Discovered at the Bar

It was 9 pm on a Friday night and I was just getting off work. It was a long day of running meetings and I really needed a drink. I was out of town and didn't know anyone so I decided to go to the bar by myself.

As I sit down at the bar I take off my suit coat, untuck my shirt and loosen my tie and ask the bartender for a Jack and Coke. The first drink didn't last long and I had another one. I was keeping to myself and watching the baseball game.

From the other side of the bar I see a women staring and smiling at me. After a long day of meeting I really wasn't looking to hook up with anyone, so I just gave a friendly smile and went back to watching the game.

About 10 minutes pass and I see her walk past me and as she did she smiled again. She was a gorgeous, tall, skinny, blonde, wearing a tight green dress with the perfect ass. I watched her enter the bathroom and went back to my drink and the game.

A few minutes later I heard a whisper in my ear that says, "You're mine sissy" as she snaps my bra strap. I was lost for words. How did she know? Was my bra strap showing? Who else saw it?

She sat next to me and told me to show her my panties. I denied I was wearing panties but she told me "I know no sissy wears a bra without panties." I knew I was caught and unbuckled my pants at the bar and exposed my panties to her.

She reached down and started to rub my penis and leaned over and said to me "I love a good sissy in panties, you are gonna do what I say tonight or I'll tell everyone tomorrow what a sissy their boss is. Nod your head if you agree and follow me." I nod my head yes and we get up from the bar.

What did she mean she will tell everyone tomorrow? Was she in the meeting today? I had no idea who she was.

While walking toward the elevator she snaps my bra again. I turn to her and she is laughing. As we get to the elevator to head to her room I remember I didn't pay my tab. She tells me it is taken care of.

While on the elevator she tells me to take off my shirt and pants. At first I was hesitant but she was not taking no for an answer. "Strip down to your bra and panties now sissy!"

This time I don't say no. I strip to my matching pink bra and panties, black thigh highs and garter belt. She giggles and grabs all my clothes as the door opens. I try to grab them from her but she won't give them back to me.

She smacks my ass and tells me to walk. I don't want to leave the elevator but she is standing in front of the door to where it won't close. I have no choice but to exit.

She tells me her room is at the very end of the hall. As we are walking a group of girls exit their room. They all stop and stare and me and giggle. She says to them "you girls like my sissy?"

They all laugh and tell her have fun. I head on of them say "I want myself a sissy. I'm gonna try and find one tonight. Or maybe I'll see if I can barrow him."

We finally get to her room and we go inside. As soon as we get in she grabs me and bends me over the bed and I feel a whack on my ass. It stings at first but it feels good. "That's for not showing me your underwear at the bar when I asked. *smack* That's for not striping on the elevator. *smack* That's for not get getting off the elevator right away."

"Now who's gonna be a good sissy panty boy?" "I am" *smack* "I am what?" "I'm gonna be a good sissy boy."

After another smack she rubbed my ass, teased my asshole and grabs my hips and fake pumped a few times. I have always cross dressed but I have never had anything in my ass but have always wanted to try it.

I was already bent over so I figured tonight was the night to pop my cherry. I started moaning and pushing my ass back. She reaches down and starts rubbing my dick, "if you do what I say you will have the best orgasm of your life tonight."

A few moments later she pulls my panties to the side and she starts rubbing my asshole. I feel her slip a finger in and I let out a big moan. It felt so good, everything I imagined it would. I was hoping this wasn't the only thing going in my ass tonight.

As we start getting in a motion I hear a knock on the door, she pulls out and tells me to go answer it.

I walk over to the door and open it.

There stands the bartender from earlier. She runs over and gives him a big hug and kiss. I asked what he was doing here and she tells me that he here because he paid my tab for me and I'm going to repay him.

He comes in the room and closes the door behind him. She tells me to unbuckles his belt. Instead of saying no like I thought I would have I didn't even hesitate and walked over and grabbed his belt and undid it.

As they fall to the floor I see his cock outlined in sexy pink panties. I was really turned on and wanted his panty covered Cock in my mouth. I reached out and started rubbing it and dropping to my knees.

Instead of pulling his cock out right away I rubbed and licked it outside his panties. I loved the feel of lacy on my tongue. I knew I wanted to suck a cock but didn't think I wanted it as bad I did.

After a few minutes of teasing him, and myself, I released his straining cock from his panties. I started at the tip and swirled my tongue around it. Little by little I put more and more of his cock in my mouth.

After a few minutes of sucking I pulled his dick out of my mouth and started licking his balls. He moaned as I did this. I could tell he really liked that. As I went back to sucking his dick I made sure to keep playing with his balls. I was really getting into a groove when I felt the girl from the bar grab my head.

She held my head still and the bartender started mouth fucking me. I let out a huge moan. "Does sissy like sucking cock?" I moan "yes". "Are you gonna suck his cock while I fuck your sissy panty wearing ass?" I nod my head and she pulls his cock out of my mouth.

She stands me up and tells the bartender to go sit on the bed. As he does she bends me over and I start sucking his cock again. While I'm sucking I feel her slide my panties to the side and I feel her rubbing lube on my ass.

She sticks a finger in and I let out a huge moan on his dick. She sticks another in and it feels so good. I'm pushing back wanting more and more. All of a sudden she pulls them out. I groan in disappointment on his dick. Moments later I feel something pushing up against my ass.

It wasn't her fingers this time. It was hard and plastic. She had strapped on her dildo and was about to enter my ass. I let a giant moan on the bartenders dick. It felt so good.

I could tell she was slowing putting it in me but I want the whole thing. I pushed my ass back and she grabs my hips and slams the whole thing into me.

I was in heaven. One of my sissy fantasies was coming true. I was in the middle of a Mmf Eiffel tower while dressed in women's clothes. I had a dick in my mouth while a dildo in my ass. Both my sissy holes filled.

All three of us got into a rhythm. Me sucking the bartenders dick like in have been doing it for years.

Her pulling my bra strap to arch my back while fucking my ass with the 7 inch realistic purple dildo.

Me pushing my ass back wanting the dildo to go harder and deeper in me.

Me massaging his asshole making him groan even louder.

Her calling me her sissy panty boy.

I could hear him starting to moan and felt his dick start to swell. I knew he was about to finish. I sucked faster and started to jack him off at the same time. She saw that he was about to finish too. She reached around and grabbed my panty covered dick and started jacking me off. "Finish at the same time as him sissy."

He let out a final groan and my mouth filled with cum. As soon as I tasted him I cummed in my panties. It was the hardest I have ever cummed in my life. Still sucking I made sure to not let any of his cum spill and swallowed all of it.

As I was pulling his dick out of my mouth the let go of my dick and pulled her dildo out of my ass. She pulls my panties back over my ass and gives it a smack. "That's a good sissy panty boy. I can't wait to watch you tomorrow give a speech knowing what you are."

I laid on the bed still in my bra and panties trying to catch my breath while the bartender and her got dressed. As they walked out the door she turns to me as says, "you better wear your sissy clothes again tomorrow, and be ready sissy because tomorrow you get a real dick in your sissy panties ass."