“Bailey? Are you asleep yet?” Came his ritual whisper in the dark. This was the third night in a row that David had asked me that question after we had already gone to bed. He always waits a few minutes in silence, then he asks me that same question over and over. I couldn’t understand why the hell he kept doing that. Doesn’t he EVER just…go to sleep like normal people?
“No. Not yet.” I whispered back. “How come?”
He says, “No reason. You just…you got quiet, and I thought…” Then he’s like, “Nevermind. Just wondering. That’s all.” His voice trailed off into a whisper, and I didn’t think much more of it once he rolled over to turn his back to me in the bed. We were both a bit sleepy, and his bed was big enough to give the both of us more than enough room to be comfortable, side by side, but I wasn’t going to be able to drift off any time soon with him constantly asking me if I was asleep yet. Who does that? Honestly?
See…my parents were taking an extended trip to Las Vegas for their anniversary, starting the weekend just before the end of our Summer break from school, and while their original plan was to leave me with my grandparents, I practically begged them on my hands and knees to let me stay with my best friend, David, instead. That would be SO much more fun!
My grandparents go to bed at, like…sunset. Like a couple of reverse vampires. It’s weird.
My mom said, “I don’t know if we can guarantee you that, Bailey. What about David’s parents? Did you ask them first? We don’t feel comfortable just dropping you off on somebody else’s doorstep for the week without asking them first. Maybe next time, ok?” But I was persistent in pleading my case. I kept grinding on my parents’ nerves and wearing their will power down to its weakest point on a daily basis, making sure that David was doing the same thing with his parents too. Working together, how could they possibly say no? We were just determined to make this happen. Heck, David was even more eager to make this a reality than I was. We’ve been best friends since we were ten, and now, over three or four years later, we were more inseparable than ever. It’s not like we’ve never had sleepovers before. We’ve had tons of them. But this one seemed special for some reason. I don’t know…it was just a bigger adventure, you know? It felt different somehow. We were both only children, so it would be like having a twin brother or something in the same house.
How awesome would that be???
David and I probably spent ninety percent of our time together giving each other shit and giggling until our bellies hurt. Hehehe, and the other ten percent of the time? We spent competing with one another in one way or another. Mostly by wrestling on his bedroom floor, trying to better one another with whatever burst of testosterone fueled strength that we could muster at the time. Sometimes I won, ometimes David won. I’d be willing to guess that we were both pretty evenly matched in that regard. I think David was stronger than me in a lot of ways, but I had better stamina. So, while he was going all out in the first few minutes of us rolling around and getting all hot and sweaty…he’d get weary eventually, and I’d be able to overtake him in the long run, as long as I kept my edge long enough for him to tire out. It was fun, though. Hehehe, win or lose…we always had a blast! I think we used wrestling to solve every dispute we ever had. Hell…it’s better than a simple coin toss, right?
However, while we having a dispute over who should play the next game on his Playstation earlier on in the evening, David did something that I thought was a big out of character, even for him. I mean, we were already on our third day of an eight day sleepover extravaganza. So nothing should nothing should feel awkward about us being together like this, right? But…as we were horsing around, David managed to get the upper hand, and he pinned my arms down to the floor while he was on top of me. Then…as I tried to wiggle my way free, he pressed my wrists down to the carpet, and suddenly…his smile faded a bit. He just looked down at me, and he’s like, “Jesus, Bailey…your eyes are SO blue. Do you have any idea how blue they are?”
I struggled a bit more, but I thought the comment was a bit strange. It just came out of nowhere. I was like, “What? What are you talking about?”
And David says, “They ARE! they’re just…super super blue! It’s kinda weird.”
He’s still on top of me at the time, and I’m giggling like, “Dude, I think that’s the ‘gayest’ thing that you’ve ever said to me. Seriously.”
He’s like, “That’s not GAY! I’m just…I was just saying…” Then he says, “I’m NOT being gay!”
“Hehehe, I don’t know, dude. That’s pretty gay.” I was joking around, of course. We give each other shit all the time, but…I don’t know, today he seemed to take it a bit more seriously than usual. Then he just kind of let me go and got off of me without any further roughhousing from me at all. I asked him, “What? What did I say?”
“Nothing. Forget it.”
“So this means that I get first crack at the game then? You did give up, after all.” Again, I was just kidding around, but he sort of got up and made sure to turn his back to me.
Then he says, “Yeah. Go ahead.” It was just kind of weird, the way his mood changed all of a sudden. “I’ll be right back.” He said, and then he went into his bathroom and closed the door. I hope he wasn’t upset with me or anything. I just…I never had another boy comment on the ‘blueness’ of my eyes before. I can’t say that I have any practice in handling a situation like that. You know?
It turned out to not be much of a big deal, though. After about ten or fifteen minutes, David and I pretty much got right back into the swing of things and picked up right where we left off. We played games, we made microwave popcorn and watched a few scary movies on TV, and we continued to laugh and enjoy one another for the rest of the night. We stayed up until about two in the morning before getting weary enough to strip down to our t-shirts and boxers and climb into bed. We’d had a pretty long day and were planning to hit up the Rec Center tomorrow to see what was going on over there. We didn’t need much sleep, but it would be a good idea to get enough rest to have some energy in reserve in case we needed it.
So…there I was…laying in bed on my back with the covers pulled up. It was Summer, but David’s parents couldn’t stand the heat, so they always kept the air conditioning on high, and it could be downright frigid in that house sometimes. And even though I had my eyes closed and was beginning to drift of to ‘dreamland’…I felt David shifting around a bit next to me. Then he was still for a moment…then shifted a bit more until he was on his side, facing me.
“Bailey?” He whispered softly. “Bailey…are you asleep yet?”
I thought about answering him like I always do, but I was all comfy and snuggled into the covers already, and I didn’t want to start up a conversation that was sure to keep us both up for another hour onc we got into it. So I just kept my eyes closed and stayed quiet this time. I figured he’d just roll over and go to sleep. We’ll talk later, right?
“Bailey?” He whispered again. I was silent.
Then…he did the wierdest thing! He reached his hand up, and poked my cheek with his finger. Hahaha, what the heck? What is he DOING??? I almost snickered out loud, but did my best to hold it in. I found it hilarious that he would do something like that just to see if I was awake. It was just plain freaky.
Then…a really long pause. So long that I actually thought that he might have dozed off on me. But, David shuffled a little bit closer to me. Close enough for me to feel his warm breath on my neck. Then, he kind of touched my chest. Right above my nipple. I had a t-shirt on, but…when I didn’t respond, he just put his hand on my chest and spread his fingers out a little bit. He left it there for a minute or two, his breathing getting a bit heavier…but he didn’t say anything. Neither did I. I was kind of curious as to what was going on here…but there was no way for me to find out unless I kept quiet.
“Bailey?” David’s whisper was really really quiet this time. Almost as if he didn’t even want me to respond. Then I felt his hand slowly slide down to rest on my belly. Again, he let it linger there for a bit…before scooting even closer to me in bed. It wasn’t until he gently lifted up the bottom of my shirt that I began to get a little bit nervous. Well…maybe ‘nervous’ isn’t the word I’m looking for. I just felt this sudden urge to skip ahead and find out where all of this was going. Because…well, this was something that was SO brand new to me. It’s the feeling you get when you’re trying to figure out what’s in the biggest gift box on your birthday table. You just want to know sooooo bad! But you have to wait. At least for a little while.
The sensation of having David’s hand on my bare stomach was beyond awesome. His palm was so warm. A little moist too, from the feel of it. I felt one of his fingers dip into my belly button a few times, then he circled around it a few times…which tickled a little bit. I liked it. But I didn’t ‘wake up’ yet. Is this why he asks me if I’m asleep all the time? Just so he can play with my belly button?
David wasn’t anywhere NEAR this weird a year or two ago!
Then…maybe just a quarter of an inch at a time…his hand began to slide a bit lower.
Now, I’m not…ummm…sexually ‘active’, as our Health teachers and guidance counselors would define it. I jerk off a lot, but that’s pretty much the extent of my sex life. And, to be honest, even though it feels amazing…I can’t even be sure that I’m doing that right! And that’s just when I’m touching myself. Being touched by somebody else, however? Anything below the belly button gives me a feeling that similar to that first drop on a roller coaster. Now I was REALLY getting nervous! Partially from David’s super gentle, but affectionate, touch…but also from the fact that my brain and my wiener haven’t really learned to get themselves in sync yet. I get boners every time my grandma’s cat jumps in my lap and wants me to pet it! I can’t stop them! They just sort of happen all on their own. And my plaid cotton boxer shorts aren’t the kind with a button in the front. Just an open flap. So…when I felt his hand moving down, and those familiar tingles traveled down to my nether regions…I just KNEW that I was about to spring wood! Not only that, but it was going to push its way right past that open flap and stand straight up where David might be able to see it. Or, at least feel it.
What do I do??? Should I, like…say something? Wait, I can’t say anything…I’m supposed to be asleep. Oh God…the tingles are getting stronger. I can feel myself getting hard. No no no! Go AWAY! Abort mission! ABORT!
My boner just wouldn’t listen to me. It just kept getting harder! Omigod, I know that I was blushing because my face felt all hot and flushed. It only took a couple of seconds for my erection to stand up and push its way through the opening in my boxers, the bare tip touching the sheets above it. PLEASE don’t notice how hard I am! Shit…and to think, I was the one calling HIM gay, earlier!
I started breathing hard as my shaft swelled to it’s full five and a half inches. It was SO embarrassing! But I kept still as David’s cautiously searching fingers traveled even lower down on my abdomen. No no no no…stop! Don’t go any lower! He’s totally going to bump into my hard on if he goes any lower! He’s still sliding down! Fuck! He’s going to tease me FOREVER about this! I just know he is!
That’s when…instead of finding my bare naked dick shooting up out of my boxers and being so disgusted that he felt the need to snatch his hand back with a total cringe…
He actually ‘felt me up’!
I mean, like…I could feel his warm, moist, palm and long fingers touch me down there and wrap around the shaft…gripping it and giving it a few slow strokes. I think my legs jerked and my thighs closed up involuntarily. I mean…I have never felt a touch this ‘naughty’ before. Don’t get me wrong…the electric shocks that David’s touch sent shooting through my body were like nothing that I’ve ever experienced before! I was immediately sent into ORBIT with the sensation of having someone else touch me there. I just…I wasn’t prepared for any of this. I don’t even think that I could properly explain what I was feeling at that moment. I just knew that a flurry of butterflies were banging around in my gut, and these tiny little explosions were going off inside of my heart…seemingly, without end. I was suddenly excited to see if he’d go any further. My best friend is actually holding my dick in his HAND! And I’m loving it! What the fuck???
A slow stroke is what he used. Very light in terms of pressure and grip. It was maddening. I wanted him to wrap his fist around tight and pick up the pace so I could blow already. Why so slow? I guess he didn’t want to wake me up, I guess. But…God…I was so hard at that moment. Especially once I learned that he didn’t mind sliding his fingers up and down on my junk. Wow…I don’t even have to risk being laughed at or teased for letting him do it. Technically, all I had to do was keep pretending to be asleep. Right? I could deny all involvement in any of this. He’s the one that made the first move. I mean, I’ve been curious about this sort of thing before…and I’d be lying if the idea of sharing a moment like this with David hadn’t crossed my mind before…but there’s no ‘safe’ way for a boy to start a conversation like that. Trust me, I spent some serious brain power trying to come up with one. Who knew that I’d get so lucky tonight?
I felt like I was floating above the mattress, with David’s fingers kind of checking me out. He felt around my tip for a bit, and he felt my balls too. It was hard for me to keep from squiring, but I managed to keep up the act. Then…his hand let go of me, and things went quiet for a moment. I was disappointed as hell, because my erection was throbbing and pulsing so hard that there was no WAY that I’d be able to go to sleep with it sticking up like that. But then…David’s finger poked my cheek again. What the hell? Is he still checking to see if I’m asleep? Come on, dude! It’s not like anybody could really sleep through something like this! Just finish already!!!
Please? Oh God, I’m SO fuckin’ horny right now! Please don’t stop now!
Then…I felt David shuffling around some more on his side of the bed, and I felt a bit of cool air rush over me as he lifted the covers and put his head underneath the blanket.
My eyes shot open again as I looked down to see his head moving further and further down, one of his hands on my bare stomach…and the other rubbing the soft material of my boxers. What’s…what’s going on? I tried to look down, but all I could see was David’s head under the covers. He started to lightly touch me again, and…I don’t know why…but I sort of found myself in a panic. I didn’t know he was going to LOOK directly at my boner! I thought he was just going to touch me a little bit and leave it at that. Now, he’s looking at pieces of me that only my doctor gets to see when I need a physical for joining the school soccer team! I’m getting so self conscious about this new development.
What do I look like down there? I mean, I KNOW what I look like…but what do I look like to him? Is he going to think I’m small? Is he going to think I’m shaped funny? I don’t really have much to compare it to yet, so…I hope that it’s…or that it’s not like…UGH! Now I’m embarrassed again! What if he tells somebody? Oh man, PLEASE don’t tell anybody!
I felt his fingers on me again for a second or two…and then I felt his nose brush against the side of my shaft. Is he really examining me that closely? Oh wait…he just brushed my boner against his cheek! Oh wow, that just gave me the shivers something AWFUL! Don’t wiggle! Try very hard not to wiggle! He might stop if he thinks I’m waking up! Holy shit! This is the closest I’ve ever come to sex in my whole life! This is INCREDIBLE!!!
Whoah, I think his lips brushed against the side of my hardness by mistake. Oh wait…was it a mistake? He just did it again. What the…? OMIGOD…he just KISSED it! I swear to God! His lips puckered up, and he kissed it right on the tip! This is almost too much for me to handle. This is totally blowing my fuckin’ mind right now!
Then…without much warning at all…I felt the warmest, wettest, sensation completely cover the top half of my stiffy in one slow swallow. Jesus! It felt like the entire PLANET had suddenly been snatched from underneath me! I almost thought that David had gotten his hand super wet with spit or something, at least at first. But once I felt this super soft ‘muscle thingy’ moving around on my hard inches…I realized that he actually had me in his MOUTH! Was that his tongue??? Oh wow! I can feel his tongue on me! I can’t…I can’t hold on! What’s happening? Oh shit…stay calm, Bailey! Don’t screw this up! Keep your shit together!
Omigod! Omigod! Omigod! Omigod! Omigod!
I couldn’t close my eyes! I just stared straight up at the ceiling as my entire body went into emergency mode, attempting to process the insane feelings of overwhelming joy shooting through me at that moment. I tried to keep my legs still, but I couldn’t. My toes began to flex and release, my heartbeat started pounding so hard that it was hard to breathe, and I found myself having to restrain from whimpering out loud in the darkness. His head began to bob up and down on me, his sexy lips dragging their heated surface up and down my rigid shaft…all while his wriggling tongue licked me all over down there. I didn’t know how to keep myself still, so I reached up behind me and just held on to the pillow behind my head. I clutched it soooo tightly…wrapping the fluffy pillow around my ears and trying, desperately, to hold as still as I could. Fuck…this is AMAZING!!! I never felt…I can’t believe he’s…oh GOD!!!
After just a minute or two, my butt cheeks began to clamp tightly together, practically feeding him more of my boner as I kept my wide eyes focused on the ceiling plaster above. David took a bit more of me into his mouth with every down stroke, and my butt would clench up tightly as his lips sank to the bottom of my shaft, and they’d relax as he sensually slid his way back up to the tip again. I knew that I wouldn’t be able to keep this up for much longer. It had only been two or three minutes, tops…but I was so turned on that I could already feel my naughtiest liquids boiling inside…ready for release! And when I felt his mouth slip off of me…he began to lightly kiss his way down the underside of my shaft. Which only took a few kisses, because…well…I was only five and a half inches long the last time I checked. I doubt I grew much since then.
But then…David kissed my balls! Let me just tell you…if you think a blowjob is mind-blowing??? Wait until someone takes their focus down to your balls! There’s something so much more ‘intimate’ about it, you know? I never really even knew what my balls were FOR up until that very moment! If anything, since I turned 12, I just figured they were ‘in the way’ of me doing anything fun. A cliche way of hurting yourself, and not much else. Turns out…they’re the most fucking fun you can have without a box of firecrackers and a pack of matches! Jesus CHRIST!!!
He kissed them lightly a few times…then I experienced the infinite joy of having him lick them both! I swear, I could feel the passionate texture of every single one of his tastebuds as his sopping wet tongue traveled over every wrinkle and fold of my pink blushed sack. This time…I actually did gasp out loud and stifled a boyish whimper as I felt my legs open wider involuntarily. I was worried that David would be able to tell that I was obviously aware of what was going on…but, if he was, he didn’t let that stop him. He sucked my balls into his mouth and ran his tongue all over them, his lips tugging at them slightly as his warm breath breezed over the soft, smooth, skin of my inner thighs. I gripped my pillow even tighter, arching my back a little as the wild sensations possessed me with the fury of a hell bound demon with an open invitation! I didn’t know whether to keep my eyes open or closed as he continued to suck and lick and pleasure me in ways that I hadn’t even seen in movies yet! Wow! I should have pretended to be asleep the first night that I slept over, if things were heading in this direction! What had I been missing out on!
My shaft began to jump and throb some more, and that’s when he let my balls slip out of his mouth and went back to sucking my hardness, tip to base. I peeked down to see David’s head moving up and down, all while trying to keep my guts from slithering around too much in my stomach. I was truly loving the feeling…but there comes a point where you know something major is about to happen. I was used to recognizing the build up, because this was always the point where I reach for my tissues and prepare to keep from making too much of a visible mess all over the place where my mom might find it.
But…I didn’t have any tissues this time!
I mean, I knew what was happening…but did David know?
Oh shit! What do I do??? What do I say? I can’t just pull him off of me! I can’t just tell him to stop, or he’ll know I wasn’t asleep! I can’t just…I can’t…I mean…FUCK! It’s too late! My boner muscles weren’t experienced enough to hold something like this back for more than a few seconds! I can’t move! I can’t stop it! I didn’t have much time to warn him! Oh God, David…please don’t hate me! But it feels too good for me to stop now!
I slammed my eyes shut and held my breath as my boner began to pulse and jump in his sucking mouth…a virgin torrent of seed, splashing against the warm caress of my best friend’s tongue as it massaged the shaft and encouraged the full eruption to blast into his vacuum, unrestricted.
I breathlessly held on to that pillow as I pumped my heated seed into David’s mouth…expecting him to be so MAD at me for doing something so nasty to him…even if I was supposed to be asleep. But…to my surprise…he actually took it all into his mouth. Like…ALL of it! And it felt like I had busted an entire milkshake worth of nut into his mouth, but he took it all anyway. The orgasm left me a shivering, sensitive, mess in his bed…and I was SO glad when I finished and he pulled his lips off of me to bring his head back up above the covers again.
I doubt I could have allowed him to keep sucking my tip without, legit, screaming out loud for the whole neighborhood to hear.
I was sure to close my eyes and pretend to be sleeping again once David was close enough to look at my face again. I wasn’t sure if this whole thing should be…ummm…a secret or anything. Would it be something that’s shameful and embarrassing? And if so…would it be humiliating for him…or for me? Now that it was over, the questions started to flood in.
David pulled the covers back, and I felt him get out of bed. He quickly walked to his bathroom and turned on the light. He closed the door, with just a sliver of light shining through. And I heard him turn on the water as he spit out whatever he sucked out of me into the sink. Oh man, what did it taste like? He held the whole load in his mouth? That’s crazy.
I heard him rinsing his mouth out, and then he brushed his teeth. Meanwhile, I was laying in his bed, still trying to comprehend what had just taken place between us. What was that? What does it mean? Does this have anything to do with my eyes being blue? Wait…is David gay???
Am *I* gay???
My mind shut itself off once I saw the bathroom light switch off, and David climbed right back into bed with me as though none of that had happened at all. I’m not sure what happened next, as I was feeling so relaxed…so relieved…that I’m pretty sure that I nodded off just minutes later. Was it all a dream? It was difficult to tell. All I knew was…
…That was the BEST night’s sleep that I’ve ever had!
The next morning…David and I woke up next to one another, and…there was this lingering feeling of doubt between us. Neither one of us said anything about it, but…you could feel it in the air. You know? Something tells me that we both knew what happened last night. And we both knew that the other person knew what happened last night. We just…we weren’t quite sure how to put it into words. At least not yet.
David caught me smiling at him, and he’s like, “What? What’s so funny?”
He gave me a sideways look, and he says, “You still wanna go to the Rec Center today? I mean…is that cool?”
I nodded, trying not to blush. “Uh huh. Sounds cool to me.”
Our eyes connected for another extended moment. Message conveyed. Then we both burst out into a flutter of giggles. “You’re being weird, Bailey. Hehehe, quit it!”
“No, I’m not. YOU’RE being weird!” I teased.
“I’m not the one grinning like a maniac for no reason.” He said, bashfully adding, “If there’s anything on your mind, I mean…you can tell me. You know? I’d understand.” I don’t know why he would be shy about saying it, but I didn’t want to make him think about it too much.
I just smirked and said, “Nothing on my mind. Not really. Well, except…” It turned me apple red to say the words out loud, but I told him, “It’s just…your eyes. They’re, ummm…they’re soooo brown. Do you have any idea how brown they are?”
David started snickering over the reference, and said, “Ya big ol’ homo…” Which caused us both to laugh out loud, and eventually end up in another wrestling match on his bedroom floor.
Where things go from here…I’m not really sure. This is as far as I’ve ever been with another boy before. But we’ve still got the better part of a week left of sleeping together in the same bed. So…maybe this was a one time thing. Or maybe it’s the beginning in a long list of naughty experiences to happen between us in the future. Either way…I liked it. He definitely liked it. And who knows?
Maybe tonight…David will be the one to fall asleep first. I’m thinking that might be fun.