[Fiction] Crossdress Adventure

[Truckernaut42]

As someone who has always looked somewhat feminine (think, 70's David Bowie) I've always been interested in cross dressing, and curious if I could really pull it off. I was exploring a fetish forum and posted about my fantasies when someone messaged me. We chatted a bit and he seemed like a nice guy, he mentioned he lived in my city too. I felt comfortable with him so when he asked if I would be interested in him helping me live out my fantasy, I couldn't say no. He asked for my address so he could mail me something, but that I wasn't as okay with. He told me that was fine and if I set up a PO box, that would work fine for him too, so I did that instead. A few days later, I went to check my box to find he sent me a care package of sorts. I took it home and opened it, to find some clothing, makeup, and a wig (which I didn't need since my hair was long), and a note.

If you are interested, text me at this number so we make a date to play. Enjoy.

I texted him.

Glad to see you got my package. I was hoping tomorrow you could meet me at South Mall. Shave any body hair you have, face and legs, and wear ONLY the outfit provided.

I looked through the clothes. There was a short leather skirt, a hoodie that zipped down right where there would be cleavage, stockings and garter, flat shoes, and what appeared to be C cup fake breasts that strap over your shoulder to be held in place. I noticed there was no bra or panties and texted him.

Yes, I did not make a mistake. The fake nipples on the breasts should show somewhat through the hoodie, which I expect to be zipped down. No panties. If someone gets a sneak peak up your skirt and sees your little girl cock, that's okay. Trust me, more than just me will be seeing it.

I got nervous and asked him what he meant.

Don't worry. I will keep you safe. See you tomorrow at noon. Take the bus.

TO BE CONTINUED

[deltavoyager]

Good start! I hope there’s a lot more soon

[Truckernaut42]

I spent most of the night shaving. Face, pubic hair, legs, etc. I got up early enough to do my makeup, using some youtube tutorials. It was definitely tough! Getting dressed had me horny already. That was my biggest worry, that I'd have a boner under my skirt and you could definitely tell. I ended up missing my bus the first time, waiting for my erection to go down to leave my apartment. The skirt was pretty short, but you couldn't really see anything unless I bet over, so I made note to not do that. Using some drag queen make up tutorials I was easily able to blend the cleavage to look like it was real. The nipples definitely showed through the sweater, though they weren't too too big. I took a deep breath and put on a pair of sunglasses and carefully made sure no one from my floor was around before leaving my apartment. My heart was racing. It felt like forever waiting at the bus stop, since anyone could recognize me at any time, but I got lucky. The bus driver didn't seem to notice I wasn't a girl, or if he did, he didn't care, even though I was dressed like a slut. I texted my partner to let him know I was on the way. He told me to meet him in the food court and I did when I got to the mall. I checked my phone quite often to avoid making eye contact with anyone. Suddenly, a hand went up my skirt and grabbed my ass...


TO BE CONTINUED

[Truckernaut42]

I turned around to see a young guy with a backwards hat. Was this the guy? I realized he had never sent me a pic of himself. I was nervous and realized I had agreed to this not knowing what this guy looked like. A male and female came up to me and gave the guy hell for touching me. He walked away with his tail between his legs and I was about to tell them it was okay when the man spoke.

"He was pretty close to discovering your little secret hey?"

I realized this was him... but he had another girl with him?

"This is my wife Logan, my name is Paul." He was an average looking guy, facebeard, brown hair. She was a short brunette, petite.

"I didn't realize there were two of you." I said.
"Yes, but you also didn't ask." He replied. "But she can help us you into certain areas that I can't."
"You should work on your voice a little, you look the part, but as soon as you open your mouth, you reveal yourself." She added.

Attempting to sound more girly, I asked what they had planned for me. First they wanted to go to a more private area and walked me to the bathrooms. Logan took me in and we went into a handicap stall.

"I want to see that girl cock." She said as she pulled my skirt up, exposing my penis. She took a pic to send to paul.

"It's cute and small. I wanna see if it gets any bigger." I frowned, until she put it in her mouth, which surprised me, and began to suck. It felt good and I became hard very fast. She stopped to take a pic and then attempt to pull my skirt over it.

"Damn." She said. "You aren't too big but lucky for you otherwise you never be able to pull this off!"

We left the bathroom and Paul looked amused. "Are you ready for some fun?" I nodded.


TO BE CONTINUED

[Demon Thief]

Ooh, this is getting interesting. Sounds like he's in for a wild night.