Jessie trying to find herself....

[Wearpantiesbutwantmore]

Jessie, I'm new here, but not new to dressing, so I'll add a few thoughts of mine. Let me tell you a bit about my experiences, as I think it is similar to yours.
 For years and years I was happy to dress up in lingerie from time to time, though, even say 20 yrs ago I'd had the thoughts, and urge to "Go all the way", fully dressed, makeup wig, etc. It was easy to laugh it off, and just have fun around the house in my underwear.
Till 2018 that was, when I was thinking much more about dressing up, and getting some real clothes. Then while looking for some items for my Lady for Christmas I found a website (don't know which one) that had a section for "Crossdressing supplies". Oh My! What an eye opener! So I bought a few things, for me, and her!
Last year was when I went outside for the first time, fully dressed, and it was soooo addictive, and exciting. Scary too! Nothing bad happened, a few noticed from my voice, but mostly no one batted an eye at me. CIS women come in all shapes and sizes, some are very beautiful, others, well, not so much, but they are women! Most of us, with some practice can learn to get into that spectrum.
Now I go out shopping en femme all the time. Well till this lockdwn stuff here, but it will pass sometime. I love going out dressed, and it gives me a totally different feeling than sexual. I'm relaxed and happy for a couple of days after. My situation doesn't let me dress up and go out all that often, as I almost think I'd be dressed most of the time!
The previous poster gave some good thoughts, and my experience is very similar.
The other thing that I've gets addictive, a bit anyway, is showing off some. As a regular looking guy, I don't get second glances, and no one ever wants to see more!
As a woman, I get looks when I have short skirts on, nice (Fake) tits, and have posted some  stuff online, not here though (yet), and have got a few "fans" shall I say. Not that I go too far with on line friends, but that's just me. Tempting though!
So, with your new friend, just be careful, what is he doing with the pictures you share? Saving them, sharing them? Does it matter to you? You should think about it, if you haven't yet. Sorry to be a bit of a downer, Jessie!
You sound like a really nice person, though I don't know you, but I'd hate things to get out of hand and bite you back.
Lots of caution should you decide to meet up, public places, more than once, I'd think. I understand its fun to have a fling, but be careful!
Amy

Amy 

Thank you so much for taking the time to give me your insight... it means alot to me... I just feel stuck in the same monotonous situation... I dress when my girl is not around... I have all kinds of things I want to wear including breasts in my cart from JCs...lol. I even got buzzed up and jumped into bed with stockings and panties on with her sleeping I guess hopefully getting caught. .lol..  I got up b4 her and changed but I'm starting to get more and more bold. . Latly wearing panties and stockings under my work clothes... I long for a regular that would dress me up and have their way with me... but I guess sissy porn and hypnosis will have to do for now until I find a more permanent solution.. thank you for listening 


Jessie