Interview With Katie Ann

June 4, 2009

I think of transvestites as males who become sexually aroused dressing as females.   When I first Googled the term “crossdresser” a few years ago, I found Katie Ann’s website and it was in conflict with what I thought of the sexuality of crossdressers.  Katie Ann’s website helped me realize that it’s difficult to label anyone in the transgender community.  I got in touch with her to explore what makes her tick and found out why her website The Crossdresser is one of the most popular sites on the Internet for part-time girls.

Caramel:  Hi, Katie Ann. Thanks for doing this interview with me.  I’ve known of your great site for years and I believe it’s been up and running for several years now. $24.95 is a very reasonable price for your 30 day subscription and $3.95 for a three day tour. Does charging so little allow you to turn enough of a profit to make a living or do you still work another job?

Katie Ann:  Thanks, I’m always happy to get an interview – I love talking about my site because I really do it for fun. I love dressing up, and I love taking photos! I’ve actually been doing this for almost 7 years now, though I kind of stopped counting after 5 😉 It’s definitely not my full time job though – my day job takes up about 60 hours / week and pays the bills. Most of what I make from the website just goes into site improvements and new outfits to share with my members 🙂 I could run the site on a much lower budget and pocket the difference or let someone else manage the day to day stuff like answering emails, but it really means something to me to provide the highest quality content that I’m capable of plus a level of personal interaction you just don’t find on other sites.

Caramel:  What is the tgirl scene like in Cincinnati, Ohio?  Is it a thriving one?

Katie Ann:  I really can’t recommend Cincinnati for it’s tgirl scene . . .there isn’t much outside of my bedroom 😉  Seriously though, I know of two TG friendly bars in the entire city. I’m only here for my day job.

Caramel:  Running adult websites attracts a lot of attention no matter where you live, though. I’m sure it’s not hard for you to find friends to play with in your personal life, but is it hard for you to find crossdressers and genetic females willing to do photos shoots and make videos with for your website?

Katie Ann:  Hehe, I sure wish I had more luck in my personal life!  But yes it really takes some work to find models for the site.  Crossdressing is a pretty personal subject for most gurls, not something they’re looking to share with the rest of the world.  And as for genetic females, I’ve yet to figure out how to walk up to a hot girl and ask her if she wants to do porn with a crossdresser 😉  On the other hand, most girls that I spend any amount of time with I end up telling about the site.  Sometimes it works out, sometimes it doesn’t.

Caramel: You’re pretty well-endowed, Katie Ann – a big girl down there. Do other crossdresser models find it hard to work with you when it comes to penetration?

Katie Ann:  Thank you :*) I’ve never had anyone turn it down . . . so I guess I just know how to use it well.  Actually I’ve had more problems with genetic females telling me that I’m too long, though that’s usually after the fact 😉

Caramel:  Always leave them walking laughing or at least walking  funny is what I always say.  Just kidding.  In a set named “The Prostitute” you’re getting it on with a hot genetic girl with a pretty large dildo. You have a big cock and your partner’s strapon was even bigger. Was it hard for you to take?

Katie Ann:  That’s one of my older sets with Jade I think, so yes I had a hard time with it! That thing was thicker than it looked, but it was really fun when that strapon and I DP’d Jade 🙂 She’s actually my ex, but we’re still friends . . . I’m still trying to convince her to come back and do some more sets for the site!

Caramel: How old were you when you lost your anal virginity?

Katie Ann: Um . . . technically I’m still an anal virgin :*)

Caramel:  Oh! You have a lot to look forward to if you finally decide to lose your cherry. Trust me on that.  You started crossdressing at 8 years old and at 27 now consider yourself bisexual. How early was it when you learned you were bi?

Katie Ann:  I guess I’ve always been bi, I just never realized it. I mean, when I was 8, I used to fantasize about putting on a pair of magical pantyhose and transforming into a real girl and spending all night dancing and performing for a guy, then taking off the pantyhose in the morning and turning back into an ordinary 8-year-old boy chasing after girls . . . I never admitted that I was also interested in guys though until I went to college. I was 18 and at a party in the dorms when all the (older) girls left us freshmen guys by ourselves so they could go to a frat party. So I sucked off every frustrated straight guy in the room on a bet that I couldn’t do it 😉

Caramel:  Damn, you had a lot more fun in college than I did! So, where do you get most of your female clothing, at free-standing stores, malls or online?

Katie Ann:  Honestly most of my clothes come from sales racks at mall stores. I buy all my shoes online though, and a lot of my socks and pantyhose come from online stores too. For skirts and tops though you really can’t beat the Juniors mall stores who try to turn over their stock every month!

Caramel: Tell me about it. My first management job was running a Juniors department and I was never late with taking markdowns. Those purchases were not the most age appropriate I made, but who can resist sexy schoolgirl get-ups?! But I digress. I’ve seen some of the questions you’ve asked and advice offered at pro webmaster forums and technically, half the time whatever you’re talking out goes way over my head. How did you become such a web design pro?

Katie Ann: Lol, I’m far from a pro at webmaster stuff, but I’ve always been a nerd. I started coding at about the same time I started crossdressing. Computers aren’t my forte though – I’m much better at chemistry,
biology, psychology, and sex 😉

Caramel:  I do see the connection. You do all of your photography also. How did you learn to shoot well and did you have to make an enormous investment?

Katie Ann:  I’ve always loved photography and I can’t really say why. I was never very good at it, and I have no formal training . . . if anything I was intrigued by it because I didn’t understand how to capture things the way I saw them. I read a lot of books on image theory and visual perception I guess. And I started my website with a digital camera that I got for free – so no, it wasn’t much of an investment 😉 I have some OK equipment now (a nice camera and some crappy lights), but I think it’s more about the energy you bring to the scene and the effort you put into trying to make sure it will look good. Practice and passion. Anybody can take a terrible photo with expensive equipment. Passionate people can take beautiful photos with crappy equipment. I’ve also always had a thing for sex photos. I like to remember my partners and my experiences. Nothing turns me on like a camera (except maybe making somebody else cum . . . )

Caramel: I love your answers. I also love that you include fetish and light bdsm scenes at your site.  When it comes to roleplay, would you be considered a submissive, dominant or a switch?

Katie Ann: I love fetishes, fantasy, role play, and making other people happy. I guess that makes me a “switch”.  As long as I have a character I can get into I’m a happy girl. I’m probably more submissive by nature though. I’d do some more serious BDSM, but it’s really tough to tie myself up AND work the camera!

Caramel:  You do manage to do great solo work. There’s a fun gallery at your site entitled “Night Out” where you’re being naughty outside of a hotel room at 3am. Did you do it and take that risk just because it would be good for your website, or did you get a sexual charge out of the risk of getting caught?

Katie Ann: I don’t think I’ve ever done a set “just for the website”. I can’t say that actually getting caught is a fantasy of mine, but I loved the feel of the night air, the look of the cars driving by below, and the idea that somebody probably drove home that night and jerked off to the thought of catching glimpse of a girl in a short skirt doing a porn shoot on the balcony of her hotel room. Especially since the poor guy probably had no idea what I had tucked in my panties 😉

Caramel: That’s another sexy thought. Do you take requests from fans for your photo shoots?

Katie Ann:  I love getting requests! My favorite shoots are usually member requests, in fact I just did one last weekend that I will be posting this week. There’s something awesome about fulfilling someone else’s fantasy. I like it so much that I usually take a special photo just for the member that requested the set, complete with a personal message.

Caramel:  That’s so proactive and hot!  It’s both fun for you and a great way to retain your rapidly enlarging following. So many individual models have no idea how important interaction with their members is. I know that one reason I’ve never settled down is because I’m bisexual.  If you’re not in somewhat of an open relationship, it can be hard on a couple.  Do you find that your sexuality makes it difficult for you to settle down with one person?

Katie Ann:   That’s a tricky question. It’s definitely difficult to remain a practicing bisexual if you settle down with someone. But I’m typically more sexually satisfied when I’m in a relationship. It’s pretty hard to find sex twice a day when you spend 10-12 hours at work if you don’t have someone to come home to 😛 Maybe I’m just high maintenance though! Sexuality aside, I like my personal space which is probably a bigger reason for not settling down. So if anyone out there just wants regular sex, is willing to have photos posted on the internet, and isn’t creepy . . . I’m looking 😉

Caramel: When it comes to dating, do you mostly go out with genetic females, others crossdressers, 24-7 masculine males or transsexuals?

Katie Ann:  Well I’ve only “dated” genetic females, but that’s probably because I’ve never met a guy or crossdresser who meets my criteria for dating. Most men and CD’s are either only okay with my female side or
only okay with my male side . . . which is not a problem for a casual encounter. But I spend a good bit of my life on both sides of the gender spectrum (and intend to keep it that way). And I’ve actually never met someone who would really qualify as transsexual thanks to living in conservative Cincinnati. I’m just an innocent sheltered little thing . . .

Caramel:  You would have met one if I lived there, or had the opportunity to. *hint* So when you’ve dated genetic females, have you found it hard, in the past or even now, to “come out” as a crossdresser?

Katie Ann:   It’s always a difficult conversation to start. But I can only think of one girl I’ve ever dated that I didn’t at least mention it to. You just have to play it by ear, I usually start by talking about the clothes I like to see her in, mention that I’ve tried on girl clothes a few times because I like how they feel . . . and see where it goes. If she’s not interested, I let it drop. And usually don’t date her too much longer, lol.

Caramel:  I think you’ll find the subject easier to approach with bisexual girls. The straight ones tend to go through all the drama and worrying that you’re bisexual or gay and in most cases that’s too much data to process. Katie Ann, thanks again for doing this interview with me. Your replies were better than I could have hoped for and also quite arousing. I wish you another seven years of good luck with your website and many, many more.

Take Katie-Ann’s transtastic tour of TheCrossdresser.com! 

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