As a boy, with five sisters, I was always surrounded by them and their clothes. Very early, I saw that their under wear was shiny, smooth, and frilly, and mine was much more plain. I loved the smooth feel and lacy edging on my younger sister's rhumba panties, and I would often sneak a look at the shiny panties and frilly petty coats in the clothes hamper from my two older sisters. I was just five years old when I went into the bathroom, closed the door and tried on a full petty coat with a satin top and shoulder straps. It had a tiered skirt of organza and lace that flared out around my legs. I loved how it fit my body, with a silky top and straps over my shoulders and a frilly, tiered lacy skirt hanging open around my legs. I found a pair of soft nylon panties to slid up my legs underneath the petty coat. With the satin top clinging and shiny on my chest, I lifted the skirt to see my panties in the mirror in the bathroom. I turned around in front of the mirror to see my back side and how the panties curved up and over my round butt with a glimmer of light coming off the shiny smooth nylon. My panties were exposed as I twirled around and flipped the skirt up. I was enthralled.
I tip toed out of the bathroom into my room which was right next door. I quietly closed the door and lay on my bed. First, I lay down on my side, seeing the satin top clinging to my body, and the skirt stiff but lacy along my hips and legs. Then I turned over onto my stomach, with my arms underneath my hips. I moved against my hands and arms with my hips. The rustle of the skirt and the feel of my penis sliding inside the silky panty and against the taffeta lining of the skirt was delicious. I looked at the straps on my shoulder, the satin top around my body, and the skirt moving around me. I spasmed after a while and there was a soothing feel of contentment when I was done. I stayed still on my bed, and I didn't want to move. I didn't want to undress. I laid in bed and curled up like a baby. But I had to undress before my older sisters came home from school. Lucky for me I was changed before they got home. Better still, I was lucky to always have something laying around to dress in. I even snuck panties and petty coats under my mattress so that I could dress whenever I could find a little time. When my older sisters got bras and teddies, tap pants and camis, I got to wear that lingerie too, but not as often as the petticoats.
Somehow I acquired for myself a shiny red nylon panty that I made my own. I don't know whose panty it was, but it became mine and I often put it on under my pajamas. For a long time I had this panty to wear as my very own. But, it was becoming harder to keep my sisters' clothes, and I also wanted my own pretty clothes. To have my own, I found lingerie that was on clothes lines. I really liked baby dolls with panties. I even managed to get a bra top negligee, which made me look grown up, even though I was just a boy. As much as I enjoyed the feeling when I rubbed myself, I just wanted to be dressed. I loved seeing how pretty I was, and often just stood before a mirror to see the outline of a girl in the mirror. I love how a panty would just nicely cover me and how it was shiny and silky smooth in nylon. The look of dainty straps across my shoulders when wearing a bra top, and the silky material clinging to my chest, especially with bra cups over my nipples, was something I liked to see on me. Just getting dressed up and staying dressed up was enough for me. But I had to do it alone.
Once, I was caught wearing a tank style bathing suit. My Mom was in the hallway and just some how knew to come into my room and tell me to get out of bed, after I darted back under the covers one morning. She made me take it off. She did not find the red panty, and right then I didn't have any petty coats or panties hidden under the mattress. Lucky me. She never said anything about this and she seemed to forget it. I took the lingerie that I grabbed from clothes lines, mostly negligees, and stashed them in the basement by the heater. I would dress up in a negligee every now and then, and rub my chest and stroke my nipples through the silky nylon and filmy sheath of my negligees. But the basement was dirty and after a while it was just too hard to dress up and be pretty.
By the time I was a high school student, I was so busy with school and sports, and then with dating, that I just didn't have time to think of dressing up. I lost track of the lingerie and probably just threw it away. Dressing just faded from view. I thought that it was just a passing thing and part of growing up. School, sports and dating kept me busy in high school. Also, I grew a lot in height, tall enough that I was 3-4 inches taller than my tallest sister. I went from a chubby boy to a skinny teenager. I had grown up. I thought I was a real guy when I joined other teens boys behind an old garage with a playboy magazine one day. But, this made me feel uncomfortable and strange. I was sort of sorry that we were doing this. But I went along with the other boys.
I was not dressing up in negligees or rubbing myself inside panties and baby dolls. Still, the sight of lingerie advertisements in newspapers and magazines was both interesting and embarrassing. I could not stop myself from looking, and seeing the fine detail in the lace and nylon fabric of bras and panties. I did not leer at the models, but studied their clothes. Then, I would look away if anyone was around to see me doing this. It was as if I was offended, while drawn to look. I didn't know what to make of these strange feelings. I just went to school and did the ususal things a boy does. I dated a lot, and wanted to make it with a girl. I even got a little bit lucky later on in school, although I never had sex.
When I began to work on my own after school, I got my own apartment. Dating was still something I did a lot, but was not always available. Now that I had my own place, I drifted back to dressing. Again, lingerie ads snared me. I started slowly, with negligees. I actually pretended to buy lingerie gifts, even having them gift - wrapped. Mostly, I bought negligees for my girlfriend, so I told the clerks. I managed to buy quite a collection of gifts, including teddies, camis with tap pants, baby dolls with panties, and filmy negligees. This was almost just like what I did as a youngster. In the evening, especially on weekends, I would wear my lingerie. I liked teddies, because they had the straps of a bra top, and a tight panty feel, and smooth silky fabric around my chest. I also liked camis, because they were so feminine and smooth. Tap pants were okay, but my anatomy was out of place. So I mostly wore a nylon panty that matched, or came close to matching, both the color and style of the cami.
I would sit and read, clean the dishes, and get ready for work the next day. I loved to get ready for bed, and slip under the covers. My bra top negligees pushed up on the sheet. I pulled the sheets over me to show off my breasts. I often changed into a negligee, especially a baby doll with matching panties. I would sometimes masturbate in negligees, imaging that I was a girl, and feeling so soft and looking so pretty in the satin lingerie. But often, I just drifted off to sleep in my negligee. Also, now when I would spasm, I left a stain on the lingerie, so I needed to wipe the lingerie clean. If I could not use the apartment washer and dryer, I sometimes would hand wash and dry the lingerie in my own bathroom. I would hang the dreamy lingerie on the shower rod to dry just like a girl or woman would do.
I so much wanted a bra, so that I could have the round breast forms of a woman. I was now grown up and could not just take from others. However, I could not bring myself to go into a store and buy a bra in person. No real guy goes out and buys a bra for his girlfriend. So, I got a catalogue from which to order some of my own bras. I had fun picking out bras and matching panties. I even looked at slips and camis. I trembled when I made my first catalogue order, but thankfully, no questions were asked. The delivered package was discrete and waiting for me one day after work. I raced up stairs and opened the package, unwrapped and then laid the new bras, panties, camisoles and half slips out on my queen-sized bed. I tried on everything, and laid one set back on the bed when trying on another set. I even tried to make a better look by pushing my penis into the crotch of the panty. I then had the smooth front panty line. My favorite panty was a white, full back hipster panty, with lace at the hips and a little dainty pink bow on the waist band in front. This had a coordinating, white, front hook, contoured, lined bra. This bra had a lace outer cup and smooth, lined inner cups. I filled out the bra with some panties to look better. When I wore the matching cami and half slip that I ordered, I was in heaven. I was tall and thin, and wearing a size 36B bra, size 5 panty, and a medium slip and cami top. I wanted this so much, and I needed to share this.
One night, I called one of the 800 telephone numbers that I often saw in magazines. I hesitated when I started out, but was happy to find a girl to share my fantasy and take me all the way in dressing. She helped me dress in my matching white bra and panty and filled my lined cups with implants. She dressed me in the cami and half slip that matched - my own. She asked if I even went out dressed. I said no, but that I would be interested to try. She picked smooth and shiny cream - colored stockings and gave them to me to put on. They came up my thighs to almost my panty, and had an elastic and lace edge to hold them up. She had me put on a set of strappy tan sandals that hooked around my ankles. She helped me get all made up, and gave me a wig with hair to my shoulders gently pulled back into a soft ponytail. A white and pink polyester skirt with a sheer overlay of white and a belted waist was topped with a shiny, white buttoned blouse. With a gold choker collar, pierced ears with small gold rings, and a few blouse buttons undone at the neck, she said that I was ready to go.
We went to a piano bar, and soon we were talking with some men. She said that there was a tall, handsome guy who asked me to dance. He helped me out of my chair and escorted me to the dance floor. Once there, he softly pulled me into him. He held me tight, and pulled my waist to his legs as we danced. My skirt pulled and flipped up at times, almost exposing my panty, but just revealing the layers of slip, skirt liner and sheer skirt overly that rode up my shiny legs as we danced. I was dancing. He was getting hard against my skirt, and pushing into me. There was nothing I could do but just hold onto him while dancing. She told me how pretty I looked in a dress, dancing and being held close, my breasts pushed against his chest, and the laced edge of my slip just showing as I reached up to him on my heels to kiss him. I was so relaxed, laying my head on his shoulder with my arms draped around his neck.
He took me over to a corner, and held me close. We kissed, and he ran his hands over my shoulders, down my body and to my hips, pulling up my skirt. I was scared that he would find out. So I put my hand on his growing erection, and he kissed me slowly and deep, letting me caress him through his pants. I pulled back a little, and turned to one side, to slow this down, still caressing him. I told him that this was not a good time to be in me, but that I wanted to give him the release he needed. So I let him hold me and used my hand to unzip him and expose his penis to my skirt. I slowly pushed and moved my hips against him, holding him in my hand. My skirt tugged on his erection, so I lifted my skirt and slipped my skirt and slip over him. He was now rubbing up my leg and my hand coved him with my silky slip and filmy skirt. He relaxed to let me do this, and asked to come from behind. I was afraid of this, since I never had been taken before, but I turned around for him and hoped to escape being penetrated or discovered. His penis just kept poking against me because he was so hard.
Then I felt him hard on my hips. He wrapped his arms around me, and held me from behind. I then leaned back onto his chest. From behind, I could feel him hard on my panty, and he was pulling my skirt up and over to one side. He cupped my bra-covered breasts in one hand, and opened his pants even more to push his rigid penis against my panty-covered butt.
She saw him take me over to the corner next to a phone, and that he was behind me. I was leaning my head back on his chest and shoulder, and I was pushing back against his hips. All of this time, she said that I smiled at the feel of his penis against my silky skirt, slip and panty. When he lifted my filmy skirt, skirt liner and the lace-edged slip, my hips were full and round like a woman's hips. I was covered in the pretty, white panty that shined bright even in the dim light.
I leaned over a bit to let him get to me. When I did this, she could see the lace edge of my contour bra at the open neck line of the white blouse. My breasts were pulling tight against the blouse, and the lace of the bra pressed through the blouse. He pulled my panty aside and rubbed himself in the crack of my butt. I pushed back against his pushing and his penis slid up and hit the satin slip dangling over my hips.
My own penis was sliding against my panty and my hips were swinging around in the slip. My penis was hitting the waist band of my panty and then coming back, in rhythm with him and just as fast as he was. My hand was moving the tip of my penis sideways against my panty. I also pulled against my penis with the silky panty. I moved my hips around in the slip while doing this, and it felt wonderful moving inside the layers of satin that were floating around my hips. I was also able to hear the rustle of the slip and skirt as I was on the bed.
She saw him going faster and trying to find my opening, pushing against the rim of my butt opening. I held him in my hand, and flicked the underside of his penis when it hit the satin slip and skirt. I felt him get wet, and cooed to him. He knew. He was pushing against my hips and I was pushing back against his pulsing rod. The rim of his penis was poking against the rim of my butt as he slid forward on my smooth round butt. I could fell him shorten his thrusts and pick up speed. I lightly tightened my fingers on him, but let him pull back on his own. The tip of his penis began to swell and fill my hand. His penis popped up and away from my rim. He was now furiously pumping my butt crease. I licked my fingers with a mouthful of moist saliva, and draped my hand under him, catching his tip in a wet grip. He pushed through my wet fingers for what seemed like a long time of short, strong thrusts and pulls. All of a sudden he grabbed my hips back into him and pushed deep, stopping right at my opening and gushed warm cum at my opening and over my butt. I felt him warm all over my hips. I came in my panty at home. He dripped from me, but I pulled my panty back up over my hips to hold his cum close to me. At home, my panty was soaked, and leaked onto my slip, but it felt so comforting. I pulled my panty tightly over my penis and held my cum close to me.
I thanked the girl for the call and fell to sleep dressed in my own bra and panty set, with a panty full of cum just like the girl I wanted to be.