Anal Retentive Asshole

Sam had a drink in each hand as she stepped into her bedroom. Dickless was naked, one foot on the bed, facing away from her. So she had an excellent view as he pressed the small metal plug against his asshole. He was nervous, excited, working blind as he slowly pressed the pre-lubed ovoid into his rear—which slid home with the ease of long practice, his anus clenching about the thin neck, the flared butt of the plug the only part still visible.

By the time Dickless turned around, Sam had already begun sipping her whiskey. She handed the other glass to him, trying not to make contact with his fingers, more to keep her from drinking it as well.

"I...I don't really get a lot of pleasure from...penetrative sex," Dickless said, after he took a sex. "I can get off, but I like...I like a little something in my ass. You know?"

Sam nodded. "I've put a few things up my butt. Not as a regular thing. Just experimenting."

The small confession seemed to embolden Dickless. His eyes grew bright, some color returned to his cheeks. He took another sip of whiskey.

"Do you think you might...want to try it again? Tonight? I've never...but I've always wanted to...with a woman, you know?"

A pleasant buzz settled in Sam's brain. Whiskey always made her feel warm, and she let the robe slide off her shoulders and onto the floor. She stared down between his legs. A one-inch dick was not something she was going to feel with her pussy. On the other hand...for anal sex, a smaller dick might be a bonus. Less painful, certainly. Impossible to push too deep. She wouldn't even have to look at it, and could play with her pussy at the same time. Perhaps it was the ****, but the more Sam thought about it, the more this seemed like an ideal route forward.

"If we're doing anal, I have to prep," she said. "Give me a few minutes."

"Good," he said. "Perfect. Yes."

By the time she had emerged from the bathroom, clean inside and out, the pleasant buzz had spread throughout her body, and Sam smiled as she realized her sense of balance was off a bit. She blinked as she stared into the darkened bedroom, wondering why Dickless had turned off the lights...and then hands caught her and pulled her into the darkness, kicking the door shut.

Things happened quickly. Heavy breathing. Something soft tied over her wrists, which were bound behind her back...probably her pillowcases. Sam stumbled forward, not sure she was okay with where this night was heading...and then her legs hit the bed and she fell, tits first, into the mattress.

"You mocked me. Just like all the other bitches. But now you'll see...you'll feel me, you cunt, you whore. You'll feel me and scream!" Dickless said. A twist of fabric was **** between her teeth, but it was an amateurish gag—no knot, nothing to keep her screaming if she wanted to. Something told her that Dickless hadn't tried this stunt before—and if Sam was less ****, she might be more alarmed. As it was...getting tied up and ****-fucked sounded pretty good right now. As he slopped some lube down the crack of her ass, working mostly blind in the dark, Sam decided to see how this played out.

Dickless' thumbs spread the cheeks of her ass. He was breathing heavy. Something rubbed against her ass...moved down the crack until it found her asshole. It felt like a finger or a thumb...but of course, both of Dickless' hands were occupied. Which left only one option.

Sam knew from experience that anything pressed against your asshole feels bigger than it is. She'd noticed it with fingers, vibrators, and dildos. While she hadn't yet had a live cock up her butt, she had a feel that the same thing would be true here...except if what was poking her in the butt really was his dick, than it felt small even by that standard. A part of her felt sorry for Dickless...and then he pressed forward.

It was stiff. Rubbery. Instinctively, Sam squeezed tight...and then she remembered that she wanted him to fuck her in the ass, and relaxed. Almost immediately, the tiny dick slipped into her anus, like a cork in a bottle of wine.

Except, that was it. Fully sheathed inside of her, Dickless couldn't even reach as deep as Sam did when she got bored and put a thumb up her ass.

"Take that! Feel me stretch out your little hole! Pray that I won't break your ass, you slut!"

Sam rolled her eyes, glad he couldn't see her do it. He began to pump. His buttocks rose and fell, pushing her into the mattress, but Sam could feel that there just wasn't much travel to the cock that slid in and out of her ass. It didn't hurt—small dick plus lots of lube meant that Sam had experienced more painful bowel movements—but it also didn't do much of anything else for her. Up above, Dickless panted and moaned, humped her like a dog with a favorite pillow. Down below, Sam could only stare into the darkness as the dicklet pushed in and out of her ass, never enough to do more than start a kind of burning itch. With her hands tied behind her, she couldn't even play with her pussy.

"I'll bet it feels good, doesn't it?" Dickless said, still talking to himself, lost in his own little world. "I'll bet you never knew it could feel so good! You'll probably cum ten times from your ass alone! I'm going to make you my little anal slut, constantly begging to feel me ruin your shithole! And when you finger your ass so that you can sleep at night, it'll be with thoughts of my cock pounding away at you that you'll nod off to dreamland..."

It was a kind of hell. More than once, Sam thought about throwing him off, or at least asking him to untie her hands so that she could diddle her clit, or they could try a different position, but...the whiskey began to tell. It was dark, Sam was warm...the gentle rocking motion of the bed set her eyelids to fluttering...his voice was a soft monotonous whine, endlessly repeating the same puerile fantasies...and in truth, Sam didn't even remember when she closed her eyes and began to snore.

Wakefulness came some hours later. Dickless had untied and ungagged her before he made his exit. Her head pounded as she rolled off her stomach...and grunted in pain. She wasn't sure how long he had been fucking her ass, but it turned out even a little dick could make her sore, if left unattended. Worse, she felt something wet and nasty down there...and she hadn't heard Dickless mention a condom. Sam shook her head and headed out of the bedroom and back toward the liquor cabinet.

One drink and an asswipe later, Sam realized she was right back where she started at. Unhappy, unsatisfied, terminally horny...and staring at the Fuckr app and wondering if she was willing to roll those dice one more time.