Charity Relations - 01

Charity Relations

Disclaimer: This story is meant to happen in a more understanding world. In particular, it occurs at a fictional kinky fair that caters to all kinds of fetishes, including having really outrageous contests.

If you are not into male-on-male or trans-on-male or characters with penises interacting together, this story is not for you.

If you enjoy amateur femdom, feminization, crossdressing, humiliation, and helpless submissive guys being pushed into silly shenanigans, then: I hope you enjoy this story!

And I want to thank my beta readers, some issues with the story would not have been tackled if it weren't for you pointing my eyes to it! Thank you!

I did my best at spell-checking this story, but since English is not my first language, there will be some grammar issues here and there.

DRESSING ROOM

After much begging and nagging from Sarah, John accepted to participate in a charity event at the infamous kinky fair that she seemed obsessed with.

They were together for about two years, and both were comfortable.

John was not the most buff guy around, but he was active and kept himself in shape. Sara is a petite girl with a pleasant laugh. She also has the most beautiful pair of boobs in her boyfriend's eyes, "not too big, not too small, the perfect balance," he would always say.

The event in question is a "womanless pageant." Of course, John expected something a lot worse with what he heard about this fair: people having live sex shows now THAT would be too much.

Understanding almost everything spent at the fair would somehow help raise money for charity did help in the reluctant participants' decision a good cause is a good cause. Also, Sarah did promise to allow him to have something he always wished for every year on his birthday, but now he would not need to wait for the candle-blowing party to receive his special request.

All this just to explain why John's petite and insistent girlfriend was now smiling and looking at his makeup, double-checking his appearance as he tried to accept the fact that the reflection of a woman with curves created by a tight corset that was showcasing a glistening green mermaid dress that tightly encased his legs, only flaring out down below his knees, and an enticing cleavage of boobs "not too big, not too small, the perfect balance" as she mockingly described it. His hair, a towering blonde beehive with side-swept bangs, all this was his actual image right now.

"Alright, babe, I would kiss you right now, but we can't smudge that lipstick," Sarah started.

"I also do not want none of that plumper in me right now. It is still fresh," She continued, smiling with playfulness in her eyes.

The guy with diva's hair rolled his eyes at his girlfriend's remark and tried to concentrate on not falling from his five-inch heels, two whole inches higher than they used for practice.

"Alright, but will you get me something to drink?" John pleaded, still practicing the feminine voice they had worked on for two weeks before the event.

"Of course, honey, just a second." Sarah seemed eager to care and tended to pay more attention to her boyfriend since he agreed to participate in this event.

As she walked away from her beloved boy, Sarah took this opportunity to remember. The training they had done in preparation for this event, including the cunning way she used sex in convincing him to try panties in their sexy times, some light erotic humiliation, teasing him that he indeed liked to dress up and walk in heels.

The tumescence was always somewhat present, but she thought, 'What if I add some vasodilators, not enough to force, but to facilitate his erections? ' With mischief in her eyes, she opened the pills she had researched.

Gymgoers and bodybuilders used those, but she had read people with lightly erectile dysfunction would use those. 'Harmless enough!' she thought again as the powder mixed in with the beverage she had prepared for her loved one.

Looking around the enormous dressing room, John could see a bunch of other guys, some amateurs like himself, but others were professional drag queens, willing to put on a show as actual divas and help others. He remembered the first time Sarah said she loved the shows she watched when she was single, and he also remembered all the times she pleaded with him to go with her and watch one of these shows. The music was great, and the dancing was okay, but damn, that artist was a funny one, she would mock everybody in the room, and no one felt truly offended. Everything was done with their exquisite charm.

'Ever thought of being one of us in the show, honeybun? You look like you have a good shot at this.' the diva said to John, just to get a laughing Sarah at the idea of seeing her boyfriend in drag.

Well, he was close to it right now, not with the same kind of heavy makeup on his face, but a convincing one. He also lacked the same confidence and humor shown by that artist on that night; he could not remember her name, but he remembered the giggles every time someone said it.

Even with this considerable wig designed for an actual professional show, he looked somewhat convincing, or at least. He looked "nice" from some angles, angles he did not know he would look nice from.

Sarah came back with a blue cup with a metal straw for him.

"Drink it up, babe. The show starts soon." The giddy girlfriend seemed to be having the time of her life now. John thought that being waited by her at his beck and call almost felt worth all the hassle of dressing up and practicing. He still wanted his early birthday treat. Sarah licked her lips as she watched the plumped lips of her cross-dressed boyfriend sucking on the metal straw. She held her desire to avoid showing any more physical excitement. Otherwise, that might ruin the surprise effect or, at the very least, raise John's suspicion about what she considered the best part of the show.

"Honey, I'm going to my seat now. Just remember to keep calm. This is not serious. It is meant to be fun, so people donate more, okay?"

"Yeah, yeah. Alright, alright"

"Feminine voice, dear..." Sarah said as she walked away from the dressing room.

"Yes dear.." came his attempt of a feminine reply, for a thumb's up and hand wave from his girlfriend.

Alone in a room bursting with cross-dressed guys, John checked his appearance one last time. He thought maybe if he made it to first place, she might be happier, and a happy Sarah could mean a very well-rewarded John later tonight.

Some of the mentioned crossdressers had more pronounced or even exaggerated curves with emulated distracting jiggles and wiggles, causing a sudden constriction at the front of his panties. John tried to focus his attention on his reflection and did a slow spin to get a better view of his outfit.

Turning from side to side and then slowly stopping to gaze at his image, John starts to speak with himself in his thoughts.

'I can't believe I got roped in this nonsense!'

'Who's ever heard of a womanless pageant anyway? '

' I'd be lying if I said I didn't look good in this dress, though...'

John's panties started to feel too constricting, and his engorging member formed a visible bulge, which seemed to grow as he realized what was happening.

'Uh oh. A little too good.'

'Well, that is just great. I turned myself on in the mirror!'

'How am I supposed to hide Mr. Happy?'

The growing bulge being noticeable made John anxious. This would be more embarrassing than just participating in an event like this.

"Ninety seconds to showtime 'Ladies'!"

One of the producers announced the clock to a humiliating scene. In his mind, John could imagine and almost hear people laughing at his situation. But the laughs were just from the other participants who were having fun with nothing related to his own brand of sausage.

'What will Sarah think of me now?' he thought as his alarming bulge did not seem to be anywhere near ceasing its crescendo. The bulge had long since pushed through the left of the panties and was now being hugged between the tight dress and his tights, the garments he wore underneath only further caressing his member.

Thinking about the nine yards of lingerie his girlfriend convinced him to wear was not helping with the anxiety of John's imminent presentation of Mr. Happy in a tight dress.

Worse yet. He remembered all the sexy times that had convinced him to wear some of this lingerie so they could 'play around' and 'keep up the spicy and hot bedroom'. In the end, maybe her plan to convince him to participate could have just trained him to like this kind of clothing more than he ever hoped to.

SHOWTIME

The participants formed a line of charming and smiling faces. Some commanded attention with confidence, and some wound down with trips from the unbalanced high-heel strutting they were not used to.

John was among those commanding attention, although not with confidence, just with a clear signal that he was happy to be there at that moment.

Laughs from the audience and judges who could see it soon started to poke the other judges with a 'nudge-nudge' and a smug grin.

John felt his face getting red, he always thought this fair was full of perverts, and now he seemed to be the horny guy among all the crossdressing participants! He was unsure where to look until he noticed a flash near him as he approached the middle of the runway that extended the stage.

Sarah had just taken a picture close enough to be able to tell if John could win a race with a few inches of advantage that did not come from the prosthetic breasts he wore. He could see her laughing as well.

His mind, trying to escape away from the flashes, started a day nightmare. 'What if the picture gets to my office?'. "Hey, hey John, you look really fine in a dress! I'm thinking of promoting you for Office Eye candy" With that, John saw himself dressed in a slutty secretary attire. His was way smaller, and his heel was too high for balance. He would bring coffee to Mr. Karsen, his boss, and once served, he would feel the sleazy hand of his manly boss groping his rear. "This girly booty is the perfect anti-stress feature. Well thought, Sarah." he looked away from his boss to see his girlfriend, a huge grin on her face as she counted money. "I'm glad to do business with you, Mr. Karsen!".

It took John the time to go all the way around and back to stand on the stage to notice she was not being mean. She was having fun. Her eyes showed some mischief shortly as she bit her lower lip while looking at his dress's front, but she looked at him with the same adoring eyes she had shown earlier when she met his gaze.

A woman dressed in adjusted-to-her-figure smocking walked to the center of the stage, holding a microphone.

"Ladies and gentlemen, welcome to today's womanless pageant!" She called up the attention of all present.

"Today, we got more than a handful of dear husbands and boyfriends as the beautiful contestants." She pointed to the figures, including John and some other crossdressed chaps near him, with all sorts of different wigs.

"First of all, they already deserve to be praised, every single one of them, for just coming here today and putting on a good show for a good cause!"

Applause from the audience

"We know that there are professionals here, and since that would be unfair, today's first and second places are reserved for amateurs!"

Applauses and whistles from the audience.

Since he was nervous, John could not pay much attention to the presentation or any of the speeches. Why was Mr. Happy so happy?

Did he like the clothes?

'They do feel nice...'

Throb throbs were the reaction in his lower half as he acknowledged the pleasant feeling of the clothes' soft material on his recently hairless skin.

Was it Sarah's smile when she saw him getting a feminine appearance?

'She seemed very happy. I love her smile.

Well, maybe...

'Maybe I'm discovering a kink!'

'Great time for that! Way to go, John! Discovering a new thing that you enjoy right in the middle of a char-' his thoughts got interrupted by a microphone near his lips and a question made by the showwoman.

"And you, lovely? Say your name for the audience." The showwoman was holding the microphone so John could answer. He just could not think properly; thus, his response was logical and incorrect.

"J-John.."

Everyone laughs.

"Alright, I know you are really excited to be with us today. You seem to be very happy here among all the ladies. Maybe there is not enough blood where there should be for proper thinking, 'John', but at least for the competition, we need you to have a feminine name, just like everyone else. Okay, sweet cheeks?"

More laughs.

John felt incapable of speaking as the woman kept mocking him for his dress being tighter in his crotch area, his face getting redder. He felt like it was burning already.

A woman mocking him while he was in panties did jog his memory of his sexy times repeatedly as Sarah called him 'panty boy' and 'sissy boy, and she did call him 'sweet cheeks' several times.

He wouldn't soon forget his girlfriend mounting his erection and asking him, "You like this sweet cheeks?" or "Who is my sweet cheeks? Who is my sissy boy?". It seemed really hot at the time, and the memory sure helped fuel his current predicament.

"Alright, why don't we decide her name then? What shall it be?" The woman with the microphone turns to the audience, making an exaggerated and comic scene of placing her hand at her right ear.

Some could hear the name propositions amid the screams, laughs, and whistles.

"Ms. Tent!"

"Jane Rocket!"

"Martha Threelegs!"

"Well, folks, I heard a perfect combination that did not come together. She will be Ms. Tent, but her first name will be 'Joy'! Now give Ms. Joy Tent some love, people!"

The audience roared with John's new name for the show, even with some laughing too much to be able to keep up with the applauding ones. He could see a few here and there mocking him.

John's endowment was not even close to being considered small, but the mocking would be enough to make him feel like he had a shrimp standing up in his panties. Even if there was barely any real 'him' visible, he felt exposed due to the simple gesture of minimal size and the other mocking thumbs being held between fingers.

When he started to breathe harder without responding to the microphone, the showwoman had already gone to the next participant. John didn't pay attention. He began to think about calling it quits and just running off stage, that is, until he looked at Sarah. She was laser-focused on his feminized form, biting her lips, clapping her hands, and jumping up and down excited about him. She mouthed, 'You are great, thank you' and then an 'I love you' in his direction.

'A happy Sarah is a good reward, John. You can do this,' The aroused guy in a dress told himself as the names of all participants were already revealed to the audience. As helpful as the thought was, thinking about the favor he wanted from Sarah as a reward did nothing to help diminish his arousal. Quite contrary, it seemed to throb yet again.

Still focused on his thoughts and fantasies, John was not paying much attention to the showwoman explaining the contests they would compete in.

"Could we all take a moment to appreciate how much Joy likes the idea of the kissing contest?" The mocking showwoman was again standing right next to John, pointing at his throbbing member in his tight mermaid dress.

"All of you ladies should feel proud of yourselves. Not even one of your own could handle the heat without a visible excitement about your presence here today!"

Applause and laughter filled the atmosphere yet again.

"And now, without further ado, let the fun begin!"

RUNWAY

The contest was now progressing to the actual competitions.

Of course, everything being for fun, they could have any sort of thing that was not needed to be in an actual pageant. That was precisely what John missed by his distracting thoughts.

"The ladies will change clothes quickly with the help of their sponsors!" the showwoman announced as the first round of activities.

Applause.

"Wait, wait, there is a catch! Everyone will pick up two costume ideas from my hat here." She gestured to a top hat she was holding, which was now up on a side table by the judges.

"Thank you to the audience for the ideas. We managed to get all the costumes available in the dressing room!"

"Now, Ladies, turn to your left, and one at a time, walk to me. Each of you needs to get a new costume for the runway, and there is one more thing! Each of you must get an additional slip of paper so that your sponsor will have a nice surprise outfit as the second one you will wear for the runaway." The showwoman continued.

John tried to filter out the noise from the cat calls and applauses from the audience as he had to turn and present his profile to the audience. People seemed to be stuck in a room full of laughing gas as her prominent name-giving attribute insistently tried to create a tent in his tight dress.

'Why the fuck actual fuck? It is not going down!'

'She, whatever her name is, said the sponsors might help. Maybe Sarah can get something to help me."

John tried to think about alternative ways that his girlfriend and "sponsor" could try to dismantle the tent on his crotch.

He started to think that maybe she was able to run and quickly get some ice, or perhaps he was able to find relief.

'Oh no, that is a terrible idea.'

Just now, the thought of actually trying to relieve himself in a dressing room full of MEN sounded worse in his mind than being the butt of a joke right now.

'I gotta relax, deep breaths and relaxation.'

He tried thinking relaxing thoughts, a lovely beach, clean waters, some exotic drinks, Sarah in a string bikini...

'No, wait, that is not helpful!'

He tried thinking about his work, being in an office, getting busy, and getting some relaxing coffee. Sarah appeared and questioned, "Why are you wearing a bikini to the office, sissy boy? Not that I'm complaining, tough." John opened his eyes and looked annoyed at his wild imagination, humiliating himself with a terrifying possibility, even if his girlfriend seemed aroused in the scene in his head.

'I can't think about anything else!'

'Alright, Mr. Happy, I will just keep breathing, be present at the moment, and wait you out!'

John slightly nodded at his determination.

He missed the second call from the showwoman that he hadn't yet caught the name.

"MS. JOY TENT! If I have to go there and get you moving, I will use this handle you proudly present!"

Ms. Tent started walking quickly just as the possibility of someone touching and maybe prolonging or worse, causing more pleasure to her tent-holding stick could be part of her reality.

John reached the Showwoman, and she presented the top hat. The mischievous grin of someone who is expecting more opportunities for cheap shots mocking him was present in the woman's face.

In his mind's eye, he could see many different dresses and costumes. He thought about the costumes he saw in the dressing room, Cheer-leader 'that looked way too small and tight'. Another costume he had seen was that of a complete showgirl, one of those bouffant skirts that were meant to be held as they did that leg-kicking forward dance, picturing himself doing the teasing number, revealing both of his hairless legs. At the same time, his third one would keep being teased by the audience.'What if I get that other one?' There was one costume he did find strange. It was full of feathers and bright with a very bright green color that would showcase whoever wore it on a whole new level. He saw himself dancing to some drum music with that specific sparkly feathered costume and how much everyone would laugh at his clumsiness.