(The characters in this story are 18 or over)
I was always a modest as a teenager, not wanting to be seen naked by anybody who absolutely didn't have to see me. Even getting undressed for a medical exam was a traumatic event. Through school I avoided sports and even phys ed classes – largely to avoid being naked, or even the risk of being naked in a locker room full of other kids. Swimming pool? Forget it – put on a bathing suit in a public locker room? Could I have my teeth drilled instead?
I'm not really sure when I became "sexually aware". I guess reading "Everything you ever wanted to know about sex (but were afraid to ask)" cover to cover two or three times might have done the trick. I was in my late teens by then. (yes, a very late-bloomer.)
My brother's similar obsession with modesty was made very clear to me even though we shared a bedroom and bath. He never undressed in front of me, in fact, if I got near the bathroom while he was shaving or brushing his teeth, he'd hurriedly kick the door closed. I shouldn't leave you thinking that he had a problem associating with his "little brother" – we got a long fine otherwise. Not that I cared about not seeing him naked – at least not at first, after all, I was discovering my own body and doing a little "experimenting" with my own cock. I quickly learned that furiously rubbing your cock to multiple orgasms will leave you chafed raw.
I don't think I set out to taste my own cum – at least not at first. It just sorta turned out one of those times I laid back and slowly stroked myself that my 18 year-old body showed me how far it could ejaculate, sending a spurt up to splash on my chin, and into my mouth. At first I was a little turned off by it, but I got to thinking, that if I someday wanted a woman to swallow my cum, I should be willing to do the same thing myself. From that point on, I tried several methods to get my cum to my mouth. (You can read about the closest I came in "His first taste of a man".) Needless to say, I realized after several fruitless tries that my cock would never reach my mouth.
I needed a surrogate cock, and I asked myself – whose cock is the most like mine? The answer was obvious – my brother's cock. This led to a much more difficult question, how to get it in my mouth. Sure – a horny teenager like me, if he asked to suck my cock, I would have said yes as soon as I regained consciousness. Though I would have insisted I get to suck his in return. He, on the other hand, didn't even like my dirty jokes, blanching if anything "sexual" was uttered. He just seemed too uptight about sex to even broach the subject.
Not being the type to give up easily, I thought and schemed and plotted about how to bring my desire about. I though about conning or blackmailing him into it, but no likely opportunities presented themselves. I didn't have to wait long for a possibility to present itself, and a plan to reveal itself. My brother's 21st birthday marked his ability to visit bars, and he tended to go overboard a bit, resulting in his arriving home late, and often more than slightly impaired. I watched as he arrived home on most Friday and Saturday nights, walking unsteadily to the bed, undressing (in the dark) and falling into a deep sleep. I saw my opportunity.
An additional challenge that needed to be addressed was my own inexperience. I needed to "practice" taking a cock in my mouth before I tried it for real. After all, biting my brother's cock or scraping my teeth over the head could wake up the soundest sleeper. I needed a way to practice before tackling the real thing.
I screwed up my courage and visited an "Adult toy store" on the outskirts of town. I self-consciously eyed the selection of vibrators and dildos and selected a flesh-colored one that seemed to be about the same size as my cock. I nervously paid the sleazy guy behind the counter and took my contraband home. I began practicing "giving head" to that rubber cock every chance I got, slowly overcoming my well-developed gag reflex so that I could take about 5 inches of the dildo into my mouth easily. I even retrieved it from it's hiding place under my bed while my brother slept on more than one occasion, fantasizing it was his cock, and imagining how I would react to him cumming in my mouth. Gawd, that rubber cock tasted awful, but it served my purposes. Feeling capable of taking a real cock into my mouth now, I patiently waited until the coming weekend for my chance.
Friday night rolled around and my first chance to act on my plan arrived. The hot Chicago nights made it fairly normal to sleep in the nude – or as close to it as situations allowed. I always slept completely naked, year round – I just never liked the feel of pajamas or even underwear when I slept, just my naked body and the sheets. Since I was alone in the room, I undressed, tossing my clothes on the floor by the bed before I slid into the sheets. Even with the window wide open and the ceiling fan on high, it was still sweltering. I laid back and closed my eyes, waiting to see if tonight would be the night.
I'm not sure when it was, but he staggered in several hours later – completely wasted. He stumbled into the bathroom, closed the door most of the way but left the light off. I heard him taking a long, long piss – you know, the one you are dying to do after that last beer soaks in and you hurry home before your bladder explodes. Eventually, he finished and the door opened. I did my best "sound asleep" imitation as he sat on the edge of the bed and undressed to his shorts, then collapsed on the bed. As usual, he slept on top of the sheets when it was hot, but with his underwear on.
I watched and waited for a while, and was soon rewarded with the sound of his deep, rhythmic breathing. I waited for what seemed like an additional eternity – probably just a few more minutes before I quietly pulled my sheet off of me and slowly slid out of bed. I crept across the room slightly hunched over – as if I was less obvious or harder to see that way – the ceiling fan giving me chills even in the hot room. I quietly knelt at the side of his bed. Luckily, he was sleeping on his stomach. This allowed me to employ my "2-step" strategy to get his underwear off. I carefully reached over and slipped my fingers under the waistband of his briefs. Taking a deep breath, I slowly slid them down, exposing his bare bottom.
I couldn't resist touching and stroking it – even though I was actually just biding my time until he turned over. I knew it would only be a few minutes as he almost always slept on his back, so any time in this position was temporary. His bottom was like mine, smooth, round – I had to snatch my hand back as he snorted in his sleep and then rolled onto his back. I gulped – it was the opportunity I had hoped for. The bulge of his cock and balls looked huge in his half-off briefs.
I carefully lifted the waistband of his shorts away from his body, freeing his cock, and lowering them to expose him completely. Even as I worked his briefs down his thighs, my eyes were glued to his cock. In the moonlight, up close, it looked imposing – big, threatening. I gulped and reconsidered what I was about to do. I paused and looked up at my brother's face. Still breathing deeply, eyes peacefully closed – I guess alcohol makes you sleep pretty well. I glanced to his cock and back to his face as I moved my hand to gently touch his cock and balls. Not a stirring, nothing. I turned my attention to his cock. I gently grasped it, it felt weighty in my hand, bigger than mine – probably both thicker and longer.