My Leiben Herr

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Innocent crossdressing leads to sex with a man.
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kinki1
kinki1
152 Followers

I'm not sure if this has anything to do with what happened, but I will start off by saying that my fiancée broke off our engagement about a year and a half ago. She didn't give an explanation, or at least not what I would consider an acceptable one, and I guess I have been pretty broken up about it. Three times since then I have been on dates that led to some fooling around, but all three times I backed away. I kept picturing my ex, and in all three cases I just didn't feel like sleeping with these other women. There I would be, fondling some good looking woman's tits, my cock not hard at all, feeling like I was about to cry.

All of that is by the way, and I am not sure if it explains the strange thing that happened to me, or makes it even stranger.

A few months ago, I was a chaperone on a trip that a local branch of a youth group made to an international gathering of the group. For reasons that will become clear, I will not identify the group. We met in Berlin, partly because of the anniversary of the wall coming down, and there were a large number of groups there from quite a few countries.

The meeting lasted four days, and all of us chaperones were pretty exhausted. However, on the last night, after all the kids were in bed, it was a tradition for the staff to put on a talent show. It seems that not enough people had signed up for the show, because the German guy in charge, call him Willie, was really trying to pressure people to perform something.

I made the mistake of telling him I might do something, and he kept asking me what I was going to do. I tried to back out, but he insisted. At one point I told him that I would like to sing a German song, but the only song I knew with even a little German in it was "My Leiben Herr," from the show Cabaret.

"Perfect!" said Willie. "I'm writing that down."

"But it is supposed to be sung by a woman," I said.

"You'll do it in drag," said Willie, "it will be hilarious!" I kept protesting, but Willie insisted people would love it. "It will be so nice for you to sing in German, and I have one of the Spanish chaperones who can play the piano for you. I will get the music."

"Where can I get something to wear?" I said. "I could borrow from the women..."

"Don't worry about that," Willie said. "I will get you clothing. Just tell me your shoe size and your waist size."

That was how I found myself in a small dressing room behind the theater where this all was taking place. Willie bustled in with some shopping bags and boxes.

"You have about forty-five minutes before you go on," he said. "I found someone to chip in for your costume, so you got a really nice one." He divided the packages into two piles. "This must be returned, but this you may keep. I will come get you before you go on," and he rushed out.

That relieved one of my two main anxieties, that I would have nothing to wear (the other was that I had not yet rehearsed with the pianist). But when I opened the bags and boxes, what was in them was almost worse than having nothing at all. I had thought we were going to play it for laughs, but the stuff in the package was very sexy and professional! There were a pair of very high-heeled shoes, fishnet stockings, a pair of small and lacy bright red panties, an outfit in black that was laced up in back with big cups in front and a very short skirt. Then there were also two large realistic looking boobs, with skin around them and this stuff called 'spirit gum' to stick them on, makeup, a razor, and a black shoulder length wig of straight hair.

I immediately left to find Willie. I was going to complain and ask him to find other clothes, but I couldn't find him. After searching for a few minutes, I realized he was not going to be able to get another costume at this late date, so I kind of said 'What the hell' and went back to change.

I only had to shave my underarms and my shins , as I am not very hairy. I stripped down to my underwear, shaved, then took my underwear off. It was a little odd being in this strange little room in Berlin naked, with a huge mirror surrounded by lights. I put on the panties. It was hard to arrange my cock and balls so that not much was hanging out, but I sort of managed it. Then the fishnet stockings. I had to put the corset thing on to see where the boobs went, but I figured it out. They looked pretty real! The corset thing laced in the back. I could tighten it, but not tie it. I figured I would have to get someone to tie it for me, but I felt embarrassed looking like myself with those big boobs hanging out, so I ran the razor over my face, put on makeup, and finally the wig. I put on a lot of foundation, gave myself pink cheeks, and bright red 'bee sting' lips. I figured people would only see me from a distance anyway.

Then I went out in the hall to look for one of the Germans running the show. When I found Hans, he seemed shocked. "Wow, David, is that you? I thought some sexy girl had come in and was running around half naked."

"I'll take that as a compliment," I said. "Can you tie me up in the back?"

"I'll tie you up anywhere," Hans joked.

"Ha ha," I said, and I turned around. He pulled the laced much tighter and tied them at the top.

"Seriously," he said, "I am almost about to ask you on a date."

"Thanks sweetie," I said as he finished tying my laces. I pinched him on his cheek. "But I don't think you're my type."

I went back to my dressing room and looked at myself in the mirror. I guess I did look hot, smooth legs, boobs spilling out of the top of my corset. Objectively speaking, I would have wanted to fuck me, although, as I said, I really hadn't been interested in sex recently.

I had about ten minutes, so I did some vocal warm ups. Willie came to get me, and he also said "Wow, you look great! So sexy!!"

I had to walk out slow, because of the high heels, and there was a lot of laughter and wolf whistles and cheers from the very beginning. I think they were surprised to find I could really sing. "Bye bye mine lieber herr, so long my lieber herr, it was a fine affair, but now it's over..."

I don't know if you know the song, but it is about a girl who is leaving a guy basically because she wants to have sex with lots of other guys. Frank, the piano player, was really good, and I really belted it out at the end. The whole audience was clapping along. I didn't move much because of the high heels, but I wiggled my boobs at them, and at the end I turned around and swished my skirt up so they could see my panties. They roared at that, and I rushed off. It was an incredible high. Willie made me go back out and take another bow. Well, I curtsied and blew kisses, and flipped my skirt up again just as I was leaving the stage. They roared and cheered. I felt great!

I tottered back to my dressing room and shut the door. I was flushed and sweating, my heart still pounding, sitting facing the mirror with my legs splayed out. "Not very ladylike!" I thought to myself, and giggled. Just then, there was a knock on the door, and almost before I said "come in," one of the German guys walked in.

He was a guy I had met a few times before, I'll call him Johan. He was tall and wirey, with a receding hairline and his hair cut very short, with piercing blue eyes. He came in clapping. "Brava, brava," he said. "That was the most amazing act!"

I laughed with pleasure. "I'm glad you liked it!"

"Liked it?" he said. "You should be a professional singer! And you are the sexiest girl I have ever seen!"

I leaned a little forward and pressed my boobs together, making some cleavage. "You like the merchandise?" I joked.

He grabbed some tit through my corset and said "Ja, you made me really hard!"

"Sorry Johan," I laughed, "I can't help you with that!"

"Why not?" he asked. I suddenly realized he was serious.

"Well... I'm not gay."

"Of course you are not!" he said. "You are not a gay man, you are a very sexy girl! And I have something that girls like!" He pulled down his pants and underwear in one move. My mouth dropped open in shock. There was the biggest cock I had ever seen in my life, including in porn movies. It wasn't fat, but it was very long, maybe 12 inches, and he wasn't even completely hard yet. He was uncut, which I hadn't seen before. It was just a monster!

"Now look at yourself in the mirror," he commanded. "You are Sally Bowles, and you know what she would do with this!" In the mirror I saw a tremendously sexy sight. I was a very hot girl, and there was a huge prick right near by. It was like a scene from porn, only I was in it. Suddenly I felt horny as I hadn't since my ex left. My heart was pounding and my face was flushed. I didn't know what to do.

"That's right, Sally," Johan said, "take it in your mouth. Give me one of your famous blowjobs. You'll never get another chance to suck a cock like this," and I knew he was right about that. I'm not really sure why I did it, I am certainly not gay, but I was overcome by lust. I was a girl, a slutty, horny, cabaret performer, and I did what she would do. I took it in my hand and pulled it to my mouth. It was heavy, and I gave it a lick. "Good girl, Sally," he said. "Roll back the foreskin." I rolled it back and forth a little bit. It was so hot and smooth! Then I put the end right in my mouth! I started to bob my head up and down, licking the underside as I went. I was pumping him with my right hand, slick with my own saliva, and squeezing my huge tit with my left. My own cock was sticking out of my panties, rock hard. I suddenly pulled off and looked up at him.

"I'm not going to be able to get all of this in my mouth," I said apologetically.

"That's okay Sally, you are doing great," and he guided my head back to his cock. I sucked him enthusiastically for some time, pulling his cock out occasionally to rub it on my face and marvel at the awesome size of it. Then he pulled away, and said "Now stand up and bend over the chair."

"Uhh, I'd rather finish you off in my mouth," I said.

"You can, but first I am going to fuck you."

I must say I felt a little thrill at those word, but I said "I'm not sure if I want to do that."

"Now don't be a cock-tease, Sally," he said. "You know you will give in, why not just admit it? All the girls are dying to be fucked with a cock like this. You can brag about it to your friends afterwards."

"Well, okay, but just put a little bit in, so I can see how it feels."

"Of course," he said, and he slathered his beautiful cock with some cream that was on the counter. "Now hold your cute panties to one side, so I can enter you."

I did, and he slowly slid his cock inside me. Every time it started to hurt, I caught my breath, and he would stop, pull back, and slide slowly back and forth up to that same point. After a bit, he would slide further in. The whole time, he was rubbing me through my panties and saying "That's it, good girl, good liebchen, you can take it, feels good, doesn't it?" After a bit, he said "Now look at yourself in the mirror." I did. I was a complete slut. My tits were hanging out of my costume, my hair mussed and lipstick smeared from sucking cock, and a tall German man standing behind me with his cock up my ass. "It is all the way in you," Johan said. "You are a very talented girl. Now I am going to fuck you."

He started sliding back and forth, and it felt fantastic! I just loved the feel of his huge cock in my ass! I started saying "Oh! Oh! Yes! Fuck me! Oh harder!"

"Ja, you like it? Huh? My American slut?"

"Oh yeah! Oh fuck me!"

He had both hands on my hips and was slamming into me at full speed. I had one hand on the back of the chair and one hand rubbing my cock through my panties. I was looking at us in the mirror, him fucking me like a piston, my huge tits swinging with the force of his stroke.

Suddenly I clenched, shooting load after load of hot cum into my panties. Maybe my clenching set him off, because he pulled out of my ass, came around front, and commanded "Open!" I opened my mouth, and he shot multiple blasts of cum on my face, in my hair, and on my tits. A little bit went in my mouth. It had a salty taste.

He squeezed the last of his cum on my cheek, and we both just panted there for a moment. Then he wiped his cock on my other cheek, and, putting it away, said "Sally, you are an excellent fuck. We'll have to do it again some time." And then he walked out.

I couldn't believe he just left! I looked at myself in the mirror. Wig askew, tits hanging out, stockings torn, panties soaking, and Johan's cum all over me. There wasn't a towel in the place. But I started to grin. I am a good fuck! I knew I would be dreaming of Johan's cock back home.

Suddenly there was a knock on the door. A voice called "Hello, are you in there?" It was Hans! What should I do?

kinki1
kinki1
152 Followers
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MonkeyWrench00MonkeyWrench008 months ago

This is my absolute all-time favorite story here on Literotica! I keep coming back to this one.

AnonymousAnonymousover 1 year ago

Think I’ll go and have a wank

AnonymousAnonymousover 4 years ago

The fuhrers spirt lives within this story.

AnonymousAnonymousover 6 years ago
the german girl lol

damn that got me hard wish it was me

AnonymousAnonymousover 8 years ago
First Time, Best Time

I'm a confirmed bisexual male now, married to a very confident and dominant wife, Lori, for the last 13 years. My first time with a man was 4 years ago when our debts had far outstripped our resources and we asked her uncle Angus for a loan. Angus had taken Lori's virginity after college when he helped her move to take a new city for a job, and I knew all about him from the many times she compared me to him. I always came up short and on the occasion of our meeting, the terms of his deal were simple: my ass for his loan. Long story short that very night I became a cocksucker, and by morning he had taken my anal virginity. My wife was thrilled - we got the money we needed and her uncle was back in charge - fucking us both. Some men, sorry to say, are just more manly than others.

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