“Well, how long do you think you can pull this off?” Mary asked her cousin Jack.
“Until after the recital.” he replied.
Jack and Mary had made a childish bet that he could not pose as a girl and get away with it during his summer long visit to her home. When his aunt found out that they were playing dress-ups and he had planned to dress up every day, she decided to enrol them both in dance classes. Both Mary and Jack loved the idea.
They were just weeks away from the recital and ‘Jackie’ was selected for a key role. He smiled and winked at Mary who was not very happy for it was a role she had wanted. But being the good sport that she was she went along with it and now looked forward to seeing him in his lovely costume of white tights, pink slippers and pink and white top and tutu. ‘Jackie’ could hardly wait either. In the meantime both children practised hard for the big day.
Finally the big day arrived and Aunt Marge took both her nephew and her daughter to have their hair done at a local beauty shop. The beautician then showed them how to set the lovely tiara on ‘Jackie’s’ head that evening.
‘Jackie’s’ aunt helped him get into his costume and did his makeup. She watched as he carefully hid his boyhood between his legs; holding it in place with his panties. The costume helped that situation as well.
When they entered the hall there were a lot of ooohs and aaaahs for the darling little girls and especially for ‘Jackie’. He did not know it but his own parents were in the audience, having returned from their European business trip a week earlier than planned. Aunt Marge had the job of explaining what was going on and luckily Jack’s parents had a good sense of humour and in fact were looking forward to seeing their little ‘girl’.
‘Jackie’ was a huge success and following the dance there was a small cast party, which included parents. When he saw his parents come in the just smiled and curtsied.
“We never realised that you were so talented,” said his father. “I must admit that you do have a real talent, both as a dancer and as playing the role of a girl.”
“Dad…. please. These people still think I am a girl.’ whispered Jack. “Please don’t give me away.”
“Sorry son,” his father whispered. “I just didn’t think about it.” His father smiled and winked at him.
“Well I think you look lovely dear,” his mother added. “Thanks Mom.”
During the party one of the dance instructors approached ‘Jackie’ and his parents and announced there would be a special garden party for her students the following Saturday and asked if they could attend.
“Why we would love to!” exclaimed Jackie’s mother.
“Since it is a formal garden party we expect proper white party dresses for the girls and garden party dresses for mothers. Fathers should wear blazers and ties.”
That evening Jackie asked his mother if she was serious about going to the party. “Why of course dear. I would not miss it for the world.”
“But Mom, I don’t own that kind of dress. I’ve been borrowing Mary’s clothes all summer.”
“Well then it is about time you get some things of your own.” The next day mother and ‘daughter’ went on a shopping spree.
“Don’t you feel kinda funny about buying girls’ clothes for your son?” asked Jack.
“Well you don’t look like my son in that pretty dress you are wearing and I noticed that you even wear panties and a slip under it.” Jack blushed and admitted that he really loved dressing and looking girlish. “I could tell.” his mother replied. “I think we should go with the flow for now.”
Besides finding a proper white party dress, complete with full petticoats, his mother bought him several other play dresses; stockings and undies for his very own. “I think it is about time you quit borrowing Mary’s things.”
The garden party was the highlight of Jackie’s visit. He was a real hit in his lovely lace trimmed dress and matching gloves. Another first was his panty hose, which caressed his legs and sent shivers all through him. His mother beamed with pride while his father maintained a sense of humour but wished it was all over. He felt uneasy seeing his son so comfortable in the role of a girl.
The summer visit came to an end but Jack for the first time in months: except that he did wear his loveliest panties under his jeans.
Back home he thought about all of the wonderful times spent as a girl. Then one day he received a package of photographs from his aunt, along with the doll he slept with at their home and a nightgown exactly like the one he often borrowed from Mary. It had been his favourite. That night he went to bed early wearing his newest nightie, his favourite lace trimmed panties and snuggled up with his dolly. It was midnight when his mother entered his room to tuck him in. She smiled when she saw what he was wearing.
The next morning Jack woke up and found a play dress hanging on the hook outside his closet with a note for Jackie to come down to breakfast. He quickly donned a slip and the dress and arrived at the breakfast table with a happy grin on his face. This would be the way he would dress whenever his father was out of town. He was Daddy’s boy and his Mommy’s little girl!
