Leona
by CB Achtland

This is a work of fiction.

I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have no problems being there. I could just have a few drinks, take in the scenery, and after we left we could pick up a couple of hookers for a blow job or a fuck.

We got there quite early and I parked myself at the bar, and watched the talent coming in. In spite of myself I was amazed that some of them looked so hot! I would normally have been hitting on them, but I had to remind myself, that there was a cock between their legs! They flowed in, in all shapes and sizes, mostly heavily made up and wearing skimpy outfits that left very little to the imagination.

Many were dancing, some with other shemales, some with the punters who had come in. I watched, and after a couple of drinks when the dancing started to get dirty, I found my cock stirring. After all, I thought to myself, I could just fuck one of them in the ass, and even get a blowjob.

And then she walked through the door. She had big eyes, a pouty face, huge tits, and an ass to die for. She wore a black item that barely concealed her tits and ass, and ultra-high heeled stilettos. She caught my eye as she entered and smiled at me. I just knew that I had to meet her. She was now at the bar, and like all men, I rushed up to offer to buy her a drink.

We got talking and I found the combination of alluring eyes and throaty voice irresistible. Her ass was huge and it suited her, she looked absolutely stunning.

One thing led to another and I invited Leona back home. I would at least fuck that ass. We were soon naked and I found her very hot! Her tits were stunning, with broad areolae. I tried not to look at between her thighs. Soon Leona's puckered asshole was staring me in the face. I have fucked women in the ass before and had no hassles. So I spat on her asshole and began to work with my tongue. I love doing this to women and consider myself to be an expert. Sure enough, Leona began to moan and writhe as I tongue-fucked her asshole. I was enjoying this and my cock was hard. She tried to reach for my cock a couple of times, but could not. As I rapidly tongue-fucked her asshole, her moans grew louder.

And then she did something which I never expected.

With one swift movement, she spun her body around by lifting her leg over my head. So she was now on her back, and yours truly's face was no longer in her ass.

It was on her cock.

Whatever men might say, being humans, they are always noticing cocks, primarily to see how theirs sizes up. Any man who denies this is lying. I had seen plenty of cocks in porn movies and had noticed them. And I had noticed plenty to know that Leona's was a fine cock. And my face was on her balls.

My gut feeling was to pull away, but I'm a gent, and her hand held my head in place. And then came the words:

– Suck me, darling

I looked up and beyond her erect cock I could see her lovely tits and her even lovelier face.

I did what any man in my place would have done. I sucked.

I started with her balls.

They were perfectly round, hairless, and big. I could barely take them into my mouth. They smelt and tasted musky and she gasped with pleasure as I sucked them into my mouth. I sucked hard at them as I wanted to give this lovely woman a good time.

– Oh yes, my love, my darling, she gasped, and I sucked away.

And then she slapped her cock down on me. It caught me by surprise, and then she did it again, and again. I released Leona’s balls, now gleaming with sweat, and looked up to see her beautiful cock waving in front of my face. There was no turning back now, and I took it in my hand.

The proverbial drop of pre-cum glistened on the tip of her cock and with no second thoughts I took her she-cock into my mouth. It filled me completely and I thought I would choke. I thought of all the girls who’d sucked me, and if they could do it, I could and would. And so I began to give Leona a blow job, me, Mr Masculine, was sucking a cock, although a she-cock.

And I was enjoying it. It felt so right. Making love to Leona, felt so right. She felt like a woman, and the passions that arose in me were the passions invoked by a sexy naked woman.

Leona moaned encouragement and her fingers running through my hair and holding my head down on her cock made me mad with lust.

– Oh darling, she cried, you make me feel so special. Oh baby I so want to cum!

And I had no second thoughts about her cumming in my mouth. She began to move her hips, fucking my mouth, moaning all the time, and then with a final decisive thrust she spurted hot cum into my mouth. I almost gagged but fought the feeling and sucked hard, tasting for the first time, cum. And I loved it, the taste, the consistency, and the feeling of sucking a she-cock, and I sucked hard, taking down every drop. And after the cum stopped spurting out. I continued to suck, squeezing her balls, and getting a few more drops of Leona’s cum into my mouth.

I just lay there kissing her now-limp cock, rubbing my face over it, as she murmured sweet nothings while running her hands through my hair. Soon Leona’s cock began to stir again. She grabbed a handful of my hair, and pulled me away from her cock.

– My turn, baby, I want to suck your cock…

I had no complaints as I was hornier than I had ever been. I wanted that face with it sexy pout sucking my cock. I lay back and watched as Leona, her cock now hard again, got between my thighs. She began with my balls and I was in heaven! There are any number of girls who’ve sucked me, but this was different. It was special, and I then realized that this was because Leona herself had a cock. Macho man or not, I was enjoying this and there was no going back for me.

She licked, nibbled, and spat on my cock and soon had me moaning and thrusting my hips at her, desperately wanting to shoot into her mouth and all over her beautiful face. She took me fully into her and began the final sucking, and in a short while I exploded into Leona’s mouth. She pulled away and I realized that she had not swallowed all my cum, but had saved some. What was she going to do, I wondered?

She got onto me and our cocks were pressed against each other. She dribbled cum onto one of my nipples, then the other, and then drank it up with swift sucking motions. Nobody had done this to me before and I was instantly rock hard. We kissed deep, all the time cock to cock. I was definitely in lust, but I was scared I might fall in love.

– Fuck me, Jake.

It was a simple statement. And I had fucked women in the ass before, so there was no problem here. Leona got on her hands and knees, and I couldn’t help admire her large ass. It was so perfectly proportioned and suited her well. That ass was made for Leona, and now it was mine. I got my face between her ass cheeks and admired her white puckered asshole. I spat on her asshole and was soon eating her ass, a task that I enjoyed. My tongue went in deep and I tongue-fucked her. She moaned and squirmed, but I held her firmly in place. She collapsed onto the bed and I drove my tongue in further. I was near insane with lust.

I held her in place and got my cock ready, lubing it with spit. I placed it at her asshole, and she moaned, yes. I began my entry and she responded allowing the whole on my 9-inch cock into her ass. I was in and Leona was comfortable. It was time to fuck my first shemale. I fucked her ass hard, fucked her like I had never fucked an ass before. Women usually began to complain, but Leona was taking it and loving it. I began to thrust faster and harder and she screamed encouragement. This made me push myself more and I was fucking her like a bit of sex-meat and she was loving it. As I was about to shoot I grabbed her tits and used them as handles, squeezing them as hard as I could.

I came inside her and gave her a love bite on her neck as I shuddered to an orgasm. She was moaning aloud. I collapsed onto her, my cock still in her ass. Our bodies were covered with sweat and we just lay there, satiated and exhausted.

After what seemed an eternity I pulled out.

– Darling let me clean your cock.

She cleaned my cock sucking on it gently. I then decided to clean her ass. I had never done this before, but it came naturally to me. I ate out some of the cum, and then stuck two fingers in, pulled out some cum and offered it to her. She wordlessly lapped it up.

We looked deep into each other’s eyes, and there was an unspoken tension. This session could only be complete if Leona fucked me. And I had never been fucked before, not even by with a dildo. No woman had even eaten my ass. But there was something special here tonight. I turned around and got on my hands and knees.

– Good boy, I never though you’d agree!

And with a throaty chuckle she slapped my ass! Leona then spread my ass cheeks and spat on my asshole. I tensed as she brought her face towards my asshole, and then I felt her tongue touch me. She began to lap at my asshole with tiny strokes, sometimes in a circle, and it just felt so good. My cock was instantly hard again. I so wanted this.

Leona was an expert and she massaged my prostrate, pulled my cock and balls behind for a quick kiss and nibble, and of course, fucked my asshole with her lovely silken tongue. And I wanted more.

She began with her fingers, gently inserting one, and finger fucking me, and then inserting a second. She knew how to do this and I was able to take her in without any discomfort. I trusted her and was relaxed. I knew that at some stage, she would cock-fuck my ass. And soon it came to pass. After a long session of finger-fucking she grabbed me by the hair and twisted my face towards her. She looked deep into my eyes.

– You want to get fucked up the ass, boy?

Yes, I wanted to get ass-fucked by this beautiful creature. She placed her cockhead at my asshole and slowly began to enter me. I was still relaxed and began to take her in. I felt like I was going to explode, but I was stubbornly determined to accept her and to give her, and both of us pleasure. Deeper and deeper she went in and I took all of her. But she then pulled out. She finger-fucked me again, and then put her cock in again. By this time I was completely relaxed. She then used her fingers again, and only on the third time did she actually begin to fuck my ass.

When she started, I though I was going to die, but the waves of pleasure began to engulf me and I began to yell encouragement. This just felt so good. The weight of her over me and my complete submission made me erotically charged like never before. I wanted this, and Leona obliged by fucking me, harder and faster, until with a long moan she shot into my ass. The hot cum felt so good and before I could stop myself I had shot a wad myself.

She cleaned my asshole and I cleaned her cock. We lay together in bed and I think I was in love. I never wanted to have anything to do with a woman again. This is what I wanted. I didn’t know whether it was right or wrong, but I really did not care. I was a changed man and I was a new man ready to experience new discoveries. And I wanted Leona to be my guide on this new journey.

story by: cham6996hard

Tags: fiction transsexual transgendered sex story

Author: cham6996hard

Related sex stories: