“Did you do your stretches beforehand?  We can stop if you need to.”  Juniper’s voice nickered in concern.

Stretched out on a lifting bench, Jack covered his face.  The fur that normally draped around his ankles drooped down over his calves instead as his hooved feet quivered in the air.  “I swear, I can take it.  Just give me a moment.  You’re just…  Fuck, it’s tough to relax that much!”  Bouncing on his belly, his cock throbbed and spat dribbles of excitement onto his chest.  His nuts sagged over the crown of Juniper’s own cockhead, shiny with lubricant and bouncing with her heartbeat.

“You would know!  You’ve got this monster right here.  I bet it’s a struggle for your other friends to fit, too, right?”  Juniper’s hands lifted the thick piece of throbbing horsecock off of Jack’s belly and gave it a few pumps.  She wasn’t wrong.  Jack had seen them all laying out before him and squinting their eyes shut as they let the incline of the bench pull them innevitably down over his thick head.  And now here he was trying to do the same.  It wasn’t as easy as it looked!

“Come on, you can do this.”  Juniper’s voice was soft but firm.  He reached out, and her fingers twined with his while her tip flared against his slick ring.  Focus on relaxing.  Breathe in, breathe out.  Let the muscles rest and stretch—and fuck she was thick.  There was a certain plush feeling to the way she prodded against him.  Her pre was glazing around the periphery of his donut.

“You know, this is a pretty great view I’ve got right here,” Juniper mused.

“I bet you do.”  Jack huffed through his teeth.  He pushed again to no avail.  Her cockhead dimpled his ring inwards.  He could almost feel himself relaxing, but she throbbed again, and he lost his focus.  “Bet it’ll look even better when you’re inside, huh?  Ergh.  Stop twitching like that.”

“Can’t.  You’re too sexy like this.  Anyone ever told you that you’ve got a really sexy ass?”  She ran one finger against him, in between where her cockhead was starting to spread his thick ring.  The added stimulation was fantastic, but it was also ruining his focus.  Juniper laughed, and the finger disappeared.  She ducked her head and whispered, “Sorry.”

“Not exactly had many people where you are right now, you know?”  He grunted.

“Shame, because you’re really pretty.  Stop laughing!  I mean it.”  Juniper folded her ears down so he wouldn’t see her blushing.  “Okay, try pushing down against me.  See if you can relax.  Oh, there you go.  Fuck you feel good.”

He could feel the rigid core of her cock sliding with the copious amount of lubricant they’d spread everywhere.  The complex crown of equine cock pressing against his ass folded back so only the cylindrical center started to slip into his puffy donut.  “There. You got it!  I’m inside! You okay?  Is this okay?”  Gazing down at him, Juniper’s long face watched with concern.  His face must have looked rough with focus and a little bit of strain.  But she was right—he could push through!

The next few seconds were a novel sensation he’d never imagined would be so satisfying.  Slick skin rubbed against his involuntarily clenching muscles.  It felt tense to stretch so wide, sure, but it also was so deliciously sensitive that he felt himself throb off of his belly, even without the help of Juniper’s fingers.

“Wow, you were right.  The view’s even better now.  Hope you don’t take this the wrong way, but you look like a natural stretched around my cock.  Not too tight.  Okay, yeah, I know it doesn’t feel that way, but I’ve had some lovers where it was just too tight, you know?”  Juniper stopped moving, letting Jack get control of himself before those throbbing pulses against his belly worked him up too much.  He did know.  He’d had partners like that, too.  “You’re nice and soft around me.  Feels lovely.  Think you’re ready for the rest of it?”

There was more?  Of course there was.  Hadn’t he heard his previous lovers say the same thing when he’d just got the head inside?  This was the best part—or at least it was the best part when he was the one doing the fucking.  Feeling that tight tail sliding up along his shaft, inch by inch, until he could feel their cheeks in his lap.  Well, that was him this time.  And it was going to be his cheeks sitting in Juniper’s lap while her balls slapped his tail.  He’d had a couple lovers who’d started cumming just from the first full push-in.  He was going to be better.  He bit his tongue and laid his head back, then nodded.  “Come on, do it!”

She did.  He couldn’t quite measure the inches as she pushed deep, but the way she filled him out made his legs quiver again.  She was so deep!  And then she kept pushing, and he realized she was barely halfway in.  There was a slick ripple against his donut as her medial ring slipped past.  He reached up for her, and she put her muzzle into his palm.  She was shaking too.  He knew how this felt from her end.  Now that she was inside, it was a lot easier to stay relaxed to let her sink deeper.  It was a stretch, but he could take it!

Focusing as he was, he still wasn’t quite ready for the meaty smack of her crotch against his ass.  With their hands held together as she finally hilted, Jack groaned.  He could feel it rising, and no amount of focus was going to stop it.  He could hear Juniper’s gusty breath nickering out through her nose.  She knew.  He must have been clenching as it began.

The first splash hit him under the chin as Juniper pulled back and gave him another thrust that slapped her balls up beneath his tail.  Considerate even in his failure, she reached down and stroked him while she moved.  Sensation from his stretched tail end made him see stars.  She rocked and pushed, thrusting her way straight through his involuntary orgasm.  He could feel her throbbing deep in his gut as the second splash painted his chest and dripped down onto the workout equipment.  Good thing they’d put down towels.

When he finally returned to his senses as his peak faded, Juniper slowly stroked the last of his gushing load from his flared cockhead.  She stayed buried deep, still throbbing.

“Feeling good there, stud?”  She joked.  Jack tried to cover his face in embarrassment, but found that his fingers came away sticky from stray strands of his cum that streaked over his face.  “It’s okay.  You fit me.  That’s progress!”

“Yeah, but you didn’t—“

Before he could continue, Juniper put a finger against his lips.  He extended his tongue and licked a few stray strands of his own liquids from her digit.  “Shhh.  It’s okay.  We can stop there.”  She smiled as he lifted his head.  A moment later, he felt her throb again deep inside him.

“No.  No!  I can do this.  Come on, think you’re gonna wear me out that easily?”  Jack scoffed, then winced as her cock throbbed again deep inside him.

Juniper smiled above him with a certain bit of glee in her smile.  “Okay, so you did your first set.  Ready for the second?”

He hesitated, squirming in discomfort as the thick horse cock stretching his pucker twitched and—if he could believe it—throbbed even thicker.  This was exactly what he’d asked for, even if he was doubting himself.  Wasn’t that what he told everyone he trained with?  He was strong enough.  He was tough enough.  He could do this!

Jack reached up and grabbed his knees, spreading his legs wider.  He’d gone soft, but renewed confidence mixed with the sensation of Juniper’s next long thrust brought him a pulse that brought him back to crooked half-hardness.  She whinneyed above him, and he felt her twitch inside him.  This time he could take it!

Story by Kandrel

Artwork by Taz