Tag: Trannies in Trouble

  • Advice for fetish models and photographers into bondage

    Advice for fetish models and photographers into bondage

    To run a bondage website or any small niche fetish site, it has to be something that you’re just dying to do and that you’d be doing even if there were no money in it. It really is a lot of work and I’m sure there are easier ways to make a living. It’s the kind of thing where a person has to be a little crazy and obsessive to keep doing it, or else after a few years you’ll find that it’s a grind and not much fun anymore and it’ll be time to look for a real job.

    I certainly have some days like that where planning the next shoot and editing the next pictures feel like a chore but for the most part it’s great, and it has been extremely satisfying. These have certainly been some of the best years of my life and I just want to keep them going as long as I can. I only wish I’d started ten years earlier.

    13

    One other thing to consider is that if you’re running a fetish website as your full-time work there’s always that little question that comes up when you meet someone new, “So what do you do?”

    When I was just starting out I gave vague answers about web design but I felt uncomfortable with the question, as I wasn’t sure that my website was really going to be successful or how long I’d be doing it. Now that it’s been online for twelve years I mostly just tell people the truth, that I run an adult or fetish website. Most of the time it’s a non-issue, but I’ve certainly run into people who’ve been uncomfortable or who have told me to my face that they disapprove.

    And I’m a pretty sensitive person so even now those responses can sometimes rattle me a little, but it comes with the territory when you’re doing something out of the mainstream. And yes, my family and friends all know about the crossdressing and my website, with varying degrees of acceptance. I just find that keeping it all a secret makes me feel depressed and anxious so I find it’s easier to just be fairly open about it when the subject comes up.


    Images courtesy of Sandra Gibson
    Have an amazing experience or tips you like to share on SimplySxy? Drop us an email at editorial@SimplySxy.com!

  • 4 Questions with Sandra Gibbons of Trannies in Trouble

    4 Questions with Sandra Gibbons of Trannies in Trouble

    SimplySxy: Can you describe what it’s like for you physically and what thoughts run through your mind as you’re being bound and gagged?

    Sandra:  For me, the element of bondage that turns me on the most is the feeling of being out of control or in a situation that’s potentially dangerous, or where I may be used sexually, or worse. But of course it’s all grounded in fantasy. I don’t really want to put myself in a truly dangerous situation or end up traumatized or injured, and of course if I do anything sexual in a bondage scene, my partner and I have probably gone over our limits and expectations beforehand and ideally I’m playing with someone I feel I can trust (of course, there have been exceptions).

    So the thing about bondage, or the type of bondage I enjoy, is that it’s a kind of role playing, although there are ways to play that are edgier than others. I’ve certainly done a few play scenes aside from picture-taking where I later thought to myself, well, that could have gone really badly. But I’ve been very lucky in that I’ve never gotten into a scene where I felt like I was in real danger, and for the most part I’m very cautious and selective about who I’ll do this stuff with.

    9

    SimplySxy: There are a variety of binding, rigging and gag materials to choose from, such as nylon, leather restraints, leg-irons, duct tape, ball gag, duct tape. Which are your favourites?

    Sandra:  My favorite is probably duct tape, especially for duct tape gags that are wrapped across the lips and cheeks and encircling the back of the head, and with a big pair of panties shoved in the mouth first. This makes for a very effective and tight gag. That feeling of being “gagged” and of having your mouth stuffed and sealed up is probably the main thing that sends me over the edge. Being taped up and restrained with duct tape is great too, although obviously I use rope the most on my website, as that’s the default bondage material that most of us love. Leather gear is also great and can give more of a fetishy look.

    11

    SimplySxy: You look stunning in the pictures. Apart from the elaborate outfits and great set, what are the preparations required before each photo shoot session? 

    Sandra:  Thank you so much. Taking the photos has definitely become a more involved process over the years. When I started out, I’d just get ready and kind of wing it and improvise as we went alone. Now I usually try to come up with a plan of what we’re going to shoot, quite often taking suggestions from what the model likes if I’m going to be working as the photographer. But there’s usually about a full day of preparation before most shoots, getting things ready, deciding on the outfits and coming up with some ideas. And quite often the idea for a shoot will be changed or even scrapped completely once we get going. A lot of it is a process and depends on who’s involved, what they’re into, how much they’re turned on by bondage, how intense they like it, and so on. I wish I could streamline things and make the process go faster but as the years pass it seems to be going in the other direction.

    10

    SimplySxy: Thank you for taking your time out Sandra and before we end off, what is your definition of “sexy”? 

    Sandra:  Thank you again for having me, this has been fun! Well, I’d say for me “sexy” is that feeling of being weak in the knees when you realize you’ve gotten yourself into a situation a little over your head. And it usually involves a tight skirt, a tailored blouse (with a hint of spandex), five inch heels, stockings and a roll of duct tape.


    Images courtesy of Sandra Gibson
    Have an amazing experience or tips you like to share on SimplySxy?
    Drop us an email at editorial@SimplySxy.com!

  • Bondage Crossdressing and why it turns me on

    Bondage Crossdressing and why it turns me on

    Thanks so much for having me here. Well, yes, I’m a crossdresser and a huge bondage fetishist. For me, the two interests have always been there for as long as I can remember. For me, crossdressing and bondage are primarily sexual fetishes. They turn me on. And the style of bondage that I prefer the most is damsel in distress bondage, which as the name suggests has an element of danger or peril in it, though quite often it can be done in a rather tongue in cheek manner. The things that turned me on as a boy were detective movies and TV shows where a smartly-dressed woman ended up tied up and gagged. I always identified with the damsel and wanted to be her. I didn’t want to see her actually being hurt or raped or anything really bad happening to her, but the element of danger and the sense that she was in a situation where she might be forced and used or come to a bad end was terribly exciting. Sometimes I would see these shows as a child and pray that none of my family there in the den with me could pick up on how fascinated I was by these images on TV.

    5

    So from an early age, I was intrigued by and attracted to women’s clothes. I didn’t have a sister, but like many crossdressers, when I was a teenager I would sometimes try on my mother’s clothes when I could get away with it and remember it being a huge thrill. I know it sounds, well, I hate to use the word creepy, but yes, some people would see it that way. But believe me, if you’re a “CD” you have to find the clothes somewhere when you’re starting out, and if the opportunity arises you’re probably going to act on it, especially at that age when all the hormones are racing.

    Many CDs will deny that there’s a sexual component to their dressing and for some of them I think that’s true, that it touches something else in them, or perhaps they have a stronger feeling of being transgender or gender dysphoric, (basically deeply dissatisfied or uncomfortable with one’s “assigned at birth” gender). But for me it definitely has its roots in fetishism. I think that’s why I now try to take sexy pictures, because I’ve spent a lot of time looking at these kinds of fetish images and imagining myself in the role of the damsel in distress.

    6

    As for gender, yes, I’ve certainly had those thoughts wishing I’d been born female, especially when I was younger. I can’t say that I’ve ever been thrilled to be male, but at the same time it hasn’t tormented me in the way that a trans person likely experiences. But so much of my dressing started out as a sexual thing so it’s pretty clear to me that I’m a crossdresser or to use the clinical term, a fetishistic transvestite. There is that whole other question – do crossdressers fall on the trans continuum? Some days I’d say yes, some days no. And in the trans community, where there is very little agreement about much of anything, you can safely say that opinions vary. One thing I remind myself though whenever I wish I’d been born female is that females for the most part are not fetishists – it’s pretty much a male game, although there certainly are women who are into bondage, some heavily into it. But they’re not into the clothes the way that a CD or transvestite is. So obviously if I’d been born female, this whole website thing most likely wouldn’t be happening for me.

    7

    As for the clothes themselves, I’ve always been drawn more to clothes that are “dressy”: skirts and blouses, stockings and high heels, and my favorite look is probably the sexy secretary or sexy librarian. I know these are clichés and some might argue that I’m just objectifying and fetishizing women, but that’s what happens with desire. We get focused on something that turns us on and there’s no arguing with it as to whether it’s objectifying or not, or politically correct. And well, I love to be objectified myself. I find it very sexy if I know someone likes my pictures enough to get off to them. That’s really my goal. And some of my favorite fan mail is to hear from guys who say, “You know, I’m a straight guy who’s never had any interest at all in crossdressers but I get really turned on looking at your pictures.” That’s just the best!


    Image courtesy of Sandra Gibson
    Have an amazing experience or tips you like to share on SimplySxy?
    Drop us an email at editorial@SimplySxy.com!

  • Trannies in Trouble

    Trannies in Trouble

    Well, for many years I had fantasies of modeling for bondage pictures, so it’s been a long path to finally get to Trannies In Trouble. I’ve been around quite a while and plan to continue on as a bondage photographer once I feel I’m too old to be in front of the camera. But when I was young and in college, I used to go to adult bookstores to look at bondage magazines – this was really before the internet had become popular – and I remember what a thrill it was and how forbidden and even risky it felt to go to these stores. The first time I saw a wall of bondage magazines in an adult bookstore, I was stunned. It was like, OMG, I’m not the only one who’s into this stuff. Nowadays erotic material is so easily available that it’s really lost some of the charge that it had back when you’d have to go to a special naughty bookstore and summon up the courage to walk through the door, usually hidden around back.

    4

    But even back then I wanted to pose for bondage pictures and take photos of other girls and other CDs. There weren’t many images of CDs in bondage but there were a few and I remember wondering if I could look good enough to take some nice pictures someday. I started rather late with dressing more seriously, and probably didn’t have a halfway decent “look” put together till well into my mid-thirties, and then when I finally moved to L.A. back in 2001 I met up with a nice group of people who ran the website “SweetTies,” which is still online. I was able to pose for some photos for them a few times, and then when they moved away, I started taking pictures on my own. It sounds crazy but I actually came up with ways to tie myself up and take photos of myself with the camera on a tripod, using a remote control. It was very crude and took forever but some of those photos are still on my website and some of them were pretty effective. I’d like to think that I’ve improved some since then and I’ve certainly met many excellent photographers and models over the years who have helped out so much, especially my friend Delilah Knotty, with whom I’ve been shooting for years. She no longer models on my site but that girl still ties my ass up tight!

    3

    But basically the whole concept of Trannies in Trouble was just to do damsel in distress style bondage but feature crossdressers as the stars of the show. This is a very narrow niche, obviously, and there are very few websites in this genre. There is some overlap though, of course, with damsel in distress sites featuring women, as many of my customers enjoy seeing both women and CDs in bondage. But like I say, it’s a fetish and many of the guys who like these sites are crossdressers themselves, or trans, or guys who simply identify with the image of a woman tied up and in danger.


    Images courtesy of Sandra Gibbons

    Have an amazing experience or tips you like to share on SimplySxy?
    Drop us an email at editorial@SimplySxy.com!