1. Brittany The Cheerleader


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

    indefinitely under the supervision of a counselor, myself. She was very shy, especially after our previous experience. I showed her the gift I got and she was delighted. I presented her the complete outfit, complete with skirt and hair ribbons for cheering. I then explained that she needed to undress in front of me and put on the outfit so I couldn't assure she was feminine and filled out the outfit. She was extremely shy, but complied after very little coaxing. Slowly she removed her necklace, placing it on my desk. Then she lowered her dress over her shoulders, revealing her tiny little breasts. Very tiny, but perky. Obviously she was taking hormones. Her perky little nipples taking up almost her entire breast, yet she had breasts. Sliding her skirt down she revealed a pair of smooth white cotton panties with just a little bit of lace around the sides. It was simple yet sexy. She was so tiny there, you wouldn't even be able to tell she was trans. If anything it looked like she was a female with a pad in. She stood shyly before me, reaching for her outfit. Her cheeks were flushed red. I smiled warmly at her and told her I would need to see all of her to assure she wasn't too big down below to compromise her skirt. She was very shy, so I told her I would pull her panties down while she focused on putting her pretty bows in her hair. She seemed a little less tense at this suggestion and complied as she set her hair into two long pigtails each with a white and blue silk ribbon ...
    I slowly pulled her panties down. I seen her tiny little penis pop out. It was soft, probably under two inches long. The smell of her naked flesh in front of me drove me insane. Softly I touched it, she moaned shyly and shuffled backwards a little. I explained to her that I was very happy she was passing all the tests so far, but I needed to see if her penis worked. I stood and lifted her up, placing my hands under her bottom and sat her on top of my desk. “Please be gentle with me, nobody has touched me before Mr. M” She pleaded softly. After I sat her on my desk I kneeled in front of her. Removing her cute sandals I slowly rubbed her feet, adoring her gorgeous french-tipped pedicure with bright green, pink, and yellow tips. I explained to her that I would be very gentle with her, and that I just wanted her to be able to cheer and be happy. She sat up and kissed me on the lips shyly, telling me I was very handsome. I kissed her cute little toes and she giggled shyly. Slowly and softly I rubbed her legs kissing her feet, ankle, calves, and up towards her things. Looking at her I could see she was slowly getting hard. I never touched another penis before, but something about her turned me on entirely. I kissed it, and I could feel the pleasure surge through her as it gently twitched. I licked the tip before gently putting my lips around it. She was getting harder. I began to suck, easily able to fit her entire length into my mouth. Then I left and gently kissed and licked her ...