Sissy Life

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A pathetic sissy blows the chance to impress his wife.
1.8k words
4.16
75.5k
47

Part 1 of the 5 part series

Updated 06/08/2023
Created 12/26/2016
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I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here....

I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, she simply rang the bell and I sought her out. 'Sissy, come to my study when you are finished here. I want to discuss something with you before you retire.' I groaned inwardly. The last 'discussion' ended with me in the chastity device I wear to this day! She left before I had chance to respond.

Once I'd finished, I headed to Mistress' study, carefully checking my appearance in the hallway mirror on the way. My uniform was spotless. I'd learnt the hard way not to dirty my uniform no matter how dirty the work I was undertaking! I was wearing black, 4-inch heels (4-inches is the 'optimum height for chores' my Mistress said), white stockings, a white garter belt and a classic-look black & white French Maid's uniform. The uniform was short, with a circle skirt trimmed with lots of white lace. The petticoat underneath pushes the skirt out giving it an even shorter (and totally impractical!) appearance. There are large puff sleeves with large ribbon bows and the bodice laces up at both sides and across the front creating a bib effect. It's finished with more lace around the neckline and satin bows to the front, covered with a small apron. I wear a matching hat. The uniform is locked at the back of the collar. Satisfied with my appearance I proceeded to knock. 'Enter.'

I went in, stood on the carefully marked out 'sissy spot' and curtseyed. It has taken a long time to perfect the slow and deep curtesy my Mistress required of me, but now it is second nature.

'Sissy, you are aware that Rob is away in a fortnight's time?'

Rob is my Mistress' lover. I haven't met him yet, but I already hate him! Ever since he arrived on the scene a month ago I have seen less and less of my Mistress and worst still, I haven't been released from my chastity device. As Mistress says, with Rob around, why should she bother? I really am reduced to just chores.

'Yes Mistress'.

'As you know, Rob tends to my....physical needs. The needs you can't satisfy.' She shot me a look. 'I had toyed with the idea of asking you to find me someone - maybe from Tinder or the like - to fill in in his absence, but frankly it was such a chore finding Rob in the first place (he was one of many blind dates) I'm not sure I can be bothered. And then I thought, before all this....sissy nonsense, you and I had managed. You were quite attentive at times in fact as I recall. So, I wondered if you would like to fill in?'

I couldn't believe my ears! Perhaps a month of no attention had been worth it? 'Yes Mistress. Yes please. I will do my very best to please you' and for good measure I added another deep curtesy.

'Very well. He leaves on Friday 14th. I will be drop him at the airport and head home. You should be waiting in my bedroom at 7.30pm sharp. You should be in your uniform. Do not disappoint me before then or this opportunity will be withdrawn. I mean it.' With that I was dismissed.

For the next 2 weeks I worked harder than ever to be the perfect sissy. I did everything promptly and with a smile on my face. Which brings us to now.....

I continued staring at the strap-on. I hadn't misunderstood had I? She had clearly asked me to 'fill in' for Rob. She didn't mention fucking me whilst Rob was away; why was her bloody cock on the dresser! I heard the door open and Mistress coming up the stairs. I concentrated on standing to attention.

'Well, well. The house seems spotless - again! I guess the prospect of tonight is good motivation! Anything to report?'

'I managed to complete my chore list and complete 3 chores from the extra list Mistress.'

'Very good sissy! Go and get dressed. Pick something slutty to wear. I'll get changed and meet you in here.'

She undid my locked uniform and I headed to the spare room - my room - and tried not to worry. Sure, she always asked me to change out of my uniform before she fucked me, but she also always asked me to dress extra feminine. Lots of pink, lace & bows. Perhaps I was going to fuck her?!

I knew just what to choose. I picked my May babydoll & matched it with black stockings, a black garter & red heels. The babydoll had red satin cups adorned with black lace and a soft, halter neck. I loved how floaty it felt and it was short - the tops of my stockings were on show. It had an open back. I felt more naked wearing it than when I was actually naked!

When I was called to come through I tried my best to march through like a strong, confident, sexy woman, but I was clearly still bothered by the sight of the strap-on. The fact that it had been moved - but not put away - didn't help.

My Mistress sighed. 'What's the matter? You should be excited. You look terrified. Come on; out with it!'

I took a breathe. I might as well be honest. 'I don't know why your cock is out Mistress. I thought you said I would be filling in for Rob. You didn't say you'd be fucking me.'

A wicked smile crossed my Mistress' face. 'I think dear, you have forgotten your place. Recite the sissy rules for me.'

My confidence drained away.... it had been a while since I had to recite the sissy rules, but I knew them by heart. Learning them had been reinforced with a paddle. '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. 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.' At this point it clicked - Sissy Rule 3 was the key. The strap-on wasn't meant for use on me, it was for me to use! My Mistress wasn't going to wear it, I was! This is how I was going to fill in for Rob! 'Sissy Rule 3: I am to remain in chastity. Requests to be released will be denied and I will be punished. A sissy does not seek pleasure through orgasm, but through service'.

'Considering Rule 3 - that we worked quite hard to remember if I recall - did you think I was going to release you? What, replace Rob's magnificent cock with that pathetic thing of yours? Really?! I meant what I said about you being attentive. You're good with you hands and tongue, but that's all. You couldn't satisfy me in any other way. That strap-on was your one hope.... I suppose this explains the improvement in your performance this fortnight. You really do need to learn your place.'

I didn't know what to say. The silence was deafening.

'Ok. You are going to learn your place. Tonight. You're going to get your wish, but you'll wish you hadn't! Go and get undressed. Come back in here naked. A 'man' wouldn't wear that ridiculous outfit so if you want to play at being a man you should at least look like one. Go on - get undressed and get back in here quick.'

I rushed out of the room. My head was spinning! I was going to be released, but it didn't seem like I would enjoy it! I carefully placed my clothes and shoes back in my wardrobe and returned.

'Come here. Stand in front of me; hands behind your back'. I did as I was told and she pulled the key - the key! - from around her neck. She inserted it into the lock and pulled my chastity device off. My response was immediate. You don't know how good an erection feels until you are denied them.

'I see my sissy thinks he can cut it as a man! Let's see. Here's the rub; I expect at least 5 minutes of pleasure. Rob can go much longer, but let's not set the bar too high. 5 minutes. That's 300 seconds. I'm going to straddle you and start the clock. For every second over 300, you get a day out of your cage. You can strut around pretending you're a man! Ha! But - and here's where you learn your lesson sweetie - for every second under 300, you will spend a day in your device. If you last 250 seconds, you have 50 days of denial ahead of you. Understood?'

'Yes Mistress.' 5 minutes! I was never going to last that long!

'Sit on that chair.' I went over and perched on the chair. I was so hard! Pre-cum was dripping fairly steadily from my cock. She sauntered over and paused above me, her pussy so close to encasing my cock. '300 seconds sweetie, that's all I ask'. And she sat down. I would like to say that month spent in chastity had increased my endurance & I gave a good account of myself, but I'm afraid it was quite the opposite. The moment she moved down on my cock, I came.

'Oh my God! OH MY GOD! Have you cum already?! Jesus! That is pathetic! I didn't expect much, but this, this is awful! I'm almost embarrassed for you! 300 days you're going to spend locked in that thing. Just wait until Rob hears about this! I should whip you for that display. I might let Rob whip you for me. Zero seconds. ZERO!'

I didn't plead. I didn't say a word. I started to try cry. I was so humiliated! And the thought that my wife's, my Mistress' lover might hear about this, laugh about it, Hell even whip(!) me for it just broke me.

'Oh for fuck's sake.' She climbed off me. 'Get out. Get out, get cleaned up and come back in here. I'm going to lock you up. The night is young; you can put your uniform back on and do one last chore - you can find me a man, a REAL man online!'

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4 Comments
AnonymousAnonymousover 2 years ago

I used to cum like he did all the time. It felt awesome for me. But I could not please anybody but me. Now I just have sissygasms all alone and It pleases me too.

AnonymousAnonymousabout 4 years ago
A double-edged sword

Sissymark- That dick in your hand at night is a double-edged sword... It can be your most trusted weapon in the battle of the sexes, and it can also be a dull, lifeless embarrassment when you need it most. My thought is just to live with it. Sometimes the "little head" has a "mind of its own" in spite of the plans that "the big head" has for it. That's cool. Just chalk it up to a lack of proper stimulation, or a partner who wasn't willing to go down on you when you needed it most. I'm pretty sure I could straighten things out for you in only a few minutes. -Lara

DianeRedfernDianeRedfernover 7 years ago
Well done and Interesting but consider a twist of what might have been

The characters and situation were interesting enough that I would have liked a first night of mistress' original plans come to reality the first night and have sissy feel oats enough the second night to try to unstrap and try to substitute himself before succumbing to the proper and inevitable conclusion you wrote so well. This is a very positive comment, sissy, because you are engaging and inspiring me to care about enhancing your fantasy. As is, plenty of merit on its own and a fun read. Just a bit too short you make me really wet. Try better next time, sissy. Air butterfly kisses to you and keep writing.

xoxo,

"Mistress" Di (just trying to get your juices going, sissy!)

AnonymousAnonymousover 7 years ago
Ignore the other comment I loved the story

Was a great story, her truly being the boss of the sissy, it's the life of a sissy to serve, and the the b____ of her. Wouldn't mind being in his place .

Thanks for a good read.

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