BondageDating

First pair of heels and a maiden voyage with my cage

I just received my first pair of heels... I'm so excited:0) Before heading out, I put on my chastity cage and fitted a medium-sized plug. It took a week to…

member_32a3b67717 8 Sept 2026 #1

I just received my first pair of heels… I’m so excited:0) Before heading out, I put on my chastity cage and fitted a medium-sized plug. It took a week to get the opportunity to test them out. They fit quite tightly since they are half a size too small. I opted for a lane that is one of those quiet stretches left behind by road upgrades. Opposite the turn into this lane, I hid my spare car keys and drove in until reaching the muddy section. (I didn’t want to ruin my shoes!) Then I turned the car around, parked it, and sat in the darkness for a bit while my eyes adjusted to the night. Behind me lies another half-mile of road, which is popular with couples on dates. I once walked naked up there and spotted a car just in time not long ago. This time, however, I hadn’t verified that I was alone. I decided to add some risk. It was also a couple of degrees below zero, adding some crispness, mmm. I started by undressing from the waist down. First, I slipped on fishnet stockings and a black lacy suspender belt. Then came my other recent buy: a sexy black mini skirt from a dance supplier. This was my first time wearing the new heeled boots. They were a bit of a struggle to put on, but they looked awesome. Finally, I took off my shirt and pulled on a lacy top from my wife’s lingerie drawer. It’s tight but fun! I stepped out into the crisp night air. I locked the car, then unlocked it again. Afterward, I tossed the keys onto the floor and shut the door. Now I had a minute or two to change my mind. So I set off walking the half-mile to retrieve the other keys. Fifty yards down the road, I saw headlights… I thought they were turning into my lane. I froze. Then I tried running back to the car. As I got close, it locked itself. Two bright flashes from the indicators lit me up in all my glory. I spun around to see if a car was approaching… phew… nothing. So I set off again. I marveled at how my hips swayed automatically as I walked in heels. The plug seemed to wiggle along with my bottom. The heavy metal cage on my cock swung as I moved, and the cold air made my skin tingle. By the time I reached the keys, my feet were a bit sore. I quite liked that sensation. I stood in the main road, daring myself to stay just a little longer. Then I headed back toward the car. It’s about 60 yards until you are out of sight, so there had been a nice risk element in my mind anyway:0) Back at the car, I was elated. I decided to take some pictures to share with everyone, so I set up my phone to record video and minced around in the glare of my headlights. Feeling bold now! God knows if anyone saw me or if there were any lovers further up the road!