Tailpipe 3 (Patreon)

Peggy searched her mind for the word for it—dildo. It was a dildo, but bigger than any of the cocks it was meant to emulate. It had to have been twelve inches long and as big around as her wrist! And Angie meant it for her asshole?

What’s more, it was not at all a realistic looking simulacra of a phallus, but wicked, evil-looking, with prickly red bumps that reminded Peggy of demon’s horns. Angie fastened the harness around her slender hips, centering the thrusting shaft so that its base rested against her own tender sex.

“I know you’re the self-sacrificing hero type,” Angie said, “but don’t you worry about trying to reciprocate when you’re taking this baby. You’ll have way too much to concentrate on getting this in your backdoor to worry about how I’m making out; trust me, I’ll be enjoying myself plenty.”

“But it’s… so big!” Peggy quavered, wanting the nasty looking thing, but not sure if she was loose enough—especially her asshole. “It’ll hurt! I don’t think I can take it!”

Angie already felt the hot blood congregating in her groin, pulsing against the base of the dildo like it was part of her body, making her feel like she was aching to bury this stiff tool in Peggy’s puckered opening.

“You can, English. Trust me. And I won’t let it hurt too much. Hell, that clit of yours looks pretty turned onto me. I don’t think you’d be so excited if you really thought you couldn’t take it.”

Peggy squeezed her thighs together, as if to hide her swollen clit, but of course the pressure just made it feel better. She couldn’t help but spread her legs wide again, trying to alleviate the radiating anticipation. She was breathing hot and heavy when Angie retrieved a tube of K-Y jelly from her purse.

“They should give this away free with a wang like this, but I suppose they sell few enough of these things as it is. Not many daredevils like you and me, Peg. With this, you could damn near take my fist up your ass.”

Peggy laughed at herself. That idea was truly ludicrous, yet she felt a tingle of anticipation anyway. Not in her pussy—that was burning in its own way—but for the first time in her ass. She stared at Angie’s weird, huge… strap-on… and tried to mentally compare its size to her anus, not that she’d ever thought about, had any idea of, the circumference of her asshole. What it could take and how much it could take. She could only suck in breath at the thought of her virgin body stretching that much, even if it could do it.

But the thought of appeasing Angie sent chills rushing over her spine. Yes, the more she thought about it, the more she knew she had to do it—had to totally give herself over to Angie and not just have a few kisses, a little rubbing. She puckered her anus tightly and then made it relax, telling herself There, you see? You can let that in. It’ll be no different than letting something out.

Angie saw her pink sphincter clenching and unclenching; her pussy swelled against the base of her strap-on with its own throbbing pulse. Peggy always turned her on, but the thought of making her tender, untried asshole stretch wide to swallow her dildo…

She didn’t like the idea of causing Peggy pain, but she knew that pain would turn into immensely satisfying pleasure soon enough, and Peggy was just the type to push through the hurt and appreciate that hard-won ecstasy on the other side.

Angie giggled lightly, imagining how eager Peggy would be for it after that first time. Maybe she’d learn how it felt—Peggy scurrying after Angie, trying to get her attention—which Angie would happily give her. She’d pay all the attention in the world to that heart-shaped ass Peggy teased her with every time she so much as turned around…

“Keep your legs high, English. Here, let’s get you situated.”

She took the headrest off one of the chairs in front and put it under Peggy’s ass. With it in position, Peggy’s butt was arched out at just the right angle for what Angie wanted to do to it. Angie looked hungrily at the girl spread out for her in the backseat of this cab—wearing a half-unbuttoned buttondown and open suit jacket, but nothing below the waist but a pair of shoes, which Angie doubted she would part with.

Even at a time like this, Peg would want to be ready for anything. She could do her job without pants, but not with her bare feet on the jagged, who-knows-what-strewn pavement by the docks. Angie giggled at the thought of Peggy running around, shoed but bottomless, toting a gun…

Peggy was not amused: “If you find the spectacle so risible…” she began, moving to get rid of the headrest under her hips.

Angie grabbed her hand and forced it down. “S’not you, English, relax. I was just imagining—“

“What?” Peggy demanded when she trailed off.

“Would you let me take your booties off?”

Peggy’s brow furrowed. “I don’t think that’s a good idea, Ang. I have a dangerous job and if someone were to attack us…”

Angie grinned.

“I’m serious! If these windows broke, the glass—“

“You’re adorable.”

Peggy jutted out her lower lip in a pout Angie would’ve rejected from her own acting for giving the cheap seats too much. “I’m glad you can find humor in my commitment to duty instead of passion in my naked body.”

“Maybe I’m a little bit in shock, Peg. You are a lot to take in.”

“And ironically here I am, not taking anything in at all.”

Smiling fondly, Angie parted Peggy’s blouse, undoing the last few buttons so she could totally move it off to the sides of Peggy’s body and see those plump, perfect breasts the way they were meant to be seen.

She licked her lips. She bit them. She almost drooled, wanting to bury her face in that plentitude, but there’d never been a better time than now to initiate Peggy into anal sin. She couldn’t let that wait.

So Angie let herself be tempted by the sight of Peggy’s naked sex, her asshole, both surrendered to Angie’s desire, ready to be used in any way she wanted. Angie’s tongue flitted through her lips while she stared between Peggy’s ample buttocks at the small, pink hole. It seemed to be frantically clinging to the tightness Angie had already reduced with her licking, the round muscle convulsing, just begging to be penetrated.

Peggy looked between her legs at Angie—she was too dignified to whimper, but there was definitely a crack in her laconic cool, a subtle tone of need to her words that Angie wished she was good enough to put into her acting. “Angie, please… do it to me… I’d like you to do it to me now. Yes, I want you to… to do that perverse thing you want to do… I want you to enjoy it… go on… it’s sick and it’s wrong and I want you to do it to me!”

She shook her fat ass—Angie let out a moan at the thought, the fact, that Peggy wanted her strap-on inside that tiny little opening of hers.

“You’re gonna love it, baby. I’m gonna make you love it.”

Peggy watched Angie squeezed a huge glob of lubricant onto her fingers. Then she touched it to Peggy’s anus, and despite what it was a prelude to, the cool touch of the slime on her nervous, reeling opening was soothing, good.

Peggy pulled her buttocks apart, felt a tremor shoot to her brain at the feel of her asshole opening with the motion, and the caress of the jelly on her taut, twitching hole… desire swamped her brain. Two of Angie’s fingers massaged the gel into her rim and she let out a gasp. It felt strong… just that little thing felt impossibly strong… maybe it was her nerves, but her pussy had never gotten that feeling from a few fingers!

Angie’s fingertips slid sensuously around Peggy’s puckered opening. The gooey lube made them glide easily along each sensitive crinkle. Angie’s touch went round and round, thoroughly smearing Peggy’s hole. Then they pushed into the area they’d just slathered. Pressing into that weakening tightness gently, but firmly, until her anus had no choice but to yield.

Peggy’s lips parted without a sound, not able to produce even a single noise to describe the feeling of being entered in a space she’d thought would never be touched. Mentally, she wanted to flee from the perverse, alien sensation, but Peggy wouldn’t allow herself to. She centered herself on the discomfort, on the pain, and made her asshole relax. Let it open to the two fingers sinking into it.

They went deeper and deeper and deeper until there was no more of them to enter her. Peggy’s body shook, her anus straining, tingling as it expanded to accept the fingers that were stretching them. The feeling seemed to go on and on and when Angie took her fingers away, ending the stretch before her asshole was fully defeated, Peggy felt a sense of disappointment. She knew that, technically, she’d just been fucked in the ass—but she didn’t feel fucked and suddenly, she wanted to be. She needed to be.

“Mmmmmm,” she sighed, feeling a sudden throb in her cunt as the arousal there pushed to the forefront of her mind, blocked out by that sensual torment earlier. Peggy could only moan, wanting that exquisite pain to come back and cut into her sex’s needful pulse.

Angie spoke softly, gutturally even, so unlike the peppy, cheerful voice Peggy was so used to. “You like that, huh English? Yeah, you like having my fingers in your butt. Well, now you’re going to have my cock in your ass. That nice, fat ass—I’m gonna leave it gaping open from having this dick all the way in it. I’m going to ruin your ass, Peg… you’re never going to sit down the same way again, ever. And that turns you on, doesn’t it? Just hearing me tell you I’m going to destroy that pretty little hole, it should be scaring you. But it’s making your pussy clench. I can see it.” She reached between Peggy’s thighs. “Open up and let me in.”

Peggy spread her legs and Angie shuffled on her knees to Peggy’s splayed ass, throwing her open legs over her shoulders. Peggy’s ass was raised even higher. She watched, keening in a not-quite-whimper, as Angie aimed the strap-on between her legs. Angie nudged it forward, into Angie’s pussy, separating her cunt lips to swallow whole the menacingly large endowment.

“OOOOPPHHH!” Peggy groaned, her sex seeming to expand hugely with Angie’s strap-on inside it. Every time she thought she’d reached her zenith, stretched as far as she could go, more of the dildo sunk into her. It didn’t stop until she felt the press of Angie’s skin against her own flaming body.

“Aaahh!” Peggy moaned full-throatedly, her usual reserve totally gone, given over to these lascivious sensations she couldn’t help but feel with Angie impaling her the way she had. “Ooohhh… oh… ANGIE!”

Angie ground hard against her, digging her strap-on as far as she could into Peggy’s sex. Peggy’s labia gripped the shaft tightly, her folds convulsing around its unyielding stiffness. Angie actually grunted as she rutted into her once-friend, now-lover—rubbing her surpassingly tender sex against the base of the strap-on.

With every stroke, she knew she was making Peggy feel what she was feeling… an almost unimaginable degree of ecstasy… she got off on seeing Peggy sweating, moaning, her face contorted in an agony of delight.

But she wouldn’t keep going, wouldn’t let Peggy get used to this pleasurable delirium and lose her dreading anticipation of being sodomized. As suddenly as she had driven herself into Peggy, she pulled the strap-on back out. It glistened with Peggy’s copious juices, shining in the moonlight like some radioactive mineral.

That wasn’t enough for Angie—she wouldn’t risk an overabundance of friction spoiling their fun. She slapped more lube onto the dildo and rubbed it in, squealing inwardly at the thought that she was mixing it with the arousal Peggy had left dripping off her strap-on.

Then, urgently, Angie got back between Peggy’s slender legs. Her strap-on thrust out from her loins like a readied weapon, straining to bury itself in Peggy once more.