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High Heels and the Computer
  • Author - Debra Darling  
  • Rating -   
  • Site Rank - 243 of 2548
  • Unique Views - 29524
  • Story Codes - F-m, M-m, consensual, bondage, caught, cbt, cross-dressing, humiliation, spanking
  • Post Date - 7/21/2010
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Author's Note: Please help me

It all started simply enough. I just loved to cross dress in lingerie and high heels. Then I bought a computer and discovered sites like this one. From there things began to expand as did my wardrobe and my interests. Self bondage, mummyfication, full crossdressing all began to fascinate me. I was spending entirely too much time and way too much of our budget on clothes, bondage gear and chat rooms.

I discovered Mistresses about the same time my wife discovered my secret stach of shoes. Although I did not know it she began tracking my activities on the computer. It was not long before she knew everything and she was truly pissed. I had more shoes that she did and a large collection of sexy night wear and that made her jealous as well as angry.

Then one night as I thought I was safe, I got caught. She had gone out for an evening with the girls was what she had told me. "Dont worry," she said. "I will be out very late and we will probably get too carried away, I will call you and let you know when I am headed home."

Wow. The whole evening to myslef and a warning before she would return. She was barely out of the driveway before I headed for my stash. It took only a few minutes to put on a satin nightgown and three inch heeled bedroom slippers. These had lovely mirabou feathers all over the top and were backless. Easy to walk in and oh so sexy. Everything was in virginal white.

I started reading stories on the computer and became so engrossed I never heard her sneak back into the house. I did not know she was there until I felt her hands on my shoulders. She bent down next to my ear and whispered, "Very sexy story. And a very sexy outfit too."

I was so startled I nearly jumped out of my skin. I tried to say something but she just held me down in the chair and began to brush my neck with her lips. "Let me see all of you,' she said in sexy grjowl. "Stand up for me."

I complied and turned around for her. She had me model the outfit and then she said, "I want you, but I want you in something even more sexy. Are you willing?"

Of course I was. I agreed immediatly and the next thing I knew she was pulling things out of my stash as well as out of a large canvas bag that she had thrown on the bed. Everything went so well at first that it was like a fantasy.

First cam a lovely satin corset. All red on the inside and green and black brocade on the outside. I had bought it from Romantasy in San Fransicso and it was pretty expensive. The laces were satin ribbon and she began to pull them tight. As the corset closed I realized how heavily boned it really was. My waist was being crushed and my chest and hips were being pushed up and out. My back curved and I slowly assumed a wasp waisted "S" shape as everything adjusted. She did not stop until the thing was completly closed, tighter than I had ever laced it. I could barely breath and bending over was out of the question.

She dusted the tops of my new, but small, "breasts" which lay in the cups of the corset. She took two large artifical nipples from her bag and glued them over mine. They made my little breasts look almost obscene.

Next she folled a paif of black silken stockings up my legs and fastened them to garters on the bottom of the corset. A long golden wig came out of her bag and she placed it on my head and threaded my own hair through the cap and braided enough of my hair to hold the wig in place.

She did my makeup using blud eyeshadow and bright red lipstick. The most painful part was when she plucked my eyebrows. I protested but the promise of unbelievable sex soon quieted me. She glued the longest artifical fingernails I had ever seen on my fingers and then painted them bright red. "Aren't you supposed to cut and file these?" I asked. She answered with a laugh, "Not for you sweetums. Not for you,"

A pair of black, crotchless panties with lots of ruffles on the bottom came next. Then a full length, black satin nightgown. All lace on the top , cups over the breasts and then satin falling to the floor.

When I said only a pair of slippers was needed to finish things off, she smiled and said, "Not quite, dear, but we will get to that soon."

She disappeared for a while into the computer room, leaving me to explore my new found feeliings and to wonder about what she was doing and what she was up to. This was so out of character for her but I loved it. I guess I loved it too much to really think about what might be going on.

When she returned she dug into her bag again. Out camer a black neck corset. She put it on me and laced it tight. It sat on my shoulders and held my head in its emprace. It covered my mouth and I could not move my head at all. A chrome rod ran from under my chin down to a fitting on the front. She adjusted the rod until I was looking slightly upwards.

She put a wide leather belt around my waist and locked it in place with a padlock. There were lots of rings and fittings around the belt to attach things.

She had me stand up and led me into the computer room. She had moved the monito and keyborad over to our stand up desk and placed them there. She had me stand in front of the keyboard and she attached chains from my waist belt to some eyebolts she had installed in the desktop. Locks made certain i would stay there.

She reached up under my nightgown from the rear and grapsed my cock. She soon had it hard and me moaning. She stopped for a minute and I felt something being wrapped around the base of my cock and balls. She told me it was a control strap and she quickly cinched it tight. She led this up to another eyebolt on the bottom of the desk and locked it in place. Now I was truly attached to the desk and standing on my tiptoes.

Back to her bag and out came a pair of women's shoes. She bent down and put first one and then the other on my feet. I could not really resist as she fastened the straps. My leg muscles cramped for a minute as I tried to adjust to the height of the heels and she told me they were six inches high. They were black patent pumps with T-straps so I could not kick them off. Stilletto heels and pointed toes. She told me they would be like torture after a few hours standing on the hardwood floor.

"Hours?" I thought. "Surely she was joking." As I found out she was not.

She then laced a strange pair of gloves on me. Black satin, thye reached up each arm past the elbow. Straps just below the elbows fastened them tightly to the arm and then to the waist belt.

Similar straps at the wrists were tightened and then fastened to rings closer to the frony of the belt. The total effect held my hands about six inched apart and kept them posed over the keyboard. Between the elbow straps and the wrist straps I could not move my hands of arms although I would be able to type on the keyboard.

The last thing she did was to open the zipper over my mouth covering and insert a large round ring. It went behind my teeth and held my mouth wide open. A final strap fastened to the to of the collar and went up over my head to the other side. When it was tightened it pulled my mouth tight around the ring and held it firmly in place.

" You bastard!" she nearly screamed in ear. "Did you think I would get off on this sick behavior? And what right did you have to spend all our money on this crap? Well, you are going to regret every minute and every dollar, starting now!.

With that she took off her panties and stuffed them into my mouth behind the ring. They were sodden and tasted bitter. "Yes," she said. "I wet them just for you. I hope you enjoy the tast of my urine." She then showed me the joystick she had used to replace our mouse. The only way I had to use it was to bend over and take it in my mouth. As I moved it around it would squeeze her panties and force a bit more of her pee down my throat.

Your job is to navigate to one of your sick story sites and write a story about what has happened to you. You will stand there until it is printed. You had better get it right because I am going to use this lovely cane I bought on your ass when you are finished. One stroke for every mistake you make.

So here I stand, typing away. Do you have any idea how hard it is to type with two inch long nails? I have been here for hours and my legs are cramping. My toes feel like they are numb and I swear the heels are pushing up through my feet. I am really worried about what comes next though. She put one of my old style microphone stands where I could see it. It has a giant dildoe on top, a pair of eyebolts on the bottom and standing next to it is a pair of ballet boots that look to be about knee high. She says they are taining shoes for the pony boots whatever that means.

Part Two (added: 10/29/2010)

Twelve mistakes. Twelve cuts with the cane. I was soon howling and dancing about as the punishment seemed to go on endlessly. In the end, I suppose I got off lightly. After all, typing in gloves with two inch long nails is not an easy chore.

What is worse is the way my wife giggled as each blow fell. It was clear she was enjoying dishing it out to me. She made me count the strokes which was so humiliating. Having to thank her was even worse. "One, thank you Mistress, madam. Two, thank you Mistress, madam. Three, thank you Mistress, madam. It was so hard to count when I was screaming in pain from every blow and crying from shame. In the middle she gave me several quick ones and I lost count. Instead of seven, thank you Mistress, madam, I said six. Of course, that meant starting over again from one. The next series I got all the way to ten, thank you Mistress madam before a particularly hard cut caused me to miss the madam. I pleaded but to no avail. We started over yet again. By the time she finally stopped I was red from waist to knees and had more than a few welts.

She left me alone to recover and stop crying. I was still attached to the computer table so I was left standing in my uncomfortable high heels. Thanks to a cameral over the monitor I could see myself quite clearly. I looked like a sissy guy in a long blond wig. My mascara had run from all the tears and I looked like a clown with all that slutty makeup so messed up.

How long I stood there I don't really know. I only know my toes felt like they were numb and my leg muscles ached all the way from my ankles to my hips. The computer clock had been disabled and she had pulled the plug on the keyboard before she left me. Every once in a while the computer would switch over from the camera to a slide show of pictures that I had thought were secretly stashed in a McAvee vault. Somehow she had found the password and accessed the files. They were pictures of cross dressers from many different web sites. Mostly they dealt with men who were forced to cross dress and then placed into bondage. They kept me in a state of tumescence but they also caused me a great deal of worry. Was she going to try to use some of those drawings and photographs? If so, how?

At last she did return but she looked almost like a different woman. She was dressed all in black. Her outfit included a black bustier, long silken stockings, black stiletto heeled boots and severe makeup. Her large breasts were pushed up and in to form a massive cleavage. She had always been sensitive about the size of her breasts, even going so far as to suggest breast reduction surgery. She knew I loved them just the way they were and now she was clearly flaunting them in front of me. She boasted a whip now, long and with many leather lashes. She showed me the metal tips at the end of each lash and laughed as she told me what they would do to me when she started whipping me again. .

I cringed in fear of this dominant woman who had been my gentle, loving wife. I knew I had brought this change about myself but that still did not make acceptance any easier.

"Like what you see?" she asked coyly, posing like a model. "Want to get some more of me, big boy? Would you like to fuck me lesbian style? Just us two girls on the bed together?"

I nodded yes, speechless as she removed my gloves, waist belt, and neck corset. She wiped my face clean and then redid my makeup. Since she had turned the camera off, I could not see myself. She removed the corset and then my shoes and stockings. My feet and leg muscles screamed at me as they cramped before they finally relaxed as the strain of the high heels went away. I was so disappointed though as I had truly thought she was going to help me with my ultimate fantasy.

"Don't get too comfortable, lover," she whispered. "I have some surprises for you and you may not like some of them. Then again, who knows. Maybe you will get your fantasy fulfilled if you are a good girl." It was that promise that kept me in line and from trying to overpower her and escape.

( link opens in new window )

The first surprise was a while corselet that went from hips to bust. It had lots of lace panels and fastened up the front with a myriad of hooks and clasps. When it was in place she pulled each bra cup away from my chest and lifted up my little fake breasts. Under each one she placed a silicon insert. When she released the bra cup, the insert and push up padding in the bra lifted my own little breasts up and created cleavage and quite a bust line. Then she went behind me and started lacing.

About then the doorbell rang. She stopped lacing and went to answer it. "Don't' go anywhere," she laughed. "I'll be right back, hon."

I heard the door open and then voices as she talked to someone. Then I heard the sound of several pairs of heels on the hardwood floor. I turned to look as she and two of her best friends from next door and across the street came into the room. They all laughed at me as they took in my plight.

The three women exchanged hugs and then some fairly passionate kisses. My wife turned to me when she came up for air and hissed, "Lesbian love. You wanted this didn't you? Well just watch and see what we can do for each other." All this time, while I had kept hidden my cross dressing fantasies she had been spending her afternoons with the neighbor ladies and they weren't drinking coffee.

The other two women quickly stripped off their jeans and blouses. Underneath they wore just sexy lace bras and thong panties. One set was in red, the other white. They quickly donned matching high heel pumps with four inch heels that my wife gave them. Just watching them play with each other's gorgeous bodies brought me to stiff attention of course.

Together they began to finish the lacing job my wife had left undone when she answered the door. With three of them, two on the laces and one working away with some kind of a lacing aide, they soon had the thing fully closed. I was now gasping for air it was so tight. Each breath was small and shallow and I felt like I might pass out from lack of oxygen.

"Now, don't' swoon," one of them said. "That would be such a girlie thing to do." They all laughed at this and swatted my exposed bottom. I yelped in surprise and pain as it was still very tender from the caning.

White stockings were rolled up my legs and clipped to the garters on the corselet. A pair of white crotch less panties with rows of ruffles on the back were drawn up. The line running from my control strap to the desk was released long enough to thread it through the open crotch and then it was refastened and locked to the desk ring. White ankle boots with lots of fancy beading were put on. They had four inch high platforms on the sole and ten inch narrow, pointed heels. I know because they told me. The toes were pointed and the boots had laces on the front that were soon laced tight and tied in knots so they would not come off. It was like standing in six inch high heels but on stilts. My leg muscles began to scream as soon as they stepped back. My toes were being pushed forward into very narrow, pointed toe boxes and I knew these were going to be very painful very quickly. When I tried to lift one foot to ease the pain, I realized they were very heavy. "Each of the platform soles is filled with ten pounds of lead," one of the women told me. "That will be your handicap in the races tomorrow."

I had no idea what she was talking about but it did not sound like anything I was going to like. I would come to find out that the races were something I would have nightmares about forever.

"What do you think, girls? my wife asked. "Does he look bridal yet?"

I blanched. Had she found it? No, she would never look there. My secret secret was safe.

The girls played with me for a while, running their hands up and down my nylon covered thighs and over my panty covered bottom. They made sure I got hard and they toyed with my equipment to keep me excited. My wife popped two little white pills in my mouth and tilted a glass of water up for me to drink. After they were swallowed she laughed and said only one word: "Viagra."

I was soon in such a state of excitement that I would have agreed to just about anything for relief. They got me to agree not to try to escape if they released my tether while they finished dressing me. My wife said, " You always wanted me to wear a sexy outfit like this and I know you've wanted to do the deed dressed as a woman. If you cooperate, it will all come true. I guaranty you the fucking of your life. As a bonus, if you are a real good girl., we might even go out together dressed as women. Maybe to one of those clubs you occasionally sneak out to visit."

Between her promises and my rising passion I could not help but agree. I did not even wonder at the depth of her knowledge about what I thought I had kept so securely hidden. How I wish now that I had thought more clearly.

I did agree and they unhooked my little leash. They quickly put a bunch of white petticoats on me and then a floor length hoop skirt. They stepped back and my wife looked on approvingly. "Very virginal," she said. There is was again. Surely she did not know. She just could not know. It would be too terrible.

My wife left the room and when she came back she was carrying a large bundle of white satin. "OH my God!" I thought. "She did know. Somehow she had found it."

She was carrying a white wedding gown I had bought on EBay and had hidden in the attic. It had cost a fortune. It was gorgeous and any girl would love to have it for their wedding. It was far fancier than the simple dress my wife had worn at our wedding. I could tell from the look in her eyes that she was really upset about this dress but she did not say anything.

They raised it up over my head and then lowered it. As it came down, the fed my arms into the lace slaves that came all the way down to my wrists. The sleeves were very tight as the lace stretched until it held my skin in a tight embrace. They fastened the back of the dress up with what seemed like hundreds of buttons. Since I could not reach them there was no way I would ever be able to undo them.

They adjusted the bottom of the dress so that it formed a white pool around my feet with the train curling about and then running out behind me. The top of the dress had lace at the shoulders and a very deep cut in front to show off my bosom. Short lace gloves went on each hand.

A bridal bouquet had been altered so that it had metal rings at the back. There were four for each hand and my fingers were pushed through them until my hands were laced together in front of me. Then the rings were squeezed down until the gripped my fingers tightly, holding them in position. The rings had some kind of friction locks that kept them from springing back to the open position. Ribbons were drawn around my waist and pulled tight and tied in a big white bow at the back. This held my hands securely at my waist.

"Do you think the bow makes her butt look big?" one woman asked. "No, her butt makes her butt look big," another one answered. "That's all right," my wife chimed in. "Guys like girls with big butts, especially on their wedding night."

Before I could think too much about that, one of them lifted up my skirts and another reached in and grabbed my leash. She brushed my penis with her hand and announced that I was still hard. Another one of them took a knife and made a small hole in my skirts and petticoats and they threaded the cord though and then refastened it to the desk ring. As a final indignity, my wife popped a large ring into my mouth. Now my mouth was held open in a big red circle which she made worse by adding more bright red lip gloss.

They all took turns playing with me, getting me all excited. I decided this was not so bad after all until I noticed my wife removing the camera and taking it away. She soon returned and adjusted the computer and monitor until the camera image appeared in front of me. I was looking at our bed in the next room.

My wife took over the role of playing with me while her two friends left the room. They soon appeared on the computer screen and I was treated to a show as they hoped up on the bed and began kissing each other.

"Like it?" my wife asked as she stroked my hot dick. The answer was quite apparent as I got even harder and began to pant with excitement. "Well, don't worry lover, it gets even better soon."

We watched them going at it as my wife kept toying with me. She kept me on the edge of a climax but she would not let me cum. I was just at the point of begging her for release when the doorbell rang. She called out to the other room, "Don't get up, girls. I'll get it. It's just the rest of our little cast of characters."

"The rest?" I thought. "What is she up to now?"

I soon found out. I heard more voices, this time rather deeper. More high heels on the floor and then I turned to see three of my cross dressing friends. All were decked out to the nines and all were smiling like silly strumpets. I was totally humiliated to have them see me like this.

"You said you wanted me to have sex while dressed this way," my wife said to me. "Well, I am. I figured out you would not like it if you had to watch me and you would like it even less if I did it with some guy who was dressed up the way you wanted to be." While she said this she set up our tripod and mounted our movie camera on it. She pointed it at me and fiddled with it for a while. When she was finished she said, "We will be filming your wedding coming out party in a little while. And I do mean "cum."

She walked back up to me and gave me a kiss on the back of my neck. "There," she said. "I've left my mark on you, you bastard." Her voice hardened. "I found the receipt for this dress. You spent move on it that we did for our entire wedding. I hate you for that and for all the other money you threw away on this stupid 'thing' of yours. Well, now you are going to pay big time for how you cheated on me. I'm going to enjoy every moment of my revenge."

She then led my three friends into the bedroom and I was treated to an orgy on the computer screen. The three women soon had the cross dressers hard and panting. Then came the domination as the three sets of legs were spread and three heads were drawn up into three wet crotches and three tongues were set to work. I could now hear the sighs and shrieks as three women came to orgasm after orgasm. I was forced to watch on the screen as the scene I wanted to be a part of so badly plaid out on my own bed.

When the women were finally satisfied, one of the cross dressers said, "What about us?"

My wife replied, "Oh, you know where you can find a virgin ass in all her bridal finery just waiting for you."

"Oh God, no!" I thought as her words slowly sunk in. I started to yell and pull at my bindings. I struggled helplessly as three sets of heels click-clacked across the floor. I tried to plead as I felt my skirts being lifted. I begged through my ring gag as I felt the end of a rock hard cock press against my anus through the open crotch of my white panties. Then I fell silent as lips pressed down on mine and a tongue invaded my throat. I nearly gagged in horror as the greased up cock forced its way up into me. It drove all the way in until I could actually feel his balls hit my buns. Then he slowly drew it out before ramming it back in.

As he picked up speed I felt a pair of hands on my breasts and another pair of lips on my bare chest and neck. That was when I remembered my wife had given all three of these guys a pair of white pills. As I heard a giggle from the other room, I managed to move my head just enough to see the computer screen. There was my wife staring at me with a huge smile on her face.

As I heard two voices from the other room reminding the guys that I had two holes to use, I saw my wife's face on the commuter screen. "Fuck you!" she mouthed. "Fuck you good!"

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Thursday, April 04, 2013  


Thursday, October 28, 2010  

GREAT UPDATE!!!!! I anxiously await further continuation of your story!!!

Friday, July 30, 2010  

Well i think we have a good session with the cane here. About 40 strokes i would say.

Friday, July 23, 2010  

W/your spelling earros , your screwed (or should I say cained).

Wednesday, July 21, 2010  

I make it 12 mistakes, so 12 strokes with the cane from your 'new' Mistress.

Let's have some more of your adventures as a CD slave

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