My New Friend: Sissy Princess Annie

Sissy Annie sent me an e-mail to compliment the blog and tell me something about her unusual life. Of course, I was intrigued. I visited her blog and that only deepened. We began a correspondence that eventually included Sissy Annie's guardian and Mommy. For the most part, this was written by Annie’s Mommy, Ms. Holly. I have done some light editing and interpolated some material she sent me at other times.

When Annie was about 12 years old her parents sent her to therapy. She was diagnosed as a "little". She had the persona of a five-year-old girl.

Her parents wondered why she was so childish and immature. Plus she was very femme and completely scared of boys. When I met her she was working in a cute children's boutique and living by herself. Dr Dotson was recommended to me by a friend as an expert in these issues.

I told her my plan for Annie. She approved and said that it would be the best possible life for Annie. I have a trust fund for her and other plans if needed.

I adore Annie.

So what, exactly, is a “little”? Here’s a short explanation from Dr. Dotson:

A little is someone who likes to act younger than they really are. It's kind of having an alter ego that's much younger than yourself. Most littles don't act little 24/7 but when they do they slip into their younger persona. It's called slipping into head space.

When a little is in head space that is when they are at their most submissive and most vulnerable. They are most prone to emotional outbursts like throwing a tantrum or getting excited about something. They are also the neediest in this state as they are not thinking like a grown-up, but as a child and need a bit more guidance and reassurance. Some littles are shyer in headspace while others may be more outgoing. Every little is different and has her own special headspace.

The age range for a little is very broad and can range from newborn baby, to toddler and young child. One to eight is mostly the agreed range. It could be a fixed age like three or a range like two-to-six.

Littles tend to enjoy more childish, babyish like items like pacifiers, sippy cups/bottles, stuffed animals, dollies, picture books, toys, games, younger looking clothing, diapers, etc.

Little space is a mindset in which a person relaxes in a state of carefree, responsibility-free safety. It may be a designated time when a person relieves childhood memories, scenarios or desires that were unachievable when younger.

And a message she sent to Annie:

A typical five-year-old is comfortable with a little more independence, which means she enjoys being around other family members and friends more. Most children your age begin testing boundaries and demand to do things on their own. You are much more complex. You still have an infantile nature. You love being nurtured and cared for as a baby. That is just barely below the surface of your five-year-old juvenile self. Your need, as a little girl, to be treated as a little princess is very natural for you--what you refer to as your "sissy self". Do you realize what it means that mommy has made a playroom for you and your dolls? She is reinforcing your status as a five-year-old little girl and expects you to behave appropriately. I expect that once your playroom is finished you will be there nearly all the time"

And, now, back to Ms. Holly’s story:

I was shopping at a local mall when I spotted this cute little sissy. He was wearing a Disney princess top and cute matching skirt with lots of pretty pastels and a Minnie Mouse backpack. I can spot a sissy from a mile away. So juvenile and adorable. I didn't want to scare him. I waited until he sat down at the food court. I approached him and gave him a sweet compliment and then asked if I could join him. No surprise that he was thrilled that a beautiful woman took an interest in him. He loved sharing his interests and talking about himself. Such a sweet baby. He enjoyed Disney Princesses, unicorns, pretty dresses and all things girly. He told me all about his home. I asked him if he would be comfortable with me visiting him next Saturday. He gave me his phone, email, and address. I gave him a warm hug and told him what a remarkable and darling princess he is.

I texted him over four or five days before Saturday. His excitement was over-the-top. I instructed him to serve me a small continental breakfast and just be in his pajamas.

When I arrived that morning he was so nervous. I gave him a big hug and told him we would have the best day of his life. I had brought a lovely wrapped present for him. I explained to him that it would be his if he was a good little girl. By then I was relating to him as a child. He was so sweet, serving me orange juice, coffee, eggs, toast, etc. like I had requested. He never assumed that he would be eating with me. Such a good girl. I told him to go into the kitchen and make himself breakfast. I told him to stay there until I called for him. I went exploring. What a cute place with lots of cute childish and girly things including pretty dresses.

His male things were few and in the back of the closet and in one drawer. I drew a bubble bath and called for him to come to the bathroom. He was nervous when I told him to get undressed. To get to the point, I bathed and dressed him in a cute pink dress, pink panties, training bra, frilly socks and black patent leather shoes.

I did his makeup and then we had a chat about whether I should let him wear a wig or not. He didn't seem worried about that until I explained that we were going out for the day. Then he cried and begged me to let him wear the girly wig. We had a lovely day going out for afternoon tea, to a movie and shopping, all the time taking the opportunity to show him off as a darling little girl sissy. When we got home I let him open the present. It was an American Girl doll. He literally cried. I gave him a big hug and asked him if he would like to have another girly outing with me. You know the answer. He was helpless to resist. We got together again in a few weeks. The rule was set that he always carried his dolly with him.

After a couple of months we agreed to sign a contract where she would live with me as my five-year-old little girl. In time I became his guardian. That was important for him because I have serious obligations to keep him safe, happy, healthy and cared for. We have been together for 15 years or so.

I believe in the FISH philosophy--Feminization, Infantilization, Sissification and Humiliation. The FISH Academy is an idea of mine. Maybe someday I will have the opportunity to devote myself to this.

Once Annie started living with me, I discovered some very disturbing behavior. He would touch his privates daily and masturbated often. I could tell by his emotional state both before and after. I am certain you understand these disgusting male behaviors. Chastity was the solution. He cried and cried for release. Infantilization also was a significant part of his regression and acceptance. Humiliation plays a significant role.

The first year was very difficult for him. I took him, one-at-a-time to visit friends and family and introduce him as my little sissy princess. I had him curtsy, introduce his dolly and share how much he loved his dresses and being a girl. He cried and cried at the humiliation. Eventually he admitted that he craved it. But, of course, no more "release. I send him to his therapist every month. Her insights are very helpful. Plus she uses hypnosis to get into his subconscious.

Ms. Holly also explained a bit about herself:

I dislike men. I find most of them obnoxious and despicable. I have always found sissies cute and fascinating. I get sexually aroused by little girl sissies. They are no threat to women. Just the opposite.They are weak, extremely submissive and can be used for women's pleasure. I adore seeing men humiliated as sissies. When I first met Sissy Annie my intentions were to use her to get my satisfaction concerning men by humiliating her.

It makes me feel awful to consider how mean I was. But over time I fell in love with her and became extremely protective. I adore her joie de vivre. She loves being a little girl and I adore reinforcing that, I am sure I have spoiled her rotten.But she deserves it! There are times I wonder if she is the one in charge. This is a trite statement. But paddling her hurts me more than her. I know that's silly. But I am a complex woman.

More tomorrow