I haven't had much exciting to write in here recently, My professional life has ledt little time for play. 

So I've decided to write up the story of my first fuck. 

For fifteen years I'd been fucking female partners anally and had become obsessed with that form of sex, prefering alternate between asshole and mouth during sexual encounters. My cock rarely if ever found its way into a womans cunt. I preferred to stimulate and pleasure partners clitoris and vagina with my mouth tongue and fiingers and save my cock and ejaculation for 'proper' sex  

One day I was thinking about these sexual encounters -and the amazing intensity that my partners experienced, and determined I wantd to experience it for myself.

This was about fifteen years ago, before internet  hookup sites were mainstream. So I posted  a meesaage on Craigslist or something similar to get a date.

Can't remember what I wrote,  but it must have worked, because  I soon had a date scheduled in a town close to where I lived. I knew nothing about my partner at all, only that he was Australian (these events happened in Dubai, where casual sex is frowned upon!)  

So I drove to our agreed rendezvous and found my date waiting for me on the side of the road. He got in the car with me and gave me directions to his apartment. As we drove we chatted a little.

The guy was about 30ish, not bad looking and had just come from the gym. He told me he was called Scott and a school teacher at the local International school.

We parked in his building carpark and walked up the stairs to a first floor apartment that seemed a little ramshackle and old fashioned  compared to my own. 

I sat on the sofa while he fixed me a drink (vodka and orange I think).  It was then I told him I wasn't gay. He looked startled, thinking that maybe the evening was going where he had hoped. But then I reassured him. I  explained that I had arranged our date because I wanted to experience being fucked. But I had never played before with another male, not even experimenting as a adolescent. So it was going to be entirely new for me. I asked if he was alright with that?

I could tell he'd been checking me out and that he liked me. Im tall, dark haired and with a fit smooth body and have been told Im good looking. Gay guys were always trying to pick me up, and I never went short of female company when I wanted it.  So I told Scott to relax, he would get my ass tonight. 

Somehow I think the prospect of fucking  a straight guy pleased him even more,

After my drink was finished I excused myself and stepped into the little shower toilet off Scott's living room.  I quickly undressed  and carefully folded my clothes. I had brought a tube of lube with me just in case and smeared some on my cock to make it glisten. I  stroked my gleaming cock to a 7and a half inch errection. Then feeling only a little apprehensive, I unlocked the door and stepped through. Scott was still seated on the sofa.

I asked if he was ready, noting that his surpised gaze was panning up and down my body and settling on my lubed cock. I do recall being a little nervous as I walked through into the apartments bedroom, lay on the bed  and waited for my lover.   

Scott bounced in like a puppy with boundless energy and once his clothes were scattered on the floor he dived onto the bed. His mouth went straight to my cock. 

Generally fucking with seriously kinky and sophisticated mature sluts, I recall that I found his oral sex technique rather amateur. But he was desparately keen and his mouth juices and sliva sooon firmed up my errection, particularly when I felt his fingers probing my asshole. I pulled his head far down onto my abdomen choking him with the pressure of my cock pushing on the back of his throat. I only released him when he started gagging and jerking to get free. He rose off my cock and gasped air like a surfacing deep sea diver,

Until now I hadn't played an active part in the proceedings, so I took Scotts cock and began sucking it. My first ever! I decided I liked the taste of it, but didnt like the wiry public hair tussled around it. His pubes threatned to get caught in my teeth. I felt Scotts cock harden in my mouth and my fingers found their way between his buttocks to probe his anus. I felt his cock harden further in my mouth. So then we were doung a 69 thing- both sucking each others cock while fingering each others' assholes. It felt pretty amazing.

Then Scott nearly killed the whole thing dead. He tried to kiss me on the mouth.  These days it wouldn't be a big deal, but back then  I was uncertain about my sexuality and it felt like a line had been crossed. So I pushed him off and told him I was not comfortable kissing. He was pretty good about it and we went back to  heavy pretting  for about 30 minutes on the bed.  We agreed that neither of us would cum and so held short of finishing each other. But it felt pretty awesome. After a while Scott rose from our haze of shared pleasure to fetch a condom and lube, It was now my time to deliver the goods. 

This next bit may sound nuts to somebody reading  this in 2021, but I told Scott I didnt want  the condom in me. Even though it was only a decade after the big HIV epidemic. My reasoning was that I was not sure if I would ever be fucked by a man again, and so on this one occasion I wanted to experience it properly. I had come so far and now wanted to go all the way.

Scotts explorations of my asshole continued with his tongue. To this day I absolutely adore being rimmed and eaten out by another guy. It feels so intimate. Perhaps  I owe that fetish all to Scott.

Scott was pretty good with my virgin asshole. He slowly worked me with lubed fingers circulating to relax my sphincter, but all that seemed to do was make my cock harder and harder until I felt it must explode. So I rolled away from him onto my belly and invited him to just get on with it. Thats how a few seconds later I felt Scotts weight on me and his cock poking its way through my sphincter.

Gotta admit. At first it really hurt, like a stabbing pain inside me, I gasped and gripped the bedsheets under me. However as the lube began to work and Scott found his pace with a gentle rocking, motion the pain was replaced with a strange out of body sensation that washed over me. After about ten minutes Scott rolled me onto my back, separated my legs and lifted them over his shoulders. He docked his cock back into my asshole again. It hurt again, and hurt more that way, maybe because of the position of my body. But I liked that I could look into his eyes as he fucked me, so despite the burning pain I encourged him onwards. I remember him mouthing fuck, fuck, fuck just as he came and feeling his cock pump inside me. That sent flashes of euphoria to my brain but also a searing pain inside me. Almost before he had finished ejaculating in me I pushed his thighs away from my buttocks...

Despite the searing pain I felt inside me ( I checked for blood -no blood), I had foiund the whole thing an amazing breathtaking experience.  

20 minutes later we were again sitting in Scotts living chatting over another cocktail. I had got dressed in preparation to leave, while Scott had a towel wrapped around him. But as the soreness began to ease, the memory of the sensations I had felt lingered and I flelt my cock harden again looking at Scott. 

So I stood up walked to the bathroom, closed the door and once again undressed until I was naked... stroking my cock fully errect again, I stepped out of that bathroom for the second time that evening top be met by Scotts gaze. So yeah we fucked again, twice in one amazing evening on my first time.

My life was never the same after that. Changed my outlook competely and my life is so much better for it.

And when I left Scotts later that evening, the condoms still remained unopened on the floor of his bedroom where he had discarded them.