This would not be the first time Matt wondered how he got where he was.
“Right this way, Mattie.”
Matt nodded. The pretty older girl led him into the old school building. As they passed by a bathroom only marked for girls with no compliment in sight, it sank in just how long of a history Felicity Umbridge Technical Academy had as a girl’s only boarding school. Matt felt like an invader – every step he took there felt like he didn’t belong, because he really didn’t. He was a guy masquerading as a girl, as “Madelyn” or “Mattie” for short. It helped having a room to himself even if it was temporary, but the main reason he had gotten away with it for the last week was the skinsuit disguise his aunt had suspiciously provided for him.
Whether by magic or technology so advanced it might as well be magic, the skinsuit transformed him into the perfect image of a real girl, and a cute one at that. “Mattie” had short brown hair that hung lightly just over her ears and the most crystal clear blue eyes Matt had ever seen. She had a fit figure with only a little flab under her upper arms and stomach. Matt also appreciated the pair of lovely breasts that sat comfortably in each hand, though their weight was already starting to wear on his shoulders and back.
The changes did not stop with his external appearance though. The skinsuit also altered his voice appropriately as well as gave him fake female genitalia. Well, it had to be as fake as the rest of the suit, but somehow the little slit between his new smooth legs sent him little electric like sensations when he touched it, produced a clear, slightly sticky liquid when stimulated, and even had a distinct vaginal cavern when he probed it with his fingers. A uterus, he supposed it was called, remembering from sex-ed. All the while, his cock seemed to remain safely hidden within the special sleeve he found inside the crotch section of the skinsuit’s interior. No matter how aroused he got, seeing his own or other girls’ bare skin in this environment where young girls were noticeably less guarded around one another, his erection never gave him away as a fake.
After his parents had been seized for reckless gambling and deemed unsuited to raise him, Matt was taken in by his aunt, the headmaster of this school. The condition of his adoption was that he would have to wear this skinsuit and attend F.U.Tech for his last three years of high school. His aunt insisted that it was out of convenience for both of them, but the whole arrangement had been nothing but an inconvenience for Matt so far.
“Here we are,” Jacqueline announced, bringing Matt back to the present. The upperclassman stood just outside a room that looked no different than the others they had passed. The old school building was used for club space as was common, so this room must be the headquarters for Jacqueline’s club which Matt had found himself invited to check out.
“F.U. Tech Academy Cheer Club,” read the plaque by the door.
Matt blinked. “You’re a cheerleader?” he asked cautiously. His voice left his lips in a light soprano that Matt was not sure he’d ever get used to. It sounded natural enough that no one had suspected him on that grounds.
Looking her up and down as discreetly as he could, Jacqueline certainly had the figure to qualify as a great cheerleader. Her collar length blonde locks led the eye down right to her pert bosom, which seemed somewhat tight behind the blouse of their school uniform. Her shirt tucked in at her tight waist to a simple dark pleated skirt which hung off of her pleasantly round hips and hid all but a sliver of her thighs before her dark gray thigh-high stockings picked up the slack. Her hair bounced a bit as she shook her head and drew Matt’s eyes back to her patient smile.
“We’re not ‘cheerleaders,’ we’re ‘cheer-givers,’” she explained. “Since this is a strict boarding school, we’re not allowed to leave until between terms and for some girls that can get overwhelming. That’s when we cheer-givers come in to help them relieve some of their stress.”
Matt was still skeptical since the explanation still failed to detail what the club specifically did.
“Well, it’s easier if I just show you, I think,” Jacqueline conceded with a small giggle. She opened the door and ushered Matt in. It appeared to be the old nurse’s office, based on the curtains hanging from the ceiling that sectioned off area around beds for privacy.
“Ah, haa… haaa…”
There was a silhouette behind the nearest curtain and with a mischievous grin, Jacqueline pulled back the curtain to allow Matt a peek.
Matt did more than peek though, he stared. Right in front of him, there were two girls making out. No, more than making out. As he watched a pale skinned girl bouncing enthusiastically in the lap of her milk chocolate skinned partner, it became apparent that there was something connecting the two. A few moments the brunette girl on top cried out, and the black hair girl underneath joined her in harmony. After a few moments of heavy breathing, the girl on top carefully climbed off a rotund shiny black shaft that Matt noticed seemed to start drooping suspiciously. Jacqueline let the curtain fall back into place, obscuring his view.
“Thank you, come again!” someone else said further inside. Matt gave yet another start as he and Jacqueline were hastily passed by a girl with a painted on face. At the door, she turned to glance back at them, giving Matt a second chance to process what he saw. It was a painted face, but it was painted because she was wearing a full head mask, and her red Raggedy Ann hair was in fact actually made of yarn.
“Some girls prefer to use our services anonymously. We offer masks like that for such clients.” Jacqueline explained.
His guide led him through another door at the back of the room which led to a vacant personal office. Furnished with two loveseats opposite each other in the center and a tidy desk at the far end, the office looked respectable but something smelled off that Matt had difficulty identifying. Almost like the whoever cleaned it was overzealous with the air freshener. Whatever it was, Matt did not have long to ponder as the dark skinned girl from a few moments prior joined them. She was naked like her client had been, save for the girthy black ‘strap-on’ that hung flaccidly from her crotch. Her rather full bosom jiggled heartily as she laughed.
“Is this the new girl?” she asked jovially. “Feels like it’s been a while since we had a new member. I’m Danielle. Glad to have you!” She began undoing the straps around her hips.
“It looks a little odd for a strap-on, doesn’t it?” Jacqueline whispered gleefully in Matt’s ear. “Well, there’s a good reason for that.”
The synthetic black material slid off Danielle’s equally dark but very much live penis and Matt gasped in genuine surprise. He had been so caught up in his own dishonest appearance that his mind hadn’t registered the clues he noticed before. The gears turning, he could not help but wonder now if the busty girl before him was not so different from himself.
“We start off new clients with these ‘strap-ons’ and only once they have built enough confidence do we reveal our toys’ true nature!” Danielle elaborated as she happily stroked herself.
“There you have it,” Jacqueline continued, leaving Matt’s side to stand next to Danielle. Jacqueline raised the hem of her pleated skirt and revealed a large bulge of her own packed into the front of her black panties. “This way, not only do we help out our classmates who need some relief, but we also get to moderate our own needs, since shemales like us have a more active libido than normal people.”
Was that how shemales worked? Matt thought quizzically. His earlier wonderings had already stoked the fires of his suspicion. I’m not sure that’s how shemales actually are… Not that he had any real experience with them.
“I’ve got one of the thicker cocks in the club,” Danielle bragged, still jerking herself off.
It’s thicker than mine for sure, Matt mused silently, but is she really going to keep going here in the middle of the room?
“You always start with that because you know you can’t beat me in length,” Jacqueline teased back. It certainly was an impressive spectacle watching Jacqueline fold back the top of her panties and almost painstakingly haul out her long dick. It proudly stood a good eight inches stiff, also beating out Matt’s own specification. The other two looked at him expectantly.
“Well, let’s see yours,” Jacqueline requested boldly. “Surely if the headmistress herself set you up with us, you must be pretty well equipped yourself!”
He would have to have a chat with his aunt sooner rather than later. Even if Matt knew how to ‘whip it out’ while wearing his skinsuit, he did not think he would have the confidence to do so in the face of these admittedly superior specimens.
Blushing with more self-consciousness than he expected to feel about his fake appearance, Matt gingerly lifted the front of his skirt to reveal his bare, flat crotch. Jacqueline stepped forward and suddenly yanked down his panties making Matt yelp in protest. But at this point his fate was sealed and his company seemed adequately convinced of his pure femininity.
“Oh, huh…” Jacqueline struggled for words. Danielle finally stopped rubbing one out.
“I, uh… I think there may be a misunderstanding,” Matt nervously suggested.
“Well, we do have real strap-ons you can use.” Jacqueline noted. It almost sounded like she was trying to console him.
Matt saw that he needed to elaborate. “Um… well, actually, I only agreed to come see the club room because I thought it was just to preview the club – I hadn’t decided whether or not I was going to join. Seeing as I… lack the required equipment though, I don’t really think I would fit in. Thank you for your hospitality though.”
“I fear you may be the one who misunderstands, Mattie.” A new voice declared.
“Oh, Prez,” Danielle greeted.
Matt dropped his skirt and turned to see a young girl with porcelain white skin and long black hair enter the office. She had a more modest chest than the other two and was still in her uniform. Based on the color of her ribbon, she was in the same graduating class as Matt, though he surely would have noticed such a dignified and graceful presence has she actually shared any individual classes with him. She seemed to glide over to the office’s main desk and alighted on the chair behind it. Behind a pair of rimless glasses, she had thin almond shaped eyes that seemed both mirthful yet serene at the same time. While Jacqueline and Danielle were both fairly easy to read, Matt struggled to figure out what the club president was thinking.
“I am the Cheer club president, Fuyumi,” she introduced herself severely. “The headmistress has already added you to the club roster and I’m sure you of all people know that defying her demands can be… difficult.”
Matt kept his face under control as best he could, but underneath he fumed. It was bad enough that his aunt insisted he crossdress in order to attend her school but signing him up for the tranny club almost seemed to him like she was making fun of him for being in the situation she forced him into in the first place!
“Well,” Matt took a breath to steady his feminine voice, “I also know my aunt to tease me like this so I’m sure she did not mean anything serious by it. I’m sorry if it got your hopes up, but I really don’t think I’m a good fit for your club,” he resisted a bit more firmly.
Fuyumi regarded him for a moment. “Before you attempt to withdraw, why not give us a try while you’re already here?” Fuyumi stood once more and rounded her desk, crossing her long hose encased legs and leaning back. “So far, you’ve seen only a small snapshot of what we do and though it is our most… popular… option, you may be surprised by the scope of the services we offer.
“Naturally, as a club member, you would have nearly unlimited access to our own services and facilities whereas our normal clients have a more controlled menu to choose from. If you’re intimidated by Jacqueline and Danielle’s presentation and were, as you mentioned, ‘worried about not fitting in,’ then I recommend you give us some more time.” She lowered her head to meet Matt’s eyes over the top of her glasses and suddenly she did not seem so dainty. “We are in the business of granting comfort and pleasure. I guarantee we can find something you’d enjoy.”
Matt gulped. There was something about Fuyumi’s gaze that penetrated him, shattering the flimsy excuses that he made to himself and seeing straight to the boy who had let shame suppress his curiosity. It was as if she knew that one of the first things he did after putting on that skinsuit was explore female masturbation. It felt different than jerking off as a guy but no less amazing and he remembered wondering if just for a moment, what it felt like if he had something bigger than his fingers. Something bigger than a tube of lipstick or a whiteboard marker to try stimulating his new organ. What would it be like for a live cock to enter his new vagina? At the time, he quickly shook away the thought since it was ‘gay,’ and Matt was not gay. He liked women.
Well, here were some women before him. Women with dicks. If having sex with a man would be gay for him, would having sex with a shemale only be ‘half-gay?’ Would it be gay at all? Matt was confused but that curiosity from before had returned as a desperate itch in his loins. He wanted to know and this was his chance.
Mattie licked her lips anxiously. She glanced furtively between the girls and the two penises that had recently returned to an erect state. Finally, she made a decision.
“Very well, I suppose I might as well give you a chance,” she conceded with a heavy, dramatic sigh.
Fuyumi’s lips curled into a knowing smile. It transformed her face from cool and businesslike to a more relaxed, although no less predatory, smug. “I promise you won’t regret it,” she claimed boldly. She straightened up and sauntered forward, stopping a few steps in front of Mattie. Fuyumi reached between her legs and began stroking herself through the fabric of her skirt, her hips swung a bit as she shifted her weight between her legs growing ever more aroused. Still petting herself, her hand slowly climbed upward. Only after she had passed her waist did Mattie see it.
Unbelievably, the outline of a cylindrical mass slowly moved up Fuyumi’s stomach to her chest under her shirt. Her hand stopped just under her breasts but a few moments later, Mattie saw her blouse tent just under her class ribbon. With a smirk, she untied her ribbon and unbuttoned the top three buttons of her blouse and there it was. The red head of her engorged, supernaturally large tool poked out, almost playfully from her cleavage, like a cherry sitting between two scoops of vanilla ice cream. It was long enough that she could believably suck it herself. Fuyumi seemed to enjoy Mattie’s reaction.
“Everyone’s jaw drops the first time they see me,” she admitted, “But no one’s ever complained that they find me lacking.” She unbuttoned the rest of her blouse and slipped out of her skirt, freeing her massive member which remained pointing proudly at the ceiling if no longer pressed against her stomach. The other two closed in on her flank and suddenly Mattie was faced with a united front of dicks.
“Here, get comfortable on this couch and take off your panties,” Fuyumi instructed, gently sitting Mattie down. Still somewhat stunned, she numbly followed orders, removing her undergarment before she could question whether that was a good idea. Embarrassingly, she found them rather wet, though no one else seemed to notice. Was she going through with this? Her head wondered but she could feel her pussy’s demands clearly.
“Why don’t we let her pick who she wants to try her first time with,” Jacqueline suggested. She shot an asking glance at Mattie. “Assuming this is your first time, right?”
Mattie nodded. Her choices were an abnormally long dick, an abnormally thick dick, or a monstrous protrusion that dwarfed both other options in length and girth. None seemed like they would go easy on her, so if she was going to do this anyway, then…!
The president blinked in surprise. “Are you sure?” she asked, bemused but also flattered when Mattie pointed to her. “You’d rather this?” she ran her hand along her shaft. Mattie swallowed, but nodded again.
“Go big or go home, my parents always said,” she confirmed, wryly reminding herself that that mentality was also why her parents lost custody of her. The apple doesn’t fall far from the tree, she supposed.
Fuyumi smiled. “As you wish, it would be my pleasure to be your partner.” The other two looked a bit disappointed, but the decision was made. Jacqueline and Danielle gave them space, though they floated about the other side of the room spectating while they consoled themselves.
Mattie felt her heart rate picking up even faster as Fuyumi lined up her giant fuck stick with her fake pussy. She had wanted something bigger and this was leagues bigger than anything she had tried putting inside herself. As it slowly forced apart her folds, the feedback had already begun fizzling in the back of her head.
“Ah…ha…. ah…”
Was… was that her own voice? Mattie thought, unaware of her own moaning. Fuyumi had only just finished easing her tip inside; there was still plenty left. The rest of the world seemed to fade away and all that was left was the oversized cock carving its way deeper into Mattie, seeming to deliberately rub and scrape against all the erogenous zones Mattie never knew her vagina had.
Eventually Fuyumi reached the dead end, and the pause in the shaft’s movement allowed Mattie a moment’s clarity to be impressed by how much of Fuyumi’s rod actually fit inside her.
“Mhm…” the president murmured, “I’m going to start moving…”
The rhythmic thrusting of Fuyumi’s hips quickly sent Mattie back into her euphoric haze. How could women feel this good? She lost all sense of time and could only gauge things by the cycle of her orgasmic highs.
Finally, Mattie heard a terse groan that was not her own and became aware of a new sensation in her pelvis. She managed to crack open eyes she had not realized had been clenched shut and saw her stomach slowly seem to swell as Fuyumi pumped an unreasonable amount of cum inside of her. A feeling of alarm numbly pierced her pleasure clouded head. What if she came so much she hemorrhaged the suit’s fake vagina? The absurdity of the thought itself snapped Matt back a bit, but the concern was still there. Fortunately, Fuyumi cut Matt a break, pulling out and letting the remainder of her obtusely long ejaculation shower Matt’s slumped form with her cum.
Matt jerked awake, a spike of alarm shooting through him at having fallen unconscious at all. A quick look around reassured him though that it couldn’t have been for long. The office was a pungent mess with jizz splattered all over the place, himself included. Nearby, Fuyumi had fallen back into the chair opposite him, her cock having shrunk back to a surprisingly unobtrusive size, and the two spectators leaned wearily against whatever bookcase or wall was closest.
With noticeable effort Fuyumi stood up and picked up Mattie’s panties from where they had been discarded earlier.
“Strip. Jacqueline will take you to our private baths and you can wash up. We’ll get you a clean uniform and wash and return this one later.” She clapped her hands and spurred the other two into action. Danielle pulled a mop and some cleaning supplies out of a closet as Jacqueline escorted Matt out. No wonder the office smelled funny.
The baths were far more robust than Matt had expected, and it was apparent that they had been updated recently compared to the rest of the old school building. Matt wondered just how much budget the club had and why.
“We live in a culture where hygiene is highly valued. Since our services can get a bit dirty, good bathing infrastructure is a must for an operation like ours!” Jacqueline explained, her bubbly mannerisms returning as she seemed to wash away her own weariness.
Matt was still getting used to bathing as a girl, and having Jacqueline nearby in the open shower area only made him feel more awkward. Not that she had seemed shy to begin with, but with her dick just hanging out like that seemed especially brazen. Matt did not have the security and confidence to do something like that. Even at gyms or at the pool he would try his best to hide behind a towel or find a bathroom stall to change in.
Somewhere in the back of Matt’s mind, he expected Jacqueline to come onto him in the shower but she minded her own business aside from making harmless chatter. As they finished and were toweling off, Fuyumi came in for her turn.
“Since I believe I neglected to earlier, allow me to formally welcome you to the F.U.T.A. Cheer club,” she offered with an encouraging smile. “We have a few other members that you’ll meet later, but I hope that this has given you a small taste of what we do and what you can expect from club activities. There’s so much more we can’t wait to share with you in the near future!”
Matt smiled back weakly and nodded, responding noncommittally with a vague thanks. He had a lot to think about that would take some time to process.
“Danielle’s not with you?” Jacqueline asked as Matt moved to putting on the replacement uniform they had provided.
“No, she did not get that messy so she elected to go back to her room and wash up there.”
“Oh yeah, she’s lucky she doesn’t have a roommate like most of us,” Jacqueline pouted.
That reminded Matt that his stay in his temporary single room was ending tonight – he had been informed in the morning that they had found a normal double to move him into. He had been dreading having to deal with a roommate but his aunt was unable to make exceptions even for him. With each incoming graduating class bigger than the last, they were even renovating the single he was being moved out of to hold two people next term.
Matt gave his departing salutations and made his way to the housing reception desk.
“Madelyn Duffy?” the attendant confirmed, looking up what his new room assignment was to be. “Right, here you are. You’re now in 308. It’s a bit of a hike, being on the far side of the building but I’ve heard girls over in that area like that it’s a bit more secluded.”
Secluded did sound nice, but it would not help with the roommate problem. Matt received his new key and the assurance that his belongings had already been delivered and set off.
The door looked like any other door along the hall, but somehow it felt more menacing. Matt hesitated in front of it. Did he just try the key and go in? Maybe he should probably knock first… He rapped on the door and promptly heard a yelp from inside, followed shortly by a heavy thud. Overwhelmed by a sudden concern for his new roommate, Matt shoved his new key in the hole and let himself in.
“Gaah! Wait, I can explain!”
Matt blinked at the bizarre sight. He had gone through a lot of possible scenarios in his head about how his first meeting with his new roommate might go, but this was not one of them.
“M-Mattie?!” exclaimed a thin white boy spilling half out of the deflated but recognizable chocolate skin toned husk that had been Danielle less than an hour ago.
To be continued
Subsequent stories will explore smaller individual cases/incidents and will probably be shorter than this introduction. The goal was to have something that would be easy to build off and make ‘quick and dirty’ short vignettes. I have five episodes currently in mind but the final number may vary with time and enthusiasm.
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