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?

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.

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

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?

It wasn’t long after Allie slipped her stocking clad toes into these sexy sandals and tied the decadent bow around her ankle that I was begging for permission to do so much as lick her satin wrapped stiletto heels. Ok, maybe part of it was the fact that she had spent the past 24 hours in our hotel room teasing me and using my tongue to reach orgasm after blissful orgasm . . . all while keeping careful watch over my engorged clitty so that I couldn’t cum myself Needless to say, Betsey Johnson and I became quite well acquainted by the end of the weekend!

I know it sounds awful, but you know how I like to be tortured . . . especially when I’m dolled up in my finest crossdresser stockings and told that I’m going to be an obedient sex slave for the weekend And speaking of the weekend, we spent it in a 5-star resort hotel. For free. So I really couldn’t complain about being forced to dress up and give my girlfriend repeated orgasms on camera. Besides, I knew she’d eventually give in and let me cum . . .

. . . And damn was it a good orgasm when Allie finally let my overfilled crossdresser balls empty their cum all over her sexy velvet gloves and my sheer 7 denier stockings I was so preoccupied with relieving the pressure that when we finally got the camera and scene all set up and I felt Allie’s mouth envelop my crotch and her gloved hands running up my thighs . . . I completely forgot about everything except cumming. Don’t worry, I did manage to hold down the shutter button on the camera at least and get some amazing photos . . . but I was worthless for anything else at that point

Ok, and don’t tell Allie about this part, but when she was in the shower cleaning up after the set . . . I tried on her Betsey Johnson heels . . . and oh my god are they amazing. Now I just have to figure out how to convince her to let me wear her designer shoes for a crossdressing shoot some day