Tropical Joys Ch. 03

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The perils of a deflowering.
3k words
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Part 3 of the 5 part series

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

The envelope lay opened on Helen's bed. Caroline was in her mother's room looking for something and noticed the formal dinner invitation from their neighbours. It was an invitation for Helen and 'friend'; an idea was forming in Caroline's mind. She wandered off into her mother's bathroom.

Her mother was sitting naked from the waist down with her legs either side of her bidet washing herself. Caroline was used to seeing her mother naked and neither thought anything of seeing each other in similarly intimate positions. At school of course things such as showers were communal so Caroline's ideas of privacy were somewhat vague.

Helen was 36 and it was obvious that she and Caroline were related. The nature of their relationship was not obvious, they could have been sisters. Completing her morning ablutions she agreed to Caroline's request that she be her 'friend' for the evening.

Helen and David were occasional sexual partners. Caroline's father was often absent for weeks on end on business and at nearly 70 was no longer able to satisfy the woman who had been a mere girl when he seduced her. He and Helen turned a blind eye to each other's little infidelities. Hugh was still putting his penis in his secretaries' mouths and Helen had a small circle of men she could rely upon for discrete satisfaction. She had flirted with the group scene back on the mainland and enjoyed the touch of a woman from time to time.

She had no idea about her daughter's desires but would not have been surprised that an 'older' man figured in then. Had she not fulfilled her desire to make love to her father by allowing Hugh to seduce her all those years ago?

Helen rang David and told him that she and Caroline would be over late in the afternoon for pre-dinner drinks and to meet his guests. Helen asked whether David might like her spend the night and he agreed explaining that he'd hired Charlotte and Sam for his business guest. Helen was not the least surprised by this. She had personally put her virtue on the line to cement deals for her husband.

Caroline was highly excited and set about preparing herself for what she hoped would be a memorable evening. She borrowed a dress from her mother but as she modelled it Helen could see the panties Caroline wore catching the material of the dress and ruining the line as it fell along her adolescent curves. The same problem would emerge if she wore a bra. Caroline's underwear drawer yielded only cotton panties, white, pink , powder blue and other girlish colours and although brief as befitted a slender teenager they would all cause the same problem.

Pulling the dress over her head her mother offered to provide a pair of her panties. Helen often went without underwear but retained a selection of silk garments for special occasions. Helen didn't like the fashion for thongs and having worn one once discarded it with the distainful epithet that it made her "feel like a whore". She was happy to wear small silky briefs and if she wanted to feel the sensual rub of silk on her sex when wearing a dress likely to 'show' she had a small selection of handcrafted silk undercovers. These consisted of a small patch of silk weave with a thread of silk running from each corner and connecting at her rear. In essence a traditional G-string. Helen's bottom was slender and girlish. She preferred that if she wore something to hide her sex that her bottom either be cupped by the cling of panties or for there only to be the merest hint of thread. The idea of a patch of cloth above her rear cleft appalled her. Her favourite was a little G-string with a silk triangle that barely covered her front from her hairline to about half way along her lips. From there a tiny strand of silk ran along and often between her lips up between her cheeks and connected with the two strands running from the front of the garment around and over her hips to her rear. This she offered to Caroline.

There was a problem. Helen by an odd coincidence was one of Rachel the intimate hairdresser's clients. Her naturally blonde curls had been tamed and now a close inspection of her sex was unimpeded by any hair. She wore her pubic hair in a small elegant triangle that tapered to the top of her cleft. Twice a week she had an 'Anal'. This involved a local therapist administering an enema and ensuring that her rear entrance remained as pink, clean and beautiful as her front. The problem was that she had not always been so bare and naturally her daughter straight from a single sex boarding school was a little unkempt below. Like many women who were lightly haired the problem was not one of density but of extent. Caroline's pubic hair ran in an undisciplined manner in the normal pattern across her pubic bone along her sex lips with a tight curl above the start of her cleft and a little further along towards her rear entrance. The result was that her nether curls escaped the confines of the exquisitely crafted garment.

Helen didn't expect that her daughter would be closely inspected that evening but was a perfectionist so after a little discussion she and Caroline agreed that a trim might be in order. The only person capable of helping was Helen so with a gentle depilatory cream and scissors she went to work on her daughter's most intimate places. Caroline's hymen was clearly visible as she lay back spreading her legs for her mother's ministrations. It took half an hour but the result was stunning. The little garment would now be a perfect fit.

There was another problem. The chosen dress was dark blue with a plunging back.

The colour set off Caroline's creamy complexion but to wear the g-string comfortably and being a little gangly in late adolescence the rear of the string had to be pulled into view. Caroline would have to be naked beneath the dress. It was obvious as she modelled for her mother that she was not wearing anything but the blue silk of the dress which sat just above the swell of her buttocks.

The pair eventually set off for David's house. The other events of the evening will be detailed later. By midnight Helen was sitting on David's face as his tongue explored her moist cleft. Helen was sucking his cock at the same time.

Caroline was tipsy. She was not used to alcohol and the few glasses of wine she had consumed went straight to her head. She had seen Charlotte and Sam depart with James and went to the toilet where she tried unsuccessfully to masturbate. The wine had dulled her senses. Twenty frustrating minutes later when she returned to the dining room empty seats were all that greeted her unsteady gaze. She was drunk horny and frustrated.

Unsteady on her slightly elevated heals she blundered about the house and gardens looking for her mother or David. She had not expected to find them together. She had not expected the cock she wanted to deflower her to be spurting into her mother's thirsty mouth. As David spent itself his tongue had brought Helen to a whimpering orgasm. Both were tipsy but not drunk Caroline was. She blundered into the bedroom as David and her mother attempted to cover their embarrassment.

They were unprepared for the tearful combination of reproach and declaration of love that ensued. Caroline fell in a sobbing heap at the end of David's bed. Caroline was an irrational hysterical mess. Helen and David were naked but both independently made a decision. Helen reached out to cradle her daughter in her arms and comfort her. David gallantly offered to leave the pair in privacy. To his surprise Helen looked him in the eye and asked that he remain. Helen asked him to gather Caroline up into the bed that she might stay the night with them.

It was a strange little tangle of limbs that evening. In the end Caroline sobbed herself to sleep. During the night she got up and had to relief herself. As she staggered back from the toilet she clambered back into bed on David's side. She had previously been tucked up against her mother.

As morning dawned Caroline was curled up against David whose cock was full of blood and throbbing while he slept. Caroline's dress was on the floor where she left it as she got back into bed. Caroline took the opportunity to slither down the bed and closely examine David's cock. Its head was red and swollen, she took a little taste. She liked it and forgetting herself began to gently suck on David.

David was dreaming about having his cock sucked only to wake as Caroline's tongue ran around the rim of his raging hard-on. What was he to do, her mother was cuddled up to him on one side and this gorgeous teenager was on him like a limpet. Helen's stirring solved his dilema. Looking over his shoulder at her daughter she smiled and settled back giving David's shoulder little kisses as she reached down to stroke the shaft that Caroline had no idea how to swallow. Speaking of swallowing Caroline was going to find out all about that soon if she didn't let up. As Helen's fingers tickled his balls David gave a sigh and began to fill Caroline's mouth with sperm.

A threshold had been crossed. After all not too many mothers assist their daughter's with their first blowjob. David lay back and Caroline moved up to kiss him. He could taste himself on her, Helen kissed his cheek as his tongue sought Caroline's. Things became a little heated as all three shared a kiss.

David's problem was that he had an important guest to take care of and the temptation of a horny mother and daughter must not be allowed to get in the way. While he was sure that James was happy he had to get down to business with him before he could really enjoy the weekend. Helen and Caroline were understanding even if the latter pouted a bit as David rose from the bed. They were invited to stay around for the day but only had the clothes they'd arrived in. It was agreed that they'd head home clean up change and come back. What would happen that evening was not discussed.

David and James sorted out their dealings by about mid-afternoon and everybody made for the beach. Helen and Caroline had been introduced as sisters rather than mother and daughter although the incestuous implications were hardly less exciting or scandalous depending upon your point of view. Nobody wore anything on the beach and James had obviously fucked Sam standing up in the water but nobody seemed to mind.

Just before the group made their way up the beach for dinner as Caroline and Helen were rubbing David's body with oil Caroline whispered in his ear that she wanted him to take her virginity that evening. As David processed this Caroline looked at Helen and asked if she would be present to help.

Things didn't really go as planned. Nobody dressed for dinner and as the cooking was being done in the big kitchen there was much grabbing giggling and rubbing. David was circumcised and James wasn't. The difference fascinated Caroline. She left the kitchen and wandered back into the living area James was slumped back in a big soft armchair with Charlotte on her knees in front of him sucking his cock. Caroline went over and sat watching Charlotte's mouth go up and down James' cock. She was fascinated by two things. Firstly when erect his cock looked very like David's and secondly that Charlotte had slipped a finger into James's rear. A little wiggle of the buried finger and her mouth was vacuuming a harvest of sperm from James.

Dinner passed and everyone bid their 'goodnights' leaving Helen and Caroline with David. James was being tended to by Sam and Charlotte. David was sitting with Caroline on his knee. She could feel his cock on her bottom. She kissed him and told him that she was ready to make love. Helen got up and walked off into the bedroom. As Caroline and David entered they saw Helen stretched on the bed patting the cover beside her. Caroline clambered up the bed and gave her mother a hug. Helen kissed her softly on the cheek then on the lips, slowly they embraced in an increasingly sensual and erotic manner. Suddenly Caroline felt lips on her ankle slowly tracing their way up the inside of her calf to behind her knee stopping as the kisses became sucks.

Slowly David moved up along Caroline's inner thigh. The way she was cradled by her mother meant that access to her little treasure was restricted. Slowly David's tongue ran across the little crease of her buttocks. Caroline whimpered into her mother's mouth. One leg drawn across her mother she felt warm hands caress her bottom and gently spread her cheeks. Her eyes suddenly bugged as a tongue ran around her little pink rear hole. It felt good, she had become used to the nudity of so many people in the last day but even her mother hadn't touched her so intimately when she cleaned up her stray hairs. Gently the pressure went on the little ring of muscle and David invaded her. This went on for about ten minutes during which time Caroline had reared up onto her knees and in consequence was now suckling at her mother's breast.

In time David's mouth moved from violating her anus to flick along her perineum to the bottom end of her virgin sex. Her lips were swollen and her opening sought his tongue. As she pressed back into his face she became separated from her mother's breast. Helen was masturbating and felt her daughter move imperceptibly south to her open lips and moist fingers. As David found her clitoris a small orgasm shook Caroline. Doing so she hunched as her stomach contracted in a spasm of pleasure. Opening her eyes she was looking straight at her mother's sex. Every other taboo had been broken why not this. Brushing away her mother's self-pleasuring hand she made oral love to her mother. David's cock was pressing against her entrance. He had had virgins before but never taken one like this or in such erotic circumstances.

Caroline pressed back onto his cock. Her sex had soon swallowed his cockhead upon which she gently rocked. Helen was shuddering in incestuous orgasm as Caroline grunted and snuffled, her mouth covered in juices. Caroline was uncomfortable as David's cock moved slowly into her. Her passage was small and tight and her position didn't help. Finally her hymen brought a halt to progress. Discomfort turned to pain. Tears of frustration welled in her eyes. Would this ever be over with she wondered. The problem was a combination of position and David's girth.

After calming down and repositioning herself on her back she tried to take David again. Frankly it hurt like hell and she had become nervous which made her tighten up the minute her lips touched David's cock. The perfect day was turning into a nightmare. David rolled off her and gathered her into his arms.

He told her that there was no way he would persist with trying to deflower her if pain was the result. Helen had slipped away and returned with some glasses and a bottle of blackcurrent vodka.

Pouring a glass she offered it to Caroline, explaining that she too had had a difficult first time and that this might help. Caroline took the drink and knocked it back. She knocked the next one back as well. Helen's plan became apparent as she lent forward and parted her daughter's legs. Slowly softly she kissed and licked between the neat little folds of Caroline's sex. David saw her beckon for a drink. Lifting her head slightly she took a mouthful of drink and returned to her task. Caroline felt her intimate space fill with liquid. It felt hot and cold all at once, her mother was giving her a vodka douche. As Helen drank from her daughter's sex she signalled for a refill. Gradually as the booze hit Caroline's head her sex while moist and aroused felt slightly numb. David had taken up residence on a chair to watch what was happening. His cock stood hard in his lap.

Helen took Caroline's hand and standing her up walked her over to David and had her place a leg either side of him. Cupping her buttocks she lowered Caroline onto David. His tip was inside her. The combination of being so open, a bit drunk and the numbing douche did the trick. Suddenly Caroline lifted her legs cried out once and sank onto David. She hugged him and sobbed into his chest. For ten minutes all she did was breathe deeply and accustom herself to his size. A little trail of fluid tinged with pink ran across David's balls. Caroline began to move slowly rubbing herself against David. She asked for and was given another drink. Even with another drink she was not able to do more than gently rub against David. When she tried to rise and fall on him she felt pain. She asked him if he could stay hard for a while and just hold her with him inside.

After about twenty minutes she actually feel asleep in his arms and slowly his cock softened and fell away from her. She was dead to the world and slept as he carried her to bed and settled in with Helen on one side of her and he on the other.

Red Hugh
Red Hugh
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