Cross dressing journey
- 4 years ago
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Sexual Awaking 2. The Cross Dressing Journey. free porn video
Cont. from Sexual Awakenings
And then, there were my sister’s clothes. I’d always had an attraction for female clothes. Even as a boy I loved looking at the women’s and girls’ section 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. Strangely, at that time, I had a fascination for directoire knickers and can remember dreaming about wearing them. I also enjoyed looking at all the outerwear and shoes etc. thinking how nice it must be to wear all those pretty things. Another thing I liked to do was read my sister’s comics and magazines. Quite naturally, (or so I think) 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” to teen and ‘True Romance’ style magazines. Not having access to any porn, these came in handy as visual aids in my wanking sessions. 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 putting myself in the situations in which they found themselves especially when it involved some vulnerability or submissiveness. Even now years later, I have a clear memory of an image of a girl in a story standing by a window at night wearing only a baby doll nightie, and another of a mini-skirted schoolgirl with her knickers down in public. The girl in the nightie had a gorgeous figure lovingly drawn by the artist. At one and the same time I wanted to both have sex her but be her too. It was a strange dichotomy. I was aroused not only by the idea of having sex with such a pretty girl but also the thought of being that girl, scantily clad in such a sexy garment. Anybody could have been watching me at that window and seen everything. Admittedly, the other image was doctored by me. 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 in that situation. How embarrassing to be in front of people with your 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 the public gaze. Thrilling!
More importantly, when my sister finished school and went to live with our gran (better job opportunities) she left behind some of her clothes. Everything (nearly) 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 still a treasure trove. I had worn her tights and shoes and tried on her school and Guide’s uniforms and some skirts, tops and dresses, but nothing more intimate. Not whilst she still used them. But I considered they were now unwanted by her and were my inheritance. She had barely left the premises when I started to enjoy my legacy. 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. There was only a few, but they were mine. I quickly undressed. Standing naked in my sister’s room, acutely conscious of what I was going to do, I was instantly erect. But what would I wear first? All my deep seated yearnings burst out. I was overwhelmed with the desire to wear everything. I felt I wanted to immerse myself in sea of femininity. I calmed myself down. Well almost. Trembling with excitement I reached out 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. 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; 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 and after a bit of fumbling, I fastened my first bra in place. I pushed what little chest fat I had above the under-wire 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 looked so sexy. I spent some time posing, sticking out my bottom and looking coquettishly over my shoulder. It was delightful. How I looked in the mirror determined my first choice of outfit. My sister’s school uniform was still hanging in the wardrobe. Short pleated grey skirt, white blouse, and red cardigan. As I was looking for the most suitable pair of tights, I found some white knee length pelerine socks. 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 (nice girly ones with a bit of a heel would come later). I found (and still do) everything about ‘dressing’ had an appeal; doing up my blouse with the buttons the ‘wrong’ way, sliding my skirt up my legs and fastening it in place, 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. Apart from my hair and with my erection now mostly hidden, I looked like any girl ready for school. I was ecstatic. I spent some time posing, viewing myself from every angle. Of course this included from behind, 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’d always wanted the girls in school to do, but rarely did. I looked, and felt, oh so sexy. I left the bedroom and walked around the house. I’d done this often in the past but the addition of bra and knickers made it all the more thrilling. By now my cock was fairly throbbing. Should I wank now, or tease myself a bit more with a change of outfit? No, I couldn’t wait. 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. 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 then 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 ceiling-pointing cock. 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 tissue paper! Quickly I pulled off my knickers and wrapped them around my swollen cock. Just in time. With a whole body shudder I orgasm-ed, spurting globs of cum in my sister’s soft white panties.
And then, there were my sister’s clothes. I’d always had an attraction for female clothes. Even as a boy I loved looking at the women’s and girls’ section 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. Strangely, at that time, I had a fascination for directoire knickers and can remember dreaming about wearing them. I also enjoyed looking at all the outerwear and shoes etc. thinking how nice it must be to wear all those pretty things. Another thing I liked to do was read my sister’s comics and magazines. Quite naturally, (or so I think) 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” to teen and ‘True Romance’ style magazines. Not having access to any porn, these came in handy as visual aids in my wanking sessions. 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 putting myself in the situations in which they found themselves especially when it involved some vulnerability or submissiveness. Even now years later, I have a clear memory of an image of a girl in a story standing by a window at night wearing only a baby doll nightie, and another of a mini-skirted schoolgirl with her knickers down in public. The girl in the nightie had a gorgeous figure lovingly drawn by the artist. At one and the same time I wanted to both have sex her but be her too. It was a strange dichotomy. I was aroused not only by the idea of having sex with such a pretty girl but also the thought of being that girl, scantily clad in such a sexy garment. Anybody could have been watching me at that window and seen everything. Admittedly, the other image was doctored by me. 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 in that situation. How embarrassing to be in front of people with your 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 the public gaze. Thrilling!
More importantly, when my sister finished school and went to live with our gran (better job opportunities) she left behind some of her clothes. Everything (nearly) 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 still a treasure trove. I had worn her tights and shoes and tried on her school and Guide’s uniforms and some skirts, tops and dresses, but nothing more intimate. Not whilst she still used them. But I considered they were now unwanted by her and were my inheritance. She had barely left the premises when I started to enjoy my legacy. 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. There was only a few, but they were mine. I quickly undressed. Standing naked in my sister’s room, acutely conscious of what I was going to do, I was instantly erect. But what would I wear first? All my deep seated yearnings burst out. I was overwhelmed with the desire to wear everything. I felt I wanted to immerse myself in sea of femininity. I calmed myself down. Well almost. Trembling with excitement I reached out 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. 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; 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 and after a bit of fumbling, I fastened my first bra in place. I pushed what little chest fat I had above the under-wire 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 looked so sexy. I spent some time posing, sticking out my bottom and looking coquettishly over my shoulder. It was delightful. How I looked in the mirror determined my first choice of outfit. My sister’s school uniform was still hanging in the wardrobe. Short pleated grey skirt, white blouse, and red cardigan. As I was looking for the most suitable pair of tights, I found some white knee length pelerine socks. 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 (nice girly ones with a bit of a heel would come later). I found (and still do) everything about ‘dressing’ had an appeal; doing up my blouse with the buttons the ‘wrong’ way, sliding my skirt up my legs and fastening it in place, 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. Apart from my hair and with my erection now mostly hidden, I looked like any girl ready for school. I was ecstatic. I spent some time posing, viewing myself from every angle. Of course this included from behind, 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’d always wanted the girls in school to do, but rarely did. I looked, and felt, oh so sexy. I left the bedroom and walked around the house. I’d done this often in the past but the addition of bra and knickers made it all the more thrilling. By now my cock was fairly throbbing. Should I wank now, or tease myself a bit more with a change of outfit? No, I couldn’t wait. 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. 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 then 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 ceiling-pointing cock. 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 tissue paper! Quickly I pulled off my knickers and wrapped them around my swollen cock. Just in time. With a whole body shudder I orgasm-ed, spurting globs of cum in my sister’s soft white panties.
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