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.
