Crybaby

By the time Sam stepped back into the bedroom, a glass in either hand, her robe fallen open, Dickless was naked, sitting on her bed...and blubbering. Sam was unable to keep a scowl off her face. She wasn't inhuman, and tears could pluck at her heartstrings, but "pathetic" wasn't exactly a turn-on.

He took the glass with a sniffle.

"I'm sorry," he moaned, eyes red with tears as he brought the whiskey to his mouth. "I just...this always happens to me. I thought...I thought I could last this time, but..."

Sam sipped her own whiskey. The warmth of her first drink was spreading out from her stomach. She sat on the bed next to him, not sure how to proceed.

"Look. So you've got a micropenis. It's not the end of the world. Penetration is like...not even the most important part of sex. Making a woman cum is the important part of sex, and there are lots of ways to do that without a big pussy-breaking dick!"

She looked at him to see if the pep speech was working. Dickless sniffed, and rubbed at the tears on his cheeks.

"But I've never..."

"And you're never going to, unless you make a woman cum!" Sam said. "That's what being a man is about, not having some huge, throbbing, cunt-stuffing, cervix-bumping third leg..."

It was the wrong choice of words. Dickless began to shake, face screwed up, mouth twisted into something between a smile and a grimace, tears leaking out of his eyes. Sam grabbed the half-empty glass out of his hand before he spilled whiskey on the carpet...and then emptied it into her mouth. She set the two glasses aside on the nightstand near the bed and stood in front of him, her shaven pussy only a foot from his face, but Dickless too busy crying to even look at it.

She grabbed his face with both hands and tilted it up to look at her.

"Look. I need to get off. Do you understand me? And your job is to help me make that happen. So I'll make you a deal: I'll help you cum, and then you can help me cum. Okay?"

He sniffed. "O...okay. B-but I was really hoping...I mean I wanted to...fuck you."

Sam looked down at the pimple. Maybe it was the ****, but she had an idea...

Ten minutes later, Sam was on her back on the bed. Dickless had finally stopped crying...but the look on his face was of profound concern.

Erect, his stub of a dick was little more than an inch long behind the head. Sam's solution to his crying jag had been the miracle of duct tape...and one of her slim, purple vibrators. An inch of tape, wrapped three times around the base of his prick, held it about as securely as possible, like the bayonet on a rifle. They'd wrapped the condom on top of that, and then more duct tape. The result was a Frankenstein's monster of a pseudo-penis, but by that point the room had begun to spin and Sam was far, far past caring.

"It's...tight," he said. The quake of the vibrator caused the tip to move in small circles.

Sam grinned and used her fingers to spread her labia.

"Don't be a fucking baby. Man up and fuck me with your hard cock, stud."

Hesitant but excited, Dickless guided his pseudoprick toward Sam's pussy. He missed, the narrow tip wiggled away from her vagina and hitting her urethra.

"Ow. Hey, watch where you're poking that," she said.

On his second try, Dickless found the right hole. Sam held her pussy lips apart and kept her legs wide. She did her best to encourage him.

"That's it...easy does it...oh, that feels nice. Come on Rich...you can go all the way..."

Once most of the dildo was inside of Sam, Dickless' tiny prickhead finally brushed her pussy and pressed inside...and that was okay, too. A nice little welcome bit of girth as the silicone rod vibrated inside of her. She grinned and moved her hands to rub at her clit. With increasing confidence, Dickless began to move on his own—shifting his hips as he hovered over her. Cautiously, he raised one hand to touch her breast...and Sam smiled and nodded at him, giving him permission to continue.

They moved like that, the two of them. His head dipped down to the hollow of her throat, to kiss her there. Her hips began to shift to meet his thrusts, which became bolder and more confident. The heat began to build up within their bodies, **** and lust mixing together. Sam felt that sense of expectation and anticipation build inside of her—the sensation that she had wanted, needed, the feeling that would make it all worth it—and perhaps that was where it all went wrong. Half-**** and excited as she was, on the cusp of climax, Sam squeeze down too hard...and as Dickless drew back, the tape, toy, and condom tore off.

He yelped...and desperately lost in his rhythm, Dickless plunged back into Sam's slit. Except Sam's pussy was plugged, and his staff-like microprick pushed into the absolute wrong target.

Sam had heard of people that inserted things in their urethra, but had never tried it herself. Now, she found out why. Sudden, intense pain shot through her as something small but still far too large tried to **** its way into a one-way hole. She shrieked and thrashed beneath him—but perhaps Dickless thought she was cumming. Perhaps he didn't care. All Sam knew was that she could hear his breath like a steam engine...feel the stabbing, shooting pain as he tried again and again to fuck her urethra...and then his entire body seized and his hips shook and she felt a hot wetness and a sudden burning need to pee.

Then Dickless started to cry again.

Tears dripped down on her as he bawled, and he held Sam close as he cried into her shoulder. Muffled words of thanks came through the caterwauling as he watered her shoulder...and down below, as Sam worked to squeeze out the vibrator, she sighed in agitation. All that, and she still hadn't cum yet...