"You don't have any homework to tend to?" Vanilla asked. "Of course not. Finished it all before I came here." Tails said. "Good boy. There's no excuse for bad grades. Not even dick." "Where are we going?" "To a friend's place." Vanilla explained. She and Tails got redressed and left her apartment about an hour later, after cuddling and going one more time. She held his hand the entire time they headed down the twisting walkway between apartment buildings; it felt awkward, like he was her son and this was his first trip to a theme park. They stopped at the first floor of one of the more isolated buildings. Vanilla knocked. A few seconds later, a young, busty bat in her early-to-mid twenties appeared at the door. "Hello, Vanilla." she said. She was wearing a crop top and panties and that was basically it. The fabric tugged at her labia, and more than a bit of the plump flesh was exposed. "And who is this?" "This is Tails. He's looking to get more confident, if you know what I mean." Vanilla explained. "Tails, this is Rouge. She's a webcam girl; one of the best, and also my friend." "H-hello!" Tails squeaked, forcing himself to look away from that revealing, amazing cameltoe. "My, you're quite the cutie, aren't you?" Rouge asked, biting her lower lip seductively. "Been a while since I had fun with a little boy like you." Tails gulped. She really had sex with boys his age before? "Like I said, he needs to get more confident having sex, so I figured you'd be able to help us. "Oh, I can help with that, most definitely." Rouge said. "Excellent. I knew I could count on you. Well I gotta head back home and think about what I'm doing for dinner. You... have a fun time with my friend, here." Vanilla said, booping Tails on the nose before turning and leaving. Her butt swished back and forth as she left. "Alright, Tails. Head inside and take off your clothes." Rouge said. "Let's see what we're working with." Tails nodded and removed his clothes after Rouge shut the door. He was not as shy this time. After all, one hot woman who wasn't his mom got to see him naked, so what was one more at this point? Of course, it was still a little awkward, and he fought the urge to cover his crotch. "Hmm, not bad, not bad." Rouge said, folding her arms and holding her chin between her thumb and forefinger like she was observing a piece of art. The thought humored him. "How big do you get?" "Huh? You mean how big my... penis gets?" Tails asked. He blushed heavily. "I mean... I've... never measured myself, before." "Really, now? Guess we'll have to take a proper measurement, then. Wait here while I go fetch a ruler." Rouge left the room. Tails checked out the apartment while she was away. Compared to the accommodations for a mother and her teenage daughter, Rouge's bachelorette pad was relatively spartan and extremely informal. There was a dinner table near the kitchen, but it only had one chair. There was a couch and chair in the living room, but the chair was more like a medical chair, with stirrups and an array of doodads and attachments folded up underneath. The couch and the padding of the chair were both made of rubber. An adjustable mechanical arm held a flatscreen monitor up where whoever was sitting in the chair could watch it. It wasn't the kind of place he expected a person to live. What was this chair for? Rouge returned with a ruler and vibrator egg in her hand, along with its respective remote control. She was naked now, as well. "Interested in my setup?" she asked. Tails blushed and backed away. "I wasn't looking!" he stammered. "Don't be shy, Tails. It's not a sin to be curious." Rouge stepped forward. "Now come on, hop up on the chair and let's see how big you really are!" "You mean... with my legs in the stirrups and everything?" he asked nervously. "Of course! Gotta get a good measurement of your dick size and everything!" Tails tentatively climbed up onto the chair and put his feet into the stirrups. Once he was in place, Rouge pulled a lever and suddenly the stirrups swung outwards, spreading his legs far apart. The position made it very difficult to try and escape when his legs were higher than his head. His dick twitched slightly. "Okay, now. Just try and relax. It'll be easier that way." Rouge instructed. She procured a bottle of lube from a basket on the side of the chair and covered the vibrator egg in a light coating. She then brought the egg down between Tails' legs and pressed it against his tight butthole. Naturally, he gasped and bucked his hips upwards. "I said be still, hun." Rouge said. "We gotta get this in you if we want a good idea of how big you can get." "How is it supposed to he-AHA!" Tails was interrupted by Rouge applying even more pressure against his sphincter muscle. It spread further apart than when he ever had to use the bathroom. It was a little painful. Then suddenly, the entire thing popped past his tight asshole and sunk into his rectum. Something about this made Tails moan in a peculiar way. He could feel the egg in his ass, occupying space in a way he was not used to. It pressed up against... something... deep inside his butt that made him feel weird and for his dick to stand up straighter, and faster than normal. "You've never had anything up the butt, have you, Tails?" Rouge asked. "N-no, I haven't. Why?" Tails was breathing heavily, though he didn't do anything strenuous yet. "Deep inside your body, between your rectum and bladder and what your urethra threads through is your prostate." Rouge explained. She leaned forward over Tails from between his legs and traced a teasing finger down his chest. His dick was nestled right on top of her enormous breasts. He wanted her to put it between them. "It's a very sensitive organ. You can stimulate it from inside your butt, even with a finger, but we've got toys for a reason." Rouge unfolded a mechanical arm from underneath the chair and extended it up and over Tails' body. At the end of the arm was a camera. Rouge locked the camera into place with a knob. From its angle, it was able to encompass all of Tails' body in the frame. "What are you doing?" Tails asked as she pressed the record button. "You know that's illegal, right?" "I won't tell anyone if you don't." Rouge said, giving him a wink. She then pressed the power button on the remote control for the egg vibrator, and it suddenly whirred to life somewhere deep in his ass. It was powerful - that was a surprise in and of itself, but the real shocker was how it felt against his prostate. It was weird, stimulating a part of his body he was never sensationally aware of before, and one that currently held more influence over him than anything else. Orgasmic pleasure built up within him almost instantly. His already erect dick throbbed powerfully and then grew another inch and a half. "Ghaaaahh! W-what is happening?!" Tails cried out. "This is what we call milking the prostate." Rouge explained. "Isn't it the most exquisite thing you've ever experienced?" "AAAAAAA HHHAAAAAHHH!" "I'll take that as a yes." Rouge giggled. She put down the remote on a stainless steel tray attached to the chair, then picked up the ruler. "Now hold still, I gotta get an accurate measure of your dick." She pressed one end of the ruler against his pubic mound and held it to the length of the shaft. "Now some guys say to measure from the base of your balls to the tip, but that's a goddamn lie. Always measure from the base of the top to the tip. Any girl that knows a good dick will be able to tell that you're fluffing the length. Some guys take it a step further and add another inch or two on top of that. Those guys aren't worth fucking." She let out a whistle. "Seven inches." she said. "Lucky you, little man. I know quite a few guys that would kill for that kind of length." Tails didn't respond. He was too busy trying to endure the vibrations to this alien region. Rouge knelt down slightly and closed her breasts around his shaft. Tails twitched in the chair from the touch. Just as he imagined, the feeling of soft, pillowy breasts encompassing his dick was absolutely incredible. Of course, it was difficult to truly enjoy it while his prostate was being assaulted like this. "My, you are really sensitive, aren't you?" Rouge asked. "We should work on that, too. Girls don't like a one-pump chump, even if they are able to go more than one round." Tails still wasn't responding. Rouge focused on massaging his dick with her breasts. She was quite talented at this thanks to years of working in porn and having sex with many different men. Since he never had a boobjob before, her talent was lost on Tails. Regardless, after a few seconds of stimulation, the head twitched and suddenly spurted out a thick gout of clear, viscous precum. It was followed by a second, then a third. "Wow, that's a lot!" Rouge exclaimed. The precum splashed over the top of her breasts, coating them in a thick glaze. "You really spurt like a cannon!" "Guuuuggghhhhh..." Tails gurgled. "If this is just your precum, then I'm really interested in seeing how much you are able to shoot when you actually blow." Rouge said. "Girls love a big, creamy finish." She continued to massage his dick with her breasts. She alternated between styles so he would not get used to the rhythm of any one of them. Tails kicked his legs in the stirrups. His dick was throbbing again, the meatus oozing out a white froth. He was about to cum. Rouge braced herself and closed one eye so he wouldn't blind her with a sudden explosion of seed. She was right to take precaution. When Tails came, he went off like a cannon. The first spurt would have splashed her right in the eyes, but instead caught her on the cheek. The second and third coated her breasts. His cum was hot, and there was a lot of it; all the more impressive, considering he had sex with Vanilla multiple times before coming over. Maybe this little squirt had some real potential, after all. "That's a good boy." she said. "Girls love a big explosive finish!" Tails went slack in the stirrups. His brain was in a foggy haze, and it was difficult to think straight. "So tell me, Tails, you've surely seen a girlcam stream before," Rouge said, helping him out of the stirrups. "But have you ever seen one that gets truly wild?" "I've... never watched a girlcam stream before..." Tails said, highly embarrassed. "Oop, you heard it here first, boys and girls!" Rouge suddenly said into the camera with the energy of an emcee. "Our boy Tails here has never seen a camgirl perform before! Let's give him a show and blow his fucking mind!" Tails rolled off the medical chair, clutching the remote to the egg vibrator in his hand. It was still buzzing away at his prostate. It was strangely enjoyable, once he got used to the foreign presence and his butthole stopped aching. Rouge retrieved a few more toys from her room before she took Tails' place on the medical chair. With the casual familiarity of someone who had done this countless times previously, she strapped herself into the stirrups. From his position, just behind the camera, Tails had a perfect view of her plump, dark brown pussy. She was already leaking from arousal. The first thing she grabbed was a long, floppy, twelve inch dildo which narrowed shortly before a prominent base. She applied a generous amount of lube to the entire length of it, then brought it down to her asshole. She pushed the tip in, her sphincter muscle opening easily to let it in. It was almost twice as thick as the egg in his butt; that was just the girth, and that felt like he was being split in half! Just how much did she stuff her butt to be able to take in something that big so easily?! "Mmmhh..." Rouge let out a soft moan as the base of the dildo plug came to rest against her asshole. Her labia flexed instinctively, and she took a few seconds to massage her clit and ride the endorphins. She quickly regained her composure and grabbed the second toy. This one was a lush vibrator. She lubricated the thin end of it, which was more than a bit unusual, based on what Tails saw in certain videos online. The reason why, however, soon became very clear. Rouge spread her pussy lips apart and, using the monitor displaying what she was streaming, guided the tip of the lush to her urethra. Tails could see that it was larger and more swollen-looking than normal. He realized that that must mean she frequently played with her peehole. He was bewildered at the idea. Did girls actually get sexual enjoyment by putting things in there? That question was answered right quick. Rouge let out a louder moan this time. She pushed the lush in all the way to the base, and rested the main body - the vibrator portion of it - on top of her clit. She rested her head back against the head rest and let out a few short, sharp breaths. Tails was finding this incredibly arousing. Even if the vibrator wasn't buzzing away against his prostate, he'd probably be incredibly hard and dripping wet regardless. "Okay..." Rouge said with a deep, shaky breath, looking over at Tails. "You might be wondering what the big deal is with plugging my peehole up like this. So, for your benefit, as well as anyone new in the stream chat right now..." she addressed the camera. Tails looked over at the monitor and saw that it was actually streaming on some sort of porn website. The chat was going bananas at the moment, but Tails wasn't going to bother reading it. "As you all know, this is the clitoris." she said, pressing her finger against her love button. "It's a very sensitive bundle of nerves that can bring a woman to orgasm very easily. Some women find it a little overwhelming, but I love being rough with it! "Then inside the vagina is the G-spot, which is where those nerves reach down and touch the top of your vaginal walls. It's roughly two or three inches in and then straight up; you could easily get at it with your fingers. Tails if you could..." "Huh? Oh, right!" Tails was so focused on taking in her naked body and the anatomy primer that it took him a moment to register that he was being addressed. He stepped forward and, understanding what Rouge expected of him, pushed his middle and ring finger on his free hand, palm up, into her vagina. He curled his fingers and probed around blindly for her sweet spot. He knew he hit paydirt when she suddenly gasped and jerked around in the chair. "Yep, he found it!" Rouge said in a slightly falsetto tone. "G-good boy. See? Even a child was able to find it, so none of you guys out there have any excuses anymore!" Tails drew his fingers out and looked back at the monitor. Among the comments, a few stood out to him, still claiming that she was faking it. He could easily attest that it wasn't. Her vaginal muscles clamped around him the instant he touched the sensitive bundle of nerves. It was very hard to fake a reaction like that. "And finally, the feature presentation... the urethra!" Rouge emphasized this by pumping the lush vibrator in and out of her peehole very rapidly. Her voice reached a high pitch as an indescribable orgasm ravaged her body. The medical chair rattled loudly as she thrashed around in the bindings. Even with the object down her peehole, she still managed to squirt past it, causing Tails to recoil and take a step back. "The... the urethra... is as close to the G-spot as you can get!" Rouge said through heavy breaths. She rested the vibrator back against her clit. The damn thing was still inert and it still brought her to tremors! "It goes right between the nerves on the clit and the nerves of the G-spot. It's also very risky to use this hole, but the rewards are beyond words!" Even if he didn't have a butt plug buzzing against his prostate, Tails would have still been hard as a rock after that little display. After making sure he was fully out of the shot, he began jerking himself off. Rouge's focus was still on the camera, but her eyes darted over to him for a second and a quick smirk flashed across her face. "To give you an idea of how sensitive this thing is, that little demonstration, it wasn't even on, and I lost count after the third orgasm. Yeah. That's how sensitive it is, even after I've been doing these camshows for this long!" Three orgasms in one minute? How was she even still conscious, Tails thought. "Okay, here we go, people! Keep a close eye on my gooch's contractions and try and count how many times I cum in the next ten minutes!" Rouge turned on the vibrator and began pumping it in and out of her peehole. The instant she turned it on, Tails could see that she came instantly. Sexually charged as he was right now, Tails kind of wished he was born a girl, if it was this easy for them to have orgasms. Rouge was surprisingly able to keep herself composed and in control the whole time, even though it was clear to Tails by her subtle twitches and vaginal contractions that she was having an orgasm at least once every twenty seconds. Tails tried to pace himself, but that was just straight up impossible with everything happening both in front of him and inside him. He thrust his hips forward and shot a new, fresh load out. He didn't think about where it was supposed to go and he ended up spurting it across Rouge's stomach. He panicked at first, but she didn't seem to mind. Hell, she didn't even seem to notice. The minutes flew by as one orgasm led to another, all from the stimulation of an erogenous zone few even knew about, much less dared to explore. Tails looked over at the stream chat. It was a blur of emojis and exclamations. His eyes, trained from years of speedreading technobabble, saw one or two troublemakers in the midst, but they were quickly silenced and banned by some taciturn mod. At the end of the ten minutes, Rouge pulled the vibrator from her peehole. The effect was like uncorking a champagne bottle, and from her stretched hole came a torrent of clear fluid that arced higher than Tails' head and very nearly overshot the monitors. Rouge arched her back and let out a content and exhausted squeal of ecstasy. She massaged her clit, pulling back at the foreskin protecting it to reveal the bright red nub underneath. It was swollen from increased blood flow due to how much she was stimulating herself down there. It looked a bit grotesque, but also quite appealing in its own way. Tails, with his prostate under constant attack from the vibrator egg and seeing this incredible display of euphoria in front of him, ended up cumming a third time. The volume wasn't as considerable this time, and the muscles in his dick were starting to get sore from all the contractions. It was the most he had ever masturbated to orgasm in such a short amount of time. And yet... he wasn't... satisfied? "Alright... how many orgasms do you think that was? That includes the initial insertion." Rouge asked the stream. "Sunbeam, please put up the poll so everyone can submit their answers." 'Fifty three.' Tails thought without hesitation. He knew; he had the best possible view to her show, and with such a close view and without the compression of video, his keen eyes were able to notice every subtle twitch and contraction of her muscles. He looked over at the chat. A new window popped up showing all of the votes of the registered members in the stream. They were very far off, initially, with most of them in the twenties. "Sunbeam" was busy in the chat banning a few troublemakers who submitted their answers as inflammatory responses, claiming that she faked them all because women couldn't cum or threatening to report the channel for having a child in it. Tails for a moment wondered if they actually would. What would be the long-term consequences of this? The channel could be banned, but if she had a VPN, there wasn't really anything the police could do to find them. The first user to vote fifty three was someone named "FreedomNuts247". The instant their vote came in, the vote shut down, their username was highlighted and a fanfare played with confetti showering in the stream window. So wait, did Sunbeam also know, or was there something in the toys that sensed when Rouge had an orgasm? "Congratulations, FreedomNuts247!" Rouge cheered. "You got it exactly right! Now as your reward, you get to choose what I do next, anything at all, as long as it's within the rules of the stream!" Tails did not know what the rules could be, and based on what she had done so far, the only things she wouldn't do were probably, like, toilet stuff. "Let that kid fuck your peehole." came FreedomNuts247's reply. Tails was taken aback by that request. It was one thing to have that thin little toy in her urethra. It was another thing entirely to get any penis in there, much less Tails' apparently monstrous seven inches. Surely this request would get rejected, right? Much to his surprise, Rouge reacted with excitement. "Oh, that's a fun one!" she exclaimed. "Well you are all in for a very rare treat tonight! You get to see this cute little young boy fuck my peehole with that huge cock of his!" It was at this point that Tails remembered he even existed in the same room, let alone was already a part of this camshow. Getting the chance to fuck a girl again was exciting, but at the same time, he could feel a twinge of nervousness. Unlike his time with Vanilla, he was performing in front of an audience, now, even if they were all online. Even with the vibrator buzzing inside his ass, the thought of actually performing in front of an audience, even a virtual one, was giving him a bit of stage fright. Was it like this for all porn actors? Knowing that it was his cue, Tails stepped in front of Rouge. She moved the camera to the side, looking down at them so the audience could get a good view of both herself and Tails as he mounted her. He stepped up on a stepstool at the front of the medical chair, placing himself between Rouge's legs. Being this close to her, he realized just how hot she was compared to Vanilla, which was saying something considering she was going to play host to his fantasies for the foreseeable future. Now he had two women that were going to live rent-free in his head. "Don't be shy, little one." Rouge said, a mix of both comfort and teasing in her words. "It's perfectly normal, and you've already proven yourself to be even better than most guys out there." She reached down and grabbed Tails by his dick. Grabbing the bottle of lube again, she applied it to the entire length of his shaft. Being this close to both her and the lube, he could smell that it was also an antiseptic of some kind. After she lubed him up, she guided him by his dick to rub it up against her pussy. The words were encouraging. So was the vibrator egg tingling his prostate. Tails' dick was still sore, but the drive to have sex again was so immensely overwhelming that he was able to ignore both his fatigue and the cameras exposing him to who knows how many people online. Tails prodded around blindly for the entrance to Rouge's urethra. He accidentally poked into her vaginal canal a few times before the tip found purchase in her peehole. It was marked by a notably tighter hole opening just enough to hug tightly around his cock, and a sharp gasp from Rouge. "Yeah! Yeah... right there!" Rouge exclaimed. There was a peculiar glint in her eyes as Tails pushed into her. "Just keep pushing in, and be mindful. This is still a very sensitive hole, no matter how well I trained it." Tails nodded and continued to push his cock inside this unusual hole. He couldn't see the chat from this position, but he could only imagine they were going ballistic right now. "Holy shit, it's so weird and warm inside your bladder." Tails said as he bottomed out inside her. He could feel a tight constriction just underneath the head; the tip of his dick was inside her bladder. It was so weird and alien and perverse that he could feel a warm tingly feeling surge through his loins, like a miniature orgasm. "Okay, now just fuck my peehole like you would fuck my pussy!" Rouge said. Tails doubled over her, bracing his hands on either side of her head on the medical chair, and began pounding into her urethra. He did a slow, tentative pace at first to make sure he wouldn't accidentally hurt her. He froze when she suddenly yelped and hissed. She thrashed around in the binds underneath her, and he thought to pull out, but before he could take even the first inch out, Rouge stopped him. "No no, it's fine." she said between breaths. "I'm just... cumming... again." Tails' heart was pounding in his chest. It was one thing that he made a second girl cum, but he was still trying to register the fact that this camgirl was able to cum at least sixty times and somehow remain cognisant, let alone conscious. Tails was pretty sure if he was made to cum sixty times, he would go insane. Now he was interested in seeing how much she could endure before she begged for him to stop. Tails thrust back into Rouge's peehole, building up the pace again. He slowly overcame his stage fright as he pumped in and out of her urethra. It was really hitting home that he had sex with a porn actress and now a camgirl, and both of them complimented him and the size and appearance of his dick. You couldn't get more validating than that! He didn't know what was going on in the chat right now and he honestly didn't care. The more this went on, the more he focused on Rouge and the less he thought about the world around him. "Here, put your hands on my boobs." Rouge said, guiding Tails hands to her enormous breasts. It wasn't until he placed his hands on her breasts that he realized this was his first time actually touching breasts with his hands. Both women buried his face and cock between their tits, but this was the first time that he actually got to feel them with his hands. It was a completely different experience. They were incredibly soft to the touch, but still with a bit of firmness to them. It felt nice touching them, especially when they were already so intimately connected. "How does it feel fucking my peehole?" Rouge asked between labored breaths. "It's really tight and warm." Tails said. "I feel my heart pounding in my chest." "Can you feel mine?" she asked. "Every other time you thrust in or out of me, I have another orgasm. If you can feel my urethra muscles contracting, that's me cumming. Each time. Every time." Tails' heart pounded even harder in his chest. Rouge was almost constantly contracting! She must have been going from one orgasm to another without a moment of reprieve in between! He wondered how she managed to stay sane through all this, and part of him was immensely jealous that she could constantly orgasm without a refractory period. He wondered if there was a way he could experience it, too. The egg vibrating in his butt felt nice in brief intervals, but it wasn't nearly powerful enough to give him the same sort of euphoria. Tails picked up the pace, thrusting into her with greater speed. The lube was extremely effective at letting him glide through her urethra. The only resistance he felt was from the tight muscle that led into her bladder, and even that was starting to resist his intrusion less and less. "Oh god, yes, keep going!" Rouge gasped. "I'm gonna... cum even harder!" Tears welled up in the corners of her eyes from the. She was about to experience a next level of orgasm. This triggered something dark and primal within Tails. Seeing her like this, and knowing that she was cumming this much and this hard because of him, spurred him on and made the heat build up in his loins even faster. He came harder than he ever had before. He continued to thrust through his orgasm. Hot, thick ropes of cum pulsed up through his urethra, and directly into her bladder. What little sense of him remained through all this wondered how he even still had anything left in his balls to fire. Rouge dug her nails into Tails' back. Her muscles contracted even tighter around his dick, and she filled the room with husky, throaty cries of pure, overwhelming euphoria. She thrashed around in the bindings, her eyes unfocused as she stared up at the ceiling. The tears were streaming down her face now, but it was clear that she was enjoying every last second. Tails remained inside her for a few more minutes after he calmed down before he pulled out of her. He popped out with a loud squelching noise. He looked down to see some of his cum leaking out of her gaping urethra. With how dilated it was, it was a wonder she was still continent at all! Rouge went slack in the medical chair for a minute or two, then regained consciousness with a loud gasp. With clumsy fingers, she reached over to the medical tray to grab the lush vibrator again. She brought it down to her clit and turned it on. Within a minute, she came again with a strained, hoarse squeal. She squirted out a thick, creamy white stream of Tails' cum. The poor boy did not see it coming, and the next thing he knew, thick, huge globules of his own sperm splashed across his face and chest. Much to his own surprise, however, he wasn't irritated or disgusted by it. If anything, he found it kind of arousing. Even if it was his own sperm, it was a mark of pride, and proof that he was able to make somebody cum. He was starting to understand why Cream was so promiscuous. In its own weird way, it was empowering. For just a second, Tails wondered what it would be like to have fresh sperm from someone else's cock coat his face and body. "Hoohhhh, that was... fucking amazing!" Rouge exclaimed, going slack in the medical chair. She looked up at the monitor with the stream chat. Sunbeam activated slowmode at some point and was busy pruning the stream of troublemakers. The emoji notification pop-ups, however, was still very active, and was an unending swarm of various emojis. "I haven't gone that hard in a long while! I think I found a new playmate! Give your fans a wave, Tails!" Tails looked up at the monitor and was taken back by how many people were fawning over him and praising... well, just about everything there was to say about him. It made him feel warm. More to the point, it made him feel confident about himself in a way he never felt before. "Wow, they... really like me." Tails said. "I gotta say, I haven't felt that good in a while, and I've been doing this since I was sixteen!" Rouge said. "You are quite the natural, Tails!" Hearing that from a camgirl was music to his ears, and not something he imagined he'd ever hear. Rouge let out a loud sigh of exhaustion and began unbuckling herself from the medical chair. She might have been spent, but Tails was strangely still good to go. He could feel the heat of arousal still burning in his loins. One more go couldn't hurt, could it? "Hey, do you think we can find something for my butt?" he asked. "Ya know, something a bit bigger?"