Ensnared by a Corset

Monday morning came and we waited for sissy boy to make his pass. He was on time and Susan was right, the corset caught his eye. He even stopped. Damn her if she was going to take the bet. For a week we watched him as he would amble past eyeing up the corset. Never the other windows contents, always the baited window. It was as if Susan had laid a web out and he was slowly getting ensnared in it. She was disappointed that the weekend ended and he didn't come in, but she headed home that Saturday claiming Monday would be the day.

The new week came and he passed by as slow as ever. I made some jibe to Susan but she just told me to wait and see. Just before 5.30 p.m she was proved right once more, the doors bell chimed and in walked sissy boy. He crossed to the sales counter red faced and shaking with nerves. This was delicious and I felt like here I could have some fun. I felt that a game had begun and we held the winning cards. I looked up at sissy boy as if only just seeing him me and smiling gave him a "good afternoon".

I could almost sense his conflict of mind, part wanting to run and the other part wanting to make the purchase and then do the run. "Can I help you sir?" Was my next gambit in the game that he unknowingly stepped into? I was finding his red faced terror quite delicious, hell even a turn on. I throw another sycophantic smile at the sissy. God he was a nervous wreck! A mumbled "yes "there's a corset in the window, I would like to buy it for my wife... girlfriend". Wife, girlfriend! I hid my amusement at his 'story. He was a pathetic specimen of the male sex, and even I could see the sad bulge in his suit trousers. He may be scared but he was 'boasting' a tiny erection. This was turning me on in some weird unexpected way; I was getting turned on by his humiliation!

Ok I needed to move this along. I knew what he wanted but a promoting was required or we could be here all night. "The delicate lacy corset?" I asked knowing the answer and I threw him another smile. The sissy actually relaxed and the sweating seemed to diminish. He thought I believed his sad tale, wife, and girlfriend! "Yes that's the one, "he mumbles "and the knickers to"

Another smile at the fly in our web and a "Yes sir, not a problem, do you know your wife, sorry your girl friends size?" He asked for a 14 to 16, the pathetic sissy. This was delicious but it was time to change the games rules. "Would the corset be for you sir?" Seven little words but I was sure he was about to pee himself. God he went red! I had to help him here or we would have a sodden carpet.

Smarmy smile and "it's ok sir, we have many gentlemen clients" (sissy, trannies...) "who share a similar appreciation of ladies lingerie as you, so please don't worry." Thank god he breathed again and my carpet was spared a soaking. The game was mine with his next words. "Well yes it is for me". Ok so now we had to take another step towards Susan's declared goal, and to do that we had to be more realistic about his sizes, if it didn't fit the game would end. "So sir is a 14 to 16 size? Hang on one moment please" I told the pathetic sissy and rummage through the coat hangers on a rail, "This is a 14 sir, which I think will be more your size than a 16".Throw him another smile and lay the corset on the counter. "Would you care" smile again "to try it on in one of our changing rooms?"

God you should have seen his face, I feared wet carpet again, he looked like someone had sneaked up and showed a cucumber up his arse. So time for more carrot, the stick would follow soon enough. "Don't worry darling we are discreet and as I say we have a number of girls like you as our cliental. Pop into the changing rooms, and if you would like, once dressed, give me a call and I would be happy to judge the fit and the style for you. "God I was such a lair, but hell if I was too loose my bet then I would do so in style, and lies only count if you're caught. The sissy went red again and the wee bulge returned in his trousers. God was that best he could do, any smaller and someone would stick a cube of pineapple and cheese on it! But my sweetness and winning smiles worked, sissy boy took the preferred corset and walked off to one of our changing areas.

The little sissy had left the thong on the counter so I passed it through to him, or should I call him her? Hell I didn't know! Then I added some stockings to. This was so much easier than I'd expected.

Susan emerged from the back room where she had been keeping low, so as not to intermediate the little sissy. I handed her £50 from my purse and whispered, "Looks like you have won the first bet, but how about a second go?" She smiled and leaned in, where I made my proposal in a whisper. Hands were shaken and round two began.

"Are you ready Hun" Susan called pulling the curtain back and an incoherent "yes" emanated from behind the curtain. He, sorry she, pulled the curtain back and stepped out. God you should have seen his face, a picture. Susan and I just stared. Truth be told he, sorry she, had a great figure and looked the part. 'Shaved his legs and he was a she' in the words of the song. I just could not believe what the silly little man had allowed himself... her, to become. I just pointed and burst out laughing. "My, doesn't he just look the pure sissy" and his tiny erection vanished at warp speed. Susan and could not stop ourselves laughing, but at least she managed to snap a few photos.

Once I had some breath back I managed to turn to Susan "another sad sissy boy who thinks a few clothes and he is a girl." Sissy boy made a move for his male attire but I was faster of the mark and swept them up. Now she started crying, real life tears and pleading. This simple bet had turned into more, and was turning me on big. I wondered how Susan felt as she down loaded the images onto the lap top. He started to remove his lingerie but Susan put a stop to that" Leave that on sissy boy" More tears from sissy and back with the pleading. "Forget it sissy, this game has barely begun". I told her. "Now while Susan stores the photos on line, we will finish dressing you and the in CCV will carry on making a record of your dressing." Another lie, but how did she know we had no CCV; she was in no state to look around for the cameras. This lying was easy." just do as we require of you for the weekend and then the photos will be deleted." Now that just had to be my third lie, so far?" You will be a free agent, and if you're really good girl you can have the corset for a 50% discount" At this point I lost it and couldn't stop myself from laughing. Such a cute sissy and the fun had barely begun.

Part three

The cows just laughed at me and I so wanted to die. The 'fucking' corset wasn't worth this, no way. My mind whirled, I knew dressed like this I couldn't run out of the store, so I needed to be a 'man 'and get my clothes of the bitches. I made a move towards the bitch with my clothes, determined to put an end to this. As I reached out, the fucking cow laughed and after that? Hell I don't know what happened; there was a blur, a falling, a thump and then pain. I landed on my back and she just laughed as she rested one heeled shoe on my chest and told me to stay where I was. A woman had thrown me! I lay there winded, defeated and feeling like a piece of sh*t in these women's hands.

She looked down at me and tutted, "that was stupid sissy boy, next time I will break a bone, so just stay where you are and be a good sissy, we haven't done with you yet" and with a casual flick of her foot the stiletto healed black court shoe flew off. I could see her stocking foot, the toes nails painted red in all there detail as she brought the foot closer to my face. I could smell the scent of a day's perspiration from confinement within a fashion shoe. The odour of a day's walking and as the foot drew closer the musk became over powering. She placed the tip of her nylon encased sweaty toes against my pressed lips and eased the nylon toe nails between them. I pressed my lips together to prevent her forcing her foot in, and moaned a protest through my clenched lips. But how long can you resist a foot being forced into your mouth? Not long, I resisted for as long as I could but the sheer pressure slowly eased the toes in. I wanted to lick my lips to reseal them and that's when I lost the fight. With a push her toes slid between my dry lips and her sweaty toes entered my mouth. I gagged on the nylon, on the musk of her foots ordure, but she just laughed and teased her stocking toes around my lips. Humiliation upon humiliation! As I surrendered and ran my tongue along her stocking toes, I felt a weird mixture of humiliation, degradation and the unwelcome stirrings of an arousal.

Part four

I watched as Susan eased her foot into the sissy's mouth, as tears welled from his eyes. I had at first felt a pity for the poor lad; he wasn't much older than what? 21, 22? But he looked as pathetic as he lay there panty and corset clad. As much as I felt pity I was also aware of an arousal, that this situation had developed a sexual element. It was turning me on. I found I was becoming wet and almost without planning squeezing my thighs together. Susan eased her foot from the sissy and told him to just lie where he was. Then I watched as she unhitched her skirt and let it fall to the floor. Her blouse followed next and she stood there in her matching panties, bra and hold ups. I have to admit from a professional point of few she looked amazing, and from the view point of single 40+ women, who hadn't been fucked in, well a long time, stunning. What had started as a bet, as a game, had with no planning from me taken the most amazing and erotic turned.

I eased the saliva coated toe from his mouth, and watched as the tears stained his face. Now I knew I would have all my fun, but I had a way to go yet before his humiliation was complete. Now I had to ease the game up another notch. Caroline was a stunning woman and I had long admired the legs and figure of my boss. But she had ignored me and been unaware of my flirting. But I could see the arousal in her eyes, the way she stared at sissy boy and pressed her thighs together. Now I had to step the game from one of humiliation to one with a strong sexual aspect to it.

I shed my skirt and blouse, standing still for the shops other two occupants to admire me. I knew I looked good as I had dressed with such care this morning. I also knew sissy would comply with my designs and lusts, but dare I hope my boss would fall in with the entire game? Dare I? Judging by the fire in her eyes, I dare.

I could not stop staring at Susan; she had a figure to die for and legs that went on forever. If asked I would declare myself to be straight, 100% straight, nay a kink in my sexuality. But I still found myself looking at the lingerie clad sissy that Susan now had kneeling before her. Then there were the curves and shapes of my assistant...

I knelt before Susan in my lovely stockings and corset. My eyes were level with her panties and I feasted them with the speculation of what the thin material covered. Miss Susan took my hair with her hands and pulled my face towards her panties. I could smell her scent and see the dampness of her excitement. With a firm but no nonsense tug she pulled my face into her panties and I became smothered by the soft material, her warmth and her scents.

I watched as the sissy was held to Susan's panty clad mound and as he was forced to inhale her sexual musk. I found my own state of arousal was becoming too much and my hands sought relief under my skirt and my own moist panties. Caroline the strait woman, the owner of the Panty Box, was being turned on by watching her sales staff dress and humiliates a sissy boy. My fingers caress the moistened material of my panties before they prized the gusset aside and found the wetness that was seeping from my long neglected pussy. The fingers caressed my swollen lips and explored the nectar that was seeping from deep within me. I leant back against the counter watching the scene being enacted before me. Sissy boy was pressed deep into Susan's sodden panties, her hands holding his head in place.

All I could smell, breath and feel were the woman's panties. Her musk was over powering and I wanted my tongue to seek the source of her honey juices. But every time I sought to ease my tongue into that panty covered well, her fingers would tighten their hold on my hair and pull me back. I would not be pulled away but just far enough so I was still buried into her lingerie but far enough back so I would be frustrated and unable to do what my mind screamed for. To sink my tongue into her warm, wet, enflamed lips, to taste her pussy. My cock was erect and ached at the frustration I was being enforce to suffer, and I was powerless to have my way.

I could not turn my head, her hold was to tight, but I could see from the edge of my vision the other woman had hitched her skirt up, eased her panties to one side and had her fingers sunk deep into the wet haven between her legs. I watched as she worked herself to arousal and I breathed in the heavy musk of those panties I was pressed into. My cock could stand no more of this frustration and I was unable to prevent it shooting its load. I moaned as I emptied my sack of my spunk and could feel the lovely thong I had been wearing being transformed into a sodden and soaked piece of material.

Part five

I had called a taxi and the three of us sat in the back. Caroline and I sat either side of the sissy boy. I had made a mistake a year ago by ordering a range of 'adult fun' clothes. You know, nurses, policewomen... Few had sold and the remnants had been consigned to a box in the back of the stock room. There until today they had they had gathered dust. But lurking at the bottom of the box were three or four blue 'Alice in Wonderland' dresses. Nice, feminine, over the top and just perfect for a sissy.

Between us sad a vision in blue satin! He or she, you can take your choice, looked ridiculous. Plenty of lace trimmed around the neck, a lovely central rosette, more lace and an underskirt that showed her panties off nicely. She looked so adorable and even had a lovely petticoat. She had retrained her stockings of course, and we had furnished him with a cheap blonde curly week from one of our display dummies. With some rudimentary make up he looked the personification of tarty. A sweet girl, her cheeks burning red and stained panties on show.

The taxi driver had one eye on the road and another on the three girls sat in the back of his cab. Caroline and I each placed a hand on sissy's legs and eased them apart so the driver got a good view of his sodden panties. Sissy was red with humiliation, but what could he do? Leap out the taxi and totter away in his high heels? He had nowhere to go and could just sit there and wonder where we were heading. His wallet had been a source of so much information and even gave us the final location for the game to end. Or for sissies chapter to end!

Caroline had joined in the game better than I had ever imagined and I had been stunned to watch her cum under the magic of her own fingers. She had seemed to come alive and once sissy boy was delivered to his destination I hoped to persuade Caroline to let me provide her with further 'pleasures' with the compliments of my own fingers and tongue. Then later on, well there were other sissy dresses in that box, and a good game should never be played just the once, should it? But first we had a bet to sort out.

Part six

I sat in the chair; my wrists were tied to the arms of the chair and my ankles to the legs. But they were tied in such a way that my satin skirt and petticoat had risen up and my panties visible. I could smell the musk of my drying spunk but that was the least of my fears. I was tied to a chair, wearing stockings, panties, and was a vision of blue satin and 'come fuck me' high heeled shoes on. The wig and the makeup were cheap and tarty, as was the entire way I looked. They had brought me in the back way, using my own keys and up a flight of stairs to the room where I now sat a prisoner of humiliation. Then they had spent ten minutes taking photos of my in my state before they waved their farewells and vanished back down the stairs.

That was three of four hours ago and now dawn was creeping in through the window. I knew that they weren't coming back and I started to cry once more. All I had wanted was a corset, a simple thing surely and I had ended up here. It was 8.30 a.m, and I was tied to an office chair and I could already hear the sound of footsteps as my colleagues walked into the room where I was tied to my office chair, corseted, sissified and humiliated.

THE END