The Pool Party

Jack and I had been casually seeing each other for a few weeks when he asked me to join him at his coworker’s pool party. We hadn’t yet ventured into the territory of introducing each other to our friends or family. In fact, he’d barely met my roommate, Christina, despite the numerous nights he’d spent at our apartment.

We’d decided early on to keep things light and fun between us. I was fresh out of a relationship when we met, and Jack was swamped with work at a startup company. It seemed like the perfect arrangement for both of us, so the idea of taking things further was a bit nerve racking.

I guess the real reason behind my anxiety was that I had deeper feelings for him than I was ready to admit, even to myself. Jack and I had an effortless, fun connection right from the start, as friends. Add to that the amazing sex, and I knew I was in deep.

So, it felt good when Jack was the one to push things forward between us. Plus, meeting a few of his coworkers at a pool party was as casual as it could get; it was a far cry from him inviting me home to meet his parents. I kept reminding myself that it didn’t necessarily mean anything.

But that didn’t stop me from overthinking things and dragging Christina out shopping to help me pick out a new swimsuit a few days before the party.

Swimsuits had always been a challenge for me. It was hard to find one that was comfortable and supportive for my DD chest and curvy ass, while still looking sexy. So when Christina held up a gold foil string bikini, I just stared back at her in disbelief.

“What’s with that look?! You would look hot in this!” she insisted.

I just shook my head, already dismissing the idea and continuing my search. “I could never pull off a bikini like that,” I said. “Even if it covered everything, I’d be paranoid about something slipping out, or it coming untied.”

“So you can double-knot it, if you’re really that concerned!”

I just sighed, wishing she would drop it. I knew she was trying to be supportive, but it was hard to take advice on that sort of thing from my petite, slim friend whose body looked much more like the ones seen modeling similar swimsuits in ads and the media.

“Will you just try it on, Jess?!” Christina pleaded. “What do you have to lose from trying it on to prove me wrong?”

“Fine. If I agree to try it on and show you why it doesn’t work, will you get off my ass about it?”

“Sure, I will. But if Jack finds out that you’re passing on the sexy bikini, I’m sure he’ll give your ass a slap or two!” she teased, smacking my butt playfully.

I rolled my eyes but couldn’t help blushing and smiling a bit to myself. “Hilarious.”

One consequence of my intense connection with Jack was that our sex was not exactly quiet. A fact that Christina never ceased to tease me about. Though I guess that was a fair trade for having to be subjected to said noisy sex as often as she was.

We kept browsing the racks until we collectively found five different suits of various colors and styles for me to try on. Then we went back to the fitting rooms. I tried them on one at a time and modeled them for Christina, knowing she’d give me honest feedback, which I could then take or leave.

I went for the gold bikini first, wanting to get it out of the way. The only problem was, once I had it on, I had to admit that it actually looked pretty good. It surprised me that the top actually covered a good amount of my boobs, and that it felt comfortable and decently secure. I knew it would take some getting used to, to not have more of a strap on my hips holding up the bottoms. But they also covered everything they needed to cover. Perhaps the biggest surprise was seeing my smile in the mirror as I looked at myself from all angles.

Christina’s impatient questions from the other side of the locked fitting room door interrupted my thoughts. “Do you have it on yet?! You have to let me see it no matter what—you promised!”

“Okay, okay,” I conceded, taking a deep breath and forcing the smile off of my face before opening the door, shaking my head. “I think it’s too much.”

Christina’s face lit up.

“Holy shit, you look HOT!” she gushed.

I tried brushing off the compliment, looking down and pointing out every flaw I saw on my body.

But Christina wasn’t having it. “I’m not kidding—you have to get it! And I demand that you take a picture of Jack’s face when he sees you in it for the first time!”

I rolled my eyes. “Well, he’s seen me naked plenty of times already. It’s not like there are any surprises left.”

“I beg to differ! Seeing you in a bikini instead of that sporty shit you normally wear is going to drive him crazy!”

I stepped back into the fitting room and looked in the mirror again, frowning.

Christina came in and stood behind me, still smiling.

“You’re getting it,” she declared. “Buy it yourself, or I’m buying it for you!”

I shook my head again but gave in and smiled back at her in the mirror. “Just let me try the rest on, okay? Then I’ll decide.”

“Sure, try the rest,” she placated me. “My mind’s made up, though. And you know what that means.”

I grumbled and gently pushed her out of the stall so I could close the door and try on the next swimsuit.

In the end, the one I felt most comfortable in was a black one-piece that felt flattering, yet sexy. It had a low-cut neckline but felt supportive and covered most of my ass. Christina agreed that the suit was sexy yet tasteful. But I worried that maybe that meant it wasn’t actually very sexy at all.

I ended up buying both—the black one-piece and the gold bikini. I told myself (and Christina) that I was only buying the bikini to keep her from spending her own money on it, adamant that I had no intentions of actually wearing it. She was kind enough to smile and nod along rather than rubbing it in my face, knowing I was full of shit.

A few days later, I left for the party wearing a bright blue, knee-length sleeveless sundress and brown leather sandals. I packed both swimsuits, unable to talk myself all the way into wearing the gold bikini and feeling comforted by the one-piece option in my bag. I told myself I would make a game-time decision when I arrived and saw what everyone else was wearing.

I met Jack at his place so we could drive together, since it was on the way to his coworker’s house from mine. When he opened the door for me, he was in swim trunks, navy blue with a pattern of little red and white fish, a plain gray T-shirt, and brown leather sandals. I felt a tingle between my legs as my eyes caught on his trunks. I’d never seen him in anything so short before, and the trunks drew my eyes to his muscular thighs, visible below the hem. That sight, and the knowledge that he wasn’t wearing anything under the trunks, immediately aroused me.

Suddenly I recalled what I’d said to Christina, doubting that Jack would feel turned on by seeing me in a bikini after having seen me naked, and I admitted to myself that I may have been wrong. There was something about seeing him in the swim trunks that was driving me unexpectedly wild.

Jack caught me staring and smiled, a playful twinkle in his warm hazel eyes. “Like what you see?”

I laughed at myself, but had to admit, “I do,” feeling the heat rise in my cheeks.

“You’re blushing,” he teased, checking me out and stepping closer.

“Am I?” I asked, biting my lip and struggling to suppress a chuckle.

“Mm-hmm.” He nodded as he reached me, putting his hands on my hips and quickly sliding back and down to grab two handfuls of my ass. He tugged me against him until I could feel his hardening cock pressed against my hip.

I had my hands on his arms as he pressed himself into me and moaned involuntarily.

“What are you thinking about?” he asked into my ear before taking my earlobe between his lips, sucking on it and nibbling lightly. Then I felt a light kiss right behind my ear, and another as he trailed his lips down my neck.

I moaned, my fingertips digging into his shoulders. “Thinking about how distracted I’m going to be all day at the party, knowing that there’s only one layer of fabric between me and your cock.”

I felt Jack’s hot breath on my shoulder and neck as he sighed. “Well, maybe we should do something about that before we go.”

He pulled back to look into my eyes as he grabbed a handful of my hair and tugged, causing me to gasp.

My lips parted. I stared back at him and nodded.

Jack pulled me into a deep kiss then, and I was happy to feel him wanting me just as much as I wanted him.

In a whirlwind of movement, Jack guided me the short distance to his couch. Before I knew it, I was on my back, my legs wrapped around him, my body humming with desire. I clung to him, my fingers digging into his T-shirt as I felt the pressure of his body against mine.

His hands began to wander, sliding up my thighs and pushing my dress up until it was gathered around my waist. He hooked his fingers into the waistband of my panties, pulling them down on both sides.

I lifted my hips, aiding him in sliding them off. My legs shot up in the air as he pulled them off over my feet.

A groan escaped Jack’s lips as he kissed me again, his body hovering over mine. His hand ventured between my legs, teasing me. His fingers traced a path along my slit before his thumb found my clit, rubbing gentle circles. He slid two fingers inside me, a slow and tantalizing rhythm that had me moaning into his mouth.

“Damn, you’re already so wet,” Jack groaned. “Were you thinking about me fucking you before the party?”

“Yes,” I hissed, my eyes drawn to his hands on me. “I always want you so much.”

A growl rumbled in Jack’s chest as he watched me, his eyes scanning my face for signs of pleasure as he continued to touch me.

“God, that feels so good,” I moaned, locking eyes with him, my face twisted in pleasure.

“You’re so sexy, Jess. I think about you all the time,” he murmured.

“Oh god,” I groaned, my head falling back onto the armrest of the couch. “You’re gonna make me cum!”

“Already?” he asked, his voice dropping an octave.

“Yes!” I cried out, grinding against his hand, feeling the buildup of an intense orgasm. “Your fingers feel so good! I’m going to cum all over them!”

“Do it. Cum on my fucking fingers, Jess. I want to feel you squeezing them. God, I can’t wait to slide my cock into you and feel you so wet and tight around me. You feel so fucking good.”

His words were the final push I needed. I cried out, my hips bucking wildly as I pushed myself farther onto his fingers. My fingers tangled in his chestnut hair, pulling as my body convulsed.

“That’s it, cum hard for me,” Jack muttered, fighting against my movements to continue touching me as I rode out the orgasm.

Finally, I came down, panting and moaning. My grip on Jack’s hair loosened, and my hands slid down to his neck, his shoulders, then his chest.

“That was so good,” I murmured, my eyes still closed, as I felt him retract his hand.

“Mmm,” he groaned. Then I heard a sound that made me open my eyes. Jack had his fingers in his mouth, sucking my juices off of them.

My surprise must’ve been evident on my face. He’d never done that before. No one had. But it didn’t take me long to realize how much it turned me on, my body reacting to the sight.

“You taste so fucking delicious,” Jack said once he’d finished sucking off his fingers.

I stared at him, lust clouding my thoughts, leaving me speechless.

“Have you ever tasted yourself, Jess?” he asked.

My cheeks flushed as I nodded slightly.

“So you already knew that.”

I just stared up at him, a small smile playing at my lips. I must’ve had a wild look in my eyes.

Then Jack reached back down and slid the same two fingers back into me.

I gasped when I felt it and clenched as he thrust them in and out a few times before pulling them back out and bringing them to my lips this time.

I knew immediately what he wanted me to do, and that I wanted it, too. So, I parted my lips for him, and he slid his fingers into my mouth, slowly at first. I sucked on his fingertips lightly, moaning at my taste and just from the act itself.

Then Jack worked his fingers farther into my mouth until they were deep down my throat.

I gagged a bit, at which point he pulled back slowly, allowing me to suck the rest of my juices from his fingers.

“Good girl,” Jack growled, his hand moving to my neck next and squeezing while he kissed me deeply.

I moaned into the kiss, my hands gripping his shirt at his waist, my thighs squeezing him.

“I want you,” I breathed during a brief break in the kiss, pulling his shirt up over his head.

He let me pull the shirt off, then his lips trailed down to my neck and shoulder. He groped my breasts through the dress, then pushed up on the gathered fabric at my waist and tugged the dress up and over my head.

Then he pulled my bra straps off of my shoulders and down, tugging the cups down too until my breasts spilled out. He cupped them both, each more than a handful even for Jack’s large hands, and rolled his tongue around each nipple before sucking each breast into his mouth.

I sighed and arched back again, loving the way his mouth felt on me and telling him so. Then, I eagerly reached for the large bulge in the front of his swim trunks, cupping and rubbing his rock-hard cock through the smooth fabric.

Jack growled against my chest when he felt my hand there.

I curved my hand around the outline of his cock and found his head with my thumb, rolling it around and rubbing the flat edge of his mushroom top, then up to the slit on his tip. That earned me another groan, and then Jack leaned back up over me and pressed himself into my hand, grinding and wanting more.

Our eyes met, both of us smiling as my hand moved on him.

“That feels so good,” he breathed, still looking right at me, into me.

I felt for the drawstring of his shorts and tugged it loose, then slid a hand under the waistband to wrap around his smooth, hard cock. I stroked him just a few times like that before pushing down on the shorts.

Jack helped me to push them down his legs the rest of the way and kicked them off without getting up. Kneeling over me, he cupped behind my head and pulled me into another deep kiss as I continued stroking him, guiding him straight to my entrance.

He groaned and pulled back to say, “I’m gonna grab a condom.”

But as Jack tried to push himself up and off of me, I held on, looking up at him and shaking my head. “I need you now.”

His eyes met mine, then scanned my face as if looking for a hint of doubt.

“Are you sure?” he asked.

I nodded. “Yes. Please.”

I didn’t need to ask again. With another groan, Jack reached down to grip his cock, then rubbed it up and down along my slit for just a few strokes before finding my entrance and pushing into me.

I gasped when I felt the bare head of his cock spreading my lips, and then moaned as Jack pulled himself back out, penetrating me shallowly a few times before letting go and sinking all seven inches into me, the full weight of his hips coming down onto me.

“Ohhhh fuck,” he growled into my ear. “God, you feel so incredible, Jess.”

I moaned, loving the feeling of his bare cock stretching me and being pinned under him like that. I wrapped my legs around his waist and dug my fingertips into his back as he started thrusting, picking up the pace.

“Oh god, that feels so good,” I moaned, looking up at Jack, my face contorted with pleasure.

He leaned down to kiss me again, pinching my bottom lip between his teeth before pulling back and leaning up to kneel. He gripped me by my hips and tugged me closer to him, causing my head to slide down from the armrest to the seat of the couch. Then he fucked me harder, holding under my ass and forcing my legs wider with his powerful thrusts.

I yelled out, reaching for his arms and chest, his thighs, digging my fingertips into him wherever I could reach him.

“Fuck!” I cursed. “Oh my god, I’m gonna cum again!”

Jack responded by reaching down between our bodies to rub circles over my clit with his thumb.

“Cum on my cock, Jess. I want to feel you squeezing around me. I’m so close already. You feel so good like this. Cum on my cock and then I’m gonna pull out and cum on your stomach, okay?”

I shook my head, looking right at him. “No, come inside me! Please!”

Jack already knew that I was on birth control, so I hoped he would feel safe enough to do as I wished.

“Fuck!” he yelled, suddenly freezing inside of me, focusing on rubbing my clit. “Are you sure?”

I glanced up at him, my expression serious, grinding against him, yearning for his movements to start again. “Yes, I’m certain! I want to feel you release inside me. I want to climax with you, Jack!”

He let out a low growl, leaning farther over me abruptly, pushing my legs back toward my chest. He continued to stimulate my clit as he plunged into me deeply, quickening his pace once more.

“Say it again,” he commanded.

I moaned, my head falling back once more, feeling the buildup to climax again. “I want you to release inside of me, Jack! When I feel it, I’m going to climax on you! Please! Fill me! I need it!”

Suddenly, Jack’s movements became erratic as he grunted and climaxed. I felt him pulsing inside me, and several warm spurts of his release shooting into me as he continued his movements.

I reached down to take over for his hand, frantically stimulating my clit until I climaxed with him moments later, writhing beneath him, tightening around him.

Then Jack collapsed on top of me with a curse, burying his face in the crook of my neck.

I let out a sigh and wrapped my body around his, smoothing his hair down, and rubbing over the minor scratches I’d left on his back.

When Jack finally pulled back, he kissed me deeply before peeling himself off of me, our skin sticking together from our shared perspiration. We grinned and laughed together when we felt it, and he gave my thigh a playful slap as he stood up, then offered me a hand to help me up as well.

“That was so good,” Jack gushed again, rubbing my hip affectionately.

“Yeah, it was.” I grinned back, giddily. “I think we’re running a bit late now, though.”

Jack smiled and nodded, pulling back to gather up our clothes.

He handed my underwear back to me and draped my dress on the couch while I pulled my bra back up. Then he stepped back into his trunks and pulled them up over his hips.

I found myself once again mesmerized as I watched him redress, pulling up his trunks and retying the drawstring. I hadn’t even noticed I was staring until Jack called me out of it.

“Okay, you’re gonna need to stop looking at me like that if you ever want us to get out of here.”

I blushed and laughed, finally pulling my attention away and apologizing, picking up my dress and bunching it up in my hands before slipping it back on over my head.

We met eyes again, grinning as we each slipped our sandals back on. Then Jack gave my ass a playful slap before going to grab his keys while I brought my underwear into the bathroom to clean up.

When I looked at myself in the bathroom mirror, I noticed I was still smiling as I replayed the last ten minutes in my mind.

But then the worry came back, too. I knew I was losing the battle I’d been waging with myself, to keep things feeling casual with Jack. But I wasn’t sure how to avoid getting too close too fast when I constantly felt like I was melting into a puddle around him.

Jack was helping me to discover things about myself that brought on pleasure like I never imagined with anyone else. From the beginning, we’d set out exploring our turn-ons together. He’d asked me what I liked and what I wanted, which were not questions anyone had ever asked me before, in a sexual context. It made me curious to ask him in return, wanting to know what I could do to make him feel the same way.

But as good as it was, it also felt dangerous, like I knew how much I had to lose. I felt tempted to hold back more, to protect my feelings. The trouble was, I really couldn’t help giving in to Jack. Every time we were together, it felt intense, and always better than the last time. And the hope that he might actually feel the same way was the most intoxicating part of all.