Tailpipe 4 (Patreon)

Peggy eyed the big dildo that had just brought her to the brink of climax and she wiggled her ass. Her cunt was wet and juicy, throbbing after it’d been stretched and then released from that ecstatic tension. Her inner muscles tingled all over; her clit was swollen and spiking.

She wanted that cock back inside her, she didn’t care if it was real or not, she didn’t care what hole Angie put it in. She wished only to return to that connection Angie and she had fleetingly shared—her getting off on Angie’s fucking and knowing Angie loved it too.

“Oh, Ang… please… let me have it. I want you to put it in me! Give it to me… God, let me feel it back inside me!” she moaned, tightening her legs around Angie’s shoulders as if to pull her in.

“That’s just what I’m gonna do, English,” Angie said, her clit twitching, her cunt pulsing wherever it touched the harness of the strap-on.

She fingered Peggy’s ass and saw, for a heart-stopping moment, that Peggy welcomed, entirely accepted the penetration. She wanted even more, just like she said! No subterfuge there; she’d gotten the absolute truth out of Peggy.

“I’m going to fuck you right here. Don’t you tense up, Peg. Relax. Keep your hole loose. I’m going to give it to you slow. You’re really gonna feel it. Look me in the eye, English. I want you to remember I’m the one going into your butt.”

“How could I forget?” Peggy moaned.

Peggy shut her eyes—the tingling between her legs was too much to bear along with the sight of Angie. She sighed, knowing only the feel of Angie fingering her ass; then moaned when she felt the strap-on touch it.

Relax, she told herself, you have to relax if you’re going to take all that.

Not that it felt like she had a choice. Her asshole was opening wider—it had to, with Angie’s dildo sinking into it. One of them had to move and the strap-on was simply made of sturdier stuff than her tender little anus.

“Oh… ohhh!” she keened. “Uhhh! Oh, oh! Unh! Don’t stop, don’t stop! Angie, yes! But gently, please, it’s—oh God, oh blimey—it’s inside me! Hnnnn! Ang, you’re really in there! You’re fucking my arse!”

“Not yet,” Angie purred. “But not long now either. Jeepers, Peg, it’s going in like you’re made of warm butter!”

Her asshole opened, opened as much as it could before it had to stretch to let in its intrusion. Peggy felt the corona of the strap-on probing inside of her. It was good, but slight. Enough to build anticipation more than pleasure. The cockhead wasn’t even all the way through her anus yet.

But Angie kept pushing and her asshole weakened more and more. Until she had half of the big knob inside Peggy’s rectum, the Englishwoman cringing from the mounting pain and how it outstripped her sense of pleasure.

“Slower… go slower, Angie, it hurts! Oh! You’re hurting me! Don’t stop, just—guhh—remember it hurts!”

“Shhh, English, I’ll go slow, I promise. But you have to relax. Focus, okay? Make that little hole go soft for me. Let me in. I’m going as slow as I can, but it’s gonna hurt at first. But once you open up and get it in you, it’s going to feel better than anything you’ve ever had before.”

Angie shifted position, arms and legs straining to hold herself up against the desire to bury her strap-on in Peggy’s fat ass. She held back though. She couldn’t hurt Peggy, couldn’t cause her an iota more pain than necessary.

The heat of Peggy’s tight asshole flooded her strap-on, running through it to Angie’s cunt, telling her how much the spy would enjoy really being sodomized. Still Angie held back, working the dildo in only a little at a time. Soon enough, she knew Peggy would be begging to be ass-fucked as hard as Angie could give it to her.

Now Peggy moaned nonstop, voicing every little bit of progress Angie’s strap-on made into her rectum. Every millimeter that her sphincter widened made her whimper and wince, and it opened wide.

Angie pushed a little more firmly with her dildo, forcing the soft, slick grommet to part over its tip. Peggy’s moans got louder. Then the bulbous cockhead was at the apex of opening her up, her anus as wide as it would go, and the entire knob of the dildo, the whole thing, suddenly popped inside of her ass. Peggy gasped in pain.

“AAHHH! AHH, OH, TAKE IT OUT! IT HURTS! ANGIE, IT’S TOO BIG! AHHH! UUUHHH—THERE’S SO MUCH INSIDE ME! I CAN’T TAKE IT, ANGIE!” Peggy cried, twisting and jerking her head about.

Her asshole stretched almost to the breaking point. Pain shot out of her violated innards to fill her mind. Her toes curled and she keened again and again, her anus throbbing, stretched taut until there was blessedly nothing else for it to engulf.

“Shhh, English,” Angie purred to her. “Be quiet. You can do it. Shh, relax. Let it open.” Peggy didn’t stop moaning, so Angie goosed her, speaking louder, more firmly. “I said open up! Let this cock into your butt, Peg! You aren’t keeping me out!”

With tears of pain dewing her eyes, Peggy’s muddled mind registered Angie’s voice. She could only think of how she trusted that voice, loved that voice, and so she did as it asked.

Her asshole throbbed, but the painful pulsations from it being reamed weren’t as intense now. Peggy calmed down, once more concentrating on not tensing up—on allowing her asshole to let in all that Angie had to give it.

“O-okay, Ang… I’m okay now,” she stammered out, shifting her legs on Angie’s shoulders. “Yes… I’m fine now… I can take it!”

Angie looked into Peggy’s wide eyes—so shrewd for all their innocence—and her heart melted for her. She hated how much Peggy was hurting, but she knew the worst of it was over. She just had to push a little more and then it would really feel good.

So she did, before Peggy had time to dread being sodomized more, before she could worry about it. Worrying was the worst part. Soon, she’d be feeling the best.

Peggy groaned, feeling the strap-on shoving further into her ass. It pained her as her rectum expanded—the taut new space filled with every fat inch of Angie’s dildo. She was being stuffed with cock and it hurt! But not as much as she’d expected. Peggy bit her lip and resolved to bear the pain, wanting to please Angie as much as Angie was trying to please her.

Peggy grunted over and over again while her asshole opened wider. She wanted to believe Angie’s promise that soon the sodomy would feel incredible, better than any sex she’d ever had. She tried to keep her asshole as relaxed as it could be when so much was spearing into it—the strap-on gored deeper into her.

Angie threw back her head, eyes closed. She most definitely enjoyed ass-fucking Peggy Carter. The sight of it was almost too much for her; she didn’t want to come while Peggy was in so much pain, but gosh, she was actually that deep in Peggy’s poor ass! She groaned with the tight, slippery warmth of Peggy’s anus coming closer and closer to her tender groin, taking more and more of the strap-on in its pained grip.

Angie just wished she were a guy so she could feel that embrace on her Johnson instead of just looking at it. But no, she liked being a girl too much for that. She slowly kept rutting into Peggy, satisfied that male or female, she at least got to give Peggy the joy of being sodomized.

The pain corroding Peggy’s thoughts finally began to twist into pleasure. The more of the strap-on fucked into her ass, the better it felt. She already felt crammed full, her asshole filled up like a balloon under a running water faucet. Her asshole was anything but empty and she was getting used to the sensation, liking it. Yes, she loved it!

“OOHH, Ang, feels b-better! Oh, it’s… it’s nice! It doesn’t hurt anymore! Oh yes!” she trilled, her strained smile spreading into something real.

Angie grinned back at her, glad to know that she’d been proven right. But of course, she’d known all along.

“Blimey, how much of it is in me?” Peggy asked. “Feels like a mile!”

Angie glanced down, patted Peggy’s splayed hindquarters lovingly. “About three-fourths is in. You want all of it now?”

Peggy pondered it for only a second. She felt the tightly stretched, pulsing walls of her rectum. They didn’t hurt—not as such—she wouldn’t say they felt entirely good, but they did feel like nothing she’d ever felt before. Like something only Angie had ever done to her.

“Do what you want,” she replied, knowing exactly what that was. “Just, please… go slow?”

“Alright, English. Nice and slow. And all the way up your ass.”

Angie eased the strap-on back a few inches, then thrust it forward again. Peggy cried out in delight, pleasing Angie.

Angie drew back again, then drove herself between Peggy’s buttocks until only a couple of inches were still outside her anus. Peggy couldn’t keep from moaning, her taut inner walls being massaged by the pumping strap-on.

Chills charged across Peggy’s spine, reminding her of her pussy, on fire, juices flowing out of it in a steady stream. Her inner folds were swollen, trembling, begging for the same attention her ass was getting. Like iron fillings pulled to a magnet, her hand snaked between her legs and she started rubbing at her slit.

Immediately, the lingering pain of being sodomized was eclipsed by twinned pleasures of both her cunt and asshole. The good feeling shot straight to her brain.

“Uuuhh, Ang!” she moaned, swiveling her hips, thrusting her ass out to Angie’s pumping. “Feels good… feels amazing… oh YESSSS!”

The pleasure in her clit and anus now filled her mind. Her asshole relaxed completely, allowing Angie’s strap-on to sink into it until only one last inch hadn’t fucked her. Her sphincter clenched shut, gripping the dildo so tightly that Angie could barely move it.