The first time I Crossdressed as a woman was actually when I was about 18 for halloween I did the whole thing short slinky mini dress curly black wig makeup lipstick hose and heels I even shaved my legs and arms everything. I went to a party and everyone thought I looked great this was years ago when I was a lot skinnier. I even had a few guys hitting on me and wanting to slow dance with me. Which I did with a couple of them and they were grabbing my ass and squeezing my cheeks and I was getting very turned on by it all. Anyways I had a few drinks, actually more than a few and I decided to leave. Well naturally, I got stopped by a cop on the way home about 2 in the morning. I thought oh my god I'm going to jail for D.U.I. dressed as a woman.
The cop had me get out of the car and do a sobriety test in "HEELS".
Well naturally I failed, the cop said looks like I'm gonna have to take you in. I was scared shitless, I begged him please don't, I won't last 5 minutes in jail dressed like this. Then he said well maybe we can work this out and he walked me over to his cruiser and sat me in the front seat so that I was faceing out the door then he stood in front of me and unzipped his pants and pulled out his cock and told me if I gave him a BJ he would let me go.
I had never gave a BJ before and was so scared yet turned on at the same time. So with out much resistance I grabbed his cock which was probably about 6 inches and I could feel his hard hot shaft pulsating in my hand. He looked down at me and said kiss it, I leaned in and kissed the head of his dick and then he told me to lick his shaft and I did as he said. Then he grabbed me by the back of my head and pushed his cock in my mouth and slowly face fucked me until he came in my mouth, most of which I swallowed while a little bit had oozed out the side of my mouth and then he made me lick his cock clean and suck out every drop until he was soft. He said thanks for the great blowjob, as he put his cock back in his pants and zipped up his fly and told me to drive safe and let me go. I was so thankful , I got in my car and drove home and never told anyone until now about that story. BTW I am still a Crossdresser to this day