Just a Summer Job Pt. 01

The summer going into my junior year of college, I was frantically searching for a job to keep up with my bar tab and utilities. I was looking more for something at a bar or restaurant for the cash tips, but ultimately ended up only getting job offers from retail stores. I ultimately chose Macy's because of the location and the 60% employee discount.

After 2 weeks, I started working in the men's business wear department and needed someone to try my measuring and tailoring skills. There was a young blond haired 21 year old dime named Rachel who also went to my university and worked in the women's shoe department who happened to be walking out of the restroom and the only person in the store after we opened at 9 am, thirty minutes ago. We were bored and I asked her if she would like to be measured for a suit jokingly and she surprisingly took me up on the offer ecstatically. I took her shoulder and sleeve measurements, but when I got to her neck measurement, she whispered "harder daddy."

I was so confused, but was standing behind her so she couldn't tell what I was thinking until she peered seductively over her shoulder and gave me pouty lips. I as naturally as I could, I laughed and replied "oh you like that, do Ya?" Although joking at first, she said "Yeah daddy," with as much seriousness as I've seen someone say something so kinky. I then measured her chest and she took my hands and caressed her perky c cup tits. Things were getting extremely raunchy in the middle of the department, so I was hoping that nobody would come in for some time.

Unfortunately, as the thought entered my horny head, an older woman in her early forties walked in, and Rachel jumped away from me and demanded that she see her suit. I went into the back and picked out a seer sucker blazer that she actually rocked really well with her light pink button down shirt, short white skirt and baby blue peeptoe pumps. She liked it so much that she decided to wear that for the rest of her shift as well as give me her number.

The next shift we worked together 3 days later, she texted me to come upstairs to her department when there was nobody in mine. At about 9 o clock, I went upstairs and she was helping some girl pick out her heels for prom. She was looking at a pair of silver strappy ones with a really high platform. I walked over and complimented her on them, and the high school girl asked me if I liked those or a sparkly 6 inch pump Better, and I said the strappy ones. Rachel smiled and asked me why? We had a conversation about her prom dress and jewelry that she was wearing with the shoes for about 10 minutes. She ended up going with the strappy heels and went on her way at about 915. After the girl and her sister left there was nobody else upstairs besides the cosmetics and the women's department shift manager who usually stayed in her office all day and night.

Rachel said she was impressed with my sense of women's fashion. I jokingly said I should've been a girl at heart and she said "you're lucky you're not!"

I, being the chauvinist I am, said being a girl is easy and that they get everything handed to them for being pretty. She then listed everything a girl has to do that sucks like shaving, makeup, doing hair, wearing heels, periods, and so on. I said I could do what a girl does, and she said prove it.

I said fine, how hard could it be...

I didn't know what I was getting myself into once those words left my mouth. Rachel said "alright put on these 4 inch heels and see how long you last. What size are you, a 10.5?" She was good at her job And judging foot sizes; I was an 11 in men's so a 10.5 in women's. When she came back, they didn't have my size in the 2 strap stilettos, so she brought out a 6 inch hot pink peeptoe stilettos. My jaw dropped when I saw them and she came back with, "you're not too big of a wuss are ya?!" As I put them On, she made me take off my socks to experience the full pain. Not only was it painful. It was like walking on my tippy toes with razor wire all around my ankle and toes. I walked about 3 steps and ate shit causing a loud thud. The cosmetics and jewelery attendant, Darcie, rushed over and shouted "is everyone alright?!" I shakily stood up and said "I'm fine, just took a tumble." Rachel pointed at my feet and Darcie looked and unmediated started dying laughing. "Why are you wearing those?!" Asked Darcie, while trying to catch her breath.

"I..." I uttered before getting loudly interrupted by Rachel.

"He's trying on heels for his drag performance next week!" With a menacing grin on her ridiculously cute face.

"What?! No I'm proving that being a girl isn't that..." But realized Darcie had an equally mischievous smile on her face, and was already asking if I need pointers on my makeup.

"No seriously I'm not a drag queen, let alone gay at all!" I said trying to convince her of the truth.

Rachel said from behind me "Oh are you chicken?! B'ucaaack, I thought being a girl was easy and you wanted to prove it!"

Being content with my sexuality and slightly turned on by the two beautiful women that were toying with me, I agreed to let Darcie do my makeup. She started with some foundation and then a thick dark eyeliner. She then put on some dark nude and bright silver eye shadow, followed by nude lip liner and a light pink lip stick and sparkly lip gloss. She then used a razor to touch up my eyebrows which I didn't even realize as they didn't hurt at all and I had been laying down with my eyes closed and near sleep. They finished with blush and contouring all over my face as I slipped asleep.

I quickly awoke to both of my ears being pierced with Rachel and Darcie on either side of me, laughing hysterically. Naturally I freaked out and complained that shit hurt. And they both started giving my pouty lips and making a crying motion with their fists. Not being able to swallow my pride, I just said "fuck it, it's really not that bad," but as I actually looked at myself, I got really scared because I actually looked like a beautiful girl in the face, much better than I think I do as a man. I smiled and said "wow, Darcie you're amazing!"

Darcie replied "I knew you were gay the minute I met you" with a huge smile.

I said " I'm really not gay I was just saying you do a good jo..."

We were all interrupted by Marla our 45 year old 6 foot dark hair shift manager saying "with all of you girls up here, who's running downstairs with the last hour before close?"

I quickly apologized and said Id get right back to work, but she wouldn't let me go back in front of customers being two genders and since the makeup wouldn't come off, I had to put on the clothes of her choosing. She took me to the lingerie section and gave me pantyhose, a bra, waste shaper and a yellow bright strapless romper. I said "do you really think this is necessary?"

She replied with the utmost seriousness, "I take my job and appearance very seriously here at Macy's. I don't want you to scare off customers looking like a hermaphrodite tranny! The girls also tell me that you think men are superior and that being a girl is a joke, and I'm here to make sure you rethink that idea." I was in shock, said nothing and went into a changing room.

When I came out, all three girls were standing there with their cameras ready to capture the most embarrassing moment of my life. They said if I didn't go downstairs and do whatever they say, I'm going to be the laughingstock of the Internet.

To be continued...