The Beginning

Today was supposed to be the initial training of Mina, my sissy maid in training.  I met him back in April during a munch I hosted.  He’s a big guy (6’4″, over 300 lbs) with dark hair and glasses.  He came under the pretense of my Littles group, but was basically discovering himself.  He came to the notion that he wants to be a Sissy Maid.  In private conversations later, he mentioned that he really wanted to be a Sissy Maid and that he wanted to clean my house at a future event.  It felt weird to me, but I asked Daddy and we said we’d think about it.

Conversations later, he asked if I could train him to be a Sissy.  He came by the house and I told him that I would check with Daddy and see what he says and outline a plan.  I drafted a training contract and he signed it on Tuesday. We went over details, like me adjusted his name to a more feminine form – Mina for short.  We went through Mina’s wardrobe and accessories which ended up being about 3 bags worth.  I advised her to list me as training her on Fetlife in addition to revamping the entire profile and posting some pics.  I took a few which included her in chastity.  Though I made it clear that I was not her Mistress, I think she has that in the back of her mind.

So today was supposed to be Orientation and Training Day one.  Mina failed miserable on remembering to address me as Ma’am.  Then she had the idea to go shopping. We spent too much time doing that instead of teaching.  I did a brief orientation of my place and how I like things.  I made space in my guest closet to house her stuff while in training since she lives with her parents and can’t expose herself there.  She’s making too much focus on her chastity cage and I don’t want to be in the position where I have to hold the key or touch his genitals in any way.  Her dick looks like Daddy’s when it’s soft and she has been aroused in my presence.

Mina is too overzealous and asked a lot of questions way out of her range. I’m unnerved with the questions about one of my friends.  Apparently she saw her profile and likes her so she wants to inject herself into her life somehow. I told her that my friend wouldn’t be interested in her and her house is no match for her current abilities.  Then she went and advertised herself on Fet without checking with me or obtaining my permission.  I told her she hasn’t even been trained yet.  Then I was getting messages from people responding to her ad. I was pissed and I let her know that.  I let her know that she would be punished for that.

We also took some measurements.  Based on her size, she is a 3W/24W around the belly area.  Sorry love, but those 1x/2x outfits are NOT going to fit!  I told her we have to work on losing the weight.  I told her that I would put both her and my husband on a diet and that they would both weigh in and she needs to beat my husband at the weight loss. She liked the challenge. We took pics for both her profile and myself.

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Walk and Talk like a lady

Mina’s day yesterday was spent leaning how to walk and talk like a lady. We watched YouTube videos from trans men and put them into practice. Mina hard a hard time losing the bass in her voice, but when i had her sing me me me me, she got it. I also had her walk on the treadmill in heels. She did pretty well!

Shopping

We went to Goodwill and Gabe’s.

Practice

Mina was supposed to come over Thursday, but had to work late.  She really needs to learn how to tell her bosses “No” when they over work her.  She wanted to come by Saturday, but I explained to her that weekends were mine and Daddy’s days.  I asked permission but he didn’t want her monopolizing our entire evening.  I let her come over even though I would be leaving to go to dinner with Daddy.  We opened the packages we ordered and discovered that the silicone breasts we ordered were too small.  They looked more like a B cup than a D cup.  We decided to send them back.

We decided that while Daddy and I were gone to dinner, that Mina would clean.  I wouldn’t give her any direction, she was to spot what needed to be done and do it.

Intrusions

So I invited Mina to my little birthday party.  In informed her that I was going to be in little space and not trainer or adult space.  I tried to make that abundantly clear but she violated that repeatedly throughout my sleepover.  She kept asking me what to wear, bringing up adult conversations, and at one point, stopped my party to show off her clothing to one of my guests.  I was impatiently waiting for them to return to play a game and finally, I got up and went in there and told her that this was my birthday party going on and that it was disrespectful and it needed to stop.  She apologized but still didn’t get it.

I wanted her to practice talking in a female voice, but that only happened when I reminded her.  She insisted on wearing her heels she just got fixed and looked ridiculous trying to walk around my guests who were in little mode.  I advised her that she could be a teenager, but even teenagers don’t walk around unnecessarily in heels at a child’s birthday party.  I need her to start thinking like a female before trying to act like one.  We will need to go back to square one.

She fell asleep sitting straight up during one of the games.  I recommended that she head to bed and she refused and fell asleep again.  When it was bedtime, she had to sleep in the guest room with two of my other guests and decided to sleep with no shirt on.  I was about to recommend she put a night shirt on when she figured it out for herself.  She also admitted that she had worn her cage for the last 2 days.  I told her that she would desensitize herself for her new mistress, but she’s not listening to me.

She was supposed to cook breakfast and did an okay job.  She left the burner on after cooking and I had to scold her for it.  By the time it was time for everyone to leave, I was ready for her to leave.  I know she wanted to stay and do makeup, but I needed time to myself.  I got to the point where I just didn’t want her to talk anymore, and my sister and friend got the same gist.  She cleaned up and took out the trash and planned to meet up on Wednesday.  We will have a lot to talk about.

Learning to be a Lady

Trying to get Mina used to structure. Saved a note in my phone:

• How is my Mina today?
  Get undressed – weigh in
  Get dressed for work
  Have you completed your assignments?
  Let me see food/exercise log
  Have you displayed feminine behavior this week?
  Review blog
  Evaluate house and start working

I was very proud of her for dropping a whopping 5 lbs! She beat out us!  She explained that she has been watching what she eats and using meal replacement shakes.

She cleaned the kitchen, put the dishes away and swept the floor in addition to vacuuming the floors.  She forgot the bedroom but I let that slide.  She’s also been more conscious of using Ma’am at me.

She set up her blog and I helped her with the setting so it will send me an email every time she makes an entry. I asked her to write about how she feels, things she wants, and emotions involved in our process.  She only did 6 of the 10 rules writings I asked for.  We will definitely have to work on that.

She’s also getting better at getting dressed by herself.  She busted out of her garter straps, and we determined that she can’t fit into her maid outfit.  I’d have to rip out the entire back and redo it.  She’s so damned intent on getting heels and got the first pair fixed.  I tried to explain that first she needed to learn how to walk in a feminine manner and then start with a low heel and work her way up.  To prove my point, I had her watch a few videos.

We went ahead and shopped online for some size 14 Mary Janes.  We negotiated on a 2 inch wide heel and hopefully she won’t break that one.  She also wanted a smaller cock cage (much to my disapproval), some jewelry and some silicone breasts.  In order to get the products from my Wish account, she needed to deposit money into my account to cover it.  That warranted a trip to my  bank.

I saw the desire in her eyes to go out dressed as she was – wig and skirt and all.  I told her she didn’t have to but she insisted.  She wasn’t going to leave the car anyway.  She did great except for forgetting to use her female voice while talking to the teller at the drive through.   We’ll work on that next time!

All Made Up

Mina has been meeting me when she has days off.  She live nearly an hour away and insists on coming to see me as much as possible.  No problem here.  The other day we met, we went to Walmart to discover that their swimwear was only $1.  We bought nearly 25 pieces between the two of us!  She thinks that wearing a swimsuit under her clothing will help make her look slimmer.  However, only one suit fit her.  She didn’t want to try them on in the fitting room.  I understood.  I told her that a lot of the 2Ws wouldn’t fit her right now but she bought them anyway.  We started a suitcase of clothing that won’t fit right now.

I did her first weigh in at 316 lbs.  We have a lot of work to do!  The first time she dressed up, she wore 4 inch heels that broke on her within 10 minutes. I keep telling her that she needs to start with a low heel and work up to a high heel.  She definitely needs to lose weight before attempting any kind of heel at the moment.  She showed me websites and I showed her some Mary Janes to start out with.

She did not compete the first assignment which was to create an online blog and give me access to it.  She also did not complete the sentence work that was due to me.  My sister came over and we did a make-up session with her.  She squints her eyes so tightly that I could hardly get eye makeup on her.  I advised her to buy creamy eyeliner instead of the 7 eyeliners she picked up from the dollar store that wouldn’t work out.  She’s so intent on looking “passable” but isn’t used to having her eyes touched.  We went ahead and took a picture of what we had.

I had to go work at the pool. Both of them came with me. Mina put on her shorts to go swimming and I dropped the bomb:  No swimming until my sentences are done. So there she sat and my sis and I swam. She came in later.  I finally got my sentences done and reminded her that I need that blog by next week!

Rules & Assignments

I needed a fitting disciplinary action for Mina to remember to call me Ma’am. So I devised some rules and the punishment for forgetting was to write (or type) them 10 times.  She claimed that she did them and they got lost. Oh well, do them again!

Rules:

1. Everything out of my mouth should end with Ma’am.
2. Every written communication should start and end with Ma’am.
3. I will not interrupt Ma’am.
4. I will not give orders to Ma’am.
5. I will always speak in a girlish manner in Ma’am’s presence.
6. I will not speak until spoken to by Ma’am.
7. I will walk femininely around Ma’am.
8. I will always smell clean and fresh in Ma’am’s presence. 
9. I will not make posts without Ma’am’s direction.
10. I will sit quietly and ladylike until Ma’am directs me to a task.
11. I will curtsy upon approaching and leaving Ma’am’s presence.
12. I will work on my weight plan and will weigh in weekly with Ma’am.

I also created a list of assignments for her:

1. Create a blog.  One entry per week on subject of your choosing and assignments.
2. Buy more feminine panties.
3. Make a food and exercise log in conjunction with a diet plan.
4. Download Google Fit or another app for tracking steps.
5. YouTube:  How to curtsy
6. YouTube:  Make-up tutorials specifically for Sissies
7. YouTube:  Bootlblacking
8. YouTube:  How to use an epilator
9. YouTube:  5 Basic Cooking Skills – Gordon Ramsay
10. YouTube:  How to do a Basic Salon Perfect Manicure
11. YouTube:  Do’s & Dont’s of Table Service – Foxtail
12. Provide service for a tea party

Going Out in Public – Baby Steps

1. Go to Fitness Room in Fitness Clothes
2. Bra & Panty Shopping
3. ULTA for make-up session
4. Play Party in full maid, makeup, wig (Halloween)
5. Play party in full dress up & heels
6. Walk mall in short wig & makeup
7. Walk mall in skirt, wig & makeup
8. Walk mall in dress, heels, wig & makeup