1. The new "Girl" On the Boat


    Date: 8/21/2015, Categories: Hardcore, Shemales, Taboo, Author: 1kaaboom2, Rating: 92, Source: xHamster

    I have mentioned in previous stories that my career was spent as a Captain of a high end 100' charter yacht working the waters of Alaska. It was a job that provided me many opportunities to 'play' with men, women and couples, most of them older, and all of them very well-off financially. Passengers and crew had to sign agreements that I could inspect their rooms and belongings for any reason whatsoever, though I assured them it was very unusual for me to do so. For the crew, my main reason for conducting such inspections would be to check for i*****l d**gs. But another reason for checking rooms was to find out more about my crew members and passengers. I have loved hamper diving since my teen years, and I loved going through hampers when passengers were away from the boat. I have found many sex toys, sexy undies, even some private photo albums that made it clear that some of my passengers were as kinky as I was. More than once an older male has asked me to &#034take care&#034 of his wife because he could no longer fuck her, or he wanted to watch me use her, and sometimes it has been the woman who asked for that 'special' service. I love being watched, and found it very erotic to fuck an older experienced woman as her husband watched and stroked his cock. But one of the highlights of my career was by way of a new deckhand. One of my crew members had to leave the boat on short notice, and I had my office send up a replacement. I normally did all of the hiring, but in this ...
    case I told my office that they were to send me the first one who was qualified. When I went to the airport to meet him, it was a young 20's, short, slightly built male that came to me and said he was the new hand. He was very quiet, a bit feminine in his speech and actions, a tad shy, and I found him very erotic looking. Once back at the boat I went over the boat rules, and had him sign the agreement that gave me permission to inspect his room and belongings whenever I wanted. A few days later we set anchor in a secluded cove, and almost every body on board went to the beach for hikes, berry picking, and bird watching. While they were gone I went to his room and start going through his drawers. There was nothing of interest there, but at the bottom of his closet, under some rain gear, was a box that had been waiting for him at the post office. When I opened it, I knew this summer was going to be a grand one. In the box was several panties, bikini and g-string style. Both black and white mesh nylons, garter belts, a short, tight dress and tiny bras. There were also a couple of dildos, a makeup kit, and a couple of porn magazines devoted to 'ladyboys.' I knew he wouldn't be back for at least an hour, so I wrapped a pair of panties around my cock and as I stroked I fucked my tight ass with a dildo. I could imagine him 'dressed' for me....he would look like a young girl ready to serve and service my cock. I shot my load, and figured out how I was going to use my newly found ...
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