Fear, it always seemed to be a part of his life. Fear was the feeling coursing through Tyler Croft at this moment as he entered the hotel and headed to the small bar just off the lobby. The initial excitement he had felt upon his arrival had faded and the fear returned.
He felt eyes on the movement of his butt under his leather miniskirt he entered the bar and located an unoccupied booth. The seat and back cushions were soft and the interior was warm, cozy, and richly appointed and he began to relax. A waitress appeared and took his drink order as he continued to settle in.
He crossed his legs in an attempt to get comfortable and momentarily forgot the fear as he admired the look of them under the black nylons stockings, they looked great. He then smoothed the front of the short skirt in a practiced gesture to banish any wrinkles.
He sat back against the cushions and started playing the if-only game. If only he had not started chatting with the male on that site. If only he had ignored the requests to post some pictures, but he didn't. How his head reeled at the comments those pictures received, not only from him but some of the others on the site. If only he had not been so weak.
" What were you thinking," Tyler said to himself as he glanced around the room. " This was never about appearing in public."
For so many years he had worked hard to kept this part of his life a secret, fear of discovery was a great motivator. Now here he was out in public for all to see.
It started when he was much younger and it began with felching a few items from his sister's room and wearing them behind closed doors. Like many, he had no idea where his desire came from, and instead of ignoring it, he obeyed it. Until that day he was a typical teenage male and did the things most males his age, they did not include having a desire to wear his sister's panties.
He recalled trembling with anticipation as he removed his outer clothing and underwear and then reached for the items that he had borrowed. Oh, how his cock began to tingle and thicken the first time he stepped into a pair of his sister's silk panties and began to slowly draw them up his legs. The sensation of his raging erection and balls being held in place by the tiny silky cocoon was beyond description.
His body tingled again as he fastened the blue silk and lace bra around his chest and ran both hands over the silky bra cups. He was a little depressed that he had nothing to fill the cups but it didn't last long. Recalling what he had heard in high school he began carefully stuffing the empty bra cups with kleenex. It gave him the look and feel of breasts and more than once he emptied his load in his tiny panties as he ran his hands over the full and silky bra cups.
The fear of discovery was always present and he did his best to overcome it. He made sure that his bedroom door was always locked and even leaned a chair against the doorknob and that he only dressed in the wee hours of the morning when everyone in the house was fast asleep.
Even on those occasions when his parents were out for the evening he still practiced this level of protection in case his sister came home early. Not that she was in the habit of opening the door to his room without knocking but better safe than sorry. He would have a difficult time explaining why he was wearing her lingerie.
Eventually, his sister's lingerie was not enough and he began to borrow skirts, blouses, and pantyhose. His sister was a clothing junkie and there were racks of her old clothing hanging in the basement which had been earmarked for charitable donations so they would not be missed. As he and his sister were twins they shared a similar body type so her clothing fit him very well.
Tyler soon lost track of the number of nights that he flopped onto his bed once fully dressed in the borrowed finery and ran his hands over his body as his teenage cock became harder with each passing minute. As usual, one hand ended up sliding under his skirt and along his pantyhose covered legs until it reached his crotch. Once there he allowed his fingertips to run over the bulge his cock made under his silky lingerie and almost immediately lost his load in his silk panties.
While he was quite happy with the way his body looked and felt he was saddened that his face still looked like a male. That's when he became interested in makeup, but there were no resources to obtain that information. He didn't dare talk to his sister as that would have raised suspicion and the family only had one desktop and he was sure that his parents kept track of the sites he and his sister visited. It was the gift of a laptop from his parents to him and his sister that Christmas that had changed everything.
"Just don't visit too many porno sites," his Dad joked even as his Mom smacked him for making such a comment.
He remembers telling his parents not to worry as he wasn't into porn and that was the truth. He began to visit sites that offered makeup and makeup instructions. He remembered taking money from his savings account and placing an order for the products that these sites recommended. He had the package delivered to his Grandmother's house as the fear of discovery still loomed and he knew that Grandma wouldn't question it.
Tyler practiced applying makeup every chance he got and over the years he became quite proficient at it. He remembered the fear of being seen with traces of makeup on his face and always took an extra amount of time when removing it. He moved out of his parents shortly after graduation into a beautiful condo as he had landed a well-paid entry-level position as an IT. Now he was free to order whatever he wanted without the fear of detection, and order he did.
Soon nighties, garter belts, and nylons filled his dresser drawers along with a collection of the silkiest panties he could find along with their matching bras. He discovered breast inserts and ordered half a dozen different styles. His closet held a collection of short skirts and blouses along with high heels and a few long brunette wigs.
A large three-sided mirror similar to what you find in department stores graced one corner of his ready room and he spent hours admiring himself once full made up and dressed.