Confessions of a Sissy Crossdresser
Prologue: When I was young, I’d place ads in Craigslist looking for men who liked sissy crossdressers. I lived out my wildest fantasies a hundred times over. This is the story of some of those nights.
Prologue: When I was young, I’d place ads in Craigslist looking for men who liked sissy crossdressers. I lived out my wildest fantasies a hundred times over. This is the story of some of those nights.
As she hopped and skipped, her ample breasts nearly burst from her blouse. A lust surged through the Big Bad Wolf. She should not be here alone. Someone should teach her the ways of the world.
It was freezing. A drizzly rain fell onto my car. I got out, to put on my thigh highs and corset, which was untied in the back. Okay, breath. Relax. Everything is fine. I checked my makeup. He probably won’t even show up. I’m late! I got my heels and wig on and pulled back onto the road. I gunned it to the designated meeting place, drove to the back and parked in front of a dumpster. He wasn’t there yet.
The wind swirled through trees. A mosquito infested pond was nearby. I felt like Marilyn Monroe. I’m skinny, with long legs, and a bubble butt that didn’t fit the rest of my body. He’s late. Headlights. A car pulled in and parked. I got out of my car and stood there for a minute. I turned around, teetering on my heels, holding my corset in place. He walked towards me, his face a blur.
“No. Too masculine” he said with a European accent. He walked back towards his car. I ran towards his car and saw the outline of a masculine face. He had one hand on the steering wheel. He had sent me videos of his body and thick cock, I had spent all week planning for this night, and he was rejecting me!
“What are you looking at I’m not masculine you loved my videos you wanted me to be smooth I’m smooth I used Nair I’m completely smooth fine I’ll just go out alone,” I blurted out. He started the car. “I’ll do whatever you want.” He sat there in his idling car. “Okay. You have one night. To prove yourself. Get in,” he said disdainfully. I walked over to the passenger side of his car and got in.
He drove away. After a few miles, he blindfolded me. He took me inside a house. I had on heels, black thigh highs, pink panties, a red corset with black trim, bright red lipstick, and a curly red wig. My panties were wet from precum. He led me to a room where I could hear a TV on. Being dressed like a slut, with my fat ass hanging out, is empowering and intoxicating.
“Hmmm, where did you find this?” a voice said. The guy on the couch, Reggie, changed the channel. Pornography came on. “Listen to me,” the European Guy said quietly into my ear. “My friend is intrigued by you. Sit on his lap. But,” he began. My mind reeled. I didn’t plan on this. I was holding my corset in place with one hand. My heart was racing. “No fucking. Your panties stay on.”
He took me to where Reggie was. Reggie guided me onto his midsection, my legs straddled him. I grinded against him some, a little, very slowly, still not sure I wanted to do it. “My corset isn’t tied,” I said softly. He tied the corset for me and gave me a hard swat on the ass. I straddled him again.
He asked me to stand up. He unlatched his belt and pants; I heard them hit the floor. He guided me onto his waist. He rubbed his thumb across my lips, I sucked it, like an obedient whore. He squeezed my butt cheeks hard, he pushed up against me, I was afraid I would cum. “Let’s go to the bedroom,” he suggested. He took my hand and led me. I banged my shin into a table, it hurt like crazy.
In the bedroom, on the bed, we made out. Reggie pulled at my panties, I held them up. “Can I, please, have something to drink?” I asked. He slid my panties out of the way and pushed his cock against my butt hole. I pleaded again. “Okay,” he said. This didn’t make sense. He was going to fuck me. But, the first guy told me not to get fucked? If he didn’t want me to get fucked, why did he leave me alone with Reggie?
The door opened. Reggie handed me a glass of wine. I lifted the blindfold and saw him, with his back to me, putting lube on his cock. He was a black bull, six foot two and two hundred and sixty pounds. “Put it back on,” he ordered. The other guy told me not to get fucked, I explained. “I’m breeding that ass,” he replied. “But, he told me,” I protested. “Shhhh, drink your wine”.
We were kissing, standing near the bed, me still blindfolded. We ended up entangled on the bed. “Take them off,” he whispered. I tossed my panties into the corner of the room. I got on top and grinded on him. The friction, skin on skin, his hands all over me, I was about to cum. It wasn’t going in. It was too big. I reached back to help guide the tip inside. “Excuse me,” came a voice.
The European Guy pulled me by the arm out the room. “You are with me,” he seethed. “Where are your panties? Keep them on!” I was dragged by the elbow back to the bed and handed my panties. They went out in the hall for a few minutes. Reggie came back in and closed and locked the door. In all the commotion, my little cock was soft and shriveled. We sat on the bed together.
He removed the blindfold. He stood up. His cock hung, bobbing, next to my face. I got on my knees and licked the shaft and balls. I put it in my mouth. Slowly, it got firmer. I got the tip to the back of my throat, gagged, took it back out. I worked it in and out, sucking and slurping, making sure it felt good for him. The mushroom head of his cock chocked me. A knock on the door startled me.
Reggie’s cock throbbed. I cupped his balls and coaxed the cum out of them. He exploded in spasms that shot cum down my throat. I didn’t taste the first few blasts, but as his cock slid backwards, my mouth filled with thick, gooey cum. I licked off the last few drops with my tongue. “Straight from the tap, like a good girl,” he said derisively.
I opened the door. “Where is your blindfold? First your panties and now the blindfold!” The European Guy bellowed. Reggie was in a jolly mood. He tied his shoes, humming to himself. He took the European Guy out into the hallway. I heard them exchange words. They were friends, on the surface, but beneath that they were simmering rivals.
I strolled away. I got to the living room as Reggie was leaving.
“Where are you going? You don’t know where your car is,” he said. I took my hand off the doorknob. “I’d like to go home now,” I replied.
He was amused by this. He got me by the throat, knocking me against the door. “Do what I want and you won’t have to walk home!” He took his hand off my throat. I gasped for air. His eyes smoldered like red diamonds. Sweat rolled down his cheeks from his unruly, greasy hair. Incredibly, it occurred to me that I hadn’t cum yet.
I was consumed by weaknesses and desires to have sex with masculine strangers. He took me to a bedroom that was lit by candles and had sex toys on the bed. He kneeled down, his face near my butt, to eat me out. My face was on the bed, my ass up, my arms stretched out. His facial hair felt like sandpaper, but my little clitty got hard. He lifted me off the bed, to my feet, and spun me around.
“Get on your knees, bitch.” I sucked his cock until it was throbbing. He looked like the male models in black and white underwear ads on city buildings. He had tattoos on each bicep. He glistened with musty sweat. I could not make him cum. He fucked my boy pussy until I squirted all over the bed. He fucked me until I could not take it anymore, then pull out, then slide a dildo up my ass.
He spanked me with whips and with his bare hands. It was unrelenting. Tears streamed down my face. My fingers clawed at the bed sheets. Please, please stop. He hate fucked me. He told me I deserved it. He finally took me back to my car. I watched him drive away. At first, I was ecstatic as I drove home. But, as usual, a gloomy depression set in. I didn’t have any dreams that night.
But, in the weeks that followed I had strange dreams. I was alone. I was in dark, dingy, disgusting places. I asked every strange face I saw for help, but no one would help me. It was all blurry and unfocused and shimmering. I saw my mom. She wasn’t my real mom, my real mom died when I was a baby. The lady I saw was my aunt, the lady who raised me after my mom died.
I was an only child and she loved and cared for me. She protected me and fed me and taught me and so when I would see her in the dream, and see that she was crying it destroyed me. I would run to her but no matter how hard I would ran, I could get no closer. I would scream out to her. All she would do is turn away from me and then I’d wake up.
Together we lie, together we pray. There never need be longing in your eyes. As long as the hand that rocks the cradle is mine. As long as the hand that rocks the cradle is mine.
The Hand That Rocks the Cradle; THE SMITHS
The Hand That Rocks the Cradle; THE SMITHS
A KIK message from GyutoBull. I wanted to meet him, but he kept ghosting me. Then, I confided, half seriously, that I had fantasies of rape role play. He messaged me daily for weeks. “Hey, the door will be unlocked. Be here at 12:30 a.m.,” it read. “No thanks. Some things are better left as fantasies,” I replied.
I unlocked the side table next to the bed. My dildo was there. All my friends were happy and getting married, I have a black dildo next to my bed. My life was a train wreck. GyutoBull hadn’t replied yet. Okay. Good. I’ll stay at home. I walked around the neighborhood. It was a beautiful, warm night. My roommates were home.
I got home and turned on the TV. I locked the door and put on my thigh highs and a wig and lubed up my dildo. My phone buzzed. GyutoBull sent me three videos. The first was his cock, hard and throbbing, cum oozing out of the mushroom head. In the second, dark and grainy, I saw he was a heavyset guy. In the third, he had his dick next to a coke can. “Ready to fuck RIGHT NOW. 12:30 a.m. don’t be late!”
No! I’m not meeting him! I was still holding my lubed up dildo in one hand. I scrolled through his videos. My willpower to deny him wilted. “Okay! I’m on my way,” I messaged back. He wanted me to wear my black corset, a bright pink cosplay wig, pink above the knee socks, a pink thong, and my regular assortment of bracelets and necklaces. I dressed nearby. When I got there, I made my way towards his front door. I thought about turning around.
I hated the life I was living. The lies. The isolation. But, it was exciting! Why not enjoy it? It was too late to be normal. This was my life and there was no way to stop it. I opened the door and walked in a few steps. He grabbed me from behind. He was wheezing as if he had run up six flights of stairs. He held a wooden spoon against my neck like a knife. “I didn’t think you’d show up,” he sneered.
He pulled me towards a bedroom. There was a couch in the middle of the room. A computer was on top of a table in the corner of the room. A closet door was open with nothing in the it except empty hangers. He pulled my thong down to my ankles, I lifted my feet, so that he could take it off. “Spread your legs.” I did as he wanted. He spanked me with the wooden spoon. “Wider,” he yelled.
I spread my ankles as wide as they would go. My stomach was on top of the couch. “Put your wrists behind your back,” he ordered. He tied my wrists with zip ties. He rushed over to the table, breathing heavily and laughing to himself, and began typing onto the computer keyboard. From my vantage point, I could see him in the darkness. He was two hundred and eighty pounds compacted into a six-foot four frame.
His face was ruddy and pockmarked. His hair was thick and matted as if a helmet was plastered onto his head. He put a studio lamp behind me. “I don’t want to be on camera,” I said. He pinned me to the love seat. I smelled grease and sweat. “Shut up, shut up! It’s a closed loop chat room. It’s just for my friends.” He spanked my ass with the spoon until I felt welts coming up. I gave up. I stopped struggling.
He fucked me while his friends watched. I hated his guts. This was the last time I’d let any guy dominate me. Yet, I loved every second of it. I dreamed about nights like this. I liked being on camera for his friends. When he was satisfied, and after humiliating me to entertain his friends, he let me go. I was ashamed as I walked back to my car. I ignored his messages for a few days.
About a week later, we went into the same bedroom and did it again while live streaming. It didn’t take him long to cum. He’d take a thirty-minute break and then he’d fuck me again. After we were both drained, I’d clean off in the upstairs bathroom. For the first time in my life, I had a Friend with Benefits. The sex was amazing. Sometimes, after sex, we’d sit around in the dark and talk.
He grew up in the Northeast. He had dropped out of an elite university that he hated, which disappointed his father, and he was as closeted as I was. He worked long hours in a restaurant. Eventually, he gave me a key to his townhouse. I’d go over there, get all dolled up, and wait for him to get off work. He’d leave a bottle of Catena Zapata wine on the kitchen table. He bought me things to wear.
He gave me a safe place to be femme. And, in exchange, I was his little fuck doll. One night, he let me sit at the desk, and chat with his friends. They showered me with compliments. They asked me a million questions such as how long I had been a crossdresser and if I had thought about “having it cut off.” It made me feel beautiful.
Maybe I was beautiful, in my own weird way. For the first time in my life, I was happy. As long as I could remember, guys have looked at me funny. They would melt as soon as they saw me. I could see it in their eyes. I was never afraid that anyone would hurt me. But, it didn’t last. Nothing ever does. He moved away to a different city.
Time passed, months, maybe years, who knows, and the dress was gone and a just a beatup skirt and sweater and the Broadway bars were 8th avenue bars, but soon even these joints with their hustlers, pushers, pimps, queens and would be thugs kicked her out.
LAST EXIT TO BROOKLYN, Hubert Selby, Jr.
It’s a gravel parking lot now. The lake, in the back, where men used to have sex, is still there. The gay resort, and all the gay bars down the street, are demolished now. Crossdressing changed everything for me. I went from having no sex, to having as much sex as I wanted. In my 20’s, my sexual exploits were almost too good to be true.
By my 30’s, I knew I was never going to have a family. In my 40’s, I didn’t know what I wanted. I knew my femme life was almost over though. I didn’t want to be saggy, wrinkled and alone in life. There are a lot of lonely and broken souls out there. On KIK, I started getting messages from a crossdresser named Taticd.
Taticd: Hey
Me: Hi, gurl
Taticd: Do you still want to dress together?
Me: Yes, if you do
Taticd: Ok. When?
Me: I don’t know
Taticd: How about tonight?
Me: Okay
Taticd: Let’s find straight guys
Me: Okay!
Taticd: Have you been to the Lava Club?
Me: No, never. Have you?
Taticd: Yeah, it sucks. All femmes. No men.
Me: Hun, we could walk around an adult bookstore
Taticd: Yes! That would be fun!!!!
Me: Which one?
After a few conversations, I stopped taking her seriously. Meanwhile, I’d venture out alone to some of the few gay bars left.
I was surrounded by gay men. I’d sit there feeling out of place. Then, one summer night, after a thunderstorm had rolled by, I met Taticd at an adult bookstore near where she lived. She was a beautiful Latina with wide hips and penny colored skin. She wore a flimsy red dress and fishnet stockings.
“Come on, let’s find some men,” she said pulling me into the store. There weren’t many people there. A few elderly men, a lesbian couple, one young unattractive guy. We were in and out. “Where are the straight guys?” she wondered. She looked like J-Lo, with her guitar shape and wide hips, if J-Lo was a trans. “The Sapphire Men’s Club is a few miles away,” I suggested.
“Yeessss, let’s go, girlfriend!” The parking lot was packed. I had on heels, thigh highs, panties, a brown short sleeve blouse and a brunette wig with red highlights. We went inside. Every table was taken. I followed her around the room. The Master of Ceremonies, in a glass encased booth, asked the crowd to clap for the ladies on the stage. Taticd whistled and pumped her fists in the air.
“Aye dios mio! Hot guys everywhere!” she exclaimed. We finished our beers, so I went to the bar, for round two. I squeezed in to the bar shoulder to shoulder with two guys. A group of college guys crowded in behind me. “The fuck!? A trans? It’s popping out! It’s the size of a tootsie roll! Faggots! These weirdos have mental health problems!” The egged each other on. The guys around me stared.
I paid for the beers and found Taticd sitting at a table with two men. I dropped off the beers and told Taticd that I wanted to walk around. Taticd pulled me a few feet away from the table, “What’s wrong? Why don’t you sit with us? Do you like these guys? We can go back to my place. Find a guy! Are you okay? Find someone!” She hugged me.
I walked around. No one seemed to pay me any attention. Throughout the bar men and women sat at tables drinking and laughing. I wanted to go home. I saw a stunning blonde dancer on the main stage. The way she moved her body was mesmerizing. Her body was perfect. She was having the time of her life and getting paid for it.
--To be continued in Excerpt #3--
