Cinna's Pirate Dreams

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A hallucinatory Halloween Night of OTK debauchery for Cinna.
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L O Reins
L O Reins
103 Followers

“Step up on this ledge, Cinna"

“No. Not there--someone might see me” she replied.

“If you didn’t want to do this you wouldn’t have answered my ad. Would you, Cinna?”

Cinna had walked the five blocks to this address in the ridiculous costume he had instructed her to wear. She felt conspicuous but the clamor of trick or treaters was a good cover. Her real fear was of being recognized by someone she knew. She thought the classic black eye mask was a hedge against that. The front porch lights would be off to dissuade the trick or treaters. The last thing she wanted was to stand at his door surrounded by neighborhood kids in costume. At least his smile when he opened the door made her feel that he was pleased with her costume.

“I don’t know. I don’t know if I can after all.” Cinna’s resolve was shaken now that she was here in his house.

“If you didn’t think you could do it why did you come? Did you think I would talk you into it, Cinna? His den was masculine in every detail. Dark hunter green walls thick carpet and the lingering smell of sweet tobacco, it all made Cinna comfortable but…

“ Maybe I should think about it. Maybe you could just explain it to me this first time.”

“You wanted to be seen like this. It was your fantasy to be spanked, naked, over my lap. If it makes you feel better you may keep your mask on. Now step up here and I’ll help you make up your mind.”

He took her hand and helped her step up onto the twelve-foot wide raised platform that was detailed into the oversized bay window. The curtains and shades were drawn back and the windows looked out across the wraparound porch and over the dormant lawn. The red and yellow of the old maples and their wind rustled leaves painted a perfect backdrop on this brisk Halloween night.

He sat down in the straight-backed wooden chair to survey the overall effect. He was satisfied with her costume. It was even better than expected. They had discussed all this over the phone and then worked out the costume at a public meeting over coffee. She was the perfect wench right out of Captains Courageous. He couldn’t wait to have her over his knee. Cinna swayed her skirt then struck a defiant stance for his approval.

“What do you think, Sir? Is this what the Captain had in mind?”

He smiled at her gesture, standing there in that tight-laced white shirt with her ample cleavage exposed, a billowing full skirt and black pointed boots. The black bandanna around her forehead was a little much but with the mask it all worked. Cinna was the perfect picture of the scullery maid.

“Perfect. Now remove your blouse for me, Cinna.”

Cinna lowered her eyes as she unlaced her white shirt--let it fall softly from her shoulders then turned away, as if to hide her naked breasts from his gaze.

“You’re testing me, aren’t you Cinna? Naughty and sassy until you’ve earned a good spanking, I wonder if you taunt me just so you can get your tail warmed all the harder.”

He smiled as she did a Shirley Temple knee twist, swinging her skirt with the motion, and gazed at him over her shoulder.

“…and the skirt and boots, Cinna—remove them.

Cinna dropped the skirt to the floor and stepped over it. Then she bent to unzip her boot. In the black bikini panties thigh high stockings, pointed heeled boots, black bandanna and eye mask Cinna was stunning.

“You may leave your stockings and boots on, Cinna. I like the effect. Now come over here and lay across my lap and I’ll sooth you a little before we begin. It’s time."

Cinna stepped towards him, eyes down, a sweet pout on her lips. “No. Not that way”, his voice more stern now, “ this way with your ass out towards the windows."

“But someone might see me, someone could recognize me, Sir"

"No one will see you around this side of the house. Besides, if anyone did see you they wouldn’t see your face. You are masked, Cinna.”

The course texture of his trousers against her tummy and her full naked breasts was exhilarating to her. Cinna had baby bottle nipples surrounded by dark areolas and the feeling of the delicate flesh on the underside of them being exposed as she lay draped across his lap was a definite turn on.

“Such lovely panties, Cinna.” He eased her panties over her ass and left them around her knees for the moment.

“Thank you, Sir.”

Cinna moaned as he gently stroked the sensitive flesh of her cheeks and the backs of her thighs. He felt her relax and loosen the tension in her muscles.

“You know you deserve this don’t you Cinna?”

“Umm Hmm.” She raised her ass up to meet his palm.

“If you are a good girl, Cinna, I might let you cum for me after your spanking. I can see you are wet already."

“Yes, Sir, if that would please you.”

“Good, now then, palms on the floor and up on your tiptoes.”

She did as instructed and felt his cool breath between her open legs. She wiggled a little to receive the fainted kiss.

He spoke softly as he applied pressure to the base of her spine with his left hand and caressed her firm round bottom with his right.

“Very nice, you open like a flower, Cinna.”

He cupped her mound in his hand. Licking his thumb and placing it at her anus, he waited till he felt her writhe gently on his lap, then slide it inside to the first knuckle.

Cinna let her breath out with a forceful purrrrr telling him that something was right.

"Do you like this intrusion Cinna? You do, don't you?" When he felt her relax he slowly twisted his thumb deeper inside her.

“Yes Sir.” she hissed trying to control her breath.

“Good, then we will get back to your little rosebud in good time.” Cinna flinched at the abrupt way he removed his thumb from her ass. "Now back to your spanking."

The rustling of leaves outside the window alarmed Cinna. Sir took the opportunity to make her squirm more.

“You know… maybe someone could see you like this, Cinna. Maybe someone is watching now. Leering at your gorgeous round bottom and your dancer’s legs.”

“Nooo. Sir! Please, I don't want to be seen like this.”

“Does it excite you to think someone would see you exposed like this?”

“But Sir my students live in this neighborhood. I could be fired.”

“Well, you should have thought of that before you came here, Cinna.”

He slid his left hand to the base of her spine and applied a firmer pressure. She knew something was coming. The anticipation gave her a chill sending goose bumps to the surface of her flesh. It seemed an eternal second until the first sharp slap to her right cheek came. It startled her more than it hurt at first but the steady quick cupped-hand pops that followed began to warm her bottom and soon the burning sensation clouded her fear of exposure. He began to increase the force of his slaps alternating from cheek to cheek, slightly varying placement to spread out the sensations.

“There, you’re warming to a lovely pink already.”

Cinna squirmed and tried to shift position as if she was trying to avoid his slaps but in fact she loved this scene. It brought back all her childhood fantasies of being disciplined by her aunt in front of her younger cousins and later her own self-administered spankings at the hands of the swarthy pirate captain. She still fantasized about being the captive slave girl, trapped in the captain’s quarters and at his mercy. These fantasies had seduced her into responding to his ad in the personals column.


“Do you yearn to be disciplined by a strict and caring man?

Do you think about being sternly spanked over my lap?

Or maybe in front of others for your mischievous behavior?

If you believe you disserve this call me to discuss your situation,

Now, while you are thinking about what you have done.

Call Sir at 888-293-4442.”

She got dreamily disconnected as the slaps rained down on her ass. Lightheaded from the rush to her head of blood and emotions, she sunk into her fantasies.

“You filthy dogs will pay for this,” she said, as the deck hands hooted and jeered. “Stop! I can’t take any more,” she cried but the cruel Captain kept punishing her bottom.

Sir was delighted with her fantasy and so perfectly keyed to her senses. When Cinna thought that three or four more stinging slaps was all she could stand he gave them to her, and then three more. He could read her like a book, and it was delicious the way he pushed to the edge of her limits. Then another rustling sound--leaves being shuffled brought Cinna to her senses.

“Captain--Sir. What was that?"

“Relax, Cinna. It’s just the sounds of the sea; nothing for a wench to be concerned with.”

And in her light-headedness Cinna fell back into her fantasy. She could see the faces of the crew as their fierce captain wailed away at her burning bottom.

“Stop it you scurvy bastard. You’ll all be sorry for this.”

He ripped her panties from around her knees and tried to pick up on her delirious bantering, “Quiet, Bitch. A good spanking is the only thing a little whoring wench like you is worthy of. Isn’t it mates?”

Cinna imagined she could hear the crew cheering him on. She was on fire from the humiliation and excitement of being forced and bared by these imagined heathens.

“Who is that?” Her fantasy was once again jarred by the sounds—the sounds of footsteps on the ship’s wooden decking. Was someone coming to save her?

“Its nothing, Cinna, just some kids coming up on the front porch to see if there are any treats left for them. Don’t let yourself get distracted.” He spanked her more slowly and more deliberately. The shouts of the trick or treaters outside on the street kept coming in and out of her consciousness. It only added to the naughty fervor of the scene. The stinging had become white hot now and Cinna squealed on the fourth or fifth slap.

She squirmed around on his lap and in the reflection of the glass she imagined she saw the faces of the crew in their pirate’s hats, blackened teeth, and eye patches, leering at her spectacle. Just as she settled she could have sworn a laugh seemed closer than the other street noises.

“There. What was that?”

“Hmmm, I heard that too. Maybe there is someone out there" and he began to rub her cheeks and soothe her worry. “Its alright Cinna, it will be over soon.” Just let yourself go with it. No one will recognize you and besides they all know you deserve it.”

Cinna squirmed and rotated her pelvis. “Yes, I can feel your showmanship kicking in.”

A long “ummmmm” and then a soft gasp as the slaps resumed and got stronger--he could tell she lusted after this roll play.

“Me thinks this wench doth protest too much, Mates. You really do like this, Wench. And you know, as the Captain of this ship and your master, I’ll take you over my knees here on deck and in front of my scurvy crew anytime I want, don’t you?”

An inhaled “YESSSSS” affirmed his question.

“YES?” Sir rained down two very hard slaps on her fiery red ass, “YES WHAT?”

“Yessss, CAPTAIN.”

“Alright, Wench, ten strokes to finish! Now count them for me. And if you miss a count I’ll be happy to start all over again.”

She was lost in the burning feeling and the excitement of imagining the horny sex-starved seafarers drooling over her barred ass. She could hear their snickers and see the depravity and lust in their faces projected on the windowpanes. Then she saw movement outside the windows, real movement. Cinna realized this was no fantasy; these were real faces outside leering in at her. And at that moment this realization sent her only deeper into her fantasy. Cinna hung her head and raised her ass to receive the first of his ten last blows and the thought of this humiliation made her pussy hot and very wet against his thighs. Her abandoned writhing on his lap was her only protest.

“One, two, three,” She began the ritual of counting that connected spanker and spanked. “four, five, six,” He loved to make each of these last spanks harder and harder. He thought of them as the real punishment for misbehavior. “Seven, eight,” The burn and the glow simmered through her. Cinna raised her ass brazenly to taunt him and whoever was outside on the porch. Nine and ten were outside her tolerance. She yelped at these last two swats, collapsed in sobs over his lap and felt her own saltwater roll down her forehead.

“That a girl, Cinna,” he soothed her, stroking her hair and her shoulders. “You did well.”

Then she felt his hand cup her mound again. His fingers entered her roughly. This time the sounds outside didn’t surprise or confuse her.

“They’re just trying to get a better look”, she thought.

Cinna squirmed off Sir’s lap to her hands and knees. Sir followed her lead. Stretching her arms, entangling her fingers in the thick rich carpet, she gyrated back as if to swallow his whole hand. Knowing they were out there, probably with their dicks in their hands only fueled her abandon. Another hoot—then that same cackle came from outside and Cinna’s suspicions were confirmed. Now she knew who was outside on the porch all this time but it was too late to protest.

“You little fuck.” She said a little too loudly.

“What did you say, Cinna?” But he was lost in his own moment. His thumb probed deeply inside her. He felt it with his fingertips through the thin separating membrane. Her orgasm swelled up behind her—began to lift her like a wave then buffeted her like a pounding surf.

“YESSSSS,” she screamed out as he brought her to her second feverish climax.

Cinna lay in the rich carpet, her bandana askew, mask misaligned and her stockings now slide down loose and twisted around her muscled calves as Sir caressed her—soothed her with compliments and encouragement. She acknowledged his words but only thought about Trent and his accomplice Mouse. What cruel fate had made them dress up as pirates this Halloween night? No matter now, they wouldn’t get away with invading her privacy like this. She didn’t know what she’d do exactly, but she’d think up some nasty retaliation for her two most obnoxious students by Monday.

To be continued…

Hello Readers and Writers,

I hope you enjoyed this story. If I did manage to hold your interest till the end please take another minute to vote. It’s the only way I have of knowing how I am doing. Feedback is great and always appreciated. If you include an E-dress I’ll be sure to write back.

L O Reins 10/29/03

L O Reins
L O Reins
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