Tag Archives: Crossdressing

Undercover Part 1

Almost twenty girls have gone missing after enrolling into a new two-year private college in town. The CIA wanted to enroll a girl to investigate but it seemed far too risky, so they sent me instead. My name is Kyle, a 26 year old guy, and I’m going undercover as Kylie, a 19 year old girl. After extensive makeup and latex work the team was able to create a totally indistinguishable college girl. I’m supposed to stay low, wear dark clothes, and not really stand out. They’ve sent me in as a sophomore so I’ll already be a year into the program.
The admissions office was beautiful, with lovely ornate furniture and tapestries. I sat in a chair across from the desk of my advisor, making sure to cross my legs so that I would look feminine. I took many classes at the CIA on feminine behavior to make sure I didn’t blow my cover.
“Kylie Shaw,” the advisor said, looking at some papers, “Unfortunately some of these credits you have listed here will not transfer without taking a placement exam.” She peered over the papers at me through her glasses, “Is that acceptable?”
“Of course,” I squeaked.
“Very well, Mrs. Shaw. If you will follow me to the testing room I can get you started right away.”
The tests were ridiculously easy. The math problems were very basic and the english test read at what seemed like a fifth grade level. The final exam, a personality test, was by far the weirdest. The questions asked where a woman’s place was in society, with answers like “Beneath men, equal to men, or above men.” I tried to stick to answers that showed equality. I exited the room, as instructed, and waited in the hallway for my advisor.
“Mrs. Shaw!” she called, “Your scores are ready.”
I entered her room and took a seat.
“Unfortunately you scored too poorly on your placement exams to allow us to transfer any credits.”
“What? That must be a mistake,” I said. How could that be? The tests were so easy!
“Don’t worry, many girls struggle on our tests when they first arrive. We will be enrolling you in some faster-paced ‘core classes’ that will help boost your scores so you can get right back on track next semester.”
— Next Week —
I filed into my first remedial class, forcing myself towards the back of the room. I felt ridiculous, how could I score so lowly? The teacher turned off the lights, put on a video, then quietly exited the room. The video was colorful and vibrant, narrated by an extremely upbeat young woman. She talked a lot about math but I couldn’t focus. The class felt so beneath me. Before I knew it the bell had rang and the class was over. Three hours, gone, and I didn’t even realize it. The teacher gave us homework to take home and I made sure I took a look at it before my next class.
“What is two plus two?” the first question said.
“What an easy one!” I thought, tracing the problem with my pencil. A minute passed however, and I still couldn’t come up with an answer. I continued to trace the problem with my pencil, searching my mind for an answer before I heard the bell ring for my next class. Looks like I might need to pay more attention in that math class.
The next class was very similar to the last. The teacher put on a colorful video and left the room. I tried to watch this video instead of dozing off like the last one. The narrator talked a lot about toys, which sounded like a lot of fun. Everything the narrator said was true and made a lot of sense, I found myself really trusting her. She told the class that girls are toys, and that, sense we’re girls, we must be toys. It kinda sounded wrong but I wasn’t about to argue. Before long the teacher gave us homework and sent us home. Maybe I’d do better on this class’s assignment.


“I’ll see you tonight, Molly,” she said with a wink. I wanted to gag. Me and my wife are known to take bets, and we often push the stakes farther and farther. After winning my last bet and making my wife dress like a dog all day, she’s stepped it up by forcing me to dress like a girl all day. She shaved my whole body, got me a wig, some breast forms, and did an incredible job on my makeup. I was already a pretty slim guy, so she had a decent canvas to work with. I had to give her though, unless someone literally took off my pants and saw my dick there’s no way they’d know.
The day was pretty boring. I didn’t want to leave the house, obviously so I mostly texted my friends. Any snapchats I got I replied with pictures of objects instead of myself. However, I wasn’t able to avoid people forever. When I went to the fridge to get something to eat I found it totally barren, my wife must’ve dumped it out before leaving for work. I went online and ordered a pizza, hoping I could make this experience as minimal as possible. Read more

Fine Print

“You’ll do anything?” John asked me with a knowing smirk that urged me to say no, but I was really short on cash after being unemployed for a month.
“Yes I will do whatever you ask no questions asked for the $500.” 500 seemed like a steal for only four hours. With little money I had quite a skinny body. Dispite doing pushups and squats everyday I was never able to put on the muscles I wanted.
“I’ll start right away what do you have planned?” I was eager to earn some quick and easy cash.
“As you know I run a modeling company and one of my models canceled on short notice, which is why I am offering you the $500. The first two hours will simply be a makeover but it is a long and boring process as I’ve been told so I can give you a tablet to let you sleep during that time and you’ll only have to work the other three. I will need your full consent to continue with the process and your signature on this paper that all my models sign and it also ensures you the $500.”
A contract only made sense as I’m sure it is standard in the modeling business so I quickly signed sat on the chair and swallowed the pill. Soon after I quickly dosed off.
As I awake I see a pretty girl in the mirror in front of me. I guess the model must have come in while I was sleeping, good thing I signed the contract so I’ll still get my money. I get up to find john and realize that I am the girl in the mirror.
John walks up behind me, ” We are short on time Jack so you need to do exactly as I say in order to earn the money so no talking and go stand over by that red wall and start posing.”
I was really desperate so hurried on over and striked poses for two whole hours. I was nervous at first but slowly got into it as nobody would possibly revognize me.
“Alright we are done with the shoot.”
“Finally now …”
“Hold on you still have one more hour. I’m gonna need you to come in my office for a moment Jackie.”

comfy at work

john always noticed how comfortable the girls in his office looked . they mostly wore leggings and loose tops. one night after work he brought the subject up with his girlfriend and she suggested that since there was no dress code against him wearing leggings that he should wear some of her clothes to see if he was comfortable in them . He borrowed her leggings and this cowl neck top but he did have to go out and buy his own knee high boots as his feet were too big for hers.

High school reunion

John had been hoping that he would see Sharon his high school love at his class reunion. He wasnt sure what she would do when he dsaw how he had changed. he now was a pretty woman. but he still had always wondered what life would have been like had he and Sharon stayed together. Sharon was in shock and could not believe that she was actually talking to John as she saw this beautiful woman telling her/she was John