Leila is a shemale erotic story of a first time experience and the instant addiction that having both male and female in one body can bring to a man
I’m an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.
It all started one rainy afternoon in Northern California as I was driving home after a party I’d attended alone the day before.
I’d stayed over at a friend’s house and after a nice leisurely breakfast, I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.
I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road was drenched. Her thin silk dress was plastered to her shapely body and her raven hair was matted to her skull as if she’d been swimming.
I quickly decided that I would pick her up. It was no great decision; I mean she was a knockout. I could tell that she had a great body because her wet dress left little to the imagination, and the 4-inch high heels she stood in made her look like a goddess.
As I pulled up to her and leaned over to push the door open she smiled at me. I was struck dumb! Her beauty was breathtaking. When she climbed into the car and the door closed I was still sitting staring.
“Hi, hunk, my name is Leila,” she said. And nothing has ever been the same for me since.
We drove down the highway without speaking for a few moments. Then to my amazement, this beautiful creature scooted over next to me and began to fiddle with the fly of my pants.
At first, I tried to pull her hand away but she was insistent and without a further struggle from me she finally popped my pants open and pushed her delicate hand deep into my open fly. I was in some kind of zone. I knew what was happening but not how to react to it. Nothing like this had ever happened to me before.
Leila leaned forward and placed her ruby red lips on the head of my dick and began to suck me off. I could feel her hot wet tongue lapping up and down my shaft. Soon it felt like I was fucking a woman’s cunt. Her lips were tightly gripping my dick and her head was bobbing up and down in my lap. I was on fire.
Just before I came I looked over and saw that she was stroking her own rigid dick. It was shaved, but it was every bit as big as mine and as I came in her mouth with loud grunts of passion I saw her dick spew hot sticky cum in an arch out onto the dashboard of my car.
Needless to say, I was in shock. I pulled the car over at an overlook by the ocean. The wind was up and big fat drops of rain beat against the windshield of my car. I sat there trying to catch my breath from the best blowjob I’d ever received in my life.
Finally, I was able to gasp out, “You-you’re a man!”
Leila looked deeply into my eyes and moved closer, right up next to me. I could feel her firm breast pushing against me, and felt the heat radiating from her body as she whispered, ‘Nah uh.’ Then she grabbed my hand and opened the car door pulling me along with her.
I wasn’t sure what to do, but I let her pull me along. I kept glancing at her perfect body, legs to die for, and an hourglass waist. How could this lovely creature be a man? I kept wondering to myself. It was agonizing, she was just too beautiful. Too perfect.
Then we were slipping and sliding down a rain-swept dune, down, down all the way to the deserted beach below. And without a word Leila pulled her soaked dress over her head and threw it to the wind.
I stood there looking at a beautiful woman, naked except for net stocking and a black braw. But damn, there was one marring effect with that vision. She had a massive hard-on, all shiny from her previous orgasm, and the rain still drenching her.
I was soon as wet as Leila and even though I was completely mystified, and a little frightened I let her unbutton my sopping shirt, then pull my pants down. When she knelt down in a puddle on the beach; I wasn’t sure what was happening. But when she went down on hands and knees and wiggled her beautiful butt at me I knew what she wanted.
I looked for a long moment. What was I doing? But as I looked at the perfect naked body displayed before me, I said to myself, ‘What the hell, just this once.’ And I knelt down behind Leila ready to butt fuck her.
To my surprise, as I positioned myself behind her I felt her small hand guide me lower. And when my dick slipped into a hot moist cunt I gasped in surprise. It was something I hadn’t expected.
Wildly I began to thrust in and out of Leila. The feeling of rutting like animals out in the open and in the rain like this was exhilarating. I’d never done anything like it before. And the wonderful feeling of fucking her “cunt” was something else that made the whole experience something special.
I had no idea how she’d accomplished it, all I knew was that Leila was incredibly hot, and I was going to come deep in here any second. And when she started to hiss, “Fuck me harder, fuck me like the male animal you are hunk. Make me cum on your cock big man, make me come!” That was pretty much it for me.
I shot my second load into Leila’s cunt this time, grunting with each thrust until I was without anything left. And as I began to come down from my exertions I noticed that Leila was sporting an enormous hard-on still.
Curious I pulled out and rolled her over onto her back in the puddle on the beach. There she was in her glory, and I feasted my eyes upon her, lust building quickly after only moments.
I quickly realized that Leila had both a cunt and a dick and they both looked good enough to eat. I felt like a sick bastard but without any further thought, I brought my lips to her shinny cock and engulfed it.
It took several minutes to figure out the best way to give my girl head, but being a guy I already had some idea what was required. Then I went to town. I wanted to give her pleasure equal to what she’d given me. So I began to wildly fuck her cock with my mouth.
Then an idea struck me. I reached down and began to finger her clit, pushing first several fingers back and forth across her sensitive clit and down into her slit, then more fingers until I had all four sliding in and out of her, with my thumb playing fast and loose with her clit.
It was agonizing to watch. Her cunt came first, but her dick erupted soon afterward, and I watched as Leila’s perfect body writhed, splashing muddy water all over the place as she rolled around in the puddle still forming ever bigger around our wrestling bodies.
That afternoon I had my first experience with a shemale. And what a shemale she was. We fucked two more times on that beach, and might have gone once more if we hadn’t been run off by the park rangers who patrolled the place several times a day.
The sad thing…
The sad thing about my story is that I don’t think just a regular woman will ever be enough for me again. I mean, imagine having a woman who knows exactly “how” it feels to be a man. She knows exactly what a male’s orgasm is like and how to achieve it. And then imagine that you have the loveliest 22-year-old woman anyone could want.
It makes it hard to tear yourself away from a relationship like that. I still can’t bring myself to do it and it’s been two years now. Regular wild sex whenever I want it. Oh, and I’ve become an expert at giving head too, by the way.
Leila is a shemale erotic story presented by eroticprose.com. The home of erotic short stories and erotica
Written by Michael