Aspiring to be Ass-fucked Ch. 01

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I really want to get ass-fucked. I've been training all year. Very few people have concrete goals in life and if they do, they're always lofty. People tell me about their dream job, their dream house, but no one ever tells you about their dream fuck. On all fours, ass in the air, panties on the ground and 175 lbs of man meat behind me. I don't really look it though, like I want desperately to be ass-fucked. I'm no more than 110 pounds on a rainy day and I'm only 20. But that's exactly why I want some guy using me like a rubber doll. I want him to fill me with his cock and then his cum. Why not a regular fuck? Well there's the funny part, I'm sort of a guy. At least, I have a penis. I was born with it but managed to grow tits too. Stranger things have come out of my mom's vagina. It was never really an issue though, people rarely saw it and I rarely mentioned it. It's been inconvenient at times though. It's one thing to get a guy to a point where he feels comfortable enough with you to want to bang, it's another thing to start getting down and dirty and stop to tell him that you have a cock, and then tell him you want it up the ass, pretty please. It's just a little weird. I've got this theory that there's a golden time to spring it on a guy. Sometime between, "Hello, my name is Holly, I have a cock" and, "Before you fuck me silly I just thought I'd mention I have a cock". It's still a work and progress though.

I've gone out with some girls too, but they're not as exciting to me. Most of the girls I've been with were actually excited that I had a cock, but wanted me to fuck them. I did it, of course, but I want to be on the other side. I want to be some guys pet that he keeps on a leash and shows off to his disgusting (but well-endowed) friends. I want to be that slutty french maid that bends down to clean and can't stand back up because her master is choking her out and his cock is in her ass. I'm not sure any of that shit actually happens outside of porn but I'll gladly be the first to find out. Like I said, I've been training.

My obsession started a littler over a year ago. My roommate, Michelle and I were had some down time and got chatting. She was hot but we'd never hooked up, she still didn't know I had a cock. Of course I'd seen her naked, she had the cutest belly and tits that she liked to call petite. She always told me how jealous she was of my comparatively large boobs. She seemed particularly nervous that day.

"Hey, Holly."

"Hey, Michelle. What's up?"

"You've had sex, right?"

The question surprised me.

"A couple times, yeah."

"Did you ever...did you ever let him put it in your ass?" She asked quite innocently.

That really caught me off guard. I'd thought about it, but since I lost my virginity when I was 16 I'd never been penetrated, I'd barely thought about it as an option. All the guys I ever dated were twinks who liked being pushed around and fucked. I finally responded,

"No, did your boyfriend want to..."

"Yeah." Michelle nodded. "Do you think I should? I'm a little scared."

"Chris is a sweetheart, I'm sure he doesn't want to do anything that would make you uncomfortable. Honestly though, it sounds kind of hot and I'm sure if you're careful you'll have nothing to worry about."

"That makes sense, I'm just worried. Is my pussy not enough for him?"

"Michelle, if that wasn't enough he'd break up with you. I think he just wants to try and have some fun. When are you seeing him next?"

"We're studying in a bit actually."

"No, I mean when are you seeing him next?"

"Oh, haha, he said his dorm is clear for the night so probably then." She looked at the clock on the wall. "In fact he should be here any minute. I'll think about what you said, Holly."

"Have fun! And remember, you have the power to choose what happens to your body."

"Are we in an after-school special all of a sudden?"

Just then there was a knock on the door.

"Michelle, you ready to go study?" I could hear the dumb smile on his face. That smile that anyone could read as 'I'm getting laid tonight'.

Michelle left and I was alone in the dorm. I couldn't get the idea out of my head. I could just picture Michelle bent over a table getting plowed by Chris's huge cock. I should say I've never actually seen Chris but you know what they say about a man with big feet. All at once I felt my penis getting harder, pushing tightly against my panties and leggings.

I quickly began to undress. First liberating my cock from its tight quarters, and then taking off my shirt and bra to let my tits hang free. I started rubbing my cock, thinking about Chris's and a thought came to my mind. I started gently moving my middle finger around my asshole. I started stroking faster and I wanted to penetrate myself but my ass wouldn't let me. Finally it went in and I nearly screamed. I didn't dare take it out though, and risk undoing my hard work. I started moving it around, enjoying the sensation of having something in a hole that was normally reserved for waste. Before I knew it I was covered in cum. Cum, there was another thing I would have to try.

I decided I'd been adventurous enough for one day though. I laid for a minute breathing heavy, cum still on my belly and my finger still up my ass. I took my finger out and laid for another minute trying to catch my breath. I felt hot, I felt like I was on fire, I felt like doing it again but I couldn't muster the energy. Eventually I got up, wiped the cum away with a tissue, washed my hands and took a long shower. As the water poured down my naked body I thought, "goddamn, I have to do that again."

From then on there was a steady progression. I went out and I bought myself anything I could think of to stimulate my ass. I bought a six-pack of but plugs, big black dildo, vibrating anal beads, and most importantly, enough anal lube to last a lifetime. At first I was only inserting objects while I masturbated but for some reason the thought of a gaping asshole turned me on immensely. From then on I would start keeping butt plugs in my ass for long stretches of time. I started out with the smaller ones but but 2 months in and I had the biggest butt plug in the set up my ass all the time. Nothing turned me on more than walking through the streets or sitting a class knowing there was a sex toy lodged up my ass the whole time. Well, nothing except the thought of actually getting assfucked by a real human cock. He would cum in my ass and pull out and it would just drip away. Needless to say, I found it difficult to hide my now frequent erections.

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Stay tuned for Chapter 2. Thanks for reading. I'd love to hear feedback.