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 jerk 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.
Her tits weren't real. Nice little rubber C cup false breast forms in a sexy pink satin and lace bra. She held my hands over them. I squeezed them. I tried to ask what was really going on. I was getting hard. Her tongue was in my mouth, like she was silencing me. She pulled the bra aside and helped me pinch her real nipples. Her skin was warm and smooth. Her big brown nipples were hard and erect. She pushed my face into her bosom. "Suck the nipples for me baby." It sounded like an order. I obeyed.
She held my head firmly in her breasts. i wouldn't have been able to pull away if I'd wanted to. I sucked and licked and tickled the nipples, one, then the other, back and forth. "Mmm you're good at that baby. Don't stop sucking." Another order, I think.
Suddenly she pulled my head back up to her face. A glare in my eyes. She smiled and said: "I'd love for you to be my bitch tonight, baby. Can you do that for me?" I didn't even know what that would be. I didn't really understand it at all. I just obeyed. "Yes, Sherry. What should I do?"
Without any more words, she slipped her tongue back into my mouth. I sucked on it a little. She responded with an approving sigh and pushed it in deeper. Her hands were on my shoulders. I could feel her pressing down. Her tongue slipped from my drooling mouth. I slowly began to move down to one knee, my face back in her chest again. She pushed my mouth over her nipple. I sucked it a little. Another approving sigh. More pressure from above. Before I knew it, I was on my knees with her dress opening up in front of me. Behind the flowing dress panels was a crotch in the same sort of panties matching the satin bra. A few garter straps were running down from her waist holding up the sexy nylon stocking she was wearing. Her hand was on the back of my head, forcing me forward. I moved my legs, scooting my knees on the floor.
"You're a beautiful man, Billy. Be my bitch and I'll love you forever." Her hands pulled my face right up into her crotch. Her cock was bulging and ready to pop out. My hands were on each of her thighs. The nylon stockings felt nice. I rubbed my hands up and down on them a little. The panties smelled nice, like fresh laundry. I slowly opened my mouth and slipped my tongue under the bulge. I licked it a little. "Oh, fuck yes, baby!" He hands pushed me in deeper. My face was under her crotch. My mouth was wide open with my tongue soaking everything underneath. She was rocking a bit rolling her balls and cock in the tight panties against my mouth. I felt her balls slide into my mouth. I had a mouthful of panties and a guy's balls. What wasn't I stopping? I wanted more. I was in a daze. Her hands on my head felt so right. I moved up in front a little and took the top of her panties in my teeth, pulling them away. Her big floppy cock slapped me in the face. Without hesitating, I took it in my mouth and sucked it as hard as I could, like I'd been dreaming and craving this forever.
Everything stopped. The music was gone, as was the gallery. It was Just Sherry and me. She took my hand and lifted me up to my feet. She tucked her cock away and straightened her dress. She leaned in and kissed me on the cheek. "What's going on now?" I asked.
"Well, baby. We are going to turn off the lights, go upstairs, and I'm going to fuck your brains out." She was pulling me by the arm as she spoke. Again, it didn't really sound like a question or a request. More like another order. I shyly nodded. She looked over her shoulder at me with a deviant look in her eyes.
The rest of the night was more of a blur. I was taken to bed and fucked like a bitch. I sucker her cock and took it up my ass for hours, with no chance to rest. She kept me guessing and exhausted until the room and the bed sheets were dripping with cum, sweat and saliva.
I learned later she is more of a top sort of person. And that made me a the bottom, or the submissive, or the bitch.
Billy
