I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with bright red hair. She had a huge rack, at least a double D, and a tight sexy ass to match. Her name was Cherry. This has to be my lucky night I thought when she asked me if I wanted to hit the bars and so I agreed.
I spent the night going from bar to bar with Cherry getting completely shit faced until she suggested we go back to her place. I was a bit worried since we'd just met, but being shit faced drunk, I wasn't going to pass up fucking this hot fucking girl if she wanted it.
We got back to her place and I made myself comfortable in her living room and we shared a bottle of wine. Soon enough I started to get drowsy and I passed out on her lap. I don't know how long I was out for but when I woke up I was naked, in her large bed and she was standing in front of me wearing leather dominatrix shit.
"Wakey wakey slut." she said.
I heard another voice from the hallway say, "Oh! Is he awake?!" in a very excited voice and into the room came 3 other girls, all dressed up like something from the rocky horror picture show.
"What the fuck is going on?" I say, but I can feel my dick getting hard, which Cherry noticed.
"Look at his tiny little prick girls, it's getting hard." And all the girls started giggling and staring at my dick which caused it to wither back to its softest."It's not your dick that's going to get a workout tonight you whore," she said, sliding down her panties, "It's ours."
As the other girls took their panties off I saw that they all had extremely large dicks, at least 9 inches each, and Cherry's was at least a foot!
I tried to get up and run but the girls tackled me to the bed and tied me up, face down with my ass up in the air. I could feel a cold slimy substance being worked onto and into my tight asshole which was being filled with one, two, three and then four fingers! As I was being violated in my virgin hole, i started to scream, but it was quickly muffled by Cherry who shoved her giant prick into my mouth.
"If you bite me I'll call my boys up here and let them tear you a new one, so either start sucking and get fucked by girls, or scream and get raped by men."
I had no real desire to get fucked by anyone at that point but I decided that girls were better than the guys who I can only assume had even bigger dicks, so I started doing my best to suck off Cherry before she could shove her big ass cock into my ass.
"Oh fuck that feels good you little cock-sucking whore. You must have done this before. Get me nice and wet so I can pop your tight virgin cherry."
I sucked for a few minutes and then she pulled her dick out of my mouth and moved behind me. "This is gonna hurt slut, I hope you enjoy getting de-virginized by the cherry popper herself. You won't be the first slut I've tamed with this man-slayer." I felt the tip of her dick against my back entrance and I clenched as she tried to force it in. "Oh a fighter, I like that in a man, but it'll be less painful if you let it happen, pleasurable even."
I felt my ass start to spread for her giant cock as I couldn't clench anymore. "Uhhhhhhh" I moaned in pain as the head disappeared into my ass, followed slowly, inch-by-inch by the rest of her dick.
"Oh my god this has to be the tightest ass I've ever had the pleasure of fucking. It feels so good to have my cock surrounded by your tight ass." I felt her balls hit mine as she finally pushed the last inch of her cock into me. She left it their for a second until the pain started to numb. Then in a quick motion she pulled all the way out. "Uhhhhh." I gasped in pain as I felt the emptiness her huge dick left behind.
"She came back in front of me a stuck her dick in my face, I could smell my ass on it. "Suck it slut." she said. "My cock needs to be nice and wet if I'm gonna pound the hell out of you like I am. So suck it. or I'll call the boys." she said threateningly. I opened my mouth and she slid her dick into the back of my throat making me gag. "Yeah suck it bitch, get me nice and wet so I can get back into your ass an pound it hard."
I was helpless as she fucked my mouth ruthlessly. "You need more work as a cock-sucker I think," she said, "girls, someone, fill this bitch's mouth while I fuck him."
She once again got behind me and as i felt her sliding back in, much easier than the first time I felt the girls grab my head and turn me so I could suck their cocks.
"Oh fuck this is hot!" Cherry said as she pounded my ass on one end while the other 3 girls took turns pounding my mouth. "You're like a piece of meat on a skewering stick, except it's our meat!"
"Don't worry girls," Cherry said, "when I'm done you can fuck what's left of his ass. I can't guarantee it'll still be tight though." she laughed.
I could feel my asshole starting to get numb and a sense of pleasure swept over my body. Cherry must have sensed it cause she called to the girls to take their dicks out of my mouth.
"Is that enjoyment I sense?" She pulled back and thrusted deep and hard, I couldn't help but moaning. "Oh ho! It is enjoyment. Does the slut like when I do this?" she thrust in and out several times quickly and I moaned with each thrust. "Mmmm I thought so." She said thrusting hard into me. "Well if you think this is good, you'll love this!" She started thrusting harder and faster and just when I could hardly stand it she pulled out and shoved her dick into my mouth. I choked as she spurted a huge load of jizz into my mouth. All I could taste was her cum and my ass. When she was done she pulled out and I was about to spit it out when the girls covered my mouth. "I couldn't do anything but swallow the mouthful a jizz which I had to take down in two swallows.
"Fuck I haven't cum like that in ages!" said Cherry collapsing on the bed next to me. She started to untie me. But when I got up to leave she slammed me back onto the bed and said "Oh no! where do you think you're going? We've only just started with you!"
I lay helpless on my back ass one of the other trannies rammed her cock into my now stretched asshole and another sat on my face and made me lick her asshole. "Mmm." I could hear Cherry saying behind me, "I hope you enjoy the taste of ass!"
I tried to think of something else as I licked her asshole but all I could think of was the hard cock ramming in and out of my asshole. I didn't have to think long though as I felt the tranny's cock swell and she pumped her load deep inside me. She pulled out and the next tranny filled the spot she left. My ass was continually pounded this way for the next few minutes until my ass was once again filled with tranny cum.
"Ok, I'm almost ready to go again," said Cherry, "but I think his ass is way to stretched out to make me feel good so we're gonna have to try something new!" She brought me over to a chair where the tranny who had cum in my ass first lay stroking her still hard cock. "Sit on it slut! And ride it like the bitch you are!" I sat on the cock and felt it slide deep inside me where I knew there was a pool of jizz swimming around. I began to bounce up and down and the hard shaft when the girl whose ass I had been licking started sucking my dick which was surprisingly getting hard. She suck on it for a few minutes as I rode the tranny and when it was hard she slid her wet ass down on top of it.
There I was, the meat of a tranny sandwich, with a tranny cock in my ass and a trannys ass on my cock. Together we bounced until I felt my dick swell up and I shot my load deep into the trannys ass.
She got off and Cherry came over. "Well well, someone's enjoying themselves. Well it's time to see how much enjoyment you can stand!" I stopped bouncing on the rock hard prick and Cherry pushed my legs back and laid her dick on top of the one inside me. "Let's see how stretched you are."
She pushed her hard cock in alongside the one already in me and together the two pounded my ass hard. I could hardly take the pain but I didn't have too for long. I felt more cum flow into my ass as the tranny I was riding blew her load and it started to leak all over Cherrys dick.
"Oh fuck we made a mess!" she said. She pushed me onto the floor on my knees. "Now clean it up!" I started licking her dick clean but it was too much for her and she pulled my head back and blew another massive load all over my face. "Ughhhhhhhh!" She moaned as jet after jet covered my face.
"That was one good fuck. You should come back tomorrow." She said smiling with her giant dick still hard in her hand.
They threw me out of the building, naked, covered in cum and oozing it from my well filled well stretched ass. I limped home that night with thoughts of maybe going back tomorrow.