My Beautiful Sissy

Dear mistresses
Just read your stories dears. Not sure I agree with you but definetly love the fact that my sherry is and has always been efeminate. Even as a youngster she would pick out only the most feminine of my attire to put on. I always thought she was a pretty little boy but tried to dissuade her. She would climb into my bed dressed in one of my sheerest nighties and would snuggle up to me. I must admit it felt good. But in the morning I would once again tell her it wasn't right. Since those days I have discovered just how feminine she is. At 11 I let her dress up whenever she wanted on the advise of a freind. I made it a rule however that she must dress very feminin and nothing remotely boyish. She was dressed as a girl from then on, except at school. She was expected to learn to be a little lady. She learned her lessons as well as any genetic girl. I knew this was no passing phase and so at 13 I took it farther and began to take her out dressed. It was so nice having two daughters out shopping.
It was at this time that I realised something else was happening. She would get moody and upset. I sat her down and eventually found out that she had heard my freind saying how it was terrible sherry would never experience everything about being a girl as she would never have a period. I have never been able to ignore my children's needs although admittadely her's were much more complex. After thinking about things for a couple of days I asked her if she would like to see somewhat what it was like. I explained everything to her as I did my daughter. That thursday my Daughter started her period and I kept sherry home. I took her to the bathroom and presented her with her own package of kotex regular maxis. It was a while before we were able to figure out the best method for her to wear a pad but when we were done she had such a look on her face and she grabbed me around the waist and told me how girlish she felt. I cried, she cried. She took to it like a trooper. She didn't have to be told to change, eventually buying her own supplies and sticking to her schedule.
So Ok it was very unrealistic, only at home or when out shopping in other cities. That is until 15 when I finally took the oportunity of moving to another city and had her dressing 24/7 and being home schooled. She was in seventh heaven. She also began having full time periods and has been since then. So from then at 15 to now at 22 she has her period and now because of the net it is almost real. she found out how by herself and I was amassed when she told me she had to change her pad for real and proved it. I thought my trying times were over until last year when she announced to us that she wanted to become a sissy. I had no idea what that was beyond the normal meaning. So she gave me some sites to go to and I was flabbergasted. Many discussions later we finally started her on sissification training ( through a very good site, me learning as well) and she is excelling. The school head is very impressed and we have spoken on the phone about her eventually spending some in house time. I didn't think it possible but I am more than happy with her.
She has become an excellent sissy maid and does exactly as she is instructed at all times. She is respectful to all women ( never otherwise). Is dressed in the prissiest of sissy dresses and is not ashamed to go out in public. She is particularly fond of her pink sissy dress and white petticoat. She spoke to me a while ago about having breast implants I agreed to 40dd if it was possible. I don't like the breast forms either. However she insists on 50eeee. I am having trouble with that but we shall see.

Well ladies and sissies, thanks for reading. Please post me if you have any comments. I'll be happy to answer.

sherrys mom

Sherrysmom Sherrysmom
41-45, F
8 Responses Jan 7, 2013

My mom sent me to live with my aunt on her farm, then later I lived with another relative in Boston. I was a sissy from then on until I reached puberty. I wrote a memoir on it "He's my Little Girl" if you care to Google it.

lovely lovely story


I think alot of us is a little bit jealous.

good story, you sound like a wonderful mom.

You are a FANTASTIC Mother! More Women NEED to Realize that Feminine Men are the Best Spouses. A Woman that Feminizes the Males in her Life creates a Better world for herself, and the males she Feminizes. It is Wonderful to see Intelligent Woman as yourselves see the Great benefits have having Feminine Males in your Lives!! THANK You for being so Wonderful!!

Love your story Sherry. I only wish my mom could have been so understanding and realized I was a littler bit different than the rest of the boys.


Very exciting story I now had to ********** and put on a disposable diaper and peed in it and then ********** again reading your story... My diaper is very wet and I am so horny... Have you this way of ************ ever? Thank you...

Hurray 4 u!
Gawd bless!