When my husband and I started our son Joe in school it wasn't long before the school was calling having troubles keeping Joe in line with the other kids. Joe started to be a real problem yelling, using profanity not used here at home and kicking and hitting other kids and teachers. Jack, my husband, and I were forced to finally send Joe to another school however that didn't work. We moved a few times with Joe causing all kind of problem with the neighbor's kids. We had Joe in therapy with the therapist at the their wits end finding Joe more than they could handle. Both Jack and I tried so hard to find a way to settle Joe down with no success until I learned of petticoat training.
My husband wanted nothing to do with his son wearing girls clothes regardless of Joe's behavior until one day he had enough. The next day I bought Joe his first dress and the battle began. Every day after school I physically forced Joe to wear his new dress and every day he ripped it off again. I sewed that dress countless times as it looked awful from constant repairs however the appearance was the last of my worries. It took weeks of spanking Joe and forcing him to wear that same dress until one day he gave in to me.
As a reward I bought him a new dress, shoes and silky panties to wear at home at all times. Oh he wasn't finished with me just yet however I wasn't giving into him either. My husband couldn't believe I finally got Joe to dress like a little girl. Jack stayed in the sidelines letting me raise Joe as my daughter at home. It was hard on me to spank my son so much but with the little girls attire it all started to work as planned.
Dressing Joe like a little girl became the norm at home as Jack also got used to seeing his new daughter. Joe was getting along better at school and with the kids in the area. There was no need to change the routine for Joe which led me to teach him how to do housework as he got older. Joe's wardrobe grew as he was getting into his teens. Having a teenager is a challenge for any parent with Joe learning negotiation skills.
I maintained control of Joe as his Mistress but he wanted to know why his father Jack wasn't a sissymaid too. Jack laughed it off telling Joe there was no reason for him to be a sissymaid too. Little did Jack know I was planning on having a husband sissymaid figuring I trained our son why not my husband. I started building his wardrobe slowly and had the same sissy dress made for Jack. I talked to Jack about submitting to me to show our son he was willing to be a sissymaid as well. It was like talking to a wall even though I could sense he was giving in to me.
A few times a week I talked to Jack letting him know it was hard for me to be a Mistress one minute to Joe and then a loving wife in another minute to Jack. I really laid it on thick about how hard it was for me to be both Mistress and wife. It got to the point with Joe bugging his father to be a sissymaid to help him with the housework. One day to my surprise Jack wrote you for assistance. Now if you ever write Auntie Helga for assistance she will always give it to you even when it may not be what you want to hear. Jack found you to be very supportive of my work with Joe causing Jack to feel guilty for not accepting my offer to be my sissymaid.
A few days went by before Jack talked to me about his conversation with you with me eager to hear all about it having been a regular reader of the monthly letters. We talked more about Jack becoming my sissymaid along side of our son with no real commitment right then and there. The next day I received a call on my cell phone from Jack after he talked with you again agreeing to become my sissymaid husband. Well when I heard that news my face lit up with the biggest smile.
Right away I told Jack to shower and shave from nose to toes as Auntie Helga calls it then wait for me to get home. I walked in the house and there stood Jack in a towel so we got to work. First thing was the chastity device I already had waiting then his new outfit which was hanging in the back of our closet. Before long Jack was looking just as pretty as or son only feeling humiliated after looking in the mirror. I didn't waist anytime getting Jack started as my sissymaid.
When Joe came home from school he changed as usual then I introduced his new sissymaid helper. Needless to say Joe was thrilled his dad was finally a sissymaid like him and to have a helper. Joe began training his father just like I trained Joe. It was the greatest feeling to own a sissymaid father and son. During the day Jack has kept busy with a list of chores I gave him and when Joe gets home each day they work together until I get home from work. Jack is learning thanks to his son Joe and my night time strapon sessions help as well. Life is good now that I have two sissymaids and I highly recommend other Mistresses to do the same as you won't regret it.
Thank you for your letter Susan. Your experience with Joe is a testament to the effectiveness of petticoating and you instituted it perfectly. Also as you noted I did correspond with your sissy husband, he only really required some gentle coaxing as it turned out because of his love and devotion for you. Not often are father and son sissymaids together serving the most important woman in their lives, but it certainly is wonderful when it happens.
(edit, please note that this is Jack's wife writing later. See Letter 8)