Crossroads

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He meets a special woman at a new club.
1.7k words
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Part 1 of the 4 part series

Updated 10/21/2022
Created 10/08/2003
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Years ago, while I was still in school, I had my first male-on-male sexual encounter. Herb was a good friend, and even better sexual teacher and partner. He and I continued our fun until he left to go to school in Texas.

After he left, I quickly became lonely. We weren’t lovers, per se, but frequent playmates, and the lack of sex was really getting to me. One night, I ventured out to a new bar that some friends had been laughing about. The place was a well-known hangout for cross-dressers and transsexuals, and the things I had heard got me a little curious.

I dressed for adventure, tight jeans with nothing underneath, and a shirt that accented my young, well-developed body. My cock stirred to life as I drove the short distance to the club, but I forced it into submission, not wanting to prematurely end my evening.

I paid my cover charge to the striking young thing working the door. He winked at me as I passed, and I glanced back to see him checking my butt as I passed. Smiling, I went inside.

The stories did nothing to describe the truth about the place. There were stages on either side of the club, with entertainers doing their best celebrity impersonations. I made my way over to the bar, and ordered a beer. The bartender, a very flamboyant gay man, gave me my beer and change with a nice smile, and a few words of greeting.

“New here, aren’t you, stud? Welcome to Crossroads, the best tranny bar in town. Okay, the only one, but still the best…”

I laughed and thanked him.

“Anything I should know about this place? Any hidden rules I should know about?”

“Everything is pretty straight forward here. The only thing you need to know, is if you are given a red wristband, you are welcome to stay for the after-hours party Serena throws most nights.”

“Serena? Who’s she”

“She’s the owner of Crossroads, and one of the most wonderful people I have ever met. She usually comes down around now, so if I see her, I’ll introduce you to her. She likes to meet the new…talent, as it were.”

He grinned, and made a point of checking my bulge.

I smiled, and thanked him for the information.

Spotting an empty table across the way, I grabbed my beer and headed towards it. It’s always been my experience that if you want to meet new people, grab a table to yourself. As a place gets crowded, people will come and talk to you, so as to have a place to sit. I settled in, and before long, a woman came to the table. She was a large woman, and quite obviously, not a woman by day.

“Hey, gorgeous. Mind if I have a seat?”

Across the room, I could see the bartender waving at me, as if to say “NO”!

“Sorry, but I’m expecting some friends to join me soon. Another time, perhaps?”

She leaned over the table towards me, and gave me a big grin.

“I’ll go this time, but you won’t always get away from Big Bertha, meat. I always get what I want, eventually.”

“I’ll be sure to keep that in mind, then.”

She laughed, and moved away.

Just as I started to flag the waitress down for another beer, the most incredible creature I’d ever seen cames towrds me, holding a beer and a cocktail.

“You look like you could use a fresh beer. My name is Serena, and I am the owner of this club. Very pleased to meet you.”

I stood, and offered her a chair next to me. She smiled.

“I have my own reserved booth in the back. Would you care to join me there?”

“Lead the way, Serena.”

We made our way to the back of the club, where it was much quieter, and easier to chat. We spent the next couple of hours getting to know each other, and she introduced me to most of the regulars, and all of the entertainers. Shortly before closing, she handed me a red wristband.

“I’d be pleased to have you join the after-hours party, if you can. I’ll understand if you need to go home, however.”

“No, no need to leave. I’d love to join you.”

The bartenders and waitresses chased all of the non-partiers out, including Big Bertha. She saw me in the corner with Serena, and shot me a dirty look.

“I wouldn’t worry about Bertha if I were you. She’s mostly all talk. She has a very respectable job, and won’t do anything to let her secret out. All you need to do is suggest you’ve seen her somewhere before, and she’ll avoid you like the plague.” “Good to know. She was pretty forceful earlier.”

“I know. That’s why I invited you to join me. She knows better than to mess with guests I’ve shown personal interest in.”

“I…see.”

Just then, a group of the entertainers came back and joined us, so Serena never said what she was about to say to me. She reached over and placed her hand on mine, as if to apologize for the interruption. I smiled, and gripped her hand.

The next couple of hours flew by. It seemed like everyone in the place wanted to talk to her, and say hello to the new guy. I eventually felt the call of nature, and made my way to the facilities. Opening the door, I found one of the bartenders getting fucked by the Cher impersonator. They started to break apart, but I waved my hand to stop them.

“Please, don’t stop on my account. Let it never be said I interefered with another man’s sex life…”

They laughed, and I finished up.

Going back to the floor, I looked around and saw that there were many spots where heavy action was taking place. I saw couples, groups, all types of sex happening, and absolutely no shame whatsoever.

Serena smiled when I came back to the table.

“I was afraid you had gone off and found a prty of your own to join, and left me here all by myself. I was going to go out and kidnap you away for myself.”

I responded by kissing her. She melted into my kiss, and our tongues met. We stayed that way forever, or so it seemed to me, then she pulled back.

“Join me upstairs. I’d like to have you all to myself tonight.”

She took my hand, and led me up a short flight of stairs to her office/apartment. The door had barely closed before she was back in my arms and we were kissing again. We moved our way towards the bed, where she pushed me down. Stepping back, she reached up and slid the straps of her dress down, and let it slide down her body. She had small breasts, very perky and natural looking. Serena cupped them in her hands, and pinched the nipples. Letting the dress fall further, she stood before me in a thong, that seemed to hide quite a package. Turning around, she bent to pull the panties down, only to find my hands at her hips.

Pulling her back to me, I kissed and carressed her body. Using my teeth, I gently lowered the thong from her tight little butt. My hands fondled her breasts, and my mouth made contact with every inch of her ass. I bent her over, and ran my tongue down the crack of her ass. I felt her shiver, and heard a moan escape her lips. She turned around, and pushed me back. Stripping my shirt off, she licked and flicked my nipples with her tongue. She undid my pants, and pulled my hard member free. Stroking and fondling me, she pushed it between her tits, teasing the tip with her tongue every time the tip came close. All at once, she swallowed my cock, taking it to the hilt.

I moaned, and she kept at it, giving me the best blowjob I’d ever had. She’d bring me close to orgasm, and back away. She turned her body around, and straddled me for a 69. I took her cock in my mouth without hesitation. It was small, but hard and ready for my attention. We went this way for quite a while, and eventually, she lifted herself off of me.

“I need this cock in my ass. Would you fuck me with it? Will you fill my ass with your hard cock?”

I responded by pulling her to her knees, and climbing behind her. She pulled her asscheeks apart, and I drove my tongue in, to moisten her up. She moaned, and pushed her ass to my face. I kept this up for a few minutes, then pulled back. I pressed the head of my cock to her pucker, and she pushed back, hard. My cock was quickly buried in one of the tightest asses I’d ever been in. We quickly developed a rhythm, and she was soon screaming in lust and pleasure.

I felt my balls tighten up in anticipation of a monster orgasm, and told her so. She responded by reaching back and pulling me closer to her, so that my cock was buried in her ass.

“Cum inside me. I want your cum in my ass, baby.”

I reared back, and gave her one last thrust. My cock erupted, filling her with hot cum. She pushed back, moaning and throbbing with her own orgasms. I reached around and felt her cock. It was covered with her own pre-cum, and I quickly stroked her off the an orgasm of her own.

We collapsed on the bed, and cuddled for what seemed like forever.

Serena rolled to face me, and we kissed again.

“Thank you. You were magnificent.”

“My pleasure. You were wonderful yourself.”

She smiled, and kissed me again.

“We should go downstairs and see what’s happening.”

We got up, and I started to get dressed. She reached out and stopped me.

“Why bother? Odds are, we’d both end up naked again anyway, right?”

We laughed, and went to join the party downstairs. Turns out, she was right. We would have ended up naked again…

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