My Little Red Skirt

Prologue: This story is freestanding but do read my biography section in literotica that would let you know the kind of individual I am and set the context of the story. I am a submissive crossdresser who occasionally meets compatible individuals for fun. I met this man at a fetish website and I became his slut. I have to call him "Sir", the following story describes my first public outing with "Sir". I love receiving comments and feedback so please drop in your thoughts after reading the story.

Sir is a strict and demanding master, and rather punctilious I should say. Well before two weeks prior to our date of meeting, Sir started to give me instructions on how I should present myself to him for our meeting. He wanted me dolled up in that tarty look, with heavy makeup, gloss, glittery eye shadows and thick eye liners. He chose an outrageous blonde wig for me with permed hair. I would have to wear a white sheer blouse which would make my black bra more obvious. To make me look even more like a cheap middle aged woman, I had to keep my blouse unbuttoned low enough, so that the junction of the two cups of my bra showed. For shoes, I am instructed to wear my black dorsy pumps with five inch heels.

In conformance with the orders received, I had to wear a black designer thong panty. But when Sir said that I should wear my little red skirt, I panicked. It was a pleated chiffon skirt and was pretty tiny. Going out in such an apparel in public would be a risky proposition for a crossdresser like me and could attract a lot of unnecessary attention towards me. I tried to reason with Sir and made him know the reason for my inhibition. However, Sir, in his characteristic cavalier style, dispelled my concerns, saying it would be fun and said that he would be there with me in public to take care of any unsavoury situation. I had to acquiesce.

On the day of the meeting I arrived well on time. I parked in the public square and had to walk quite a few yards down the plaza to the shopping complex whose top floor housed the normandin restaurant where we were supposed to meet. It was a nice beautiful day with fine weather. But I was feeling rather uncomfortable. And it was because my red skirt was just too small and flimsy!! It was so small that I was afraid that even the slightest draft of wind would raise my skirt up and my black panties would be visible for all to see. As i walked down the plaza, I kept fidgeting with my red skirt, trying to pull down its hem or smoothening out imaginary creases in the front.

After tottering around in my heels for few minutes i finally managed to reach the restaurant. Sir had already made the bookings and a corner two sitter table was reserved for the two of us. As the waiter ushered me to the table, i noticed that the other patrons of the restaurant were all looking well dressed and dapper. This made me acutely aware how minimally I was dressed and i immediately felt self consciousness and awkward.

Pursuant to the instructions of Sir, i had to sit with my skirt raised up so that my buttocks are in direct contact with the cold and sticky leather of my chair and my legs wide apart. Fortunately, the floral floor length table cloth managed to hide my nakedness from the other customers. It was well over half an hour and still no sign of Sir. Meanwhile, a man who was eyeing me from the moment i took my seat walked uninvited and sat on the chair opposite to me.

"Whats your name Madam"?. I sensed a sarcastic inflection in the last word. "Jessica" I said matter of factly and looked the other way. My demeanour clearly indicating that he was uninvited and should leave. However, he seemed to obtuse to take the hint. "I know you are not a real woman". (Big deal, i did-not even bother to tone down my husky voice). I just managed a half smile and once again looked towards the entrance making it clear to him that I was expecting someone.

However, nothing seemed to put off this uninvited cumbersome person. He started poking into my privacy, asking me indiscreet sexual questions which must have made my face red inspite of my heavy make up. I barely answered his questions, hoping to discourage him. In the middle of his interrogatories, he casually placed his hand on my thighs, moved his hands up and tried to feel my sex. I was surprised by this lascivious conduct and did-not know how to react.

Fortunately, as if by miracle, I saw Sir standing in front of the table and my uninvited guest just seemed to disappear into thin air. Sir is a tall well built man and probably his size had effect on the man.

Sir had no clue as to what was going on and I had to give him explanations. When I finished telling him about my little mishap, he pretended to sympathise with me but the huge smile he had on his face made me believe otherwise.

When the waiter came to take our orders, I cringed with nervousness and apprehension. I desperately hoped that the floral tablecloth overlaying the table behind which I was seated would hide my red skirt which was now lifted upto my waist and my little black thong panties which covered my sex only partially. What a relief for me when the waiter did-not come close to me as Sir took the onus for ordering for me as well.

When the waiter left to prepare our orders, Sir turned towards me. "Did you wear the black panties I asked you to wear?" As I said "yes", he ordered "Give me".

In the last couple of weeks, in my long telephonic talks with Sir, I had been so well prepared by Sir that I immediately knew what to do when he meted out this order in real time. Very gingerly, i placed my hands under my skirt and grabbed the waistband of my panties. I momentarily lifted my buttocks to let my panties slide down my legs and fall on the ground. Then as quickly as i could, i lifted my panties from the ground and handed it over to Sir. Sir almost displayed my little thongs in front of everybody before putting them to his nose.

Two ladies were sitting at the table beside ours. No way they missed a beat of what we had done. To my great surprise, I immediately felt relieved and even proud of myself to have gone through this first test which Sir had administered on me. But I had this premonition that Sir was only warming up and I would have to endure humiliations more intense during the rest of the day.

Sir handed me a girthy chrome butt plug and ordered me to go to the ladies washrooms and put it on. Sir was "generous" enough to let me carry this equipment in my handbang rather than carrying it openly in my hand which would have been mortifying for me. The insertion of the butt plug was troublesome but after a few attempts I managed to make it slide into my anus.

I walked to the basin to reapply some make up and adjust my blonde wig. My sex is rather small, but without the protection of my panties, I noticed that my skirt

barely managed to conceal my sex, even when not hard. A lady entered the restroom. It was one of the ladies who were seated in the adjacent table. I felt like running but could-not. I felt like my heels had been speckled to the floor. She started at me for a few seconds and I could see her reflection in the mirror. I got a shot of humiliation when I saw her face contort to show a look of contempt and ridicule, and she turned around with her hand on her mouth trying to control her giggles. I saw my own face in the mirror and saw that it was flushing red inspite of my heavy makeup.

I walked back to the table in slow measured steps to get myself adjusted to the new sensations of the heavy and rigid buttplug inserted into my button hole. But the feeling of being naked under my skirt was a rather good one. In my absence the waiter had already served the appetizers. I sat in the chair in the usual way (my little skirt raised above my waist, my buttocks in direct contact with the leather of the chair and my legs drawn wide apart). Sir immediately raised his right leg and tried to feel my sex between my legs. When the waiter came to bring our drinks, it was hard to maintain a poker expression on my face as Sir's foot was caressing my sex under the table making it grow in attention. I got so aroused and felt an irresistible urge to caress my sex but refrained from doing so by Sir.

When we had finished our main course i wanted to order my favourite desert of caramel custard but Sir announced rather abruptly that we are leaving. He then started to give me instructions for the rest of the day. He told me, while walking down the street towards my car, that i should carry a satchel without a shoulder strap in my left hand that he had brought with him and i should use my right hand to carry my mobile phone pretending to talk to someone. It took me a second to understand the import of his instructions. This basically meant that now both my hands would be engaged and i would have no way to cover my modestly if the wind raised my skirt in public. I am terrified! I gave Sir a beseeching look hoping Sir would show some compassion on me. But Sir gave me a hard stare and i knew i had to submit. As soon as the bills are settled, Sir immediately stopped caressing my sex and ordered me to get up and start walking. My sex was still hard and i wanted to wait for a few minutes for my erection to die down but again this supplication is dismissed immediately.

As i come out of the restaurant, i never felt so exposed and vulnerable in my entire life. I was wearing a tiny red skirt in public with no panties underneath for protection. Both my hands were engaged and i had no way to cover up my nakedness incase the wind played with my skirt. The huge butt plug invading my bottom hole did-not make things easy either. And my sex was not yet flaccid and the bulge in my skirt would be visible to anyone, showing that i was not the woman i mimic.

The place was brimming with people and I had the feeling that they were all looking at me. I hobbled in my high heels, taking ridiculously small measured steps through the busy street. My head slightly cocked to the right and talking on my mobile, trying to make believe that i was in a deep conversation with someone. Putting me in such a predicament, Sir was keeping a rather "safe" distance, walking some distance behind me.

I managed to reach the lane where my car was parked without any mishap. But just a few metres before reaching my car, a sudden violent gust of wind blew my skirt up, it billowed in the breeze for well over a few seconds before coming down.

My Marilyn Monroe moment was surely not lost on the passerbys who had a fullsome view of my sex or my buttocks depending on whether they were walking behind or opposite of me. I could hear a couple of cat calls from behind, not sure if I was the object of their derision, I was just too scared to look back. I was so mortified by my bold public exhibitionism that i almost ran to my car. Sir entered a few minutes after me and the smile he wore on his face showed that he was having good fun at my expense. The drive back was not uneventful either. Sir kept on caressing my inner thighs and sex and i had a hard time from preventing myself from cumming. It grew rather risky at the traffic junctions where Sir was caressing my lower body and the passengers in the adjacent vehicles would guess what he was doing to me.

Finally, i dropped Sir at his place, and turned back home. When i reached home i noticed something amazing which had never happened to me in the past. It had been well over 4 hours since i met Sir. And all this time, Sir had managed to keep my sex in almost constant erection. Relaxing in my home, i began to think of the events of the last few hours. Now that my fear and nervousness had died died, i felt a strange thrill coursing through my entire body. The fact that i had exhibited in public, and so many strangers had seen my sex and buttocks got me so excited that i had a marvellous orgasm.

Even now Sir and I do continue to meet outside irregularly, and he would subject me to daring exposures in public places. Everytime Sir would propose the idea of taking me out in a state of nudity, I would initially be scared to death and resist, but he manipulated me so well that I capitulated. I must admit that it wasn't as difficult as I thought it was and even started to enjoy myself. The adrenaline rushes were incredible and I started to get excited just at the thought of being Sir's slut and having my panties or genitals being seen by random strangers in public.