I first met Jack nearly 20 years ago. He was a long-distance truck driver that used to visit a little roadhouse that I owned. He would park his rig at my lot overnight and usually be gone before the sun came up.
“Do you want to hear something that will give you the shock of your life?” Jack asked me one Friday night when the place was nearly packed. “What?” I asked him.
“I was born female,” he told me with a smile. I figured he must be joking or d***k and I didn’t have time to play along so I just nodded and went back to my business.
As I was closing up Jack came up to me and grabbed me from behind, “You still don’t believe me, do you?”
“I think you had a little bit too much to drink so why don’t you go sl**p it off,” I told him. He then proceeded to undue his huge oversized belt-buckle and unbutton his jeans and unzip is fly.
“What the fuck are you doing,” I said, trying not to cause a scene.
Jack then pulled his shorts down to reveal his bushy, hairy pussy.
“What the fuck!” I shouted. “I told you,” he said. “You ain’t shittin, that’s a pussy,” I said to Jack, stunned.
“Can I touch it?” I asked him. “Sure,” Jack said to me.
Jack was a very tall and extremely masculine man. He had to be at least 5’11” and weight well over 200 pounds. He was very solid and muscular and one of the most masculine men I ever met. There is not a person on this planet that would ever guess that Jack was born female and there wasn’t a single thing about him that was the least bit feminine. He kept his hair shaved really short and had a couple of tats on his biceps. He even had a big, bushy beard. His voice was very deep and I bet be could lick just about any man.
We went back to my office and I closed the door. “I just want to have a better look at it,” I told him.
His pussy was the hottest fucken thing I had ever seen. It was extremely hairy and the big purple clit was huge.
When I ran my middle-finger over the slit it felt very wet and Jack started to quiver. “This pussy is hot as fuck,” I told him.
With his hand Jack spread himself open so I could have a complete look at his entire vulva.
As he was laying on my desk, nude from the waist down with his cunt fully exposed I told him “that is really the hottest fucking shit I have ever seen. You are one sexy dude!”
The next thing I knew I was fingering Jack’s twat. I was able to get 3 fingers up his cunt-slit while I jerked his erect clitoris off with my second hand.
I become so incredibly turned-on that within only a few seconds I had my pants around my ankles and my cock up Jack’s twat.
The moment I plunged my cock inside of his tight pussy I began to fuck it silly. It felt amazing. Very tight and wet and after a few intense thrusts I shot my seed deep inside of him.
After I took my spermy cock out of him, I then beat off his clitoris as I banged my cock-head over Jack’s sensitive clitoral hood.
As Jack was experiencing orgasm I knelt down and licked some of my sperm out of his man-cunt.
Jack and I talked for hours afterwards because I was so curious about him. I learned what a transman is.
He explained to me that he was born female but lived as a man. He had his tits removed but did not choose to have surgery on his bottom portion.
Jack told me that he identified as a gay man and was not attracted to women at all. He also told me that he did not consider his genital area to be a pussy.
“It is my cock, just like you have a cock, I have a cock,” Jack said to me. “Sorry, I kept calling it a pussy,” I told him. “You didn’t know so there’s nothing to be sorry about,” Jack said.
“Any time you come back into town I hope you know that I will always gladly fuck you,” I told him, putting my hands between his legs and grabbing onto his hairy cock.
And fortunately for me Jack made many more trips to my roadhouse and I had the privilege of fucking him many other times. It was truly some of the very best sex of my life.