Becoming Miss Marian Chapter 3

Feminine Fun

Over the course of the next few weeks Eli managed to get through three more quick meetings, impersonating Marian. One client did comment on how poor Marian’s camera quality was, but she just made a joke to brush it off, and moved on with the meeting. His ruse was going smoothly, until two of the clients he had already met with scheduled additional meetings. He knew he could not be seen wearing the same outfit again. Marian had a massive wardrobe and did her best to always present well. 

This meant Eli had to spend another night online shopping for clothes. He figured the skirt he had could be reused, so he ordered two more blouses. He really liked the way the satin felt on his skin so he was keen to order more of those. This time one of the blouses was a tie neck blouse with a had a large pussy bow on the front. Marian had several of these, so Eli thought it was appropriate to get one himself. He also ordered his first dress, A plum peplum bodycon dress, similar to one he found on Marian’s Instagram. 

He also needed to solve the problem of his underwear bunching up weird under his pantyhose, which had continued to annoy him. So he googled: what kind of underwear to wear under pantyhose? Well he was met with all sorts of articles talking about different types of women’s panties. Eli scowled, wasn’t it bad enough he had to wear all this other women’s stuff, now he had to wear panties too?! 

Scouring through Amazon for women’s underwear, he began to admire all the photos of the underwear models, and he did still have Marian’s Instagram open. He figured why not, and his hand was in his pants yet again.

*****

When his new set of clothes had finally arrived. He knew he had to try everything on, before he snuck them into his office. Personal curiosity drew him immediately to the panties. He bought a six pack of microfiber panties from Hanes, which came in a variety of colors. He pulled a pair on and was immediately met with a novel sensation. To his surprise, the smooth and soft microfiber material felt amazing to wear, particularly the way it caressed his genitals. He was becoming noticeably aroused. He stayed focused though, next came the pantyhose, the bra, and his new dress. He stared at himself in the mirror, still fully aware of how good the panties felt to wear. His hand was pulled downward, and he began rubbing his crotch. It felt sooooo good. Not only that, but he couldn’t help but admit while staring in the mirror he looked so good. His breasts, his pantyhose covered legs, he looked hot. It was mere moments of this before he was hiking up his dress and putting his hand in his panties. 

Maybe he liked this? Dressing as a woman was kinda sexy! It felt good, and he looked good! Eli’s head filled with all sorts of self affirming thoughts as he was in a mood filled with arousal. 

Eli was a single young man, and he spent a lot of his free time pleasuring himself, but now this was new and exciting! He had something novel to fuel his raging hormones and loneliness. Although he only needed to masquerade as Marian about once a week at work, after only a few days of this new discovery he was now starting to find his way into women’s clothing every night. He ordered himself a menagerie of new clothing, bra and panty sets, nighties, pantyhose of every shade, dresses for work and home. He did research on crossdressing, and ordered himself breastforms, and a better wig. His mind was a fog of feminine desires! 

His weekly dressing sessions as Marian at work became more elaborate, he spent more time transforming, he brought more clothes in a larger bag, for a more authentic look. All of the clients loved him, and he received nothing but positive feedback! His previous dread of becoming Marian had turned into desire and utter joy!

Chapter 2<----->Chapter 4

Becoming Miss Marian Chapter 2

A Surprise Success

That night, in preparation for his video conference debut as Marian, Eli studied Marian’s social media pages. He needed to do his best to recreate her look. He studied every hairstyle, every outfit, every lipstick color. Marian was in her mid thirties and obviously prided herself on her office attire. She was curvy in all the right ways and didn’t try to hide it. As Eli poured through her social media photos he couldn’t help but admire her beauty. Before long his hand was in his pants and he’d gotten distracted from the task at hand.

Once he’d "finished" his distraction, he returned to picking out an outfit. After a little while he had all the pieces for a look alike outfit on amazon, complete with wig which was similar to Marian’s natural hair, and a makeup kit. With his task completed his hand found his way back into his pants yet again, but hey he was a young single man who had no social life because of his dedication to his work, what else did he have to do?!

The next day when his Amazon order had arrived he carefully unpacked everything. In addition to the wig and makeup, Eli had ordered a black blazer, pencil skirt, blue satin blouse, push-up bra (with lots of padding), and black pantyhose. He didn’t think much of any of it, a bit silly perhaps, but mostly a means to an end. 

After watching a video on how to put pantyhose on, he started with those, pulling them over some of his boxers. The fabric of the boxers bunched up weird under the tight nylon pantyhose, but he could deal with the annoyance for one day. Then he put on the bra, and couldn’t help but squeeze his new “boobs” after it was on and let out a little chuckle. Next came the blouse, and wow was it comfortable to wear! Eli ran his hands down his sides, taking in how great it felt. Then came on the pencil skirt and blazer, and Eli was impressed how he looked all put together. A woman from the neck down!

To deal with the neck up, he spent hours trying to figure out makeup, it was not easy. Video after video he watched, technique after technique. He must’ve gone through a hundred makeup remover wipes in a single day just trying to fix his errors. But after hours of torment, he was satisfied. He put the wig on and opened his computer to test the illusion. He attached a cheap webcam to make sure the picture was terrible, and took a look at himself. Staring back at him was the vague image of a woman resembling Marian. He was going to pull it off.

The day of the video conference he packed his outfit and makeup in a gym bag so his coworkers wouldn’t know what he was doing. When he got to Marian’s office he closed the blinds first thing. As the time of the meeting got closer he locked his office door and began his transformation. He was far more nervous about getting caught by his coworkers than he was about doing the video conference, every sound outside his office set him on edge. 

Finally he was all dressed up and ready to go, and then it dawned on him, he didn’t practice talking like a girl! “Shit” he thought! Immediately he started practicing, raising his pitch and sounding aloof like Marian. He didn’t know if it was convincing at all, and then it was the time! The client was calling! “Oh god, he was screwed” he thought in a panicked mind. 

Eli answered the call, and did his best attempt at a smile when the client answered. “Marian’s” client smiled back at “her”. Eli took a deep breath and did his best impression of Marian’s voice to welcome the client. To Eli’s surprise, the client had almost no reaction, and proceeded to ask his questions. The client only had two questions he needed addressed, and despite the alleged urgency of the call the questions were not all that difficult to answer. It seemed more so that the client just wanted some facetime with the woman who would be managing his investments. 

Given the lack of visible suspicion from the client, Eli settled into his persona. He seamlessly answered the client’s question, and they bid each other farewell with a smile. It was over in around five minutes. He pulled it off! Later that day he got an email from the client thanking Marian for soothing his worries, and added how much he enjoyed talking with her. He also expressed his interest in scheduling regular calls to discuss the status of his investment portfolio.

“Man….” Eli thought, “I must’ve really pulled this off, that he wants to keep meeting with me!”

Feeling satisfied that his great ruse was going to work, he scheduled some more meetings with some more of Marian’s clients who were looking to meet when she was available. Eli could now look forward to a lot more time with his new “friend” Marian.

Chapter 1<----->Chapter 3