Richard the Sissy by Joney Cunningham
Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that they paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a key, just in case I was at work when she found inspiration. I didn't think much of it.
I only worked a few hours in the morning, cleaning up a local movie theater from the night before. The rest of the day, I had to myself. I tried to watch TV for a while, but quickly got bored. I tried to find some of the local boys, who liked to play football in my yard, but didn't like me. I was considered a wimp, especially since my sister was bigger than I was, even though she was two years younger. Mary was also a bully to everyone, including me. With no one to play with or no good TV shows to watch I went back into the house. For some reason I decided to explore my sister's room, so I went in to her room and start looking around. Her room was very frilly. She was also messy. Pants, skirts, panties, and her training bras were all over the place. I saw a pink, nylon, ruffled pair of her panties on the floor. I picked them up and examined them. They were very soft. I placed them up to my cheek to feel the smoothness of them. I wondered what they felt like on my cock, so I pulled down the front of my pants and underwear and rubbed them up against myself. I got an instant hard on. In fact, I had never been so stiff.
I thought, I have all weekend; I wonder what it would be like to dress as a girl. I figured to get the full effect, I would have to shave what little hair I had on my body. I ran the bath water and put bath soap and baby oil in the water as I had seen my mom do on several occasions. I stripped naked and got in. I found my sisters shaver, lathered up my legs with soap, and started shaving my legs. I took my time, because I had heard my sister complain about nicking herself. When I finished my legs, I was amazed at how smooth they felt. I decided to trim my pubic area and shave under my arms as well. I had left a small patch of pubic hair around my still swollen cock. My underarm hair was gone with four quick wisp of the razor. The baby oil had made my skin very smooth. I just soaked for a while to feel the softness of my skin.
I finally broke out of my fantasy and got out of the tub. I dried off and put my male clothes in the hamper, besides, no one was home and I could walk around naked, and no one would know. I decided I would stay in my sister's room for the weekend. I found the pink panties I had played with before. I pulled them up my legs. My cock became hard again as I adjusted them around my waist. I just stood there feeling my cock through the nylon material. I thought, "Stop, I have to put on a bra, and a?" I picked up one of her training bras. I put it over my shoulders and tried to snap it in place, but couldn't. I thought, "How does sis put this on?" I decided I could hook the bra and twist the bra around front, then pull up the shoulder straps. I tried it, and it worked. I decided I didn't want to dress all the way up, so I pulled out one of my sister's camisoles and put it on. I was really hard now. I closed her dresser drawers and walked out in to the living room. I twirled around feeling my body through the lingerie.
All the sudden I heard a voice say, "What do we have here?" I froze with fear. It was Gina and she walked in front of me with a smirk. "I see with have a girlie wannabe here." I tried to say something, but just started crying. "Now, now you little sissy, what am I going to do with you?" I just stood there. I had never been so embarrassed. I tried to leave, but Gina grabbed my arm, "Stand right there, you little sissy bitch, I tell you when and where you will be, or I'll tell your family how the son is a sissy and likes to wear his sister's panties." I just stood there and tried to stop crying. While I stood in the living room I, Gina picked up the phone to call some of her friends. "Yeah, come over, I have something for you to see." I started to cry, "No, don't let me be seen by anybody, I'll be good." Gina held my face and said, "Shut up you sissy, my friends and I will have fun with you, and you will do as we say, or else." "Got it, you baby? I just shook my head in acknowledgement.
Soon, Gina friends showed up. There was Karen, Misty, and Carol. The surrounded me and laughed and pulled at the panties I was wearing. Carol said, "Look at the sissy, he likes wearing his sister's panties." Misty pulled my bra strap and said, "He wears his sister's bra too." Gina told them, "Have your way with this sissy, he needs to be taught how to obey and serve." Karen, who seemed shy at first, pointed her finger in my face and yelled, "Kneel you sissy slut," and pushed down on my shoulder. I kneeled in front of her. She slapped my face so hard that my cheeks became red. I started to cry again. Karen then unbuttoned her tight jeans and pulled down the back exposing her tight round ass. "Lick my crack you stupid bitch!" I stuck out my tongue and just laid it at the top of her crack. She bent over and pushed he ass into my face. "I said, lick it fucking sissy!" I started licking her crack. She moved up, so my tongue would move down her crack. Soon I was at her hole. "Lick my ass hole you cry baby slut!" I hesitated, so Misty slapped the back of my head and screamed, "She said lick her ass hole you fucking cunt." I stuck my tongue out farther and stuck it into her ass hole. Karen reached her hands behind and grabbed my head and held it in place as I licked harder and harder. Then she moved away and Carol pushed me to the floor. She had her school uniform skirt on. She pulled it up. She was a wearing thong pantie. She sat on my face front ways grinding her mound into my face. "Open your mouth!" I opened my mouth a little, but she yelled, "Open wider slut!" I open really wide and she forced her panty-covered pussy into my mouth. She began to rub back and forth. Moaning louder and louder. Then she pulled her panties to the side and spun around so her ass was in my mouth. "Eat my ass you puke!" I stuck my tongue out and rimmed her hole, because I feared what was coming next. Misty started rubbing my cock through my panties. I became hard instantly. I heard her say as I was licking Carol's ass say, "I see this sissy really likes his panties and what is happening to him." The she slapped my dick, hard. I yelped, but was muffled by Carol pressing her butt hole on my mouth. Carol suddenly got up and yelled, "Get up bitch!" I started to stand, but she pulled me up quickly. "Stand there like a good sissy bitch!" I stood there with Carol's juice glistening on my face.
I heard the voices of boys coming in the front door. I froze in shock as I saw Drew and Harry standing there laughing at me. "What is he doing," he questioned Gina. Gina replied, "We have ourselves a little sissy here." Carol looked at Drew and said, "I need you to payback a favor." Drew said, "Yeah, anything for you Carol." Carol smiled and said, "Go to the sofa and take off all your clothes." "In fact, both you and Harry take off all your clothes." Drew and Harry looked at each other and said, "No way, I'm not taking all my clothes off unless I get to see some tits and ass with a lot of cunt thrown in." Carol looked at them with the look of the devil in her face, "You will or I tell everyone about your little secret!" Drew started to take off his clothes. Harry thought for a moment of what could have scared Drew so much that he would start taking off his clothes. Drew looked at him and said, "Just do it, I'll tell you later." Harry thought, "What the hell," and started taking off his clothes. Soon both off them were completely naked and sat on the couch. Gina said to them, "Just lean back boys and enjoy it." Thinking they were going to get pussy, they leaned back. Their dicks were getting hard with anticipation. The Gina looked at me and said, "Get to it bitch, suck them dry." Harry and Drew started to protest, but Carol quieted them with a look. Misty slapped my ass and said get to it bitch!" I walked over and knelt in front of Drew. I stuck out my hand and touched his cock. He leaned back to grant me better access. I started stroking his cock. I felt it get warmer and harder as I stroked it. Just then, Gina yelled, "Don't feel him up, suck his cock you fucking slut!" "Start with his balls, sissy!" I held his cock as I looked at his balls. I decided I'd better get started, so I lower my face and mouth down to his balls. I stuck my tongue out and gave them a small lick. The taste was not like I thought, so I started licking them more and more. I then took one of his balls all the way into my mouth. His started to moan. I felt his cock get hard in my hand. I left the one ball and went to the other. I was getting into it.
I wanted to have the taste of his cock in my mouth. I stared at the head of his cock and licked it with anticipation. I licked all the way down to the base. Then I took his cock into my mouth. Working the head in, then sucking all the way down. I started sucking up and down in a bobbing rhythm. I reached over to Harry with my hand and started to stroke him off as I was sucking Drew. Drew was started to force his cock into my mouth at the same pace I was sucking him. I started to feel his balls. He grabbed my head to keep his cock in my mouth. I felt his dick swell in my mouth. Then he shot his load to the back of my throat. Since he was holding my head in place, I had to swallow his whole load. He let go and slumped back into the couch. Misty yelled, "Next!" I knew what that meant. I started the same routine. I started with Harry's balls. Licking and sucking them, as I did Drew's balls. I started stroking him at the same time. Karen pointed out, "Our little sissy is still a virgin and needs her little hole fucked." Gina pulled me up and said, "Sit on his hard pole and get fucked as a sissy should be!" Gina then pulled my panties down and off. I straddled Harry facing him. Carol held his cock as Gina pushed me down on top of his rock hard cock. I felt a little pressure at first, but soon his cock, which was lubricated with my saliva, slid into my virgin ass. Karen said, "Pump up and down on his got you sissy!" I did as she said, feeling everyone of his thrust into my sissy hole. I pumped and pumped as hard as I could. I liked they way it felt as his manhood pushed in and out of my ass. My cock was getting really hard as well. I didn't know who was going to explode first, Harry or me. I found out I couldn't hold my load and shot all over Harry's chest. He kept thrusting into my ass harder and harder. The her grabbed my waist really hard and thrust me down on his cock as he filled my ass with his hot cum. I pulled off and put my panties back on. Gina said, "Your not done sissy, you need to lick up you mess." "So get to licking, bitch!" I leaned over to Harry and started to lick cum off his chest. When I was finished, Harry surprised me by grabbing face and started kissing my cum soaked lips. Carol, said, "I guess you all figured out Drew and Harry's secret, they love fucking and sucking each other." "I guess they have a sissy slut to include in their gay games." Gina said, "Don't forget, we own the sissy, and his parents and sister won't be home for a few days."
I was ordered to clean up and put on fresh lingerie. The girls made me sit in a straight chair in the middle of the room while the planned what to do with me for the rest of the weekend. Gina has ordered me to stop writing for now, but she told me I would have to tell of all my humiliation later on.
(the end)