Miss Teresa of Strapped in Silk has an advice section on her web site called Ask Teresa.  Recently, a sad and lonely cross-dresser wrote to her: E : I give up Teresa. I’ve been through several relationships, and 2 marriages, and no longer think I can find a woman to accept me for who I am. I’m a cross dresser and I can’t deny it. Its part of who I am. I am resigned to living alone for the rest of my life. What can I do?

Miss Teresa wrote a thoughtful and encouraging response and used ♀ as living proof that such women really do exist. ♀ & I were both flattered to know that Teresa thinks so highly of us. I was even tempted to forward it to my mother (son, if nothing else you can always be a bad example), but thought better of it. ♀ suggested I send Teresa the post that describes how I broached the whole issue with her. I spent a lot of time searching through the archives, but was unable to find the one specific post. I’m guessing that I wrote about it in little bits and pieces.

I’ve been thinking about how we got from there to here and what advice I might give to someone in a similar situation. So if you can stand it, here’s a brief pre-♀ recap:

I’ve always been attracted to ‘girly’ things. When I was very young I would play dress up with my mothers wigs and shoes. I can remember when we had guests over and their coats were tossed on my parents bed, I would rummage through purses and smell the perfume on the coats. I have no recollection of every getting busted, just an insatiable curiosity of all thing feminine.

After puberty hit,  I knew of and had tried on every piece of lingerie my mother owned. Even then, I knew I didn’t want to be a girl, I just loved how it looked and felt. My uncle lived in our basement and had a large collection of Playboy and Penthouse. I can remember being as fascinated by the lingerie they wore as I was by the beautiful women. In fact that’s how I  learned how many of the pieces were supposed to be worn.

Adolescence was tough. Girls only wanted to be my friend. I wasn’t into sports and all my male friends were basically guys I got loaded with. Most people assumed I was gay. I didn’t think I was gay, but men hit on me constantly and girls weren’t intrested and I did like ‘girly’ things and with no internet…it was confusing. Right up into my early 20′s when I was starting to have some success with girls, men were still hitting on me. And in the strangest places. I can’t tell you the number of times I was propositioned in strip clubs. That still baffles me…I’m watching pretty girls take their clothes off, why would anyone think I was interested in men?

So during my 20′s and 30′s I would never buy lingerie, I would steal it from the women I was dating (mostly panties and pantyhose) use it for masturbation fodder for a while. Eventually, be over come with guilt and disgust and throw it out. I lived with the mother of my son for 10 years. She had no use for sexy lingerie. I’d buy her things. She’d wear them once (can I take this off now?) and I’d ’use’ them after that. I bet lots of this sounds familiar.

I met ♀ online  8 years ago. We dated for about 4 months before I moved in with her and her 13 yr old son. It wasn’t long after that when we went lingerie shopping together for the first time. I encouraged her to buy sexier bras and panties than what she had ever owned and within a day or two, I’d ‘used’ her panties and felt guilty as hell about it. Same old, same old, right?

But, it was different this time. How?  Well, we had a connection that I had never had with anyone else before. I was head-over-heels in love and I didn’t want to have any secrets from her. Also, her first husband was gay and she didn’t find out until after the baby was born. I knew that trust was a huge issue with her and if she accidentally found out about my little fetish…she’s told me she would have kicked my sorry ass to the curb.

Telling her was one of the hardest things I’ve ever done, but when I look back on it now I really didn’t tell her all that much. I mean I told her everything I’ve just told you, but compared to what it has evolved into it was hardly anything. Her first reaction was, ‘Oh crap, I’ve turned another one gay.’ I assured her that I wasn’t. She was skeptical. I asked her if her ex-husband ever wanted to have sex with her 2 or 3 times a day, like I did. No, not so much. She asked why I didn’t tell her sooner. I told her I really hadn’t thought about it until we went lingerie shopping. I also said (and really believed at the time) that it was just something I liked to have sometimes when I jerked off. She asked if I had any of my ex’s lingerie. I did. She asked me to throw it out. I did. 

Once I’d actually admitted it to her and she started asking questions it became quite apparent that I wanted more.  I was constantly asking to wear her panties in and out of the house and eventually we started buying them just for me. We started looking at cross-dresser web sites, joined message boards, ordered some books, but it just didn’t feel right. The whole focus of cross-dressers seemed to be passing as female. They had female names and (imagined or real) entirely separate lives as women.  We bought some outer clothes for me and a wig and ♀ did my makeup, but I didn’t want to be female.

It wasn’t until I stumbled upon ‘sissy’ that the light went on. I ran upstairs and woke ♀ up. I was so excited. The more I read, the more obvious it was…the cross-dressing was just part of being feminized…no that’s derogatory towards the Goddess…let’s say emasculated. The need to be submissive to a dominate woman, to serve her, to be her bitch.

As we started exploring ‘sissy’ I could see countless examples of freakishly bad decisions made to satisfy my need to be dominated. Patterns repeated over and over that I was unable to explain or stop. I know this will sound sexist, but I think a submissive male who doesn’t know himself is more at risk of being used and hurt and taken advantage of then a submissive female. All those bad things can and do happen to women, but being a submissive female is socially acceptable. Both the man and the woman know how it’s supposed to work and most decent guys don’t take advantage of that. But when it’s the other way around there’s no frame of reference and it can lead to bad bad things.

So, if the information highway had blasted through my life 25 years sooner then it did, I would have known that ‘hetero’ doesn’t need to be ‘alpha’ and life might not have been any easier, but I certainly would have made different choices. ♀ is a firm believer in ‘everything happens for a reason’. To me, that smacks of not having a choice or some kind of master plans beyond our control.  I don’t believe that, but I will admit that if I’d made different choices ♀ & I probably would have never met.

Now back to our friend, the sad and lonely cross-dresser. What advice can I give him? Well, because I didn’t know who or what I was when I first met ♀,  I was able to be completely honest with her. It turned out that ‘sometimes I like to jerk off in pretty panties’  was just the tip of the iceburg, but it was something we’ve explored together over the past 8 years. What it means for me to be a sissy and ♀ to be a Goddess continues to evolve and I doubt that evolution will ever stop.

But what if I was in our friends situation now? Sitting in front of the computer night after night. Listening to Teresa’s stories, following the links from blog to blog, to message boards to the lingerie sites and it all gets clearer and who what when where how and why becomes more and more focused and I want to be honest, but the few women I’ve dated freak out when I tell them even a little bit of who I am…

Gawd, sad and lonely cross-dresser guy… Yes, ♀ is a Goddess and amazing and wonderful and I tell her every day how lucky I am and how much I love her, but if I knew then what I know now and I told her all about it…I really don’t know what she would have done.

Cheers,

sss