Complex Relationship Ch. 07

Story Info
Brandon begins to worry, Katy and Ashley try anal.
3.5k words
4.71
42.8k
9
0

Part 10 of the 16 part series

Updated 09/22/2022
Created 06/19/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Thanks to luvtaread for editing

A couple of weeks had passed since that memorable first trip to the natural hot tub. In that time Brandon had been able to develop a few more things to make life a little easier for him and his companions.

One of the first things he had to work on was a way to divert and clean the stream water before it reached the pool. This had become an issue when Katy had bathed in the pool one morning. After that they had begun taking water from upstream and used the pool there like a natural bathtub, a cold bath but a bath tub nonetheless.

In the process of diverting water he was also able to develop a crude shower. It worked pretty well, but it was solar heated so really only one person could use it per day. As a result they cycled through with each one getting to use it every four days. Funny thing was Katy never got fully clean on her days, usually because she would invite someone in to 'help' her and never quite got around to the shower before the limited water ran out.

All and all the group had settled into island life pretty well. They had grown accustomed to their diet of mostly fruit and fish, of which Brandon was now quite good at catching using a combination of a spear and a small net. They would occasionally use some of the canned food for a treat as well.

Despite their comforts, the growing amount of time spent on the island weighed on Brandon a bit. While he certainly enjoyed spending time on an island with three gorgeous women, the fact it had nearly been a month since the storm landed them here and there had been no sign of planes, helicopters, or boats in the area concerned him.

When they first landed Brandon had prepared for the worst, but hoped he was over reacting. His initial thoughts were that it would not be long until Katy's family noticed she was missing and sent out a search, but that hope died in the week they were building the shelter. As it was unlikely that their island, with the signal fire he silently kept lit, would have evaded notice from searchers.

After that first week he became concerned that something had had happened to the ship. In that case it was likely to take a few weeks to get every thing sorted out and figure out that four people were missing. Even if you assume that, for some reason, something had happened to Katy's family to prevent them from sending help and you took into account that Ashley's cared little for her, there still were people who would notice their absence. Mel's mentor and mom would probably raise a fuss about Mel and Katy. Not to mention he knew his family would try to find him.

The problem was it had now been almost three weeks from when the cruise was supposed to end, so even that possibility was fading by the day. Brandon was beginning to fear their absence would never be noticed and began to wonder if he would need to set out on a raft to find help soon. He was also greatly stressed by the fact that it was now hurricane season by his rough estimate.

He sat alone staring out to sea wondering just how much longer the four of them could sustain their existence on the island. He also felt guilty because a part of him, specifically the part getting showered with the attention of two hot women nightly and potential a third, did not want to return home. He suspected it was this part of him that kept him from building a raft and searching for help.

Brandon was so lost in his thoughts that he failed to notice someone behind him until a soft hand touched his shoulder and he looked up to see Ashley behind him.

"Dinner's ready" He heard her say before she apparently saw the look on his face. "Brandon what's wrong?" she asked with concern on her face and in her voice. Brandon thought about denying it and Ashley seemed to interpret his silence, "And don't tell me its nothing darling, something is seriously bothering you." She said as she sat down facing him and took his hand in hers.

He looked into her blue eyes and seeing the concern in them began lining out an abbreviated version of the thoughts he had been pondering for the better part of an hour. He did leave out his guilty feelings though.

After he had finished she said, "I hadn't thought about it that way."

"I know that was kinda the point, I didn't want you three to worry about it."

Ashley looked a little upset at this and said, "What us innocent little girls can't handle the truth is that it?" with a hint of anger in her voice.

"NO, NO it's not that at all." Brandon said defensively, "It's just that most of survival is mental, keeping a cool head and the less you think about the worst, the better. The more you believe you're going to be okay, the better you handle the mental strain. So my thought was better to keep this to myself and not instill doubt into the camp. It's not a criticism on any of you three, you are all pretty tough and I have no doubt you can handle these thoughts. In fact you all may have had them like I have. I think its best to not broadcast them."

"Just like a guy," she said smiling and shaking her head. "You do realize that Mel and I have been discussing this topic for weeks now?" Brandon looked at her surprised and she said, "Thought not, well we have and we agree that telling Katy is probably not the best idea as she might not take it too calmly."

"But..but..but you just said..." Brandon stammered out in shock.

"I know what I said, and I was making sure you weren't losing sight of the type of women on this island with you darling."

"So then why not tell Katy?"

"I love Katy, she is my new best friend after all, but she would panic. Mel and I, not so much, we've dealt with hardships in our lives and we're realists. Katy, she's been pampered she does not deal with adversity too well. Between the three of us we have given her a kind of island vacation.

"The thing I have discovered about her is that as long as she's getting laid frequently she's pretty laid back and easygoing. It's when she gets horny that she gets irritable and pessimistic; I swear sex is like a drug to that girl and boy is she ever addicted."

"I'm going to go out on a limb here and guess that that discovery had something to do with your sudden interest in other women and the plan that landed her in my shelter after that 'bet' you guys had a few weeks back."

"Well sort of, my interest grew out of the fact that while being held captive the three of us would comfort each other and after giving it a try I found it was fun. As for the bet, I'll admit it was my primary reason, but now I have others."

"Oh like what?" Brandon asked intrigued.

"Like the fact I knew you'd enjoy it, but she has made you a better lover, and now that you have become a bit harder to keep up with, it's good to have another outlet for you."

"Have I now?"

"Yep, of course Katy had her own motives there I think, word is they involve a certain redhead."

"You know about that do you?" Brandon asked surprised.

"Oh, so naïve darling," she said then continued. "Know about it? I'm helping her plan out a strategy." Brandon was floored by this.

"So let me get this straight not only are you okay with me fucking Katy regularly, but you are intending to help me fuck Mel as well? This has to be a trap, it's a trap right?" Brandon asked when he had recovered from his shock.

"No, seriously no trap, I love to watch you and Katy fucking and I love the way you make her cum so hard every time. As for Mel I have seen the looks she gives you when she thinks no one is looking. Not to mention the way she fucks Katy or I while you're looking or just after you've done something hot. Trust me, she wants you as much as Katy and I do, she's just in denial about it. I can't wait to be there when you blow her mind."

"Seriously?" Brandon said, now down right astounded.

"Yep, in fact I think the next step of the plan is going down tonight. It'll be pretty fun for all of us I think, could be a first for you as well."

"What?" Brandon asked intrigued

"You'll find out soon enough darling, right now its time for dinner." She walked away and he just stood their puzzled.

"You coming darling?" Brandon just nodded and headed off to dinner. After the short meal the four retired to the shelter. Once they were on the group bed and had begun their usual fooling around Katy tapped Brandon on the shoulder.

"Brandon I want to try something with you and Mel," she said. Then after a beat she added, "I want to fuck both you at the same time. So, will you fuck my ass while Mel fucks my pussy?" Brandon was floored by the request, Ashley had warned him it would be something new but he little expected this.

Ashley, who was sucking his cock at that moment brought him back with a hard suck before she gave him a wink.

Then taking her mouth off his now hard cock and said for him, "Yes, Katy he'd be glad to, won't you darling?" Brandon still dazed, nodded.

"Oh goody!" Katy said obviously excited, "I was hoping you'd want to. Mel and I will get started, Ashley could you take the edge off and prep him?" Ashley agreed and as she resumed sucking him off Katy positioned Mel on the bed on her back before straddling the plastic cock and lowering herself on to it.

Shortly afterwards Ashley shifted positions and lowered herself onto his hard shaft. She began to lift herself up and down at a rapid pace. As a result it did not take long before both were very close to orgasming. A few minutes later he could not hold back his release any more and came in her; she did not slow down and kept thrusting around his spasming shaft. Soon after she too cried out in release.

She then dismounted him and began working him back to hardness with her hands. While she worked Brandon watched Katy and Mel slowly fucking each other. Between Ashley's hand job and the incredibly sexy sight of the blonde and redhead fucking it took little time for Brandon to be at full mast again.

Once he was hard Ashley silently signaled for him to take a position behind Katy. As he did Ashley tapped Katy on the shoulder and understanding the blonde bent down, while maintaining contact with the strap-on. When she had finished moving she was lying against Mel's chest facing the sexy redhead with her head buried in Mel's shoulder. As intended the move exposed her small toned ass to Brandon.

Despite this being a first for Brandon he remained calm and positioned his cock head at her entrance and before he pushed in he asked, "You sure about this Katy?" He saw her nod enthusiastically against Mel's shoulder and said, "Okay, then just let me know if you want me to stop or slow down okay?" She nodded again and he began pressing forward into the tight hole.

He barely had the head in when he heard a muffled shriek from Katy and he paused. He waited then pushed a little more in. Hearing no cry of pain he decided to pause anyway. He repeated this process of push and pause until his whole shaft was buried in her tight ass.

"It's all the way in Katy," he heard Ashley say and after a few seconds he felt the blonde's hips moving below him as she worked her way off the strap on buried in her pussy.

Brandon began pulling out of the tight hole and as she lowered herself back onto the strap-on he slowly thrust his cock in her ass. The second time he did this he saw that Mel's hips were also moving. Soon Katy's movements stopped as Brandon and Mel traded thrusts working the cocks out of Katy's two holes. It only took a few minutes before the double fucking started sending the small blonde over the edge and soon after she was riding a wave of multiple orgasms.

The sight of the blonde thrashing around between them crying out in ecstasy began to take its toll on her partners as Brandon was soon fighting to resist coming and Mel too looked to be close to her own climax.

In that moment, as he looked down at the impassioned Mel and his thrust into Katy was met by one from Mel, he realized that Katy had succeeded in her goal. Only Katy now separated the pair from truly fucking each other. As he gazed into Mel's green eyes he saw them full of lust and wondered if deep down somewhere inside her it was for him as well as Katy.

As this washed over him he felt a new bond with the sexy redhead and it was enough to overwhelm him so that he lost the battle against his orgasm he had been fighting. His vision failed him when his cock erupted into Katy's tight ass, he saw only those lust filled eyes as if they were burned into his mind. Not long after he heard Mel cry out as she too came.

Brandon pulled his now soft cock out of Katy's ass and rolled onto the bed and was soon joined by Ashley taking her usual place on his right. Soon after he felt Katy roll onto top of him and lean down to kiss him. When she pulled away though he saw the tear tracks, crying, she had been crying, what he had done had hurt her?

His elated mood left him and seeing something was wrong Katy asked him, "What happened Brandon? What's wrong?"

"You...were crying. I hurt you. I am so sorry," Brandon said.

Katy smiled, giggled, and said, "No silly you made me feel better than I ever have. Sure it hurt a bit, it's bound to. I have not done that that much and you are kinda big, but you were very gentle and understanding. You were great and it was far more pleasurable than painful. Thank you and I mean that." Brandon nodded and after another quick kiss she took her typical position to his left, before a very silent Mel joined the group snuggle behind Katy.

The operation had been a complete success according to Katy and Ashley. However, Katy wanted to strengthen the feeling between Brandon and Mel, so they did the same thing the next night. This time she wanted Brandon to fuck her pussy.

Both Mel and Brandon agreed and the evening started with Brandon fooling around with Katy, as Mel fucked Ashley. Katy started off by sucking off Brandon, which Brandon returned later by playing with and sucking on the blonde's boobs. When he was finished with that he buried his face in her crotch to eat her out. After both had cum Katy had him lay on his back so she could straddle him.

Soon after she began working up and down on his shaft he heard Ashley cry out in orgasm and knew that Mel would be joining soon. As with the night before he saw Ashley tap Katy on the shoulder and as she had done the night before Katy lowered her body so she lay against Brandon. Brandon felt the heavy breasts press against his chest as the blonde buried her head in his shoulder.

Brandon looked down the blonde's body to see the sexy red-head pushing the plastic cock into her wife's rear entrance. It did not take Mel nearly as long to bottom out in the tight ass. As with the previous night Katy started the proceedings and soon the three had a good rhythm going. Once again it did not take long for Katy to be pushed over the edge. The fact that Brandon's hands had located her sensitive boobs did not hurt matters. After a while Ashley too joined the group and began playing with and sucking on Mel's exposed tits.

Twenty minutes, and several of Katy's orgasms later, Brandon could no longer hold off cumming. He felt his cum rocketing out of his shaft into the warm tunnel as it again flooded and contracted in orgasm. Mel also came, helped to a second orgasm by Ashley sucking on her tits.

Soon after Mel removed the strap-on from Katy's ass and Brandon and Katy lay together for a while as Brandon waited for the blonde to stop shaking from her orgasms. When she had recovered she lifted herself off his cock and again straddled his chest and kissed him in thanks.

"You had a pretty sexy view eh?" She asked to his surprise.

"Yeah, but I have zero interest in getting fucked with that strap-on." He said seriously.

Katy giggled and whispered in his ear, "Oh, I wouldn't worry about that, you're under her skin and I can definitely tell her pussy is developing an ache for a nice hard cock, and not the plastic kind either."

Brandon was going to ask how she knew this, but did not get a chance as two things happened at that moment. The first was that Mel returned, the second was a bit more surprising to him. He felt a warm mouth envelope his cock and through process of elimination figured it was Ashley.

Sure enough Katy moved to reveal the sexy brunette hard at work sucking the hardening shaft.

"Ready for another round darling?" She asked when he was hard. He nodded and she positioned herself on all fours presenting her perfect ass to him. He got up and lined up his cock with her pussy before she looked over her shoulder at him and said, "I think I want to try the other hole tonight darling. The way you did Katy's last night kinda made we want to try it."

"You sure hon?" Brandon asked surprised.

"Yes, just please be gentle darling. I have not done this before," then he heard her say under her breath, "well, willing anyway." As she turned her head forward to ready herself, Brandon noticed she was rigid.

He slowly began working her pussy with his fingers until she began to moan. Soon after Brandon saw the tension leave Ashley and he began to insert his cock into her warm ass. She cried out a bit, but he knew she was not really hurt and just like with Katy the night before, Brandon began slowly working his cock into her until finally he was all the way in. By this time the pain in Ashley's cries had been replaced with moans of pure pleasure.

Ashley began crying out for him to go harder and faster. He obliged and soon both were crying out in pleasure. A few minutes later his hand found her tits and he played with them as he pounded her ass with increasing speed. Some twenty minutes later he could hold back no longer and exploded his load into her tight ass. This set off Ashley as soon after she too came hard.

As the pair recovered they heard moans of pleasure coming from the other pair and noticed that Katy and Mel had buried their hands in each other's pussies and were working each other to yet another orgasm.

As their friends neared orgasm Brandon and Ashley separated before lying on the bed to cuddle together and watch the other two. After both women had cum and lay recovering Brandon and Ashley kissed.

"Thank you darling that was wonderful, better than I imagined it could be." She whispered.

"You're quite welcome, I'm just sorry you have bad memories to compare it to, you never have to feel that way again, you know that right? I'll be here for you anyway you want, as often as you want, for as long as you want you know that right?" Tears welled up in the beautiful blue eyes as Ashley nodded and cuddled closer to him. In that moment he realized what he had said and realized that he was not only talking about sex.

He loved this girl, really and truly loved her. He had not said the words nor why he was so sure of the fact, but he was sure that is what he now felt. The big question now was- did she feel the same way?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Gift From His Father Ch. 01 A young man receives a strange gift with unique powers.in Mind Control
The Most Valuable Gift Ed wants to give the ladies a special gift for Xmas.in Erotic Couplings
A Shepherd Afield Pt. 01 Ben struggles with his new notoriety.in Erotic Couplings
A Techies Wonderland Ch. 01 A computer tech gets the surprise of his life at an interview.in Erotic Couplings
Charity Begins Next Door Life isn't fair. So when you fight back, fight dirty.in Romance
More Stories