Carlotta's Captivity Pt. 03

The Master next took a marker and drew a line in the middle of each of Carlotta's cunt lips. "Your stroke has to hit within those lines, so I would aim for the exact center of her cunt if I were you, otherwise the stroke is disqualified," he told Anna. He moved over to the wall and selected the same thin flexible crop he had used on Carlotta a few days before and handed it to Anna. Anna swished it through the air a few times getting a feel for the crop. Anna played a lot of tennis and she was sure she could win this one. Finally ready, she moved between Carlotta's legs, raised the crop and brought it down with all her might.

The "crack" of the crop was almost immediately drowned out by Carlotta's scream as the cruel crop hit exactly between her cunt lips, shoving the outer lips aside and impacting directly on her tender core and clit.

"Excellent," the Master complimented her. "That was 93 miles per hour. Some pitchers can barely do that." He had to speak up since the room was filled with the sound of Carlotta's moans and crying. The Master lowered Carlotta's legs to the mat and released them. Next he directed her, still sobbing, to a long table, rather like a gynecologist would use. He had her stretch out on the table and fastened her feet in the stirrups, and pushed the two arms out, spreading her legs wide. Satisfied, he slipped off his clothes and walked round to her head. "Get me hard," he ordered.

Anna watched all this nervously. She had previously had no idea how large the Master's endowment was, and her eyes got large as Carlotta sucked him fully erect. "God this is probably going to hurt," she thought, thinking about that cock burying itself in her ass.

In the meantime, the Master was fully hard and moved back around between Carlotta's legs. He placed his cock at her entrance and began to slowly push in. As usual, he eventually came up against the barrier of her cervix. Carlotta was not really surprised when he kept pushing, and groaned as her cervix was once again forced to open and admit his fat cock.

Anna was continuing to watch and was puzzled at first when he kept pushing after it was obvious that the Master was already against Carlotta's cervix. "He's got to be already all the way in," she thought. "Where does he expect more to go?" Carlotta's groan answered her question as the Master's cock once again started to move deeper in Carlotta's cunt. "God," she thought. "He's actually fucking past her cervix. That's got to hurt."

The Master was enjoying the "double fuck" every bit as much as he had the first time. Standing between Carlotta's wide-spread legs, he felt like he was able to go even deeper than before. He began a shallow fuck, moving just enough to force his cock in and out of her cervix. Eventually he lengthened the strokes and began pulling all the way out, and then slamming all the way back in to the hilt, accompanied by a deep sucking sound with each sloppy stroke. After another ten minutes, he began to get close to cuming and motioned Anna over, and told her to get on her knees. At the last moment, he pulled his cock from Carlotta's cunt and shoved the first inch or so into Anna's mouth, and then began to shoot shot after shot into her mouth and down her throat. There was so much that Anna couldn't swallow it fast enough and some ran out of her mouth and down her chin. The Master pulled out and shot the last spurts on her face. Anna started to wipe it off with her hand, but the Master stopped her. "Leave it," he ordered.

The Master unfastened Carlotta's feet and helped her up off of the table. "Lick Anna's face clean," he ordered her, forcing her to her knees beside Anna. Carlotta blushed, hesitated and the sighed. Defeated, she leaned forward and stuck her tongue out, licking the ropes of cum off of Anna's chin and face. "Don't swallow it," the Master ordered. When she was finished, the Master ordered her to open her mouth and show him the cum. She complied, expecting what the next order was going to be. "Now kiss Anna and share it with her," he ordered. "And I want to see lots of tongue from both of you."

Reluctantly, the two women kissed, each of their tongues invading the others mouth and tasting the Master cum. The Master watched closely. "That should be enough; it's time to move on to Anna's punishment."

At the Master's orders, Anna positioned herself on the same apparatus where Carlotta had lost her anal virginity. He strapped her legs to the vertical wall, spreading them wide and secured her torso to the inclined front part. Just like he had with Carlotta, he left Anna's hands free. Next he raised the back portion pivoting the entire stand so that Anna's ass was pointed directly at the ceiling. Finally he positioned the chronograph and handed the crop to Carlotta. "Reach back and spread your ass," he ordered Anna. Anna complied, blushing almost as furiously as Carlotta had in the same position. He placed two marks, one on each side of her ass, about an inch out. "There's your target," he advised Carlotta.

Carlotta stepped up and regarded Anna's ass for a moment then raised the crop and brought it down directly on Anna's tender little asshole. Anna shrieked loudly, releasing her hips and frantically rubbing her throbbing asshole. "That was only 81 miles per hour. You're going to have to do better than that," the Master advised Carlotta. "Anna, get that ass spread again unless you want more punishment strokes." Still moaning, Anna reached back and reluctantly spread her tight little ass cheeks open again.

Carlotta nodded and brought the thin crop back up. Taking a deep breath, she brought it down with all her strength. The "crack" of the thin rod hitting flesh was cut off immediately by Anna's shrill scream, although this time she managed to not let go with her hands. "That one was 87 miles per hour; better, but still not good enough," the Master advised.

Angry, Carlotta raised the crop and again slashed it down on Anna's unprotected little ass. Anna's whimpering cut off immediately as she screamed again; after a moment the whimpering began again. "89 miles per hour; you're getting there," the Master encouraged.

Carlotta began to worry. She had thought that since she had five strokes to Anna's one, she would be able to win this. Now she was not so confident. She looked down at Anna's ass, preparing for the next stroke. Anna's asshole was already an angry red and looking swollen. Carlotta was sympathetic, but also didn't want to lose and get another five strokes herself. She raised the crop. "No, please, no more," Anna begged. The crop slashed down and Anna screamed again.

"That was still just 89 miles per hour. You've only got one more stroke. You'd better make it count," the Master advised.

Anna was sobbing at this point. Carlotta reflected that when she had gotten her strokes like this, at least the Master had spread them out. Anna's were all coming directly on her poor little asshole. Nevertheless, Carlotta took a deep breath and gave the last stroke all she had. Anna's scream was the loudest yet, and momentarily Carlotta thought she might have won.

The Master shook his head sadly. "See, that's why you should exercise more. That one was better, but still just 90 miles per hour. That means you lose, Carlotta."

Anna had quit sobbing, and was now merely whimpering and gingerly rubbing her abused little asshole. The Master gave her a minute and the rotated the platform back and positioned her height properly for her ass fuck. "I've decided not to use lubricant, Anna. Instead, I think we'll have Carlotta get your ass nice and wet with her tongue. I'll also have her suck me hard and leave my cock wet. That should help, and I'll have her here to suck me again if it gets too dry in your ass. By the way, Carlotta, I suggest you do a good job. I've decided to have Anna do your last five strokes. If you don't get her asshole, including the insides, nice and wet and keep me lubricated, she might take it out on your own ass afterwards."

Carlotta almost cried. It was bad enough when she had to lubricate him repeatedly during her own ass fuck. Now she was going to have to repeatedly taste Anna's ass as well. Still, she recognized the implied threat, and decided she would have to do the best she could. On top of that, now she was going to get five more strokes from Anna, and Anna was probably going to want payback for the five strokes Carlotta had just given her. Carlotta sighed, realizing she was well and truly fucked, in more ways than one.

"Well, Carlotta, time for you to get to work. I'm sure Anna wants to get this all over with," the Master said, stepping back.

Reluctantly, Carlotta knelt behind Anna's wide-spread and still red ass. Tentatively, she stuck her tongue out and licked the outer crinkle. "More," the Master ordered. Carlotta began lapping Anna's asshole, swirling her tongue around the little star. Finally, taking a deep breath, she began inserting the tip of her tongue directly into Anna's little asshole. She had to push hard to make any progress. Realizing how tight she was, Carlotta knew that Anna was definitely not going to enjoy her coming ass fuck. Over the next several minutes, she tried to get as much saliva as she could, as deep in Anna's ass as possible, pushing her tongue deeper and deeper, despite the nasty taste, as Anna's ass became looser and more lubricated,. "I think that enough for now. Get me wet," the Master ordered; he was already rock hard.

Carlotta took the Master's cock in her mouth, again trying to coat it with as much saliva as possible. The Master drove deep into her throat a couple of times, then pulled out and moved over behind Anna's defenseless ass. "Kneel over here so you can suck me again when I need more lubrication." The Master pressed the fat, wet tip of his cock firmly against Anna's ass. Anna hissed in pain as he began applying more and more pressure against her still sore portal. Anna yelped as the fat head finally popped past her sphincter, and then groaned as the Master pushed further into her tight ass, straining the walls of her bowels until Anna was afraid they would split. She had been fucked in the ass a couple of times before, but never by anything even close to this thick. Every couple of inches, Anna had thought there couldn't possibly be any more, but still more of the rock-hard cock invaded her bottom. Eventually, long after Anna thought it should have happened, the Master finally bottomed out, his coarse pubic hair pressed firmly against her still-throbbing ass.

He began a slow in and out, gradually taking longer strokes until eventually he was popping his cock completely clear of her stretched-open little star, then plunging back in before it had a chance to begin closing, accompanied by groans from Anna with each thrust. After five minutes or so, he pulled completely out and sank his rampant cock deep in Carlotta's reluctant mouth for more lubrication. The second time he did this, he also forced Carlotta to thrust her tongue deep in Anna's now wide-open asshole. With little choice, Carlotta obeyed, but the taste of Anna's ass was even worst than her own.

After ten minutes or so, the Master realized he was already close to cumming. Not wanting to cum too soon, he withdrew completely and released Anna from the apparatus. At first Anna was relieved, thinking that her ass fuck was over. To her consternation, he ordered Carlotta to lie on the mat and positioned Anna over her head, which was propped up by cushions.

The Master explained. "Carlotta, I want you to suck Anna's cunt and clit while I fuck her ass. If you can make her climax before I do, I will take away two of your strokes. Anna, if you do cum, I'll add another thousand to your car fund. Remember though, with my cock in your ass, I'll know if you fake it." The Master stroked his cock in and out of Carlotta's mouth a couple of times, and then lined it up with Anna's ass. Her ass had closed up during the repositioning, and she grunted as he began penetrating the still-tight portal. Anna dropped to her elbows, spread either side of Carlotta's outstretched body, as he began to thrust brutally. Anna's nipples rubbed on Carlotta's stomach with the force of each thrust.

The Master kept up his long, ass-stretching strokes in Anna's butt, every once in a while pulling out, shoving the nasty cock in Carlotta's mouth for more lubrication, then back in Anna's ass. Carlotta meanwhile was licking Anna's cunt and clit for all she was worth, trying desperately to earn her strokes back. To Anna's surprise and dismay, the combined assaults finally began to have their effect on her, and just before the Master was ready to climax, Anna screamed out her own climax, the spasms of her tight ass finally setting off the Master's own peak. After the first spurt, the Master pulled out and shot the rest of his cum all over Carlotta's upturned face.

"I've changed my mind," the Master told Anna, presenting his still-dripping cock to her face. "You clean me, then go lick off the rest of my cum from Carlotta's face. Anna sighed, but reluctantly did as she was told, tasting her own ass combined with his cum. "Very good," the Master complimented both women. "Anna now has $10,000 toward her car fund, but she still owes Carlotta three strokes; three good strokes," he emphasized. "So, how do you want her?" the Master asked Anna.

"I guess with her legs in the air," she replied, thoughtfully. The Master positioned Carlotta on the mat and strapped her torso down and her arms extended above her head. Next he attached cuffs with ropes to each ankle and hoisted her legs up until they were straight up and spread wide, leaving her poor cunt totally exposed.

Finally he set up the chronograph. "OK, you managed 93 miles per hour on your first stroke. If you fall below that, I'll have to give you a stroke for slacking off. However, if you can top 98 miles per hour, I'll add another $2500 to your car fund," he told Anna. Carlotta listened to all this with dismay. She had been hoping Anna would go easy on her this time. Clearly, that wasn't going to happen.

Anna took her position between Carlotta's outstretched legs, looking directly down on her spread and defenseless cunt. Anna smiled and raised the riding crop. Slash! The crop hit directly on the center of Carlotta's spread pussy, wrapping from the base of her cunt all the way to her clit, accompanied by a shrill scream from Carlotta. "94 miles per hour; not bad," the Master commented. Anna got a determined look on her face and raised the crop again. Carlotta moaned in terror. Slash! Again the cruel crop fell and again Carlotta shrieked. "Still only 95 miles per hour. You've only got one more try; better make it count," the master advised. Anna limbered up her shoulders, swishing the evil crop through the air a couple of times, and then turned back to Carlotta's sorely punished cunt. Slash! This time the strike was noticeably sharper and Carlotta's scream louder and more shrill. "97 miles per hour; not quite good enough. I guess that means we're through for the day, the Master stated. He reached over and released Carlotta's suspended legs, the unstrapped her hands and torso.

"So Ann, do you want to play again, get the rest of the money for your car?" the Master asked as he worked on releasing Carlotta.

Anna thought for a minute. "Absolutely," she finally said, eyeing Carlotta's body, but rubbing her own ass. "But maybe in another week or so."

Carlotta was seething. Finally released, she stepped up to Anna and said "You bitch. You didn't have to hit me that hard, just to get another thousand dollars for your lousy car. I glad you didn't get the money."

The Master looked at the two women. "I'm sorry, Anna. I thought she was better disciplined than that. I suppose tomorrow, we'll have to use the stocks. Why don't you plan to come down tomorrow and help punish her for her little outburst?"

Carlotta looked stricken as the other two turned and left the rooms. She sighed and then hobbled off to her rooms as the door bolt was locked again. She needed to learn to keep her mouth shut.