The Good Guy Always Loses Ch. 02

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Jeff's sweet dreams, and bleak reality.
15k words
3.24
67.7k
63

Part 2 of the 2 part series

Updated 10/30/2022
Created 04/02/2014
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Continued from: "The Good Guy Always Loses - Part I"

Thank you for joining me again, hope you enjoyed part I!!

(Disclaimer for the story is included in Part I)

Again... ENJOY!!

*****

CHAPTER IV: SWEET DREAMS

After a while, I slowly jerked off to thoughts of Jenny and other girls in my class, still miserable. I hated how I had to go slowly, because if I tried to jerk it fast, my hand would slip of the tiny length. 'God... Jenny was right,' I thought painfully. 'It's skinny as shit.' I thought of Todd's enormous, muscular dick, and felt a pang of anger and agony. 'How does he have everything?' I asked desperately in my mind.

My thoughts changed, 'Since my sister clearly had no respect for me, Why should I respect her?' I thought. Suddenly the image of her jumping back in shock when she saw me in her room, and the entrancing way her boobs wiggled like jelly, entered my mind.

The image of her flawless butt-crack entered my mind too. I remember when she bent over, and those cheeks slowly spread to reveal the treasure within. My sister's sweet, sweet butthole, that was a place where I would choose to live all my life if necessary. No matter how cramped, no matter how wet and warm. At least I knew I would be surrounded by perfection.

'If I can't have Jenny, please god, please at least let me have my sister...' I thought.

'Allow me to taste her sweet asshole and crack and her puss, and let me suck her tits. Please... please...please...' I thought as I jerked myself asleep.

When I awoke, I was back in my old house where I grew up. I noticed I was in my sister's room, and got up off the chair I was sitting on. She entered the room in her towel.

"Oh... Stacey—... What the hell?" I asked.

"Oh my god, Jeff!" Stacey exclaimed and jumped back, causing her red towel to drop to the floor, and making her jello-like tits bounce wildly. I stared right at them, as Stacey slipped on her towel and fell and hit her head, causing every moving part on her body to jiggle uncontrollably.

"Oh shit Stacey!" I shouted and ran over to her help her up. Once she was up I said, "I'm sorry Stacey, I didn't mean to make that happen."

"Uhhh... It's ok Jeff, it wasn't your fault," she said softly as she rubbed the back of her head with both hands, where she hit it on the wall. Her face was contorted in pain and she looked beautiful even then. That was when I realized that my hands were on my naked sister's waist, gripping her tender love handles and as she rubbed her head quite vigorously. This in turn caused her tits to bounce some more. And since she was scrunching her face up in pain, and I was so close to her, I technically had front row seats to watch my sister bounce, and she had no idea I was ogling her hungrily.

After a good minute of her rubbing her head in that odd way and me feasting my eyes on her moving parts, she slowly brought her hands down and to her sides and gently opened her emerald eyes. The second I looked into them, I was totally lost and forgot how close I was to her or that I was even touching her naked body.

She slowly smiled that deadly smile and looked down at my hands on her waist. I was so stunned at that point that I just couldn't move. She looked back up at me and again, raised a single eyebrow. I was dumbfounded, realizing that I must have grabbed her by her waist when I lifted her off the ground, but now I couldn't move.

All I could do look back and forth between her gorgeous green eyes and her flawless tits. Over and over, for 30-40 seconds, I kept looking between them, till finally I decided to choose her eyes, those emerald depths of her soul.

She gave a little cough and a quick giggle and made a sly pouting face and very slowly moved her hands down to mine, on her waist. Lightly, she removed them and placed them by my side.

She whispered, "It's ok, just keep your hands to yourself from now on ok?" and gave a playful wink.

I nodded like a dumb fool with my mouth open and stepped back a little. She laughed a little at my slack-jawed silliness. She spat on the tip of her two fingers, made sure they were very moist and wet and then slowly inserted them into my mouth, where she rubbed them on my tongue. Feeling the warm foreign saliva on my tongue, I closed my eyes and savored the taste, then quickly swallowed it down. She giggled at the silly look I made while swallowing, then put her hands under her tits and began jiggling them a little, strictly for my amusement.

After a couple of seconds she stopped and turned to leave, but looked down and paused dead in her tracks.

"J—... Jeff... Holy Crap Jeff!" she stammered.

I stopped and looked at what she was looking at. Apparently the entire ordeal had gotten me rather excited, and as I looked down now, I could see the bulge in my pants. 'There's a bulge in my pants!' I thought to myself, 'Ho—How the hell?' I was dumbfounded.

As I looked and Stacey, my suspicions were confirmed. Her look of bewilderment slowly transformed to a look of pure exhilaration and I knew what that meant. I looked up at the sky and quietly thanked god for this gift, and the presence of my sister at just the right time.

As the bulge in my pants grew larger and more uncomfortable, the look of thrill and admiration on Stacey's face grew stronger and stronger. I was ecstatic watching her, because looks like that are generally reserved for other men, or other things. There was nothing about me that was spectacular enough to warrant that look. 'Nothing until now,' I thought to myself.

By some miracle, god had heard my prayers and brought my sister to me, and had given her a reason to love me properly.

"Jeff, Where the hell did you get that sweetie?" she asked as her steely green eyes snapped to mine.

She came closer maintaining eye contact, and I grew harder. Stacey bent over slightly to get a closer look and turned to look up at me as she studied my new member. She looked back down and made both a kissing gesture with her lips and the sweet kissing noise. Se repeated that gesture and noise simultaneously 5-6 times while still ogling my bulge, and then got up to look at me eye-to-eye.

"It looks like you have a problem down there sweet brother... Would you want to handle that on your own, or perhaps with a little help?" she asked seductively.

"HELP!, HELP!" I wanted to scream out, but I was struck silent, and my mouth had gone dry. The combination of circumstance, coupled with those horribly exciting kissing noises, her steely green stare and smile, and of course the fact that she was completely naked, caused my higher order thinking to shut-down. I finally managed to power my bucket of neurosis to convince my body to squawk out, "Help."

A relieved, yet pleasant smile came over her face and I could see her mouth the words, "Thank you," which made me very excited.

She locked the room door, so that there would be no interruptions and again reached for my hand with hers and held them, while slowly leading me to the same chair she had near her bedside table. She straddled me and held my face between her hands. I was in such a state of ecstasy at this point, that normally, I would have cum multiple times and almost felt like I did, but due to this newfound virility, it seemed I could last much longer, while still feeling the same pleasure.

'It was a dream come true. Beyond a dream, beyond of my wildest fantasies,' I thought to myself, as I got hopelessly lost in my sister's aquamarine irises.

This was a look that I had never seen before though, a sinful, sensual look. The kind of look reserved for very few people, definitely not a look for guys like me. It was a look that said, "Things are going to go very well for you now." I welcomed it, as I sat there, still spellbound by here lust.

Slowly she leaned forward, and pressed her lips to mine. She opened my mouth with hers, and her warm, wet tongue entered, uninhibited by my mouth, of course. It felt like an eternity that our tongues rubbed against each other and tasted as much of the other's saliva as possible, till she finally broke the kiss. One strand of saliva hung between our mouths as she pulled away, which she quickly sucked into her mouth. I giggled like an idiot at that and she smiled, licking my lips again.

She leaned back, away from me and tilted her head back, arching her body and sticking her chest out, clearly to give me a splendid view of her luscious tits. I stared for a long time, but this time, when she looked back and saw me, she had a pleasant smile, a sort of smile that indicated she was giving me permission to ogle her. And ogle her I did... I saw her perfect pink puffy areolas and erect nipples, a sight that would make most men weep.

I was suddenly reminded of Jenny, with her gorgeous pink nipples as well. I pictured Todd chewing on them, and staring into her sapphire eyes unappreciatively with his douchebag grin, and felt suddenly sick. But I immediately pushed the thought out of my head and concentrated on the masterpiece in front of me. Forget Jenny, I had Stacey now, and she was enough to keep me satisfied for life.

I slowly cupped her gelatinous tits into my hands and squeezed, and she closed her eyes and moaned slightly. I was amazed at how firm yet fluid they felt. Sort of like squeezing a water-balloon, except Stacey's skin was very smooth.

When I let go she lifted her index finger in front of my face, as if to say, "Give me a second." She moved back on my lap a little in order to clear some space for herself and softly said, "Enjoy the show." She placed her hand under her tits and began bouncing them.

Again my hands naturally found her love handles, which I gripped as I watched in awe. The ferocious bouncing of her tits was absolutely mesmerizing. I quickly stole a glace at her eyes, which were looking directly at mine, probably to see my reaction. Not wanting to miss any of the action, I looked back down at her tits and just stared in wonder.

My entire life, had led up to this one moment, where I could sit back without being ashamed, grip my sister's love handles and watch the beautiful sight of her bouncing boobs. As she watched me, she knew how mesmerized I was, and so kept the jiggling session going for extra long.

It had been around 6 minutes and I could tell her tits were starting to hurt, so I slowly held onto them, not allowing her to bounce them anymore. She knew exactly why I did it, and gave me a grateful smile.

"You like watching me bounce?" She asked.

I looked at her with a sarcastic expression, to which she giggled a little and asked, "All of me?" This sparked my interest and I gave her an inquisitive look.

She smiled knowingly and said, "My titties are starting to ache, but I can jiggle something else for you. Not my ass, you'll see that later," she promised.

Half out of curiosity and half out of pure excitement, I agreed. She told me to support her back with my left arm, so while I sat on the chair facing forwards, her legs faced my right and her back, my left so she was sideways. I gladly wrapped by my arm tight around her waist as she put her right arm around my neck and shoulders for support.

She was trying to lift her leg up in an awkward angle. I was in absolutely no position to complain, because her clumsy contortions on my lap gave for some truly beautiful views of her body that I would have never even dreamed of seeing before. I enjoyed every second of it. Once she had finished raising her left leg clumsily in the air, which looked absolutely spectacular, she looked at me and laughed a little. I joined in the laughter to make her happy, but the truth was, there was nothing funny about her stunning body.

She told me she was going to need support once she removed her arm from my shoulders, which I was more than ready to give. If what she required of me, was to find yet another reason to put my hand on her, how could I ever complain in my right mind?

She removed her arm and immediately I grabbed around her waist from the back and put one hand on her tummy. As she tried to balance herself, I took advantage of the opportunity to rub her tummy and her back and feel more of her skin.

She leaned her right side into my face as I helped her balance and I immediately found myself licking and kissing the side of her right tit. Upon feeling that, she looked down at me and smiled. Then she used her right hand to reach under her left thigh, which was now raised high in the air giving me a great view of it.

I continued to hungrily kiss and lick the side of her tit, completely unaware of what she was trying to do, when she began slowly jiggling her left thigh. I was completely shocked, and fascinated at the same time. She continued to jiggle it and looked down at me, to see how I was enjoying it. I looked up into her gorgeous eyes for a second and just made a "pleasant surprised" expression, at which she giggled. I looked back down at her thigh bouncing and continued to kiss her tit.

As I considered how much effort she went through just to satisfy my need to see jiggling body parts, a warm feeling came over me. It was a mixture of love and absolute wonder. I continued to stare at my sister's beautiful wiggling thigh and began to feel captivated.

'Holy fuck!' I thought, 'It's almost as good as watching her tits jiggle.' I continued licking her tit, and I reluctantly lifted my right hand off her sweet, soft tummy and put it under her calf for support, my left hand still tightly supporting her back. She continued to jiggle and I continued to watch, awe-struck, at how beautiful it looked. I could even hear the inner thigh slap against her leg with each bounce.

I looked up at her and she leaned in to kiss me, causing her right arm to awkwardly bend, but since I never stopped supporting her body, she never stopped the jiggling. As we rubbed our tongues together, I could hear her thigh still slapping.

With my eyes close and tongue deep in her throat, I tried to picture how the scene looked, from far away. The lewd thought of her contorted body on my lap performing that strange action was enough to send a shiver down my spine, and normally, I would have burst in my pants.

Reluctantly I pulled away from the sloppy kiss, took one last ogle at her tasty thigh bouncing, and gave her tit a quick kiss before letting go of her calf.

She slowly brought the leg down and turned to face me again. I began hungrily sucking and nibbling her tits. These were unconsciously the tits I dreamed of sucking all along. In the middle, Jenny's replaced them for a short while, but here I was back where I belonged, eating the tits I loved.

I ran my tongue around her areolas a short while before chewing her nipples between my teeth. I looked up at her while sucking and saw her green eyes meet mine. She gave me a sweet, gentle smile before moaning and tilting her head back. I took that as a sign to close my own eyes and concentrate on sucking these milk-sacs.

I switched each into my mouth biting, nibbling and sucking for a good 10 minutes, before stopping from jaw pain. She slowly got up and had a twinkle in her eye. I knew exactly what she was thinking. She got on her knees and began to undo my belt. Once pulling it down, she saw the bulge in my briefs and gasped. She began massaging it slowly, while studying it lustfully.

Finally she pulled my briefs down and it sprang to life. I was as curious to see it as she was. It was a massive appendage sticking straight up in the air and she laughed nervously as she marveled at it. I had no idea how I got it, but I was not about to slap god in the face for giving me a gift.

She put her warm hands on my thighs and my dick hardened a little more, which she clearly noticed. She looked into my eyes with a yearning I had never seen from any girl in my life. It was a magical look, one that was reserved for men of the highest pedigree. She kindly spread my thighs wide, and my balls immediately dropped low and dangled under my cock.

"Oh my god!" She exclaimed. She watched my sac sway slowly from side to side, all the while licking her lips. She reached out and cupped them, slowly rolling them in her hand. The lust in her eyes was overflowing at this point and my dick was only getting harder and thicker, while pointing to the sky. As she continued to roll my balls around in her soft palm, the overflowing lust in her eyes was at unimaginable levels, and began transforming into a hunger.

She suddenly had the eyes of a malnourished African child. She looked at me and said, "Jeff... Jeff sweetie, I need to eat, I'm so hungry." I looked at her and nodded, to which she gave a relieved smile and let my balls dangle down again. She watched them sway for a moment longer and smiled again.

She placed her hands on my thighs again, further up this time and slowly crawled in closer between my legs. Her face was right up against my meat and I loved every second of it. 'So this is how Todd feels all the time eh?' I thought to myself. 'Well fuck you Todd, I got a nice big cock now too.'

Stacey dropped her hand to the sides of my thighs, and motioned to give her mine. Once she held my hands, she gave a quick wink and a smile, before proceeding to lick my meat from the base till the tip, over, and over, and over. I could feel my cum sloshing around in my nuts as my sister held my hands and lovingly serviced me. Again, it felt like I spurted, but nothing came out. I looked down into her beautiful, eager green eyes, and I saw her lips curl up into a joyful smile, all the while meticulously slobbering my staff.

'God she looks good,' I thought. I finally understood how Todd felt with Jenny between his legs gorging on him. It truly was glorious, and I felt like a champion. I threw my head back and laughed to myself, and then looked back down at Stacey. She seemed to enjoy that.

She let go of my hands lightly and slid hers very slowly along the inside of my thighs. Once her hands reached their destination, she gently began tickling and massaging my love-orbs, but never-ever stopped licking my cock. After a good 10 minutes of meat licking and ball tickling, all while I stared into those deep green eyes, she let go of my nuts and started rubbing my thighs again. She stopped her licking for a moment and admired my drenched love-stick.

"God, that's one good looing dick..." she said, and laughed.

I joined in her laughter for a while as she continued rubbing my thighs, then she gripped her hand around my dick and lifted it up. She began slobbering my balls with an expression of pure delight on her face. I tilted my head back and sighed, while I put my hands behind my hair and interlocking my fingers.

'Is this much pleasure even humanly possible?' I asked myself.

My eyes suddenly opened as I remembered my nightmare from the other night: The wingless angels in shackles, sobbing and miserable as they were forced to taste the demons' cocks. 'But wait...' I thought. Towards the end they weren't crying... No, no. They were happy and content, and adored licking those thick demon dicks.

I looked down at Stacey whose eyes were closed as she affectionately ate my nuts.

"Stacey... Baby," I said softly, almost hesitating to call her that.

She dropped one of my balls from her mouth and looked at me with concern, "What's wrong sweetie?" she asked softly. Her gentle voice and that twinkle in her eyes was so cum-inducing.

"Oh... nothing really. Just uhh... can you keep your eyes open when you do that?—I uh... I like it when you look at me," I said.

She turned her head a little and gave me a sly grin. "You dirty boy... Of course I can, lover." My heart jumped with joy and she went back to sucking my balls but kept her pleasant green eyes locked on mine. She smiled as she sucked and I chuckled to myself shamelessly.