tagTransgender & CrossdressersAbandoned Parking Lot Pt. 01

Abandoned Parking Lot Pt. 01


It begins...

Well, I found out that Anne fucked that professor again. She came to my dorm drunk at 3am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won't even get started on what she was on about. I tried calming her down, but whenever I said anything she just slapped me, or if I tried to stop her from drinking more from her loaded thermos, she pushed me. She said, "I'm going to F*** that professor again. By the way, his cock, is like, way bigger than yours."

I didn't care to chase her down, I just stood in my doorway watching her drunk ass stagger down the hallway. I never cared about Anne, but this just pushed me over the edge with girls.

I've been contemplating following through one of those casual sex listings on Craigslist for the past year, and been browsing those kinds of websites during bathroom breaks or before bed. They get me really hard. Well, I posted one about a week ago and had at least twenty people respond that they were down to meet up. They were a batch of all the races and heights, but all were hung as confirmed by their dick pics.

I don't know what it was, but I just wanted to suck a cock all of a sudden.

I shut my dorm room and the checked the emails on my phone. I sent a mass-text to all of old men, black guys, and fit alphas. Three replied, an old man and two black guys. I decided to meet with the least creepy one, the old man, named "BigBoner". He was a 6'3" bear-type with a 7" cock and a hair-white chest. From his pictures, he seemed sane. He was surprised I messaged him, he said it was late and he didn't expect me to reply since it was already a few days since I posted my advertisement.


Do you want to meet or not? - 3:33AM


3:33AM - Yes baby, of course. Where?


The Wal-Mart's parking lot near Chester Street. - 3:34AM


3:34AM - On the way.

I took my cross-dressing shit out of my hiding spot under my bed, stuffed it in my gym bad, and put on a hoodie. I left the dorms through the fire exit where there's literally no lights so I'm sure nobody saw me. Thank god nobody was out for a smoke.

There was a red car parked at the far end of the parking lot. I looked at the car with my heart racing, looking at the fluorescent parking lamps that led to the car like a cookie trail. The only civilization in sight was the gas station, but that was about good minute run further down the street. I told myself that I already gone this far, I'm not turning back. My heart was pounding. I pulled out my phone. Three text messages from him.


3:40AM - I'm in the red Honda.

3:42AM - Where are you?

3:44AM - Are you still coming?

Sheesh, I thought to myself.


Is that you? - 3:52AM

The car's head lights flashed twice. When I got to the car, I knocked on his window. He rolled it down and he didn't look exactly like his picture. He looked a bit bigger. But I didn't care if he gained a few pounds, cocks don't change size. I walked around to the other side and got in the passenger seat.

When I got in, he just looked at me in awe. Like he was surprised I showed up.

"What is it?"

"Nothing, I'm just excited."

I laughed after noticing the bulge in his sweatpants. "Give me a second." I said, and pulled out the pipe from my jacket and filled the bowl with some weed. "You don't mind, do you?"

He shook his head. I ripped a bowl and asked if he wanted some. He said no.

It didn't take long before the weed hit, and I was fucking horny. I started feeling tingly, light, cute, and becoming more aware of my body. "Let me dress up before we do this."

I put my gym bag on the dashboard and unzipped it. I took off my hoodie, shirt, and jeans and placed them on the dash. Inside the bag, I pulled out a pair of silicon breasts, a bra, a button-up white shirt, a cardigan, a wig, a grey cross-hatch skirt, and some thigh-high white stockings. The outfit resembled a conservative blonde girl from church I always thought of when I masturbated.

End of Part 1

Thanks for reading guys!! I'm working "HARD" on finishing this story, so let me know if you like it so far!

Report Story

bysissyscarlet© 4 comments/ 20013 views/ 4 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartlockee, h0rny_hubby and 2 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by sissyscarlet05/26/18

Thanks so much for your kind words!

I submitted part two!

Also, i'm releasing my novella (20k) soon, so please follow my newsletter for details! sissyscarlet.com/newsletter

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous05/13/18

Great Beginning

I will be looking forward to the next chapter. A very good beginning...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous05/12/18

Oh yeah!

LUV the way this is developing. A nice balance of detail. Maybe a little bit more on what the main character's body type is though.

Is he passable as a blonde church girl or just looks like a dude inmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by sissyscarlet05/09/18

hey guys, thanks for the kind messages :)

you can read more of my stories at: sissyscarlet.com/literotica

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 4 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: