A crazy idea comes true

I’m just a regular middle aged guy from the northwest. I’ve dabbled in gay and cross dresser websites and chat rooms. Who hasn’t? 

Last year I was on a golf vacation in Seattle. Nice golf course. I traveled with a buddy who knew a few guys there who we golfed and ate dinner with. My friend unexpectedly had to leave a day early so I booked a flight the next day, cause I wanted to play one more time there. So the next day, after our round, I found myself in Downtown Seattle with nothing to do all afternoon and over night. My flight doesn’t leave till 4 the next day. I’ve got a lot of time to stay out of trouble. 

It turns out there is a new drag club right around the corner from my hotel. I’ve never been to one. I’ve only dreamed of being with a cross dresser or a trans gal. What could it hurt to have a look?

At 5 in the afternoon there wasn’t anyone there. The lonely bartender poured me a Seattle brewery hazy IPA.  A few people wandered in and out  I found out the show didn’t start until 9. Well, this is a bust. 

As I was about to leave, a tall middle aged man sat next to me. He is Sherry. “Not Jerry?” I asked with a laugh. 

Sherry dances there tonight. She looks like a regular guy. She says sometimes it takes her 3 hours to get ready. She has the bartender pour me another beer and she joins me. We chat about stupid stuff. The she asks why I am there. I lie telling her I walked into the wrong bar. She leans in close and whispers in my ear. 

“I know you’re in the right place. Wait for me after my show. I’ll be done at 11. 

i wank off to sissy porn back in my room. I have a late dinner and wander back to the bar . It’s 1030 now. The place Is wall to wall people. Mostly gay couples. Lots of them. I’ve never been to a gay bar before either. I find my way in just in time to catch Sherry finishing her set. She is just walking around the small stage seductively in a long white gown singing karaoke to ‘ I did it my way.’

her long shapely legs  showing from behind the long gown through long slits in the dress. Her white thigh highs lace tops are easily seen under the dress. Very sexy. She has large breasts showing through the see through lace dress top. Sherry is wearing a long blonde wig and a lot of make up. I suppose that’s a signature of drag queens, but I’m not so thrilled with the over done look. 

Suddenly she notices me by the bar. She motions to the bartender and i immediately get a fresh beer. “It's nice to know someone.” a guy tells me, with a wink. 

Embarrassed, I blend into the crowd and drink my beer. 

There is a hand on my shoulder. It’s a crowded bar so I didn’t think anything about it at first. Then another tap. “Oh!” It’s Sherry. 

“You liked the show? We have a place in the back for drinks. You want to join us?”

Without a response from me, she takes my hand and leads me through the crowd to the back of the bar. Behind the stage is a door and a hallway. We go into a back room that is actually another bar that you can access from another street around the corner. It’s much quieter. We sit with 2 other drag queens and their boyfriends. One is an older guy about 50, like me. We sit and chat and have some drinks like regular people. Suddenly I feel like this is just a nice time with a few nice folks out for martinis. 

Things wind down as the clock strikes 12.  Seems we are breaking up the party. Everyone heads back to the gay bar with me assuming that’s the end of the night. I’m disappointed, and relieved. But I’m wrong of course. The bar is closing down, but the party isn’t over. With the doors locked and most of the lights off, the music comes back on. One of the drag queens takes her date up on the stage, slow dancing and kissing. Soon the dress she is wearing falls to the floor. The guy’s shirt is open and mostly off as well, She is wearing very sexy burlesque style lingerie. Very sexy. We all watch as they grope each other and kiss deeply. Before I realize what was happening, she drops to her knees and starts sucking his cock through the opening in the front of his slacks. Everyone is commenting and laughing. Apparently she had need rubbing his cock in his pants for a while. After a few minutes of this, she stops and takes her man, cock still hanging out of his pants, back out of the room, disappearing.  

“Where did they go?” Everyone just laughed.  

Sherry was holding my hand. She moved toward the stage, pulling me along. I looked around for support by I only received a “Go get her, stud!” And a “It’s your turn, big boy.”

On the stage, a slow sweet song began. Chris Isaak’s Wicked game. 

Her hands were on my face holding my face gently. She leaned in, giving me a soft kiss on the lips. I barely kissed her back. I was embarrassed. “Go on, Bill, kiss the girl.”

Sherry looked me shyly in the eyes. Hoping she hadn’t made a poor decision and picking a guy who wasn’t interested in her. She looked sweet, vulnerable and like someone needing a friend. I leaned in and kissed her back. Her lips tasted like cherries. We held the kiss. I slipped my tongue between her lips. Not sure if that would be allowed or received with approval. She took a deep breath and sucked it deep into her mouth. She was needy and affectionate. I’ve made her night I felt like. Her arms wrapped tightly around my shoulders and neck. We took a moment. She whispered to me as she kissed my neck. “I was afraid you’d not like me. Thank you for being a good sport.”

Her tongue slipped into my mouth. I’ve never had someone kiss me like that. She held me close. I felt like the tables turned. She was on top so to speak. “Will you do what I want?” I looked fondly into her pretty blue eyes. “Whatever you want, Sherry.” She took my hand, sliding it down to her tummy, then lower. Her dress was split open. My hand slipped right up under her crotch. I was cupping a large cock and balls wrapped tightly in satin and lace panties. “You know I’ve got a cock. I’d like you to suck it for me.” The small crowd was pretty much home. Only two people left. One queen and her man. They were kissing. They weren’t paying any attention to us. 

A kiss and a cock.