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16 Mayıs 2023, 21:04
Christmas break at the Boarding School. It was December 15th, the dorm was empty and I was alone in my room. My parents sent me away to an all-male College/Boarding School in the Northeast, USA. They suspected I was Bi or Gay and wanted me out of sight and out of their way. They informed me I would be in school until the summer break. My name is Timmy. I am eighteen years old. I am green eyed, five foot ten, one hundred forty pounds, quite skinny, very feminine looking and not well endowed with only a five inch thin cock but I am told I have a great ass. My body has zero hair except on my head which is blond and on the long side. The only area I need to remove hair is on my pubic area and that is very light blond. I love to wear pantyhose and panties because they feel good on my skin and I feel so sexy when I do. I am comfortable as a closet cross-dressing young man. Many have said my face is so pretty I should have been a girl and I agree. That is why when I am servicing someone I call myself Tammy. That day I was feeling low because all my friends went home for the holidays. I hadn?t had sex for three days and was sitting on my bed and feeling very horny. I had just reached inside my shorts to stroke my boner when my cell rang. ?Hello, Timmy,? Mrs. Longinbeckerstien Escort izmir (http://izmir.t2bro.net/) said. ?I hope I am not disturbing you on this crisp Saturday morning.? Holly shit why is Mrs. L. calling me I wondered? ?Hello Mrs. L.? ?Timmy or should I call you Tammy,? Mrs. L. said. My brain was screaming, ?What the fuck is happening?? ?Your silence is speaking volumes Timmy. Don?t be frightened, I know all about you. My husband shares all the videos with me. Oh, I guess you hadn?t realized his office has cameras to record all his adventures. I watch them every time as he pleasures me. Timmy I am not calling to embarrass you but I am calling to ask a favor.? ?Sure anything you want Mrs. L.? ?Call me Vicky and when you talk to my husband call him John.? ?Tonight we are hosting a cocktail party for our closest friends and some work associates. One of my staff has come down with something and can?t help with our guests. Suzy is a tall young thing and we figured Suzy?s maid outfit will fit you quite well. Come over our home at six this evening. I will help you with hair and make-up and get you dressed. Is that alright with you, Tammy?? Good God is that all right? My cock was hard as a rock as I feverishly jerked off as I stammered, ?Yes, Vicky izmir escort (http://izmir.t2bro.net/) whatever you want.? ?Good then, see you at six,? she said, as she hung up. I only stroked my girly cock a few more strokes when I erupted all over my belly and hand. I brought my cum drenched hand to my mouth and savored my sweet load. I couldn?t wait until it was time to leave. I showered, then made sure what little velvety blond hair had sprung up on my pubic area was removed. I used my electric Epilady Hair Remover. It lasts longer and I don?t get those red bumps you get when you shave. I put on a pair of hip hugger black silk see through panties and over that jeans and a pullover shirt. Grabbed my coat and gloves and headed cross campus to the Dean?s residence. I was shaking with excitement when I rang the doorbell. A young woman answered the door. She was wearing a maid outfit. She looked great in a low cut black corset top, French style short skirt, black stockings with garters and high heels. She told me to enter and follow her. I obeyed like a little puppy dog. She led me to a room off the kitchen. It was a separate maid?s quarters complete with bedroom, bath and a kitchen. She told me to sit at the dressing table and wait. ?Hi Timmy or soon izmir escort bayan (http://izmir.t2bro.net/) to be Tammy,? Vicky said. I turned to see a really beautiful woman standing at the door. She was a tall redhead with a perfect body. She looked about thirty years old. I thought if I was a woman I would want to be her. Vicky went to work on me. She applied makeup, lipstick, and a red wig. I must say I looked like a sweet virgin school girl. I wasn?t a virgin anymore, at least with men. She then helped me with my outfit. It was the same as the maid who let me in at the door. The corset actually made my chest look like I had small breasts. It slimmed my waist even more then my twenty two inches. It also made my hips appear bigger. My legs looked long and beautiful in the shear black stockings and four inch heels. I looked in the full length mirror and saw a really hot girlie boy. Vicky explained, ?You are to serve the guest drinks. You are also to cater to their every need. You have catered to my husband?s needs along with the needs of some professors and most of the rugby team so I am sure you understand what I mean. Do we understand each other?? ?Yes Vicky, I believe I do.? At that point my little cock sprang to attention pushing up out the top of my panties but was restricted by the tight maid skirt. The guests arrived on time. I knew some of the professors but no one else. I served drinks for about two hours before things started to heat up. The guests were getting loud. Some were groping each other or even feeling up the other maids. That is when Mr.