
Start Your Cross Dressing Journey With Mistress Alina Sky
Cross Dressing For Beginners
What’s Up Buttercups?
So today I want to get into Cross Dressing Play, and Address your needs in this brief Cross Dressing For Beginners blog post.
If you are curious about cross dressing, and don’t know where to start, this is the blog entry for you!
WHAT EXACTLY IS CROSS DRESSING?
Cross Dressing has been around for centuries, and there are endless examples and insistence where cross dressing was utilized throughout history for different reasons.
So please You take a look at the illustrious history of cross dressing in this Wikipedia entry.
I WANT TO CROSS DRESS BUT HOW DO I START?
I’m glad you asked!
I’m delighted to tell you that spending years perfecting my Cross Dressing knowledge and play is very beneficial indeed.
So Cross Dressing For Beginners with me is where you want to start exploring this enticing kink, with me.
I understand you might feel a bit lost by your need to cross dress. However, please read on, and we can start your cross dressing journey together!
THE MANY STAGES OF CROSS DRESSING
In my opinion, cross dressing play can be very minimal, enough to get you into your naughty mood, or it can be extremely elaborate.
You can start small and evolve at your own pace.
However, we can start your Cross Dressing Play with just a few items, that are very easy and inexpensive to get!
So later on we can develop your wardrobe and changing needs, so you can reach your best cross dressing potential.
IF I WANT TO CROSS DRESS, DOES IT MEAN I’M GAY?
ABSOLUTELY NOT !
Whilst SOME cross dressers are bisexual or gay.
Hence, not all cross dressers are interested in a same sex experience when cross dressing.
Many Cross dressers use the process to sort of transform into a different persona for themselves!
And so drawing great arousal from wearing women’s panties, bra, stocking, and heels.
These cross dressers are very much attracted to women, so cross dressing is not all about your sexual orientation!
I DON’T WANT TO SPEND A LOT OF MONEY TO CROSS DRESS
And you don’t have to!
When I start one of my clients on his cross dressing journey, they can get very intimidated with the vast amount of women’s clothing and lingerie choices (Girl clothes are MUCH more fun, aren’t they? *Wink*).
So if it’s all too much to start with, I recommend those two items:
Get a cute thong in pink and try to find a matching lipstick to go with it ! Not very difficult is it? And TRUST ME you will feel divine, as matching your hot naughty thong to your lipstick!
Color coordination proves you’ve got your cross dressing game well in hand already!
LET’S BEGIN YOUR CROSS DRESSING JOURNEY TOGETHER!
Working with you is my pleasure!
Whether you are a novice cross dresser versus a full spectrum experienced cross dresser.
And so embarking on this adventure, we can discover all the endless fun we can have while you dress for me, and for my pleasure!
Together we can choose the most exquisite items, and even wear your naughty ladies thong RIGHT under you business suit at work, AND NO ONE knows how naughty you are but the both of us!
Trust that I can handle all your needs. As a Lifestyle Mistress I have perfected my knowledge of all matters kink, and that includes the illustrious fun and games of Cross Dressing!
Looking forward to some exciting Cross Dressing fun with you!

What a delightful post Ma’am
I’m very pleased you like it ! Chat soon xo
My first experience with this a girl made me. I was like a deer in headlights. I knew she had decided to do it and that she did not do this to most guys. The feeling of having to do what she wanted was over powering. I knew she was embarrassing me but could not stop her.
Interesting xo By all means feel free to call me and we can discuss this experience and where to go from there!
I’ve got to call you to be part of my ongoing permanent feminization training/therapy with the other ldw mistresses!!! I’ve been cross dressing since 1998, where I was waiting to do laundry and both machines were full and as I walked out I noticed bra in corner of my eye. I felt how soft it was and went to bathroom to try it on. There was lipstick in bathroom also and I tried it on my lips then I noticed how hard I got them went to my room and got off. That moment was where it all began. Now I’m wearing bras panties leggings dresses wigs makeup lipstick boots heels slips all the timd at home. I’ve even gone out dressed visiting my friend who’s now selling women’s clothes and wants me to buy them from her all the time which I’m going to. She even called me her sissy boy. The only negative is she’s married but told me not to worry about her husband or care what others think. I agreed with her. She even took pictures of me with her phone dressed up as a girl as I asked her to. With her doing this to me I’m not boyfriend material anymore as I’m fine with this and I’m going to get more into dressing in women’s clothes more.
She asked if I dressed up for therapeutic reasons and I told her I did. Do you think she knows I dress up to get hard and off? I think she does otherwise she wouldn’t have asked me and therapeutic reasons is g rated way of saying I do.
I’ve had hugs from her but I’d like to get harmless lipstick kisses on my cheeks from her but don’t want to ruin relationship with her or her marriage. She did say at concert she went with husband she had friend sit on her lap and kissed her. I want that to happen to me along with going shopping with her dressed up holding her purse and shopping bags as well her helping me pick out lipsticks and try them on my lips. It’s to difficult to resist and say no to her especially now she’s my stylist and calling me her sissy boy.
Thank you for your detailed insightful input ! This comment is almost as long as the blog itself ! Fantastic !
We decided that I’m going to be buying/wearing women’s clothes from her all the time as it’s what’s best and needed for me Ms Alina. It’s to difficult to resist and say no to especially when she called me her cabi boy. I’m not going to worry or care what others think anymore. Seeing how I look dressed up as a girl I really do look better this way then I do as a guy and I’m going to start dressing up more. I will call you and be part of my ongoing permanent feminization.
Oh I can’t wait to speak with you !
I’m sure we will have lot’s to chat about and a fantastic time doing so, Paulina !!!!
I have tried to go to the lingerie department in stores but get quite nervous. I know you can order on the internet but shopping in person feels more right or good. I also get a bit overwhelmed in the stores. Everything looks amazing and my head starts to literally spin. I feel jealous that women can just go in to places like that and stay calm and just shop. For me it is like landing on the moon. The other thing is salesladies/girls. Some can be rough with you. Once I had a lady who was gentle and it helped a lot. I don’t know that they “know” but I feel like they do. I wish I had a female guide who could take me and take the lead – keep me calm, show me what to do.
By all means, feel free to call and chat, I am an excellent guide !
Various people would feel the need to Cross dress to different levels. While some people would just wear Nail Polish and some discreet Lipstick, others may feel the need to go much further. Some people may feel the need to increase their level of Cross dressing. People can go at their own pace and go with what they feel comfortable with.
Yes that was my point!
Each experience is as individual as a fingerprint and ever evolving. Thank you for chiming in !