First Experiences

For a long time I finally wanted to test the reactions as a transvestite on the street. But how should I do that? I had to appear very inconspicuous and not attract too much attention. I had to think of something else. Since I'm only 27 years old, dressing up shouldn't be a problem.

However, I can't go out on the street in my favorite fetish clothes. Even a woman in boots and a leather skirt catches the eye. What to say about a transvestite in rubber clothes. All considerations did not help.

I had to confide in a very dear friend. She knows my inclinations and should support me in my outdoor activities. So I called Laura and she was home too so I was with her that same evening. Laura is around 40 years old, not married and looks great. I've had some nice thoughts in my head.

But I'll wait a little longer. Now we sat with a coffee and she asked me again about my last sexual contacts. Laura likes my stories. After a while I got to the point of my visit.

I explained to her that I finally want to go outside as a transvestite but don't have enough make-up experience yet. That's definitely not a problem for her. You confirm that immediately.

Laura just said, of course, I'll do your make-up and we'll take the first steps together." But I didn't want to be 0815 as a normal transvestite, I wanted it to be provocative.

That made her think a lot. Suddenly she started laughing. She didn't explain her laughter to me, though. I asked several times, but always the statement: "Let yourself be surprised".

But since I didn't have any make-up utensils yet, we had to go buy something first. For this we drove to the city. Since she was heavily made up herself, we didn't stand out at the register with $165 for makeup kits. Since I like the color blue myself, everything for the eyes was of course blue.

I baked everything in my car and drove her home. We arranged to meet at my place the next day. A kiss on my mouth and she was gone. In the morning the phone rang and it was Laura's turn. She just told me she'd be over around noon and she'd bring a shaving kit.

Since I was still overgrown on the body. And punctually at 12.45 p.m. Laura was at the door. As always, she couldn't help it and was once again dressed like a whore or simply put, she let men's cocks grow.

First, we devoted ourselves to my hair. She shaved me on the easy spots and the rest was removed with depilatory cream.

Now there wasn't a hair on me. Then Laura did my makeup. She made it nice and slow and explained everything to me. Up to a point in time I still came along.

I was actually done, at least I thought so. Then Laura said: "This is how a decent transvestite would wear make-up, but you need it wicked". So my eyes got highlighted, lips redder than red. Then I got a racy, permed black wig.

I was allowed to look at the work in the mirror. I was able to jerk off at this sight. Laura just said: "Not bad, but now the right outfit". And she was already gone in my closets.

I thought now that she just wanted to take a picture of me in my outfit.

She took the following items out of my closet: blue latex corsage, black thigh-high latex stockings, white latex panties, red latex mini skirt, red latex bolero jacket, red latex gloves, red patent leather handbag and pink thigh-length patent leather boots with 10 cm heels. I should wear all those things. Of course it's not a problem for me, but it takes a lot of time. It was now almost 9:00 p.m. I had put everything on and Laura was very excited.

Unfortunately, my make-up suffered a bit and had to be renewed. Then I waited for the camera. This one hasn't come yet. I ask and Laura just said: "There's still a part missing".

She took out the handcuffs. Since I'm into SM, that wasn't a problem for me. And already my hands were fastened behind my back. "Well my little whore, now we can start and you'll see," said Laura and was happy. I couldn't resist.

The handcuffs didn't allow anything. A thought slowly came to me. She didn't want to push me out onto the street like that. At that point, not even my neighbor would have recognized me, but I was terrified.

“Your fear is unfounded, we are going to a somewhat remote place and there you will be walking up and down.

So Laura guided me through the dark stairwell to her car. I had a little trouble getting in, but it worked. We drove towards the train station and then we stopped briefly. Laura got out, rummaged in the trunk and came back.

She had a silk handkerchief in her hand and this was placed over my eyes. So I couldn't see anything anymore. I didn't even ask why she did this now. We drove a few more minutes and then she stopped.

Then Laura said some funny things to me I'll take off your handcuffs in a moment, leave the blindfold where it is and you get out of the car. I will then step on the gas for a moment and when you hear this, you can take off your mask". What should I think of that?

But I had no other choice. I just hoped that it really is very far away and that nobody is on the street anymore.

According to the latest news, it was just 10:30 p.m. So I got out and closed the door. Immediately afterwards, Laura accelerated, but not just for a moment. She just drove off.

I immediately tore the blindfold off my head. And then what I saw was awesome. For a long time she had just driven me in circles and then ended up in the industrial area. There was the well-known street prostitute.

I stood at the beginning of the side street. On the sidewalk there were women every 10m, looking for suitors. There I stood and saw Laura driving away. But I could tell that it stopped at the end of the round 600m road. It could only be her car as there was no car further down the road.

So she wanted me to get back to the car and cross the line in the process. I wanted to go home as soon as possible. So I started carefully. The whores were not enthusiastic about me, as I was "competition" for them.

I ran faster and faster, because the whores made me really stupid.

I started to freeze a bit. Because rubber doesn't exactly keep you warm. Then I dropped my handbag and opened. The contents scattered on the street.

I picked up all the condoms again. When I looked up, a minibus pulled up just in front of me. A man rolled down the window and said to me: “Is that something all latex? You're a horny little whore. We wanted to do something harder in the studio tonight, but don't you want to give us head?"

I could think properly.

Unfortunately I had to have said something. They got really cheeky. Then they must have noticed that I am a man. Because I have a pretty deep voice.

Then the two jumped out of their cars and came towards me. One held a $500 bill under my nose and asked me what the options were. Stupidly I reached for the money and so the men thought that we are already in agreement. However, I just wanted to check the authenticity.

Then the men grabbed me and I was gone in their minibus. I thought I was in a bad movie. Since the thing had no windows, I couldn't call Laura for help. I squatted on the floor and waited for what was to come. After about 20 minutes the guys stopped.

I ended up in some garage. I was pulled out of the car without the slightest word. I still had the $500 in my hand. Then one of them took my handbag and put the 500 dollars in it and said what's the matter with you? Did you smoke a bad herb or why are you so nervous.

We'll bring you back and if you do everything as we imagine, then there's a bonus." I told them that I don't actually do it and that I don't intend to be a prostitute.

"Oh I see. you're still a beginner”, said one of the guys. I nodded and didn't want to go at all.

But it was also clear to me that if I didn't do what they wanted, the 500 dollars would be gone and I'd have to go out on the street in my clothes. So I went with you. A path led through the garage directly into a basement. We got there and I was amazed.

This was a fully furnished playroom. Unfortunately, it seemed very brutal to me. Everything there was fairly roughly processed and the play equipment also indicated the hard pace. But I figured we're all grown up and is already a level to be expected. I actually wanted to leave right away.

But before I knew it, I was trapped in a cage. The men left the room and I was alone. After more than 30 minutes they came back. Both were fully dressed in leather.

They had studded bracelets, leather pants and leather shirts and boots. So they changed. They ordered me to take off my skirt and bolero jacket. I took it off and gave it to them.

Then they locked it in a closet. I should put on a 10cm wide leather collar and attach a chain to it. i did it Then the cage opened again.

I was immediately put on an existing gynecological chair.

The chain was fastened to the wall. Immediately my legs and my hands followed. They were tied to the chair.

Then the two started laughing. They got a pair of scissors and cut my latex panties and my not too small swollen cock came to light. Then one man said you know hell? Then you will meet her today or why do you think that you got 500 dollars from us?”. I got sick all of a sudden.

And then one man pulled up a trolley. A blanket lay over it. He covered him. All sizes of dildos lay on it.

There were huge pieces. Even a ponytail wouldn't get that thick. I couldn't fight back or run away. The two sat right in front of the chair and made jokes. Then someone fetched a pot with drippings.

It was Crisco. They both put on gloves and reached into the pot. Without saying much, they smeared my buttocks with it. A good handful was slowly sunk into my ass.

Then they hit me all of a sudden on my now tied hangers. I winced and cried out. It was more the shock than the pain. This only happened after a few seconds.

And immediately one of them hit it with a whip. "That doesn't hurt, does it? It's just the beginning and are you already screaming? Do we want to do something about the pain? I just nodded. And then someone held a small bottle under my nose. I should take a very deep breath and I won't be in pain anymore.

However, I know the effect of this remedy and did not like it. I just held my breath and turned my head away. I got an unwelcome hit on my hangers. I continued to refuse. Then someone fetched a gas mask and I got it pulled over.

Then I had a problem. Now they held the tubing directly over the vial. Unfortunately I couldn't hold my breath. They held it in front of the hose for too long.

I took a breath and thought they're going to take the bottle away now. But nothing happened. I inhaled the stuff for at least 5-6 breaths. I got a little weird and relaxed.

Then the man took the bottle away and waited a good minute. The mask was removed from me. At the same moment I saw the whip fly in the direction of my hanger. I hardly felt any pain.

I also no longer felt general touches. And again the bottle was held under my nose. I was momentarily dizzy.

Now they both sat down in front of me again and rubbed my butt again. I didn't feel much of it.

Then the first fingered something in me. Now a man took a dildo about 30cm long and 5cm wide and slowly pushed it inside me. I didn't feel any discomfort. This was pushed so deep into me that only the last tip looked out.

This was quickly removed again. Now the next size followed. It was a short but quite thick dildo. I kept this in for a while.

However, they insisted that they can cum on my face. I did not care. After they were done, I was also allowed to jerk off. This went very quickly.

After we were all satisfied I went to a corner.

There were paper towels. With that I cleaned myself up. Unfortunately, my make-up was broken. Since they cut my panties, I had to leave them out.

I got my skirt and jacket back. Since I was slowly starting to leak, I pressed some towels between my legs. Crisco liquefied and wanted out again. Without a word, the men withdrew and came back dressed.

They blindfolded me again and I was driven back to the bar.

I opened the pad and Laura was gone. What should I do now? So I asked the men to drive me in the direction of where Laura lived around the corner. The men liked doing that.

Her car was parked in front of Laura's door. I sneaked into the house and rang the bell. She opened up and was totally spoiled. You were angry with me right away.

I explained what happened and she started laughing. Because it was her fault too. She wanted to see my hole right away. It was still quite large and very wet.

Laura said "You'll be walking around with me for the next few days, have fun with it". That was my first outdoor experience. Unfortunately, I had some problems with my cunt for the next few days and a headache from the bottle.