Note from myself: This is an account written by my ex girlfriend relating to a public dare I set for her about four years ago. She was unaware that I had followed her and was in fact watching her from a distance. She was also unaware I managed to take a couple of mobile phone photos of her from behind. 

This is written from her perspective:

Well where to start? Okay, well you will be pleased to hear I completed my dare as instructed and even though I surprised myself I managed to go through with it to the letter I think. I have to admit to you how nervous I was once I had parked in the car park but at the same time very excited and horny as well. The butterflies in my tummy were like nothing I have experienced in ages so I hope you understand.

Okay, got myself dressed around 5pmish after showering and shaving my legs and pussy, perfumed and painted my nails first then got the steel plug ready, I touch of lube and slipped it inside me. I love how it is always so cold at first and I can feel it intensely inside my ass. Next I did my make up, a little heavier than normal day wear, darker eye shadow and dark pink lipstick, pinned my hair up loosely with a pony tail at the back and wore some dangly oval hoop earrings and a Bohemian necklace plus my little silver ankle chain.

Then put on my heels, I decided on a dark blue pair with cream heels, higher and strappy. Then slipped on my dress remembering to leave the top two buttons open as you had asked plus the one at the bottom leaving only three buttons done up, looked in my long mirror and must say it felt so sexy and slutty and the dress barely covers anything really!

I turned round to have a look in the mirror and did a test bending down pose, legs slightly parted as instructed and the dress rides up a lot! I could clearly see my bum and the plug too! I also noticed how thin the top part of the dress is, I could see my nipples were poking through the material and with two buttons undone some cleavage as well. I felt very very sexy!

Nothing more for it but to take the plunge as I said I would not back out for you so grabbed my handbag and shopping bags then walked out of the house to my car.

It is a nice warm humid evening here tonight, so perfect for the type of dress I had on for this. No need for a jacket or anything so I walked to my car.

On the drive to Tescos supermarket I kept thinking of where to park away from the store so I could play with myself in the car as instructed without being seen. Found a spot in a far corner then parked the car front in towards a wall and as it was fairly quiet I could play , get myself wet . I reclined the seat and parted my legs , checking no one was around I closed my eyes and started teasing myself between my legs, it felt so sexy having no knickers or bra on and knowing all I had on was the dress, I shifted my ass in the seat and could feel the plug going in deeper.

After about five minutes, I could feel myself getting very wet and so I did not make myself cum I stopped then to looked at my fingers which were soaking, no doubt there was a wet patch at the back of the dress by now. I composed myself, grabbed my bags then opened the car door taking care to swing my legs out slowly, slightly apart then stood up. I could feel a little wet patch at the back of my dress, too late to do anything about it now.

Locked the car, took a deep breath then started walking towards the store feeling very nervous now, it’s been a bit windy all day here but has picked up a little now, not strong gales type thing but random gusts every now and then but I knew I had to walk and ignore the dress blowing up as you had told me to. As I walked the gusts did tease the back of the dress, twice lifting it high enough for me to know my bum was on show, I could tell, I left it alone though and carried on walking.

I could feel my braless tits bouncing against the front of the dress and the open top part flapped a little as I walked.

As I neared the store the front of the dress blew up suddenly but I kept my promise and ignored it. I finally made it into the store, I had got one or two looks from people on the way in, men mostly and a guy smiled at me too. I then grabbed a trolley and walked down the first aisle, heels clicking on the floor as I walked.

After going down the first three aisles I managed to pluck up the courage to do my first bend down for some sugar. I stood legs slightly parted then bent only from my waist as instructed. I could easily feel the dress ride up my bum as I did so. Not sure if anyone saw me the first time as it was busy but not in the aisle I was in at the time but it did feel good doing it in public.

The next aisle I walked down more slowly as it was busier, there was this guy (about fifty or so) who began looking at me sideways and smiled at me once. I needed something off a high shelf so I stretched on my shoes but could not reach it so he kindly offered then placed it in my trolley smiling again, I thanked him and he said ‘any time love’ His eyes seemed to be fixed on my tits then as I had not realized how much my nipples were poking through (it must have been the playing with myself in my car)

He then said, "That’s a very pretty little dress on you." I thanked him and he replied, "I love your shoes too, really sexy." I smiled at him then pushed my trolley onwards. I then walked on further but could see and feel him staring at my legs.

At the end of that aisle I thought then would be the perfect time for bend down number two so I stood again legs slightly parted and bent down fully to the bottom shelf, as I did so I glanced sideways and he was staring straight at my legs! (probably a lot more) LOL

Next aisle was busy as well, I had to dodge round a few people but could see some stare at me as well, then I noticed the guy was back, he had followed me round the corner and was looking straight at me once more. So I carried on walking away slowly then turned the corner then moved further on to a different aisle as I wanted to find out if he was following me.

After about five minutes or so I found myself in the milk aisle and the milk I buy is always on the lower shelves. So I went for bend down number three and thought I would do so more slowly this time, again legs slightly parted on my heels and bent at the waist, down to the milk shelf, I felt the dress ride up again. At that point could feel myself leaking again, it was sudden and I saw a drip from my pussy hit the floor I think some leaked a little down my left thigh. I did as you instructed though and kept my legs parted a little and let it happen.

I could feel I was sticky and wet by now so I slowly stood up with the milk then noticed my old friend was back again. He was way back at the end of that aisle staring right at me! His mouth wide open! How long had he been there I wonder? What had he seen? This only made me more excited and wet knowing I had a bit of a stalker I guess you might call him

After twenty-five more minutes I had nearly done all my shopping but I had one last aisle to do (remembering that you had told me to do four bend downs in the store). So I went down the Wine and Champagne aisle, making sure I selected a red wine on the bottom shelf.

Again I stood legs parted, took a deep breath then glanced over my left shoulder and then there he was once more, standing with his own trolley staring right at me smiling. I smiled back this time then parted my lips a little. I let my hand move slowly down my tummy and onto my hip and then went for it. Turning away slowly I then bent right down at the waist keeping my legs straight and parted them making sure my bum was facing the guy.

The dress rode up once again. I could feel the plug move slightly as I clenched my cheeks, I leaked a little more this time it ran down my leg further as I grabbed the Wine I looked behind me sort of under my arm pit then as I stood up he was staring right at my bum and legs smiling at me. He then mouthed some words to me which I think were, ‘You are fucking gorgeous’ or something like that as he only mouthed them to me. He then shook his head from side to side and winked at me. I smiled back then blew him a kiss. I then walked off to pay for my shopping.

While at the checkout the guy was in the next lane of course. He had his eyes on me all the time and every time I glanced at him he smiled and winked at me and kept staring at my legs.

After walking outside I knew I had one more task to do so I walked to the ATM to the left of the store. As I stood there typing in my password etc. to draw out some money I could feel the wind gusting the back of my dress up in little billowy blows. Then one stronger gust blew it up over my back a little. I knew my bum was on show, it quickly fell down again though but before I left the ATM there were two or three more nice little gusts that teased the dress hem higher.

On the way back to my car I got a few more looks from people. I heard a wolf whistle but I could not see who had done it.

As I loaded the back of my car with my shopping I had to bend over slightly and lean into the boot and heard a very quick toot from a passing car. I looked up at the driver and it was him! As he drove past he blew me a kiss then mouthed some words again but I could not make out what they were this time but I am pretty sure he mouthed the word ‘fuck’ in the middle.

Driving home I could not stop thinking about the whole experience and how thrilling it was also that I had actually had the courage to do it as instructed. It felt so slutty and I want to do it again soon but maybe wearing stockings and suspenders next time as you have suggested before.

Lastly when I got home I checked the back of the dress. It has a massive wet patch and I then pulled out my steel butt plug to discover it was glistening with wetness and quite sticky too!

I wonder if the Tescos guy saw just what was inside my ass?