Jack and I had only been hooking up for a few weeks when he invited me to his coworker’s pool party. I was surprised - we hadn’t taken any next steps to introduce each other to friends or family. Hell, he had barely met my roommate Christina, despite having spent the night on multiple occasions. In fact, we’d agreed in the beginning that we’d keep things simple and fun between us. I was just getting out of a relationship when we met, and he was too busy for one, working at a startup. What we had together seemed most convenient for us both, so I was nervous to take any steps further.
Though I suppose the real reason I was nervous was that I had stronger feelings than I was admitting, even to myself. We had a really fun, easy connection from the start, as friends. Then adding on the extra layer of sex- the best I’d ever had, by far- I already knew I was in trouble. So, having Jack be the first one to nudge things along between us did feel good. Besides, meeting a few of his coworkers at a pool party was about as casual as it could get, a far cry from inviting me home to meet his mom. I reminded myself that it definitely didn’t have to mean anything.
However that didn’t stop me from overthinking things, dragging Christina out shopping to help me pick out a new swimsuit a few days before the party. Swimsuits had always been tricky for me, wanting something that felt comfortable and supportive of my DD chest and large ass, while still looking sexy. So when Christina held up the gold foil string bikini, I just stared back at her incredulously.
“What’s that look?! You would look hot in this!” she argued.
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 managed to cover all of my bits, I’d be paranoid about something slipping out, or it coming untied.”
“So you can double-knot it, if you’re really that concerned!” Christina retorted.
“No,” I said firmly. “Bikinis like that were not made to hold my boobs.”
“Well, I beg to differ. They have it in your size - why would they make ones for big boobs if they couldn’t hold big boobs?”
I just groaned, wishing she would let it go. I knew she was trying to be supportive, but it was hard to take advice on this 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,” I conceded. “If I agree to try it on and show you why it would never 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 it 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. “Very funny.”
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. I was surprised that the top actually did cover a good amount of my boobs, and that it felt comfortable and decently secure. I was a bit uncomfortable to not have more of a strap on my hips to hold up the bottoms, but they also covered everything they needed to cover. I was surprised to see myself smiling in the mirror as I looked at myself from all angles.
My thoughts were interrupted by Christina’s impatient questions from the other side of the locked fitting room door. “Do you have it on yet?! You have to let me see it no matter how bad it is - you promised!” she whined.
“Okay, okay,” I conceded, taking a deep breath and forcing the smile off of my face before opening the door, shaking my head. “It’s too much, I think,” But then I watched Christina’s face light up when she saw me and knew I was in trouble.
“Holy shit, you look HOT!” she gushed.
I couldn’t help laughing and trying to brush off the compliment, looking down and pointing out every flaw I saw on my own body, and the way it looked in the bikini.
But Christina wasn’t having it.
“I’m not kidding - you have to get it! Jack will just die! And I demand that you take a picture of his 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 ‘full coverage’ shit you normally wear will surely give him a very pleasant surprise!”
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 very flattering, yet sexy. It had a low-cut neckline, but felt supportive and covered most of my ass. Christina agreed that the suit was cute, and sexy in a tasteful way. But I worried that maybe that meant it wasn’t actually very sexy.
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.
In the end, I decided to wear a thick-strapped sundress to the party, which was white with thin teal stripes, horizontal across the top part and vertical in the skirt, with a sash tied in a bow in front, and strappy sandals. I packed both swimsuits, unable to talk myself all the way into wearing the gold bikini. I told myself I would make a game-time decision when I arrived and saw what everyone else was wearing, feeling comforted by the one-piece option in my bag.
I met Jack at his place, since it was on the way to his coworkers house from mine, so we could drive together. When he opened the door for me, he was already dressed for the party 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 my eyes were drawn to the muscles of his tan thighs, visible beneath the trunks. Gazing up just a bit from there, I was also immediately aroused by the thought that there was nothing under them. Just one layer of fabric between me and his big, gorgeous cock. Suddenly I recalled what I’d said to Christina, doubting that Jack could be 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 wild in an unexpected way.
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 in turn and stepping closer.
“Am I?” I asked, biting my lip and struggling to suppress a chuckle.
“Mmhmm,” he nodded as he reached me, his hands coming to my hips and quickly sliding back and down to grab two handfuls of my ass, tugging me against him until I could feel his hardening cock pressed against my hip.
My hands came to his arms as he pressed himself into me and I heard myself moaning 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 admitted.
I felt Jack’s hot breath on my shoulder and neck as he sighed. “Maybe we should do something about that before we go, then,” he breathed.
He pulled back just a bit to look into my eyes as he grabbed a handful of my hair and tugged a bit, causing me to gasp, my lips parted. I stared back into 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.
This was the sort of thing that worried me. Every time we were together, it felt so intense. I wasn’t sure how to keep things from getting too close too fast with Jack when I was constantly feeling like I was melting into a puddle whenever he touched me. 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 somehow not questions I’d ever been asked before in a sexual context. It made me curious to ask him in return, wanting to know what I could possibly do to make him feel the same way. Jack was helping me to discover things about myself that brought on pleasure like I never imagined when I was with anyone else.
He swept me along the 3 or 4 steps to his couch and gently pushed me down to sit before kneeling beside me and leaning over, urging me onto my back. I leaned back against the armrest and wrapped my legs around him, moaning into the kiss and gripping a handful of his t-shirt as I felt him grinding into me. His hands slid up my thighs from my knees, pushing my dress up until it was bunched around my waist, then gripping the waistband of my panties and tugging down on both sides. I lifted my ass to help him slide them down, and then raised my legs straight up as he pulled them up and off over my feet. Jack groaned as he kissed me again, holding himself up over me with one arm while the other hand slid between my legs to start teasing my pussy. He brushed the back of two fingers up and down along my slit before finding my clit with his thumb and rubbing gentle circles over it. Then his middle and pointer fingers slid between my lips, rubbing, before slipping into me a little at a time, sliding in and then back out.
“Fuck, you’re already so wet,” Jack groaned. “Have you been thinking about wanting me to fuck you before the party?”
I gasped and moaned, pulling back from the kiss to look down and watch his hand on me. “Yesss,” I hissed. “I always want you so much.”
Jack growled and watched me. I felt his eyes scanning my face, watching for signs of pleasure as he fingered me.
“Fuck, that feels so good,” I moaned, meeting his eyes, my face already furrowed in pleasure.
“You’re so fucking sexy, Jess. I think about you all the time, too,” he breathed.
“Ohhhhh god,” I groaned, my head rolling back onto the armrest of the couch. “Fuck, you’re gonna make me cum!”
“Already?” he asked, his voice suddenly huskier.
“Yes!” I yelled, grinding on his hand, feeling myself building up to an intense orgasm. “Fuck, your fingers feel so good! I’m gonna cum all over them!”
“Mmmm fuck, baby. Cum on my fucking fingers. 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.”
That was all it took for me. I yelled out, my hips writhing and bucking wildly as I slid myself further onto his fingers until I felt his knuckles pressing into my pussy lips. My fingers combed up into his chestnut hair and tugged as my whole body convulsed.
“Fuck!” Jack muttered, fighting against my movements to continue rubbing my clit and fingering me as I rode out the orgasm.
Finally, I started coming down, moaning and breathing hard, my grip in Jack’s hair loosening until my hands were sliding back down to his neck, his shoulders, then his chest.
“Fuck, that was so good,” I smiled, my eyes still closed, as I felt him retract his hand.
“Mmm,” he groaned. And then I heard a slight slurping sound that encouraged me to open my eyes. When I did, I saw Jack with his fingers in his mouth, sucking my juices off of them.
My face must’ve shown my surprise. He’d never done that before. No one had. But it didn’t take me long to realize how much it turned me on, feeling my pussy clench at the sight.
“You taste so fucking delicious,” Jack said, once he’d finished sucking off his fingers.
“Fuck,” I muttered, suddenly unsure how to form any other words.
“Have you ever tasted yourself, Jess?” he asked.
My cheeks burned as I nodded my head just slightly.
“So you already knew that.”
I wasn’t sure how to respond and just stared up at him, a slight smile playing at my lips.
Then Jack reached back down and I felt him gently sliding the same two fingers back into me. I gasped when I felt it, and clenched as he thrusted them in and out a few times before pulling them back out, bringing them to my lips this time. I knew right away what he wanted me to do, and that I wanted it, too. I parted my lips for him and felt him slide his fingers into my mouth, slowly at first, just up to his first knuckle. I started sucking on them lightly, moaning at my taste and just from the act itself. Then Jack started working his fingers further into my mouth, bit-by-bit, until he was pushing them deep, down my throat. I gagged a bit, at which point he started pulling back slowly, allowing me to suck the rest of my juices from his fingers.
“Mmm, good girl,” Jack growled, bringing his hand to my neck next and squeezing while he kissed me deeply, sucking on my bottom lip.
I moaned into the kiss, gripping his shirt in fistfuls at his waist, squeezing my thighs around him. “I want you,” I breathed during a quick break in the kiss, starting to tug his shirt up, over his head.
He allowed me to pull the shirt off, then resumed kissing me before his lips trailed over my jawline to my chin, then back down to my neck and shoulder. He started groping my breasts through the dress, then rushed to untie the sash in front before pushing up on the bunched fabric at my waist and pulling until I was leaning up and holding my arms up, allowing him to pull 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 large breasts spilled out. He cupped them both, each more than a handful, even for Jack’s large hands. Then his lips and tongue trailed down my chest until he was rolling his tongue around each nipple and sucking each breast into his mouth in turn.
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 then rubbing his now rock-hard cock through the smooth fabric.
“Fuck!” 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 was leaning back up over me and pressing 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 want more,” I responded before looking down to find the drawstring of his shorts and tugging. As soon as it was loose, I hooked both pointer fingers into the waistband of his trunks and tugged, loosening the cord, before reaching inside and wrapping my hand around his smooth, hard cock. I stroked him just a few times like that before pushing down on the shorts with my other hand. Jack helped me to push them down his legs the rest of the way, until he was kicking them off without getting off of me.
Then, he got back up on his knees over me, cupping behind my head and pulling me into another deep kiss as I reached down to keep stroking him, guiding him to my entrance right away.
He groaned and pulled back just a bit 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 was reaching down to grip his cock and then rubbing it up and down along my pussy lips for just a couple strokes before finding my entrance and pushing into me.
I gasped when I felt the bare head of his cock enter me, and then moaned as Jack pulled himself back out, penetrating me like that a few times before letting go and sinking all 8 inches into me, the full weight of his hips coming down onto me.
“Ohhhh fuck,” he growled into my ear. “God, you feel so fucking incredible, Jess.”
I moaned, loving the feeling of his bare cock inside of me, and being pinned under him like that. I wrapped my legs around his waist and my arms around his back, my fingernails digging into his skin as he started thrusting, picking up pace.
“Ohhhhh 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, one of his legs sliding out so that he could brace his foot on the floor like a kickstand. 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 my head against the armrest as he continued to fuck me, holding my legs against his chest with one arm, my feet dangling in the air by his head, while his other hand reached down and he started rubbing circles over my clit with his thumb once again.
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. That feels so fucking good.”
Jack just groaned. “Yeah, cum on my cock, Jess. Fuck, I want to feel you squeezing around me. I’m so fucking close already, you feel so good like this. You cum on my cock and then I’m gonna pull out and cum on your stomach, okay?”
I shook my head, looking right into him. “No, cum inside me! Please!” I begged. Jack already knew that I was on birth control, so I hoped that he would feel safe enough to do as I wished.
“Fuck!” he yelled, suddenly freezing inside of me, focusing on rubbing my clit. “I’m so fucking close. Are you sure?”
I looked up at him and nodded, my face furrowed, starting to grind on his cock, wanting to feel him thrusting again. “Yes, I’m sure! I want to feel you cum inside of me. I want to cum with you, Jack!”
“Fuuuuuccckkk,” he growled, leaning further over me suddenly, pressing my legs back towards my chest. He kept rubbing my clit as he thrusted into me deeply, picking up speed. “Tell me again,” he ordered.
I groaned, my head rolling back again, feeling myself building up to release again. “I want you to cum inside of me, Jack! I’m gonna cum on your cock when I feel it! Please! Cum inside of my pussy! I need it!”
Jack let go then, his thrusts becoming spastic as he came. I felt several hot spurts of his cum shooting into me as he continued thrusting, and I reached down to take over for his hand, rubbing my clit frantically until I was cumming moments later, writhing under him, squeezing around him.
He collapsed on top of me with a final curse, burying his face in the crook of my neck.
I sighed and wrapped my body around his, combing my fingers through his hair once more to smooth it down, and rubbing over the slight scratches I’d left on his back.
Jack kissed me again deeply before peeling himself off of me, our skin feeling stuck together in places from our shared sweat. We grinned and laughed together when we felt it, and he gave my thigh a playful slap as he stood up, then offering me a hand to help me up as well. I let him pull me gently to my feet and pulled him into another kiss before releasing his hand.
“That was so good,” Jack gushed again, rubbing my hip affectionately.
“Yeah it was,” I grinned back, giddily. But then the worry came back, too. It was still crazy to me, how good everything felt with Jack. And to think that he was feeling that too was the most intoxicating part of it all. But being with him felt dangerous. I knew how much I had to lose, which made me wonder whether I should be holding back more than I was. The trouble was, I really couldn’t help giving into him. It was always like this, every time we were together. Still, I felt a need to force us out of the moment. “I think we’re running a bit late now, though.”
Jack smiled and nodded, pulling back to start gathering up our clothes. “Just a bit.” He handed my panties back to me and draped my dress onto the couch while I pulled my bra back up, then stepped back into his trunks and pulled them up over his hips.
I found myself once again hypnotized, watching 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, then retying the sash.
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. I brought my panties into the bathroom to clean up a bit, and then we were finally ready to head out to the party.