Crossdressing Confession to Mary

I’ve crossdressed for as long as I can remember and love wearing stockings, suspenders and panties under my male clothes as often as I can.
I love being daring and risky and often indulge when I have visitors at the house.
Last night my friend Mary came over to use the gym as she regularly does.
As usual I was wearing silky polka dot panties under my jeans having decided not to wear the matching bra as it showed through my shirt.
While Mary was in the gym I stripped off and dressed in some of my sexiest lingerie and took some pics as a memento.
When she’d finished she sat next to me on the sofa and had a glass of wine as usual and watched some TV.
I was just wearing panties but I had a real urge to change into a pink bra, suspender belt and panties that I bought a few weeks ago but didn’t have the nerve.
She’d joked about me needing a training bra when we were in the gym a while back and much to her surprise I said I quite liked the idea!
We joked about it a few times and in a text one night I jokingly said I was online buying a polka dot training bra and panty set. She encouraged it and told me not to forget the matching panties which made my heart race!
Anyway, last night I was extremely h**** and after a couple of glasses of wine I steered the conversation around to our training bra conversation.
She was most receptive so I pushed the boat out and confessed that I was wearing panties right now!
The fact that she was so accepting of my dirty little secret prompted me to confess some of my darkest secrets to her about my fascination for lingerie and that I’d slept with transvestites before.
I even told her about me having a mistress from the north who gave me sissy tasks to perform at different times of the day and I had to send her pictures to prove I’d carried them out.
The tasks ranged from wearing a chastity cage and a lingerie set under my male clothes all day and not taking them off under any circumstances to going into department stores wearing sexy lingerie under my clothes, go into a changing room, strip off to my lingerie and send her pictures. There were more daring tasks too!
It felt so good to be able to tell someone about my dirty little secret that I felt totally relaxed.
I was building my confidence to ask her if she’d mind if I changed into my pink lacy bra, suspenders, panties and stockings under my clothes (which was a massive step for me) when she said she was leaving to go home.
I was so disappointed but as soon as she was out of the door I stripped off and changed into my lingerie.
I messaged her to say thank you for listening and accepting my confession without thinking less of me and she replied by telling me it was really sexy that I was in touch with my feminine side.
This was unbelievable to hear so I went completely out of my comfort zone and asked if I could send her some pictures of what I was wearing right then and what I’d changed into while she was in the gym.
I was really nervous waiting for her response but it was all good and she said the lingerie looked great on me and she found it very, very sexy!
The rest of the night was spent fantasising about dressing up for her and how she’d react if I asked her to give me sexy tasks to perform during the day and demanding pictures as proof.
When I eventually got home this evening I immediately changed into some sexy lingerie as usual when I’m on my own (a green lacy matching bra, suspender and panties set with grey seamed stockings.
I took some sexy pictures and then messaged Mary to thank her again for being so understanding last night.
I had no response so I guessed she’d gone to bed.
Feeling brave that I wouldn’t get a response to my messages immediately I sent her a couple of pics that I’d taken earlier that she’d see when she woke up.
I also asked her if she’d go shopping for lingerie for me as the thought of a girl buying sexy lingerie with the idea of me wearing it is a major fantasy!
I’ll just have to wait until the morning before I hear her response but I feel a sense of relief asking her!

What she doesn’t know is that on occasion I like to fully transform into a sissy maid.
I wear a tight corset to give me an hourglass figure before putting on my girdle, longline bra, panties and stockings.
Then I apply French manicure stick on nails which make me feel super feminine and then settle down to do my makeup. I love taking my time to perfect the look, false lashes with plenty of mascara and eyeliner, dark eyeshadow and perfectly blended in. The finishing touch is lip liner and lots of lipstick so I can feel it every time my lips touch together.
Next I apply my clip on earrings, necklace and rings.
After that I slip on my satin French maid dress and make sure everything is adjusted perfectly in the mirror.
Last of all I slide on my freshly brushed long auburn wig to complete the look and slide in my favourite butt plug.
I feel so feminine and sexy that I get the urge to be ultra submissive.
I do the housework and love feeling this way, not necessarily sexual but feeling like I need to do this and it feels right.

Eventually I want to confide to Mary that I like to fully transform occasionally and for her to help me transform but I think it’s early days for that.

I want to be her French maid and serve her for the day to feel what it’s like to feel feminine, look feminine and be dominated at the same time.

Maybe I’ll email her a link to this story?

Mar 27, 2021

Related Posts


  • newest
  • most popular
  • oldest
  • I wish you were my neighbor

  • Looser

  • Learn to spell !
    I assume you meant loser meaning not a winner, NOT looser which means less tight.

  • What is it with you disgusting strange effeminate blokes ?
    You make me feel sick.
    I don't understand your weird fantasies and don't want to.
    You are a disgrace to normal men.

  • Men do not get it But women do understand.
    And why would a woman understand that a guy has a soft side or called a female or feminine side. Cause she has one also and she can relate as you can to her female side.
    But men just do not or do not want to know why a guy would want to do this.
    Then I told my wife I like panties she git some out for me to wear that night and she said to me " I'm A Girly Girl To ".
    And I feel the same way, so for many years were married and sharing clothes and jewelry and body lotion and many other things..
    The funny part us she never asked me why I like to dress up she just accepted this part of me and our life goes on.
    Now many years later, we are so close that is shows in our relationship and others like to see us and be with us because we are so close.
    Is it the secret or your just able to be your true self with confidence.
    I love my wonderful wife and she loves me, we cuddled lady night while I wore a long pink night gown and bra and pantie and she said when i started to wear a bra all the time, she like me better it allowed me to be the real me with out being judged.
    But men will never get it ever!!!!!!

  • What the h*** kinda 'normal man' seeks out sissy stories?

    Doth the lady protest too much me thinks?

Account Login
Is this post inapropriate?
Reason for reporting this post
Report this comment
Reason for reporting this comment
Delete this post?