Dirty Dianna
Copyright© 2026 by JDlit71
Chapter 4
BDSM Sex Story: Chapter 4 - 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 Lesbian BiSexual Heterosexual Sister Father Uncle BDSM DomSub MaleDom FemaleDom Humiliation Rough Spanking Gang Bang Interracial Black Male White Male White Female Anal Sex Cream Pie Double Penetration Exhibitionism First Facial Oral Sex Sex Toys Public Sex Small Breasts
Trains, Gangs, and All the Free Feels
My Uber picked me up at 1:00, her name was Liza. She was blonde with big titties and wearing a tee shirt with no bra, which I could clearly see from the back seat in the mirror. We made the usual small talk and she asked me about my trip. I didn’t want to give too much away but I told her I was visiting relatives in Toronto. She said that I looked way too young to be on a big train by myself. I didn’t reply. The awkward silence was broken when she told me she had relatives in Toronto as well and then the conversation took a turn.
“Your sister has an amazing set of skills, did you know that?” she asked.
“No, what exactly do you mean by skills?” I asked innocently.
“I mean she licks pussy really good and I’m wondering if her younger little slutty sister, who’s visiting relatives in Toronto, is as good with her tongue.”
More awkward silence. I was speechless and it was obvious. She was glancing at me in the mirror and I was suddenly nervous.
“How about we pull over and find out why they call you Dirty Dianna?” she said smiling.
What the actual fuck? How did she know that? I didn’t even think Pam knew that they called me that. I didn’t have time to think, she pulled over into a vacant lot and opened my door and shoved me over. She wasn’t wearing anything but the tee shirt and she basically shoved me down, climbed over me and planted her pussy on my face. She smelled sweet and I didn’t waste any time licking her beautiful pussy. I licked her like a dog thirsty for water, not Duke though, and she seemed to be enjoying herself. I reached up and grabbed her big tits and played with her pierced nipples. That was a first for me. I only knew one other person with a pierced nipple and he was an older guy I met at the pool one summer a couple of years ago. She had these big rings looped through her nipples that I pulled on. She moaned and pulled my face into her saturated pussy, so I made a meal of it. I opened my lips and let her violate my mouth. She already expected me to be dirty, Daddy says you might as well exceed their expectations, or something like that. I was pulling her nipple rings with one hand and stroking her clit with the other while licking her with everything I had.
She was squirting all over me within a few minutes, burying my face in her waterfall. I kept pinching her nipples and pulling on her nipple rings. The harder I pulled and pinched, the more she clinched my head and ground her pussy in my face. She finally finished after like 10 minutes. She didn’t waste any time returning the favor. She put me in a 69 and attacked my pussy like a dog in heat, this time just like Duke. I didn’t last more than 5 minutes before I exploded, soaking her shirt.
We straightened up and continued to the train station and when we arrived she told me I was a mess. My hair was wet and my shirt was saturated with her juices. I forgot to pack an extra outfit so I didn’t have a backup plan. We exchanged texts and she said if I needed an Uber to request her from now on. She kissed me on the mouth really deep while I was standing in front of the train. I never thought about anyone watching but later I found out why I should always be aware of my surroundings.
I checked in with my phone and boarded the train and immediately noticed something strange. This train was filled with men. I scanned the entire car we were in and didn’t see one other woman. I wondered if Pam knew this when she booked my seat, but it didn’t matter. I was stuck here for the next four hours, which wasn’t a bad thing especially since several of the men saw me kissing Liza and assumed I was a lesbian. Now, I obviously hadn’t thought through my situation but as I was sitting and waiting for the trip to start, I got a text from Pam.
“Whatever happens, just go with it.”
I sat wondering what the fuck that was supposed to mean. The answer came almost immediately.
“Hey, you’re that lez from the Uber, right?” a greasy looking business guy said.
I looked at him like he had three eyes and I guess he assumed that I was. I mean, how many women were kissing another woman next to a car with an Uber sign on it facing the train? Probably not many.
He followed up with, “So, are you a switch hitter or strictly a carpet muncher?”
Again I gave him a crazy look, which he evidently took as angry, but I had no idea what he was insinuating or anything. I just played dumb. Daddy says guys always want a dumb cunt, so play your role so you can get what you want.
“Carpet muncher? What’s that even mean? I like–”
That was all I was allowed to say. A group of about five guys immediately jumped me and had my saturated shirt off me before I could say, “Please and thank you!”
They pinned me down on the floor and dicks were stuffed in my mouth and hands. My pussy was being fingered and my ass was slapped as they folded me up so that my shoulders and head were pinned to the floor by the guy fucking my mouth and my ass and legs were being spread in the air. Someone was jamming my cunt with four fingers, and it was tight, while they were spanking me and tickling my feet. Now that was weird. I couldn’t see because the guy fucking my mouth had my arms pinned with this knees and his balls were slamming into my eyes as he fucked my throat.
Every chance I got I would shout, “Just wait until butch finds out about this! She’s gonna find every fucking one of you and –”
That’s about all I could get out before another cock was stuffed in my mouth. It was like a “train on a train” and I loved every second of it. I’ve had rough sex at Mr. Butch’s trailer before, but this was like getting fucked by a herd of buffalo inside a moving car. The entire three hours was spent with at least three guys fucking two of my holes. Did I mention at least one of those hours was spent with 8 BBC’s? They all worked for the same company and they had plenty of experience banging little trailer park white girls like me. I think they could tell I wasn’t a lesbian but I never argued with any of them about that claim. They all wanted to “turn me” and make me want dick instead of pussy. Something tells me that either my sister Pam or Liza, or maybe both of them, had planned how this went down, and I do mean down.
These 8 black men came into the group one by one, until they were all surrounding me. Here I was, this little tiny white “lesbian” that they all wanted a piece of, just laying there, getting fucked up beyond all recognition with no way of escape. I had them right where I wanted them, or at least I’m sure they thought otherwise. My jaw muscles were already sore from the previous two hours of sucking men, now they were getting a real workout with these big dicks. Once they took over, my holes were stuffed to the max with thick black dick. None of them were less than 8” long and a full 2” thick. Then they decided to see if they could get two of them in each hole. In all the chaos I did notice that at least one camera phone was recording the entire time, not to mention all the other businessmen holding their phones and narrating my abuse in a “play by play” style like calling a basketball game.
“There goes one up the middle. He stuffs it! It’s a slam dunk!” I heard one guy saying.
“She can’t get enough, talk about a layup! Nothing but net here guys!” another guy said.
“Looks like two on one here with multiple bank shots hitting that ass! That’s a three pointer, in more ways than one!” another commented.
“I’ve never seen a backdoor cut like that! Talk about a box out! He’s got that whole lane covered!” another guy shouted.
“Oh no! It’s another turn over!” one guy said as they flipped me over in the middle of a three on one.
Somehow I managed to get 2 dicks in my pussy and one in my ass several times. These men were stretching my holes beyond their limits. Little did I know they were just getting me warmed up for a night in Toronto.
Back to the train. Once every man on that train had taken my pussy, ass, and mouth, they tied me to the sink in the tiny bathroom, using a couple of businessmen’s ties, and whenever someone needed to piss, I was the lucky toilet girl.
Of course I complained about it every time they came in. I’d say things like, “You’d better not piss on my face! Liza knows where I am and she’ll fucking find every one of you if you do ... gulp ... gulp ... gulp!”
It worked like a charm every time. They would aim for my face with their dicks and I had shower after shower of glorious piss washing over me. It was the best train ride ever.
When we arrived at the station in Toronto I was still tied up when one of the conductor guys opened the door to the tiny bathroom. There I was, covered in piss smiling and tied to the sink.
“What the fuck are you doing in here?” he asked.
“Waiting for you, Daddy!” I answered.
He pulled out his cock and fed it to me. I sucked him off and then he pissed all over me after I begged him to. It was the perfect ending to my train on the train.
I didn’t realize just how bad I looked until I got off the train. Thank goodness someone left me a shirt and some sweat pants and a tie. I looked ridiculous, but I smelled like a walking urinal. It was humiliating, but of course it made me wet. Several homeless men grabbed me as I was walking through their section of the train station, but they let me go once they smelled my disgusting stench. I couldn’t blame them. I found the women’s restroom but it was out of order and I had to use the men’s restroom instead. Of course, you guessed it, once I was washed off using the sink, several men walked in while I was naked. They pinned me to the wall and fucked me standing up, one at a time. When they were finished with me they shoved me in a bathroom stall and barricaded the door closed. One of the cleaning crew men found me and let me out. He was so nice and he even found me some decent clothes, but then he wanted to whip me.
“What do you mean by whip?” I asked him.
“You know, like whipping your ass with a belt? You ever had that before?” he asked.
Now my father had whipped me several times when I was younger, but I never got wet or enjoyed it. Now that I was older, I had seen other women getting whipped like those in the videos. Also, Daddy had asked me if I wanted to try it. He said that I should experience it, but it needed to be controlled and he would talk to my sister, Pam, about having a “session” with me. That seemed like the best plan.
“I appreciate the offer, Daddy, but I think I’ll pass on the whipping,” I replied without a hint of judgment. I noticed the patch on his uniform said, ‘Darryl’ but I decided not to call him that just yet. “I do appreciate you getting me out of that stall and for the clothes. I would be happy to give you something in return, Sir?” I offered.
“Call me Mr. Clean. So, what exactly do you have in mind, young lady?” he asked in a somewhat timid voice.
“Well, Mr. Clean,” I said giggling, “I think if you’d like to fuck me that would be something that I could make worth your time. Or a blowjob, or a hand job, you can pick. I’m just thankful that you came along and I want you to see how much I appreciate you.”
“How about you suck me off in my office and we’ll call it even? Sound good?” he asked, smiling.
“Absolutely! Which way? I’ll follow you.”
I can’t believe how naive I was. Even after all the training from Daddy and Mr. Butch, and all the humiliation from my “friends”, I feel like I was as dumb as a box of rocks. I followed him to an office that had a sign that said “HEAD CUSTODIAN”. Like a true gentleman, he opened the door and held it for me as I walked in.
I woke up hours later and he had tied me up in a bundle. I had a massive headache and my knees were pressed against my chin. My arms were tied behind my back and I was naked, blindfolded and freezing. I remember thinking at that point that this was my life. No matter where I was or what I was doing, it seemed pretty obvious that I would eventually wind up bound and blindfolded.