Craigslist CD Hookup

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensationalize or b.s. in any way. All is true, factual, and really happened. I'm actually going to begin my first story with my most recent experience that just happened two days ago (at the time of this writing). I will also spare you the long drawn out descriptions that most stories have. I'll basically get right to the point in what I want to share so you can enjoy without reading a lot of crap.

I like going out for a drive while dressed. My wife knows I dress so it's not hard to get out. I also really enjoy getting fucked by guys while dressed! I have had many sexual experiences as a CD. This most recent one was one of my best ones, and this prompted me to finally submit a story.

So I have been having cock withdrawal for some time now, it's not easy finding someone who is sane and will actually follow through with meeting up after the arrangement has been made. Been let down many times. Well, my dry spell ended two days ago when I had put an ad on Craigslist. I was surprised at the response. I usually get 2 or 3 replies, nothing of which ever comes of it, but this time was different. They were almost begging me.

I picked the one who seemed the most serious and went from there. He is also married and was OK with meeting up late at night. I'm not passable so I go out at night and drive around. I enjoy that and how it makes me feel. We agreed to meet up. This is the point where the butterflies come out in full force. You just don't know what you're getting into so it's a risky thing to meet someone for the first time. But off I went to meet him where he told me he would be...his house! He wanted to fuck me in his van while his wife slept in the house! That was a hot prospect! But there were some other things that made this whole experience the hottest one yet.

I was wearing a black mini dress, black panties, black Vasserette pantyhose and my favorite black heels with a strap over the top of the foot. I also had a small purse for my keys, cell phone, and lube (in case I needed extra, but I'd already lubed up before leaving the house. I've always had a fantasy about showing up to meet someone while already dressed up. I lived this out once, a while ago but I parked right beside his house and only had 2 feet to get to the door. This was gonna be different, very different indeed. He asked that I park across the street at the fire hall, walk across the street to his van and get in...and have our fun! So I arrived and parked in the parking lot at the fire hall. I got out and locked my car, took a deep breath and with each click of my heels in the night air I was living out one of my deepest fantasies.

Across the street I walked, probably 100 feet or more, and got in his van. He was waiting, pants off, stroking a nice size cock. As agreed, there were no words, and no condom! He was married and had car seats in the van so I took a chance and trusted that he was OK and safe to bareback me. So without words, I lifted my dress and lowered my pantyhose and panties, and he fucked me good, for a good 5 minutes. It was incredible! He professed he was going to cum, and that's what I was there for! Being barebacked was also a fantasy, so here I was living out TWO fantasies at once! He exploded in me, it was a wonderful feeling! When he pulled out with a pop, I felt his cum running down my ass crack. It was an amazing feeling! I then took care of myself, cumming in my panties and pantyhose (pulling them up just before blowing my own load). We thanked each other and now I had to walk back across the road to where I parked. His cum was leaking out of my ass for the next day. I had heard so much about being barebacked and I can tell you, it IS as awesome as others have said it was!

I'll add more stories after this one, of my past (and first of course) sexual experiences with men while dressed, and also some things I don't solo as a crossdresser. Hope you enjoyed.