Sissy Life Pt. 03

Put simply, I was terrified. Things were escalating beyond what I had ever anticipated. I had been serving my wife, my Mistress as a sissy now for about 3 months. Every minute away from work was spent serving. The first month was good fun. I enjoyed being dressed and it was a bit like living out a fantasy. That changed when my Mistress decided I would be more dedicated, keener, more eager if I wore a chastity device. 'The only thing stopping you being more attentive, is that thing between your legs' she said. I admit I had started to get a bit lax. Doing chores in heels was hard!

I'll never forget that first night in the chastity device. I didn't sleep a wink I was so uncomfortable. My cock and balls ached. Ironically, they ached so much they were literally the only thing I thought about! I'll admit I became keener though. The thought of doing a good job and earning release really spurred me on.

Then came Rob, my Mistress' lover. That was another shift in our relationship. The time I was allowed for erections & masturbation was already less frequent because of the chastity device. Now this time simply evaporated overnight. Mistress said didn't see the point in releasing me now. I was keen, eager, did a good job. The house was clean & tidy. Rob took care of the physical side of things. If I wasn't happy, tough - she was.

Then came the events of two days ago. With Rob away on a business trip I was released. Given the chance to be a man. But I couldn't give my Mistress the pleasure she wanted. I came the moment she straddled me. I was so embarrassed, so mortified I cried. My Mistress was annoyed. She didn't think it reasonable for me to fail her so completely. So, she endeavoured to find someone to 'fill in' for Rob via FetLife. That someone was Tony. Tony was due at the house in an hour. At Tony's suggestion, their first 'date' would be at my Mistress' home - with me cooking and serving.

I looked at the clock. An hour. A measly hour! I was terrified. The cooking was done, now it was simply a matter of getting myself & my Mistress ready. Neither would take long. I had already helped my Mistress pick out her outfit for the evening. She'd gone for a triple boost plunge bra in red with a matching thing & a short dress that was so tight it hid nothing. I had 'helped' by rating each of the things she tried on. We'd been at it for more than two hours when she settled on the 'perfect' look for Tony. In the end she dismissed by thoughts though; after all, I couldn't tell her what a man would find sexy could I? 'You're probably trying to figure which would feel nicest on your sissy tush!' she said.

Picking my outfit was far quicker. When my wife had decided to embrace feminising me, she had been keen to encourage my serving as a maid at home. She purchased the clothes she felt I'd need. One purchase was a classic-look black & white French Maid's uniform that locked at the back. 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. A matching hat was bought too along with a pair of black, 4-inch heels. It was to be worn with white stockings and a white garter belt. A similar outfit was bought; except instead of black & white it was pink & white. This was matched with white stockings and a white garter belt too, but with pink, 4-inch heels. 'This set is for when we have guests' she said on revealing them. That was the outfit for tonight. If I thought my usual attire was humiliating, this was worse still! I couldn't believe a man I had never met - beyond briefly saying hi on Skype - was going to see me in this. I didn't have time to waste worrying about my outfit mind. I needed to get dressed and then help my Mistress.

I put the stockings on first. I needed to be quick, but also careful - snags & runs would be punished. I'd been whipped on this issue before. I certainly didn't need to give my Mistress an excuse to whip me in front if Tony - or ask Tony to do it! I put the garter belt on next taking care to ensure it was symmetrical. I picked up the uniform. It looked shorter than my classic-look one. I stepped into. It was shorter! I had to admit it felt gorgeous though. Just insanely short. It barely covered my ass when I was stood stock still, everything was on show when I moved. That was no more obvious than when I bent down to put my heels on. God, Tony was going to see everything! I added a white apron & a pink and white maid's hat. Dressed, I checked myself in the mirror. I looked ridiculous! My Mistress had been clear from beginning that I wouldn't be expected to wear makeup. 'Makeup is for women and you are a sissy not a woman'. The effect of that decision right now was I was very obviously a man in a pink French Maid's outfit!

I headed into my Mistress' bedroom. To my surprise she was dressed. She must have noted my disappointment. Since Rob came on the scene helping my Mistress to dress was a rare treat. Otherwise it really was just washing, ironing & cleaning.

'Don't look so put out. You get to reveal yourself in the presence of a real man tonight. You have plenty to be thankful for. Besides, I needed some time for these.' With that, she pulled something out of a bag. I couldn't tell what it was immediately. It looked like a dog lead. A pink dog lead.

'It's a ball-gag. I was texting Tony last night and we can't see why you need to talk tonight so I picked this up for you. Well?!'

'Thank you Mistress. I understand Mistress. I'm very grateful.' I curtseyed deeply trying to rescue the situation.

'You don't look it. I will correct your attitude in front of Tony if I need to you know.' I didn't doubt that! 'Stand in front of me.' I did as I was told and she started to fit the gag. The ball was massive! It really hurt my mouth to be that wide open. My Mistress wasn't gentle with securing it either. It was very tight.

'Turn around. Wonderful! Try to say something'. I just mumbled. I had a hard time swallowing let alone speaking.

'That's great! Really suits you. I love how it's making you dribble! Now, as you can't talk, Tony & I will still need a way to know you've understood any instruction we give you. So, it's one curtsey for 'yes', two for 'no'. Got it?'

I curtseyed once. My Mistress clapped her hands! 'This is such fun! I might use this more often. I mean, do you need to talk when you're doing your chores?' I reluctantly curtseyed twice for no. 'Exactly! Now, one last thing. She produced a collar. It was leather-look but again bright pink. And it had a big bell on it. 'I saw this when I was buying your gag and I couldn't resist! I thought the tinkling of the bell might be a nice reminder of your place. You're a plaything. An amusement. Let's get downstairs.' The bell tinkled with my every step.

15 minutes. In 15 minutes Tony would be here and I would be exposed. I couldn't figure out if it was better that I didn't know him than if I did. If I knew him maybe I could convince him to stay quiet? As it is, he's an unknown quantity.

'Now, when Tony arrives, you'll know because a car will pull up on the drive & pip. He's arriving by taxi. You need to go out, pay the driver and show Tony in. Tony's aware of this this. I doubt the driver is!' The terror on my face must have been obvious! I was panicking about being exposed in the privacy of my own home, let alone being sent out to be seen by a stranger!

'Don't look so worried. The journey should cost £30, I have that in cash. Just hand it over, open Tony's door and guide him in. Of course, if the taxi costs more you're pretty much screwed! Ha!'.

With impeccable timing I heard a pip. 'Go on. Don't make me tell you twice.'

I didn't have a choice. I opened the door, and walked out. In the drive was a black BMW. I approached and knocked on the window. The driver simply burst out laughing when he registered me. I could have died. I handed over the £30 hoping it was enough. He took it without a word. Opening the door for Tony was trickier. The doors at the back were blacked out so I didn't know where was sat. Inevitably I opened the wrong door so had to scurry round the other side to try again. All the time the bell on my collar was jingling.

Seeing Tony in the flesh was quite an experience. You could see that even if I wasn't dressed as I was, this was no contest. He was tall with broad shoulders, but more importantly he carried himself differently. And he looked so strong! He had a real presence. Perhaps the situation fed into this, but I wasn't so sure. I suspected he was always like this. I was a bit in awe. I couldn't talk so I pointed like an air hostess towards the house (jingling as I did), then walked that way hoping he'd follow. And damn, if I wasn't putting a little sway in my walk!

'Tony! How lovely to meet you.' My Mistress quickly pulled him in close and kissed him on the lips. 'You have met my husband already. Quite the spectacle isn't he?'

'Ha! Yes. Quite something.' I was dying of embarrassment. Thankfully my wife was keen to crack on. 'Lead the way' she said to me. I lead them to the dinning room. The table had been sent for two. There were candles and flowers. It was quite the romantic setting for a meal. And it passed without incident. I served the food, waiting stood to attention in the corner providing service - filling drinks, removing plates etc - as necessary. It was when they moved into the living room that things picked up pace.

'So tell me Tony, are you enjoying yourself enough to want to stay? I was saying only yesterday to my dear sweet sissy husband that I could, to be frank, do with a good fucking. You won't be surprised to learn that isn't something he can provide' she said shooting me a look. 'Even out of that contraption he fails miserably in that department. Tell Tony what happened yesterday. Tell him.'

I approached the sofa. I couldn't of course say a word; I was still wearing the gag. 'Oh, your gag. Ha!' She undid my gag. My jaw felt like it was on fire! I started to tell the story but I was interrupted, 'No, no. That's not how a sissy tells a man a story. On your knees dear.' The drink was taking hold now. I got on my knees and started again. 'No, no! Look at Tony when you address him. Jesus!'

I wanted to cry! I started again. 'Yesterday I failed my Mistress completely. She allowed me the opportunity to prove I could be the man of the house. She released me and....and, when she straddled me I came. I gave her no pleasure.' Now the tears were in full flow. Clearly this wasn't to my Mistresses liking because I felt the gag being put back in. I whimpered into the gag.

'See what I live with Tony? Let's go upstairs. You', she pointed at me, 'tidy up and then go to bed. Serve breakfast as usual. That's something you can manage.' She unlocked my uniform and took her new lover upstairs.

After I tidied I headed up stairs. I didn't know if I was supposed to take the gag off so I left it on. And the collar with the bell. I didn't want to upset her if she had cause to see me before the morning. I took everything else off.

In the morning I followed my usual routine initially. I showered, picked out some underwear (a white ruffled set), added some stockings and heels and headed downstairs to make breakfast - for two. I didn't know what Tony would want so I simply did extra coffee and toast, but also added some jam and marmalade to the my silver serving tray. I headed upstairs, took a breath knocked on the door of my Mistress' room. There was a reasonable wait before I was given permission to enter.

I tried to keep my composure but the scene in front of me was something I was unprepared for. I knew my wife had sex that didn't involve me, but I had never witnessed it. Tony was naked on top of the covers. On top of him was my wife, my Mistress; with his cock in her mouth. She and he both looked pleased. I just stood there in my underwear, my cock straining in it's cage. It was clearly just for show because my Mistress stopped after a few moments. 'We're going to get a shower. Tony needs his suit ironing for work. I want you in your uniform working on that whilst we do.'

I still had the gag on so I simply curtseyed. 'Tony can lock you in whilst I use the loo.' Clearly no-one was interested in taking my gag off. I was in agony! I took my uniform off the back of the door, stepped into it and then knelt by the bed. Tony didn't know what to do and I couldn't speak. After an awkward moment I handed him the lock on the bedside table & he figured it out. A new first; locked into my Maid's outfit by my wife's lover.

I ironed Tony's suit, shirt and for good measure, boxers and socks whilst he and my Mistress showered. Then I waited stood to attention until they had finished.

'I'm sorry I have to dash' said Tony.

'No worries. I've had a fun time. We can do this again.' Looking at me she said, 'Time for a treat - you can dress Tony.'

'What are you waiting for? Dress me sissy!' I snapped into action. I pulled his boxers on, fixated by his cock. It was soft now, but still looked powerful. I couldn't help wondering what it must be like to have a cock like that. Next was his trousers, his belt. Then I put his shirt on and buttoned it up. He smelt good. He did his tie whilst I put his shoes on and finally I helped him put his jacket on. I lower my face to the floor when finished.

'Say goodbye sissy. Curtsey for Tony.' As he headed downstairs my Mistress turned to me and said, 'let's check out what Mike's up to.'