Author: Cindy_CD

More Cindy adventures! [xpost /r/cdstoriesgonewild] [TM]

Cindy had herself one hell of a night!

A new haul from a Target run finds Cindy in a new black lacy dress, a new wig, some sexy new heels, her usual pink fishnets, and a bad attempt at some make up. She had herself a nice hotel room for the night and after getting herself all dolled up, she was ready for action.

The first action of the night was a gentleman who asked Cindy to come his way. While the comfort of her room was nice, there’s always something slutty about heading around town dressed like a slut. 15 minutes up the road, and a few text messages later, “Al” came out to meet Cindy in front of the hotel and escort her to his room. Al wasn’t a tall guy, but he was handsome, and ready for fun. I had Al take a few pictures of my new outfit, and soon enough, Al couldn’t keep his hands off me. His cock sprouted out soon after, and before she knew it, Cindy was on the bed with his cock in her mouth. Al got the jist of what Cindy wanted, and started to fuck her mouth some, getting more aggressive as he went. He took a break to not pop right away, and went to town on Cindy’s little fuckstick, licking and sucking it nicely. Soon Cindy needed her mouth back on his cock, and Al didn’t argue. A minute of two later, Al expressed his need to finished, and Cindy begged for it on her face. Cindy flipped onto her back, head hanging off the bed, and Al jerked that cum all over Cindy’s little slut face. She made she that Al took a couple of pictures of her used, spent, and covered in his cum. Read more »

Crossdresser Cindy takes a long walk for cock. [TM] (xposted to /r/cdstoriesgonewild)

It starts with another night of it being late and Cindy being horny. I had posted on Craigslist, but most of the reply were duds and flakes. One gentleman, we can call him Matt, emailed late and wanted to go right to text. That’s usually not my style, but I cut him a break. As it had it, he was in a tricky part of town, one where it would be hard to park in, and just about the hour of bars letting out. He seemed innocent but eager, and I next thing I knew, I had my short jean skirt, pink fishnets over black pantyhose, cute plaid shirt and tight top on, with these new little Mary Jane heels on.
I drove into town full dolled up, wig and makeup all done, pink press on nails and all. It took a good half hour to park, and I continued to send Matt updates so he’d know I wasn’t flaking. My spot wasn’t even legal, residents only, but I’d be damned if a ticket was going to stop me now! Read more »

Cindy sneaks up to a small hotel room to play [T/M] (xpost /r/cdstoriesgonewild/)

As many of Cindy's adventures start, I took a bit of a shopping day to myself to find some new cute outfits, and specifically some new wedge heels. After exchanging a few emails with a few gentlemen, I got a pretty good vibe from Tony, who was staying at a fancy hotel downtown. Already dolled up and having teased myself, I jumped in the car and headed to him.

Now, as I've noted before, I'm not fully passable, so going to meet someone in public or a hotel can be a little tricky if I'm going while already dressed, but it can be quite a rush! What I didn't was that this night was the craziest of all. The hotel is in a section of downtown knowing for having as little parking as possible, and as I started to circle the blocks around it, the police had blocked off a few streets. I had to mange to not look too suspicious while driving, try to park discreetly, and not walk by all of the cops (who would have clearly taken me for a lady of the night in the tiny micro skirt and fishnets I was wearing: http://imgur.com/SW0rBeu). It was about 2am on a weeknight, so most bars had closed up, but there were a few cabs and late stragglers on the streets, and I got my fair share of looks as I tried to be discreet and pass as much as possible. There was no avoiding the lobby of this upscale hotel, however, and once inside, I walked through like I owned it and charged right into the elevator. Read more »