A practice walking trip over a long distance

A long-distance walking practice I’ve been quietly observing this community for a good while, and I figured it was time to take action. My idea was simple: a long walk. I have the spot picked out, but after reading through all the advice and warnings here (thanks, everyone), I felt like testing the waters first. My environment is somewhat different from what most of you experience. I live in a very rural part of Maine, which means no streetlamps, paved roads, sidewalks, or other structures nearby. The road we share with three other homes raises my main concern: someone driving home late might spot me and recognize me. Even when cross-dressed, I’m the only one on that stretch of road who fits my build. So anyone seeing me won’t just see something unusual—a person in women’s clothes—but will likely know exactly who it is, which heightens the nervousness significantly. Visibility is another factor. When I usually walk at night looking for a dog or doing chores, I carry a flashlight, but that doesn’t work well when my hands are cuffed behind me. My initial thought was to use a headlamp—those LED lights on a strap worn around the forehead (or wig in this case). But then I realized that standing quietly in the woods by the roadside wouldn’t work with a bright light shining forward, especially since my hands are tied and I can’t easily reach up to turn it off. So for plan two, I grabbed one of those keychain lights attached to a lanyard so I could hold it in my hand; if needed, I can angle myself sideways to shine the beam ahead. Next came footwear. I wanted heels, but since this is a gravel road, narrow pointed stilettos are out. They would sink into the ground and leave tracks that look nothing like our local deer’s hooves, which might give away my route from and back to my door. The solution was a pair of platform sandals featuring a 2-inch base and a 4-inch heel—high enough to feel substantial but stable on loose dirt. Regarding restraints, I have four leather cuffs. Based on the forum tips about locking them using a luggage lock through one of the holes in the strap’s loop, that issue is resolved. I chose a chain for my belt so it’s easy to attach things, plus another long chain running from the back of my collar down to nearly ankle level. This splits into two chains connecting to the ankle cuffs and prevents dragging. Since this was a trial run, I decided not to leave the keys out at home yet; instead, I need to retrieve them later but will carry them with me in an evening purse. Starting to get dressed, I inserted a butt plug (plug), then put on panties, pantyhose, and a tight panty girdle over them. After that came a bra and large silicone breast forms. As someone who has been cross-dressing since childhood, clothing isn’t hard for me. I layered a black full slip under a blue dress—it’s long-sleeved and reaches mid-thigh. It’s not so much about discomfort showing more of my somewhat non-girlish figure; there are mini skirts and crop tops available if needed—but it is October, getting chilly around 50°F with wind picking up by the time I head out. Makeup comes next: lots of blue eyeshadow, long false eyelashes reminiscent of 60s girl groups, pink blush, and bold red lips. Then big hoop earrings and a penis gag (gag), topped with a long brunette wig that goes over the gag strap. The shoes are already on as I attach the collar and the long chain using luggage locks to connect everything to the ankle cuffs and cross-chain. It takes some fiddling to shorten the cross-chain just enough so it’s bothersome but still allows movement. The waistchain slides on easily, then things get interesting. I planned to use all luggage locks (lock)—I have eight of them—but trying to thread two cuffs and a chain through that tiny metal hasp behind my back proved impossible without help. Of course, I couldn’t find any larger replacements anywhere nearby, so I ended up using just 2 locks, which means things are looser than originally planned.

Finally ready, I head out toward the road. The first hurdle is the front yard; it’s not perfectly flat, and bumps do strange things to platform heels. I kind of lurch forward onto the main road but make it without damage, though my heart rate spikes. Once on the graded gravel road, progress gets easier. Walking was possible within the limits of my hobble (cuff), and holding the extra chain in my hand kept it from hitting my ankles too much. Between the evening purse and that small flashlight, I didn’t have to move my hands excessively. Fortunately, there was enough moonlight for me to see the road clearly. The first 100 yards go well with steady progress, although keeping the chain tight enough to avoid ankle strikes remains tricky. The wind blows my wig hair everywhere, constantly getting in my eyes—something I can’t fix since my hands are locked behind me. Turning into the wind and shaking my head just right helps somewhat but slows me down further. I don’t know how girls seem to master that quick little head flip to rearrange their hair by age eight or so. I start finding a rhythm and relaxing a bit when something crashes off beside me—it sounds like someone had a violent sneeze followed by rustling noises, causing me to jump straight up in surprise. Landing back on my feet while staying upright on the heels sends my heart pounding again. I soon realize I’ve startled a deer that hadn’t smelled me due to the wind direction; it snorted to catch my scent and then bolted. Deer are common here. Had it been daylight, I’d probably stop to watch, but at night it was quite startling. I waited a minute for my heart rate to settle before continuing. In total, I covered just over a mile while staying locked the entire time (restraint). Returning home, I opened the evening purse and pulled out the keys. It took another 20 minutes of effort to free my hands because the locks wouldn’t stay put while inserting the key, but eventually, I managed to pin it against the chest freezer and got loose.

As a training cruise (walk), I learned quite a bit—for instance, using tape around the hips or wearing the recommended belt helps shorten my stride. I tend to overthink these details because planning is half the fun. Also, hobbled ankles combined with drainage ditches could pose real risks if a car approaches. Shoes remain an issue; next time I’ll likely switch to boots for better stability. As long as they aren’t stilettos, I should be fine regarding tracks and sinking too much. Next time, I plan to leave the keys out at my destination but will probably still carry the purse—it’s one more girlish touch (master) and a minor annoyance, which is another reason to do this. Thanks for reading and all your suggestions on the forum. Deidra