Their Third Time

Their first time was painful and awkward.

There wasn't anything sexy about it. It didn't feel good and when Kaleb said he wanted to stop (thank God), they soon realized the liquid dripping from Dean wasn't cum. He bled all the way to the bathroom, a few droplets hitting the carpet and staining it. It reminded him of his period, a major trigger of his dysphoria since he had to wear a pad for the rest of the night. He'd never been penetrated by more than a few fingers, and his body clearly wasn't prepared for the thickness.

His boyfriend felt awful, apologizing profusely as though it was his fault. The guilt in his eyes squeezed at Dean's heart. He was the one who wanted to go all the way, his testosterone shots heightening his drive. Kaleb had said over and over they didn't have to, how they didn't need to pail to have a fulfilling relationship.

He had been more than willing to wait but no, but Dean wanted to go to Pound Town, ticket for two.

Their second time was better, and Dean was even enjoying himself, although like the first time, there was no kink. It was painstakingly vanilla with Kaleb pestering him every other minute.

"Are you okay?"

"Does that hurt?"

"Was that a good noise or a bad noise?"

Dean eventually told him to pull out, and he did immediately.

"I'm just not in the mood anymore," Dean said. "I know like, ten minutes ago I was begging for it and humping you like a bitch in the throes of heat, but... I dunno. I just... just--"

"Dean, it's fine. You don't have to explain."

"I'm sorry."

"It's okay." He flipped over so he was on his side, and pulled Dean into his warm, broad chest. "Everything is okay."

But was it?

When Kaleb gets home from the grocery store, Dean is sitting, waiting for him on their brown leather couch.

"Yo. I've been thinkin'."

"That's a first. About?"

"I want you to be..." he drops his voice to a mumble, "less gentle with me."

Kaleb stares at him silently for a moment, a tell-tale sign that he can't hear shit. "What?"

"I want you to not be as gentle," Dean says, louder. "Ya know, when we're having sex."

Kaleb sighs, puts the paper bags down on the counter and holds up a hand. "Help me put these away. Then we'll talk."

Once the frozens, orange juice, and the rest of the food is put away in the cabinets and the lazy Suzan, Dean has his head in Kaleb's lap. It's warm, there, and he nuzzles into his thighs as Kaleb cards his fingers through his hair. It feels nice--like home, probably because it is. Wherever Kaleb is, be it in a college dormitory's twin bed or in the living room of their house, he's safe. He's home.

"You know all those other times we've done sex stuff without actual sex?" he starts. "You've been in top mode. Like, you were a too hot to handle dom daddy and I could just let go. I think the fact you're clearly scared scares me, too. And I don't want you to touch me like I'm a piece of glass, either. I want to be grabbed and thrusted into because the second time felt good, it was just--just the constant checking and the contagious anxiety that was getting to me."

"What can I do better?"

Dean closes his eyes and ponders it. More confidence would be a start.

"I wanna have it like when you used to make me cum. When you fully take the reins of the crazy Fooling Around carriage without any hesitation because you know what I like and know how to get me there."

Kaleb's nails scratch gently at Dean's scalp, and if he could purr, he would be a motorboat, totally blissed out from the relaxing touches. "I think I can manage that."

Dean sits up so he can look into Kaleb's green eyes, his irises frosted with brown around the edges. "Really? Not that I should be surprised. You're pretty awesome, dude. An A+ partner. You could get a gold medal for Boyfriend of the--"

Kaleb taps a finger to his lips and shushes him. "Bedroom. Now."

Dean gulps at the order, the command activating something deep down in him. "Yes."

"Yes what?"

Dean flushes. "Y-yes, Sir."

"Good boy." He kisses him on the forehead. "I'll be there in a minute. Be naked when I get there."

Dean rushes to the bedroom and pulls his shirt off with ease. It's the binder that's a piece of work, having to peel the tight fabric off his torso, his small breasts springing free. He used to be self-conscious of them while being intimate, but he's discovered his pink buds are usefully sensitive and that having them out doesn't make him feel like less of a man as long as Kaleb's there.

Kaleb enters the room in nothing but his sweats, the white scars on his arms on full display. Dean knows this is like baring his heart, letting him see marks from his old demons, and he loves him fiercely for it.

"Lay down."

Dean does as he's told. His head is spinning and holy fuck, Kaleb is suddenly pinning him down to the mattress like a Victorian woman on her wedding night, her hungry suitor more than ready to deflower her and holy shit, he's going to fuck him, isn't he? Dean feels blood rush to his face and realizes he's been breathing out his mouth in stuttering pants.

Dean licks his dry lips. "Please," he whines. "I want--I want you, please."

"Please...?"

"Sir! Sir, M-M-Master, pretty please with extra sugar and a cherry on top, I needed you inside me yesterday, plea--"

Kaleb shuts him up with a kiss, sucking on Dean's lips hard enough to bruise his mouth. Butterflies flutter deep in his stomach as Kaleb puts a hand on his throat, not tight enough to choke him but enough to say without words, You're mine. No one else can have you.

Dean moans into the kiss, Kaleb straddling him. He may be short, but he's stocky, just heavy enough to be a delightful, comforting pressure on Dean's body and when he starts thumbing at his left nipple his hands go to his scars, tracing them lovingly and wishing he could kiss them but he can't from this angle. Kaleb shudders against him before pinning both hands to the bed and detaching his mouth, a string of saliva between their lips before it inevitably breaks.

"Did I say you can touch me, baby?"

Dean shivers at the pet name. He'd picked it up from a porn fic he sent him at one point, and he'd integrated it into his vocabulary just for him. "No, Sir. I'm sorry."

"Take off your pants."

Dean's heart pounds as he yanks off his jeans.

"Underwear, too."

He nibbles at his bottom lip, not helping but look at the mess that he made in his black panties. He tosses both articles of clothing off the bed and Kaleb rubs at his clit. Dean starts to bite at his lip harder, trying to muffle his noises but he can't help it, it feels so good, it feels-- it feels--

"Shades, too."

Dean forgot about those. He hands them to Kaleb who delicately places them on the edge of the mattress, far enough away from them not to get rolled on. He knows they're from his best friend Jack, how they replaced the sunglasses from his brother and are a big part of who he is.

"Your eyes are so pretty," he purrs.

"Can I touch you, Master?"

"Yeah, sweetheart. Good job asking."

He presses his hands on his caramel chest, fingers brushing the dark hair there. Kaleb reaches out and presses a hand to his cheek, brushing his thumb below his eye. "You're my best friend," he gushes.

"I know," he whispers, and Kaleb touches his pussy again, playing with the wetness. He gnaws at his bottom lip.

"Don't hide your noises from me," he says, pushing a finger inside.

"Sorry, Sir," he croaks. "Ah, hah, mmmh." The squishing sounds of his cunt grow louder as Kaleb slips another finger, then another.

"Can I lay back down?"

"Such a good boy asking for permission. Yes, you may."

Dean gets on his back and spreads his legs. When Kaleb pulls his hand out, he wipes the pussy drool on Dean's upper thigh, letting him feel how wet he is. When he reaches for the top of his pants, he gives Dean a questioning look.

"I'm ready," he says, knowing Kaleb needs the clarification.

When Kaleb's cock springs free, it's rock hard.

Kaleb lines up his dick with his hole and slides it in him nice and slow, letting Dean get accustomed to the stretch before he flashes him a thumbs up to let him know to keep feeding it into his pussy. The third time feels even better than the others and Dean throws his head back and groans as the dick penetrates him, plunging in and out as Kaleb pumps his hips, and suddenly Dean can't stop from babbling.

"Feelsh so good, M-Master. Shoulda stretched m-my cunt last t-t-time 'cause this feels divine. Angels are singin' and I'm in sex heaven, f-fuck!"

"Keep talking," Kaleb growls out and fuck, the sound is so primal and sexy Dean is now clawing at the sheets and when Kaleb starts rubbing at his clit his eyes roll back into his head.

"Master, Sir, baby! I love this, want y-you to fuck my pussy for-forever and ever!" He goes on and on, yelling non-stop about how much he's in love with Kaleb's dick until he can't help but beg for what he wants in the moment more than anything.

"Fuck! I need to cum. Can I, Master?" He realizes he's crying, and immediately adds, "Good tears, getting f-fucked to oblivion tears. I wanna cum so bad, I--"

Kaleb slaps his thigh so hard he yelps. "Not yet. Flip over."

Dean flips onto his stomach, ass up. Kaleb slaps his ass and he whines, shaking his bubble butt without shame as his boyfriend spanks him until he's red and sore. Then he slides in, and if he was in heaven before he's now in hell, being tortured so sweetly by an evil, sexy devil who won't let him orgasm.

Kaleb uses Dean's hips to push himself even deeper, his balls slapping his clit that's craving more stimulation than he's getting.

Finally he grunts out, "You can cum when...I bust..."

"Yes, cum in me! I need it! Oh, God, please, fill my pussy up, plea--"

Kaleb fucks him more roughly as he dumps his load. Dean screams and crams his hand beneath the mattress, rubbing vigorously at his clit and when Kaleb pulls out, squirt and warm cum is mixing together while he sobs and shakes as his cunt clenches around nothing, squeezing around the memory of Kaleb's fat cock.

Dean drifts into a loopy haze, panting and heart racing as he comes down. Suddenly, he's being rolled over and his eyes meet Kaleb's pink face as he pants just as hard as him. He scoops him up and Dean makes a questioning noise.

"Bathroom."

Oh. Yeah, they're both a mess.

"Love you," he manages, nuzzling into his neck and peppering it with breathy kisses. "Love you, Kale. Best... fuck ever.