Red High Heels Pt 2

Inspired by my friend and HIS red shoes… Please comment I know he would love to hear what you think.

Two months later Jim was wearing heels, skirts, and pantyhose under his work table at home, he even started taking zoom calls from fellow workers, while wearing them. Everything had changed since his first adventure in to wearing female clothes, he didn’t feel bored as much anymore, it was exciting to know what he was wearing under his desk, he even started using a female name, not to his co-workers when he was on zoom of course, just to himself, his work name was now Carol.

After taking a new name he started to use other parts of his female persona, he could buy everything on line, he even set up an account at Bennetts in town, in Carols name of course, he thought it would be easier to order female things like make up and even a couple of wigs, Jim was going all in.

Shoes, dresses, pantyhose, bras, pretty panties, that would hide his maleness, and his favourite thing was make up, he became quite skilled at transforming his face from male to female, one time, when he was talking to a new client, he zoom called her as Carol, the excitement he felt was through the roof, his voice wasn’t perfect but he told Shelly (the new client) that she had a cold, that seemed to satisfy her.

“Nice speaking to you Carol, I look forward to working with you again, and I hope your cold gets better”

“You too Shelly, and thanks” said Carol

This was when things started to snowball, Jim loved being Carol too much, he gradually began to deal more and more with clients as Carol, so much so that he decided to apply to his company for a job as Carol, the application was on line so he wouldn’t even have to leave the house, he knew he had all the experience, and the extra income he would get as Carol would pay for all his female clothing, it was an easy solution.

Carol easily passed the interview on line, she couldn’t believe some of the questions they asked her, a five year old could answer 50% of them just by guessing, this was going to be so much fun, she thought.

Until one day, Carols boss (Jack) phoned her and told her that she would have to go and meet a new client, he said she would be so much better meeting a new female client than anyone else on his staff. “Its only lunch, nothing may come of it, but it could be huge” Carols voice was so much better now after using an app on his computer that helped people with speech issues.

But Jim was freaking out, he had never left the house as Carol before, he looked through his clothes, he couldn’t believe how many dresses and skirts he had bought on line, even the male clothes he had looked old and creased, not surprising he thought, he couldn’t remember the last time he had worn any of his male clothing.

He needed a drink, as the day went on he became more relaxed, looking through dresses and heels that would be suitable for meeting a new client, Carol would have to look professional, so not the slutty clothes Jim had worn when sitting at his desk, no, Carol should be a smart, young professional, but the more he looked, the less he saw, he had to do something drastic, he decided he would take the rest of the day off and go outside to a brave new world as Carol and buy a suitable outfit.