This is my 3rd and final post of the series on "how I got started". Any posts after this one will be only about my on-going experiences as a cross-dresser, MTF. The first post in this series described how I got started with panties. The 2nd one described sleepwear. This 3rd post describes some encounters with my then-girlfriend Carol when we were both 20. Those encounters became the start of the "outerwear" part of my cross-dressing.
She discovered quite by accident one day that I was a panty boy (I had been so since I was 6). So she said that she wanted to "finish the job", by "turning me into a girl". I resisted at first, although to this day I don't know why. She was persistent and wouldn't take no for an answer. Of course I'm glad she won out, I'm eternally grateful to her. She "turned me into a girl" fairly often, as she'd rather hang out at her place and do that than go out on a "real" date.
Deleting the sexual part of this account, here's how she "turned me into a girl": She'd say "C'mon Marilyn, its girlie time!". Then she'd take me into her bedroom and remove all my clothes and dress me in a spare pair of her own panties and a lacy bra with "big girl" inserts, followed by garter belt and nylons after she shaved my legs. After that, she'd put a skirt and blouse on me. She left my blouse partially unbuttoned to show off the lace on my bra. All of her clothes fit me well. She finished "turning me into a girl" by doing my makeup, perfume, lipstick, eyelashes, nails, diamond ear rings and other jewelry and the "Marilyn Monroe" wig and those 4-inch stilettos which were so hard to walk in. The shoes were black patent leather with swirls of Rhine stones on them.
After she was done, she'd admire her handiwork by slapping me on the outside of my skirt with her bare hand and whistling at me and telling me what a "hot babe" I had become. I hope all the women I have whistled at throughout the years have enjoyed it as much as I did when Carol whistled at me. She'd then parade me in front of a full length mirror so I could admire her handiwork and also flirt with myself.
After I became "Marilyn", we'd go into her living room and she'd put on some music. She had me "perform" for her by having me walk in my stilettos and dance to the music. After a couple of times, I got the hang of it. She especially enjoyed the scratching sound that the tops of my nylons made when they rubbed together under my skirt as I walked or danced. When I wore a certain white pleated miniskirt, she'd have me walk "heel to toe" and stomp in my stilettos, which made my skirt flutter on my hips and made my booty jiggle. When I walked that way, she'd whistle at me and call me "Jiggles". When I wore a different pink miniskirt, the hem would tease me by rubbing against my thighs as I walked or danced. When I wore a longer full skirt, she'd have me "twirl like a girl", until my skirt lifted high enough to show my garters and panties. I stumbled a bit, but managed to stay on my feet when doing my "twirly-girly". She whistled at me when I did that. When she had me wear a "pencil" skirt, then I'd do the "Marilyn Monroe wiggle" when I walked, also accompanied by flirting and more wolf whistles from her. Sometimes she'd have me wear a different tight mint green patent leather miniskirt that had cutouts of heart shapes, one on each side in the back. The cutouts were bigger than a golf ball, but smaller than a tennis ball. The cutouts let my panties be seen while I wore the skirt. I totally enjoyed prancing around in that skirt, simply because she'd continue whistling and flirting with me.
When we were all done, she'd take me back into her bedroom and open her panty drawer. She'd say: "Since you've been such a good girl, you can pick out a new pair of panties for yourself." Of course I had the option to keep her panties which I was already wearing. My choice. She'd then keep my original ones for herself.
Have a good day, stay healthy and thanks for reading
Originally Posted by lindapantyboy
I wanted to quote Linda but honestly didn't know where to start. I fixed it now.
