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You already know that my fellow 12th grade classmate, Dean Winchester, had pulled me by my arm into a warm, dry school storeroom leading me gently into my first intimate adult experience. Explosive!
After that, I expected him to ignore me, deny the incident or give me a hot keep-away look, sending me packing any time I got too close. The reality: he let me (actually encouraged me) to hang around him. He kept the bullies away and treated me as if my existence actually mattered. I couldn't understand why but who cares? I wasn't about to jinx it with questions.
My crush on Dean began that first day in the storeroom, but really took off one day in the school hall. One of those bullies I mentioned pinned me up against the lockers to get my lunch money. When he put a hand in my pocket he felt the money alright but he also felt me getting hard. He was so angered by that that he looked into me with pure rage and raised a fist aimed at my face.
Out of nowhere, Dean clobbered him like a football tackle, pinned him against the lockers and did almost the same to him as he had done to me. Dean got me back my money and a small profit. I'll never forget the look Dean gave me as he put the money in my pocket – like a big brother who really cares. To me, he became The Dean Man. When he was anywhere near, it was tough to think about anything else.
What an act and what a strain being that close to him so much of the school day but unable to let the other kids know about this crush I had on Dean Winchester. So unfair – the difference between my state of affairs and the silly girls who clung to and fawned over their straight guys (or the other way around) right there in front of everybody.
You know why it's called a crush, don't you? It starts with a twist in your stomach, floods across your chest, makes your heart pound, turns your insides inside out and drains everything else. Most of you feels like a grape on its way to a wine bottle – a crush.
During one of Dean's and my irregular Saturday “study” sessions at my house, we abruptly paused (as expected) when Dean and I heard Mom and Dad's car exit the driveway on their way to one of their all afternoon times away that Dean and I had plotted and planned on.
He looked at me dead serious from across the breakfast table, gentle but in total control.
Oh, man I thought. What this time?
Rising from his chair in a way that reeked of a bravado that was totally overkill, he took four steps around the breakfast table, lifted his backpack with one arm and me with the other. The two of us were just standing there.
“Did you decide whether you're able to trust me, Charlie Boy?”
What do you say when you've already said to yourself a million times whatever Dean wants, I want?
“Um, Dean? Is it OK if I start with - a little bit scared?”
He smiled, “No, you're right. You need to see what's up.”
He opened the backpack to reveal the jumble, mumbling something about most of it being borrowed (despite it all looking brand new): a black mask, an orange ball attached to a black strap and some well padded handcuffs with metal clips (I learned much later they were called carabiners). I wasn't sure I'd seen everything (let alone understand the point of it all) before he closed the backpack and guided me toward the door that lead to the basement. One thing I was sure of: I had never touched any of that kind of stuff before in my life.
If hearts had gear shifts, all that backpack stuff had shifted mine from fourth to first.
The old basement was dry and dusty, smelled of cinder blocks, cement and laundry cleaners. The basement copied the outline of the whole house but with only support beams in sight – none of the walls that the upper floor had. Halfway along, we passed the old furnace that stood silent and cool in the late spring air. I missed the comforting whoosh of its hot air rising toward the floor above.
Dean pulled me over to the half-dim farthest corner away from the windows that looked onto the back yard, not that it mattered much; no neighbors lived all that close.
An old abandoned bed occupied the farthest corner, dusty and worn. Dean let go of me and the backpack. He needed both hands to pull his secret stash out from under the bed frame. When he had unfolded it all the way, there it was, a modified wooden chair with strong arms, thick heavy legs and a seat; but a seat that wasn't all there. Only the front half of the seat slats remained.
“Still gonna trust me, Charlie Boy?”
“What's not to trust about a chair, Dean? But how did it get there?”
Dean answered with a glint and a smile.
“Remember when I volunteered to help your mom with the laundry?”
“Of course, last week. She couldn't stop talking about it. She called you 'gallant' or something.”
Dean turned my chin so he look right into me. He raised and lowered his eyebrows – another unnecessary emphasis of his cleverness.
I had to admit that something about the stark plainness of the chair, its weird modification and Dean's repeated questions of trust made my stomach tighten even more, but I was still right there with him and still in one piece.
That's when the rest of it all took shape. Dean took off his shirt and told me to do the same, then shoes, then socks. Leaving his cargo shorts on, he made all the rest of what I was wearing disappear as easily as throwing away old paper towels.
He guided my totally naked “boy bod”, as he had called it a time or two, into the chair and sat me down in it. After he arranged me the way he wanted, I had to take a deep gulp when I realized that my tenderest underside felt like it was trapped inside some kind of weird indoor outhouse.
He squatted down in front of me and looked at me as seriously as he ever had.
“Did you do all that cleaning out stuff I wrote down?”
“Dean,” I stammered, “it wasn't the easiest thing. I've never had to do anything like that before.”
“And?” he pressed.
“Yes,” I sighed, “all of it. Everything I could figure out.”
He smiled, knocked my shoulder approvingly and looked down toward the target of my ultra thorough cleaning.
“This could be pretty awesome, Charlie Boy.”
“You wouldn't mind telling me the point of all this. I mean, if I can do all this – this stuff without any complaints – ”
Words were becoming more difficult for me but so were my breathing and my swallowing.
“Good point.”
He covered the technicalities of the prostate that he had researched but in such rapid fire that I couldn't possibly remember it all. I didn't know what else to do so I just nodded.
“One more thing, Charlie Boy. Remember how we decided on a safe word? When it's too much you say Kansas or something?”
“Always Kansas, Dean Man” I grinned.
“That won't work this time.”
Dean pulled the backpack over, opened the deepest pocket and pulled out the black strap attached to an orange plastic ball. He put the ball up against my lips, nodded at me and pushed it gently but steadily. It went into my mouth and I giggled a bit. It seemed silly at that point. It turned more serious when he looped the black straps around both sides of my face and I felt the tiny buckle and strap at the back of my head pull the whole thing tight.
There would be no more talking on my part; I realized that was the point. Dean did all the talking as my heart shifted into yet another higher gear making me wonder how many gears there could be.
“Now,” he started, “still trust me?”
I took another deep breath and nodded even though something deep inside me wanted to fly like a startled bird. I didn't want my eyes to look terrified. I so wanted to prove to Dean that I could do it, whatever “it” was. I wasn't going to let myself become some kind of chicken liver, some easy giver upper.
“You need to pick a safe signal,” he continued “something we can both be sure of, some action that's nothing to do with your mouth.”
I nodded and looked down at the rest me. My hands had been gripping the seat of the chair as if my grip was all that kept me from fleeing. I raised my two index fingers toward him, twiddled them a bit and nodded.
“Two pointers, huh? Cool.”
I nodded and we both smiled. Nothing dire so far.
“OK,” he continued, getting really close up. “I want you to see this.”
He showed me the back of his right hand. I looked up and down it from the base the wrist to the tips of the fingers, seeing nothing unusual about it. In my eyes, he saw my mistake.
“Not my fingers, Charlie Boy, my fingernails.”
He understood the confusion that colored my face.
“I filed all my fingernails down to nothing like the old magazine said. I don't want to slice you up somehow.”
Now I understood. I hoped my face showed enough gratitude to get through. Dean's sensual smile took me in (so what else is new).
Then the rest of it happened without another word. I sat there mesmerized at the seeming ritual of it. He reached into the backpack time and again: first a pair of padded cuffs around my left ankle with one of his pinkie fingers used as a spacer to close it but not too tight, its carabiner clasping the left leg of the chair; the second pair, ditto on my right side; the third pair on my left wrist with its carabiner attached to a rung just underneath the front of the seat. I could still hold onto the seat so I looked down and twitched my left index finger just to prove to myself that I could get myself out of this whole shebang if I absolutely had to, trying not to let Dean see that I was the least bit unsure.
Dean finished the same cuffing with my right hand and then squatted in front of me.
“Do that finger thing for me, Charlie Boy, I need to make sure” he whispered.
So I did and nothing so far felt as good as looking at Dean looking back at me, caring so much.
Dean's hand made one more trip to the backpack. He pulled out the black blindfold, held it with both hands and squatted in front me again.
“Still trust me, Charlie Boy?”
This time it took a very full deep breath, then a long exhale that bought me a different kind of courage than I had ever had to face. With a second big breath, I nodded and down came the blackout of everything around me plus the tight feel of elastic around the back of head.
“Shake your head for me, little guy.”
I shook my head almost hard enough to get dizzy but it was obvious that Dean wanted to make sure it would stay put.
With all he had done, I couldn't imagine what else he could secure, tie, restrain or prevent.
I felt all ten of his non-fingernails running down my back, up my legs, across my chest and down both sides of my face. With all that, the best feeling was Dean running both hands through my hair and then going momentarily silent.
I heard him shuffle once more into the backpack and then came the familiar snap of the cap, the lube.
I jumped when his first finger felt cold against my hole. He moved his fingers round and round; it felt soothing, sexy and dangerous. Despite all the new danger, I suppose I eventually relaxed just enough for Dean to try pushing one whole finger inside. It still made me jump.
Dean felt around, making me understand what I was like inside.
“Just try to relax, my little Charlie Fuck.”
His voice was irresistible. I sank a little more into the open seat.
Then came a second finger. The two started moving in opposite directions from each other and that's when I began to wonder whether I could stand such a feeling for long.
It was when a third finger joined the other two, that I let out my first yelp, not from pain but from something new and weird and wild. I had no words for that feeling. There was no pain at all, just the boy who used to be me evaporating, leaving behind a bundle of sensations, up and down and all over me from my ears to my toes and everything in between. I gripped the chair even tighter, breathing even faster, still determined to see it through, no chance of index fingers yet.
Dean hadn't made the slightest move toward my ultrahard cock as badly as I wanted him to. It had to be pointed right at him. No, so far it was all about the underneath.
Dean moved his fingers in and out, side to side, round and round somehow and then came a THWAP.
One of his fingers hit me dead center of some part of me that wanted to beg, scream and come all at the same time.
For the first and only time, I heard him chuckle a little. I got it: he was sitting that close to me, right between my wide open legs, reaching under the chair.
He started up again, stroking, pushing, pulling and those incredible thwaps, again and again.
I was out of control, flailing and ripping against the restraints, screaming behind the orange ball. Without the orange ball they might have heard me screaming and yelling in Kansas City. Without the cuffs, I would have kicked over everything around me including Dean. In my blindfolded blackness, I couldn't even guess what he might do next.
I lost track of time with all the building of it; it didn't ever seem to stop or even slow down. Was it hours or seconds? I wanted to come so bad. I wanted to beg Dean to stroke me so really really bad. But maybe he knew that. Maybe that was why the orange ball. I couldn't think of anything but how much I wanted it or what I could do to come.
My knees flailed; my throat screamed, laughed and cried. Every ounce of energy inside me concentrated on just that one spot inside me that Dean somehow knew about and what it screamed for – what all of me was screaming for.
And then it all stopped.
Have you ever cried and laughed all at the same time? I cry-laughed right through the orange ball, begging and out of control. I wanted to come so bad. I wanted to beg for it so bad, but there was nothing in me left to beg with.
I was a bundle of out of control panting, begging privates and cry-laughs. I thought this pause might be nothing more than Dean's gift of letting me recover a bit before starting up again.
No.
One by one, Dean took out each finger, leaving me empty and panting and begging in my silence to finish it all. But then I heard him touching the cuffs on my left leg. He was taking them away. I couldn't believe it.
One by one all of the cuffs came off. When he lifted the mask away, even the dim light of the basement made me squint my eyes closed. And finally, slowly, gently he took out the gag, leaving me free to look around and pant with my mouth wide open all I wanted.
“You were awesome, Charlie Fuck.”
Dean's voice flowed across me like salve on a sunburn.
When you sweat, little beads of water form and when there are enough of them, they join and run down your face or neck, cooling as they fall. I felt a lot of little cooling drops all over me but they weren't flowing, just stuck where they were. I focused my eyes a bit better and looked down. Little white drops were scattered everywhere, knees, legs, arms, tummy, chest, even some of it on Dean. The guy in charge must have made me shoot like a mangled lawn sprinkler, maybe more than once.
Dean squatted in front of me again shaking his head and smiling. I couldn't tell whether it was pride, disbelief or just enjoyment. He used a soft towel to wipe away the many remnants, even kissing away one stray white drop from my chin.
“You're free, Charlie Boy. The restraints are all gone.”
It didn't matter. I was spent, a lump of slumping boy and nothing more. I started to lose my balance. Gravity brought me forward on my way to the floor to become a pile of boy pulp. But then I realized it wasn't gravity; it was Dean. He was pulling me forward and over his shoulders – a fireman's carry.
As he lifted me, I saw the floor move away and I thought of gliding on the wind. The moving basement floor ended, becoming the steps that raised us toward the upper floor. I thought this must be what death is like: when your life is spent and there is nothing left, an angel as beautiful as Dean lifts you over his shoulder and flies you helplessly upward toward whatever comes next.
I remember the feel of Dean's hand on the back of my neck, unwinding me down from his shoulder onto my pillow – my own pillow, my own bed, my own covers that I could feel him tucking loosely around me.
A moment later, Dean slowly, gently scooted under the covers with me. I felt his knees on the back of mine, his cargo shorts against the tenderest part of me, his bare chest against my back. In all that time in the basement, he had never been naked, never done anything for himself or to himself, just me.
In a flash, I realized that as given out as I was, Dean could have done anything to me he wanted right then and I'd be hopelessly unable to stop him. Instead, I felt his lips whisper against the edge of my ear.
“You really were awesome, Charlie Boy.”
My body let out another cry-laugh all on its own. You'd never guess that a simple thing like spooning would create so much emotion. With Dean behind me and after everything he had put me through and how helpless I was, feeling him close against me made me think again about angels. What force could possibly make me confuse Dean sex with thoughts of the afterlife I will never know.
As I felt the blanket of dreamland weighing me down, I had one last thought: after some eons of sleep, I might somehow wake up close to normal. I was determined that I would slowly roll over, face Dean making sure that my blue eyes met his deep green ones, raise both of my fists between his face and mine and flip him two index fingers.
(Yes, index.) 👨