This is how I became a ladyboy With Pain

A submitted story and her experience. He became a ladyboy. It did not say whether it was a real story. You may find out. 😉 The photo is by Masha.

I call myself Masha, I am married, and I have a preference for women’s clothes. This is how I became a ladyboy. I like to dress as a woman, I like being a woman, and sexually I love women. The beginning: The reason why it came about the way it did was actually given to me by my wife. One day she said she wanted to go to the carnival with me, but I’m not really the carnival type, I said I didn’t feel like it and I didn’t know what I should go as. But she didn’t accept that and said we could swap roles, she would go as me and I as her. I was flabbergasted, but she kept on asking, said there was a big carnival in town in 3 days, she had already booked tickets and if I cared about her I would come along.

She said she would get everything I needed, but we didn’t need much anyway, as we are almost the same size. So I said yes because somehow I liked the idea. On the day in question, my wife told me around lunchtime to go and take a bath. I had a bad feeling my wife is an absolute perfectionist. As I sit in the bath, she comes with a wet razor and starts to shave my legs. I protest, but she says it wouldn’t look right otherwise. She shaved not only my legs but also my cock, my torso and wherever else you can find hair. She put some cream on me and told me to come into the bedroom. There was the black corsage I loved so much on her, I got a hard-on. She just said not now. I had to put the corsage on, it was tight as hell, I thought I couldn’t breathe. She gave me stockings with seams, which I put on and fastened with the garter straps.

Then she stuffed my breasts and gave me a white frilly blouse with a stiff lace collar. She said you always want me to walk around in it, now you can try it yourself. She gave me another black skirt that came to just above my knee andlooked at me and said that looks quite good. Now she put make-up on me, stuck on long false nails in a bright red, gave me some ear clips and a pearl necklace around my neck. Then she put on a long curly blonde wig, the hair went far over my shoulders. Finally, she gave me a pair of black pumps with 7 cm heels. I put them on and said I could never walk in them. Then I was allowed to look at myself in the mirror and I was shocked, my wife had done a great job, in front of me stood a sexy woman.

Pulled up my skirt

She pulled up my skirt and put a bandage in my silk panties. She told me to walk in the shoes a little longer, I still had an hour to practice. She would get dressed in the meantime. Before we set off she said, the way you look now we’ll christen you Masha. And then we started, my wife drove us into town, a little away from the hall where the meeting was taking place, she parked the car and we got out. I felt very strange after all. We went to the entrance of the hall, everyone who entered got a plastic armband, women in red, men in blue. My wife went first, she got a red one, then I came to the man who was handing out the bracelets and he put a red bracelet on my wrist. My wife said, I did a good job there.

We took our seats and the session began. The session lasted quite long and since I had already had a few champagne glasses, I had to go to the bathroom after 2 hours. You had to go to the toilets in the basement, the corridors were empty because everyone was still having fun at the meeting where the royal couple had just moved in. Three middle-aged men who looked quite drunk came towards me. One of the men said to me, Beautiful woman, don’t you want to come with us? I said nothing and walked on with an uneasy feeling in my stomach.

I became a ladyboy and met horny men

Then two of the men on my right and left got behind me and held me down. The third man stood behind me and said come with me or I’ll stab you. They dragged me through a door and closed it. There was only a table and a chair in the room. One of the men said, “What a cute little thing we have here. They actually thought I was a woman. I didn’t know what to say. I couldn’t think of anything better than to say that I was having my period and that it was all pointless anyway, the men grinned. One of the men sat down on the table took his already stiff cock out of his trousers and said come here, I resisted but suddenly I felt something sharp in my back. My head was pushed towards the cock, then my nose was held shut and before I knew it I had the cock all the way in my mouth.

The man was fucking me in the mouth, I couldn’t believe it. Then I noticed how another man lifted my skirt and then held his cock against my cunt. He said at least this way we won’t get in the way of your days and laughed derisively. Then he forcefully pushed his cock into my ass. There I stood or rather bent down, in front, I sucked a man’s cock and from behind, I was fucked hard in the ass. Then I noticed how the third man was taking pictures, I wanted to protest but the man whose cock I had in my mouth held my head and said don’t let a drop go by, I don’t want to mess up my clothes. I felt strange, I got a hard-on, a great feeling spread up my backside, I couldn’t believe it.

Then the first one came, he shot a full load into my mouth, I wanted to spit it out but the man only said don’t dare or you’ll get a surprise, so I swallowed it all and then I had to lick his cock clean. Then the man from behind came and shot his warm juice into my ass. Now the men who came from behind switched to the front and the photographer took me from behind. The photographer seemed to have a huge cock and although I must have been really slippery I thought my ass was going to fly apart, but the tingling feeling was even stronger, I thought I was about to come although no one had noticed my cock, let alone touched it.

Then the man who had fucked me in the ass before put his cock in my mouth and fucked me in the mouth. The third one was busy taking pictures again. The two who fucked me came quite quickly. And again I swallowed all the cream. And again they swapped positions so that each had fucked me once in the ass and then in the mouth. The man who now came forward and almost tore my ass apart really had a huge cock. I hardly knew how to get it into my mouth, but it didn’t help, he stuck his cock right down my throat and fucked me in the mouth like a man possessed. Then we all came at the same time, first the warm juice of the two of them shot into my mouth and ass. Then my own juice shot into my silk panties, I was confused and scared of myself.

Without really noticing, the three of them were suddenly gone. There I was, the juice from me and the three guys running out of my ass down my thighs. I as a man was raped by three men because they thought I was a woman and as if that wasn’t enough, I also had an orgasm. How was I supposed to tell my wife? No, I couldn’t. I went to the ladies’ room as a matter of course and cleaned myself up downstairs, straightened my wig, my lipstick was smeared. I tried to fix everything with what my wife had put in my purse. Then I went back upstairs, the taste of the sperm still in my mouth.

I was thinking that I had often asked my wife to give me a blowjob or to let me do anal, but she never wanted it and now three men had fucked me in the ass and in the mouth. I came upstairs and sat down next to my wife, the program was still running. My wife looked at me briefly and said, what took you so long, you must have enjoyed yourself without me. I mumbled something about a champagne bar and was quiet. But the weirdness wasn’t over yet. When the event ended, my wife said she was hungry and we should go out for something to eat, I should wait for her in the foyer, she would just go to the bathroom. It took a while, and when she came in I was surprised because she had changed back into her normal clothes.

I said, and me, but she just said you look so good, let’s go out for dinner. We went to an Italian restaurant and the waiter took us to a table and we ordered some food. I looked around, no one seemed to notice I was a man. We finished our meal and my wife paid. My wife was eager to get going and dragged me to a nearby taxi rank. We got into the only taxi there and my wife told the taxi driver to take us somewhere where two lonely girls could dance and have a good time. The driver drove off and my wife said that taxi drivers always know their way around and that she wanted to have a drink and that we would pick up the car tomorrow.

The taxi driver dropped us off at a place that looked like a dance for lonely hearts, he probably didn’t think, as conservative as I looked in my white frilly blouse, skirt and pumps, that we wanted to go to a disco. But my wife was apparently all for the idea. So we went inside, surprisingly there was a lively atmosphere, the band was playing party hits. We found a free table and ordered something to drink. The band leader introduced the new rules for today if you were asked to dance you had to accept the invitation, if you didn’t want to join in, you should pay now and go home.

I looked at my wife, but she just smiled. Nobody left and the band started playing again. Then suddenly, two men stood in front of our table and asked us to dance. My wife said, of course, we’ll dance, we’ve been waiting for this. One man held out his arm to me and I raked myself under, then we went to the dance floor. He grabbed me around my waist with one hand and pulled me close to him, I had to concentrate at first as I wasn’t used to dancing like a woman and being led. His hand went down to my bottom, he pressed it briefly and let his hand go up again, he repeated this again and again. I felt shivers run down my spine and my cock started to work itself out again, hopefully, my dance partner wouldn’t notice my bulge. I looked over at my wife, she just beamed at me and gave me a thumbs-up, which probably meant she liked it, she didn’t seem to mind at all that I was being buried by the man. She seemed to be having a great time.

The next song was a slow one and the lights dimmed. My dance partner was half a head taller than me and quite strong. He pulled me close to him and put one hand on my bottom and the other on my back. I had no choice but to embrace him as well and dance cheek to cheek with him. He started to nibble my ear. I wanted to free myself, but he held me close. Then suddenly he kissed me on the mouth, he stuck his tongue in my mouth, I tried to resist but it was useless, he had a firm grip on me, then he grabbed my stuffed breasts. He didn’t stop kissing me, again and again, he stuck his tongue deep down my throat. Then the song was over and he let me go, I was about to bark at him when my wife came over and said, “Masha, you seem to have found a great admirer.

I had found a new admirer. The two gentlemen invited us to their table and I said that we would like to come to their table. I was speechless, I didn’t know my wife anymore. So we went to their table, they ordered us something to drink, it was a mixed drink and it was probably very strong. The food had been very spicy and so I drank far too quickly. I got a good buzz and my inhibitions fell, I thought what the hell. After a while, we were actually having a good conversation, my dance partner put his arm around me, pulled me to him and kissed me again, we were sitting in a rather dark corner and he started to fondle me. I heard my wife say, look at those two lovebirds, they are doing it right, show us what you can do. He started to undo two buttons of my blouse to get at my breasts, but he couldn’t get over my corsage.

So he stayed under my blouse and kneaded my breasts, not noticing that they were not real. He didn’t even take his tongue out of my mouth, he got more and more excited, he took my hand and led it to his zipper, I opened it as a matter of course and immediately his cock jumped out of his trousers. I took his cock in my hand and jerked it off, quickly pushing his foreskin back and forth. It couldn’t be much longer and he would cum. But then my wife came and said don’t you want to go somewhere else where it’s a bit quieter. The man got up and said to my wife, you’re right, we’ll go into my car. He led me out to the car park, I couldn’t believe my wife had made that suggestion. We went to his car, it was a big van that was quite out of the way.

He opened the back door and let me get in first, reaching under my skirt and luckily only getting hold of the sanitary napkin I still had on. He asked, “Are you having your period? Never mind, we’ll work something out. He sat down on one of the seats, I wanted to sit on the seat opposite but he pulled me down on the floor so that I was kneeling in front of him. He undid his trousers and immediately his bulging cock jumped out at me, as I was really quite tipsy I didn’t care about anything by now. I took his cock in my mouth and sucked and sucked on his cock, then I took his balls in my hand and kneaded them gently. I pulled his foreskin all the way back with my other hand and played around his glans with my tongue, a little of his juice was already leaking out and I licked it up greedily.

Then he turned me around and took me from behind. Again and again, he pushed his cock into my ass, as if he wanted to push his balls into me too. I myself had a stiff cock again and a thrill ran through my body, then I came and filled the bandage that I luckily had on with my juice. Then he came too, he felt me off, he shot his white sauce into me. Then he pulled his cock out of me, I turned around again and licked his already quite limp cock clean. My licking made his cock stiff again and I blew it until it came again, he squirted his juice down my throat and I swallowed it neatly. Then we sat down next to each other, and he said he had never met a woman who could suck as well as I could. Then there was a knock on the window and my wife and the other man were standing by the car.

My wife said it was time to go home, the men offered to be the drivers but my wife declined. So we called a taxi and drove home. On the way, my wife asked me how I had stopped the guy from doing what he wanted to do, she had specifically intervened in the pub to get me out of the predicament. Outside, I could have clearly told him what I thought. I was irritated if I had misunderstood my wife that way. I told her that he had already cooled down on the way out and that I had told him in the car that I didn’t want to, he understood and we talked for a while until you arrived. When we arrived home, my wife said that if we had already swapped roles today, we should do the same in bed.

She undressed and to my horror, she strapped on a huge rubber dick that had two ends, one side she inserted herself and the other bigger one was probably for me. She said she had got it, especially for today. I should stay dressed and kneel on the bed, I was so perplexed that I followed her instructions. She came behind me and pushed my skirt up and my silk panties down. Then she said oh you’re already wet and I was startled, I must still have juice from the last guy running out of my ass. But she didn’t say anything but pushed the rubber dick into my ass with strong thrusts, I thought my ass would tear but she didn’t let up and fucked me hard. Again I got a hard-on and my wife grabbed it and said that you seem to enjoy being fucked as a woman. I felt ashamed somehow. She took a condom and put it on me, but without stopping to fuck my ass.

She pushed me relentlessly in the ass with loud moans and powerful thrusts. I was so horny by now, my wife held my cock from behind with a firm grip to delay my orgasm. But it didn’t help at all, we were moaning and my wife was thrusting faster and harder. Then we both came, I had an orgasm like I hadn’t had in a long time and my semen filled the Parisian. My wife pulled the rubber dick out of my ass, then she pulled the Parisian from my cock and turned the Parisian inside out over her rubber dick so that the inside was now on the outside. I didn’t understand immediately and my wife said in a tone that didn’t allow any contradiction that I should lick everything clean and free everything from my cum, I couldn’t believe what was suddenly going on with my wife. But I did what she said and licked the rubber dick that was covered with my cum clean. I shoved the prick into my mouth and sucked and licked it, getting a hard-on again, I couldn’t believe it. But then my wife pulled the rubber dick out of my mouth and we sat down on the bed.

Then she suddenly changed the subject. She said she had been asked by her boss if she wanted to work all day with a much higher salary and she had already accepted. Since she would now be earning considerably more than me, I should talk to my boss immediately and tell him that I could only come half a day so that I could take care of the household. I tried to talk her out of it, but she just said I should do it that way and that was that. She also said that I would like it very much to be fucked in my ass cunt and that she would have a much better orgasm this way than if we slept together normally, so we should stick to that. Then she said she had another surprise for me, she took a package out from under the bed and out came an object I had never seen before and didn’t know what it was for.

My wife told me to stand, then she put the thing around my cock and balls and closed it. So, she said, so that you don’t waste unnecessary energy, it will prevent you from playing with yourself or fucking anyone. You can still keep your little friend clean and go to the toilet but only while sitting down, but that would suit me as she had experienced me tonight. Then she told me that if I ever needed to get rid of it, I should ask someone for help because I couldn’t get to release myself.