By Elise Wooton

 

Click Here for part 1 of Mrs Wooton’s story – “The making of a sissy maid husband”

 

After two months since she signed her life over to me, Sissy Glenda had settled into her new role quite well. Her life was work and chores then more work and more chores. It was only broken up by punishment and humiliation to keep her focussed on her tasks. Throw in a healthy dose of chastity and I had one hard working obedient sissy husband. I was getting very used to not lifting a finger around the house. Occasionally I may cook dinner if my best friend Amy was coming over, only because I enjoyed it but Glenda would serve it and do all the dishes and only eat the leftovers.

 

Amy’s idea of a chastity device was brilliant. The longer Glenda stayed in chastity the more obedient and docile she seemed to become. I had recently bought a dinner bell and Glenda would have to stop what she was doing and come running to wherever I was. It was such fun to interrupt her while

she was beavering away at a chore like scrubbing the bathroom just to make her pick up the TV remote off the coffee table that I could have easily reached myself. I was enjoying be  a treated like a spoiled princess. She knew punishment awaited if she dare show any sign of resentment. I must admit she became quite good at accepting gracefully whatever I dished out.

 

Up until now the only other exposure she had as my sissy maid had been to my best friend Amy. Amy enjoyed bossing her around and I enjoyed watching her do it. Before her new life began Glenda had given me two tickets to see the musical ‘Wicked’ as a birthday present. I knew very well that Glenda wanted to see the show as well, she was a big fan of the leading actress Amanda Harrison. Finally the date for the show was drawing near. My first thought was to take Amy instead, just to put Glenda in her place and reinforce that she had not earned the right to such privileges yet, however I was disappointed to hear that Amy had to go interstate that night and was unable to attend. I then thought something wicked myself. There was a guy who had just moved into our street called Marcus. I had chatted to him a few times and found out he was new in town and single. At a guess I would say he was 35. He looked after himself, was well built and I would often see him cycling. He was quite handsome and very friendly. Whenever he rode by his powerful legs and well shaped behind always caught my eye. He had met Glenda in her male garb but was unaware of her sissy maid status. I was a little apprehensive about asking him out, I had been faithful in my marriage for over 15 years but with Amy’s encouragement I decided I would ask him to the show.

 

I was taking my morning walk the next day when I saw him cycling and gave him a big smile and he stopped to say hello.

 

“Good Morning Marcus.”

 

“Good Morning Elise, how are you today?”

 

“I’m great Marcus, I am glad I saw you this morning, I wanted to ask you, I have a spare ticket to see ‘Wicked’ on Saturday night and I was wondering if you would like to join me?”

 

“Would I ever! I have heard it is booked out months ahead, I have heard great reviews and I believe Amanda Harrison is sensational,how did you get tickets?”

 

“Glen bought me two tickets for my birthday a few months back and the date has finally rolled around.”

 

“Can’t Glen go with you, does he have to go away?”

 

“No no, musicals just aren’t his cup of tea I’m afraid, I’d rather go with someone who appreciates them.”

 

“Thank you so much Elise, I haven’t had a night out since I moved in, it will be a real treat. what time shall I pick you up?”

 

“Why  not 6 p.m. and we can have an early dinner before the show?”

 

“Are you sure Glen won’t mind me having dinner with you?”

 

“Not at all Marcus! Glen likes me to be happy, you know what they say, happy wife, happy life.”

 

Marcus joined in with my laughter at my little joke. I found the flirting quite exhilarating.

 

“I insist I buy you dinner then Elise.”

 

“Sounds wonderful Marcus!”

 

With that I bid him farewell with a kiss on his cheek.

 

 

 

Saturday came around and I could sense Glenda was a bit distracted. I hadn’t told her anything about the show, I am sure she knew quite well that this was the day and was hoping I’d say something. After serving me my lunch on the balcony, her impatience got the better of her and she asked me,

 

“Mistress, aren’t the tickets to ‘Wicked’ I bought you for tonight?”

 

“They sure are Glenda, I am really looking forward to it.”

 

“What time do you think we should leave Mistress?”

 

The next few moments were priceless! The change in her demeanor was extraordinary!

 

“We…. Did you say ‘we’ Glenda?”

 

“Yes Mistress.”

 

“Where on earth did you get the idea that you would be going? The tickets were a gift for me Glenda, did I ever tell you that I would be taking you?”

 

“No Mistress.”

 

The look of disappointment on her face was something to behold, Her shoulders fell down and her head bowed tot he floor. I really had to fight back the urge not to laugh out loud. I couldn’t resist rubbing it in further.

 

“That is quite an assumption you have made there Glenda. A good sissy maid never makes assumptions do they?”

 

“No Mistress.”

 

“You will have to be punished for that.”

 

“Yes Mistress.”

 

I was really enjoying this interaction, She was squirming with disappointment and now hearing she was going to be punished was like throwing oil on the fire. 

 

There will be 12 strokes of the cane when I return from the show tonight for that display of arrogance.

 

“Yes Mistress.”

 

 

If she looked disappointed now, the next news would devastate my little sissy!

 

“For your information Glenda I have asked our new neighbor Marcus to go with me, apparently he is a big fan of Amanda Harrison.”

 

Glenda went pale, I could tell she was absolutely fuming inside but too scared to show it. The frown on her face and her hang dog eyes told the story. I kept rubbing it in.

 

“Marcus hasn’t been out on a date since he moved here and was so grateful he has offered to take me to dinner before the show, isn’t that nice of him?”

 

I could tell it pained Glenda deeply to have to say her dutiful,

 

“Yes Mistress.”

 

“After you clean up these things you can return to cleaning out the garage and at 4:30 p.m. you will run my bath.”

 

With that I dismissed her and went shopping for a new dress to wear to the show. I found the sexiest “Little black dress” imaginable and a new pair of stiletto’s. I returned home buzzing with excitement. I couldn’t resist a little more fun with Glenda. After she had run my bath I called her into shave my legs. It was quite divine to lay back in my warm bubble bath and have my sissy ever so carefully shave my legs. It must have been killing her to see me naked and know she could not have me, her role was to prepare me and help me look beautiful for another man! I am sure her clitty was being crushed by her chastity device as she tended to my legs.

 

After she dried me off with a fluffy towel that had been heated in the dryer, I told her to fetch my black G- string and black half cup bra. Glenda had bought them for me two Christmases ago and I had never worn them. It was the sort of present a husband buys more for himself than his wife and there was no way he was going to see me in them! Now he was sissified things were different. She could see but she could not have. I felt like a real bitch as I made her hold open the G string so I could slip into it. He must have felt devastated that I would wear them on my first date with Marcus but never wore them for him in over two years. I was loving this!

 

Finally the clock struck 6 and Marcus knocked on the door.

 

“That must be Marcus Glenda, open the door and ask if he would like a drink.”

 

“But he will see me dressed as a sissy Mistress, please don’t make me.”

 

“Come now Glenda, we can’t keep your true life a secret forever and besides I am hoping Marcus will be around a lot more often, he is bound find out anyway. Now remember to thank him for taking me to the show and don’t forget to call him Sir.”

 

Glenda went pale, she wasn’t expecting this! She gave me the most pleading look imaginable and hesitated. I gave Glenda a look that said I certainly meant business and with a measure of great reluctance she opened the door.

 

Marcus was surprised at the sight that greeted him and at first did not recognize Glenda. He stammered a little and then said,

 

“Oh..Hello is Elise there.”

 

“Yes Sir, please come in, can I get you a drink.”

 

“No thank you.”

 

I then came into the hall and said,

 

“Marcus, so good to see you! Are you sure you won’t have a champagne with me?”

 

“If you are having one Elise sure.”

 

I went up and gave Marcus a kiss on the cheek right in front of Glenda, then turned to say,

 

“I believe you’ve met Glenda when he was masquerading as Glen.”

 

I could see the penny dropping for Marcus and a big grin spread across his face.

 

“I didn’t recognize him Elise.”

 

“I think you mean you didn’t recognize her.”

 

With that we both had a laugh and poor Glenda went bright red with embarrassment.

 

“Come Glenda, hurry up with the champagne we can’t stay for long.”

 

As Glenda went to fetch our drinks Marcus was still looking very surprised and said,

 

“What is with the maids outfit?”

 

“It is a bit of a long story Marcus, I will tell you all about it over dinner.”

 

Anyway we had a pleasant chat while we had our champagne. I had never seen Glenda look so red in the cheeks before, she was burning with shame and embarrassment and could not bring herself to make eye contact with Marcus. As we left for the restaurant I couldn’t resist shaming her further by saying,

 

“Now I expect all the ironing to be done and put away by the time we are back and make sure you are waiting up for us Glenda, we may want a nightcap on our return and there is the little matter of a punishment we have to care of isn’t there Glenda?”

 

“Yes Mistress.”

 

With that we went off to the restaurant. I had one of the most enjoyable nights in a long long time. Marcus was great company and wasn’t fazed by hearing all about Glenda’s position in my household. In fact he said how much he admired my ability to take control, that it took all types to make up this world and that Glenda was lucky to have someone who understood what she really wanted! He added being a submissive sissy wasn’t his thing but live and let live was his motto. He even said half jokingly that he could use a sissy maid to help him with some of his chores! It certainly gave me food for thought!

 

Once he realized Glenda was not a threat he began flirting with me quite overtly. There was a longing look into my eyes over dinner, he praised me for my looks and my mind and rubbed his leg against mine under the table. During the show he had his hand on my thigh for quite a while and it moved closer and closer to my crotch. I was becoming very excited. 

 

I had no hesitation in inviting him back in when we came home. I ordered Glenda to make us coffee. As she was in the kitchen, Marcus sat next to me on the lounge and put his arm around me, I gave him the look that said ‘kiss me’ and he did. A long warm passionate kiss followed, I had not felt so excited in years. Glenda came in with the coffees and interrupted us with a polite cough. Oh how this must have been killing her! She actually had tears in her eyes. I do not think in her wildest sissy fantasies did she ever think that this would be the outcome! After handing us our coffee I said,

 

“Now Glenda, we have the matter of your punishment to deal with.”

 

“Yes Mistress.”

 

“What has she done to deserve this Elise?” asked Marcus.

 

“She made an assumption that I would be taking her to the show tonight, very disrespectful.”

 

“Extremely Elise, you can’t let her get away with that!”

 

I loved how Marcus was joining me in humiliating her, it made him seem so much more attractive, I was becoming drunk with power. I then had a brainwave.

 

“You are a fit young man Marcus, how would like to do the honors and cane her for me?”

 

“I am not sure Elise, it is not something I have ever done…I am not sure it is my place to do that. Couldn’t Glenda accuse me of assault?”

 

“Glenda would never do that, she would see it as a favor, it would be saving her Mistress from having to exert energy due to her misbehavior. Isn’t that right Glenda?”

 

I gave Glenda the look that told him to say.

“Yes Marcus,  Mistress is right.”

 

Marcus still hesitated,

 

“I don’t know Elise..”

 

I looked Marcus in the eyes with my most pleading look and placed my hand in his crotch,

 

“Please Marcus, I am sure you could do a good job, won’t you do it for me?”

 

I pursed my lips and mimed a kiss and then licked my lips seductively. I had never acted so provocatively in all my years with Glenda and she just had to stand there and watch.

 

“OK then Elise, just for you.”

 

“Go fetch the cane Glenda!”

 

Glenda returned with the cane.

 

“Offer the cane to Marcus Glenda.”

 

She presented the cane to Marcus in upturned hands.

 

After all his hesitation Marcus took to his role with a relish that surprised me. Once the cane was in his hands he took control.

 

“Right Glenda! Bring one of the dining room chairs into the centre of the room NOW!”

 

He raised his voice, and it even gave me a shock. He had Glenda scurrying to do his bidding. I was becoming more excited. Once the chair was placed Marcus continued.

 

“Panties down Glenda and bend over with both hands on the chair and legs straight. You have the most wonderful wife who lets you indulge your fetish for dressing up Glenda. You need to be taught to be grateful not resentful!”

 

“Yes Sir.”

 

Marcus was getting into this and I gave him the most approving stare, licking my licks seductively, urging him on.

 

“You need to be punished to learn a lesson, don’t you sissy Glenda.”

 

“Yes Sir.”

 

I was becoming weak at the knees over this interaction. Marcus was brilliant. He then

lined the cane up on Glenda’s right bum cheek and after two or three light taps drew back. The cane sizzled through the air then,

 

Crack!

 

Glenda let out a squeal that would have woken the dead. It was a ferocious cut and immediately a red weal developed on Glenda’s right bum cheek.

 

“Count them Glenda!”

 

“One Sir.”

 

The next stroke was harder and struck Glenda on the left cheek. There was another squeal before Glenda managed to say,

 

“Two Sir.”

 

“Stop that squealing or we will start again.” Marcus spoke firmly and he had me feeling very moist in the nether regions. The thrashing continued. It was far worse than any caning I had given Glenda. I was liking the thought of being able to call on Marcus to deliver a punishment. I am sure it would be a very effective motivator to ensure Glenda complied to my every command.

 

Once the caning was over, I sent Glenda to the corner to think about her punishment. I was so turned on, I beckoned Marcus to me and we engaged in a hot session of passionate kissing. About twenty minutes later I sent Glenda to bed and made sure she was left with the image of me in a hot embrace with Marcus.

 

While part of me would have liked to bed Marcus there and then, I have never been a believer in going all the way on a first date and with a some reluctance I sent Marcus home. There was plenty of time to explore this relationship further. It was an important first step for me in my new life and I didn’t want to go too fast too soon. The important thing was that Glenda probably thought I had gone all the way!

 

To be continued…….

 

Click HERE for part 3

 

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