Waiting Outside The Lines - 22. Chapter 22

​ I was amazed when I looked down and saw the circumcised tip of my rock hard shaft actually slowly burying itself in Greyson's hole. I was fascinated by the sight of it. The ring of his entrance was gripping me soooo tightly...the sexy lips of his eager anal cavity, blushing the darkest shade of pink as his virgin pucker did all it could to tolerate the sensual penetration of his most intimate spot. I couldn't believe this was happening right now. I really couldn't! I could see the roundness of his upturned cheeks, and when I placed my hands on them...his body shook with a lustful urge that invited me to keep going. So...I did.

But slowly. Oh, so slowly.

I think I sank in another two inches, but stopped when Greyson's body tensed up a bit and I heard him gasp out loud from the pressure. "Are you ok?" I asked.

"Uh huh..." He nodded, breathlessly. "...Just...go slow. Ok?"

"M'kay." I whispered, and rested for a moment while he got used to me being lodged in his snug little tunnel. The strange thing is...even though Greyson's body was perfectly still, his insides were alive and quivering wildly with boyish excitement...his slick hole, softly sucking at my throbbing hardness from all angles as the intense warmth of his insides nearly caused me to break out in a light sweat.

"Yeah...ooohhh....omigod, this feels awesome..." He said softly. Really? Does he like me being so...ummm...ok, I'm thinking too much. Let me just be romantic, or whatever, about this. I've come so far. I don't want to ruin it now.

Greyson's hands reached back and touched the tops of my thighs. I guess it was to keep me from pushing in too deeply before he was ready for it. But it was a gentle touch...not a 'preventative' one. He wanted more of me...just a little bit at a time. I think I can handle that.

My mind flashed back to those naughty afternoons, watching Asa thrust himself into Chandler's hungry body in that off-set trailer...and I wondered if maybe Greyson was expecting me to do some of those same things to him in bed. I mean, as hot as it was to watch, I wasn't really one of those 'hair pulling', rough riding, boys that thrusts away with the intent of really giving it to Chandler and messing up the way he walks for the next few days. I mean, there's nothing wrong with that, I just...I don't know if I can pull off an act like that just yet. I've never been embedded so deeply in another boy before in my LIFE! I don't know if I want that to be my first instinct when it comes to sex with someone I really care about. You know? I love Greyson. I love him with all my heart. I just want to share something really special with him tonight. Something beautiful. And I'm in no hurry for it to end.

I felt Greyson push his butt back up against me, and another inch of my hardness sank even further into his depths. WOW! He was so hot inside. My legs began to shake from the pleasure I was feeling at that moment. I could only hope that I could balance myself through this experience, because I was already losing my equilibrium, big time.

I was just a little more than halfway into him now. I don't have that many inches to work with at my age, but...he was truly enjoying what I was giving him, and his little vocal cues told me that I was doing this right. I think. Whatever. He only wanted more.

So did I...

Gosh! The very 'squeeze' of him was intense! Greyson's body made me realize that the grip of my own fist over the past few years since I learned to stroke myself has been doing it all wrong! Why masturbate at all when there's a sexy release like THIS out there in the world? You know?

I was breathing so hard, but I hadn't even started humping him yet. Just...this was a whole new vibe for me. This was blowing my mind.

Ok, I'm doing this. I'm almost all the way in. I have a willing partner who's so damn cute that I could reach an orgasmic high off of his smile and a few kisses alone. We're together now. In bed. In his hotel room. This is what my life is now. I'm having actual SEX! I spent years thinking about it, but never felt ready for the real thing until this very moment. I just wanted to remember every last detail. I didn't want to miss a thing. No time to be shy about this, Evan. Just follow your heart, and let you body take control. What is it telling you? Let it guide you and tell your boner what to do. It'll be great.

It's ALREADY great!

God, I'm trembling so HARD right now! Hehehe! Greyson Chance...my lover. Holy shit! This is so CRAZY!

A little whimper escaped Greyson's pretty lips, and I was surprised to feel him push back a little bit further. The hands that were once placed on my thighs to set a boundary against my assault, were now gripping the flesh to pull me in further. I let him set the pace, but it wasn't easy. Already, I could feel my balls being drawn up tight between my legs...ready to fire away the moment this intimate coupling got to be too hot for me to handle any longer.

Then...suddenly I sank into him all the way. Almost as if he took the plunge and decided to surrender to my entire length at once. I think it was an unexpected leap forward for the both of us. We both released a high pitched moan as my baby soft pubes found themselves pressed tightly against Greyson's delicious cheeks. My hardness was lost in another world, and I could tell that Greyson was both thrilled and frightened about how good it felt to have me inside of him. There are moments in life when the sensations within are SO incredibly magic that it scares you. It leads to a loss of control that you're not used to, and it makes you wonder if you ever had any control at all before experiencing the bliss of being so helpless against your desires in that moment. I know how he feels. I was feeling it too.

I remember feeling his sexy inner muscle swirling around my shaft. Flex...and release. Flex...and release. I rubbed my hands on his back, and felt the gentle texture of teen goosebumps on his skin...an innocent response with a naughty flair that drove me crazy.

And then...I pulled an inch or two out of him. WHOAH! I had to stop moving immediately! I didn't think that I could get any more aroused. I didn't think that this could feel any better than it already did. But I was wrong.

As the ridge of my hardness began to withdraw from his fevered confines...my entire shaft became overwhelmed with a series of tingles that nearly made me want to fall right off of the bed. Especially once Greyson's constricted ring attempted to hold me inside. He was so sensitive. So responsive. The slightest movement from me set his inner biology ablaze, and we were both left SO breathless.

If sex is this good, and it exists in the world...how the hell does ANYBODY have time for anything else?

I almost felt the need to ask if he was ok again, but didn't. I wanted this to be...you know...hot. For both of us. I looked down to watch my erection as it pulled out just a little bit more. The skin was glistening with lube, and I could actually see Greyson's pucker moving slightly...suckling at my sensitive tip...waiting for more. So, I slowly pushed back into him. Ohhhhh God...if you thought pulling out of him was a mind-blowing sensation...pushing back into his warm, gelatin, mixture was majestic beyond description. Jesus...did he get even tighter? I could hear the air being pushed out of Greyson's lungs, and he slightly readjusted to raise his hips a bit more and spread his legs. His chest lowered even more to the mattress, the sensual dip in his back resembling the 'good morning' stretch of a lazy kitten as his body invited me to give him even more.

Another withdrawal...rhythmically followed by another gentle push. I repeated the motion, hoping that I didn't lose it too soon. Greyson was sooooo hard! I reached underneath, and the second I touched his excited shaft, it throbbed, swelled, and nearly jumped right out of my hand...angling itself tight against his belly. I could feel a warm dollop of nectar on the back of my thumb, and I knew that he was excited enough to be leaking his passionate seed down onto the sheets below.

I pushed into him again, and my hips actually began to take over for me. Now pumping almost involuntarily. I gradually picked up in speed. Not in an overly aggressive way...but it was clear that my bashful experimentation with the idea that I could claim to be any good at sex was melting away. Quickly being replaced with the serious thrill of, 'HOLY SHIT!!! I'M HAVING SEX!!!' Greyson and I were breathing as though we had run ten laps around the hotel, but never once felt winded or dizzy. His clutching sheathe held onto me as I looked down again and saw a sensual 'ripple' in his bottom as my groin made repeated impact tremors with his bubbled cheeks. This is AWESOME!

Greyson's intimate cries were as emotional and heartfelt as anything that I had ever heard from him on stage. I saw his hands clutch at the sheets, and he really got excited as I leaned forward to put my hands on either side of him and raise my hips even further off of the bed. Now pulling almost all the way out of him and pushing back into him with a vigor that pleasantly surprised us both.

"Omigod! Unh...yes!" Greyson panted beneath me, only encouraging me to take license and drive myself into him as though I was some kind of 'pro' at this butt sex thing.

The thing is...my arms tired pretty quickly. I was going to fake it and just...keep plugging away, but my arms were actually starting to shake now, and dip at the elbows. I wasn't really sure what to do, but once I slowed down the pace of my thrusting hips, Greyson took a moment to catch his breath...and I just moved in and out of his clenched muscle with a more measured rhythm. I guess Greyson's knees were getting a little bit tired as well, so we both had the simultaneous urge for him to lay down flat on the bed. Seriously, not a word was spoken between us! It was like...I leaned forward and rubbed my nose and lips softly on the back of his shoulder...and Greyson carefully lowered his hips to the mattress...my body molding to his so as not to lose our sensual penetration. I lay flat on his back, and he grinded his hard erection into the soft, sticky, sheets beneath him.

I wormed my arms under him to hug him around the chest, and Greyson wiggled with approval as I slid as deeply into hi as his pillow soft cheeks would allow.

Can I kiss him? I'm pretty sure that I can kiss him.

Thankful that my shaky arms weren't trying to support my body weight anymore, I placed my weight on Greyson's back and didn't get any protest. In fact, he only squirmed a bit beneath me to make sure that I could keep making love to him the way I was. He clearly didn't want me to stop. If anything, he was getting even more enthusiastic about being my bottom boy tonight. That is so much of a turn on that I'm afraid my brain would explode trying to describe it to you. As my hips began to side in and out of him again, I hugged my sweetheart tight, feeling the vibrations of his whimpers as my chest covered the length of his back. Ok...I can't stand this anymore! I'm going to kiss him! Let's see if this works!

I moved my head to the side, and first kissed Greyson on the side of the neck. Then on his cheek. His vocal cues got slightly higher in pitch, and his cute little mounds tightened up to squeeze my boner as the cutest smile spread out across his lips. He LIKES it!!! He likes my kisses! So I keep doing it. And even with his eyes closed, Greyson moans and cranes his neck back, reaching up to caress the side of my face to pull me in for a full blown French kiss on his sexy lips. Our tongues mingled, our breaths heavy, all while I'm still experiencing the most intense sensations of my life by the grip of his once virgin hole.

I wasn't sure that I could take much more of this. The sex part was hot as FUCK! But...Greyson's kiss? Oh wow. There was something in his kiss, a personal flair that revealed his true self to me in ways that even the most explosive sexual fantasy couldn't. The very taste of him drove me wild. The way that his lips molded to mine, his tongue moving in ways that expressed Greyson's personality perfectly...it was baffling. The way we kissed each other told our whole story. Of how we met, and how we flirted, and how we reached the point where I could be locked sooooo deeply inside him right now, ready to let loose at any moment. Greyson's kiss was sensual, passionate, and delivered with a confidence that let me know that he meant it with all his heart. And yet...there was still this 'purity' involved. Greyson's kiss never felt lewd or invasive. It was a gentleman's kiss. An angel's kiss. Just naughty enough to be sexually enthralling, but never crossing the line into feeling dirty or crass. It was the kiss of a boy that truly wanted you to know his true feelings about you, and who wanted to know your feelings in return. A symbiotic liplock that brought joy to your heart through its balance and understanding of who you are. I've never known anything like it.

The sex was the main event...but his craving tongue kiss was the catalyst that took me over the edge.

The feelings inside increased tenfold! I started by huffing and puffing so hard that I was hardly getting any oxygen in my lungs at all. My hips actually began to slam into Greyson's squeezing hole until the sounds of my lap smacking up against his soft white cheeks began to echo off of the walls of his hotel room. There was this extreme yearning for release that was building in my loins. It caused me to pump harder, thrust faster...a tightening was happening, and I licked Greyson's cheek as I knew that I was rapidly reaching the point of no return. Our lips disconnected, my frantic humping of my boyhood into his sexually humid embrace...and I began to let my voice express the impending orgasm to come.

Do I just...? I mean...can I just blow a load inside of him like this? I mean, we're boyfriends and all, but...this being our first time, I had to wonder, is that, like...rude? Should I warn him? Do I have enough time?

Ugh! No! Not enough time! Oh shit! Baby, I'm sorry!

I can't...I can't hold it...

Suddenly, my entire body locked itself up in a frozen position. My toes curled, my arms crushed Greyson's lithe body against mine, my hips were pushed as far forward as possible. The only thing moving was the almost painful thumping of my shaft as a torrent of orgasmic seed shot out of my expanded tip and flooded my boyfriend's insides. I gasped, kissing and licking the back of his neck, my hips still pushing into him as though the added thrust would make me cum even more forcefully than I already was.

Time stood still.

I kept splashing his insides with continuous ropes of overzealous boy nectar...and Greyson took it all. Purring beneath me as his beautiful body rested beneath me.

I didn't realize that I had been holding my breath until my erection stopped thrashing inside of him and the spams began to subside. I rested y head on the back of his shoulder, and we remained like that for a few minutes. Greyson still obsessed with the feeling of me lodged deep inside of him, and me still feeling the fragile aftershocks of a legendary virgin experience. Even as I began to soften a bit, the tender walls of Greyson's amazing ass worked to keep me at half mast. Almost as if they wanted more...now that his body knew what being penetrated was all about.

"Wow..." I whispered under my breath, too relaxed to move.

"Yeah..." Greyson whispered back. "...Wow."

"That was...that was really..."

"I know...right?" We both tried speaking while still catching our breath. But I noticed a subtle sigh of disappointment when Greyson felt me slide right out of him. "Awwww..."

"I'm sorry..." I said.

"For what?"

"I shouldn't have..." How do I say this to him? "I thought about warning you that I was gonna...you know..." I started. "But, while I was thinking about it, things kinda got out of control, so..."

Greyson giggled in the cutest way, and turned his head to kiss me on the lips. "I would have been SO upset if you pulled out of me at the last moment. Hehehe! Don't you ever do that to me."

Shocked, I asked, "Really? I mean, I didn't want you to think that I was being 'gross' or anything."

"No. Not at all. I thought it was hot." He said, moving a little bit as we rolled over to lay in the bed side by side. "I always wanted to know what it was like to have somebody do that to me."

"So...what's it like?" I asked.

"Ummm...slippery. Hehehe! But I kinda like it." He blushed. Then he moved closer to me to kiss me on the lips. "Wait...scoot over a bit more."

"I'm on the edge of the bed already..."

"I know, but...it's all cold and sticky over there." He grinned.

I looked over his shoulder and saw a huge wet spot on the sheets. He lightly grabbed me by the chin and said, "Don't look at it! Hehehe!" But it was hard not to at least take a glance at it. It was an actual puddle of Greyson Chance's cum...right here on our sheets! A dark spot mostly but I could see the white globs of it on the surface anyway. "Hehehe, quit it!" He said, kissing me on the lips.

"Sorry, I just...I didn't know that you...'did your thing'." I stammered.

"I came before you did. You felt...ummm...really good, Evan. I mean, hehehe, wow...I didn't even touch it. It just sort of...'happened'. You were so hot."

My eyes widened. "Whoah! Really?" Ugh! What a totally VIRGIN thing to say after sex! Dammit! "Ahem...yeah well...as long as it felt good. That was the...like, the 'plan'." I said, hoping he was willing to ignore my initial surprise.

Greyson laughed a little, then kissed me on the lips. We stared into each other's eyes for a few moments, smiling for little to no reason at all. Then he said, "This is cool."

"What is?" I asked.

"Just laying here with you. Being able to share some time with you. I like this."

"Me too."

We kissed again, and he snickered to himself. "I guess...well...I don't think we're virgin's anymore."

"Omigod, you're right." I giggled. "We're not, are we?"

"Nope." He said. "So...'this' is the story we're going to be telling people for the rest of our lives, huh? The time we lost our V-card in a hotel room with no apologies."

"No apologies at all." I said.

"Good." He smiled.

"GOOD!" I smiled back.

Then, he asked..."Can you get hard again?" He turned red, but said, "I kinda want more. So much more. Let's do it again. Hehehe!"

Can I get hard again?

I think I started getting hard again the second he asked me that question!

DAMN!!! Being a gay teenage boy is the shit! Don't you ever let anyone else tell you otherwise!

Woo hooooo!!!