The Pros & Cons of Cross-Dressing

A Starter For 15 And Personal View from Kathy Martin

There is so much angst, self-doubt and guilt that I’ve been through on my travels through the maze of Transvestia and so I thought it would be fun to ponder on both sides of the conundrum as I’ve moved from Self-Awareness, through Acceptance and now into Celebration!

So, in no particular order is my “Starter for 15”. Consider it ‘Work In Progress’ and please feel free to comment, or add further to the list. It is by no means the definitive article as we’re all unique with different experiences, thoughts and feelings in our Cross-Dressing, Transvestite, Trans-Gender journey!

1: Pro: Discussions with Real Girls (RG’s) that you would NEVER have, or be allowed to have, when dressed in male mode!

Con: Why can’t we have these sort of deep conversations with our male mates without being seen as ‘soft’.

2: Pro: Time in my female role helps to alleviate the stress associated with ‘being a MAN’ – all that GRRR Alpha Male macho ‘stuff’. Also being able to acknowledge that we’ll never be real women and so appreciating the stress of hormones/ menstruation that our partners go through.

Con: Having to sit tight-lipped with your mates when you’re bored stiff with conversations about cars and traffic directions, the latest gadget for the computer, and in some cases sport, when you’d rather be asking their wives where they bought their shoes and handbag!

3: Pro: The delight that comes when you have found the right image, style and persona that captures the REAL you (this is not meant to be sycophantic but ‘Thanks’ Femesque)!

Con: It can cost a fortune to kit out a whole new wardrobe to suit the new image – worth it tho’!

4: Pro: Shoes!

Con: Not enough wardrobe space!

5: Pro: Taking high heels off at the end of a long night out has to be one of the best feelings in the world that mere mortals never experience! NB, Top Tip: only wear flatties on day-long shopping trips because heels are a dead give-away during the daytime! And cobble stones are finding a way back in the town planner’s armoury, which can lead to very embarrassing experiences when you’re laden with shopping bags!

Con: Buying shoes and then realising they’re too narrow for your feet, but only when you’ve been wearing them for a while. NB, Top Tip: shoe wideners do help with time and can be a good investment!

6: Pro: Being relaxed in your own mind and body.

Con: Can’t think of a negative to this one!

7: Pro: The ability, and opportunity to be more understanding, sensitive, kind, gentle and empathic than the average Joe.

Con: Can’t think of a negative to this one either!

8: Pro: The transformation from ‘him’ to ‘her’ never ceases to amaze me, especially when it all comes together. NB This is also where the chance to visit a salon like Femesque is invaluable, cocooned in a totally safe, relaxed environment is a major benefit.

Con: The time it takes to transform! Having said that, experimenting with new ideas and looks is a large part of the enjoyment for me.

9: Pro: Shopping without inhibitions. NB Top Tip: remember that shops are there to ‘sell’ things and your money is as good as anyone else’s, and it is not illegal for men to buy ladies’ clothes, shoes, handbags, make-up, lingerie, hosiery, or perfume. The conversations with shop-keepers can also be enlightening and VERY enjoyable when they know you’re buying for yourself! If they don’t want your money, go elsewhere with no recriminations!

Con: Spending too much money on a new wardrobe (see also 4 above). NB, Top Tip: I buy probably 90% of my stuff now in Charity Shops and it satisfies my male Hunter-Gatherer need and my girlie ‘bargain hunting’ need. I’m also from Yorkshire so I know what I’m talking about!

10: Pro: Appreciating the power of a cleavage from the owner’s perspective. NB: it’s not only men that stare at boobs!

Con: Having to convince people that you haven’t had a boob-job, although I’ve had tremendous fun with these sorts of conversations, so I’m not sure if this is a negative really?! NB, Top Tip: small blazer buttons act as fantastic nipples when placed strategically inside soft T-shirt style bras! You do have to keep checking their placement tho’ as they move around a bit, so try not to make it too obvious when you adjust your nipples – take it from one who knows! And don’t use massive buttons that look like ‘Chapel Hat Pegs’ – it makes it look like you’re constantly cold!  

11: Pro: The feeling of elation when you’ve been complimented on how you look and present yourself is hard to beat a) from other Cross-Dressers, but more importantly b) from real girls! The ultimate goal for me is to ‘pass’ in normal society without being ‘read’ and being able to blend in unnoticed. I don’t fool myself that I can do this ALL the time, but my ‘strike rate’ is so much better nowadays, after a long time dressing, and even more so with the new image – ‘Thanks again’ Lynne, most sincerely!

Con: The assumption that you’re homosexual (most cross-dressers are not) and that “you must be dressing like that to pick up a bloke?!” That said, again, I’m happy to educate anyone about my journey if they’re happy to come to me with an open mind.

12: Pro: The amazing people I’ve met on my journey and hearing all their unbelievably funny stories, and the help I’ve had in coming to terms with myself from these people.

Con: No negative here at all!

13: Pro: The adventures I’ve had and personal insights I’ve gained that I would never have had if I hadn’t cross-dressed.

Con: The initial feelings of guilt, fear, self-doubt and heartache that I’ve had to go through to get where I am today – all good character-building stuff tho’ – GRRRRR!!

14: Pro: Knowing that I have made life-long friendships along the way and have my REAL FRIENDS’ support in whatever I do.

Con: Losing a few friends along the way, tho’ not many, but realising that they weren’t true friends after all!

15: Pro: Helping to keep my mind active as I’m constantly on the alert for new styles and experiences ‘en femme’. I love the quote “Do something every day that scares you.”

Con: Can’t think of a negative to this one either.

Well, there you have it, my first post on the Femesque site. Hope you found it enjoyable and enlightening and I’d be delighted to hear your thoughts and additions – maybe together we could build up a massive list over time?! If everyone who reads this can add one comment, we’ll be cooking, but please keep it clean!!

Big Hugs and Best Wishes to all

 Kathy

 xx


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