Caliban had his misgivings when he was roomed with Skoll, especially learning he would turn into a woman at times. But Cal knew what it was like to be mocked, or otherwise talking bad about him.
And...Skoll was a decent guy, girl...whatever they were at the time.
Skoll still cared about his wife and kids, sending them money, it was...different from Cals experience with his own old man.
And..somehow, it ended up here, in their room. And holding each other, only in their underwear.
Skoll helped Cal realize he liked men, and when Cal finally confessed, Skoll offered to let Cal get adjusted to being touched by a man in a ‘non-violent’ manner.
They just spent days, hugging each other, and Cal got to enjoy it. Skoll never pushed, and Cal soon instigated the hugs.
And in time, as they laid together, just holding...cal would explore with his hands. Allowing himself to feel Skoll’s muscles, the older skin being more pronounced then Caliban was at the moment.
Skoll had allowed it, he even took off his shirt for Cal, so the younger man could feel Skolls muscles more intimately.
“At anytime you feel uncomfortable, we can stop,” Skoll promised.
But Cal, he just squeezed at Skolls back, traced his shoulder blades, traveled across his shoulder to palm at Skolls pecs. Caliban breath getting heavy, as he saw his fingers card through Skoll’s chest hair, and Skolls pointed nipples dragging under Caliban palms.
Soon it escalated, and Caliban was kissing Skoll, both of them practically naked, and swaying together, alone in their room.
Caliban hands clutching at Skoll’s body, his firm, round butt, pressing himself hard against Skoll with a almost desperate whine of heated arousal.
“Skoll...please...” Cal whispered heatedly.
“Do you want want something?” Skoll asked, teasing Cal by dragging his own hand down Cals back to cup and squeeze his ass.
“Please...you know what...” Cal gasps.
Cal buried his face into Skolls shoulders, whimpering as Skoll pressed his lips to Caliban’s neck.
“Tell me, I won’t do otherwise,” Skoll growls as he nibbles on Cals ear.
“I want..you to...make love to me,” Cal almost wept, rubbing his forehead against Skolls, almost desperate.
Skoll lowers Cal onto his back against the bed, and tugs off Caliban’s boxers. All while he ducks and licks at Caliban’s nipples, the young skin huffs and whines in pleasure as his exposed cock is fondled by Skoll.
“I’ll do it, I’ll make love to you,” Skoll whispers against Caliban’s chest. “You feel such pleasure, your eyes will roll into your skull.”
Caliban let out a surprised Yelp, at the words, and feeling Skolls hand on his cock. A man, another man, older, he was touching Caliban’s intimate part. His cock was stroked, and his balls cupped and fondled. Skoll sucking and tugging on Caliban’s nipples was matched by tugging on Caliban’s balls.
His toes curled, whimpering erupting from his lips, Caliban grasped and stroked at Skoll’s head and shoulders.
“My sweet boy, you are too wonderful, too pure, and...” Skoll paused, looking up at Cal with his deep, blue eyes. “How I ever got to meet you, I don’t know...but I’m grateful.”
Skoll leans up, both his hands stating to play with Cals dick, as Skoll sealed his lips against Caliban’s.
Caliban squirms, shifting in pleasure, as Skoll kisses his lips, his jaw, his neck, down his chest to his cock.
“Is it alright, if I lick you?” Skoll asked.
Caliban stare down at Skoll with a heavy blush on his face, nodding, before he tosses his head back in pleasure as Skoll licks a stripe up his dick.
The blond, blue eyed Skin, laps always at Cal’s cock, earning whimpers, whines and moans from the younger as his cock was serviced.
Cals cock drips precum, coating Skolls fingers, and sucking on the tip of Cals leaking cock.
“I’ve dreamed of this moment,” Skoll whispered, lowering himself further and lifting Calibans legs.
“Skoll! I...this...you dreamed...” Caliban pants out.
“Yes, of course. Of your legs up in the air, your cock twitching from arousal, and your sweet, untouched ass hole, quivering and exposed for me to ravish,” Skoll licks his lips. “Please, allow me to be the first to savor and loosen this virgin bud.”
Caliban was speechless, he never expected anyone to speak to him this way and it left him dizzy with ecstasy. He nods, eyes trained on Skoll, who’s face with exuding joy, as his face disappears between Cals legs.
Cal tosses his head back, breath heaving out in joyful pleasure, as Skoll licks and laps at his hole, one of Skolls hands keeps Cals leg up in the air, while the other jerks Cal off. Slicking up Skolls fingers, as Skoll hums in pleasure, relishing the taste of Calibans virgin ass. How it clenches, then yields to Skolls ravenous mouth and skillful tongue.
His ass opens up to Skolls experience and soon, Cal wails as he feels a finger work it’s way into his ass. Calibans thighs tremble under the sensation of a tongue and finger in his ass for the first time.
“Skoll...Skoll...oh Fang, it’s...” Cal tosses his head side to side. “So good...Skoll...”
“That’s it, pup.” Skoll teases in husky voice, still working a finger into Cals ass. “Just relax, accept the pleasure, and my fingers inside of you...you’ll need to try fingering your self on occasion. Loosen yourself, so you’re not so tight when we do this again.”
“Again?” Cals head looks up in surprise. “You’d want to do it again?”
“As many times as you’ll let me,” Skoll said, slipping another finger into Caliban’s ass, while sucking on Cal’s balls. “There’s another finger.”
Caliban shudders and shakes, so exquisitely pleasured by the ministrations of his older roommate and now, lover.
“Just have to get you open enough for me, Cal.” Skoll moans against Cal’s cock. “And then, I’ll slip inside of you so sweetly, and it’ll feel great.”
“Please...let me touch?” Caliban reached out to Skoll, pleading to be able to return the pleasure.
“Sure thing, Pup. Go for it.” Skoll beams.
He climbs up onto the bed, and was sideways to Cal, resting on his side, upside down so he was face to face with Calibans cock. But Cal could see the blondes own bulge, the older males cock straining against its cloth prison.
Excitedly, Caliban cups and fondles Skoll through his underwear, earning a moan form Skoll, who stifles it with Cals cock in his mouth.
The moans vibrates around Cals cock, who yells in eager ecstasy, as Skoll worked a third finger into his ass.
Cal trembles, shutting his eyes briefly, before tugging down Skolls briefs to reveal his engorged dick. The swollen dick head, a drop of precum on the tip. Cal grapes the member with his hand, needing a second hand to grasp the heavy dick. It was a fat thing, Caliban needed both hands to hold it, and admire its shape and heat.
“Aaaah!” Cal then yelps, as Skolls fingering hit a particularly sensitive spot in his ass.
Cal in retribution, leans forward to lick at Skolls cock. The older skin stops in his actions, groaning heavily as Cal pressed the flat of his tongue to the tip of Skolls cock. Stroking it with both hands, as the veiny, girthy meat oozed out its sweet, and salty syrup.
Cal whimpers desperately, sucking on Skolls cock, as the dilf proceeded double his efforts in ruthlessly stretching out Cals ass. The young virgin, eagerly, happily, accepting the ministrations of Skolls hands and mouth. He slathered his tongue on Skolls cock, hands cupping Skolls, orange sized balls. He breathed out heavily through his nose, whining as Skolls mouth was merciless in its attempts to drag out Caliban over the threshold from ‘virgin’ to ‘experience’.
Cal pulled Skolls cock form his mouth, panting for breath as he pumps and strokes at Skolls cock.
“It’s so big, will it really fit?” Caliban asked, eyeing the turgid girth he was pleasuring with his shaking hands.
“It’ll fit and then, it’ll feel...incredible.” Skoll pulls off, but spreading one of Caliban’s cheeks.
He mercilessly worked in one more finger, spreading his fingers in Caliban’s ass. Exposing Caliban’s virgin hole to Skolls hungry gaze.
“Please...please, Skoll.” Cal begs. “Don’t stop...”
“What do you want, Pup. Tell daddy what you want.” Skoll huffs in arousal.
The words, so filthy, and wrong, it....was too much for Cal.
“I want your Dick, Daddy!” Cal weeps. “Please...take me...”
“Oh, Caliban.” Skoll growls.
Lustfully, and overwhelmed by Caliban’s mere pretense, Skoll flips over, so he could put Cal on his back and pressed his legs till his knees touched his chest.
Cal gazed up at Skoll, eyes brimming with love, lust, and some fear in the blue moonlight. Skolls chest rose and fell with barely restrained hunger as he gazed at Caliban’s naked form.
Skoll pulls away, patting Cal on the thigh.
“Hold your legs, Cal for just a minute.”
Cal did as Skoll asked and watched as the older fetched a bottle from his dresser drawer, and hurried back over, cock bouncing in the air.
“Now, we can really begin.” Skoll said.
He purrs slick, goop onto his fingers, and holding both of Caliban’s legs up with one hand by the ankles, he slid one into Cals ass. And another finger, and another, earning wretched moans and pleading from his helpless, handsome, roommate.
“Skoll...Skoll...daddy...please...” Cal beseeches.
“Just a little more, I want you to be absolutely prepared,” Skoll promised. “Then you’ll get this hard cock inside of you, I’ve wanted to slide it into you for too long. You’ve no idea the effect you have on me, and other hungry men out there.”
“But Aahh! None ohhh-of them aaah-re you,” Cal promised.
This earned a ecstatic kiss of joy from Skoll, drilling his fingers inside of Cal, who’s mouth opened to scream in arousal, only to have Skolls tongue in his mouth.
Their tongues swirled around, wrapping around each other, before Skoll pulls his fingers out. He then leans back, letting Caliban’s legs rest on his shoulders. Planting his tree hand on Caliban’s chest, stroking and fondling Caliban’s chest. While his other hand, greased up Skolls cock.
“It’s going to go in now,” Skoll told Cal, pressing his lips to Cals forehead. “You just relax, but push out as I push in...and soon it’ll feel ‘amazing’.”
Skolls words had Cals eyes shut, eyelids shuddering in dizzy ecstasy from the words Skoll spoke.
And then, he opened his eyes, as Skoll grasped Cals one hand, lading their fingers together tenderly.
“Just squeeze my hand, and we’ll get through this,” Skoll then Pressed his dick against Cal’s ass.
Caliban bit his lower lip, whining as Skoll’s mushroom head pierced his tight ring of muscles, Forever steaming away his virginity in that moment. Cal squeezed his hand, gasping, as the cock searing hot, slid further into Caliban’s deepest regions.
“Aaaah!! Ohhh...Caliban,” Skoll opened his mouth in a heavy groan, eyes shut as he plunged deeper into Cal. “Oh...I-I...fuck, so tight.”
Skoll growls, placing his face into Caliban’s neck, as the younger skin coos, whimpers and gasps with pleasure.
“Easy, easy, there...there....” Skoll grunts.
“Ahahhhh! Skoll! Skoll! Daddy!” Caliban cried out, opening his eyes only to shut them against the lurid sight of Skolls face twisted in pleasure.
Skoll thrust gently at first, but as he felt Caliban’s Vice like grip on his cock, loosen a bit, he picked up speed. Sliding back, and then all the way to the hilt.
Cal gasped heavily, turning his face as Skoll nuzzled his cheek, before turning to pucker up his lips pleadingly. Skoll capturing his lips, rocking his hips up, rigidly, driving his dick inside and wriggling his hips side to side.
Caliban began to shift his hips too against Skoll, his ass flexing and squeezing down on Skolls cock.
“Please...don't...please...don’t stop..” Cal begs.
“I won’t stop, Cal.” Skoll moans, rapidly slapping his hips against Cals. “NOT UNTIL YOU’VE CUM!”
Skoll barks the last sentence, drilling into Cal, who’s cries get higher, more wrecked and desperate.
“Oh this... this is it,” Skoll moans. “Should I cum inside you, or outside?”
“In me!” Cal answered without thought. He arched his back, his butt quivering around Skolls cock.
“That’s right, I’ll fill you up,” Skoll kept his hand laced with Caliban, but his other clutched Caliban cock and pumps him fervently.
“Aaaah! Daddy! Skoll!” Cal leaned his neck back, crying out as he shot stripes of white across his chest.
It also splattered on Skolls chest, the older skin, panting and bellowing as he soon slammed in balls deep. His balls shrunk up, as he pumped his load after load inside of Caliban’s ass.
The younger whimpers and mutters almost delirious as he trembles from both his own orgasm, and Skoll’s steaming hot load in his ass.
“Oh! Oh Gods...Oh My Gods,” Skoll pants, pressing kisses to Cals forehead. Before the older, hunk, just lays out on Cal. The younger allowing it, moaning happily from the heavy weight of Skoll on him as both passed into deep sleep.