Tag: Crossdressing

  • 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.

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    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
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  • 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.

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    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.

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    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.

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    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
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  • 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.

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    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.

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    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.

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    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
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  • 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.

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    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!

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    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

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  • Crossdressing, Sissification, and Genderf*cking

    Crossdressing, Sissification, and Genderf*cking

    Cross dressing is not in itself an act of submission. It has different meanings for everyone who puts on (or gets put in) typically feminine clothing. It is a mask for some and a reveal for others. The particular way I enjoy playing with it is through the lens of dominance and submission. I would like to share what I do and what I get out of it, and what I imagine my partners get out of it.

    I like to make male identified people (referred to as men from here on) wear girls’ panties. A man with no clothes on is still a man, but when I begin to dress him, his masculine identity melts away. Of course the newly minted she has no experience being a girl, so it is up to me to train her, give her tips and tricks on being girlish. In this play I use the word ‘girl’ to mean someone inexperienced, naive, and fairly dumb. She has no power, she is a flimsy stereotype, and she is very slutty.

    Lace garters and dainty stockings frame and perk up her bum so sweetly. A corset defines her waist, perhaps shoes are slipped on to lengthen and slim the legs. These clothes are confining; they restrict and streamline movement to force her body into a more female pose. Sometimes make up is necessary and depending on the mood of the scene, I will paint her face carefully (the elegant missy) or crudely (the sloppy tart). Wigs have an incredible effect on framing and softening an angular face. What used to be considered male genitalia, I know refer to as a deformed or engorged clitoris. There are a rare, dedicated few who will take the extra step to receive a temporary—and very safe—breast augmentation with a saline infusion.

    The man has disappeared completely. He is locked behind the identity I have forced or coerced him into. She is my sissy.

    As I dress and powder the girl, I talk her into a state where she understands what her duties are: to be demure and polite, to obey whatever demand is made of her, and know that she deserves whatever she gets. She is “asking for it” by looking the way she does. It can feel very humiliating.

    Anything can happen from here, from runway coaching to gestures, seduction techniques to slut training. We may simply sit in the parlour and have tea. I may want to see them spread themselves out before me. Wherever the scene goes, the underlying idea is that I have transformed a man into something I find pleasing and quite amusing, and I am using her as my plaything.

    If this is something you’d like to explore for the first time, I recommend starting with underwear. It’s easy to find and quick to take off if it gets uncomfortable. If the notion of getting a hold of feminine underpants is not where you or your partner are at, start by playing with language. Wiggle those hips and play on.

    Mistress Isobel is a lifestyle and professional Dominatrix from England. She is living in Toronto, a gloriously kinky town. She has been exploring BDSM for 6 years and is always learning new ways to get into people’s heads via their body. With a respect for strict traditions and a spirit of cheeky fun, she whispers to the secret part of you that wants to stretch out and play.

    Visit www.IsobelHerself.com for more writings and information on live sessions. Mention this article and get a complete cross dressing session at a loyalty rate.

    Follow Mistress Isobel on Twitter @IsobelHerself


    Feature image courtesy of Mistress Isobel
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  • The Intimate Thoughts of a Crossdresser

    The Intimate Thoughts of a Crossdresser

    The truth is that there is simply no straightforward, one simple answer as to why men crossdress.  If there was, you probably wouldn’t be reading this article: the discussions on this taboo subject would have been settled a long time ago and many men would be free to express their femininity without fear of ridicule and rejection.

    In my personal experience, the fascination with woman’s clothing started when I was very young.  I must have been about 5 or 6 years old, and I remember going to great lengths to get access to my mom’s lingerie.  My most vivid recollection goes back to my teenage years, anxiously and secretly purchasing pantyhose from a local shop and then wearing them under my clothes while walking home.  I felt and still feel to this day, a need to wear woman’s clothes almost on a daily basis, whenever I can find the private time.

    To be honest, I can’t quite explain where these feeling come from or why they started in the first place. Many times I find the feeling hard to control, especially if I go a few days without dressing up.  The mass media likes to reason that crossdressing is a sexual perversion, and so they naturally see the desire to crossdress as purely for sexual gratification.  The problem with this theory is that when I (and most other crossdressers) first felt the desire to crossdress at a very young age, we didn’t know what sex really was or had any sexual feeling.  I often would go to sleep wearing my homemade stockings and carefully taking them off in the morning under the bed sheets and hiding them in the drawer under my bed before my mom would walk into the room.

    There are many misconceptions and stereotypical views about crossdressers, one of them being that most people believe crossdressers are homosexual and desire to be with other men.  Although there are cases where this is the fact, the truth is that most crossdressers are heterosexual men.  A lot of them are married, have families and lead regular lives.  For many, crossdressing goes through several evolution stages and sometimes ends at the point when the crossdresser desires a transition to living full-time as a female.  Many crossdressers describe the need to crossdress as ‘feeling more comfortable wearing woman’s clothes’.

    This is sometimes coupled with the desire to be seen as a woman.  To not simply dress like a woman, but behave like one as well, to wear make-up, lingerie, shoes and otherwise, pass as a woman.  Then there are others who crossdress purely for sexual excitement.  Crossdressing covers a wide spectrum and therefore it is hard to define them as any one group.  Some men crossdress because they are unhappy being men and wish to escape the male role.

    Let’s face it, women have way more selection when it comes to fashion and are allowed to express themselves in many distinct ways.  Just walk into any women’s fashion and beauty mall and then walk in the men’s section and you’ll know what I mean.  For me, I love feminity! I love the feeling of being a woman and wearing all the gorgeous makeup, soft sexy dresses, high-heeled shoes and exploring the female realm. It’s such a real thrill for me and countless other crossdressers.  I highly admire women and their beauty and their many feminine qualities. I regard the female physique as a work of art.  There are also others who don’t mind the male state, but like to put on women’s clothes occasionally. Some men crossdress simply to make a passing social or fashion statement, and some because they have emotional needs that can only be met by the comfort that wearing women’s clothes gives them.

    Sex, particularly with other people is not the main reason why most men crossdress and masturbate because they are now themselves, the ideal woman, and the man no longer has to fear rejection, criticism or disappointment which might come with attempts of intercourse with a woman.  The fact is that women crossdress all the time and are free to wear men’s clothing without fear of ridicule or turning heads.  It is not uncommon to see a woman walking down the street wearing men’s apparel.

    Men on the other hand are supposed to fit into a very rigid gender role and are not able to freely express their femininity beyond maybe, crying at the movies.  The true reason why men crossdress remains somewhat of a mystery to this day.  Crossdressing is an intensely personal activity for many men, often done in secret, late at night and sometimes guilt-ridden.

    Crossdressers usually will do this in secret when the wife and kids leave the home.  They have their day planned!  They will even go so far as to shave off their body hair, take a hot, perfumed, bubble bath, and dress in something silky.  However, many crossdressers just enjoy the feeling of certain material against their bodies and go no further than dressing up as a woman.  More and more crossdressers are “coming out of the closet” and if lucky, their wives will accept the way they are as long as they keep it private and away from friends and family.

    In my particular case, my girlfriend knows that I crossdress and she has accepted it, which I am very appreciative of her for doing so.  Apart from my girlfriend, no one in my family knows to this day, and this can be psychologically challenging for me at times.  For the past 45 years, I have done a good job of concealing my other self.  Most crossdresses become very good at being Dr Jekyll and Mr Hyde.  Today, I enjoy being Marcy whenever I can and have taken many steps to perfecting my female persona.

    Marcy’s biggest goal is to be as passable as a woman as possible.  I haven’t ventured out of my house as a female but strongly hope that one day soon, I will be able to freely be Marcy in and out of the house in a place where I will not have to fear weird stares, ridicule and rejection.  I’m optimistic that as our society grows more accepting of diverse gender expression, we will see more crossdressers stepping forward to share their stories and feel more open about discussing the topic of crossdressing with family and friends without the need to justify their behavior, and are no longer shamed by everyone.

    I know some people out there will mock me and say that I need help.
    I say to you, you have never have never walked in my high-heeled shoes.
    Judge me if you want, it makes no difference.

    Marcy Simpson

    Founder of Crossdresser Society.com

    Featured Image courtesy of Marcy Simpson.

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