My Night Out As A Woman

Johnnyt

Johnnyt

Burn all jump cues
Silver Member
Back in the 1960’s in Oceanside, NY three sisters dressed me as a woman. They put a dress on me, a blonde wig, and make up. Then the three sisters and some other friends that were at the house went to our hang out at the Club 400/Town Tavern in Oceanside. After many drinks we came up with the idea to take me to the next town (East Rockaway) and see if I could hustle some guys on the bar table.

When we walked in there were at least six people that knew me there. Not one of them caught on who I was or that I was a guy. The sisters had really done a great job on the make up and other stuff. I played two guys, beating them for small amounts of money, which I think I gave back a few days later. I am going to see if I can locate one or more of the three sisters to see if they have any pictures of that. I believe some pictures were taken at their house before we went out.

My point is it can be done pretty easily. Johnnyt

PS: Cookie, Duffy, or Flossy, if you or someone that knows them could PM me, that would be cool.
 
Blue Hog ridr said:
Johnny, I want to see pics. Did you have a G String and black nylons on?

You little hottie.
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I really don't remember, but if one of them helped me on with them, then the answer is yes. They were the hottest girls in town. Johnnyt
 
If they had made a video of that it would be titled, "I Led Three Lives: A kindly old gentleman, a pool player, and a hooker." You old dog, you. :smile:
 
Johnnyt said:
Back in the 1960’s in Oceanside, NY three sisters dressed me as a woman. They put a dress on me, a blonde wig, and make up. Then the three sisters and some other friends that were at the house went to our hang out at the Club 400/Town Tavern in Oceanside. After many drinks we came up with the idea to take me to the next town (East Rockaway) and see if I could hustle some guys on the bar table.

When we walked in there were at least six people that knew me there. Not one of them caught on who I was or that I was a guy. The sisters had really done a great job on the make up and other stuff. I played two guys, beating them for small amounts of money, which I think I gave back a few days later. I am going to see if I can locate one or more of the three sisters to see if they have any pictures of that. I believe some pictures were taken at their house before we went out.

My point is it can be done pretty easily. Johnnyt

PS: Cookie, Duffy, or Flossy, if you or someone that knows them could PM me, that would be cool.
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You know what's funny. Pancho wanted to do that with me. He told me I was cute enough to be a girl. He was serious too. He had a plan for us to play scotch doubles in a joint where they always played doubles. He laid the whole trap out to me and it did sound promising. But when the time actually came to getting dressed like a girl and putting make-up on, I chickened out. Pancho was really pissed at me but I just couldn't go through with it. Johnny, you're a braver man than me! :thumbup:
 
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jay helfert said:
You know what's funny. Pancho wanted to do that with me. He told me I was cute enough to be a girl. He was serious too. He had a plan for us to play scotch doubles in a joint where they always played doubles. He laid the whole trap out to me and it did sound promising. But when the time actually came to getting dressed like a girl and putting make-up on, I ducked out. Pancho was really pissed at me but I just couldn't go through with it. Johnny, you're a braver man than me! :thumbup:
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I'm not braver than you. You don't drink. I did. Johnnyt
 
jay helfert said:
You know what's funny. Pancho wanted to do that with me. He told me I was cute enough to be a girl. He was serious too. He had a plan for us to play scotch doubles in a joint where they always played doubles. He laid the whole trap out to me and it did sound promising. But when the time actually came to getting dressed like a girl and putting make-up on, I chickened out. Pancho was really pissed at me but I just couldn't go through with it. Johnny, you're a braver man than me! :thumbup:
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Mayyyyyyyyyyy Be Smarter............:grin: What name did Pancho have planned for ya?
 
Island Drive said:
My guess, you look Mooch better ;) than Kieth McCready it that frikin' gladiator outfit, but maybe NOT :thumbup:
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Well, truth be told, Keith wasn't too happy about it, either. :o
 

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Interesting story. I'm not so sure I would have told it to this crowd!!!

P.S. I was too busy standing in line at Nathans getting some hot dogs and then going on the rides at their amusement park. I'm sure you remember that place on Long Beach Rd.
 
questions questions

which did you enjoy more the pool playing or the dressing up

and do you still on occasion dress as a lady ?
 
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