Tropical Joys Ch. 06

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Nicki crosses a boundary.
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Part 5 of the 5 part series

Updated 09/22/2022
Created 06/03/2003
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Red Hugh
Red Hugh
62 Followers

Nicki had enjoyed the feeling of being held tightly in a helpless and exposed condition by David while Caroline attended to her pussy. This fact had not escaped David's notice and, combined with Caroline's desire to play the schoolgirl for David, would lead to a very satisfying interlude for all concerned.

First of all Nicki had to recover from her time on David's penis. Unlike Caroline she was tender but not sore and her deflowering had been the most sexually satisfying experience imaginable. Her stomach was a little sore from all the flexing of her muscles during orgasm. She had lain beside David and Caroline as they made love the morning after but had not bothered to play with her pussy. It had been nice to watch and any stored up erotic feelings could be tapped later.

David had to go out for the day and so the girls breakfasted showered and headed for the beach. There they discussed what had gone on and Caroline told Nicki about having sex with Helen. Caroline had a close look at Nicki's nether regions especially around her entrance. Everything looked fine. They talked all morning and swam. Caroline asked about what Nicki had done with her school uniform. In fact it was in her luggage as she had not been home since the end of term. Nicki asked why Caroline was interested and had some of David's proclivities explained to her. Nicki was quite surprised to discover how she had enjoyed being held helpless by David and between the uniforms and this the girls cooked up a little surprise for David upon his return.

That evening they slipped over to Caroline's and changed into their school uniforms. They wore a pleated tartan skirt, stockings, undergarments of course and a white blouse with a little tie in the school colours. Caroline wore her most girlie white cotton panties and matching little bra. She really didn't need a bra but it was a school regulation so she wore one. Nicki wore her usual silky panties and today hers were an ivory colour. Her matching bra was just visible trough her blouse. She had thigh high stockings rather than the correct pantyhose that Caroline wore. Caroline wore her hair in pigtails and Nicki drew hers back in a bun. She also decided to wear her glasses instead of her contacts. David was in for a treat! The girls headed down the path to David's. They knocked on the door and soon he answered. He did a double take and before saying anything Caroline spoke.

"We're very sorry to disturb you sir but the headmistress said we should come and see you as the Dean of Discipline and take whatever punishment you should decide."

"I see." David replied starting to catch on. "You had better come in then girls. I assume this is serious or I would not be bothered at home. Come to my office."

The girls entered and followed David to his office off the living room. Nicki shuffled uncomfortably from foot to foot. She felt odd but could quite figure out what it was that was going on inside her. She felt a little scared of what might happen yet her breasts were feeling full and sensitive. Her nipples pushed against her bra at David's imperious tone

Caroline had composed a note explaining what she had done, but Nicki had decided to tell David what her misdemenours.

David read the note and told Caroline that she was likely to be expelled for what she had done. She had been caught smoking for the fifth time and had lied about it to her form mistress. Nicki confessed to sneaking out to see a boy but as it was her first offence it would only result in suspension. This evening both girls would receive a physical punishment and tomorrow their parents would be informed of their misdeeds and the consequences.

To Caroline most of this was a game and she was happy to play along gaining some sexual satisfaction along the way.

Nicki was entirely different, something happened here for her. From a full feeling in her breasts and her nipples extending to strain against the lace of her bra with each step she took she felt her little sex lips pout and fill. She began to moisten. As her sex lips expanded with increased blood flow she became aware of the soft cloth her panties were made of. So began a cycle of arousal, which brought a flush to her cheeks and a slight confused hesitation as she tried to process her reaction to what was happening.

David who was now referred to as "Sir" sat behind his desk. He was still in a suit and looked quite imposing. Even seated her was as tall as Nicki and could look her in the eye had she looked up. Caroline was looking directly at David. This decided him that she should be the first to be disciplined.

What was going to happen was explained carefully to the girls again Caroline felt nothing much other than the desire to have those big hands on her and for him to fill her. She was not unaroused but in nothing like the state Nicki was in. Had her panties been inspected they would have been found to contain only the sweet subtle scent of her sex. Nicki's moisture was now on her panties and because of the silky nature of the cloth there was now a little stain where her opening allowed her dampness to contact the material. There was no gusset. Her panties were not intended for daily wear. They were designed to appeal to a lover and as such were designed to be worn for a short time only. Needless to say her underwear was in breach of the school's rules. She would be punished further when this was discovered.

Nicki was ordered to the corner. Without hesitation she obeyed only to be stopped by Sir.

"You know what must happen." It was not a question but Nicki treated it as such and in her confusion looked questioningly.

"Take down your pants!" Was the stern command.

Nicki whimpered almost imperceptibly. She obeyed blushing even more. Sir was horrified at what he saw. Nicki hiked her skirt and exposed thigh high stockings and as she lowered her panties to her ankles it was obvious that she had broken the school dress code.

"Do you realise that you will receive additional punishment for these infractions?"

She bit her lip and nodded.

"What' I didn't hear you!"

A soft "Yes sir." Issued from her lips.

"Go to the corner!"

Nicki shuffled off to face the book-lined corner with her ankles shackled by the silk of her now damp undergarment. It was all she could do not to masturbate such was the pressure on her clit which had escaped its hood to throb with each shuffle she took. She thought that she might orgasm before she reached the corner but made it there panting and with her sex fully aroused and open in a delicate pout between her legs.

Caroline meanwhile had been unceremoniously summoned to place herself across the desk for discipline. Caroline wasn't overly excited at the prospect of being whipped, caned or whatever was in store for her. She was excited about pulling her panties down and what that might lead to. However it seemed that tonight was going to be a big night for her lovers.

What Caroline liked was exposure. The lifting of a skirt, the taking down of some panties, being naked in front of someone, all these things were exciting for her. Somehow the Dean of Discipline knew this instinctively. As Caroline stood at the front of his desk and bent forward gripping the other side of it he outlined her punishment to her. She was going to have her pantihose and panties taken down and while her schoolmate listened in the corner she would be spanked five times. For her the spanking meant little or so she thought before it was delivered!

Leaning forward and stretched across the big mahogany desk, her toes just touching the floor, she felt her les being moved slightly apart. A hand went up her stockinged led inside her knee and up her inner thigh it went on, on, on, upwards towards her well covered sex. She felt her skirt lift as it was thrown across her back. A hand on either side of her waist and the elastic of her regulation pantihose was slowly pulled down. There was an approving palm run over her rear, which was still covered by the school regulation, white, cotton panties.

A finger ran along the top of them at the rear then moved down along the natural depression made by her two firm little cheeks until it reached the gap between her legs. Next there was a hand on each of her hips and her panties were rolled away from their natural position to just below her buttocks. A big hand caressed her bottom and a stern voice commanded that she not cry out or worse would happen. The hand lifted away and a split second later Caroline was receiving her first corporal punishment since she was a little girl.

Caroline was caned because her crime was the greater or had been until Nicki's undergarment was exposed.

The first stroke stung and Caroline winced as a red line appeared across one entire cheek. Suddenly she felt the second stroke and so on until suddenly the episode was over. Caroline didn't move. Her slender cheeks stung but there was an odd feeling of warmth. Arousal would be too strong a word but after all she though there might be something to this after all. She found herself wishing for a spanking. She was told to stand up but not let her skirt drop. She gathered it forward and held it above her lined cheeks at the rear and clear of her cleft at the front. Caroline was told that she had to witness Nicki's chastisement. Nicki was called from the corner she shuffled over with her panties at her ankles. She didn't look up. She was moist and excited. Every stroke of the can on her cousin's taught bottom had sent a little thrill through her as she imagined it on her own tender cheeks.

She was told to assume an immodest position across the desk. She couldn't quite reach the other side with her hands. Standing on he tiptoes she was still a good six inches shy of it. Caroline was summoned to hold Nicki in position. She made her way to the opposite side of the desk. It was impractical for her to hold up her skirt and try to secure Nicki with one hand. She was ordered to remove her skirt but not to pull up her panties or hose, there was more punishment for her one Nicki had been taken care of.

Nicki was not to be caned. For her a riding crop had been chosen. It was covered in soft brown leather and its tip was about two inches of the softest hide available. Nicki was now held securely across the desk. Her buttocks raised, toes just touching the ground. She had her head tilted to the side and her eye's closed. Her breathing was steady if slightly heavy - not the only betrayal of her excitement. The way she lay and was held put pressure on her breasts which ached for the touch of a mouth as they pressed to the desk. The first stroke of the 20 she would endure was a long time coming. She heard the crop being taken from a drawer and the soft approach across the Persian rug.

Suddenly something soft was at her ankle. The tip of the crop trailed up the inside of her calf, then to the back of her knee. It paused and slowly moved up her inner thigh just where her buttock jointed her leg it ran sideways and over her little globe. Pausing at the top of her crease it traced a path between her cheeks, over her back entrance to the rear of her pink folds. It was so incredibly soft. The tip didn't quite enter her. She was open with arousal and the leather tip sat at her opening growing darker with liquid evidence of her excitement. Nicki tried to rub against the crop. She was stopped by the crop, which departed her lips to land softly but firmly on her anal pucker. She was instructed sternly not to budge or her punishment would increase. She wanted to press against the crop but dared not. A long 30 seconds later it was back at her sex slowly making its way to her distended little sex trigger. As it slid along it found its target.

Nicki felt the soft pressure on her clit. She shuddered. The crop was back at her sphincter telling her that movement was unacceptable. Nicki was sweating and the anticipation of what was due to happen to her little tail.

There was no more waiting. With a swoosh the crop landed and left a red line across both little buttocks. Nicki strained against her cousin's grip and grunted. It stung but so delicious was the feeling that her bottom bent up for the next stroke. When the second stroke came Nicki very nearly did as well. She was making noises which were forbidden. Caroline was instructed to let her go, remove her own panties from around her ankles and put them in Nicki's mouth as a gag. Caroline did so and then resumed her position and restrained Nicki.

The strokes began to rain down upon Nicki's little bottom. By the fifteenth stroke her bottom was a crisscross of red lines. Moisture was obvious all over her exposed sex lips. At the other end of her body her face was red, tears streamed down her face and little muffed noises still escaped her mouth. Her hair was matted to her face by sweat and tears. Within her she was conflicted by the searing pain on her bottom and the small orgasms that had begun with each stroke beyond the fifth one.

With two stokes left to go Nicki spat out her panty gag and sobbing hysterically begged for the last strokes and for what ever other punishment she deserved. Her clitoris exploded on the twentieth stroke, it was too much and she fainted. This was not uncommon for women David had disciplined. Nicki was in no danger. She came to cradled in Caroline's arms her mouth at her breast. Caroline's blouse was undone and a lowered bra cup exposed one little breast. Nicki sobbed and suckled like a baby. Coming to her senses she realised she could no longer be on the desk. Her legs were spread and she was on top of Nicki with her nipple in her mouth. Her bottom ached and her pussy felt the tip of a penis begin to enter her.

Her legs were interlaced with Caroline's and so with her knees drawn forward and her position at Caroline's breast forcing her body back along her cousin's supporting torso she was obscenely spread. Her bottom laced with red lines continued to sting and her entire rear end was moist with a combination of sweat and sex juice. Her master was soon fully inside her and beginning a steady thrusting rhythm. Nicki grunted with each trust. She was in a daze of arousal. On and on she went just like a battery charging and discharging as each orgasm shook her.

Looking down on Nicki from above and behind David watched his big cock push in and out. The rim of Nicki's little cuntal opening gripped him tightly and as he pushed into her it disappeared only to become visible as he withdrew and it let him go only after puckering out. The skin between the back of her pussy and her rear entrance was stretched tightly and as he withdrew her little sphincter would almost wink at him.

David knew of course that such a chance would not present itself again for some time to come. Nicki was leaking like a tap. She was al over his cock and crotch, her moisture was on her thighs. It was simply a matter of dipping his finger in it.

Doing so he began to tease her with little tickling circles around her hole. The gently massaged the little tight crinkle and as it stretched open a little when he withdrew from her cunt with each stroke he would dip into it and leave a little moisture. Soon it was a wet little pucker and he could gently force a finger in. Soon it was two and then three.

Both Nicki and Caroline were clean and empty thanks to their enemas. In the morning Nicki would be thanking God for taking such care with hers.

The impossible was happening. This little thing barely five feet tall in shoes and with a body perfect in all manner but just so tiny was impaled on David's huge cock. She had three fingers in her rear prizing her open for her first anal encounter with the cock that pushed right up inside her spasming cunt.

Then it came or to be precise so did she. David gave an almighty thrust and the almost comatose Nicki lifted of Caroline's breast with a shriek and pitched forward. David came out of her with a wet sucking noise. She shuddered and fell across her cousin. David's cock bounced in the air as he pulled her back to him and Caroline slithered forward to put her sex at Nicki's face. Nicki was now at a slightly lower angle and had she been sensible to sensations from her private areas she would have felt the massive buggering head of David's cock replace his fingers.

He didn't quite know how he got inside her. Her sphincter was relaxed because she wasn't expecting anything more inside her and the onslaught was swift while she gasped for breathe as an orgasm of titanic proportions hit her so hard she lost control.

David was in her and preparing to go further. Nicki lay sobbing at the sex-lips her cousin offered her. She was unable to do anything she felt limp and helpless. As her feelings below her waist began to return.

Full was not an adequate description of how she felt. Nicki thought she would burst while at the same time the gentle strum of David's finger on her over-wrought clit kept her loins boiling. She was in pain but not uncomfortable. It was the same quality of pain that had brought the gut-wrenching climax on the last stroke of her caning.

Four inches of David was inside her. She could feel each little bit of progress. There was no part of her that didn't scream out what was happening. Her bottom stung, her breasts ached with arousal, her nipples stung. The wet emptiness that was her little cunt was more than offset by the enormity of her buggering. Finally the finger on her clit reminded her of the exhausting burning centred there that spread through her abdomen and threatened to make her lose all control.

As David made it all the way up her backside she struggled for breath and control. All she had on were a pair of black stockings with ladders in them. A huge cock was lodged in her arse and her face was pressed to her cousin's bald little cunt.

She was in no condition to lick Caroline. Sensing this Caroline just held her and let her gasp for breath against her sex.

It was twenty minutes since David had entered Nicki's most private hole. He was now thrusting deep within her colon and the pressure on her clit from his finger increased with his tempo and level of excitement.

The tightness that enveloped David's cock made him aware of every fibre of it as Nicki gripped him. His breathing increased to become a ragged counterpoint to his thrusts. The noise from Nicki was just a long extended cry. David's finger dug into her she started to feel herself failing completely as the orgasm hit her. She couldn't hold on any more. Her cunt and lower abdomen rippled, her rectum pulsed in rhythm to the jets of hot seed that David began to deposit with a yelp. The strength of her colonic ripple expelled David and she pulsed forward onto her cousin. Her legs slammed together and she twitched and cried. It was all too much and a little stream of fluid left her cunt as her bladder failed.

No experience could top this she would recall later when she came to her senses. She was lying in he cousin's arms in a bubble bath a soft hand massaging the sting from her little bottom.

Caroline had enjoyed the evening but felt a pang at the thought of a sexual mountain she had yet to climb. She wondered about what might flick her buttons the way she had seen happen to Nicki.

Red Hugh
Red Hugh
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