Sister-in-Law Affection

This story is continued from a previous chapter.

The past few days had been a rather wild ride. I consider myself emotionally grounded, but recent developments had me anxious and excited. Cheating on my long time girlfriend with her sister had me in utter turmoil. This love triangle was killing and thrilling me.

So many options to consider, angles to calculate and problems to resolve.

Losing my girlfriend Kay was the one consequence I absolutely dreaded. We really loved each other. We essentially agreed that marriage was in our future even though we weren’t engaged in the traditional sense with rings and all. We were still in our 20’s and were holding it off purely for financial and work reasons. I ran my own company and it required a good amount of my attention; it just wasn’t the right time to get married.

Giving up my relationship with Ashley, Kay’s older sister, was just about as unthinkable. We’d had a thing for each other for years since we’d met. Now that I’d finally given in to the inevitable biological urges, I wasn’t prepared to let her go either. The dam had burst and things were a mess, but I was determined to make this right.

I wanted Ashley ferociously, but losing Kay wasn’t an option either. There was a way to win this, I felt it somewhere inside me. I just had to solve the equations. The thrill of pursuing Ashley was wreaking havoc in my head though. How could I be expected to think straight?

She was a sexy little honey pot that had been cruelly dangled ever closer yet impossibly forbidden. Until now. We’d broken taboo. It just kind of happened and now our relationship was sexual. Just like that. I had no idea throwing away all my honor would be so fantastic.

Of course, I’d yet to pay the piper. It was a bill I couldn’t realistically pay, so I needed to dodge the consequences somehow. Fortunately, I was working through the chaos in my head and plans were taking shape.

Easy stuff first. Ashley definitely wasn’t going back to work at that restaurant. In fact, I’d decided she wasn’t going back to work ever again. Neither was Kay for that matter, but I couldn’t tell her just yet. I needed to play this right. I let Kay go to work the next morning for her Saturday shift as usual. When she and Laura were both gone, I went to wake Ashley.

She was still sound asleep. I approached gently and sat on next to her on the bed. As usual, I let her fill my senses.

The musky scent of the stale semen I’d soaked into her hair was a reminder of how naughty we’d been last night. It was my mark; it pleased me that she smelled of my seed. I could see her hair was a sticky mess, still damp from the shower and globs of my cum. I wanted to run my fingers through her hair, but there was no way that was going to work with it glued in clumps. I leaned across the bed, over her chest and grabbed a handful on the far side. She woke to find herself pinned under me and face to face.

I’d startled her awake and mixed in a little pain as I yanked her hair hard. She handled the shock so effortlessly and with such allure I lost focus on my plan for a moment. Our eyes met and we shared a smile. She bit her lower lip and made it perfectly clear she was enjoying being awoken like this as much as I was. She let out a playful whimper and rolled her eyes back as I tugged her cum-soaked hair.

I could not believe how incredibly sexy she was. I was overwhelmed by her charms. She had just woken up, her hair was tangled and her eye shadow and liner were smeared from cum, but she was still turning me on. All I could think of was mounting her missionary and pounding her petite body into the bottom of this mattress. I let that scene play mentally for a brief moment.

Of course, we’d never actually had sex….yet….and unfortunately now was not the time either. I had the initial workings of a plan to keep this fantasy-come-true going and I couldn’t get derailed now. I absolutely needed to pull this off; to me this was a make it or break it point in my life. Handling two women, sisters no less, would either go so right or disastrously wrong. Concentrate on the task at hand I told myself – work now and play later.

“Hey, listen Ashley. I know you just woke up, but I need to talk to you real quick.” I put my finger over her mouth. She always had something to say, but right now I just wanted to lay this all down for her without interruption. It really was unlike me to talk over anyone, except when I was executing a plan. “Just listen and nod. Everything is going to be OK, I’m working on it, but for starters I don’t want you to go back to work at the restaurant. I know that guy from last night works there so you’re done with that place. I’ll send a tow truck for your car and in the meantime you can drive mine. I’m leaving for New York City for business in an hour or so. I’ll have one of the other guys drive so I probably won’t need it all week. Don’t worry about money either; I’ve got a plan – something big that you and Kay don’t know about but I can’t tell you yet. Just hang out. I’ll be back here in a few days. When I get back at the end of the week everything is going to be fine. Got it?” Ashley nodded yes. “You OK?” Another nod.

“I love you, Ashley” I told her with all sincerity. Then I kissed my girlfriend’s sister for the first time full on the mouth. I left it at that and retreated before anything else spoiled the moment.

I called my two chief programmers and informed them we were going to New York City to sell the company on Monday. I told them to pack for the week and come pick me up right away. They were surprised at the abrupt deviation from our long term business plan but they never really questioned me when it came to executive decisions. I wouldn’t have let them talk me out of this anyway; I was on a roll and it was time to strike while this streak was hot.

My business had been subsisting on consulting fees for the past 5 years, but the real plan was to write a killer piece of software that hadn’t been done before. We’d made a breakthrough a year ago and were now decades ahead of the competition. With my two brilliant programmers doing the actual coding and my epiphany for the scheme; my little company had done what multi-billion dollar software firms had been failing at for years.

The software itself was boring; it really just sat in between databases and linked them. It doesn’t sound like much, but it was almost completely automated, intuitive almost. The software and an operator could do in a week what armies of consultants took months to finish. The only difference was that our software did it better. Fortune 500 companies were going to pay billions of dollars for this.

Our planned strategy was to continue our testing secretly, get the software to a polished product and then publish it out of nowhere. We’d planned to cash in via the ensuing bidding war between software giants. The problem with that plan was that pay day was still a year or two away. Given recent developments in my personal life, I figured now would be a really good time to get rich. I had every intention of buying a yacht, a private island and sailing my women off to live in luxury.

The core concept worked and we could demonstrate it now. Although cashing in early meant that wouldn’t be quite as wealthy, we were still going to be millionaires by the end of the week. I’d demand royalties plus stock and the three of us would live like emperors for the rest of our lives. Well, maybe not emperors, but kings and at some point, what’s the difference?

I explained my new action plan to the other guys on the way down to New York City. Normally reserved and a man of few words, I was downright chatty - energized by my conquest of the sisters. The new love, the lust, the thrill and the hormones; everything had me amped up and I was ready to knock all the dominoes down. We’d built a better mouse trap and pay day was imminent.

Saturday we travelled, Sunday we came up with the financial numbers and Monday morning I made an appointment with one of the biggest companies in our market. We proceeded to demonstrate the pure power of the software for two days. Once we had them convinced it was no trick, negotiating our asking price was a slam dunk. Buying it was a no brainer for the. We weren’t beholden to sell to any one company, and the one who landed our software was going to trample the competition into dust.

Our first prospective buyer realized this and met all of my ridiculous demands: cash on the spot, ongoing royalties, stock in the company and two seats on the Board of Directors. We called in the lawyers and accountants who arrived Wednesday afternoon to seal the deal, but all that were left were formalities.

By the time I called my girlfriend Kay Thursday night, I was a genuine millionaire. She of course didn’t believe me. The software project had been a total secret. She knew I made OK money running my consulting company, but all that was really just to pay the bills while we shot for the moon with the database software. Me as a wealthy entrepreneur was a far cry from what she’d known since we met.

I had to hang around until Friday morning to sign documents, but as soon as it was over I jumped in the brand new car I’d bought myself and drove 3 straight hours to our apartment. They were both there waiting for me. Ashley had done as I told her and had quit the waitressing job at the Tex-Mex place. Kay hadn’t exactly quit yet, but she had called in sick knowing I was on my way home. They were both excited to see me and it certainly was nice having two women there to greet me upon my return.

The girls had lots of questions and I had much explaining to do. I’m not much for explaining verbally so I’d made sure the bring lots of examples of my new wealthy status. The new car was the first. When I told Ash she could have my old one, that probably would have been sufficient, but I’d decided to go all out to make my point.

I’d booked Kay and I a trip to Tahiti. It was ridiculously expensive and I’d never really spend money that foolishly but I guess that was the point after all. It took a few hours but I finally convinced her that the reservations and plane tickets were real. Now the realization was setting in and the girls were euphoric.

Kay pulled me aside at one point. “Top, we can’t just fly away and leave Ashley out of all the excitement. We should take her with us to Tahiti”.

Now, I’d never heard anything I desired more than what Kay had just unwittingly suggested. Take a trip to a tropical island with your girlfriend and bring the mistress along for good measure.

If I wasn’t trying to keep up the appearance of a proper behavior, I would have booked Ashley on the trip without a doubt. But when I was making the reservations, it just didn’t seem like any man would invite his girlfriend’s sister along to one of the most romantic places on the planet. Who gets to do that? Me apparently.

It seemed at every turn Kay was making this affair happen as surely as if she were shoving my dick into Ashley with both hands. I played along letting her think she was getting her way bringing her sister with us.

“Sure, we can bring Ashley along with us. I’d better call the travel agency now so they can get her a plane ticket. We’ll have to see about a room for her when we get there; otherwise she’ll just have to crash with us. The travel agent said it was hard getting us into this resort on such short notice, I’m not sure they’ll have another room.”

The three of us spent the rest of the afternoon getting ready to fly out later that night. The two girls were absolutely giddy. Ashley was packing too even before we had heard back from the agent about her plane ticket. I’d told the travel agency to get her on the plane at any cost. I figured they could make that happen but I was sweating it until they called back with her confirmation an hour later.

I absolutely needed them to come through on the plane ticket, but as for the separate room for Ashley I wasn’t exactly trying too hard to get it done. I made a meek request for them to look into another room, but when they pushed back I let it drop without further protest.

“Good news Ashley, they got you a plane ticket!”, Kay yelled at she literally bounced down the hallway to Ashley’s bedroom. She stopped bouncing when she got to her doorway. With a slightly subdued tone she explained “You’ll have to stay in our room though. They couldn’t get you another one on such short notice. Apparently the place is quite exclusive and they’re booked full. No worries, we’ll hardly be in the room at all. They have private beaches, a spa, a lagoon, tours…….” Kay was waving the resort brochure and read off the full list of amenities. I was enjoying them enjoying themselves and we hadn’t even left New York yet.

It was a long trip there but soon enough all three of us were kicking back and sipping drinks in our own secluded hut on the beach. I’d answered all the questions about the sale on the 14 hour flight and now it was time to relax.

I was even feeling a bit more at ease with Kay and Ashley and the mess I’d made of our relationships with one another. I felt the bond between Ashley and I becoming more intimate even as we could not be intimate. Kay was with us the whole time and that obviously prohibited anything physical other than a light touch here and there.

I was anxious to be alone with Ashley, but we had 10 days on the island and we’d just gotten here. Our chance would come no doubt and the waiting simply meant it would be better when I finally took her. I was tempted to take Kay back to our hotel room and rail her like she was her older sister, but I’d decided to hold off as long as I could.

Here I was, waiting and lounging on the beach next to the two of them, my fantasies running wild while they chatted and got drunk on fruity concoctions. I was drinking too and together with the dulcet lapping of the gentle waves, I was feeling downright euphoric – for me anyway. I was serene and felt like nothing could go wrong. A made another major life decision right then, I had to confess.

“Kay, I have a confession to make”, I announced out of nowhere. I was going to do it. Come clean about Ashley and all the dirty things we’d been doing behind Kay’s back. It was the right thing to do and besides I figured sequester on a tropical island was the optimal time and place for any hope at recovery.

“Oh, sounds serious”, Kay drunkenly mocked. The girls giggled. They had no idea of the gravity of the situation.

“It is, Kay. Listen, I’ve done something you’re not going to like very much.” That got her attention and she looked over at me. Ashley propped herself up on her elbows and looked over Kay at me. Now they were both attentive to what I was going to say next.

Even on the brink of disclosure, seeing Ashley propped on her elbows like that reminded me of our first encounter. She’d assumed the same pose as to catch my cum blasts full in the face as she jerked me off not just a week ago. Here she was in her tiny bikini with as much flesh exposed as I’d ever seen. I wanted to climb over Kay and fuck her even as I was mid-confession about cheating with her. I was truly scum.

“Sorry Ashley, I have to do this…..Kay, Ashley and I have cheated behind your back. Twice.” I blurted out and then stopped talking, waiting for the backlash.

Kay turned away from me to face her sister on the lounge chair on the opposite side. They shared a look that I couldn’t quite see but something was amiss.

“pfffft” They both broke into a relived laughter, like one does when the tension finally breaks following drama. What the hell was going on here?

“He did it!”, Ashley burst out. “And we doubted him. Not even a week, days if you don’t count the trip to the city”. They were hugging. Kay finally rolled back over and faced me with a smile.

“Uhhhhh”, was all I said.

“I already know, Top. Ashley told me as soon as you left for your business trip.”

“What?”

“Yeah, I knew like 5 days ago. Did you enjoy cumming on my sister’s pretty little face?”

I thought she might have been torturing me, but her question seemed sincere, even affectionate. What the fuck was going on? I was shaking off the booze and starting to calculate the angles. They seemed relieved. Obviously they had some secrets of their own and I’d been the fool. They were both lay there for a second watching me working it out. I didn’t quite get it at the moment but now I definitely knew there were still mysteries to be revealed.

“Wait, I’m not done yet. One more thing. The other day when you came in and gave me a blow job under my desk; I was watching a picture of Ashley on my computer monitor.”

“Oh, you dirty dog,” Kay replied calmly. Ashley bit her lower lip and raised her eyebrows in genuine surprise. God damn she was cute. “So, did you like staring at a picture of Ashley while I gave you a blowjob more? Or blasting her real face with sperm after her handjobs?”

How deep did this rabbit hole I fell into go? There was no anger, in fact they both seemed pleased. Pleased with me even. I was pretty sure they were impressed that it only took me a week to confess.

I ignored the question. “I love you both and I desperately want this to work out for us.”

Kay sat up, leaned over to my lounger and kissed me. She kissed me again and then put her mouth up to my ear. I though this couldn’t get any more twisted, then she asked me another question and I was again mistaken.

“Do you want to stare at the real Ashley this time while I blow you?”, she whispered. She nibbled my neck. I ran my fingers to the back of her head and grabbed a fistful of hair. I glanced over at Ashley, who was still leaning on her elbows watching the proceedings with intense interest.

I forced Kay’s head down to my instant erection while I looked into Ashley’s eyes. She was so alluring staring back at me; it drove me crazy. Fuck it, I was going to rock this and ask questions later. Once again lust trampled higher reason to a distant concern in less time than it takes to get stiff.

Kay was into this and more than willing to suck me off right here on the beach. Our little beach hut was rather secluded and it wasn’t like anyone was watching us, except Ashley of course. She pulled down my bathing suit and grabbed a hold of my throbbing shaft. I’m not sure I’ve ever been so hard so fast in my life. She ran the head across her wet lips and continued to rub it on her cheeks. Her face made little orbits as she smeared my cock all over her face. Her tongue would lick me as my dick passed over her mouth.

I wasn’t watching Kay though, I was staring at her sister who was watching the action from her lounger 6-7 feet away. She was just lying there, watching her little sister go to town on my dick. I could see her well, even in the fading light of sunset.

Ashley looked up from the scene and met my gaze once again. She seductively bit her lower lip again. I felt a large dollop of pre-cum leak out and lubricate her sister’s face. “Oooohhh,” I growled.

This only encouraged Kay. She gave me a hard tug and I felt her lift her face to look up at me. I pried my eyes off Ashley to look down at the girl between my legs with my dick in her hand. I could see a glistening strand of saliva or pre-cum stretched between her chin and my tip. Her face was slick with our mixed fluids. Then she shoved it in her mouth as she stared up at me. I felt another big spurt of pre-cum boil into her mouth, which she swallowed.

There isn’t much more I enjoy than a woman staring me down as she pleasures me. I find it intoxicating; the shared bond of a lover’s gaze during that moment of fellatio is so intense. I ogled Kay bobbing up and down, the tip of my cock going in and out between her lips. Pre-cum was oozing, which she alternatively swallowed or smeared on her lips. She lifted her head completely off my dick, a string dangled off her lips to the tip. She attempted to lick it up, but that didn’t work, so she took her other hand and cleaned off her face a bit. The she shifted and straddled the lower half of my lounger so she could take hold with both hands. She began pounding away on my meat and used a twisting motion for extra stimulation.