Dirty Dianna
Copyright© 2026 by JDlit71
Chapter 1: Trailer Park Tryouts
BDSM Sex Story: Chapter 1: Trailer Park Tryouts - There's not a lot to do in Canada besides hockey and drinking. Daddy keeps me busy though...
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Ma Fa Teenagers Coercion Consensual NonConsensual Reluctant BiSexual Heterosexual Sister Father Uncle BDSM DomSub MaleDom FemaleDom Humiliation Rough Spanking Gang Bang Black Male Anal Sex Cream Pie Double Penetration Exhibitionism First Facial Oral Sex Sex Toys Public Sex Small Breasts
“No Daddy, not my dirty hole! He’s too big, he’ll hurt me,” I said, begging him not to let the guy fuck my ass.
Of course I knew he wouldn’t listen. I was the entertainment and they probably wanted him to ruin my ass. They haven’t been nice to me since before my first time, but I’m getting ahead of myself.
It wouldn’t be my first time, but it would be the first time with Daddy and my father’s friend, I’ll call him Mr. Butch. My father had no idea what we were doing at Mr. Butch’s trailer, they were friends and I’m sure he trusted his friend with his youngest daughter. He also didn’t know about Daddy.
So Daddy wanted Mr. Butch to have me, for my first time, instead of being with some idiot boy my age who wouldn’t know how to treat me or which hole to put it in. Daddy doesn’t live near me, but he knows what I need and always has a plan for me. We found each other online through my older sister, Pam, which I’ll get to later.
A little background on Mr. Butch, he was perfect for my first time. He went slow, he was gentle, he took time to make sure I understood what he was about to do with me. Before I even went to Mr. Butch, Daddy told me it would hurt, I checked with my sister and she said it would. I was scared then, but Daddy calmed me down before I ever made it to Mr Butch’s trailer.
Mr. Butch is my father’s friend who lives around the corner. He fucked my sister and they made me video and take pictures while they were doing it. He’s got a very large cock and he’s a nice enough older man. He has some rules while we’re at his place and Daddy says I have to obey his rules.
Daddy says, “His place, his rules”.
Rules like we have to be topless or naked whenever we’re there, me or my sister, and if we need to borrow something, we have to give him a blowjob or he gets to fuck us if it’s something big or valuable to us. Like one Tuesday, before my first time, I forgot my jacket and it was supposed to rain. I usually go to his place in the morning before school and I realized I didn’t have my jacket.
“You’re welcome to borrow mine and you won’t even have to bring it back,” he said with a smile. “You just have to suck me off before you take it, ok?”
I was speechless trying to think about what he had just told me, plus, he had a cool blue jean jacket with all these military patches on it. I could have just picked up my own jacket as I passed my place on my way to school but I had never sucked a dick before and I was curious.
“Clock’s ticking ... tick tock. You’re gonna be late for school, what’s it gonna be?” he said to me, winking.
This was before the first time he had me and right before he made me go topless when I visited, so I was really shocked. I didn’t want to say no, but like I said, I had never sucked a dick before. I just stood fidgeting and looking out the window of his trailer. I wanted to ask Daddy but it was kind of a weird situation.
“Ok, but I’ve never done that before, Mr. Butch. Will you tell me how to do it and what to do? Daddy says I have to obey your rules when I’m here, so I guess it’s ok?” I told him, although I wasn’t sure if I should have.
I was really kinda scared, but I had seen my older sister suck guys and she made it look easy. He made me get naked and that was a little weird, but he kept telling me how beautiful I was. He didn’t push me or touch me, he just watched. I guess I thought sucking him would be easy for me and I got in a little over my head. When he pulled his shorts down I couldn’t believe how big he was. It was the very first real dick I had seen, in person, except for the guys my sister sucked off. I got on my knees and quickly opened my mouth, mainly because I didn’t want to be late for school, but also because I was anxious to try and suck him. I didn’t even touch him at first, I just opened up and sort of closed my mouth around the tip. I wasn’t sure what to do so I just sat there with his cock barely inside my mouth looking up at him trying to remember what to do next. I knew I was supposed to be sliding it into my mouth, but my brain went dead for some reason.
“Look,” he said quietly, “grab and hold the base of my dick and start sucking it like a lollipop. You’ve sucked a lollipop, right? You’ve got this Dianna!”
I shook my head up and down, his dick was still in my mouth. I cringe when I think about this and how dumb I was at the time. He gently grabbed my head and began to pull my mouth onto his massive cock. I’ve got a pretty wide mouth, so I let it slide between my lips, slowly at first. I didn’t want my braces to accidentally scratch him, that would have been the worst. It was smooth and it tasted a little salty, but I liked the feeling of it inside my mouth. I let my tongue glide over it. It made my (down there) hole tingle. I looked up at him and sorta smiled. I was so inexperienced. Then as I started to realize he was controlling my head and I wasn’t in control, I was having trouble breathing naturally through my nose. It freaked me out, I swallowed, he stuck his dick deep down my throat, not all the way, but far enough that I gagged. Then it got worse. I lost all control and couldn’t breathe right. I totally freaked out and coughed, then I puked all over his floor. He was so kind though. He apologized but he made me clean it up with paper towels. He made me stay naked while I was cleaning and I think he took some pictures for Daddy.
Once I settled down he asked if I wanted to try again and of course I did, but I had to go to school. The next morning he went slower and I actually got to taste his cum. It was salty but I liked it. A lot. Plus I hadn’t eaten breakfast so I was already hungry. Looking back, I think that maybe why I love the taste, but honestly it’s so tasty regardless. Sometimes it’s still in my braces and I can taste it an hour later. It makes me wet.
Anyways, one other time, a few days later, we needed to borrow a software program called WORD or Microsoft something, I can’t remember, to do some homework. My sister offered to suck him but he wanted to negotiate and she ended up fucking him. She’s a whore so it didn’t bother her, but they made me video it. She said it was worth it. He is a nice man. We’re fuck buddies now and he uses me for different fantasies he has. He says I’m good at it.
Now about Daddy. To be fair, I had never met him in person, but I talked him into being my Daddy online. I wasn’t a whore like my sister, yet, but I liked doing his tasks, which he gives me plenty every day. Sometimes his tasks involve Mr. Butch, I think because he’s my Father’s friend and he has a big dick. Daddy likes to see me with a big dick in my mouth, and other places. He thinks it’s hot and, to be honest, I do too. Daddy’s a writer and writes stories for a lot of women. I found out about him from my sister because he wrote something for her. She thought I needed someone to train me, so she suggested I convince him to do me. Now he’s my Daddy, but he also has my sister. We both do tasks.
So fast forward, there I was, on my knees naked and blindfolded with my mouth open. Mr. Butch had told me to put my hands behind my neck because he said it makes my little tits jut out and my nipples get really hard. He keeps his trailer cold all the time so I always have goosebumps anyway. I figured this would be like other times when he had me like this and his buddies would come over and I was their entertainment. I like being the center of attention. A lot. He has four friends and they like to use all my holes. I like it when they do me like that. Especially when I’m forced to take their cocks all at the same time. It’s a challenge, keeping grown men hard all at the same time when you’re blindfolded, but they say I’m really good at it. Of course when they think I’m not listening I hear them say that I’m “just a set of holes”, or I’m “just their Tuesday night whore”. I have to laugh. They think they’re using me. Men are so dumb.
So there’s a knock on the door and I hear Mr. Butch pass by me and I feel the cold wind on my boobs as he opens the door.
“Come in. Take a seat,” Mr Butch says.
I hear him, and someone else following him, pass by me. Neither of them touched me, but I heard a clicking sound. Nobody speaks, nothing, not a word for a long time. I’m wondering if they’re still in the room with me. My arms are starting to ache and my mouth is dry from the cold air. My tits are freezing and my knees are killing me, even on his carpet.
It felt like forever and I was starting to get nervous with no sound, no breathing or nothing. All of the sudden a loud knock at the door and I jumped it scared me so bad. Then I heard footsteps coming down the hall and Mr. Butch passed me and opened the door. I knew it was him because of his cologne.
“Hey, you’re finally here. Come on in. You want a drink?” Mr. Butch asks.
No answer. I just hear footsteps circling me. A new cologne. They must have circled me three or four times. I just sat there on my knees with my hands clasped behind my neck, breathing. More clicking. Suddenly, a stinging on my left nipple.
“Ouch! FUCK THAT HURTS!” I shouted.
SMACK!
My face was stinging. Someone slapped me with something. It didn’t really hurt, but it got my attention. Then my left nipple had another sharp pain and I heard a bell ringing. The sound came from my nipple. Another stinging pain, this time on my right nipple. Then a sharp pain and another bell ringing, this time the sound came from my right nipple. I wanted to scream and rip that blindfold off, but I just grabbed my nipple and another swat to my hand. I was able to tell that someone had put nipple clamps on me with little bells attached. It stung, but I was managing the pain, right up until several hands were flicking those fucking bells, over and over. I screamed and another slap to my face.
“Shut the fuck up, slut!” said a voice.
It was a female voice, one that I have heard, but never like this. My brain was thinking about every voice I had ever heard before but it came up empty. I couldn’t put it together.
“Make her do it. Make her stuff her pussy and I’ll–,” a female voice whispered.
You’ll what? What will you do while they make me stuff my pussy? I was craving for the answer. Who was this? How many other women were in the room? How many men? Was I the only one naked? I was confused. Was I surrounded? Wait! Was I being video taped? Was I being live streamed? Now I was nervous and shaking.
And just like that I was picked up by my waist and held in the air.
“Stand slut,” another voice commanded, strong and authoritative. It sent shivers down my spine.
I straightened my legs and stood up, my hands still locked together behind my neck. An arm was taken and I was led to a wall in Mr. Butch’s living room. My back was pressed against the wall and something long and thick was placed in my hand.
“Squat down and don’t move,” the stranger demanded.
I leaned back against the wall and squatted, my knees spread wide as I sat wondering what they had in store for me next. I didn’t have to wonder long, a pinch to my pussy lips jerked me out of my wondering brain. Then another. Then a quick sharp pain and I instantly heard the familiar sound of tiny bells. FUCK! Now they had clamps and bells on my nipples and my pussy lips. What next?
“Stuff that cucumber in your pussy and start fucking yourself and don’t you fucking stop until I tell you to, you hear me?”
This time it was Mr. Butch, but I had never heard this tone before. My fuck buddy was giving me orders now. Instead of both of us pleasuring each other, he had control of me. I suddenly realized I was wet. I slid the cucumber inside me and there was no resistance whatsoever. It felt so good, and so shameful at the same moment. I had no idea who was watching me stroking my own pussy in that room. My own father could have been in there and I was willingly doing whatever I was told to do.
“Faster slut, Daddy wants to hear those fucking bells ringing on your pussy lips,” she whispered into my ear.
Wait. Did she say, “Daddy”? Was Daddy here? Was he here right now? How was this possible? Surely not?
Again, someone was flicking those bells on my nipples. Over and over, just flicking them. My hand was working the cucumber in and out of my pussy. It felt so good, but those bells were ringing too, and that was hurting.
“A symphony of bells!” Mr. Butch announced.
They stopped flicking or ringing the bells on my tits and it got quiet except I could hear sucking or smacking of lips. I paused to try and figure it out.
WHACK!
Something swatted my tits and made the bells ring again.
“Did I say to stop stuffing your cunt with that cucumber slut?” a deep voice asked in a very mean tone. I remember thinking that it might be Daddy
“No Daddy.” I replied.
“Back to it then. Until I say to stop,” he barked.
I quickly continued jabbing my wet pussy with the cucumber, as instructed. I was so happy that Daddy was finally in the same room with me. I couldn’t stop smiling. I was curious about the sucking sound though. I could hear moaning and slurping sounds, even with the bells dangling between my legs. I could hear voices snickering and I was starting to think they were doing it towards me. Every few minutes someone would flick the bells on my titties and laugh. More clicking. There were different laughs each time.
“Hey, instead of us flicking those titty bells, why not make her do it herself?” someone asked. “She’s got another hand.”
“Ok slut. Flick your own fucking bells and ram that cucumber in your pussy faster while you’re at it.” Mr. Butch ordered.
I was so humiliated. There I was, squatting down fucking myself with a cucumber and flicking my own nipples while people were watching and laughing. I could feel my face turning red as I flicked and pounded myself shamelessly for the entertainment of whoever was in the room. At the same time I was gushing while pretending the cucumber was Daddy or Mr. Butch.
“Open up slut. Time for dinner. It’s a slab of sausage followed by some homemade cream!” Daddy’s voice said.
My mouth was pulled open and a dick slid across my tongue and down the back of my throat. I could feel the heat of his body in front of me as his balls began bouncing on my chin. I was beginning to match the rhythm of the cock fucking my mouth with the cucumber in my pussy. It was majestic and reminded me of getting pounded by two guys at once. Suddenly I didn’t care who was in the room, I needed him to fill my mouth with his tasty cum. I increased the suction of my lips and I could feel his massive balls tense up as they slapped against my chin just below my lower lip and the hairs on his belly tickling my nose. I felt his hands grab the sides of my head and then his pubic hairs were smashed against my nose. He held my head still as his cock began spewing his thick warm cum into the back of my throat. I swallowed most of it, but some was dripping out of the front of my lips and down my chin as he backed away. I felt like a total whore, still pounding my own pussy with the fat cucumber. It felt amazing, but my brain knew it wasn’t a real dick.