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A very special lady

Transgender
2012-03-30

     I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and willing holes. Unfortunately, all the sexy teen pussy  had graduated from high school, and had gone on to college. With the pickings mighty slim, and me not compromising my standards, there was no choice but to head for a bigger city.  

     Jake, one of the few people that I had gotten to know reasonably well, had set me up on this blind date. Her name was Chantel, he said she was a knock out, a wonderful, sexy blend of her mother's Thai and British heritage, and her Dad's Swedish. That got my cock eager, if nothing else, at least I'd have a date with a very exotic looking lady.

     The door opened, and there she was, smiling at me. Oh my god, Chantel looked as good as Jake had told me. Jet black hair, parted on the left, and hanging down to just below her shoulder blades. Her face was a knock out, her Asian and Europian features in a wonderful blend of sexiness, with very blue eyes, from her Dad's Swedish heritage, no doubt. Being that I am 6 feet, I lust after tall women, and with Chantel being 5 feet 11 inches, oh yeah, perfect. Her chest was small, proportionate to her height, and I was relieved to see no hint of artificial enlargement. I CANNOT stand fake tits, if a woman isn't secure enough to be happy with the melons that Mother Nature endowed her with, that is a deal breaker.

     "Dennis, hello, welcome, please come in" Chantel said, with a definite English accent.

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     I did as she asked, watching as she turned to lead me. Oh yeah, what a knockout, Chantel was wearing a black, loose flowing dress, that hid her charms somewhat, but just made me the more eager to uncover those naked charms and assets. She was wearing black stockings, I hoped it wasn't pantyhose, so unsexy. The world lost a good deal of female sexiness when pantyhose replaced stockings and garter belts.

     In her living room, Chantel gave me a martini, and we clinked glasses. The martini was smooth, and I quickly downed it, and she was happy to refill my glass.

     She surprised me when she suddenly asked, "Dennis, what do you expect from our date, what are you hoping for?"

     I was nonplussed by such a direct question, and I tried to collect my thoughts.

     She said, "Perhaps it would be better if I told you what I want. I want something different, I'm not interested in some plain, vanilla sex, if that is all you are hoping for, well, we can say goodnight right now. If, however, you are willing to try something very different, we could have a wonderful time. "

     With her body, her voice and her face, I'd try to swim the English Channel, and I eagerly agreed. She smiled, and led me upstairs, in her bedroom, she slowly stripped me down, planting soft, delicate kisses, bringing my prick up to a ready, stiff 7 inches.

     "Lay down Dennis. "

     She smiled, reached up to her neck, and started to undo the collar holding her dress together. As the dress fell away, I got a look at her melons, nice, orange sized, with stiff, excited nipples.

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   She was indeed wearing stockings, with a black garter belt. I gazed towards the triangle of her sex, it seemed something was blocking my view. I was confused, then realized that she was sporting a hard, stiff 7 inches! Holy Shit! 

     "Yes Dennis, it is a real penis. I was born with both male and female organs, though I am more outwardly female, my cock is more than just an appendage, it gets as excited and as ready as yours does. My parents thought that since nature made me this way, why subject me to surgery, to correct it to some societal norm? I was brought up with a good sense of self worth, of course, my difference was kept concealed from a world that would be quick to make a harsh judgement. In my teens, when my cock started to develop, my panties had a pouch at the front, that I could tuck my cock into, then make sure it was pulled up tight against me. If you are still up for something different, I'd like to take your asshole. Are you still an asshole virgin, Dennis?" she cooed.

     Wow, what a date. I was still an asshole virgin, and never thought I'd end it. I had been having darkly exciting thoughts, about having a girlfriend strap on a dildo, and bust my back door cherry, but working up the nerve to actually ask that? And here was an absolute knock out, female enough for me, who wanted to break me open with a real cock. I nodded, eager for her to take me up the ass.

     She smiled, and told me to turn over. On my hands and knees, I felt her pull my cheeks apart, then the electrifying sensation as she applied her hot, wet tongue to my asshole. I growled with pleasure, the feel of her tongue teasing and running over the tight rim was nothing short of mind blowing.

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   She brought a finger into play, and I could feel it push in to the first knuckle. I worked on relaxing the tight muscle ring, as she continued to lick and finger my asshole for a good long time. I could feel myself starting to relax more.

     "Turn over Dennis, I slipped a valium into your drink, just something to relax you and make your virgin breaking a little easier," she whispered.

     "Yeah, I'm ready for it Chantel" I whispered.

     She smiled as slid a large pillow under my hips. I was lifted up, with my ass free of any obstruction, and I felt well greased fingers sliding slippery lube over my tight rim, then a finger worming its way in, spreading it around the tight walls. Chantel slid a coating of lube up her stiff cock, the lube making her erection gleam in the dim light.

     "Grab behind your knees, and pull them towards your chest. "

     I did so, feeling my asshole spread apart slightly, ready for her cock. She got into position, her legs straddling the pillow, pushing another, smaller pillow under my ass to raise it up for the right level, setting my ass up for cornholing. I could feel her lubed up cock head pressing against me.

     "Now, just relax baby, you'll love it" Chantel whispered huskily, "I'll bust your cherry gently. "

     I felt the push, then the lubed head slipped in. I hissed a bit, she held it steady, and urged me to relax.

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   I worked on it, and told her to go on. Inch, by inch, slowly, slowly, she pushed into me, my tight ass walls getting their very first fuck. The pain was noticeable, but not unbearable, and I was grateful for the valium she had slipped into my drink. She stopped with about an inch left.

     "Ok baby, one last push, and your virgin busting will be complete, are you ready baby?" she cooed.

     "Yeah, I'm ready, complete my cherry busting!"

     Chantel thrust her hips forward, and I felt my ass get the stretch as she buried the last inch, going in right to the balls. I let out a moan as I felt it, it was actually feeling pretty good, the pain of my asshole cherry being busted was mixing with a pleasurable pulsing, and as she paused, I urged her on.

     "Yeah, oh yeah, keep fucking me, I want my asshole to get fucked good, yeah, give it to me Chantel!"

     She smiled down at me, and leaning forward, my legs went over her shoulders, and she started a slow, steady rhythm. I pulled my hands down and curled them around the sexy cheeks of her ass, pulling her against me, letting me know that I was starting to enjoy it more and more. The relaxation of the valium, and my tight asshole giving up the clench, adjusting to the plunges of her cock, let me enjoy it. The fact that I was being taken just like a vanilla female, and the stroking of her throbbing cock over my prostate was turning my cock into a red hot poker, it was harder than ever. Chantel grinned as she saw my eager hardness, she grasped it, and started to stroke my cock. I growled with pure pleasure, oh, her hands knew what they were doing, she stroked me in time to the plunges of her cock up my ass, and Chantel started to make noises of pleasure, her growls and gasps of joy letting me know that she was closing in on her climax.

     Chantel grunted, "Are you ready to cum baby?"

     "Yeah, oh fuck yeah, blow your load up my ass, and make me shoot!"

     "Yeah, oh yeah baby, here it cums, gonna blow, gonna fill your tight ass baby, yes, yes, yes, FUUUCCCKKKK!!"

     My cock swelled up tight, just as Chantel let out a drawn out shriek, and I felt her cock pulsing wildly as she went off, over and over, and the feel of her cum gushing, filling my ass with her heated load, drove me over the edge. I growled as my cock erupted, three large ropes shot out, splattering against my chest, my cock continued erupting over Chantel's milking hand, a geyser of hot, white cum spilling down over her curled fist and onto my belly.

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   I was thrusting and grunting, spilling even more cum as it slid down the length of my shaft. My ears were ringing and my breath was coming so fast I could barely control it.

     When I got my bearings back, Chantel was smiling at me, and she slowly withdrew her cock from my ass. She started to lick up the cum that was splattered over me, eager to get every drop. She flopped down next to me, and grinned.

     "I must make sure that your yummy load is not wasted on a towel, not when my mouth is so eager to swallow it all", she purred, "Dennis, would you like to join me in the shower?"

     Soon we were under the hot spray of water, soaping up, and it was a surreal experience to be in the shower with such a gorgeous lady, watching as she soaped up her hands, and carefully washed her cock, wild.

    As I soaped up her gorgeous curves, she sighed with pleasure.

         She said, "So Dennis, did you like it?"

         "Oh yeah, I fucking loved it!" I enthused.

         "Excellent, I want you to do me now. I do have a vagina, if you'd like, but I love getting my ass fucked, would you like to fill my tight ass Dennis?" Chantel cooed.

         Just the thought of taking this gorgeous creature's ass drove me up to rock hardness, and Chantel smiled at the rise.

         "I take it that means Yes", she purred, "Let's get dry, then take me back to bed, and let me have it. "

         Back in the bedroom, I put her on hands and knees, and got my tongue down to her asshole, running over the tight twitchy rim, again and again.

         "Fuck, oh fuck I love it, lick and finger my asshole lots, then fuck my tight hole, I'm gonna love it!" Chantel growled huskily.

         I brought my fingers into play, and licking that tight hole, and running my fingers into her, feeling the tight grip and listening to her moans of pleasure, kept my cock granite hard, so ready to return the fucking.

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       She rolled over, lifted her legs up, and placed herself in the exact same position.

         "I want to get it the exact same way, take my ass the same way I took yours, let me have it Dennis, I want your cock up my tight hole!"

         I lubed up, and placing it at the entrance, started a slow and steady push.

         "Yes, yes, fill my hot, tight hole, I love it, drive it in Dennis, bury it NOW!"

         I did as she wanted, letting out a growl of pleasure. Chantel's asshole was the tightest, hottest hole I have ever had the pleasure of driving my cock into. The heat and the tight clamp of her smooth ass walls surrounded me as I buried my cock in one bold thrust. Chantel let out a drawn out cry of pleasure as I went in right to the balls.

         "Yes, yes, oh yes, just what I needed, now give it to me Dennis, fuck my ass, really ride me, and flood my tight hole with a thick, juicy load!"

         I had her ankles up by my shoulders, her ass spread around my cock, and I gave her what she needed. I plunged in, over and over, my cock buzzing from the hottest, tightest grip I had ever had. Her cock was back up to rock hardness, and I quickly wrapped my hand around it, eager to stroke her to a shattering climax. She started to grunt and moan as my hand stroked up and down her prick, in time with the driving fuck of my cock surging up her ass.

         "Fuck, yeah, fuck my ass, fuck me fuck me!"

         My cock was ready to blow, I felt the jerk and the swell of my cock head, Chantel let out a cry of pleasure as her ass hole was stretched to the max around my cock, and I felt the cum surging up. With a wild groan of pure pleasure, my cock erupted, I could feel my cock pulsing and pumping a fresh volley of cum, filling up Chantel's tight ass.     The feel of my cum pouring hotly into her set Chantel off.

         "Fuck, fuck, fuck, fill my ass, yes, yes, yes, YEEEESSSSS!!"

         Her drawn out howl of pleasure filled the bedroom, her cock pulsing in my hands as she erupted. Two shots of thick cum flew up, splattering just below her breasts, the rest flowed out like a fountain of hot, white spunk, spilling down the length of her shaft, over my curled fist and onto her belly.

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       I stroked her until her cock was dry, then, with her seeing what I was doing, I quickly brought my hand up, and licked off all the cum. Her eyes glowed with pleasure, as I slid out of her well ridden asshole, and quickly got my mouth busy, licking up thick, gooey trails of her cum, relishing the taste. She had done it for me, so it was only fair that I clean up her incredible body, too.

         I took a quick side trip into the bathroom, washed off my cock, marveling at my good fortune. A blind date, who would have ever thought I'd discover such a diamond in the rough?

         This may have been our first date, but it was not going to be our last, the sight of her in bed, stretched out, inviting me between the sheets, would bring me back eagerly.                          

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