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, [...]

  • 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 [...]

  • 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 [...]

  • Happy TGirl Holidays

  • It’s the most wonderful time of the year – being on vacation from the day job for the holidays means plenty of time for crossdressing and taking sexy photos Allie is getting in on the action this year too, as I’m sure you can see from the grip she has on my cock in my [...]

  • TGirl Panty Drawer

  • I did this a while ago now, but it’s been forever since I’ve posted on the blog . . . so I thought I would start up again with the announcement of my refurbished Katie’s Closet area of TheCrossdresser.com (sorry, members only. but don’t worry, it’s easy to join if you click the link ). [...]

  • Designer Shoes in a Designer Hotel

  • I’ve always enjoyed my slightly trampy teen look and turned my nose up at most refined designer fashion. Which in retrospect is a bit strange, since I have an absolute obsession with pantyhose and stockings, and I find vintage lingerie and makeup quite attractive . . . anyway, I suppose I just never thought I [...]