Sex Confessions, Sex with Strangers

Hawaii hotness with [m]y (kind of) cousin [f]

I’m on a trip in Hawaii right now, and all I can think about is what happened the last time I was here on a family vacation when I was 19. All the reminiscing inspired me to share this little story about me and my cousin.

First, some background. I’ve always known my cousin (we’ll call her Sammy) is cute. Even before I knew what it was to be attracted to a girl, her freckles and tomboy attitude drove me crazy. And as we grew up, her just one year behind me in school and age, that feeling grew too. She changed from an adorable little redhead with a big gap between her front teeth to a total knockout by the time she graduated high school. And I was enamored the entire time. We didn’t see each other that often, so every time our family got together it seemed like she had developed some new enrapturing feature. Her braces came off and she had a beautiful, lily-white smile. Her bright red hair began taking all sorts of interesting and enticing shapes as she got involved in cosmetology. Her shirts started getting lower as she developed a pair of perfectly perky and squeezable boobs. And her jeans got tighter as her volleyball-playing butt got ever rounder and firmer.

(Luckily for me, her look is strikingly similar to that of a certain Playboy model I had the great fortune of finding a while back.)

So needless to say, there’s been a sexual attraction there for me for a very long time. Prior to the events of this story, I’d never gotten a solid sense that the attraction was shared, but there had always been a tiny hint of tension between Sammy and me.

I should probably also note that she’s not my “real” cousin. We’re only related by marriage, so any hardcore incest haters shouldn’t be too frightened off by this story. But still, we’ve been in each other’s lives for as long as I can remember.

Okay, thanks for bearing with me through all that background. Now, to the fun stuff!

It was the summer after my first year of college, and my whole family was taking a big vacation to Hawaii. I hadn’t seen most of my extended family, including Sammy, since the previous summer, so I was super excited to catch up with everyone and just relax together like old times. And, as you can probably guess, the thought of hanging out poolside with my hot cousin for a week wasn’t making me mad.

The week went as you might expect. Lots of laughs, fun family dinners, long days at the pool and beach, and only mild family drama between aunts and uncles. It was a downright dreamy trip.

But, being 19 and constantly horny, I wasn’t totally satisfied by just family time. And all the girls in bikinis (my cousin included) had my libido at dangerous levels.

So when all the cousins (Sammy and me being the oldest by about six years) decided to have a sleepover one night in a suite the family had rented, things came to a head. We all watched some kids movie in the suite bedroom’s king-sized bed for a bit until the younger cousins passed out, exhausted from another day in the sun. Sammy and I were the only ones left awake, our parents and grandparents all blissfully distant in some other hotel room. I looked at Sammy and said, “Are you tired?” She said “no,” and we decided to head out onto the balcony off the suite kitchen and just talk for a while.

We talked about college, my experiences in my first year there and her nervousness about starting in the fall. We talked about girls I’d crushed on in my dorm and her on-again off-again boyfriend who she’d finally broken up with for the last time just before graduation. It was nice. We’d never really had the opportunity to connect as young adults before without parents or younger siblings around to bother us.

“What time is it?” Sammy asked. I peered through the screen door to look at the microwave clock inside. “About 10:30,” I said. “We should go down to the hot tub,” she said. “It’s still open for like another half hour.”

I tried, probably in vain, to contain my excitement at the thought of a late-night hot tub session with Sammy. For a second I thought to myself, “Maybe we shouldn’t leave the younger cousins.” But I quickly came to my senses and decided in favor of some private time with Sammy and her bikini. (I remember it being a little yellow strapless number.)

We rode the elevator down to the pool in just our suits, and I kept sneaking glances at her ass in the elevator mirror. God, she has a nice butt. And she had her arms folded in a way that pushed her boobs together in such a subtly sexy way that I hoped she was doing it on purpose but knew it was probably just a habit.

Still, I was hopeful when we arrived to an empty hot tub that perhaps something would happen. Some snuggling, perhaps? A back rub? Hell, even a kiss?

But things remained innocent besides some playful splashing and my insistence that a passerby was checking her out because she “looked good,” followed by furious backpedaling so as to not let on that my penis was getting chubby just below the water’s surface. Her hair was pulled up in a messy bun to keep dry, exposing her long and slender neck and beautifully angular shoulders. Each bead of water clinging to her chest was an entire world I could have explored for hours with my eyes, even if only at three-second intervals to avoid getting caught staring. The ocean breeze muddled with hibiscus and the hotel’s coconut shampoo on her hair had me 100-percent intoxicated. I wanted her. Right then, right there. But I couldn’t make a move. It was too risky. I was just a kid, relatively inexperienced with ordinary girls, let alone supermodel-level cousins.

When hot tub closing time came at 11, Sammy egged me on to stay an extra three minutes longer. Always the rebel, that one.

“We could be doing worse things in here than just sitting an extra few minutes,” she reasoned. God damn, the teasing. Was she hinting at something, or just making a comment to someone she’s comfortable with.? This question had haunted me in countless similar situations over the years.

We got out and dried off, and I tried to hide my now-deflating boner. As she toweled off her bottom half, her bottoms wedged up a little and I could see more of her tight, round cheeks and her newly acquired tan line. I tied my towel around my waste, as my dick had reversed directions again.

When we made it back to the room, Sammy pulled out the the hide-a-bed from the couch in the suite living room and changed into her pajamas – cute little plaid boxer shorts and a camisole. “You cool to share the pull-out?” she asked. “Are you fucking kidding me!? YES! YES! YES! FUCK ME YES!!!” I thought. But I kept it cool. “Yeah, no worries,” I said.

We took turns in the bathroom and got ready for bed, settling in with a few more minutes of light conversation about who-knows-what. I was hardly paying attention. My mind was fixated on what could happen in that bed if I only had the guts to make a move. We were all but alone, our siblings and other cousins tucked away behind a bedroom door. I was picturing her spooned up next to me, her pants pulled down, her big ass sliding over my dick while I rubbed her boobs and kissed her neck. I was picturing her on top of me, her hands pressed hard into my chest while she rode my dick and moaned my name.

I’d had these fantasies a hundred times. Hell, probably a hundred times on that trip alone. But they were never so vivid, never so…close…as they were with her lying right next to me.

Just like that, I was hard again. Fully hard. Like, don’t-let-her-leg-bump-you-or-your-life-will-be-ruined hard.

But all I could do was lay there and try to fall asleep. About 15 minutes went by, and I was still throbbing. Then another 20 minutes. Then 10 more.

As far as I could tell, Sammy was asleep. So I decided to take care of my dick with a little trip to the bathroom, where I could stroke one out to my fantasies in private. I pulled off the sheet and I was at full mast, sticking straight up through my boxer briefs. A little dab of precum had darkened the fabric already. This was going to be a good wank.

Just as I began to stand up, Sammy whispered, “Where are you going?”

She shocked me a little, to be honest. I’d thought she was long-gone into sleep. So I stumbled a little when I explained that I had to pee and was going to the bathroom.

“Didn’t you just go before bed?” she said. She had me there.

“I drank a lot of water today,” I lied. She gave a scoffing little laugh. “You’re so full of it,” she said.

I didn’t know what to say, so I got up and started walking toward the bathroom, feeling bummed that I probably couldn’t get away with jacking off now. But then Sammy said, “I see you, you know.”

“You what?” I said.

“I can see your boner,” she said.

I was stunned. I couldn’t speak. I couldn’t move. Absolutely mortified. Everything I’d ever tried to hide from Sammy was suddenly cast out in the open in the form of my still-throbbing cock.

“Come back,” Sammy said. And I did, equal parts confused, horrified, and delighted that she wasn’t apparently disgusted.

Sammy sat up in bed to meet me and she just hugged me around my torso for a minute. My dick was fully pressed into her boobs. I had no fucking clue what the hell was going on, until she started to kiss my stomach and said “I like you too.”

From there, something awakened in the both of us that must have been dormant for years. I leaned over and kissed her on the lips. Just sweetly and still at first, and we looked into each others eyes when our lips parted, each apparently accepting what was finally about to happen. We kissed again, this time more deeply and with tongue.

As we made out, she started to stroke my cock outside my underwear, and I could feel each of her fingertips as they massaged the ridge of my head. She didn’t seem nervous at all, and her confidence put me at ease too.

She pulled off my boxer briefs and I pulled off my shirt, and she told me to lay down next to her. We kissed some more and my hands began to wander over her body, tentatively at first. I didn’t even want to come close to going too far or too fast for her comfort and risk ruining this fantasy come true. I rubbed my hands over her back and toward her ass, just barely grazing the top of her curve. She pressed into me and told me she could feel my cock on her leg, and that she liked it. I told her she was an amazing kisser, and she squeezed my ass, so I did the same to her. Fuck, it felt perfect.

She took off her shirt so I rubbed her boobs over the little cotton bralette she was wearing. She got on top of me on all fours and we kissed some more that way, her moving to my neck and chest and me taking nibbles at her ears, neck, and breasts when ever I got the chance.

Then she laid back down next to me and took off her shorts and bra. “Let’s touch each other, okay?” she said. I slid my fingers inside her underwear and began to gently massage her lips, paying only quick visits to her clit until I started to feel wetness start to seep from her tight little hole. Her pussy felt so puffy and smooth, like a pretty, pink marshmallow I just wanted to live inside.

She stroked my cock and played softly with my balls, pumping slowly so as to help make it last. Thank God!

She spit in her hand and rubbed it over my head and shaft as lube, and it felt so good another pearl of precum dribbled out of me. She rubbed it into my head with her thumb, and resumed the most beautiful handjob cadence I have ever experienced, whispering “finger me” as her hand traveled up and down my cock.

She was soaking wet inside, and so enthusiastic about having my fingers in her pussy. I could feel her moving her hips against my hand, rubbing her clit on my palm and fucking my fingers back as I slid them in and out. I’d only ever fingered my ex before, and she’d never liked having fingers inside her. So getting such a positive reaction from Sammy made it even better.

I needed a breather. Her gorgeous body and fantastic technique had me dangerously close to orgasm from pretty much the moment she hugged me. So I asked her to bend over on the bed so I could finger her from behind for a while, something I’d always wanted to try.

I fucking loved it. It was like I was fucking her from behind but with a better view. I leaned around the side of her to watch her titties swing while she backed her pussy up on my fingers. It was better than in my dreams.

Without even thinking about it, I pulled my fingers out for a moment and put them in my mouth. I could taste a little chlorine from the hot tub, but otherwise she tasted good, and I asked her if I could eat her out. She said she wasn’t sure about that, but I didn’t have time to be too disappointed because she proposed something equally exciting.

“Can I grind on you for a while? I think I’m gonna have to do that to cum.”

Before she could finish the sentence, I was laying on my back, eagerly waiting for her to slide her slit over my cock. She giggled at my enthusiasm, and she crawled on top of me, kissing me all the way from my pelvis up to my mouth.

She was already so slippery from me fingering her, and she glided so sweetly over every inch of my cock, pulsing a little every time she rubbed her clit over the ridge of my rock-hard head.

I was loving every moment of it and soaking in the sight of Sammy on top of me, her boobs hanging in my face, shuddering as her body twitched and bouncing as she worked her hips into my cock. Her lips were so puffy they felt like they wrapped half way around my cock.

She started to moan a little. “Oh shit, I need to be quiet,” she said. But she didn’t quiet down to much, and I didn’t mind. She said my name a few times, and I got the urge to fuck her. But I wanted her to make herself cum on my dick, so I let her be in charge.

“I fucking love this,” I told her, kissing her boobs and sucking on her nipples. I bucked my hips up into her, and she gasped.

“Do that again, I’m gonna cum I think,” she said. So I raised my ass off the bed pumped my hips into her. She collapsed on top of me, her tits pressed into my chest, her hair falling out of her bun and over my face, her moans muffled by my neck, which she nibbled and kissed as she made herself cum.

She was breathing heavy when she sat up, and the sheets were crumpled on either side of me from where she’d gripped them in pleasure. “That was hot,” she said. “Fuck yeah it was,” I said.

“How far away are you?” Sammy asked me after catching her breath by playing with my balls a little. “I was actually getting pretty close when you came,” I said.

“Oh my god, I’m so sorry!” she said, and she started to stroke me again, this time laying on her stomach with my cock just inches from her face. “No, no. Please don’t be sor..” I trailed off, enjoying her too much to speaking complete sentences. It was only about a minute before I started to feel my balls tense up as she quickened her pace, grinning at me and biting her lip to coax a big load out of me.

“I’m gonna cum, Sammy,” I said. And she began to encourage me, saying “Cum for me, please. Give me your cum. Give it to me. Yes,” until I shot rope after rope into the air and all over her hands and my stomach and the sheets.

The tiniest little splash landed on her cheek, and I immediately began fantasizing about what I hoped would be our next sexual encounter, hoping I might be able to someday land a little more than a splash of cum on her beautiful face.

But that’s not to say I wasn’t satisfied by this wholly unexpected, mind- and dick-blowing experience. She was phenomenal, everything you would want a sexual partner to be. Sweet, fun, giving, receiving, enthusiastic, sexy, and fucking good! I told her as much, and she kissed me and said she really enjoyed it too. We didn’t talk about what was next. There was only that moment, and we held each other for a moment before cleaning up and falling asleep holding hands beneath the blankets.


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