot his jizz onto the seat he was kneeling on top of.
While her tongue managed to push away at his prostate, Sylvia loved the sounds of Issei as he growled from the intense release coming through his teeth. The release from his cock was just as wonderful, watching how it stained the seat. There was a pool of his creamy load, all begging to be eaten and licked at, just for the sake of cleaning the chair off. It wasn’t meant to be merely cleaned, no, it had to be devoured.
When he finished his release, Issei rested on the chair, his body loosening up afterwards. He exhaled loudly, heaving from such a heavy load being unleashed by Sylvia’s tongue that he could barely stay awake. But he had to remain awake, since he still had the rest of the school day to go through. Yet he was in heaven, blissful to feel such a climax that even he had never been able to give himself whenever he had time to masturbate.
“Fuuuuck me, that was good…” Issei said with an exasperated sigh. “I need to take a little bit of rest.”
“Awww, poor thing…” Sylvia said as she petted his head. “I can’t let you rest here. In fact, you’re looking really tired. I don’t think you’re looking hot enough to continue your school work.”
“You sure…?” Issei asked, his voice weary from the blissful sounds it made moments prior. “I got swimming classes later on.”
“Sorry, I’m giving you an excuse to go home now,” Sylvia said, going back to her desk to rummage through her drawers. “But I’ll give you something as a treat for being such a nice sport, if you promise not to perv on the ladies again.”
Issei lifted his head off the seat. “If it means I get to have more bits of fun like this, well, I can’t really argue against that, huh?”
“No, although we’ll see how you’re feeling before I let you have any more of these experiences. In the meantime, I want you to wear these home.”
After being handed the item in question, Issei looked stunned at what her request was; a pair of panties, like the kind that any girl would wear. “This is...why?” He asked sincerely. “Why panties?”
Sylvia shrugged. “I figure at the very least, you might be able to get a better understanding of what women deal with when you get perverted with them. Don’t you agree?”
“I can’t say I agree, no, but...well, if it’ll lead to more stuff to do, I can’t argue with that.”
Issei made sure to hold onto the panties, putting them on in place of his normal boxers. After he put his pants back on, he blushed at the knowledge that he was wearing something so emasculating, it was almost embarrassing. But to be so close to something worn by women also managed to arouse him. And as his dick started to rise back up against the bulge of his pants, he came to realize why Sylvia wanted him to take the rest of the day off from school.
“R-Right, I better get running! Bye, Sylvia! Thanks again for your help! See you tomorrow, maybe” Issei then rushed out of the office, footing it out of the school so he could make his way home and hopefully jerk off there. Sylvia smiled as she watched the boy vanish, rubbing away at her own crotch after having a delectable feast.
“Oh, not a worry,” Sylvia giggled, sniffing at his boxers, “you’ll be seeing me a lot sooner than you think.”
##
When Issei ran to his room, he slammed the door behind him. He was thankful that his parents were out of the house, likely working on an errand of some kind. He was hot and sweaty, having gone through a lot of traffic just to get here. He had a difficult time hiding his bulge, as it was so present against his pants that it was hard for anyone else to ignore it. In fact, he was certain that it had grown larger than it already was.
Once he kicked off his shoes and yanked his pants down, Issei sat on the edge of his bed, in disbelief over what he was seeing. Pushing out one of the legs of the soft and cotton panties was a big and massive cock. It was even larger than what he had previously, almost twice as thick and five times its original length. The worst part was, he could only imagine how it must look when he was flaccid.
Keeping the panties on, Issei couldn’t help but hold his massive shaft up, in awe of what it had grown into. The member was immense, almost ready to tower even over him. The devil’s eyes rested on the shaft, mesmerized by its majestic state of being. He knew he just had to play with it for himself, see what it was like to jerk such a big slab of meat.
He laid back on his bed, resting his body as he reached for his newly grown cock. As he tugged away at the member, he realized that it was too much for just one hand to do work on. He was going to have to do something that he had never done before: He would have to use two hands.
It was a dangerous feeling to tug his rod with both hands, but it was something he was willing to do if it meant he could bust his nut. He grew heavily aroused by his masturbation session, and soon his mind began to drift. The Breast Dragon Emperor couldn’t help but fantasize, let his mind flow into the fantasy realm and daydream about how badly he wanted to put his dick inside so many of the girls in his life.
He thought about how he could stuff this big beast inside Rias’s pussy, finally showing the president that this was what he was worth to her peerage. The idea of stuffing it up Akeno’s butt was also prominent, giving her the blissfulness of heaven while mixing with the agony of hell at the same time. With Koneko, he could likely stuff it all the way through her tiny body, finally getting back at her for all the snark she gave him over time. Asia could experience heaven at long last, although really, that could fit Xenovia as well…
He thought especially hard about Rossweisse, how her curvy body would fit tightly against his shaft. She would be calling him ‘Zeus’ instead, crying out “Oh my Issei!” instead of calling for God. The thought made Issei grin, his hands starting to run across his torso. He rubbed from the base of his shaft up towards his collar bone, running over some bumps along the way. From his abs to his boobs to his chest, he-
Issei stopped fapping, his eyes opening wide as he realized something was wrong. No, different. While he could still see his giant weiner, he realized there was something blocking the way. It seemed to be some sort of mountain range, but how could that be when they were right before his eyes? Then the pawn touched them, felt them, and even squeezed in the pointed tips…”Nph!”
Wincing, Issei realized that they actually belong to him; these were his tits now. This astonished the young devil, who never thought that such a growth was possible for his body. “Boobs? Me…?”
Once he sat up, Issei realized that he had grown in more than one way. True, the tits were a noticeable asset of his body now, hanging from his chest in a way that made them jiggle, but he felt his thighs squeezing into his ball sack. Even when he spread them apart, it was impossible to loosen the grip on his nuts, as he realized that his upper legs had grown thicker as well.Even his waist felt a little different, but he couldn’t quite see it for himself with his massive mammaries making it impossible to see for himself what changes had been made to him.
He had to try and glance at himself in the mirror, which itself was hard to do. When he stood off the bed, he stumbled around, as all of his weight had been shifted around all over the place. Not only did he have tits and a larger dick, but now his ass was massive, too. Not even just thick or huge, even fat, but massive. It reminded him of two air bags that went off in a car, growing so big that it was nearly comical in its effect. He could barely see his full torso, back or front, as a result.
“Geez, this is crazier than I thought,” Issei said as he studied his body. “I never had these before, but it’s kind of fun to play around with everything.” He shook his ass back and forth, watching as his cheeks swung around with him. They did clap together from time to time, which made a wonderful sound to his ears. He hummed as it warmed his mind, feeding into the arousal he had already been witnessing.
“Man, if only I could fuck myself,” Issei said. He paused, asking himself where such a statement had even come from, as he would likely never have said that among the rest of Rias’s peerage. Even his tits were bigger than Akeno's, something he didn’t believe that was even possible. Not even the largest JAV had titties so huge.
That was when Issei looked again at the panties, still wearing them around his waist while his cock stuck out the leg. Pulling at the hem, he couldn’t help but notice there was a cartoony drawing of Sylvia drawn on the inside, with the counselor winking at him. “What gives with these panties?” he asked as he massaged his nipple, which enlarged with the rest of his boob.
“Isn’t it obvious? My panties have changed you greatly!”
From out of nowhere, Issei found his tits groped from behind. He gasped as the hands pushed them into his chest, almost suffocating him with his own melons as the excessive softness almost pushed into his face. Looking in another mirror, he could see that it was Sylvia, which made him extra startled. “Wha-wha-wha-whaaaa?! How did you get in my house?!”
“It comes with the panties,” Sylvia assured him, nuzzling her cheek against his. “You were getting horny, and you turned into a slut.”
“That’s the second time you called me that,” Issei noted.
“And when you get horny while wearing those panties, that’s when I come in and help get you off.”
“But why?” Issei asked.
“Because I really like you perverted types. And I enjoy giving you a feel for what you should expect to give when you’re the one in charge.”
“I dunno, I don’t feel like I’m in cha...harge…” Issei hummed, sucking his lip as he felt something protruding between his legs. It didn’t belong to him, though he didn’t imagine that Sylvia had any sort of additional appendages.
Then he looked behind him, and saw that she did have her own ball sack and cock, which looked larger than his own while he glanced at it in the rear mirror. So he wagered that it was her rod bucking against his scrotum, unable to push past his own giant sack. He could hear a softened pounding against his nuts, with a little moisture being left behind by her own shaft.
As Sylvia continued to dry hump Issei’s dump truck size ass, she took notice of something that wasn’t so apparent to the young man himself. “Oh, sweetie, are you sweating? I think you were sweating when you tried to beat your meat.”
“Is something wrong with that?” Issei asked.
“Well, no, but you must have worked up a lot of that on your way home. Why don’t I help clean you off?”
“Wait, whoa! Time out!” Issei said, tapping his fingers against an open palm. “I don’t want to go out there looking like this.”
“Not a problem,” she said with a smile, “I can help you out with that.” All Sylvia did was snap her fingers, and she and Issei were directly in the shower, much to his surprise. He was still fully naked, aside from the panties, but she had her dress vanish without trace. “Much better. Now why don’t you join me here…”
Issei found himself pulled into the shower with Sylvia, who already had the water running. So much was happening within that time, from the realization the counselor was magical to the fact he almost lost his balance thanks to how his new body build threw him off. “Hang on a minute!” Issei shouted. “At least let me get the panties off!”
“No no, my dear child,” giggled Sylvia, getting Issei on his knees before her cock, “the panties stay on. Otherwise you don’t get to keep that shapely body of yours.”
Issei moaned as the tanned woman slapped his face with her cock, which was only half the size of his own. Yet it packed a wallop against his cheek. “Now go ahead and try to suck on it.”
Doing as the counselor was told, Issei tried his best to push his lips over the glans, though he had some trouble as he had never taken a cock down his throat before. His spit flew out of his mouth, though Sylvia seemed to love the sight of that. “Aw, baby’s first oral blowjob. Don’t worry, I’ll help you out.”
Sylvia grabbed Issei by the head, pushing his mouth further against her dong. The saliva worked well as a lubricant, helping to smooth his throat out as she helped him bob back and forth along her shaft. He could feel his throat bulging outwards whenever the girth hit, just so he was able to fit it within his orifice.
Issei did at least try to do something to feel as though he was doing something of his own accord, grabbing his tits and squeezing them around the shaft. As the shower water started to run over their heads, it began to rain down on their bodies, which helped the Breast Dragon Emperor move his tits along Sylvia’s shaft with ease. The tanned woman was relaxed, playing with her own mounds while the young man helped her to get her dick fully erect.
While Issei might have been growing adjusted to it, it was still strange that he was wearing female panties and letting them get sopping wet, worried that they might fall off with how the water weighed it down. Though he had to ask how she planned to do much more with him while he wore them.
When she was finally ready to move on, Sylvia backed away from Issei, grabbing him by his hair to pick him up to his feet. The hard tug on his head hurt him, though not as much as when the counselor shoved him into the shower’s walls. She managed to pull the panties to the side, staring at Issei’s anus as it puckered about. But that wasn’t what her gaze was looking around for; indeed, she found the hole she was looking for, and it had formed just underneath his scrotum.
“Oooh, look at that pussy oozing cum,” Sylvia said, “I bet you didn’t even know you grew one, did you, Issei?”
“I guess I didn’t…” Issei moaned as Sylvia tried her best to get the shaft under his panties to reach his new hole. The stimulation he felt was something wild, allowing him to hit a new sense of pleasure that he had never laid witness to before, even after letting the tanned counselor rim his ass with her tongue.
Issei tensed up when the shaft finally punctured the folds of his new pussy, feeling it stretch his canal out. His eyes rolled back as the eyelids twitched wildly, all while his fingernails tried to claw against the tiled wall. Sylvia was able to fit the whole of her cock inside of him with ease, though the girth caused it to bump out against his stomach lining. It was a new experience, though every moment made him wonder if this was all natural for any woman to experience.
“Mmm, what a nice fit you are for my dick,” Sylvia said, giving Issei’s wet ass a hard smack. The young man yelped, sucking on his lip as he absorbed the pain from the palm strike, too focused to realize she was pumping away at his rear end while her cock slid around the cavern. “Such a good pussy you are, Issei. I really love how it squeezes on my cock like any good onahole would be.”
“Yeah, that’s nice to hear…” groaned Issei, doing his best to adjust to the thickness pumping away inside his tunnel. As he took the brunt strength of Sylvia’s pelvis ramming into his plump behind, he could only wonder if this could get any more humiliating.
“Issei? Are you in here?”
Issei jolted as he heard Rias’s voice inside the bathroom, the door opening and closing as she stepped inside. He whimpered, embarrassed that his crimson haired president would find him in here being pegged by the guidance counselor. He might as well answer her, of course. “Y-Yeah, I’m in here! I wasn’t feeling good so I left school early.”
“I figured as much,” Rias said, standing in front of the sink as she examined herself in the mirror. “I do hope you feel better, we’re going to need you in our next rating game. Don’t worry, I won’t push you into any training today.”
“Great, thanks!” Issei groaned as Sylvia pounded him harder. The dark skinned woman was in love with his pussy, smiling wickedly as her cock punched harder into the young man’s stomach lining. Though she was drooling, it was hard to tell while the shower water ran over them, drenching them while giving their skin a lovely sheen. “So what are you doing here?” Issei asked Rias, wondering how she couldn’t hear the violent claps against his ass cheeks.
“I just had to check my makeup and make sure that it’s all in line,” Rias replied, “her eyes looking directly in the mirror. The ignorance of what was going on in the shower behind her amazed Issei, as if she either was intentionally being oblivious about what was happening in there, or Sylvia had somehow cast a spell to leave her unaware of the situation. In any case, even as his moans of pleasure grew louder, there was no curiosity coming from the crimson haired devil about it.
“Ah, shit…” Issei growled as Sylvia fondled his tits.
“Did you say something, Issei?” Rias asked. “Are you out of shampoo? I could give you some if you need it.”
“S-Sure! Yes! Please!” Issei shouted, though he had no idea if that was him begging for more from the counselor or not. What he did know was that his cock had finally rubbed up against the wall, which pushed up against his belly. Sylvia’s cock also pressed in from the inside, which created more friction from both sides. As Rias approached the shower curtain, he reached out to grab the shampoo bottle from her, ready to bring her in or even pull the curtain back to reveal what the heck was going on with him. But just as he grabbed the bottle from her, the ORC president let go, making her way out of the bathroom.
“Get rested, Issei,” Rias said as she opened the door, “I’d go right to bed if I were you.”
She shut the door behind her, leaving Issei to be pegged by Sylvia and her own giant cock. “I don’t get it…” Issei hummed, his hands reaching for his cock as he felt himself getting close to his peak.
“Oh, why she didn’t know you were here?” Sylvia laughed. “Honestly, I’m not so sure myself. I guess my magic works much better than I thought it could. Oh well. At least I know you’ll be able to handle my seed when I burst.”
“Wait, I don’t know if I can-” Issei groaned, his feet leaving the ground while standing on his toes. His body was at its most tense, with his cock throbbing just seconds before release. It shot off just after Sylvia let her seed flow inside of him, exploding like a geyser while it aimed upwards at the ceiling. The goo shot upwards, raining down on them harder than the shower water, although that was thankfully around to cleanse them of the substance. All the while, the Breast Dragon Emperor felt his stomach swelling up, inflating with all the seed she was dumping into his new pussy. Body parts he never had before today were being filled with jizz, with his stomach growing like a balloon with how much cum was being dumped into his pussy.
Sylvia soon depleted her cock, pulling it out of Issei’s cunt to finally let him relax. The young man fell backwards, letting his giant tits, inflated belly, and deflating cock resting on top of him. When he was able to see things, his eyes were dulled, worn down from the amazing climax and filling that had happened in the last minute. Soon, all of his exaggerated traits shifted back to normal, his body returning to his default state while the panties were still on him. The seed he had expelled washed into the drain, though he hoped after all that devil construction that the pipes were able to deal with the seed without clogging them up.
“Feel better?” Sylvia asked, watching her own shaft deflate.
“Yeah…” Issei sighed.
“Good to hear,” she said with a giggle. “Now don’t you dare take those panties off. I want you to wear them to school tomorrow.”
“But aren’t they dirty?”
“Oh, no, they self-clean in every sleep. And trust me, I know you’re going to get heated sooner or later again. Bye, honey!”
With that, Sylvia faded away, leaving Issei with his thoughts while he took the time to regain his strength. The constant thrashing of his pussy and the cum he unleashed was a lot for him to handle, so he clearly needed to take some time and think about matters.
In fact, he was curious; his body had returned to normal, but did he still have a vagina?
Upon checking under the panties, Issei found that no, that was gone too. Though it was likely to appear again when he was horny. Though he was going to have to do a lot to subdue his hormones for a while…
##
“Issei, are you okay? You’re walking a bit weird today.”
“Yeah, fine. I’m just trying something a little different with my boxers. Fresh new pair, so they need some breaking into.”
Issei followed behind the rest of the Occult Research Club, best known as Rias’s peerage, as he didn’t want it to be obvious that he was wearing cotton female panties underneath. Although it was starting to grow apparent that he made a big mistake walking behind a bevy of attractive women like the devils he was with.
From the rear, he could get a good glimpse at the ladies and their cabooses, watching Rias and Akeno in particular sway their hips from side to side. Their cheeks bounced back and forth, leaving the Breast Dragon Emperor distracted by their posteriors.
They had arrived at the train stop, making their way to school from there. It was a little different from their normal walks to school, but due to some construction going on downtown that made it harder to travel. The trains were the only reasonable means of transportation, so this may as well be the next best thing for them.
“Well, at least the trains don’t seem so crowded,” Akeno said with relief. “Plenty of room for us to spread out.”
“Right, that sounds great!” Issei said with relief. He didn’t mean for it to sound so desperate, but the fact he was starting to get hard from staring at the girls’ butts was too much. He needed some space, especially after yesterday where Sylvia pounded his pussy and Rias couldn’t do anything about it.
Just before the doors to the train could shut, a long, tanned leg stopped it from shutting, allowing the owner of such thickness to walk into the car. She approached Issei, who had decided to sit by himself while the rest of the peerage had separated off into their own directions. “Excuse me, sweetheart, but is this seat taken?”
Recognizing the voice, Issei gulped as he lifted his head up, slowly studying the tall, curvaceous woman that was right on top of him. His lips quivered as he saw Sylvia smiling at him, the guidance counselor having her own bulge push against her dress. “Good morning, Issei,” she said, “surprised to see you here. Taking a different route?”
“Uh, kind of…” Issei said as Sylvia took a seat right next to him. “It’s kind of a long story. What about you, Sylvia?”
“Well, I sensed someone was getting aroused,” she purred, running her hand over his pant leg, “so I naturally had to arrive at the source of such horny powers.” She watched as Issei relaxed from her touch, rubbing away at the shaft while it remained under the fabric of his pants. She watched on as the length grew underneath, the shaft stretching itself out while more attention was brought onto it. “I’m so glad to know you’re still wearing the panties, by the way.”
“Sylvia,” moaned Issei, “I’m glad you’re here and all, but not right now. My friends are gonna notice…”
“Are they?” Sylvia laughed, looking up at the sight of the others in the peerage. Koneko was too occupied feeding Gasper some sweets, Kiba and Rias exchanging notes for their classes, Akeno in her own meditative state, with Asia and Xenovia discussing the different takes of religious scripture that they had taken on thanks to their respective upbringings. Rossweisse was off on her own business, which meant that nobody had even become aware of the fact that Sylvvia was even present, playing around with the young pawn throughout. “Don’t worry, Issei, I’m going to keep you occupied while we’re on the way to school.”
“Thanks, I guess,” Issei sighed, his eyes shutting for a brief period while he allowed Sylvia to massage away at his dick. Soon enough, he felt something strange about things, as he felt the train’s air conditioning brush against his legs. But he hadn’t felt Sylvia remove his pants, nor did the zipper get pulled down. As far as he was aware, he still had the school’s pants on him.
Though when he opened his eyes, he realized that it was more than just his body that had undergone some changes. Issei jolted as his pants turned into a shorter version of the school’s skirt, with his normal button down turned into a blouse that tied above his midriff, with the buttons undone to allow his breasts to fill out. Indeed, his body had regained its feminine shape once again, though his breasts hadn’t fully grown out like they had the previous day. His dick had expanded, however, growing massive in length and thickness alone.
“I changed again…” Issei said to himself.
“All that horny energy has to go somewhere, doesn’t it?” giggled Sylvia as she slapped her palm down on his member. Issei jittered at the repeated strikes to his shaft, which had grown immensely sensitive as a result. His legs raised up as a result, which he took note of just how feminine his outfit had become. While he may not have been wearing pants anymore, what covered his long, thick legs were fishnet stockings, which reached up to his knees, and high heel stiletto sandals. The outfit’s transformation was something else to him, like nothing else he could have imagined.
“Geez, these panties really are something magical…” purred Issei as he continued to receive a cock massage from the dark skinned woman.
“That’s not the only magic you’re going to experience,” Sylvia said as she removed her dress to reveal her own massive erection. “Now come on, be a good girl and sit on my dick. Let’s watch how it stretches you out.”
Issei gulped, seeing the size of the shaft for himself while she sat down. He knew from feeling it in him firsthand that it was giant, but he didn’t get a proper glimpse until now. He was more nervous than before about taking it, but he was going to have to do his best to satiate the guidance counselor.
As he sat down on the tip of the shaft, Issei bit his lower lip, feeling his pussy stretch out from the girth. Sylvia let out a relaxed sigh, resting her head on the seat while she filled up his canal. For the young devil, it was something unusual that he felt his virginity being taken for a second time, since that particular part of the body had vanished after their last session together.
It hadn’t fully fit like a glove on him, but Issei definitely had some familiarity with her rod being inside him. Once it was deep enough, Issei found his giant ass sitting on Sylvia’s lap, with none of the other devils being wiser about his lewdness. He rocked away on Sylvia’s lap, moving back and forth against her lap while you felt the cock squirming around inside your fresh hole.
“It’s not so bad a second time I guess…” moaned Issei, the crown throbbing against his stomach lining. It was quite clear where Sylvia’s shaft stood while the midriff was exposed, and yet none of the others on the train car were aware of the presence of something lewd and strange.
“No, I always make sure that it’s as wonderful as the first time,” Sylvia assured him as she reached around to fondle your breasts, squeezing away at them through the blouse. The young devil felt his nipples as they were ready to pop out of the top, though Sylvia kept teasing the idea of fully exposing his overgrown melons. They rubbed against his shrunken blouse, with the areola barely peeking out of the cleavage. His tits were going to spill out in due time, and by then someone was bound to notice.
Then Sylvia pulled on the tied up part of the blouse, allowing Issei's boobs to fall, jiggling as they relaxed themselves. She played with his jugs more freely, hearing Issei moan in delight of having his shoulder boulders played with so elegantly. He took another glance around the car, noticing that his fellow devils were still completely unaware of the fact he was being fucked, let alone the fact he had a much more feminine appearance over him.
Issei did the best with his new shape and outfit, deciding to try and work away at Sylvia's shaft. She hummed through thinned lips as the Breast Dragon Emperor started to lift his ass off her lap, only to drop it down with an impactful clap against her legs. His cock bounced along with him, while his mammaries shook around as a response to the shaking about. "Oh, boy, are you a natural," Sylvia said in a seductive tone, "you've been wanting my dick for a long time, haven't you?"
"It's kind of hard not to think about it," Issei replied, "and it was only just yesterday that I got introduced to it."
"And yet you seemed to adjust to your assets rather quickly." Sylvia eventually found the nipples on Issei's enlarged tits, her fingers squeezing down on them with as much strength as she could muster. The Breast Dragon Emperor shivered, his legs squeezing in on his balls while he felt the sensitive pinching coming from the guidance counselor.
There was a bit of horror rolling down Issei's spine when the train came to a stop, as they had reached the next station. There was still time between here and their next stop, which they had to get off to get to school. The young pawn gulped, worried over what was to await him. He grew nervous at the fact that more people were going to get on board, see his current state of being, and laugh their socks off. Already he could feel his face turn red from the humiliation that awaited him.
At least one person had made it in, though she looked quite unique. The woman herself was very top heavy, yet just as curvy as Sylvia was. She had paler skin to her, dressed in a tight white gown while two horns curved in adorned her forehead. Once she took a look in Issei's direction, she lit up, and immediately marched over to meet with him and the counselor. "Oh, Sylvia! Let me guess, another horny boy to play with?"
Sylvia hummed as she nodded. "Oh yes, a naughty slut who needs to be taught a little bit of humility. Issei, this is one of my friends, Albedo. She likes to join me in my mischief from time to time."
"Ch-Charmed…" Issei shivered, Sylvia's crown spiking against his cervix that time. He reached his hand out to the horned woman, expecting her to shake it. But he received a laugh and a shake from her head instead.
"I know what you're expecting," she said as she pulled up on her dress, "but if I'm being honest this is the only thing you're going to use your hands on." Once her legs were uncovered, Issei gasped as her own dick sprang to life, the tip just an inch away from getting right in his face. "Okay, NOW you can shake."
Sylvia remained amused, entertained by what she was seeing from the young devil as he wrapped his fingers around her shaft. It was thicker than the guidance counselor's, but not as long. It was still a shock to Issei, who had never seen any other dick than his own, whether the panties grew it or not. He hummed as he looked at Albedo's urethral slit, watching a clear yet thick liquid pooling up on the very tip. It was different from the cream he was most accommodated to, but it made him want to give her a try.
Issei then pushed his lips over Albedo's cock, his eyes looking around the car at his fellow devils. None of them noticed the huge women that were using him to keep their cocks warm, which was a surprise to him. Even when he squeaked loudly from Sylvia shifting him around her dick once more, his voice was barely audible thanks to the rod muffling him. Even if he weren't plugged by two huge dongs he pondered if they would realize something was wrong.
Even Albedo took notice of the absurd ignorance of the others on the train, puzzled by their lack of shock and surprise. "Well this is a new one," said a puzzled Albedo, "I've never seen such nonplussed voyeurs of our activities."
"I'm perplexed as well," Sylvia shrugged, bringing her fingernails to the young man's nipples, "but nevermind that. Since you're here, perhaps we should see if our little pervert is seasoned well enough."
Issei whimpered, almost melting as Sylvia pushed her nails against his nubs. As this caused her to push in against his breasts, the softness and sloshing milk was enough to help her push against the nipples until, at long last, she was able to puncture through and penetrate the breasts. Caught off guard, Issei twitched while his scream was muffled by Albedo, showing off that they were able to do much more on his body.
"Oh, delightful!" Albedo said with unusual glee. "His nipples are ripe and ready for fucking! I can't wait to push my cock in his tit."
"Dough whaft?" Asked a concerned Issei. The horned woman stepped back from the young devil's mouth, though thanks to the tight squeeze of his throat it ended up setting her off. Once she got her dick out, she ended up spraying Issei in the face, with Sylvia collecting some of the fluids as they splashed back against him. She loved the taste, as anyone could expect, but was amused at how easily she was able to let her fluids shoot from her staff.
"Albedo! You must have been immensely pent up!" Sylvia cackled, with Issei eyeing his ignorant buddies as he thought surely that was going to be what caught their attention. "Why else would you shoot your load so easily?"
"At least I'm not the one wearing yolk on my face." scoffed Albedo.
"Actually, this is yours."
"Oh, oops! Sorry about that. But now that I know his tits are fuckable, let's try to give it a good reaming."
"Are you sure this is safe?" Issei asked with concern.
"Don't worry," Sylvia said as she ruffled his hair, "you'll likely return to normal like yesterday."
"Likely isn't reassuring enough…" whimpered Issei as Sylvia helped him off her cock. But much like what Albedo experienced, getting the young man off her cock was tougher than she expected. There was suction due to the tightness of his pussy, with a long queef coming from his canal.
With just the tip stuck in the folds, Sylvia finally let her own load shoot in his muff, causing the canal to fill up quickly. There was so much seed that like before, inflated his belly with the jizz. Issei whimpered as he shot his own liquids from the canal, drenching the dick while making a puddle of his own fluids. Sylvia's legs were smothered in it as well, though she didn't seem to mind it too much.
The crown finally popped out of Issei's pussy, letting Sylvia's seed flow out of his cunt while adding to the mess on the train's floor. The dark skinned counselor held him up while Albedo gave his belly a squeeze, just to watch and see how much of the fluids were able to gush out. With so much spunk, it trailed its way closer to Rias and the others, yet even then they were so absorbed by the activities they were performing with one another that they didn't even notice.
At least the panties Issei wore were still intact.
Sylvia let Issei drop to his knees, with his giant jugs sloshing about. She and Albedo looked at their cocks, noting how they were starting to shrink down. "Oh dear," Sylvia sighed with mock shock, "it looks like our penises are shrinking and we aren't at our destination."
"Guess you're going to have to suck it up and fondle our cocks so we can fulfill ourselves until the next stop," teased Albedo.
Issei rolled his eyes, opening his mouth wide while waiting in anticipation for one of the girls to slip their dick in first. To his surprise, they managed to force both cocks straight past his lips, even stretching his throat out to cause it to bulge with their combined girth. Issei's eyes teared up, swearing that they had twisted their rods around one another like a strand of DNA.
"Mmm, so tight!" Albedo said with glee as she pumped her hips against Issei's face. "I love how it feels so much more snug inside him now that we're sharing the same hole!"
"Oh, my, yes," Sylvia said as she played with her nipples, "I forgot what it was like to have your cock rub against mine, Albedo. We really should try to work on doing that more often."
Despite how stuffed he was with their shafts, Issei did his best to bring pleasure to the two ladies, using his tongue to flick and lash away at the underside of their genitals. That seemed to do the trick for them, as Sylvia and Albedo held each other close while they moaned in delight. Their breasts were practically pushing up against one another, the nipples swirling around the other like fleshy cogs. The young devil's mouth began to salivate, drooling down his chin the longer he had to keep up with the oral services while their veins pumped away inside his throat.
After they finally reached their stiffest point, both Albedo and Sylvia were ready to try and penetrate the nipples of the boy with their big thick dicks. Issei watched on as their tips pressed against his boobs, pushing them in while they remained against his nubs in particular. They were adamant about using his breasts as their next sex toy, which did worry him. Despite the fingernail penetration he had experienced, he never thought about nipples being a fuckable asset of his body, even with all the cosmetic changes he had witnessed.
But Albedo and Sylvia had finally managed it, their dicks passing through the tiny space on the nipples while occupying the space inside his breasts. It was weird and unnatural to the Breast Dragon Emperor, though everything that has happened throughout the last day may as well be summed up as such.
“Yes, that’s it, slut,” Albdeo laughed, “hold those nice titties up so we can keep fucking them! What a delightful feeling to ream your boobs with the milk sloshing against my cock!”
“I haven’t felt this good in a while,” purred Sylvia, grabbing hold of Issei’s breast as she reamed away at it, “oh, his pussy was great, popping his cherry was fantastic, but I can’t resist the good feeling of having a nipple to fuck! So good! It’s so good!”
Issei hummed as he kept his tits up for the two women to plow, watching them shake and jiggle with every impactful force. They two tall and curvaceous ladies were eager to plow the young man, though the measures at which they were willing to do so was beyond him. He was at least relieved that his belly had managed to drain of Sylvia’s seed, though it was really his cervix and canal that had inflated inside his stomach. The pool of cum had spread out so far that it touched against Kiba’s shoes, which still surprised him that none of the devils noticed how the ground was covered in a white and milky substance that offset the usual colors of the car’s floor.
Albedo and Sylvia were getting rougher with his melons, with his nipples having grown so easy to penetrate that they were starting to pump out milk from inside. Issei had no idea how that might have been possible, but now his lactation had begun to mix in with the jizz left behind by the women and their fixation on using him like an onahole.
The strangest part for the Breast Dragon Emperor was that all of this nipple fucking had made his cock as hard as it could get, the veins throbbing hard as it slowly started to hit its breaking point. Issei was breathing heavily, trying to hold back the chance to bust his nut. He loved the feeling of having a big cock so stiff and erect, yet at the same time he oddly didn’t want this transformation of his body to end. He was certain once he shot his load that would be the end of it, though he reasoned with himself that he would look really weird being so slutty while at school.
That was finally what set Issei off, deciding to cave into his pleasures rather than bottle it up. His cock shot off between the legs of Albedo and Sylvia, hitting against one of the unoccupied seats on the train car. The women grinned at this, watching his face contort while he let his load shoot out, as it was clear that they had finally found his breaking point. “What do you think, Sylvia?” asked Albedo. “Shall we milk him for all he’s worth?”
“Be my guest,” Sylvia said, herself holding a wicked grin.
The two women came at the same time, with their jizz flourishing inside the tits while they remained already milky in their size. They grew out as part of the expansion of the seed, which grew in the end to be almost as big as his own body. He was amazed that something like this was even capable of reality, wondering why he had never seen Rias’s tits grow so ginormous.
The two ladies finally pulled out of his nipples, watching as Issei collapsed on top of his own enlarged melons. His tongue stuck out from exhaustion, his eyes glazed over as he felt the afterglow of ejaculation was over him.
“Mm, a very satisfying one, Sylvia,” Albedo said as she stretched her arms out, “I think you’re going to have to invite me the next time he’s wearing those panties.”
“Oh yes, but I’ll leave that up to him,” said Sylvia, “he doesn’t have to wear them all the time, just when he prefers to experience the fun of being a fucktoy again.”
Issei finally relaxed himself, getting a bit of sleep. Or so he assumed.
“Issei? Wake up, the train’s at our stop.”
Issei found himself awoken by Rias, with the other devils making sure the train’s door remains open for the sake of buying time on getting the pawn up. “Oh, geez, what happened…?” As Kiba helped him to his feet, Issei found that he was completely normal; no feminine parts were out and about, and even his clothes returned to their normal state. Nothing slutty about him after all that he endured.
“Nothing, as far as we’re aware,” Kiba replied, “you’ve been asleep the whole ride is all.”
“Well, that’s good, I guess,” Issei sighed, “it must have been a hell of a dream then.”
“Yeah, but you still have a few things to answer about,” Koneko said as they finally got off the train. “It looks like you’re gonna need a change of pants.”
With an audible gulp, Issei reached for his butt, realizing that the jizz from before had ended up seeping out of a hole that hadn’t even been used. Worse, the panties didn’t do a very good job holding it in.
“Yeah, uh, that’s gonna be a long story…” said an embarrassed Issei.