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Secrets of a shy, sensitive boy. When my pals would be playing sports after school, my unstable (or rather “eccentric”) young single mother, didn’t think anything of dressing herself and me in her clothes and makeup, to imitate her favou

Confessions of a shy, sensitive schoolboy. When suffering from acne, my stepmother at the time (a makeup artist) was more than happy to conceal my zits for me, and regardless of the daily comments on part of fellow students to the contrary, I believed

Situations of shy, sensitive boys. You know what it’s like to have an eccentric makeup artist for a mother, because you are secretly so used to seeing yourself as what all the boys supposedly find so “attractive”, that you can’t

What father never knew… When mother should have been maintaining my medication to deal with my hormone imbalance, she was rather more interested in seeing whether I fit into her old wardrobe.

Things a shy, sensitive boy can relate to.Of having grown out of your friend’s Playboy magazines, and onto your mother’s Playgirl magazines

Having a single mother who danced for a living, meant a childhood of poverty. As soon as I was “old enough” (old enough to fit into mother’s various sets of lingerie, costumes & high heels), I was learning her & her dance partner

Father always had forbidden mother from exposing me in my vulnerable boyhood years, to her world of dance and countless other feminine (& homoerotic) things she so loved. He would angrily warn her that such things would make me into a “faggot”.Father

Mother always thought it was particularly amusing, when the boys were round the house and she saw me mimicking gestures regarding the attractiveness of particular girls we went to school with.I would later come to wonder whether her insistence over the

It was gradual, stepmother always had a preference for me wearing tighter fitting clothing, and the clothing I particularly was unsure of, she concluded that I could simply wear around the house. She was the type of woman that wore heels around the house

Stepmother’s relationship with father had been on the rocks for years before they finally split. She had long done things out of spite of him, but nothing she was more proud of than what she did to me, his only son. When alone together, she had encouraged

Mother thought it was adorable seeing me do the routine with the girls. It took some getting used to, being a shy boy in a girl’s dance class, especially the sight of my delicate thin body in a leotard, propped up in very high heels, mastering effeminatel

Recollecting days in my childhood spent with my single mother. Her amusement in dressing me in her clothes, to imitate her favourite iconic actresses. The first time I was dressed in her clothes, a skinny, preteen boy, looking down at his thin legs envelo

colleeneris: Halloween Surprise by rocketXpert A thin boy early into puberty, is seldom aware that it is simply a matter of clothing, that he would be seen unmistakeably as a girl. Perhaps in the future, activists of feminine-positivity for boys,

Reminiscent of the times as a boy that I would spend across the country, with my eccentric, rich & glamorous aunt. No one at home would ever have imagined, what the small, painfully shy boy that they knew, would get up to under his aunt’s influence.

With father always having been so ashamed of me, it terrified me to imagine what he would think of me when I was alone with mother… the makeup, skirts, dresses and my first exposure to her erotic magazines of men in the nude. Join the Masochistic

It makes big difference to a young boy, not having a father around. Instead of playing sports outside, mother, a theatrical costume designer and makeup artist, enjoyed helping us effeminate boys put on elaborate reenactments of her favourite music videos.

Upon arriving back from school, mother said my halloween costume was to be a surprise and that I would have to cover my eyes whilst she dressed me. All kinds of exiting ideas ran through my mind, of superheros and warriors, so the anticipation was great.

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When the larger boys chased me home, and mother opened the door I let in a sigh of relief, knowing my tormentors would be in for it. I told her how they called me a fairy. How they said that I liked boys! Where a normal mother would defend her child

Of course father would never know when he was away for work, of the evenings out with mother, not to mention her dressing me in her clothes & makeup, and my earliest exposure to her sexualized picture books of naked muscular men.(Image above) The

That I was so adamant that I was into girls, (and not in any way boys!), mother took great pleasure in showing me photos of “hunky” men in the nude, to witness my involuntary reactions, that showed otherwise.#gay Join the Masochistic Emasculation

There was a great sense of panic when I eventually realized the place that I had accompanied stepmother and her friends to. The discomfort I felt as a young boy, when the muscular physiques emerged, dancing on stage, and there was no escape to this situat

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Many things changed when mother was granted sole custody of me and father no longer had any say in my life. Nothing epitomized this time as when I experienced my first haircut of mother’s choosing.It was quite an experience, despite mother’s dismissal

This vegan single mum swears by sperm smoothies every morning keep her healthy

Mother loved our weekend trips we went on together. Often when arriving home from school, she had my suitcase already packed for me, so it would only be when we would arrive at our hotel, that I would find that among my clothes, she packed a few articles

Mother thought it was “harmless fun”, when she dressed me in her clothes, quite reasonably dismissing father’s concerns, in that it was little more than a pair of tight pants. That in no way in meant that somehow this would result in me wearing

Reminiscent of what mother liked to do with me when father was away. As much as a boy, it would horrify me, it would be all the worse, in how I knew that over time, a part of me was coming to like wearing skirts and kissing boys. Also that mother was

When I was alone with father, there was always things he liked to do which mother would never approve of, to which she was never to know of. From the violent movies, sports and video games, to exposing me to the occasional magazine or video tape containin

In looking back, how naive I seem at that time. Having granted mother subtle, gradual clothing adjustments over time, that there I was, a boy who had come to grow his hair long, to wear high heels, lingerie…. makeup. Yet still thinking it was meani

I remember how overwhelmed and shocked into silence I was on the drive back, following the second occasion. I could no longer deny to stepmother (and myself) that I liked boys. She, of course, was overjoyed, gushing over every shameful detail that she

Father had been gone for over a year, and mother knew she was slowly winning me over. She had for a long time prior, gushed over how my figure (much to my horror), was “made for dresses”, and on many an occasion, pleaded for me to allow her to get

Like mother, like son….Mother always wanted me to take after her, rather than my father. When they split up and she gained full custody of me, I would progressively come to take after her in ways which were impossible before, and we had never been

Having split custody between my mother and father, came to be like spending time between two different worlds. For the whole of my childhood, I was used to sleeping in pajamas and my dreams being filled with thoughts about girls, but with mother, I came

As a young boy, I had long hated it, but had become resigned to indulging mother in her love for dressing me in girls clothes. When she organised for me to spend an evening out with one of her friend’s sons, she dismissed my claims that she was sending

“Mother’s glamour boy.”It is amazing to think what time can do. Where quite typical for a boy, I was so appalled by mother’s love of dressing me in her clothes when father was away, but with time, things would changeIt isn’t the only way that

One of my few early memories of my father before he left for good, was of him in a heated exchange with my mother, claiming that the way she treated me was unhealthy, that it would lead to me becoming a fairy, and my mother dismissing his worries, angrily

I made sure my mother could see my look of discontent. That while after school, I was coming to dress in the clothes she bought me, of my own free will, I didn’t want her to believe, that I was actually coming to like it. That while letting my hair

World’s apart, the time I would spend with my father or mother.There was much father didn’t know about the time I spent alone with mother. While he had me take up baseball, he never knew that mother liked to indulge in very different things with me.

When mother photographed me, as she often did after applying her makeup on me, by pulling faces and making light of the situation I found myself in, I was able to distance myself from how uncomfortable it made me, knowing not only that I was a boy in

Mother was always eccentric, but when father left, there would be a number of ways in which mother, would have to make do with less money. Ways which would make a young boy, very uncomfortable.There was a time where I had long suspected that much of the

Mother, visibly so delighted and proud. “In love” with my first boyfriend, before setting off for our first date.There was a time where understandably, for a boy, I was so disturbed by the nature of romantic desire that she always appeared to have

Father always worried that my mother provided an feminine environment that was much too inappropriate for an impressionable young boy. When mother gained full custody of me, and I would only see him every few weekends, I would wonder what he would think,

Being a thin young boy, mother delighted in that I was the same measurements as her, excitedly dressing me in her wardrobe, in increasingly elaborate manner, on the evenings father was out bowling with friends. I would come to realize when mother was

“Mother’s glamour boy”It was always mother’s favorite activity, that she secretly indulged in on the evenings father was away from home, of dressing me in her most glamorous lingerie and makeup. But nothing so delighted her on these occasions,

Very much like the deserts mother used to make for me in my younger years. It would always be firm at the center, but a little softer on the outside, but not so soft that I could bite into it. The tip was my favorite, being extremely fizzy, so I would

The evenings spent made up by mother, in her most glamorous lingerie, it does something to a boy. Finding himself in utter delirium, thinking thoughts he never imagined he would entertain. Thoughts not of girls, but of things forbidden, of unparalleled

When father left, there would be nothing that stopped mother, a woman that always wanted a daughter, finding any excuse to dress me in her clothes. Halloween was always an uncomfortable time, knowing the likelihood that I would end up in matching outfits

A mother any boy should be lucky to have.Dressing him in her clothes when his father was away, and nurturing in him a sense of curiosity about men. And the moment a mother should be proud of. With one of her “special friends”, guiding him from

When alone with mother, she was always a formidable obstacle to the vulnerable developing masculinity of my boyhood. So when father was gone, and my aunt, who was just as eccentric as mother, moved in to help raise me, I stood no chance.Within the first

Bizarre to me, mother always appeared to delight in anything effeminate that could be related to me. When father moved away, my hair grew so long, that when I finally was taken to get my haircut, I was appalled to find that I had the same style as all

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