1. Brittany The Cheerleader


    Date: 9/1/2015, Categories: Fetish, Hardcore, Shemales, Author: wedgietime, Rating: 93, Source: xHamster

    It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany. One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown hair down past her bottom that matched her large brown and glistening doe eyes. She was dressed cute yet modestly. She had a light yellow top on, and a pair of dark blue jean shorts that covered her thighs well, yet showed off her gorgeous legs and drew attention to her beautiful neon french-tipped pedicure and sexy laced sandals. She looked entirely adorable, yet radiated innocence. I have no idea what came over me, but I knew I needed to have her. Usually to address a students problem they would sit across from me as I sat behind my desk in a typical and unexpected manner. This time however I sat beside her on the couch and an genuinely asked her what she needed help with. I then became aware of her problem. I had heard about Brittany through the g****vine. She was a trans woman, and much more beautiful than I could have imagined. Despite living in such a small conservative community, ...
    she was able to blend in and be accepted very easily, it was probably because she filled in the role of a women so well. She was able to use the woman's restroom, use the girls locker room, and joined the women in gym classes instead of the men. Her current problem though, is she wanted to be a cheer leader and she was being barred from it. Something about a young helpless woman needing my help drove me wild in my young male brain. I knew I could help her, find a law, or even vouch her and get her into cheer leading. I put my hand on her knee and whispered that I would be happy to help her. She then placed her hand on mine gratefully and thanked me profusely. I gently slid my hand up her thigh a little telling her it would be a pleasure to help someone as beautiful as her blossom into a woman. She began to blush profusely, and when I went to kiss her she quickly and shyly got up, saying she was sorry, but she was never touched like that before and left. I felt foolish and guilty for my actions, but immediately began the work on helping her and knew I needed to have her. One day after classes were over I summoned her to stay after school when it would be empty. She walked in wearing a sundress that covered about three quarters of her thigh, It was light blue with orange flowers, and she had a pretty silver necklace. I sat beside her once more and went over the paperwork. In order for her to become a cheerleader she must currently fulfill the role of a woman and remain a woman ...
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