Finding My Level

Story Info
Trans Woman helps a closet crossdresser.
2.6k words
4.71
12.3k
13

Part 1 of the 2 part series

Updated 06/11/2023
Created 06/05/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
leeanna19
leeanna19
674 Followers

This is a story about a trans woman helping out a closet trans woman. NOT a sex story.

Dan waited outside his boss's office bedside the door. He could smell the sweet perfume coming from Cindy, his boss's secretary. He looked at her as she faced away from him photocopying. She was slim but had a nicely rounded bottom. She wore a narrow black skirt and black stockings. He wasn't sure. He knew she did sometimes, as he had seen the bulges of the clips outlined in her skirt before. She had a silky white short sleeved blouse on and 3-inch heels.

She looked like a textbook secretary. Oh, how he wished he could have been her. He had struggled with his gender identity all his life. His father had caught him wearing a towel around his waist and one over his head pretending to be a girl and spanked him until he screamed.

His mother soothed him and patiently explained he was a boy, and he would never be a girl. He hid his pain and cried himself to sleep that night. He used to pray every night that he would wake up the next morning as a girl.

Being an only child, he was often left alone at home in his teens. He used his time to explore his mother drawers and wardrobe. He always hated the clock. He would be obsessed with checking the time so he would not be caught. While he was dressed in his mother clothes he would dream of another life. A life full of colour and feelings, a life where he could express himself, tell people how he felt. His heart used to sink when he had to go back to being a dull teenage boy.

Cindy turned her head, and Dan hastily looked away. Soon after he was sitting in his bosses office.

"Right Dan, not got much time, so I'll be brief. I want you to look after a new member of staff. She will start tomorrow morning and I want you to make sure she doesn't have any problems."

OK, but why not let the other girls in the sales office take care of her? Why the special treatment?"

"Well Mandy is a trans woman. I know, before you say anything, I don't agree with all that gender change crap. Bunch of weirdos if you ask me."

Dan knew all about "that gender change crap". He had realised he was not the only one who felt the way he did when he first went on the internet in the late 90's. He knew he should be one of the "weirdos". He had kept quiet and now had a wife and teenage kids.

"Look Dan, we can't afford her to get upset by anyone. We have hired her to tick some boxes. We have been hiring a more ethnic workforce, as you will have noticed."

Dan had noticed. When he had started, everyone of the thirty three employees was white. He did think that was odd. Recently he had noticed the workforce had thankfully been more diverse.

"Now with this.. creature working here, we tick the LGBT box. It will look good for when we float the company. The only thing is, I have seen what those Stonewall fanatics do when any trans people are criticized. We can't afford the bad publicity. So you make sure that she has nothing to complain about, got it?"

"Yes Mike. I'll look after her. There won't be any problems."

"Look I know a man like you may be sickened by having to be nice to a person like that, but if it all goes well I'll look after you at your next salary review."

Dan went to work looking forward to meeting this woman who had done what he never could. She was true to how she felt inside. It would be fascinating getting to know her.

When he finally met Mandy, he was impressed. She was a confident woman in her mid-thirties. She dressed stylishly and he only noticed a slight masculine hint in her face. If he didn't know he would not have noticed. He felt a slight twinge of jealousy.

He introduced her to the rest of the staff in the sales office and she interacted with smiles and jokes. She was obviously comfortable in her skin. He couldn't help feeling drawn to her. After a busy morning showing her how the computer system worked he asked her if she wanted to go out and get lunch.

They sat in the café just chatting about the company. Dan was aching to ask her about herself. Mandy seemed to sense this.

"Before you burst Dan, I won't be too upset if you ask me about myself."

"Is it that obvious? You honestly fascinate me. You are so feminine. I never would have known if I weren't told. When do you transition?"

"First, thank you. It is always nice to hear that. I seem confident, but sometimes I'm a mess inside. I have doubts and fears like everyone else. I transitioned five years ago. I have been on hormones for ten."

"I know you are probably used to people saying you are brave, but it couldn't have been easy coming out like that to your family."

"Well that part was easy. I grew up in care so I never needed to ask anyone's permission. With me it was just a case of being able to afford it. I had my surgery in Thailand."

They had a frank and in-depth conversation about surgery and recovery. On the way back Mandy asked Dan a question.

"Dan, you seem to know an awful lot about the different surgical techniques. Can I ask you? Have you considered it yourself? You haven't asked the usual questions about my sex life that many people ask."

Dan panicked. Was he this easy to read? He didn't know what to say. He had carried this secret his whole life. It would be so nice to talk to someone to share how he felt. He barely knew Mandy, but he was aching to tell her. He instinctively knew she would understand.

"Well it's just.. I er."

His phone rang and saved him the need to explain.

He couldn't get to sleep that night he kept going over what he would have said to Mandy. Should he tell her? Or should he just muddle along with his life as it was. He was afraid, it was like he was about to unlock Pandora's box.

The next day Dan was very wary around Mandy. She of course sensed this and asked him out to lunch. At first, he refused, but then thought it was unfair. It was his problem, not hers.

Sitting in the café the conversation was muted. Dan was wary of her. She seemed to be able to look into him. He suspected that she knew he wanted what she had.

"Dan, I think I understand what's going on. You dress or have dressed as a woman before, haven't you?"

Dan could feel his face flush red. He could barely look at her.

"Look Dan. I have been where you are. I won't judge you for how you feel. How could I? Your secret is safe with me. Just know I understand, you have a friend and an ally. You're a nice guy, but I can see that you're sad inside."

She put her hand over his when she said this. Dan froze. His innermost "dirty" secret was out to a woman he barely got knew. He felt a mixture of fear and relief. It was so confusing.

He just looked at her, not knowing what to say.

"Dan please come to my flat after work. Tell your wife you have to work late. I'll explain. I know I can help you. Please trust me."

Dan's heart felt like it was going to explode in his chest. Did she want him? Was she going to threaten him? No that was so stupid. He knew she was a nice person. He just felt so vulnerable with her knowing his secrets. She could ruin his life.

"OK, but I can't be long. Two hours at most."

"Please Dan. Don't worry. I know I can help."

After work he gave her a lift home. Mandy lived in a private tower block on the other side of town. Dan worked out it would take around thirty minutes to get home. When they arrived at her flat Mandy sat him on the sofa and asked him if he wanted coffee. She put the perculator on and the busied herself while he watched the news on tv.

"The coffee will be ready in a few minutes. Please come with me, I want to show you something."

She led him to her bedroom. Dan started to pull away. She was attractive, but he was faithful to his wife.

"Dan we're not here for that look what's on the bed."

On the bed there was a black summer dress covered with red roses, a pair of silky black knickers and a pair of dark tights.

"What's that for?"

"For you silly. I know from what you told me about your family life you have very little chance to dress at home. It must be so difficult for you. These should fit you. No pressure, if you don't want to. I'll leave you here and finish the coffee. See you when you decide."

His heart was thumping. He had not been able to dress for years. Now there was a chance to do it in front of someone. This had never happened before. What if she took a picture of him?

Mandy waited in the living room. There were two steaming mugs of coffee on the table in front of her. Dan appeared in the doorway looking like a deer caught in headlights. The dress fitted him well. he had even put the tights on.

"That's better. How do you feel?"

Dan's heart was thumping. His throat was dry.

"Er. Ok I guess."

"Come on sit down and really tell me about yourself."

Dan slowly opened up. He told her about how he always felt he should have been a woman. How he knew he never could be, but the feeling never went away. He told her how he had put his wife's knickers on in the bedroom once. She had got very upset, so he said it was all a joke. He felt so bad for upsetting her.

"This is the first time I have worn a dress since I was eighteen. It feels, so right, but I feel guilty. I'm a man. I have to be a man for my family."

Tears were streaming down his face as he said that. Her heart went out to him. She had felt all these feelings. She crossed over to his chair, went to her knees and hugged him.

"There, there. Its Ok to cry. You're going to be fine."

He buried his head in her shoulder and sobbed loudly. He was wailing like a baby. She held him tight.

"It's OK. You're doing fine."

After five minutes he was cried out.

"Come on drink some coffee."

He gulped his coffee and coughed.

"I'm so sorry. I don't know where that came from. What must you think?"

"I think you are a nice person that needs an understanding friend."

"Men don't cry. I made myself look stupid."

"Men do cry silly. Humans cry. You have just been taught that men don't cry. I actually think it was the girl inside crying though. You have denied her for years."

Dan knew she was telling the truth. He had longed to be a woman. He thought about it all the time.

He explained all this to Mandy.

What could he do? He had a wife and two children to support. He couldn't let them down. Their lives would be ruined if he popped up and said, Hey, guess what? I am a woman now. From today you can call me Danielle.

He knew he would lose his wife, kids and job. It wasn't an option. He felt trapped. It was no one's fault but his own. He remembered his mother telling him he would never be a woman.

"Dan it isn't your fault. Its just the way we are made. It took me years to accept that. I know what you're going through."

"I suppose you're going to tell me to be true to myself. Tell everyone I'm going to live as a woman? Well, I bloody well won't So you can forget that. I have too much to lose!"

He spat out the last few words.

"Hey, friend here remember. No, I won't tell you that. We all have to find our own way. What is right for me may not be for you. Now honestly tell me how you feel wearing those clothes."

"I er, I feel normal. It feels like I should be like this all the time. I feel calm. It would feel better with a wig and a bit of makeup, but I haven't done that since I left my parents."

"You have spent half your life fighting what's inside. It won't go away. It's part of you. It's what makes you Dan. The nice guy that all the guys and girls in the office like."

"So, what do I do?"

"That's for you to decide. I would suggest you don't supress Danielle. Let her out every now and again. I promise you'll feel better for it."

Dan sipped his coffee. So much had just happened. He was sitting there in a dress and women's underwear, and he felt better than he had for years. Confession really was good for the soul.

"Would you let me come here sometimes and dress? I know it's asking a lot."

"If that's what you feel would help. You do what makes you feel better. What ever makes being you easier. There was a line in an old Cat Stevens song. But it's them they know, not me. It's very true. Well meaning people will give you advice, but we aren't all the same. You need to find your own level. Some compromise that makes your life as good as it can get. Life is all about compromise. Very little is absolute."

Dan was silent. His head hung low. She saw tears dripping down onto the dress. She put her arms around him and drew him to her.

"What's the matter. You're going to be fine. Shush now."

"It's not that. Why couldn't I have met you years ago? It has been so good talking to you. You seem to see right into my soul. I want to thank you for what you are doing for me."

"If you had met me years ago. I would have been a mess. We learn as we go along. I have just passed what I learned along the way. Some need to go the whole way, some through necessity can't. It doesn't make you less of a person, or even a woman. It's not a competition."

Dan glanced at the clock. He had to go. He reluctantly put his suit back on. At the front door he gave Mandy a heartfelt hug.

"You are one wonderful woman Mandy. Thank you for tonight."

As he drove home, he felt lighter than he had ever felt in his life. He couldn't help smiling. He knew he wasn't the only one. There was now an outlet for his feminine side. Just telling someone about himself was like lifting a huge weight off his shoulders. Now all he had to do was find his own level.

leeanna19
leeanna19
674 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
27 Comments
ColonelinguistColonelinguist4 months ago

The Literotica trans/cd stories that l have read up to now are typically fantasies, or perhaps partially autobiographical with a little fantasy mixed in. Let’s face it; most of us wouldn’t be interested in them if that were not so.

This one however, was uniquely different than all those other stories that I have read here so far, because it addresses the fears that people who desire to connect with their internal female or male selves as well as those folks who find themselves physically attracted to transgender people. And not to be hating anyone, but since I first discovered this site I could not for the life of me understand why someone would add their comments about these story as an ‘Anonymous,’ reader, since we’re required to sign-in with our synonyms anyway; also fear I think, but then that’s something you could probably write a whole other book about too. Anyway, thank you for putting your finger on the elephant in the room that so far, no one else has talked about.

leeanna19leeanna19over 1 year agoAuthor

Not sure who you are , but you would be surprised how many there are like us. Take care and good luck

AnonymousAnonymousover 1 year ago

Wow that hits close to home. I always knew that there were others that feel that way even though many of us feel all alone and don’t think anyone would understand and accept our situations. Considering all the violence and negativity against transgender individuals is it any doubt that we are scared. Thanks leeanna for helping me to feel more normal.

AnonymousAnonymousover 1 year ago

Wow that hits close to home. I always knew that there were others that feel that way even though many of us feel all alone and don’t think anyone would understand and accept our situations. Considering all the violence and negativity against transgender individuals is it any doubt that we are scared. Thanks leeanna for helping me to feel more normal.

leeanna19leeanna19almost 2 years agoAuthor

Thanks for all th positve comments. I have been coming to terms with "me" and this story reflects what I feel about myself now. x

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Caught with My Stepsister's Clothes I was caught with my stepsister’s clothes and forced...in Transgender & Crossdressers
Hit the Button Pt. 01 Loving Couple - Wife helps Hubby live his dream.in Transgender & Crossdressers
Feminized by Girlfriend A curious boyfriend gets feminized by his girlfriend.in Transgender & Crossdressers
More Stories