Jamie tells Alex he wants to fuck someone whilst being fucked at the same time. Alex arranges for Sam to join them the next evening, and Jamie gets exactly what he asked for. By Harlan Maddox-Powell.

Warning: this story contains scenes of a sexual nature, including: a pre-arranged threesome between consenting adults, oral sex, fingering, bareback anal sex (all partners tested), a man topping while being topped and internal ejaculation. This story is written for adults and is not for minors.

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Jamie was twenty-five and still new to most of this, and he’d been working up to the question all evening. When he finally turned to Alex in the living area of the flat, it came out in a rush.

“I want to know what it feels like to fuck someone whilst I’m being fucked at the same time. Have you ever done that?”

Alex looked at him over his glass of water, and his mouth curved. “Yes. Both ways. I’ve been the one in the middle and I’ve been on either end of it.”

Jamie’s cock gave a hard pulse in his shorts. He could already picture it, a cock opening him up whilst his own was buried in someone else, every thrust from behind forcing him deeper into the body in front. He kept his eyes on Alex and let the words come before he lost his nerve.

“I want that. I want to be the one in the middle. I want to push into someone and feel them grip me whilst someone else is stretching me open, and I want every thrust from behind to shove me deeper into the man in front. I’ve been thinking about it since the last time I was inside you.”

Alex set the glass down on the counter and came over properly. The line of his cock was starting to show through his shorts. He stopped a few feet from Jamie.

“I know someone who’d do exactly that with us. Sam. I’ve hooked up with him before. He’s thirty-four, three years older than me, and he’s clear about what he wants. He’s done the middle himself, so he knows how to keep the rhythm working for whoever’s in it. He’d top you whilst you top me. You in the middle, me underneath, him behind you. Is that what you want?”

“Yes,” Jamie said, his voice rough, his cock obvious now against his shorts. “That’s exactly it. I go into you first, so I’m all the way in when he starts on me. Bareback. I want to feel both ends with nothing in the way.”

Alex nodded. “Bare’s fine. We’re all tested. The only other thing is timing. He’s free tomorrow evening, and I can message him now if you want it that soon.”

Jamie’s gaze dropped to the outline in Alex’s shorts and came back up. “Message him now. Tell him the exact setup. Tell him I want to fuck you whilst he fucks me, and tell him tomorrow works.”

Alex pulled his phone from his pocket without looking away. His thumbs moved over the screen in short, sharp taps, and Jamie watched the muscles shift in his forearm and his shorts tent further as he typed. Jamie was fully hard by now, the head of his cock pushing up under his waistband, his balls aching.

“Done,” Alex said. “I told him the order, that it’s bare, and tomorrow evening. He’ll answer fast. He always does when the offer’s clear.”

They stood there waiting, and Jamie couldn’t stop picturing it, the rim of Alex’s hole stretching round the head of his cock whilst Sam forced his way into him from behind.

Alex’s phone buzzed. He read the reply and looked up with that same controlled little smile.

“He’s in. He said yes to the setup and he’ll be here tomorrow at eight. He asked if we wanted him to bring anything, and I told him we’ve got everything we need.”

Jamie’s cock jerked. By this time tomorrow he’d be buried in Alex with Sam buried in him, and the thought made him light-headed.

“Good,” Jamie said. “Tell him we’ll be ready. Tell him I want him to push in once I’m already inside you, so I feel him opening me up whilst you’re gripping me.”

Alex typed and sent it, and another buzz came almost at once. He held the phone up so Jamie could read it: a simple yes and the time.

“Eight o’clock tomorrow,” Alex said. “You’ll be in the middle, exactly how you want.”

Jamie’s cock pulsed again in his shorts. Now all he had to do was survive the wait.

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Sam knocked once and Alex let him in. Jamie stood in the living area and took him in as he stepped through the door. He was solid through the shoulders and the same height as Alex, and he looked at both of them like a man who knew exactly why he was there. Jamie’s heart was going so hard he was sure it showed.

“Sam,” Alex said. “This is Jamie.”

“Jamie.” Sam’s voice matched the rest of him, deep and plain. “Alex says you want the middle.”

“I do,” Jamie said. “You behind me, me inside him. I go into him first, so I’m all the way in when you start pushing into me.”

Sam nodded. “Got it. If you want to stop at any point, say so and we stop.”

“I won’t want to stop,” Jamie said, then grinned at how keen he sounded. “But yes.”

They went straight through to the bedroom. The door shut and the clothes came off fast. Alex’s cock was the length Jamie knew well, already filling out. Sam’s was heavier and thicker through the middle, and it began to rise under Jamie’s stare.

Jamie took Alex into his mouth first, the salt of him instant on his tongue, whilst Sam closed a hand round Jamie’s cock and stroked him from base to tip in firm pulls. A moment later Alex turned his head and took Sam’s cock into his mouth. Jamie pulled off long enough to speak.

“Keep that going. I want both of you hard before we start.”

Alex answered round Sam’s cock. “We’re getting there. You’re leaking already, and he’s filling out in my mouth. Just keep going.”

Jamie went back down on Alex and took him deeper. Sam’s free hand moved between Jamie’s legs and pressed two slick fingers against his hole, and the rim gave under the pressure and let them in. Jamie reached for the bottle on the nightstand, coated his own fingers and pushed two into Alex, whose hole fluttered round them and then held on.

They worked each other open like that, mouths busy, fingers sliding deeper. When Sam added a third finger the extra width burned sharply, then settled into a fullness that made Jamie’s cock throb in Sam’s grip. Jamie did the same to Alex, scissoring carefully, watching his cock jerk against his stomach each time his fingers curled.

Alex spoke first. “I’m ready. Get inside me. I want you buried before he starts.”

Jamie pulled his fingers free. Alex rolled onto his back and drew his knees up wide, his hole soft and loose from the fingering. Jamie slicked his cock with more lube and climbed between his thighs. He lined up and pushed, and the rim stretched tight round the flare of his head, resisted for a heartbeat and then gave. He kept the pressure on, inch after inch, until his hips met skin and he was all the way inside, Alex’s muscle fluttering round the base of his cock.

Jamie held himself there. Behind him, Sam’s hands settled on his hips, and the blunt head of Sam’s cock pressed against his hole, slick and open from the fingers.

“You’re ready for me,” Sam said. “I’m pushing in now. Stay where you are whilst I get the head in, and I’ll give you the rest once you’re used to the stretch.”

Jamie’s rim fought the thicker head for a second, stretched wide round it, then gave way. The head sank in, tighter than the fingers had been, his muscle clamping hard just behind it, and a rough sound tore out of Jamie’s chest. Alex was clenching round his cock whilst Sam worked into him from behind, and Sam kept the pressure on until his hips met Jamie’s ass and he was fully inside.

Jamie was locked between them. He was buried in Alex and Sam was buried in him, the thick shaft stretching him open with the base pressed flush against his hole. Every breath any of them took moved all three.

He spoke without moving. “Fuck. That’s it. I’m inside you and he’s inside me. Don’t move yet. Just hold it so I can feel how full it is.”

Alex’s hands came up to Jamie’s shoulders, fingers digging in. “We’ve got you right where you wanted.”

Sam’s grip tightened on his hips. “Whenever you’re ready to move, we move.”

Jamie gave himself one more breath. Then Sam pulled back, and Jamie felt his rim drag along the shaft as it slid halfway out. Sam drove in again, and the force of it shoved Jamie forward, driving his cock deeper into Alex until their hips met with a sharp slap.

Alex clenched hard as the extra depth forced Jamie in, and in the same instant Sam filled him completely. Jamie’s breath caught. He drew back halfway out of Alex and thrust in again just as Sam drove forward behind him, and the timing locked into place. Every push from Sam forced Jamie harder into Alex, and every stroke Jamie made into Alex pulled against the cock moving inside him.

They found the rhythm fast. Sam’s thrusts came in longer drives, the thick base of his cock stretching Jamie wide each time, and Jamie matched them, his hips working between the two bodies. He dug his fingers into Alex’s thighs and spread them wider. Sam kept his hands on Jamie’s hips, controlling the depth and the force so each thrust from behind landed exactly where it drove Jamie deepest.

“Fuck, that feels good,” Jamie said. “I can feel your hole gripping me every time he pushes me deeper. Don’t stop. Keep driving me into you.”

Alex was short of breath. “Keep that angle. You’re hitting me right where I need it every time he forces you forward. Keep fucking me exactly like this.”

Sam’s voice came from behind Jamie, the words timed to his thrusts. “You’re so tight round me. Every time you push into him you clench harder on my cock. Keep taking it.”

The pace climbed. The wet sounds of two fucks at once filled the room and the slaps of skin got sharper. Sweat ran across Jamie’s chest and shoulders. He shifted his hips, searching, and on Sam’s next drive the head of his cock dragged across the spot that made Alex’s whole body tighten. The squeeze that answered it was fierce. Sam matched it from behind, pulling most of the way out and slamming back in so the force drove Jamie forward at the exact moment he needed it.

Jamie looked down at Alex on his back with his knees spread and his cock leaking precum across his abs, and at his own cock disappearing between those thighs. He couldn’t see Sam, only feel him, hips working in the same drive and his breath hot on Jamie’s neck. Precum from Alex’s cock had run into the lube and made every slide slicker.

“So full,” Jamie said between thrusts. “Your hole keeps pulling me back in every time he drives me forward. I can feel him stretching me whilst I’m stretching you. Don’t stop.”

“You’re so deep,” Alex said. “Every time he pushes you I feel all of you hit that spot. Take his cock and give me yours.”

“Feel how deep I am,” Sam said. “I’m going to keep pounding you whilst you pound him.”

They were both working on him now, Sam fucking him from behind and Alex clenching round him in front, and Jamie’s abs flexed on every thrust. He could tell how close Alex was from the way his muscle started to spasm round his shaft in tighter pulses.

“Fuck, I’m so close,” Jamie said. “Keep driving me into you. Keep stretching me whilst I fill you.”

Alex went first. His hole clamped down in fierce, rhythmic spasms and his cock jerked, spilling thick ropes of cum across his abs. Jamie fucked him through it with short, deep thrusts, staying buried so the squeeze never eased, and it dragged a rough sound out of his throat.

Sam kept thrusting behind him, and that tipped Jamie over. He drove in one last time with his hips flush against Alex and held there as his cock pulsed hard, pumping thick jets of cum deep into Alex whilst his muscle spasmed round him and Sam kept moving in long strokes through Jamie’s hole. Jamie’s legs shook. Cumming with a cock inside him at the same time wrung a noise out of him he didn’t recognise.

Sam fucked him through the whole of it, then pushed in one last time and held deep. His cock throbbed inside Jamie as he unloaded in heavy spurts, whilst Alex was still clenching round Jamie’s spent cock, so that Jamie was being filled at the very moment he finished filling Alex.

They stayed joined for several breaths, aftershocks running through all three of them. Alex’s hole twitched round Jamie’s cock in smaller flutters and Sam stayed buried as his last pulses faded. Sweat ran down Jamie’s chest and his thighs trembled from the effort.

Jamie spoke first. “Fuck. I felt every pulse of mine going into you and every pulse of his going into me at the same time.”

Alex kept his hands on Jamie’s shoulders. “That was the middle you wanted.”

Sam’s grip on Jamie’s hips loosened but didn’t let go. “You stayed tight round me the whole way through. I felt you cum whilst I was moving in you. Now you know what both ends feel like together.”

Sam eased back first. The head of his cock dragged past Jamie’s rim one last time and a slow trickle of cum ran out of him onto the sheets. Jamie pulled out of Alex more slowly, and Alex’s hole stayed open, leaking a trickle of Jamie’s load to match.

Jamie looked at the mess on the sheets and across Alex’s abs. He grabbed the towel off the nightstand and cleaned them all up, Alex first, then himself, then Sam. When he’d finished he lay down between them, and the three of them cooled off against each other, the sheets sticking a little where the sweat and cum had dried.

His voice came out hoarse. “I want to do it again. God, I’m already thinking about next time.”

Alex draped an arm across Jamie’s chest. “We’ll do it again. Sam’s already said he’s up for it whenever you want the middle.”

Sam rested a hand on Jamie’s thigh. “I’m in. Same setup. Whenever you’re ready.”

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© 2026 Harlan Maddox-Powell. All rights reserved. This story is the intellectual property of the author. No part of it may be reproduced, distributed, or transmitted in any form without prior written permission, except for brief quotations in reviews or other non-commercial uses permitted by copyright law.

This and all stories are works of fantasy. Any resemblance to real people is purely coincidental. All characters depicted are consenting adults. Some works may be inspired by other creators, but all work is entirely original and written by Harlan Maddox-Powell. All characters are adults and have fully consented to the depicted roleplay scenario. In real life, always practise safe sex and enthusiastic consent.