Better Late Than Never
AUTHOR'S NOTE: I found this story on my hard drive; I wrote it a while back. Thought someone might enjoy it. It's not my best work but hey, I've got no shame 🙂
Brian's date was late. He paced up and down in front of his door impatiently, waiting. He had met her in a bar just a day ago; they had hit it off so well that she had asked him out. She was a forceful woman that way; it was one of the reasons he was attracted to her. Another was her body: jet black hair, curly and full, pouting lips, a cute tiny nose, short, powerful muscles, small firm breasts, a nice ass, a real athlete's figure. He had wondered what she was like in bed: acrobatic, would she take charge, would she ride him like a motorcycle. But now it seemed like he would never find out.
As he turned, he heard a knock. Finally, it was her. Smiling in spite of himself, knowing that it was his personal magnetism that drew her to him, made her this eager for him, he turned to open the door. As he did he also acknowledged that his muscled frame, chiseled features, and incredible physique might also have something to do with it.
He was shocked as he opened the door, for there stood his date, but she was wearing a black mask. "Dianne…" he began, wondering what was up, but she put a hand over his mouth, slammed the door behind her, and growled, "Mistress to you, slave!"
Brian couldn't imagine what had gotten into her. She seemed to have gone insane. Grabbing him by the arm, with powerful strides she pulled him down to the basement, to the rec room, currently empty with the ping-pong table folded to one side. Still glaring at him, she took off her backpack and pulled out another black mask for him. "Put it on, slave!"
"Now wait a minute…" began Brian, but he was starting to be aroused by all this domination, and he recalled that, last night, both he and Dianne had drunk a few and chatted about what their sexual turn-ons were in a slightly tipsy manner. They both had been into domination. Now Brian understood, or at least hoped he did. "Yes Mistress," he finished, taking the mask and putting it on.
"Now, the slave will answer a question. Who am I?"
"Wrong, slave!" She pulled out a riding crop; Brian couldn't believe she had one. "Bend over!"
He did so, hoping she wouldn't be too violent. "Pull down your pants." He complied, gritting his teeth. "Now, repeat after me. 'I am the slave.'"
The crop flicked down, leaving a line of fire on his left buttock. "I am the slave," he gasped in pain.
"Good. Now, if you are the slave, who am I?"
The crop hit his ass again, burning. "The Mistress," he managed through clenched teeth.
The pain descended again. "Good. Now beg me to stop, slave!"
Again the crop. The pain was just on the edge of brutal, but Brian found his penis hardening. "Please Mistress, stop!"
"No! I must punish you! You deserve to be punished, don't you, slave?"
Once more the crop struck. "Yes Mistress."
The crop descended more slowly this time, then she brought it around to his face. "Very good. You learn quickly. Now, lick my tool, and maybe the Mistress will lick yours to reward you for your efforts."
Brian was really warming to the part of the slave. He stuck his tongue out and ran it up and down the head of the crop, then down the base and back. He noticed as he did that Dianne had not yet removed her long coat, but she seemed pleased.
"Very good slave. Now, strip for your Mistress, but if you do not please me, I will punish you again."
Brian slowly stood and slipped his shirt over his head, baring his chest, powerful and sweaty, then slipped his pants and boxers down, revealing his already-growing manhood. Dianne seemed excited by the sight of his naked body, and he stood, flaunting himself, until she had seen her fill. "Bend over slave and let me see your ass." Brian turned and bent to touch his toes, and Dianne came up behind him and looked at his red buttocks and his large cock hanging down.
"Mistress has hurt the slave's buttocks with her tool. She must heal them. Beg me to heal them slave!"
"Oh please Mistress, heal me! Please Mistress!"
"Very well slave." From between his legs Brian could see Dianne bend and kiss each cheek lightly, then lick up them and down the crack, running her hands over his stinging flesh. Then she grabbed his cheeks and violently spread them, causing him to cry out in pain.
"The slave is naughty. Mistress did not give him permission to scream. He must be punished again. No more healing." Dianne stood behind him, with his cheeks spread wide, and pressed a finger into his anus, making him wince, but he did not cry out again. Then she pushed in another, un-lubricated, and spread him painfully. "Beg me to punish you, slave!"
"Oh Mistress, I deserve to be punished! Punish me!" Brian was getting very hard from the pain and the anal pleasuring. Dianne withdrew her fingers and took her crop, smacking it down hard on his anus, making him wince, but he gritted his teeth and took the pain.
"Who am I?"
"The Mistress!" he cried in pain.
"Who are you?"
"Thank me for punishing you."
"Oh thank you Mistress, I deserve every stroke."
"Good slave." The blows stopped. "Now, the slave will be rewarded. He will let me taste his cum."
"Oh thank you Mistress."
"Lie down." He did so in a rush. Dianne knelt beside him, bending her head to kiss his already-swollen member. This sent a rush of arousal through his crotch, followed by another as she licked him all over, then sucked his cock, harder than he had ever been sucked before. He was close to cumming in an instant, then she pulled off and with her nails lightly scratched his shaft, then ran her hands down and grasped his balls, taking his cock into her mouth and leaving it there, not sucking. She took his balls and twisted, and he moaned. She smiled at his pain and squeezed, and this was too much for him. Brian ejaculated with such force that it spilled from her lips, his white treasure filling her mouth. She swallowed it with relish as the second spasm rocked through him and he shuddered as another stream, and another, spurted into her open mouth. She took it all in, the excess running down her chin, and kept up her pressure on his balls until he finished cumming. Then, smiling, she rose to his lips and kissed him, passing all his semen from her mouth to his, then commanded him again.
"The Mistress, because the slave ejaculated so well, will reward him again." She opened her coat and for the first time Brian, with his salty semen in his mouth, saw what was underneath.
She was wearing a black leather bra with the nipples cut out and black leather boots. Nothing else. Her shaved pussy was beautiful to behold, pink and wide, and wet-looking he was pleased to see. Her skin was tan and her body looked as good bare as he had hoped. Almost immediately, the taste of his head in his mouth and the site of her pussy made him harden.
"The slave will pleasure Mistress with his jizz. Kneel and pleasure me!"
Brian wordlessly did as she commanded, putting his hands on her pert thighs, feeling the powerful muscles clench as she opened her legs a little and squatted slightly, then putting his face in her pubis and smelling the scent of an aroused woman. He kissed her pussy lips just as she had kissed his lips, passing the semen into her cunt forcefully.
"Deeper, harder, I want to feel it!" she commanded, and he complied, pulling her labia open with his thumbs and probing his tongue deep into the folds of her mons. She would not be satisfied with mere clit licking, he knew, so he plunged his tongue deep into her vaginal passage, pressing up to find her g-spot. He tasted her sweat and arousal, tasted what had to be juices from a pre-date masturbation, and his own cum, spreading through her. He pressed the right spot and she arched her back and moaned "Yes! The slave pleases his Mistress very well!" He ran his tongue over the spot again and again, feeling her walls tighten and loosen, then he slipped a finger down to massage her anus as she had done, but softly at first until she opened, then pressing in.
"Oh Yes!" she screamed above him, and from her taste and feel he knew she was building to orgasm, so he took another two fingers and pinched her clit, which had emerged from its hood. His other finger quickened the pace of its anal penetration, and his tongue lapped at her g-spot. When he pinched the clit she spilled over the edge, screaming unintelligibly, wailing, and palpitating hard on his tongue. He kept pressing, tasting her head and his spilling out onto his mouth and face, feeling the hard orgasm that he had hoped for, and still hoped for, on his dick. She came for several minutes as he kept licking, then panted to a stop.
"Oh my slave," Dianne gasped, "you have pleased your Mistress. Now she will reward you again."
"Thank you mistress," Brian replied, wondering what the reward would be.
"Would you like to drink my piss?"
"Yes Mistress!" Brian wanted to taste her; he had tried piss-drinking with other girlfriends, always great, but not as fulfilling as piss combined with domination.
"Open your mouth, slave, and I will give you my gold. But first, who am I?"
"Good. Thank your Mistress for her piss, slave!"
"Thank you for pissing on me Mistress!"
She smiled. He leaned back on his knees and held his mouth open below her cunt, and she reached with a hand to spread her lips open, then seemed to relax, and a warm golden stream arched out of her pussy to splash onto his face. It soaked him, but he drank all that went into his mouth. She tasted warm and sweet, quite unlike a dominatrix should taste, but good just the same. He could taste her arousal in her piss too, and he wanted more of her.
She halted the flow after a moment, after it had covered his face, and smiled. "Does the Mistress please her slave?"
"Yes Mistress," Brian said, wanting more.
"Then the slave must please the Mistress."
"What is it Mistress?"
"I want to taste your piss, as I tasted your jizz."
"Thank you Mistress."
"Stand up. Don't use all of your piss up or there will be none left for other things." At this Brian wondered what Dianne meant, but he stood and she knelt before him, holding his cock in her hands, still quite hard. Brian found that he had quite a bit of piss in his bladder from the orgasm and the wait, and it was easy to call some up for her. The warmth spread through his cock as he pissed into the mouth of this beautiful woman, piss running down her breasts, in her hair, on her face, and into her mouth, where she moaned and drank.
When she held up a hand, he stopped, much harder to do. "Very good, my slave. Now, for that, Mistress must give the slave another reward. Or does the slave deserve punishment?"
This was a weighted question. "Punishment Mistress. I have been bad, not stopping when you told me to stop."
"That's right slave!" she growled, going to her bag again. "Bend over on your knees and I shall punish you."
Brian expected more spanking, but instead she pulled out a strap-on, put it on, and got behind him. The strap-on was knobby and long, and he hoped she wouldn't drive it all the way into his ass.
"The slave must be punished. Do you want to be punished, slave?"
"Yes Mistress, please!"
"Who is it who punishes and rewards you?"
"Receive your punishment!" she cried, and forcefully tried to press herself into his tight ass. She was rejected, and she growled and pulled him wider apart. The pain was incredible, but also beautiful. When the dildo finally penetrated his virgin ass, Brian moaned in spite of himself. He had never been bi, had never been taken up the ass, but he liked it, even un-lubricated, which was quite painful.
"No talking!" she growled, then pressed in further until his rectum seemed about to split. Then she pulled back and pushed in again. He could feel himself bleeding a little, and it burned, but at the same time it felt wonderful. She began slowly fucking him, widening him painfully each time, but making him a little looser as well. She fucked him harder, pressing her entire length into his anus.
"Who gives the slave pleasure and pain?" she grunted.
"The Mistress!" Brian cried out in pain and pleasure as the rectal penetration carried him to new heights.
Then she pulled out, satisfied. "Thank me for the pain, slave!"
"Thank you Mistress!"
"Has the slave learned his lesson?"
"Then Mistress will allow the slave to fuck her, bring her to orgasm, and cum in her pussy. If the slave cums before the Mistress says he may, more punishment."
She lay down, pulled the strap-on off, and spread her legs, revealing her wet pink pussy. This sight made his cock jump, and he hoped he could hold out. The pain in his anus was bad but fading, and he knelt before her sacred alter of flesh and mounted her.
"Deeper and harder!" she commanded, and he did his best, pressing his hardened penis deep into her hole. He fucked her hard, pressing so deep he breached her, and growing harder and harder until it was all he could do not to cum. He took hold of her hips and raised her rear, pounding into her wildly as she gasped beneath him, her arms outstretched. Finally after an eternity of pounding he pressed what must have been her g-spot, setting her orgasm off again, riding the powerful waves.
Her orgasm on his tongue had been puny compared to that his penis had caused. Her powerful feminine muscles caught his penis in a vise, threatening to crush it. Her legs wrapped around his back and pulled him so deep that his balls were caught painfully between his legs and her buttocks, and all he could do was grind as her powerful muscles spasmed on him.
In the midst of her climax, just as Brian could take no more, Dianne screamed, "Who am I?"
"The Mistress!" he groaned, fighting back orgasm.
"Cum in my pussy slave! Fill me with your juice!" She was already almost full to bursting with him and the other juices, but he released and shot his whole load deep into her vagina, deeper than he had ever cum before. All his past sex melted before this; this was really an orgasm. She was so hot and powerful beneath him and around him. She screamed with the force of his ejaculation as they both were drenched in sweat and the orgasms finally subsided.
She did not release him from the grip of her powerful legs or muscles when they had finished though. "Who's pussy do you cum in?" she asked him breathlessly.
"And who's pussy do you worship?"
"As a reward for your powerful stamina and even more powerful orgasm, which gave the Mistress great pleasure, she will let her slave piss in her pussy."
"Thank you Mistress." This was a new wrinkle for Brian, but it sounded fine, with her tight muscles around him.
"Don't use it all up; there's more for the slave's piss to do," she grinned softly.
"Very well Mistress."
He let the last drops of semen spill from his cock, then opened his bladder, much harder to do now. But still, he managed a trickle, then a stream, then with force. It jetted into her deepest space and she moaned, then screamed as the powerful jet filled her completely and pressed her muscles away, spurting out of her lips. Her pussy was all warmth and wetness now, but just as Brian was about to run out, her muscles clamped down again, cutting him off, and Dianne had another shuddering orgasm from the force and fullness of his urine. The palpitations were weaker now, but they served to re-energize his penis, hardening it again as she rolled over him, the liquid from all the sex and the piss spilling out onto her legs, her stomach, him, and the floor.
"Oh yes slave!" she moaned after a minute. "Your piss is hot in my cunt. But now the slave must learn a lesson. Too much pleasure will make the slave soft. Kneel and bend over!"
Brian did as she commanded, seeing her pull the strap-on back into position over her dripping cunt. "Does the slave love his mistress?"
"Does the slave want Mistress' dildo up his asshole?"
"Yes Mistress, please!" Brian's anus still hurt from the last time, but he wanted more.
"Since the slave has been so good, Mistress will loosen him so the lesson is not too painful." Brian was relieved and happy. Dianne knelt behind him and bent to put her face on his buttocks, then she darted a clever tongue into the crack and licked his tight hole, sighing with pleasure when she tasted blood. His ass was still tight, but her tongue made him smooth and wet and opened him slightly. Then she rose. "Who am I?"
"Where does the slave want Mistress?"
"In my asshole!"
"Good." Then she thrust her dildo several inches into Brian's rectum, bringing the pain back. It subsided as she worked her way in and out of him, more slowly, loosening him gently until he was wide enough and then she began fucking him, reaming his asshole with her long studded dildo. Brian sank onto his elbows with weakness as the studs rubbed his flesh, feeling it penetrate him deeper than ever, feeling her pure power behind the thrusts. His cock hardened, then he realized that she was stroking it with one hand.
"Cum slave! Cum with me up your ass! Cum all over the floor!"
He was close, and with effort he did as she commanded, the orgasm building deep within him where he was being probed, then exploding through his balls and out onto her hands and the floor. His and her ass were bouncing as she continued to fuck him harder, thrusting until he was sure she must break through and puncture the place where his semen still welled from. Then she moaned and jammed into him, taking her hand from his dick and rubbing his jizz all over herself as she had a shuddering orgasm above him. Her hips shivered, her pelvis thrashed, and she buried her strap-on deep in him again and again, forcing more cum out of him onto the floor as both panted to a standstill.
Brian was too weak to stand, but Dianne pulled out of his now-wide-open anus, shucked the strap, and purred, "The slave makes his Mistress very happy. Has the slave learned his lesson?"
"Yes Mistress," he panted.
"Then let me reward the slave again. I will piss in his anus so he knows what it's like to have cum inside him."
"Oh thank you Mistress." Brian was excited. The anal sex had been great; he was eager to find a man to try it with now, or maybe two, or a man and a woman. Now she wanted to piss on him again, in his ass, which he was sure would be just as good as everything else had been that night.
He arched his ass into the air and spread his legs to give her a better shot at his asshole, which felt like it was miles wide. She smiled, stood, opened her lips with a finger, and seemingly effortlessly began to piss. She must not have taken a piss for a week leading up to this, Brian thought as the golden stream arched onto his buttocks, then she adjusted her aim and sent the golden warmth deep into his asshole.
It filled him like nothing he had ever felt before; as full as her dildo but softer, warmer, wetter. It caressed his abrasions and filled him with warmth. She stopped, but let him sit for a moment, ass in the air, with the hot piss filling every cranny of his rectum, then she grinned. "Quid pro quo, my slave," she murmured softly, as if the lines between slave and Mistress were blurring. "You must take me up my ass."
As she knelt and Brian stood, he felt the warmth drain out of him onto his legs, and he hoped the soon he could feel that fullness again, maybe with her piss, or maybe with another man's cum. He knelt behind her, and she girlishly waggled her rear as she opened her legs, to bare her beautiful pussy, dripping wet, and her tight brown anus. Without being told he licked her, running his tongue over her musky ass, dipping it into her rectum to ease his entrance. His cock, he knew, was already dripping from other sex.
"Mount me, my slave!"
He complied, opening her cheeks with his hands, getting behind her, then slowly pressing his cock into her tight hole. It was as tight as her pussy when she came, and he hardened, widening her as he pressed in deeper, feeling his penetration, feeling her reflexive contractions around his penis. He had never taken a woman up the ass before, and it was pleasantly surprising. He eased all of his large shaft into her and they both sat for a moment, as if growing used to the penetration.
"Fuck me harder!" she groaned, and he pulled back and slammed himself back into her rectum again. She screamed and tightened on him, then got control and loosened slightly, allowing him to pull out and thrust again, more easily this time, and again, until they had built up a rhythm.
She moaned with every thrust and tightened, but her ass muscles were weakened by constant assault and her tightness remained only pleasurable to Brian, not impossible. His hips pressed into her firm round ass with every thrust and he held her around the waist to secure her. Slipping an hand down, he teased her open pussy then pressed a finger in, then another, spreading her wide, until she screamed again, but not a command, just a scream. Her ass spasmed and then opened wide and she came, her cunt rocking on his fingers, her breath coming quick with every thrust of his penis into her asshole. "Cum in my ass!" she moaned in the midst of her orgasm, and Brian, who had been approaching again, was happy to oblige, filling her tight anal passage with his warm thick head. He took his hands and rubbed her juices all over her back and him, and they both bounced to a standstill.
"Oh yes, my slave, you have done well. But I think you haven't filled my anus up as much as you filled my pussy. I shall have to punish you…" She giggled in a most un-dominatrix-like way. "…Unless you can complete what you started. I've had your beautiful warm piss up every hole except one." She tightened her anus.
Brian was overwhelmed with pleasure. He was going to fill this beautiful woman's tight rectum with both his head and his piss. The urine welled up inside him without his bidding and sprayed like melted gold from his dick straight up her asshole. He felt the warmth well up around his cock and gush out onto both their bodies as she moaned and he emptied his bladder hard into her wide open anus. She screamed as it jetted into her, filling her to bursting, and the added pressure made her cum again without him even touching her pussy. Her frenzy of orgasm, the pressure of her muscles, and the warmth and wetness of his piss drove him over the edge too, once he'd finished pissing, and they both moaned as one, his jizz spilling into her already full anus, making her gasp in pleasure.
When the climax ceased, she moved until he slipped out of her and they lay side by side, too spent to do more. "Dianne, that was…" he gasped.
"Next time we should invite some friends," she laughed dryly. They both slipped into blissful unconsciousness, dreaming of next time, and the time after that.