Caught crossdressing in self bondage by ex girlfriend

August 19, 2021

Elec winch mounted to roof beam in shed. Powered by battery charger plugged into timer witch once power point is turned on will give winch power for 10 min then no power for 1hr. Then power will back on for winch after 1hr. I will have wireless remote for up and down in hands reach.

After a Enema clean out and shave down there I will start off by locking on cock cage and inserting pump up butt plug to start stretching my hole.

Then I go out to shed to attach folding spreader bar to winch. (that when pressure is applied to rope in center of spreader bar it can no longer fold in half.) Then run straps from both sides of shed to attach to ankles keeping them a shoulder width apart. Finally hang pully in center with ratchet strap fed throw it with so the 2 hooks hanging down.

Remove plug and cage put electric pads on each ass cheek, elec ring around balls and one around shaft. Then insert remote controlled plug and pull on tight fitting panties. Followed by tanned sliming body dress. Then put in water balloon tits and tie rope harness on. Making sure the crotch rope is pulling the plug in deep and the knot in harness is be behind balls pressing on my taint.

Then I’ll put on stocking and 5 inch heels with locking ankle cuffs. With a chain running under arch of each heel padlocked to ether side of ankle cuff locking shoes on. Then I put on corset and lace as tight as possible. If needed to support boob balloons put on bra then put on black and white dress.

Then I put on locking wrist cuffs with winch control attached. Next I put on posture collar followed by pink bondage hood tightly laced. Next I stuffed a pair of panties in my mouth followed by the cock gag tightly buckled and padlocked. Then I did the same with collar on hood. Then i turn on power for timer giving me 10mins to finish. I attach straps to leg cuffs holding my legs apparat. Then I grab hooks from ratchet hanging down hooking one to top of rope harness (at back of shoulders) and other to back of bondage hood then tightened.

Finally I buckle and padlock on blind fold. Then I turned on butt plug and elec pads and rings to random. Then I clipped wrist to spreader bar before stretching out arms to slot spreader bar back to gather holding arms shoulder width apart.

Now the moment of truth I raise the winch until I’m stretched out. By doing this it pulls on center rope of spreader bar locking it in to place. Leaving me unable to escape on till the winch is lowered. So I’m able to fold spreader bar in half again to be able to unhook wrist off bar. After all that hopefully it’s close to ten minutes be up. After a little struggle I decide to make it a little tighter going up on the winch. Now I’m real tight so I decide to go down a little but after pushing bottom there is nothing. Meaning now I am stuck with a butt plug working away on my prostate, by being randomly shocked to my dick and balls as well as ass cheeks making me clench on plug. Which also makes me jump a little and because my rope harness attached to roof by ratchet this keeps on driving the plug even deeper.

So here I am. Tightly laced in a corset and dress with fake boobs and 5 inch heels. Locked in a bondage hood with a penis gag jamming a pair of panties deep in my mouth. Making me unable to hardly make a noise or see anything knowing I have a hr of this mmmmmmmmmmmmm.

So after what feels like hrs but seen as the winch is not working yet so I can release my self i know it’s less then a hour. But regardless I am dreading choosing the spiked 5inch heels as my feet are starting to hurt. I am now approaching my 3rd orgasm due to the plug now being pressed right into the sweet spot. Because the butt plug is smashing my prostate. All of a sudden I think I hear a car I stay as still as I can and fuck yes it is a car. Ohh no I think by staying as still as I can. Then I hear the door open and shut. But to my horror right at that moment I am shocked by full power to the dick, balls and to the ass for a good 30 sec. Not realising to it stopped that I was moaning and thrashing in my bonds. Resulting in my horror to the garage door opening then closing. Then I can hear some one walking around me and touching me here and there and checking my bonds. Then all of a sudden I hear the beep of a iPhone vid recording at the same time as the plug just gos crazy pounding my prostate. Which pushes me over the edge and I cum so hard that I half go limp in my bonds. As I recover I try the down bottom for the winch again to my surprise it starts to lower me until the control is taken from my hand and I’m lifted back up. Before the control is removed from my wrist cuff leaving me no way out. Then finally the silence is broken by a voice saying “not so fast I’m going to have some fun with you”. “First I know from facebook that Jody is away for 2 more days and I was hoping that u have not changed. An that you would be doing a little self bondage. But I did not imagine finding you like this my little slut. I am going to have some fun with u now my little slave.

Omg its ash what is she going to do to me I wonder. To my surprise she cuts the crutch rope and nicks and removes the elec rings from my dick and balls. Before just going to town sucking my cock and licking my balls and taint by moaning and looking up at me saying “ohh how I have missed this cock”. To my surprise I could actually fell another orgasm starting to build. When all of a sudden she stops and takes some rope and ties my cock and balls leaving me so hard. Then she grabs the ball parachute wraps it around my balls and attaches a 2lt water bottle to it. This pulling my balls down ***fully then I hear her say you have had some pleasure now time for some *** as she begins to whip my ass with what feels like a belt. Which with every blow makes the bottle swing pulling my balls even more. After atleast 20 good slaps with the belt she stops and my ass feels like it is on fire. Yet my cock is still rock hard. After going back to sucking my cock and slapping and pulling on my ball parachute she stops and leaves me on the edge again. I feel her tie a chest harness on me then a rope is tied around my neck. Then she pulls it to the point where she is choking me and she says. “Just a bit of insurance u don’t try anything by I re-tie your hands”. As she says this my hands are lowered unhooked from spreader bar and retired behind my back. Then as I think I’m about to black out the rope is removed from my neck allowing me to breath.

After catching my breath a wide belt is placed around my waist with a strap attached to the back of it. Which is fed through a winch hook then attached to chest harness. Followed by a spreader bar between ankles wondering what was next. A strap was hooked to center of spreader bar then to front of my posture collar. Then it was pulled tight. Forcing me to bend over 90 degrees. Then I hear the winch turn on and go up to the strap between belt and chest harness is tight this supporting my weight and not allowing me to fall over. Then Ash says “you look a little bit too comfortable” To which she puts a strap to the top of my hood and connects it to my wrist. Then pulling it tight so my head is ***d back even more. With a evil giggle I hear the shed door open and close then I am left alone. Then I hear the sound of heels followed by the door opening and closing. Then she walks around me a few times then stops and unlocks my gag. Then removes it giggling as she realises it’s a little cock gag. I then try push panties out witch she sees and finishes pulling them out for me. To which she tells me she is going to give me some water witch was a struggle to drink but much needed. Then after she has a quick fondle of my cock I am rock hard again. Then I hear the jingle of of my keys for all the padlocks. To which she uses to unlock and remove blind fold. Then I see her she is looking good and if I wasn’t already hard well seeing what she was wearing would of fixed that. She looked to of been wearing a corset my short black dress garter belt fishnet stockings and my strappy 5 inch stilettos. Next she removed my hood this was when I made the mistake of asking her to let me go and we could forget it ever happened. To witch she just looked straight at me and said did I give u permission to talk. Plus I have not even started to have my fun with you yet slut. She sits down in front of me on some milk crates. Lifting her foot towards my face she says if you know what’s good for you you better start tongue cleaning these shoes. And make sure you pay plenty of attention to the stilettos as it won’t hurt you to get some practice sucking cock before u have the real thing. To which on hearing that I start to struggle to get free to which Ash gets up laughing as she walks right up to my face and lifts her dress and to my shock I’m face to face to a life like strap on cock. She then grabbed a hand full of my hair and pulled my lips to the tip of her strap on and said we can do this the easy or hard way. But ether way u are taking this cock. I give in and slowly start to open my mouth. But I was obviously not fast enough for her coz soon as the tip was past my lips she just drove it in to the hilt and holds it there. Choking me by looking down at me saying. “When I say to do something u do it straight away slut”. Then she just starts thrusting in and out face fucking me for for what felt like for ever.

Once she finally stopped I had tears and saliva running down my face. But to my surprise as she pulled the strap on from my mouth. She squeezed the balls of the strap on witch made it shot at load of semen look a like substance all on my face and in my mouth. Before I know it she shoved her wet panties in my mouth followed by a ball gag. Then she grabs the tape and starts to wrap it around the lower part of my face. Sealing my mouth completely. Then to my horror she had a look on her face I had never seen before as she lowered a plastic bag over my head and tied it around my neck sealing it. Which made me panic i was thrashing around trying to get any air I could. Just when I though I was going to black out Ash removes the bag allowing me to breath. After I caught my breath she says to me that if I don’t do as I’m told and try anything when she unties me in a second next time the bag will stay on and I’ll be found in selfbondage like that.
I replied yes mistress best I could by being gaged to witch she smiled and said good sissy.

Ash 1st tells me that she has just taken plenty of pic and vids so best I do as I’m told. 1st she unties me completely and has me strip naked. After going to toilet and showering. I put on pink panties and bra with my balloon boobs in. Next the suspender belt then some fishnet stay ups which I still attach. Then the tan sliming short dress. Next goes on the 5 inch chunky heel shoes followed by the ankle cuffs with strap running under heel witch Ash then padlocks on locking shoes on. Next I’m sat in a chair to which my hands are cuffed behind back and legs tied to chair. Then ash walks out after a while she returns smiling saying it’s makeover time. 1st she dose my eyes with eye shadow eye liner and fake lashes. 2nd I lost track of how many layers lipstick and lip gloss and what ever else she put on there. Now she puts my red wig on me then puts it in to a high ponytail. Ash takes the ball off the ball gag and puts it in my mouth. Next Ash takes a roll of vet wrap and begins to wrap my head she makes sure to cover my whole head. Except my eyes, lips, nostrils and pony tail exposed. Once finished she said time for a reward to which she blindfolded me and pulled my cock out and gave me the best head job ever.

Once i was flaccid I feel her locking me in my plastic cock cage with the final click of a padlock she was done. Next she pulled ball from my mouth and before I could say a word. She had shoved her very wet panties in my mouth followed by a ball gag head harness which she buckled tight and of course padlocked all the buckles. It was now she burst out giggling saying those panties were so wet coz I spat your load on them before locking them in your mouth to in joy. She then said we better start hurrying up as it will be day light in a few hours. So she removed my blind fold and untied me. Then told me to go to the shed and tie my hands together and hook up to winch. So after 10 mins or so she comes in snatching control and says. “ you will now pay for being so relaxed. She wraps corset around my waist and takes up a little bit of slack next the winch starts to rise and dose not stop till I’m pretty much hanging by my wrists as I’m on the tip toes of my heels for relief. Ash just starts lacing my corset tighter and tighter to the tightest I have ever been then ties it off. Then finally lowers me down a little so I can stand flat on my heels. After a couple of mins she goes over the laces one more time using her knee to get it that last bit once done she tied it all off and released my hands. Next on goes the black figure hugging knee length dress. She then takes the metal belt which has a short chain where it joins which she padlocks shut. To then remind me that the belt will have to be unlocked before I’m able to loosen and remove corset. To finish off I put on a long sleeve meshy top posture collar which is also padlocked on. Then my hands are pushed into bondage mittens witch are buckled tight and padlocked. A wide belt is added just under my breast and then ash locks my mitts behind my back . She then opens shed and hooks a leash on my collar and walks me to her car and opens the back door. Ash lays me face down ties knees together then ankles. Then to top it off ties a rope to ankle feeds it under belt and pulls leaving my heels nearly torching my bum and ties it off. Still not happy she grabs my pony tail pulling my head back and ties it to extra rope leaving me with my head pulled back.

She shuts shed after loading boot with some stuff. Finally she opens back door near my head kisses me on my gaged mouth and puts blind fold on me. Then after i have no idea how long of driving around the car is turned off my pony tail is untied followed by my legs. With some effort I am out of the car trying to keep up with ash as the leads me down some gravel tracks.(now I know why she put chunky heels on me ) we stop my lead is pulled I followed then I am stopped my ankles are spread wide and tied off to bars then my knees also. My lead is pulled again making me bend over to my fake boobs are pressed against something the lead is tied off keeping me in this position. Next my waist is tied down now I can not move a inch. To which i hear Ash say let’s see if u can move then she flips my dress up and starts belting my ass to its on fire and I’m crying like a little girl. Even once she stops I am sobbing she lifts up blind fold and gets in my face and says on a good note u did not move a inch. But seeing u cry like a bitch has made me decide you really are just a sissy Littie Bitch and I’m going to leave u here with a note saying. Hi I’m sissy Tiffany fell free to use and *** me as u see fit. As she finishes saying that she lowers my blind fold. I try struggle but can’t move a inch.

Next thing I hear is Ashes car start up beep the horn and drives off. I just stand there bent over the table for what feels like ages I had given up sobbing or trying to get out when I think I hear the Russel of gravel. I stay still listening then I hear a deep voice say. What do we have here time to get me some sissy pussy. My dress is ruffly flicked up and my nickers are ripped down. Then I hear him say I’m gunna need a handle as a belt is put around my neck pulled tight and then dropped on my back. next I feel a lubed finger in my hole then 2 then 3. Then it hits me that theses fingers feel more feminine. As if she read my mind the blind fold lifts off and a phone is dropped in front of me playing a men’s voice. Once it stopped Ash moans in my ear your sissy hole is still going to get fucked but it’s going to be by your mistress. Next I feel the head of her strap on pushing on my hole and she says just so you know sissy this strap on rubs my clit so the harder I go the better it feels so luckily your a *** sissy that can’t runaway. As I relax for 1 second it pops in then she slowly at 1 st starts to pump in and out of me until she has the hole 9 inches in me to the hilt this is when ash leaned down in my ear and said time to tear this sissy hole up and with that she grabs my pony tale and starts to pound the shit out of me. After about 10 min of this she swaps the pony tail for the belt and as she is half choking me it’s coursing me to tense my ass. which just turns her in to full beast mode. As it makes it feel better for her when i tense on it. To which I hear her scream mistress wants to cum and sissy will do what it takes for that to happen won’t she SLUT. I nod my head yes best I can to hear her say damm right u will. Then all of a sudden she pulls a a plastic bag out puts it over my head and ties it off followed by a stocking over my head and she is going just driving it in and out of me she she has also grabbed hold of the belt and is riding me hard. I feel a orgasm coming and so must she as she is screaming. I start to cum like I never have before

First attempt at a story if you’d like me to continue please comment sorry about the grammar if someone would like to rewrite it properly feel free