Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years.
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I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a little bi, and had only every played with myself; anything i could use for a dildo from time to time, jerking off to sissy and CD porn. That kinda thing. Almost always though, after I came, I lost interest and went back to being 100% straight. Sound like you? Well let me tell you, just do it. ONCE. And you'll see that you want to do it again. At least, if you had a similar experience for your first time.
I was living in Charleston, SC at the time (alone) and would drive up to Virginia to see a few girls I knew semi-regularly (like once every month or so). So before i leave for another trip up north, I'm extremely horny, looking at sissy hypno and found myself getting more and more emboldened by it. Now, I had been crossdressing for a few years, so I had a few outfits, heels, a wig, etc. but had never ventured outside wearing any of it. Totally closeted. I went to the shower to get ready and found my razor (I like to keep things totally shaven down below and since I use my ass from time to time, that's shaved also), but this time I said fuck it. Its winter, I can get away with it, so I totally shaved my legs, face and downstairs. Hey, if any one says anything, I'll just say I lost a bet. Who cares?
Well as I'm doing this, I again, said fuck it and instead of boxers, I opted for a cute little pink thong and some knee high white stockings (which were on under my jeans and under my socks). I packed a bag full of my girlie clothes (and my regular clothes) and set out.
I'm now just coming up on South of the Border (NC-SC Line) and I notice a car coming up behind me, which was unusual because I was moving along about 80. Not being a complete asshole, I pulled into the middle lane and as the car came up alongside me the driver and I locked eyes and he just gave me the head nod and kept moving. Well. I wasn't about to be shown up, so I floored it and caught up to him. For the next 50 miles or so (no cops thankfully), we were hauling ass, following one another and in general being a couple of idiot kids. I saw him pull over into the far right lane so I was about to make my move to pass him and noticed he was slowing down a lot; too much to just give a casual wave, he was going to take the next exit. Not really thinking anything of it, I just pulled alongside him, going to give him the thumbs up and smile when he looked at me, smiled and did the unmistakeable signal for sucking a cock.
At this point I'm torn. I recognize that I don't know this guy, I'll never see him again and I'm already dolled up a lil bit and had been fucking my ass just earlier that day with my 6in dildo...why the hell not now? I'm still horned up, and thinking, its just a BJ and at least you'll see whether or not you like it, and so I flashed him the thumbs up and nodded and he motioned for me to take the exit with him.
About 10 mins go by of us driving down some small city streets, I see him point his arm out the window signaling to park along the street. I do it and I get out of my car as he pulls into the parking lot of an apartment complex across the street. I follow and he gets out of his car and looks me over with the elevator eyes; hes a good looking guy. I've never considered myself able to say "he's cute", but I am comfortable enough saying when a guy looks good. He's about my age, in shape and slightly taller than me. He just says, "lets go hotshot". And that was about the extent of our introduction. No names, no back and forth banter, no "do you have a significant other" etc etc. It was just, lets get down to business.
We get upstairs and fortunately he lives alone also, and he just says, "what do you wanna do? What are your limits?"
