Formative Development of My Sexual Self

 

My recent correspondence with others has lead to a number of the men I am sharing my life story with has lead to questions about my status as either a sissy or cuckolded man while married.

Although previous blog posts I have talked briefly about my experience spying on my mother having sex as well my disastrous attempts at dating I thought I would expand on my feelings as well as when I went for therapy in later years what impressions I was given by the therapists.

I knew nothing about sex at the time, I was about as naïve as a 10 year old when it came to sex I hadn’t even seen a Playboy or Penthouse magazine at that point in my life. I didn’t have male friends growing up and learned about the basics of sex like most guys did by talking and hearing about their time exploring sexual feelings with girls our age. Instead I was almost an adult and now I was learning about sex and to make it more unusual it was from frank discussions with my mother, spying on her having sex and then with my first sexual relationship with Dr. Allen.

That period from 18 to 20 year of age had a huge effect and lasting on my sexuality, how I viewed sex and how I saw myself in sexual relationships. I was now an adult and my mother was very open with me about sexuality and my identity. She was very reassuring and  encouraged me to be open with her. She even arranged for me to see a therapist who dealt with gender identification issues. The therapist did not feel that I was transgendered but rather someone who enjoyed crossdressing with a desire to regress. I remember the therapist explaining to me that being a TV or CD did not mean that I was gay or even bisexual it was a fetish towards women’s clothing.  

I did some research at college but everything was very clinical and did very little to help me understand if what I was feeling was normal or not. What I did know was that I definitely leaned towards enjoying the female or effeminate side of sexual relations rather than the male.

The timing of this partial awakening coincided with my mother beginning to date a pastor from our church and for the first time in years there was a male influence in my life. My parents were not affectionate towards each other but Pastor Eric was extremely affectionate with my mother when he came over on weekends and one or two evenings a week. They were constantly holding hands, he would whisper into her ear and she would giggle or blush. When they were side by side he would often squeeze her bottom when he thought I was not looking and other times when I was I the other room I could hear him give my mom’s bum a sharp slap and she would playfully say something. Even when they watched TV or just sat on the sofa together they were always side by side and his hand was on her thigh and sometimes I spotted it up higher and inching under the hem of her dress. Mom would playfully push his hand away but I still noticed it and shortly after she would tell me that it was time for bed.

At first I hated going to bed but soon I didn’t mind because when she sent me to bed it meant they wanted privacy to make out which lead to sex which I always listened to from my bedroom next to hers and increasingly would watch through the partially open bedroom door.

The very first time I watched them having sex from the dark hallway I was caught and that lead to a very embarassing and frank discussion about sex from my mother. It was not a clinical discussion but rather about how couples enjoy sex and some of the things they enjoy which are all part of a relationship.

I was fascinated by their interaction together, he had a strong influential demeanor and my mother seemed to be so happy in his presence. I often fantasized about being treated that way by a man rather than being a man and treating a woman like that.

We had many very frank and open discussions about sex and male/female relationships. It was a very stressful time for me because I started to realize that I was different than other men but I was terrified to tell her  because I feared what she would think. One evening she asked me to come to her bedroom and she asked me since I did not think about girls if I thought about being with a man. I immediately blushed and shook my head but she persisted and I broke down in tears and told her that I thought of myself as being a girl not just dressing like one but also in other ways.

She was very reassuring and told me that she figured that might be the case years ago because I never objected to dressing in the frilliest of girl’s clothing plus I really took to doing domestic chores that women traditionally did. She brought up me watching her with Pastor Eric and gently asked if I liked what he was doing with her. Being naïve  I thought she meant about him kissing her, holding her hand and other things and told her that I did. She asked about what she saw them doing in bed that one evening and I blushed even more. I said I did and imagined myself being the woman.

I was pretty upset by this all and she told me everything was fine and she explained homosexuality and bisexuality to me. She reassured me that she was not upset and that she would help me learn about how to please a man because before I knew it I would possibly meet a man. She explained to me that I was quite effeminate and what people call a “sissy”. I loved doing the traditional female chores and roles within the house. I loved cooking, cleaning, going grocery shopping and I even loved to tag along with my mother when she went shopping for clothing. All things a normal 18 year old boy would enjoy.

This was the early 1980’s and there was minimal openness towards crossdressing, transvestitism but certainly not homosexuality and fetishes in general. I remember feeling very relieved  when she explained to me that men can also take the role of being a “wife” in a relationship with other men, I told her that I liked that idea of dressing and being like a wife to an older man. She vaguely talked to me about what being a “wife” or sissy entailed and that it would be difficult to find such a relationship.

I know it sounds bizarre and creepy but I was fascinated by the sounds of them having sex. You would have thought that the fact I was caught spying on them would end my voyeuristic desires but it had the opposite effect. Since my bedroom door was open and our home was quite small I could hear them chatting and giggling in the living room. It was not long before the chatting stopped and I could hear soft moans and the sound of kissing. Soon after I could hear them go into my mom’s room and the sounds were much louder. They always had sex with the bedside lamp on and the door partially open. When I started to hear the bed squeak and the headboard banging against the wall I would sneak out of my room and peek into their room from the dark hallway. The way the bed was situated in relation to the door made it that I was slightly behind the, so they could not easily see me.

They almost always had sex doggie style and Pastor Eric would make love to her very aggressively. He would grab her bum, her breasts and sometimes her hair as he made love to her. He would tell her what to do and physically flip her over to change positions. I found this so exciting especially when she was on he back and he would kiss her as he pumped his cock into her.

Oral sex confused me and frightened me again he was always quite aggressive and almost demanding. He would hold her head as she sucked him and often it looked like she was making love to her mouth.

About a year later when I just turned 20 I had my first sexual contact with a man. To say I was frightened that first night would be a huge understatement but I knew I was ready and I desperately wanted to experience being the “woman”. Looking back I was so fortunate that Dr. Allen (or Uncle Allen which he preferred to be called) was kind yet forceful. His demeanor with me was so similar to Pastor Eric’s with my mother that I could feel myself drifting into a totally different headspace very quickly. He was very kind, soft spoken and caring however if I misbehaved he was like a very strict daddy. Sexually he was assertive and did not take kindly if I hesitated or shook my head and said “no”.

The first time he held me, slid his hand up my leg and under the dress I was wearing I remember at first tensing and pushing his hand away tentatively but he persisted and gave me a warning look. He held me, cuddled me and I remember feeling very relaxed in his arms. When it was time he took me to his bed and undressed as I sat on the bed. Without a word he took my head between his hands and pushed his cock between my lips. I started to do what I saw my mom do to Pastor Eric but I clearly was terrible at it. My teeth raked across his cock a few times which angered him and he pulled out of my mouth and gruffly told me to lick and suck his penis as if it were an ice cream cone on a hot summer’s day.

I immediately loved the taste of his penis and I really liked the soft skin of the head. IT was not long before something happened that I was completely unprepared for, without warning he pushed his penis into my mouth and it filled with his cum. I was mortified and frightened as he filled my mouth. I never had seen Pastor Eric cum in my mom’s mouth and I started to pull away. Uncle Allen firmly told me to swallow everything and any that leaked out he wiped with his fingers and put in my mouth.

While I was initially revolted by this sexual act he was so reassuring after, he held me, stroked my head and then gave me my first passionate kiss. His tongue explored my mouth and I felt so girlish for the first time. I let out a soft moan and again felt limp and safe in his arms.

Later that evening me made love to me for the first time in a manner that I had witnessed with Pastor Eric and my mother. I flinched when he inserted his lubed fingers as I kneeled with my bum high I the air and my chest against the mattress. I could not imagine receiving his cock and without warning I could feel him pressing it against my “sissy pussy”. Like any virgin I let out a gasp when he slowly pushed inside me and after a few minutes to allow my sphincter muscles to relax he started to make move to me. Yes it hurt initially but soon it did not. I felt like I was in my sexual place having a man inside me. I loved the thrusts of his hips, his thighs and balls slapping against my bum and especially his weight against me. I remember my male persona drifted away as I closed my eyes and experienced what it must feel like to be a woman. This orgasm inside me felt lovely, he held me and kept his penis inside me while it softened and soon there was the feeling of his cum dripping out of me as we cuddled in bed.

After that day I knew that what I had been feeling as a teenager was indeed true and that I was happiest as a submissive sissy in the care of an older man.

The Next Step - Meeting a Man (Part 1)

I was 20 years old, working after graduation and earning decent money but I still was living at home and had no real desire to move out. Wile no longer close to being passable as a girl I was still dressing at home every evening and weekend.

We had moved back to our home in North Vancouver, my mom and I were still attending the “Mission Traditional Christian Family Church” and she seemed to have a steady stream of men that she was dating and bringing home all of whom she met at the church.

I had started to try to date some girls hat I met in my final year at university but being much younger than them proved to be problematic. In the romance department I was a disaster and I really was not into being the sexual aggressor. By chance I stumbled upon a newspaper at the local magazine store on Lonsdale Ave called the “Vancouver Star Weekly”, it had articles but it’s primary function was for sexually oriented ads focused towards various kinks and fetishes. I bought it religiously for months and loved reading the ads and was amazed at all the different fetishes people had. I hid them in my closet and for the longest time thought my secret stash was indeed secret only to find out later that my mother had found my pile long ago.

By this time in my life I was fantasizing more about men than girls, but I was still unsure of where I was leaning. I loved feminine clothing and dreamed about being touched, kissed and the fact that almost every weekend I could hear my mother having sex I often dreamed about being in her place.

I will never forget it was in early September an ad appeared that basically stated;

“Older, professionally employed widower seeks an effeminate acting younger male under the age of 25. Prefer him to be respectful, shy, soft spoken, enjoy cooking become my house boi and dress like a young girl.”

I was stunned because that sounded like me, but I did not have the guts to answer the ad. The ad appeared for weeks but I just didn’t have the courage until one day my mom approached me holding the newspaper opened to the page with the ad that I had circled. I was mortified but my mom was not angry at all she asked if I had answered the ad I shook my head and when she asked if I wanted to I slowly nodded.

She sat with me and reassured me that part of my love of being a girl also has developed in wanting to be treated like one by a man. I was confused because my Catholic upbringing was dead against homosexuality and at the MTCFC it was so family oriented. After dinner she sat with me and helped me write a response to the ad.

About a week later I received a long letter from a gentleman; he was in his early 60’s, lived alone in West Vancouver, was a semi-retired doctor and he said he was very excited to meet me and that I was the only response he received that he would even consider meeting. His name was Dr. Allen and I was always expected to call him either Dr. Allen or Uncle Allen. He provided me with his telephone number and to call at precisely 9pm on weekdays.

It took me a few days to get the courage to call and I was unbelievably nervous and very timid when I did call. Thankfully he was talkative, was not intimidating and made me feel comfortable. There was no discussion about my desire to be a sissy maid or sex instead he asked me if I would like to go to a Vancouver Canucks game on Friday evening.

He picked me up a couple evenings later at my house and I think he was taken aback when my mother answered the door against my objections. I will never forget my face getting beet red when she invited him inside and reassured him that she knew about his ad and she had no concerns.  Dr. Allen was tall, heavy set, had a friendly face and looked about his age. I can’t say that I felt an attraction towards him, but he was a good-looking man who probably got lots of attention from older women.

That first weekend I went to the hockey game with him on Friday evening on Saturday he took me to the horse races both of which I had never experienced growing up and I was completely at ease with him asking questions about the two sports and talking about my job. When he dropped me off at home on Saturday he invited me to attend the ballet on Sunday afternoon followed by an early dinner at his favorite restaurant.

My mom insisted I wear a suit which I resisted but she relented, and I am glad I did because during dinner Dr. Allen told me that he was very impressed that I chose to wear a suit and that he puts a lot of importance on how a person dresses as well as their table manners at a fancy restaurant. The restaurant was indeed a very formal French restaurant with numerous courses. The meal took hours and we were seated in a quiet booth. This was the first time he asked about my teenage years and love of being dressed like a girl. I was completely embarrassed and when he asked me if I ever fantasized about being with a man my face went red. Before I could even answer he asked if I had ever sucked a man’s cock at the same time he slid his hand onto my thigh.

I shook my head and jumped all at the same time. He went on to explain quietly that he would love it if I would be his sissy maid and stay on weekends.  He told me that I would be expected to do the grocery shopping on Saturday mornings while he saw patients at the hospital then I would be cleaning and cooking for the remained of the day. We talked about the foods he enjoyed and what I liked to cook, it was obvious that he had very high expectations and I would not be cooking easy or simple meals. In return I could wear pretty dresses like I wore growing up and he wanted me to wear French Maid uniforms while doing chores.

I nodded my head and told him I really wanted to be a Sissy Maid. It hit me at that point that I would have to tell my mother because now I would not be home on weekends. I started to have second thoughts, but he reassured me that my mom would be happy for me. He confided that my mother had sent him a separate letter when I wrote him and in it she shared my upbringing with him and they even had spoken on the telephone. I learned later that he was a member of the same golf club as my dad and he had my mother had met at before at club social functions.

Looking back....My Relationship with my Mother

Being a normal teenager is a trying time but in my case it was far more complicated because I was being raised like a girl under the watchful eye of a very strict mother with high moral values.  She was a devote catholic but in my ways she had belief's more in keeping with some Christian Fundamental beliefs. She was very active in a Catholic Women's Group and often hosted meetings at our home.  I often heard her lecture at this 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.

By this time my parent's marriage was falling apart for many reasons including my dressing as a girl but more so because of her beliefs and his desire to become more successful. The last week my father was in the house was very tense with lots of arguing between my parents and then one day I came home from school and my mother informed me that my dad was gone for good.  At the time I was very upset that he left without saying good-bye to me, however I had never felt close to my dad for obvious reasons. Those first few months were difficult however if anything his deciding to leave for good made me feel closer to my mother rather than resenting her for breaking up our family which never really was much of a family.

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.

I have been asked if I fought or resented the way I was raised or treated by my mother growing up and I actually did not I did have more difficulties in my twenties when I met the woman I married and my mother was not supportive of my decision.

In my teens I had no friends my own other than some of the girls in the dance groups I belonged to and through the new church, it turned out that my mother learned about this church from some of the mothers of girls in the “Clogging Dance Group” who were always very supportive of having me as part of the group even though I was a boy in an entirely girl group. I also felt much more comfortable being around girls and especially younger ones and it had nothing to do with sexual attraction.

This being the mid 1970’s when long hair was in fashion for boys plus I was very slight at that age I actually did have features that made me look quite girlish. As I entered puberty my love of frilly dresses, satin panties, pantyhose and tights and diapers grew more and more.

My mother’s opinion on masturbation remained the same and was the reason for most of my discipline as a teenager. She went so far as to purchase a baby monitor and hid it under the skirting of my bed. It was many months of her barging in while I was masturbating in bed at night even though I thought I was being very quiet before I discovered her surveillance method. Once found she just placed it in plain sight on the night table because if I shut it off her receiver notified her.

As I got older the sexual connection to feminine attire and diapers grew and while I tried to hide it from my mother I am certain she was aware because there were many times she saw that my penis was erect inside my panties, or when she changes my diaper, the worst was when I would spontaneously become aroused while wearing a leotard at dance class. Later in my teens she had a very frank talk with me about “The Birds and the Bees” that was more involved than just reproductive sex.

My mother put a huge emphasis on my education and was always pushing the school to allow me to work at a higher level. While smart I my social skills were limited, being small and having longer than normal didn’t help so I was often teased and bullied. It came to a head early in high school when one day in the cafeteria some older boys snuck behind me and pulled my pants down in the process I fell over and they pulled them off me completely. I was wearing pink panties that day so you can only imagine the humiliation I felt.

My mother was very supportive and understanding she removed me from public school and gave me the choice of going to private school or to be home schooled. She sat me down and told me that she was very sorry about what had happened. I was never required to wear panties to school but I did so by my own choice. She told me that if I wanted I could choose to give up my feminine clothing and ways. Even after this incident I did not want to. Yes, there was a sexual component that it was enjoyable but what it really was was that I felt at home and comfortable in feminine clothing and activities. This seemed to make my mom very happy and she really spoiled me for quite a while.

She was very strict her expectations were very high in everything from my school marks, chores I did around the house, how I acted towards her and especially how I responded. Even the slightest slip up or sign of disrespect and I would either be lectured, spanked and her other old-fashioned punishment was having my mouth washed out with soap. Her strictness and the severity of her spankings were balanced by her tenderness especially after I had been punished. She would often hold me close, cuddle me and stroke my hair while consoling me.

Once day I will always remember was after I had been spanked and she was cuddling me she slipped the nipple of a baby bottle between my lips which surprised me I immediately pushed it out of my mouth with my tongue but she encouraged me to suckle because it would feel better. I remember the taste of warm milk with honey filling my mouth and it really did feel very soothing.

Through my teenage years I had wonderful times with my mom as she taught me how to do all the things mothers traditionally taught daughters. I learned how to do laundry, ironing, properly fold clothing, change bedding, she even taught me how to sew and I actually became quite good at it. Household chores were always left for me to do and the one domestic duty I adored was cooking. I would watch all the various cooking shows on TV and the favorite books I checked out of the library were cookbooks. Mom and I even attended cooking classes together at a local gourmet shop which I loved. One of my favorite ways to spend a weekend afternoon was to cook and serve a fancy dinner for my mom. She would always want it to be very formal with candlelight and we would both dress up.

As I grew older she would teasingly say,  “You will make a very good wife one day.”

The new church became a very important part of our lives, at the start of the next school year it was decided that I would a traditional Christian school near Abbotsford and it would be supplemented with home schooling from some church elders and teachers associated with this religious group. Home schooling was very common within this church and parents were encouraged to accelerate their children’s studies.

At this time mom moved us to the town Mission and our social lives revolved around the church. My mom was very forthcoming and everyone in the congregation was made aware that I was actually male but by my own choosing wanted to be raised as a girl. The church elders had no issues and I was expected to attend lessons and services designed for the girls as well as for the boys. A few parents were initially apprehensive and I recall a few evenings parents would come to our home along with church elders for an open discussion about my circumstances. Initially these mortified me but mom as so reassuring, and she’d ask me to bake cookies and serve coffee or tea for our guests. I enjoyed this part but a t first I was terrified of having to dress in a very fancy dress. Mom favored (and so did I) dresses that were white or pale pink with lots of lace and ruffles along with white tights and black Mary-Jane shoes. I will never forget how proud I felt when a few of the ladies said they wished their daughters were so willing to dress and act like prim and proper young ladies. 

 

This was a style of dress I wore often complete with tights, ruffled socks and black patent leather shoes.

I ended up finishing high school 2 years early and immediately entering university before my 16^th birthday. My mother was very supportive yet on the other hand she was extremely protective of me during my first year at university. I loved school the mental aspect of school but socially I was even more out of touch than during high school. Being socially inexperienced in high school was traumatic enough but now going to university and having very limited social skills drove me deeper into my cocoon of being a sissy where I felt safe and secure.

There definitely was some growing interest in girls at this point but now I was a boy among young women and this made me even more insecure. My mother drove me to school each morning and would pick me up each evening which I loved, the only times I felt secure was with my head buried in my books or in the company of my mother.

At the same time I really found comfort in being diapered each evening and during the weekends. I didn’t have the traditional university escapes available to me like socializing, partying and drinking for me the escape was regressing into that comfort zone.

When I was 18 entering my third year at University I was really beginning to experience sexual awakening and confusion. While I felt a sexual attraction to women I was confused because that attraction was very much a fetish type feeling towards the clothing they and for that matter what I wore and I had had an attraction to mature, full figured women not the young, skinny girls that I saw at school. The flipside to those feelings was that I had a stronger yearning to be in the company of older men and my fantasies almost always involved me being dressed very femininely and being the nonassertive participant wither with older women and more and more with older men.

Growing up my father was not around for the dreaded “talk” about sex and now at age 18 my naivety and confusion were difficult to understand during this pre-internet time and books in the libraries on the topic were very dry and clinical in nature. At this exact time of my awakening and confusion my mom had begun to date one of the pastors in the church who recently lost his wife to cancer. When my parents were still together there was never any outward signs of intimacy to each other and I never hard them in their bedroom. Now all of a sudden there was this man coming to our home and I was constantly seeing him hold my mom’s hand or they cuddled on the sofa.

While not my mother this was exactly what I saw. The woman is of very similar body type as my mother at the time.

 

Unbelievably I was so naïve at age 18 that I had no idea what was the first time I was awakened in my room to the sound of my mother’s bed, which shared a common wall with my room in our small house, banging against the wall, the bedsprings squeaking loudly and the sound of my mother moaning. I actually got out of bed went to my mother’s bedroom door opened it and stood there in shock at the sight of my naked mother on all fours and Pastor Eric thrusting his penis into my mother over and over. 

I will never forget that sight and me standing there in a nightgown and night diapers underneath and immediately getting an erection. What happened after Pastor Eric noticed me standing there was much worse. Both he and  my mom screamed out in shock and I dashed to my room. A little while later my mom came to my room and sat with me to explain the “facts of life” and to my embarrassment what they were doing and how couples show their affection by “making love”.

My mother was very open with me about sex and she told me that since I was 18 I should know more than the basics than “where babies come from”. She not only talked to me about how men should show their affection towards women but also how to please a man. I remember being totally shocked when she told me about how men love to have women take their penis’ in their mouths.

Mom continued to see Pastor Eric for quite some time and they had sex often, I would lay in my bed listening to them and I started to make a habit of peeking through their partially opened bedroom door watching them I bed. It was then that I was becoming very aware that I was fantasizing men’s cocks  and about being the “woman” not the aggressor male.

One of the most embarrassing conversations I ever had was when I finished University and one day my mom asked me if I had ever been with a girl. She obviously knew the answer because I rarely went out. I remember being mortified when she asked me if I thought about them and I did not answer. She looked at me and asked me point blank if I fantasized about being a girl and being intimate with men. I got beet red, nodded by head and started to cry. She was very reassuring and told me that often young men and women don’t know what their preferences were and they explored bisexuality.

Shortly starting my career I ended up having my first relationship with an older man that lasted almost 2 years and I was his sissy. This is a large chapter of my life of and was completely supportive. During this period it was the first time I was away from my mother for the first time but now I was under the guidance of quite a strict older man. Interesting that in many ways was a male version of my mother.

After he retired and moved South I started to have my first encounters with women which for the most part did not go well. My mother was not very welcoming to girls in my life and she was often cool towards them. It was then that I started to develop some resentment towards her and her meddling into my personal life.

Eventually I met the woman I married and even to this day my mother was cool towards her but she would never say why.  By my late 20’s I had severed most of my relationship with my mother especially when she moved to Vancouver Island. I did seek counselling to help deal with my feelings towards her and it took many different counsellors to help me come to grips with my relationship and upbringing. I always suspected by mother had some mental health issues stemming from the loss of an infant daughter before I was born had I became a replacement for that daughter. I loved being a sissy girl growing up and I still do, for me it’s an escape from reality and the pressures of life.

My mother and I had limited contact for 20+ years and only in the last 5 or so as she developed dementia did we reconnect mostly out of my feeling of duty to assist her during this disease. Only in the past couple years when I was In the process of selling her home and all it’s contents did I have regular contact with her again.

 

 

 

 

Moving Forward

A few followers have asked me to move forward a few years to enter the period of my life when major changes started to occur.

I will now post more regularly albeit the posts will be shorter.

Lesson Learned

For the next week if I was not at school, doing chores, studying or attending dance classes I was writing  the scripture over and over. Each evening my mom reviewed my work and  in the morning the pages were on the breakfast table with the total of passages she accepted as being properly spelled and neat enough.

I whined and complained which she ignored initially but by the end of the week I went to far and earned my first ever mouth washing with soap an experience I will never forget.

Saturday began like every other with the morning spent at square dance/clogging lessons which I loved. It was primarily girls who were all very nice, my long blond hair which my mom always styled in a girlish fashion, my thin features and soft voice and she demeanor did not hide the fact that I was actually a boy they accepted me and did treat me like one of the girls. I will save these details for an upcoming blog post.

I had a particular love of the square dance dresses and skirts we wore with big puffy crinolines and especially the rhumba pants we wore under it all. My mom had many different styles and colors for me and my favorite were definitely the style with the longer leg. To top it off the Mary Jane style shoes made me feel even more girlish. While the other girls generally did not wear pantyhose during practice my mom always insisted I did because she told me it looked more feminine.

When we returned home from class that day mom immediately came into my room carrying a large bag of disposable diapers and began placing them into the same dresser drawer that held the cloth diapers. I asked why she had disposables and with an angry voice which caught me by surprise she said,

“Because I you I really don’t feel like washing dirty cloth diapers until I find a diaper service who supplies adult cloth diapers.”

            “What!”, I screamed

This was the first time I saw her so angry, she turned around holding a disposable diaper I none hand and plastic pants in the other,

“I will not put up with your masturbation, I know you have still been sinning this week even after confession therefore my solution will be simple. Diapers give you joy therefore the solution is to make them a little less comfortable and fun. From now on bathroom privileges have been suspended except for bathing and brushing your teeth.”

I screamed at her,

            “You can’t be serious there is no way I’m going to shit my pants.”

Swearing was another sin in her eyes and without a word she gave me a hard slap across the face. The shock was worse than the pain and in the next instant she took me by the arm with the other she pulled down the rhumba pants, pantyhose and cotton panties and whacked my bare bottom 3 or 4 times.

            “You’ll be going to confession again young man.”

Once the disposable diaper was taped on she pinned on a thinner cloth diaper over top followed by a pair of white plastic pants. As she left my room she told me to put on my proper blue dress shorts proper shorts and a white short sleeved dress shirt because we had errands to run and the church for her Catholic Women’s League meeting.

A few hours of tagging along with my mother dropping off dry cleaning, going to clothing stores, a quick lunch at White Spot and the big weekly grocery shopping at the then Woodward’s Food Floor and the disposable diaper was becoming more and more uncomfortable. The paper liner was sticking to my skin which was damp with perspiration and I was becoming very aware that people were noticing the loud swishing sound of the plastic pants and plastic covering on the disposable.

Mom ignored my pleas to go home and by the time we were standing in line at the checkout I soaked my diaper. Mom noticed and quietly whispered,

            “Do you feel better now?”

I just nodded and looked at my feet.

We dropped the groceries off at home before heading to church mom checked my diaper and apologized that she did not have to change me before her meeting. We arrived while confession was still going on and I sat in the pews nervously waiting for my turn. I confessed to swearing at my mother and the priest asked me why I swore. I lied to him because I certainly was not going to tell him the truth. I did my penance and waited in the back pew for my mom to finish her meeting.

As it neared 5pm my stomach began to slip and turn which for me were the signs of a bowel movement. For 15 minutes everything was fine but the urge was getting stronger and to make matters worse it felt like diarrhea. Mom was still in the basement meeting room when it struck me that I could go to the washroom remove the diaper do my business and she would not be the wiser.

I had just started to go towards the hallway where the bathrooms were when I heard my mom’s stern voice.

            “Where do you think you are going?”

I told her to get a drink but from the stressed look on my face and my near run she doubted me.

            “Do you have to make a “stinky” sweetie?”

All I could muster was a weak,

            “Please mom I really need to go.”

            “Okay Stevie let’s take you home then.”

I made a dash for the car but she took her time and even stopped to chat with a few ladies outside the main doors. The drive home was only a few minutes but she hit every light and then to she drove right past our street.

I screamed,

            “Where are you going?”

“I’ve decided I’d like some wine with dinner tonight so we are going to the liquor store near the mall and while we are there let’s go to the bakery and get a nice cake for dessert.”

No amount of pleading would change her mind and I was now squirming in my seat. I actually began to cry as she pulled into the parking lot but she ignored me. It was a busy Saturday afternoon and we parked a long distance from the liquor store. She took me by the hand as we walked between the cars and whispered to me,

            “Have you learned your lesson about masturbating in your diapers?”

I nodded  but she just kept on walking briskly. I felt my stomach turn again and I stopped in my tracks I let out a cry, squatted slightly and my bowels emptied in my diaper. Mom could hear the farts and I began to cry.

 

            Without a word she took me back to the car retrieved a large changing pad and placed it on the passenger seat in case I leaked and told me to sit down. The feeling was horrible as my weight squished the poop over my bum. The smell was horrible but mom said nothing as we drove home and she pulled into the garage.

“Let’s get you into the tub and all cleaned up. Don’t worry you’ll eventually get used to it if you continue to defy the Lord and my rules about no masturbating”

Caught by Mom

Perhaps it was that my hormones were starting to come to life or the clothing I was now wearing had struck a chord with me but now in addition to feeling more comfortable as a sissy I was almost always in a constant state of arousal. As soon as the soft touch of satin panties or other clothing touched me especially my penis I immediately became aroused. My greatest fear was my mother discovering me erect or worse masturbating which I did often. I would tell my mom I loved my new room so much I wanted to spend more time there when in actual fact what I wanted was to play with myself.

Weekdays after school and in the evenings were always filled with dance lessons either ballet, square dance or Appalachian clogging. I really loved the square dancing and Appalachian clogging because it was fun, the dresses were frilly and most importantly the girls were very friendly. Here's a video clip  of the clogging style and dresses:

 

 

 My days were so busy either I had to immediately do my homework followed by dance or vice versa. Thankfully mom took me to lessons almost 50 km from home to avoid attending classes with girls from my school it meant that lots of time driving. As soon as I got into my tights and leotard I would get aroused which was embarrassing thankfully the initial arousal subsided.

It was later in the evening, during bedtime and on weekends when I would have plenty of opportunity to play with myself and could cum to my heart’s desire in my diapers without detection. What I discovered very quickly was that wearing diapers and plastic pants gave me the greatest arousal and if they were wet it was even better. By now I was no longer occasionally wetting by accident instead if I woke up in the middle of the need with the urge to pee I would purposely soak my diapers then savor the feeling by rubbing my penis through the plastic pants and cloth diapers until I fell back asleep.

Every  morning  I would slide my pillow down and lay on it facedown and rub myself and “hump” against it until I would cum again into my diapers. My self-gratification didn’t go unnoticed though because I had not noticed that my enthusiastic masturbation and humping caused the plastic sheet on the mattress to make a loud swishing sound and the bedframe has pushed against the wall and was now banging against the wall.

One Sunday morning my newly discovered fun was exposed much to my horror and humiliation. I was humping away when suddenly my mom shrieked,

            “What on earth are you doing?”

I looked up and standing in the doorway with her hands on her hips was my mother. In her right hand she held her favorite spanking implement the dreaded wooden spoon. She marched in grabbed me by the arm and pulled me up to my feet. It was summer and I was wearing a cotton baby doll nightie and the cotton briefs that were covering my plastic baby pants were down around my ankles causing me to lose my balance and fall to the floor.

Mom was angry and screamed at me,

“You little sinner you know from church that masturbation is a very serious sin! You will be going to confession this morning and I’m sure the penance Father Nicholas will give you will be nothing compared to mine.”

My mom was a devoted Catholic and required me to attend church with her every Sunday and now I would have to face the humiliation of telling Father Nicolas about my masturbating. Mom gave my arm a jerk and within a few seconds she had me over her knee and had my diapers pulled down. Mom believes in spanking but thankfully they are short but painful. She gave me 5 or 6 sharp smacks with the wooden spoon which made me yelp in pain and rub my bare bum.

“Get showered  and I will have your clothes ready for church after confession we are going to have a little chat”.

Confessing to masturbating was the most embarrassing thing I had ever done, mom was clearly angry after church and she did not stop to chat with her friends while I had to stand beside her and listen to church lady chatter. No sooner did we exit the church did she take me by the elbow and march me straight to the car. We weren’t even out of the parking lot before she began lecturing me how disappointed she was in me and how she was mortified that she had raised what she called a “sex fiend”. Thankfully the drive home was less than 15 minutes but she ranted the entire time and grew more angry by the minute.

Once inside the house she gave me a swat on the bum and told me to go to her room and wait for her. When she arrived she was decidedly calmer and she asked me why I masturbated. At first I just shrugged but she pressed me for an explanation over and over until I was in tears and blurted out,

            “I like the feeling of wearing diapers and it makes me feel good.”

This started her on a lecture about giving into desires for enjoyment even though they are evil which went on and on. She then informed me that I was not in diapers to give me enjoyment but because I could not keep my bed dry. She informed me that she would make sure I did not enjoy wearing diapers as much from now on. I would find out later that day what she meant by that remark.

My mom punished me by making me write a passage of scripture 1000 times that dealt with the evils of masturbation. To this day I still remember it:

Corinthians 6:18 “Flee from sexual immorality. All other sins a man commits are outside his body, but he who sins sexually sins against his own body.”

I spent my entire Sunday writing this short piece of scripture, by dinner time I had only done it a few hundred times. I was required to write my lines after school once my homework and dance classes were completed. It took days and when she reviewed my penmanship once I was finished any lines that were too messy had to be repeated.

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.