Should Have Known Better Ch. 03

He pushed my head forward, still holding my waist, and I put my arm against the wall for balance.

"Don't move."

He stepped away and picked something up, stood behind me, and I gasped as I felt the cold drizzle of lubricant on my anus.

Something pushed against me. Not a finger, some kind of dildo. It felt too large to fit, and it widened as it pressed into me, and then it sort of slid in and stayed there. I felt uncomfortably full. This was... not hot. It was just gross: There was something in my ass.

"You've never used a plug like this before, have you? Don't let it fall out. Now stand up."

I stood up, and felt the plug move, clenched my cheeks to keep it inside me.

"Listen carefully, because I want you to do exactly as I say. Get dressed and go back to your dorm. Leave the plug in as you walk back. If it slips out, put it in again. You can take it out when you get there, but I want you to wear it for a half-hour tomorrow morning, and a half-hour tomorrow afternoon. No jerking off, no coming -- just put it in and stretch out that asshole for me. And I want you back here at ten tomorrow night."

"Why are you still here? And why are you still naked? Get dressed."

I bent over to pick up my pants, and the plug squirted out of my ass and hit the floor. I finally saw it: Purple, flanged at the bottom, and it didn't look as large as it had felt.

"Pick it up, whore."

I'd never been called a whore before. But here I was, lifting a purple butt-plug off the floor, slick and warm from my own asshole, knowing I'd have to cram it back in. I reached behind me and pushed, but it didn't seem to want to go in.

"You'll want to squat down a little."

I squatted, and pushed, and gasped as it went back in, pushing against my prostate, and feeling, this time, a little sexy. Then I got dressed, clenching carefully to keep it from falling out. He gave me a small tube of lubricant for the plug, and opened the door, slapping my ass as I left.

As I walked down the hall, it seemed like the dorm-mates I passed were giving me knowing looks, but I shrugged it off. I felt like I was walking funny, but I wasn't walking THAT funny, just a little slow. I was feeling guilty, and ashamed, and even though I'd wiped the come off my face I still felt sticky and obvious, but I was pretty sure I wasn't. I definitely needed another shower, though, at least so I could wash the butt-plug off: I couldn't wash it in the common sink, and risk being seen by the other people on the hall.

Halfway across campus, I started going up a flight of stairs and the plug came out, staying in my underwear. It was a relief to be able to walk properly, and I reached the top of the stairs before remembering Erik's instructions. I looked around furtively, then reached into my pants and crammed it back inside.

That's when it hit me: Erik wasn't even there to check. I was doing this because I wanted to, just like he said.

Back at the dorm, showered, with the plug hidden safely in my own sock drawer, I fell asleep faster than I'd expected.

The next day, my roommate had classes in the morning, and I didn't, so I had the room to myself. I made sure the door was locked, stripped and got out the plug. It didn't look so big. I sniffed it-- I'd washed it off well last night, so it didn't smell like shit. Still. It was dirty by definition. I rolled it around in my hand before realizing that what I wanted to do was put it in my mouth. I sucked on it, getting it wet with my saliva, remembering Erik's cock in my mouth.

Sitting on my bed, I rolled back a little and lifted my legs, I drizzled the toy with lube and rubbed some more on my asshole, fingering myself, getting hard, getting ready to fuck myself. Getting ready to break my promise not to masturbate all day. Which wouldn't normally be a huge promise-- I usually did it at least once a day, but there were plenty of days when I didn't, when I was too busy or just didn't feel horny. But here I was, with the room to myself all morning, an enormous erection, lubricant all over my hands and my cock and my asshole, somehow thinking I would manage to not jerk off.

I put the tip of the toy against my ass and pushed. It felt harder to get in this time, I guess because last night I'd already been stretched out and ready. Still, I pushed again and it went in. This time it felt good, and when it pressed against me the right way, it felt like it was pushing more pre-come out of my cock, which by now was positively drooling with it. I gave my cock a couple of experimental tugs, and the sensation was incredible, especially if I rocked myself forward, sitting on the base of the plug.

Erik's words echoed in my head: Don't come until I say. Get dressed.

So, I got dressed, holding the plug against my ass until I could put on pants and underwear. It was nine thirty. I had homework to do before my afternoon classes, and if I could focus on that, I could avoid jerking off and still wear the plug like I'd been ordered. Still, with my ass wet and full, and my cock hard and drooling, I knew that Erik had been right: I was going to beg him to fuck me.

After the allotted half-hour, I got undressed again, wrapped a towel around myself, and walked carefully to the bathroom to shower. I knew the hall would be empty, but it still felt like a huge risk: A barely concealed hardon and a sex toy in my ass, and I was walking down the hall in flip-flops and a towel carrying a bar of soap. Our bathrooms, like our dorms, were co-ed, and I wasn't sure whether I was more afraid of a girl seeing me, or a guy.

But like I said: I had known nobody would be in the hall: Everyone with morning classes was at them, and everyone with afternoon classes was asleep, and I had the bathroom to myself. The only surprise was how hard it was not to masturbate right there in the shower. In the afternoon, after classes, it was a little easier to avoid: My roommate was in, and there were people awake and about all over the place. I still managed to slip into the bathroom with the toy and the lube, slide it in, and keep it there for a half-hour, then wash it off surreptitiously in the sink.

As the hours ticked toward the time I was supposed to meet Erik I found I could barely sit still. Even my roommate noticed, and complained, that I kept getting up and pacing around the room. I apologized and left, thinking I would walk around campus. Of course, I wound up over at Lincoln Hall, about fifteen minutes early. I wandered into the common area, unsure whether I should be there early, unsure whether to wait there or go to his room, or what. You'd think I would have wanted to run away, or just not come back, but I didn't even consider it. I wasn't thinking really clearly at all, in fact. If I had tried to sort it all out my head would have exploded from the confusion: I'd thought I was straight until two days ago, and here I was, showing up at an upperclassman's dorm with a hardon and hoping I'd get fucked.

A girl I'd seen the night before was sitting outside, and she looked at me and smiled reassuringly.

"Aren't you Erik's new protege?" she asked.

Well, maybe that smile wasn't so reassuring. Was she staring at my crotch? Was my hardon that obvious?

"I ... I guess?" I said, blushing.

"Awww, and shy, too. Well, go on then, he's in his room."

Although I'd forgotten it the first night I saw Erik, I was suddenly reminded of the fact that secrets don't keep well in a dorm. Other people on my hall would play loud music when they were having sex, so people couldn't hear them, but everyone knew what they were up to. Erik hadn't put on any music.

Confused and embarrassed, but still aroused, I walked down the hall. Erik's room was only a couple doors past, and his door was open. He was sitting at his desk, wearing a pair of jeans, but no shoes or shirt. He got up as I came in and came to the door. "Hey, you're early! Do me a favor and take off your shoes before you come in?"

I knelt down and untied my shoes, and he stood close to me, closer than someone would normally stand to a guest, with his crotch right in front of my face. I didn't dare look up but I wondered if he was already hard like I was.

With my shoes off I stood up.

"And your pants, too," he said, softly.

I hesitated.

"I know you heard me."

I looked up and down the hall. Nobody there, but the common room was really close, and anyone could come in and see before I'd have time to hide.

"I said, strip. Now." He wasn't loud, but he wasn't exactly whispering either, and I was afraid that the girl who smirked at me earlier would be able to hear the whole thing clearly.

Red with shame and, yes, acutely aware of how turned on that shame made me, I shucked off my jeans as fast as I could, and he let me in.

Shutting the door behind us, he asked, quietly again, "So, did you do what I said?"

"Yes."

He stepped toward me, embracing me and smelling my neck and biting it gently, then grabbed my ass, pushing his crotch into mine. His fingers were searching insistently for my asshole, still slick from the afternoon session with the butt-plug. I couldn't move. He wiggled a finger inside easily, and I moaned quietly.

"Dirty boy! Are you ready to be my slut?"

Not quiet. There was no music on. I didn't have a choice, though. Because I was, and he knew it.

"Yes," I whispered.

"Say it."

"I'm ... I'm ready to be your slut."

"Louder."

"I want to be your slut."

"Good."

He motioned to his desk chair. "Sit down here and put your legs over the arms so I can see your ass. You're gonna love this."

I was terrified, but obeyed. He opened a drawer and rummaged around, pulling out a large bottle of lubricant, squeezing some onto my cock and letting it drip down my balls.

"Rub that in. Yeah, get it on your ass."

"Put your fingers in. Yeah, I want to see you finger your ass like it's a pussy. Get it good and wet. Two fingers at least. You think you're ready to be my whore? You better fuck your asshole like you mean it."

He slapped at my thighs, scolded me loudly. "Keep those thighs spread, I need to see that whore ass when you fuck it."

I did my best, curling my ass up towards him, spreading my legs. He put a little more lubricant on my hands.

"Three fingers, Jonas. That asshole's starving to be fucked and I want to see you do it."

"Don't stop," he said, going back to the drawer and withdrawing a dildo. An alarmingly large dildo, easily bigger than his own cock. He pressed it to my lips. "Suck it."

I sucked. He jammed it in and out of my mouth, just like he'd fucked my face before, for what seemed like several minutes. All the while I had three fingers in my asshole, sliding back and forth, my cock stiff and slick and brushing against my wrists. I tried to rub it but he slapped my hands away.

"Not till I say!"

When he stopped, he pulled it from my mouth and showed it to me.

"Think you can fit this in your ass?"

"No."

"You can, and you will. Now get up."
He set it on the floor, where it rested on its base, sticking up. "Get on your knees."

I knew where he meant me to be, and knelt over the rubber cock, staring at the crotch of Erik's pants in front of my face. The dildo was wet with my saliva and my ass was wet with lube, and the very tip fit into me, but it widened rapidly and I was sure I couldn't go further.

"It's too big!"

"Oh, your poor little slut asshole's too tight? Here, breathe this."

He held something under my nose, and I inhaled, and felt immediately dizzy.

And the dildo slid inside me. I gasped. I wasn't sure what was happening, except that Erik had finally taken out his cock and put it into my mouth, and I was filled and stretched from both ends, dizzy with the sheer sensation of it.

"Oh yeah. You like those poppers, little slut? You've got potential to be a real whore. I think you're ready and willing and eager. Do you wanna get fucked?"

I nodded and moaned assent.

"Do you want me to fuck you?"

I nodded and moaned again.

He pulled out of my mouth, held the small bottle under my nose again, letting me inhale deeply, then rubbed his cock on my face. He was naked now, too. I hadn't noticed him take off his pants. He hadn't been wearing any underwear.

"Lick my balls." I licked. I took one into my mouth and sucked. He seemed to like that, tugging at his cock, bouncing it against my forehead with his clenched fist.

He turned.

"Lick my ass."

I wasn't ready for that, but he put one leg up on the chair, twisted around, and pulled my head towards him. "A real whore rims a man, you bitch. Now lick me. Yeah."

I gave it a few tentative licks, and it wasn't so bad, and I loved the way he moaned. The scent of poppers and sweat and lubricant and his balls became intoxicating and I licked his dark anus, feeling it twitch beneath my tongue.

When my face and his ass were glazed with my saliva, he stopped and helped me up. The dildo slid out of me and hit the floor with a damp thud. My asshole burned and gaped, and yet I wanted him to fuck me. I was still dizzy from the poppers he'd given me, and he held my arm as I went over to the bed, and then laid me down on my back.

I watched as though I were dreaming as he took his pants the rest of the way off, knelt on the bed near my feet. I started to lift my legs, but he pulled them back down and crouched over my own crotch, rubbing against it. And then I was inside him. This, I had not expected. I was ... well, confused wasn't strong enough a word, and probably too clear. I loved it, but I was surprised, and I wasn't sure what was going on, but I knew that Erik was on top of me, enveloping my cock with his asshole, definitely fucking me, totally in control. I didn't last long, but I'm sure I moaned loudly enough for the whole hall to hear.

And then he was crawling up toward the head of the bed, bringing his balls and asshole towards my face. "Lick me," he commanded. "Lick me again, and suck your come out of my asshole."

Disgusting. Maybe I'd have liked it if I was in that weird fog of being about to come, but since I'd already shot my load, I was horrified. But he was on top of me, and I could see his asshole stretched from my cock, my semen dripping from it slowly. He rubbed against my face, and I held out my tongue, and he pumped away at his cock, mashing his balls against my nose. It wasn't comfortable, and it wasn't a turn-on, but I couldn't resist, borne along on his lust and will to control me.

"That's good. You're a good little ass-licker aren't you. You love that come, don't you."
I couldn't respond with anything but a grunt.

He stroked my flaccid, lube-soaked cock and it stiffened a little, despite me.

"I'm gonna come all over your pretty little face."

He did, and then crawled off of me, looking down at my red, come-spattered face.

"You like that, whore?"

"Yes," I answered, honestly.

"Good."

He gave me a towel and I wiped off my face, and then he asked me the most confusing question.

"You wanna go to a party?"
"Tonight?"

"Yeah. Buddy of mine is having a thing. I can bring a guest."

I hesitated. "As, like... your date?"

"Whatever you want. We can just go to a party. I think you'll like it."

I didn't say anything, but when he handed me my pants, I put them on, followed him out, passing the girl smirking in the common room with her laptop.

The party was at one of the not-quite-frats just off campus, where a bunch of unaffiliated students lived. Erik got us both beers, and the guys all seemed glad to see him and to meet me. He introduced me as "his buddy Jonas," and although I got a couple of knowing looks it seemed like the most normal thing in the world by now. I was ... I guess I was Erik's new protege. It was mostly guys, but there were some girls there too.

By midnight the crowd had thinned out a little, and I'd had a couple of drinks, just a little buzzed. Erik pulled me off to one side and said "hey, let's go to the basement." I followed him down a set of stairs to a low-ceilinged room with a ratty couch and a steamer trunk set up as a coffee table. He kissed me. I know it sounds strange but this was the first time he'd kissed me. The first time I'd kissed a boy. Even though we'd already fucked.

At first I was afraid that someone else would come in, and we could definitely hear everyone upstairs walking back and forth. There was absolutely no insulation. But Erik seemed sexually ravenous, and I was swept up in it, doing whatever he wanted, pulling out my cock for him, sitting on the coffee table while he stood up and fed me his cock. I tried to stop when I heard feet coming down the stairs, but he held my head and kept fucking my face.

A voice I didn't recognize. "Allright! We got a show!"

Erik responded. "Yeah, bro. You want a turn?"

"Hell yes."

I couldn't do anything but make a few noises of alarm before Erik thrust again into my mouth, hard. "Jonas here will do what I tell him. Won't you Jonas? Because you're a cocksucking slut and you need more dick."

The new guy sat down on the couch and undid his belt, pulling out an uncircumcised penis that curved slightly to one side. He slid his hand back and forth on it a little and then said "Come here, Jonas. Let's give you some of what you need."

I started to stand up, but Erik held me by the shoulder and guided me to my hands and knees. "Crawl. Get down on your hands and knees and go worship my friend's cock there."

I did what I was told. I'd never seen an uncut dick before, not in person, not this close. Not erect. Definitely not in my mouth. The smell of it wasn't bad, but a little stronger than Erik's. He moaned as I put him in my mouth, holding his cock by the base to keep it from gagging.

The come tasted just about the same, though, dripping out of my mouth and onto the floor. I sucked what I could off his cock, my own erection brushing pre-come onto his pants leg.

"Jesus, dude, this guy really is dying for it, isn't he? You gonna let him come?"

"Not yet. I want to save it."

"I got some Viagra if you want."
"Well, I still want to make him wait, but I'll take one. Hell, give him one too."

This was rapidly getting out of hand. Two guys were deciding when I was going to be allowed to come, and what drugs I was about to take?

The stranger buttoned his pants and headed back upstairs. I stood up, and started to put my penis back into my pants.

"What the fuck, Erik?"

"Do you not like that? Don't tell me you don't like it. I can see how hard you are."

He stepped toward me, hooked my pants gently by the waistband, and pulled me close.

"Yeah."

"So, are you going to do what I say?"

"Yeah."

He unbuttoned my pants, letting them slide down, and rubbed my asshole with his left hand while pressing softly against my cock.

"And when my friend comes back downstairs with the Viagra and the poppers, you're going to do what he says too."

"Yeah."

"You don't even know his name, do you?"

"No."

"How does that make you feel?"
"Bad."

I meant good. Or, naughty. Or, ashamed and also turned on. I was having an increasingly hard time thinking because Erik's finger was tickling just inside my asshole, thinking of pushing its way in.

"Like a slut?"
"Yeah."

"Well, it's Steve. Now let's get those clothes off."

When Steve came back, I was sucking Erik's cock again, like before, but this time totally naked. I did what they said: Swallow the Viagra and the beer, then get on my hands and knees on the couch. Both of them kept their clothes on, just unbuttoning their pants. Steve rubbed his hands along my sides, rubbed lube into my asshole. I'd never been so hard in my life, and I don't think the Viagra had kicked in yet at all either.

"He's never been fucked before."

"Really?"

"Yep."

"Well, you've got dibs on that, then."