BondageDating

A Late Night Outdoor Adventure in Leather and Silk

With so much else happening in my life right now, I'm struggling more and more to carve out time for Mira. When the rare chance comes up to dress up, I…

member_2ec0e08e46 6 Sept 2026 #1

With so much else happening in my life right now, I’m struggling more and more to carve out time for Mira. When the rare chance comes up to dress up, I never want to let it slip! Here is a true story about an outdoor adventure I had late one night recently. My girlfriend was leaving for work, which meant I’d have the house entirely to myself from evening until well into the morning. Since I knew this date was coming, I made sure to prepare thoroughly so as not to squander this special opportunity. The week leading up to it, I had already chosen my outfit but decided to splurge a bit more. I ordered a beautiful pair of black silk seamed stockings and some long faux eyelashes because my current set needed replacing badly. After seeing my GF off at the airport, I headed straight home to retrieve Mira’s gear from its secret spot. I went for that sexy businesswoman look (once again!), but with a twist: instead of my usual pencil skirt, I wore my tight leather mini skirt—a piece I’ve never worn out before—and swapped my favorite Le Bourget lace top stockings for the new seamed ones. The outfit was spread across the bed. I hopped in the shower to get ready for my long night as Mira! Since it’s been a while since I shaved, I first put on tan tights to smooth and silkify my legs. Then came the black lace French knickers and my lacy black corset. I opened the pack of expensive silk seamed stockings, gathering each one gently in my hand before slowly pulling them up my legs; making sure the seams were aligned and fastening all six metal suspender clips. The breast forms went on next. I put on my white blouse, followed by the tight black leather mini skirt that ends just above mid-thigh, and finally my patent black cincher belt, which I tightened a couple of notches extra to really accentuate my figure! Over this, I wore my black suit jacket before tackling the makeup: foundation, plenty of black eyeliner, dark eyeshadow, blusher, and then my wig. I clipped in long dangling earrings and applied the finishing touch—deep red glossy lipstick. The scented formula makes me feel incredibly feminine, especially when I purse my lips to spread it evenly. Back in the bedroom for a couple of squirts of Tommy Girl perfume before stepping into my 5-inch patent black stiletto heels. I checked myself in the mirror; Mira was now fully realized. To ensure my seams stayed straight and practice walking like a woman, I did some light chores around the house. This also helped my calves and feet adjust to these skyscraper stilettos. Once the tasks were done, I went back upstairs for one last mirror check. Everything looked good except that the hem of my skirt had ridden up just a tiny bit, so at certain angles you could tell I was wearing stockings—not that it mattered much given the rest of the ensemble! Image The time wasn’t too late yet, so I decided to kill some time on Yahoo Chat, teasing my outfit and showing off via webcam to friends and admirers. Before I knew it, 3 AM had arrived. I was eager to step out into the real world for this little adventure. Usually, I’d just hop in the car for a late-night walk, but because I planned something special this time, I decided to leave on foot en-femme all the way up the street. To avoid nosy neighbors and curtain-twitchers, I swapped my stilettos for patent black flat pumps so I could stay relatively stealthy. The stilettos went into the handbag along with an open padlock (no key yet—you’ll see why later). As always, unlocking that front door was the hardest part. After several aborted attempts and watching from various upstairs windows to survey the street, I finally committed. Quietly as possible, I unlocked and opened the door, peering up and down to ensure the coast was clear. I stepped outside, quickly locking and closing the door behind me, then made my way down the drive onto the street. I began walking up the road, trying to keep a feminine posture—shoulders back, chest out, head high, legs crossing with small steps. I kept stealing sidelong glances at both flats and houses to ensure no neighbors were staring. I was also very conscious of just how short my skirt really is, frequently brushing my hand past the hem to check it hadn’t ridden up too much. After a few hundred meters, I reached the end of the street and turned right onto the main road. My breathing was still rapid and my heart pounding with excitement. I walked about 50 meters further before stopping at the next junction under a lamppost. I scanned around to make sure no one was watching from windows or walking by before quickly retrieving my 5-inch stilettos from the bag and placing them gently on the pavement in front of me. The lamplight shimmered off every curve of the shiny patent leather, making them look much taller than they did against a bedroom mirror! Kicking off the flat pumps, I slipped my feet into those gorgeous heels. Holding onto the lamppost for balance, I placed my flats back in the bag, zipped it shut, and looped the hook of the open padlock around the zipper, clicking it closed so it was now permanently secured! I had no choice but to continue walking in these 5-inch killer high heels. My only option if they became too painful would be to take them off and walk in my stockinged feet, but since I paid a small fortune for them, I didn’t fancy ruining the look. I adjusted my skirt once more to cover the stocking tops and took one last glance around before taking my first steps down the street in stilettos. The sensation of being so high up on my toes was amazing. I teetered slowly downward with small feminine strides. Within 30 seconds, I could already feel a burn starting in my calves but pushed through it. Occasionally, I glanced down to see streetlights bouncing off the pointed patent tips and heard the deafening click-clack of heels on each step, plus the occasional scrape when I didn’t lift my feet high enough. A few minutes later, I reached the end of that street. To get onto the next one, I had to navigate a path between two houses, enclosed by a tall fence and lit only by a single lamppost. I couldn’t linger too long in front of other homes, so I kept looking back while walking to ensure no one was following before heading down the path. The heel clicks echoed louder here as they bounced off the high fences. The pain in my calves increased, but I continued toward the end of the path and slowed slightly to give my legs a brief rest. Again positioned between two houses, I didn’t want to loiter too long lest the occupants get suspicious from the noise and peek out their windows. I moved onto this new street and turned right, which would eventually lead me along another path into a small park. Climbing up the road, I remained acutely aware of the clicking heels on the concrete. Paranoia grew as homeowners looked out their windows at what was happening past 3 AM on a weeknight! Image Image As I neared the end of the street, I glanced back to ensure no one had tagged along as a stalker before stepping down into the dark path. My heart pounded hard as I stepped away from the safety of the well-lit residential road to walk through the park wearing an extremely sexy and slutty ensemble. A girl in a tight leather mini skirt, seamed stockings, and 5” patent high heels certainly didn’t belong here or at this time. Yet, despite knowing I was taking a massive risk by being so reckless and exposing myself like this, the thrill of looking so desirable pushed me to stretch beyond my usual comfort zone. The street lights gradually faded as I entered the park; sensing that I had passed all the potential curtain-twitchers in their homes, I slowed my pace slightly. My feet, calves, and legs were beginning to ache from walking such a distance in those 5” heels. With my pumps safely secured inside my handbag, I endured the discomfort and kept moving forward. Halfway through the park, the road at the other end came into view. After one more quick scan of the area, I paused for breath and relief - stretching each foot alternately to relax my calf muscles while looking down to admire the gorgeous pointed toes, the shine of the patent leather, and the seams of my stockings. God, I felt so sexy! I reached into the side pocket of my handbag and pulled out my lipstick to reapply it quickly, rubbing my lips together again to ensure an even coat of that glossy, scented red hue. Then came another spritz of Tommy Girl perfume, a scent that reminded me just how feminine and alluring I felt. I continued on toward the exit of the park, pleased that this little adventure had proceeded without issue so far - the only sounds being my heel tips clicking loudly against the path and the jingle of my earrings, audible only to me. My next destination was the subway tunnel. To reach it, I needed to walk about 200 meters along the main road, which was well lit. As I approached the end of the park, I stopped briefly to listen for approaching cars or traffic. Satisfied that my path was clear, I made my way out onto the main thoroughfare. By now, my legs and calves were burning and starting to cramp from having my feet elevated so high in those heels. Eager to get this section done quickly, I picked up the pace slightly, though it nearly caused my legs to buckle several times as I teetered down the street. The downhill path leading to the subway was visible ahead. Unfortunately, because it ran parallel with the road, I couldn’t peer through the tunnel to confirm it was clear and safe. This felt like the most vulnerable part of my journey. There were no houses nearby for cover, and my legs were growing extremely weary from all that walking. If any neds or weirdos were lurking down there, they would get an early warning with the clicking of my heels as I approached; but until I was right alongside the tunnel, I’d have no idea if anyone was actually following. Once I passed it, it might be too late to turn back easily. On one hand, I knew it was unlikely anyone would still be around at that hour mid-week, yet there were no guarantees of emptiness. I approached the tunnel entrance with great caution, walking on the outer edge of the path for a wider angle so I could peer inside first and decide whether to continue forward or double back up the opposing side if needed. Thankfully - just as my legs were about to give out completely - the tunnel was entirely empty. I stepped inward and stopped to rest each leg and calf in turn, giving them well-deserved relief. Standing there alone again, looking myself over from head to toe, I felt incredibly exposed. If spotted while entering or followed along the way, I’d have little warning until my stalker appeared behind me. And if someone approached from the far end, I would need to retrace my steps back where I came from—but they would be treated to a full view of my mini skirt, seamed stockings, and 5” patent heels! After resting for a few minutes, my heartbeat slowed enough for me to prepare for the next phase. I retrieved my digital camera and mini tripod from one of the side pockets in my handbag. Working swiftly, I set up my gear so I could capture footage of myself walking back and forth through the tunnel in this slutty outfit. In the narrow confines of the tunnel, the click-clack of my heels echoed loudly with every step. Even the sound of individual gravel grains beneath my feet seemed amplified to deafening levels. Since I was essentially putting on a show for the camera, I knew I had to really strut and display my sexiest wiggle as I paraded up and down. It’s hard to describe the feeling of freedom that came with acting this way. Dressed in my tight, provocative secretary attire while loitering in such a risky spot at an ungodly hour made me feel incredibly sexy. I glanced down occasionally to see light bouncing off the pointed toes of these fuck-me shoes, my feet and heels arched unnaturally high above the ground. The sensation of my suspenders pulling taut against my stockings, the tight leather of my mini skirt caressing the tops of my thighs with each step, my lacy lingerie doing its duty to maintain my feminine silhouette beneath the business suit, plus the sweet scent from my glossy red lipstick and perfume—all contributed. Link to vid!

Once I had captured a few minutes of footage, I quickly packed up the filming equipment and put everything back into my handbag. Before emerging from the tunnel, I needed to recompose myself. I touched up my lipstick once more, adjusted my skirt to ensure I wasn’t flashing my stocking tops, and then set off again. The next leg of my walk would be the toughest and longest stretch without much opportunity for a break as I passed two rows of houses. To make sure I could manage it, I waited at the tunnel exit for a few minutes until my legs were sufficiently rested. During this time, I took another moment to admire myself and plan ahead for the final part of my walk. I emerged slowly from the tunnel along the dark path toward the bottom of the residential street. A quick glance up and down the rows of houses on either side confirmed no one was awake—all lights were off—after all, it was approaching 4 am! I made my way up the street at a leisurely pace, taking small feminine steps to really savor what would be my last outing for quite some time. About halfway along the street, my legs began cramping again and I stumbled a few times. My calves were nearly spent, leaving me with two choices: remove my shoes and walk barefoot (ruining my stockings) or slow down even further. I chose the latter option, which left myself even more exposed as I teetered along the street. Image At the end of this road lies a T-Junction. Opposite it are some concrete steps leading down into a dark lane and woods—you can probably guess which direction I chose… I glanced quickly around the house windows once more, and when satisfied that the coast was clear, left the main road and headed down the steps into the darkness. I didn’t wander too far in—just enough to avoid being seen by anyone from the houses or the street while still retaining some light from the streetlamps. This marked the penultimate part of my plan. I’ve always been curious/confused when reading about forced feminisation—as a TV, it’s probably something I’ll never fully grasp because being ‘forced’ to dress in women’s clothes feels more like a dream than humiliation! In short, after admiring myself one last time, I hitched up my skirt, reached under my lacy panties, and began pleasuring myself amidst the darkness of the woods. Dressed like a streetwalker, it didn’t take long for me to relieve myself… and now I found myself feeling w

hat countless other TV’s / CD’s do as well immediately after ejacualtion… guilt and shame; when you quickly remove all traces of your feminine self and stash everything away back in its hiding place. Unfortunatley for me, I wasn’t in the safety of my house. I was a 15 minute walk from home, in the woods, dressed up like a slut feeling ridiculous. After contemplating my predicament, I had no choice but to make my way out of the woods and make my way home - the walk of shame. I had a quick look around at the top of the steps to make sure no one was around before heading for the T-Junction. The 5” stilettos were now more of a major nuisance but I couldn’t get into my handbag for my flats and taking them off would only ruin an expensive pair of stockings so I just had to endure the humiliation of continuing to teeter down the street in shoes - which at this time of night - were only fit for a street walking prostitute. The rest of my outfit in my mind had now also shifted from being ‘sexy’ to ‘cheap whore’. The walk back was along a main road so I couldn’t just forget my feminine mannerisms or I would be read so I had to reluctantly keep up the pretence and carry on with the small steps and sexy wiggle even though I was desperate to tear off everything I had on and return to “normal” as soon as possible. By now, my legs, feet and calves were in complete agony which made it even harder to remain composed and appear feminine with each step I took. Link to vid!

I let out a sigh of relief as I finally arrived home and locked the door behind me - I was safe! My heartbeat was going crazy with the adrenaline and my feet were ready to buckle and collapse. I instinctively wanted to kick off my shoes but convinced myself to remain in character and get myself upstairs to give myself a once over in front of the mirror just to appreciate what others may have seen had they ran into me. I lay down on my bed and finally kicked off my shoes, the balls of my feet and toes were in so much pain that they didn’t want to actually straighten out again so I had to massage them to bring some feeling back into them. I laid back and began replaying what I had just achieved in my head, before drifting off to sleep; still en-femme.