Sissy Life Pt. 04

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A sissy prepares to be whipped.
2.5k words
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27.9k
15

Part 4 of the 5 part series

Updated 06/08/2023
Created 12/26/2016
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I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here again.

My Mistress looked up from the papers in front of her. I had no idea what they were. 'Have you washed and ironed the outfits for Rob's return tomorrow?' Rob is my Mistress' main lover. Tony was an internet hook-up. There have been several of these hook ups over the last month.

'Yes Mistress. There are 5 complete outfit options washed and ironed for you.'

'5?'

'I have washed and ironed the 4 recent purchases, but also the Tatiana Peep Bra & French Knickers set that Rob said he liked after your third date Mistress. And the red dress you wore that night also.' I'm expected to remember the 'official' names of all the lingerie my Mistress owns. 'It's the sort of thing a sissy enjoys isn't it?' my Mistress had said.

'Oh you are good. I must say, your performance since our little incident has been very impressive. It almost makes me think I shouldn't ask Rob to whip you...'

No, no, no! I winced at the words. A month ago I was released from my chastity device. I was given the opportunity to please my Mistress and I blew it. Big time! I had cum the very instant my Mistress had straddled me. She was angry - I was upset and in big trouble. She threatened to have Rob whip me on his return. I had hoped and hoped that if I performed well, was the perfect sissy between now and his return, she'd let me off. Or forget even.

'Recite Sissy Rule 2 for me.'

I curtseyed and began; 'Sissy Rule 2: I am your sissy. I must obey you without question. You may humiliate me, but you would not harm me. I should not be fearful of you; I should honour you through my behaviour.'

'I promise I won't let any harm come to you; not real harm anyway. A few temporary marks are to be expected in your position I think.' She sighed. 'I have a part to play with your sissy rules too. This needs to happen sweetie. As tempted as I am to let you off, how would you ever be able to respect me if I went back on my word? And if you don't respect me, how can I expect you to honour me? This needs to happen. You need to know your place; what better way for you to learn than have the man fucking me teach you?'

'Please Mistress. Please! I'll do anything. Please don't let Rob whip me.' For want of another idea, I did the most elaborate of curtseys. 'Please!'

'That needs to stop now. I have explained my reasoning. I won't be discussing it further. Perhaps if you beg Rob he'll go easy on you. I won't sway him either way. Maybe you can offer him a little something in exchange. Take some inspiration from them stories you like to read so much!' She laughed. 'That's between you two. Now, the sheets need changing in my room and your guest uniform needs ironing for tomorrow. And polish your heels; I want to see my face in them. Dismissed!'

A month of working my socks off had helped me in no way at all. I was still going to be exposed to Rob and I was still going to be whipped. If you thought being exposed to Tony made the prospect any easier, you are wrong. I had hoped Tony would be a one-off; being exposed again made this feel awfully like...like this was going to be the way of things from now on.

I changed the sheets as directed and I ironed my guest uniform. If you have never ironed a French Maid's uniform, you have no idea how hard it is! Perhaps one of those cheap Ann Summers types is easy, but my uniforms are tailor-made and thus quite elaborate. My guest uniform for example has a short circle skirt trimmed with lots of pink lace. Lace is very awkward to iron well. It creases very easily. Then there is complication of the petticoat underneath the skirt out; it adds considerable volume making it a nightmare to iron! The puff sleeves have large pink ribbon bows and there is more pink lace around the neckline with (yes, pink!) satin bows to the front. It takes a good hour to iron. Then there is the matching hat and the small apron too.

Once finished with the ironing I polished my heels. I'll be wearing pink 4-inch heels when I'm whipped by my wife's, my Mistress' lover; the humiliation! All done, I was just ready to retire when I heard Mistress' service bell ring. I hate that bell! I often struggle to tell which room the sound is coming from and tardiness is very much frowned upon. Only last week I was spanked for not responding in a 'timely fashion'. It wasn't for want of trying!

Fortunately I got the right room - the living room - this time. 'Is your uniform ready sissy?'

'It is Mistress, yes.'

'You haven't worn it since you served Tony and I. I'd like to see you in it. I want to ensure it is...the right look for your whipping.' This was BS. This was because I had asked her not to expose me to Rob and not let him whip me. She was showing me just how in control she is. She also knew if I worn my uniform - even if only for a short time - it would need ironing again.

'Yes Mistress. Of course.' I curtseyed and then knelt before her so she could unlock my current uniform. As I went to get changed I heard her shout, 'And wear your bell collar too!' I wanted to scream in frustration! I hated that collar; tinkling as it does with every movement.

I stripped off. My classic-look uniform is paired with black stockings and a black garter belt. My guest uniform is paired with white stockings and a white garter belt; this little event meant stripping completely. She was doing this to punish me!

Once ready I headed back towards the living room. 'I hear a sissy coming!' Mistress shouted. I went in and curtseyed. 'God, I love that outfit. When I went to buy it I thought, that is going to look ridiculous - and it does. But it's just perfect for a sissy husband like you. No man or woman could respect you dressed like that. I can't wait for Rob to see you in it! I love it! And that bell collar; I had forgotten just how much that delights me. I love hearing it. I'm going to get a black one to go with your regular uniform. You can wear one all the time!'

I curtseyed, 'Thank you Mistress. I'm glad I amuse you.' I couldn't help noticing the dreaded pink ball gag in her lap.

'Don't worry about this. You're not going to wear this tomorrow night - at least not all the time. Not like when you served Tony. You'll need to be able to talk tomorrow. I want to hear you explaining to Rob - in full detail - exactly why he should whip you. He gets the full story of what went on that night, not the edited version you gave Tony. Plus, I wanna hear you beg & plead!

'Now, have you thought about what I said earlier? About offering Rob a little something in exchange for going easier on you?'

'I don't understand Mistress.'

'Can you recall those stories I found on your laptop? When I became aware of your...interests? The ones where sissies sucked cocks and got fucked by real men?' I gulped. I must certainly could. They were pretty standard sissy stuff. Maid outfits, chastity devices, chores and yes, blowjobs and sissies being fucked!

'I want to be clear that I consider we have an open marriage - if marriage is still the appropriate word. I can - and do - see other men. I think it is only fair I make it clear that you can see men too. Now, I know you may be resistant to hearing that, but you have a long stint in chastity still to go. You might find yourself changing your mind after 200 days! I bet sucking a cock to get a little attention won't seem so...overwhelming then. So, if you want that to start with Rob, if you want offer him your mouth or more, you have my blessing. Understood?'

I was gobsmacked. The final indignity had come; my wife was happy for me to serve other men. 'I don't want that Mistress' and I curtseyed. 'I don't want to suck Rob or anyone else's cock. I want...I want you.'

'We are not going to discuss this' she said in a stern voice. 'You didn't want me when you were jerking off in front of your laptop. You didn't want me then, you don't get me now. You are a sissy. Recite Sissy Rule 1.'

'Sissy Rule 1: I must endeavour to think & act in accordance with my position. I am a sissy. I am not a man. I am not a woman; I am a sissy.'

'There you see? You just said it yourself; you are a sissy. Sissies may desire women, but they don't get them. They may serve them, but that is all. If you want any sexual pleasure, you need to be thinking about men. Now, Rob will be here at 10pm tomorrow night. I will be collecting him at the airport at 3pm, we will go to his house and 'catch up', we'll eat out and then we will come here. You will be waiting my the door dressed in your guest uniform just as you are now, ready to receive your whipping. Go to bed'.

*The following day*

I looked at the clock - 9.55pm. I was dressed as directed in my guest uniform. For the second time I was about to be introduced to a man wearing a pink French Maid-style uniform. This time was going to be worse though because this man was going to whip me! I fiddled with my garter straps nervously. Then I heard the key in the door...

I couldn't see Rob very clearly when they first came through the door as they were so entangled in each other. Clearly they had been drinking.

'Welcome Rob, to my Mistress' home. I am her sissy husband Mark' and I curtseyed my slow deep curtsey.

'Haha! So you are' said a very handsome man striding towards me. 'Let's get cracking! Or should that be 'whipping'!' If he was at all phased by my appearance, he wasn't showing it.

As discussed with my wife that morning, I led him to the old spare room, now my room. Once there, I asked them both to be seated and started my memorised speech. 'Rob, you have been invited by my Mistress to punish me. The punishment is to take the form of a whipping. The number of lashes is to be decided by you. If you will allow me, I would like to explain why there is a need for punishment.'

Rob looked highly amused, 'Go on.'

'On the 14th April my Mistress gave me an opportunity to spend some intimate time with her. Her intention was to allow me to please her by wearing a strap-on and fucking her. She knew without a strap-on I would fail miserably. She asked me to dress 'slutty' and I chose my May babydoll & matched it with black stockings, a black garter & red heels. The babydoll has red satin cups adorned with black lace and a soft, halter neck. I chose it because I love how floaty it feels. It makes me feel sexy.' I felt ridiculous! What must this man think of me?!

'However, I failed to realise my Mistress would expect me - quite rightly of course - to wear her strap-on. I thought I could pleasure her myself. Amazingly, my Mistress granted me this opportunity. She was very kind to do so. I failed her though. When she straddled me I came; I gave her no pleasure at all. Not a single second.'

It's funny what floats boats. As I stood there in my pink French Maid-style uniform explaining to a man - my wife's lover - who I had never met before and who was going to whip me, how spectacularly I had failed to please my wife sexually, pre-cum was pouring from my caged cock. I actually felt damp between my legs. I had never been so turned on and frustrated in my life!

'This is why my Mistress has quite rightly asked you to whip me. My behaviour was shameful.'

'I see' said Rob. 'I guess we should start then? I understand there are hooks in the floor that can used to put you in position?' Are there I thought?! I wasn't aware if there were!

'They are over here.' My Mistress who had said nothing since we came into my room was now stood by my wardrobe. Sure enough, in the floor were 4 silver hooks. 'They can be used to lock one down on all fours with arm & leg cuffs'. When had these been installed?! My Mistress had clearly given this event some thought!

'I...er. Um...' God, how did I say this? I mean, I didn't want to offer him my mouth. I didn't think. I didn't want to be whipped though of that I was sure. Plus, he was handsome. And I was so frustrated in my device...although, how would giving Rob pleasure help that? 'Rob...Sir, is there anything I could do to persuade you to not whip me? Or go easy on me? Please.'

'Like what sissy?' He sounded distracted; was busy attaching the cuffs to the hooks.

It was all or nothing, 'Like making my mouth available to you Sir.'

Rob didn't look up. 'Have you ever sucked a man's cock before sissy?'

'No Sir.'

'No Sir' he mimicked. I thought not. Tell me', he was looking at me now, 'why would I want use of your mouth if you have no experience, no skill? Your wife here, she gives amazing head. And I have that on tap. Your mouth is of no interest to me.' He straightened up. 'This, prancing round in a pink French Maid uniform, your useless dick locked away, may be your fantasy, but it isn't mine. You are of no interest to me. Your wife is, because she's fucking hot. You're pathetic.'

My wife, my Mistress looked triumphant. Her lover had very much just put her sissy husband in his place. I literally couldn't give myself away. I had tried to whore myself out to avoid a whipping - and I had failed!

'Get on all fours over her. Keep your uniform on; I'll whip you through it. Sarah, pass me the gag, your sissy husband is gonna scream like you won't believe!'

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4 Comments
AnonymousAnonymousover 2 years ago

I hope he goes real easy and just gives him playful little whip play that will just sting and make his cheeks a little pink. That would be fun for sissy too.

BrendaNWBrendaNWover 7 years ago
very good

nicely written.. if it was me as the sissy I would make it a test of wills.... I would not beg or hollar when being whipped.. I would turn the tables on her and be a better lover than she is.. cock sucking and being fucked while being so feminine and sexy that she just looks so masculine and butch that he becomes turned off.. how pissed would that make her to realize I can be a better woman than she is and a better man also.. what about when her friends tell her I munch pussy so well they almost faint and beg me to stop.. that would be so sweet.. she would just piss herself into such a state she would run off or beg to be taken back into trust and be a good wife...

AnonymousAnonymousover 7 years ago
Wow

Great! How diabolical and utterly emasculating. Every little step is a bit deeper into the hole. Now, offering to deflowerxhis little mouth with his Wife's lover.

You're wrong great stuff

sara

AnonymousAnonymousover 7 years ago
Great addition!

I love the humiliation!

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