The First Time

If you have read my stories before you know that I'm Finnish guy who doesn't write in English as well as someone who is from an English-speaking country. So, I apologize beforehand about my mistakes or odd lines. Without good editor helping me I couldn't publish this story. So thanking her very much! My stories consist of some elements that many can think of as weird or perverted. If that's your case, then you are warned! ;-)

I have always been interested in kinky stuff in sex and submission. I often try to find new things to experience. Once you have tried something you like, you want it more and you are ready to take steps that you didn't imagine taking. Small steps can take you places that would have been no-no's in the past. That has happened to me.

One of the biggest turn-ons to me has been anal pleasures. When I was younger, I fantasized about being a lesbian girl taken by woman with her strap-on. This fantasy grew from a porno I saw called Paprica. There the brothel Madame fucked one of her girls with a strap-on. I had never seen anything like that before. It affected me a lot. Years later, the internet came and gave me a lot of information about sex. Then I found out that I could also be fucked with a strap-on, even though I'm a man.

I had only few tries with my own fingers when I decided to meet an escort who also did kinky stuff. She was a nice person, but the experience was quick. She grabbed my cock and put her finger in my ass and I came at once. I was young and very horny. I would have liked it to have lasted longer, but it let me know it can feel very nice. It didn't take much time before I decided to have a new experience with a professional domme. She fucked me with a little strap-on and massaged my cock at the same time. Again I didn't last very long, but it was a nice experience, too. Then, through the years I had more experiences with bdsm and anal play. Most of them were good.

In my head I had been fantasizing that I could give great pleasure to my fucker. I think a few women can get orgasms when fucking with strap-on. Maybe with vibrator attached to it or something but not directly from my ass. Then I came across transsexuals on the internet. When I was young and read porno magazines, I had seen trans people there, but the dick on the girl had been a big turn off. But now it felt a little interesting. I looked at pics from them and had seen a few movies. Most I found too manly, but there were also very feminine ones who I found sexy. The next step I took was trying to find transsexual escorts. There were a few foreign ones, but most of their appearances didn't excite me.

One day I found an ad that belonged to a trans escort who had leather clothes and looked like a very feminine domina. I decided that if some day we were in same town, I would see her. It was an easy decision. Her tour only went through the bigger cities in my country and I lived in a smaller town. One day my boss said that I should take a business trip to another city and stay there overnight. At home I looked on the internet to see if there would be an interesting companion for me at night. And there she was, the transsexual escort who I had fantasized about meeting.

When I arrived at my hotel in the afternoon I thought and thought. Could I see her? I had sent her an email and she had answered my questions nicely. I thought I had no excuse. Nervously I called her. We agreed on meeting at her hotel.

She gave me the opening codes for the hotel doors, and before I knew it, I was behind her hotel room's door. It was little open because she knew I was coming and wanted to get me in without noise. She stood behind the door and let me in. She looked like her pictures. She had very little on. She was ready for action. I nervously gave her the money and she ordered me to undress and put my clothes on one chair. She saw my nervousness and "fucked" me with my clothes on from behind and laughed when I was bending to take my socks off.

When I was naked she asked me to go shower and to use plenty of shampoo between my legs. I did go to the bathroom. Suddenly she came into the bathroom, too. She told me to bend over the sink. When I was in the position, she penetrated me with a small syringe, and gave me little enema. She ordered me to evacuate that first and then clean myself in the shower. I did as told.

She was waiting for me sitting on the bed. When I came in she stood up and pushed me against the wall. She started kissing me and her tongue was soon in my mouth. She was a very good kisser. My nervousness went off and I was turned on. While kissing, she took my hand and put her semi-erect cock in to it. It felt odd. I had never had a penis in my hand other than my own. But it also felt familiar because it's something I had, too. I massaged it slowly and cautiously. She also took my penis in her hand and made more demanding moves.

The next new experience came when she asked if I would prefer a condom also in oral sex or not. I have always practiced safe sex, so I said I would like condoms. So, she took a condom and put it on her penis. I then realized that it would be me who would take the penis in the mouth. I tried to say, "I don't know if I'm ready to do that because it's my first time." She looked in my eyes and asked me if I was a virgin. I said, "This was my first time with transsexual." She had a wicked smile.

She said that everybody wants to at some point take a cock in the mouth and give her oral, and I should do it also. She promised to give me a reward after.

Slowly I went down and took a grip from the base of her cock. Then I took little of it in my mouth and sucked it. She didn't like my effort. She asked me to take my hand off her penis and instead pushed her cock all the way in, taking a firm grip of my head with her both hands. She fucked my face and I tried not to gag.

After a few minutes of oral sex, she ordered me to stand next to the bed and bend over it. I did what was asked and knew what was coming. "Have you taken other things in your ass?" she asked. I told her that I have a little experience but never took anything big inside of me. "Okay, we will soon know if you are a liar." I heard a snap that came from a disposable glove. Then came a small syringe again, which I think sprayed lubricant in my ass. "Relax!" she said and slapped my bottom. Maybe she saw that I was everything but relaxed because what she did next was she went on her knees behind me and I felt her tongue on my anus. I had never experienced that before. I jumped a little in the air when that happened, but then her slow movements with her tongue relaxed me and it started to feel very pleasant.

After she felt I was relaxed enough and even more turned on, she placed her index finger on my anus and pushed it all the way in with one movement. I was so relaxed that I didn't have time to react before it was in. It felt immediately good. "You are tight like you said but can also relax. I think I will have good time with you. Hope you are not in a hurry," she said. I answered something about having plenty of time.

She massaged my ass with her finger for some time and added another finger when I was relaxed for the intruder, and then more when I was adapted to that. At the end, I had four fingers inside me and she teased me also with her thumb next to my opening saying, "Let's turn this into a fisting session!" She must have seen my horrified look when she started to laugh.

"I think you are as ready as you can be," she said and took her fingers out and took off the glove. "I will put a better condom on," she told me. I saw the package had text that read 'analsex'. They were thicker and lubricated. It had a transparent pink color. "Little girl power for you," she said when she saw me looking. "Stick that ass high, elbows on the bed, and arch you back," she commanded.

She guided her cock from the base to my hole and her other hand spread my ass cheeks. I felt the pressure. The cock was a harder instrument than I had thought. It wasn't soft meat. She increased the pressure little by little and changed her angle a little to find the way in. Then I felt it coming in a little. I felt sharp pain. She was big. I had never had any big toy inside so this was the biggest I had ever had. She eased a bit but she was quickly pushing again. A new sharp pain happened, but it was not as bad as the first time. She must have felt that because now she didn't stop. She pressed in slowly without stopping until her hips were against my bottom. "Ooohhh, you are tight indeed!" she said when pausing her movement when all the way in. Then she made little movements back and forth. Little by little the movement was longer. Still, she moved slowly. It felt a little uncomfortable but there was no pain. I remembered having pain with a lot smaller dildos in the past. She must be good at her work. She relaxed me and got me so turned on that I could adapt quickly to her monster.

Slowly she took her penis all the way out. It hurt a bit when her glans went through the backdoor. She put more lubricant in me with a syringe. This time she smeared my ass with a big load of it. "And then the real fucking begins," she announced.

Her penis was again pressing against my anus. Without stopping, she just pushed it in and not as slow as before! When in, she ordered me on my hands and knees on the bed keeping the cock inside whole time. "Put your legs a little closer to each other so I have a better angle." She trained me. And then it began. She fucked me just pleasuring herself without thinking much of me. We changed positions many times and when I was on my back, she lifted my legs on her elbows. Then I had a condom on my penis and she gave me oral at the same time when she was fucking me! That was amazing. It was intense prostate stimulation and awesome oral sex at the same time. It didn't take long to fill my condom. When she had sucked every drop from me she just turned me doggy again and fucked me faster than ever. I felt a little pain because I had orgasmed. But this was just for her. She had decided to take her pleasure from me. When I felt I couldn't take any more, she pumped her semen inside the condom. I felt the jets and pulsating of her cock. It was amazing feeling this in my ass and also in my head. Someone had orgasmed inside my ass.

She rested lying on my back. When she was completely limp, she stood up to lose the condom. I did the same. Then we lied on the bed caressing each other. There were no words. Then we went to shower and washed each other from head to toe.

When I was putting my jeans on and leaving, she suddenly stopped me and took my jeans off. "You will give me round two before you leave," she announced. She was stiff like a rock again and put on a condom. She fucked me against the wall kissing and biting my neck. She had decided to make it fast. She fucked fast and massaged my penis in quick pace. I came again and soon she was also in her orgasm. That was even more amazing than the first round. This time it certainly wasn't just a job to be done for her. It was something she wanted and that something was me.

We kissed and I did a quick cleanup in bathroom. I left to my hotel with kisses at the door. I maybe have had the best sex ever and I had not penetrated anyone. I was the only one who was used but it felt so good.

My ass felt odd a few days after. I had never fucked so much and with something so big. I saw her almost ten years later in another city. She immediately remembered me and we continued from we had left off years ago.

If anyone liked my story, I would like to know. My stories are for little audiences. Not a mainstream. So, if someone liked it, I would be glad to know. :-)