Monthly Archives: June 2014

I don’t venture out crossdressed often but since it’s nice out I figured I would give it a whirl. I posted my ad on Craiglist for car or outdoor fun. Quickly the responses flowed in from all the horny men interested in using my mouth or playing with the cock in my panties.

I already chose my outfit. I wanted something comfortable and tight. I had black sweat pants that were loose at the bottom but tightened on the way up my legs and around my ass. I wore a short sleeve shirt with a pair of red lips across the boobs and then a tight pink hoodie to put over it. I supposed a looked like a comfortable slut.

I started chatting with one horny guy that was nearby. He was very interested in sucking my cock. I made it clear to him that I was a crossdresser—not a tranny and that I wouldn’t be wearing any makeup. I sent a photo of myself in my outfit. He didn’t seem to have a problem with any of that and gave me an address to go to. I thought we would be meeting up in a parking lot for a little car fun but little did I know I was in for a surprise.

We exchanged messages I headed towards his location. He was helping me navigate the way as I did get lost for a little bit. Finally I arrived at a parking lot a few towns over. I was sitting in the car with my hair on and suddenly two guys were walking down the street. I looked down at my phone as they passed and they didn’t seem to notice me—thank goodness. I wish they did notice me because I would have sucked them both!

The guy I was meeting was starting to delay. I suppose he was just as nervous as I was! I asked him to come out to my car and he wouldn’t. That’s when he asked me to get out and go to the house next door to the parking lot. I wasn’t planning on getting out of the card and going into someone’s house. This was going to be a challenge for me.

Well I was already there so I figured what the heck. There wasn’t much activity going on besides cars driving by. This will be an adventure—hopefully I won’t get killed. I did tell him that he must be in my view once I get closer to the house and he was. I quickly darted out of the car and into his backyard where he took my hand as if I was his date and guided me to the side of the house.

I stood in front of him with the street light shining on my face. I wonder what he was thinking of me? He mentioned that I was tall. Well he was shorter than I. He asked if I was nervous. I said yes—it’s not often that I dress up as a woman, drive around, park in a parking lot then get out and end up in someone’s backyard.

Well, I didn’t come all this way to chat so I quickly embraced him and began to rub his cock through his jeans. I felt it twitch and become hard. I moved closer pulling him into me. Rubbing, grinding…we both got hard quickly. I dropped to my knees and pulled his hard cock out of his pants and began to suck it. After sucking for a few moments I got up and then he went down and began to suck my cock. It felt so good.

He pulled his pants up. That was it? No. He then asked if I wanted to go inside. Sure, that would be better…that way we don’t have to be worry being spotted by curious neighbors. He told me I had to be very quiet. I wondered if his gf was upstairs sleeping. Should could have been. Too bad she doesn’t give him the attention that he needs. I’ll give him what he wants though!

He quietly led me downstairs to the basement. I picked a spot by the washer and dryer that looked like there was enough room to play. We then both unleased our hard cocks…rubbing them together, stroking them…taking turns sucking each other. It was dark and intense. I wanted to taste his tight virgin as so I turned him around and bent him over the washer. I spread his cheeks and buried my face in his tight ass…penetrating it with my warm wet tongue—he moaned in pleasure.

Next we fell to the floor. I was on my back and he sat on my face. His large cock and balls taking turns in my mouth. Then his asshole was bouncing up and down on my tongue while he jerked and sucked my hard cock. We were both hot and sweaty. What to do next?

I propped him up on the washer. His legs up in the air and spread. I rested my cock between his cheeks and grinded it into him. I massaged his hole with the tip of my cock while I jerked him off. I rimmed him some more…pleasuring his tight ass with my tongue. He was about ready to cum and he did—all over himself. I tasted some of it by licking it off the tip of his cock. As he shot his load I stroked him slowly making sure I emptied all his seed out of his balls. Once it was all out I caressed his cock and balls some more—making sure he felt supported after his naughty little encounter with me.

He cleaned up and lead me back upstairs where I quietly left. I found out later that he was upset that I didn’t cum too. I told him it was okay and that I was happy he got off good. I consider my outdoor crossdressing adventure a success and looking forward to another one!

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