Sexual awaking 2. The cross dressing Journey.
Cont. from Sexual Awakenings
I've always been attracted to female clothes. Even as a boy I loved looking at the women's and girls' sections in my mother's catalogues. I mostly looked at the underwear. It was exciting to see girls and women in bras and knickers. I loved slips too. They looked so smooth and silky. I also enjoyed looking at all the outerwear and shoes, etc., thinking how nice it must be to wear all those pretty things. I often dreamed about exactly that.
I lived with Mum and my sister, who is three years older than me. When I was about eleven I started to wear some of her things when home alone:- little dresses, panties and tights. At first it wasn't very often but became more regular over the next two years. I'd take her things to my room, dress, then walk around the empty house. I loved how naughty it made me feel.
Another thing I liked to do was read my sister's comics and magazines. Quite naturally, I read the stories from the perspective of the protagonists who, of course, where all female. As she got older, my sister changed from reading "Mandy" and "Judy" comics to teen 'True Romance' style magazines. Not having access to any porn, those came in handy as visual aids in my wanking sessions once I hit puberty.
Over time I realised that as well as being aroused by the images of the girls, I was identifying with them more and more. I enjoyed imagining myself in the situations in which they found themselves, especially when it involved some kind of vulnerability or submissiveness.
Even now, years later, I have a clear memory of being very aroused by an image of a girl in a comic book story standing by a window at night wearing only a baby doll nightie, made see-through by the light from a lamp. She had a gorgeous figure lovingly drawn by the artist. I wanted to have sex her but also be her – especially as anyone could have been watching – her – me – scantily clad in such a sexy garment and seen everything.
Another very clear image I retain is of a mini-skirted schoolgirl with her knickers slipping down in public. Admittedly, I’d doctored it myself. After my sister left home I spent many happy times, pen in hand, making subtle alterations to the pictures in her old comics to make them more sexual. It thrilled me to think of being a girl in that situation. How embarrassing to be in front of people with my knickers down. What an exquisite feeling of vulnerability that would be. At any moment the wind could lift my little skirt and expose my intimate parts to everyone.
More importantly, when my sister finished school and went to live with our gran, she left behind some of her clothes. Nearly everything was there, some skirts and tops, a couple of dresses, bras and knickers, nighties, a robe, tights and some shoes. No slips or stockings but, to me, it was still a treasure trove. They were hand-me-downs by default; if she hadn’t wanted me to have them, she should have taken them with her or thrown them away.
She had barely left the premises when I started to enjoy them. The first time I was alone in the house I went into her old room. I opened the top drawer and took in the sight of my lovely bras and panties. I quickly undressed. Standing naked in my sister's room, acutely conscious of what I was going to do, I was instantly erect, but paradoxically, suddenly indecisive. I was overwhelmed with the desire to wear everything. I wanted to immerse myself in sea of girly-ness.
I reached out excitedly and took the closest bra from the drawer. It was white with padded cups. I held it up by the straps and looked at it. It was just a plain white cotton bra, but to me it was adorable. I loved the way the cups held their shape, already defining a bust; the little bow where they came together, so cute and girly; and the open back band hanging loose with its hook and eye fasteners, so feminine.
I slipped my arms through the straps and checked they weren't twisted. I reached behind myself and after a bit of fumbling, I fastened my first bra in place. I pushed what little chest fat I had above the underwire and straightened the band. The feeling of the straps on my shoulders and the tightness across my torso felt wonderful. I matched the bra with a pair of white cotton knickers. It felt so nice stepping into them, drawing them up my legs, and snuggling them in place. The waistband held my hard penis against my tummy.
I looked in the wardrobe mirror. With my panty-bulge and the top half of my shaft sticking out of my knickers I was obviously a boy from the front; but viewed from the back I could have been a slim teenage girl. I've always loved the look of a bra band taut between the shoulders, and of course a lovely pair of panties stretched across the hips. I looked so sexy. I spent some time posing, sticking out my bottom and looking coquettishly over my shoulder. It was delightful. My reflection in the mirror determined my first choice of outfit.
My sister's school uniform was still hanging in the wardrobe:- a short pleated grey skirt, white blouse, and maroon cardigan. As I was looking for the most suitable pair of tights, I found some white knee length pelerine socks and immediately knew they would be even better. I couldn't resist. Her school tie was in amongst some odds and ends in a drawer and I had a pair of black loafers that would do for school shoes.
I find everything about 'dressing' has an appeal; doing up my blouse with the buttons the 'wrong' way, sliding my skirt up my legs and fastening it in place, and the feel of the hem brushing my bare thighs, all helped me slip into a female persona. Fully dressed with tie and cardigan, I stood in front of the mirror. With my erection now hidden, I mostly looked like any girl ready for school; the only issue was my hair. I spent some more time posing, viewing myself from every angle.
Of course that included from behind, whilst leaning forward, to give a glimpse of my knickers. I felt my hard penis twitch, a natural reaction to a panty-flash, even if it was my own. I sat on the bed opposite the mirror and crossed and uncrossed my legs the way I always wanted the girls in school to do, but that they rarely did. I looked, and felt, oh so sexy. I left the bedroom and walked around the house.
By then my cock was fairly throbbing. That I would wank was inevitable; the only question was could I hold off for another outfit change. The answer was no. I returned to my sister's room. I sat on the edge of the bed facing the mirror. I put my hand under my skirt and confirmed that I had leaked a copious amount of pre-cum. I stroked myself through my panties. I was so aroused I knew I would cum quickly. There would be no time for role play.
Raising my bottom off the bed I pulled my knickers over my hips and on to my thighs. Released from constraint, my cock sprang up and tented my skirt. Watching myself in the mirror, I eased my knickers down my thighs and out from under the hem of my skirt. Momentarily resting them on my knees, I allowed them to slip down my legs to pool at my close-together ankles. It all looked so sexy. I lifted my skirt and placed it behind my cock which was sticking straight up I pulled my panties back up to just below my knees, opened my legs and parted my feet. The panties stretched between my shins. The image in the mirror stirred me deeply. Just a few strokes and I was on the verge. God, no tissues! Quickly I pulled off my knickers and wrapped them around my swollen cock – just in time as it turned out. With a whole body shudder I orgasmed, spurting globs of cum into my sister's soft white panties.
I've always been attracted to female clothes. Even as a boy I loved looking at the women's and girls' sections in my mother's catalogues. I mostly looked at the underwear. It was exciting to see girls and women in bras and knickers. I loved slips too. They looked so smooth and silky. I also enjoyed looking at all the outerwear and shoes, etc., thinking how nice it must be to wear all those pretty things. I often dreamed about exactly that.
I lived with Mum and my sister, who is three years older than me. When I was about eleven I started to wear some of her things when home alone:- little dresses, panties and tights. At first it wasn't very often but became more regular over the next two years. I'd take her things to my room, dress, then walk around the empty house. I loved how naughty it made me feel.
Another thing I liked to do was read my sister's comics and magazines. Quite naturally, I read the stories from the perspective of the protagonists who, of course, where all female. As she got older, my sister changed from reading "Mandy" and "Judy" comics to teen 'True Romance' style magazines. Not having access to any porn, those came in handy as visual aids in my wanking sessions once I hit puberty.
Over time I realised that as well as being aroused by the images of the girls, I was identifying with them more and more. I enjoyed imagining myself in the situations in which they found themselves, especially when it involved some kind of vulnerability or submissiveness.
Even now, years later, I have a clear memory of being very aroused by an image of a girl in a comic book story standing by a window at night wearing only a baby doll nightie, made see-through by the light from a lamp. She had a gorgeous figure lovingly drawn by the artist. I wanted to have sex her but also be her – especially as anyone could have been watching – her – me – scantily clad in such a sexy garment and seen everything.
Another very clear image I retain is of a mini-skirted schoolgirl with her knickers slipping down in public. Admittedly, I’d doctored it myself. After my sister left home I spent many happy times, pen in hand, making subtle alterations to the pictures in her old comics to make them more sexual. It thrilled me to think of being a girl in that situation. How embarrassing to be in front of people with my knickers down. What an exquisite feeling of vulnerability that would be. At any moment the wind could lift my little skirt and expose my intimate parts to everyone.
More importantly, when my sister finished school and went to live with our gran, she left behind some of her clothes. Nearly everything was there, some skirts and tops, a couple of dresses, bras and knickers, nighties, a robe, tights and some shoes. No slips or stockings but, to me, it was still a treasure trove. They were hand-me-downs by default; if she hadn’t wanted me to have them, she should have taken them with her or thrown them away.
She had barely left the premises when I started to enjoy them. The first time I was alone in the house I went into her old room. I opened the top drawer and took in the sight of my lovely bras and panties. I quickly undressed. Standing naked in my sister's room, acutely conscious of what I was going to do, I was instantly erect, but paradoxically, suddenly indecisive. I was overwhelmed with the desire to wear everything. I wanted to immerse myself in sea of girly-ness.
I reached out excitedly and took the closest bra from the drawer. It was white with padded cups. I held it up by the straps and looked at it. It was just a plain white cotton bra, but to me it was adorable. I loved the way the cups held their shape, already defining a bust; the little bow where they came together, so cute and girly; and the open back band hanging loose with its hook and eye fasteners, so feminine.
I slipped my arms through the straps and checked they weren't twisted. I reached behind myself and after a bit of fumbling, I fastened my first bra in place. I pushed what little chest fat I had above the underwire and straightened the band. The feeling of the straps on my shoulders and the tightness across my torso felt wonderful. I matched the bra with a pair of white cotton knickers. It felt so nice stepping into them, drawing them up my legs, and snuggling them in place. The waistband held my hard penis against my tummy.
I looked in the wardrobe mirror. With my panty-bulge and the top half of my shaft sticking out of my knickers I was obviously a boy from the front; but viewed from the back I could have been a slim teenage girl. I've always loved the look of a bra band taut between the shoulders, and of course a lovely pair of panties stretched across the hips. I looked so sexy. I spent some time posing, sticking out my bottom and looking coquettishly over my shoulder. It was delightful. My reflection in the mirror determined my first choice of outfit.
My sister's school uniform was still hanging in the wardrobe:- a short pleated grey skirt, white blouse, and maroon cardigan. As I was looking for the most suitable pair of tights, I found some white knee length pelerine socks and immediately knew they would be even better. I couldn't resist. Her school tie was in amongst some odds and ends in a drawer and I had a pair of black loafers that would do for school shoes.
I find everything about 'dressing' has an appeal; doing up my blouse with the buttons the 'wrong' way, sliding my skirt up my legs and fastening it in place, and the feel of the hem brushing my bare thighs, all helped me slip into a female persona. Fully dressed with tie and cardigan, I stood in front of the mirror. With my erection now hidden, I mostly looked like any girl ready for school; the only issue was my hair. I spent some more time posing, viewing myself from every angle.
Of course that included from behind, whilst leaning forward, to give a glimpse of my knickers. I felt my hard penis twitch, a natural reaction to a panty-flash, even if it was my own. I sat on the bed opposite the mirror and crossed and uncrossed my legs the way I always wanted the girls in school to do, but that they rarely did. I looked, and felt, oh so sexy. I left the bedroom and walked around the house.
By then my cock was fairly throbbing. That I would wank was inevitable; the only question was could I hold off for another outfit change. The answer was no. I returned to my sister's room. I sat on the edge of the bed facing the mirror. I put my hand under my skirt and confirmed that I had leaked a copious amount of pre-cum. I stroked myself through my panties. I was so aroused I knew I would cum quickly. There would be no time for role play.
Raising my bottom off the bed I pulled my knickers over my hips and on to my thighs. Released from constraint, my cock sprang up and tented my skirt. Watching myself in the mirror, I eased my knickers down my thighs and out from under the hem of my skirt. Momentarily resting them on my knees, I allowed them to slip down my legs to pool at my close-together ankles. It all looked so sexy. I lifted my skirt and placed it behind my cock which was sticking straight up I pulled my panties back up to just below my knees, opened my legs and parted my feet. The panties stretched between my shins. The image in the mirror stirred me deeply. Just a few strokes and I was on the verge. God, no tissues! Quickly I pulled off my knickers and wrapped them around my swollen cock – just in time as it turned out. With a whole body shudder I orgasmed, spurting globs of cum into my sister's soft white panties.
8 years ago
