xxx-I Was My Brother’s First Boyfriend

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By Lauren McAllister

Okay, I admit it. I’m a fuck up. But, just because I’ve dedicated most of my eighteen years to sloth and indolence and empty pursuits, that doesn’t mean I don’t have ambition. I really want to go to Harvard. Alas, to get there, I needed to ace – and I mean knock it right out of the fucking park – my AP Chemistry exam. My only problem was…I hadn’t lifted a Chem Book all year. Let’s just say that my myriad social obligations and farting around on my I-Phone just didn’t leave sufficient time for the rigors of academia. I found myself in a real bind if I didn’t want to spend the rest of my life handing out Frappuccinos and Goddamn lattes at some jerk-off coffee emporium. And I didn’t. Trust me on that one.

That’s when I had this idea. This awful idea. I got a wonderful, awful idea. (I also spent some of my should-be-studying time watching old Dr. Seuss cartoons.) Double alas, up rose another perplexing problem. You see, I had never been very nice to my little brother. I’d basically treated him like an annoying and subhuman piece of shit from the day I was old enough to treat him like an annoying and subhuman piece of shit. He was a year younger than me and an absolute weed. Not the kind you smoke, that would have been cool and Rick was anything but cool. So, now I needed a huge favor of him. A massive favor. So big that, even if he liked me (which, indeed he did not), he would have turned me down flat.

Let me explain.

Rick, except for being a guy, looks a lot like me. He’s slender, has the same hair color and has sort of a soft face. Stick a couple of tits on him and plop him into a dress, and he’d make a fairly reasonable girl. Plus, he’s also got a brain the size of the Iberian Peninsula. You probably see where my mind was heading on this. If I could somehow convince this genius who despises me, to dress up in drag and take that exam for me, I might just make it to the Ivy League. But what did I have to offer the little twerp?…I mean, dear boy.

It couldn’t be money because he had all of his and I’d spent all of mine. Perhaps I could borrow some of his to bribe him with? That was about as likely as finding a Canadian who doesn’t like donuts. I racked my brain for days – days that I could have been studying for Chemistry, but what good would that have done me? Time was rapidly running out and so I came to the only solution that realistically had a chance. I was a pretty good looking girl with a body that even I couldn’t keep my hands off and he had a penis. I’d never seen Rick with anything even remotely female, so I thought offering to hand over a little sister sugar might be the bargaining chip I needed.

Surprisingly, even when you’re desperate, and I most certainly was, offering to “give it up” to your brother isn’t as easy as it sounds. I mean, EWWWWWWW!!!

It’s just the thought of your own brother looking at you and thinking, “Yeah, she sucked my cock,” was pretty off-putting. Imagine every breakfast, every morning, and him looking over at your mouth and thinking, “Yep, I stuffed my dick in there.” And then coming home for Thanksgiving dinner, when I’m old and 40, and having him still looking at me, knowing that we’d done the business. Having him on top of me, looking down into my eyes, as he pumped his lap lizard into my sin silo. Yuck. Knowing what his spew tastes like. Gross beyond gross! I wondered if I could buy a condom that would fit over my brain.

Procrastination never felt so good. I left the hideous deed for as long as possible (like I do almost everything else in life) but there came a moment when things could be delayed no longer. One Saturday morning, when my parents headed out to do some grocery shopping, I took off all my clothes and put on a short robe. It was made of a thin, silky material – I wanted to wear something a little sexy to try and make myself more horny than suicidal. It didn’t work but off I toddled to the little asshole’s room, anyway.

Knock. Knock.

Rick knew I was the only one left in the house, so he didn’t answer. I took a deep breath, tried very hard not to throw up and entered his boudoir.

“What do you want?” he sneered, not looking up from his book.

To be fair, I probably deserved that.

“I need a favor,” I politely answered with a hopeful smile.

“Well, you can fucking forget it,” he encouraged me.

God, I felt sick. My heart was beating like a jackhammer. “I’ll trade you.” I almost hurled but spoke calmly and did not let my friendly smile wane.

“Trade what?”

Well, at least now I had his interest. I took another deep breath and slipped the robe off my shoulders. It took all the strength I had to keep my hands at my sides to allow him to fully review the freshly shaved goodies. “You do my AP Chem. final and I will let you do anything you want to this.”

Rick got up from his desk, stood about three inches in front of me and gave my all-you-can-eat sexual-salad-bar the once over. I didn’t know whether he was going to say yes and fuck me standing up or punch me in the snatch.

“I’m gay,” he announced.

Well, I certainly wasn’t expecting that but it did explain the paucity of harem honeys hanging around him.

“Gay? As in, you’re doing guys?”

“No. Well, not yet. This town is too fucking small. I’m waiting till I go away to college.”

I indicated my primo penis-portal and the be-nippled nachos. “So, I guess none of this is of any interest to you and I’m going to spend the rest of my life wearing a brown-stained apron.”

“How badly to you need to pass this exam?”

“I’m standing naked in my brother’s room, offering to let him fuck me. How badly do you think I need it?”

He looked me up and down again. God, I felt exposed. It was like my gynecologist had just invited his poker buddies into the examination room to grab and eye-full.

“There might be something you can do for me, in return.”

Yikes! I could feel a righteous ass-fucking in my near future. “And that would be?” I enquired as enthusiastically as I could.

“Teach me how to suck a cock and I’ll take your stupid exam for you.”

Could it be that easy? Had Mother Luck shined down on me from up on high? I thought I’d better break the stickiest part of my plan to him while he was still being so agreeable.

“Ah, you’d have to wear women’s clothes….”

“That won’t be a problem.”

“No, I guess it won’t.”

So, I put on an old suit of my father’s, stuffed this big dildo Rick had hidden in his mattress down my borrowed jockeys and waddled back into his room. Little brother smiled nervously and looked down at my visibly-aroused crotch. I rubbed my bogus boner up and down suggestively a couple of time to indicate my interest in getting friendly and he dropped to his knees. Rick undid my belt (better than I’ve ever done in that situation – man those things are as tough as bra straps to unhook) and slowly unzipped my pants before taking out this big wad of cyberskin manhood. I was pretty well hung for a girl. He licked and sucked on that thing like it was a dick-shaped Dove Bar (or maybe I’m just projecting…).

As he continued to slurp and work it, I’d throw in the odd helpful suggestion. After all, I have received some fairly positive reviews for my own oral ministrations. To give the whole, bizarre proceedings a little more venereal verisimilitude (and to give me something to do), I started to diddle myself to match his simulated blow job. If he increased his mouth action, I’d bash my bobbin with equal force and frequency. Sigh. Moan. Now I was really, really getting into it. My pulsating pud was soaking wet from his saliva and my homegrown sauce. I had this strange urge to jam my cock down his throat till it reached his intestines. The room started to spin and little and my legs started to wobble. I started yelling at him to “Suck that thing!” and “Blow me!” and BAM!!! I came like that time I stole my mother’s vibrator. Rapid-fire rounds of orgasmic artillery rocketed up my vagina and exploded in my abdomen. Wow! I grabbed Rick’s head and rode those womb waves hard as I spasmed all the way to the floor of his room. All in all, I gave him a pretty close approximation of a same-sex encounter. The only thing I couldn’t do was fill his mouth with a load of junk juice. A girl can only do so much. After my breathing had returned to normal and the room came back into focus, I smiled at him. “I think you’ll do just fine.”

So that night, it was me looking over the dinner table at Rick and thinking, “He just sucked my cock.” Visions of the top of his head rocking back and forth filled my mind causing my girlie-gulch to tingle. I was beginning to see what guy’s like about it so much. From then on, the second my parents left the house, I’d be in his room getting my not-really-a-knob polished. I even went out and got myself a “boy” haircut so I could return the fellatio favor. His spunk didn’t really taste any different than the guy who gave me my driver’s test (I never could figure out how to parallel park.).

Last week, Rick donned the dress and wrote my Chem. exam and, if I get into Harvard, I said I’d let him fuck me up the ass. Hell, I can probably use the practice as much as him. Another year and he’ll be able to move on to real guys and not just his sister playing dress-up and all will be right with the world.

Now, I just have to find a boyfriend who wouldn’t mind giving me the odd blowjob cause the last guy I had completely flipped out. Sigh. Straight men can be sooooo closed minded.

Copyright 2014 Lauren McAllister

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