One reason I joined this online community was to share some of the experiences and insights I’ve gained from 10 to 15 years of public crossdressing, including what I refer to as “extreme” crossdressing. I have frequently took this behavior to the extreme, including sexual extremes at bars (straight and gay, picking up guys and girls), strip clubs (the kind with regular female dancers, where I’ve worked the floor with the girls dressed like a stripper and even danced on stage), and hotels and motels (where I’ve had sex, got drunk, and did drugs with guys and girls I picked up)…. you get the idea. I lived a very wild and crazy gender-bending life for many years. I took risks that most people would not take. I do not encourage this type of behavior, but I did it, and I don’t regret it. Although I got into a bit of trouble with the law a couple times, I had a total blast, and I can truly say that I have lived all my sexy female fantasies. Best of all, I’m still alive and healthy (at least physically, mentally might be subject to debate).
I didn’t start most that crazy public CD stuff until I was in my late 40s. Before that, I was a private crossdresser. Now, as I approach age 59 in a couple months, I have left that crazy life behind. Frankly, I got too old for it, and it got too crazy for me. But I feel I have gained some wisdom, or least entertaining stories, from living the wild life. And I would like to share some real-life stories with you, in the hope that, as fellow crossdressers, you might find some of them interesting. As I said, I do not encourage this kind of reckless behavior in others, but…
Here’s one example of my extreme crossdressing… something I did in early 2018.
I went dressed up like a stripper to a “lingerie bar” in Melrose Park, Illinois, called Bobby’s Bar. Such places are a cross between a regular neighborhood bar (with pool tables, TVs with sports on, and a jukebox) and a strip club (with a small stage with a pole, and chairs in a dark corner for lap dances). The girls who work in these places walk around in sexy underwear or short dresses and hit on the male customers for lap dances (about $20 for a three-minute dance) and tips. Generally speaking, these ladies are not as attractive as the girls who work in real strip clubs. My dancer friends say that places like Bobby’s are “where old strippers go to die.”
On the evening I was there, I was actually the best-looking “woman” in the place (except for one sexy blonde named Stephanie, who I paid to give me three lap dances early in the night). I was looking pretty hot, wearing a shoulderless black leather minidress, big fake boobs, long blonde wig, lots of eye makeup, fishnet pantyhose, and silver strappy heels. But anyone with eyes and basic perception abilities could still tell that I was really a guy. My big hands, big feet, and big nose always give me away, as does my voice (which I can make sound feminine if I want to, but I usually don’t bother). Despite not being “passable,” I have found that straight, horny men – even if they’re not particularly drunk – will be quite eager to screw a “tranny” if “she” looks sexy enough. Plus, the way I wear makeup makes me look about 20 years younger than I am, so I am often approached by guys in their 20s or 30s.
So as I sat there at the bar feeling sexy but minding my own business and sipping my chardonnay, guys kept coming up to me, buying me drinks, and asking me for lap dances. I kept telling them that I didn’t work there, so I couldn’t do that. But finally, with about the fourth guy that asked me, I said yes. I took his hand and walked him to a chair in the dark corner, I sat on his lap, and I starting grinding against his privates. I know how to give a good lap dance. He had his hands around my waist, and we were about a minute into it, when the manager rushed over and shouted at me, “No no, you can’t do that. I’ll give you 15 minutes to get out of here, and then I’m calling the cops!” I didn’t argue, because I knew I broke the house rules. I just grabbed my purse and immediately left. I actually thought the manager was being pretty nice giving me those 15 minutes. All I needed was a couple. I felt sorry for the guy I was giving the lap dance to, though. He seemed to be enjoying it, and he did give me 20 bucks.
I must say that I walked out of that bar in my high heels feeling fabulous! Like a naughty rebel chick! Then I ubered to one of my usual real strip clubs, the Gold Room, to tell my dancer friends about it. They thought it was hilarious, and they laughed their pretty butts off!
A couple weeks later, I called up Bobby’s and talked to the bartender, Amanda - the same girl who was there the night I got into trouble. I apologized for breaking their rules, and I asked if I could come back there again in drag. I liked that place, because it seemed warm and welcoming. Before I was naughty that night, one guy came up to me to congratulate me on being there dressed the way I was. He told me, “I like what you’re doing!” So Amanda told me over the phone that I was welcomed back there anytime – but I couldn’t give any more lap dances! That was cool with me.
This story provides a good example of an observation I have made many times. As a crossdresser going to new places, people will generally treat you with respect and even admiration –provided that you, in turn, respect other people in the establishment, as well as the rules of the establishment. That’s the best way to have fun and stay out of trouble.
Nevertheless, a little trouble can feel good!
I was together with my wife for 35 1/2 years and took the term, "happy wife, happy life", seriously, so I couldn't do what you did, but I can sure fantasize about it! Thanks again for sharing!
Originally Posted by JessicaJelena
