Transexual, Adult Friends, oral anal, M/Tran
This story is a work of fiction and contains descriptions of explicit sexual acts between a consenting an adult male and an adult transsexual- pre-op. If this type of content offends you or you are under the age of 18 do not read it.
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Copyright 2024 Jan, all rights reserved.
You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
John and a Trans
By
Wolf
My story began when I was in the military. It was common to bring erotic paperback novels, aka "Skin Books" and swap them among the guys in the barracks on the Naval Base. During one such swap, I was given a book about a straight man who is introduced to the world of pre-op trans women. This topic fascinated me to the point of squirreling it away from prying eyes. While I considered myself heterosexual, the idea of having sexual relations with a transwoman intrigued me including all possible combinations of activities that were in that novel.
Once my military obligations were completed, I concentrated on a college education and earned my degree as an electrical engineer, employment, and marriage, and family. During one of my web surfing exercises, I came across a dating site that included transsexuals. Recalling my days reading that particular-novel, my curiosity made me contact one trans that appealed to me. She was a Latina pre-op, and lived in the Los Angeles area. We arranged for us to meet at her apartment.
I told my wife that I would be working late and I drove to her apartment located in the Silver Lake area. It was located on a hillside and split level. I had to leave my car parked on the road and walk up to the second level and ring the doorbell. When the door opened, I was looking into the face of a raven-haired Latina beauty. She greeted with: "You must be John!"
I responded: "And you must be Veronica!"
She stepped back and allowed me into her apartment. Once inside, she greeted me by taking both hands into hers and reaching up to give me a deep kiss using her tongue. Her red lipstick marked my lips. I was captivated by the way she was dressed. Veronica was wearing a transparent black dressing gown that allowed me to see her black bra, a hip hugger thong, thigh high self-supporting nylons, and black stiletto sling pumps. She was a petite woman who was attractive enough to be a fashion model.
Veronica escorted me into her bedroom where soft music was playing and a lovely smell of her perfume permeated the air. A king-sized bed greeted my eyes while a low hassock was to my right.
Once again, Veronica approached and she and I were kissing and groping each other. She reached around and grabbed my ass with both hands. I did likewise.
After kissing, Veronica whispered in my ear. "John, remove your clothing. I want to see you naked."
That command had me quickly striped. I looked down at my cock which was erect, far more erect than it ever had been with my wife.
"Well, someone is very happy to see me," Veronica said softly.
After her statement, I put my left arm around her back and pulled her close against me, kissing Veronica on the mouth. My erection pressed against her thong covered pubic bulge. I smelled her perfume and hair as it cascaded over her shoulders to rest on her chest just above her breasts. When I stuck my tongue back into her mouth, I sucked the air out of her lungs and held the kiss until she struggled to breathe and I filled her lungs with the air from my lungs. She got very romantic while we kissed. I was curious about her small breasts.
I placed my right hand on her left breast and felt the bra covered tit. Not being satisfied with that, I slipped my hand into the dressing gown covering her left tit and slipped my hand into the pocket of the bra and covered the youthful tit that was about the size of a 12 or 13-year-old girl. The erect nipple was poking the palm of my hand. Veronica told me: "As soon as I can afford it, I will get breast implants but I am happy to keep my cock and balls away from a surgeon."
I looked her in the eye and said: "I love you just the way you look today. I would feel uncomfortable having sex with another man, but the idea of having sex with a woman that just happens to have a cock and balls is such a turn on for me. I have had that fantasy since I was twenty years old."
Veronica chuckled. "I'm happy to please you, John! Very soon your fantasy will become a reality."
There was that pregnant pause before someone took the next step. Fishing inside a nearby stand, Veronica pulled out a small vile which contained lube. She squirted a few drops on her right hand and went to her knees before me. Veronica placed her red manicured right hand around the shaft of my cock, coating it until it shined in the light. Looking up at me, she began to stroke it. "John, I love circumcised cocks."
My response was quick. "Veronica, I love uncircumcised cocks. They look so erotic to me. I wish I still had my foreskin but the doctor removed it shortly after birth."
Veronica continued her stroking to the point where I was feeling an orgasm approaching. Looking at the expression on my face, she stopped.
Getting to her feet, she walked over to the hassock and sat down. I followed her, kneeling between spread nylon covered thighs.
Veronica whispered, "I think it's time for the unveiling!" She slowly pulled the negligee off her shoulders and let it float to the floor. She reached behind her back with both hands and unhooked the bra and let the loose straps slide off her shoulders while she held the cups and slowly lowered her hands revealing the budding breasts of a young girl.
I was curious: "How did you get those tits without an operation?"
Veronica said: "I have been getting estrogen shots for years. I'm at a point that they are not going to get any larger. I don't want to go the rest of my life looking like my maiden aunt."
I reached out and felt them, marveling at how real they were. I even sucked on her nipples until she was moaning. When she had enough, she pried my head away from her tit. I wondered what she was going to show me next. After all, there wasn't much left. If she planned to remove the hip hugger thong there would only leave the nylons and heels. Veronica kicked off her heels revealing red painted toe nails encased in black nylons. Looking at her crotch I wondered where her cock was. There was only a large bulge. The black thong was low rise and there was some black pubic hair showing above the top. So far as I could tell there was nothing, she had shown me that wasn't anything but that of a beautiful young woman.
That was when she reached down with her left hand and pulled the thong to the side and used her right hand to reach back under her crotch and pulled out her cock. When she let go of it, I was duly impressed. The shaft was at least eight inches long with a distinct bend to the right as it dangled from her hairy pubic area accompanied by a pair of large balls. She sported foreskin that only covered about half of the large mushroom head. The urethra had a bead of shiny precum.
I was amazed that she had been able to hide a tool like that and an equally impressive scrotum, the size of large eggs. I asked: "How are you able to hide a tool like that?"
Veronica proudly exclaimed: "I simply tuck it between my legs and stuff the head into my asshole."
I involuntarily licked my lips. I couldn't resist reaching out and taking hold of her cock and feeling the soft flesh covering the stiff core. Veins were popping out around the shaft. As I masturbated her cock, the foreskin slid back to expose the complete mushroom head.
"John, it's time you sucked my cock." Bringing her hands behind my head, she applied light pressure and brought my mouth to within an inch of the tip. She removed her hands. "I'll let you finish what I started because you don't need my help, do you John? I think you could be a born cocksucker."
Those last words spurred me into action. Closing the final distance, I found myself taking the head into my mouth and sucking on as much of her cock as I could. This was pure joy and I felt my cock spasming in pre orgasmic fever. Using my right hand to masturbate her eight-inch cock, my left hand fondled her testicles.
This action continued for several more minutes.
Veronica interrupted my efforts before she could ejaculate. She was in no hurry to cum. She wanted to prolong the sex as long as possible. She removed her thong leaving her as naked as me.
Getting up from the hassock, she had me lay on the bed with my head over the edge. Straddling my head with her nylon thighs, she fed her saliva covered cock back into my mouth. In this position, I was able to take her more deeply until her entire length was inside my throat. "John, you took it all. Not many men have been able to do that in their first attempt. You're a born cocksucker."
Veronica began fucking my mouth slowly. As she almost withdrew, I swirled my tongue around her cock head before she plunged forward again. Her balls covered my eyes and the odor of sweaty male genitalia flooded my nose, exciting me even further.
Sensing she was near orgasm, Veronica looked down at me: "John, I going to cum in your mouth. Swallow every drop. When we are done, you are going to be rewarded by fucking my ass."
Grunting, she picked up the pace then moaned as I felt her shaft swell and throb. Within microseconds, she ejaculated ropes of salty thick semen down my throat. I swallowed and gulped all- of her love spunk with some escaping, forming a small stream on my cheek.
Once Veronica recovered from her orgasm, she removed the now flaccid semen and saliva covered cock from my mouth. The foreskin once again covered apportion of the mushroom head.
Bending down, she cleaned my face by licking up her semen from my cheek.
Our activities eased as I sat up, hugging her tightly to me.
"Care for some water before we continue, John?" Veronica asked.
Our sweaty bodies were proof we were in need to hydration.
Veronica went to the kitchen, returning with two bottles of cold water. While I drank, my mind was thinking about what we had done and what was next. That caused my flaccid cock to rise.
Veronica finished her bottle of water and looking at my erection, commented: "It does appear your cock is anticipating its next destination. Have you had anal sex before, John?"
Taking one last sip of water, I replied: "No, I've never done that before."
"Well, you are in for a new sexual adventure. I've been told by other men that it's a better experience than any pussy they have ever fucked. Let's see if you feel the same way, John."
She sat on the bed and turned her body sideways and rested her head on a pillow, lifting a leg. I gathered up my body and knelt on the bed between her nylon covered legs. I lifted her limp cock and laid it on the crease between her trunk and her left leg. I asked if she wanted me to use a condom. She said that she liked it bareback. She passed me a tube of lube which I rubbed on my erection. Her body smelled of a quality perfume that rose from the sweat of our previous activities. If it weren't for the slack scrotum and cock laying on her body it was like I was about to have anal sex with a woman. I guided my cock to the opening and pressed forward and her face grimaced but she didn't complain as I finished easing my shaft balls deep. She grunted with every stroke. It was very satisfying to finally be indulging the fantasy I had been harboring for decades. Her rectum was hot and tight around my cock.
"John, is it better than pussy, your wife's pussy?" she moaned.
How could I not tell her the truth.
"Yes Veronica, it is so much better than pussy. Your asshole is like a hot, velvet sleeve that is sucking on my cock."
There we were, a male and transwoman in sexual intercourse. In and out of her clinging rectum, I fucked her until that feeling of nearing orgasm quickly approached.
Speeding up, I gave one final lunge keeping my cock deep inside her. I ejaculated what felt like a quart of semen into her spasming ass. I had an immediate feeling of total satisfaction.
We hugged while we recovered, my whitish load leaking out of Veronica's gaping asshole. We showered together before we got dressed. I discussed my future visits before I kissed her and exchanged goodbyes before I made my way down the steps to the road and drove home.
I enjoyed the feeling of sex with a transgender female so much I visited her many times. We repeated the activities I described. Of course, she introduced me to being a bottom as she took my anal virginity.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com
If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available.