When I wake up, I notice it’s raining again, just like last friday. I haven’t got any classes today, but as I have got a lot of studying to do, I get out of bed and wander into the shower. After lifelessly standing there for about ten minutes, I come into terms with the fact the hot water will once again fail to cure me of the slight hangover that marks most of my friday mornings, so I turn off the taps and walk to my room. I make sure to lock the door behind me and open the drawer beneath my bed. I assemble an outfit for the next couple of hours and start by putting on my bra. Next, I take the panties I’ll be wearing and, after squishing my genitals into place, I quickly put them on. After hoisting my skinny jeans over my not-so-feminine mountainbiking-thighs and putting on a top and a blazer, I take an apple, turn on my laptop and sit down at my table. Now, even with my genitals being squished even further, the underwires of my bra carving into my ribcage and the label of my top itching away on a place I can’t reach, I am more comfortable than I have been for the last couple of days.
Saying that female clothing is uncomfortable, can be quite an understatement in some cases. No wonder most women seem to spend their days off being braless and wearing baggy sweaters and jogging pants. Being a crossdresser though, I like to spend my days off wearing the clothes most women tend to avoid when they can. For me, being mentally comfortable doesn’t necessarily involve being physically comfortable. As a matter of fact, they regularly seem to rule each other out.
For me, the urge to crossdress reaches a peak about once a week. I am able to ignore this urge up to a certain extent, but after a while, the thought of crossdressing starts to clog up my mind. When I’ve reached that point, I know the only way of getting things done is by doing those things whilst crossdressing. At those moments, looking down and seeing myself wearing a cute dress or a nice top satisfies me and makes me feel comfortable in a way nothing else will.
For me, there are moments when simply the only way to get comfortable is to get uncomfortable.
ps: I got inspired to write this post whilst reading this post from fellow crossdressing blogger jessxdress
Crossdresser's quirks 
I’m glad I could be an inspiration. I can relate to your post though I have rarely had roommates simply because I always preferred to have the freedom to lounge around in the other half of my wardrobe. I like the title the original title I was going to go with was “Uncomfortably Comfortable” and so it appears that great minds think alike.
My husband, just got married 🙂 kinda long story but we were reunited after 15 years! I love him sooo much! I knew he was a cross dresser when we were together back then. We split due to my drinking and his drug use. We both no longer party and know the Lord! However, he still like to dress up. I do not judge anyone, not my job. But I’m trying to understand what makes him want to do that. He said it makes him feel good. He says he feels attractive and wanted. He is all man! And he is attracted to women. So hes not gay or bi. But likes to wear women’s panties. Dresses and heels. He also likes make up. So I guess what I’m asking, from your perspective, how can I understand better? I’m his best friend and wife! I love him dearly. I just would like to know what I could do to make him feel wanted and secure as his wife. Instead of the clothes doing it for him. Like what goes on mentally in your head when u dress up? Where did this idea come from? How does it make you feel good about yourself? Not trying to get up in your business or anything lol, I’m just trying to understand that’s all. If you have any information you can give me about this I would really appreciate it Im really just wanting to understand what drives this type of behavior and im not condemning anybody by any means. I just don’t fully understand and maybe you could help me to do so. Thank you very much! 🙂
Can talk on the phone? This promises to be a long conversation.
You said you would like to talk on the phone Esteban? That would be nice 🙂 I don’t have anyone to talk to about this particular jazz! what is your phone number?