The Evolution of Cassandra, part 10 – The Frat

Hello My Lovelies,

It’s proper, present-day Cassandra. I’m in awe of how many reads and likes the recountings of my adventures have gotten. I also want to apologize for some of the grammatical errors; they’re especially embarrassing for someone who works two different part-time jobs as an editor. In my defense, my new Dom is making me write these while I’m absolutely trashed and getting fucked by a machine. It’s hard to form coherent sentences when you’re that distracted. I’m slowly working my way back through to fix my typos.

I’ve gotten a couple questions about when I’ll get to the situation from the beginning of part 1. That happened Spring Break my freshman year of college, there’ll be a time skip soon. I’ll give you one spoiler to hold you over until I get there: I was tied up or tied down for half that weekend. Actually, I’ll give you a second spoiler for free: the four inch wide toy I woke up with in my ass wasn’t the biggest thing I took that weekend, not by a long shot.

Thanks for reading. Let’s get back to the end of the summer.

XOXO

Cassie

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I’d just spent more than two weeks at Mary’s house while her parents were away. Those sixteen days had been utterly amazing. Mary and I spent the time drunk, high, and fucking like crazy. We’d gotten more and more depraved over time and even started involving the random guys who delivered our meals. I really never wanted it to end.

I’d been texting with Daniel, or as he’d been introduced by his fellow frat boys, Big D. We’d been texting since I’d met a bunch of them while camping and I’d fucked all fourteen of them, more than once. I’d learned two things since then: he and his friends weren’t the whole frat, they were just the rising seniors, about a quarter of the whole fraternity, and that they all hoped I’d come visit them. Uh, yes, please.

I asked him to introduce me to his frat brothers because I was hoping they could all entertain me for the entire weekend. He convinced me to take the train down to Richmond, VA on Thursday. He was hoping he could spend the day, and night, with me before, well, before they all fucked me senseless.

I flirted with him a little, but made my intentions very clear: his dick was absolutely massive and I wanted it back in my ass, and back in my throat. He asked about fucking my pussy but I warned him I was worried it wouldn’t fit.

We talked a lot, about ninety percent of it was sexual or at least flirtatious. He’d asked me to send naked photos of myself, but Katie had forbidden it. The most he got was photos of my face, me in my underwear, and a series of photos of me swallowing Mary’s fourteen inch dildo.

We also talked about what kinds of things I’d like to have ready for me when I was there and if anything was off limits. I told him he and his friends could do just about anything they wanted with me. I also told him I expected to be fucked nonstop from when we started Friday afternoon until, at least, Sunday morning. I ordered a return ticket for Monday afternoon.

My parents were away for another couple weeks. Katie and I were going to go shopping for some new outfits.

Our parents left early the next morning. They’d barely closed the door when Katie made me strip out of my clothes and handed me some brownies to eat. I ate them, standing naked in the kitchen and washed them down with a big glass of milk. Then she brought me upstairs.

Katie locked the collar in place. She knew I’d be away Thursday afternoon until Monday evening, I wondered if I’d just be wearing it until I left or until I got back. She put my old friend, the saddle, on my desk chair and equipped it with the double dildo. She pulled the plug out of my ass and ordered me to sit. Once I’d impaled myself on both dildos, she tied my ankles, wrists, and neck to the chair.

I liked where this was going, but Katie surprised me. She put the saddle on the lowest vibrational setting. Everything buzzed deliciously inside me but I could tell this would only rev my engines, it wouldn’t make me cum. I started to complain, but Katie left the room.

She came back maybe a minute later with a blindfold and something I didn’t recognize, it looked like a ring. A really wide ring with straps. She had me open my mouth and pushed the ring in. It stretched my lips open wide and I could tell it covered my teeth. I felt her buckle the gag closed behind my head. Then she pushed a small dildo through the ring and into my mouth. It filled my mouth fairly well but fell short of reaching the back of my throat.

I felt a pinch on my left nipple as she attached a small clamp on a chain. On the other end of the chain was a ring, two other chains with clamps were also connected to the ring. She connected the second clamp to my right nipple. I flinched, and yelped into the dildo, as she attached the third clamp directly onto my clit. Then she put the blindfold on me.

“I’ve got things to do, I’ll check on you in a few hours.”

She left me like that, I never heard the door close.

I was in agony. Well, the agony of extreme sexual frustration. The brownies started kicking in after maybe twenty minutes. Over the next half hour, everything felt fuzzy, sensation started echoing through me, and everything started to spin. The entire time, the saddle buzzed the dildos inside me. I desperately wanted to cum, it was all I could think about, but I knew the current level of vibrations would never get me there.

My eyes were blindfolded but I could feel the world spin. The feeling got stronger and stronger as time marched on. I lost track of time, which wasn’t really surprising since every minute felt like it lasted forever but passed in a second. I squirmed in place as I grew more and more turned on and more and more frustrated. Drool dripped from the opening between the dildo and the ring gag.

An eternity later, I heard movement. I felt someone pull the toy out of my mouth. They replaced it with a dick.

Out of my mind horny, I sucked on the mystery dick. It moved in and out of my mouth, but didn’t reach my throat when I felt my face press against his body. The owner of the mystery dick fucked my face for maybe ten minutes before he came in my mouth. I did my best to swallow but the ring gag kept my mouth open, I felt some cum spatter onto my breasts.

“Cuh uh cung, ease?” I asked through the gag.

I heard Katie’s voice, “Maybe later, if you’re good.”

A second mystery dick pushed into my mouth. This one was longer, it fucked in and out of my mouth and throat. I moaned into his dick and sucked as much as I could. I lost track of time but, eventually, he pushed his dick as deep into my throat as he could and I felt cum flowing down it. I was disappointed I hadn’t gotten a taste.

A third dick fucked my mouth, then a fourth, then a fifth, then a sixth. I was delighted at how much delicious cum I got to enjoy, but I was going crazy not getting to cum.

“Ease, ceh uh cung? Ease,” I begged.

“Maybe after another dozen dicks,” Katie replied.

Another dozen? Six guys I’d never seen had fucked my face and cum in my mouth and there were another dozen on the way? The thought of being exposed like this made me even hornier.

I moaned loudly, really loudly, it was half whimper.

“Hush now, take some more dick like a good girl,” Katie commanded.

A seventh dick entered my mouth. I sucked and was rewarded almost immediately with a mouthful of cum.

Sadly, the eighth dick never made it into my mouth. I heard a guy curse and I felt cum spatter on my face and chest, some dripped onto my legs.

I took another ten dicks from owners I never saw. I was desperate to cum.

“Ease, a’ie, et ee cung,” I begged again.

“Well, you definitely earned it.”

Katie turned up the dial. I’d have been satisfied with the vibrating getting just a little stronger, I knew anything more than the lowest setting would get me off. Katie was an overachiever, she turned the dial all the way up to ‘world-shattering.’

I felt the climax build rapidly; I’d been getting driven insane for hours, especially for what must have more than two hours of getting facefucked.

I was just about to cum when the vibrations turned off completely. I screamed in frustration, at least as much as you can scream through a ring gag.

I sat there, frustrated. I heard laughter.

Once I’d cooled down, she turned the vibrations back on and cranked them back to max.

Again, she turned it off before I could cum. I sat there, my sanity slipping.

She turned the saddle back on, and I prayed I’d get to cum.

Again and again she’d turn it off before I’d cum and turn it on after I’d cooled down.

I begged and begged for release as I felt the world spin.

Just when I’d given up hope, she let me.

As I was getting close, convinced she’d leave me hanging again, I felt something very long and rubber slide into my mouth and down my throat. It was insanely long, I felt it slide and slide over my tongue, it hit the back of my throat and just…kept going. It slid all the way down. Seriously, I felt it poking on what I realized was the entrance to my stomach. I could tell there was more still sticking out of my mouth. God help me, I loved it.

The orgasm that hit me was massive and lasted an eternity. I came like crazy. My limbs tried to thrash but they just strained against the bindings. My scream was muffled by the endlessly long toy in my throat.

My limbs jerked and my back arched as the orgasm took me. Eventually the chair and I fell over. My body spasmed uncontrollably. I was still cumming when the oxygen left in my lungs ran out and I fell unconscious, cumming harder.

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I don’t know how much later it was when I woke up.

I was still blindfolded and still bound to the chair. The only difference between when I’d passed out was that the toy in my throat was gone and the saddle had been turned off. The cum on me was still wet.

I just lay there for a while, my world was still spinning.