Sharing is Caring

Punishments were agreed on before being administered. Sasha was especially turned on when Caitlyn told her how obedient she chose to be sexually. She had to please Miles in every way, which of course brought her own pleasure. Sasha could only dream of being spanked until she was dripping with lust.

Again Sasha stilled Caitlyn and said she needed a bathroom break. Caitlyn did too and accompanied her to the restroom. At the vanity as they were washing up, Sasha looked into the mirror to see Caitlyn looking back at her. "Does he ever leave marks on you?" she asked Caitlyn's reflection. Caitlyn nodded and quietly added, "But they don't last long."

"Can I see?" Sasha asked. Again Caitlyn nodded and broke their stare in the mirror to glance surreptitiously at the door. Without being asked Sasha latched the door against intruders and turned toward Caitlyn. Taking a deep breath, Caitlyn began inching up the back of her dress and instinctively bent ever so slightly over the vanity counter top and spread her high heeled feet apart in a well learned stance.

Caitlyn could see Sasha's reflection move directly behind her and she blushed at the thought of the sight she would be revealing. If Sasha was surprised at the lack of panties covering Caitlyn's treasures she did not let on. However when the six horizontal stripes across both perfectly formed cheeks of Caitlyn's ass were revealed, she inwardly gasped and covered her mouth with her hand. She did not turn away though.

After what seemed to Caitlyn like an eternity Sasha again met Caitlyn's eyes in the mirror. "Did it hurt much?" she whispered.

"Yes, at the time but not now." she replied.

Sasha returned her gaze to the striped buttocks and again in a whisper asked, "Can I touch?" Caitlyn nodded, unable to form words.

Sasha traced the angry looking lines with the soft pads of her fingers completely from one end of each stripe to the other end, including the valley between the cheeks. Caitlyn held still for her inspection. "But you also liked it?" Sasha asked. Again Caitlyn nodded 'yes'. As if she just noticed, Sasha blushed and smiled impishly at the reflected image and said "Yes, I can see somebody liked it."

Caitlyn knew Sasha could see just how excited her pussy had become at the thought of exposing herself so blatantly, but his was part of Mile's order on not hiding the truth. "Does he make you keep yourself totally bare and smooth like this?" Sasha questioned. Now Caitlyn definitely knew Sasha was inspecting her intimately.

"He prefers me that way and I like to make him happy, so I like it like this too, and it feels amazing during sex," Caitlyn confessed.

Sasha's hand was still caressing the warm striped cheeks, as if trying to erase the marks, "Why did he do this?"

Sasha composed herself trying to find words that would make sense to Sasha. Finally she said, "I told him how I felt about you and how I wanted you to join us on our vacation."

Sasha eyes flared angrily as she barked, "And he whipped you for that!"

"Oh no, he would never punish me for telling the truth. He corrected me for hiding the truth from him for so long. At first I didn't know how to tell him how I felt about you."

Sasha's eyes softened and a tear formed at the corner of her eye. She embraced Caitlyn close from behind, her breasts warm against Caitlyn's back. and asked, "I was the cause of your pain? You would endure this for me? I wish you had told him and avoided this."

Caitlyn said, "I wasn't sure, and I'm still not sure how you feel about all this."

Sasha leaned into Caitlyn and softly kissed her lips, and said with a smile, "I think I'm pretty sure how I feel about you, but give me a few days to digest the whole obedience situation." With that said she firmly swatted the perfect butt cheeks she was previously caressing, eliciting a cute yelp from Caitlyn. "Now lets go finish our wine and talk about shopping for a Jamaican beach."

The plane ride was pleasant but worrisome for Sasha. The trio sat all three abreast with Miles in the middle. Sasha could tell it was an easy and close relationship between the other two but wondered how she would fit in.

The memory of the stripes from the crop across Caitlyn's backside weighed heavily on Sasha's mind. Was she doomed for the same experience? Could she endure it? Did she want to? Would she cry? Why did the thought of it make her clench her thighs together and create a deep longing in her nethers?

The mild vibration of the plane was just enough to remind her that she was newly shaven beneath her panties and even the soft caress of her panties was maddening. She wondered if she had gotten too carried away with the razor. The vision of Miles' hand on Caitlyn's bare thigh just below the hem of her short flirty skirt made Sasha lust for a warm male hand on her thigh also, and again her loins burned with desire.

Many questions but few answers flew through Sasha's mind. She decided to have a good time on the trip and not fret the consequences. And just as quickly she sighed and wondered if this whole trip was a huge mistake.

Miles must have heard her soft sigh because he turned to face her and asked if everything was all right. Sasha nodded yes and smiled and understood how Caitlyn could get lost in those deep eyes and sexy smile. Miles patted her leg and left his hand there, a few inches above her knee, totally respectful but protective and warm against the chill of the plane. His touch sent a flame of desire directly up to her very core.

Sasha now wished she had worn a flirty skirt like Caitlyn, instead of her sexy skinny jeans, and that the warm hand would find its way under her skirt and then higher. Then her mind flashed to the vision of Caitlyn who she knew was bare beneath that cute skirt, pantieless and probably anticipating Miles's touch. She clenched her thighs together at the thought of his touch and the seam of her tight denim jeans provided only a hint of relief. Maybe she was glad she had worn them after all.

Sasha's fantasies played out in vivid detail on the inside of her eyelids as she nodded off, her head leaning on Miles's shoulder. Just before closing her eyes she noticed Caitlyn leaning on his other shoulder. Miles was happily in the middle of a beautiful trio, and the plane flew on.

They had not yet explored beyond the overly opulent hotel room and had not been there long enough even to unpack when Miles called to Caitlyn, "Are you happy, baby? Is it what you wanted?" Caitlyn and Sasha stood side by side at the patio door admiring the awe inspiring view of the beach and the turquoise water. Two beautiful women who were very different looking but somehow very similar in stature to each other, like two bookends, turned to smile at him.

One a dark brunette and one a dark blonde, but both strikingly beautiful, they looked like twins from a yoga or Pilates class. Both were fairly tall. Caitlyn was nearing 30 but looked younger and Sasha a few years behind, both slim and not overly endowed, but perfectly formed breasts on both and well proportioned derrieres indeed. Both looked like they could rock a pair of yoga pants also. And both were beaming a broad smile.

Caitlyn was elated that Sasha enthusiastically accepted her invitation to join in their vacation. Explaining the relationship between Caitlyn and Miles was extremely difficult and at first Sasha was hesitant to embrace their happiness. After all she had just left an unpleasant relationship with a messy departure.

"Oh yes, love, it is perfect. May I thank you?"

He answered "Yes, but first let me reassure Sasha that she is in no way expected to participate if she is not comfortable. She is welcome to participate or not, her choice. She is welcome in our room or there is another bedroom if she desires it."

Sasha smiled up at him and mouthed a silent "Thank you."

Then she blushed mightily and shyly glanced away as she noticed Miles's gaze was focused on her lipstick glazed lips. She wondered what was running through his mind that could cause him to look so lustily at her. She bit at her bottom lip and cursed her own libido for even suggesting such things.

Sasha meekly followed Caitlyn's lead as she disrobed. Miles drank in the sight of the two women and how they looked when they got naked. Caitlyn confidently stripped out of her travel clothes and Sasha reluctantly relinquished her protective coverings. There was just no way to sexily strip out of skin tight jeans and Sasha again wished she had worn a skirt as she tugged at the legs of her jeans and fought to keep her balance.

How different they were in the same task. Caitlyn blatantly removed her skirt and blouse and folded them before placing them on the nearby chair and proudly displayed her nude body. Sasha looked like she wished she could disappear into the furniture. She battled the urge to turn her back to Miles as she unconsciously stuffed her panties under the rest of her clothes, out of sight, and fought the urge to cover her newly shaven mound. Unbeknownst to her it would be the last time she wore panties or tried to cover herself on this trip. Miles appreciatively watched both women.

Only Sasha knew her smooth vulva was only yesterday covered by her finely trimmed pubes. After packing last night she couldn't sleep in her excitement and ended up in the bath tub, planning on masturbating to help her sleep but ended up with razor in hand, intending to just touch up her 'landing strip'.

Minutes later she looked in the mirror at the totally smooth image of her mons, just like Caitlyn. Except her lips were swollen in excitement and her nub was standing proud and screaming for attention. And then she furiously masturbated, loving the newly discovered feeling of her bareness.

So it became that Sasha and Caitlyn were naked in the plush Jamaican hotel overlooking a beautiful sandy beach crowded with skimpily clad vacationers worshiping the sun. The balcony doors were wide open and a brisk ocean breeze fluttered the curtains. The atmosphere was heavy with tropical humidity and sexual anticipation.

Any curious onlooker had a good chance of seeing into the room that was only three floors up. That thought fueled a burning fire in Sasha's libido, knowing there was a possibility of being seen entirely naked in a very compromising position for the first time in her otherwise boring life.

Not fully comprehending how she got in this position, she followed her friend's lead and was kneeling on the carpeted floor beside Caitlyn, so close their legs and comely hips were touching each other. Before them stood Miles. Sasha watched wide-eyed as Caitlyn calmly unbuckled, unzipped, and lowered his trousers, allowing Miles to step out of them.

He was left standing only in his boxers that were tented in front by an obvious erection. Caitlyn next hooked her fingers in the waist band of the boxers and slowly lowered them to the floor to join the trousers. Sasha did not even see the boxers hit the floor. Instead she was staring at a handsomely hard cock that was now mere inches from Caitlyn's face.

Both women were close enough that Miles could feel their breath wafting over his shaft but neither had moved. Finally Caitlyn moved toward his shaft and extended her tongue. Sasha watched in wonderment as Caitlyn's tongue lapped at the base of Miles's cock, just above his scrotum, and slowly licked up the shaft to the plum shaped head.

When she reached the top of his shaft she twirled her tongue around the head and laved it in her saliva. Looking up into Miles's eyes she trapped his shaft between her lips and confidently began a slow trip back down the length of his cock, taking it in deep. After devouring at least half of his length she sucked hard, causing her cheeks to cave in, and traversed back up his shaft.

The shaft now appeared wet and shiny. Reaching the very tip she again laved it with her tongue and finished it with a french kiss before letting it pop from her hungry mouth. With the tip of her pink tongue she nudged the shaft toward Sasha.

Miles's cock seemed to throb with every beat of his heart as it bobbed in the air between the women. Caitlyn turned toward Sasha and smiled and nodded, silently giving Sasha permission to share her prize. A blowjob was not entirely new to Sasha but sharing it with her girlfriend definitely was. The size of Miles's erection and Caitlyn's skill were also of some concern to her. She did not know if she could measure up to her friend.

The moment seemed frozen in time as Sasha looked at the object of her desire looming in front of her. She watched as a clear drop of pre-cum bubbled up at the head of his cock and start to form a long stringy droplet. That seemed to spur Sasha into action and she leaned forward and trapped first the droplet and then the shaft itself between her lips.

Yes, this was definitely more cock than she ever experienced before, she quickly decided. Caitlyn wrapped one arm around Sasha as if to lend encouragement and strength to her. Caitlyn and Sasha each had one hand on Miles's hip as if to steady themselves and Miles had one hand on each of his devotee's shoulders, making the erotic circle complete.

Looking into Caitlyn's eyes Sasha took more of the shaft into her mouth and tried to mimic Caitlyn's technique, hoping she was providing as much pleasure. She was burning with desire and savored the wickedness of the new experience but gagged as she got too adventurous.

Miles drew back from Sasha, his shiny cock dripping with her saliva was suspended between the two expectant women. He turned and whispered to Caitlyn, "On all fours, pet," and she spun around and assumed the position.

Sasha was kneeling beside Caitlyn who was on hands and knees with her arms stretched above her head towards the pillows, her breasts pressed into the bed linen and her naked ass posed high in the air. Sasha gulped in surprise at how exposed and vulnerable Caitlyn left herself, all of her privates were now totally bared and available. Sasha did not know if she could ever be that brave.

Miles was on his knees behind Caitlyn and Sasha watched in amazement as he forged his raging hard cock forward to slowly but firmly split open the preferred wet pussy lips and press in until he was buried halfway in her hot cavern.

Sasha's gaze was locked onto his hard shaft right at the point it was captured by Caitlyn's shaven smooth pussy lips that hugged it tightly. Never had Sasha experienced such a wanton sight and her eyes were big and her breath was erratic. Sasha was only inches away from the erotic sight.

Caitlyn pressed herself back until her hips smacked into Miles's pelvis, forcing her pussy to entirely engulf the hard shaft. The sight was almost more than Sasha could comprehend and she shifted her gaze, trying to see Caitlyn's face, wanting to make sure she was all right.

Miles lifted Sasha's chin with one finger and pulled her face back to where her eyes were mere inches from the junction of his cock and her friend's cunt. It was like living porn with real sights and smells. "Watch and learn for when it is your turn," Miles instructed her.

Sasha blushed, nodded and then concentrated on the vision of Caitlyn being ravaged. Miles held still and let Caitlyn do the work. Sasha's eyes were fixated on the large shiny shaft being swallowed by the seemingly too small pussy of her friend, entranced at how the wet lips stretched to accommodate the rigid cock, clinging tightly and smoothly sliding at the same time and causing her ass cheeks to smack against his pelvis, and her breasts to sway with each stroke.

Sasha's own nipples were achingly hard and her core was desperately wet with need. So far no one had touched her to relieve her desire and she was too shy to touch herself.

Miles stilled Caitlyn's hips with only half his cock buried in her pussy. "Sasha, grab the bottle of lube beside Caitlyn's pillow and open it," he instructed. Sasha glanced at him in wonder as she could plainly see that Caitlyn's pussy was soaking wet and coating his cock profusely and that lube was definitely not needed.

Miles returned her look with a stern stare that said "Don't question me," and she immediately reached for the lube, opened it and handed it to him. He did not extend his hand for the lube but calmly said, "Take Caitlyn's cheeks and spread them for me."

Sasha was slow in obeying because she was trying to process the instruction. "Sasha," he muttered and she reached down Caitlyn's back, over her hips, and gently cupped each of the gorgeous ass cheeks in her hands, caressing them as she did. She looked up at Miles and he nodded at her to continue. She slowly and uncertainly spread the cheeks that were mere inches from her face and bared the dark star of Caitlyn's asshole.

"Now squeeze one drop of lube directly on her hole," he instructed. Sasha's gaze jumped to his face and she froze and couldn't follow through with the order. She looked pleadingly at Miles and he just nodded and patiently waited for her to continue. With trepidation she raised the bottle of lube and holding Caitlyn's ass cheeks apart with one hand forced a single drop of lube from the container.

Unfortunately her hand was shaking so badly from either excitement or fear that her aim was not good and the drop of lube landed at the junction of Caitlyn's soaking wet pussy and the angry looking shaft of Miles's cock. "That's not where we need it pet, she is sufficiently wet there."

Miles reached down with his thumb and scooped up the drop of lube from his cock along with a healthy dose of the copious juices of Caitlyn's excitement. He reached his essence coated thumb to Sasha's mouth but she just raised her beautiful questioning eyes to him. He slowly painted her pale pink lips with his thumb, coating her lips with the mixture of pussy, cock, and now lube. The mixture made Sasha's lips glisten.

Suddenly it was like she understood the implication of his actions and her face looked unsure but she slowly slipped just the tiny pink tip of her tongue out of her mouth to taste the feminine elixir on her top lip. As if deciding her first taste of pussy was ok, she smiled shyly up at Miles and licked a circle around her mouth, savoring the taste.

Miles was studying her as she did this and asked,"Taste familiar?" Sasha nodded. "But different?" he continued. She again nodded and smiled at him. Twice more he offered his essence coated fingers to Sasha and she immediately opened her mouth to hungrily suck his fingers clean without being prompted.

Miles pummeled Caitlyn's pussy again and after a few strokes, he stilled Caitlyn's hips and slowly pulled his cock completely out of her tight tunnel. He moved ever so closer to Sasha until his hot cock was wavering and bobbing with his heartbeat in front of her face, almost touching her lips. Again Sasha looked up at him, not understanding. He moved closer until his cock was brushing her lips and she suddenly comprehended.

She opened her lips and her tongue lapped at the proffered shaft. Miles did not plunge into her mouth, but waited for her to make the first move. He wanted it to be her desire to please him instead of him taking his pleasure by force.

As if she realized he was waiting for her she tentatively moved forward to capture the head of his cock with her lips. Her tongue explored the portion in her mouth, savoring the texture of his shaft and tasting the excitement of their coupling. Both Sasha and Miles sighed pleasurably. She moved forward now with more purpose, sucking in more of his cock. The taste of Caitlyn's pussy and Miles's cock seemed to please her.

She bobbed back and forth on his cock enthusiastically until she went too deep and gagged on his shaft. She spit his cock out and looked up at him with tear sparkly eyes like a schoolgirl who has done wrong. He merely smiled at her and said, "Don't rush it. It will come. Now put me back inside Caitlyn."