“Thirsty?” Pete asked as he came around to the side of the chaise, holding out a glass of water.
I looked up at him and couldn’t help smiling, thanking him and accepting the drink.
He smirked back, sitting down beside me as I drank. “Feels like I’m one of those guys standing on the sidelines at a marathon, handing out water to the racers.”
I started laughing mid-sip, then choking as the water went down the wrong pipe.
The others called over when they saw and heard us laughing, and me choking. “You guys okay over there?” and, “What the hell is so funny?”
We didn’t answer.
I finally caught my breath and playfully warned Pete to “Keep your mouth shut and let me drink!” as I took one more sip.
He held his hands up in mock surrender, then leaned over onto one of his elbows so that he was lying on his side in front of me.
I set the glass down on the little table that held the lube and condoms. Suddenly, I felt emboldened enough to flirt and joke back a bit. “So, do you have to stitch a few of these regular condoms together to make one that fits you? What’s your trick to do it without poking them full of holes?”
“Actually, I usually just go for those giant balloons that clowns use to make balloon animals and shit.”
I started cracking up. “Seriously,” I said, once my laughter died down enough for me to speak again. “Those normal-sized condoms don’t look like they’ll fit. I hope you’re not thinking about trying to go without one.”
Pete rolled his eyes then and leaned over towards the table, sorting through the condoms until he found one labeled “Magnum” and held it up to me.
I recognized the brand. Jack usually wore them, and he was a good couple of inches smaller than Pete. My doubt lingered, and I looked back at him incredulously. “I’ll believe it when I see it,” I flirted.
“It covers enough, don’t worry,” he winked at me. “Not my first Magnum rodeo.”
Now it was my turn to roll my eyes. “No, I don’t imagine it is.”
“For instance, I knew well enough to let all these other guys warm you up for me first,” he added.
“So kind of you,” I chuckled.
We kept joking around and flirting, making each other laugh so loud that the others thought we were losing it.
My eyes found Jack as he came back out to the deck holding the drink he’d gotten me, only to notice that Pete already had it covered. He looked uneasy, sort of glaring at Pete, watching his every move. Pete paid him no mind, though, his attention focused on me as we continued joking around together.
I could sense Pete’s cockiness seeping back in, but it felt different now, somehow. Or I felt different. I responded to him. Every blow we exchanged, and every joke felt like foreplay.
He reached out to me then, the backs of his fingers brushing against my hard nipple, causing me to shiver, my whole body shuddering, embarrassingly. Pete smiled and pinched it between his fingers, twisting lightly.
I gasped, my hands coming to his arm instinctively. But I resisted the urge to pull his hand away. I felt the pleasure between my legs, stronger than the pain.
He studied my reactions, then repeated the process on my other nipple.
I had to bite my lip hard to keep from moaning out too loudly. Instead, it came out like more of a whimper. I knew he could tell that I was holding back. He smirked up at me again, his eyes taunting me, causing me to blush harder. My face felt like it was on fire.
“Is little Avi the only one you’d want to have in your ass, then?” Pete asked.
I scoffed, laughing again. “I hope you’re asking for a friend.”
Pete laughed, too. “Don’t worry, I’m not planning on putting you in the hospital.”
I just shook my head.
Then he looked over my shoulder. I turned with him to see that a couple of the guys were still sort of hovering, waiting to finish.
“What do you say? Still have any juice left?” he asked, barely hiding a smirk.
I chuckled again. “I might. Are you wanting a turn, then?”
Pete seemed to contemplate it for a moment, looking me over. His eyes roamed over my body slowly, appreciatively. “Hmm. I think I’ll keep watching for now.”
Hearing him react that way, turning down a chance to fuck me, should’ve made me feel insanely self-conscious. But there was something about the look in his eyes that let me know he was just messing with me, and letting things build up between us.
“Bend over for them,” Pete said with a twinkle in his eye.
I looked back at him, getting the feeling that he was trying to play off of the way he’d heard me taking orders from Jack, wanting to see if I’d obey him, too. If I’d be his slut, too. I felt uneasy, but played along.
“Like this?” I asked as I leaned forward, resting my face down on the chaise cushion, arching around in order to watch the action. I slid one knee over just slightly to spread my thighs a bit more, my ass sticking straight up in the air.
Pete’s cock twitched as I assumed that position. He chuckled, knowing I’d seen it. “Yeah, that’ll do.”
I just bit my lip as I looked up at him, trying not to laugh again.
“Form a line, gentlemen,” Pete told the others.
My chest heaved as I watched them follow Pete’s lead. Dan was first in line and came up to kneel behind me again. “Which hole do you want me in, babe?” he asked.
“You can pick,” I told him. “But I’ll probably come on your cock if you fuck my pussy.”
“Mmmm, sold,” Dan groaned. He put on a fresh condom and then started sliding his cock along my slit before slipping into me and fucking me hard and fast right away.
“Ohh fuck!” I yelled, feeling him pounding into me like that. I reached down to rub my clit, then felt Pete tapping my arm as he held out the lipstick vibrator.
“Here,” he offered.
I thanked him, turning back towards him a bit as I turned the vibrator back on and held it down against my clit, watching as he stroked his huge cock so close to my face. He held himself loosely, his fingers lightly sliding all the way up and down his impressive length.
I risked a glance up to Pete’s face and found him staring back down at me, watching me watch him stroke his cock.
“Keep watching me,” he breathed, barely audible.
I sighed and kept my eyes trained on him, feeling close to coming again as Dan kept pounding into me.
“Does it turn you on, watching me stroke my cock while I look at you? Watching you get fucked like that?” Pete asked, gripping himself tighter now.
“Yessss,” I breathed, pressing the vibrator onto my clit harder. “That turns me on so much.”
“Have you ever had a cock as big as mine in your mouth before?”
“No,” I answered, honestly.
“Not in your pussy either?” he guessed.
“No, I haven’t,” I breathed.
Pete groaned. “Tell me how badly you want to feel my big cock inside of you.”
“Fuck!” I cursed. And then I was coming, writhing over the edge, bucking and yelling out as I felt Dan pressing himself all the way, deep into me and coming, too, our curses overlapping.
Dan pulled back slowly, telling me how good that felt, how hard he came. And then he was making room for the next guy in line.
Johnny pushed in fast and hard, too. I moaned and started getting worked up again, but then with just a few more thrusts, Johnny was already coming, pushing in and finishing inside of me, in the condom.
Pete smirked down at me when it happened, and I bit my lip to keep from smirking back.
“How long were you holding that in, buddy?” Pete asked.
“Longer than I thought I’d be able to,” Johnny admitted, not even phased by Pete’s teasing. Then to me, he said, “Sorry, Jess. But I’m sure at this point you don’t mind, with a whole lineup behind me.”
I laughed with him. “No worries.”
Ari and Scott each took their turns next, refreshing their condoms and then fucking me until they were coming inside my pussy. I looked around for Jack after that, and noticed him hanging back for now, still giving Pete an uneasy look as he hung out near me and watched it all up close. Claire yelled something about wishing she had a strap-on right about now, and the others all laughed.
Then I looked back to Pete, who was still stroking. “Are you tired of being on your knees yet?” he asked.
I shrugged. “They’re getting a little sore, I guess. Why?”
“Because I want you to be as comfortable as possible while I’m fucking you. I want to make sure you feel good. But I also want you to be in charge, in a position to only take in as much of me as you can handle.”
“What makes you think I won’t be able to handle you?” I asked, glancing back down at his cock as he continued stroking near my face.
He just smirked back at me, his eyes twinkling. “I like a girl who’s up for a challenge.”
I laughed back.
Then Pete started moving into position, sliding onto his back, moving under me. I climbed onto him, straddling his waist while he tore open the Magnum condom wrapper. I watched as he rolled it down onto his cock. He was right that it fit most of the way on. But it was stretched tight around him, and stopped a good two to three inches above the base. He saw me watching and smiled again, then gripped my ass and started tugging me forward so that I was high enough for the head of his cock to reach my pussy.
I groaned, looking down and back as he started rubbing himself along my slit. I closed my eyes, squeezing them shut as my face contorted in expected pleasure, focusing on the feeling of Pete’s cock pressing into me.
When he found my opening, he let the head of his cock slip inside and then stopped.
“Fuck!” I groaned, already grinding back onto him further.
“That’s it. Take as much as you can,” Pete said, his hands squeezing my ass and guiding my hips to slide on his cock.
I gasped and groaned as I worked my way down onto Pete’s cock, cursing along the way as I felt him stretching me. I was so wet, with my cum and Jack’s, that he slid in fairly easily, considering his size. Finally, I felt the head of his cock bumping the back wall of my pussy against my cervix.
“Fuck!” Pete yelled out when he felt it, his head rolling back. “Holy shit, that’s so deep.”
I moaned and cursed too, grinding on Pete’s gigantic cock. It was almost too much. I was tempted to ease off of him, but he cupped my cheek, looking into my eyes and pressing himself up into me even further. I looked down at Pete and held his gaze. My lips parted, face furrowed with pleasure. His thumb slid from my cheek towards my mouth, then dipped inside. I moaned, sucking on his thumb, feeling him pressing down, holding my mouth open, pinching my bottom lip between his fingers. I could see in his eyes how badly he wanted to kiss me just then, and worried that he could see how much I wanted it, too.
Instead, he removed his thumb from my mouth and slid his hand down between our bodies. Then I felt him pressing his thumb against my clit and rubbing while he encouraged me to keep riding him.
That was it for me. Feeling the stimulation on my clit on top of the intense feeling of whatever was happening with Pete sent me rolling over the edge again in the most intense orgasm yet. I felt my muscles clench and the quivering of my thighs, which seemed to spread up through the rest of me as I held Pete’s gaze.
He smiled up at me and kept rubbing as he felt and watched me coming.
I felt weaker after that, nearly collapsing onto Pete’s chest.
He seemed to sense that the last orgasm had taken a lot out of me. “Okay?” he asked, his cock twitching inside of me as my pussy continued clenching while I came down.
I just nodded, my head hanging a bit.
“Can you take any more?” he asked. It felt like a sincere question, no longer taunting.
“Yeah,” I said, knowing I wanted more.
“Fuck,” Pete groaned. “Start riding me again when you’re ready. I don’t want to press in too deep and hurt you.”
“It’s okay,” I told him. “I want to feel you fucking me.”
Pete growled. “Are you sure?”
“Yessss,” I hissed. “Please.”
“Fuck,” he cursed again, then rolled us so that he was on top of me. “Wrap your legs around me.”
I breathed out a moan and followed directions, squeezing my legs around his waist. Then he held himself up over me and started fucking me with slow, shallow thrusts at first, sliding deeper and deeper into me. “Fuck, you’re so tight,” he exclaimed. “So fucking good.”
My eyes started rolling back again, mouth hanging open. I shifted my hips as my back arched, feeling Pete’s cock rubbing against my clit as he thrust into me, creating just enough friction to bring me over the edge again. I felt myself building up, my fingernails digging into his waist and back as I squeezed around him, my breasts bouncing as he fucked me. And then I was coming again, clenching and spasming and shouting my release.
“Fuck!” Pete yelled, picking up the pace and force of his thrusts.
I gasped and cursed again as he fucked me through my orgasm, feeling like I might roll straight into another. “Oh my god, don’t stop. Fuck, keep going! I’m gonna cum again. Fuck! Holy shit, that feels so good.”
Pete growled and kept fucking me, daring to press in deeper and deeper as I encouraged him with my moans.
“Ohhh fuck, you’re so deep! So fucking big! That feels so fucking good!” I yelled, losing control. I knew I should’ve been more careful about what I was yelling, knowing that Jack was hearing it all, but I was lost in the pleasure and unable to screen my thoughts or words any longer. I let go, giving in to it, letting myself roll over the edge again and again, losing track of where one orgasm stopped and the next started as I was overtaken by the waves of pleasure.
“Jesus, I’m gonna come,” Pete yelled at some point.
And then he was, as I continued writhing under him.
“Holy fucking hell!” Pete yelled out, grunting and bucking on top of me. “Shit!”
When he stopped thrusting, I finally allowed myself to collapse under him, all of my limbs falling flat on the chaise cushion.
“You okay?” Pete chuckled, feeling me turning to jelly under him.
“Yeah, I think so,” I breathed. I smiled and laid my head back, eyes still closed.
He waited to move off of me until I opened my eyes and looked up at him, only to find him smiling back down at me. I blushed and bit my lip, feeling overcome by the intensity of what had just happened. My ears were ringing, all the sounds around us suddenly distorted, an after-effect of the intense orgasm.
Then Pete gave my hip an affectionate squeeze before easing himself out of me and getting up. He smiled over his shoulder as I watched him go inside to get cleaned up.
Then I met Jack’s eyes as he made his way over to me and my smile faltered. He brought me a towel, handing it to me as I sat up.
I thanked him, standing up slowly to wrap the towel around myself. I noticed Jack watching Pete walk into the house, looking uncomfortable, and I tried coming up with a joke or something to break the tension.
Claire seemed to pick up on the discomfort and helped me out. “Just throwing this out there, but if you ever decide to join me for a lesbian orgy, I can promise you won’t leave as sore as you’ll likely be tonight!”
Everyone around us laughed, except for Jack. But I caught the hint of a smile playing on his lips. I gave Claire a thankful smile.
***
It was fairly awkward after that, as we all unanimously, but wordlessly, decided that the party was over. Everyone who hadn’t redressed yet did so. I went back inside to the guest room to change back into my dress. I wondered if Jack would follow me, but he didn’t. That made me nervous. I hoped he was just giving me space and not avoiding me. I couldn’t help feeling anxious about what he’d have to say once we were alone again.
There were awkward goodbyes all around, the others all saying they’d see each other at work on Monday. There was a tension in the room that made me think Jack might’ve said something more to all of them, or at least to Pete, while I was changing.
Claire was the only one to come up and check in privately as we were getting ready to head out.
“Hey, is everything okay? How are you feeling?” she asked, sincerely.
I laughed a little and admitted. “I have no fucking clue. Overwhelmed, I guess.”
She laughed, too. “Yeah, I get it. I remember having a lot of mixed feelings the first time I tried anything like this.”
“Any advice?” I asked.
Claire thought for a moment. Then, “I would recommend going to sleep and not thinking about it anymore tonight if you can help it. Give it time to sink in. Maybe when you wake up, you’ll have a clearer idea of how you’re feeling about everything, whether it’s something you enjoyed and might want to try again or not.”
I nodded. “That sounds like a plan.”
“Here, let me give you my number,” Claire offered, reaching out a hand for my phone. “You should call me if you’re still feeling weird about anything or just want to talk. Or, you know… call me anyway, if not.”
I blushed and unlocked my phone, handing it to her. “I will.”
“I know it’s too soon for you to think about this now, but if you decide to try anything again, even if it’s just you and Jack next time, I’d be really interested.”
I smiled, biting my lip. “Yeah, I like that idea.”
Claire smiled back as she entered her number into my phone and handed it back. “Cool. Oh, and don’t worry – I’ll make sure those guys behave themselves at work.”
“Yes, please,” I laughed.
Jack came outside then. My smile dimmed when I saw him, nerves still rattling inside of me.
“Have a good night, you two,” Claire said with a wink as she went back inside.
Then we were finally alone again. “Ready?” Jack asked, motioning towards the street where his car was parked.
“Yeah, let’s go,” I answered, walking up the driveway.
***
The drive home felt awkward at first, like neither of us really knew where to start.
Finally, Jack spoke up, taking his eyes from the road for a moment at a time to look at me. “Are you okay? About… everything, I mean?”
I looked back at him. “Yeah, I think so. Just kind of processing everything, I think. It was a lot.”
“Too much?”
“I’m not sure,” I admitted. There was a beat of silence. Then I felt a need to ask, “What about you?”
“Yeah, I don’t really know either. I thought I was fine, but that seemed pretty intense with Pete at the end.”
I felt myself blushing harder, my face turning red with the memory of what I’d felt with Pete. How obvious my pleasure must’ve been.
“Did it feel better with him than it does with me?”
This was the question I’d been anticipating and fearing. I knew I had to tread carefully. “No,” I said right away, not wanting to stall or pause before responding, which would’ve surely caused him to doubt my answer. “It was really good, I’m not gonna lie. But it’s not the same as it is with you.”
Jack seemed to contemplate that. I was expecting him to ask more, and was surprised to hear him apologizing instead.
“I’m sorry,” he started. “I know I’m being confusing. I’m just feeling jealous.”
“Are you upset that I went through with it?”
He thought for a moment. “No. I don’t know. I guess in hindsight, I’m not sure I like the idea of half the guys and one girl on my team at work having slept with you. It’s just… weird, I guess.”
I blushed. It felt like a bit of a jab, but I knew Jack probably didn’t mean it that way.
“But I know that that’s on me. I was the one who started this whole thing.”
The uncomfortable feeling lingered for most of the drive back to Jack’s apartment. Then, as he took his exit off of the highway and we came to a stop at a red light at the end of the ramp, Jack apologized again. “I’m sorry for being so weird about all of this.”
“It’s okay. I do enjoy knowing how you actually feel about things, you know,” I smiled, hoping to ease the awkwardness.
He smiled back. “Be careful what you wish for.”
I laughed, happy that the tone of our conversation seemed to change back to the fun, flirty warmth I was used to. “I also really enjoyed hearing the rules you made for the others. The things you weren’t okay with.”
“Oh, yeah?” he smirked, looking over at me. “That was okay, then?”
“Yeah, very okay. That made it all feel like just another thing you and I were doing together. That’s mainly what it was for me, you know.”
“That’s good,” Jack responded. Then, after another brief, more comfortable pause, “I don’t think the guys will ever stop bugging me about it, though. Wanting to hook up again.”
I shrugged that off. “Well, I wouldn’t want to do it again, knowing it might make you uncomfortable.”
“Yeah, but I’m not your boyfriend or anything. I don’t really have a say.”
There were the butterflies in my stomach again. I leaned in the direction he seemed to go with that comment. “What if I want you to have a say?”
Jack looked back at me, uncertain. The light changed to green. I kept watching his face for a reaction as he made the turn, then continued towards his place. Sensing my eyes on him, Jack smiled and reached over to put a hand on my thigh as he drove.
