*NOTE: The following takes place after the events of my three-part series, "The Cherry Ceremony." I'd recommend checking out that series first before reading this story. Thank you!
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I finally understand why my ex-girlfriend screamed the first time we tried anal.
"Oh my God, it fucking hurts! Shit shit shit!"
I took my ex's ass virginity surrounded by the pink floral walls of her bedroom during one summer break. I lost my own behind a nightclub pressed against a dumpster at 2 in the morning. My anus was pried open by a fat cock that only wanted to dig around my insides, so, I can't say that my first time bottoming was very romantic.
"Oh yeah, take it pretty boy...," my lover spanked my ass cheek, then gripped my hips with his calloused hands. We would've alerted people with our fucking if they weren't distracted by the music blaring indoors.
This guy lifted me off my feet and kept me pinned between himself and the smelly waste bin until he was totally satisfied. His hips were relentless, grinding his cock harshly on my prostate, which was bordering on being more painful than pleasurable. I was twisted however he wanted.
"Get ready...Imma make a mess outta you."
There was no foreplay in the beginning; he didn't give my dick the tiniest bit of attention. He just seized my hips harder and tensed up, arching his back and howling into the night sky as the rush of his hot cum shot through his dick and poured inside of me.
He had to have pulled out after that, but I had "Phantom Dick." I could've sworn he was still fucking me, but I was just twitching along the dumpster recovering as he zipped up his jeans. To fill the awkward silence, he bent down and took both my ass cheeks in his hands and pulled them apart to inspect the damage. I winced in discomfort. His spent cum was just about to topple over the edge of my asshole and spill down my thighs, but he rescued it by pressing his face on my hole and slurping it up.
This guy actually slurped out his cum from my gaping asshole...I didn't even know that was a thing. The sensation left me even weaker in the knees. He swirled his cum around with his tongue and was able to clean nearly all of it out of my hole; that was the most gentle he had been with me the entire night.
He stood up again and wiped his lips with the back of his hand, releasing a satisfied huff of air.
"Now, I don't gotta pay for a drink," he joked.
I used my depleting energy to pull up my pants and face him.
"I didn't cum," I said.
"You sound like that was part of the deal."
"Is that something we have to discuss?" I grimaced, "I thought that was a given."
A vein in the guy's neck was exposed from under his skin and he brought his hand up to rub at it. "You don't have a right to cum with what you did, so quit your complaining."
"What I did?" I approached him, "I didn't force you to beat him up, Don!"
I was pushed against the brick wall of the nightclub for what I said. Don's eyes grew dark.
"What you expect me to do when you say that motherfucker raped you? You're not innocent in this. You talking about how what he did ruined your life, when you ended up ruining mine!"
Don's arm was blocking one side of me and another was down low, his hand grabbing at my crotch. He clawed into it like he was ready to rip it off my body.
"I lost my fucking football scholarship to save your ass, and then to turn around and say that was all a lie? At least if it was real it would've been for a good cause, but this? I took the fall for your fucking stupidity!"
At the words, "fucking stupidity" Don spat in my face. His hand was still cradling my crotch. I shuddered under the touch.
"Dirty fag," Don growled, "I'm about an inch away from beating you and you're about to cum..."
I grabbed Don's wrist and guided him under my jeans to stroke my throbbing length. His hand took to it naturally, starting from the base of my cock down to the tip where precum had been leaking. His fingernail pressed into my leaking slit.
"Oww!"
"That's right," Don said, "Get used to the pain, cause that's all you'll feel every time I fuck you..."
His nail pressed in just a little more, to where I felt a surge of pain rush through my body, making me break out in a small sob.
"You ready to cum, Pretty Boy?"
"Yes yes!"
Don's nail went away from my slit and started scraping along my shaft, right along the veins that were poking out from under it. Don licked up my throat and groaned.
"You think you get to cum like a man? No fucking way..."
He tugged on my shaft just a couple more times, before his hand was slathered in my precum. I had to force myself not to bring him closer to me, just keep myself pressed aganist the wall.
"It's coming..." I gasped, "Don't stop...ah-!"
A rush of hot cum spilled onto Don's hand. It was fresh and thick; I thought Don would wipe it on my pants, but he kept it resting on his hand.
"Open," Don said, instructing me to relax my jaw and accept his fingers into my mouth so I can get the full taste of my own semen in my mouth. I sucked on his two fingers and moaned at the salty taste.
Don snickered. "Oh, I'm gonna have fun with you..."
Fucking me was Don's way of taking his anger out after I sabotaged his chances of getting into a good college. It was a fair deal. He gets to sort out his own feelings by fucking my ass and I received proper punishment for how I betrayed him.
It took a long time to accept that I liked men, but through that journey I hurt a lot of people. I framed my best friend, Brandon, of assaulting me just cause Don and his buddies were on my ass about whether I was gay or not. They accused me of spending too much time with Brandon after school and that there was obviously much more going on between us besides studying. They were only half right.
Brandon and I had been study buddies for years, but right before we graduated high school I asked him for a favor. A sexual favor that confirmed my sexuality, but I was a coward and said he forced himself on me for the sake of my reputation.
I was a dumbass. You could even call me evil if you like. All of the things you'd label me are nothing compared to what I've called myself. I had no way to apologize to Brandon for what I did because I didn't think I even deserved to talk to him. The guy got beaten up over a lie! I doubt he would've accepted any apology then.
I was ready to live life without Brandon once he moved out of state for college, and with him gone I had to find forgiveness somewhere- and no, confessing in a church wasn't enough. I've tried that already, but it didn't give me the satisfaction I needed, but with Don, I got my deserved punishment.
As much as I hated to admit it to myself, the thought of being tortured sexually like this turned me on. It was satisfying to be degraded- I was being absolved of my sins. That first night together by the nightclub was my own version of Dante's Inferno, where my stage of Hell meant releasing my body to anyone who would have me until I felt I've been forgiven.
That road to forgiveness would turn out to be a long time.
"Aw fuck yeah. Your ass swallows me right in!"
A voice cheered among a crowd of naked men circle jerking around me. I responded to the enthusiastic voice with my ass cheeks, squeezing them around his skinny cock that was pumping in and out of my asshole. Barely any preparation was done, so this motherfucker had me crying from the beginning.
Don was fun for a while, but because my father had a job opportunity in another state, we had to part ways and I transferred to a new college where I found the right people to treat me poorly.
"Don't take too long, yeah?" a guy in the corner told his buddy who was 6 inches deep, "I need a piece of that."
A piece of "that" as opposed to "him." The line between human and object had been long blurred. I have a cousin who gave me all the details about the fraternity, Alpha Kappa Phi, before I transferred. They used to have this ritual called, "The Cherry Ceremony" where they had to fuck somebody in order to be inducted into the club.