It had been a couple days since Tails fell into the rabbit hole. He's searched up so many websites and forums dedicated to crossdressing boys. He even mustered up the courage to ask them questions. Surprisingly enough, they were a very supportive community. Giving Tails, a wannabe crossdresser that has yet to take the full plunge, all sorts of advice. Eventually, his heart was ready, and he bought his first outfits online.
It started out small. Regular girl clothes. Nothing sexy, just cute. Normal panties, long skirts, blouses, and other accessories. He also started learning how to use makeup, of course, the first thing he learned was how expensive the stuff was. Nevertheless, he continued. Eventually, he went ahead and bought a few risque things. Clothes that showed more skin. Lingerie. Etc.
When Tails finally thought his skills with makeup were good enough, he considered posting his first photo. He opted for something simple, he wasn't ready to let people see his unmentionables just yet, and chose an off shoulder sweater. It was long enough to cover his crotch, so he decided not to wear pants, just panties, so long as he kept the angles right. And of course, a very popular article of clothing, thigh highs. So many crossdressers wore them, he might as well join the bandwagon.
Of course, the finishing touch was a mask. Though he doubted any of his friends browsed this site, he wanted to be careful. Tails even went the extra mile and got a mask that read out: BITCH. It made him feel naughty, but that was what he was going for.
He got in front of the mirror, showed off his ass and the bump of his little balls hidden behind striped panties, made sure he got a good angle of his bare shoulders, and click. He took his first photo. He had already taken several other photos, but this one would be the first for the forums.
Tails took a couple more and posted them online. Heart racing, his mind tried to degrade him. Telling him that he wasn't pretty enough to do this. That people would find him ugly, repulsive, and perverted. That this was a mistake.
Next thing he knew, comment after comment telling him how beautiful he was appeared below his photos. Numbers appeared next to the thumbs up button. And for the first time in Tails life, he wasn't ashamed of his feminine figure.
Seeing the love, he decided to risk it all. Well, not all-all, just a bit more. He knelt in front of the mirror and lifted his sweater to show off his tiny dick. He rubbed it gently, letting the blood flow, until a two inch pecker erected itself and stretched his panties.
Tails also pulled down his collar to reveal a single nipple. He wasn't wearing a bra, there was no need of course. With that pose, all he could think was, he was perfect.