Road Trip to Boston

"Hey Jenny," my older brother Sebastian called from the living room. I could hear the question in his voice; I could almost see the blush on his face. With a rush of adrenaline I realized what he was about to ask. "Do we have time for a quick wank before we go?"

I finished washing up and closed the bathroom door behind me. My twenty-five year old math genius brother was sitting on his couch, peering anxiously at me from behind his large, owl-like glasses. We were supposed to be leaving right now. We were supposed to be going downstairs to my illegally parked Jetta, and then swing by my friend Jessica's place, and then drive up to Boston where Sebastian would be attending a mathematics symposium and Jess and I would be catching our friend's band playing their first out of town gig.

"Of course we have time," I said, unable to keep the smile off my face, "But we have to be quick about it."

Sebastian is so cute, all 6'4" of him. I don't understand why he's never really had a girlfriend. I guess he just needs to find a girl who is smart enough to appreciate his geekiness, and aggressive enough to cut through his shyness. He is kind of like an over-sized Tigger; full of energy and innocence and enthusiasm and hilarity. And then in the presence of an attractive girl (I should know, I've tried to set him up before), he gets all stiff and sober and starts going off about Set Theory and Imaginary Numbers and the Calculus of Newton. I swear, sometimes that boy is impossible.

Speaking of being impossible, he already had his jeans down, and his penis was sprawling across his lap, all plump and firm and delicious looking.

We hadn't done this in a long time, not since he started grad school. Sometimes I thought he must have outgrown our little game, and though I had certainly had my fair share of encounters since I had been in college, I have to confess that I had missed playing with him. This was something special, just between the two of us.

I sat down on the futon couch next to Sebastian. "We have to be quick," I reminded him, "we're already late to pick up Jess."

"I know," he said, "Don't worry, it won't take long."

For just a moment, I contemplated dropping my head onto Sebastian's lap, sucking that cock, making him come with my mouth, really blowing his mind. I had had this nasty thought many times before and I had never acted on it. As much as I love giving head (and I do love giving a great blowjob), this was my brother we were talking about. And the rules of the game had always been: As long as it's only touching, we weren't doing anything wrong. As long as we just masturbated each other, it wasn't incest.

It's amazing, how good the human mind is at rationalizing.

I peeled my olive tank top off so that he could watch my breasts jiggle while I worked. He always seemed to appreciate that, and frankly I liked him watching me.

His cock certainly appreciated the gesture. It was standing straight up, and leaking a little clear precome. I wrapped my hand around his familiar, comfortable girth and started pumping.

Because I was in a hurry and wanted to bring him off quickly; hell because I was turned on and horny and curious about how he'd react, I slipped my free hand between his thighs; caressed his balls tenderly for a moment, and then slid further back into uncharted territory. Probing gently between his ass cheeks, I found his anus. My last boyfriend had taught me this trick and I was anxious to see if Sebastian would like it too. As I stroked his hot dick, I tentatively circled that little hole. He arched his back and moaned. I took that to be a go-ahead signal. Very gently, I worked the tip of my forefinger up inside him. At the same time I pumped his dick hard and fast until my shoulder ached, squeezing him for all I was worth.

I thought it worked just fine. Sebastian arched his back and yowled like a tiger. I felt his body squeeze my finger as he came, which I thought was sexy as hell. Fortunately Sebastian had pulled his own shirt off already; he shot a big fat load of semen all over his belly. Some droplets made it all the way up past his nipples! I released him from my grip and went to work slurping up his salty, slightly bitter juices. Hey waste not want not, right?

Normally this would have been the part where I would have pulled down my Capri pants and climbed onto his lap and Sebastian would have gotten his finger nice and slippery and driven me crazy drawing tiny circles around my clit and finger fucking me to a humongous orgasm. But we were already late and Jessica hates it when I'm late and traffic would only be getting worse anyway. So regretfully I pulled my top on and Sebastian got his clothes back together and we headed downstairs to my (mercifully unticketed) car.

We stopped uptown and picked up Jessica (who was late herself and therefore had no grounds to be annoyed) and got on 95 headed north. Sebastian, who doesn't drive, sat in the passenger seat next to me while Jess sat in the back. Traffic was heavy, and I had to concentrate on driving for a while. It took me some time to realize that Sebastian, ordinarily a chatterbox, was being quiet as a mouse. That could only mean one thing: he must think that Jessica was cute. Well, he wasn't the only one.

Jessica was a little shorter than me, red-haired, curvy as all hell, smart, and funny. She was my best friend at college, and I had more than a little bit of a crush on her. We had booked a hotel room in Boston together, and until Sebastian had asked if he could come along for his math conference, I had entertained nasty schemes of seducing her.

For a while, Jess and I talked about school and our friends and the band we would be seeing that night, while Sebastian sat and listened. Then the driving got monotonous, and Jess settled back with her ipod for a nap.

I felt something tugging at the drawstrings of my Capri's. Oh My! Sebastian was being a little frisky... not that I minded; I was still horny from our little escapade early on in his apartment. I glanced in the rearview mirror: Jessica was slumped against the window, eyes closed, earbuds tucked into her ears. I skootched my ass up to give Sebastian better access.

"You think she's hot, don't you?" I whispered.

"Maybe." He whispered back.

"Maybe means Yes." I breathed back at him, but by then his exploring fingers had found what they were looking for, and I needed all my concentration just to keep the car on the road.

All the way through Connecticut, and halfway through freaking Massachusetts, Sebastian drove me crazy with his long, probing fingers. I couldn't ever quite come- he couldn't get quite vigorous enough with his hand inside my pants; and I couldn't let go enough (I was driving after all). It was exquisitely frustrating, delicious and naughty and tantalizing. By the time we started to get close in to Boston and traffic started to get really intense again, I was quite sure I'd made a big sticky puddle in the drivers' seat and that the car must absolutely reek of excited female. Sebastian took his fingers back and licked them off for me, looking equal parts sheepish and pleased with himself.

Damn, if I didn't have an orgasm soon...

We dropped Sebastian off at the University to go play with the other math geeks, then Jess and I parked the car and went to the show. Our friends' band rocked, there were a lot of people there, and we had a great time. By the time we got back to the hotel, it was after midnight and Sebastian was already asleep on the other twin bed, snoring softly.

We turned out the light and tumbled into bed. I was bone tired, a little drunk, and sexually wired for sound. I had been hyper-aware of my poor swollen clitoris all night long, and I thought there was a good chance I could come by just squeezing my thighs together. I wondered if I had it in me to screw together my courage and make a move on Jess.

Harsh neon light spilled through the curtains from the building across the street. I could make out Jessica lying on top of the sheet across the bed from me, wearing an oversized white t-shirt.

I rolled over, closer to Jess. I wondered if she could see my erect nipples through the thin fabric of my bedtime shirt in the dim light. I could feel her breath on me. This was it. I had to say something. I had to make a move.

"I saw what was going on in the front seat today," Jessica whispered to me "Tramp."

My heart sank down into my toes. I felt my ears burning.

"You little twat," she giggled, "He's your brother."

I didn't know what to say. How could I explain to her that it was just a game that Sebastian and I played together?

"So.... Are you fucking him?"

"No..." I felt tongue-tied, "It's just a game... between us... that we play sometimes..." I trailed off lamely.

"Are you sure?" she smirked. I nodded sheepishly. "I'd fuck him. For sure."

"You ought to," I said, "He thinks you're hot."

"Really? Are you sure you wouldn't mind?"

"Mind?" I said, "Of course I wouldn't mind!"

"I think he's really cute." Jessica rolled over onto her back "It's too bad he's so shy."

"I know, I know." I sighed.

"He finger-banged you all the way from New York to Boston, didn't he?"

"Pretty much." I admitted.

Jessica sat up in bed. Her large breasts jiggled pleasantly under her t-shirt. Sometimes I wish mine were big like hers. "You're nasty Jenny," I could see the smile on her face, "You sure you're not fucking him?"

"Jess!" I said, "He's my brother! I couldn't do that! We just, you know, play sometimes."

"I see." she said, though I wasn't sure that she did at all.

A little while later, Jessica was asleep. I was exhausted, but I couldn't sleep. I was way too worked up, way too frustrated. It was late, and my eyes ached.

All too aware of Jessica's presence in the bed next to me, I squirmed my panties down around my knees. Just the feeling of the night air on my (very!) wet pussy drove me deliciously crazy. The idea of illicitly masturbating next to my best friend (who --gasp- now knew my most deep, dark secret!) just added to the sexiness of it all. I ran my fingers up and down my slit, which was absolutely drooling, and stroked my clit. Sure enough, pretty much right away I was coming, and hard. I tried not to shake the bed, tried not to make too much noise. I bit down on my lip hard.

But one wasn't going to be enough. My body wasn't about to allow that. Even as the last spasms from my first orgasm passed, my fingers were busy again. I allowed my fingers to penetrate my pussy, spreading my wetness up down and all around. God, I was exhausted and turned on, drifting in between dreaming and consciousness.

And maybe I imagined it, or maybe I dreamed it or made it up in my head, or maybe it was real after all, but Jessica snuggled up against me. I felt her large, heavy breasts press warmly against my back. She kissed my neck and stroked my hair and her fingers found their way down to that sticky slippery place between my legs, and then they were all over my ass, exploring that secret place between my cheeks where I so longed to be touched, and then her fingertip was working its way up into my asshole and I was so excited I was in tears and she was penetrating me and I felt so full and turned on and I wasn't sure I could take any more and I didn't ever want her to stop...

...and when I woke up the morning sunlight was streaming in through the window and I was all twisted up in the sheets and I had kicked my panties off so they were hanging from one ankle and I was alone in the bed.

I heard them before I saw them. I looked over and there they were: Sebastian was lying on his back on his bed squinting as he always did when he didn't have his glasses on, and Jessica was straddling him on all fours, her red hair a wild mess, her breasts hanging down into his face. I have to admit it- the first thought that went through my head was "Damn, she has beautiful tits!"

As I watched, Sebastian sucked and licked on Jessica's boobs. I felt a twinge of jealousy. My brother's cock was nice and fat and hard, lying on his flat stomach. I felt bad for feeling jealous. I wanted him to have her.

Jess looked over at me and grinned. She climbed up off him and clambered off the bed and over to her overnight bag. She caught me staring at her nakedness and grinned again, a big happy horny smile. I couldn't believe what was happening. She looked so sexy!

She tore open a condom and rolled it carefully onto Sebastian's erection. "This is our second round," she smirked, "You slept through the first one."

I couldn't believe it. My fingers found their self-conscious way downstairs to my pussy which I discovered was already copiously wet. "You're too far away," Jess informed me. She was rubbing Sebastian's latex-clad penis up and down her pretty pussy, which I was interested to note was a slightly darker auburn red than the hair on her head.

Ditching my t-shirt (and the last shreds of my modesty), I climbed onto the bed next to them. Jessica had positioned my brother's cock right at her opening. Her lips were purple and pouting open hungrily; I could see her wetness literally dripping down onto him in sticky strands. It was downright pornographic.

As I watched, she lowered herself onto him, swallowing his cock until their pubes were kissing. I couldn't believe what I was watching. It was so hot! Sebastians' eyes were open, but unfocused. His hands were on her boobs, which jiggled nicely as she moved. I thought I might melt! Jessica was bouncing up and down, grinding herself on Sebastian's nice big cock. I held my breath and reached out, cupping her ample, jiggling ass. It felt good in my hand, soft and sexy.

"Do it to her," Jessica rasped, "Finger her. I want to watch."

As if in a trance, Sebastian removed one hand from her breast. Her nipple was fat, pink and erect. He reached over, in between my legs where my own finger was already busy on my engorged clitoris, and then he slipped his long, talented forefinger up inside me.

"Oh fuck yes," Jessica gasped, "Make her come!"

Sebastian knew just how to rub me, and between his finger and mine and watching Jess' body bounce up and down and the smell of sex and her girl juices all over his condom, I was in the stratosphere. I think I actually screamed out loud when I orgasmed, which was kind of embarrassing, but it felt so good I didn't care.

"Come over here," Jess told me. I don't know how, but I knew exactly what she wanted me to do.

Sebastian's finger was still up inside me. Jessica raised herself up onto her knees so that only the head of Sebastian's cock was still inside her. I'd never seen another girl's pussy so up close before. I could see her clit and everything, straining out from behind its little hood. I wrapped my thumb and forefinger around Sebastian's familiar girth and started pumping, short fast strokes like the wings of a butterfly.

It felt weird to be jacking him off through a condom. Weird, but in a good way. He was very hot, and all slippery sticky with her come. I loved the smell of their sex. I pumped harder, faster. Sebastian was super excited, I could tell from the heaving of his stomach and the way his balls were drawn up tight. Jessica had her clit pinched between two fingers and was jilling for all she was worth.

Sebastian's finger curled up inside me as he shot off, triggering another little orgasm from deep inside me. Jessica was coming too, flushed red and breasts heaving, her fingers a blur on her clitoris. She was so beautiful when she came.

As she settled down and as Sebastian's cock shyly shrank, I sat up on the bed, feeling self-conscious and exquisitely naked. Jess kissed Sebastian on the lips, long and smoldering and sensual. Then she turned, and taking me utterly by surprise, kissed me hotly on the lips.

"That was the most beautiful thing I have ever seen," she whispered in my ear, "We are going to have a lot of fun together. I just know it."