Interview With Sandra of Trannies In Trouble

April 24, 2010

I’ve known about Trannies In Trouble from Sandra Gibbons since not long after it launched in 2003. That’s about the time I developed a serious interest in bdsm. After finding her Yahoo group and seeing her profile at another bondage-themed website, I jumped at the chance to ask Sandra questions I’d been developing over the past few years.

Caramel: Hi, Sandra and thank you for doing this interview with me. I absolutely love BDSM-themes, your brand of it in particular.  I’ve seen a lot of trangender bondage websites, but you run one of the few bondage sites with crossdressers and transsexuals on the Internet and I think it’s the best one out there. I know why Trannies In Trouble is a huge success as a member, but I want to get to the bottom of the history behind it – what makes Sandra Gibbons tick. I know that your interest in dressing as a girl and being tied up began to develop when you were a small child. However, you stifled the urges to crossdress for years. How old were you when you finally began to dress as a girl?

Sandra: First off – Thanks so much, Cara, for asking me to do this interview!  I’m really flattered to be here!

Well, as for crossdressing, I actually started pretty late. I would occasionally sneak into my mother’s closet when I was a child, and I owned a few dresses and things when I moved out of my parents’  home, but it was all very casual and secretive.  I didn’t really start playing with makeup and trying to put together an actual “look” till I was probably in my early to mid thirties.  I really wish I’d started in my twenties, but I didn’t have a clue back then in so many ways!

Caramel: Well, you were raised in the very conservative, middle-class Colorado Springs – the suburbs and home to several military bases.  It must have been difficult knowing you were different as a child and not being able to express yourself.

Sandra: Yes, it was difficult.  I think it’s difficult for most crossdressers and trans girls. I hear from a lot of people through my website and hear so many similar stories. The shame and secretive way of life are really common.  Some of the most heartbreaking stories are from the crossdressers who’ve decided to never share their secret with anyone in their day to day life.  I’m not usually a bold person myself, but somehow I knew that I couldn’t stay in the closet all my life or I’d be completely miserable. So I always recommend to CDs who write for advice that they should try to find at least one person that they can open up to, and just take baby steps from there.  Living with such a big secret can be really painful.

Caramel:  Have you ever felt that you were born the wrong sex or trapped in the wrong body?

Sandra:  To be honest I really haven’t ever felt that. I certainly have some transgender feelings inside, but I’ve always pretty much felt like a guy – a guy who really likes women’s clothes!  Being a crossdresser or transvestite I’d say that 80 percent of my dressing has its roots in sex and maybe 20 percent is rooted in gender, though it is hard to pin down exactly.

Caramel: When you finally began crossdressing at home and developing your own female wardrobe, you managed to never get caught.  Were there any close calls?

Sandra:  Well, when I was still living at home, I was always really careful about trying on my mother’s clothes only when I knew I would be alone for a while and never had any close calls.  Once I did get stuck doing some self bondage, but I was able to get free after ten minutes or so.  And then later when I started to get more serious with dressing, I was living alone so there was no risk there.  I guess I just always covered my tracks really well.

Caramel:  Most people I know who are into bondage and discovered it on their own, including myself, seem to remember their first bondage fantasies. Yours began with watching detective movies as a child at home with your family. The scenes with women being bound and gagged, struggling against their restraints had a strong effect on you. Most of those movie scene scenarios consisted of the damsel in distress being used as a man’s unwilling and helpless girlfriend. Since you fantasized about abduction, did you worry that you might be bisexual or gay?

Sandra: I did wonder if maybe I was gay and I tried having sex with guys quite a few times, and have since.  It’s always been okay, but never really rocked my world.  I like the term “heteroflexible” quite a bit, as I’m really attracted to women, but I also like the fantasy of being tied up by a guy against my will.  Sometimes reality doesn’t really match up with the fantasy, though I have known a few guys who were very skilled at the bondage Dom role and have had some fun times with them. One of my favorite scenes was with a very creative male Dom who took the mattress off of one of those fold-out sofa beds, tied me up on the frame, then wrapped me up inside of it back inside the sofa and put the cushions on top, so that you couldn’t even tell that I was inside the sofa!  Then he left me in there for about two hours without any communication, though he was watching for any signs of panic or difficulty breathing. It totally blew my mind and straddled that edge between excitement and complete terror!  Oddly enough, it didn’t involve any actual sex, which some people don’t get at all, but a lot of times bondage doesn’t even have to have real sex to be a thrill. Sometimes just the mental and psychological aspects of it can be just as satisfying, though I know that’s not for everyone.

Caramel:  Oh, I can totally understand and appreciate the power of the mind fuck.

Mummification is considered strange even among some BDSM circles. I think that’s because it hasn’t been explored by a lot of bdsm lifestylers and kinksters, or at least not so openly discussed. To me, the act of having a bound captive is highly erotic and I get a charge out of seeing people fully restrained and almost completely sheathed in clear plastic. Can you tell me about your first experience with mummification?

Sandra:  Oh yes, I love mummification!  One of my first attempts at mummification was when I was young and one evening alone at home I tried to wrap myself up in a clear plastic shower curtain, using double stick tape along the edges. I did a pretty good job and once I was inside the plastic I realized I might not be able to get myself out!  I totally panicked and thrashed around and after maybe fifteen minutes I was able to get my wrists free and struggle out of the plastic.  I was just bathed in sweat and vowed that I’d never do that again – which lasted about two weeks, of course!  Though I was a little more careful about having a means of escape the next time I did it.

Caramel: That sounds like some seriously erotic fun.

I’d imagine that you were always very attractive, yet you were actually shy around girls, weren’t you?

Sandra: Yes, I was terribly shy growing up. I remember some friends at school saying they thought this or that girl was interested in me and I never had any clue at all.  I was the kind who never dated in high school and didn’t go to the prom – I was pretty hopeless!

Caramel:  Don’t feel bad. I was a late bloomer, too.

Most people don’t know that there’s a difference between crossdressers and transvestites. Most crossdressers I know don’t experience sexual stimulation in female clothing but transvestites do. Personally, I find transvestites more fun and interesting than crossdressers and that’s just me. However, mainstream society views transvestism as forbidden and perverted. That said, did you first identify as a crossdresser and do you have any problems with the term “transvestite”?

Sandra:  Hmm, that’s a tough question. I do like the term transvestite a lot, as it just sounds more sexy and more fun, like you say. And I guess technically a shrink would probably label me a fetishistic transvestite, which is perfectly fine. I do tend to use the word crossdresser more often lately, though, as it just seems to be the more common term, and sometimes people who aren’t very familiar with the TG scene find the term transvestite a little confusing, or they want it defined – say, as opposed to transsexual – whereas crossdresser often just goes over easier. For me though, I’ve always found it sexy to dress up like an attractive woman.  It’s not the same as when I was 18 years old and would get a raging hard on from putting on a dress, but there’s still usually a sexual element to it, and I especially like the attention I sometimes get when I dress and go to the clubs, although I’m a terrible tease – all talk and no action!  Unless the guy’s really into bondage!

Caramel: One of the conflicts I had early on was that I wished I’d been born female, yet I was sexually aroused by wearing female clothing, so I didn’t know if I was transgendered or a transvestite. At any rate, my sexual awakening developed with my dressing. Masturbation and dressing up went together like bread and butter to me. However, I went through a lot of guilt and purging every small collection I’d developed of female clothing. Did you go through the same sort of ordeal?

Sandra:  Oh yes, I was terribly guilty about masturbating, and went through those same purges getting rid of the few items of clothing that I’d acquired, and also getting rid of the bondage magazines that I’d bought at the adult bookstores. That puritanical streak and guilt over sex that we have in our culture just causes a lot of unnecessary pain, and obviously doing something taboo like crossdressing just makes it even worse.

Caramel:  Did organized religion play into the feelings of guilt you’d experience after dressing up and masturbating?

Sandra:  My father was Catholic and as a family, we’d sometimes go to mass, but only in a very casual way, so the full-blown Catholic guilt never really got to me. But I do think I inherited some of my parents’ sense of guilt and repression. I remember reading a book as a teenager about sex being something sacred, and that really got to me – I should have purged that damn book instead of the clothes and magazines!

Caramel:  You’ve always been attracted to women, but knew that most wouldn’t be interested in having a transvestite boyfriend. However, you eventually found a girl who was okay with it. Was it just something she was okay with or was it a turn on for her as well?

Sandra:  It’s funny, as I’ve gotten older, I’ve found that it’s really not as hard as I’d thought to find a girlfriend who’s into the crossdressing. My last couple of girlfriends were quite into it and even found it a turn on. In fact, the relationships ended for reasons unrelated to dressing and bondage, though I’m still friends with my last girlfriend, which is really nice. I’d say that the more out of the closet one is, the easier it is to find a woman who’s into the dressing. And with my website being so visible there’s really no way I could keep my crossdressing a secret. In fact, most women whom I’ve dated lately I’ve met at BDSM clubs or BDSM munches, where a group gets together for dinner, so they usually know right away that I’m a crossdresser, even if I just show up in guy mode.

Caramel:  I think the statistics are rapidly changing about women interested in cds, tvs, tgs, and ts’s for the better. And I love that you attend BDSM clubs and munches, too.

So, after you moved out on your own to California, you contacted a transgender support group. You’d made leaps and bounds getting over that self-inflicted torment many transvestites experience and were hoping to become even more comfortable with your inner feelings and sexuality. I know that you weren’t seriously interested hormones and SRS (sexual reassignment surgery), but were the meetings helpful in letting go of the shame of transvestism?

Sandra:  Yes, they were very helpful. The first group I went to was actually in Colorado Springs, and that group in particular was a big turning point for me. Then I went to a few groups in L.A. but by that point I was further along on my way. But yes, I always recommend these kinds of groups for anyone who’s wrestling with shame or self-doubt around crossdressing or gender issues. It can be a huge help to just meet and talk with people who have some of the same issues in common.

Caramel:  I agree that there’s something to find at TG/TS live support groups you just can’t get anywhere else.

In 2001, the transsexual woman who ran the support group you attended put you in touch with a production company that was looking to interview crossdressers for a documentary show for MSNBC called “The Secret Wardrobe”  At first, you refused to do it but changed your mind and told your friends and family about it before it aired. When they saw the show, did they freak out or were they supportive?

Sandra:  It’s funny, I usually wince when I see that show now, but it was a good experience, though I’d like to think I’ve made some more progress in my presentation since then. I basically used the show as an excuse to come out to my family, as I didn’t want them to stumble across it on their own without knowing about it. The funny thing is I still don’t think any of them have actually seen it.  My family all know about my crossdressing and they know something about my website, but for the most part we don’t really discuss it that much, except for my Dad, who surprisingly turned out to have the least problem with it, which was very cool.  He’s a unique guy with a very open mind.

Caramel:  You started shooting self-bondage photos, wrote to the webmasters of Sweet Ties and then had the chance to take bondage pictures with a professional photographer. Were you a bit nervous about having those photos on the Internet?

Sandra: I was really nervous when I first met with my friends at Sweet Ties. I think I had sweat dripping down my face during that first shoot! I really wanted to do the shoot, and it turned out to be a great experience, but yeah, driving back home afterwards I had all these worries that maybe this was going to haunt me the rest of my life, which of course was a waste of energy getting all worried like that. But of course I don’t have plans to run for County Commissioner anytime soon!

Caramel: I think a career in public office is pretty much shot for me too! “Majority Whip” means something entirely different to me than is does to most people.

So, how did you choose the name “Sandra”?

Sandra:  Sandra was the name of my favorite babysitter back when I was a child. I thought she was so worldly and sophisticated and I really had a crush on her.

Caramel:  That’s sweet. I have some babysitter fantasies, but no crushes that I can remember.

After living in L.A. for several years, you returned to Colorado and settled in Denver. What influenced your decision to move back to Colorado?

Sandra:  I always had mixed feelings about L.A. for all the years I was there. It’s a great city with a lot going for it, but it’s a hard place to live if you’re not rich and the congestion and pressure of the place can really grind you down. The last few years, I started wondering if I could continue running my website living someplace else and maybe coming back to visit L.A. from time to time. I spent the summer in Denver last year and had a really nice time and did quite a few shoots, so it just seemed like it might be time to make the move.  I’ll know in a year or two how it’s working out but I’m pretty hopeful.

Caramel:  I think that with the continued success of  Trannies In Trouble, you’ll be able to live anywhere you choose someday. You certainly look well-off enough. I love your sense of style. Sometimes the clothing you wear is what most people would expect to see at a bondage site. However, you sometimes look as though you stepped out of a Neiman-Marcus catalog. Do you have an adoration for couture women’s wear?

Sandra:  I’ve always loved women’s business suits and office wear, so that’s the kind of look I’m most drawn towards. If I had the budget, everything would be Neiman-Marcus!  But to be honest, a lot of times I’ll just find amazing things at thrift stores. A while back I found this amazing black velvet dress with tulle inserts for ten bucks and several people have written and commented on it.  I always love that feeling when you discover something like that hidden on a rack somewhere.

Caramel:  You’re a non-smoker, very athletic and I understand you enjoy hiking. When did you start hiking and what else do you do to keep in shape?

Sandra:  Hiking up mountains is my main interest, which I’ve really only done more seriously the last five years or so. When it’s not hiking season, I just go for walks or use the elliptical machine.  But my favorite thing is to be out in nature and hike to the point of exhaustion at the end of the day.  I love that feeling. And yes, I’m not a smoker but I recently did some smoking pictures and really enjoyed how they turned out. I’ll have to be careful about doing more, as I really enjoyed puffing on that cigarette! They do sooth the nerves and I love how smoking looks, so I should find some herbal cigarettes or something or I could easily get hooked!

Caramel: I’m not going to advise you to smoke, but you do look killer in the smoking photos. It brings back to mind glamorous images of the 30’s and 40’s and the smoking fetish world is ginormous today.

There’s an erotic mix of transvestites, transsexuals and genetically born women at Trannies In Trouble. How do you go about finding other models to work with for your website?

Sandra:  Quite often, people will just write me and send some pictures to be considered for the site. Sometimes girls will write who have a really stunning look put together, which is always a delight. Other times I’ll meet people out at the clubs or at play parties, but it just varies. My least favorite task with the site is when I have to turn someone down for modeling. I always wish I could shoot with everyone, but with running a paysite, I have to be rather picky, but it never feels good saying no to someone who’s into bondage and wants to be photographed, as I know what it’s like to be there.

Caramel:  There are well over 150 high quality videos at your site. Do you shoot all the work yourself or do you enlist the help of other photographers also?

Sandra:  I’ve shot with quite a few different photographers, and have worked with a few regulars who are also good friends. My friend Chainguy is terrific and I’ll shoot with him every chance I get back to L.A. But I’m always looking for fun and sane people who like bondage photography.  Finding photographers who are also skilled bondage riggers can be tough, but I’ve met many good people over the years.

Caramel:  I’m sure that if some professional photographers in your area read this interview, you’ll get some new requests for shoots. If you do, and it produces good results, I hope we’ll talk about that in our follow-up interview. But personally, I think your content is superb and needs no outside help at the moment.

Where do you acquire the clothing and gear you use for Trannies In Trouble?

Sandra:  The clothes I usually get at thrift stores or from catalogs. I like Venus and Express and some others, or sometimes I’ll just go shopping at the mall or at Ross.  here was a thrift store in Hollywood called “Out of the Closet” that I just loved, which was incredibly gay and I found quite a few things there. As for bondage gear, I’ll sometimes get things online or from vendors at events like DomCon. I’ve had several generous friends who have given me bondage gear too, which I always greatly appreciate!

Caramel: The content at your site is highly erotic but there’s no hardcore action.  Did you make a conscious decision not to do hardcore for any particular reason?

Sandra:  Yes, that was a conscious decision. I have nothing against hardcore action, except that personally it doesn’t do a lot for me, and I know if I went there, I’d feel uncomfortable with it. I’ve had moments where I’ve thought of doing some hardcore shots, but my heart’s never really in it. I know some people would love to see that, but I also hear from quite a few members who say that they like the site because it isn’t hardcore. And obviously if someone really wants to see hardcore action they have lots of sites to choose from other than mine.

Caramel: I love hardcore action, but your content is so intense, I don’t miss it at your website. There’s more than enough sexuality there to get off on. When you’re struggling against your restraints, I can literally feel the tension, especially between my legs.

So, what perils are coming up next for Trannies In Trouble?

Sandra:  I’ve always wanted to do an extended kidnapping scene. videotaped over the course of a day or weekend, though the logistics and safety concerns would have to really be worked out.  Something like that would be a real thrill though.  But I’ll keep shooting bondage for many years, I’m sure. Heck, I’d be shooting pictures even if I didn’t have a website for them. I’ve just always found bondage photography to be super sexy! I still remember the first time I walked into an adult bookstore way back when and saw my first bondage magazine and my pupils dilated. I just knew that someday somehow I wanted to do that.

Caramel:  It’s crystal clear to me that what you’re doing is something you’re passionate about and I know your other members feel the same way.  Thank you so much, Sandra.

Show your support for Sandra’s independent website Trannies In Trouble!

11 thoughts on “Interview With Sandra of Trannies In Trouble”

  1. So nice to see my friend Sandra–for over 2 years I went to the Trannies in Trouble Friday night parties that Sandra hostessed –so fun–she has been so sweet to so many people, especially to this ole tramp!!! Thanks for the great interview, Cara–thanks for the memories, Sandra!!!

    1. I’m glad you enjoyed it, Blair and those parties must have been fun! I wish I knew about your sexy blog earlier. I’ve just added it to my blog roll (Friend’s Blogs). xoxo Cara

  2. Love the professionalism and neatness of all the bondage photos. I am straight but love dressing up and hav been in one of my maids dresses all day. Wife doesn’tind aong as i am busy cleaning the house.
    She will bind and gag me but prefers the locking hospital restraints to save her nails. We have experimented with chasity

  3. Great interview Mistress Caramel, and Sandra you really have a great site!
    I really enjoyed the range of questions presented, and Sandra you even answered a few of the questions that I was quite curious about. Best wishes and continued success to both of you!

  4. Great interview. Sandra is the best bondage model in the business today and I look forward to her updates. I would love to see a video about an extended bondage fantasy. Thank you.

  5. As a friend of Sandra’s from L.A., thanks for a great and very thoughtful interview, Caramel. Also, love your site which I was not aware of before, so congratulations to both of you! 😉
    Sandra is a special and super-nice person, so I was lucky to meet her and become friends.
    Blessings to you both,
    Kim

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