Forced Sissy

 I met Craig on the Cape about 10 years ago. He appeared to be a normal, older man who was looking for a younger playmate. I was mildly experienced, but at 27, was looking to enjoy a more regular hookup, where my comfort level would allow me to explore my full sexual appetites. I was living with my girlfriend at the time, but felt these urges strongly.          

 We spoke over coffee initially and he explained what he was into. Craig said he was dominant and verbal while he played, and while never rough, he enjoyed total control over his sub. I was new to the lifestyle so we started slow.           

He gave me simple instructions in the coffee shop to follow- He had me go to the bathroom, sit in a stall, and text him pics of my pants and underwear around my ankles while I played with my cock. He told me I was a good boy and that he'd give me a shot.           

These commands escalated to tasks that I was to perform, record, and send to him almost daily. I had to ask for permission to masturbate and was to send pics of my cum each time. Once he ordered me to cum in my girls panties, let them dry, and replace them in her drawer. One night he had me record her and I having sex. It was a turn on to send him the vids and when he and I finally hooked up, he did to me what ever I had done to Cindy in the vids.           

Cindy was very submissive to me, which is probably why I liked to relinquish control to Craig. He'd have me enter his house, kneel with my palms up and head down and wait for orders. He liked to tower over me running his hands over my head and putting his fingers in my mouth. After attaching a collar, he would then lead me to his bed, undress me, and place me on a fucking pillow. He'd play the video as he deep fucked me like a woman. Since I always came in Cindy, he always bred me or came in my mouth. It was the first time I had ever felt what cum felt like inside of me. I liked it-I liked being Cindy for him, but I think he wanted more.          

We made plans to get to P-town for the weekend while Cindy was away. On the drive there, he picked up a few friends, introduced us, and headed east. We drank and loosened up. As we approached the town, Craig pulled into the garage of a beach house and suddenly my hands were pulled behind my seat. Craig reached over and cupped my mouth. "Shhh my darling. Welcome to your conversion." I was ushered into the house from the garage and brought to a room with an exam table. 3 men held me down on it while Craig removed my tank, shorts and underwear. I thought they would rape me right there, but I wasn't prepped yet.         

My hands were bound up over my head as I saw razors and shaving cream. I stopped struggling and became compliant. "Do whatever you want, just be careful." I said. They proceeded to lather the cream from head to toe and with 2 razors, shaved what I could never reach. When they spread me open to remove the hair around my hole, I could feel fingers enter me. In 20 minutes, I was hairless. They fed me a large glass of vodka and one of them showered me free of the residual cream and used a douche to clean me out. When dried off, I was dragged into a room where I saw a dress, panties, makeup kit and small metal cage on the bed. I wish he had just asked, but this process was a turn-on for him.         

Craig and I were alone now as he applied some makeup to me. After caging my cock, he slid the panties up my smooth, lean legs and had me put on the sundress. A brunette wig was the last piece along with flip flops. He gently held my face and kissed me. " There are some guys I'd like you to meet, my sweet Cindy." 

I was escorted around town by the 4 men and about to experience sex from a new perspective...