James & Emily: The Lesson

After my mom died when I was ten, my dad never liked leaving me alone in the house. He had to travel three or four times a year for work, though, which put him in a bind. My grandparents, aunts and uncles pitched in for a while, but eventually, for one reason or another, they became unable to housesit, and I hated having to live somewhere else for three to four weeks while my dad was gone on yet another business trip.

So my half-brother, James, seemed like the perfect solution. My father had had James in his early twenties out of wedlock with a woman named Judy, and he and my mother had had the rarest of things with Judy: a civil relationship.

James had been a fixture in our house since well before I was born; Judy was very much aware that, although my father was an excellent parent to her child, she would not have been happy in a relationship with him as a husband. James lived with her and his stepfather most of the time, but he spent half his weekends, four weeks during the summertime and a fair allocation of holidays at our house, as well.

The year I turned fourteen and James was twenty-eight was the year he took over what he jokingly called "Emily Duty" for my father. James was a freelance designer, so he just carted his laptop with a large screen attachment and several weird computer hookups along with him and set himself up in the guest room.

I liked it when James came to visit. It was kind of like a mini-vacation. He let me stay up as late as I wanted; he didn't fuss at me about my diet or my boyfriend.

Also, he was super cute. He worked out regularly and had a disarmingly sweet smile and a charming disposition. I had a big-time crush on James.

It wasn't until about four years into his regular stints on Emily Duty that things changed between us, and our relationship took on a new dimension. Some people might think it's wrong, and I don't deny it, but he taught me things I'll never forget -- and don't want to forget.

It started the night my boyfriend, Brian, dumped me. I had turned eighteen a few weeks before -- my late-September birthday meant I was always one of the oldest in my class, so though I was legally an adult, I still had a good eight months of school left before I was free.

Brian was twenty, and I'd been so pleased with myself for landing a guy with a job and his own place as a boyfriend when I was still in high school; my blooming curves and pretty face no doubt had a lot to do with that, but I was young and insecure, unaware of my own beauty.

We were at a party at his best friend's house; we'd been drinking, and he pressured me into going upstairs into his best friend's parents' bedroom with him.

Brian was constantly trying to fuck me, but I always refused. I'd let him finger me and eat my pussy before, and he'd never made me cum. He first told me that something must be wrong with me, then he said that if I would just let him fuck me, I would be able to cum. Like his cock was a magic wand. Brian was kind of stupid, and he thought I was, too, but I had an Internet connection and the ability to read -- and I was able to get myself off with my fingers just about every night -- so I was pretty sure he was full of shit.

And I wanted my first time to be special. I knew most women didn't cum when they lost their virginity, and I didn't necessarily expect to, but with Brian, it wouldn't be special. It would just be over with. Probably in the grimy, tiny two-bedroom duplex he shared with two other guys, one of whom slept on the sofa.

I refused him again that night, after he'd halfheartedly licked at my pussy for an entire five minutes. He'd asked me to shave it for him, saying he'd eat me out more often if I did, but so far, I wasn't having any luck. I was beyond bored and offered to suck his cock, instead. He'd had a lot to drink, too, and it was hard to get him erect; I tried my best, but he was disappointed with my performance, as usual, even though I'd pulled his cock all the way into my mouth this time, my lips pressing against his balls and his body.

"Get off," he finally demanded. "I'm not going to cum. God, Emily. You're really bad at that, you know?"

I felt tears welling in my eyes. I wasn't drunk, just slightly buzzed, but it was enough to loosen my tongue. "It's not like you've ever made me cum," I shot back. "I got you to last time. You've had too much to drink."

"No." Brian was belligerent. "You're the worst I've ever had. Hands-down."

Now the tears were spilling down my cheeks. "Fuck you, Brian."

"Shut up, Emily," he spat in return. "None of my friends even know why I date you. You're not even attractive; your tits are half-grown and you won't let me fuck you. You're a dog. Woof, woof."

Brian stood up, shucked his pants on and buckled his belt. "It's over, you dumb bitch," he said. I stared at him in shock. He smiled at me nastily and swooped up my panties from the floor where they lay.

"Those are mine!" I protested.

"Not anymore," he smirked. "Souvenir."

I realized what this meant -- even though I hadn't fucked him, he was going to use my underwear as proof that he had. Even though he'd graduated two years before, Brian still was friends with pretty much all the guys in my high school.

But I was so frustrated and angry that I didn't really care. I was wearing a skirt, and it was loose, but knee-length, so I figured I could walk home without flashing anybody. The cold air sobered me up and caused my nipples to strain uncomfortably against my sheer bra and baby tee.

I made it back and banged in without announcing myself. Normally, if I left at night, James and I had an arrangement -- I would let him know when I came back, by knocking or ringing the doorbell in a specific pattern, and then take my sweet time opening up. Or, lately, texting him. Occasionally, James had lady friends, and we had come to a mutual agreement not to mention it to Dad.

There was a funny smell in the air. "James?" I called, shakily.

I heard a muffled curse and made my way to the guest room. He'd been smoking something out of his bong, resting on the bedside table -- I'd never smoked pot, but I knew what a bong looked like -- and there was a porno playing on his laptop. He'd clearly quickly pulled his boxers and shorts up, but he was shirtless. I felt the familiar stirring of interest I always felt when I saw James without a shirt on.

"Whoa -- sorry!" I exclaimed, starting to turn around and head out, but in the split-second before I did, James had caught the agony on my face. I felt horrible that I'd walked in on him, and I was turned on, but more than anything, I felt overwhelming sadness when I saw the girls on the screen. I was achingly jealous.

Not of their bodies or that they were showing them or anything. I'm not a Puritan. I wasn't sure anyone would ever want me like that, would ever think I was sexy like that.

I know, it sounds ridiculous. It was; it was teenage girl drama.

But at the same time, Brian was very popular -- and a bit of a bully. If he spread it around that I was frigid and undateable, none of the guys at my school wouldn't bother with me. At least not in public.

"Hey," James said as I fled out the door, and the softness in his voice was probably the only thing that could have made me stop.

A ball of angst and pain was rioting in my stomach. I did stop, hunching my shoulders, hiccuping.

He laid two gentle hands on my shoulders, stroking them softly. I slowly relaxed at the familiar sensations -- James gave me backrubs every once in a while, only when I begged him. In retrospect, he must have found those isolated incidents as erotic as I did.

But I could also feel his still-erect cock through his boxers and shorts every so often, brushing against my skirt. And I wasn't wearing panties. I felt a shiver run down my spine that had nothing to do with my issues. I even started to think that maybe I should secretly thank Brian for his unintentional facilitation of this covert -- and arousing -- proximity between us.

"What happened, Em?" James coaxed.

"B-Brian b-broke up with me," I finally managed to choke.

He laughed a little and turned me around, putting his fingers under my chin. "Is that all? That guy was a douchebag. You should be celebrating, not bawling."

"Yes, that's all," I told him, but evaded his eyes.

James knew I was lying. He knew me well.

He seemed to think about something, then made a decision. "Come in," he invited, tapping his computer and pausing the video. Ironically, on a woman whose mouth was full of a man's cock. He blushed and shut the laptop abruptly.

I did, taking a seat on the bed where he patted beside him.

"Were you drinking tonight?" James asked me. I didn't hide things like that from him.

I shrugged. "Kinda. I had a beer when I first got there. Brian was trashed, but I don't like getting drunk very much."

"Ever smoked hash?" he asked.

My eyes widened. "No," I said, smiling a little. We lived in Colorado, and even though my dad grumbled good-naturedly about James's habit on occasion, he didn't seem to mind my half-brother bringing his stash with him when he was on Emily Duty.

"I'll show you," he offered, smiling back. "But for God's sake, don't tell Dad!"

"I won't," I assured him.

He had a whole attachment for his bong, a nail with a globe and a torch. It was all very intricate, but I didn't have to do anything but inhale. He packed me two dabs of some strong honey oil, and I was completely blazed.

It felt good; I was very relaxed. I started giggling, and James giggled with me.

We talked for a while in his bedroom about nothing, but then my eyes caught the laptop again, and even though it was closed now, a throb of pain went through me.

"Seriously, Emily, what's wrong?" James asked, noticing.

I might as well tell him, I thought. He might even have some advice.

"Brian said some things when we broke up that are kinda bothering me," I admitted.

"Like what?" James probed.

I wasn't sure how much detail I wanted to go into -- but it was James. I knew he fucked girls; I'd heard them moaning downstairs once or twice. "He said I suck at giving head." I was surprised how hard it was to say it. My voice caught in my throat and I felt the tears prickling again.

"Oh, Em-" James started, but I held a hand up and he closed his mouth, waiting for me to finish.

"He said I was a dog, that I was ugly and no one would want to date me. And he took my panties away. By Monday, everyone in school is going to be convinced I fucked him, and I didn't."

I thought I saw James flick his eyes down to my crotch and back up when I told him what had happened to my panties. We sat there, silent, for a while before I sighed.

"Maybe he's right. I'm probably never going to have another boyfriend in high school. And by the time I get to college, I won't know how to do anything."

"That's not true, Emily," James told me firmly. "You're a very attractive girl."

"You have to say that," I replied glumly. "And you're biased."

"I'm not," he insisted. "You're adorable."

"'Adorable' hasn't gotten me very far," I muttered. There was another long silence. "Plus, I still suck at giving head."

"I doubt that," he answered quickly.

"You wouldn't know. You can't know until you've tried it," I sighed, almost defeated.

Wait a minute. In my hash-addled brain, that sounded like a plausible scheme.

Plus, I think the smoking had done something to my libido. Every time I remembered I was sitting on a bed with James, with no panties on, and he knew I wasn't wearing any, I felt a tingle. And it was difficult to forget it the way he kept shifting and eyeing me uncomfortably. His cock was growing once more against the cloth of his boxers and shorts, I could see it.

"James," I ventured, and he shook his head, laughing breathlessly.

"No, Em. That's not on the table."

"Why not?" This sounded unreasonable to my current frame of mind.

"It's wrong, for a start. You're my sister."

"Half-sister," I jumped in quickly. "We weren't really raised together; you went to college when I was in pre-school. It's not weird. Most people could understand that."

"You're eighteen," he said. "I'm thirty-one."

"That means you know what good head feels like," I riposted. "You could really help me."

James shook his head. I wasn't sure how much hash he had smoked before I arrived, but I could tell my logic was starting to make sense to him. "Em, I really think it would be better if you found someone your own age, someone at school."

"I can't." My voice was growing desperate. "He has my panties. He's going to tell everyone that he fucked me and that I'm a skank and horrible in bed and no one will date me!" I slid off his bed onto my knees and turned around to kneel in front of him. I parted my knees automatically and watched his gaze widen; I met it and didn't bother to screen my eyes for anything, trying to put all of the anxiety and desire and uncertainty and pleading I felt into them.

"Please," I begged, unashamedly. "Please, James, please show me how to do this. I won't ask for anything else, it's just this one time, one lesson. I'll be okay with being a virgin as long as I know how to give head. And once I've got the basics down, I can practice on other stuff. Please?"

I had been babbling, but I saw how my words affected him, and I reached out one hand, tentatively. He didn't help me, but he didn't pull away, either. He didn't try to stop me. I unbuttoned his shorts clumsily, not familiar with undressing others yet, and pulled his shorts down. He lifted his hips and allowed me to draw them down his legs and off, but he didn't assist in any other way. I focused my gaze on his dick, which was flipped up on his stomach, rock hard, leaking pre-cum into the band of his boxers. I traced its outline with one hand, fascinated by it, and was just about to slip my fingers into his waistband and pull off his boxers when he caught my wrist in his hand.

He was breathing heavily, and there was a look in his eyes I'd never seen before. I stared up, transfixed.

"If we do this," he said, "I want you to learn from it. I want this to be an experience you will never forget, and hopefully never regret. Is that what you're committing to?"

I felt that this was important, but I couldn't imagine what he meant. "Um, sure," I said.

He smiled. "Stand up."

He was asking me to stop already, and that made me feel a little nervous again -- was he not enjoying what I'd been doing to him? -- but his voice had held nothing but approval, and ... it was James. I trusted him completely.

So I stood up, wobbling a little bit on my high heels.

"Take off your shirt," he said, in the same almost-conversational tone.

I flushed. "Wh-what?" I stammered.

"I'm going to ask you again, Emily, because I'm not really willing to take 'um, sure' for an answer when you're asking me to do something that Dad would absolutely murder me for. Like, no shit, murder me. If I'm going to teach you how to suck cock, we're going to do it my way. Can you commit to that?"

I swallowed, but met his gaze and nodded. "Yes."

"All right. Take off your shirt."

I toyed with the hem of my tee, suddenly super self-conscious, not sure if he wanted me to just, like, take it off normally, or try to be sexy with it. I wasn't sure what that would look like. And I was nervous; I didn't want James to back out now that we'd reached an agreement. "I'm sorry," I told him. "I want to, but I can't. I'm overthinking it. I think it's the hash."

"Come here," he beckoned, inviting me to stand between his legs while he sat on the bed. I took a half step forward. "Would you like me to help?"

I nodded, caught myself, gave a half-smile. "Yes," I said.

He removed my top by skimming his hands up my stomach and ribcage, grazing over my aching nipples and breasts still encased in my sheer bra.

He sat back for a minute and savored the look of me, his pupils dilated wide. "Emily," he said. "Brian is a fucking moron. You are gorgeous. You are so hot."

I blushed and looked down, then felt his fingers on my chin again, drawing it up. "Can you take your bra off for me now?" he coaxed. "Or do you want me to help?"

"Help?" was all I said, and he reached around and quickly unfastened my bra strap. I hadn't even learned to do it that fast yet! "Slip one strap down your arm," he instructed.

I did, squirming, feeling wetter than I knew I was capable of getting.

"Now slip your left arm out of the other strap."

I complied, holding the cups to my chest -- more or less futilely; my bra didn't cover much.

"Give it to me," he said. I obeyed him, my tits jiggling as I did, nipples hard as pebbles, and I saw him tense with want for me.

That helped convince me he was telling the truth, and he wasn't finished.

"Reach up and pinch your nipples," was his next request. I felt my cheeks flaming again, but my head was still swimmy from the hash, and I did it.

His breathing had quickened and hardened. "Now unzip your skirt and step out of it."

I hesitated, and it was as if he read my mind. "I'm not going to fuck you, Emily, I promise. I'm not even going to try. There's a reason for this. Trust me."

I did trust him. I unzipped my skirt and stepped out of it, feeling ashamed of my long, coltish legs, and slightly awkward in my heels.

James sensed it. He didn't seem to agree. He drank me in with his eyes and sighed happily.

"Fucking gorgeous," he repeated, vehemently. "Get back on your knees."

I did, feeling the hard, heavy pit of hurt that had gathered in my stomach since Brian hurled those words at me starting to dissolve. I'd never seen a cock as hard as James's cock was now.

"Do what you were just doing."

I smiled, reached out and began again to gently explore the outline of him through his boxers. He was the second male I'd ever touched, but the first real man; Brian hadn't had anything like this length or girth.

He was definitely harder than before; I could feel his heartbeat throbbing through his raging erection. He laughed.

"Lesson number one," he said. "Put on a bit of a show beforehand. Personally, I feel, the dirtier the better. Getting the mood going before you even do anything with your mouth is half the battle. Take as many of your clothes off as you reasonably can before you kneel down." His voice grew softer. "Maybe even beg a little bit, like you did before."

I shot a startled glance at him. "D-do you want me to do that?"

He laughed again. "It's OK, Em, you already did." His voice was rich with desire.

I started to feel nervous -- what if I was truly terrible at this? How embarrassing would that be? He was bigger than anything I'd practiced on.

But I didn't want to stop. I was so wet I could feel dampness coating the insides of my thighs, and James didn't try to hide his gaze as he watched my pussy twitch. He smiled.

"Now you can pull my boxers down," he told me.

I did, and his cock sprang out, almost slapping me in the mouth. I grabbed it as it grazed my lips and felt awkward again. "What should I do?" I asked him.

"Why don't you just do what you normally do first?" he suggested. "Then we'll know for sure if Brian was right or not."

That made sense. I started by gently licking his cock all over, then began to work my lips over his length. Now that he was in my mouth, it wasn't so bad, but I wasn't sure I could get him all the way to the back of my throat.

"Wrap your hand around the base of my dick," he instructed. "You can even use both hands. That way, you can still stimulate the whole length, unless you want to work on your gag reflex so you can deep-throat."

I nodded, my mouth full of his cock, wrapping my right hand around its base and massaging it as I bobbed up and down.