Why Halloween is my Favourite time of the Year !!

Halloween was Dave’s favourite time of year. Before he was married he dressed up as a woman every year. It started at age 12, and every year he grew more and more girlish. But when he got married, his wife did not understand his need to dress and his dressing was cut back more and more every year. Then right after they married, a son came in and there was no chance to do his stay at home and dress for a few hours anymore. Now, his son was 12, and it was Halloween again. Dave’s wife said that her mom was sick and she was going to see if she could help. Dave’s mind went pink. A chance. but what to do with his son. His mind was racing. Dave stood in the guest bedroom where he kept Diane’s things. He touched and caressed her things, wishing to find a way to dresss and be Diane for Halloween. His day dreaming was interrupted by a  sound behind him. He turned and found his son dressed in some of his wife’s lingerie and flirty maid uniform that she wore one year. The white gartered stockings were fully exposed on the slender thighs. Bobby was nervous as he toyed with the hem of the uniform. He had tried to put on make up, but as cute as the attempt was, it was very crude. “Dad, can I dress up in this for Halloween. I saw photos of mom wearing it in a book I found and she had another woman with her.
They looked like they were having a lot of fun at a party and.. well, I kinda thought if its ok with you I can dress as a girl this year. Please daddy, just for tonight okay? Mom is gone and she does not need to know. Pretty please?” Dave’s heart melted. His son was just like he was. He was afraid of the hardships that lay ahead of him if he let this continue. “Dad, you know, you could dress up too and you could pretend to be my mom when  we go trick or treating. I can be the maid and you the mommy. Please daddy. ” Dave gave in and helped bobby finish his make up and hair, and found a pair of 2 inch heels that would fit his feet. ” Okay tonight your name is Bobbi, with an I. You practice walking around while I see if I can make my self up too. 1 hour later Diane made her appearance as a nurse. Bobbi was shocked at how pretty his daddy was.

“Wow daddy you look just like the girl in the pictures when mom my wore this.” Diane set up the camera on the tripod and set the timer and as they were posing for photos all over the house, they did not hear the garage door opening. Diane sat on the counter, her dark stocking tops showing a bit and Bobbi stood playing with the ties of her cute little uniform, her young thighs displayed more than when Diane first saw her in it. Just as the flash went off, they both looked up to see Sharla, wife and mother, standing watching the little photo show they put on. She just smiled softly, and said, “let me go get ready and we can all go out to dinner and then trick or treating. Give me 30 minutes girls and we will all go.” Both girls were shocked at what had just happened. Diane took Bobbi’s hand and they went up stairs to find purses to carry on the first family girls night out. There would be many more to come….


(Visited 147 times, 2 visits today)
Liked it? Take a second to support TG Transformation on Patreon!

Be the first to comment

Leave a Reply

Your email address will not be published.


*


This site uses Akismet to reduce spam. Learn how your comment data is processed.