The Pool Party – Part 5

"Jess is worried that meeting Jack's friends at a pool party will affect the casual nature of their relationship, but the surprise that Jack has planned is not at all what she was expecting."

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I froze, looking at Jack, and then at Dan.

Dan came up to us cautiously, giving Jack a look. “Is this okay?” 

Jack was still breathing hard, looking at me. I wasn’t sure it was okay, but he nodded and stepped back. “Yeah, go ahead.” 

Dan turned back to me next. “Is it okay if I touch you, Jess?” 

I felt sudden, intense butterflies in my stomach as he approached, but I was too curious and excited to think twice. “Yes,” I nodded. 

And then he was gently urging me to lie back further on the table until I was leaning on my elbows. He pushed back on my thighs and then stared down at my pussy, cursing. I looked down to see that he was apparently watching Jack’s cum leaking out of me. 

Then the other guys gathered around, too, each of them looking at me and asking if it was okay. 

I couldn’t help laughing then, overwhelmed by the attention. But I nodded and said, “Yes, it’s okay.” 

Ari and Scott took over holding my legs down and back while Dan started rubbing my pussy with his entire hand, rubbing in Jack’s cum, then teasing my clit with his thumb. 

I started breathing harder once again, my chest heaving. 

Then there were hands on my breasts, squeezing and pinching my nipples. 

Dan’s fingers slid into my pussy, and he cursed. “Fuck, she’s really fucking tight,” he told the others. Then he retracted his fingers, slick with Jack’s come and my juices. He brought them close to my mouth, hovering near my lips and just waiting, knowing that I knew what he wanted. 

I sighed and leaned in to lick the tips of his fingers, then started sucking them into my mouth. He growled and pushed them in further, stroking his cock with his other hand. 

On Dan’s fingers, I tasted myself and Jack’s cum, as well as a hint of chlorine left over from the pool. I moaned and sucked his fingers clean, holding his wrist to make sure he wouldn’t pull back before I’d finished. 

“I want to feel your mouth on my cock like that,” he said, stroking as I sucked his fingers. 

I shuddered a little and finally pulled his hand back, sitting back up on the table. “Okay,” I agreed, scooting to the edge and standing up, feeling all the guys circling around me. I looked for Jack and found him standing back and watching, stroking his cock, which looked like it was damn near hard again. I licked my lips and smiled at him, knowing I likely had a wild look in my eyes as I realized what I was about to do.

He just smiled back and started stroking faster. 

“Here,” Pete said, picking up a towel and folding it, setting it down on the cement as a cushion for my knees. 

“Thanks,” I said, smiling slightly at him and blushing as I knelt down once again. 

And then I was surrounded by cocks, just like in the porn videos I’d masturbated to time and again, as all the guys circled around me, stroking my face. I squeezed my thighs together as I sat back on my heels, my pussy throbbing. Then I tentatively reached up to take over for the closest two guys’ hands. 

I had Johnny in my left hand. His cock was smaller than Jack’s, maybe about six inches. He was circumcised and curved just slightly upwards. 

Scott was in my right hand. He was closer to seven inches, and thick. Also circumcised, with a bigger head. 

I started stroking them both in synchronized movements, looking back and forth between the two cocks and then up at the guys’ faces, noticing their furrowed expressions and moans. 

Dan was standing right in front of me. He took a step closer, and I took in the details of his cock. He was also between six and seven inches, also circumcised, not as thick as the others. Without a free hand, I just looked up at him and waited, licking my lips as he took another half-step closer and started pressing himself into my mouth. I parted my lips around him, wrapping them lightly around his head, rolling my tongue around his cock until he pressed himself further, deeper down my throat suddenly, causing me to choke a bit. He pulled back briefly before grabbing hold of my head with both hands and thrusting into my mouth, groaning. 

I moaned, sucking him and leaning forward to take him deeper, trying to let him know it was okay to push in deep like that. 

But before he had much of a chance, he was getting tagged out. Scott moved in front of me next and I kept stroking him as I took him in my mouth and started sucking until I felt my hand being pulled away and placed around another cock. 

I tried looking to the side as Scott held my head and started thrusting his thick cock into my mouth. I glimpsed Ari in my peripheral vision. His cock felt smaller than the others, maybe five inches, and circumcised. In my hand, I could feel that he had a slight curve to the left. He held my hand in a fist around his cock and started fucking it, then brought it down to cup his balls, which felt huge in contrast to his small-to-average cock. I heard him groan as he cupped my hand around his balls and took the hint, playing with them in my hand. 

Then I felt my left hand gripping something much bigger than the others. I knew it was Pete and again attempted to turn and look as much as I could while my face was being fucked. He just placed my hand on his cock gently and let me do the rest. I took my time stroking him in long, slow strokes, feeling his entire length. I had never been with a guy that big before. I conservatively estimated that he was at least nine inches long, and fairly thick, too. It was intimidating, and I felt my attention drifting towards him from the other guys. When there was another switch up near my mouth, I took advantage of the brief break to turn towards Pete and look up at him as I stroked his gigantic cock. All (or at least most) of the arrogance seemed to have finally worn off, and he looked at me intensely, face furrowed as my hand moved on him. As much as I hated to admit it, there was definitely something there that drew me to him and made me want more. 

Pete didn’t press for a turn with my mouth. Each of the other guys must’ve gone around at least twice before Ari noticed and asked if he wanted a try.

I looked up at him to see his response, only to find him staring back at me with that same intense look. 

“Yeah,” he answered finally, after a pause. “If that’s okay?” 

I just nodded slowly, still stroking him. “It’s okay.” 

So Pete traded places with Ari and stood before me, reaching down to cup and squeeze my breasts as his enormous cock swung around in my face. 

I laughed a little after leaning back to avoid being slapped with it. 

He laughed too and apologized. 

One of the other guys commented about his ‘dangerous weapon.’ 

Then Pete reached down to cup my cheek, stroking it with his thumb. I shivered a little at the touch. He slid his thumb over to my lips and pressed it into my mouth, pressing down a bit to get me to open wide. 

I clenched my pussy, feeling it throb once again as Pete brought the tip of his cock to my lips and started rubbing it on them. I felt the wetness of his pre-cum as he rubbed it into my lips. 

He didn’t push his cock into my mouth like the others had. Instead, he waited, as if wanting to feel me taking it on my own. 

I wrapped my lips around him and started sucking, gradually taking him deeper, leaning forward onto him. I had to pull one of my hands back from the other guys for a moment to reach for Pete’s hip and tug, urging him a little closer. I kept sucking him, taking him as deep as I could on my own. 

Pete seemed content to let me do so and refrained from pulling me onto his cock or thrusting into my mouth at all. I figured he was being cautious, knowing he was on thin ice already. It felt good to see that he was at least taking me seriously and being respectful for a change. So, I decided not to encourage him to take more just yet, and held myself back from doing so, too.  

It felt intense and overwhelming as the guys continued rotating around me, my focus split in so many directions. I did my best to keep up with the stroking, letting the guys take charge of my mouth, sucking and choking as they took turns thrusting down my throat. 

After what could’ve been ten minutes or two hours, I heard Claire call out from the sidelines. “Alright, let’s move this along! Give Jess’ poor mouth a break already!” Then to me, “Your jaw has got to be killing you right now!” 

I laughed a little as the guys pulled back and finally saw her, lying back on one of the chaise lounges beside the pool. “Yeah, it’s getting a little  sore, I guess.” 

Jack was sitting on the same chair, near her feet, a towel around his waist. He was smiling, but it didn’t quite reach his eyes. That made me worry. 

Claire seemed to notice and reached over to pat the chair beside her, telling me, “Come, have a seat!” 

I got up slowly, my legs stiff from kneeling down for so long on the hard deck. The towel “cushion” had helped, but only so much. I stretched a bit as I walked out of the circle of guys and over to where Jack and Claire sat. Rather than taking the seat next to Claire right away, I came to stand in front of Jack, my hands coming to his shoulders. 

“Okay?” I asked with a soft smile, looking down at him. 

His smile felt more sincere as he looked up at me. “Yeah,” he said, simply. “Having fun?” 

I laughed a little, which made him laugh, too. “Yeah, I’m having fun.” 

“Good.” 

“Are you?” I asked, looking down at his towel. I thought I could see that he was still hard underneath, but couldn’t quite tell with the way it bunched up. 

He followed my line of sight and chuckled again, adjusting himself under the towel so that I could see his erection poking up. “Yeah, still having fun. Just trying not to gross Claire out too much.” 

Claire laughed beside us and kicked Jack a little playfully. “Oh, please! I could not be here if I got that grossed out by cocks. Besides, you have a pretty nice one.” 

I laughed and voiced my agreement. “He does.” 

Jack blushed a little, which only made Claire tease him more. 

“I want to feel you inside me again,” I told Jack, once the teasing settled down. 

Jack’s eyes roamed over me, followed closely by his hands. “Yeah?” he asked. 

I nodded.

“What if I told you to let the others fuck you first?” 

My chest tightened again. I stared at Jack, waiting to hear it as a command. “Is that what you want?” I prompted. 

He swallowed. “Yes. I want you to let them each fuck you while I watch. But no one else gets to feel you without a condom.” 

I shook my head. “No. Just you.” 

“No kissing either. And they can’t come in your mouth, or on you. Only in the condom, or in their hands,” he ordered, loud enough for the others to hear.

“Okay,” I agreed easily, smiling back at him.

“Good,” he nodded, smiling back. Then, “You want to feel two of them inside of you at once?” 

I sighed and nodded, squeezing my thighs together again. 

Jack and Claire both looked down at my pussy, noticing my reaction. 

“Three?” Jack asked next. 

My eyes widened. “You mean one in my mouth, while two others are in my pussy and my ass?” I asked.

Jack nodded slightly. “Sure. Or maybe two in your pussy and one in your ass, if they can manage it.” 

My chest started heaving at the thought. “I’m not sure that would fit,” I said, blushing and smiling. 

Jack smiled back. “Maybe not. Do you want to try?” 

I shrugged. “Yeah, maybe.” 

“Not sure?” 

“Just nervous, I think.”

“I can help,” Claire offered, then. “I can help guide them in.” 

I felt another tingle of pleasure in my pussy when Claire said that, getting wetter still. “Yeah, okay,” I agreed, swallowing. 

Pete came around to the lounge chairs and asked for Claire’s help to lower them. She got up and helped. Jack got up too, so they could push the chairs together, creating a larger surface area, almost the size of a queen bed. Pete had also apparently snuck inside to get a bottle of lube and a bunch of condoms, setting them on the small table that had been between the chairs. 

“Way to be prepared,” Claire teased, with a playful punch to Pete’s arm. 

He grinned at her, and then at me, before stepping back again to await further instructions. 

I turned to Jack, who pulled me into a deep kiss, groping me and pressing his hard cock into me as it tented his towel. I moaned into him, wrapping my arms around him, wanting him. 

He reached down to feel me up between my legs, moaning when he felt how wet I was. “I think you’re ready,” he announced. Then he told me to lie down. 

I reluctantly let go of Jack to follow his directions, lying width-wise across the lounges, on my back, knees bent up. Jack watched me and removed his towel, stroking again as his eyes poured over me. Then, he stepped back, looking at the other guys who had all been standing by, waiting eagerly, yet patiently. With a slight nod, he let them know it was okay for them to approach me again. I leaned up onto my elbows to watch them circle around yet again. 

“Is this okay?” Dan asked as he came to kneel right in front of me, moving between my legs. 

I watched as he pushed my thighs apart, up and back again, his hard cock poking my stomach, resting there. 

I nodded, laying back once again, feeling a bit flustered as he reached for a condom and quickly applied it. Then he reached down and slid two fingers into me again, rubbing my clit with his thumb while his fingers slid in and out. He groaned when he felt me squeezing around them. “You’re so sexy,” he gushed, his eyes roaming over me. “Jack’s so fucking lucky.” 

I sighed and arched my back as I felt his fingers moving inside me, my hands coming to his chest. 

“So fucking tight and wet,” he muttered. 

I moaned, grinding on his fingers. 

“I want to feel you squeeze around my cock like that.” 

“Yesss, fuck! I want that, too. I want to feel you inside of me now.” 

Apparently, that was the enthusiastic consent Dan had been waiting for. Without another word, he pulled his fingers back out of me, gripped his cock, and pushed into me steadily, sinking his cock all the way in until I felt his balls resting against my ass. 

“Ohhhh fuck!” I moaned, looking down to watch as Dan started thrusting in and out. 

He sighed, breathing hard as he fucked me. At some point, he let go of my thighs to hold himself up over me and just kept thrusting, cupping my face and staring down into me. For a moment, I thought he was going to kiss me, so I pressed my hands against his chest to hold him back. 

I wrapped my legs around him, hands roaming on his chest, then around to his back. 

“Fuck!” he groaned when he felt me tighten around him again. “You feel so fucking good.” 

I moaned and rolled my head back, feeling the friction of his cock rubbing against my clit as he thrust at that angle. “Fuck, so do you!” I replied, honestly. “That feels so good.” 

Dan growled and took a few more thrusts before slowly easing off of me, apparently tagged out again. 

Scott came up next, smiling as he asked me to sit up. 

I obeyed and watched him bring his hands to my chest, squeezing and playing with my breasts. “Your tits are perfect,” he said sweetly.

I laughed a little, blushing, but thanked him, getting a bit lost in his beautiful blue eyes. 

“I want to feel them around my cock. Would that be alright?” Scott asked.

I looked at Jack instinctively, seeking permission. He was preoccupied, stroking himself, but he nodded and gave me the go-ahead. So, I looked back up at Scott and told him it was okay, holding my breasts together for him. 

Scott groaned and knelt down, looking straight at Jack this time, sensing that I was going to check with him, anyway. “Can I suck on them?” he asked. 

Jack took an extra moment to contemplate that but ended up consenting. “Fine.” 

“Is that alright?” he asked me then. 

I just nodded, watching as he leaned in and started flicking his tongue around my nipple, then wrapping his lips around it and sucking, taking in as much of my breast as he could. He kept stroking himself as he moved to my other breast.  

There were some other groans and comments from the other guys, complimenting my breasts as well, talking about wanting to feel them like that. 

Then Scott stood back up and brought his bare cock to my chest, first slapping it against my nipples, then pushing up between my large, soft breasts as I held them together. He gradually started thrusting harder and deeper, taking over for my hands and holding my breasts together himself, his cock poking through the top of my cleavage. I rested my hands on his hips gently, looking down to watch his movements, then holding my tongue out to rub against the head of his cock as it pushed through my breasts.

“Fuck!” he hissed. “That’s so hot!” 

“Don’t come on her, Scott!” Ari yelled, clearly taking Jack’s rules seriously. 

“Fuck, I won’t!” Scott groaned back. He pulled back soon, then reached for a condom. “Still okay if I feel your pussy, too?” 

I nodded, smiling and laying back, taking a moment to look around at all the other guys, still stroking, while Scott applied his condom. Then he was kneeling over me and sliding into me right away, grunting and thrusting away, hard and fast. 

“Ohhh fuck!” I moaned, feeling turned on by the way he was pounding me, feeling the lounge chairs skidding a bit on the pavement.

“Shit!” one of the other guys muttered when they noticed, laughing. 

“I love the way your tits bounce when you’re getting fucked hard like this,” Scott groaned, not letting up. He kept going full force, pushing my thighs back against my chest. 

Then Claire was suddenly sitting up by my head. “Figured I’d put some more weight on the chair to keep you guys from sliding all the way across the deck,” she joked. 

We all laughed. 

Scott slowed to recover. 

Then Claire started sliding her hand down over my chest. She took some time to play with my breasts, too, pinching each of my nipples before trailing her fingers down my stomach to my clit. As Scott’s thrusts picked back up, Claire started rubbing me there, looking down at me and smiling. 

“Are you gonna come on his cock?” she asked. 

“Fuck!” I yelled out, my head rolling back as I felt her touch and heard her words. 

“Come on it, Jess. Feel how much you’re turning him on, how hard he’s fucking you. Look around at these guys lining up to feel you. Watching, seeing how sexy you look while you’re getting fucked. Come again, Jess. Come on Scott’s thick cock.” 

“Ohhhhhhh fuck!” I yelled, suddenly spasming and coming. I kept yelling out and moaning, squeezing around him, my thighs shaking as I felt Scott pressing them down.

Before the waves of intense pleasure subsided, I felt and heard Scott going over the edge, too. 

“Fuck, I’m coming,” he growled, thrusting into me again deeply and grunting, groaning his release. 

I squeezed around his thickness, feeling him twitching inside of me as he came. 

Scott smiled down at me and smacked the side of my thigh playfully as he slowly slid out and got up, cursing again and double-checking that the condom was still in place and hadn’t leaked. 

I smiled back at him, then lay back and cursed, smiling up at Claire as she kept rubbing me. 

The other guys teased Scott and gave him a hard time for being the first one to ‘fall,’ but he brushed it off. “I’d like to see you hold on while she’s coming on your dick like that!” 

“I’ll take that challenge!” Ari laughed. 

The other guys all laughed, too. 

I looked up and smiled at them. 

Ari came up to me next, still stroking himself. “Alright if I ask you to get on all fours? I’m dying to play with your ass.” 

I smiled, biting my lip and already sitting up. “Yeah, I’d like that.” 

“Can I…” Johnny started, coming up to the other side of the lounge. He still looked nervous. “Maybe you could ride me while he plays with your ass like that?” 

“Yeah, okay,” I smiled. 

Claire got up to make room. “Go to town, boys.” 

Johnny came to lie on his back across the middle of the chairs. 

I handed him a condom.

“Oh, thanks,” he blushed. 

“No problem,” I smiled back, climbing onto him and sitting up on his thighs.

“Fuck,” he cursed. “It’s really hot seeing you sitting on top of me like that.” 

I smiled, watching him roll the condom on. “Thanks. It’s pretty hot watching you do that, too.” 

“Yeah?” 

I nodded. “And watching you laying there, stroking yourself. Just waiting for me to slide down onto your hard cock.” 

“Mmmmm,” Johnny moaned, his hand moving on his cock again. “Yeah, that’s fucking hot. I can’t wait to feel you sitting down on it.” 

I leaned up over Johnny and watched as he kept stroking. “Slide your cock on my pussy,” I told him. “All along my slit.” 

“Fuck!” he cursed, doing what I’d asked. 

I moaned as I felt the head of his cock pressing and sliding between my lips. When I felt him pressing up into my clit, I reached down to stop his progress, holding his cock there and grinding on him. “Mmmmmm that feels so good.”

“Oh shit,” Johnny cursed. “Fuck, that’s so hot. You’re so hot,” he gushed, his eyes pouring over me as I sat up on him like that, his hands running over my thighs. 

I felt Ari’s hands on my ass, squeezing and cupping it. Then a finger dipped down and rubbed along my crack.

“Fuck!” I yelled out, feeling him pressing his fingertip against my asshole. Then I was grinding in both directions, wanting to feel more of Johnny’s cock rubbing on my clit, and more of Ari’s finger teasing my ass. 

Finally, I leaned up further and slid Johnny’s cock into position, sitting down onto him, taking him all in. He groaned and held my hips still, asking me to give him a moment. 

I moaned and smiled in response, so turned on to feel and see how close he was already, just upon sliding into my pussy. So I tried not to move on him too much as I leaned forward over him, reaching down to rub my clit, giving better access to Ari to play with me more from behind. 

Both guys groaned when they saw and felt me rubbing my clit. I heard Ari pop open the bottle of lube and squeeze some out into his hand. Then a big drop of the cold liquid right into my asshole. He rubbed it in and spread it around, then slowly inserted a finger into me. 

I reacted right away, writhing and moaning, unable to stop myself from grinding on Johnny’s cock. 

Noticing my positive response, Ari went for more right away. He slapped my ass hard, causing me to yelp, but then curse with pleasure, my thighs quivering. 

“Yessss, fuck, that feels so good,” I groaned, grinding more on his finger, pressing back, wanting more. 

“Mmmm, that’s so hot. Your ass is so hot, Jess. I’ve been thinking about feeling it all day,” Ari gushed, sliding his finger deeper into my ass, then pulling back to rub circles over the hole. 

I moaned and kept cursing and writhing, rubbing my pussy frantically. “More!” I begged. 

Ari smacked my ass again, even harder than before, and started plunging his finger in and out of me, pushing deeper with each thrust. I could feel his middle finger sliding into me past the second knuckle, almost all the way in. 

I breathed and moaned as Ari continued pressing into my ass, once again building up a tempo, sliding in deeper each time. “Does that feel good?”

“Yesss, so good,” I moaned, already writhing on his finger, reaching down to rub my clit while he played with my ass. 

“It’s not too much?” he asked, feeling me writhing.

“No!” I answered quickly. “Keep going! Fuck, I’m close…” 

“That’s so fucking hot. You’re gonna come on his cock with my finger in your ass?” 

“Yesss!” I yelled. And then I was, writhing and coming, my whole body shaking, squeezing around Johnny’s cock. 

“Shit!” Johnny cursed, holding my hips as I came down, evidently trying not to come with me. “Ohhh fuck, Scott wasn’t lying!” he groaned.

The others all laughed. 

“Told you!” Scott yelled from somewhere in the background. 

“Are you ready to feel me in your ass?” Ari asked, retracting his finger as I came down. 

“Yesss, please…” I moaned. 

Then I felt Ari kneeling down behind us, sliding right up to my ass and pressing himself into me there. 

“Ohhhhhhh fuck!” I yelled right away when I felt Ari pressing into my asshole. Then a smattering of other groans and curses flew out as he held my hips still and pressed harder into me, forcing the thick head of his cock into my tiny opening. He started up a tempo of pulling out and then pushing back in, my asshole expanding for him more easily with each penetration. 

Ari did most of the thrusting. Judging by the look on Johnny’s face, his eyes closed, eyebrows furrowed, mouth hanging open slightly, he was holding on for dear life. But as Ari thrust gradually deeper into my ass, I felt myself sliding up and down on Johnny’s cock as well. I felt so tight with both of them filling me like that. 

The sensation was overwhelming. Though there was some discomfort the further in that Ari went, the feeling of his cock sliding in and out of me there was also causing wonderful friction. I looked over my shoulder to watch as best I could. I was so turned on just knowing that this was happening, that my fantasy of being with two guys at once had become reality. The thought itself was almost as arousing as the physical feeling I was experiencing. 

But then, as I looked down at Johnny beneath me, it suddenly felt all wrong. I realized I wanted it to be Jack underneath me for this. I wanted to experience this first with him, to look into his eyes and feel that intensity, to feel him holding me and kissing me. And then I reminded myself that I could have that. I just needed to speak up. So I did. 

“Wait a second, could you guys stop, please?” I asked, reaching back to Ari’s hip to stall his thrusting. 

Both guys stopped moving immediately. 

“Yeah, what’s wrong?” Johnny asked. 

“Want me to pull out?” Ari offered. 

“Yeah, for a minute, thanks,” I said. 

So he did, both of them asking if I was ok. 

“Yeah, I’m fine. I just… want Jack,” I admitted, climbing off of Johnny carefully. Then I called him. 

Jack came over right away, looking concerned. “What’s wrong?”

“Nothing,” I smiled, reaching up and pulling him down to kiss me. Then I told him what I had been thinking. “I just feel like I want this with you. I want you to be inside me while another cock is in my ass. I want to feel you fucking me, and I want to feel your hands and mouth on me. I want to be looking at you while I feel someone else pushing into my ass like that.”

Jack seemed to be hiding a smile. “Yeah?”

I smiled back broadly and nodded. “Please? It doesn’t feel right, not doing it with you first.”

He leaned down to kiss me again. 

Johnny had taken the hint and gotten up by then. So, Jack knelt and then sat down on the chaise “bed” as we kept kissing. I climbed onto him as soon as he was settled, sitting on him gently as his hands ran over my thighs and squeezed my ass. 

“Were you watching?” I asked, pulling back from the kiss for a moment.

“Yeah, of course, I was fucking watching. And I was thinking the same thing, too. That I wanted to be doing that with you.”

“Why didn’t you say anything?” 

“I don’t know. I just want you to have whatever you want.”

I smiled, feeling a flutter in my stomach with his words. “Well, I want you.” 

“That’s good,” he smiled back. 

Then I pushed on his chest until he was lying on his back. I leaned up over him and reached down to stroke his cock, angling it towards my entrance right away. 

“Fuck!” Jack groaned when he felt me taking him in. “God, you make me feel so good, Jess.” 

I smiled and moaned as I slid down onto him, loving the feeling of his bare cock sliding into me. The feeling of excitement I got from being with him seemed to increase over time rather than fade. I’d never experienced that before and just wanted more. 

Jack’s hands grabbed my ass and squeezed, guiding me as I started riding him. We were both moaning and cursing. I combed my fingers into his hair and tugged as I leaned over and kissed him again, feeling him thrusting up into me and dragging my hips to slide back and forth on his cock. I could feel and hear how wet I was, my juices once again audible as Jack fucked me. He groaned and reached around to press a finger into my asshole. It slid in easily, following Ari’s prep work and penetration. 

Jack cursed and looked up at me. “I love feeling how wet you are for me. You want him in your ass again now? While you’re riding me like this?” 

I nodded, smiling down at him, feeling like my face was on fire. “Yes.” 

“Are you gonna come on my cock when you feel us thrusting into you from both ends like that?”

“Fuck!” I muttered, my pussy already clenching. 

Jack groaned. Then he called out for Ari. “Ari! Still ready?” 

“Fuck yes, if it’s still okay?” Ari asked, still nearby. 

Jack looked up at me, wanting to make sure it was my final call. 

“Yes, it’s okay,” I said, arching around to look at him. “I want you to keep fucking my ass now.” 

That was all the invitation Ari seemed to need. I felt him kneeling back down behind me on the chaise, his hands taking over for Jack’s on my ass, spreading me and applying some more lube to me and himself, rubbing it all over and inside of me. Then he was slowly pressing back into me as Jack pressed deep into my pussy and then stopped thrusting.

“Fuck!” I yelled out, feeling Jack impaling me on his cock like that. 

Then Ari pressed in, the head of his cock slipping in more easily than before. He resumed thrusting right away, pushing in gradually deeper. This time I felt both guys’ cocks thrusting together, silently working out a rhythm. My eyes started rolling back as I got lost in the pleasure. 

“How does it feel?” Jack asked.

“So good. So crazy,” I breathed, barely able to focus enough to form words. 

“Fuck, we should’ve brought one of your toys,” Jack muttered then, smiling up at me. 

I smiled back and laughed a little, my face furrowing. 

“I might be able to help with that!” Claire called. 

A few moments later, she was coming over with what looked like a tube of lipstick. “I like to always have one on hand, just in case,” she chuckled, holding it out to us. 

Jack took it from her, laughing. “Clever of you.”

“Don’t worry, it’s been cleaned since its last use. Oh, and just twist it a little to turn it on,” she added with a wink. 

“Thanks, Claire,” Jack said. 

I added my thanks as well. 

“Sure, happy to help,” she smiled at me. 

Then Jack twisted it on and slid it down between our bodies. I arched up and back a bit as I looked down to watch him sliding the tip of the lipstick on my pussy, pressing it up against my clit. The movement also caused me to press back further onto Ari’s cock. He groaned and pressed a little further, and then I could feel my ass pressing against his pelvis and knew he was fully inside me. 

“Fuck!” Ari yelled. He held my hips and pressed himself into me as hard as he could before pulling back and thrusting in hard again. 

“Ohhhhh god!” I yelled, suddenly very close. The buzzing of the vibrator and the feeling of Ari’s hips slamming into me like that were about to throw me over the edge again. 

“That’s it. Come on my cock, Jess. I want to feel you squeezing around us. Your pussy already feels so fucking tight around me, so swollen, and with Ari’s cock in your ass. It feels so fucking amazing.”

“Fuck, I’m gonna come!” I yelled, forcing my eyes open to look down at Jack. 

He was grinning up at me, then glancing down to focus on rubbing the vibrator on my clit. “Yes, that’s it. Fuck, you’re so hot. I love how turned on this is making you. You love being my slut, don’t you?”

“Fuck! Yes, I love being your slut! I love the way you make me come all the time. I love having you tell me what to do. I love that you set up this party to give me what I’ve been wanting. So fucking good. Fuck, I’m coming!” I kept talking as I built up until I felt myself roll over the edge, and then all I could manage were moans and curses, yelling out loudly. 

Both guys tensed as they felt me coming, writhing back and forth on both cocks. 

“Ohhhh fuck!” Ari yelled. 

Jack groaned, fingertips digging into my thigh on one side as he handled the vibrator with his other hand, watching me writhe on top of him. 

“Mmmm, so hot. That sounded really good,” Claire said, coming around and smiling again as I came down. 

I laughed a little. “Yeah, that was really fucking good.” 

“Want to try more?” she asked, gesturing one of the other guys over. 

I looked around to see who she was signaling and saw Johnny stepping around the chairs. He’d taken the condom off and was stroking his cock once again. 

“Another cock in your mouth, maybe?” Claire asked. 

My chest started heaving again at the thought. “Yeah,” I breathed. 

Claire smiled and licked her lips. “So hot.” 

Then she reached to take one of my hands, giving me a moment to rebalance before putting my hand on Johnny’s cock. I started stroking him right away, causing him to groan. 

“Don’t worry, I washed off a bit. Shouldn’t taste like condom chemicals anymore,” he explained.

I laughed a little. “Okay, thanks.” And then I looked up at him, smiling, as he took another step closer until I could wrap my lips around him. 

“Oh fuck,” he groaned once he was in my mouth again. 

I felt Jack adjusting the vibrator as he and Ari resumed thrusting, rubbing it around my clit, his other hand playing with my nipples, pinching them between his fingers. The sensation was so intense. I had to bring my other hand back down to hold myself up as both guys continued thrusting, leaving it to Johnny to hold my head and control the blow job himself. 

Then I heard Claire again, now standing behind us, behind Ari. “Can you move up a bit? To kind of hover over her?” she asked Ari. 

And then I felt him moving up to stand on the chaise and straddle me, his hands holding around my waist, then sliding up to cup my breasts from behind.  

“Here, come up and stand at the edge. Can you reach from there? Or maybe if you take Ari’s spot and kneel?” 

I could tell Claire was talking to another of the guys and could only guess what was about to happen. But with Johnny holding my mouth on his cock, I wasn’t able to say anything or ask questions. 

“Yeah, I think this’ll work,” another guy said behind me. It sounded like Dan. 

Then I felt the head of another cock brushing against me. 

“Here, let me help,” Claire’s voice again. 

Then a groan from Dan, as it sounded like Claire had taken over stroking him, and was helping him to press into me, to share space with Jack’s cock in my pussy. 

The sound that came out of me was somewhere between a groan and a whimper. It was enough to get Johnny to pull back for a moment, letting me breathe and talk. I felt my saliva dripping onto his cock and brought my hand up to my mouth to wipe it away once he pulled out, hoping that I hadn’t also dripped on Jack. 

“Fuck!” I cursed. “Did I drool on you?” I asked, looking down at Jack then.

He just laughed. “No. Don’t worry about it, though. Do you feel what’s happening now?” 

“Yes,” I breathed. “I still don’t know if it’s going to fit,” I said this louder, directing it back to Claire and Dan.

“Okay if we try?” Claire called back.

I just laughed a little and cursed again, feeling so overwhelmed. I looked down at Jack, who was still smiling back up at me, pressing the vibrator harder against my clit.

“Fuck!” I yelled. 

“Do you want them to try?” Jack asked. 

“I really don’t think it’ll work.”

“That’s not what I asked,” Jack winked.

I laughed again. “Fuck… I guess so. I don’t know. It might be too much. You’re already so big.” 

“Do you want to try with two of the others?” 

I hesitated. I didn’t really want to do it without Jack but also didn’t think it would be possible with him. “No… I don’t know. I didn’t mean it like that,” I stalled. 

“You should try,” he said with a smile. 

I just looked back at him as he gave one more hard thrust before asking Ari to pull back again. 

“No, wait,” I called before Ari had time to respond. “It’s okay, just try it.” 

“Are you sure?” Jack asked. 

I nodded down at him. “I want to try it like this.” 

He leaned up to kiss me again, squeezing my hip affectionately. Then he thrust up into me again sharply, causing me to groan into the kiss.

“Fuck!” I muttered, pulling back. 

“Okay?” Claire asked again. 

“Yeah, okay. Go ahead,” I called over my shoulder, to her and Dan.  

And then there was a third cock pressing against me, attempting to push into me. I felt them pressing Dan’s cock against Jack’s, attempting to share the same tight space. None of us were moving, all bracing to see if he’d fit into me with the others. It didn’t seem to work. 

“Maybe if Dan gets in first,” Claire suggested. 

“Okay,” Jack agreed. Then Ari was pulling out of my ass as Jack lifted me forward enough to slide himself out as well. 

They tried it that way instead. Dan slid into my pussy first, then Ari pressed back into my ass. Jack groaned and cursed as Claire was evidently stroking his cock and helping to guide it back into me. But then I heard Claire moaning, and Jack started writhing under me. I tried turning around to see what was happening. I couldn’t see much at that angle, with all the other guys around, but I could tell enough to know that Claire was sucking Jack’s cock. 

“Mmmm tastes so good,” she moaned, pulling back. 

“Fuck!” Jack cursed.

I felt a pang of jealousy then, knowing that Claire had Jack’s cock in her hand, and in her mouth, and seeing that Jack was responding. But hearing her moaning and enjoying tasting me like that was such a turn-on at the same time. 

Either way, I hardly registered what I was feeling before Jack’s cock pressed back into me, attempting to share space in my pussy with Dan once again. Claire helped Jack get the head of his cock inside of me, and I could feel him thrusting, attempting to fill me more. But it was a tight squeeze. None of the guys could thrust all that much while I was so full with all of them like that. 

“Take her mouth again,” Jack told Johnny, who was still standing by our heads, stroking.

Johnny looked at me, and I nodded, smiling. “Yeah, you should. I want to feel you thrusting into my mouth again, too.” 

So he did, and suddenly I had four cocks filling my three holes, all at once. It had definitely become too much to take in at the moment. I just tried to capture as much of the sensation as I could, so that I’d have the memory to look back on while masturbating later, indefinitely afterward. 

All the guys continued attempting to thrust a little while longer before pulling back until it was just Jack and me again, and the lipstick vibrator. I sat up on him, stretching my back. 

“Feeling sore?” Jack laughed.

“A little,” I laughed back. “It’s okay though. Definitely worth it.” 

“Did you like that?” 

“I smiled down at him and nodded, still grinding on him. “Yeah, it was really hot. And overwhelming,” I admitted. 

Jack just smiled, groaning a little as I wriggled on his cock. “It was really hot to watch,” he added, once again adjusting and rubbing the lipstick vibrator on my clit, then sliding it down to where his cock disappeared into my pussy. 

“Mmmmmm,” I moaned, grinding harder on him, reaching up to play with my nipples. 

“Fuck, you’re so sexy, Jess. I know I’ve said that a lot today, but you just really fucking drive me crazy.” 

I started breathing harder, picking up pace and riding him again. 

“God, I’m gonna come inside of you again,” Jack warned. 

“Yeah, I want that,” I moaned. “I’m gonna come, too. Keep rubbing that on me.” 

Jack growled and kept rubbing me, thrusting up into me, too. “Fuck, you still feel so fucking tight, squeezing around my cock like that.”

“Yeah,” I breathed. “You always turn me on so much.” 

“Fuck! Come on my cock, Jess. Fucking come on me, then I’m gonna fill you up with another big load. So fucking hot.” 

I groaned and nearly buckled over, but kept riding him, my hands on his chest as my hips slid up and down on his length. I reached down to press his hand and the vibrator harder against my clit and then I was coming undone, cursing and yelling out, writhing on him, my thighs shaking, squeezing around his cock. 

“Fuck, I’m coming, Jess!” Jack yelled. And then he was. 

I felt the hot spurts of cum shooting into me and heard his growl, extending my orgasm.

“Fuck, you guys really need to make videos,” Claire said as we came down, not a hint of a joke in her tone. 

Still, we both laughed, along with some of the other guys. But there was a consensus that they were all enjoying the show. 

I smiled down at Jack as he scooted to sit up, holding me there in his lap. I cupped his face and kissed him again once we were sitting up together, his hands squeezing my ass.  

“I’m glad you asked me to join for that part. It was really hot to hear you wanting me to be the first one you tried that with. I know I would’ve ended up feeling really jealous afterward if I wasn’t… even though I was telling you to go ahead with the other guys.”

“I really wanted it to be you,” I told him. 

“That’s good,” he said, kissing me again. 

Then, I climbed off of Jack’s lap slowly, feeling relief as I came down off of my knees. He got up and offered to get me a drink. I accepted and watched as he headed over towards the kitchen, where most of the others had also drifted. It felt like a sort of natural stopping point, and I wondered if that would be it. 

But then I met eyes with Pete as he came back out to the deck, and suddenly there was still an elephant in the room. Or an elephant-sized cock that hadn’t yet had a turn, anyway. Despite everything that had already happened, I felt another shiver of pleasure and anticipation run through me at the thought of Pete’s giant cock inside of me. 

Published 3 years ago

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