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jenniesissy · 2 hours
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Yup ☺️
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jenniesissy · 20 days
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Nighties for Nancy-Boys
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jenniesissy · 28 days
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"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.
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jenniesissy · 1 month
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“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!”
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jenniesissy · 1 month
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jenniesissy · 2 months
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Release Day
by LeaRose87
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jenniesissy · 2 months
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jenniesissy · 2 months
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Growing up in an all girl family...sissy had no choice...but to be girly....and her sisters had So much fun femming girly up every day....making prissy look the total pantywaist sissy 24/7...sending her off to sissyschool in pretty frilly pink outfits and a tiara....humiliating her with excessive face makeup and soon...tattoos....as girlie gets her first butt tat today....with a pretty red heart and "Panty" printed on one side...and "sissy" printed on a pink ribbon on the other cheek...to mark her as Their sissy...and the first many humiliating tattoos to come!
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jenniesissy · 2 months
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Put on a dress for the first time. Mum just wanted to take a few photos. At first it was embarrassing, then I felt more and more comfortable and I even enjoyed it. Only my sister looked a little envious.
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jenniesissy · 2 months
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How to think like a sissy:
Right: I can’t decide which dress I like more!
Wrong: I can not decide which girl I like more!
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jenniesissy · 3 months
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jenniesissy · 4 months
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Put on a dress for the first time. Mum just wanted to take a few photos. At first it was embarrassing, then I felt more and more comfortable and I even enjoyed it. Only my sister looked a little envious.
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jenniesissy · 5 months
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Brigitte Bardot in La mariée est trop belle // The Bride Is Much Too Beautiful (1956) dir. Pierre Gaspard-Huit
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jenniesissy · 5 months
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jenniesissy · 5 months
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Keylin’s Mother was a strong advocate for her son’s feminization.
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jenniesissy · 6 months
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This will gradually become your everyday look, precious. Pretty skirts and feminine blouses. Flowery dresses with full skirts and petticoats. Smooth legs (completely smooth all over) in pantyhose or stockings. Women's shoes (because that's all you have now -- all your men's shoes were discarded long ago). Feminine skincare and fragrance, every day, keeping you all soft and smelling lovely. You're beautiful now. Inside and out. Really no longer a man. Not at all. Never again. Just as you always dreamed.
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jenniesissy · 7 months
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