I was never the type to back down on a challenge, and you knew that. We have been friends for long enough that you understood just how little boundaries I had with the people I trusted. That meant admitting to all sorts of embarrassing things you somehow always found a way to dig out about me.
That night in front of our friends, it meant exposing my new favorite toy, "a massive dildo I bought just out of curiosity", and why I loved it so much, "I guess it's the largest thing I've ever been able to take and I like the feeling of being stretched." Needles to say I instantly regretted it, but you have this way of emboldening me to do shameful things. The adrenaline can be addictive.
Everybody got curious about how big the dildo was and you made me go get it in my bedroom and show it to our friends. The girls gasped. "It's kinda crazy, I know, but I promise it fits after slowly working it in and out the entrance for a while", I said, trying to disguise my shame. You asked me if I meant the entrance of my pussy and I felt compelled to overexplain myself and clarify that while I do stretch my pussy on it often, I never tried it in my ass, my asshole could never take something like *that*
So you asked me if I'd like to try that sometime. I said that was impossible. You took the dildo from my hands and told me there was no need to lie, we were all among friends here. "It's a nice idea, but that would be insane, it's too big, it could never fit. Right, guys?" I looked around and nobody seemed convinced by my lack of faith. So I was told to take my ass out and I allowed my friends to all come and inspect my asshole. They made me kneel on the couch and spread my cheeks and used some spit to lube their fingers before testing my hole. Everybody seemed to agree that it was possible, actually.
A tongue got pushed inside my ass, and the surprise made me moan. Looking above my shoulder I saw you coming close with the toy pointed at me. "Wait, I mean it, I still struggle to fit it in my pussy, my asshole is too tight for this", but you told me to have some more faith in myself. You were all here to help and support me. You told me I was so strong and determined.
And you pushed the tip of the dildo against my sloppy wet rim, circling it in an angle, trying to get it to break through. I tried to protest, but one of our friends pushed my head on the back rest of the couch, making me shut up. I felt hands on my wrists and ankles and I was sweating in anticipation.
The thick round head started to sink in with all the pressure you were putting on it. My irregular moans started to blend together in a long continuous whimper. When my hole was finally able to swallow the whole girth of the tip, no words came out, just one long crescent scream
Our friends cheered, they were so proud of me. They told me I was brave and good and asked me how I was feeling. "It's, I– shit, oh my god," I tried to article as the girls stroke my cheeks and took the hair off my face. "Yeah it feels good, fuck it's too much, it's overwhelm–", I was saying, but you had the habit of interrupting me. You were always annoying like that. Before I could finish my sentence, you resumed your task to push and pressure that toy against my ass so rough it made me yelp.
One third of the length was already inside and my soaked rim offered the dildo no resistance. "Please! It's too much, I can't–" was what I said as you worked the toy further in, twisting it and making sure there was enough spit to finish the job.
You asked me to explain how I did it to my pussy again, "I work it, fuck, I jerk it in and out, slow– slowly, ah ah", and you did as I said, except with half the patience and gentleness than I have with myself. Our friends said I looked so hot with that thing in my ass, and I was encouraged to say how much I loved having it stretched by an object so large. I said "I love it, I love it I love it, I love it" so many times it became almost like a mantra.
You asked me how far did I think we went, and I said it felt like the whole thing was inside me at that point. You laughed and said with fake sympathy in your voice that the dildo was just halfway in. "I mean, it's enough, isn't it? Fuck, I feel so full, please, I'm clenching so hard around it", but our friends sounded disappointed. "Guys, please", I insisted, but everybody was so excited to watch me get fucked. They didn't want it to end, and hey, I was already there, might as well go all the way now. "I really hate disappointing you guys, you're the best friends in the world", I barely finished saying when multiple hands grabbed me and repositioned my body on the couch to the face the other way.
I was kneeling on the seat, facing all of you, and I could feel my whole face blush with embarrassment. You put both your hands on my shoulders and, with a smirk, started to pressure me to sit down on the toy. "Oh my god, no, it won't fit! Stop, stop it's too much!", I tried to protest, but you were relentless. My whole body was sweaty and shaking and now the blank look on my face as my eyes turned to the back of my head was visible to everyone. I was moaning so loud to the feeling of the dildo pushing and dragging forcefully my insides I could barely hear my friends' praises and encouragement.
One of the girls positioned herself in front of me so she could touch my clit as I took the last centimeters of that massive dildo inside, her fingers worked fast and sloppy from all the spit and juices running down my pussy. I tried to mumble "thank you", but I believe nothing coherent came out, just a long series of screams and gasps and prolonged moans blending together that signaled the longest orgasm I remember having.
The waves of the orgasm slowly dwindled out and spasms shocked my body for not getting used to something so big being clenched so tight. Our friends kissed and caressed my sweaty face as you looked at me with very little mercy in your eyes. "W-wha, what do you mean keep it in here a bit longer...?" I stuttered trying to understand your suggestion. We worked so hard to get it to fit, you calmly explained to me, that it would be a waste to empty my pretty hole now. I nodded. I love the feeling of being stretched, and I'll do anything for my friends.
