Well, I knew I had been taking a big risk by joining a females-only dating site. I had been cross dressing for two years, and my mirror had been telling me for months that I was every bit as good looking as many of the girls I knew in the office where I worked. Much better than half the girls on the web site had joined, I was sure of that. Perhaps there was one problem, however. I was obsessed with having a huge bust whenever I dressed myself as a woman. My wardrobe was filled with clothes that could accommodate my 52 inch, J cup boobs and with my 32 inch waist my figure was distinctly hourglass. But I wasn't about to make any concessions with my first date as a club member. His name was Achal, and if he didn't like what he saw or was embarrassed to take our relationship further, well that was his bad luck.
For my profile on the dating site I had posted photographs of myself in a much more modest bra size - a 44F cup, so that was what Achal was expecting to see tonight. However to say that he was definitely not expecting the surprise he would get from lower down was more than an overstatement.
I parked my car in the after hours parking bay along from the Starbucks cafe where we had agreed to meet. Making a final check on my lip-gloss and long dark hair in the mirror above my head, I ventured into my own version of the unknown. I had chosen a jet black, fully-lined pencil skirt in a wool blend with a pale gold roll neck sweater. As I walked along the sidewalk in my 4 inch patent court shoes, I experienced the thrill I always felt when the hem of a tight skirt caught the back of my stockings. At home, that sensation alone had made me cum into my panties on several occasions without any assistance from me.
The cafe was almost deserted as I pushed open the door, but Achal was not hard to spot at the far end of the line of tables. He stood up when he saw me, and as he pulled out a chair for me I could see he was already taking in my golden globes. I could feel the eyes of the other diners, both male and female, drinking in my shape. My butt was also pretty hot as I always wore specially enhanced panty-girdles under all my skirts and dresses.
We ordered Cappuccinos. I felt I had passed the first test a female as we faced each other and I began to relax, although I kept brushing my hair from my eyes, as I kept looking down at the table to avoid answering Achal's unasked question about my bosom's change of dimensions from all my dating site pics.
"You came by car" I asked "No, I live close. I just walked. How about you" "Car. I've parked it less than a block from here in that deserted car lot round the corner. We could go for a drive if you like when we've finished these," I offered.
We strolled back to the car, with Achal a little reluctant to take my arm. He's probably worried about brushing up against my breasts, I thought. He seems to be so much shyer than I had imagined. My calves, stroked again by the tight skirt, now that we were taking longer strides, set off my juices. How women can walk in slim skirts and not feel randy this way I found had to imagine, I teased myself.
As I set about placing the key in the ignition, I felt Achal's hand on my cheek. "You're beautiful, you know that" said Achal. "So much more than in your photographs. They don't do you justice at all."
"You're very nice too, Achal. You're so gentle with that hand. I wasn't expecting that at all. Men are often so rough with me," I lied. Achal was my first ever date with a man.
"Kev. Call me Kev." His words caught a little in his throat as he said this and I knew he was struggling to work out how to make his next approach. He surprised me again, however, by suggesting we move into the back seat of my car, "So we can have a bit more room."
We slipped into the back of the car, Kev sitting on my left. He began kissing me so gently that I found this unexpectedly mild approach exciting in the extreme. No grabbing for my boobs, no hand up my skirt, just a soft pair of lips on my earlobe. I was warming to this man. But then if he is too nice, I thought, he's going to discover the secret beneath my skirt, not to mention the silicone fraud that the contents of my sweater would reveal. I had envisaged only a night with some over-sexed male who would expect me to suck him off and leave me when he had zipped up his jeans without any need to enquire any further into mere issues of gender.
Achal's quiet approach could prove much more of a problem than some randy no hoper. I was beginning to feel distinctly nervous. That makes two of us now, I thought, as Achal now caressed my face with his left hand, his right somewhere out of sight, but distinctly inactive. Perhaps if I gave him a little encouragement, I could direct him in the quickie in the jeans and escape with my gender intact!
He still hadn't ventured a hand on my boobs, so some direct action was required. "Achal, don't you like my big bust Is it too big, do you think" With this, I moved his hand from my cheek and rested it on my right breast.
Achal's reaction as he kissed my ear was both unexpected and stunning.
"Oh God, Oh God, Oh God, Oh Jesus." His words were barely audible, hardly words at all in fact. More of a strangled gurgling sound as he continued to repeat the words. His hand, still barely touching my sweater, he began lightly circling my huge melon, roaming over my massive boob with only two fingers. Then he kissed me with such passion as no woman or man for that matter had ever done. I felt my cock rising under my skirt, although I was willing it to stay soft. His hand then reached under my sweater in a frenzied attempt to feel my left boob now.
Here we go, I thought. Now all will be revealed. Perhaps if he stays feeling me only through my bra, I might get away with it, but he kept searching for my nipples - which I may say looked and felt like the real erect thing. The huge enhancers I had bought recently were amazingly realistic not only to look at but also to the touch. I had attached them with the new adhesive that had been supplied with them. But when Achal slipped my bra strap from my right shoulder, easing the silken cup from the silicone mountain beneath I knew the game was well and truly up.
Ryan Le Bar Achal's reaction was even more startling than when he first touched me.
"Oh, Holy Jesus, baby. They're silicone! Oh, fuck you wonderful woman." And with that he began pulling my brassiere down to my waist as his two hands filled themselves with his own uncontrollable pleasure".
By now, I was desperate for him to wank my throbbing dick. The psychological effect he was having on me by his furious hands, made me almost black out with my own need. I pulled his right hand from my heaving tit and dropped it on my skirt. He began to work me through the skirt's material as I cried out for him to "Undo my fucking zip, for God's sake. Hand job, give me a fucking hand job, Kev. Hand job me for Christ's sake."
But there was no directing Kev from his main objective. His face was buried in my silicone B52s, and I barely heard him murmuring, "You do it baby. Wank yourself off for me, I want to hear you go for me."
In a frenzy of need, I pushed my hand down the waistband of my pencil skirt, feeling the precum on my panty girdle as I began to madly stroke my 7 inches, holding myself through the nylon underwear until I exploded in foam and noise, soaking the silk lining of my skirt. I kept pounding myself as if the stream would go on for ever, hearing Achal's moans in my massive breasts as he to jerked himself off with a fury that left me gasping at his intensity.
We held each other in sticky wonder for another 20 minutes, before, reluctantly, I said it was time to go,
"Did you enjoy the practise run" I teased. "Practise You call that practise" "Sure," I laughed. "I'll wear my Double L cups next time - if you have the strength!"
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