On the Streets of Chicago – Crossdressing in the Rain

  • I recently made another visit to Chicago. Seems to be one of my favorite cities to crossdress in Allie and I stayed downtown again, and it’s so easy to walk out on the street as a gurl there. Of course it always makes me a little nervous, but other than a couple looks (I mean, [...]

  • This Little Tranny is Moving to China

  • Phew, I’m a little behind on this whole blogging thing! Luckily I’ve managed to keep more-or-less up to date on TheCrossdresser.com, but blogging has clearly not been a priority lately. And frankly my crossdressing has suffered as well – I only spend half as much time dressed these days as I used to But hopefully [...]

  • European Crossdressing

  • Well it only took 2 trips to Germany to finally get to take some sexy crossdressing photos in a European hotel room . . . but I think it was worth the wait I had this whole plan to do a neat bathtub shoot (bathtubs in Germany are particularly well suited to taking photos, with [...]

  • Sexuality Map

  • I just found this thing and had to post it . . . especially after I wasted 30min building mine, lol Anyway, I think it’s a pretty cute idea to map out your sexuality, and it was fun thinking back over all the things I’ve tried! Well, and maybe a little scary too when I [...]

  • Crossdressing in Public – Downtown Chicago

  • Yikes, I haven’t posted on my blog in a while, but don’t worry – I’ve still been crossdressing In fact, not long ago I was out for a night on the town in downtown Chicago all dolled up, so I thought I’d share a couple of the candid photos I took that night. Allie took [...]

  • My Girlfriend Peed on my Sissy Cock

  • Allie and I haven’t had much time recently to take crossdressing photos, but last night we finally found some free time and were both in the mood. I’ve been waiting forever to see Allie dressed up in black stockings and her new red leather t-strap heels (I was so excited when I found those for [...]

  • Shut Down by YouTube :(

  • Ok, I guess it couldn’t last forever, but I’m a bit upset that YouTube shut me down so abruptly. They didn’t even tell me what they found offensive about my videos Bah. Well I guess the upside is that I started looking for other places to post my trailer videos (obviously the full versions always [...]

  • Crossdressing Teaser Videos

  • If you’ve ready any of the posts on my blog, you know I’m always up to something new. I usually have more projects than I can keep track of (but thank goodness I always keep track of updating my members area ) – some of my projects work out, some of them don’t. Anyway, I [...]

  • Deviant Crossdresser Art

  • The stuff I post on TheCrossdresser.com is all super high resolution purely pornographic crossdressing photos. And while I love my job as an amateur porn star, deep down inside of me is a beautiful artist Ok, really I just love photography and playing in Photoshop . . . which mind you are pretty useful skills [...]

  • Crossdresser Cooking – “Whore” Pasta

  • Perhaps you don’t know this, but I’m really a multi-talented girl Not only can I do make-up, shop, and lift up to 2 lbs with my cock . . . I can also cook! And I know you might be asking what the heck cooking has to do with crossdressing (other than I love running [...]