My Dinner with Andre's Little Sis

I feel like a fucking creep-- there's no other way to say it. I know she's 18, and I know I'm 30. He's my best friend, and it's fucked up that she's his little sister. But I can't deny that she might be the best thing to ever happen to me.

Let me start over, with a little history for perspective.

I never knew Hope growing up. That's Hope with a capital H; I actually had a pretty spoiled childhood. I grew up with Hope's brother Andre. We were, and still are, best friends.

I don't really remember much about her the few times I was over at his place. She would have been really young. We would usually hang at my house, since I had a bigger, nicer home. Andre lived in a trailer park. He was poor, and I didn't really realize our class gap until I was a bit older.

I didn't even think of it at the time. I just thought he just liked my place better. In reality, he wanted to escape from his claustrophobic mobile home as often as possible.

Andre was a sweet kid growing up. He was funny, and we shared similar tastes, like sci-fi movies and cartoons that we liked.

As we grew, our tastes changed. Andre and I drifted for a bit at the tail end of high school. But we both realized that friends with history were stronger than new friendships. We went to college together, got jobs at the same marketing firm, and ending up being roommates for almost a decade.

We had girlfriends, usually at different times than the other. Somehow, one of us was always single.

Last year, Andre's parents were killed in a car accident, back in his hometown. It hit Andre very hard. Worse, his sister Hope was home alone when the cops told her the tragic news.

She wasn't even out of high school yet. Long story short, she had to finish her final year of high school in a new city, rooming with her only living relative in the state: Andre.

And, by default, me.

We shared a two bedroom condo in the city, and when Hope suddenly became homeless, I offered my room up, and moved to the couch.

It wasn't ideal for anyone, as it was a small apartment for two, let alone three. Their parents' home didn't sell for much, as they owed quite a bit on their mortgage still. It was a recent upgrade for them. Andre and Hope got a medium chunk of change, but it didn't make up for the sudden loss of their parents.

We were already getting an okay rent rate for staying so long in one place, so moving out wasn't really fiscally viable.

We just had to stay the course for a while. Hope went to classes during the day while Andre and I were at work.

We'd come home to Hope, who often made dinner for us, seeing as she beat us home by a couple hours.

So, months after they became orphans, is arouns where things started to go wrong for me. Or right.

At first, I didn't think much of Hope's presence.

When she first moved in, I realized I remembered nothing of her growing up. She would have been a scrappy little kid. Now she was 18, and kind of a curvier girl. Not fat, just baby-fat. She had a little upturned nose and doe eyes. She was blonde, like Andre.

She was shy, emotional, and kept to herself for the first few months. I didn't give her too much attention-- I didn't want her to feel like I was her brother's creepy friend. I never hit on her, or talked with her when Andre wasn't near.

That seemed to work okay for a bit.

But I started looking at her differently. At first, I told myself she was family, and mentally off-limits. But after a while she got comfortable around me. I thought, at first, that this was the catalyst.

One night, when Andre had gone to bed early, she appeared next to me, by the couch. I was still up, watching TV. She was wearing pajama bottoms and a baggy shirt.

Hope sat next to me on the couch.

"Hey," she said, not looking at me.

"Evening," I said, doing my usual, by saying weirdly gentlemen-like things to avoid coming across like a perv. Still, I always felt like one whenever I talked to her.

"What's on," she said, barely a question.

"Nothing," I said, staring at some rerun I didn't care about.

"I'm sorry about your room...sorry I stole it. I never said that before." She quickly glanced at me, then back to the TV.

I turned on the brother's friend voice, trying to seem easy going and aloof.

"No worries. Both of you had the worst thing ever happen. I'm just sleeping on a couch."

"Yeah," she said softly. "But still, I just never said thanks."

"No worries, Hope."

"You say that a lot," she said, this time looking at me.

I looked at her. Her face was illuminated by the TV. She was a very cute girl. For years I've tried to avoid viewing younger women the way I looked at Hope now. She was 12 years younger than me, but she was very attractive.

She smiled, and looked back at the TV. If I wasn't crazy, I would have guessed she found me attractive too.

She watched TV with me in silence for an hour before going to bed.

"Night," was all she said as she slipped into my old room.

Days passed without much noteworthy differences in Hope's personality. She was a little chatty with Andre but didn't say much to me.

I started staying up later, and I could barely admit to myself that it was because I wanted Hope to hang out with me on my couch.

Another night almost passed by without her company. I had turned the TV off, and started to get comfy when I heard her door open.

Maybe she was getting some water.

"Hey," she whispered, "I must have just missed TV time."

I could barely see her in the dark. "Hey," I whispered back. "Um. Yeah, well..."

I didn't know what to say.

"Can I sit with you?" She spoke softly, likely not wanting to wake her brother.

She didn't give me time to answer. She came around to the end of the couch where my feet were. She has shorts on that came up mid thigh, and a tighter shirt than I was used to seeing. She lifted my comforter and crawled under.

She kept her distance, but we were sharing a blanket.

"Do you want your room back?" Tonight she was dimly illuminated by streetlights from outside.

"No," I said slowly, also with a hushed voice. God forbid Andre walked out here. "It's all good. No--"

"--Worries," she said, interrupting my predictable phrase. "I know. But I mean it. I could stay out here instead. Maybe I should sleep on the couch for once."

I just stared at her, confused. Did she mean now? With me?

"It's fine, Hope. I'll survive. It's comfy."

She nestled under the covers a little more. Her bare feet touched mine. She didn't move them.

"It is cozy," she said, leaning back, her feet sliding past mine, resting against my thigh. "But no privacy."

I couldn't reciprocate any of her advances, if that's what they were. Sure, she might be flirting, but it was my place to stop it. To say something.

"Hope..." I started to say. Before I could finish my sentence, she sat up, and walked past me. I wasn't on her way back to bed. But still, she almost bumped against me as she walked past. I was face-level with her waist. I still sneaked a glance at her crotch. She just smirked as she walked by.

She said nothing, and disappeared into her room.

I laid awake for an hour trying to make sense of things.

My sleeps were terrible for too long. I slept in, forgetting to set my alarm. Andre tried to wake me but I must have fallen back asleep. I woke up an hour late, feeling awful. We didn't carpool, so he must have assumed I'd be at work not long after.

I ended up calling in sick, taking the morning to nap for a while. I never took days off, so I didn't feel guilty. When I got up, I had assumed Hope was at school. It was Friday, after all.

I was wrong. When I walked naked out of the bathroom, Hope emerged from her room wearing PJ's and a bra.

I stopped dead in my tracks, taking a moment too long to cover myself with my hands.

"Jesus," she said bluntly, "nice dick."

I stared at her, mostly exposed and in a sort of shock.

"Sorry!" I said, backing up to the couch and covering myself with the blanket.

She was smiling, but not laughing. Damn, she had a nice rack. Not huge, but still sexy. I tried to look away but she had seen that I had noticed her cleavage.

"Hey," she said, coming over, "my bad. You thought I was at school."

She knew I was still here? Why was she only wearing a bra?

"I didn't know you were here," I said, blushing. "I slept in, took the day off."

"Me too." she said, sitting down next to me. What the hell was her deal?

"But...I'm not tired. Or sick. I just..." She looked at me with no specific expression for a bit.

She quickly leaned in and kissed me. I pulled back.

"Hope," I said, flabbergasted, "what are you--"

"Don't pretend," she said. "I know you like me. Or at least you check me out."

I found it hard to lie to her.

"You're...attractive. But you're young, and Andre is--"

"--Your best friend. I know. I'm the little sister who usurped your room. And we barely talk. But I..."

I watched her bite her lower lip. Christ her skin looked smooth.

"I like you. I just thought I'd see if you like me too. I don't care that you're my brother's age. I'm not a kid, so you're not like a...you know...creeper, for liking me back."

I was lost in the moment. She wouldn't take her eyes off me. I wasn't even clear on my emotions. Sure, she was a guilty pleasure to behold: young, blonde, and curvy. And she seemed...horny.

But I barely knew her.

"Andre would--" I didn't get far.

"He doesn't have to know." She kept her eyes locked on mine. In that moment, my feelings were clear. I wanted to fuck my best friend's little sister.

She made the move for me, again. She leaned forward and kissed me harder this time. She tasted like bubblegum. She took off her bra.

Then, surprisingly, she got up and walked into her room.

The sight of her naked tits was fresh in my mind. For a chubbier girl they were smaller, but quite perky.

"You coming?" I heard her call.

So, I thought, I'm throwing out all my morals. Very good.

I got up, naked and hard as hell. I walked into her room.

I wasn't a pro, but I had enough sex to know what I was doing. I just didn't know what she knew.

She was naked on her bed; Her PJ's lay on the floor.

"I'm not a virgin," she said. Her legs were together but I noticed that she was shaved. Maybe waxed.

"So, you can fuck me hard."

I approached. I was already committed to this, I didn't hesitate.

I crawled up onto my old bed. I started kissing my way up her legs.

"I don't like the soft stuff as much," she said. "I like it rough. You can choke me."

Hell's bells.

I wasn't used to this kind of attitude. I spread her legs, and put my fingers to her wet pussy. Damn, every part of her body felt nubile, and soft. She was very wet, and I sampled her pussy with my fingers. I pushed in, watching her expression. It said, hurry up and fuck me already.

I kept telling myself I was about to fuck an 18 year old and it was both turning me on like crazy and weirding me out just as much.

"Put it in me," she begged.

I positioned myself, and pushed my way in. She was tight, and she whimpered a little as I thrust inside. She grabbed my ass with both hands, urging my to fuck her immediately.

I started to think of Andre, but I had to stop. Feeling guilty right now was a waste of my time. And a total mood killer.

I started thrusting, slowly at first because she felt so tight.

"Harder," she said, her blue eyes daring me to do my worst.

"Yeah?" I said, getting in sync with her specific vibe. I was new to this, to be so forward. With zero foreplay. "Like this?"

I increased my speed, as well as my impact. I was trying my best to be what she needed.

"Yes," she moaned. "Keep going."

I did as asked. I put my hands on her left tit, and gently massaged it.

"Pinch it," she said, in between her breathy moans. "Hard as you want."

I pinched her hardening nipple between my fingers and squeezed. Her jaw opened more, and she threw her head back.

"Choke me," she said. I had never done that. I was hesitant. I placed my hand on her soft neck, and squeezed firmly.

"Harder," she gasped, clearly needing more pressure. I did the most I felt comfortable with. "Mmm," she managed.

Her face was getting flushed so I relaxed my grip. It wasn't for me. But it did the trick for Hope, it seemed.

"Hit me," she said. Suddenly, I wasn't enjoying myself like I was at the start.

"No," I said. "You're beautiful, I'm not hitting you."

She looked up at me. "Fine. Just keep going. Harder."

Anybody who's ever been told to "go harder" when they were already at their limit can perhaps feel my pain.

"I can't," I said, instead of trying. I was actually exhausted.

"Come on," she said, leaning back again, "don't be a pussy."

It pissed me off, but I ignored her and kept going.

"I'm gonna come," she said, "don't stop, don't stop, don't--"

Hope clutched me tightly and moaned loudly and with a little exaggeration into the empty apartment.

I wasn't close to finishing, as I had started out too rough, and Hope's bedroom talk didn't do it for me so much.

After her climax was dwindling, I slowed, and removed myself. That's when Hope started to cry.

I'd never had a girl cry after sex, and I gotta say, I was not prepared. None of the past five minutes was what I had expected from Hope, but to watch her transition from ecstasy to a teary state was a little jarring.

"Hey," I said, laying beside her with my hand on her face, "What's wrong?"

I would have guessed it was about her parents. I would have been wrong.

"Fuck," she sobbed, looking away, "I'm a fucking mess, huh. Aw..." Her words turned to louder sobs. I did what seemed right, and held her gently, stroking her shoulder.

She spoke in between her tears.

"I think...I fucked that up..." she said, trying to calm herself.

"I think I...freaked you out..." She tried to turn away but I tilted her cheek back to me.

"Hope, it's okay," I said. I forgot we were naked. I just felt like I was consoling someone I cared about.

"No," she said, starting to sound a little more like herself.

"I came on strong, and I talked you into sex. Then I'm telling you what to do, and calling you names...I don't even know WHAT the fuck I like. I just..."

She tried to catch her breath. I waited patiently.

"I've only been with a couple guys. Just this year. The first guy was a total noob and it was barely sex. The second was into rough sex, and choking, but he was...I dunno, too into it, but I still, and I..."

"Hope, it's okay." I tried to sound compassionate.

"Sounds like you had a guy who didn't treat you right. Maybe even abusive. You thought that's what you had to be. But clearly it's not. If it's what you like, that's okay. But I think it probably isn't, not all of it. I didn't want to hurt you."

She looked at me, with teary blue eyes.

"You're such a nice guy. You must think I'm fucking crazy."

"No," I said, "I really don't."

I held her in my arms for a while until she had fully calmed down.

"Thank you," she said. "I'm sorry for all that. I understand if you...need space from me after this. I wish I just told you how I feel instead of acting like some slut who--"

"Hope, please." I looked her in her eyes. "I've been looking at you in a way I shouldn't have, before you came on to me. I barely know you, and you're so beautiful that it's intimidating.

"I don't feel bad about any of this. Other than having to keep this a secret from Andre, which...I think, is obviously mandatory, for now."

"Yeah," she agreed, sniffling a little.

"I think you just need someone that can treat you with respect, and will take care of you instead of taking advantage.

"I don't know if I'm the right guy for that, but I would love to try to be."

I wasn't sure if my intentions outweighed my actions. I just asked out an 18 year old, in the name of "being a good dude." What was wrong with me?

"So," she said, "we could maybe...start over?"

"I'd like that, yeah," I said, and hugged her close.

I took a walk after that. I figured it would be good to get some air, and use the excuse to get some groceries nearby as well.

I also needed a pause from Hope so I could regroup, analyze my thought processes in case I had lost my mind. But other than betraying my best friend by sleeping with his kid sister, I was just a guy in a hopefully legal relationship with a girl. Simple.

When I came back, we talked on the patio. It was a nice day, and we were seated in comfy patio chairs while we snacked on some fruit I bought.

"So, I just realized you didn't finish," she said, smiling. "Sorry. The crying probably didn't help."

I laughed. "I stopped before that. I was sorta off, and I usually don't go that hard."

We both smiled.

"That was amazing, though." She said it like it was a vivid flashback. "I was mean, but you were really good."

"It was good," I said, "I just think next time we can take our time. Unless you don't like--"

"Just ignore what I said. I don't know what I like, really. Maybe you can show me some basics. More sensual. I just skipped all that. I think my ex ruined it for me." She looked off into the cityscape.

"I've just always been more...giving," I said, trying not to appear like a white knight. "Sometimes to a fault. I had an ex say I was too romantic. She wanted me to be an asshole. I couldn't force it. Didn't mean I was never an asshole, but not the way she needed."

"How many girls have you been with?" She ate a strawberry, slowly.

I didn't really want to tell her, but she asked.

"Like...nine? Ten?"

"That sounds like a normal amount," she said. That's like one a year for ten years."

"It wasn't evenly paced, maybe a few more in the beginning but less lately."

"How many girlfriends did you have?" She just seemed interested, not judgmental.

"Maybe five? Only two lasted more than a few years. My last ended early this year. Usually Andre is dating while I'm single, and vice versa. But we've both been single for almost a year now. Until...now."

I looked at her. What a fucking cutie. Why did she have to be his sister? How the hell could I pull this off?

"Do you actually want to date me?" She tilted her head at me. "I know we've done...all that...already, but...If you don't feel--"

"Listen, Hope," I said, "I don't know how I can make this work, living here, but I know I want to try. I want to get to know you better, and start slow. Like you said, start over. But I really like you. I can't believe you actually LIKE me. I'm the worst!"

"No," she said, laughing, "You're a sweet guy. I can't believe I didn't scare you off."

"Where would I go?"

We chatted until Andre was coming home. I tidied up a bit, and Hope pulled out some homework.

Andre wouldn't be too weirded out by us alone for two hours, max. But if he knew about our morning together?

I don't even want to know how he would react...

"Hey, man," Andre said, coming through the door, "feeling okay?"

"Better," I said. "Bad insomnia lately. I napped all day."

"Right on. Didn't miss much," he said, "Henry said some dumb shit and almost got let go, but that's a weekly thing with him."

I nodded, trying not to think of having sex with Hope.

She came around the corner, wearing a hoodie and jeans. "Hey bro, how was work?"

"Fine," he said, "School went okay?"

"Yup," she lied. He didn't push further. Excellent.

"So," he said, looking at me, "You guys have fun without me?"

I stared blankly.

"The last couple hours? Did you even talk once?" He laughed. When asked about Hope's presence, I always downplayed my annoyance at having to sleep on the couch. And he knew that we didn't talk, ever. Until lately that was.

"Yeah," she said, "he told me all about his childhood, growing up, every time you guys talked about girls, yada yada..." She laughed, but winked at me when Andre wasn't looking.