I've had very strong feelings since reading the posts, and even adding two posts to the Discussion, When Did You First Go Public. It has brought back so many memories - so, incorporating and augmenting my posts to that discussion, here goes.
Like everyone here, I always knew I was supposed to be a girl, and when I was little really didn't understand why I wasn't. I wanted to be treated as a girl, wear the pretty clothes, grow my hair and be just like my mom. I would put on her shoes all the time and ask why her why I couldn't wear dresses. When I was in the bath with her I asked her why we were different - why I had a thing sticking out of me and she didn't. I also asked her why I didn't have breasts, though I didn't know that was what they were called. She told me that it was wrong, that I was a boy, not a girl, and not to talk to my father about it.
First time out - I was 5
However, I found an accomplice when I was around five - my aunt Laura. When she stayed at our house I would sleep with her and she would let me wear her slip as a nightie.
She lived close by and I was allowed to visit her and sleep over sometimes. Whenever I was there she would give me a slip to put on that she had altered to fit me, let me pick out jewellery to wear (clip on earrings, necklaces & bracelets), do my face (blush, eye shadow & lipstick), spray me with perfume, paint my nails (bright red) and let me pick out a pair of her heels (too big) to wear. I would clump around in the heels and we would have tea. I loved to notice my red lip stains on the tea cup and re-apply my lipstick. Obviously, I was very happy (ecstatic really) when we had these times alone and I would talk to her about wanting to be a girl, just like her. She always told me that I was too pretty to be a boy. She would show me her beautiful lingerie, stockings and dresses, let me play with her jewellery, and tell me that when I was bigger I could wear things like that.
Caught in the act
My days of bliss came to a crashing end the day my father came over early to pick me up, caught us and went bananas. He tore the slip and jewellery off me, slapped my face and told my aunt that she had turned me into a pervert. He took me home, told me he was ashamed that I was his son, that I was a sissy, and gave me a severe spanking. He had my mother come in to my room while I was sobbing from the beating and shame, to tell me that what I wanted was wrong, that I was a boy, not a girl. She told me to wash my face and to never to put makeup on again, I was a boy, not a girl. Then she used polish remover on my fingers and toes, and told me not to ever use nail polish, that it was for girls. This was the start of my feelings of deep shame and instilled in me the thoughts that what I wanted was very bad / evil, to hide my true feelings from everyone and try to bury them from myself.
Little girl can't stop
Not that it really stopped me. I would sneak into my parent's room and go through my mom's dressing table. I knew in which drawer she kept her panties, bras, girdles and stockings. I knew her shades of lipstick, foundation, powder, blush, eye shadow and liner. I also loved watching her put on her undies, do her face and get dressed, until she wouldn't let me when I got older.
Whenever I could I would slip into their room and put on a pair of panties, a panty girdle, stockings and a bra. From about ten I "stole" such items from her and hid them in my room so that I could wear them to bed and under my clothes when I thought no one would notice. Mom would find them from time to time and take them back, but say nothing. I would wait a few days and "steal"them back. But all the time I was filled with shame, that what I was doing was wrong, perverse.
As a young teen
When I was 13 I got a part time job, and immediately started shopping. I finally had the money to buy my own lingerie, pantyhose and makeup, all carefully hidden. I also bought girls jeans, shorts and tops, penny loafers and top-siders. I was amazed that no one seemed to be able to tell the difference when I wore the jeans, shorts, tops and shoes. I started shaving my legs at the first sign of hair. I heard about breast forms when my mother and her friends were talking about someone who had a mastectomy, and got myself a pair (very carefully hidden). I wore perfume and lip gloss and soon discovered the necessity of panty liners, douche and tampons. I hid everything from my family and friends. I was absolutely alone.
My first real time out was when I was 13 years old and home alone from school. Whenever I was home alone I would put on a selection from my secret stash (panty girdle, panties, pantyhose and breast form filled bra), do my makeup (also stashed) & slipped on some clothes, shoes and jewellery from my mom's collection. One day I knew I had to go further. I put on my undies and pantyhose, did my makeup and raided mom's collection. I remember everything I wore - tight black skirt above the knee, mauve ribbed cashmere turtleneck, black silk scarf, low black pumps, clip on gold earrings, heavy gold chain around my neck, gold virgin pin, gold Hermes bracelet on my left wrist and gold bangles on my right wrist. I checked myself out in the mirror, put on a pair of big Jackie O shades, slipped my mom's Birkin bag (fake) over my shoulder and headed out the door. I walked about 10 blocks, nodding to people on the street. I was shaking with excitement. I've never forgotten the fabulous feeling of the breeze on my legs that first time. I didn't want the moment to stop, but made myself turn around and go home before someone would beat me home and find me out. I repeated this as often as I could. I did this alone, I had no confidants, no one knew.
Friends get to see
Then came a big two-school (one boys & one girls) Halloween party when I was 15. Everyone was in a tizzy about what to wear - pirates, clowns, period costumes, etc. Linda, a girl I knew, told me that her brother (Larry) was going to go as her, and suggested that I go as his (her) girl friend - girls always travel in pairs or packs. My best friend, Anthony, a really hunky, absolutely straight guy (or so I thought), said it would be a great, fun idea, and that he'd be my "date". So, I "reluctantly" agreed, as long as Linda would help me. Actually, I was shaking with excitement. As far as my parents knew, I was going to the party as me, a normal boy.
In preparation I went to a department store and bought a sassoon-style dirty-blonde wig, two rings (a wide silver friendship band and a large cosmetic ruby ring), a strand of fake pearls and several silver wrist bangles - it almost broke me. I also bought a pair of black 3" stiletto heels. Linda was to supply my dress.
Late in the afternoon on Halloween day I went back to the department store wig department, which also pierced ears, and asked to have mine done. The older woman in charge was extremely sympathetic, but told me that, as a boy, I would be putting myself in all kinds of danger. I told her that I wanted to try if for just the party, and then take them out and let my ears heal. So, she did it, including replacing the keepers with a pair of fake diamonds.
I went straight to Linda's with everything I'd bought, as well as black panties and matching bra, breast forms, black Wonderbra panty girdle and sheer black pantyhose and makeup. She was stunned that I'd pierced my ears and amazed when I came out of her bathroom in my wig, jewellery, lingerie, pantyhose and heels. She told me my undies were nicer than anything she owned, and wondered where I got the breast forms and how I'd learned to walk so easily in heels. I sat down at her dressing table and "let" her do my makeup. I surprised her by taking over to do my eyeliner in a flash and over-ruling her choice of lipstick color. She also commented on how smooth my legs were, and my skin overall. I tried on 3 or 4 of her dresses, and settled on a sleeveless ruby red with black detail chinoise sheath that was slit up the right side to mid-thigh. She gave me a small black alligator clutch (her mother's) to complete the look. I put my lipstick, blush, perfume, a panty liner and $20 in the clutch. I looked at myself again in the mirror and started to shake and cry.
All the while Linda had been running back and forth to her brother's (Larry) room, helping him get himself together, and brought him in when I was done. He looked like a boy in a dress, I looked like a teen queen, and couldn't wait to go to the dance.
Anthony, Larry's girlfriend and Linda's boyfriend showed up shortly, and we were off. Everyone was stunned by my look, which pleased me no end. At the dance people didn't recognized me until they were told/introduced. I got teased by a lot of the guys and complimented by a lot of the girls. Linda and her friends treated me as one of their gang. Some girls gave me a hard time and a few jocks started hinting about BJ's, which made me feel both terrified and excited. I danced mostly with girls and a few times with Anthony, including a slow dance, which was dreamy. I did not want the evening to end.
But it did, and Cinderella changed back into a pumpkin, creamed off her makeup, removed the wig, jewellery and piercings (took a few days to heal), and put on her boy clothes (over her unmentionables) and her penny loafers (girls).
Caught again - shame, guilt and pain
A few days later my father heard about my "costume" tore into me in a rage, and actually hit me. My mom told me again that what I had done was wrong, and was breaking my father's heart. All I felt was shame, guilt and pain, which was so acute that I blocked my feelings for years.
To be continued....