fifilou

[fifilou]

“Thank you for teaching me to be a good little girl Miss Beaty. I’ve learned my lesson and I promise never to be a naughty boy ever again!”

[fifilou]

You made your choice, Dylie, be like the other girls, with no shame, for the time of the preparation of the dance. This is a unique chance for you to share intimacy with the girls, be their closest fried, accepted as one of them. Embrace feminity as they do, you will return as a boy after the show (believe it! 😂😂😂)

"So, Dylan, what will it be, eight or nine?", Sarah asked.

Dylan hesitated a moment longer, but Sarah's gaze betrayed impatience.

"Nine," he said.

To tell the whole story briefly. Dylan and Sarah are in a class of 18 kids, ten boys and eight girls. A few weeks ago, the kids chose what act they would perform at the school dance, and it ended up being a folk dance. For this, however, nine couples had to be formed, each consisting of a boy and a girl. This meant that one boy would then have to be found willing to make the "transition".

At first, no boy was a candidate. They all shuddered at the thought, which the girls found very lame. "We would have no problem playing the boy," they argued. The teacher then decided that the girls could decide who would be the chosen one. However, she insisted that clear criteria be established first.

The girls came up with a list of three criteria. The first criterion was the boy's physical girlishness. He scored higher the more he did have certain feminine external characteristics. The second criterion was the boy's social girlishness. He scores higher if his attitude and behavior are more aligned with the feminine. Finally, the third criterion was the boy's attitude toward gender and gender equality. He scores higher the more he thinks in stereotypes. This last criterion seems to contradict the other two somewhat, but they often turn out to match up fairly well.

Based on these criteria, Dylan was chosen. His recent statements about possible occupations for women made him score high on the last criterion. The girls also found that he has soft facial features, is not very strong, and has a girlish way of walking (which they meant very positively). They also appreciated that he often dared to be openly emotional, such as the grief he felt and the tears he showed when his dog died. In short, he had many qualities, but his ideas about girls still needed some fine-tuning.

The teacher agreed to the choice. All the other boys were relieved, so Dylan was the only one not so happy with his selection. He did realize there was no point in protesting, though, and hoped it would all be okay.

On the day the costumes were handed out, he did panic, and not a little. The white blouses were made of a super soft silky material, and were full of ruffles. But the worst were the dresses, in the pinkest pink imaginable. Again, the material was super soft and also super light. And that skirt was way too short and way too wide. The disappointment was read clearly off Dylan's face.

"Everyone is going to see that I'm a boy, in a dress," he said.

None of the girls immediately denied this, so it had to be true.

"Tell you what," Sarah said, "we'll put some pins and a bow in your hair, and with some eyeliner, mascara and lipstick we'll make you a girl."

This is a typical dilemma for a petticoated boy. Either be a boy in a dress, or try to go all the way, but then you have to ditch all your boyishness. Dylan thought about the many people who would come to watch the performance. He thought he would stand out less by trying his best to look like a girl.

"It's fine," he said. Sarah couldn't suppress a broad smile.

They had practiced the dance a few times, without the costumes, but suddenly Dylan thought about the many spins they had to do. Would people then see what he was wearing under the dress?

The girls realized this too, and came up with what they thought was a fantastic idea. How about we all just wear the same panties? With this, all the girls immediately agreed. A uniform is a uniform, they said.

Dylan paled at the thought. He realized that if he wanted to be passable, he would have to join in, but at the same time he also found the thought humiliating.

"Dylan, will you join us?" asked Sarah. "Are we ordering eight or nine panties?"

Dylan didn't know what to say at first.

[fifilou]

[fifilou]

Yes I do. Especially if that someone is a woman!

[fifilou]

How lucky! It must have been excellent for your self-identification as a whore, by your sister and by the whole family. Impossible to go back or to pretend. Your future as a slut was unavoidable!

www.captionedsissyporn.tumblr.com

[fifilou]

I’m glad you notice it and encourage me.

Indeed, I feel incredibly happy now that I can live as a woman and nobody ever objects!

[fifilou]

I confirm. From 14 to 18, I only had sex with (older) men, which penetrated me once or twice a week. Then, though I sentimentally love women and got many relations with them, I had to admit that I am a woman inside. Now that I started my transition, it makes all sense. Man’s cock is really powerful!

[fifilou]

Sure my love. I’m getting used to my anal trainings, and my orgasms are so different now. I see I am starting a profound change!

Only anal stimulation for you ❤

[fifilou]

Thank you, sis, I’m dreaming to receive your education and be yours.

[fifilou]

…Don’t worry, I knew it for long. You were pathetic pretending to be a guy. Don’t cry, just accept you must belong to a strong man. I support you, tiny bitch!

[fifilou]

Please, go ahead!

[fifilou]

You know exactly what I need, I’ll do whatever you say!

[fifilou]

True! I have never been so confident since I express as a woman, though I am more sensitive and emotional.

[fifilou]

Now, put on this white shirt. Yes, I know it’s quite transparent, but who cares?

Too tight? But it needs to fit your beautiful feminine shape. Now, hurry up, sweetheart, or you’ll be late and everybody will notice you.

I will wait impatient to listen how was your day, while I’ll look for other pretty things for tomorrow…

Oh come on. It’s just a bit of secret cheeky fun. No one will know.

It won’t peek between your clothes. It won’t bulge out mounds in your chest. It won’t be visible through your shirt. It won’t bunch up. It won’t show outlines at the seams.

Stop worrying. Start enjoying a beautiful feminine day under your boring drab boy life.

[fifilou]

It was the age I had my first long-term boyfriend as well !

[fifilou]

You mean, you had this in mind when you started dating him? Everything went so quickly since you invited him home, pretending I’m a girl mate from college on visit for a few days, and arranged me so girly.

I thought his flirt was just a game, to avoid I get jealous. You know it will be the first time a man fucks me.

Ok my dear, I can’t argue. Yes, please stay close to me!

[fifilou]

Don’t regret, the important is to do it now, when tou are ready.