My New Bedroom

From the time I was very young, I've known I was "different". I was fascinated with women's and girls' clothing and diapers which in my day were primarily cloth and plastic baby pants. Like all little sissy-boys, I loved girlish "dress-ups". Looking back on my boyhood, I laugh at how much of a stereotypical little sissy I was right from the start. I was flamboyant in my speech and gestures, and feminine in the way I ran and threw a ball. I adored playing with Barbie dolls and combing their hair. The most distinguishing trait I had that I was a was quite emotional, easy to cry at the slightest teasing or pain. Even at a young age the neighborhood boys avoided playing with me and by the time I reached 11 or 12 I was subjected to teasing and bullying by the boys.

When I did play with neighborhood kids it was often with the girls and I especially enjoyed spending time with the girl next door who was 2 years younger than me and had the most elaborate doll house and Barbies.

I remember at about this time when I was approximately 12 when people asked me what I wanted to be when I grew up I mentioned traditional careers such as; nurse, dancer, fashion designer. The looks I received were always a little puzzled followed by the comment,

               “Oh, that’s nice.”

After the traumatic experience of my dad being told about my desires to dress like a girl I really did feel a sense of relief now that he knew and while his reaction was far from positive it certainly could have been worse. He was away more often than at home leaving just my mom and I in our large home.  For the first few weeks my mom was busy purchasing all the necessities of dressing mike a girl and Saturday morning after she picked me up from ballet class she told me that she would be converting the spare guest room into a new bedroom for me because there was not enough room in my regular room for all my new clothing and she thought if I probably would want a girl style bedroom instead of my regular room which was full of models and boyish items. I could hardly believe my ears and agreed immediately so while we sat in the kitchen eating lunch we went through the Sears catalog to choose my new bedroom furniture. It didn’t take long because as soon as my mom flipped to the page with canopy beds she let out a squeal of delight. She chose the bedroom suite pictured except the canopy was all white.

I remember her immediately placing the order on the telephone and then announcing that we had to go to the fabric store to pick out material for the drapes and paint store to paint the walls. We picked out pale pink paint while for the window coverings mom went for lots of white ruffles and lace. I was actually quite excited to have a special room and when we returned home we immediately started sewing the curtains.

Within a few days mom had arranged for some men to remove the guestroom furniture and store it in the basement and by the next weekend she had painted the walls and put the window coverings in place.  The following Friday my mom picked me up from school which she normally never did, it had been a bad day at school because once again I had to endure teasing at school from other boys. Even though they were not aware of my sissy desires I was still often called a sissy because of my docile and effeminate nature. Before I could even pour my heart out and tell her about my day she excitedly told me that she had a big surprise for me at home.

She took me upstairs and told me to close my eyes as she lead me by my hand down the hallway when she told me open my eyes I was blown away by my room (see the photo….this is the actual page from the Sears catalog that I saved for 40+ years and had posted onto Pinterest a few years ago. Now the photo can be seen all over the Internet. I know it’s my photo because of the clearly visible verticle fold on the right third of the page).

 

My room had the exact same furniture except the canopy fabric and bedspread were pure white. I literally let out a squeal of delight and hugged my mom thanking her over and over. She showed me that the dresser at the foot of the bed was filled with cloth diapers, disposables, plastic baby pants, tubes of diaper rash cream, baby powder, and diaper pins. There was even a diaper pail in the corner decide the door. The bottom two drawers of the dresser had babyish clothing such as sleepers, rompers and little girl style tops which the remaining three drawers were filled with panties, training bras, ruffled panties, slips, tights, my dance leotards and all things feminine. The unit that had the desk had more clothing along with my school supplies because this is where I would be doing my homework. The biggest surprise was the closet which was had skirts, blouses, all type of dresses that were ultra-feminine with ruffles and lace. She showed me each item and held them up for me to see. She saved the best for last because she held out a ballerina’s tutu followed by a white crinoline and pink crinoline along with a square dance dress.

I was ecstatic and my little penis was erect from the excitement. My mom probably noticed but did not let on. She told me to enjoy my new room and pick out a special dress for tonight while she prepared by favorite meal which at the time was spaghetti and meatballs. I sent the time before dinner trying on different outfits and was in pure heaven, my penis was erect the entire time and I worried about my mom barging in and seeing me in this aroused condition. I chose to where a frilly white dress similar to the one in the photo along with white panties, white tights and frilly white rhumba pants to cover the tights.

 

When I entered the kitchen I was beaming from ear to ear which was not something my mom was used to seeing from me. I tended to be very quiet and sad due to all the teasing and bullying I went through. My mom smiled and gave me the biggest hug of my life and asked,

            “Are you happy now sweetie?”

            “Yes mommy I feel so much happier now”, I replied.

She gave me a playful pat on my bum and ten lifted the hem of my dress up to peek underneath?

“Oh sweetie this is supposed to be a little toddlers outfit and you are wearing big girl panties instead of diapers. Why don’t you go take over your panties and pin on a diaper and some baby pants then cover them up with your tights and rhumba panties? Hurry up dinner is almost ready.”

I could not believe what she said in fact my face got beet red from the embarrassment and I stood there in shock for a few minutes before hurrying off to do as I was told. Dinner was on the table when I returned to the kitchen and mom immediately tied a large bib around my neck and we dug in to my favorite dinner. She asked me lots of questions about how I felt and what I thought of my new room and all the clothing. I was at a loss how to describe how I felt about this change in my home life, I felt a little more comfortable talking about the clothing and the room. I was definitely happy albeit at a loss and confused.

After dinner my psychologist came over for a short visit and talked with only me and essentially asked the same questions my mom had asked plus a few more about how I felt. Was I happier now than when I dressed as a boy, etc? For the next few months I would see her weekly and she was satisfied this was what I wanted and she agreed that I now was much happier and at ease with myself.

By the time the psychologist left I was feeling very tired from what had transpired that afternoon and evening. Mom suggested I have my bath and get ready for bed and she would read to me until I fell asleep. I took a quick bath and when I let the water out of the tub my mom came into the bathroom which I was not use to, normally I put myself into my night diapers and got ready for bed by myself. Without a word she dried me and took me by the hand to my new room,  there in the middle of the floor she had laid out a large plastic covered diaper changing pad that she had sewn and beside it were a couple of cloth diapers, baby pants, diaper cream and baby powder. Without a word she pointed to the changing pad, I laid down and in a matter of a few minutes she had me double diapered and was helping me into a footed sleeper that had a zipper up the back.

She pulled back the comforter and sheet and as soon as I got into my new bed I heard the distinctive rustling and crispness of a waterproof sheet under my bed sheet.

            “I don’t want you ruining your new mattress if you leak in the middle of the night.”

I laid down on the bed and mom laid on top of the comforter beside me then handed me a bottle of warm milk with honey, this was something I always had loved. She read to me from my “Hardy Boys” novel, I don’t recall much of the story because I was so entranced by my new surroundings, the rustling of the plastic sheet, the thickness of the diapers which seemed thicker than what I had worn before and that I now seemed to have a constant hard-on.

Perhaps it was the onset of puberty or becoming comfortable and content with my clothing but this was the start where I began to notice that I was beginning to associate the diapers and the feminine clothing with sexual arousal and excitement.

The next blog post will begin to delve into those feelings and my adventures involving masturbation.

Dad Returns to a Daughter

It was a few weeks before my dad returned from a business trip to Toronto during which time I was beginning to feel more and more comfortable with my feminine persona. I would go to school dressed as a boy but during the evenings and weekends my mom allowed me to dress how I wished and there was no discussion about my attire other than when I would attend the ballet classes which mom had signed me up for. Thankfully, they were not near our home so there was no chance of me seeing any girls from my school.

I would always wear white satin panties because my mom said boy briefs would show through the leotard along with white tights and a black tank top style leotard. The first class was very embarrassing, a few of the girls giggled when they saw me dressed like them but to my amazement there was also another boy about my age in the class wearing exactly the same leotard.

It being the 1970’s I had long blond hair and the instructor immediately told me that I would either need to cut my hair or tie it back, I chose the latter.

More on ballet and square dance classes in another posting.

My mom did not tell me the exact day my dad would arrive home because I was already anxious about it, he came home late on a Friday evening after I had gone to sleep the next morning when I walked into the kitchen wearing my favorite short nightie over my night diapers I let out a scream when I saw him sitting at the kitchen table with my mother.

 

They told me to come sit with them as my mom did all the talking explaining the situation to my dad. He was not happy to say the least which my mom expected so she had arranged for the counsellor/therapist I was seeing to come to our home later that morning. She was better at explaining my situation to my dad and from what I recall his biggest concern was having a gay son. I didn’t even know what gay was at that age and hadn’t even had the sex talk with my dad parents yet.

During the two week period my dad was home we saw the therapist a few times a week and while my dad was still very disappointed with my desire to dress like a girl he was not ranting and threatening not to allow me to dress in his home. Like most European men he was quite a macho man and far from open minded or progressive thinking. We were far from close before this and now he was even more distant. Many nights I lay in bed worrying because I could hear my parents in the living room discussing me and how this was going to affect their lives. Some evenings it was discussions and other times it was more like arguing and yelling. My mom was the voice of reason and reassured my dad that everything would be fine. It struck me one night when I heard her tell my dad that she enjoyed being able to buy girl’s clothing and if I wanted to dress like a girl that was fine with her.

Out of frustration my dad commented,

“What is with the diapers? He’s not a bloody baby is he?”

Mom calmly told him what the therapist said,

“It’s his way of receiving the love and affection which he did not receive from us because we were too distraught over losing Naomi. The guilt I feel is horrible and if this helps him feel loved and makes up for us being distant while he was a toddler then so be it. Besides he needs them because he wets the bed and I’d rather wash diapers than bedding every morning.”

I distinctly remember starting to cry when I heard my mom defending me and truly loving me. It was not tears of sadness but rather tears of relief and happiness. Yes it was true I still wet many nights but it was really just mild leakage at night. The next morning I woke up completely dry but there was no way I was going to let my mom know before getting up I voluntarily soaked my diapers like never before. From that day forward I began to consciously soak my diapers every night. I would drink lots before bed and if I woke up dry I would purposely wet my diapers before.

 

My dad started travelling more shortly after this weekend and looking back I believe it had more to do with avoiding the situation at home than actually needing to work. My mom was perfectly content with the situation and I began to develop a closer and closer relationship with her.

This closeness grew and grew through my teens which I will share in future postings.

That fateful day when I choose to dress like a girl

My first blog post dealt briefly with my younger years now I share the day my mom asks me if I really want to dress like a girl.

This was a time in my life when rather than my mother merely guiding me towards diapers and feminine attire I was now keenly interested in all things feminine and babyish. On top of feeling safe and secure while dressed up I also began to feel the stirrings of sexual desire.

As my father became more successful he travelled more and I remember that while when I was younger he would usually come home on Friday nights and leave again on Monday mornings now he was gone for weeks on end and when he did come home on weekends my parents were busy entertaining guests or spending time at the country club.

His constant absence didn’t seem to bother my mother who continued her active social life even when he was away and many of her days were spent at the company’s main office here in Vancouver.

While I loved my dad he was a typical European dad who was distant and did not show much affection towards me. By the time I was 10 or 11 most of my life was with him being absent so I really did not have a strong need for a father figure in my life. While at this age I still did gravitate towards girlish toys I was beginning to participate in sports like soccer, swimming and baseball to be honest I was not very good at the sports especially soccer which required some physical attributes. I remember being teased and being called a sissy by some of the boys because I often would end up crying during a game if I was knocked over or hit hard by the ball or another player.

After one particular bad teasing from some boys on the team I nervously suggested to my mom that perhaps sports like baseball and soccer were not the best for me. I was already taking piano lessons and  my mother asked what sports  I had in mind I rather sheepishly suggested ballet and square dancing because they needed boys and I didn’t enjoy contact sports.

 

I remember my mother being very happy about my choice and within a week I was attending my first square dance class. I could not have been happier because all the kids were very nice and the boys were like me; they were insecure around the girls and for a lack of a better words they were geeks just like me. From the very first class what had me in heaven were the big puffy crinolines the girls wore under their dresses. I was so happy when my mom picked me up I told her all about the nice girls and boys and then she asked out of the blue,

“Did you like the girl’s pretty dresses?”

I nodded and just kept going on telling her about what we did and learned as we drove home. A few days later my mom called me into her bedroom because she wanted to talk to me about something. She sat beside me and held my hand,

“Sweetie not all boys are like the other boys in school or in our neighborhood just like not all girls are the same. Many girls do not like doing the normal girlish things like playing with dolls, wearing dresses, baking, they like to play rough like boys, dress like boys, etc. Our society accepts that and because it is perfectly acceptable and we call them “tomboys”. “

“The same sort of feelings and interests happens with boys and even grown men. Society expects all boys and men to be tough and manly by playing sports, acting tough, being interested in cars and tools, the list goes on and on. However not all boys or men have those interests which is quite alright. In fact many men love to do and enjoy the types of things that women traditionally do like cooking, cleaning, caring for children, designing and sewing clothing, etc again society is okay with that. It goes even farther because some boys and men feel more comfortable and love dressing like girls and women because they enjoy the feeling of the soft clothing and it makes them feel happier and more in touch with their real feelings.

“Do you understand what I am saying?”

I nodded my head but didn’t say anything.

“Unfortunately our society does not feel as comfortable with boys and men dressing and acting like girls or women, there is no equivalent word for “tomboy” other than “sissy” which is not quite as nice.”

“Sweetie would you like to dress like a little girl while you are at home? Mommy does not mind at all, you would still dress like a boy at school and when we go out. Would you like that?”

I recall looking down in embarrassment but at the same time having mixed feelings relief. As I grew a little older I started to feel like I was different from the other boys my age for being such a wimp and also enjoying when I was dressed up and being diapered. If what my mom said was true I was not weird. I looked up at my mom as tears started to flow uncontrollably and I started to cry,

        “Yes mommy I want to be like a girl.”

My mom hugged me and reassured me for a long time, I remember for the first time feeling a sense of relief. I  then blurted out between my sobs,

        “Can I still wear diapers and baby pants too?”

 

 

There was a long pause before she answered,

“If you are still having accidents at night and it will make you feel better then yes you will need to be in night diapers.”

“I just want you to be happy and know that your father and I love you very much. I will call your father tonight to tell him about our discussion and how you’re switching from sports to ballet and square dancing.”

 

 

The thought of my father knowing and what his reaction made me burst into tears again because he was always pressuring me to be tougher and more assertive. A few hours later I could hear my mom talking on the telephone with my father and explaining everything. I dreaded to think of what he was saying and thinking.