JOIN
The price of gambling just got high
My wife, Jessie, and I like to place bets on sports events. It has never made a lot of sense to either one of us the bet money since we share it anyway. Therefore, we usually place bets for "favors." I won the last bet, and with it, I won an evening during which Jessie would do whatever I asked.
I picked a Saturday night for the adventure. We went out to eat. I had Jessie dress for the occasion by wearing a button down shirt with a see-through bra underneath and a loose, short skirt that ended about halfway between her waist and her knees. Jessie is nearly 5 feet 8 inches tall and weighs approximately 140 pounds. Her 36 C breasts and rounded bottom look great in virtually anything. Her shoulder-length brown hair and dark brown eyes and full lips give her a sensual appearance that I adore. Looking at her as she got ready, I could hardly wait, knowing what I had planned.
We were seated at a table toward the back of the room. Our waiter was a young man named Kyle. I told Jessie to position herself so that if Kyle stood in the right place, he would be able to see down her shirt. It didn't seem to take Kyle long to realize the opportunity as he slid a bit to his right while taking our drink order.
I told Jessie to unbutton one extra button before he came back with the drinks. Her shirt was open nearly to her breasts, and I suspect you would be able to make out her nipples if she leaned forward so that the shirt fell away from her a bit. When Kyle returned, she did just that. Kyle leaned down and over her shoulder a bit as he gave Jessie her drink. His eyes were clearly looking down into her shirt as he placed the drink on the table. He blushed when he saw I had caught him staring down my wife's shirt.
By this time, Jessie was getting into the spirit of the evening. She started flirting just a bit with Kyle as he explained the specials to us.
While he was taking our order, Jessie "accidentally" dropped her spoon on the floor. Kyle quickly knelt down to pick it up, and was hidden from my view by the table. Jessie told me that he was looking at her thighs as he stood back up. She didn't give him a glimpse under her skirt at that point, but enjoyed the attention enough that I thought she might as the evening wore on.
Nothing further happened until Kyle asked if we wanted an after dinner drink. We ordered and he quickly returned. As he placed the drinks on the table, Jessie again "accidentally" dropped something. This time a tube of lip gloss that she had just used. Kyle again knelt down in front of her. I could not see what was going on, but Nicole told me she opened her knees a few inches. Her skirt was short and she said she was certain that Kyle had looked directly up her skirt. He must have, because when he stood up his ears and face were red as a beet.
