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Best Friend's Sister, Part Seven

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Offline Jon Grey

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Best Friend's Sister, Part Seven
« on: July 05, 2018, 08:44:30 PM »
Tiffany finally released Darla, panting, and allowed the woman to rush to the bathroom, presumably to clean the slick glaze off of her face. Tiffany's breasts heaved, but she seemed to be able to tell that the moment had passed, and began to stand, looking for her clothes. I helped her, and had just about gotten everything together when Emma returned, wearing a t-shirt. The barest hint of a nipple stood out from her chest.

"Thanks for coming by," Emma said, her defeat still present in her voice.

"Thanks for the invite." Tiffany began to walk towards the door. "You put up a better fight than your sister," Tiffany whispered. Emma couldn't keep the grin from her face as we strode towards the door.

We walked down to the car, and when we got in, Tiffany let out a yell and leaned over to kiss me. It quickly became an aggressive, attacking kiss, and I struggled to put the car in park as I realized we weren't going anywhere. I felt her hands at my pants, and soon her hand circled my semi-erect cock.

"Well," she whispered, the excitement in her voice palpable, "drive." I couldn't keep the grin from my face as I shifted back, and began driving towards her house.  The entire drive home, she slowly and deliberately stroked me, and I was easily as hard as I'd ever been when I got to her front door. I did notice Dan's car in the driveway, which meant that he was home.

"Huh," Tiffany asked, her hand still stroking me very slowly. "I wonder if Dan's brought his new lady-friend home. If they're making enough noise, we could go in and I could take care of you." My brain melted with disappointment as I realized she was right. There really wasn't a whole lot to do. When I looked at her face, she had a smoky, expectant sort of grin.

I still don't know what possessed me to do it, but I gently pushed her head down towards my crotch. As soon as I started it, I felt part of my brain expect resistance, or a proud angry woman to shove me away, and at the least throw me a glare. But she smiled as she opened her mouth, and treated me to a very nice blowjob.

I sat in the car bewildered (and very happy), and when she finished she smiled. After a moment, she looked into my eyes, and I suddenly understood her motive.

"Who was better?" she asked. My mouth went dry as Tiffany included me once again into her competition. Although it wasn't really a challenge.

"You were," I breathed. Tiffany's face went impassive.

"No shit. I meant between the sisters." My face went pale, and I wondered for a moment if I'd crossed a line, and pulled the competition too far into the relationship. I started stammering, but saw her eyes twinkle, and her mouth twitch.

"Gotcha. Thanks, lover." I groaned at her ill-timed humor, even as she put my spent dick back in my pants. "Should we go in and break up any crazy games?"

"Would you leave him alone?" I said, joking. She grinned.

"Oh, relax. It's not like I'd walk in on him when he wasn't expecting it. Only one of us has that talent down." She started to get out of the car, giggling as I flipped her off. I did take a moment to admire her ass, but immediately jumped out of the car and followed her into the house.

We heard the TV on, and Tiffany motioned for me to follow her upstairs. As we passed the living room to get to the stairs, we noticed Dan and a young girl. We could see next to nothing of her as they were both reclining on the couch, her head leaning on his shoulder. It was, all in all, a pretty chaste scene, and I smiled as I followed Tiffany towards her bedroom.

When we got upstairs, I immediately kissed my girlfriend, and felt my hands wander to just under her still sore breasts. She winced, and I pulled away.

"Sorry, stud," she whispered. I smiled at her and we kissed. We made out in her room for a while. Every time I made a move below her belt, she shifted, bringing my hand to her waist. I only tried twice. I had noticed that sex was off limits, but I kept reminding myself that we really hadn't been "together" that long. Even as a horny teenager, I knew that that step was a big one if it was going to be meaningful. And if truth is a factor, her amazing blowjobs and handjobs were enough to quell those desires on my end.

When I pulled away, she looked into my eye and smiled, then closed her eyes and sighed.

"You are really a great guy," she whispered. I looked at her, thinking of every single break-up story I'd ever read and tried to remain calm as I answered.

"Uh, what — why do you say that?" I asked as calmly as I could.

"You've been really patient about the physical stuff. More so than any guy I've been with. I'm ashamed to say that I'm usually on my back at this point." I still hadn't gotten used to the frank nature of her language, and blushed slightly. Thankfully, it made me look normal, as I was still pale from the break-up thought.

"Which doesn't make me a slut," she said, mortified that her honesty could be misconstrued. "I mean, I've only been with..." she looked at my face, and I was pursing my lips and looking as sternly as I could. "Wow, do you not want to know." She sputtered and I laughed and kissed her again.

"Look," I told her. "It's fine. I'm happy with you, and you are more than generous. You've taught me to be an unselfish lover already. You give a lot, Tiff. And you've invited me into a very intimate part of your life. Don't get me wrong, I'm loving your physical attention, but I'm glad we're actually more than that."

Tiffany smiled, and I swear I saw I thought her eyes get wet, but she blinked once, then grinned widely. "I guess you've got the whole 'thanks for the blowjob and titfight' market down for greeting cards, huh?" I leaned in and kissed her, glad that she was coming through the emotional confessions and that I still had her as my girlfriend. She pushed me off the bed.

"And now I've got to kick you out. It's late and I've got to work tomorrow." I stood and headed towards the door. "Thanks," she whispered.

"For what?" She grinned.

"I've been really happy lately," was all she said. I let myself out of the house, whistling as I got into the car, and drove away.

When I woke up in the morning, I noticed I had a text from Tiffany instructing me to check my e-mail. I got out of bed, turned on the computer, and waited about two minutes before I was able to get onto the webmail account I checked so often.

The e-mail had a video attachment. The e-mail simply read "I got this after you left. Thought you'd like to take a look."

I knew what it was, but my excitement was still making my hands shake. I clicked on the video and waited for the whole thing to load. Then I pressed play. Tiffany's flaccid tips immediately came on screen, bending and twisting over Emma's rock-hard nipples. The zoom worked well, and gave me a much better closeup of my girlfriend's loss. As quickly as it started, it stopped, but I immediately took a shower to wash away my arousal.

I didn't see Tiffany for two days, but I was able to get a job for the rest of the summer with my dad. Thankfully, he ran a small business that was open until 4 every day, so I could still go out. Tiffany was excited for me, and Dan, with his new girlfriend, seemed relieved that he didn't have such divided loyalties.

The job was mind-numbing, but my father paid well. Probably because he remembered doing what I was doing. I'd essentially be moving large boxes in the storeroom as they came in, keeping inventory, and cleaning up. Such a small store didn't need more than one person, but it felt like what I imagined working in a warehouse would feel like.

When I saw Tiffany, she'd come to the store right about 4:30, as that was the usual time my dad and I left. My dad looked surprised to see her but let her in.

"Well come in, Tiffany. You here for that worthless laborer I picked up this week?" I rolled my eyes.

"Yes sir," Tiffany said, far more brightly than I usually saw from her. "I'm here to see if I can twist his arm and we can go be entertained this evening. Unless he's got a lot of work to do." My dad grinned at me.

"Nope. He's free to go. I can close up shop." As I walked by, my dad grabbed me and shook my hand.

"Just yanking your chain, son. Thanks for the hard work." I felt the paper, but knew that he'd meant it just for me, so I nodded. When Tiffany turned, I slid the money into my pocket, unwilling to look at it while she was so close.

"Thanks dad."

"If you stay out late, please be quiet when you come home. Your mother thinks I'm a burglar when I pee at night."

"An image that will haunt me forever. Thanks!"

"Shelter, food, and emotional scarring! Parenting rules, son. Now get out of here. You've got a gorgeous woman who actually thinks spending time with you is worthwhile. Don't let her realize the mistake."

As we walked to my car, Tiffany had a look of shock.

"I've got to be nicer to you. Your dad's kinda on you all the time."

"No," I said. "He's like that all the time. It's his sign of affection. When he's mad, he doesn't say anything." Tiffany wrapped her arm around my waist and leaned in quickly, slowly licking my neck and ear.

"Can I be nicer to you anyway?" she breathed. I groaned. We made our way to the car and I opened the door for her, which made her roll her eyes a little. She accepted the chivalry anyway, and as I got in the car she smiled.

"So what's on the entertainment agenda?" I asked.

"Well, are you busy this weekend?" I looked at her, incredulous.

"Parents are gone this weekend, so the girls have a place to meet. It'll be easier to hide you in the house this time."

"What about Dan?"

"Seems like Dan's getting some special treatment from his new girlfriend. He's going to be 'out with friends' this weekend," Tiffany said, framing the words with her fingers. I shrugged.

"Sounds like a plan," I said, trying not to sound too excited. Being there the whole time probably meant seeing two or three more fights. "Do you know who's going to be there?" Tiffany laughed.

"What are you thinking, that I'd spoil the surprise? I'll be there," she said, changing her tact and pursing her full lips into a nice pout. "Isn't that enough?" I chuckled and put the car into drive.

We hung out a couple of nights, but she was working on getting the group together. To my own credit, I actually got some work on college applications, knowing that I was taking a year off so that I could save some money for the reckless partying and occasional hung-over test taking event. It also kept me out of some serious trouble. My parents left that weekend for a small-business owner's trip. Dad invited me but I declined, saying that they should have time together, and implying that even the thought of them together in one room while I was there horrified me.

I was amazed at how well the weekend was coming together, and Saturday morning, I heard a knock on my door. Tiffany was there, wearing a workout outfit. "Just out for a jog, and figured I'd stop by and say 'hi'" she said, her voice a little heavy with breathing. Her normally pale skin was flushed, and she was sweating. I invited her in.

"Also, get to my house by five. We're going to have quite a few visitors tonight." We talked for a while, and she jogged back home after a glass of water.

I left the house at 4:30, hoping to get there with enough time. When I knocked on the door, I waited for a few seconds before a towel-wrapped girlfriend opened the door. "Just got out of the shower," she explained. "Come on in."


I followed her upstairs, grinning stupidly (so widely I could feel it). "I'm going to get dressed," she told me as we entered her room. "Are you going to watch?"

"Oh, sorry." I turned around, averting my eyes. I heard the rustling of clothes, and she was wearing a t-shirt and shorts when I turned back around.

"I kinda figured you'd watch, perv," she said, grinning. She kissed me. "But it's really nice that you didn't. Kinda makes me feel special." I smiled at her. "Of course, you're going to see me and about five other girls topless tonight, so I don't know why I'm giving you so much credit."

I snickered and kissed her back. "I thought you were going to be nicer to me," I said, winking.

"Oops." We chatted for a while, and at 5:15, the first knock floated through the house.

"Come down by 6. Stay on the stairs again. I couldn't even see you that first night. And root for me." I smiled, feeling my heart rate climb ever so slightly as I began anticipating the action of the evening.

The minutes passed slowly, and I listened for names as I heard conversation filtering up the stairs. I couldn't hear anything but voices; the closed door blocked the sound. As soon as the little red five turned into the little red six, I slowly opened the door. The barest of clicks marked the opening, and the door swung open silently.

The voices were a quiet clamor, though louder than they were the night I first heard the contest going on. I sneaked down, worried that the light was too much, but the sun had already fallen behind most of the houses, and the first landing on the stairs was back in the hall far enough that I was able to hide behind the first banister. As it opened to the front door, only a small sliver of light even came into the hallway, and seemed even to deepen shadows that I was sitting in. Once I felt as safe as I was going to feel, I turned my eyes towards the living room.

A relatively short blonde and taller (by about two inches) redhead were squaring off already. The blonde's smaller tits were lined up with the redhead's large ones. The blonde's small, pear sized (and shaped breasts) were beautiful, topped with almost brown nipples that stood out just barely.

Of course, the descriptions were made relative to the larger breasts of the redhead. They sagged, but given the size it wasn't an unnatural or strange thing. They were full and looked heavy and thick, and their nipples were pink on top of the pale orbs. The redhead was curvier than the blonde, who despite her height had an almost supermodel look to her. Had she not been standing next to the redhead for direct comparison, the blonde would have seemed taller.

But the blonde was standing next to her. I didn't see a way that the blonde's tits would hold up to the redhead's massive pair. But part of me didn't care, as I felt myself drawn into the competition. Even as a spectator, when the two women strode towards each other, the tension became almost palpable.

"Get her Cindy,” I heard a voice yell, and it shook me from my reverie.

Apparently, Cindy's opponent (I had no idea which of the girls was Cindy, because neither responded) also had support, because "crush those titties, Faith,” came back in response.

Faith and Cindy then went after each other. The shorter blonde stepped forward, obviously wary of her opponent's larger bust. "I'm gonna crush them,” the redhead said confidently. The blonde said nothing, her face impassive.

My confidence was solely with the redhead in this contest, so I was surprised when the blonde thrust her tits into the redhead's. "The fuck you are, bitch,” the blonde whispered. "You're gonna get those fucking bags popped" The redhead grunted as she thrust back, and the sheer mass of the redhead's rack thrust the blonde backwards just a step. But the blonde pushed back and the redhead took a step. Then both thrust their chests forward. With sheer mass, the redhead's pale tits swallowed the blonde's smaller pair, but judging from the equally uncomfortable expressions on their faces, the ocntest had at least started out as a draw.

The redhead pulled back first, just slightly, and the first emotion crept onto the blonde's lips as she began to smile. The smile was interrupted by a vicious strike from the redhead's large pair and the blonde staggered back, before stumbling and falling down. The blonde scrambled to her feet to one of the girl's encouraging the redhead. "Way to go Cindy,” I heard.
Cindy seemed to be standing taller as she watched the blonde gather herself, and even Faith seemed a bit stunned by the fall.  So she reacted just a step slowly as Cindy moved in, and was unable to defend against the massive hug the redhead trapped her in.

"Oh, shit,” Faith whispered. I held in a groan as I watched Cindy's larger, heavier tits begin to envelop her opponent's breasts. Her flesh slowly spilled over Faith's smaller tits and the redhead began grinding to the left and right as she held her trapped opponent.

Cindy wasn't about to let up. She thrust back and forth violently. While Faith tried to fight back, her lack of leverage with both her arms trapped and the lack of weight and strength to escape didn't bode well for the blonde. I realized as Faith's legs sread our just a bit that I hadn't seen her tits since Cindy's had swallowed them in the bearhug. To this point, I couldn't recall a more one-sided match. The redhead's massive chest was easily overwhelming her rival's tits. Watching the ample flesh shift and jiggle without revealing  the blonde's smaller breasts lent credence to my thoughts. Still, I felt myself completely enthralled, knowing that one of the women was experiencing what had to be an amazing high in her inevitable crushing defeat.

I saw Faith realize that she was trapped. Something was making her fight, though, and I made a note to ask Tiffany about it. A note I quickly lost as Faith made the only move she could, and one I hadn't seen coming, though I realized I should have as I watched it.

Faith's shorter leg slipped between Cindy's, and I saw her calf tighten as she pushed forward, obviously hoping that Cindy would lose her footing. The redhead grunted, but was able to react quickly enough to stabilize herself.

"Oh, you bitch. I'm going to flatten you now" Cindy lunged forward, and Faith's leg trapped as it was, lost her footing. Cindy demonstrated considerable strength as she held the falling blonde, but lowered her to the ground swiftly. The redhead moved her hands just before contact, pushing her hands into the blonde's shoulders to the carpeted floor. For a split second, I saw the red, sore breasts of her opponent appear from under her seemingly unfazed tits.

The other girls were just as shocked, though it was easy to pick out the Cindy supporters in the crowd. Several of them were smiling as their friend dominated her rival. Faith, for her part, looked incredibly uncomfortable, but Tried twisting away from the wrecking balls that Cindy's tits had become. The redhead pulled back, lowering boom after boom with her heavy udders. Cindy's own flesh distorted as it struck the ribcage of the young blonde, but not a lot. The firm breast tissue pushed back just slightly as Cindy buried Faith's tits again.

I wondered how long Faith would be able to take the pounding, grinding assault of the redhead. Cindy slowly pulled off of her foe, and revealed the red, soft-looking sacks of her beaten rival.

"Stand up,” Cindy said, reaching her hand out. Faith shook her head in the negative, and Cindy made a point of sighing before reaching down and grabbing both of Faith's wrists. The way Faith sprung into action, twisting her hips to the left, I was almost certain that she'd mount an offensive, but Cindy used the momentum of the twist against her opponent, and soon had the blonde face first on the floor, her pear-like tits just squeezing out between her sternum and the carpet. "Do you really want carpet burn on your tits, Faith? Stand up and we'll end this quickly" To emphasize her point, Cindy placed a foot (seemingly gently) between Faith's shoulder blades.

"Okay, okay" Her voice was muffled, as her face was pointing towards the wall opposite my hiding place. I realized I hadn't seen Tiffany, and assumed she was out of view, probably sitting on the couch or one of the chairs lining the walls. My attention quickly refocused as I watched Cindy pull Faith up, apparently disappointed with the speed Faith had chosen to meet her humiliation. The blonde was jerked roughly to her feet and Cindy whispered something to her that I couldn't hear. I got the gist quickly enough when the blonde gently cupped her obviously sore tits and looked down to watch Cindy's impressive left breast squish Faith's right breast, moving through the beaten tit as though it wasn't there.

"Flatten that little tit,” I heard a call come from the room.

Cindy grinned and did just that. Faith let her right hand fall as her beaten sack was pressed against her bones by the superior tits of her opponent. "Keep holding the other one,” Cindy said, loudly enough that I could just make it out. Cindy repeated the same humiliating move on her blonde rival's right tit, flattening it against her ribcage with no mercy or sign of remorse. Faith's titflesh fell, sagging to her body as Cindy pulled away. The once pear-shaped tits fell as though the fruit was trying to escape its skin. Cindy apparently couldn't resist one more show, resting her large udders on the very top of Faith's breasts, then cupping them from below. The blonde's breasts seemed to simply flow around the heavier and obviously better pair before her.

"Now, what do you and your tits have to say for yourself,” Cindy asked, a malicious mirth dancing in her voice.

"Nothing, Cindy,” Faith began, her voice tinged with pain, humiliation, and something a bit deeper. "Just like you said. My tits are nothing, and I'm nothing. There's no way Marcus would ever want me and my little tits when yours are there" Cindy made a motion with her hand and made a deft catch of a cell phone.

"Call him and tell him so" I was shocked. Apparently the girls were in on it, too, because everyone crowded in. I even caught my first glimpse of my girlfriend, as her head came from around the closest corner to listen.

"Please Cindy,” she asked.

"Hey, you said you wanted a titfight for him. That he loved your tits. Tell him they aren't all that great" Faith sighed, but nodded. The code that bound these women fascinated me. The stakes they were playing with were pretty big in some cases, and I began to realize that each fight was an entity unto itself. I still found it essentially arousing, even as Faith began dialing. But these women were doing this almost like one would do a fight in the backyard of school. Sometimes for bragging rights, but in the case of Faith and Cindy, for much more.

Marcus apparently answered. "Marcus? Yeah. It's Faith. Remember how I told you that I had better tits than Cindy?” A pause indicated a lengthy response, or that Faith was screwing up the courage to say something. "I was so wrong, Marcus. She just proved that her big, full tits are better than mine" Another pause. "She crushed mine with hers. She beat them" The short blonde listened for a moment, then shook her head. Her voice cracked as she spoke: "Not with her hands, Marcus. She crushed my tits with her better pair" Another pause. "You wanted the best, Marcus. Cindy's the best"

Cindy took the phone and pulled it to her ear. "Oh baby, we are going to be great together. You love the best tits, right?” I can only assume that Marus had answered in the affirmative as the redhead's face brightened. "Hold on. Let me get my phone, too" Faith stood there, almost dazed as Cindy took everything from her. I was in shock as I watched Cindy use her phone to snap two photos: one of Faith's chest, beaten and weak on display and one of Cindy's pair simply enveloping Faith's weaker breasts. As she took the photos, she continued to demean her opponent.

"I'm snapping one right now, just of what her tits look like after I smooshed them. They're all saggy and floppy now" Then, "Oh yeah, I'm just overwhelming them again. God, it feels like there's almost nothing there. You wanna hear?” As she pressed her chest against Faith's, she dropped the phone. I couldn't hear anything but apparently there was some sound that a tit getting squashed makes, because Cindy immediately pulled the phone back to her ear.

"I'll be right there, Marcus. No, leave it there. I'll give it to her tomorrow. I don't want her seeing you anymore" She closed the phone. By this point, Faith was sobbing. Cindy lightly thrust her breasts into the blonde's beaten chest one more time.

"I don't know why you asked for this, blondie, but you lost fair and square" Faith nodded, and I shook my head as Cindy pulled the now-demure blonde's face to her breasts. Faith began gently kissing the big tits even as Cindy rained more humiliation onto her.

"Imagine your ex doing this to me from now on. Worshiping the best pair, I mean" Cindy pulled away, leaving a string of spit from her tit to Faith's mouth for just a second, and leaving the beaten woman as she walked away.

Immediately, two or three of the women comforted Faith, among them Tiffany, ushering her behind the corner I could not see. While I expected someone to say something, I was disappointed. I heard murmurs and I heard a few whispers of names but they didn't have a connection that I could recognize. Another girl stepped out, wearing a blue sports bra that didn't hide the fact that she had large breasts. I recognized Kara, and I also noticed that she had lost some weight, none of it seemingly from her tits. I wondered whom she was going to fight.
« Last Edit: July 05, 2018, 08:49:43 PM by Jon Grey »