Shy Guy

I was online a few days ago, chatting away in the erotic chat rooms, when I got a PM from a young, bi-curious man. He was 21, living and working just an hour or so away from me. We started talking a little, and I proposed the idea that maybe we could meet up sometime. He agreed, and we started setting some things into motion.

We agreed to meet on a Friday night when my wife had gone out of town for a bridal shower. I was left to my own devices, and my own carnal desires. I invited the young guy over around 7:00 p.m. I gave him my cell phone and told him to call for directions when he got close.

Around 6:45 p.m., I got a call.

"Hello," I said, recognizing his number.

"Hi," his voice shook. I could tell he was nervous. "I'm on my way. I think I'm close."

I talked him the last few blocks to my place, and met him down at the parking lot in my apartment complex. As he shut off the car and fumbled around inside with his keys, I watched patiently. When he finally got out, I had a chance to peruse him with my eyes.

He was taller, about six feet high, probably about 180 pounds. His hair was blond, and it was cut short and styled. He wore a t-shirt and some basketball shorts, and he carried with him a brown paper bag.

"What's that?" I asked.

"Oh. I brought over some stuff. Some DVDs and magazines... porn." He swallowed a little bit. I looked down at his crotch and could see the small bulge of his dick pressing against his shorts.

"Come on inside," I motioned, leading him up to my place.

Once inside, he sat down on my couch and looked up at me. "You really are a nervous wreck, aren't you?" I smiled.

"Yeah," he said, "I'm sorry. This is my first time doing this."

"Well," I smiled coyly, "that's okay."

He sat there looking at me, and I shook my head slightly trying to figure out how I was going to get this guy's dick into my mouth, or finally get him to work up enough courage to let me fuck him. Finally, I said, "Why don't you start by telling me some of your fantasies. What are some of the things you've been thinking about?"

He swallowed, and started to speak hesitantly. "Well, I think of my office where I work. I sometimes have to work late to get caught up on filing and things. The place is a mess with boxes everywhere. I think of someone coming in and asking if they can help."

"Mmm hmm," I encouraged.

"The guy comes in, and as he's helping me put away boxes and files, he brushes up against me. At first I think it's a mistake, but then I feel him pressing something hard into my butt. I look back and realize that he's pressing his crotch against my butt."

"You can say ass," I said smoothly.

"Okay. He's pressing himself against my ass." I watched as his body trembled a little. Quietly, I lowered myself onto my knees in front of him and started to pull down his shorts and boxers, exposing his now fully erect cock.

"Oh God," he muttered.

"It's okay," I encouraged. "Just go on with the story."

"Well," he wet his mouth, "the guy reaches around and starts to rub his hands against my crotch. My I'm already hard—" At that, I lower my mouth onto his dick, and feel it throb as his body shakes and bucks a little. "Oh God!"

I moan into his dick, slowly sliding my tongue around his shaft to get it wet. I can feel it moving in my mouth, and I can tell he is trying to fuck me.

"Your cock tastes so good," I breathe, sucking on it.

"Oh yes," he moans. I looked up to see him leaning back, his hands gripping the couch cushions. "Tell me that you want it."

I smiled. He was getting even more excited, and his eyes were closed as he was playing out a fantasy in person. I licked the head of his dick slowly and said in a low voice, "I want your cock so bad."

He grunted, and I lowered my mouth onto his shaft. It was hard and thick, and I could smell the sweat of his crotch hair as I lowered my mouth to the base of his dick, swallowing him whole. "Mmm, suck my dick. That's it..." His hips were moving now, and he was pumping his dick into my mouth faster.

I moaned at his words, and lifted my mouth off him briefly to gasp, "Oh. Your dick is so hot, so hard. Mmm." I lowered my mouth back on it.

"Oh God," he trembled. "I'm so sensitive. I'm going to cum soon."

I moaned, making sucking noises along his cock.

"Do you want it?"

"Mmm hmm."

"Say that you want my cum."

"Please," I moaned, taking my mouth off his dick, breathing hot air across its rigid, wet skin, "please let me taste your cum. Shoot your hot load into my mouth."

He forced my head down on him, and he ground me along his shaft like a $20 ho. I even choked a little at the force of taking his whole length into my mouth, but I still sucked at him, sliding my tongue along the bottom of his shaft. Soon he was tensing, and he screamed out as he came, "Oh shit! I'm cumming!"

His load hit like a series of soft bullets against the roof of my mouth, my throat, and my tongue. He held me all the way onto him, and I did my best to swallow every drop of his load. He had a lot of cum, and it was hot and salty, viscous against my taste buds.

"Mmm," I sighed, finally freeing myself from his grip and lifting my head off his cock. "You came so much. I could barely take it all." I reached a hand forward to gently stroke his flaccid dick.

"Oh God, oh God," he panted.

"Don't tell me you're all done already." He looked down at me, trying to catch his breath. "Let's get your dick hard again so you can put that big monster of a cock inside me. I want to feel you in my ass." Again he moaned, and I watched as his dick twitched a little.

In encouragement, I grabbed the bag of porn he had brought, and walked over to pop in one of the DVD's into my DVD player. As it started playing, I took out my own cock to start stroking it, and caught him looking at it eagerly.

My dick was shorter, but it was thick in girth. I gripped it with my hot hand and started stroking it slowly. As I watched the scenes of the DVD, I could feel it tingle and respond, aching and throbbing in my hand. In just about 10 minutes, I was startled from my own masturbation when I heard him say, "I'm ready now."

"Good," I smiled, looking over at him. His dick was indeed rigid again, and I licked my lips as I felt my asshole tense, eagerly awaiting his cock. I quickly moved over to the couch where he was and crawled onto it after pulling off my pants and boxers, exposing my round ass for him. I motioned over my shoulder and said there was a bottle of lube there. He asked about condoms, and I said no. I told him I wanted to feel his semen seeping into my ass.

I heard him squirt a handful of lube into his palm, and heard it squishing as he rubbed it along his shaft. He must have put a ton of it on, not sure how much he would need. All the while, we were both getting turned on by the moans and screams of the DVD in the background.

"Line it up," I instructed as he stood behind me, holding his slippery dick in his hand. "Shove that thick cock inside of me." And I pushed my ass towards him.

He definitely had too much lube on, because his dick slipped a little as he tried to get it into my hole. Finally, though, after I could feel lube between my ass cheeks, he finally started to get the head inside. "Push hard!" I grunted, and he did. He pushed himself hard, and his dick popped inside. His dick was bigger than I had had in a while. It was long and thick, and it stretched me. I moaned at the feel of it, and started squeezing it and working it inside my ass.

He gasped and moaned, and I felt him place his lube covered hands on my ass as he started to fuck me. "Do you like that? Do you like having cock inside of you?"

"Mmm, yes," I moaned, grinding myself along him. "I love having a big, fat, hairy dick inside of me. Fuck me harder. Please. Please let me feel your balls slamming against me as you ram me inside."

He grunted and groaned, and he fucked me harder and deeper than before. I could feel him straining with the effort, and his feet were slipping a little once in a while on the carpet. Still, I let him fuck me, and moaned and groaned at the feel of his dick sliding in and out of my ass.

"Oh, oh, oh," I whimpered. "Fuck my ass. Fuck it hard."

"Yes... unn..."

"Oh God... you're tearing me apart. You fill me up with that big, hungry dick of yours."

He grunted, and I could feel him making harder, slower, heavier thrusts. He was panting now, and I knew he was working towards orgasm.

"I want to feel you cum inside me. I want to feel your hot load in my ass, feel it squirt inside me."

He groaned, and didn't stop slamming inside of me, even when his dick burst, and its small load exploded inside my ass. I tenderly milked his cock with my ass, squeezing him tight and then loosening up. Finally, he stopped, pulling his dick from inside me, and sat back down on the couch, exhausted.

"Mmmph," I breathed. "I can still feel your cum in my ass. It feels so good." I smiled as I looked over at him.

"Oh God. You're so good at turning me on."

"Well, don't get too comfortable yet. Now it's my turn."

He looked nervous again.

"Hey, don't expect to be able to just cum and go. You got off twice, I think I'm entitled to some release myself."

He looked sheepish and reluctant, and I knew he felt trapped.

"I'll go easy on you. Trust me, you'll like it."

He looked unsure, but he nodded silently.

"Get on your hands and knees on the floor," I ordered.

Quietly he complied. As he did, I moved to get on my knees behind him, and quickly yanked his shorts and boxers down. Now it was going to be my turn to use him.

I reached over and grabbed a little lube, swirling it over the head of my cock and the shaft. Then, gently, I lined my dick up with his hole and started to press the head inside.

He was tight. Really tight. He clearly was a virgin ass. I could hear him wince in pain as my head eased in, and I started to rock it gently back and forth, trying to loosen him up a little. His head was lowered, and he was panting as we were joined together on the floor, my dick sticking from his ass, hard and throbbing. It took probably about 15 minutes of slow, steady work with my cock before I was finally able to force it all the way inside. When I did, he gasped, and I felt his ass contract on my shaft. I held it there, letting him feel my girth.

"Now it's your turn to get fucked."

He moaned.

"I bet you've fantasized about this. I bet you've been waiting to get a hot dick shoved up your tight little ass. You want it, don't you?"

He moaned and whimpered, "Yes."

"You probably sit at home and stick your finger up your ass, wondering what it would be like to have a full dick ramming you raw, right?"

"Yes yes yes," he moaned, and now he was bucking against my crotch, urging me to move inside him.

"Well, now you're going to see what it's really like. I'm going to fuck you so hard you won't walk straight."

He groaned, and I leaned forward to grab his shoulders, driving my dick in and out of him hard. He moaned and whimpered, and despite loosening him up I knew it was causing him pain. I didn't care, though. I only cared about the tight skin of his anal pathway sliding along my dick, and the feel of precum dribbling from the slit of my head inside him.

I rammed him. I moaned and grunted and swore, feeling my body sweat from the effort of taking his virginity. He rocked against the floor, and I could tell he was gripping the carpet to keep from falling forward with the force of my thrusts.

"Are you ready for it, bitch?" I grunted.

"Yes," he moaned.

"Are you ready to take my hot load? Do you want to feel it shoot into your ass?"

"Yes yes yes! Please, oh God!"

That was all I needed, and I pushed and fucked his ass as hard and deep as I could. And when I came, my load burst forth like a river, shooting loads and loads of cum inside of him. I was surprised by how much I came, and I could feel it pool around the head of my dick even as it still squirted out, not able to go very far into his ass.

When I was done, I bucked feebly against him, grinding my cock in his ass. He was panting, and I could hear him breathing threw clenched teeth, wincing in pain. Finally I pulled out, and stood up victorious over his ass, watching some of my cum ooze out of his hole.

"There," I commented. "I popped your anal cherry. Now you're a dirty little cum whore ready for the fucking."

He whimpered, and I watched him reach back to feel some of the cum dripping out from inside him.

"Now get up and get out," I ordered.

He didn't resist. I could tell he enjoyed being dominated, just as he also enjoyed dominating me. He stood up, pulling his shorts and boxers back up, shifting uncomfortably as the cum continued to seep from his ass.

He looked at me.

"Go get cleaned up. Call me when you've showered and had time to sooth that ass of yours. I'm not done with you."

At that he moaned again, and turned and left my apartment.

I grinned as he left, smiling at my triumph, knowing that I had just secured a tight little ass for myself to use and abuse. I turned, watching the porn that was still playing, and sat down on the couch, stroking my wet, stinky cock as it grew hard again. In no time, I was bucking into my hand as I came again. Finally, after I was spent and exhausted, my dick finally limp, I climbed from the couch, turned off the DVD, and headed to shower. After all, in just a few hours, I'd be seeing my new sex toy again and I needed to be rested and prepared.