Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

... threatened to go out to the bar without me if I didn’t play along. Soon Michelle had me dressed up Madonna style in a Fishnet crotchless bodysuit, black satin panties. a ruffled denim miniskirt, and a black leather and lace corset with rhinestones which she pulled really tight in the middle. This pushed up my pecs and squeezed them together, giving me small but respectable cleavage, and made my hips flare out a bit. Next she had me put on Kayla’s leather “biker” ¾ jacket and bl**d red stiletto heels . When I saw myself in the mirror I was surprised at how girly I already looked and we hadn’t done my hair or makeup yet. Next Michelle curled my hair with a curling iron and used a brush to tease it into a big hair style that was very popular back then, finishing it with a red ribbon hairband with a cute bow. She had some dangly red clip on earrings (they were a lot easier to find back then) and several necklaces and bracelets that she had me put on. Next came a couple belts with studs she wrapped around my waist, completing the Madonna look that was so en’ vogue at the time. After this she glued fake nails on me saying it would help my hands look more feminine.( I didn’t realize at the time how hard it would be to get them off!) These she painted the same red as my heels calling it CFM red with a smirk. After this she did my makeup, applying it rather heavy with lots of eyeliner and mascara, making envious comments about the length of my lashes, which women have always remarked ...

... upon. The blush really made my cheekbones stand out, giving my face a more feminine exotic appearance. She even used some on my cleavage ,after putting pads in the corset , making it look deeper and giving me the appearance of decent B cup size breasts. Lastly she applied lipstick and lipliner to my lips with a heavy dose of gloss atop the bl**dred lipstick which made my lips look sexy and pouty. “There you go, perfect little cocksucker lips! The guys at the bar are gonna go crazy over you” she said laughing, as she finished this. “Hang on there MikkiI!” I protested “I’m not gay!” I never said that, but you sure do make a hot girl with my help! I’m rather proud of my work if I do say so myself” She replied with a wink. “Take a look for yourself!” as she led me over to the full length mirror on her dorm room door. I stumbled a bit in the high heels but not too much as I had some practice from borrowing my mom’s from time to time. When we got over to the mirror I took my first real look and was shocked at what I saw in the mirror. I didn’t recognize myself , there was a hot, sexy, slightly slutty, young woman looking back at me. The corset had given me a curvier figure, and my legs looked fantastic in the high heels and fishnet body stocking. My nagging worries that I would be recognized by someone I knew vanished in an instant. I realized there was going to be at least one problem as I felt my erection spring to life. “Oh my, we can’t have that now, can we?” Mikki exclaimed. ...