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I sat there dreamily thinking about what had happened. I was happy because my mistress had told me I had made her happy. But at what price? I looked completely different – no, I was completely different: I had become a girl to please her. She said I was pretty – I was indeed very happy.

Some time ago I had admitted to her my fantasies of a beautiful dominant girl forcing me to be the prettiest possible sissy. I had no idea that she would take it so far with me. She had simply smiled at me and said she would be delighted to help me!

We had agreed that I would give her some money to buy a wardrobe for me. She did this with apparent relish, telling me how pretty I was going to be. I didn’t think much of it, in fact I looked forward to it, but I assumed there would be a couple of dresses to try on with some make-up, and not much more.

Five days before the night my transformation was to take place, I visited my mistress as she had instructed. I wasn’t quite sure why she required my attendance in advance, but after a little chit-chat things started to become somewhat clearer. She produced a chastity belt and dangled it in front of me: ‘no more wanking for you,’ she said with a little smile and a massive glint in her eye. She had done this to me before. She knew how horny I became in the mornings and how my penis woke me up with its screams to become erect – and the suffering that being unable to because of the chastity belt caused. I had complained to her about it and she had responded with a simple, ‘I am so glad you are suffering,’ response.

Once she had dangled the chastity belt in front of me, I immediately became hard and she couldn’t put the belt on me. She left the room for a little while and came back with a bucket. ‘Close your eyes,’ she whispered to me. After a brief moment she began to stroke me and then gently tug on my penis in a gentle rhythm. I was slowly getting harder and harder, closer and closer to cumming. ‘I am going to cum Mistress,’ I warned her. Suddenly she stopped. ‘Please let me cum mistress!’ I pleaded.

All of a sudden I felt an incredible coldness on my penis. I winced and stepped back. ‘Stay still!’ she hissed. I never wanted to upset her, so did as I was told while she applied the ice cubes to my penis. As if it was trying to escape from the ice it began to shrink quickly. It hurt terribly. Soon, it had shrunk enough for her to put on the chastity belt. ‘You’re going to be my horny little girl now, and when you return in five days time l'm going to make you very pretty,’ she whispered into my ear.

‘That was so so cruel mistress,’ I mumbled. She giggled once again and gave me that sweet smile: ‘I know, but you like it as much as I do darling,' she told me. 'You’re going to have to get used to denial dear: when you are pretty you can’t cum like a man’.

Her words scared me. Was she going to let me out? I knew better than to ask what she meant. ‘I know how much you wanted to cum dear, and while your cold little penis cannot be hard for a little while, your horny mind will be working overtime – just like the next few days with your chastity belt fastened securely in place! Perhaps even worse now,’ she giggled. She looked so beautiful when happy, and she certainly seemed to be very happy indeed! 

‘Now, when you come back, you need to be wearing these clothes laid out here.’ She showed some sissy panties, a bra, suspender belt and stockings, all in a matching pink colour. ‘I also want you to buy yourself two pairs of black satin stockings and a pink silk nightdress. Make sure they are the right size for you. I know you’ll love buying this stuff with the sales ladies looking at the large size you are buying and wondering if it is for you or your girlfriend. Try not to blush when buying it dear – that would give it away.’

She took a note of the number of the plastic lock on the chastity belt and ushered me out before I could say anything. On leaving she whispered in my ear, ‘think of me when you are horny dear, and send me an email each day explaining how badly you sleep,’ she said with a little giggle. She was clearly thoroughly enjoying my emasculation. ‘And, text me half an hour before you think you will arrive for your next visit.’

Over the next few days, my mind was a whirl – I was busy with work, but I could never forget the cage around my penis. 4am in the morning was always a terrible but sweet agony as I woke up horny, but my penis could never get erect! I was tired most days, but that in turn made me horny…

My other problem was that I had to buy the pink silk nightdress and stockings. I wandered through several shops to find the best place. I wanted to buy the things all at once and it wasn’t easy to find a pink nightdress. The thought of being forced to wear the pink nightdress made me horny without being able to get hard – she certainly knew how to torment me.

On the day, when driving to her place, I stopped at a service station and put on the panties, suspender belt, bra and pink stockings. The feel was strange, but I believed nothing would show. I sent her an SMS message half an hour before I expected to arrive. On receiving my SMS she called me. ‘Hello sissy, are you all pretty for me?’ My little sissy heart thumped very hard, ‘yes mistress’ I responded with a dry mouth. ‘Are you wearing all the clothes I told you to wear?’

‘Yes mistress,’ I responded.

‘That's a good sissy. But there is a slight change of plan – I want you to wear a pair of the black stockings and your pretty nightdress under your clothes. And wear it properly sissy!’ ‘Yes mistress,’ I responded. ‘I’ll give you a little extra time - 40 minutes in total. Be here within 40 minutes or else,’ she said ‘don’t be late because I have a guest here you need to impress’. 

The problem was, I didn’t know where to change and I was terrified of being seen. Of course she knew this. I was also terrified of being late after her warning, and who was this guest of hers and what did that mean for me? I was in such a panic.

Eventually I managed to change in a semi-secluded place by a park. The stockings were relatively easy, but the nightdress required me to take off my top and I was terrified of being seen. The diversion had made me late, and I didn’t know what she would do to me as a result!

As I arrived, she smiled and me and asked me why I was late. I didn’t know how to respond – ‘your poor nipples will later wish you weren’t late,’ she said smiling, knowing that I loved her torturing my nipples. ‘Entertain my guest and make sure she is happy – she’ll leave soon,’ she mentioned quickly before I could respond.

She took me into her living room where there was a stunning girl. ‘This is Olga,’ she said, ‘Please introduce yourself, I have a phone call to finish,’ and she left the room.

Olga was truly stunning – almost as beautiful as my mistress, she looked like a model – long blond hair and wearing an elegant dress to accentuate her curves; she was confident with it and knew she looked good. I introduced myself with a dry mouth, totally unsure of myself – did she know I was serving my mistress? What could I say about myself?

Suddenly I was very aware of the panties, bra and nightdress on me.

‘How do you know Natasha?’ she asked me. I didn’t know how to answer. Did she know Natasha was my mistress, or was she teasing me? Olga had a smile in her eyes, but was that because she knew my predicament or not? I mumbled something about meeting at a railway station, not thinking of anything better to say.

‘That’s interesting,’ said Olga, moving over to sit next to me on the sofa and putting her hand on my knee. She was extremely forward – I knew that Russian girls can be very open-minded, but was she Russian? Did she know the full situation? She was so beautiful! – my head was spinning and my penis throbbing in its cage.

‘I love English men,’ she whispered into my ear, ‘they are so amusing, and they always know how to make a girl happy.’ Her hand rubbed up and down my trousers and she leant into me. ‘Do you know how to please a girl?’ she whispered to me. ‘I think so,’ I mumbled. I must be dreaming I thought – a cruel dream that my mistress would thoroughly enjoy given my current predicament!

Olga made a further move on me: she sat on my knees, faced me and looked into my eyes. ‘Do you know how to please a girl Mart?’ she asked me and then gave me a passionate kiss. I responded rubbing my hands up and down her back. My penis was about to break my chastity belt. She took my hands and put them back where they had been. ‘Naughty boy,’ she said, "keep your hands to yourself! I rub you!’ She then continued kissing me and rubbed my back. All of a sudden she stepped back. ‘Are you wearing a bra?’ she asked me open-eyed. Yes’ I responded terrified. ‘Why?’ she asked.

What could I say? This could be a diplomat’s daughter for all I knew – the last person I would want to offend! I did not know who she was or how my mistress knew her. I didn’t know what to say, how I could explain wearing women’s clothes to this beauty.

Is that all you are wearing, or are you wearing any other female clothes?’ she asked me with a mischievous grin. ‘I have more on,’ I muttered, scared senseless, hoping that my mistress would reappear and rescue me.

‘Oh really! Excellent, let me see!’ Olga said chuckling loudly. ‘Take off all your male clothes, and leave on all your girly clothes,’ she told me. I got up slowly and took off my trousers, socks and t-shirt to reveal the nightdress and stockings.

Olga looked me up and down clearly enjoying the situation. She got up and gave me another kiss ‘Why do you wear these clothes? Do you enjoy this? Are you some kind of pervert?’ She rubbed her hands up and down my body, slipping her hand underneath my nightdress and discovering my chastity belt. ‘Oh what is this?’ she exclaimed with unconfined joy. By this time I was pure crimson with embarrassment. Olga was the kind of girl I would dream about, but this was a total humiliation for me: her fully clothed and I dressed like a girl with a chastity belt on.

At that point my mistress returned and burst out laughing. She said something in Russian to Olga. ‘I see you are trying to seduce Olga’ she said to me sarcastically. ‘She loves being fucked with big cocks,’ she said. ‘But you are lucky she is bisexual, so you might have a chance: its not as if she can use your cock is it?’ she asked with a massive smile. They both exploded with laughter.

By this time, I was mesmerised and terrified by these beauties. I didn’t know how far they would go with me.

‘He is so cute, where did you find him Natasha?’ asked Olga. ‘She, Olga, she – she is a girl tonight, that is why that thing between her legs is locked up tight and won’t be coming out.’

‘Please mistress, I am so horny, please let me cum!’ I begged. ‘OK, OK’ she said surprisingly – I didn't think for one moment that she would actually have pity on me.

She then asked me ‘Have you ever been milked?’ Before I could answer she said, ‘Well, you’re about to be now!’

‘I really want to see this,’ said Olga. ‘Mart – would you mind if I put some nipple clamps on you? It is a fantasy of mine to see a man completely compromised!’ she said with sarcastic emphasis on the ‘man’.

‘Olga, you do what you want,’ smiled my mistress before I could respond. She is our horny little toy this evening, and she is so desperate to be a good little girl for you.’

How right she was!

The End
 

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