Ryan was just starting out on his own, in his early twenties, with his own apartment and living alone. He had a few jobs, enough to pay rent and bills but was barely making it by. He saw an ad for a male or female secretary for a women’s magazine, so he thought he’d give it a try. He went for the interview and saw mostly girls about his age there also applying for the job but there were a few other guys.

He was finally called in and she introduced herself as Lori and said that she was the head of the company. She was a very attractive woman, as she wore a button-down blouse, a black pencil skirt, and heels. He could also tell that she wore hosiery by the tone difference between her legs and arms. She mentioned that she was surprised she had as many male applicants as she did. He answered all her questions and told her about himself and his working habits and that was the end of the interview. Lori said she had to finish the last few females outside before she would make a decision. Ryan went home expecting nothing.

A few days later his phone rang, it was Lori from the magazine telling him that he had gotten the job. She said it was his honest answers, and that he appeared to be a hard worker, that got him the job over the girls that had also applied, and the other guys just didn’t impress her. She told him we would start the next week and company dress was business casual every day, some nice pants and a button-down shirt.

Monday came and he started the day like any other first day, filling out forms, learning the layout of the offices and meeting everyone. Ryan quickly noticed that ninety percent of the employees were women, and all were excited to meet him, all saying it’s going to nice have another guy in the office. He did meet a few other guys there and they were just as nice. At the end of his first day, he was taken back to Lori’s office where she told him about his job.

She told him he would be her assistant and would be answering her calls and running small and short errands around the city for her. She finally laid down the final rule of no dating in the office. Ryan went home and thought about his new job and was kind of excited about it. He started the first few days a little slow but was getting the hang of it. Every day he noticed she dressed almost the same, and she always looked stunning.

He started to feel out of place in the office with all the women wearing skirts and heels or a nice pant suit and heels, so he thought he would try an experiment and see if anyone would notice. He was making extra money now, so he was able to do this. He started with the basics and bought some bras and matching panties and started wearing them every day under his regular clothing. He really liked the feel of the panties, but it took some time to get used to the bras.

After a week of that, he started to get a little bold and bought some women’s pants to wear with his shirts. He tried them on and loved how they hugged his ass. He wore different styles and textures every day with his shirts, and no one said anything to him. He took it another step and bought some women’s button-down blouses and with the pants it was beginning to be noticeable that we was starting to wear women’s clothing.

On Monday he went in basically fully dressed, minus the shoes, which he hadn’t thought about. Lori called him into her office to send him on an errand. Before she sent him off, she told him he looks good in what he’s wearing and to keep it up. He wasn’t sure if she noticed that it was women’s attire or just how nicely he’s dressed. He finally made the switch to women’s shoes, starting with small black kitten heels to get used to them. His socks didn’t work with women’s shoes, so he bought black pantyhose and the shoes fit better.

He went the next week fully dressed and none of the ladies he interacted said anything to him. In and out of Lori’s office and every time he walked in she was smiling. But nothing was ever said about his attire. Friday came about and it was the end of the day, just as he was about to leave, Lori called him in.

“You look good in women’s clothing.”

He was shocked and asked, “Am I in trouble?”

She said, “No, but I had an idea about halfway through the first week when you started with the pants. When you started wearing the shirts, it was almost obvious and the other girls in the office noticed then, too. You looked good and seemed happier. I’ll let you continue wearing women’s clothing, but as my assistant, you’ll be dressed the similar as me: skirt, blouses, and heels every day. You can start small, but I want you in 3” heels as soon as you can walk confidently in them. If you do this, I’ll increase your pay so you can afford nicer things, if not, you’ll continue dressed as you are but no pay increase. You won’t be fired, so basically no change to your job. You can think about it this weekend and how you come to work on Monday will be your answer.”

Ryan was shocked that everyone noticed and didn’t say anything. He went home to think about it. He had gotten so used to women’s panties that was all he wore. He went to the mall to see what he could find, browsing the women’s section and looking at all the skirts. He picked a pencil skirt similar to the one Lori wore the day he first met her. Then he went to a shoe store and asked for a black pair of 3” heels. He made his purchases and went home.

He put on his black hose and pulled the skirt into place. Now that he could see his legs, he decided to shave. Once that was done, he put everything back on, loving the feel of hose against his legs. He put on the skirt and blouse and loved the way everything looked together. He decided to try the heels now. He put them on and was surprised at how sexy he looked. He tried walking and was very wobbly, so he went back to the smaller heels.

Ryan decided he wanted to do this, so he put his women’s pants and blouse back on and went back to the mall for more skirts and heels. He picked up a few more skirts, some a little shorter than others but not too short. Figured out he could comfortably wear 2” heels all day and walk in them and got a few pairs in different colors and styles . He went back to his place and waited for Monday to come around.

Monday morning he got ready by putting on his red bra and panty set, followed by black hose, the pencil skirt he first bought, a red button down blouse, and his black 2” pumps. When we walked in all the ladies commented on how great he looked, which helped boost his confidence. Ryan was called into Lori’s office.

“Close the door.”

He did as instructed.

“I am proud you took this step. You look amazing,” she said.

She moved around to the front of her desk.

“Sit.”

She reminded him of his job description and that he was to do what she needed. As she said this she place her heel next to him on the armrest, making her skirt ride up. He got a full view of what she was wearing underneath. 4” black and red heels with bows on the back, black stockings with red lace accents at the top, a red thong, her red blouse matched. He looked around.

“We won’t be bothered,” she said.

He caressed her leg and she let out a moan. She unbuttoned her blouse revealing a red lacy bra which matched her thong. He slid his hand up her stocking clad leg to her inner thigh. Lori hooked her leg around his neck, pulling him in. He moved the thong to the side and started to lick her pussy. She was wet and turned on, moaning from his sucking and licking.

He backed away as she stood up. She pulled her thong down and handed them to him.

“Keep them,” she said.

She hiked her skirt up and lay back down. He went back to licking her pussy. Licking and sucking, making her moan loudly. He tried to back off, once again worried someone will hear, but she used her legs to pull him back in.

“Don’t worry - keep going,” she pleaded.

He went back to licking her wet pussy, sucking on her clit. He darted his tongue in and out of her pussy as she squeezed his head with her legs and pulled his hair. He flicked her clit fast while sucking on it, bringing her to her orgasm. She released him and handed him a towel from her desk to wipe his face.

Lori stood up, fixed her skirt and blouse, pulling her hair back to a ponytail. “You did an excellent job. Your raise is effective immediately.”

She handed him a bag and in it were a pair of heels matching hers.

“Those shoes will be required attire every Friday with stockings and my red thong, which I just gave you. Please go start your work as you are behind because of me.”

Ryan could not love his job any more than he could when he started.