So he continued wearing dresses and skirts for the rest of the three weeks. Every night he would grab a box of tissues and relieve the erection that had been there the whole day.
As the end approached, he started to grow sad. Detecting this, Mrs. Edgar told him “you can stay with us for the whole summer if you like.” As usual Frank was torn. The idea of another five or six weeks in nothing but dresses was thrilling but he still felt guilty for wanting it.
But would he ever get a chance like this again? He was able to wear whatever pretty, frilly, girly clothes he wanted. He continued to be embarrassed by the funny looks he got in public but just couldn’t help himself. He had no interest in wearing sensible pencil skirts or ordinary t-shirts. What was the point in being a girl if you couldn’t wear the prettiest dresses?
He opted to stay and his mother was happy enough with that. If her plan was to hope that he would grow tired of it, it didn’t work. Every day he still thrilled at the feel of tights and petticoats or at the thought of the lacey underwear that lay beneath.
With a week to go he was starting to get that sad feeling again. Mrs. Edgar sat him down one day. “I’ve spoken with Sister Brigid at the convent. They’ll take you in to the school if you like.” Frank was taken by surprise. A chance to continue wearing dresses. But if he did this, would he have to finish his four years of school as a girl?
He still had confusing feelings. He was a boy. He didn’t actually want to be a girl. He just wanted to be able to wear pretty frilly dresses. It wasn’t the same thing. But to go to school every day would mean that he would have to act convincingly as a girl - perhaps for years.
But there was probably no other way he could continue to wear dresses and skirts. If he refused, next week he would be back at home in the boring grey trousers of his school uniform. “You’d have to wear the uniform”, Mrs. Edgar said with a little smile. He was definitely interested. “It’s a blue plaid pleated skirt.”
On the first day of school, he examined himself in the mirror. He straightened the knot in his tie and tugged at the collar of his crisp blouse. One of the pleats in his skirt was kinked so he smoothed it out. The skirt fell a few inches short of his knees. He took care to wear simple blue panties – there were boys at this school too. He pulled up his white knee-high socks and checked that his t-bar shoes weren’t scuffed. Finally he tugged the lapels of his light and dark blue striped blazer. He loved this uniform. His pig tails poked out either side of his head with blue ribbons tied in bows.
His mother looked at him proudly as he stood to go out the door. His uniform was perfect but she fiddled with it anyway and sent him off.
He marched down the road looking down at how his skirt rippled beautifully. He turned onto the main road. Some girls appeared on the other side. He frowned at the state of their uniforms. Their skirts came almost to their ankles. Their off-white socks sagged. Their blouses were often not tucked in and their ties were very loosely tied – if tied was the right word at all.
Others joined them on the way. None of the girls wore the smart blazer but shabby cardigans and sweaters instead. He could see them look out the sides of their eyes and snigger at his prim and proper uniform.
He tried not to let it bother him and he continued towards the school. In the school yard he was the centre of attention. “Look at Pippy Longstocking”, someone sneered. He was relieved when teachers appeared and the teasing stopped.
He continued to get stick because of his oh-so-perfect uniform. But wasn’t going to give in to them. He wasn’t interested in going to school as a girl unless he could wear a smart pleated skirt and snow white socks. He wondered just how strongly he was committed to spending the whole year as a girl.
He became quite unhappy. He wanted so much to wear pretty dresses and skirts but, other than Lisa, her mother and his own mother, everyone else teased him and made fun of him. He complained about the continuing hard time he was getting at school.
One Saturday he was rummaging again in the trunks. Right down at the bottom he found some patterns for dresses. They seemed to be even more sissy than his party frocks. Then he realised that they were baby dresses. Just then Lisa came in. “What’s that?” She went over to him and took the magazine. “Oh my! Does Francie want to be a little baby girl?” “No, don’t be silly!” “You mean you wouldn’t like to wear one of these really pretty dresses?” He put his hands on his lap trying to hide the answer. But Lisa knew him well enough.
She laughed it off and left the room. He couldn’t help wondering afterwards though what it would be like to wear such babyish dresses.
That afternoon Lisa called him into the lounge. She had some shopping bags. “Look what I’ve rented for you.” She produced a big pink baby dress, flared at breast level and covered with layers of lace. It was obviously an exaggerated fancy dress costume. But he couldn’t take his eyes off it.
He was so embarrassed at the thought of wearing a baby dress that Lisa had to cajole him for ages. But she knew he wanted to.
Eventually she was buttoning up the back of the dress on him. She took him to a mirror. It was really really short on him. It barely covered his panties. She produced a matching bonnet and placed it on his head, tying it under his chin in a bow. Then she popped a big pink soother into his mouth. She stood back and looked at him and smiled.
He was so thrilled. He knew he must look so ridiculous but it felt great. He had such an erection. Lisa called their mothers. He cringed but they appeared almost immediately. “Look at our pretty baby girl”, his mother said. Frank went beetroot. He suc-ked on his soother to complete the effect.
“There’s one more piece”, Lisa remembered. She took out a pair of huge matching panties. She pulled them up over the panties he was already wearing. The thick lace of the baby panties could be seen below the hem of his dress.
Betty Pearl's Sissy Stories 20.1
Topic: Dream Come True (Read 35197 times)
