Island of crossdressing

2015 it is. Valentine’s day.

I am thinking of times during college. 2011. I am stuck in past. Momentarily, though. It is 2:05 AM. I am alone in my bedroom. It’s quite cold. I can hear the sound of distant speeding vehicles on highway. My brother is watching a popular film on TV. Dogs bark occasionally. I tried chatting with a pretty girl and it seems she has fallen asleep now. Not her fault. She had a long, tiring day at work. She needs rest. On the other hand, my mind is thinking on so many different levels.

I miss 2011 sometimes. Life has changed. I haven’t cross dressed since 2013. It feels as if I am different person now. I no longer get the craving of silky long smooth hair wigs, a feeling of bra strap on my back, the softness of feminine under garments, the delicate clothes, the powerful and overwhelming high heels, the smell of lipstick and the act of painting my lips red. I am no longer there – in the phase.

Life is strange.

I had young skin. Boyish features. I was fit.

I am old now. Over weight. I have masculine features that are hard to hide. Some of hair is grey. My facial skin is ruined because of shaving accidents. I am just 27 now and yet, I feel old.

I turn on my laptop sometimes. Go to that folder with computer-like name. It has my pictures. Not many have seen them. I feel as if it is my treasure. It means so much to me. I click and open the folder. So many pictures. I was young and stupid. But, I think I was beautiful. I did what I can with what I had. I smile and find it funny that no one ever thought that there was this side to me.

Once when I was Rebecca Watson…

Gradual Coming Out Journey

Hello once again!

I hope you all are doing well. I have been away, not because I was busy but because I am so lazy.

I was doing a mental review of what I had done last year pertaining to my CD life. And I realised that I had slowly came out to many people, unknowingly. This was not planned. In year 2012, I came out to 2 people. In 2013, I came out and told about my crossdressing habit to 4 people. I know the number is not that big but I feel it is a progress. I also realised that most of the people I have told were females. It seems like I am more comfortable coming out to women than men. Do you also share same feelings?

I have not yet told to my family members and even some of my close male friends. Though, I have not been dressing since June 2013, partly because I have gotten rid of my girlie stuff, I have been regularly in touch with “feminine side” by visiting different blogs, watching YouTube videos and so on.

I have no idea what 2014 hold for me. All I want to do this year is to lose a LOT of weight and get back in shape. I also want to take care of my skin. I hope to “transform” myself into a skinny, muscular guy so that I can also fit into small girlie outfits. ;-)

I guess I went from coming out analysis to weight gain issues. Haha! So sorry for that. I hope I write more this year.

Thanks for reading.

Guilt, Desperation and Sympathy

Part I: Guilt:

I was just having a conversation with my female friend. She’s a very bubbly type of person, pretty, have brown eyes, long dark hair and very girlie types. She does not really have an idea about my cross-dressing desires. For her, just like most of the people in my life, I’m a masculine, non-emotional guy.

We both were talking about the book “Fifty Shades of Grey”. I downloaded it today because we had a brief conversation on the same book yesterday as well and my curiosity woken up again and I decided to finally download it on my iPad and read it eventually. Again, in our phone conversation, we ended up talking about the book. I told her why I plan to read this book – which was to understand what attracts women, what they want from guys and how they like to be treated. I’m fully aware that I was generalizing all the women around the world and, in fact, many women don’t like to indulge in BDSM lifestyle. She too pointed out that to me.

This topic led me to finally ask her what do women in general discuss about guys and their personal sex lives. I had known answer but I wanted to find one more assurance from my female friend. As expected, she said that most women discuss about most parts of their lives with each other. Of course, here she meant that the conversations like these only take place between two trusting and close female friends. I expressed my disappointment because I feel that’s unfair to share every tiny detail of one’s sex life with another person. Guys don’t do that, women do. You know why I felt that way. As a cross-dresser, I sometimes feel guilty. The guy side of me wants kill the girl within me. He wishes she never existed. Another thing, which I haven’t told to anyone yet except three close friends, is that I have never been physically intimate with a woman. Once when I did, I was not able to perform. She has no idea about this – about my sex life and cross-dressing. Yes, I’m a virgin. I do like women. I’m almost 26 now. It sucks. My insecurities about myself, my sexuality and my inability to perform while having sex burst in one second. To add to my disappointment, she also told me how women sometimes do make fun of guys who couldn’t perform or who are treated as guys-to-be-avoided.

This, by now, has crushed my already wounded self-esteem. I imagined how a woman might tell her friends about me, how sissy I am (because most women are not into cross-dressers and assume them to be gay) and how I couldn’t perform as a man – may be because I am a girl deep inside – is what they might conclude among themselves. I’m so dead.

Part II: Desperation

Trust me, every time I see a pretty woman, I feel desperate to show her my feminine side. I want to sit with her in a pink room, get slightly drunk, and whisper in her ears that I love to dress up like a girl and then I want to see her reaction. Reactions get me. The reason sometimes I dress up like a girl and broadcast myself on webcam to strangers on internet is to see their reactions. I love that part for some reason. Also when I see a pretty woman, I get confused whether I should have sex with her or turn myself into pretty looking woman like her. Getting back to the “desperation” point, I find myself always wanting to tell every pretty female friend I have about my cross-dressing habit. I’m not sure why.

Part III: Sympathy

Yes, the second word that comes to my mind is – loser. I crave for some sort of sympathy because I’m poor, little guy who couldn’t find a woman because he likes to cross-dress. Not that I like this part of me but maybe it’s the girl inside me who wants to be too sensitive, make fuss about her problems and want someone to cuddle her up and tell her “it’s going to be alright, baby. I’m here for you”, and then protect her like she is one weak (and very pretty) girl in a problem!

Phew! I’m done with the crying and complaining. Now I’ll get back to my guy life. Thanks for reading.

Straight Cross-dressers & Women – Part II

A few months ago, I asked my friend what she thinks of “men who like to dress-up like girls”. Her response was – “I don’t have any to do or say about such people”.  It is strange how a piece of cloth and makeup, or an accessory wore by a man can suddenly change people’s perception about him.

Another incident that happened to me last week – I was with my friends, having dinner. Sometimes, my lips tend to appear pink and that gives it a feminine look; or that is what my friends say. In middle of our conversation, one of my female friend giggled and said – “you will feel bad when I tell you this… but your lips looks like you’ve applied lip gloss”. First thing, I was flattered. Second, I know this isn’t an insult. But then, can you sense the underlying, subtle thoughts? Why the giggling? Why she thought I should feel bad about it? Why there isn’t a sincere, appreciative gesture? I feel it is, again, a form of being perceived as “inferior” just because I somehow displayed a feminine aspect of my physical self. Or may be I’m just over-thinking!

I am saddened by the fact that I never met a girl in my life that isn’t fond of cross-dressers and still encourages and takes it positively, rather than seeing it being inferior, laughable, funny or demeaning. Of course, girls who like cross-dressers do not count because they, obviously, don’t see this as disrespectful or funny. What I would really like to see is a woman or a girl who isn’t into cross-dressing men and still sees it positively and considers it normal.

Straight Cross-dressers & Women – Part I

One of the thoughts that always bother a straight cross-dresser is finding a woman who not accepts him but also actively indulges in him cross-dressing lifestyle. I have always had fear that I will be perceived differently by women if I tell them I’m a cross-dresser. This also applies to men who know me. [Watch this video: Scene from film ‘Ed Wood’, I completely relate to Johnny Depp’s character] I’m moderately muscular, have interests in gadgets, and keep myself busy reading and researching on topics which appeal to me. You wouldn’t see feminine or ‘pansy’ quality if you ever meet me. Deep down I have this secret that only few of my female friends know. Why is it difficult to find women who are into cross-dressers?

On the other hand, women are allowed are wear jeans and shirts. If a woman works in office, or even works as a soldier, she is congratulated and looked highly upon. While taking on female behavior by any man is considered humiliating, degrading and, often, these men are labelled being gay or faggot, or a sissy.

So the whole point is that – society celebrates anything that ‘becomes masculine’ and rejects anything that ‘becomes feminine’. I came across his awesome video (Click here to watch) blog by Laci Green that you guys should check it out.

So the divine question is – How straight cross-dressers will ever find their dream girlfriend or female companion? Sure there are some extended thoughts on the same topic which I will be sharing in new blog posts. But I will like to know the answers from you. Please do share your thoughts in the comments section below.

Rebecca Watson

Who am I?

Hello readers,

I have no idea how this blog is going to turn out. I feel this blog will be my personal space. A place where I will express myself fearlessly.

So who am I?

I was born in India, in a city very close to Mumbai. I am 25 years old now, and I’m an occasional cross-dresser!

I have great, loving parents. They have always been my inspiration. I wouldn’t use words like “blessed” or “fortunate” because I am a non-believer and also don’t have any faith in luck or destiny. I believe in free will and leading your own life, rather than just living the way it shows up. Having said this, I am completely okay with other belief systems.

I first cross-dressed when I was 12 years old. I put on my mother’s makeup. It was a lipstick and some blush on my cheeks. Like any cross-dresser, or transgendered person – I felt happy, but at the same time I was confused. I didn’t think much though. I had other things going on in my life that occupied my mind and I didn’t take my cross-dressing seriously.

In this blog, I will try to connect with many cross-dressers and cross-dresser loving people. I am up for discussions and expanding my online social circle. I won’t be disclosing too much information and my thoughts on this blog entry as I consider it an introductory post.

See you soon guys! And yes, I will always say this – follow your heart and do the damn thing that makes you happy! Goodbye for now.