A Transman's 1st Hot Anal Fuck!  

backdoorfrenz2 43T
4 posts
11/24/2021 4:45 pm
A Transman's 1st Hot Anal Fuck!

As a Female to Male; "transman", one of the most exciting sexual experiences I've ever had is the first time I was fucked in the ass by a man.

Several years ago when I was still living in a condo, every summer like clockwork, the central air would go out. For three years in a row, the company the HOA used, sent the same HVAC guy to take care of the problem.

Tony, the HVAC guy was a nice looking Italian fellow in his late 20s. And he and I would always have pleasant conversations when he came to repair the system.
This particular time, we were making small talk and he commented on my strong resemblance the comedian Kevin Hart. I playfully responded that I didn't agree, since I'm far more handsome than that guy.

We had a good laugh, but I thought I sensed a "moment" pass between us. At that point, I'd never been with another man, and knew almost nothing about accurately reading flirting signals from guys.

Being Flirted With & Getting Turned On

Next, the conversation turned to how he usually wakes in the morning with a hard-on... so he doesn't like to interact with his other family members until after he's had time alone in the bathroom.

As oblivious as I was to being flirted with by guys... even I was beginning suspect that he might be coming on me. I wasn't quite sure what do next... but I realized that I was starting to feel really turned on.

I had known for a couple of years that I had begun feeling sexual attraction to other guys, but I'm married, I love my wife... and I had no intention of acting on these sexual feelings towards men.

Meanwhile, Tony said he had identified the HVAC problem and asked me to step closer to the HVAC unit and take a look, so he could explain what was going on and what he needed to do to fix it .

A Very BOLD Gesture

I did as he asked and stepped in front of him to peer inside the unit. I thought he would step back a little to allow me to peer inside, but he didn't. He continued to stand very close behind me. Pointing to the faulty mechanism inside the HVAC unit, he explained what he needed to do to repair it. We were standing in a very cramped space, the HVAC unit was in a large closet in a fairly narrow hallway. And when he leaned in closer to touch the faulty part and demonstrate the poor condition it was in, he was standing so close behind me that his crotch brushed lightly against my backside.

My first impulse was to step away... but I didn't move. In that cramped space, I could feel his cock growing firmer as it pressed lightly against my ass cheeks. But I still didn't move. I "couldn't" move... my t-cock was getting hard, and my asshole was literally tingling. Suddenly, I wanted his hard dick in my ass so badly, I was almost trembling.

Then I felt him press his bulging crotch "firmly" against my ass. And without even thinking, I found myself grinding my ass back against his rock hard bulge. And in that moment, I "knew" I was about to let this hot, Italian guy shove his big, throbbing cock, deep inside my quivering, virgin asshole... Balls Deep!!!

I was now on fire to get my asshole fucked and filled with hot dick. Still standing behind me, Tony put one arm around my waist and pulled my ass<b> tight </font></b>against his crotch, and ground his hard cock against my now, very eager ass. Immediately, I pushed my cock-starved ass against his hard dick, signaling that I was ready to take that big cock in my ass, to the hilt!

Let The Fucking Begin!

He turned me around to face him and the next thing I knew, we were kissing passionately, urgently... I feverishly rubbed his crotch with my hand. His cock was huge! I quickly unzipped his fly and pulled out his enormous cock. I stroked it and felt it pulsing in my hand. Without even thinking about it I slipped my knees and slid his thick, warm dick into my mouth.

I had never sucked cock before... but it felt amazing! A mouth full of warm meat sliding over my tongue. I was sucking the head, encircling it with my tongue, and licking the shaft... it was all so sensual and exciting to me. It wasn't better, but very different from the oral sex I'd had with women.

After a few minutes of feasting on his cock, he pulled me to my feet, took a condom from his wallet, unfastened his belt, and dropped his pants and underwear to the floor.

I had dildo fucked my own ass enough times to know I was gonna' need lube. I grabbed a bottle of silicone lube from my bedroom closet and stepped back into the hallway where he was still standing with his pants around his ankles, and his huge, 9" cock fully erect. He had put on the condom, and clearly, he was ready to fuck.

Amazing--Marvelous--Awesome Anal Sex!!!

I quickly pulled the drawstring of my Banana Republic lounge pants and watched them flutter the floor. I applied a generous amount of lube to my very excited asshole, then hugged the wall right in that hallway... waiting to take Tony's big, Italian cock in my very eager hole.

And I didn't have to wait long. Within seconds I felt the head of his thick cock probing my asshole... pushing gently against the slippery opening... then easing back... and pushing forward again. Each time, that big cock slipped in a little deeper.

I was glad I'd been fucking myself with dildos for a couple of years, because once he worked the head in past the sphincter... with a single thrust he drove 9 inches of cock into my ass, balls deep!!! And it felt awesome!!! That first thrust felt so good, it actually took my breath away.

My asshole opened wide and took every inch! Tony fucked my ass like a freight train for over half an hour... and every thrust was utterly thrilling. I never wanted it to end. The rhythmic slapping of his big balls against the back of my pussy, and the feeling of his huge cock filling up my asshole was intoxicating.

It was almost magical! It was like I was on some kind of fucking magic carpet ride... the wonderful sensation of having my asshole stretched to the MAX. And finally, the amazing anal orgasm that started deep in my ass and continued until it seemed to encompass my entire nervous system.

From that day on, I was hooked!!! Tony and I fucked many times over the next couple of years. Sometimes as often as 2-3 times per week. And the ass fucking, just kept getting better and better.

A Surprise For Tony!

On our second hookup, he wanted us both to get completely naked and 69. So, I was compelled to fess-up and tell him that I'm a transman. And I must admit, I was pretty worried that he might be upset or feel like I had deceived him. And at first, he really didn't believe me.

But when I got completely undressed and he saw my massive, free-swinging clit, felt my wet pussy behind it, and saw the scars on my chest from the double mastectomy... he was even more turned on than before... and for the next 2 hours, that man nearly fucked my brains out!

Well, I hope you enjoyed my 1st anal fuck story... it's certainly one of my fond memories. And I hope you'll share your exciting "1st Anal Fuck Story", too... Most of us love to hear them!

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