Port Jeff will never be the same

Recently my 27 year old s****r Samantha stayed the weekend at my parents house, where I still lived, because her boyfriend of two years had recently broken up with her and she needed a place to stay. She was depressed and frustrated about the breakup and a bit of a mess overall. I felt bad for her.

Why anyone would break up with her is beyond me, she’s a lovely girl if I’m being honest; long brown hair, tall (5'9"), slender, and softly feminine. She is a hidden gem in that she’s attractive yet demure and soft-spoken, one of those girls who’s pretty but doesn’t really know it, or at least, doesn’t know how to use it. I was 22 at the time, and because of our age difference we didn’t have a typically antagonistic b*****r-s****r relationship, instead we got along well, plus I was mature for my age.


We were sitting around bored and she said needed to get out of the house, so she asked me if I wanted to go to the mall. Sure, let’s go. At the mall, we walked around people-watching and casually checked out the stores and clothes. I found that I enjoyed walking side by side with her, if people mistook her for my girlfriend, hey that was fine by me. Even better, she was wearing a white mini skirt, surprising for her, which showed off her best feature: her lithe and lengthy legs. Guys who prefer “more meat on the bones” and muscle tone may not care for them, but they’re perfect in my opinion as I like slender legs. Drives me crazy... but... she is my s****r, so I’m not that crazy, just making an objective analysis is all.

We sat on a bench in the middle of the mall and talked. She told me about her ex-boyfriend, wistfully going over a few details of the hows and whys of the break up.

“I’m getting old,” she said.

“You’re twenty-seven, that’s not old. Twenty-seven is the new thirty-seven... wait, I got that backwards. Never mind.”

She laughed, which made me feel better. “What about you? How’s things with Alyssa?” she asked. Alyssa was a girl I was seeing for a few months.

“Ah, not bad. I’m trying to keep my options open.”

“What does that mean?” she asked.

“I’m trying to build a harem.”

She lightly punched my arm.

“But seriously,” I said, “I’m looking for a girl... well, you know what? To be perfectly honest, a girl kind of like you...”

“Like me?”

“Yeah, except less high-maintenance.”

She smiled and punched my arm again.

“Were you this abusive with your ex?” I joked as I rubbed my shoulder.

“No. But really, what do you mean like me?”

“Hmm.” I gave it some thought, this weird conversation was unprecedented but I went with the flow. “Let’s see... elegant... feminine... shy... likes to make sandwiches...”

I covered my shoulder before she punched it.

“Grrr..” She made that cute sound girls make when they’re frustrated.

“Thank you, though,” she said. “So what else?”

“Hm.. I’m a big fan of long, thin legs.” As I said that she glanced down at her crossed legs, smiled and looked away. Awkward? I smiled and let it sit there, allowing the tension to percolate. I was enjoying this.

“But I need more than beauty...” I sighed wearily and glanced at the people strolling past. “You can find that anywhere...”

I was being sincere, but I also said the line purposely to let it soak in her bones. I had the stark realization I was hitting on my own s****r.

The conversation ended and we sat quietly for awhile. I saw an ice cream place a few stores down and asked if she wanted something. She did, but waited on the bench because the line was fairly long. I eventually got two cups of ice cream and walked back slowly to give myself a chance to size her up. She was still sitting on the bench gazing off in the opposite direction, lightly bouncing her crossed leg, brown wavy hair flowing, looking lonely and... alluring. And that was that. Something came over me, a strong desire for this girl, my s****r, this wonderful feminine creature. No. Noooooo!

We ate our ice cream in silence. When she looked away, my eyes found their way to her legs, uncrossed now and knees separated by about two inches, and I traced a line up her smooth inner thighs to her hips area, covered by a skimpy white skirt, and the thought of her pussy flashed in my mind. Whoa, easy! Eeeeasy. First, my s****r doesn’t have a pussy, she has a vagina, if that, and second, I shouldn’t have been thinking about it. My mind disagreed, and I wondered what my s****r’s clit was like. How erotic that is, my s****r Samantha’s clit, right here, a foot away from me between her legs. I suddenly wanted to finger fuck her right here on the bench, maybe I’ll drip ice cream on her pussy and lick it off. Sam’s pussy juice and ice cream. Sounds delicious. Fuck!

“So, you want to start heading home?” I said after I gathered and discarded my obscene i****tuous thoughts. Little did she know.

“And do what, sit there? Ugh. Let’s do something.”


She thought for a moment. “Hey, let’s go to Port Jeff and walk around.” She was referring to the docks on Port Jefferson, Long Island, about fifteen minutes away. Near the ferry docks there’s a boardwalk, quaint stores and shops, and a few bars and clubs. It’s a popular place to visit and walk around for couples and people in general.

“Sounds good, let’s go,” I said. The thought of walking around that place with my s****r was kinda odd, it was more for couples and families. Wait we are f****y. Anyway.


We got there, I found some parking, and we strolled around the town. It was a Friday night so it was busy with people talking, laughing, and having fun. My s****r’s mood lightened up which was nice to see. I caught quite a few guys checking her out, which was not surprising when you consider the mini skirt and her endless legs. The sidewalk was crowded so sometimes when we had to pass through people, we bumped and rubbed against one another, lots of body contact, more than siblings are supposed to have. A few times I put my hand on her back to “guide” her. You know, that move. There was a sexual tension building between us, I sensed it.

“Let’s get a drink,” she said. There’s this club/bar she wanted to go in, a place with loud music and people dancing. A real meat market. We went in and grabbed two drinks at the bar and found some couches along the wall to sit on. Now I really felt like I was with my girlfriend, and I was hoping the guys in this place thought so too because I didn’t want anyone hitting on her. We were two stiff boards sitting there, not talking, and I was hoping the alcohol would kick in because this was getting uncomfortable. What were we doing here again?

She said loudly over the music, “I’m gonna get more drinks, be right back.”

As she was standing at the bar some guy started talking to her. I fucking knew it. I felt pangs of jealousy, which is ridiculous, I didn’t think he had anything over me anyway, but I stared intently at them, actually trying to read their lips as the music faded into a haze of low noise and the people around me became a blur. I almost got up to grab and confis**te her, but after a few minutes she edged herself away from him. I acted as cool and unconcerned as humanly possible when she got back.

“So did he get your number?” I smiled.

“Nah, I told him I had a boyfriend, and I pointed at you.” She looked at me with a sly smile.

Interesting, things were heating up here.

“Good girl.”

“He wasn’t my type anyway.”

“Why, what’s your type?”

She took a big swig of her drink and leaned toward me.

“Someone like you, except less high-maintenance,” she said.

I laughed. “Good one. What about me?”

“I don’t know... you’re my b*****r, but... I have fun hanging out with you.”

“Same here,” I said. “Too bad you’re too young for me.”

“And that reminds me, you make me laugh,” she said. “You mean, too bad I’m your s****r.”

“Eh, minor inconvenience.”

She smiled and shook her head.

We sat for awhile quietly amused at that conversation and the buzz from the drinks started coming on. We were sitting close together so our legs were touching, and there’s no way that was an accident. I had a decision to make. This chick, my flesh and bl**d s****r, was definitely hitting on me now. What was I gonna do? Isn’t this supposed to be gross?

We went outside to a much quieter patio area where people were hanging around flirting, hugging, lightly kissing, and we wandered over to the perimeter and she leaned against a wood railing. I noticed she had an extra shirt button open, exposing a sexy amount of upper boob and a piece of white bra. Perfect. I walked right up to her with purpose and stood a few inches away, and she looked at me with a curious smile.

“Yes?” she said.

“You shouldn’t walk around like this, it’s kinda... too open.” I reached my hands up to her chest and slowly fastened the button. The sexual energy like electricity passed from her tits to my hands. She looked down.

“Oh, thanks,” she said, blushing. When she looked up I moved in and kissed her, lightly pressing my lips to her soft and moist lips, just for a few seconds. I got lightheaded and fell into a s****r-lust dream state, and when I pulled back I felt nervous as hell about how she might react. She kept her eyes closed for a bit until sl**pily opening them. Suddenly she went pale and an alarmed expression crossed her face. She put her hand to her chest as if she were feeling her heart.

“I have to sit down.”

We found some seats. “You okay?” I asked her.

“Yeah. We should go.”

Man, she looked like a wreck all of a sudden. Well this took a bad turn, I was supposed to be helping my s****r get her mind off things and instead she’s going to end up in therapy. We walked to the car and sat inside.


“I have to sit here for a few minutes and let the buzz wear off before I drive,” I said.


We sat in silence for awhile until she spoke up.

“You shouldn’t have done that,” she said.

“Why not?”

“It’s just... not right. And what if somebody we know saw us?”


“Shit.” She sighed. “Why are you my b*****r... and twenty-two.”

“Wait, which one is worse, the b*****r thing or the twenty-two?”

She chuckled. “Both. You shouldn’t be hitting on me, you know... your older s****r.”

A faux confused look crossed my face. “When did I hit on you?”

“Psh, it started at the mall. Remember ‘I’m the type of girl you’re looking for’?

“I was just being honest,” I said. “You asked me a question and I answered. I didn’t mean I literally wanted you. I just meant–“

She cut me off. “And I’m not high-maintenance.”

“You coulda fooled me after tonight.”

She smiled and punched me in the arm. I grabbed her wrist before she pulled it back, not like a maniac, but lightly, and I expected her to wrestle free but she didn’t. I kissed her hand.

“Come here,” I said. I one-hundred percent didn’t expect her to listen, but she looked forward, her eyes darted back and forth as if her mind was racing, and she slid over. Wow, her mental hamster got a workout on that one. I put my arm around her, which felt incredible, and pulled her into me. She smelled heavenly.

“See, this is nice. No big deal.”

“This feels weird.” she said.

I kissed the side of her head a few times. She giggled.

“Why is that funny?” I asked.

“You’re kissing my head.”

“That’s what... people do in these situations. You’re not a virgin are you?” I teased.

“Yeah, right,” she said incredulously.

“Damn, oh well. I’ll let that slide.”

She laughed and looked up at me. I kissed her, and the kisses were slow, romantic, and loving, but rapidly intensified until we were tonguing like horny fucks that couldn’t hold back anymore. I put my hand down her shirt and caressed her supple tits, soft as pillows. Amazing, my s****r’s tits. When I reached under her bra, her hard nipples grazing against my hand sent shivers up my arm. She looked around at the car windows to see if people could see us, but we were in a fairly secluded area of the parking lot. Plus the windows were steaming up.

“Let’s go in the back seat, there’s more privacy back there,” I said.

She moved aside and I climbed back there. Bad move.

“Why?” she asked. “What are we gonna do back there?”

“I’m gonna fuck you.”

“Oh really!? Psh! Psh!” She was exasperated!

“Alright, we’ll just talk then. It was just an idea.”

I sat back there by my lonesome and she stayed up front.

“No, we’re not doing that,” she said. “Here? No. I mean, do you even have a condom?”

“Actually, check the glove box,” I said.

She shook her head and checked. “Even if there is a condom in here it doesn’t matter, it’s not going to happen anyway. I’ve never, like, seen this side of you. I’m surprised. It’s funny. I can’t believe my b*****r...

“There’s nothing in here,” she said.

I sat there, looking relaxed, meanwhile I was a mess inside. I had a view of her legs and I wanted those lovely sticks straddling me as I watched her tits bouncing around while I fucked her. I figured if I had some patience, maybe she’ll break down again. So we sat quietly for a few minutes, and sure enough, she hopped in the back with me, and laughed the whole time. Surprising me even further, she climbed on my lap facing me, straddling me with her spectacular spider legs, and looked at me with a devilish grin.

“Well, look who came out of her shell!” I said.

“Shut up!” She planted a big fat kiss on my mouth and we tongued like desperate teenagers. I took the initiative and reached under her mini skirt and rubbed my hand between her legs. She had on what felt like cotton panties, and her pussy was hot and mushy and glorious, I could feel and hear the moisture through the cloth. I made the quick decision not to finger her, I wanted the first dramatic entrance to be my titanium cock. So, I moved my concentration to her tits and unbuttoned her shirt, and she got with the plan and reached around her back to unfasten her bra as she looked around outside nervously.

Her tits were slightly less than medium size, cute and round, and she was skinny enough that you could see her ribs, which had the effect of accentuating and clearly defining her tits. I love that. I dove in and sucked those s****r tits like a man who just found an oasis in the desert. I rubbed my face all over them, sucked on the rock hard nipples, nibbled, licked, getting my saliva all over her chest. She threw her head back and let out strong, quick exhales and also watched in fascination, as if she couldn’t believe her young b*****r was going to town on her tits.

Suddenly she dove off me! She ducked and hid adjacent to me. “People! People are coming!” she whispered loudly.

I ducked too, and she was laying on her back with her legs partially open. Perfect, while I was down there I nestled my head between her legs.

“Wait!” she said.

Fuck that, I thought, they can’t see us down here, the windows are steamed up pretty good anyway. I reached my hands up and began the process of removing her panties, which turned out to be cotton, light blue, and I noticed a little bow on the band. Aw. I expected resistance and protest, but instead she giggled and lifted up her ass and let me slide them all the way down her epic legs. Have to smell the panties, it’s a requirement. I held them up to my face and breathed in deep and said ahhhhh. She tried to kick them away from my nose.

“No, stop!” she said, laughing.

I ignored her and looked between her legs, but she was shyly covering her pussy with her hands. Adorable. I kissed her knee and worked my way up to her inner thigh, and if you put duck sauce on this leg I would’ve eaten the entire thing. I peppered her pussy-hiding hands with kisses and I reached up and removed them, she gave token resistance, and there it was, revealed. A magnificent pussy it was, a s****r pussy at that. She even had a little bit of neatly trimmed hair, nice. Who woulda thought I’d have my face an inch away from it. I didn’t tease and go lightly, I smashed my face in there and licked her soaked clit and labia like a hungry dog. She arched her back and let out a load moan. Hearing a sex moan from my s****r was a pleasure to my ears. I quickly had her pussy fluids all over my face, but I didn’t finger her or tongue fuck her, I really wanted my cock in there, and I wanted to fuck her now while the going was good. That reminded me of the lack-of-condom situation. We’ll see how it goes.

After swallowing about a cupful of Samantha’s pussy juice, I leaned back and sat upright in the seat, taking a breather, hoping she would do something. And like the good girl she is, she leaned forward and got on her knees next to me, and began opening my pants. I love this chick.

I helped her take my pants and boxers down, and my rigid cock sprang out, and she looked at it in awe, and not awe because it’s eleven inches, it’s not, but it’s a good size, don’t worry about it, but awe because she was seeing her b*****r’s cock for the first time, so erotic, forbidden and naughty. She didn’t waste time and engulfed it, and oh that’s good. She slid her wet lips up and down, and the feel of my s****r’s lips on my cock gave me otherworldly sensations, add the sight of her head bobbing up and down and her lovely brown hair flowing down to my hips, and this was as good as it gets. I held the back of her head as she sucked, and she twisted her head around and I felt her tongue on my skin; she wasn’t giving me a blow job, she was making love to my cock with her face. It’s just not something I expected from my quiet, shy s****r, but it’s often the quiet girls who are the most sexual.

I needed to fuck her. I put my hand under her chin and turned her face toward me, and she looked at me like a curious puppy, her mouth area wet with saliva and my pre-cum.

“Come here,” I said. I guided her up and she got on top of me again, straddling me, dick and pussy only a few inches apart. We tongued with love and I tasted myself, not bad. She leaned back and we sat there for a moment, catching our breath, probably thinking the same thing. She looked outside the car windows again, and then we stared into each other’s eyes.

“Are you on birth control?” I asked.

“Yes,” she said. I was relieved, that was good enough for me at that point.

I squeezed her ass and pulled her forward, and grabbed my cock and rubbed it up and down her pussy lips, waiting for a reaction from her. Nothing, no protests, no words, nothing. I guided the tip near her dripping hole, and didn’t hesitate, I slid my cock in her slippery cunt, and lifted my hips up, pushing in as far as I could. Wow. She threw her head back and let out a series of strong and sharp exhales with her eyes closed tight. Unsurpassed blissful sensations went through me, being deep inside her smooth and warm pussy, skin on inner membrane, b*****r inside s****r.

“Oh my god,” she whispered, and began rhythmically moving her hips up and down, riding me slowly. She bowed her head to look at the unique and exotic sight of b*****r and s****r fucking, her mouth was hanging open, lips wet, hair hanging down, tits exposed. She was an enthralling sex bomb. We both watched the penetration in fascination, taking it all in.

We steadily picked up the pace, until she was bouncing on me and I was pounding her clit, mound and wet cunt hole. Her tits were all over the place and I grabbed and massaged them to keep them steady, just helping out that’s all.

“Pull out before you come, okay?” she said breathlessly in a dead serious tone.


“Promise me.”

“I promise. Let me know when you’re gonna come,” I told her. I was going to try my best to let her come first, hopefully I could last that long. I felt my body building up to orgasm.

“I’m gonna come...” she whispered. That was fast.

“Look at me,” I whispered back.

I grabbed a clump of hair on the back of her head, tightly, prompting her to face me. Our eyes met, and every time hers strayed I held her hair tighter as a way of reminding her to stay focused on me. I pumped her hole at a steady, fast pace, our hips smacked together, I could feel and hear her sopping pussy gushing fluids. I studied her face, falling in sex love with my s****r. Her breaths were faster and shorter, her eyes had a drowsy sex look and they began to glaze over and I knew she was coming. I felt her cunt tightening around my cock, her mouth was shut tight, she was whimpering and moaning, her eyes kept closing but she desperately tried to keep them open because I kept my gaze locked with hers, then she let out long f***eful exhales, and it was if the soul of her eyes disappeared into an orgasmic abyss. She came. I saw it in her eyes... it was amazing.

That put me over the edge and I frantically nudged her hips away and pulled my cock out, wondering if she was going to do the right thing, otherwise we were going to have a mess. She quickly scrambled off my legs and sucked me like a crazy chick, as fast as she could, as if she was desperate to get every drop of my cum. Every inch of my body filled with intense orgasmic pleasure, the sight of my lovely s****r sucking away magnified it a thousand times, and I pressed down on her back with my hand and came like mad in her mouth. She swallowed it all, and slid her mouth up and down my cock to gather up whatever cum was left. I pulled out and was clean as new. A legendary orgasm, an incredible s****r.

We sat side by side in the back seat for awhile, in silence, settling our emotions and catching our breath.


We didn’t talk the first half of the drive home, feeling exhausted... thrilled and disturbed about our adventurous night. At least that’s what I felt, but judging by the look on her face, I’m sure she felt the same. She broke the silence.

“So, am I part of your harem now?” she asked sarcastically, but it almost sounded as if she thought I was serious about the harem comment earlier, like I had tons of girls I was juggling. I did okay with girls, but not that good.

“Yes, you’re part of my harem, but you’ll be my main girl, don’t worry.”

She smiled and punched my arm. When we got home, we both went to our separate rooms and slept.


The next morning, we sat at the table and ate breakfast with my parents. My s****r and I were unusually quiet and kept nervously glancing at each other, trying to hide our smiles and suppress out giggles. We were both in an invisible love cocoon and the rest of the world didn’t matter. I was hoping our parents didn’t notice anything... and I wondered what the future held for us.

Later that day my good friend Tyler called me.

“What’s up Tyler,” I said.

“What’s goin’ on b*o. Hey ah... I saw you and Samantha at Port Jeff last night.”

The bl**d drained from my face.

“Oh... yeah, we hung out there... a bit. Where did see us?” I asked nervously.

“Umm, I saw you at that bar, man... on the patio in the back....”

I felt nauseous. I remembered that was where I kissed my s****r, standing by the wood railing, in full view.

“Oh. Okay, yeah... So, why didn’t you come over and say hello?” I asked.

He was silent for a moment, then just said, “Dude...”

97% (45/1)
Categories: First TimeTaboo
Posted by jaymz76jaymz
3 years ago    Views: 3,649
Comments (13)
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2 years ago
Top notch!
3 years ago
Powerful story
3 years ago
Wow!! That was one of the hottest brother/sister stories I've ever read! I am rock hard right now and can't wait to get to part 2!
3 years ago
this is excellent
3 years ago
wow, thanks
3 years ago
great story so hot!
3 years ago
Great story, now go for it and fill her cunt and arse with as much cum as you can muster, and pump it deep and hard.
3 years ago
3 years ago
Great story
3 years ago
That was great!!
3 years ago
Dump a load in her pussy, dude. Then another load up her ass.
3 years ago
One of the best I've ever read. It was so HOT and sensual. Thanks for posting.
3 years ago