It’s Halloween time. Beware of Crossdressing

It’s Halloween season.  It’s a crossdresser’s paradise.  Many of you might be thinking about dressing up because your wife or friends won’t actually think less of you for doing so.  Some of you might even have wives or girlfriends who would have a lot of fun dressing you up in a women’s costume.

But beware.   You know that crossdressing is not just a simple fun thing in your life.  You know that it has a hold on you.  Resist the temptations.  It seems harmless but it’s not.  It’s a deep addiction in our lives and we must resist.  Other people might be dressing up as women in order to have a fun costume.  But for us that is never simply the case.  I am disturbed just seeing a man dress up as a woman for fun.  But it is far more disturbing when we do it because we get a sexual thrill out of it.  It is far more disturbing when we do it because we are obsessed with the clothing and think we NEED it.  It is far more disturbing when we do it because we would rather be a woman than the man that we are.

I know some of you don’t think crossdressing is wrong and you will ignore this post.  That’s fine.  But for those of you like me, be careful this Halloween.  Resist the temporary pleasure of crossdressing.  Sure you could have a night full of frills and thrills.  But if you are like me, you would regret it later.  It will only more deeply entrench you in your bondage to crossdressing.  Don’t deceive yourself.  Don’t do something you will regret.

Ask God to give you the strength to make it through this Halloween season, whether your temptation is to dress up, or to read stories about dressing up, or to fantasize about dressing up.  You don’t have to do anything you don’t want to do.  If you don’t want to give in, then don’t give in.  Ask God to give you strength and courage to fight the temptations.   Do something else on Halloween to distract yourself.  Do something else fun with friends.  Watch a scary movie.  Have a good meal.  Play a board game.  Have a wine tasting party.  Have a romantic time with your wife.   Do something else and resist crossdressing.  You’ll be glad that you did.


11 comments on “It’s Halloween time. Beware of Crossdressing

  1. Nicky says:

    Yea for Halloween, it’s liken for Trans to come out of the closet. It’s like their annual holiday for them.


  2. thorin25 says:

    Nicky, I don’t know if I would call it a holiday for transgendered people. But it certainly is a time of big temptation for people like me who used to be crossdressers and are trying to never do it again.


  3. Nicky says:

    For trans people Halloween seems like their version of national coming out of the closet day.


  4. ikthys says:

    I could not believe that my wife, of all people, suggested to me that I should dress as a woman for fun this year! I was floored, and I turned her down. She wasn’t even thinking about my struggle at all, not like, “hey you deserve a little outlet for all your efforts”, etc. No, she was just thinking it’d be funny. For some reason, the “halloween logic” is so deeply entrenched in people’s minds that they can even overlook the humongous red flags in front of their faces, like a husband who would totally compromise his own conscience and health in such a situation. I truly could not believe it and felt bad having to say that I am not strong enough to handle that, but I am very proud of myself for doing so, because I know I would have been seriously set back in my struggle for a while if I followed up on her offer. Thanks for being the clarion voice in a hard time.


  5. thorin25 says:

    Ikthys, no offense to your wife, but honestly I am disappointed in her for not realizing what a horrible thing that would be to suggest, even after you’ve talked to her about your struggle. At times I have been frustrated with my wife for not being more supportive. Even after explaining to her at times why I won’t wear an apron or why I don’t like it if she wears an article of my clothing, she still has trouble understanding and even has gotten frustrated with me. It’s like crossdressing is so odd, even after explaining it to people with tears and long talks, there is still much that they don’t get. One thing I do appreciate is that she doesn’t find crossdressing funny, ever, in any context. She says she never did, but I would guess she doesn’t find it funny also because she knows about my problem. I think both of us just need to be strong and be patient with our wives even when they lack understanding. It is an odd problem and one that is hard to understand without experiencing it and it’s something women don’t even want to think about to try to understand because it is such a disturbing image.

    That aside, well done for staying strong! What you described would be about the strongest temptation I could face. My most pleasurable crossdressing dreams and crossdressing fantasies are about exactly what you described. And you had the reality. But I do wonder if crossdressing with your wife, or with my wife, would be much more awkward and not pleasurable in reality than the fantasy of it would be.


  6. Ralph says:

    Believe it or not, I completely agree! If crossdressing is a sexual addiction for you, dressing on Halloween is like a recovering alcoholic going to a bar on St. Patrick’s Day. Just as those who don’t have a problem with addiction and can exercise self-control when having a drink with friends aren’t in danger, those who don’t have a deeper psychological bond with crossdressing really can just do it for fun and forget about it. I sure don’t dare give in to that temptation; for all my comfort in dressing at home I already know what giving in on Halloween does to me.

    When I was 20-something, I did just that — used Halloween as an excuse to do in public what I had previously kept private. I even had my mother help make a costume for me… I think I was Dorothy from the Wizard of Oz. She thought it was hilarious and took me to her (Methodist) church fall festival and everybody laughed and got pictures of it. I thrived on the positive attention and over the next couple of Halloweens I very nearly made it a public part of my life because it was so great to be accepted by friends and family while dressed as I wished.

    I didn’t actually go all the way. I kept dropping hints here and there but some remaining shred of self-preservation kept me from actually telling them I liked to dress up all the time. I’m so glad I didn’t; I can only think how it would have devastated my family and reduced my chances of ever getting married and settling down.

    So yeah, take it from one who’s been down that road — don’t go there, because all the social approval and positive reinforcement you get will give you the false belief that it’s just as acceptable the other 364 days a year.


  7. Vivienne says:

    Interesting points, as always. I’ve never lived in a country where Hallowe’en was that big a deal. I haven’t dressed up at Hallowe’en since I was about ten years old. I have never considered Hallowe’en a carte blanche excuse to get glammed up and go out in public dressed. So I never have: not done it; not mentioned it; not even really thought about it (certainly never been invited to do it!). Somehow, the actual prospect seems more than a little distasteful.
    I echo Thorin’s points to you, Ikthys. Your wife probably hadn’t intended to be hurtful, but I can really see how she hit a very tender spot with her comment. Good on you for holding back; I can imagine how much effort that cost you.
    I agree with just about everybody that crossdressing isn’t funny. Not Tootsie, not Mrs Doubtfire, not Sorority Girls, not The Birdcage. It just isn’t funny. When I see bad crossdressers I am nauseated. When I see good crossdressers (attractive or passable) I am envious, but never amused. There’s really no way to win. Yet it seems to exert some sort of permanent fascination on the human psyche; if there were no demand for this sort of “entertainment”, there would be no supply. But that’s another topic.


  8. Ralph says:

    (Ralph makes a note never to invite himself over to Vivienne’s house whilst crossdressed) Seriously, Vivienne, you have probably seen links to my blog but I urge you to avoid the photos section. You will need eye bleach and probably one of those memory wipe things from Men In Black to recover. I am a very, very bad crossdresser… I wear a satin gown like some guys wear their old high school football jersey — wrinkled, doesn’t fit right, looks horrible on me, but it’s the most comfortable thing I own so I wear it all the time. If I bother to wash it at all it gets wadded up on the floor with my jeans and t-shirts and week-old socks and kicked around until I remember to throw it in the washer and dryer (my people have no words for the concept of “dry clean only”, so I ignore that part of the label).

    But yeah, that’s next in line among the many reasons I don’t ever let anyone but my wife see me dressed. I don’t make the effort to shave or comb my hair when I’m out in t-shirt and jeans, why would that change because I’m wearing a dress or a skirt instead? So for the sake of decency, I spare the neighbors the sight of a gorilla lumbering around in taffeta.


  9. Vivienne says:

    Hi Ralph! Your post made me laugh out loud. Feel free to drop by any time you are in the neighbourhood; although I suspect our neighbourhoods are quite far apart!

    I’ve read quite a lot of your blog, and I’ve even seen quite a lot of your pictures! I can’t quite figure you out at all. I have a few precious crossdressing items, which are carefully (you might say lovingly) folded away when not in use. My jewellery and cosmetics are in neat little boxes decorated with little pink high heels. When I dress, I try to make myself look as feminine as possible: initial efforts were basically grotesque, although some professional makeovers have been wonderful (as you know from some of my blog posts). All human activity improves with practice, and my fem appearance has been no different. (When I used the phrase “bad crossdresser” I was referring to men who are trying to look like women, but for one reason or another, overcook it and end up looking dreadful; you, on the other hand, make no pretence to be a woman whatsoever, if I am any judge. So I wasn’t including you in that category).

    I can appreciate that your appearance doesn’t seem to matter to you, which is fine, but why then did you post the pictures at all? One of the things which struck me (and I posted about this) was that we seemed to have so little in common when it came to our dressing, yet so much in common when it came to our outlook and our moral point of view. I have to say, it was this latter thing which impressed me the most about you. You really can’t judge a book by its cover!

    Best wishes,



  10. thorin25 says:

    Hi Vivienne, Ralph was going to post a comment about his specific clothing choices and pictures, but I told him to write to you separately about that elsewhere. I appreciate you both, but I want to keep somewhat on topic, and don’t want to derail other readers who might get wrapped up in fantasies and temptations by reading too much about clothing specifics and so on. So please don’t take offense. Thank you for understanding!


  11. Vivienne says:

    No worries Thorin. I quite understand; and apologies for derailiing this thread.



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