sissyWalk

Stepping Out of the Hotel Room

lanna | 07.17.2019 | Reports - Getting Real

This girl has been a crossdresser since as long as she can remember. she was no more than four the first time she tried on a pair of her Sister’s shoes or the shoes of Mother. It wasnt long that she came to the conclusion, her desires must be kept a secret. Given the disapproving though amused looks she perceived from her parents.

During the school years how this girl longed for an afternoon by herself at home. An opportunity to partake of the pleasures of Mothers clothing. To lose herself in the excitement and pleasures the silky panties and bras brought. The feel of a dress or skirt over them. How the pantyhose shaped her legs so beautifully.

Always there was the lingering fear of being caught. What if her parents or siblings came home early?  There was one day she was 14 and skipped school early to partake of those joys. No sooner was she dressed and admiring herself in Mothers full length mirror. The sound of Fathers truck pulling into our driveway, the crunch of the gravel. Heart racing, stomach sinking in fear, as my shaking fingers fumbled with the ankle straps of Mothers shoes. They wouldnt unbuckle instead this girl pulled off the dress over her head and began struggling with the bra which mercifully came undone quickly. I had but one minute more before Father was in the house. With resolve this girls hands stopped shaking despite her fear. This girl quickly unbuckled the heels and kicked them off and remover the panties and nylons. Quickly dressing, the back door opened as i quickly placed the precious garments and shoes back where they belonged. So many close calls in that old house.

This sissys early years in her 20s were a lonely time, she could bring herself to tell noone of her desires. Even at times hiring escorts to watch her dress and at times be her Dominant.

In time she married and expressed her desires to her Wife only to find it made quite clear She had no interest and suggested this girl forget about it too. Which she for many years was forced to do to keep the peace. In time the Marriage ended.

Finally in the middle years of this sissys life she met an amazing Woman through a dating site. On one of our earliest dates, we were discussing kinky things we had tried. This girl never brought it up but She asked an amazing question of this girl, “”have you ever tried wearing Womens clothing?””she asked. And there it started. So many years of hiding and fears of being found out led me to Her, this girls Mistress.

her fondest memory is of the first time She helped this girl dress for a night on the town in that hotel room. A little black dress over black satin bra and panties. She completed this girls outfit with thigh hi boots with 3 inch heels and lastly a white blonde long straight wig and clutch purse. I knelt before Mistress as She lovingly applied this girls makeup. Lastly she produced a red leather dog collar and fastened it around this girls neck. She bade me to rise and follow her to the door. How this girls life changed when she opened that hotel door and stepped outside as her true self for the first time.

A.true story,

Your humbled supplicant,

sissy lanna (curtsey)

Discussion?

  1. princess sissy

    wonderful story! congratulations! princess sissy believes most or perhaps most sissies share some similar experiences. sister’s story just brought to mind a strip poker game in the bedroom of a school friend at about age 10. Greg was winning and sissy nearly naked when his Mother swept in and banned sissy from ever seeing Her son again.

  2. gina

    Lanna, Thanks for a great report which reflects experiences many here have had, almost to the point of being formulaic! It’s wonderful to have resources available like The House of Sissify and others to help and guide.

Something to share sweetie?