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!
What I didn’t anticipate was how my new heels would slow me down. I parked a good 6 blocks away from his place. The freshly bought heels and tighter than I realized skirt made for a very, slow, walk. A few post bar drunks eyed me, which would normally turn me on, but I could only focus on trying to keep balanced on two feet. It was the longest walk I’ve even done dressed, and once it was done, I didn’t even realize the thrill it was.
That thrill slowed when I read his text that told me he was on the 4th floor. 4 floors in heels? My ascent was even slower, but just made me want his cock more. Matt was sweet and let me in, and gave me a few to freshen up, as the walk disheveled me a bit. He was full of compliments, and agreed to take some pictures of me. Sadly, I’ve learned many gentlemen claim to have an eye for photos and creative positioning but in fact don’t. Matt, as nice as he was, didn’t have a great eye or the creativity, but we made due. He had me sit first, then slowly open my legs to tease myself through my pink panties. I then suggested laying down on his couch, which lead to some nice pics of me on my stomach, legs in the air. Matt found himself straddling me, and I couldn’t ignore his cock. I brought him aside me on the couch for a bit of cock sucking, eventually moving to the floor and being on my knees.
What Matt lost in creativity and eye, he made up for in volume. For one, his cock was a perfect size. Secondly, he took a ton of pictures. A lot. So much that when I flip through them, it looks like a flip book. I would have asked him to take video, but that seemed a bit too complex for him, so i moved him to the couch to really get down on his cock.
My one other slight compliant is one I find with the gentlemen who’s cocks I end up sucking. I try to make it clear beforehand that I want to be told how much of a slut I am, how I want a cock slapped on my face, to spank me hard…but none of them are up to the task. It takes a bit to get face fucked, way more than I thought would be an issue. So it was up to me to take charge, and talk dirty each second his cock was out of my mouth, and then get it back in. Matt laid back and let me do the dirty work, and before I knew it, I was taking a load of cum on my face and in my mouth.
He was so sweet to offer clean up, and I took a towel to wipe my hands. But my face was to be left with cum. I took a quick look at the pics and thanked him politely (I was happier with them when I really reviewed them later, but I didn’t express any dismay to him). I Grabbed my coat and walked back down those big stairs, back down another 6 blocks to the car, cum all over my face. I went home to review my new collection of pics, and get my cock off in my pink panties to them…
Source: reddit.com/r/gonewildstories/comments/75er9l/crossdresser_cindy_takes_a_long_walk_for_cock_tm