Sissy Sorority, part one

Jeremy knew he was different by the time he was 12. At that age, he realized he was much more comfortable wearing dresses and skirts than pants and jeans. Of course, he never told anyone about it. But, whenever he had the chance, he would “borrow” something from his older sister and spend some time “being pretty,” as he called it. He wasn’t gay—he knew that. He enjoyed the company of girls and wished he could spend more time doing the things they did. He didn’t want to be a girl, either—he just preferred looking and acting like a girl.

Now he was a college freshman, spending Saturday afternoon in his favorite way—lounging on the bed in his off-campus apartment, wearing a delightful satin nightgown, scrolling through the internet on his laptop, looking for websites about boys like himself. Most often, those sites featured photos of guys wearing bras and panties, sometimes fully dressed as girls. They were fun to look at, but Jeremy was hoping for more, hoping for information about activities such males (often referred to as “sissies”) could safely engage in.

Today, he finally lucked out, when this advertisement popped up.

“Wow!” he thought. “Is this real? Does this group have a chapter on my campus?” He clicked on the link for more information.

Phi-Pi-Beta has chapters on scores of campuses around the nation. Key in your college’s name to find out if we’re active there.

Jeremy did so and was surprised to find out there was a chapter there. He clicked on the link for it to find out more.

The Phi-Pi-Beta chapter house in your community is located at 55 Rivington St. It holds introductory get-togethers every Saturday at 7 PM. Dress is “coms as you are,” as feminine or as masculine as you feel up to. Come on by!

Jeremy checked the time. He had three hours to be ready. “What should I wear?” he asked himself. “I have plenty of girly clothes, but I’m not sure I’m confident enough to show up in public that way.” In the end, he decided to “underdress.” He put on a pretty pair of panties in a floral print and a matching bra. He filled the bra just enough to have a soft curve under his chosen shirt. Getting a bit more daring, he pulled on a pair of tight stretch jeans (designed for girls, of course) and pink low-cut girls’ sneakers, letting his bare ankles show.

As it came time to leave, Jeremy looked at himself in the mirror. “Makeup? Or will that be a step too far?” Eventually, he decided a light coating of soft pink gloss on his lips would be enough. The chapter house was just under two blocks away and it was a warm spring evening. He took a deep breath, feeling the constraint of his bra, and stepped outside. Thanks to the weather, the area around campus was quite busy, but no one seemed to take notice of this mildly effeminate young man as he strolled to the Phi-Pi-Beta house.

He arrived to find a large home, probably at one time a wealthy family’s mansion. He walked up the steps, rang the doorbell and, in short order, the door was opened by a pretty thing in an a-line dress. Not until the figure greeted him—“Hi! Welcome to Phi-Pi-Beta!”—was Jeremy aware that this vision of femininity was as masculine as he was.

“Uh, hi…” he stammered. “I’m here for the introductory get-together.”

“Then come on in,” the greeter replied. “My name is Adelaide…and yours is….?”

“Jeremy,” he answered.

“Oh, really now,” Adelaide laughed, noticing the curve of his bust and the style of his jeans and sneakers. “What’s your femme name?”

Jeremy was taken aback. He hadn’t considered that he would need a girl’s name. “Ummm… well, I guess you can call me Jemma!”

“Jemma! I love it,” Adelaide gushed. “Come this way.” She led him into a large room filled with people. Most of them were dressed in party clothes, feminine party clothes, but a few were clad more casually, like Jeremy. Even so, it was hard to tell the males from the females, though Jeremy supposed that most were the “pretty boys” spoken of in the advertisement that brought him here. He also realized that not all of the attendees were students. Despite their unusual garb, he recognized a few of his instructors and professors and—isn’t that?—yes, it is the Dean of Students in a stunning cocktail dress!

Just as he was having that realization, Adelaide introduced Jeremy to the one person in the room who was undoubtedly female. “Jemma,” she said, “this is our house mother, Ms. Vera Demanden. We usually call her ‘Ms. Vera.’” The very attractive woman, in her early 40s, extended a well-manicured hand to Jeremy. “Ms. Vera, this is Jemma. She is here for the first time.”

“Pleased to meet you, Jemma,” said Ms. Vera, as he took her hand. “But why do you look so…so…masculine?” She stopped for a moment and then smiled. “Ah, I understand! This is your first time to acknowledge in public that you are a sissy, a nancy-boy, a pansy! There’s no need to be frightened, dear. Even the real women in this group, like me, hold lovely things like you close to our hearts. Most of us are members of an affiliated society, Phi-Delta-Phi, the Foundation for Dominant Feminizers. We are all lesbians who delight in turning men and boys into male lesbian playthings.” She ran her hand lightly over Jeremy’s slightly curved chest and then down to the crotch of his tight jeans.

Jeremy blushed furiously.

“I think you could be just as pretty as Adelaide here,” Ms. Vera told him. “Why don’t you come to my salon and boutique before next week’s gathering and I’ll show you.” She handed him a card, smiled and walked away.

TO BE CONTINUED