The First Day On The Train [M28/F26] [Transgender] [Anal] [Romance]

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Trains are my thing. Since I can remember. I have at all times been fascinated by them. So I spent the bigger part of my free time – no, I wasn’t working for a railway business, I spent my time in a research lab working on methods to safe the environment – on trains, in railway stations or looking at trains in some rail yard.

I was perfectly happy with my job and my life. But it lacked one thing: A significant other. A girlfriend. A woman on my side. It took until I was around twenty eight years old to discover a qualified partner. And this here, is the story how I met her, or to be totally honest with you, how I got hooked up with her.

It all took place in the middle of the fall. About six years ago. I was spending my weekend on a steam powered train that was doing a trip through the gorgeous autumn colored landscape. I was more than just looking forward to it for months. I even bought some new camera gear to get better shots of the train, the landscape and the people on the train.

But before I could board the train I had to jump onto a plane. An about two hour flight from the town I was living in towards the starting point of my train journey. Or at least as close to the starting point as efficient.

Some friend of mine picked me up at the airport and we drove towards the final destination. We went directly to the railway station where the train was already getting prepared for the three day journey. After saying hello to all the people there I joined them in. My fellow train enthusiasts and me we cleaned the train, filled up the supplies in the dinning car and help bunking the coal. The last one especially was really hard and dirty work, so after we were done, it just was a shower and then we all fell in our comfy hotel room beds.

After a night filled with nothing but sleep the hole crew met up again. We got together next to the train, we had a short briefing about the upcoming days and then we went to work. For me it meant to go to my compartment, yes, I had one for my own and prepare my camera gear for the upcoming days: Yes, my job was to document it all. To get some good shots of everything that was going on.

The paying guests were already boarding while I was cleaning my lenses and dusting off my camera bodies. I was focused, concentrated on what I was doing. When all of a sudden it knocked at my compartment door. I wasn’t expecting anyone, so I asked: “Who is there?”

It was one of my friends playing the train officer. He asked me if he could come in for second or two. I told him that the door was unlocked. To my surprise he hadn’t showed up alone. An about twenty six year old woman stood next to him. She had a gigantic smile on her face. And curves to die for.

The train officer then asked me one question. He really struggled to do so, but in the end he was able to pull the stunt: “I know that you prefer to have a compartment on your own. But well, we accidentally overbooked the train. Don’t ask how it happened. And so we have one person too much. And by the looks of it, the only empty bunk is in your compartment. So is it okay for you when she shares the compartment with you for the trip?”

My eyes were still on her, I was still checking out her when my mouth opened: “Yes, sure. No problem. Always glad to help out.”

A smile appeared on my friends face: “Thank you.”

Then you introduced the two of us. She was the daughter of a fellow train enthusiast who was due work reasons not able to join us on that trip. I knew her father. And yes, he casually mentioned his daughter in the past. But he never told me that she was that good looking.

After the train officer had left, after he had closed the compartment door behind him it was only the two of us in the room. Some awkward silence was between us. Then she began to talk. She told me that she was sorry. And she told me that it was her first over night train trip ever. Initially she wanted to spend some time with her parents on here, but well, no she was all on her own. And while she told me that, she excused herself for intruding into my private space.

I listened to her. At least I tried to, because she was bending over a lot while she was unpacking her stuff. Yes, she was unpacking. She brought a whole suitcase for a three day trip. When she was done unpacking and talking, she asked me one thing: “Are you always that quiet?”

Her question was a surprising one. I had no clue what to answer her. So I nodded with my head. A smile appeared on her face when she saw my reaction: “No problem. I like the quiet ones.”

I blushed a little bit. And she kept on talking: “You got a lot of camera gear laying next to you? Are you an amateur or a professional?”

Her last question finally broke the ice. Without thinking I gave her an answer: “Just a humble amateur photographer. But I try my best to get the best shots possible on the train journeys that I am part off. And well, I spend some time in some rail yards taking pictures too.”

She nodded with her head: “So can you take a few awesome pictures of me too on this weekend?”

Then she went into a sexy pose for me. Again, I had to stare. Yes, she caught my eye. And I totally forgot about picking up one of my cameras, attaching a lens to it and taking a picture of her. She noticed what was going on. And commented onto it. With a gigantic smile on her face.

After some time holding it she left the pose and sat down on the bench of the opposite side of the compartment. Once she had sat down, she looked over to me: “Next time you take a picture instead of enjoying the view.”

As soon as I realized what I had done, I blushed once more. Then I excused myself for my error. Luckily she was a forgiving one. And one that knew what she wanted: “Can you show me around the train? We could take one of your cameras with us.”

I shrugged my shoulders and off we went. She let me take the lead and I showed her the meanwhile moving train. From time to time steam was passing by the windows and the very rhythmic, very relaxing a train is moving noises were everywhere were it was quiet enough.

We explored the whole train together. I explained her a lot, I took some pictures, most of them had my roommate on them, a few were showing some other passengers and even less than a few were random train shots. She clearly was in the center of my attention on that afternoon. And she did everything to stay there.

We spent the bigger part of the afternoon in the panorama car. We were talking – yes, after a while I was able to have a conversation with her – we got to know each other a little bit and yes, I kept on checking her out at whenever efficient. And yes, I got the hots for her.

It was a fun, a relaxing and an entertaining afternoon. We enjoyed each others business. We smiled at each other a lot. And yes our eyes meet more than just once. When it happened, we both had butterflies in our bellies. She later told me that when we were talking about our first afternoon together.

When the afternoon turned into evening it was time to move into the dining car. There we had a table for the two of us. It was already prepared and had our compartment number sitting in the middle of it. So we sat down. And ordered our food.

Everyone passing by us looked at us. They all had a smile on their face. Some of them, especially those who I knew had a certain suspicious smile on their face. As if they knew something that I wasn’t. It didn’t took me to count one and one together, to understand that it all was nothing but a set up. So far, their plans worked out. I was more than just thankful for their doing back then.

My room mate and I we enjoyed dinner together. We kept on talking and talking. Rarely ever that I was able to talk with someone about that many things. And yes, as she later told me, it was the same for her too. We got along more than just well.

After dinner was over, after we had our dessert and a drink, maybe two, we moved over into the lounge car. Many people were hanging out in it. Enjoying conversations, having drinks together or just spent some time people watching.

But as soon as my room mate entered the room we had their full attention. Partly because most people knew either me or her and partly because we were the attraction of the trip. Two young people – yes with twenty six and twenty eight years we were the youngest human beings on the train – probably falling for each other.

We hung out in the lounge car for a couple of hours. We had a few more drinks while socializing with the rest of the crowd. But at all times while standing next to each other. We got touchier and touchier with every hour. Our eyes met more and more. We both knew what would be next. So it was time to say good night. We went back into our compartment.

Back in the compartment we sat down. Next to each other. As close as efficient. She came up with the great idea to turn off all the lights. So we sat there, our bodies touching while the dimly lit landscape was passing by the window: Shadows of trees, the light of a house and sometimes you could even see the stars. Nothing but romantic.

It didn’t took long and we were into each others arms. It didn’t took long and our eyes met. And stuck with each other. Seconds later we shared our first gentle kiss. A first gentle kiss followed by another one. And the next one. And the first passionate one. Our hands began to explore each others bodies.

Then out of nowhere, full stop. She gently pushed me away. She even turned on a small light and looked at me. She had a more than just serious expression on her face: “I am very very sorry, but I have to tell you something really important. And please, swear me that you won’t be mad at me.”

The moment she had finished speaking my mind went crazy. I was thinking about everything and nothing. From stuff like it was to good to be true to things like how have I fucked it up this time. I had a minor anxiety attack. But I played it cool. Or at least I tried to: “I am all yours. And I won’t be mad. Promised.”

All that she gave me back was a more than just insecure: “Really?”

I repeated her answer in a very assuring tone while looking her in the eyes: “Really. I won’t be mad at you.”

Then she told me her tale. She told me that she once was trapped in the wrong body. And that she began changing that when she was around twenty. She told me that she was trans. And she also told me that she still had a dick and a pair of balls between her legs.

It honestly took me more than the blink of an eye to process what she just had told me. Once I was done with it, I took her hands and looked her in the eyes again: “It is okay. What you tole me is no reason for me to be mad at you. Or find you disgusting or anything else. But I must admit, I am a little bit nervous now. Because you are my first trans woman. And first times just make me nervous.”

I was able to see how the tension left her face. Her concerned face turned into a smiling one. She hugged me. Then she looked me in the eyes: “Don’t worry too much about your first time here. I’ll guide you through.”

Then we hugged each other. We looked each other in the eyes for some time. We listened to the calming train noises. And then we kissed again. Gentle kisses first, passionate ones later. Our hand were all over each other’s bodies again.

It didn’t took long and passion took full control of us. Horny was in full swing. Clothes were flying through the room. We were tearing the clothes off each others bodies. Some of them got destroyed. But we didn’t mind. We wanted each other.

Soon her hand was on my rock hard dick. She jerked me off while her other hand was squeezing my balls. We kept on kissing always. Her hands on my dick, they felt nothing but awesome. And it clearly wasn’t her first time jerking someone off: She knew the spots she had to hit.

Soon after my moaning was filling the room. My dick was spitting pre cum. I enjoyed every second of it. But I wanted more. I wanted everything. So did she. She whispered the following into my ear: “Lay down on your back. I grab a condom and some lube.”

I laid down. My rock hard dick was pointing towards the ceiling. Then she pulled a condom over it and drowned it all in lube. She also put some lube on her asshole, then she climbed on top of me. She bowed down and we began to kiss again. Long passionate kisses.

Then I could feel her asshole pressing against my glans. Then I could feel my dick sliding up her ass. I was moaning out loud, so was she. We didn’t gave a damn about the fact that the whole car probably was listening in on us. We were lost. All that mattered was feeling the other and feeling my dick sliding in and out of her asshole.

Fuck it felt good. Her dirty hole wrapped itself around my dick. Then she went up. She rode me cowgirl. My hands were on her tits, or on her ass. Her dick, her balls and her perfect boobs were bouncing up and down with every hard thrust she gave me.

Damn it, we lost it. We were gone. It felt so good. One thrust after the other. Our moaning got more and more intense. We both came closer and closer to an orgasm. Fuck, it felt so good.

And then one more hard and deep thrust, boom my balls emptied themselves. It came hard, it came good. Unfortunately for me only. She wasn’t able to finish. As soon as I was myself again, as soon as I realized that only I was able to finish, my conscience showed me the middle finger. I felt terrible sorry. I excused myself. More than once.

And her reaction onto it, she just pulled my half hard dick out of her asshole and then she bowed down and gave me a gentle kiss on my cheek: “Don’t worry. It was an awesome ride. Next time you will turn me into an orgasm filled trembling mess.”

She said it all in the right tone, so I believed her. Then I got rid of the condom and we cuddled next to each other, or onto each other until we feel asleep.

NSFW: yes

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