Pretending to Be Her (Gif) Patreon-Only (Patreon)

Bryan was out of town for a business trip staying at a one-bedroom AirBnb. The decor and items in the closet indicated that the host must be a woman in her early-20s even though the profile for the host seemed to be a company name. Bryan missed the days of being around woman that age. As women became older, they seemed to want to settle down, get a steady schedule, and maybe start planning for adult things like buying a house and having a family. Since he turned 30, he had been through the whole long term relationship thing and found that dating was much harder at his age even with an abundance of what seemed to be unlimited dating potential on apps such as Minder. Although the idea of reliving those days while out of town where there are no social risks sounded fun, it would be time-consuming going out to a random bar in hopes that there would be young ladies there that he could charm for a night.

Why go out into town to find a girl that age when there was one living right there! Bryan had never crossdressed before, but something about being in the feminine room made him want to experiment. He was out of town after all and surely no one would see his newly-shaved legs at the conference tomorrow since he would be wearing suit pants. The owner of this room seemed to have a large makeup collection he could experiment with and after watching a few makeup tutorials on TikTok, seemed to master the practice of blending, contouring, and doing his eyebrows. The hair extensions found in the vanity section seemed to work well with his hair giving him a natural feminine look. He tried on various clothes in her closet and even panties in her dresser drawer but his favorite was this pink dress that made him feel very feminine. After finding the perfect dress, nice heels, and painted his nails he changed his mind and decided many hitting the town could be fun for a bit to see how people would treat him as a woman!