Forced to Crossdress, Tied Up, Fucked

Brittany and I had been friends since late college. She was tall, strong, and desired by many guys. I had befriended her in my computer science classes and had helped her cheat on the exams. In exchange, she would get me into exclusive frat parties. We had maintained a good relationship after college and happened to both be working in New York. She was working as a software engineer at Amazon and I was working as a data analyst at a small finance company. I hadn’t heard from her since I moved to New York until one day when she called me. I heard her high pitch voice come over the phone, “Heyyyyy! Long time no see! So I am having my birthday party at my apartment and would love for you to come by. I showed some of my girlfriends your Instagram and they think that you are super cute!” I said, “Ya, I can stop by after work. What time should I come.” Brittany said 8 pm and sent me her address. I had been single for the last few years and thought that this would be a good opportunity to meet some new people. The rest of the day passed by quickly. I went home and watched some TV before falling asleep. I had to wake up early for work and worked a good 12 hours before I was let off at 6 pm. The finance industry was really taking a toll on me in New York and I was having second thoughts about it. I took the subway home and stopped at Victoria’s secret to get Brittany a gift. I decided to just get her a gift card since I really didn’t know her size. I had thought Brittany was attractive since when I first met her but had always been too scared to act on it. I imagined Brittany in Victoria’s Secret lingerie on the way home. I showered and changed into jeans and a dress shirt. Brittany’s apartment was only a few blocks from where I lived. I walked over and entered the lobby. Her apartment was one of the tallest in Manhatten. Everything was super clean and I was taken aback by how grand it looked. I called Brittany to come get me and a few minutes later she walked out of the elevator. She was wearing a pink dress. She had her makeup done and looked hot. She rushed up to me and gave me a big hug. “OMG! I missed you so much. How have you been??” I responded, “I have just been working. You look good.” Brittany smiled and led me into the elevator. She clicked the 27th-floor button and the elevator began to rise. I said, “Wow! Your view must be nice.” She said, Ya haha. Watching the city at night is something else.” We arrived on her floor and walked down the hallway. She was wearing heels and I thought they were so sexy. Before she opened the door to her apartment, I handed her my gift. She said, “Awww, how thoughtful! I had been meaning to buy some more stuff from Victoria’s Secret.” She opened the door and walked it. Her apartment was massive and had a big glass window overlooking the city. There were 6 girls that were already there. They were all sitting around the living room waiting. Brittany said, “He is here! Now we can begin.” I asked, “Are there more people coming?” Brittany shook her head and said, “ I wanted to keep it small.” I thought it was odd that I was the only guy here, but didn’t say anything. Brittany instructed everyone to sit in a circle on the living room floor. She announced, “Okay we are going to play truth or dare. Is everyone down?” We all nodded. She looked at me and continued, “Since you are the only boy, let’s start with you. Truth or dare?” I said, “Dare” She said, “I dare you to let me tie you to a chair. I paused. That was such a random dare. I didn’t want to seem like a pussy in front of all these girls so I said okay. Everyone cheered. Brittany got up and took me to her bathroom. There was already a chair in front of her bathroom sink. I thought it was odd that there happened to just be a chair lying there. All of the other girls piled into the bathroom after us. Brittany instructed me to sit down and close my eyes. I obeyed. I felt my hands being tied together behind the chair and my legs tied to the legs of the chair. It seemed like there was multiple peopling tying me up at once. Suddenly Brittany spoke up, “So we are going to actually change the game a little bit. We are now going to play dress up!” Everyone laughed and I opened my eyes. Brittany said, “We are going to just put a little makeup on you and a wig. It’s not gonna be a big deal and we can take it off right after.” I said I didn’t want to do it. Brittany took her hands and ran them up against the front of my jeans. I instantly got hard and blushed. Brittany smiles and said, “If you want more of that, you have to listen to me” I nodded. A few of the girls opened various drawers and took out lots of makeup. Brittany applied lipstick on my lips while another girl put mascara on me. Foundation was put all over my face. This went on for 10 minutes until my face was entirely covered with makeup. I looked in the mirror and couldn’t even recognize myself. I felt really pretty and wasn’t sure if I liked looking like this. I winked in the mirror. Brittany noticed and said, “Glad you like your new look.” She then took out her phone and snapped a picture of me. I freaked out and struggled to break loose. I said, “You can’t post that! Please don’t” Brittany smiled and said she won’t post it as long as I obeyed her. I said, “okay.” She said, “We are going to untie you now, but don’t try to escape. If you try anything, I am going to post the picture.” I nodded. Two of the girls untied me and each held me by one of my arms. I secretly liked all of the attention but wasn’t sure where this was going. A hairnet was put around my hair. I felt a wig being lowered onto my head. I looked in the mirror and was surprised by how real it looked. Next, I was taken to the living room. I was moved to the top of the living room table. My hands were lifted up and handcuffed. The handcuffs were connected to the fan.  The girls stepped back and let go of me. I felt everyone’s eyes on me. Suddenly, Brittany walked up to the living room table. She had scissors in her hands and began cutting my shirt. I struggled around to try to get out of the handcuffs and all the girls laughed at me. My shirt dropped to the floor. Brittany’s arms wrapped around my waist and undid my jeans. She pulled them down to the ground so that I was just in my underwear. I then felt her hand enter my underwear and pull it to the ground. I was completely naked now. Brittany started grinding on me from behind. All the girls cheered. Brittany’s hands moved down my body until they were on my dick. She stroked it with her hands and I got super hard. Brittany said, “Wow you are so horny for me. Don’t worry I have something special for you. Brittany moved in front of me. She bent down like she was about to suck my dick then stopped. She said, “Just kidding. You really thought I was going to do that.” She stepped back and slid her thong down from under her dress. She told me to open my mouth. I opened and she put the thong inside of my mouth. Another girl handed her a cloth and she wrapped it around my mouth. I couldn’t speak now and could just make a humming sound. Suddenly, a box filled with clothes was placed on the living room table. Brittany took out a black thong first. She put my legs into it and slid it up. She grabbed my dick and tucked it into the thong. Next, she took out a schoolgirl skirt. She said, “Since you helped me study so much, I thought I would let you be a schoolgirl tonight.” I made a noise through the cloth around my mouth, but it was barely heard. The skirt was put on me and another girl put on the top. White stockings were pulled up my legs and I was forced to step into some red heels. Suddenly, I was unhandcuffed and rushed to the bedroom. I was forced face down on Brittany’s bed. I felt myself being spread out. My legs and arms were tied to the 4-bed posts. I felt a hand reach around my stomach and lift me up. A pillow was placed under me so that my back was arched. I felt my skirt being lifted up. Suddenly, I heard more pictures being taken and girls laughing. I struggled to escape. Someone came up behind me and began playing with my ass cheeks. I felt them being squeezed by multiple people. Suddenly, Someone slapped one of my cheeks really hard and I felt my whole body shake. All of the girls took turns slapping my ass and it began to turn red. This continued for another 10 minutes. I heard whispering and everyone left the room. I laid there in bed with my skirt still pulled up. Someone had turned on the fan and I felt the air against my bare ass. I secretly liked this position. All of the girls returned and I was scared for what was coming next. One of the girls got on top of me and removed the cloth around my mouth. I spit out the thong. Brittany whispered in my ear, “I hope you liked the taste of my thong. You are going to need to be a big girl for this next part.” Brittany got off of me and sat behind me. Her hands grabbed my ass again and I felt them pull off the thong I was wearing. Brittany slowly pulled the thong down to my thighs. She then repositioned me so that my legs were spread out. I felt waxing strips being placed near my asshole. I shrieked as they were pulled out one by one. My ass felt clean after they were done. Next, I felt some oil being applied between my asscheeks. I think I knew what was about to happen next. I felt a finger slip inside of me and I moaned slightly. It was Brittany. As she moved her finger around she said, “You like that baby girl? Are you ready to get fucked? Don’t worry, I know a big girl like you will be able to handle it.” Brittany’s finger slid outside of me and I heard her strapping something onto her. Suddenly, I felt something press up against me then slide into me. I moaned loudly as Brittany fucked me with a dildo. I heard other girls laughing in the background and cheering me on. Brittany had her hands on my waist and thrust in and out of me. I arched my back and continued to moan loudly. I felt like Brittany’s bitch and secretly liked giving up control to her. She paused and slid out of me.  She leaned over me and whispered in my ear, “You want some more pussy boy?” I nodded my head. I felt more oil applied and Brittany re-entered me. She went deeper this time and I shrieked. She slapped my ass as she rode me. This continued on for a few more minutes until she stopped. I felt a paper towel wipe off the oil and my thong was pulled back up. I was untied from the bed and escorted back to the living room. Brittany said, “Thanks for coming to my birthday party. The rest of the night we are doing some girls-only things so I am afraid you will have to go.” My hands were handcuffed behind my back and I was taken out of the apartment and down the hallway. They put me in the elevator and clicked floor 1 then left the elevator. I didn’t know what to do and waited for the elevator to arrive at floor one. The elevator opened to the lobby. It was mostly empty and I ran outside. I quickly rushed back to my apartment. I had to have our security guard let me in. He looked me up and down and didn’t say anything. He helped me break out of the handcuffs. I got back into my apartment and took off the outfit. I quickly laid on my bed and fell asleep. Since then, Brittany and I have not talked. I hope to go back to her place one day and do it again.