A Learning Experience Ch. 02

I checked on my girlfriend one more time- she was sound asleep. Her shift at the bar wiped her out, she didn't even get up after our quickie.

She laid there with her ass up, her cheeks red from where I thrusted against her.

My cock straightened, more due to the thought of where I was about to go than the site of her freshly fucked pussy.

I gently closed the door to my apartment and tiptoed down the stairs. My cock stretched my shorts out in front of me. Two girls coming home from the bar walked past me, and before I could cover it they saw my bulge and giggled.

I put my head down and ran across the street. My face was flush and my heard pounded in my chest. Only three hours ago I had only thought of touching a cock, now here I was going back for round two.

This guy, I didn't even know his name, got me to do things I never thought I would. The nerve, shoving my mouth down to his ass to lick his dirty hole, and holding my head while he used my mouth to catch shot after shot of his load.

Now here I was, with his cum still warm in my belly and the stench of his ass crack spread across my face, heading back.

I pushed my cock down, trying not to make it so obvious, by my gym shorts didn't stand a chance. It stuck out for all to see.

I told myself I was only going back because he had pictures. Those pictures could wreck everything. He threatened to show my girlfriend. He was blackmailing me, I didn't want to do this, I wasn't a cum craver.

I tried to convince myself, but my erection gave it away. I wanted to do this again. He didn't need to blackmail me, but that made it even dirtier.

I reached his door and pushed it open, just as I did only hours ago. I had gone in curious, and had come out a different person. What was in store for me this time?

I crept in and whispered "hello?"

"You're awfully shy for someone who stuck his tongue up my ass hole," he laughed.

I cringed a bit. Hearing myself described like that would take some getting used to. This guy had used my face, humiliated me, and now he gloated.

But he had pictures, I had to comply. Again, I tried to convince myself that's why I was doing this. It couldn't be that I wanted to, right?

I walked halfway across the room and he stopped me. "Hold it. Take your clothes off."

I paused, still looking at the floor to avoid eye contact.

"Now."

"Why?" It was an honest question, I thought I would be blowing him again and leaving.

"Because I told you to. Unless you want me to show your girlfriend why your tongue tasted funny last night."

Again I felt a sting, but he was right. I lapped up his ass hold and wanted more, I couldn't take that back.

"OK." I said as I pulled of my shirt. I looked down, my cock straightened even more and felt like it was going to rip through its skin.

I pulled down my shorts. The waistband pulled down my head before releasing it to spring back up.

"Turn around."

I did so without protest.

"Hands against the wall, and push out that ass."

I reached for the wall, and arched my back. He didn't say anything as he stared at my ass and stroked his cock. This was more humiliating than having my face held in his ass cheeks. I had nowhere to hide, no privacy, just my ass sticking out for a stranger to gawk at.

"Pull apart your cheeks."

"I...don't want... why? What does this have to do with giving you head?"

"Shut up and do it."

I reached back and pulled my ass open. I could actually feel a draft, my ass had never been this exposed. My sphincter tightened, then relaxed a bit. What was this guy doing? He was just staring at me, pulling on his dick. Maybe I would get off easy and he would just jerk off and send me on my way.

"Wait, didn't I tell you to bring a pair of your girlfriend's panties?"

"Yes, they are in my pocket."

"Give them to me."

I handed them to him, and he spread out the crotch. He brought them to his face and took a deep breath. "mmmm, nice. She wear these at work?"

This guy was sniffing my girlfriend's pussy. I'm not the violent type, but I get jealous when guys check her out, now he was comment on her cunt's scent. My head bowed slightly in shame. "Yes."

"I can tell, she must sweat, it's nice and ripe." He took another deep breath, then handed them to me. "Put them on."

I didn't bother to argue, he would just bring up the pictures. I pulled them on, and the thong split my ass cheeks. It felt weird, like I had a wedgie. The front failed to hold back my cock and sock, which stuck out from all sides.

"Skimpy little underwear, huh? She a dirty girl? She looks like she could be, I bet she is a great fuck."

Again, the comment stung a bit. I guy was talking about fucking my girlfriend while I stood in front of him wearing panties. How had this happened?

He was right though. My girlfriend was a bit wild, and had a sexual history that made me jealous. I know she sucked off a few guys in her neighborhood in high school. They would have her over after school, and at least two but up to six guys would be down there and she would blow them all. And she had had threesomes, including girl only. She also liked anal, which I wasn't big into. To be honest, it kind of bothered me that she liked it. It didn't like the idea of my girlfriend being dirty. How weird is that? I had a girl willing to do anything, and I wanted her to be boring.

She was just more sexually adventurous than me. Until about three hours ago, that is. Now, that doesn't mean I was bad in bad. In fact I know she had told all her friends how good I was. My cock was a good size, and I liked to pound. Maybe I was a bit vanilla, but I could throw some dick.

"You just fucked her, right?" he asked.

"Yes."

He leaned forward on his couch and grabbed my cock.

"Wait!" I yelled as I jumped back.

"What is your problem?" he demanded.

"I've never had a guy touch my cock before, I didn't think you wanted..."

"I couldn't care less about your cock. I want to taste her pussy. Now get back here, unless.."

"Yeah I get it, the pictures." I said as I moved closer.

"You're catching on."

He pulled out my cock and wrapped his lips around it. I could hear him moan as he lowered his face down my shaft.

"Oh god," I whispered. I was already so horny I almost came as soon as he took my dick in his mouth.

He slid his lips back along my shaft and over my head. He released my cock and sat back.

"Mmm, she's tasty. We'll have to share her some time." He spread his legs and grabbed his hard cock. "That's the last time we'll be using your dick today, get on your knees and suck me."

I hesitated a moment, though I mouth watered as I stared at his crotch. I also thought about what he had said, and I was fine with it. I wasn't here to get off, I didn't want to be touched. I wanted to take care of him.

"Don't test me. Do your job."

I dropped to me knees, grabbed his shaft and opened wide. His thick cock filled my mouth for the second time that night.

I lost myself in what I was doing again. I resisted at first, but I knew what was going to happen, and mostly wanted it. He flipped over, spread his ass and scolded me, "What are you waiting for. Lick that ass hole you slut."

I blamed the pictures again- I had no choice right? The first time I did this it was dark, and he was on his back. I never saw his hole. Now he was on his knees, face down, with his ass cheeks pulled far apart.

As clear as my own hand in front of me, there it was. It was a tight hole, darker than the skin around it. He flexed it a few times, seeing it move made it even more real. This was a man's ass hole in front of me, and I was going to lick it. Again.

I lowered my head and stuck out my tongue. I flicked it a few times as he squirmed.

"Oh my god that's good. Get your face in there you pig."

I lowered my face, with his cheeks pulled apart there was nothing to hold me back. I cupped his hole with my lips, and danced around it with my tongue.

I grabbed his dick and stroked. Oh my god, I'm giving a rusty trombone! I am such a fucking whore! I smiled a bit, but that pulled my lip away from his hole for moment.

"Put your lips back!' he demanded.

"mmmh," I agreed, but it came out muffled.

I stuck my tongue in and out, up and down and all over his hole. I lapped at it and poked it, every move drawing a moan.

After a while he pulled away and turned around.

"You really are a slut. A talented slut."

I again avoided eye contact as he looked me over. His cock bobbed as he stood next to me.

"Did you bring that lube like I told you to?"

"Yes, it's in my shorts."

I covered my cock as I walked away, as if that modesty meant anything now.

"Oooh, nice. I like this stuff. Put it on the couch, he said."

He positioned himself on the edge of the cushion and told me to kneel in front of him.

I did, but he stayed sitting up. The angle made it hard to suck his cock, it was easier when he laid back. He must not want head now, I thought. "Is the lube to jerk you off?" I asked. I wasn't being innocent, I actually thought that. I liked to use lube myself, and I assumed that is what he wanted. I had no idea he might want something else. I guess I'm naïve.

"Ha, you're funny. You actually think I brought you over here for a hand job?"

Before I could say anything he pushed my head down. He leaned back slightly, and kept pushing me until his head was in my throat.

I licked his tip, but I couldn't move my mouth. He leaned forward, and my head was stuck between his crotch and his stomach. What is he doing?

I heard the cap of the lube bottle click, then he put it back on the couch. He leaned even further forward, his torso pushing my head further onto his cock as he reached.

If my head wasn't stuck it would have leapt off his cock so I could find my clothes and run across the street. His finger, covered in the frigid lube, was suddenly pressed against my ass hole.

"Mmmphh," I protested, but his dick smothered my words.

He rubbed his finger up and down, and pulled my ass cheek over with his opposite hand.

I squirmed and wiggled, but just like when he made me lick his ass and take the surprise load in my mouth, my head was stuck and there was nothing I could do.

"Ohh yeah, look at that as wiggle. No one has ever played with your ass before? Not even that freak girlfriend of yours?"

I shook my head no and again tried to pull back, but it was useless.

His finger stocked rubbing and pressed against my hole. Oh nooo, I thought. I could feel the pressure building, then the tip of his finger pushed in up to his first knuckle.

It didn't hurt, it just felt weird. I had never wanted ass play. My girlfriend had tried once and I jumped off the couch.

He pulled it out and smacked my ass. "I don't want to spoil the surprise."

I was confused what he meant, but in one quick motion he leaned back, spun around me, and shoved me forward onto the couch.

I caught my breath, and turned back to him as put his hand on the back of my shoulders to hold me down.

"What are you doing?" I begged.

"What do you think?" He took a hand away and I again heard the lube bottle click open. At this point the naivety was gone. I knew he was spreading lube over that throbbing cock.

"I'm not into this, let me just suck you off, OK?"

"Again? I've already come in your mouth, slut. What else can you do?"

"Nothing man, come on, this isn't fair."

"Fine, when your girlfriend moves out after telling all of your friends that she saw a picture of you with your tongue up my ass hole, maybe I'll help you move. Maybe I'll invite her here and fuck her, then send you pictures to jerk off to."

"Fuck you!"

"No, fuck you," he said as his body fell on mine.

My faced pressed into the couch as his chest pinned me down. His hand slide down to my ass and his finger again probed my hold.

"Trust me, you're going to want to relax," he whispered. Then he lowered his voice even more, "this is hot, if you're really not into it, let me know, otherwise I'll keep going."

I stayed silent. Maybe I was in too much shock to speak, maybe I was curious. I honestly don't know. I just kept quiet, and let him take charge. I had realized that about myself- I like to be used.

He pulled his finger out, and my hole closed in relief. Then, my eyes widened in terror. I felt pressure on my virgin ass hole as he pushed his cock head against it.

The pressure grew, and I grabbed the cushions, "Uhhhhh," was the only sound I could make as the pressure became intense.

He lifted his chest off of me and held himself up with his arms. He pushed his pelvis into me again, and I squirmed forward.

"Get back here," he said as he grabbed my shoulders. With one more thrust he opened my hole.

The pressure was replaced with shear pain. I yelped and squirmed but he held me down. My hole burned, torn open by his thick cock.

It was much worse than I thought. I remember the first time I did it with my girlfriend it went in pretty easy and I fucked her good. How did she do that? She must have had more experience than I thought.

What a strange thought to have now. Who was I to think of her as a slut while this guy had his dick in my ass? Maybe I was just jealous of her, I should have experimented long ago. Things would change now, I was going to treat her like this guy treated me.

He pushed forward a little and the pain grew even more.

"There we go, the outside sphincter is the easy one, the inside one is sensitive."

He thrust one more time and ripped through my inner ring. My eyes watered in pain and I clawed at the cushions.

"Smooth sailing now," he laughed.

He pushed in further, but the pain didn't get worse. It eased a little, though I still barely handled it. He was right, it got easier. Once the head was in, the hole wasn't opened any wider. His length wasn't an issue. He went deep, and pushed deeper.

I could feel his pelvis against my ass, then his sack against mine. As he pushed the last inch, I felt a different pain deep inside me. This guy was all the way in.

He leaned down and whispered, "Tell me where my cock is."

"In.. It's...uhhhh... it's in my ass," I managed.

"That's right. Your ass is mine now." He kept his cock all the way in and moaned. "You'll get better, and be able to take it like that sexy little girlfriend of yours."

I winced as he pulled back, then thrust forward again. Now I was getting fucked. This guy, who I had just met a few hours ago- and still didn't know his name- was completely using me. He came in my mouth, made me lick his sack and stick my tongue in my ass, and now he was fucking me. A man was fucking my like a little bitch.

And I mean really fucking me.

He thrust back and forth. The pain was now more of a burning, I guess my sphincter had given up fighting back and relaxed. It was still weird, but OK.

I could hear slapping as he picked up the pace. His hips slammed into my house as his cock destroyed my taboo hole. I was now a man who took it in the ass, whether I did it again or not there was no going back to being a virgin. And I started to like it.

He picked up the pace even more, he was fucking me like I would fuck my girlfriend's pussy. I had relaxed to the point where this guy could do whatever he wanted. I was broken in.

He grunted and fucked even faster, I whimpered and moaned in both pleasure and pain.

I could tell he was going to cum. I didn't bother to protest, he was going to do what he wanted anyway.

I cried out as he gave a last hard thrust and let go. I could feel the warm load filling my butt. It felt so strange, but awesome. My sphincter screamed again and again as he as already thick cock pulsed even wider.

He poured load after load as deep into me as it would go, then collapsed onto me.

I could feel his dick twitch inside me, then start to soften. I welcomed the relief as my ass hole went back to normal. But it felt strange when he pulled out. I felt- empty. Despite the pain and violation, it's seemed like my ass was disappointed not to have a cock in it.

A stream of cum followed his cock, and dripped onto my sack. I lay there as he disappeared into the bathroom. I didn't move for a few moments as my body and mind recovered.

I reached back and wiped my hand across my ass. It came back glistening with a mixture of sweat, lube and cum. I reached down for my sack and wiped off his juice. I put my hand to my mouth, and licked it off.

"Can't get enough, huh?" he asked as I scooped a load of his cum from my freshly fucked hole.

"Well you have pictures, I have no choice, right," I laughed.

"That's right. Now clean me off."

He held out his soft dick, which he had not yet wiped.

My stomach tightened for a bit. It was one thing to lick his ass, but that cock was just deep inside mine. And I mean deep. Wasn't it dirty down there? I had heard that porn stars clean themselves out, and don't eat certain foods, before taking it in the ass. I made no such preparations as this night came as a complete shock.

I hope there isn't any..

He broke my train of thought by shoving his cock against my mouth. He pushed hard and it squeezed between my lips.

What the hell, I thought. Am I going to pretend to have some dignity now? I leaned forward, and licked him spotless. Clean or not, this guys did belonged in my mouth whenever he wanted.

I climbed the stairs to my apartment as dawn started to break through the windows. The climb was slow, my legs were wobbly and my ass hole felt like someone held a lighter up to it.

I gently opened the door and bee lined for the bathroom. He didn't let me use his to wash up, he liked the idea of me walking across the street squeezing my loosened ass hole so cum didn't leak out.

He watched when I crossed. I saw an older person heading off to work and managed a smile as I struggled to keep my hole closed.

He knows, I thought. I was walked like I had a wedgie, and I was visibly hard again. The old man just smiled back.

I turned back to my neighbor's window and laughed, then waddled up the stairs.

"Honey?" my girlfriend called out.

"I'll be there in a minute," I said as gave one last wipe and flicked off the lights.

I didn't wash my mouth or face, as he instructed, before climbing into bed.

I gave her a long kiss, and she gave me the same look as last time, trying to figure out what those new tastes and scents were.

"Oh my god, you're so hard!" She gasped as she reached into my shorts.

"Thinking of you, dear," I answered.

"Don't think of me, fuck me," she demanded.

I happily complied, tearing off my shorts and sticking my throbbing cock into her already wet pussy.

I flipped her over into the doggie position. She liked to hold her ass high in the air when getting fucked from behind. I had a nice view of her ass hole. It stared up at me, winking.

I thought of my neighbor as I pounded her. My ass cheeks flexed with each thrust as the last drops of his cum dripped from my sore hole.

What a night.