Be Careful What You Ask For...

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Crossdresser is taken control of by a Mistress.
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I've been living with Janet for ten years now and for the first eight all was well. But over the last two years things have changed completely, and not for the better. I started looking at various sites over the years, you know the type, and I concentrated on cross-dressing and transvestite sites. But this would only be every now and then. I did look at other 'normal' porn sites also, but the CD and TV sites seemed to fascinate me. I had been into cross-dressing before I met Janet but shelved it once she moved in. The small wardrobe I owned was put into the attic as I knew she would not go up there as she hates even the idea of spiders.

Some three years ago Jan got promoted and was now managing a team of people. She received training on how to manage people and teams, assertiveness training it was called. It gave her more confidence, made her seem more in control and provided her with skill like being able to give orders without seeming to. This training was reflected in our relationship as she became more assertive, self-assured and confident. Jan was always the pushy one in the relationship but the training extended this. She organised holidays, weekends away and took the lead in things like organising a spring clean of the house. I would be given the orders - she would help out mind - but she was the one in charge.

About the same time I found myself working from home and Jan's promotion meant she was travelling to the US for a week or so every eight weeks. The urge to dress came back and once, when she was away, I give in. I began to dress and surf the net looking at sites and getting ideas for dressing, putting on make up and so forth. Sometimes I would dress for the complete day and I began to buy more clothes.

I also got into the idea of Domination and read up on various things that went on in a FemDom relationships. I liked the idea, to an extent, but did not see a way of making it happen in real life. Jan was a very heterosexual person with strict ideas of what was allowed and what was not. Now, don't get me wrong, she was not a prude or anything, and she would get into 'interesting' games or situations, but I knew cross-dressing and the like was not on - she had seen a picture in the Sunday Times magazine once where a man was made-up and dressed like a woman and she was very derogatory towards it. As for Domination - in bed, the man was always the man as far as she was concerned.

Over the course of a year, I gradually got more and more into the fantasy of being Dommed while being dressed as a woman and was wondering how I might bring it up with Jan. I should have remembered what an old friend of mine used to say, 'Be careful what you wish for because you just might get it', and he proved to be right.

In January, two years ago, Janet and I took a week off and went to a hotel in the west of Ireland. I was not on the web for the whole of that week and missed it badly. We arrived home on Friday and spent the rest of the week-end together as she was flying to the US on Monday morning. Again I was not on the web so I really missed my little fix. On Monday morning Jan took off for the airport and about an hour later I was dressed and surfing the web pages. I have my own PC and Jan has hers so I was never worried about history files, etc. If she did need to use my PC she had a log-in with very little rights so she could not view my account. So I was sitting there in panties, bra, tights, skirt and blouse wearing a pair of kitten heel shoes and surfing my favourite sites and logged in to my Yahoo Groups, enjoying myself.

I was about to go to one of my favourite TV pages when I heard a car door slam. I was puzzled for a second as the postman had already left but I reckoned it was some guy selling stuff and I could just let him knock. Just to be sure I thought I'd take a look and I opened the living room door a bit to peek out into the yard (we live in a house on it's own bit of land and it is out in the countryside). To my horror, Janet was unloading her case from the car and heading for the house. I had fifteen seconds to get into the bathroom where I could safely undress and hide the clothes. I had to go through our bedroom so I could grab a dressing gown: not getting dressed is one of the perks of working for yourself.

Running past the PC I turned off the monitor as I hadn't time to reach behind the tower and turn the whole thing off. I closed the bedroom door as the front door opened and Janet called down the hall.

'Steve', she yelled, 'I had to come back. Gary called to say the meeting was cancelled and put out to next week.'

'I'm in the bathroom,' I called, 'be out in a second.'

I tore the clothes off and gave my face a quick wash. I had not bothered with much make-up as I had to go into town for food later in the day. Throwing on a dressing gown and leaving the bathroom, I bundled the clothes into a bag I use for fishing and which had been lying in a corner for a week or two.

I came out of the bathroom with the fishing bag and stuck it in the hall press, knowing Jan would never go near it.

'What happened?, I asked as I went over to her and gave her a kiss.

'Oh, the Americans had not got their work completed on Thursday, so Gary cancelled the meetings. Word went out by email but they forgot I was on leave. He cancelled the flights and everything but it was just as he got into the office this morning he realised about me.' she explained. 'Anyway, how come you're not dressed?'

'Joys of working from home!' I said.

'I am going into the office for a few hours, but I did not want to leave my case in the car.' she explained. She then said she needed to re-enter her travel request and sat at the computer. She had noticed that only the monitor was off and said it would be quicker than unpacking and powering up her laptop, which anyway was out in the car. What could I do?

She flicked on the monitor and ten seconds later her jaw dropped as a picture of a woman in a short leather dress, fishnet stockings and knee-high boots and holding a cane stared at her. She quickly started using ctrl-tab to view the other pages and then went into history and began clicking on my previous selection. Looking up at me she told me angrily to 'Go Away'.

I went and sat in the kitchen not knowing what to do. Every now and then I'd hear a curse or swear as she came across something else. She eventually came into the kitchen and told me not to touch the PC. She said if anything was missing or erased that would be the end of us. She went off to work and I wondered what was going to happen. I decided to come clean with her once she came home.

That evening she arrived back about 5:30 and went into our bedroom. She came out in a short dressing gown and sat at the computer telling me to get dinner ready. When I had the food ready I went in and told her and we sat and ate. I tried to begin a conversation about what was on the PC but she held her hand up without raising her eyes from the food and shut me off. I'd only seen her anywhere near this angry once when I had forgotten her birthday present six years into the relationship.

When we were finished eating she told me to wash up and put away everything and then to come into the living room. When I arrived in half an hour later she was still flicking around the net, but she looked a lot more relaxed and positive than earlier. She spent the next hour looking at various sites, keying in different search words and going through different screens.

She then turned to me and gave a small smile - then her face hardened. She told me I was to answer her questions immediately and not to think before answering or try to deceive her. She told me I was to be completely honest with her and any lies would be recognised. When I agreed with these statements she asked me the following.

'Have you worn my clothes?' I told her no as she was much smaller than I was.

'Do you have clothes in this house? Women's clothes?' I told her I did.

'Go get all of them.' she ordered.

I went off and returned a short time later with everything. Three skirts, five blouses, two dresses, various bra and panty sets, stockings, tights, one wig, four pair of shoes and two pair of boots. She told me to lay them out on the couch with the shoes and boots on the floor. In a bag I carried up were some tops and camisoles and a garter-belt as well as a small collection of make-up. When I had done this she looked through the collection making comment on how suitable/unsuitable they were. She looked into the bag and took out the make-up, placing it on the table. She picked through the clothes, flicking some to the side and some others on the floor. She then sat down and paused for a while.

'I am disgusted at you for a number of reasons.' she said in a calm voice which was under laid with anger. 'You have kept something important from me, something to which I believe I had a right to be made aware. You have obviously been masturbating while dressed and looking at your porn,' she continued, 'and don't you try to deny it.' she said, pointing at the clothes on the floor, which I saw were mostly panties and which I knew had dried cum stains on them.

'There were many nights when I would have liked to make love but you were never in the mood, and now I know why. You'd pleasured yourself through-out the day and left me wanting. Well that stops now!', she said. 'What do you have to say for yourself? If anything!'

I apologised to her and explained that is was just a passing interest and that I would get rid of the clothes immediately. She raised her finger and swung it back and forth and said, 'No, no, no, no, no. That is not my plan at all. I like some of what I see here and I am going to get some level of recompense from you. I don't believe that this is a recent, passing thing, either. The group you were logged into shows you've been a member of for five years and there is another one for cross dressers which you've been a member of for longer than that! But I love you and I will make things such that both of us get what we want.' She paused. 'At the very least, both of us will get what I want.' she finished.

I didn't know what to do or say. I could only stand there feeling foolish and feeling that I'd betrayed her but also feeling relieved that she had not stormed off to stay with either Donna or Francine, her two best friends, neither of which had much time for me. Donna was a fun-time girl, always wanting to party and having a different boyfriend every month, and Fran was single and looking like she would stay that way. I sometimes felt she was perhaps a closet lesbian as she never seemed to have a boyfriend.

Jan looked at the time and said, 'OK, it's now just nine o'clock. I want you to stand there and take all your clothes off.' I paused for a second and she said 'Move it, Steven, I have plans for tonight and I still need my beauty sleep.'

I stripped and stood in the middle of the living room. Of course I'd often been naked in front of Jan all over the house and even in the back garden, but I felt very vulnerable in these conditions. Jan picked up a clean pair of panties, a matching bra and a pair of black hold-ups. She also took a black dress and handed the lot to me.

'Dress yourself for me!' she instructed and sat in an armchair, crossing her legs and leaning forward, resting her chin on her hand.

'I only wanted to dress for me,' I sort of stuttered, 'if you know what I mean. It was just a bit of ......' and I faded off as I could see she was not interested in hearing my pleas.

So I slipped on the panties and the bra and then the hold-ups. Jan leaned forward and picked up the black pair of knee high boots I owned and handed them to me. 'Put those on also,' she said. 'What do you use for padding for your bra?' she asked. I pointed at the spare stocking, grabbed some and pushed them into the cups.

I put on the dress and then the boots and I was embarrassed to feel my cock growing hard, as it always did when I was dressed. Jan did not seem to notice the small bulge in the front of my dress, and I was, for some reason, quite relieved.

'Now, I am going down to our bedroom. I want you to put these clothes into the empty press and drawers in the guest room next to ours and not in the attic where you've kept them hidden to date. Throw those soiled items into the wash basket and wash them by hand tomorrow. I'll be back in about ten minutes. Oh, come here a minute.' she said as she reached for the make-up on the table. She quickly applied lipstick to me told me to get about my business. 'And pour us a glass of wine.' she instructed as she walked down the all.

I completed putting the clothes away and was sitting taking my second glass of wine when I heard Jan's heels clicking up the hallway. She came into the room and I could not believe my eyes. She was wearing a black basque, which I had not seen before, black satin panties and her knee high, shiny black patent leather boots. Her hair was tied back in a ponytail and she had applied what she described as her 'knock 'em dead' make up. She looked very like the Dominatrix I'd been caught watching earlier that day.

'Now, I am going to be the Dominatrix you've probably been wanting all these years,' she said, 'and I will set the rules for you to live by. OK?' I could only nod in consent. She took her glass of wine and took a deep drink. 'You will now tell me what it is you think you want from a Domme/Sub relationship.'

I outlined what I thought, and she listened. I mentioned serving her food and drink and massaging her feet, washing her clothes and her body, if she was in the mind for a bath instead of a shower. I mentioned her telling me what she wanted in an authoritative manner and for her to deny me ejaculation, for a time anyway. As I said earlier, I had not ventured too far into the Domination stuff even though I'd been touching on it for a number of years.

Jan smiled at me and said we would do all that and a bit more. She told me to sit beside her on the couch and she began to rub my leg, stroking gently from my knee to near the top of my thigh. I had adjusted my cock while she was absent and it was able to become erect without Jan seeing it.

'We will be doing all the things you mentioned, as I said, but we will be doing a bit more. Starting tonight, I am going to punish you for keeping this secret from me. Now, before we go on, is there any other 'foibles' you want to tell me about? Are there other sites you've been visiting that I should know about? Hmmm?' she asked and then took another sip of wine.

I thought as quickly as I could. I had visited sites where cross dressers had sex, but I did not feel an urge to have sex with another cross dresser; it just appeared to me that the cross dressers on those sites were much better looking than on other 'normal' sites. I could not be sure what Jan had seen or come across so I had to tell her the truth.

'Oh, show me so.', she said mildly. I showed her one particular couple together. One TV was called Maria and was very sexy looking but had an enormous cock. The other was very pretty and the only way you knew it was not a real girl was the six inch penis protruding from her panties.

'I see what you mean,' Jan said, her eyes glued to Maria's eight inch monster. 'Move slightly to the left,' she said, 'I want to see more. She clicked on the 'next' button and more pictures popped up.

'Tomorrow you are going to shave your legs, chest, arms, crotch and ass,' she said, 'I want you looking as smooth as possible.'.

I was a uncomfortable with this as, while I was not overly hairy, I did swim twice a week in the morning and I knew it would be noticed in the dressing room. I started to say this but Jan cut me off saying, 'I've made my mind up. Hair under nylon stockings is disgusting looking. You can make something up in case anyone says something. Tell them you've developed an allergy to your own hair.'

'From now on, I want you to be dressed when I get home from work. I will call when I am leaving the office and that will give you twenty minutes or so to get ready. Also, when you go into town to shop tomorrow, wear tights and panties under your trousers. Understand?'

Again, went to object as I was afraid something would happen when I was out and I had always avoided being dressed in the early evenings as that was the most likely time for one of our friends to call, usually for a quick drink and to say hello.

'Don't keep putting up barriers and making objections.' Jan said, obviously annoyed, 'You'll do as I say and to make sure you understand that, come with me. I said I was going to punish you and it starts now. Every day from now on you will be punished until we reach the number of days you were deceiving me. So, we'll say, eight years from now that punishment ends. In the meantime. any other 'sins' or misbehaviours will earn you an additional set of punishment. Now follow me.'

We went down to the bedroom and Jan told me to stand at the end of the bed. She went into her drawer and took out some stocking and tights. She tied my ankles to the bed legs, one either side. She then told me to bend over and she tied my wrists to the lower part of the bedposts. As there is no board across the end of the bed it was not too uncomfortable. Jan slipped on a long, black lace dressing gown and walked out of the room. I heard the back door open and she went across the yard, her high heels clicking on the limestone slabs. She was obviously heading for the main shed, an old cow byre some forty feet long and twenty feet wide, in which all manner of stuff was stored.

She returned after a while and entered the room telling me to keep looking ahead or down as she came through the door. She stood to the side of me and said. 'Right, you are going to be punished for keeping your dirty little secrets from me,' Her voice was very hard and calculating. 'I have wanted to spice up our sex life for a long time and this was one of the things on my menu. For you to have kept this to yourself is un-forgivable. So, tonight I am going to cane you and after each of the strokes of the cane I will give you an order ,or rule if you prefer, which you will remember and obey. Do you understand?'

I was a bit shocked as I felt all control was now lost to me and I hesitated for a second or two. 'Don't make me wait, answer me now.' she hissed and I heard a swishing sound followed by a very hard crack across my backside which made me leap and shout out in pain. I looked at her and she was standing with her legs apart, the nightgown flowing down behind her thighs and she had a very harsh look on her face. The basque made her slim waist look even thinner and pushed her D-cup breasts into an amazing cleavage. She swung her hand back from behind her body and she had her riding crop in it.

'Now, sweety-pie, do you understand what I just said to you?' I nodded and said 'Yes.'

'Yes, what?' she asked.

'Yes. I understand.' I answered.

She swung the crop behind her and again lashed me across the ass, again causing me to cry out.

'The correct answer is 'Yes, Mistress.' she panted. 'Yes, Mistress. I understand, Mistress. That is how you will answer from now on. OK.'

'Yes, Yes, Mistress. I understand. I will answer correctly from now on, Mistress.'

While I'd imagined being caned or spanked by a Domme, I did not ever imagine that it would be anything like this. Two swings and I was in agony. I had to try and reason with Jan.

'Please, Mistress, can we stop this now?. I won't be able to sit for days.' I said.

She crossed her arms, still holding the riding crop. A small smile grew on her face and she said. 'You will take, accept and enjoy your punishment. On the other hand ,if you like, we can forget the whole thing. I will move in with Donna or Fran and you and I can see, from a distance, if there is some way to salvage our relationship. 'Course, I would be bound to tell whomever I move in with what happened and those two don't keep secrets very well. So, you decide. Shall I untie you and pack up my things or shall we carry on? Hmm?'

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