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Becoming Cassandra Moonlight

13 Posts
7 Users
20 Reactions
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Posts: 74
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Topic starter
(@Anonymous 94586)
Trusted Member
Joined: 1 year ago

Hello All. I first want to thank everyone who has welcomed me so far. You are living up to the billing of being a supportive community. With this post I am killing two birds with one stone. First, to give some background on this newcomer to your group, but also to help me think about how I got to the point of joining you as Cassie Moonlight.

Present day -- I am AARP age (but not retired) and living in Southern California. I have experienced about 20 years of closeted crossdressing over my lifetime, comprised of 3-4 distinct "eras." The first was, like many of you, at a fairly early age. I vividly remember playing with my mother's bras, panties, and pantyhose as a pre-adolescent. As I recall, there was a period where she actually supported my experimentation, but as I got closer to middle school age I was told it was time to "grow out of it." So I stopped.

I did very little crossdressing in my high school and college years, but I do remember dressing up as a cheerleader one Halloween and loving being made up. I also remember that in my last year in college, when I was dating someone about 6 years older than me (and having the best sex I've ever had in my life), there were at least a few instances where I wore her lingerie for "role play".

One thing I did notice about dating just after college and before getting married is that I was super turned on seeing my lover in lingerie and going to buy it with them. Increasingly I got curious about how I'd might look wearing it. A few years into my marriage, after getting into the best shape of my life, I started secretly trying on my wife's lingerie (including what she wore on our wedding night), panties, bras, stockings, leotards, and eventually swimsuits and dresses. It was intoxicating and frightening at the same time. I eventually got the courage to buy a few items of my own, including a black lace bodystocking I absolutely adored. I eventually got the courage to share this with my wife, explaining my history and showing her the outfits and me in them. The response was not terrible but not great. She basically told me that I could do it in secret, but she really didn't want to engage. So, I looked for other outlets, including trying to connect with other crossdressers. However, after a while it seemed like an impossible juggling act and I just gave up / got busy with other parts of my life.

While there were occasional flirtations with crossdressing, particularly when my wife was away on travel, it was basically not on my mind much for a decade. Then about four months ago, when my wife was again out of town, something (I don't know what) hit me like a bolt of lightening and I went on an intense dressing spree. It felt wonderful and so stimulating and exciting. However, there was guilt in wearing my wife's things, so I decided I needed to have my own that I could "stash" and pull out when I had the opportunity. First I bought some panties, then a lacy nightie, then a couple of silk kimonos, then thigh highs, and most recently some strappy shoes. It has been simultaneously exciting and scary shopping and doing it as secretly as possible. 

So now I think is this just another era/phase that will die down soon, or am I in denial of something bigger. I don't really think of myself as someone who would fully transition, for a variety of reasons, but what is the right path for me? That's a big reason I'm here, to learn from your experiences and insights. Thanks for letting me share. Hugs, Cassie

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12 Replies
6 Replies
(@dovemtn2016)
Joined: 1 year ago

Honorable Member     Tucson, Arizona, United States of America
Posts: 307

@cassiesccd 

Thank you for sharing your story, Cassie. I know a lot of thought went into it. Quite amazing, actually.

With affection,

Christine

 

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Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@dovemtn2016 Thanks Christine. Felt good to jot it down.

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Lady
(@jillannquinn)
Joined: 4 years ago

Noble Member     Reno, Nevada, United States of America
Posts: 627

@cassiesccd Welcome Cassie, you’re very welcome indeed. All of us here can share our stories m, and those stories may help you understand yourself better and where you’re willing or unwilling to go with your cross dressing. But that’s just it, YOU have to figure out for yourself just who Cassandra Moonlight is and what that means to you. No one else has a right to define and characterize her for you.

I’ve been Jill Quinn for two and a half years now and I’m still figuring things out, but I have a much better and stronger understanding of who Jill and I are together. And for me, there is no more room in my life to shove Jill down some dark hole in my mind and deny her and the feelings she brings to me. I’m done with feeling ashamed and guilty and I’ve moved on to a healthier and happier attitude of acceptance of my feminine half. For me, dressing up makes me feel incredibly happy, safe, and relaxed. Sometimes I even feel a little sexy!

I wish you the best of luck and happiness on your own journey of self discovery. Feel free to ask any questions you want.

Hugs, Jill

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Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@jillannquinn Hi Jill, thanks for your message and sharing your thoughts. Much appreciated. Hugs, Cassie

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Ambassador
(@jacquelinelarkspur)
Joined: 1 year ago

Famed Member     Gateshead, Tyne and Wear, United Kingdom
Posts: 1497

@cassiesccd 

Thank you for sharing your experiences, Cassie. Your "bolt of lightning" comment really resonated with me, as I'm sure it will have done for many of us. The feeling is quite a powerful one when it strikes. The "juggling act" is all too familiar as well, and your description of it is perfect.

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Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@jacquelinelarkspur Thanks Jaqueline. It helps to hear I am not alone in these feelings. When you are closeted and very secretive as I am with friends and family, it's hard to know whether anyone "gets" you. Hugs, Cassie

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Posts: 2098
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Cassie -

Thank you for sharing your story. We each have our own journey and as such I think you need to se where yours takes you. This is a good place to get advice and support on your journey but as to how you feel that is very personal. Think of the Robert Frost poem " two roads diverged in the woods and I took the one less traveled by and that has made all the difference". There is much to consider and only you know the answers to the questions. Be sure to check out the articles, forums and chat to see what others have experienced.

As for my story - I intermittently dressed throughout my life. It has only been in the last few years that i have started dressing on a regular basis. My wife is aware and it has taken her a long time to accept my dressing. She has gotten to the point where she helps me with shopping, selecting outfits, assisting with make up, spending days at home with me dresses (not very many but enough for now), going for mani-pedi's together and other things. It took me a long time to get where I am and don't know where I'm going but I am enjoying the journey.

Best of luck

XOXO
Suzanne

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1 Reply
Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@cdsue Hi Suzanne, Thanks for your message and sharing your experience and thoughts. Much appreciated and Hugs, Cassie

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Posts: 3404
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

Yes we all have our own story and want to understand where we are and how to progress ourselves. You have come into a very friendly area where you can look at others experiences and ask questions that will no doubt help you. Primarily it is a connection to a wonderful community and the first step to understanding yourself better and help you on a path to fulfill your aims.

You are most welcome here.

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1 Reply
Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@ab123 Hi Angela, Thank You for the warm welcome. Hugs, Cassie

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Posts: 209
Lady
(@lillie)
Reputable Member     South Carolina, United States of America
Joined: 4 years ago

Cassandra, Welcome, this is a very warm site. Girls are great and very entertaining.

 

Lynne

 

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1 Reply
Guest
(@Anonymous 94586)
Joined: 1 year ago

Trusted Member
Posts: 74

@lillie Thanks for the welcome an wig tip. Hugs, Cassie

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