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 than many of the girls I knew in the office where I worked.
Better than half the girls on the web site had joined, I was sure of that.
Perhaps there was one problem, however. At 34, I was obsessed with needing to have 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 Kevin, and if he didn't like what he saw or was embarrassed to take our relationship further, well that was his bad luck.
He was much younger than me at only 22. A boy really. For my profile on the dating site I had posted photographs of myself in a much more modest bra size a 44F cup, so it was that bust size that Kevin was expecting to see tonight.
However, to say that he was definitely not expecting the other 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 caf?here 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 cut just to below the knee matched with a pale gold roll neck sweater. As I walked along the sidewalk in my 4 inch patent courts, I experienced that 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 as I paraded around the house. The caf?as almost deserted as I pushed open the door, but Kevin 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.
Kevin, wearing a stylish red shirt and jeans ordered our Cappuccinos. I felt I had passed the first test as a female. As we faced each other across the table I began to relax, although I kept brushing my hair from my eyes, as I kept looking down to avoid answering Kevin'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. Finishing or coffees quickly we strolled back to the car, with Kevin 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 expected. My calves, stroked again by the tight skirt, now that we were taking longer strides, set off my juices once again.
How women can walk in tight 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 Kevin's hand on my cheek. "You're beautiful, you know that?" said Kevin. "So much more than in your photographs. They don't do you justice at all" "You're very nice too, Kevin. So gentle with that hand.
I wasn't expecting that at all. Men are often so rough with me," I lied. Kevin 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 boy, no mistake. But then if he is too nice, I thought, he's going to discover the secret beneath my skirt, not to mention the silicone babes that the contents of my sweater would reveal.
I had envisaged it would be a night with some over-sexed male who would expect me to suck him off then leave me when he had zipped up his jeans without any need to enquire any further into mere issues of gender. Kevin'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 Kevin 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 towards that quickie in his jeans and so escape with my gender secret intact! He still hadn't ventured a hand on my boobs, so some direct action was required.
"Kevin, don't you like a really 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. Kevin'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, barely words at all in fact. More of a strangled gurgling sound as he continued to repeat the words.
He was almost crying.
His hand, still barely touching my sweater, 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 urgently 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. But when Kevin 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. Kevin'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 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 tits and dropped it on my skirt. With a deep moan 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. Handjob, give me a fucking handjob, Kev". 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 for me, I want to hear you go for me". In a frenzy of need, I pushed a hand down the waistband of my skirt, feeling the precum all over my nylon panty girdle as I stroked my 7 inches like a crazed person until I exploded in cream and noise into my nylon undies, soaking the silk lining of my skirt and stockings. I kept pounding myself as if the stream would go on for ever; Kevin's moans were being lost 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 practice"? "Sure", I laughed. "Next time I'll wear my Double L cups for you if you have the strength"!