The cropping began almost immediately. The first cut made her gasp, the second one made her cry out, the sound caught against the cloth in her mouth, and the third one made her eyes water.
Soon, the men were striking her in perfect timing. Cock would hit her front, her pussy, her breasts or the tops of her legs, and seconds later Nut would hit her back, her ass and thighs.
Lia lost count after a while. The captains laid the crops down harder and faster, and soon her entire body felt as if it could be used for a stove. She twisted and turned, trying to get away from them. The movement only meant that the crops sometimes landed on areas where it shouldn’t have, places where it burned worse than her bottom.
The crowd yelled and screamed for them to “Give her more,” with each cut. To Lia’s amazement, their words excited. She’d never wanted to be on display before, because she was larger than most women. But hearing this crowd yell out their appreciation for what they were watching, and for the way she was taking it, was pure pleasure.
Adrenaline flowed through her, building to a crescendo. If one of them touched her clit, she would come. Instead, the cropping ended abruptly and Captain Cock ordered his men to take her down and bend her over the table that was off to the side.
The table was long and thin. They bound her legs with ropes leading to the legs, and tied her hands behind her back. The wood was cool as she pressed into it.
When she was secured, she glanced over her shoulder. Captain Nut had his cock out. He was already hard. When he stepped behind her and slid his dick into her wetness, Lia closed her eyes and savored the feel of him. He still had the crop in his hand, and he rubbed it over her back and shoulders as he slowly slid in and out of her.
The crowd went crazy, yelling at him to “Fuck her harder,” and “Give it to her like she’s a true slut.”
But he didn’t. He kept the pace slow, and if she’d been able to, Lia would have joined in the chorus of “Faster, faster, faster,” that filled the room.
The fucking didn’t last long, and her muffled cries of disappointment filled the room. Seconds after Captain Nut left her, Captain Cock took his place. His fucking was harder, and faster. Captain Nut was off to the side, rubbing the crop against her back. She wasn’t sure how they’d done it, but somehow they’d managed not to hit any of the places on her body that could cause her true harm.
She glanced at Captain Nut. He watched her intently, and she felt as if he knew exactly what would make her come. Seconds later she knew he did, because he knelt down and rubbed the tip of the crop between her outstretched legs. A few fast movements and the leather tip caressed her clit.
The gag swallowed Lia’s scream of pleasure, and Captain Cock fucked her harder. He stepped away seconds later, and the two switched places. Captain Nut rubbed her clit, and Lia thought she might explode. She came again seconds later, the intense sensation bringing tears to her eyes.
The room seemed to rotate as she soared , and as she came down to Earth, she realized no one was inside her, and the two of them were cropping her ass, once again setting up a perfect rhythm. The strokes stopped, and hands caressed her aching ass. She could hear movement behind her, as if someone were stroking a cock. Lia jerked her head from side to side. The captains had her bookmarked, and they were jerking off. Part of her wondered if it were some sort of contest, to see who could come first.
If she’d been able to, she would have yelled at them to put their dicks in her again. She had two holes back there. One could take her ass, the other her pussy. But something told her they wouldn’t listen. As she lay there, helpless, streams of cum, from both sides of the table, hit her welted bottom.
It seemed like such a waste to her, but when four hands started to stroke her ass and thighs, she thought she would come for a third time. Their touches were gentle, and it increased the pleasure soaring through her.
“I think we’re done for now,” Captain Cock announced. The crowd applauded, and Lia turned her head enough to lay it on the table. She could hear people shuffling out of the room.
“She’s a tight little bitch,” Captain Nut said. Rather than be offended, she flushed at his words.
“She is. Tonight, we’ll see how she takes both of us,” Captain Cock said.
“I have no doubt she’d learn to love it,” Captain Nut said.
Lia wanted to tell him he was right. She was ready for both their cocks inside her.
She had two pirates. This vacation was more perfect than she’d ever imagined it would be.
* * * *
Arch stared down at the sleeping woman. The marks on her ass had faded somewhat, but he and Keifer had already discussed that they wouldn’t be able to have another scene like this afternoon’s too soon. She might have signed up for it, but too much pain was not a good thing.
They would have to be creative in their next few scenes, until they thought she was ready to take another flogging, or a cropping. The scene they’d just done was perfect. Arch had been sure when he’d seen the audition tape that she was the sub for he and Keifer to share on this event. What had just happened proved that, in spades.
She was so different from the women he dated at home. The only similarity was they were all subs. But the ladies who he took to his dungeon in Boston were tall, thin and mostly blonde. He met most of them through his contacts at work. He wasn’t the only Dom at the firm; there were two others, and they’d both introduced him to three women, who had been fun to play with, but had never really captured his attention enough to want to collar them. None of them had feelings for him and had been content to play and then move on to someone else.
Arch wondered about Lia. She was a paralegal, but that was all he really knew about her, except for what he’d seen on the tape. Her application had been light on information, only touching on her sexual needs. Obviously she didn’t have a Dom, or she wouldn’t be here. Unless her Dom had sent her here to learn a few things. But from what Arch could see, she didn’t need to learn too much.
They were supposed to stay in character for the entire trip, so asking her these questions was, well, out of the question. He needed to find a way to pry into her personal life and not take away from the fantasy they were living out.
“What the hell are you doing over there?” Keifer asked. “You’re staring at her as if she’s a steak and you haven’t eaten in months. You just had a taste of her.”
“An appetizer. I think it’s time for the main course.”
Keifer chuckled. He and his friend were at two different ends of the spectrum. They always had been, even when they were boys. Their parents ran in the same circles, and they went to the same private school as kids. They’d even attended Harvard together, but that was where the similarities ended.
When Arch went to law school, Keifer decided he’d had enough school, and didn’t care to find a job. He’d traveled, first in Europe and then in the States, buying a motorcycle and taking to the highways. Sometimes, Arch wasn’t even sure where his friend was staying. But when he came home, they always got together, always went to a club and found a woman they could share.
It had been two years since Keifer had stayed long enough in Boston for them to have fun, though, so Arch had proposed the Fingertip Fantasy trip. He could tell already this was going to be a perfect vacation.
“Shall we plan a few scenes? Of course, you’ll be alone with her tonight, right?” Keifer asked.
“Why don’t we just take it as it comes,” Arch replied. “And I think we both need to stay with her tonight.” His friend started to cough, hard, and Arch shifted his gaze to him. “Something wrong?”
“You,” Keifer said, pausing to catch his breath. “You want to take it as it comes? Who are you and what have you done with Arch. Are you not the man who planned your birthday parties down to the minute, saying when the clown could come in and when he could leave?”
“Maybe I’m up for a change in pace,” Arch said. “You plan the next scene.”
“I’ve nev
Arch looked back at Lia. “We should start on the interrogation next,” he said.
“I’ll go get more rope,” Keifer said as he stood. “Anything else you might need?”
“A few clamps, if they have any that match the time period.”
“I’m sure they do,” Keifer said in his usual jovial manner. He left, and Arch continued to study the woman in the bed. It would be interesting to see how she reacted to the remainder of the vacation.
If the last scene were any indication, things would be incredible.
* * * *
Lia could hear the two Doms talking quietly. After the scene in the playroom, they’d brought her back to the room and let her sleep. She could tell by the way the two men interacted with each other that they were friends, and not someone who had just met on this trip. That meant the blond, called Captain Nut, would be staying with them.
Her body tingled at the idea of being double penetrated. Listening to them made her wonder who they were, and where they were from. They seemed so different, both in looks and mannerisms. The blond was obviously controlled, with his short hair and the stark looks he’d given her while they were playing.
The long-haired Dom was strict, but something told her he could be laidback when he wasn’t doing a scene. Both of them knew how to push buttons and give a sub exactly what she wanted. They’d proven that during their last scene.
She wondered what was next. They weren’t talking loud enough for her to hear, but she’d been partially awake when a few of the crewmen had moved something into the room. She didn’t open her eyes to see what it was, but now Lia wanted to sit up and see what they had planned for her.
Instead, she decided it was best to continue to play the sweet virgin. She kept her head on the pillow and her eyes closed.
A soft moan escaped her lips as images of taking the two of them at the same time filled her mind.
“I think the wench is awake,” said the Dom she’d met first.
“Get up,” the second one ordered.
Lia sat up, letting her gaze shift between the two of them. It was dark outside, and the only light filling the room came from several hurricane lamps and a few candles.
“The captain of this vessel tells us you know where the jewels are,” the dark haired Dom said. “Tell us, and we might spare you further pain.”
There were several ways she could play this, she knew. It took Lia a few moments to decide to change the way she’d gone earlier.
“Please, sirs, I don’t know what you’re talking about.”
“What a little liar,” the blond said. “I don’t care for liars. Do you, my friend?”
“No, I don’t.”
Lia scooted back on the bed as they approached, two hulking figures in the dimly lit room. Her nipples hardened, and her juices started to flow.
“Come now, Lia, don’t make this any harder than it has to be,” the blond said.
She cleared her throat. “Please tell me your names. I don’t think I can go around calling you Captain Cock and Captain Nut.”
They exchanged a look, and the mutual understanding that ran between them confirmed her suspicion that they were longtime friends.
“I am Captain Keifer,” her first captor said. “This is Captain Archer.”
“Sirs,” she whispered. “I know nothing of jewels, I swear it.”
Captain Archer was the first to speak. “Did you miss what we said earlier? Lying does not become you, little one.”
“It’s the truth,” she said. “Let me talk with the captain, and I will call him out for a liar.”
Damn, that was something she would have read in one of her mother’s books. She was rather proud of herself for keeping in character.
“Perhaps some other time,” Captain Keifer said. “But first, we’ve devised a way to see if we can get information out of that pretty brain of yours.”
As much as she enjoyed a good spanking, Lia wasn’t sure now was the time for one. She was still sore from their earlier play, but she wasn’t quite sure how to say it without sounding like a whiner.
“Get up,” Captain Archer ordered. Lia was slow to follow his command, and the tall man slapped a leather strap against the bed’s post. The noise made her jolt and she hurried off the bed, wincing at the pain in her bottom.
“To the chair,” Captain Keifer said. Off to the side, nestled in a narrow space that barely left room for a person on either side, was an old-fashioned barber’s chair. This one had been fitted with ropes.
“Sit,” they said at almost the same time.
Lia gingerly lowered herself onto the leather. The men wasted no time. They tied her arms and legs to the chair, and Lia was pleased to see that she wasn’t spread eagle. Something told her there would be no whipping in this scene. But what would they do? The old familiar tingling surged through her, despite her soreness.
Captain Keifer stroked her breasts, and when Captain Archer’s hand moved between her legs, Lia moaned.
“What a little whore,” Captain Archer said. “The easy way she is aroused will come in handy during our time together.”
“Definitely,” Captain Keifer said. The two men withdrew their hands in unison and Lia moaned again, this time in disappointment.
Captain Archer stayed by her side, while Captain Keifer moved around the room.
“I have something for you,” the dark haired pirate said, his tone jovial.
“What is it?” Lia asked, hesitantly. He opened his hand and placed it directly in front of her face. Lia’s eyes widened, but she didn’t say a thing.
“Do you know what this is?” Archer asked.
Oh yes, she knew, but she wasn’t about to tell them that. Lia stared at the objects. There were three of them: small, horseshoe shaped clamps with screws attached to one side. Most nipple clamps she’d tried wouldn’t stay on her large nipples, but something told her these would.
“We’re going to ask you some questions,” Archer said. “Each false answer equals a turn of the screw, one for each nipple, and one for the pretty button between your legs.”
“No,” she whispered.
“Yes,” Keifer said. “Let’s not put things off any more. Tell us, Lia, why are you in the tropics?”
“To visit my family,” she replied.
“I don’t believe you,” Archer said. “One turn. Try another answer.”
“It’s the truth.” She tried to rise from the chair, but the ropes kept her in place.
“Two turns,” Keifer said. “Be truthful.”
“I am!” This time she yelled.
“Three turns,” Archer said calmly. “Let’s move on, shall we? This question is getting us nowhere.”
Keifer leaned in, his face inches away from hers. When he spoke, she felt the heat of his breath, and caught the scent of apples.
“Where are the jewels?” his tone was soft and seductive.
“I swear to you—”
Before she even finished the sentence, Archer said, “Four turns.”
“Tell us,” Keifer said in that soft tone that made her nipples harden.
“I can’t tell you what I don’t know,” she said, pleadingly.
“We’re up to five,” Archer said. “You’re nipples and clit are going to be very sore.”
Keifer stood upright, and put his hand on her hair, stroking gently. This was unlike him, and she steeled herself for the yank she knew was coming. But it didn’t happen.
“Maybe it’s not jewels we’re searching for,” Keifer said. “Perhaps her father entrusted her with something else, like a deed to property down here? Or maybe money. Lots of money.”
“There is nothing—” Lia yelped as Keifer gathered a section of her hair in his hands. He didn’t pull, though.
“That’s six,” Archer said. “I think she’s lying to us on purpose. I don’t think we’re going to get any answers out of her. I say we shoot straight to ten and get down to brass tacks, or brass clamps in this case.”
“No, no!” She thought about the items Keifer had shown her. Ten was a lot of turns when the clamps would be on the sensitive parts of her body.
“Ten it is,” Keifer said. Lia tried, unsuccessfully, to wiggle her arms out of the ropes.
“If you fight us, we will increase the number,” Archer said. “Stay still.”
“Shall we go one at a time, or do it together?” Keifer asked.
“Together, definitely,” Archer said. “And you, Miss Lia, will stay absolutely still as I said. If you move, we will add turns. Do I make myself clear?”
“Yes, Sir.” Lia tried to stay as still as possible, and at first it was easy, until they reached six turns of the screw, which brought uncomfortable pressure to her nipples. Still, it was exciting, having two men play with her breasts, their large hands manipulating her hard nipples and soft, large orbs. On the seventh one, Lia couldn’t control the soft screech that left her mouth. The pain shot through her. Both men ignored her and quickly tightened the clamps, counting to the number twelve. She wanted to tell them it was above the number they’d agreed upon, but she was afraid it would earn her more turns, so she kept her mouth closed.
Her nipples throbbed, the discomfort far greater than what she’d ever felt with modern-day clamps. They’d placed them toward her areola with the hard bud extending out from the clamp.
She moaned a few times as she tried to get hold of the feelings, let herself adjust to the sensations. It was hard, though, especially when both of them started to rub the tips of their fingers over her breasts, sliding from one side to the other, the gentle touch a huge contrast to the tightness in her nipples.
“She’s not even begging for them to come off,” Keifer said.
“Rather extraordinary, really, for a supposed virgin,” Archer said.
She needed to play into the fantasy, rather than just let herself savor the feel of the clamps.
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