Where it happened: In bed
Langauge: English
Sex: Female
Rating: 7
Category: Straight
I was 24 at the time and he was 17. We will call him Billy I was working leading a group of volunteers in the upper east side. He was one of two young men and we had between 15 to 25 young women who went door to door always in teams of two. He was very personable and one of the best workers. When I trained him he had no confidence with pretty women his age. When I looked at his work he had the highest success rate with men and took in more money than most. Every co-worker said he stumbled when a pretty woman came to the door and they had to take over. So one day I ran a route with him and sure enough he fell apart at the first pretty smile. This happened four times and I had no problem getting their support they were easy. Being a supervisor I was concerned and started breaking my own rules and started asking personal questions. I went no where. Well every two years the top volunteers are flown to a vacation spot and treated to two weeks of hospitality. Well it was during last years snow and Billy was chosen as the New York top sales person . I sent him and one very pretty young woman to Saint Thomas island in the Caribbean. I told them company rules were suspended hoping they could have fun together. She called me at the airport before they left and said he was great to work with but can’t look her in the eye. He can’t even talk. When they landed she said Billy was miserable and wanted to fly home. I packed my sun tan oil and bathing suit and paid my way to rescue Billy. He was sitting by the beach and surprised to see me. I had my bikini on and Billy wouldn’t look at me. It was like pulling a stubborn tooth but he said he was from a sheltered orthodox family. So he never had a girlfriend. My plan was to get him laid as fast as I could. I put oil in Billy’s hand ordered him to oil my back. I could feel how anxious he was. I tanned and he left. I called him to my hotel room and in my bikini I locked the door behind him. You have to get over your fear of pretty little girls . I know he said across the room leaning tight to the wall. He admitted he had never been kissed and looked like he was shaking in his sandals . I had been tapped as early as junior high and a had occasional one night stands here and there. I never had a desire for a real boyfriend and never had never slept with any one more than twice. I never fell in love.
I didn’t know how to continue never being a pursuer before. So I just turned down the lights and calmly talked
Once you get past this you may be a world changer. His face was red and we were just talking. You can do this I coaxed . He took my head and hurt my lips kissing so hard. I had to direct him . He untied my top and I untied my bikini bottom. It was 95 degrees and his hands were cold . He was ashamed as I pulled down his pants. He had just dribbled it all in his boxers. That’s the way it is first time. His circumcised penis bounced with his every heartbeat. I held him and kissed him and worked so hard poking around with his wet penis. We have to lay down I told him it’s easier. He was looking at the door and I told him failure is no option. He was a quick study and learned what he needed to know to get my or any woman’s juices flowing. He got it in and was by far the worst ever. I slapped him with all my might to get him under control. Do what I tell you no more no less. He fired off a round in me and flopped down on the bed. I knew he needed more work and so I snuggled in to his arms telling him how wonderful he was. In a while we went at it and I showed him different positions. He got better and better and by the end of the evening he had done it perfect twice in a row. I had never had so much sex my self and I was enjoying teaching him. I gave him a few lines that were leading and told him they would land many a pretty girl in bed if he wanted. I asked him to use them on the pretty co-worker that flew down with him. Sure enough that evening they went to her hotel room and showed up together at breakfast . She admitted he was a different man and he held his own in bed. Billy asked for more experience and I and the pretty 17 year old co-worker gave it to him. Well I had only a week and said good bye and he threw a large beach blanket over me and we made love on the sand of the crowded beach under it. It was another week before he came back to New York and the new Billy tore in to the business like never before. We had to drop him from volunteer status and he in six months earned the company some very large numbers. I screwed up and fell in love with the young man breaking the company rules. I am now pregnant with a boy and Billy is bringing in six figures.
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