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Description
I was thrilled when my office assistant suggested we switch clothes. I’d been secretly crossdressing for years and occasionally indulged myself by wearing lacy lingerie under my suit on the weekend. Elise was the first one to actually notice.

“Mr. Parker, you’re wearing a bra? That’s so interesting. Do you always wear it?”

I’d intended to finish the presentation alone, but then I realized that I needed help to print and collate material for Monday morning. Elise agreed to come in for a few hours in the afternoon. Did I forget or did I subconsciously want her to notice the bra straps under my shirt? Elise was intrigued rather than shocked and said she’d always wanted to wear a man’s suit.

“I’ll let you try on my skirt and blouse if you’ll let me try your suit.”

My heart was pounding, and I felt light-headed as we undressed and exchanged our clothing. Elise is tall and fit, and I’m smaller than the average man, so her blouse fit me surprisingly well. I stuffed a couple of foam stress balls into the cups of my bra to produce a more convincing shape. The skirt had an elastic waist that easily accommodated my slender build. I was even able to squeeze my feet into her three-inch heels.

Elise looked quite natural outfitted as an account rep. Her shirt sleeves were slightly long and her collar was a bit loose, but the jacket and tie effectively disguised her small breasts. The trousers were a bit tight in the seat, but she pulled her belt a couple of notches tighter and the cuffs fell right where they should on her wingtip shoes.

Elise surprised me by lighting up one of my cigars from the credenza. She seemed to want the full experience. I was even more surprised when she called me by her name.

“We may have crossed a line here, Elise, mixing personal and business issues, and I think we should return to a more formal basis. It would be better for you to refer to me as Mr. Parker from now on. After all, I am the account rep.”

“Uh, yes sir - Mr. Parker, sir” I stammered, unsure how to respond.

“So, if you’ll get back to your copy machine, I’ll put the final touches on this presentation. Oh, feel free to take your purse to the lady’s room and powder your nose if you need to. I understand how important that can be for a woman.”

“Of course, Mr. Parker, I’ll be right back.”

It was my first visit to the lady’s room. I sat in a stall and looked through what seemed to be my purse for the time being. It was exciting to sort through the feminine personal effects. I found a cellphone in a pink case, makeup, and a tampon. I looked at the driver’s license and wondered if I could really pass as Elise Johnson. I wasn’t sure when this would end or whether I even wanted it to end.

I stood in front of the mirror and applied lipstick generously to emphasize my lips. I found mascara and eyeliner, so I used those as well. When my face looked presentable, I returned to find Mr. Parker practicing the presentation.

The unmistakable odor of cigar smoke accompanied a deeper, more assertive tone of voice than I was used to. And I could see a glass of whiskey, neat, on the desk. Everything was just the way that Mr. Parker liked it. I felt a new thrill of excitement as I anticipated what Monday might bring.

Description
I was thrilled when my office assistant suggested we switch clothes. I’d been secretly crossdressing for years and occasionally indulged myself by wearing lacy lingerie under my suit on the weekend. Elise was the first one to actually notice.

“Mr. Parker, you’re wearing a bra? That’s so interesting. Do you always wear it?”

I’d intended to finish the presentation alone, but then I realized that I needed help to print and collate material for Monday morning. Elise agreed to come in for a few hours in the afternoon. Did I forget or did I subconsciously want her to notice the bra straps under my shirt? Elise was intrigued rather than shocked and said she’d always wanted to wear a man’s suit.

“I’ll let you try on my skirt and blouse if you’ll let me try your suit.”

My heart was pounding, and I felt light-headed as we undressed and exchanged our clothing. Elise is tall and fit, and I’m smaller than the average man, so her blouse fit me surprisingly well. I stuffed a couple of foam stress balls into the cups of my bra to produce a more convincing shape. The skirt had an elastic waist that easily accommodated my slender build. I was even able to squeeze my feet into her three-inch heels.

Elise looked quite natural outfitted as an account rep. Her shirt sleeves were slightly long and her collar was a bit loose, but the jacket and tie effectively disguised her small breasts. The trousers were a bit tight in the seat, but she pulled her belt a couple of notches tighter and the cuffs fell right where they should on her wingtip shoes.

Elise surprised me by lighting up one of my cigars from the credenza. She seemed to want the full experience. I was even more surprised when she called me by her name.

“We may have crossed a line here, Elise, mixing personal and business issues, and I think we should return to a more formal basis. It would be better for you to refer to me as Mr. Parker from now on. After all, I am the account rep.”

“Uh, yes sir - Mr. Parker, sir” I stammered, unsure how to respond.

“So, if you’ll get back to your copy machine, I’ll put the final touches on this presentation. Oh, feel free to take your purse to the lady’s room and powder your nose if you need to. I understand how important that can be for a woman.”

“Of course, Mr. Parker, I’ll be right back.”

It was my first visit to the lady’s room. I sat in a stall and looked through what seemed to be my purse for the time being. It was exciting to sort through the feminine personal effects. I found a cellphone in a pink case, makeup, and a tampon. I looked at the driver’s license and wondered if I could really pass as Elise Johnson. I wasn’t sure when this would end or whether I even wanted it to end.

I stood in front of the mirror and applied lipstick generously to emphasize my lips. I found mascara and eyeliner, so I used those as well. When my face looked presentable, I returned to find Mr. Parker practicing the presentation.

The unmistakable odor of cigar smoke accompanied a deeper, more assertive tone of voice than I was used to. And I could see a glass of whiskey, neat, on the desk. Everything was just the way that Mr. Parker liked it. I felt a new thrill of excitement as I anticipated what Monday might bring.