On the Streets of Chicago – Crossdressing in the Rain

  • xdresser 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, who wouldn’t look at a hot girl like me strutting down the sidewalk!) I was perfectly comfortable. I even worked up the nerve to ask the concierge at the hotel for an umbrella as we went out, which he provided with a smile :)

    In spite of the rain it was a rather pleasant night, and we walked the mile or so from our hotel to The Baton, the location of Chicago’s famous drag show. It’s a bit of a seedy bar with very overpriced drinks, but it’s right downtown and the show is worth it. Somehow we managed to score front-row seats! Nothing like looking right up the skirts of some of America’s hottest drag queens only inches away ;) It wasn’t our first time to the venue, as you might remember from a previous post about crossdressing in public. And after quite a few of those overpriced drinks, I managed to convince one of the stars of the show to pose with me for a photo. Unfortunately it’s not the photo you see to the left, as I’ve managed to misplace it somehow during my travels :(

    Speaking of quite a few drinks, after I stumbled out of The Baton Allie managed to convince me to stop for another drink at a downtown bar on the way back to the hotel. So there I was, all dolled up in my wool tights and high heels, walking in to an ordinary bar full of unsuspecting patrons who had probably never seen a crossdresser before, lol. If people were staring, I certainly didn’t notice – I was having the time of my life out on the town, fully dressed and pretty darn passable I’d say.

    Heading back to the hotel the rain let up a bit and became just a little drizzle. So I decided to snap a few photos dancing with a streetlamp under my borrowed hotel umbrella. Pretty classy, don’t you think?

  • 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 all that’s about to change, and this post is proof! Ok, well I shouldn’t get ahead of myself I suppose, but I’m going to try and do better keeping up.

    crossdressing in China

    So here’s the reason I’m so far behind. 2 years ago my day job sent me to China again. Clearly evidenced in the photo above – I mean, where else do you find architecture like that outside your window? And not for some little 3 week trip this time, but for a 6 month “extended” business trip. Extended of course being a rather severe understatement. Well 6 months turned in to 8 months, and then there was some debate about actually moving me to China for a couple years . . . And then finally after about 15 months in China they officially moved me here. That might not sound so terrible, but remember that China and porn don’t exactly get along. Nor does China and crossdressing. And on top of that, I spent 15 months without my wardrobe or computers. Which needless to say made crossdressing and updating websites a little challenging.

    Of course, I wasn’t about to embark on a 6 month business trip without any of my Katie clothes! I certainly brought some along and continued posting updates to TheCrossdresser.com . . . I just didn’t have quite the variety and selection I’m typically accustomed to. Not to mention that it became a lot more difficult to pick up last minute props for sets and stuff like that.

    Well anyway, I’m not in China with all my stuff. I’m starting to settle in to my routines and re-organize all my files. And with a little luck, I will be posting like crazy again here soon :)

  • European Crossdressing

  • European Crossdress SexWell 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 the little glass half wall for the shower and a detachable showerhead), but when Allie and I walked in to our gorgeous hotel room everything changed. This room was built in to a 1000 year old stone wall surrounding the little city we were in, and was decked out with antique hardwood and leather furniture. The only thing better than the room was the view we had overlooking the entire river valley below us.

    But enough about the room – it was just there to set a perfect stage for some kinky European sex :) Allie and I luckily both had outfits to match the scene: tiny little miniskirts, layered tops, some eye-catching heels, and of course the stockings. Allie was sporting a pair of black cashmere wool tights with a cableknit pattern (it was winter in Germany afterall), while I wore sinfully sheer vintage nylon stockings with a gartered waist cincher. I felt so incredibly sexy in my outfit, and I couldn’t stop rubbing myself against Allie’s legs, feeling the soft fabric of her wool tights.

    I had fully intended to fuck Allie in one of the overstuffed antique chairs in our room, but after I pulled her to the floor and licked her juicy clit to a super powerful orgasm as she laid on the soft shag rug in the room, I couldn’t help but rub my throbbing crossdresser clitty against her sopping wet pussy. And of course one thing lead to another, and pretty soon I was going to town banging my girlfriend on the hotel room floor with her tights still wrapped around her knees. Luckily I had enough willpower to grab her and flip her up on all fours, planning to finish doggy style with one of my famous crossdresser cumshots all over her ass. Allie had slightly different plans though, as she quickly turned around and swallowed my cock, sucking her own girl cum off of my massive clitty, then pulling my panties aside and deep throating my clitty so she could lick my swollen balls.

    I guess the hotel room and our Eurpoean outfits (and perhaps her massive orgasm too) had really gotten to Allie – she was acting like a full blown porn star, and I was in crossdresser heaven. I didn’t have much left in me at that point, but don’t worry – I did manage to get Allie turned around again and pound her sexy pussy doggy style before cumming all over her ;) You should have seen all of my cum dripping down her ass and running over her gaping pussy! Well, actually you can see it. I’ll be posting ALL of the photos and video over at TheCrossdresser.com now that I’m back home in the States again.

  • 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 checked off nearly everything on the map :P

    Find out where I've journeyed
    on the Map of Human Sexuality!
    Or get your own here!

    I suppose I still have a few places to visit . . . I guess I should use my sexuality map as inspiration for the next shoots that I do for TheCrossdresser.com :)

  • Crossdressing in Public – Downtown Chicago

  • Crossdressing at The Baton LoungeYikes, 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 me out to The Baton Lounge as a sort of late birthday present. The Baton is a famous drag show right in the heart of downtown . . . and within walking distance of our hotel. So there I was strolling down the streets of Chicago in my tights and heels – probably the farthest I’ve ever walked in heels before actually, but I was pretty proud that I made it with no problems :) I don’t go out crossdressing in public very often. In spite of the website, I’m still pretty nervous of people staring at me. Plus I don’t like to do it unless I’m traveling – have to keep up appearances with the neighbors (and co-workers, etc) if I’m out in public in my hometown! I do make an occasional exception for a little local drag show, but it’s not the sort of place I can hang out at every weekend.

    The Baton in Chicago is a bit past its heyday, and the drinks are super overpriced . . . but overall it was still a good time. The place was packed for the show, and it was clearly a serious production for the performers – this wasn’t your typical hole-in-the-wall bar type of drag show. One of the girls was drop dead gorgeous too. Service is a bit crappy, but the staff seemed to appreciate the fact that I had dressed up – it was definitely a comfortable place to be dressed. The one downside is that they don’t allow photography – I had all these plans of taking a bunch of pics of me crossdressing at the show, but unfortunately I had to keep the camera hidden :(

    Crossdressing in Downtown Chicago
    The rest of downtown wasn’t quite as comfortable – I got a couple interesting looks on the street. But it still didn’t keep us from stopping for a few photos on the bridge over the Chicago River. Overall I was impressed though – I guess you see all types in a big city like Chicago – most people didn’t bat an eyelash at passing a crossdresser on the street. I wasn’t exactly at my most passable that night. I’ve been trying to grow my natural hair out so I don’t always need a wig, but the pigtails perhaps weren’t the best choice for fitting in. Oops :P Ah well, the only particularly nerve-wracking part was walking back in through the hotel lobby and waiting on the elevator with a large crowd of people. Would I do it again though? Absolutely!

  • 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 her :) ). I didn’t have anything particularly inspiring to wear, but we decided to do matching outfits so I dug out some red sandals and black thigh highs as well. And we had these adorable matching purple skirts that needed to be put to a good use.

    You’d think with outfits like that it would be pretty obvious that we were up to no good ;) We headed out to the club to try and find someone to come home with us, but we must have picked an off night because the crowd was pretty dull. So Allie and I both came home empty handed. Not wanting to put such scandalous outfits to waste, I set up the cameras and tried to convince Allie to take some photos with me (and in the process get some pussy for my aching crossdresser cock). Lucky for me, Allie was both drunk and horny, so convincing her was no problem. Convincing her to give me a turn even after 5 orgasms on the other hand was a different story. Guess she was more horny than I had realized at first.

    Well I finally got Allie to put down her magic wand and let me fuck her. She even climbed on top and rode me reverse cowgirl. I was just thinking I was the luckiest crossdresser ever when I felt her start to squeeze her pussy in the strangest way. It didn’t feel bad, but Allie was really tight after 5 orgasms, and I could tell she was up to something. So of course I asked what she was doing, and she looked back at me completely straight-faced and said that she was trying to pee on my cock, but she couldn’t get it to come out! So here’s a photo of my girlfriend trying to piss on my cock because she was drunk and wanted to get back at me for cutting her off at 4 orgasms :P

    girlfriend riding crossdresser cock

    Yes, I took a photo just because I thought it was funny she was trying so hard to pee on my cock and couldn’t do it. Well apparently I shouldn’t have laughed at her so much, because a few minutes later Allie started to moan a bit and my cock started feeling really warm. And then I felt something splashing on my legs and dripping on my white panties. Pretty soon I was laying in a puddle of Allie’s warm pee that had collected in my skirt as she emptied her bladder down my cock while I fucked her.

    Ok, I admit, I really enjoyed how warm and wet it felt, and as Allie stood up and I saw the last little dribble of pee fall from her pussy onto my chest I grabbed by pee soaked cock and started jerking hard. I ended up cumming all over my girlfriend’s black stockings, right across her foot. Yeah, it ended up being a good night after all ;)

  • 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 have and always will be available in my members area) . . . and now I’ve found a tube where I can even post the explicit versions! So keep an eye on my xHamster profile to find my latest trailer videos, like this one of me making out with another crossdresser and giving her a nice handjob :)



    At least there’s some people in the world still who don’t mind high quality adult videos, :lol: Non-adult businesses can be pretty rough on the porn industry though. Personally I’m proud that I sell my explicit photos and videos, and I love knowing that people get off watching me – I don’t think it’s anything to be ashamed of.

  • 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 started something new recently that seems to be working out pretty well. I’m posting teaser clips of my crossdressing videos on YouTube. Of course I have to keep them pretty tame in the interest of not getting banned, but I think they’re a fun glimpse in to the content available in my members’ area. Obviously my members-only videos are considerably more . . . explicit ;)

    So I only have one teaser video up on my YouTube channel so far (plus a couple other odds-and-ends crossdressing videos you might want to check out), but it seems to be pretty popular :) I’ve embedded it below, Two Crossdressers Kissing:

    I’ve got another teaser video all lined up to post this weekend, so be sure
    to sign up to my YouTube channel to get all the updates! And if you visit my site I’ll also be posting a slightly more risque version of the teaser that you can download. Of course if you want to see all of my steamy crossdressing action, you should probably just sign up for the members area ;)

    In the meantime, enjoy the free video and let me know what you think!

  • Deviant Crossdresser Art

  • garden crossdresserThe 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 :P Ok, really I just love photography and playing in Photoshop . . . which mind you are pretty useful skills for a girl running her own porn site . . . but sometimes I like to show off my not-so-explicit images too. Like this one Ok, maybe this one is a little explicit, but it’s more erotic than hardcore at least. Right?

    I do have some very tame self portraits though (of course members of TheCrossdresser.com get access to these as well), and even some still life and landscape work that I do . . . which I don’t suspect my members care that I don’t post on the site (if you do, let me know – I’d be happy to share my photos of flowers and mountains with you! Anything to keep my members happy of course :) )

    So in the interest of not boring you too much with my other not-even-erotic images (and perhaps to show off some of my tastefully erotic crossdressing images to a new audience), I thought I’d join DeviantArt. I just came across the site a week or so ago, and so far it seems like a pretty fun place. There are lots of people browsing and commenting on art, and there really are some pretty talented artists that post on the site (along with some very amateur ones as well :P )

    Of course, I’ll save my kinkier photos for the blog (and the kinki-est photos for my members only area!), and I’ll inevitably post a selection of my other random images here as well. But if it seems like your sort of thing, check out my DeviantArt profile too. And leave comments, I love to hear what people think!

  • 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 around the kitchen in my panties and heels, and I’ve been known to use kitchen utensils as sex toys), but I promise you there’s a connection!

    I’ve never been much of a fan of spaghetti sauce, to the point that when I was a kid I would eat my spaghetti plain. So when I started learning how to cook I experimented with different things I could put on pasta to make it a bit less boring, and I came up with a mixture of diced tomatoes, garlic, and olive oil that worked pretty well for me. Over the years my recipe evolved a bit, and then one day I found out that I wasn’t the first person to discover this recipe. Apparently it’s more or less a traditional Italian sauce known as Puttanesca. Which wouldn’t be very exciting if it weren’t for the fact that Puttanesca translates roughly as “whore style”. Yes that’s right, for as long as I can remember I’ve apparently been eating my pasta whore style. Go figure.

    Ok, that’s the whole story, I just had to share. Even my cooking is slutty :lol: But in case you’re curious, here’s the recipe I use and a nice photo I took of my Capellini Puttanesca :)

    Capellini Puttanesca, aka whore spaghetti

    1 box Angel Hair Pasta
    1 lbs Crawfish (tail meat), or substitute shrimp, crab, etc
    2 cans Diced Tomatoes (get the kind with green chilies, and drain most of the liquid)
    1 bulb Garlic
    1 cup Fresh Basil
    2 tbsp Olive Oil
    1 tsp Oregano
    Salt and Pepper to taste
    Garnish with Parsley and Grated Parmesan Cheese

    Chop the garlic into rough slices (This will result in garlic that maintains a bit of it’s raw flavor. If you don’t like that, mince it instead). Shred the Basil and set aside.

    Boil water per directions on pasta box, salt to taste.

    While the water is heating, add olive oil to a large pan and warm over medium heat. When the oil thins and begins to flow, add the garlic. Saute 2 min, then add oregano, salt, and pepper to taste. Continue to saute until garlic begins to brown around edges.

    Turn heat to high and add tomatoes, stirring until mixture begins to bubble. Turn heat back to medium and add basil. Mix in basil and let cook 2 min. Cover and turn heat the medium-low.

    Add pasta to boiling water. Cook to short end of package directions, or about 6 min. Drain pasta.

    Add pasta and crawfish to sauce pan, mix thoroughly. Cover and cook 5 min.

    Serve immediately, garnish with parsley and grated Parmesan cheese.