first time with a trans women (M24)

mobile flash banner


Apologise for what may be an unfulfilling story, this is my first try but I hope to not only advantage from getting it off my chest, but from hopefully entertaining you guys.

I have been in a straight relationship from the age of 17-22. I have all the time considered myself straight, or if I’m honest it’s just not something I gave a wondered too. However, as I went through puberty and was exposed to the world of porn, it became apparent to me that I was at least, to an extent, curious about sex that goes beyond male/female sex.

This initially began to come to fruition when I was around 16. Stumbling my way through pornhub, hiding away in my room stroking, became a daily activity, I was completely sucked in. I love everything to do with sex, feeling horny and being myself filled with hormones, I delved and explored deeper and deeper into the vast complexities of fetishes and categories.

What really turned me on, and what has stuck since this day, was a clear attraction to trans women, crossdressing, and more recently a complete lust for femboys. But still, this lust was confined to my room, my head, no one knew or knows. Even when I had and loved girlfriends, I still found myself throbbing to these forms of porn.

I still am entirely attracted to femininity, but femininity that isn’t confined to heteronormativity, this binary. I go crazy for femininity whether there is a pretty pussy to eat, or if there is a cute hard cock to play with.

Anyway.. MY FIRST PHYSICAL EXPERIENCE. This happened after I downloaded Grindr.

At the age of 18 I finally grew the balls to put my fantasy to the test. I was at university, living in student flats, and matched with an older approx. 28year old trans lady. After sending her photos of myself she asked me to come to her aparntment in town to see what happens together. I remember how hard my cock became at the wondered of potentially meeting someone for real, to actualise what I have spent years fantasising over. I agreed, she told me she was versatile, at the time I didn’t really know what this meant but I confidently replied, me too..

I quickly showered, sprayed deodorant and dressed, and left my dorm quietly to start walking to the apartment, which took around 15 minutes. The whole way I was leaking from my rock solid cock, I could hardly hold my phone I was shaking with anticipation, excitement and overwhelming horniness. I arrived and texted her, it was a large building complex.

At level 5 I was at her hall, her apartment was down the corridor, I was riddled with fear but still aching from my stuff cock. I knocked, and I waited, silence until I slowly heard the knocking of high heels walking to open the door. She opened and greeted me in, she was stunning, slim and tall figured, long black hair and a small feminine body. No surgery, but an immense feminine beauty. She was wearing a black nightdress, sillky and a pair it red heels. We walked to her room, and she told me we had to be quiet, her friend was asleep in the other room.

We entered and she told me to take a seat, she left the room and quickly returned and closed the door behind her, standing still as she did whilst looking me up and down as sat on the bed. She was in full control, my inexperience and jitters of intense horniness contrasted her calmness and confidence… and I loved it.

She told me to undress, I did as I was told, sitting back down excitedly waiting for my cock to be finally sucked. She walked over slowly, smiling and licking her lips. I was throbbing, laying back slightly on the bed. But, when she stood infront of me she took my hand, and told me ‘I want you to suck my cock’. I was shocked and confused but I had no time to think, in seconds I was on my knees staring up at a thick but short cock that hung hiding beneath her dress. Without thinking I opened my mouth and took sucked the tip. It was soft and smooth, I immediately let loose and sucked her how I had all the time liked being sucked myself by girls. I tried to perform what I had seen in all the porn I had watched, sucking on her balls and running my tongue up the back of her shaft. All the while she ran her hands through my hair and pulled me in. She was quite forceful in trying to make me deepthroat, I choked and nearly threw up but I kept sucking, loving every moment of it. Squatting and sucking a gorgeous cock whilst grabbing onto her soft ass, I was in heaven.

Then it went to the next step.

She lifted me, looked me in the eyes, a young boy charged with sexual delight, animalistic with desire and dribbling from my first taste of cock, and said ‘lay on your back in bed’. I did as I was told, she laid me on the bed and swiftly raised my legs to her shoulder. This took me by complete surprise, I wondered at most maybe 69, or she’d face fuck me, that would pushing things. But without a chance to react she was playing with my asshole, spitting on her fingers and tracing the ring of my virgin ass. To this point I’d at most put a small finger in my ass out of curiosity, that was it. But she was driving her index finger in and lubricating her hand, she quickly was forcing a second inside of me. I gripped the bed and winced in pleasure and pain. I can still remember the feeling in my balls as she finger fucked me. I payed back and she lent over me, kissing me and my neck, and whispered in my ear ‘now I’m gonna fuck you’

I just moaned, I was hardly conscious with the overwhelming horniness, the pleasure and the fantasy fulfilment. She put a condom on (i had said whatever we did this had to happen prior to meeting) and slowly began pressing the tip of her cock against my now twitching asshole. She drove it inside me, relentless really but I was in no position to say anything but moan. After readjusting, reapplying lube and pressing again I felt her slide into me, and I let out a gasp to which she quickly covered my mouth. My eyes were watering with pleasure and pain, she begun to consistently drive her cock in and out of me and then it hit, THIS FELT AMAZING.

Opening my eyes and pushing out as she drove in, I was beginning to take her cock more comfortably. She fucked me for 15 minutes or so, kissing me and spitting in my face. I felt her balls slap my ass, I stared at her gorgeous figure and the amazement of what was happening. I can’t describe how amazing it was. But I wanted more, she appeared to be getting close to cumming, so I finally spoke up and said, ‘please can you fuck me in doggy style’. She laughed and agreed. I swiftly got onto my knees and push my ass up into the air like I had seen in porn. She gripped my hips and got back to fucking me hard. And within a few minutes she began moaning loudly and came, filling her condom that was deep in my ass, I could feel it. She flipped me over gasping for breathe, but I was rock hard and desperately horny. She lubed her hand and rubbed my cock until I spurted my biggest load all over my chest, which started up into my face. And it was done. She got up and showered and told me to get dressed and leave when I was ready.

Since then I have been with women and with a few trans and femboys. I love it and I’m glad I took the first step. Although this plays on my mind a lot, I really liked being dominated like that, and I really liked being fucked. Anyways, very long I know but I hope you enjoy the story, it’s 100% honest and a true recollection.

Let me know if I need to do more

NSFW: yes