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?

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

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 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!

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

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

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:
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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!

Turns out that all these years I’ve just been using the wrong lube for anal sex. As you can see from the screen cap above, Allie gave me a thorough ass fucking last night with her feeldoe dildo. She really went to town on my tight tgirl ass . . . and it felt good I mean really good. Like good enough that I almost came from her rubbing against my prostate without even touching my engorged clitty. (If you’re wondering, I managed to hold off my orgasm until we got the cameras arranged for the finale, and I jizzed all over my silk tank top with Allie’s fake cock up my ass)

So what is this magic lube that I found? Vaseline. Seriously. Not that I haven’t used good old petroleum jelly on my ass before, and sure I know that it’s a good thick non-drying lubricant. But it’s oil based, so not good for sex and not good for toys, right? Well, sort of. It’s not good for vaginal sex, that’s true. And it will wreck a condom or any “jelly” rubber toy, so no good there. But turns out it’s perfectly fine for silicone toys. So from now on I’m sticking to only silicone or glass toys so I can pamper my delicate ass hole with Vaseline

And one other thing I learned . . . turns out that greasy film that jelly rubber toys get coated in as they age? It’s a plasticizer added to the rubber to make it soft, and it separates out over time. And it’s also a known skin irritant and has a tendency to “melt” other rubber toys that come in contact with it. Great stuff. So screw all those jelly toys I have that aren’t compatible with my new favorite anal lube and are coated in skin irritants to boot. I’m sticking with silicone

Of course, when I first heard about this miracle of the lingerie world I suspected it was more marketing hype than miracle . . . until my girlfriend got fitted for one on a whim. Rest assured, I am now convinced that Victoria does in deed have some Secrets – the Miracle Push-Up is aptly named, and 2 cup sizes is no joke! Returning home with our new purchase, Allie immediately suggested that I try it on (yes, here comes the crossdressing part of my blog entry ). I hesitated a bit, being partial to my breastforms and still holding on to a bit of doubt about the bra . . . but eventually I gave in. Really I couldn’t turn down the opportunity to steal something from Allie’s panty drawer anyway

Let me tell you, the Miracle Push-Up will work miracles even without any natural breasts to work with. I went from washboard flat to an attractive and realistic B cup in a matter of seconds. And it only set me back $50 as compared to the $300 I paid for my latest pair of breastforms. On top of that, I went an entire photoshoot without once worrying that I was falling out of my bra (and if you’ve ever worn breastforms and seen one of my photosets, you know that’s saying something!). So while I won’t be completely replacing my silicone breasts with the Miracle Push-Up (I do still like the weight and bounce of silicone), I will definitely be taking advantage of it when I travel or wear low cut shirts

I don’t think China’s too fond of crossdressers either, as they are still slow to accept even homosexuality . . . and at least from a social norms standpoint, I think transgenderism is probably a bit farther out there. I certainly didn’t want to push my luck while I was there.

Anyway, I at least didn’t waste my time while in my all-expenses-paid 5-star hotel room, and I didn’t forget about my members while over there I took advantage of the nice couch, great view, and oversized shower to do some fun shoots like the one below. And I kept the site updated by accessing my databases via my hosting provider. Hey, a gurl’s gotta have priorities!

Told you it was a nice view, didn’t I? I felt pretty classy in my pattern printed nylon stockings which seem to strangely match the lights of Beijing from my hotel room window. I topped it all off with a nice corset and designer heels that I had originally brought along for my girlfriend Allie to wear in a shoot . . . but she couldn’t stay with me the whole time I was there, and we ran out of time. Sad day. So I had to solo my shoots. Don’t worry, I’m sure you’ll still enjoy them

If you’ve been out of the loop for a while, Allie is my girlfriend and is quickly becoming a significant part of my website. So I thought it was only fitting to give her a little room on my site where members can rummage through her panty drawer as well

In honor of all this panty drawer talk, I thought I’d show off a bit of my own panty collection for those of you who aren’t lucky enough to be site members. Whenever I update my closet with thumbs from a new photo set, it never ceases to amaze me just how many pairs of panties I’ve worn in my life, hehe. And really these aren’t all the panties I’ve worn, just the ones I’ve taken pics of! I guess a real girl wears a lot of panties and never thinks twice about it, but as a crossdresser, each pair of panties is kind of special. And I imagine most crossdressers haven’t worn nearly as many pairs as I have. Anyway, here is just a small sample of the panty pictures you can find inside my site.

And a post like this just wouldn’t be complete without some samples from Allie’s panty drawer as well. I know Allie has worn a lot more panties than I have, but since she’s new to the site (and to having someone take pictures of her in her panties ) she doesn’t have as many pairs in her virtual panty drawer. Yet. Don’t worry, I will be adding more regularly! She looks almost as good in panties as I do, don’t you think?

Anyway, I always wished that I needed orthodontic braces. I know, a very strange thing for a kid to wish for. But probably no stranger than wishing that I could put on a pair of magical pantyhose and transform into a real girl at will So naturally when I started making the transforming into a girl fantasy come to life by sharing my crossdressing photos online, I also started looking for cosmetic braces. And I’m proud to say that after years of searching, I’ve finally found some!

I’m pretty excited about my new orthodontic braces, so I’ve been wearing them a lot. Though don’t worry, if you’re not into braces these aren’t permanent – they are a veneer that I can put on when I want and take off when I want. How cool is that? And they actually look pretty realistic, don’t you think? I spent a ton of time searching for these things.

Generally there are only 2 types of cosmetic braces in the world – halloween costume braces, and retainers made by dentists. The former look like crap, and the later you really have to be comfortable with your dentist to request (and that’s no guarantee he will know how or be willing to make them). Real retainers are also uber expensive, and don’t expect your insurance to pitch in for them! Anyway, I found these veneers I’ve been wearing at Dental Distortions. They make orthodontics that are used in Hollywood – including fangs, missing teeth, and you guessed it, braces! So if you’re into braces or any other type of orthodontic modification, and you want a non-permanent but realistic effect, I highly recommend them