Monday, May 4, 2026

Becoming Miss Marian Chapter 4

A Day Full of Surprises

To accommodate all of the different things he needed to bring in for his transformation into Marian, Eli needed to bring a duffle bag into work. When his coworkers took notice he was doing this once a week, he just brushed it off as his gym bag. Of course to sell the illusion, Eli also brought a set of active wear to change into after work. One of his more perceptive coworkers, Chloe took notice that the bag seemed far larger than necessary for a single change of clothes, and began joking around with Eli about how huge the bag seemed.

Chloe was another one of the firm’s Client Relations Managers, despite having joined the company after Eli. She was formally Sofia’s personal assistant and was promoted because of her charm, and work ethic. She was a young dirty blond woman who obviously prided herself on her makeup. All of Platinum Investments Client Relations Managers were beautiful women, and having masqueraded as one himself, Eli could tell that many of the clients just enjoyed talking to the various beauties at Platinum Investments. In several of Eli’s meetings Marian’s clients had flirted with him, and Eli being in such newfound euphoria wearing women’s clothing happily obliged by doing a little flirting back. 

One afternoon one of Eli’s meetings was running a little long. He and his client had been having some fun and a little flirty banter which had kept the meeting going longer than scheduled. But he had been wearing one of his favorite outfits, with an exceptionally soft and sexy set of panties underneath. The whole situation aroused him, the flirtatious compliments, the soft panties hugging his crotch, the satin blouse caressing his false breasts. Eli felt euphoria!

But it all came crashing down when to his intense fright, Chloe had let herself in his office. Closing the door behind her she stood with her arms crossed, an eyebrow raised, and a coy smile. Eli practically screamed. He quickly signed off with his client and rose to address her.

“It….It’s not what you think!” Eli said waving his hands and walking from around his desk. 

“So this is how you haven’t lost a single client, they all still think they’re with Marian?” Chloe said with a smile of disbelief.

“No, no, no….” Eli started.

“Oh come on, you’re dressed exactly like her!” Chloe said gesturing to Eli.

“Ok well I ugh…. I was just desperate to not lose any clients! Sofia said I’d lose my job if I lost one of Marian’s clients, I don’t actually like this!" Eli screamed in self defense.

“Um, I think you do” Chloe said, pointing to Eli’s waist.

Eli looked down, only to see that he had an erection tenting his skirt. He quickly put his hands down to cover himself and fled back behind his desk.

“No….uh……please……” Eli started stammering, on the verge of tears.

Chloe sighed, “Look, why don’t you get yourself cleaned up and I’ll come back a little later and we can talk about all of this?

Eli nodded, unable to articulate any further words. Chloe left, and Eli let out a sigh of relief. At least Chloe didn’t say she was going to rat him out to their boss Sofia, but she still knew. At any point his grand ruse could come crashing down around him.

He quickly undressed from his feminine wear and into his men’s clothing, and spent the rest of his day in nervous anticipation. Finally hours later there was a knock at the door and Chloe let herself in once again.

“Soooo, are you ready to finally talk about what the hell I walked into” Chloe said with a slight smile.

Eli went on to explain everything that had happened, his deal with Sofia, his fear of losing clients, the crazy escalation to having to physically impersonate her. All the while Chloe sat without giving much reaction. Eli had no idea how she was going to respond, she wasn’t giving giving him any clues.

At last Chloe responded by saying “none of us in the office knew that Sofia gave you that ultimatum, we all thought you just seemed so stressed all the time because you couldn’t handle the job. What she did wasn’t fair to you.” 

Both sat in quiet contemplation until, at last Chloe clapped her hands and exclaimed “Alright, I’m going to help you!”

“What!” Eli cried in disbelief.

“Yup! Your secret is safe with me, and I’m going to help you with your makeup, cause girl you need some help!” Chloe said with an air of excitement.

Chloe had a massive stash of makeup in her office, and the two stayed late at work the next few days so Chloe could teach Eli how to improve his makeup skills. They spent hours talking about tips, tricks, hairstyles, how to talk to clients, their favorite outfits and styles. Chloe’s love of makeup and fashion made Eli the perfect friend to educate and talk with.

It all felt so normal to Eli, just two girls chatting about makeup and clothes. His life as Marian, although completely abnormal was beginning to feel normal. He couldn’t help but admit he found himself liking it all more and more. 

Monday, April 20, 2026

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!

Monday, April 6, 2026

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.

Monday, March 23, 2026

Becoming Miss Marian Chapter 1

An Unconventional Solution to an Ultimatum

After working for years in a low level position at Platinum Investments, Eli was finally up for a promotion which might finally change his life for the better. He was desperate to prove himself, and took on any opportunities to demonstrate his hard work ethic. His moment to prove himself finally came when Marian, one of his firm’s Client Relations Managers was going to go on extended maternity leave due to a challenging pregnancy. Eli readily volunteered to backfill Marian’s role to maintain relations with several notable clients. Sofia, the Director of Client Relations at Platinum, agreed that it would be a good metric to measure Eli’s skill, but still risky. She gave him full reign over Marian’s role, with one contingency: lose a client, lose your job. Eli had to put it all on the line to prove that he was worthy of a promotion. To Eli’s shock when finally assuming Marian’s role, was how many of her clients invested at Platinum purely because of their relationships to Marian. Her kindness, hospitality, and warmth put investors at ease. Eli could not believe in how many of Marian’s emails where her clients cited her character as the main factor for their continued investment. Eli was screwed, he thought there was no way he could possibly maintain relations with all these clients as a newcomer. Panic set in, what would he do?! After quite a while of contemplative thinking, the answer he came up with was: NOTHING. There was no reason the clients had to know there was anyone different handling their investments, he could still keep signing the emails as Marian. Sofia did not specify how Eli had to keep all Marian’s clients, just that he couldn’t lose any.

So Eli’s mind was made up, he would become a digital version of Marian, to maintain the illusion to her clients that she was still the one handling their accounts. Well the first few days of this illusion went totally fine, Eli carefully studied Marian’s emails to match her cadence and vernacular. Thusfar none of his clients were any the wiser. He had taken up residence in her private office, and could not get over how easy this ruse was. He was practically guaranteed a promotion at this rate. Then came a rude awakening, an email containing an invitation to a video conference with one of Marian’s clients. Eli obviously knew he could not accept this invitation, so he declined and asked the client to reschedule for a later date. The client almost immediately responded that this was a pressing issue that he wanted to discuss, and could only delay by two days. Two days. What could he possibly do? Marian’s success as a Client Relations Manager was her positive relationships with her clients. He couldn’t possibly divert this client to another manager, or keep delaying the meeting invites. The client was nervous about his investments, any missteps on Eli’s part and the client might take his business elsewhere. He had to handle this on his own, but how? The stress was driving him crazy, and the idea that came of it was crazy too. He was already digitally impersonating Marian, what’s a little physical impersonation as well? A poor quality web cam, a wig, a little makeup, how hard could it be?

----->Chapter 2

Monday, March 16, 2026

A Great Crossplaying Brothers Comic

Hello There,

    Anna and Elsa, the classic Disney Princess sisterly duo, or should I say Roger and John?! In this comic two brothers attend a pop culture convention and are presented with a machine that automatically cosplay's them, but things may not go as Roger expects. I've always loved this brief comic and just had to share it with all of you!


    Isn't that ending just the best?! Seems like the two of them are going to have a blast as Anna and Elsa. I just couldn't help but share this comic because it's such a great show of support in embracing the joy of femininity. We'd all be so lucky to have as supportive a brother as Roger!

-Carly

Monday, March 9, 2026

The Queen of Mary Jane Crossplay: Spidey_fish

 Hello There,

    I'm highlighting another exceptional crossplayer today, none other than New Zealand based crossplayer Fisher known by the Instagram handle @spidey_fish. Obviously with "Spidey" in his Instagram name, Fisher is quite the fan of Spider-Man, and has an assortment of Spider-Man themed cosplays webbed all over his Instagram profile (see what I did there LOL). But the cosplay by far I think Fisher excels at is his crossplay of Mary Jane Watson-Parker AKA Spinneret! 

    In an alternate universe Peter Parker reverse engineered his spider powers as a gift to his wife Mary Jane. Now with the same powers as the Amazing Spider-Man, Mary Jane Watson-Parker fights crime alongside her husband and daughter as the mighty Spinneret! What a fun alternate take on Mary Jane's story, and a great costume to boot! This is why I've crowned spidey_fish the queen of Mary Jane Crossplay's, Spidey chose perhaps Mary Jane's most unique depiction and ran with it! 

    Also I think It's safe to Fisher has a trademark pose as Spinneret! Hey can you blame Mary Jane? If I had ASSets like that in a skin tight suit I'd show them off too! Go get 'em tiger!

    While Mary Jane's Spinneret fights crime an the alternate Marvel Universe, in the Main 616 universe she has also donned Peter's costume a few times for one reason or another. Spidey_fish goes the extra mile and brings us these versions of Mary Jane as well! Gotta say Mary Jane rocks the red and blue way better than Peter does!

    Everyone knows one of Spider-Man's greatest feature's is his great sense of humor, and Fisher is no slouch in that regard! Many of the photos featuring Mary Jane are enfused with plenty of humor, and it's just infectious; Fisher seems to make crossplaying lots of fun! First she steals his suit and now his wit?! Mary Jane is out for Spider-Man's job!

    I also couldn't help but share Fisher's debut video as Mary Jane. Fisher's excitement over seeing the crossplay come together is amazing, and an absolute joy to watch! I'd be giddy too if I could pull of a skin tight suit like that!

    Well there you have it, my tribute to Fisher's incredible Mary Jane Spinneret crossplay. Fisher has created the best and most inventive Mary Jane crossplay i've seen. You can still see tons of amazing cosplays and crossplays on Fisher's instagram account, many of them Spider themed. Give the page a looksee and you'll be saying "Face it tiger, you just hit the Jack Pot!"

-Carly

Monday, March 2, 2026

Danny Phantom, Secret Crossdresser?

 Hello There,

    As I discussed in a past post there's a huge library of crossdressing themed fan art online. I previously discussed Ash Ketchum's crossdressing habit in my last post of this series, but we've got a new crossdressing cartoon to discuss today! Following a lab accident Danny Fenton gained ghost-like super powers and became the hero known as "Danny Phantom", staring in the cartoon of the same name. The show was full of action, comedy, teenage drama, and no shortage of ghostly antics.

    Danny only ever actually crossdressed once in the entirety of the show, and it was meant to be a joke. After accidentally falling in a pile of clothes Danny found himself dressed in a Little Bo-Peep inspired outfit. Although the moment was extremely brief and meant as a joke there would be no stopping fan artists online from jumping to the conclusion that Danny is a closeted crossdresser.

`    Fan artists portray Danny's crossdressing habits having expanded to far more than just Little Bo-Peep however. A lot of Danny's crossdressing is often depicted with his friend and eventual girlfriend Sam Manson. A self proclaimed Goth, Sam is used to going against societal trends; so dressing up her boyfriend in women's clothing certainly seems like something right up her alley.




______________________________________________

    Although Sam is the original model for Danny's transformation partner, more recently Sam's mother has actually become the predominant person to enable Danny's crossdressing! Pamela Manson is your typical wealthy Stepford wife, who has it all, accept a regular daughter. Pamela has an enormous disdain of Sam's nonconformity and constantly try to steer her away from it, such as pushing her to wear clothing that suits her pretty pink tastes over Sam's black and gothic one. Throughout the course of the show Pamela continuously tries to get Sam to wear pink dresses instead of her typical outfit. Perhaps it is Pam's desire to have the perfect pretty pink daughter which inspired so many fan artists to portray her as crossdressing Danny. Through Danny she can have the daughter that she never had, and always wanted!


______________________________________________

    That's not to say that Danny only has feminine fun with either of the Manson girls! How could Danny deny how fun it is to be feminine. Inevitably, he has taken his feminine interests into his own hands and has begun crossdressing on his own! I'd say when he dolls himself up he makes a pretty convincing girl.




______________________________________________

    With looks like those not even town bully Dash Baxtor can resist a kiss from those ghostly lips!

______________________________________________

    Danny Phantom, yet another cartoon crossdresser. He makes quite the convincing girl doesn't he?! I hope you enjoyed my little foray into this fan art community; eventually I'll be back with another one of these cartoon character posts. There's certainly no shortage of fan art featuring crossdressing characters to choose from. But who to choose is the real question?!

-Carly