Teenage Years – (Chapter 2)

Being a normal teenager is a trying time and like every teenager I started to have some behavioral issues. Being raised under the watchful eye of a very controlling mother with her high moral values made it worse.  She was a devote catholic but, in my ways, she had belief's more in keeping with some Fundamental Christian beliefs. She was very active in a Catholic Women's League and often hosted meetings at our home.  I often heard her lecture at these meetings about the importance of discipline in the home and she was in the minority.

Eventually when I was about 13 or 14 years old one day she sat me down and told me that we would be switching churches and attending a church that was more in line with her beliefs and that she thought I would be more at home there among other kids my age who had a similar upbringing.

I found out later that one of the reasons she left the Catholic church was that the church was not open to her ideas of traditional family values that she was pushing on members as well as they had issues with her and raising me as a girl.

This new church was near Abbotsford, BC. which was considered our version of the Bible Belt. The church went by the name of “Mission Traditional Christian Family Church” or “MTCFC” which no longer exists. I will share more details about our time at the “MTCFC” in an upcoming post.

My behavior changed very quickly, and it first started with me starting to talk back to my mother; something I never did when I was younger. She dealt with it by washing my mouth out with soap, which was horrible, but it had the desired effect. It only took a few mouth washings before she put an end to me disrespecting her.

The other thing that changed was that within a matter of a few months I went from being very slight to being a kid who was constantly snacking and eating sweets which caused me to become quite chubby or to be blunt fat.

I started high school at about that time and didn’t take long for word to get out about me that I was being relentlessly teased and called “girlie boy” or “diaper boy”. It didn’t help that my mom had always dropped me off at the front of the school every morning and was there waiting for me when school was over. I was upset most days and she usually just encouraged me to ignore the other kids and if I didn’t react, they eventually would just stop teasing me. One thing my mother was, was very comforting and reassuring she would always comfort me at home and have a treat which of course added to my weight issues.

Things did not improve at school and I became argumentative with my teachers and I was also being disruptive at the Square Dance Club. Looking back my mother never really scolded or dealt with me acting badly in front of others but talking back to her was dealt with. My mother often defended or made excuses for me when I acted up in front of others and especially so at school.

The most traumatic day for me at school was when I was coerced to go to the boys locker room and a group my pants were pulled down exposing my diapers and took away my pants, I was relentlessly teased and laughed at, I lashed out and started a fight that sealed my fate. It was made even worse because when I was so upset during the whole incident I soaked by diaper.  Uncontrolled wetting was something that occurred when I got upset and even as I got older it still happened on occasion.

As a result of the incident my mother was called to the school, and we were told that I would be suspended from school for 2 weeks. On the way home my mother was very supportive and understanding she removed me from public school and gave me the choice of going to a private Christian school or to be home schooled. She sat me down and told me that she was very sorry about what had happened. She reassured me that I would not have to wear diapers to the new school if I thought I could stay dry and if not, she could provide me with training pants.

She told me that if I wanted, I could choose to stop being a baby and give up my feminine clothing and activities. I had a big break down that afternoon and was bawling and really felt very babyish and I told her that I wanted to escape being a teenager and just be babied.

Mom asked me if I wanted to give it a try for a few days and that maybe it would help me feel better about the day’s events. I was still crying, and I nodded my head, she gave me a big hug guided my head so that my face was right against her breast for a few minutes until my crying slowed down. I don’t recall what transpired next but the next thing I knew she had unbuttoned her blouse and now my face was against her left breast. I remember starting to pull away and she reassured me that   it was okay, and this was part of being a baby, moments later I felt her nipple against my lips, and she whispered to suckle, and I would feel much better. I felt very weird, but I was still upset, and it was not long before I began to gently suck on her breast. I don’t recall how long it lasted but it was not long. When I stopped crying and my breathing slowed, she pulled my head away and told me to go lie down on my bed and rest while she made dinner.

I was confused by what happened it was not as if I enjoyed it or disliked it I was just numb. At dinner my mom acted as if nothing happened, she just acted like normal, and life just continued. The breastfeeding was never happened again nor was it ever discussed.

However, I did notice as time passed, I became much more orally fixated on things such as a pacifier, baby bottle or even my thumb when I became stressed or anxious. In my early 20’s when I had my first girlfriend I was obsessed with sucking and nursing on her nipples.

Assignment From Madam; How I am feeling as the day approaches?

 

My first blog post that will delve into my feelings as Madam Jamie and I are finally nearing the day when my development as her Sissy will actually begin. It’s been over two years since the journey began and I am blessed that Madam Jamie firstly has taken me back but also has had the patience to train me. While we have discussed many things and unfortunately many times my behavior and comments have not been the best,

I am excited by what lies ahead but also there is trepidation.

The trepidation relates to the severe punishment I am going to receive for my disrespectful conduct at our first meeting and then the stupidity of leaving Madam Jamie for another Mistress.

Leaving Madam was one of the most ridiculous things I have ever done.

I realized that I had made a terrible mistake and after a lot of soul searching, I decided to contact Madam Jamie again. I was so relieved when Madam Jamie responded to my messages although the reception was very cold and remained cold for a long time.

Madam’s continuing coldness and overall demeanor still keeps me off balance and I have a hard time dealing with it. I have a hard time being ignored and it makes me feel unwanted.  Every time I want to let Madam know that need her, I get snapped at. I know it’s poor judgement to ask for more attention which only leads to more coldness and a quick written reprimand. Even the written reprimand shocks me a bit which makes me wonder what the verbal one will be like.

Am I afraid? Absolutely, in fact I am terrified. I have been terrified a few times as a submissive but that was at the hands of male dominants. I have this habit of acting up and acting assertive when I am afraid which I keep telling myself not to do especially with Madam because of her no-nonsense character.

I have never shared this before but the other thing that I am so anxious about because it is so embarrassing is that the few times I have been chastised, humiliated to the point of being very afraid or ashamed is that I have actually wet myself like some little boy. If this happened in front of Madam, I would be so mortified.

After a lot of soul searching, I have realized that Madam is what I have been needing my entire life. I have been unreliable, lazy, disrespectful etc. towards women all my life. I have grasped that I need to change, and I am blessed to be taken under Madam’s wing.

All my life I have wanted and needed a strong willed and demanding woman. Someone who will not put up with my lies, games, and disrespect. One thing Sissy’s all have is in their fantasies they have this ideal Madam for most of them it’s more like the dominatrix of their dreams in leather or latex. Not me however I had visions of a business lady who in the real world so her as a successful yet conservative woman. I preferred the idea that my Madam believed in domestic discipline. Someone who would think nothing of slapping my face, washing my mouth out with soap. leading me by the ear, and using whatever was handy to discipline me such as a hairbrush, wooden spoon, her hand etc.

From all indications Madam Jamie is that type of disciplinarian as well as so much more. At the risk of sounding shallow I love that Madam Jamie is full figured and that if she is upset or angry her face shows it. Madam Jamie is a no-nonsense woman who will not put up with any of my attitude. I have needed a woman who could easily overpower me not just physically but also mentally. A woman who just by putting her hands on her hips and staring at me will extract an explanation from me. The fact that Madam does not care if her neighbors hear her smacking my bottom and my cries probably means she would not think of humiliating me in public if the need arose.  Many days I think the humiliation of neighbors or eventually her friends hearing and seeing me being punished would be worse than the physical pain.

Up to this point Madam Jamie has said that she is strict, won’t put up with my habit of talking back or being disrespectful and believes in humiliation and discipline.  I am pretty sure this is the case and she won’t suddenly go soft on me. This would be disappointing because I am going into this wanting to change and be a Sissy, she would be proud of.

I want my Madam to know that in spite of my tears and cries for mercy or compassion I recognize that if you were to give in to my pleading my training would be compromised, and you will not achieve the desired effect.

I love that Madam Jamie has made it very clear that there is no equality in the relationship. I once or twice was upset that she expected me to contact her daily, but she would ignore me for days. When I complained I was put in my place and rightly so.

Every day I think about my first day of training with Madam Jamie. Not knowing what it will be like is so difficult because I do not feel in control. I understand that as Madam’s Sissy I will not have any control and the sooner I resign myself to that the better. This will be a huge hill over me to overcome and a struggle.

I think about arriving and how you act towards me. I doubt it will be in a friendly manner nor should it be. I need to be prepared to confess to you in person about all my prior conduct and lies. It will be very challenging for me to do both emotionally but also the penalties to follow. I will be relieved once it has been dealt with, we will start with a clean slate.

I am very afraid about being humiliated and you making fun of my tiny penis and as silly as it sounds being put into chastity will be horrible. I have never been in chastity before in front of a woman! Madam I have never asked but am I expected to be clean shaven down there too? You have no idea how embarrassing it is going to be to be standing in front of you with my dress pulled up so you can lock me into a chastity cage.

I am grateful that you are open to diapering yet on the other hand I began to realize that it has been at least a decade since I last was diapered by a woman and those times it was with a “mommy” so it was in a nurturing environment. With Madam Jamie diapering can either be as a reward but also as punishment. I expect that because of your demeanor even when done as a reward I will feel humiliated. I can’t even imagine when the day comes that I am diapered, given laxatives and expected to use my diapers. I have only messed once with a mommy, and it was very emotional and draining. To experience it as punishment will definitely have me in tears and I have wondered if the effect will be the same as a severe spanking or worse.

With the help of Maid Jenn, I have been focusing on basics to make a good impression. Simple things like not being late, behaving appropriately and submissively right from the moment that I arrive. I am ashamed to say that I don’t think there ever has been a time where I have not questioned something when the women in my life told me to do something or questioned me about what I have done and why. I know that I really need to learn to remain silent and must never talk back to you.

I am also grateful to Madam Jamie is that for the most part was quite patient when I have one of my online temper tantrums however lately even minor behavioral hiccups upset her and she expresses disappointment and doubt about me. I understand the disappointment as in many ways it’s quite like a mother dealing with an obnoxious child which is another thing I admire about Madam. Decades of not being taken to task will be difficult to undo but Madam will make sure it is undone swiftly and permanently.  I would hope that initially there is some leeway the first time it happens by mistake in person, but I am fearful about how Madam will put an end to any outbursts.

I try to improve because I want Madam to be proud of my accomplishments, I think there are times that she is but when I slip up especially when I ask for attention, she becomes very angry. I hope she realizes that these pleas for attention are because I want to be with her, but she treats them as me being intolerable and a nuisance. I suppose like many things I need to learn I will be taught quickly and definitively by Madam.

While I understand that there is no escaping the punishment, I will receive on my first visit. I know my fate is sealed and no amount of pleading is going to change the outcome. How severe will it be and for how long? I have always hoped that Madam will have a change of heart, but I understand why it must be done. It’s to teach me a lesson but I also think she wants to clearly establish that there will always be consequences to my actions. I still regret my moment of stupidity where I challenged and bet Madam that she could not make me cry in less than 5 minutes. This stupidity sealed my fate and guaranteed my misery.

All my life I have been a pathetic and inadequate lover. Having a ridiculously small cock didn’t help but the real issue my selfishness but also my laziness and lack of desire or caring about pleasing my partner. Chastity will take care of part of the problem and Madam is definitely not going to accept my laziness or lack of effort. My future is now in pleasing Madam not only orally but also with a dildo gag. How fitting that this Sissy will be locked up so that I have no release or even pleasurable sensations in my penis so I will focus my attention on my Madam.  For this reason, I feel that I should remain in chastity until I have mastered the ability to worship Madam’s pussy.

Yes, oral service frightens me for many reasons. One is that I have never enjoyed it, when I did it I did it poorly and without enthusiasm leaving my partner unsatisfied and lastly, I always thought it was demeaning or submissive to have my head between a woman’s legs. How ironic is that because what I truly am is not just a Sissy but also a disrespectful and ungrateful man. Therefore, my place is with my lips and tongue worshiping Madam’s pussy and as Jenn has reminded me, I should always look up at Madam and maintain eye contact so I know my place.

Pussy worship is one of the cornerstones of a Madam/Sissy relationship and it’s non-negotiable. I fear that the first visit I may hesitate or refuse to worship Madam properly out of fear or habit from the past. I know this will be viewed as a sign of disrespect and insubordination and the consequences will be severe either by being forced to worship or punished. Madam, please do what it takes to break me of this disrespectful behavior or phobia.

Once a Sissy told me that he once refused to worship his Madam, so he was punished so severely that after a few minutes he literally fell off his Madam’s lap and immediately crawled up under his Madam’s dress and began worshipping her pussy. It’s safe to say that he learned his lesson.

I know that with training I will be a Sissy who will worship Madam wherever and whenever she desires and make her proud of how she has transformed this high maintenance man into a devoted Sissy

Since I know I am a pathetic and emasculated man my future is having only “sissy sex”, no more penis stimulation and only have my nipples and “sissy pussy” played with like a woman/sissy but also, I will be expected to suck Madam’s dildo. These acts reinforce Madam’s dominance over me as well remind me of my place. I am petrified about sucking Madam’s cock it will be difficult because I am a gagger and there will probably be lots of tears.

Madam’s demeanor and expectations will play the biggest part on my training, but I can’t forget that as her Sissy she owns my pussy too. We have not discussed plugging much or perhaps we have, and I have just forgotten so it’s a bit of an unknown at the moment.  Although Madam may doubt this, I cherish her and am grateful to serve for this reason I think that when she decides to stake her claim on my sissy pussy and enter me with her finger, plug or dildo it will be very significant moment in our relationship.

It probably sounds silly but for me it will be very emotional to have my legs spread like a virgin then lubed up and Madam mounting me missionary style so she can overpower me, see the look in the eyes, kiss me and have me experience what it’s like to be taken.  

All the thoughts I have had so far still leave have not addressed the one issue every Sissy I have corresponded with and learned about their experiences and that is if their Madam will expose them to others. It’s an unknown that will always be at the back of my mind and because it’s unknown it becomes a form of blackmail. As mentioned before even the thought of Madam’s neighbors hearing my punishment and cries is terrifying for me. Since Madam does not care it’s reasonable to assume she would not think twice of embarrassing me or exposing my situation to others in a public setting or even in front of one of her close friends.

I have been blessed to have been selected by Madam Jamie I will never forget how fortunate I am and soon my training will begin.  Thank you, Madam

Respectfully:

Sissy

The Teenage Years - (Chapter 1)

 

Fast forwarding now to when I was about 12 years old.

My mom sat me down to let me know that she and my dad were getting divorced and that she thought that it would be for the best for us both because of the stress he was causing me and how unhappy and unloved she had felt for many years. I was a little confused because my mom was a devout Catholic and very active in the church as well as the Catholic Women's League. I became even more confused when she went on to tell me that she would be starting to go on dates with men and hoped that I would understand.  

She then told me that as a treat she would be getting me a new bedroom suite from Sears and that my dad's office which was located next to her bedroom would now become my bedroom. she then showed me a picture of it from the Seats catalog and I must admit that it was one that I had seen quite a few times while flipping through her big stack of catalogues.

 

It was a very girlie style of canopy bed in white with matching desk and dresser. In fact, it was very similar to the one my friend Erin had. The one she purchased was very similar to the one in this photograph except that the bows and skirting were 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.

I wondered why I needed to move my room because I liked being at the other end of the house, she told me that my new room would be bigger, and I would need a bigger room now but my old bedroom would still be there for when family visited.  I learned later that she was concerned that people would think it was very odd that I had a girlie room and that my new bedroom would be our little secret.

My mother always asked how I felt about how I dressed and was treated, I never felt as if I was forced to dress like a girl or like a toddler and be treated like a baby. Now that I was 12, she said that I probably would not be able to dress like a girl in public. While I was younger, I was quite short and very slight. In the last few months, I was starting to grow and while still not much taller I was becoming heavier and to be honest a little fat.

She told me that while I still would be able to be part of the square dance and clogging club she did not think it was a good idea for me to be doing ballet after the spring classes ended in a few weeks. I remember having a bit of a temper tantrum when she told me. I loved wearing tights and leotards I liked how it felt and how it made me feel.  She persisted and she told me that it was for the best. I persisted and then she told me that she noticed that my "winkie" was erect inside my leotard at class. Winkie was what she had called my penis.

I remember getting very embarrassed by her telling me this and then having another temper tantrum. Up until this point in my life she had never told me there was something I could not have or do.  She didn't really do anything to stop me other than saying that I was acting like a baby.  I wore her down and she told me that I could still go to ballet.  

She reassured me that if I wanted, I could still dress in little girl clothing at home and if I wanted, I could wear diapers and be treated like a baby. I recall her taking me by the hand and asking me if that is what I wanted. When told her that I wanted that she gave me a big hug and called me her little baby.

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 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 led me by my hand down the hallway when she told me open my eyes I was blown away by my room. I literally let out a squeal of delight and hugged my mom thanking her over and over. The canopy bed was just like I the catalogue. There was even a diaper pail in the corner on the far wall and beside it was large changing table that was painted white to match the other furniture. 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. 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 if I was feeling better and was happy now.

I recall that she gave me a playful pat on my bum and then lifted the hem of my dress up to peek underneath. Then she told me that this was supposed to be a little toddler’s outfit and I was wearing big girl panties instead of diapers. She then told me to take off the panties and pin on a diaper and some baby pants then cover them up with my tights and rhumba panties.

I recall being very embarrassed by this, 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 into 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 I watched TV like I did most Friday nights, and it was not long before 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. Without a word she pointed to the changing table, I climbed up and laid down, 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.

Mom surprised me when she suggested to me that if I wanted to really feel like a toddler she would not be upset if I messed my diapers just like a real toddler or baby. I shook my head and told her I did not want to, and she told me that it was fine and up to me.

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 was puzzled and she told me that she did not want me ruining the new mattress if my diaper leaked during 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 erection.

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 be about when something happened that surprised me as well as begin to delve into those feelings and my adventures involving masturbation.

Early Years at School (Chapter 3)

 

With my dad now less and less in the picture the atmosphere around the house was much less tense. He was often away for weeks at a time and when he came home if was often on a Friday evening, he then would spend the weekend golfing and then on Monday morning he was away on business again.  Those were always a very tense few days and I remember my parents having many heated discussions.

This was a time 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. I would often have erections while I was dressed up and I was always touching myself when I was alone.

My frequent wetting was definitely stress induced and with no stress at home my diaper wearing was not required during the day while at home or out but when I went to school my mom still put me into a cloth diaper and plastic pants. While the novelty of teasing me at school wore off most of the boys and over time the instigators moved away, and life was not quite as horrible.

Erin and I continued to be friends in fact she really was my only true friend while I was attending Elementary School.  I really did enjoy spending time with her and doing things girls would do in terms of playing and helping around the house. I was becoming very evident that I did not relate or feel comfortable with traditional boy roles and forms of play.

It was about six months to a year into our friendship we began to occasionally have sleep overs. It was that first time I learned that Erin was also a bed wetter and wore diapers and plastic pants under her night gown. It now makes sense why she befriended be and did not ever comment about my diapers. She too was a diaper wearer. That first sleep over she told me that she was wearing diapers under her nightgown. I remember not feeling like a freak for the first time in my life.  We would have sleep overs a couple of weekends a month and it was during one I discovered from the dance outfits in Erin’s closet that she was active in ballet and square dancing. I immediately fell in love with the huge petticoats and ruffled dresses along with her tutus, leotards and tights.  She even coaxed me into wearing one not that I needed any coaxing.  The next day I asked my mom if in addition to my piano lessons I could join ballet and square dancing with Erin.

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 explained to me that 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”.

She went on to say that 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.

I nodded my head but didn’t say anything mostly because I didn’t know what to say or really how I felt. I just knew that I preferred acting and dressing like a girl.

She told me that 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.

She flat out asked me if I would  like to dress like a little girl while you are at home? Mommy does not mind at all; I would still dress like a boy at school and most of the time when we went out but there would be times that I could dress up like a little girl. She warned me that I would be teased but she would always make sure it was okay that I could be out in girl clothing.

 

I recall looking down in embarrassment but at the same time having mixed feelings relief. As I grew a little older, I started to realize that I identified with being a girl and therefore 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 and told her that I would rather be dressed and treated 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?”

She did not respond at first and then told me that if I was still having accidents at night and sometimes during the day and It made me feel better I should still be in diapers.

She told me that she would speak to the ballet school and square dance group about my wishes to be dressed like a girl rather than as a boy.                          

Looking back my mom was decades ahead of the rest of society when it came to gender identity and the openness to let our children and adults dress how they identify with themselves rather than strict gender roles.

A few weeks later my mom told me that we would be having a visit from someone who would ask me questions about how I felt about the way I dressed and wanted to act. I remember the lady as being very kind and spoke softly. She came every week or so for many weeks and then a few times a couple of other people came with her.  Many years later I learned that she was a child psychologist, and the others were researching gender identity.

Later that summer my mom told me that I would be starting ballet classes as well as would be able to join the square dance club and that I could be dressed like a girl. Looking back, I can surmise that part of the process of being accepted as a girl was the evaluation by the child psychologist.  My the time the school year arrived my hair had grown quite long being the early 1970’s hair styles were long for boys so it .  not unusual but for ballet she pulled it back into a small bun and for square dance she combed it so that it was straight.

I actually loved ballet, it was very structured and of course I loved wearing the white tights and wither a pink or black leotard. Since I was a beginner, I was with mostly younger girls and there were other boys. Initially the instructor was quite pleasant however she did not take kindly to kids who talked in class or goofed around. One day I was singled out and received a stern talking to. To my horror I wet myself in class and began to cry out of embarrassment. It only was made worse when my mom came in to speak to the instructor and she explained that I had “accidents” if I felt stress or was embarrassed.

The next Saturday my mom laid out my tights and leotard along with a thin cloth diaper and plastic pants. I had a fit and that morning I received a rare spanking from my mother, and she took me to class with a diaper on under my leotard. She reassured me that no one would notice but all the kids did, and I heard lots of giggles, snickers and heard whispers of, “he’s wearing diapers”.

I was embarrassed and by the end of class I was near tears and has wet a few times.  I was required to wear diapers often because my mom’s rule was that if I continued to wet, I would need to stay in a diaper to avoid wetting my leotard. It was literally a Catch-22 the only way for it to stop was not being diapered but the embarrassment and teasing caused me to wet out of shame, so it was a never ending problem.

The square dance youth club was like heaven for me, since it was not close to where Erin and I lived either my mother or hers would take us both there. Within a month my mom had purchased some outfits with coordinating crinolines, petti-pants, tights and shoes. I absolutely loved the feeling of the crinolines as well as how they swished when I moved. The club was primarily girls, and the few boys were there only because their sisters were also members. More often than not the girls all danced with other girls as the male partner and it was a sea of swirling dresses and rustling crinolines.

What I really loved was that I could wear thick diapers under my dress, and no one would be the wiser.  I was really starting to enjoy wearing and wetting diapers. I more importantly I felt sexual stirrings and spent considerable time touching and rubbing myself in my diapers and frilly clothing

In addition to the wonderful feeling of the square dance dresses what I loved about the dance club was that I felt accepted and was not being judged because I wanted to dress like a girl.  My mom also became acquainted  with a few of the parents and it was not long before my mom decided to accept their invitations to come attend their church. My mom was active in our Catholic church and at first she accepted their invitations out of courtesy.

Things began to really change as I reached 7^th grade and my next step was entering High School. The content and happy times with my friend Erin, the Square Dance Club and my innocence were about to change drastically.

Early Years at School (Chapter 2)

 

I continued to play sports in the hopes of winning approval from my dad, but it became a source of more tension for me and the harder I tried the worse I got. Around the house my mom was always around and acted as a buffer, but my dad was always angry about something either with my mother, his business and increasingly me and how I was disappointing him. I heard many conversations between them that my mother needed to stop with the babying and letting me dress up like a little girl. She stood her ground and told him that I was not like every other boy, no harm was being done and that in her opinion I enjoyed it. 

At the time I don’t know if I enjoyed it entirely, but I did love the attention I was receiving from my mother and I wanted to please her. For me it was an escape and it felt like I was escaping my reality and I did like the sensations of the soft fabric and ruffles of the dresses.

One particular Saturday was a horrible day. I had caused our baseball team to lose a playoff baseball game because I missed an easy catch.  After the game, my teammates made comments about “the baby not being able to catch the ball” and that “I preferred to play with girls”. I remember parents being upset and to make matters worse I peed my pants which caused players to laugh, and my dad had to come down from the stands and rather than console me I took me by the arm and marched me to the car.  During the ride home he lectured me and told me he would put an end to my bay and girlish behavior once and for all.

I started to cry, and my dad said those famous words,

“When we get home, I will give you something to cry about.”

When we arrived home my mom was not home, and my dad told me to take all my clothes off and put them in the washer. When I came back upstairs my dad was waiting for me at the top of the stairs, he took me by the arm and marched me into my bedroom. He sat on the bed and pulled me over his lap and without a word began to smack my bare bottom with his hand.  I let out a yelp because I had never been spanked before and I was shocked at how much it hurt.

I was kicking, struggling, and crying within a few smacks. I don’t remember how long the spanking was but I doubt it was more than 25 smacks, but I do remember that it hurt so much and he was done he told me to stand up and I put my hands on my bum because they were burning.

He told me that he thought I was wetting on purpose to get attention and that I probably like the feeling

of wet diapers. He was going to teach me a lesson and that I would not find them as pleasant today.  He left the room for a few minutes and when he returned, he put me over his lap again. I thought I would get spanked again but instead he spread my butt cheeks apart and I felt him push something against my bum. I struggled and clenched my bum tightly which earned me a smack. When he did that, I felt him push something inside my bum causing me to cry out struggle again.

I had no idea what he had pushed in but I could feel it get a little softer and being to move up. I tried pushing it out, but he clenched my bum cheeks together and warned me not to push it out. I recall being upset and crying but he ignored me. After a few minutes he told me to stand up and put on 2 diapers and a pair of plastic pants.  I was very confused because I thought he was mad that I wore diapers and now he was telling me to put them on. I hesitated because I had never worn 2 diapers at once and was not sure how to do it. My dad told me to lay down and he pinned on the first diaper followed by a second and then pulled up the plastic pants.

He told me that I would remain in my diapers until my mom returned home later in the afternoon and the bathroom was off limits.  He left and closed the door behind him, at first, I was not sure what I should do so I just put on some shorts and a T-shirt. I remember the bulkiness felt a little odd at first but then I started to like the feeling and especially how it filled out the plastic pants.  For the first little while I played and read in my room and then I decided I wanted to watch TV downstairs in the family room.  My dad asked if everything was all right and I told him I was fine. However, about an hour later my stomach started to rumble and feel a but uneasy and it was not long before I felt like I needed to go to the bathroom.  My mom always let me use the bathroom if I had to poo but when I got to the door my dad asked me where I was going.

I told him, he shook his head and told me that the bathroom was off limits. I started to complain, and he told me to be quiet. When I complained again, he took me by the arm and gave my bum a couple of swats. The thickness meant it di not hurt but the sound was loud. He led me to my room here he had laid out one of my footed sleepers. I was told to take my shorts and shirt off then put the sleeper on. I did as I was told and once it was on my dad zipped it up and then put some wire through the looks and twisted it tight.

He said to me know I could not remove the sleeper or my diapers and I was soon going to learn what it felt like to be a real baby.  I remember pulling on the zipper frantically and pleading with my dad to let me use the washroom like mom did. He just shook his head and left once again closing the door behind him.

 Had already wet my diapers a couple of times and I loved the feeling but now my stomach was starting to really gurgle and rumble. It was only mid afternoon, and I had no idea when mom would be home. I went looking for my dad and found him outside I the backyard I pleaded with him that I had to go poo.

He told me to hush up again and reminded me that if I wanted to act like a baby, I would be treated like one and that meant messing like a baby. I started to cry, and my dad told me to be quiet. This only made it worse, and I started crying louder so he took me by the arm and lead me to the house.  As he was taking me up the back steps, I felt horrible cramps and I filled by diaper with a large load of soft poop. I remember putting my hand behind me and feeling the back of my sleeper. My dad told me to go to my room and stay there until my mother got home.

It was a horrible feeling, I remember standing in my room with my legs spread because of the gross

feeling inside my diapers. By the time my mom got home I had pooped a couple of more times and I began to cry loudly when I heard her come home and begin talking to my dad. It was talking first but soon she was yelling at him, and she came into my room. She was exceedingly kind and reassuring, she quickly removed my messy diapers and told me to take a nice long bath to clean up.

When I got out the bath my mom asked me if I wanted to be rediapered or if I had had enough for now. I told her that I still wanted to be I was not so sure that I wanted to continue playing baseball on the team anymore.

That day was the start of many changes at home. My dad began to “travel” more again and it was not long after my parents separated.  While the stress and anxiety at home decreased things at school became worse. The saving grace was my friendship with Erin and being able to now avoid sports and do some other new activities that suited my demeanor more.  

Early Years at School (Chapter 1)

The first couple of years in elementary school was incredibly stressful for me in fact school in general was a source of considerable trauma and stress in my life. The lessons were not particularly difficult in fact I remember thinking it was so easy and wondered by others were having so much trouble with reading and arithmetic. For me socialization was incredibly awkward, and I just did not relate to the boys. At recess and lunch, I tried to fit in with them and their games, but I was inept at everything and as children can be they immediately spotted my weaknesses and being different and I quickly became the source of teasing and bullying.

At the same time my dad was travelling for business less and having him home made my special times with my mom less frequent. My dad was a typical European dad expected his son to play soccer and every other sport. At first my mom convinced him that sports might not be the best for me, but he relented and by 2^nd grade I was forced 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.

He and my mom argued constantly about why I was being diapered every evening and about why she was encouraging me to help her cook and my interest in “girl things” along with why she was letting my hair grow so long and what infuriated him the most was why I was often wearing girlish looking outfits and especially dresses.

I woke up I the middle of the night many times to the sound of them arguing about me and him insisting that I learn to a normal boy.   I was very stressed whenever my dad was home, and I began to have more and more accidents not just at night but also during the day. Stress began to manifest itself with me uncontrollably wetting myself as soon as I felt nervous or threatened. I began to have accidents at school and as you can imagine only made things worse. The teasing from the boys and some of the girls was horrible and I was being called “baby” constantly.

My mother’s solution was to diaper me during school days and if I had an accident, she would change me when I came home for lunch. This solution stopped embarrassing wet pants, but it was only a matter of time when a boy named Eric spotted my plastic pants sticking out from the back of my pants. To make it worse he was the class bully and a few days later when we were outside he knocked me to the ground, pulled down my pants to expose my diapers and plastic pants then pull my pants right off so now I was fully exposed for all to see.

After that incident school was pure hell, I pleaded with my mom not to make me go to school, but she insisted I go which lead to many morning of me faking illness or a stomach ache.  I ended up having just one friend during my first couple of years in elementary school. A girl named Erin who was sweet and would spend time with me on the school grounds at recess and lunch.  I recall being so happy when I told my mom that she had invited me over to play. I was confused when my mom showed concern and then she went over to speak with Erin’s mom who was also at the school picking her up at the end of the day.

I don’t know what she said to Erin’s mom but that weekend I had my first “play date” at her house. I will always remember that morning how my mom constantly reminded me about table manners, saying please and thank you, offering to help clean up, and every other thing a kid could possibly forget. Just before leaving she called me to my room where she had laid out my clothing. I was a little surprised that the clothing was one of the outfits she had made for me. It was similar to a little boy’s sailor suit and the shorts were baggy and had a slight bubble effect.   

When she went over to the dresser and pulled out diapers and plastic pants I objected. She persisted and told me they were necessary just in case I had an accident, and these would prevent any possible embarrassment.

She reminded me that Erin already knew I wore diapers because of the incidents at school and she had discussed my occasional wetting with Erin’s mom at school the other day.

I was very nervous when my mom dropped me off, in addition to the faint sound of the plastic pants when I walked and the bulkiness of the diaper the other thing was the distinct smell of the baby powder. My initial nervousness was for not and within a few minutes I forgot about my diapered condition. I had a great time I remember we baked cookies, played some board games in her room, etc. it was the first time in my life I had fun playing with someone else. When my mom came later in the afternoon to pick me up I pleaded with her to let us finish the game we were playing. I recall that she and Erin's mom had coffee and chatted for quite some time and when Erin and I came back into the kitchen the quickly changed subjects. 

Erin's mom said to me as we were leaving that I was welcome to come over anytime and that it was nice for Erin to have a friend who was so similar and liked the same things.

The Photo Albums

 In my early 20’s my mother accidently left behind a few small photo albums when she moved. I discovered that I had a sister who appeared to be a few years older than me.  In almost all the photos of me as a baby and toddler I was dressed like a little girl and my mother dressed my sister and I alike in matching outfits and matching frilly dresses.

The photos of my sister began to diminish when she was about 5 years old and I was 3 then there were a few photos of her looking very frail and finally a few photos of her in hospital and her headstone. 

The other albums contained photos of just me all of which I was dressed up as a small girl and always in clothing that was truly little girlish in soft pastels or white and with lots of frills and lace trim. The photos were most plentiful up until I was maybe 6 to 8, I remember her loving to take photos and at the time I did not mind as I grew older, I became more self-conscious about it and there were less and less taken.

I asked my mother about it she had a difficult time discussing her and the whole situation. It was a time of very mixed emotions for me, I learned she had passed from Leukemia. My relationship with my mother began to get strained for many reasons. I resented having this part of my life hidden from me and also in my personal life I started to move away from my sissy interests. I also began to question why I was raised like a little girl and babied. While I enjoyed it at the time and never did fight it I also began to realize that i was not a normal young man in his early 20’s. I had developed few male friendships as my interests were so different and I was not obsessed with girls and sex. At the same time, I still felt more comfortable being around women particularly older women. The younger women I knew felt comfortable around me because I was not threatening or interested in sex. However, I actually was but just was too inexperienced and fearful of how to broach the subject.  I did develop some friendships with older women is a topic for another post.

I eventually reached out to my aunt and asked her about my mom and my sister’s passing. What I discovered was that even when I was a baby my mom treated me and dressed me like a little girl. My mother had confided in her even when I was an infant that she wished I were a little girl that she had no idea how she would raise a son.

Initially my aunt thought it was a mourning phase that my mother was going through and she did not push the issue but as time passed it became a contentious issue whenever they saw each other. I recall that every time we went over to my aunt’s home or when my aunt came to visit my mom would change have me dress in more normal boy’s clothing however, I was always still diapered. My aunt would ask why I was still wearing diapers even though I was already in primary school. My mom would always tell her that I still had accidents during the day. When my aunt would ask me, I would always just meekly nod my head.

Eventually their relationship became more strained they occasionally spoke to the telephone, and I rarely saw my aunt again.