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I just wanted to give him something different and unexpected this year. Something that I knew he’d love and never forget. He’s usually the one who plans the evening, but this time I made the reservations at a hotel restaurant and booked a room for us upstairs. I bought him one of the usual Valentine’s Day gifts – a pair of black silk boxers with red hearts on them and an Italian watch he’d been eyeing for the past three months. Aside from me doing all the planning, everything was going as usual. I was wearing a backless shin-length red dress with spaghetti straps resting on my shoulders. It was made from a glittery fabric that sparkled a little when the light hit it. Underneath I wore nothing. I pulled out the suit I wanted him to wear that night – including the silk boxers. We both got dressed then headed over to the restaurant. We sat at the candlelit table surrounded by other couples just like did last year and every year before. We drank the same champagne, talked the same. I think she notices. We get to the master bedroom and look out the balcony that over looks the pool. She says she could see me in this place during the summer checking out the hot young girls at the pool. At this I realize this hot mature woman maybe into me. I want to tell her that I want her but I am way to shy. So instead I make a stupid comment about how it has been so long since I have had a girlfriend, or even a date. Moving to the area has been tough. She proceeds to tell me how I am a very attractive young man and girls my age should be all over me. She says the fact that I can afford to buy a place at my age should make me extremely desireable. I tell her about how I am shy and don't meet new people easily. Then she tells me as an older woman she knows the nice shy guys are the ones that are most attentive in bed, and she wishes should would have realized that at a younger age. At this I finally get up the balls to tell her what I wanted too: I would much rather.
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