from Sissy D

Dear Auntie Helga,

I have had mixed feelings about my mother over the years (she died over 30 years ago now under suspect circumstances), and perhaps talking about her now in light of my current situation will be helpful. I am a psychologically and spiritually minded person which helps me navigate understand and survive this world. I am on a path of individuation and realization and the process of becoming whole comes in fits and starts. We become aware of bits and pieces of the impact on our experience and then in some magical moment a synthesis occurs and we understand something in a larger context.

When I look at the fragments of experience with my mother that impacted me they all add up to the realization that the sissy archetype (and I do see the sissymaid as a modern version of the castrated effeminate eunuch servant that has appeared throughout history) has been cultivated in my psyche from early in my life. The experiences that follow are not much like the stories I have read on your site. They are not part of a continuum but are isolated events sometimes with years in between. Nonetheless they are my true memories and as will be seen were enough, when the right triggers were present to constellate a totality of persona which prior had not been known to me.

My first memory stems from an experience when I was between 2 and 3 years old. It was early evening and there was some kind of social event going on with guests in our home. My mother was 'dressing me' for the guests and for bed. I remember being dressed in very fancy blue satin Chinese pajamas with embroidered white silk button hooks. The outfit had matching blue silk open toe slippers with large white furry puffs covering the part you slip your foot into. My Chinese pajamas were very feminine, like something a geisha girl would wear. I remember my mother buttoning up the top and told me to slip my feet into the slippers. I can still remember the feeling as she fixed my hair. The feeling I had wearing the pajamas and especially the slippers was my first actual sexual feeling. A prominent feature in the experience was the pleasure and lust I sensed from my mother as she was dressing me as her little sissy and telling me how cute I looked. Looking back and I have many times as it was a very pleasurable experience especially wearing the slippers made me feel like a little girl. It was my first erotic experience and my mother's 'lust' was part of it.

The next significant experience occurred when I was about 6. My mother took my younger brother and I to buy shoes. I wanted new sneakers. Instead my mother told us both that we were getting a 'different kind of shoe'. She me fitted with red leather sandals with maryjane style buckles and straps and they were RED!. I was mortified and humiliated because boys did not wear shoes like this! There was nothing I could do and I was clearly pouting the rest of day. When my father got home from work that evening I was spanked for the hard time I gave my mother about the shoes. I avoided wearing them as much as possible but when I was forced to wear them I would experience a feeling similar to the erotic feeling from the silk Chinese slippers but not coupled with a sense of humiliation and shame.

The next significant experience occurred when I was in the first or second grade. We lived on the east coast and it was one of the days in early spring when the days were becoming warm and sunny. My mother would usually lay out our clothing for the day. Instead of the usual chino pants I was accustomed to wearing every day to school, my mother laid out a pair of red plaid Bermuda shorts and a white oxford button down shirt. I asked her why I had to wear these shorts because none of the other boys ever wore shorts to school. She said I did not have a choice and that I would be cooler and the other boys would be jealous of how 'cute' I looked. I had to walk to school and of course I was the only boy wearing shorts which was humiliating and some of the other children laughed at me and called me a sissy which of course was TRUE!

The final childhood experience I remember occurred when I was about 7 or 8. It was summer and very hot. All of the children in the neighborhood usually played out in the street after dinner until it was time to go bed. Most of the kids on our block my age were girls (more on that in a bit). I do not remember the circumstances of whether I was being punished or my mother was just in a bad mood, (or both) but I was told by my mother that I had to stay in my underwear for the evening which were 'tighty whites'. I was not allowed to wear regular clothing and I was sent outside and could not leave the porch. Of course I was the laughing stock of the neighborhood and all of the girls were laughing at me. It was quite humiliating. My mother was quite pleased with the situation. Somehow she got my father to support her in this and if I raised a stink I would have been given a spanking with a strap.

The next phase of influence occurred during my elementary school years and it bore little resemblance to the prior period. It was marked by the fact that I did not play sports with other boys. All of my friends were little girls my age. My closest friend was a girl who lived in a lot behind our house. We would spend hours together playing with Barbie dolls which I really enjoyed. Whenever her father looked in to check on us I would toss the doll away as if I was not playing as a little girl and felt great shame. During this period I also spent a great deal of time with my mother and grandmother. I did not have many male friends except for cousins that I would see occasionally. My parents had a very conflicted relationship and my father in addition to being an idiot and a boor was a very angry man. There were many screaming arguments between my parents during which my father accused my mother of coddling me and turning me into what he called a 'mamby pamby' . I was mostly sullen, withdrawn and probably depressed. I was also very effeminate. I was also a cruel bully to my younger brother which I regret to this day. I was not a happy child.

I can remember my mother seemed to take great pleasure in taking my temperature with a rectal thermometer and giving me enemas when I was ill. She took my temperature that way well into my teens. It was also during this time that I took on the role as my mother's confidant against my father who neither of us liked. By the time I entered puberty I became more social and belonged to a click of neighborhood boys. We were all intellectual and very cynical. It is important to note that my first sexual fantasies of this period involved being dominated and dressed by my mother and grandmother in feminine lingerie wearing an apron with a big bow in the back and high heels with other women present, or being dominated by my father as a young man.

I do not remember ever cross dressing at all or even wanting to and I had no external imagery relating to sissies or sissymaids EVER. I had no idea where this internal imagery was coming from the fantasies faded. However, I did idealize my mother for her intelligence and standing up to my father. I did love her and wanted to please her. She appeared to defend me against my father. I identified with her. She was the main bread winner and my father who was self employed was home more of the time and did all of the cooking, ostensibly because he did not like her cooking because she did not like to cook.

During my high school years I was very social and had many friends both male and female. I became interested in theatre and acting and was in several high school plays. Most of my friendships with girls were platonic. I dated only 2 girls and felt very awkward in that area. My mother was somewhat critical of my girlfriends and sometimes made fun of me in an odd way for having them. It was like she was jealous or something.

During my college years I hated both of my parents and lived at my school. I was very sexually awkward and felt inadequate. I had a very beautiful girlfriend my freshman year who was much more mature than me sexually. I was a virgin and she was very experienced and worldly. The night I was to lose my virginity to her we took psychedelic drugs. We attended a party in our dorm prior to attempting to have sex. We were both tripping on mushrooms. At the party a very effeminate male who was also very beautiful and notoriously 'gay' starting flirting with me at the party, I got so turned on and felt so completely humiliated that I was unable to have sex that night with my girlfriend. It took me months to recover and I did have sex with her the next semester.

During this time my mother start who was always promiscuous and having affairs outside of her marriage asked me if I could help to arrange places for her to meet her lovers at the apartments of my friends. I would arrange it and she would pay them for the use of their space. Towards the end of college I fell madly in love with 'the girl of my dreams' it took almost a year for her to acknowledge me beyond that of a platonic friend and I would do anything to please her. We finally consummated our romance in my senior year of college. She was very critical of me in every way yet I only wanted to please her. I was house sitting for friends of mine that Christmas vacation and had a big plan to have sex with my girlfriend there on new year's eve. My mother begged me to let her use the house for an afternoon tryst that day. Of course I set it up thinking how 'cool' my hip mother was and felt cool myself for helping her. However, she took the key to the house with her when she was done, I think on purpose. Not only did my plans to have sex with my girl get ruined but I had to drive to the other side of town in order to get the key back from her at that party she was attending WITH MY FATHER - very awkward, we both had to concoct a story on the spot to explain why I was there. My mother put me in awkward situations like that with my father all the time forcing me to collude with her against him.

Much later in life I found out that I was not his child in the first place! I believe that my mother was a closet DOMME and hyper sexual and constantly reminded my father that he was sexually inadequate . I was a symbol of that for both of them. I also think my father was a closet homosexual who could not begin to satisfy my mothers sexual appetite and that was on of the sources of their conflict. My father once confided in me that my mother wanted to dominate him and play a game called 'follow the leader'. He wanted no part of of it. I don't know why he told me that.

My girlfriend broke up with me a year later for another guy. She did not hesitate to let me know that 'having sex with HIM was very different than having sex with me' . Of course I know now that he was a REAL MAN.

Fast forward to 1999, I was in graduate school in psychology. I was in a gay bookstore one evening ( I assumed I must be gay and came out in 1979, I was always a total bottom and wanted to be dominated). As I was in a long checkout line that went all the way through the store, I passed by a rack with a small catalogue that caught my eye. It was called 'Apres Noir' and it was a catalogue of the most feminine lingerie made for men and modeled by very masculine men wearing very feminine lingerie and heels - no wigs or makeup. I grabbed it and practically consumed it right there.

Up to that point I had never had a desire to crossdress but once I saw those images IT WAS ON. I couldn't get enough. Soon after I began to experiment on my own with feminine lingerie, sissy dresses and high heels. It was not about being a drag queen, it was about being a submissive sissy. Since then I have accumulated and purged several collections and learned about sissymaids and cuckolds . I have never had the pleasure of dressing in the presence of or serving a Dominant woman but would like to be able to. I believe that my mother trained me for all of it. Now looking back as a result of this inquiry I am grateful to my mother and find some value for this part of my nature, this inquiry also informs my relationship to men as a sissy cuckhold

Thank YOU for YOUR attention and consideration Auntie Helga. I hope this all makes sense to you and does not waste your time. It might not be the kind of account you would publish but telling about my sissy origins with my mother has been very helpful to me. Any advice or feedback would always be welcome and treasured.

In submission,
Sissy D

Thank you for your letter Sissy and for writing about your childhood, I am pleased to learn that by relating this history you are more comfortable with your mother's memory. It is interesting how talking about our lives often informs us more than the listener. I hope you are able to find and form the types of relationships that bring you peace and joy.

Auntie Helga

Return to Index
Letter 9