It All Happened So Fast

I had sex with my trans friend and it was nothing like how I had imagined it!

When I was 3 a new family moved in next door. They had a boy the same age as me. His name was Jaxon. We were best buddies instantly! In fact, we’re in our 40’s now and still very close. As a matter of fact, we’re closer than ever. Here’s how that happened.

Back in high school, Jaxon always talked about being a woman and we always shrugged it off like he was just a big fag. We all knew he was gay but what we didn’t know is that he was already considering transitioning. It was the late 90’s though and that kind of thing was still foreign even to us 90’s kids.

Fast forward to about 3 years ago and Jaxon gathered myself and a couple other of our close friends together and finally told us he was trans. We all knew he was into wearing women’s clothing and would openly discuss how he was a bottom and rarely held back on details of his sexuality, so we weren’t surprised by it but it still caught us off guard a bit.

As the months went on and she (now known as Jessica) went further and further down the avenue of transition, more and more of our friends began to distance themselves from her. My stance was and always will be: we came from the sandbox together and I’m not abandoning my friend just because things have changed a little bit.

A few months ago, I woke up in the middle of the night with an absolutely raging hard on! I rolled over and nudged my wife and asked her for some quick sex. Being that it was 3am she said no and immediately went back to sleep. I made my way to the basement and sat in my comfortable chair and began scrolling through endless porn sites looking for the perfect thing to stroke my cock to. Shortly into my searching, Jessica texted me and we began talking. About what? I don’t remember. During our conversation, she randomly sent me a picture she took in of herself in the mirror. The caption along with it said: “I’ve always had an ass but my tits are starting to get bigger!”

I have always been.. bi-curious. Very much into women and never had sex with anyone that had a penis. But, had always considered it had the right opportunity came along. Seeing that picture of her made me see her in a physical way for the first time in 40 years of friendship.

I didn’t tell her because I just figured it was silly and it meant nothing. I mean I was sitting naked in my chair stroking my dick already so I assumed I was just extremely horny.

The next night I had an incredibly vivid dream about the two of us having sex. I had her bent over the arm of the couch and I was pounding her ass! A few nights later I had another one of her blowing me. Then another a week later. Every time I had an incredibly dream about her, it made me more and more curious and willing to consider putting it out there. The situation is beyond complicated with me being married and her being my best friend for 40 years!

We had a party at my house a couple weeks ago and invited Jessica and an assortment of our friends and family and my wife’s friends and family. There were at least 20 people there and we had all eaten some gummies. As they began to kick in, my tongue started loosening up.

I had casually let slip in a private conversation between Jessica and I while in my basement that I had a few sex dreams about her. Without hesitation she leaned in and kissed me quickly. We were the only two in my basement so no one saw it. Stunned I said nothing and she apologized and went upstairs without another word. I stayed in my basement for a few minutes while I processed what had happened.

For the next half hour we awkwardly avoided each other. All the while the memory of her kissing me stewing in my head along side my vivid and graphic sex dreams about her!

As I passed her in the kitchen a few minutes later I jokingly pinched her butt. She quietly gasped and turned towards me biting her lower lip. She had a look in her eyes like she wanted to fuck me. I knew the look well.. I was suddenly looking at her the same way!

As I stood therein the kitchen my cock began to swell. I was wearing sweatpants so it wouldn’t take much to be noticeable. I quickly made my way upstairs to the private bathroom in my wife and I bedroom. As I closed the door behind me I reached for my phone. I was going to look for something to jack off too.

Before I could get started the bathroom door quickly swung open. Jessica slipped inside and shut the door behind her and locked it.

“What are you doing?!” I asked slightly agitated but my heart also racing wondering what was going to happen next.

Jessica didn’t say a word. She grabbed me and we shoved our tongues in each other’s mouths. Our hands groping each other. My dick had never been so hard! What was going on?!

We kissed and groped for a minute or so when everything was suddenly flipped upside down and I got something I wasn’t prepared for.

Jessica turned me towards the mirror and stood behind me. In one swift motion she yanked my sweatpants and underwear down to my ankles. Then she lifted on of my legs up to the countertop, squirted a small handful of my wife’s hand lotion in her hand and began stroking her dick. Seconds later I felt her 6” cock pressing against my suddenly eager asshole. I had put my fingers up my ass, I had even masturbated with my wife’s dildo when she wasn’t home from time to time but I had never had a real cock in my ass before!

Jessica had a firm grip on my hips as she began to slowly thrust herself deeper and deeper inside my ass. Watching her bend me over the countertop and fuck me in the mirror was the single hottest thing I have ever been apart of. I couldn’t believe how much I was enjoying it! So unexpected! Such a turn on!

Within a minute Jessica moaned quietly in my ear: “I’m going to cum so hard!”

“Do it! Cum inside me!” I softly moaned back.

I felt her cock begin to pulse as she thru stone last time. I could feel her pumping shot after shot of hot cum inside my ass! It was intoxicating how good it felt. Maybe it was the gummies enhancing things but this was the most exhilarating minute of my life!

As she pulled her cock from my ass, I felt her hot semen spilling out of my stretched hole. Jessica quickly buttoned her jeans and left the room leaving me still bent over the countertop, out of breath, full of hot cum and utterly shocked by what had just happened. It felt like it lasted for an hour but in reality she was only in there with me for a minute or two!

As I returned to the party a few minutes later, Jessica had left abruptly and we didn’t get a chance to speak. We haven’t spoken to each other since it happened but I hope she comes around and starts answering my texts and calls because I want MORE!