Forced Feminization - Sissy Office Slut

by Alice Lloyd

  Dear Helen,

  I expect you’re wondering what the hell is going on. Well, I’ve had something I’ve wanted to tell you for many years now and if you’re reading this you’re about to find out the big secret I’ve been longing to share, but have been too scared to tell you.

  Don’t untie me until you’ve read the whole letter and have acted on the advice I give you. I can’t stress this enough. As soon as you untie me I will inevitably start denying everything and seek to limit the impact of whatever actions you have taken. I will make up some ridiculous story about having been set-up and that this is not what I really want. Do not believe me, no matter what I say. Know that the truth is in this letter and in the evidence I have provided. It has taken a lot of courage and effort to finally go through with this and I don’t want you to allow me to back out.

  I will no doubt be very aroused. If you undo my ball-gag I’ll probably claim I’ve been forced to take viagra and that is the only reason I am excited. Again, this will be untrue. Trust your eyes. I will be excited by the humiliation of you seeing me this way. I like it, in fact I love it. I want to be humiliated and controlled by you. I crave it. It excites me. I’m sorry, so sorry to have treated you badly all these years but it was only because I didn’t want you to see what I’m really in to. I’ve been worried that it might disgust you, but I’m taking the chance now because I can’t deny what I want any longer.

  I was always too embarrassed to ask you for this kind of lifestyle. I want to be your little sissy. I want to be your maid, cleaning the house in a little outfit. I want you to beat me if I don’t do what you say. I want you to keep me in a chastity device when you go out and I want you to bring back lovers to make me jealous. Lovers that, if I’ve been good, you might allow me to watch you have sex with. Lovers with whom you will laugh when you make me serve you drinks dressed as a sissy waitress or maid.

  Helen, this is what I want and what I have always secretly wanted women to do to me. It’s what I’m begging of you now.

  I have bought all the items you need to make this happen – the outfits, the chastity device, the restraints and the whips... they are all hanging up in the wardrobe that I’ve left open...look, it’s all there... all the sissy outfits I’d love you to make me wear and the chastity device I want you to use to control my cock.

  If you do this for me I will never cheat on you again. Instead I will earn money for you and you will decide what we spend it on, I will do all the housework for you – all the cooking and cleaning, ironing and shopping, everything – absolutely everything - and you will be free to lead the life you have deserved all these years. I will treat you as my princess, my mistress, my goddess. Whatever you want is yours.

  But first you must act. Remember as soon as you untie me I will surely deny everything. Helen, you must act now.

  I have recorded myself having sex with a transvestite. Yes, that’s a man in a blonde wig. At the end, when I’ve cum, he takes his wig off. This video would ruin me if it got out. You can rewind it to the start and see me tying myself willingly to the bed. I wanted to make this video. It made me very excited. Look at my erection I loved it. There is a hard copy in the machine and I’ve also emailed you an electronic copy from ‘Erica the sissy slut’ to your account. I suggest you forward it to someone you trust and, I hope, will keep my secret, and perhaps help you to humiliate me.

  The second thing I have done is to sign bank transfer documents putting all our savings and also the deeds to the house in your name. Once you take the gag off me I will surely claim that I was somehow tricked into signing these documents. Do you really believe a lawyer of my experience would fall for that? Of course not. I want you to control our finances. I want you to decide if I have pleased you enough to have earned some pocket money, or not.

  Finally, Helen, darling. I have thrown out all my male clothes and am willing to work from home in future. Contracts can be done online these days and by post, and I will never have to wear male clothes ever again if you so wish. I will let you decide.

  So please, please, leave me tied up tonight, put the chastity device on me when my cock finally stops being erect, and ensure that the papers are filed and the DVD stashed somewhere safe. You might also want to take pictures of my current predicament and save them also for a rainy day with a trusted friend, or relative.

  I love you, Helen. Please do this for me and I will give you everything in return,

  I declare that I sign this freely and without duress,

  Eric Norwood

  For a moment or two I said nothing and stared into space wondering whether this could possibly be a hoax. Then, on the DVD I saw and heard Eric orgasm (ugh!) and, as anticipated, the ‘blonde’ takes off her wig and we see quite clearly the face of a man.

  Then I went to the wardrobe to examine the outfits and whips and restraints, including the promised chastity device all neatly arranged. If he had been set up, someone had gone to an awful lot of trouble....

  And then I saw the documents all signed by Eric. It was his handwriting or an incredibly good forgery. Surely he couldn’t have been forced to sign them and surely he couldn’t have been tricked in to signing...... could he……?

  Or could he?

  Was it an elaborate set up...? Perhaps he had been tricked or was under duress of some sort? But why then would I be the sole beneficiary? I didn’t see anything stolen or any bruises on Eric. Apart from his wrists and ankles which were now looking as red as his face, with his constant pulling and yanking at his bonds, there wasn’t a single mark on him.

  Or perhaps it was all true. Perhaps this was why he had had so many affairs. He did this kind of kinky thing with other women so I would be spared. That didn’t sound like Eric at all....

  My head was spinning, so I did what any sensible woman would do in this situation - I went and made myself a cup of tea. I wanted time to think.

  And then I made a couple of phone calls.

  If Eric was annoyed with me when I left him there to make a cup of tea, he was furious with me by the time I returned to the bedroom almost an hour later and quietly supped a second, fresh cup of Earl Grey.

  “Ok, Eric,’ I said finally, running a hand lazily up his stocking-clad thigh, noticing that his cock was still very hard indeed, “you should know that I’ve made my decision and have already set a few things in motion.”

  I finished my tea and put down the cup and saucer. With my hand reaching inside his panties (his panties! I giggled internally, but kept my very best poker face) I put my hand around his cock. I saw him close his eyes, desperate for it not to be so hard. I played with it gently, up and down. He closed his eyes, but he couldn’t deny that he was turned on.

  “I’ve come to the decision that I don’t actually care if you’re being set-up or blackmailed or whatever. The bottom line is this. I want to do the things in the letter. If you’re really into it, great. If you’re not, tough. It’s happening. All of it. I’m leaving you here tonight and I will sleep in the spare room. I’ve already forwarded your email to my sister Susan and she replied immediately to say that she will be here in the morning. I want her to help me take care of you. You never got on with her did you? Then, first thing tomorrow I’m off to the bank. I’ll be here just until Susan arrives.

  Mick and Geoff will be here too - you know the gay couple that I play poker with – the ones you always suspected were not actually gay and that I’d been sleeping with both of them in a threesome. They are gay, I can assure you of that and I hope one day they show you just how gay they are – it turns out they might be more your cup of tea than mine. They will be there when Susan and I untie you. Two ex-army gay guys might help dissuade you from doing anything rash, just in case you’re tempted.

  You know what, Eric? Or should that be Erica, now? Your hard cock tells me that you probably do want this to happen, at least on some level. You always were a kinky old pervert.

  However, part of me hopes that this is an elaborate set-up and that some fa
iry-godmother has given me a present I’ll never forget for the rest of my life..... and, I also have to admit, there’s a pretty evil, vengeful bit of me that hopes you’re absolutely hating this.”

  I serenely kept wanking him gently, but just smiled at him for a while, letting those words hang in the air for him to digest. For once, with that big gag in his mouth there was no way he could argue back. I decided I liked gags. Eric in a gag – what a marvellous idea. I would be buying more of them for him. That made me smile all the more.

  “I’m actually quite excited by the idea of you running around after me as my simpering little sissy maid and slave…. And I love the idea of tying you up and thrashing you with a whip. I suspect we’re going to be doing that a lot. My sister would like a go too…. And she’d like you to clean her house for her.

  I also think it’s about time I took a lover. I never thought I could or would break my marriage vows – not that there haven’t been plenty of offers over the years – plenty of men have made it clear that they think I’m still very desirable, as you did once upon a time - but reading that letter has persuaded me to have a re-think. I’ve been faithful to you all these years while you’ve been shagging any piece of skirt who will let you. I think it’s time to even things up now. I’m not going to divorce you, but you will be my slave rather than my husband from now on.

  So, yes, if in fact you are actually hating this and you have been set up... well that would make all this so much the sweeter.”

  I sped up my hand wanking his cock and with my free hand took a picture of him as I made him cum. It was so easy and took no time at all.

  Maybe he did like it.

  Then I smeared his semen on his face and took another. And then another.

  Even though he had just cum, he didn’t lose his erection when I took the photos – that would add to the humiliation I supposed - and his cock was still peeping resolutely upwards like a flag-pole out of his panties when I turned to leave. Perhaps it was a massive turn on for him....... or maybe he was just full of viagra that someone – probably the man in the DVD - had tricked or forced him into taking.

  I smiled to myself as I switched off the light and he was still straining at his bonds, screaming behind the gag. I really didn’t care why my fairy godmother had visited, but I would accept her present gratefully.

  “Save your strength for the morning. I have plans for you. ‘Night ‘night, Erica. Sweet dreams.”

  Chapter 10. [ Nick / Nicola speaking ]

  When Sarah and I got married the wedding was a small affair with just a few friends and family and a short meal at lunchtime. We told everyone we wanted it to be low-key and to be able to get away in the afternoon to go on honeymoon.

  Most of that was true enough.

  However, instead of going on honeymoon and having a plane to catch – which was the impression we had given - what we actually planned to do was to attend another wedding, that of Jane and Holly.

  At the first service Jane and Holly acted as our bridesmaids and at the second, that would be Nicola and Sarah.

  These days I have no authority to object to any suggestion that comes from one of Sarah, Holly or Jane and I have no chance whatsoever once they start giggling and plotting between them. That had been the case when Sarah had shared her plan with us for dealing with Eric Norwood and if they wanted me to be a bridesmaid, that is what I would have to do. They promised me they would pick a gorgeous dress for me and that I wouldn’t be the only boy dressed as a girl on their invitation list. The way they smirked at each other was not at all reassuring.

  Sarah and I booked in to a suite at the hotel where Holly and Jane were getting married. On the bed the girls had left for us two exquisite matching bridesmaid dresses in raspberry-coloured silk with frouffy petticoats, together with expensive lingerie and heels that Sarah said she had chosen with them to go under our matching outfits. I can’t deny these clothes excited me and the fact that I would be wearing the same clothes as my beautiful new wife was also a thrill. They were all so deliciously feminine and so, so pretty.

  My new bride, Sarah, took great delight in videoing my transformation from bridegroom in a smart suit into Nicola, the bridesmaid – complete with make up, false breasts, eye-lashes, feminine curve enhancers, wig, jewellery, the works. This all seemed strangely appropriate for our relationship on our first day as a married couple. I felt so utterly girly and very aroused. Sarah knew that look and smiled as she led me by the hand to admire myself in the mirror. It was always a source of amusement for her when she caught me lusting after my own reflection (‘Slut!’ she would say, ‘you’d even fuck yourself if you could!’). She was right. I almost swooned with pleasure as my whole body was caressed with silk and nylon, net and lace and frills….. and I did fancy the girl looking back at me in the mirror.

  It crossed my mind that this was a lesbian wedding and that was how I’d started to see my relationship with Sarah. It was as if I were her little, lesbian, submissive wife. I cooked and cleaned at home in a maid’s outfit and serviced her every need. She liked that I had become her sex doll. I would frequently be required to dress in a full rubber suit, usually as a girl doll, occasionally male, with a strap-on over my chastity device. She had also trained me to be an expert in licking her pussy – sometimes she got me to go down on her for hours. For these duties I would always be either in chastity or restrained in such a way that I could not touch my erection. Cumming was always on her terms.

  More often than not, though, her main source of sexual gratification was to bend me over and fuck me with her favourite vibrating strap-on. She had conditioned me to like these fuckings. When she donned her strap-on and had me restrained, that was the only time I was ever allowed out of chastity and able to feel something – usually the bedsheets or a pillow – against my erection in my panties. It amused and pleased her greatly the first time she inspected my condom and discovered that I had filled it, cumming as she fucked me and my cock rubbed against my silk crotchless panties – that I’d cum from being fucked hard from behind by her cock. It happened more and more frequently to the point that it happens almost every time now when she fucks me. I just can’t help it. My ass feels like it is now my pussy.

  I started to crave it and Sarah loved it when I admitted how I felt. She kissed me and said that this admission made her very happy indeed. One of her favourite things was to restrain me in vulnerable positions in inescapable bondage, and then parade around me wearing her big strap-on, stroking it menacingly and whipping my arse until I begged her to fuck me. Now she knew I really did want her to fuck me, that I genuinely craved it and that it would almost inevitably make me fill my panties with cum....... well that was almost too perfect, Sarah said, hugging me.

  I loved her. I loved my mistress.

  I told her I wanted to make her happy in any way that I could. Anything she wanted, I would do. She told me to be careful what I said and that she would remind me of my words when we got married.

  Jane and Sarah’s wedding was much bigger than ours and I felt nervous walking down the isle with them. I was still a guy in a dress, no matter how often I kept telling myself that I looked pretty convincing as a girl and that hardly anybody, particularly in this generally broad-minded congregation, would mind anyway. I was also nervous because Sarah had promised me a night to remember and that I would need to keep reminding myself that I was prepared to do anything she wanted. Anything is a big word, darling, she had now said several times.

  When Sarah felt the need to remind me of things like that it spelled trouble.

  Jane and Sarah looked gorgeous in their bridal outfits and I felt constantly aroused in amongst all the feminine silk, satin, and taffeta and all the lace and frills and particularly when the two beautiful, newly-wed women kissed each other. My own silk and net full, flared petticoat, together with my chastity device was all that prevented what would have been a large, unsightly bulge ruining the line of my beautiful bridesmaid’s dress.

  I blu
shed. I blushed because I was so horny. Up until recently I had been allowed to cum once a week, but now I hadn’t been allowed to cum for over a month and Sarah had taken great delight in edging me for hours to the point of orgasm and then denying me every time, a bag of ice cubes at the ready to put on my straining cock and then straight back on with the chastity cage around my shrivelled, frozen penis. I must have had a gallon of spunk stored in my aching balls. She said I needed to save it for my big day.

  I also blushed because I recognised that the image in my mind of how I would like to consummate my own marriage to Sarah was driven far less by the receding memory of her riding me, impaled on my cock, as we sat in my office chair, and very much more by the desire for her to ride me from behind with her strap-on.

  I kept blushing. I’d become her sissy bitch, heart and soul, ..... and I liked it.

  After the service there were photos and then it was straight on to the evening meal and entertainment.

  The object of their collaboration and plotting gradually revealed itself as the meal progressed.

  The first course and main course were complete and a fair bit of alcohol had been drunk by Jane, Holly and Sarah, when my new wife said she had a surprise for me. With a wink she said my dessert would be waiting for me in one of the bedrooms. As I got up to leave I could see her turn to Holly and Jane and they all creased up in hysterical laughter.

  Anything is a big word.

  Appropriately enough I was sent to bedroom number 101 on the first floor and Sarah told me I would be met by a woman I would address as Mistress Amber. I was to do whatever she said, no matter what. She would be carrying out instructions issued by her, the wife I had just sworn to obey. When Sarah had kissed me goodbye she had said I’d hate it, but I’d also love what she had planned for me. Either way tonight was going to be a night I’d never forget.