[PICS] Heading to the mall dressed like a prostitute... what now?

[Kali_CD]

Feeling pretty pleased with myself I drove home to finish the last warm up tasks before my trip to the mall tomorrow. My first task was to jam the massive zucchini I had bought into my ass. I changed my stocking for some thigh high pantihose, got down on my knees, pulled out my butt plug and lubed up the zucchini. I had never inserted anything with this much girth into my ass, and I had my doubts I could fit it, but I was under instructions to push it all the way in no matter how long it took.

As soon as squatted over it and started trying to slide it in I knew I was in trouble – it was huge! But I gritted my teeth and kept pushing my weight down onto it. Progress was slow and painful. Every time I managed to relax enough to slide it in another 1 or 2cm the pain of my ass stretching wide open would overwhelm me and I would have to take it out again. Slowly but surely I managed to slide it all the way in.

Now that I had it all the way in, my task was to fuck my ass for 10mins. I was allowed to start gently with little strokes, but had to build up to pounding the entire length as hard and fast as I could, completely removing and re-inserting it every 2mins. It wasn't long before I was glistening with sweat and wondering if my poor little ass would ever be the same again.

Keep reading Part 3...

[Kali_CD]

My last task for the night was to juice the ginger and inject it to my newly loosened asshole. I had tried figging before and found that inserting a little finger of skinned ginger produced only a mild warming sensation, but nothing too intense.

I was curious how this would be different. I prepared 11mL of pure ginger juice, inserted the syringe all the way into my ass and pushed the plunger a little bit. The burning sensation was immediate and intense. I hesitated before pushing any more in – I hadn’t heard of anyone doing this before and was worried it might actually injure my ass. I quickly decided I was already committed, and pushed the plunger all the way. I removed the syringe, lay prone on the bed and handcuffed my hands behind my back in the hogtie position. The burning sensation continued to build as the minutes ticked by. I watched the timer count down, determined to ride out the full 10mins, but at about 8mins I was approaching my threshold, and I could feel my ass starting to involuntary contract to expel the fiery juice. The timer finally zeroed out and I unlocked my cuffs and sat on the toilet. As soon as I expelled the first few drops the burning sensation doubled as the juice coated the sensitive skin around my rectum. My whole body was wracked with the most intense contractions – it was like my my ass had gone into labour. They were absolutely uncontrollable, lasting about 10sec each, with maybe 3 seconds in between. It felt like my ass was trying to expel all my internal organs, I had never felt anything like this before. After the 3rd one I was honestly worried I was going to prolapse my ass. I don't know how long this went on for – probably only a few mins, but I honestly can't remember much because I was so overcome. After the contractions subsided I remember thinking I would never do that again, but now as I sit down to write this I'm not so sure...

Late the next afternoon I got dressed back up for my trip to the mall – and my first ever visit to a dominatrix mistress...

I got in my car and drove for nearly an hour to meet the mistress. At every red light I had to put my window down and try and make eye contact with the people in the car next to me. I was so nervous I would pull up to someone that would recognise my car! At one red light I pulled up next to a pickup truck with two young guys in it, the passenger had a perfect view down to my mostly exposed thighs. I couldn't help but look away as he leaned out his window to get a better view and try to start a conversation. Thankfully the light went green before I had to respond, but for the next 10 mins they kept trying to drive next to me and get my attention. At first I was a bit flattered, but I started to worry they were going to follow me all the way to my destination. Eventually I took a turn they didn’t follow me down and I calmed down a bit.

I finally arrived at my destination, parked in the underground car park, got out and did my best to confidently strut in my heels to a nondescript looking door. My heart begins to pound as I'm buzzed in, I'm shown to a waiting room and sign a disclaimer before being introduced to the mistress.

When she arrives she looks me up and down with piercing green eyes, introduces herself and tells me I look very pretty. I feel naked under her gaze. She is quite young - maybe mid 20's, petite and pretty, but before I could take in more details she motions for me to follow her. The only thing louder than the sound of our 4 high heels echoing along the hallway is the pounding of my heart in my ears. As we walk she tells me she has read my email about the session and is pretty sure she knows what I want. She shows me into a room, enters behind me, closes the door and asks if I'm ready to start. The word yes is barely out of my mouth when she pushes me towards a table and bends me over. Each of my hands is placed behind my back and she expertly binds my wrists together with rope. She begins explaining the rules and safety words as she works. I can feel her wrapping the rope higher and higher up my forearms, slowly but surely bringing my elbows together. This forces me to arch my back and stick out my ass. As she ties off the ropes she asks if I have any questions - 'no mistress'.

I'm instructed to spread my legs which I quickly do. There is a loud slap, and half a second later my right ass cheek is burning with pain, she quietly instructs me "wider". I comply, spreading my legs so wide my heels are barely taking any weight, and I can feel my breasts pushing into the table.

I hear her snap on some latex gloves, then she pulls aside my g-string and begins rubbing lube into my ass with her fingers. "Lets start with a little plug shall we?" she said, and begins gently pushing the tip in and out before pushing the plug all the way in. "That was far too easy, I'm going to have to get out my big strap-on later". I silently curse the darer who made me stretch my ass with that giant zucchini, but simply say 'Yes mistress'.

She tells me to bring my feet together, stand up and walk into the middle of the room. I do so very carefully as I've never been tied up in heels. She walks around me a few times taking me in, pinching my ass, squeezing a breast, stroking between my legs. I notice she already fitted her strap on while I was bent over - if that was her 'small' one I was in big trouble.

She puts her hands on my shoulders and pushes me down to me knees, I didn't resist but is was quite difficult in 6" heels with my hands bound behind my back. When I look up I'm face to face with her big black cock. "Suck the tip" she says as she pushes her hips towards me. I part my lips and take the head into my mouth. After about a minute of this she tells me to look up and begins to gently thrust. With her cock still in my mouth and our eyes still locked, and she tells me I'm going to learn to deepthroat. "You have to do your best to relax your throat, stick your tongue out, breath through your nose and trust me, ready?" She didn't give me time to answer - not that I could have with a dick in my mouth. She firmly but not aggressively grabbed the back of my head and pulled me towards her. I tried to do as she said but before I was halfway down the shaft my gag reflex kicked in. I pulled back and she released me shaking her head "that's not nearly good enough, your going to learn to take this whole cock". She grabs my head again and I open my mouth, she slides her strap-on down my throat, again triggering my gag reflex, but this time she does immediately not let me go and my whole body shudders with 2nd gag. It finally dawns on me that I am completely in her power, absolutely helpless to stop her from doing as she pleases.

"You are not relaxing" she chastises me, "I can tell you're new at this, so this time I'll stay still and you swallow as much cock as you can". I'm determined to please her so I take the cock down my throat, as I feel a gag coming I stick out my tongue and breath in through my nose, the gag subsides and I take in another inch before a big gag comes and I pull away. With each gag I can feel my ass clenching around the butt plug.

We keep doing this for a few minutes until I'm nearly taking the whole thing down my throat. "My turn again" she says and puts one hand around the back of my neck, and one behind my head. The helpless feeling returns as she forces herself down my throat. She isn't rough, but is unrelenting this time, my eyes begin watering and within a few minutes I can feel tears dragging my mascara down my cheeks. Every time she pulls out, a string of slimy saliva connects my mouth to her strap-on as I gasp for air. Before long, strands of goopey saliva stretch from my chin all the way to the floor, and I'm no longer thinking about pleasing her, but just getting through this.

Finally, after pulling me in balls deep and holding me there for what felt like forever she said "good little sissy, that will do for now". She helps me to my feet, reaches under my skirt and pulls down my g-string. As she does this I catch my reflection in the mirror and am shocked by how utterly abused I look - my mascara has turned into panda eyes, with little black streaks running down my cheeks. She directs me over to a piece of furniture that looks a bit like the horses gymnasts use. I'm instructed to mount it, and realise its puts me into the perfect doggy style position. My ankles and knees are strapped in before she unties my hands and straps my writs and elbows to the horse as well. I am completely immobilised.

Bent over like this, my mico skirt barely covers the top of my ass cheeks. She wanders over to the wall and plugs in a magic wand vibrator, before resting it on the small of my back while she blindfolds me. Now in complete darkness I hear the hum of the vibrator as she turns it on. She tells me that she is going to give me a treat for being such a good little cock sucking sissy and touches the wand to the end of the buttplug which I had almost forgotten was still inside me. The sensation was very arousing, she kept swapping between stimulating the base of my clitty and the plug until I was writhing in pleasure. Eventually she slowly pulls out the plug. "You've had your fun, now its my turn again".

I sense her getting into position behind me, she pulls my cheeks apart and slides her strap-on inside my ass. She pushes all the way in until I can feel her thighs right up against my ass. After a few test thrusts she says "Oh you definitely need a much bigger cock to fill this ass". She withdraws and I'm left in darkness as I listen to her adjusting her harness and fitting a new strap-on. She removes my blindfold and tells me she wants me to see what is about to go in my ass. She walks around in front of me and slaps me in the face with it. I'm told to open my mouth and I try to take it in but I can't fit the head past my teeth.

She walk back behind me and asks "you remember the safe words for 'near my limit' and 'stop'?". I reply 'yes mistress'. "Good, because while I work this into your ass, and for the next 10 minutes all you are allowed to say how good it feels, how much you love cock in your ass, clear?".

I watch her in the mirror in front of me as she grabbed the big black cock with one hand, and spread my cheeks with the other. As the head begins to slide in, my ass stretches and I'm overcome by the intense pain. I cry out 'oh*fuck me that hurts', she pulls out, slaps me 3 times hard on my right cheek and says "you means fuck me that hurts so good?"
'Yes mistress'.
"I want to hear you say the words".
'Fuck me that hurts so good'.
"And?"
'And can I please have some more dick in my ass mistress'.
"There's a good little sissy!".

She again pushes herself inside me, this time I bite my lip and just moan out in pain.
I feel hot all over and beads of sweat break out over my entire body as she slowly but surely advances.

"You need to push back against the cock like you are trying to push it out"
As soon as I follow her instructions I could feel the strap-on sliding in more easily, but the pain only increased.

Just as I thought I couldn't possibly take any more, and was about to use a safe word, the cock cleared the resistance and was inside me. The pain was still intense but she stayed perfectly still to allow me to get used to it.

"You're being very quiet sissy, if you don't start talking I'm going to take it out and put it back in again"

The thought of going through that again terrified me so I quickly told her how good it felt and begged her to to push it further in.

She slowly pushed deeper and deeper inside me until I could feel I was fully penetrated. I told my mistress how I could feel her against my colon and how much I loved it. "Are you sure its in all the way?" she asked as she pushed even deeper. Because I was tied to the horse I had no way of pulling away so I just moaned 'god yes you are so fucking deep inside me'. For a few minutes she just stayed there doing tiny baby thrusts tapping my colon. I began moaning with pleasure and encouraging her - no longer having to fake it.

Almost imperceptibly her thrusts got longer and longer until it felt like the whole shaft was sliding all the way in and out, with only the head remaining inside. She was still going very slowly and gently and my pleasure was building, with only a hint of pain. She kept fucking me like this for quite a while before telling me that from now the only words I was allowed to say were 'harder' or 'deeper'.

I obliged and so did she. Soon every thrust was coming harder and deeper than the last. The pleasure I was feeling a few minutes ago became a distant memory, I was now in my own little world of pain. Over the next 5 minutes I had to use my 'getting close to my limit' safety word twice, both times she checked I was ok and eased up just enough to prevent me from having to ask her to stop.

After another 5 minutes I used the safety word a 3rd time, she paused and told me "my poor little sissy is almost fucked out, I think I have a pretty good idea of where your limit is now - Ill make you a deal, you let me gag you and fuck you as close to your limit as I can for 2 minutes and then I will release you. Because you're gagged you can't use the safety words, but if you think I'm injuring you just shake your head and the session will be over. Do you trust me?" I simply replied 'yes mistress'. She withdraws, gets a ball gag and fits it to my mouth. I'm already regretting my decision - I didn't realize she would have to take the stap-on out and put it in again.

She tells me to look at her in the mirror as she slides back inside me - it was not nearly as painful this time. I could already feel saliva starting to dribble out the side of the ball gag. After a few gentle thrusts to get all the way in she tells me "your 2 minutes start now". She thrusts hard and deep, impacting my colon so hard my whole body jumps in an attempt to get away, but there is nowhere to go. She reaches around and grabs the inside of my hips to get better leverage and continues to pound me. I break eye contact, bury my face and grit my teeth against the gag. I already want to shake my head and make it stop, but I cling to the thought that there can't be long to go... and resolve to hold out to the end.

The 2 minutes felt like an eternity, I was sure she had gone over time - I could hear her starting to pant with exertion, and the pain I was feeling was well past where I thought my limit was. The thought occurred to me that maybe she planned to just keep going indefinitely to see exactly how long it would take for me to break and shake my head. But a few seconds later she slowed and then completely stopped. She leaned forwards and undid my gag. "Good little sissy! How was that?". I can't even remember what I replied.

"Now before I let you go, I have one final thing I need you to do for me, if you don't agree I'm going to put the gag on and give you another 2 minutes"
'Please I will do anything mistress'
"You've got to stay dressed exactly as you are now, and on the way home you have to drop into a mall and do a walk of shame through it - can you do that for me?".
'Yes mistress'
(I had requested this task in my email to her to match in with the rest of the dare)

She withdrew her cock from my ass, undid the restraints and said she would give me a few minutes to clean up, then to sit in front of the dresser when I'm ready and she would come back in. I did as instructed. I glanced at the clock - I couldn't believe the session had gone so quickly. I had survived 45 minutes of solid deepthroating and ass fucking.

She came back in no longer wearing her harness, but carrying what looked like a tool box. She put it on the dresser and opened it up to reveal a full cosmetics kit. "I've ruined your makeup and I need to get you looking nice and slutty for your trip to the mall". She wiped off my panda eyes and all the mascara that had run down my face, then started to reapply foundation, blush, lipstick, heavy eyeliner and mascara. For some reason out of everything this felt the most intimate and made me the most embarrassed. As she worked we talked about the session, and when she was done she admired her work, then told me to make sure that I spent at least 20 minutes inside the mall. She then got me to stand up, bend over and wrote "Spank me!" on my ass. I straightened up and checked out my ass in the mirror and saw her message was still a tiny bit visible when I wasn't bending over. She showed me to the door and gave me one final slap on the ass, wished me luck and told me to email her some selfies from the mall.

I felt a bit shell shocked as I walked back to my car. I sat down and lit a smoke thinking about what had just happened, and what was still in front of me. I knew I had to put my plug back in for my walk of shame, but decided to do it once I arrived - I couldn't contemplate doing it now. When I parked at the mall I realised I didn't pack any lube for the plug. So I just spat on it, it slid into me with surprising ease.

Keep reading Part 4...

[Kali_CD]

I had parked in an undercover carpark maybe 100 meters from the mall entrance. I was starting to get nervous so I decided to get out before I chickened out. I stepped out and locked the car. I was very focused on keeping my stride small, my shoulders back and not swinging my arms too much. A few cars drove past but I keep all my attention focused on the entrance.

Before I knew it the automatic doors were parting for me and I was inside. I took a ramp escalator up into the mall, and immediately wished my skirt was longer and my heels were shorter - it felt like every man within eye sight was checking me out. I felt my cheeks burning with embarrassment at all the attention I was receiving. Last night was Saturday night, it was dark and all the girls were dressed up, but here at the mall I really stood out. I must have made quite a sight, I was definitely turning heads. I knew from behind I must have looked dam hot.

I began strutting in the general direction of the bathrooms on the other side of the mall, resisting the temptation to take the most direct route. Along the way I would catch my reflection in shop windows and get a rush of adrenaline - I couldn't believe I was actually doing this! I passed two women in their 30's who stopped walking to watch me, one of them got out their phone and started filming or taking photos. After I passed them I threw a glance back and they were still starring so I gave them a little wave and kept walking. As I got closer to the toilets I considered the dilemma of going into the mens dressed like this - should I wait outside for a minute in the hope it would be empty when I entered? What if someone was right behind me and followed me in? Before I had made up my mind I was in the little service lane that led to the bathrooms, it was much busier than I would have liked, so I just plunged straight into the mens room. There was a middle aged man washing his hands, he watched me in the mirror as I made a bee line for a stall, closed the door and locked it. I sat still as I listed to him leave, then considered the task at hand. I started by taking a bunch of selfies. I got a bit carried away and did this for quite a while, stopping and sitting still every time I heard someone enter. I knew I was just procrastinating starting the next task... I was really nervous to open the 'spank stall'.

Keep reading Part 5...

[Kali_CD]

I knew this was the task I was most likely to fail, so I had set some punishments if I sissied out; on the way home from the mall I would have to go to a park, and spend 10 mins on my knees with my wrists handcuffed behind me to a pole, eyes closed, mouth open. If no one had come past by then I would have to spend another 10 mins handcuffed to the post on hands and knees. When I got home I would leave my handcuff keys in the letter box, get the spare key which were now frozen into a big block of ice. I would cover the big zuccini in hot sauce, insert and secure it in my ass, then handcuff myself, trapped with fire in my ass until the ice melts and releases the key.

These punishments were running through my head as I starred at the lock on the stall door. Obviously after my ginger experience last night I wasn't keen to do the 2nd punishment at all. But I still couldn’t bring myself to open the door wide open, blindfold myself and bend over the toilet so my ass with "spank me" written on it would be on show inviting anyone who came into the restrooms to slap my ass.

So I started making bargains with myself, I wouldn’t blindfold myself, and I would leave the door only slightly ajar and bend over for 5 mins. In exchange I would only have to do the first punishment task. I felt this was a fair compromise, and got ready.

I pulled down my pantihose a few inches to expose my bare ass make the 'spank me' more visible. I waited and listed until the restroom was empty, then reached out and unlocked the door. To my horror the door kept wanting to swing wide open. I managed to get the door to stay about 6" ajar - much wider than I had imaged when i made the bargain with myself. But I was committed now, so I turned around, straightened my legs, bent at my hips, grabbed the toilet seat and stuck my ass out. I stood there watching the timer on my phone tick down, straining to listen to what was going on behind me.

Worst case scenarios started running through my head. What if somebody called security? What if a group of teenage boys came in, they would never leave me alone! Would anyone take photos of me? What would I do if someone came into the cubicle and locked the door behind them? I heard several people come in and leave over a few mins but so far no one had tried my cubicle door. I was starting to loose my nerve when I heard footsteps approach and the door squeak open. I strained to listen, and tried to steel myself for a spanking, but for what felt like forever nothing happened. Had he walked away? I was about to look over my shoulder to see what was going on when thwack! The slap caught me off guard and I had to clutch onto the toilet to stop from over balancing in my heels. I waited to see what would happen now. I felt a hand grab my ass cheek and squeeze, I had no idea what to do so I just stayed very still. Just then I heard someone else enter the bathroom and suddenly his hand was gone and I heard a few sets of footsteps. I stood up and turned around to close the door, there was a 30 year old guy slowly walking towards the urinals, starring at me. I don’t know if he was the one who groped me, or the one who just entered and saved me, but I shut and locked the door and sat back down. I checked the timer which showed I still had 90 seconds to go. I decided to wait until the restroom was empty before I unlocked the door and bent over again. When I did I left it halfway open this time.

The final seconds passed without anyone else opening my cubicle door, although another person walk past, and I can only assume they saw me through the half open door. When the bathroom was empty again I walked out of the stall and took some selfies in the mirror. As I was doing this a middle aged man walked into the bathrooms, he gave me a look but I ignored him and kept taking a few more selfies before leaving.

I walked out into the mall again, taking a different route back to the car park. I stopped and took a few selfies as I went. I was starting to gain confidence, and really enjoy the walk. A 60 year old lady even said “you look fabulous” to me as I walked past her! At one point I got the zucchini out of my handbag and dropped it on the ground, bending over to pick it up. Then just as I was nearing the exit I stopped, keeping my legs straight as possible I bent over and undid one of my high heel straps, tightened it one buckle and did it back up. The whole thing would have taken me maybe 10-15secs. I definitely flashed my ass and the sparkling tip of my butt plug to a bunch of people who were walking past.

Keep reading Part 6...

[Kali_CD]

I got back in my car and drove to a park to carry out my punishment. On the way I stopped at a gas station to fill up my car, and went inside pay the cashier without incident. For my punishment I had chosen a park that fronted onto a main road. I chose a light pole about 20m in from the road, right next to a footpath that ran through the park. I kneeled down and took some selfies of me in position before starting the timer on my phone, which I stuffed into my bra on vibrate so I would know when my time is up. I secured my handcuffs, closed my eyes and opened my mouth. Now that I was here was starting to regret my bargain – this had the potential to be much worse than the spank stall. But it was late by now and not many people were around.

I was alone in the dark with my thoughts which started to run wild. If someone came across me what would they do? Roll me? Beat me up? Stick a dick in my mouth? I've never sucked a real dick before. I was half petrified half electrified.

After 10mins the timer went off and no one had come past, so I changed position and got down onto my hands and knees.

Just after I had changed position my heart skipped a beat when I heard someone walk past along the main road. I couldn't see them because my ass was pointed in that direction, I don't know if they saw me but they didn't take the little footpath through the park past me. The timer again zeroed out and I was nearly home free.

I went to a dark corner of the park, lay on my back, swung my feet over my head and began to fap. As I reached climax I opened my mouth to catch the jizz. I hadn't cum in 10 days leading up to this so when it came to load was huge. About half ended up in my mouth, the rest splattered onto my face. My last task was to walk about 1km back to my car with cum all over my face, and a hobble rope around my ankles which allowed only half a stride and was connected to my cuffs around my wrists. But along with with my orgasm, all my confidence had disappeared. So I left out the hobble rope, and just cuffed my hands in front of me, swirling the warm salty cum around in my mouth as I walked. Lots of cars drove past, and I got a few horns, but I made it back to my car without actually walking past anyone. Before I got into my car I used a finger to scrape the remaining cum off my face and into my mouth. With a gulping swallow all my dares were complete.

Thanks for reading! Please post your comments, or even better – some more dares! If they are creative I will send you pics of proof.

[thenewslave]

Oh my god I can't believe you've done this, you are so brave!
Also you are very hot
Great job on the reports, too, they must have taken ages just for our entertainment :P

I got one question: Do you think the people that saw you actually realised you were a CD or did they just look because you were dressed so slutty?

[Kali_CD]

Thanks! This dare was ages in the making - TBH I didn't know if I could go through with it - I'd never done anything like this before!

To your question: I think most people that saw me from the front would probably realise I was CD - from behind I could have easily passed. But who knows? I definitely had some guys checking me out as I walked passed them.

[thenewslave]

This sounds like so much fun.
Do you plan on doing anything like this again soon?

[Kali_CD]

I would love to! But im all out of ideas... I was hoping people would post some new ones for me here...

[Maximus11]

Wow. Just wow. That report left me speechless. By far the best I have ever read on this site. I am in awe of your bravery. Seriously, you deserve a medal for that shit. Both the dare and the report.

[SissyXcandy]

Go to a clothing store and find 3 very beautiful ladies and copy their clothing, then go to a dressing room and try them on. after every outfit go out of the dressing room and ask a female to make pictures of you for your mistress, pose 3 time on a sexy way..

[Kali_CD]

After what I just did you would think your dare wouldn't be so daunting SissyXcandy, but the idea of having to approach other people while CD still scares me! I'll see what I can do.

I'm toying with the idea of spending some time on public transport for my next outing... anyone want to start a new dare based on that?