Monthly Archives: August 2026

life in general, websites

I’ll Do It Someday

Leave a comment

I was already working on this blog post when someone I’ve been emailing with for a while left a comment on Fetlife regarding modeling. They wrote that we would shoot someday, implying that they weren’t quite ready to commit. I get it. It’s a big decision to be on a website like mine that’s seen all over the world. And that decision at the time can feel very significant. I remember the first time I shot with SweetTies way back in the day before Trannies in Trouble even existed, and just how nervous I felt driving down to that first photoshoot in San Diego. (Back then they also had a small site that featured CDs in bondage though it’s no more.)

So I understand the hesitation. At the same time, I really think the risk of being recognized and outed on my site is very small, especially if you’re a crossdresser. When I’m out and about as a guy, I’ve never been recognized by anyone. If someone saw me in boy mode and said, “Say, are you Sandra Gibbons by any chance?” it would absolutely blow my mind. That has never happened even once after all these years, and I doubt it ever will. (Similarly, I keep my body fully shaved—arms, legs, chest, everything—and no one has ever noticed or commented about that, even when going to the gym.) Those of us who are crossdressers tend to look SO different anyway once we’re dressed so it’s very doubtful anyone would ever recognize us.

Of course, if you’ve transitioned and are taking hormones that’s a different story, but even then, the chances of being recognized are probably quite small unless you go a fetish or trans event where there may be people who are bondage fans. At the same time, if someone recognizes one of the models out in public, it probably means that that person is into CD and trans bondage—there’s no other reason anyone would ever look at my website unless they were turned on by it or at least intrigued.

I’ve had so many experiences running my website but there are still things I think of doing but then invariably put off. Some of them are just mundane things like hikes I’d like to take up some of the taller mountains around here, someday. I’ve also thought about how cool it would be to make a documentary about crossdressers who are into bondage, but it’s one of those “Yeah, when am I ever going to get around to that?” kinds of thoughts. Besides, it would be really hard to find a group of CDs who would be willing to go on camera and reveal themselves in the candid and vulnerable way that the subject would deserve (blurring out everyone’s face just wouldn’t work). It’d be a good idea, but I know it’s just another thing that’s not gonna happen.

The funny thing is that over the years there have been probably thirty or forty crossdressers and trans girls (and probably even more) whom I’ve said yes to about modeling, but when it came time to put a date on the calendar it was difficult for them to commit, or they were too busy, or any number of things interfered, and so eventually the opportunity slipped away. If someone repeatedly says, “Well, not right now,” then after a while I finally just have to move on. Somewhere out there there’s an alternate universe with a whole group of new models and never-before-seen galleries on Trannies In Trouble that just never happened. Some of those girls were really cute and would have made terrific models on the site. But I’ve found that if a year or two passes and someone still hasn’t committed to it after I’ve said yes then it’s probably not going to happen.

When I was younger, one thing I wanted to do in life was become a good crossdresser. At the time I had very little experience, and I didn’t want to grow old and realize that I’d never gotten that good with makeup and dressing. There are certainly plenty of crossdressers who are more skilled than I am, but I do a pretty good job. And that desire, to be a good crossdresser, was one of the main motivations behind making Trannies In Trouble. I’ve certainly been tied up so many times that if I never did it again I’ve still had way more than my share of excitement. At the same time, as I’ve gotten older I have far more interest in tying up other girls rather than getting tied up myself. But if I hadn’t improved my dressing skills and hadn’t learned how to do bondage photography it would have been a big regret for me later in life.

One thing I have learned from running my website is that if you have persistent dreams and desires—wanting more experience in dressing, for example, or wanting to get tied up for real with a rigger who knows what they’re doing—well, it’s a good idea to make those things happen and not put them off too long. It’s a cliché because it’s true: Someday never comes. And this message is aimed at myself as much as anyone. Besides, the time is going to pass and leave us behind whether we fulfill our deepest desires or not.

colorado, life in general, movies

The Chance Skydiver

Leave a comment

One evening when I was about ten years old, my friend Robby and I wandered over to this traveling amusement park that was being set up a couple miles from home near a shopping center. The place was empty and not yet fully set up. I’m surprised there wasn’t a fence, as you could walk all around the deserted grounds. There in the dark was this Ferris wheel called the Skydiver that looked like the coolest thing I’d ever seen. The way the sleek cages spun horizontally blew my mind. I wanted to ride it once the fair was up and running but the problem was that I was a scaredy-cat! It looked so exciting, but I never worked up the courage to go on it. I was afraid it would turn into a puke-fest or that I’d otherwise freak out. Robby thought it looked pretty cool too, but he wasn’t exactly racing to go ride it either. I think if he’d been more enthusiastic, I probably would have followed his lead.

Even when we went back the next day and the rides were up and running, I still chickened out. In the grand scheme of things it’s of no importance, but in a funny way I still regret that I never rode that thing since most of the Skydiver rides have long since been retired and I haven’t seen one at an amusement park in decades. I do enjoy watching this POV video on YouTube though and yeah, that horizontal spinning motion does look vomit-inducing.


It was only later that I learned the ride was manufactured by Chance Rides Company, who also made the Zipper, which has apparently had a much longer production history. I rode the Zipper (twice, I think) decades ago, and while it was scary, I handled it well enough and didn’t lose my lunch. I’d never do it again though!


One ride experience that was pretty awful for me though was riding the original Mr. Twister roller coaster at Elitch Gardens in Denver way back when. It’s long since been torn down but was pretty legendary at the time. I had no idea what I was getting into. The first drop absolutely terrified me, and I remember the friend I was sitting with looking over at me and laughing at the look on my face. The other drops weren’t nearly as bad but that first one must have messed up the balance in my inner ear or something, as I felt off and queasy the rest of the day at the park. I tried to act like I was fine, but I couldn’t find a way to feel normal again till probably that evening. Everyone else seemed to be having a good time but I just felt dazed and a bit guilty that I couldn’t join in the fun. I didn’t want to be a buzzkill, but I just felt like crap. If I’d had access to a bed in a darkened room, I would have lain down for the rest of the day. I’m glad I rode it but if I’d known I wouldn’t have.


The Skydiver though is the one ride where I still wonder why I chickened out. (As an aside, it shows up in the background at the end of the classic movie The Warriors.) If I were to see one at a traveling amusement park, I would have to stop the car and go look at it, but I’d probably still not have the nerve to get on it, especially at my age. I still think it’s probably the coolest looking ride ever made—more aesthetically pleasing than the Zipper. I probably should have ridden it at the time even if I’d hurled.