Quote:
Originally Posted by housepics
How'd the date go? Did you ever post about it? If so I missed it.
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Hey - So it went well. She ended up wearing the short skirt, no panties, a sheer plaid buttondown top with a cupless bra underneath. The bra added a whole different element, because it made it obvious that she was trying to show her tits and not just a braless woman.
We had a few drinks while she got ready. The babysitter arrived and we hopped into the car. We headed to a small downtown area about 20 minutes from our house. It has several restaurants and bars with outside seating. We walked along the street and when the sun shone at our face the shirt was Extremely see through....quite a bit more than I had planned. She started to act a little nervous at the looks, but I assured her that it was her imagination (It wasn't by the way). We picked a restaurant and sat with her facing the sidewalk. My first dare came when she went to the bathroom. (The goal is to achieve 10 dares in the evening). I dared her to send me a picture of her with the shirt unbuttoned from the bathroom. She did...My second dare I asked her to leave all but the 2 middle buttons unbuttoned and walk back to the table like that. She also agreed. Her boobs were practically hanging out.