vintage schoolgirl crossdresser
crossdresser in the kitchen
Hi, I'm Katie. Do you like my pantyhose and short skirts? I just hope you won't mind the big cock tucked in my panties! Yup, I'm a hot little crossdresser. Want to see what's under my skirt?

naughty princess crossdresser2017-11-27: Katie-Ann is the naughtiest princess in the whole land. Nothing the King and Queen do will keep her clitty from growing, and the bigger it gets, the bigger the trouble it gets Princess Katie in! Today I'm locked in my tower wearing my punishment panties to try and keep my clitty in check, but I can still feel it throbbing and growing. What are punishment panties? Well here, I'll show you. Just let me slide out of my hoop skirts and hike up my petticoats... hey, you're not going to try and get me in any kind of trouble, are you? Well anyway, these are my punishment panties. See, underneath my tranny clitty is all wrapped up in plastic wrap with sliced ginger. The queen says frigging is good for me. I think it tingles and burns, but sometimes it just makes my clitty hard anyway. I think I'm going to have to find something tighter to wrap up my naughty clitty in today - it's already breaking its way out of the punishment panties. Here, give me a hand, will you? This should really teach it a lesson. Pull it tighter! Oh, woah, I think we made it mad! It's turning purple and soooo hard now! Oh now I'm really going to have to punish it... Watch as I kick my swollen purple balls with my soft stockinged soles to one... two... three ruined orgasms to drain them of their naughtyness! Actually, that last orgasm might qualify as a real one complete with squirting and a shoe full of cum. But no touching other than some well placed kicks to my balls. Talk about some serious CBT!

VIDEO - 2017-10-31: Sexy secretary Katie-Ann offers desk side ball draining services, and looks like you're going to be her first client today! While wearing stockings and heels to the office every day seems to get me pretty far in life, it can be a little problematic when the boys spend more time staring at my long sexy legs than they do actually working. I mean, I realize it must be tough working all day in close quarters with a beautiful crossdresser pornstar, but sometimes I have to, well, take matters in to my own hands. When a coworker drools over me a bit too much I have to call him over, give his nuts a good squeeze so he remembers who's in charge around here, and then rub one off for him all over the soft soles of my stockings. Then for the rest of the day whenever he looks my direction I can teasingly slip my foot out of my shoe and show him the strings of his jizz still stuck to my tranny toes. That usually works pretty well to keep everyone in line around the office. I feel bad for the guys, draining their nuts in such a business like manner, but what's a gurl to do? So I decided I'd make a video and email it out to the office showing the consequences of spending too much time staring at your crossdresser coworkers. I really hope it works, because I don't know how much more cum I can fit in my shoes... By the way, there's no sound in this video. It's not your computer. Sorry about that!

office crossdresser2017-10-23: Sorry, Charlie, it's all business with this orgasm ;) There won't be any fun in this office as I strut in front of my desk in my sharp white stiletto heels, click, click, click across the wood floor. You see, I hear you have a bit of a performance problem, and I intend to fix it right here and now. I'm not one to sit behind my desk all day and just talk - I'm a woman of action. As I scoot up on the desk and cross my legs you catch a glimpse of the long lines of my back seamed stockings disappearing under my A-line skirt and wonder what kind of action a gurl like me might have in mind... don't worry, you won't have to wait long to find out. Soon that skirt is riding up over my hips to reveal a soft satin slip and a second pair of patterened stockings underneath my cuban heeled nylons. And beneath than a pair of sheer Wolford pantyhose. What in the world did I have in mind when I came to the office today?! As I slip my lace panties aside you quickly discover exactly what kind of action gurl I am though. What you thought was going to be a sultry tryst with your boss becomes a lesson you won't soon forget as you find yourself faced with a raging hard cock throbbing out from under my panties. Oops, how'd that get in there? ;) Now lick my heels and worship my toes as I kick and crush both your balls and my own in some naughty crossdresser office cbt play. When you're ready to cum, make sure you squirt it on my soles so it mixes with my spunk. I just love walking around the office all day with cummy feet in my high heeled pumps!

VIDEO - 2017-08-05: Crossdresser Katie fills her ass with bananas and learns about figging! I really had a hard time with this video. I was trying so hard to be cute and innocent while teaching you about fruits and veggies, but I was feeling ever so naughty! Hopefully you don't mind too much as I switch back and forth between my innocent bubbly teen voice and begging you to punish my dirty boy balls by whipping them with a ginger strap. Yes, I might have really said something along those lines to the camera during this shoot ;) I definitely got caught up in the sensation of my tight teen ass being packed full of bananas and forgot my manners a few times, hehe. You'll also get to enjoy some excellent footage of me spanking my balls with a massive carrot before stretching my ass wide (really wide) with its 2-inch girth. Plus some brutal self ball-busting kicks - you can really see my tranny nuts bouncing around and swelling from this extreme CBT video. In addition to the beautiful close-up shots of my crossdresser ass getting fucked and stuffed with carrots and bananas, and some pretty hefty ball busting, I take things one step further in this video by introducing figging. Figging is a form of medieval torture involving fresh ginger which burns and stings when it contacts sensitive parts. And while anal figging is fun, today I decided to make a urethral sound out of ginger and insert it deep inside my clitty! WOW does that tingle. That's the point where things got a little out of control ;) After some desperate ball kicking, spanking, and ginger slapping I decided to force a second whole banana up my sissy pussy. After swallowing both bananas whole up my ass I could barely move without risking cumming everywhere. The feel of my nylon-encased legs rubbing against the hem of my cute satin dress was about all I could stand. The perfect time to wrap up my clitty in plastic wrap with a few extra slices of burning ginger and pull my purple rhumba panties back up. I definitely won't be forgetting what a naughty gurl I was today!

xdresser fruit fucking2017-07-17: Katie-Ann sure knows how to get her fruits and vegetables! My newest ultra high def photos will show you how I stay so fit and sexy - I get plenty of fruits and veggies every day ;) Of course, each fruit or vegetable has it's own role to play in a balanced diet, and it's important to know what each one is good for! Today I'll be introducing carrots (monster-thick mutant carrots that is), bananas (especially double penetration bananas!), and a secret mystery root good for keeping unruly crossdressers in line ;) Bet you never knew that good nutrition could be this much fun! Dressed in a super sissy outfit of platform sandals, lace anklet socks, and sheer nylon stockings under a flirty silk dress, I could totally be the star of a kid's TV show... but shhhhhh - this show is for adults only! Oops, did you get a peek at my purple ruffle rhumba panties? Sigh, ok ok, I'll take them off and pass them around so everyone can get a sniff. Hey! No licking my panties, sniffing only - there will be plenty of time for licking after our lessons ;) Ok, so first up are carrots. Big, fat, 2" wide carrots. I have no idea who grew these things, but clearly they knew what carrots are best for. That's right, stretching! A nice carrot fucking keeps my virgin sissy pussy well dialated so I can accept even the biggest of toys. Once my ass is comfortably stretched, it's time to move on to our next superfood - bananas. I don't care how much banana-fucking you've seen before, you're going to want to watch me take this entire banana deep up my gaping ass until... until... yep, I swallowed the whole thing (plus a couple fingers for good measure). And let me tell you, there are some really good photos of that banana disappearing inside of my virgin crossdresser hole ;) Ok, so are you ready for the mystery root? It's kind of big and knobby and hard... just the way I like it. Well, let's slice it down a bit to get a nice firm 6-inch stick. Ooh, can you smell it? That's raw ginger. It was used in a popular form of medieval discipline called figging - a plug of raw ginger was inserted in a victim's pussy or ass to induce a violent burning sensation. But I bet it would be even more exciting as a urethral sound! That's right, watch as I insert a 6-inch long piece of ginger right up my clitty. And just to make sure I can feel it, I wrap more ginger slices around the outside of my raging burning cock and encase the whole thing in plastic wrap (if you don't know, this intensifies the burning sensation - don't try this at home!). Finally, shaking and burning and desperate, I stuff a second banana (yes, that's a banana dp) up my tiny crossdresser ass. Barely able to stand, I squirm back in to my frilly sissy panties and strut off stage, nearly cumming in my panties in the process. How's that for a food fetish? ;)

VIDEO - 2017-07-06: You didn't know your girlfriend was a tranny!? I know Katie-Ann's a cute little thing, but all the girls at school talk about how her clitty is longer than their boyfriends' cocks! I can't believe you didn't know until she asked you to go down on her. So, um... what was it like? Everyone's been wanting to hook up with her to see for themselves, but you're the first to go all the way... you did go all the way, right? Uh huh, you definitely get to go all the way in this video ;) If you've ever wondered what it would be like to be tranny tricked by your school sweetheart, you are really going to love this interactive film. My parents aren't home today, and it's our first time together. I boldly flash my girly panties at you, but I'm nervous about pulling them down... you first! Enjoy the POV angle as I pull your boxers down and your real man cock pops out. It looks surprisingly like... well, nevermind. I've got something special for you that I want to try. I give your prick a few sensual sucks before announcing that it's my turn. I guess your precum really set me off, because I'm out of my panties in no time, showing off my cute little muff that I trimmed up for you this morning. You'd think I was a real girl, but you're having a hard time finding my clit down there... Oh! There it is :) I hope my overgrown clitty didn't smack you in the face too hard... You're still going to fuck me, right? It doesn't matter that my clitty is bigger than your cock, I still want to feel you inside me. It's going to be really special. Oh, before I forget though, we better use protection so I don't get pregnant. Err... maybe we should both use protection ;) Ok, now be gentle with me... This crossdressing video climaxes with some intense condom play as I pull my rubber all the way over my big swollen balls. Soon your cock in my ass is enough to push me over the edge hands free as a huge bubble of cum forms in my condom. And then between your warm cock and the pressure on my balls I orgasm a good 10 seconds after my ruined orgasm, still without any stroking. This was completely unplanned as you can tell by me desperately trying to hold back! Well, what can I say. Good thing both of us wore protection ;)

xdresser condom play2017-06-08: Teen crossdresser learns about safe sex... sort of :) So, my parents aren't home and I was thinking... maybe today would be a good day to, you know, do it. I wore my thigh high toe socks for you today, I know how they drive you crazy ;) Oh, and I found these condoms in the girls locker room, I guess we should probably use them. C'mon, pull your pants down and get ready! Wow, that's a nice looking cock you have. Here, I want to try something I read in a magazine. Close your eyes. Glmph. Gulp. Mmm. It tastes good. Do you like when I suck on it? Ok, my turn! Don't be shy, pull down my panties! My clitty? Oh, it's right here, I always tuck it in my butt during the day so it doesn't bulge out of my panties. Big? Well, I know it's a little bigger than most girls, but... oh, I think you're making it grow! Oh my god, I think it's even bigger than your cock, hehe! No, no, it's ok. I guess you've never been with a crossdresser before, huh? You're still going to fuck me, right? But maybe we should both wear these condoms ;) Ok, now put your cock in my ass, go on. Oh. Oh shit that feels good. Oh... Watch young crossdresser Katie-Ann blow her load while being fucked in the ass without even touching herself. Ok, so it was a bit of an accident, but I was desperate to cum, and the combination of my prostate being probed and that tight condom squeezing the hell out of my tranny balls just sent me over the edge! Enjoy the sexy crossdressing photos :)

VIDEO - 2017-05-17: Your crossdressing mistress just raided your wife's panty drawer! What're you going to do about it? Yup, that's right. I stole these wool tights from your wife, and took her knee-high boots too. I even made a little modification to her patterned tights to accomodate my panty bulge ;) You love me enough to let me keep them, don't you? I mean, I look better in these boots and tights than your wife does anyway. You can have her panties back though, now that I've dribbled pre-cum all over them. Think about my juices rubbing against her pussy next time she wears them, ok? What, are you going to punish me for stealing your wife's clothes and crossdressing in them? I just... ow, hey! That boot's really heavy, ok? And my tranny balls... oof. Oh god, I'm getting all hard from you kicking my balls with your wife's boots! You know how I like CBT. It hurts, but I can't help getting turned on. And now I have to kick my own balls with my boot-socked feet? Yes sir... Harder? I... oh shit, I'm going to cum from kicking my nuts with these socks on... no no no, don't stop! And that's just the begining of the cock and ball tortuture in this extreme crossdressing video! Next up is a bit of ass fucking with a double-sided dildo, while I use the other end to slap my balls. Then comes an extreme 1/4 inch urethral sound to dialate and plug up my poor tranny cock. Finally there is a sensual tease and denial session, bringing me right to the edge of climax in super closeup... and then an incredible ruined orgasm a good 7 seconds after I stop touching myself ;) Ok, to be fair this one is only semi-ruined - I had fully intended to have a retrograde ruined orgasm with the urethral sound firmly plugging my engorged clitty, but the force of my semen building up shot that sound out of my cock like a rocket! And the sensation of the heavy steel sound surging down my urethra was enough to put me over the edge and orgasm... sort of. It was still intensely un-fulfilling, don't worry (you can tell by the way I stay hard and keep trying to rub my cock afterwards!). But I did create a pretty impressive gyser of cum too. I suppose that's the best of both worlds ;) In fact, I was still soooo horny after I finished this crossdressing video that I needed to cum again. And the idea of kicking myself to orgasm earlier was such a turn on that I decided I'd go all the way just by kicking my balls with my stockinged heel. So while I was downloading the files for this shoot, I set up my video camera again and recorded a candid film of me totally crushing my nuts to orgasm. I think it's pretty impressive, so I included it in this week's update :) Enjoy the bonus footage!

xdresser steel urethral sound2017-05-01: Extreme teen crossdresser in ballbusting photos! Your firey little redhead mistress has gone a step too far this time, stealing your wife's favorite boots and strutting around the house wearing them. What're you going to do, hmm? You know you can't deny me what I want. Watch, I'm even going to rub my sissy cock all over your wife's boots, fucking the buckles and dribbling my pre-cum all over the expensive leather. Ooh, did I mention that these wool tights I'm wearing that I cut the crotch out of came from your wife's panty drawer as well? I bet she'd love to know that you're drooling all over my hard cock because your tranny girl looks better in your wife's clothes than she does! Oh, you're going to punish me now? You want me to kick myself in the balls with your wife's thick boots? You know that just gets my slitty harder and splatters pre-cum everywhere. Maybe you should find something really big to stuff up my ass. No, no, the glass dildo isn't big enough today. I need to really be punished. Get the giant double-ended cock dildo. Yeah, now spank me with that giant dildo, right in my sissy balls! Tell me what I naughty gurl I've been, snooping around in your wife's panty drawer! And once my balls are purple from the beating, then you should ruin my orgasm. That thick steel alen wrench should do the trick. No, not that one. The quarter-inch size. Oh fuck that fills up my clitty. I have a really big load today, where's it all going to go?? OH god, that steel shaft in my pee-hole is going to make me... cum! I hope you last until the last photos to see me launch 4 inches of solid steel out of my crossdresser clitty like a rocket as I spoil your ruined orgasm plans ;)

VIDEO - 2017-04-09: Cheeky crossdresser interviews to be a porn star! Watch as I test Cheeky's limits in this real-life audition for a spot on TheCrossdresser.com. Ok, well actually I already knew that I was going to hire her, but I couldn't resist the chance to shoot another sexy video with my new crossdressing friend ;) Cheeky's interview starts out with some innocent requests, like picking up my morning coffee and rubbing my stockinged feet after a long day of walking around in my white patent leather pumps. But pretty soon Cheeky lives up to her name and bravely reaches a hand under the hem of my business skirt to brush my panties! My apprentice crossdresser quickly found out just how big of a surprise I keep in tucked in my panties. No sense in hiding it now, I pulled my lace panties asside to reveal my growing clitty. After that, Cheeky found it a little difficult to focus on the interview ;) I didn't mind though. I had fun teasing her by rubbing my nylon clad feet in her lap until she literally tore her shirt off to get closer to me. I managed to hold her off for a little while, alternating between sucking Cheeky's girly little clitty with my soft lips and crushing it under my silky nylons... but before long I was having too much fun sucking cock. You know how I get with a cock in my mouth, at some point there is nothing you can possibly do to prevent me from sucking out a big load of warm cum whether you want to give it up or not ;) I did at least stop to adjust the cameras though! I let Cheeky spurt a nice sized load of crossdresser cum across my lips and nose. I have to say, she did a pretty impressive job of coating my face with warm spunk, considering it was her first time to give a facial as a crossdressing porn star. Well, that was about as much as a gurl can handle - I had gotten all worked up giving blowjobs, and now I had warm sticky cum running all over my face, and I had been saving up my own cum for this scene too. I was about to burst as I wriggled in to position to deposit my own load on my face as well. Cheeky was kind enough to hold my ass up in the air, and within minutes I was spurting buckets of thick spunk in my mouth, my hair, and even right in my own eye (oops!). You would have thought I came twice the way I kept squirting ;) Between Cheeky and my loads, I have never had that much cum on my face, and I loved every minute of it. See what happens when you let me suck cock? ;)

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