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"Hope you didn't make plans," she said, "because I've made reservations for us at the Maxwell House. Not the best hotel in town, but still very nice and not much chance anyone we know will see us there." I can't tell you how happy this made me - the Millenium New Year in a fine hotel with a beautiful woman I'd been dreaming about. She wanted to meet me there, so I packed an overnite bag, slowing down only long enough to jack off thinking about her. That day I splurged on a new sport jacket, tie, slacks, and even new shoes. She was a classy lady and I wanted to look my best. I was over an hour early in my excitement, so I went on up to the room and hid my overnite stuff away, so as not to appear too anxious. I met her as she parked her car, and as she got out she flashed me with those beautiful legs encased in black hose. Her dress was a skin-tight beaded expensive-looking number in a deep blue which accented her blue eyes. As she popped the trunk she bent over to retrieve. She dropped (jiggled) next to me on that couch.I asked him about his life again. He was a shy and didn't get dates to hear him tell it as in the bar the night before. Because J told him we would all go out on the town one night while he was in town, so he could have some fun and get a date one way or another. AND Here he was wanting to go out.....and now look at J's tits. I told him not now, but maybe he would like some of the wine we have been drinking tonight and we could talk about going out and stuff like that. I did this knowing he was watching her tits through the shirt. This gets me going like nothing else!J offered to get wine. As she was walking back to us he was looking at her nipples through the shirt. He was trying to be discrete about it.I pulled her next to me and d****d my arm over her shoulder to ask her how she would get him a date "one way or the other" staying in our hotel room? J told us the next night was the night to go out. He got a sad look before telling us.
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