This story is about 95% true. The location has changed and some elements of the story have been altered to reduce any identifying details.
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Growing up, I knew something was different about me. I liked the feeling of being feminine; the movements, the clothes, the panties, and the feeling of being penetrated, having something inside me.
I lived in a rural area of the Texas panhandle, a collection of trailers outside of a small town in tornado alley. The trailers were all on 2-3 acre lots, so they weren’t exactly close together. This afforded some privacy for my sexual antics as a kid, but also allowed for plenty of gossip to get around.
When I was 6 or so, I discovered the feeling of lace on my body. Around 8 I discovered anal penetration. Around 10, I was tired of playing with myself and deep down inside, I knew I wanted to be intimate with a man. Small town Texas in the late eighties didn’t afford many opportunities, and you couldn’t really just come out. So what was a bottom boy to do? Raid your mother’s panty drawer, find household objects to stick inside you, and be ready to take advantage of any opportunity to dress that became available.
I was 11 or 12 in my room doing my homework one early evening when I overheard my mother on the kitchen phone. She was talking to a neighbor who was a mom of two kids, one older than me and one younger, when I heard her mention the word molested. I could feel my pulse quicken at the possibilities that word might contain. I heard her hang up the receiver and heard her come down the hall. She walked through the door and sat down on my bed. She patted the bed for me to come over and sit next to her, so I got up from my desk and joined her. She put an arm around me and then she began to share with me the details, not gory details, but enough to “scare me” without being graphic. It was mostly a warning, do not talk to the old man in the peach trailer, he touched someone my age inappropriately. I was to tell her if he ever tried to talk to me. I assured her that I would avoid him, and that I would tell her if he even so much as waved at me. After she left, I waited to see if she went to go warn my sister, which she didn’t do. That must mean Jesse, the neighbor’s boy whose mom had called mine was who got touched. I got excited.
As soon as she left my room, I dug into my closet to find my secret stash of clothes and toys. Being 10 and there not being such things as the internet or Amazon made it hard to find “toys”. They weren’t sex toys, they were other things that I had re-purposed. A hairbrush with a smooth tapered handle, a curling iron with a busted plug, a wrench, and a screwdriver with a particularly robust handle. I also had an outfit consisting of lace thong panties (the high-waisted 80s kind), a black lace demi cup bra, a pair of too-short jean cut offs, and panty hose. My little dick was straining against my sleep shirt as I anticipated playing with my toys tonight, imagining I was getting molested by the Peach Trailer owner. I waited for the sound of my mother going to bed before I started dressing. I didn’t have any body hair yet, so the panties slid right up between my ass crack without any resistance. Next, I put on the hose, carefully rolling it up before I stuck my feet in it, then sliding it up my legs carefully to avoid any more runs. Then I slid the bra over my shoulders and hooked the clasps together behind me. Pausing to look in the mirror, I could see my balls slipping lewdly out either side of the thong panties. I took a second to push them up inside my body while tucking my little boy pecker between my thighs, then pulling the hose above my waist locking them in place.
Looking back at the reflection in front of me, I was satisfied with what I saw looking back. I modeled for my own amusement, shaking my ass cheeks, and posing like the models I saw in the Sears catalog. I started dreaming about the man in the Peach Trailer. I wondered when I was going to get the chance to let him molest me, and how it would play out. I started grinding against the edge of my bed, working myself up. Staring at my reflection I slowly pulled the nylon off my ass. Sucking on my finger to get it wet, I reached back and pulled the thong out of ass crack, exposing “pussy” hole. Closing my eyes, I slid the finger into my rectum, my little dick jumping with the excitement. I worked it in and out of my ass, before stopping to sneak out of my room. I needed lube, and castor oil was my favorite. Hiking my nylons back up, I opened the door up and peeked into the hall. No one was making a sound and there were no lights under the doors to indicate anyone was awake. I tip-toed into the kitchen and opened the cupboard. I enjoyed leaving my room in drag, it gave me a chance to work on my mannerisms. As I reached up to grab the castor oil, I jutted my chest and ass out while kicking one nylon clad foot out behind me, bending it at the knee. I grabbed the oil and closed the door slowly. Attempting my best catwalk, I sashayed back to my room walking on my toes as if I was wearing heels.
Closing the door behind me as I enter my room, I knelt down and poured some oil in the cap and set the the bottle on the night stand. First I rubbed some on the hair brush. Squatting on the ground, I pushed he handle of the brush inside me. Pausing for a moment to get used to the intrusion, I pushed it up till the bristles touched my ball sack. I slid it in and out a few times before moving on to the curling iron. It was cool to the touch and much thicker than the brush. Even though I had opened up myself, it was still tight, and it pushed on my asshole before I was able to relax and let it slide in. The thickness in my little pussy was delicious. All of my nerve endings in my entire body felt like they were linked directly to my hole as I opened up to accept the entire width of the shaft. I looked in the mirror at the scene I was presenting. Thong slide to the side, asshole stretched tightly around the metal phallus, my boyish cheeks gripping as I drifted up and down.
My erection had subsided, but I was hornier than ever. Precum oozed into my panties as I walked around the room with the curling iron hanging out of my ass, cord trailing behind me. I wasn’t fully aware of what sex would be like, I just knew that I loved the feeling of a full asshole. Suddenly, I had a wicked thought. Just inside the back door, Mom kept one of those huge d-cell police-style flashlights. It was considerably bigger than the curling iron, as heavy as the wrench but thicker than anything else. I wondered if that would fit? Not wanting to lose the progress I had made so far, I kept the curling iron in my ass as I quietly stepped out into the hall. I snuck over to my mother’s door and listened for any sounds. Satisfied she was out, I strutted to the backdoor, curling iron deep inside my little ass. I found the deep black with a checkered handled toy and it was bigger than my imagination had recalled, I was sure it wouldn’t fit! It was bigger than my wrist! I carried it back to my room, one hand holding the light, the other keeping the curling iron in my ass so my asshole wouldn’t tighten back up.
I placed the flashlight down on the carpet and sank to my knees before it. It was almost even with my rib cage! There was no way I was going to take the whole thing, even if I could get it inside me. I didn’t let that stop me though as something deep inside me urged me onward, oiling up the cold metal, pulling out the curling iron while being careful not to squeeze my asshole shut, centering the light under my ass, and trying to push it inside. IT didn’t work. The light was too tall to kneel and sit on like I did with the curling iron. I was going to have to squat. As I braced against the bed, I pushed the curling iron back inside me to open my hole up for my new boyfriend again. Using one hand to hold myself up, I used the other to push the back of the light up against my cunt. I whimpered out of desperation as I couldn’t get it in. I took a deep breath and pushed my body weight down on it. I felt something give and a half-second of pleasure before a searing pain in my ass lifted me off. Frightened but still dripping precum I turned around to check for blood. I found the end of the flashlight to be dry of blood but also dry of the cooking oil! I slathered some more on the light, and on my whole crack before trying again. Squat, curling iron, wiggle it around, pull it out, place the light, sit on it.
This time I put almost all of my weight. I could feel the intruder pushing against my body trying to get in as I grunted and tried to force myself on it. Finally, my pussy gave and I started sinking into a new sensation of fullness like I had never experienced before. I hit the checkered part of the handle and the sensations it created along the rim of my ass before I bottomed out. It felt like a someone was had punched my stomach from the inside before I lifted off of it. The light slid out of my ass from its own weight and the suction sensations it was creating were another new feeling. I loved it immediately. I grabbed the light and tried to push it back up, but the angle was too awkward for something that heavy. I held it as I re-positioned on to all fours and placed the head of the light in between my ankles. Squeezing with my ankles, I leaned forward and off the light, feeling that delicious suction inside my ass before pushing back against it, sinking back down onto the checkered handle. I repeated the process. This must be why the girls in the magazine were on their knees in front of the camera. This must be what sex is! Excited I sped up, clear liquid practically spewed from the tip of my dick in steady streams to the carpet. I rocked back and forth until my legs started to shake and my eyes kind of went dark around the corners before they rolled a bit back into my head and I moaned loudly. I was shook. I sank back on the light but the oil had worn off. It burned. I tried to stand but my legs were too weak so I just kind of flattened out on the floor, smearing my tiny wet dick across the carpet as the flashlight pulled out of my asshole.
I was hornier than ever, but physically spent. I cleaned up my toys and got them into my closet. Exhausted, I sat down on the edge of my bed and laid back. I passed out, still in my mother’s underwear. I woke up the next morning under the covers as the events of last night replayed in my head. How did I get into my bed? Pulling my hands across my body, I found I was still in my Mom’s thong and bra! I heard the door open as my mother walked in the room to wake me up. I was busted, I was going to be in so much trouble! She was going to catch me! She bent down and picked up my discarded sleep shirt and tighty-whities off the ground and stood up. She tossed them on the bed and said, “it’s time to get up. When I come back in here you better be out of bed and ready for breakfast!” I exhaled the breath I had been holding from the moment I heard the door handle in relief that she didn’t pull the covers back like she normally does. I leapt out of bed and stripped the lingerie off my body and squirreled them away in their hiding place. I grabbed my clothes and darted across the hall into the shower. I washed the night before off of me. I scrubbed the oil off my ass and tried to process the morning. Did she know? Surely she didn’t know. How did I get into bed? Why didn’t she wake me up? My mind was a wildfire of thoughts as I tried to calm myself down. She couldn’t have known. She must’ve realized from the close on the ground that maybe I was naked and that’s why she didn’t wake me up like normal. That seemed logical enough to calm me down and drag me back to the morning. I finished my routine and went to the kitchen. Mom was pouring creamer in her coffee, the special creamer we have to go to the next county to get because of what Mom called, “Blue laws”. I grabbed what I needed for cereal as I thought about what go me horny yesterday, the molester in the peach trailer. As I sat down to eat, Mom asked me what my plans where for the day. I looked up confused and told her I was going to school, like always. She said thought it was a holiday and I remembered it was a teacher in-service day. There was no school! Holy crap, I could go to the Peach Trailer today! I said, “Oh yeah! well I guess I’ll go over to Shawn’s house and play!” Shawn was my best friend and lived far on the other side of the park, putting the peach trailer in my route!
Mom said that was fine, but I needed to change out of my school clothes and into play clothes before I went. I could change into my panties! Scarfing down my cereal quickly, I ran to the sink to wash my bowl and spoon before sprinting off to my room to change. I stripped down and dug in my closet for my panties in a rush. They weren’t were I thought I left them in this morning’s rush. I found my toys, but couldn’t find my bra and panties. I decided I was wasting too much time and would look for them later as I threw on my play clothes and bolted out the door.
I sat on the corner of his lot behind some bushes, hidden from the other trailers in the are as I watched his house. I could see his wife move about the house from the windows in the trailer. About nine am, she got in her car and left. I stood up and looked around for cars, then scanned the other trailers in range for people who might be watching, and decided to make a break for it. I ran to the shed behind his trailer and then looking around one more time, walked right up to the back door and knocked. The old man grunted and asked who was there. I found my voice and squeaked out my name. “Who?” came the gruff reply. I told him what trailer I was from and I heard him start walking to the door. I stood in front of the half glass and screen door as he opened the back door. I stood there, looking at him. He was wearing a stained wife-beater and grey boxers and he walked with a cane. “What do you want?” he growled. I looked up at him and said, “Sir, I’d like to have a glass of water. I got some dust in my throat and can’t stop coughing.” I coughed for effect. He pushed the cane into the door and pushed it open. I stepped back to let it swing out and then stepped right inside the door jamb. He smelled old and stale, and I could smell the dried piss on his boxers. I was shaking internally as I walked in the door. Was I going to get molested? I hoped so. Nothing Mom said about him sounded violent so I wasn’t worried about that.
He headed back to his old yellow recliner and back to the show on TV. He gestured toward the kitchen with his cane, but the layout of his trailer was pretty similar to ours. I knew where it was. I went into the kitchen and turned the tap on for a second and then shut it off. I tried to figure out how to do this when a wicked voice told me to just undress. I did as the voice suggested and stripped down. I walked back on my tiptoes to the living room, my pulse drumming loudly in my ears. My heart was leaping out of my chest as I touched the back of his chair. I cleared my throat and said, “Thank you, sir. That’s much better!” He waved his hand without turning around. “Can I ask you a question, sir?” He turned his head slightly and gruffed something. I spoke up again, “Please don’t get mad, but did you touch Jesse? My Mom said you touched him in a bad way.” He scoffed and forced himself around to the sound of my voice. When he turned around, he was presented with a completely naked twelve-year old boy with his head down avoiding his gaze and a twelve-year old little stiffy jutting out and his hands clasped behind his back. “WHAT THE FUCK ARE YOU TALKING about ohhhhhh” he quickly calmed as he saw me presenting my self to him. “So you’re a dirty boy who heard about an old pervert in the park and wanted to get some, huh?” I nodded my head.
“Look at me.” he demanded sternly. I looked up. “I never fucked them.” I looked confused. He said, “Catherine and Jesse, I never fucked them. Their Mom would leave them here for my wife to watch them. I would see them playing grab ass and one day when my wife went to the store I asked them if they ever fucked each-other. Catherine said they tried but that their Mom and Dad never left them together alone long enough to do it. I told them that they could do it there. I said they had to do it here in the living room where I could see them. They were worried about getting caught but my wife is old and slow. She’s going to be gone for at least two hours and that’s plenty of time for two virgins to fuck each other. So they did, and I watched. I can’t get hard anymore, so I didn’t even touch myself. I just watched two kids fuck each other. Maybe I told them some things to do, but that’s it.”
I must have looked sad as he asked if I wanted to fuck my sister. I said no, and he said, well what do you want to do. “I want to pretend to be a girl and be dirty with you.” He laughed and stood up. He walked right past me and said, “It’s good you want to be a girl with a little cock like that. Follow me.” I followed him back into the room that would have been mine in at home. It smelled like mothballs and stale books. There were pink girly things from the ’70s all over. “This was my daughter’s room, and her drawers are over there. Put on what you like and come back out to the living room.” He walked out of the room and left me alone. I stood there for a second, marveling at what had already happened. I grabbed my little dick and started squeezing it. I heard him shout, “you don’t have much time. Hurry up!” I snapped out of it and ran to the chestadrawer in the corner of the room. Starting at the top I found panities. I dug around and found a pair of thongs hidden in the bottom. They were purple and the crotch had a double row of pearls down the middle. I pulled them out and put them on. The pearls separated and my little dick and balls dropped out of them! They were crotchless! I opened the next drawer and found bras. I found a purple lacy one that matched and grabbed it. The next drawer had slips in it and the next had hose. I grabbed a pair of thigh highs and pulled them up. The rest of the drawers has clothes in them, but he didn’t tell me to get fully dressed as a girl and I didn’t have a wig or anything so I kept opening drawers. Then I wandered over to the closet and opened it. I saw a bunch of dresses, but I also saw shoes! I grabbed a pair of black platform heels. Slipping my feet into them the way I saw my Mom do it, I was delighted to find out they fit! I stood back up. I was kind of tall for my age, so most of the stuff fit, but when I put the bra on, it just hung there. Oh well. I walked around gingerly on the heels before heading back into the living room. He was waiting for me in the living room. He whistled but then laughed. I blushed and got hard at the embarrassment. He got up and said to stay there. He wandered off in the other direction and came back with something that looked like raw chicken. He said “My wife has these falsies that she used to use. Stuff them in that brassiere and I think we have a girl!” I did as I was told. After I got them in and adjusted the straps, I saw a flash of light and the mechanical wirr of a Polaroid camera! He was going to take pictures of me! I suddenly loved the idea. He sat back down to shake the picture. He asked if I jacked off before. I shook my head. He made the motion of jacking a dick at waist level. I hadn’t really though about stroking. I said that normally I just squeeze it while I put things in my butt. He handed me a silver bullet shaped object. I got down on my knees and spit on the bullet. I pointed it at my bum and pushed. My ass quickly gave way as it sunk in. I thought about the night before and decided to stroke the bullet in my ass as I squeezed my dick in the middle of his living room floor. He hobbled over to the chair and told me to keep going. I bent over on all fours but I was starting to feel stupid. “That’s good, that’s very good. I’ve got a little slut fucking herself right in front of a perfect stranger just because she needs it.” I was invigorated. He called me over to him. I got up and walked over. “Can I put your dick in my ass?” I asked. “No, I don’t do that.” was his response. I was desperate, “Can I hold or kiss it then?” I was desperate. I needed to feel his cock inside me. Something was driving me toward him, with more and more desperation. I wanted to be fucked by a man in these girl clothes. “My dick don’t work anymore. I don’t want that. Do you want to be fucked? Is that what you want?” I nodded my head. He said to lay down on the floor by the arm of his chair and throw my legs over my head. It was a weird request but I did what he asked. “Now scoot over here so your ass is up in the air on my chair, and give me the vibrator.” I did as he directed. “Now I’m going to put this vibrator inside you and you stroke your dick just like I told you. If you like it, keep going. You can stop whenever.”
I did like he said and he started fucking my ass with that little silver vibrator. Having someone else do it was like nothing I had ever felt. I started stroking like he had pantomimed and the feelings intensified. I became lost in the feeling for a bit. I found a rhythm that matched his pistoning speed and suddenly I could feel something building. I opened my eyes and drank in what I was seeing. I could feel the weight of my tits on my chest. I could feels the pearls from the panties massage the base of my dick and the vibrator sliding in and out of my ass. The shoes on my feet and the feeling of the stockings against my arms were too much. I started tensing up. The building up feeling was getting more intense. Suddenly the thing in my ass started vibrating. I felt like a sneeze was building, but in my body instead of my nose. My asshole was tingling and my dick felt extremely hard. Suddenly, something shot out of my dick and hit me right in the forehead. Then something else shot out and landed in my open mouth. I stopped stroking my dick and a feeling of relief swept over my entire body. The old man pulled the vibrator out of my ass and laughed. My ass felt dull and empty all of a sudden, but the taste of the fluid in my mouth brought me back to reality. “WHAT JUST HAPPENED?!” I screamed. HE told me to calm down and asked me if I knew what cum was. I said I had heard of it, but didn’t know what it was. He said it comes from happy dicks and pretty girls like you love the taste of it. He asked me what I thought of it. I had to admit, when I calmed down, I kind of liked it. Sweet, salty and tangy at the same time. He said I should eat what had landed on my head. I swiped with a finger and sucked my finger clean. I did like it. “Do all dicks do that?” I asked, he laughed and said, “Just the happy ones. Now, go get dressed before my wife gets home.”
I got dressed and put the clothes back in her room. I came back out and he had a cold coke on the table. He said, “Drink that to clean your mouth out. When you’re done, I want you to leave. If you ever come back, I will show this picture to your mother. I don’t want any trouble, and if you keep sneaking over, I’m going to get arrested. Go on and git, little sissy and don’t ever come back!” I was hurt and ashamed and horny. The “little sissy” echoed in my head, causing my heart to race. The fear of him showing the picture to my Mom was too great though and I ran out of there fighting back tears. By the time I got home, I was calm and wondering how I was going to get to taste more cum.
Source: reddit.com/r/eroticliterature/comments/eli73h/my_first_sexual_experience_bimale
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