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 Kevin, 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 Kevin 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 café 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 café was 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.
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 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.
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 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 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. You’re 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.