If you found out that your future employer was into crossdressers,
would you dress up to secure the job? Would you wear makeup too?
It was a sunny Friday morning in Florida . My girlfriend, Molly and I lived together in Tampa at the time. She was a very feminine girl who worked at a mall beauty kiosk with her also feminine best friend, Leanne. They were both very passionate about cosmetology and often practiced doing each other’s makeup and nails in their free time. Leanne lived only four houses down the road in our suburban neighborhood.
As I woke up to bright sunlight beaming through the open blinds, I noticed sparkly red, tan, blue and brown blobs along with black smudged lines on my pillow. Upon lifting my head, I realized Molly’s makeup had smeared all over both of our pillows while we slept. I was hungover and I knew she would be too, as the previous night we had some friends over for a small party. “Molly, wake up.” I said as she started to roll over and open her eyes. “You fell asleep with your makeup on again. It’s everywhere.” “Ugh,” she says, “if only I slept still and facing up like you do, I wouldn’t make such a big mess.” I laughed and got up to brush my teeth. I looked at the clock and was surprised with how early I had woken up: it was 6am.
I had a job interview at noon, which meant I could exert some energy, shower, shave and take a nap all before the interview. I grabbed my skateboard and walked out the door without waking Molly, who had fallen back asleep on our colorfully dirty pillows. I got a quick breakfast and met up with some friends at the local skatepark for a two-hour long session. Around 8:30, I said bye to the homies at the park and skated home. I was sweaty by the time I got to the house and was surprised to see Molly and Leanne up and partying again.
The two girls were dancing around the kitchen while cooking breakfast, drinking mimosas, and singing along to some girly music. Maybe it was Miley Cyrus, who knows? I noticed Molly had cleaned her face but she was still in her underwear. Leanne was fully dressed, fully made-up, and was wearing glasses and an American flag bandana in her hair, a look that she knew I really liked. “Hey, so I hear you’re interviewing with Chrissy today!” shouts Leanne from across the room. “Well I’m interviewing to be a bartender at Cloud Nine (a local dive bar) in a few hours. I don’t know who Chrissy is.” I said. Leanne goes, “She’s my mom’s friend. She’s also the manager who you’ll be interviewing with today. We love her!” Molly agrees, “Yeah she’s the best. And, she’ll probably like you since you skate and have tattoos.” Leanne interrupts, “She loves skateboarders for sure. But she also weirdly has a thing for guys that can be dressed up into passable crossdressers. Have you ever noticed how many transsexual women work behind the bar? She loves them. I bet if you ever get her into the bedroom with her, she’ll try to dress you up and do your makeup. After shaving your face and legs, of course.”
“Oh stop it, Leanne. Chrissy simply loves things that are misunderstood by popular culture. She’s weird in a good way and appreciates other weirdos too.” says Molly. “Well it’s true,” says Leanne, “she LOVES crossdressers. If we put you into a dress and slapped some lipstick on you, you’d definitely get the job.” I laughed and told both girls that that was never going to happen. Even if I made a good-looking girl, I wouldn’t go out in public like that just to guarantee my interview goes successfully. I tuned them out and went to take a shower and shave.
I got out the shower, put on an undershirt and boxers and immediately started yawning. “I shouldn’t be tired for the interview.” I thought to myself, “Since I still have three hours to kill I should definitely take a nap.” I walked out of our shared bedroom and into the kitchen. Standing there, smiling and combing a blonde wig was Leanne. Molly was right beside her, looking through a box of jewelry. “Come here.” says Molly. I reluctantly walked over to her as she pulls out a weird-looking rocky red necklace. She put it around my neck and goes “Ohh that’s pretty.” Before I could turn around, Leanne says, “Hold still,” as she squeezes the blonde wig onto my head. I felt the locks caressing the sides of my freshly shaven face. It felt warm and comforting, and smelled like a Leanne’s perfume, which was actually pretty nice.
Leanne used two scrunches to give me blonde pigtails. I joked around with the two girls, mimicking a valley girl using a high-pitched voice. We all had a good laugh and I laid down on the couch. My eyelids got heavy and it was tough to keep them open. “Isn’t she pretty?” I heard Leanne proclaim as I heard the sound of a camera clicking. I opened my eyes to see Leanne standing over me and looking down at my face, giving me almost a seductive look while wearing her glasses and bandana. “Is she into me?” I thought, confused.
Molly was mixing up a couple more mimosas on the kitchen counter, still in her underwear. I realized that I had passed out, but for how long? Did they really think the wig and necklace I was still wearing were that funny? “Good morning Princess!” Molly says from across the room, “Why don’t you go into our bedroom and see what I laid out for your interview!”
I walked into our bedroom half expecting a freshly dry-cleaned button-down shirt and slacks on the bed. Half of me also expected feminine clothes since the two girls were such jokesters. Of course! Lying on the bed was a plaid skirt, floral pattern stockings, pink panties and a matching bra, and a small mirror. “You should definitely wear those with your regular shirt, socks and shoes so Chrissy knows you skate!” Shouts Leanne from the other room, “Trust me, you’ll look so pretty and she’ll totally dig your style.” Still a bit groggy from the nap, I go to reach for the skirt and stockings when I catch my reflection in the mirror on the corner of the bed. “Oh what?!”
Is that me? I open my eyes wider to realize that the girls, or at least Leanne, must’ve put makeup on my freshly shaved face while I was napping. They gave me the works, just like they would’ve to a female client at their kiosk. I was stunned.
Despite being so surprised, I was also impressed with how feminine I looked. Molly walked into the bedroom and slapped my ass as she walked by. “Hey beautiful,” she said as she picked out her own clothes for the day from the dresser, “Are you going to stay pretty for your interview?” “Sure” I said. Molly got dressed quickly while I stood there contemplating my decision. “Good,” she says while walking towards the door, “because Chrissy already knows you’ll be interviewing en femme. We told her. Also, stop by our mall kiosk so I can get a photo of you in your full outfit before your interview. Leanne and I have to get to work now, but you look so pretty!” She gives me a kiss goodbye while grabbing my ass. “Oh well.” I thought, “Fuck it. I guess I’ll dress up en femme to secure my employment.” I put on all the clothes the girls set aside for me, even the bra under my shirt, and walked out the front door towards my car. The mall was on the way to Cloud Nine, where I was applying, so it wouldn’t be a problem stopping there. As soon as I walked up to the kiosk, Leanne sees me first and tells me to pose for a quick photo. Click!
“Well, I’m off to my interview. Wish me luck!” I shouted as I left the mall. As I walked to my car, a group of bimbo-looking girls in the mall parking lot whistled at me and catcalled. Somehow it made me slightly aroused. I was in a good mood and ready for the interview. I parked in the parking lot at Cloud Nine and walked towards the front door. As soon as I walked in, Chrissy was already sitting at the bar with a Heineken in front of her, reviewing my resume. She turns towards me and I immediately could tell she liked what she saw. Her eyes gazed up and down my body as she smiled seductively. It seemed like we were wearing the same shade of red lipstick.
“Well hello missy. You look adorable! Shall we begin your interview?” Says Chrissy in a seductive voice. “Absolutely.” I said…