My name is Anna. I am a closet crossdresser. I love tight bondage and role play. This is a true story about one of my adventures a few years ago. I decided to have a bit of a risky self-bondage adventure. Tying myself at home was fun, but I wanted something more to really keep me on edge. Something that would scare me. Something where I could potentially be discovered.
I lived in a village in the UK, and there was a wood with trails about 1km from my house, in which I had cycled and jogged numerous times. Most of the time, there was absolutely nobody. One November day, as the weather was quite good, it had been dry for about a week, I decided I could risk it. At about 3pm, I took my bike and went to the woods. I entered through a little public footpath between 2 houses in a posh residential neighbourhood. I went into the woods for about 100m on the main path, to the first junction, before turning right onto another smaller path. Then I cycled 1.5 km straight down that path to a spot I knew well. There, I went off the track to a small clearing about 20m from the path. I left a bin bag at the base of a tree with some toys and a message and went back home.
At 8pm, it was dark. At that time of year and that time of day, I was pretty sure to be completely alone in the woods. But there was still the chance of a late dog walker or that an evil pervert had found my bag and message. The moon was shining and there was enough light to see a bit of what I was doing. Time for action. After a shower and a thorough enema, I locked my cock in the smallest cage I had and placed the key on my night stand. I would not need it tonight. I placed a big black butt plug in my rectum and started dressing myself: I put on black seamed stockings, a black suspender belt, matching black bra and thong. I filled the bra with fake boobs. I then tightened a low waist corset over the white blouse I had just put on. I applied my make-up, with dark eyeshadow and bright red lipstick. I then put on a black tracksuit bottom and a black baggy jumper over my slutty clothes. 9pm. Perfect. I grabbed a bag and a cap, took my bike and cycled to the woods. The streets were empty in the residential neighbourhood, as planned. The plug was very noticeable when I sat on the saddle, bordering on painful. I cycled on the path ahead of me for about 300m, past the junction to the track leading to the bin bag I had left earlier, then went off the track to another clearing, really close to the track.
In the clearing, I removed the tracksuit bottom, the jumper and the cap and placed them inside the bag. I changed from my trainers to 7 inch black platform stilettos. I put on a very short PVC mini-skirt and a blond shoulder length wig. Lastly, I put on a black collar with the word “slut” written on it that I padlocked around my throat. As a final act, I made sure that I had keys in my bag. I took another padlock and closed the bag. I also chained my bike to a tree. The key for the chain was inside the bag. As a final touch, I left a written note pinned on the bag.
Now I was in the woods, dressed as a cheap whore. If I wanted to avoid walking through the neighbourhood dressed like that, I needed to retrieve the key to my bag. That key was 1.7km away, in the bin bag that I had left in the afternoon, alongside other toys.
I started walking on the path straight away. It was such an exhilarating experience. I loved being able to strut on my stripper heels for a long distance. I felt like a cheap whore beating the pavement. I could feel the plug moving in my ass. All my senses were on alert. The moon was bright enough to give me just enough light. It took me almost 30 minutes to get to the clearing where I had left the bag as I had to take shorter steps with my heels. My heart was pounding. I was about to start phase 2 of my adventures. Phase one was the easy one, with low risk. In the bag, I had left a big ball gag, metal handcuffs, a chain with 2 padlocks, leg irons, and the key to my bag. I had also left a note:
“If you find this bag, please leave it there. Between 9.30 and 10pm tonight, a slut will come and get the contents of this bag and chain herself. If you want a free fuck, this slut is more than willing to suck your cock(s) and get fucked roughly (the way she prefers). There are condoms at the bottom of the bag. If you want a suck, the slut is happy to do it without and get a mouthful of cum. See you tonight.”
Everything seemed calm and there was no strange noise in the clearing. I started by securing the leg irons around my ankles. The noise of the clicks as the cuff locked around my ankles seemed deafening. I locked the cuffs so that they were tight but not too tight that they would cut into my ankles. I had reduced the chain to a mere 20cm, meaning that it was going to take me a very long time to get back to my bike. It would also make it impossible to outrun anybody. The key for the leg irons was in my bag next to my bike. Next, I padlocked the chain around my waist, with the padlock in front of me. I secured the second padlock to the one link between my handcuffs and the chain in the middle of my back. I then put a big sticker on the corset which read; “PLEASE FUCK ME HARD!”, then I placed the big ball gag in my mouth and secured it around my head and under my chin. I was almost ready. One more step. I took the key to padlock the bag containing all my keys and my clothes, and handcuffed my hands in the small of my back. You probably guessed it; the key to my handcuffs was also in the bag next to my bike. I was really trapped. I had to walk 1.7km this way, hoping not to meet anybody. The choice of a white blouse was also deliberate: it would make it a lot harder to hide. I also had to make sure I did not drop that key or I would be in serious trouble. I did not want to walk round the neighbourhood dressed as a whore, let alone a chained whore!
It took me a full hour to get back to my bike. My senses were working in overdrive as any little sound made me jump. Twice, I hid behind bushes as I thought I had heard someone. The combination of high heels, short hobble and hands handcuffed in the small of my back made the walk quite difficult. I could only take very small steps and I did not want to take the risk to fall and hurt myself or knock myself unconscious. My ankles were hurting as the cuffs were chafing my skin. But I was loving every minute of it. I had never felt so alive.
Eventually, I found my bike. I looked around carefully, straining to hear any suspect noise when I approached the clearing as the note I had left on the bag read: “If you wait patiently around 10.30 tonight, a chained whore will come to try and free herself as her keys are in this bag. She wants to be used roughly. Her two holes are free to use. Enjoy her...”. I went to my bag but nobody jumped on me. I felt both relief and disappointment. I managed to unlock my bag and find the keys to my restraints. I unlocked myself. I started with my handcuffs, then the gag. Despite the pain, I kept the leg irons on.
Then, I spread a small blanket on the floor. In my bag were two big black dildos. I took them, and put them on the blanket next to me. I went on all fours, removed my plug and licked it clean. After the thorough enema I had given myself, it was all clean anyway but the thoughts of what I was doing, on all fours, dressed as a whore, in chains, in the wood was making my cock strain against the confines of my cage. I could just imagine doing that because a sadistic Master was forcing me to… Then I took one big dildo and started sucking it. I wanted it all wet and shiny from my saliva, I played with it as I would a real cock then deep throated it a few times, making me gag. I was lost in my fantasy of being used in the woods… When I was happy it was all wet, I pushed it in my ass, slowly. The feeling of penetration was so nice, I could feel myself being stretched properly. I grabbed the other dildo and started sucking on it as I was fucking myself with the one in my ass. At that stage, I had never been spit-roasted by 2 cocks (that would be another story to tell…). I kept swapping the two dildos and I fucked myself for a long time. If a man had come, I would have done anything at that point… Eventually, I stopped. I finally got what I had wanted all along: getting fucked in the wood. I put the plug back in my ass, removed the ankle cuffs, put the tracksuit and jumper over my slutty clothes, changed my footwear and cycled back home.
I was still in my fantasy though. I was fully satisfied from my escapade in the woods. (although at the back of my mind I was almost disappointed that some old pervert(s) had not found the note and abused me properly…) In my fantasy, I was the cheap whore of a mean and nasty pimp.
As soon as I was at home, I removed my “street” clothes”, put my slutty shoes back on, put the key to my handcuffs/ankle cuffs on the table in the lounge and went to the kitchen. I opened the freezer and took the jug out. A key was trapped in the middle of the block of ice, at the end of a string. I took my bag of toys and went to the laundry room. I had put a thin mattress on the floor and had a chain connected to the wall on the mattress. The key to that padlock was in the block of ice. I put another padlock from the chain to my collar, put my ball gag in my mouth and handcuffed my ankles again. I pulled a leather hood over my head that had lacing in the back. I secured the lacing as tight as possible. The hood was made of leather and only had 2 small holes for the nostrils. Once trapped inside, you could not see a thing and breathing had to be controlled so that you got enough air. I loved spending long periods of time in it, especially whilst gagged. As the final touch, I handcuffed my hands behind my back. This was the way my pimp kept his whores when they were not working.
Needless to say, I spent a very uncomfortable night but loved every minute I was awake. I managed some broken sleep. I checked on the jug from time to time with my hands. Eventually, the key was free and I unlocked the chain to the wall. I managed to stand and navigate my way to the lounge where I uncuffed myself. It was not easy as I was completely blind because of the hood. I looked at the clock and it was 7am... I was sore all over but with the right kind of soreness, the one reminding me how naughty I had been.
Unfortunately, I moved from this house a short time afterwards and never repeated the experience...