The Best Christmas Present Ever

I found myself with my mouth open, just staring at the half-naked woman lying down in front of me. Jess had her bedside lamp on, which provided dim illumination for the room, enough for me to still clearly see her body. I had a growing hard-on from admiring that pert ass and those taut thighs. I just hoped Jess couldn't see it with the low lighting.

"Zach?"

"Uh, yeah. What's the favor?"

"My bum is feeling so sore. The ice helps a little, but I think what I really need is a massage for it. And I can't exactly reach my butt very well, so I need you to do it."

My heart fluttered. This was unexpected, and very, very welcome.

"Uh, okay. If you feel like it will help."

She turned her head back to look at me. "Thanks Zach. You're seriously the best brother ever."

I gulped and walked over to Jess' double bed. I climbed up and got on my knees. I moved so that I was kneeling between her spread legs.

"Just work your hands in. It'll make me feel so much better," Jess said, drawing out the "so."

I couldn't imagine how I had managed to get myself into this scenario. I had fantasized about being right here between her legs for the past month. But now that even a portion of that had become a reality, I was nervous and almost frozen.

I reached my hands our and gingery placed one on each butt cheek.

Jess gave a quiet "mm-hmm" of approval. I had to take a few deep breaths to calm my nerves. I was literally groping my sister's ass right now. It was crazy.

I didn't really ever give massages, but I was determined to do my best for Jess. I pressed my palms down into her skin, pushing hard against her tight muscles. I ran my hands over her butt, squeezing her skin and kneading it with my palms and fingertips.

Jess gave a low moan. Clearly I was doing something right. But it sounded almost like a moan of pleasure. Like she was turned on.

I worked my fingers along the small of her back, over her tailbone. It was probably hurting the most there, I thought, based on my past knowledge.

"Oh, yeah, that's the spot," Jess said.

I stayed where I was, massaging her ass at the very top of her crack.

"You really know what you're doing, don't you?" she asked.

"Uh, not really," I truthfully responded.

"I think you're lying. You're telling me you've never squeezed a girl's butt before?"

"Not exactly," I chuckled, trying my best to not sound awkward or nervous.

Jess turned her head back to look at me. My hands never stopped working over her butt. "Oh come on. Seriously? You're so handsome and smart and charming. And you had a girlfriend for a while. How are the girls not draping over you?"

"Um, I mean, I guess I've had some opportunities. But I wasn't really looking for a while, and I don't just want to hook up with any random girl."

Jess turned her head back, resting on the soft pillows. "Yeah, I guess that makes sense. Still, there's no way you're going to stay a virgin for much longer. When you get to colleges, every girl on campus will be lining up to suck your dick."

"Oh, sure," I jokingly responded.

"I mean it. Especially if you give them all he treatment you're giving me."

Sweat dripped from my brow. It really felt like Jess was flirting with me. But maybe I was just reading too much into it, trying to create something from nothing. I had to find out for sure. This would be a defining moment.

In the heat of the moment, my curiosity and horniness won out over my better judgement. I decided to make a move.

"Hey, uh, your panties are kind of making it difficult for me to really give you a great massage," I started.

"Well, you can take them off if you want to. If you think it'll be easier," Jess said, cutting in before I could finish.

My heart was racing. She was the one who suggested going further. Oh god, could she really be having the same thoughts about me as I was about her? The talk about my virginity, the flirting, now this?

I wasn't one to look a gift horse in the ass, so I didn't delay. My fingers curled into the soft waistband. I gently pulled the fabric down Jess' body. She lifted her hips up to make it easier, giving me an even better view of her ass.

I shifted my body and slid the panties off Jess' legs. Sadly the shadows of the room and lack of light obscured the real jackpot between her legs, but her naked ass was now fully in my vision.

Jess lay on the bed, waiting for me to return to my duties. She wasn't looking at me.

Taking the opportunity, I brought her panties up to my face. I could faintly smell an odd odor, one I only ever recall smelling before in the bathroom Jess and I shared growing up. My eyes scanned the fabric, and could faintly make out a small patch of wetness on the crotch.

I may have been naive, but I wasn't that thick. Jess was legitimately turned on by me. She was wet.

"Are you going to get back to the massage or are you just enraptured by my butt?" Jess playfully asked. She lifted her hips and gave her ass a shake for me. I nearly came in my pants. God, I was so fucking hard right now.

Not wanting to waste any more time, I discreetly slipped Jess' panties into a pocket on my shorts. I would certainly be using these later.

I moved back between her legs and began running my hands over her firm butt once again. Jess let out the occasional sigh or moan, but those were the only disturbances to the uninterrupted silence which covered the room for the next ten or so minutes.

I was trying not to be super obvious, but whenever I could, I took the opportunity to spread Jess' cheeks a little bit. It gave me just a fleeting glance of that tight, puckered rosebud she was hiding. I had never watched her do anal. I wonder if Jess had ever done it. That might be a little too forward of a question to ask though.

It seemed like Jess was very gradually spreading her legs further open for me. I could just barely make out the folds of her pussy in the dim light now. Was she giving me the go signal? I was struck by nervousness, and wasn't trying anything more.

Time almost got away from me, but I returned to reality when I glanced at the digital clock by Jess bedside. It was almost midnight. I had been in her room for over an hour.

Realizing the time made me also realize how heavy my eyelids were. I needed to go to sleep. Jess seemed like she was almost dozing off.

"Um, hey, are you feeling better?" I quietly asked as I got off her bed.

"Yeah," Jess answered. "Although I do wish you'd gone a little bit deeper."

This particular entendre went over my head at the time. "Oh, well, I did my best."

Jess gave a slight chuckle, and rolled over onto her side. Se was facing me, but she kept her top leg draped over her bottom, again obscuring that sweet box. "You were wonderful, Zach."

"Thanks. Well, I'm glad to hear you're doing okay. I'm heading off to bed."

Jess sighed. I couldn't tell if it was an exasperated one or one of contentment. "Good night. I love you."

"I love you too, more than you will ever know," I responded as I left her room. It was something Mom said to us both all the time as kids, but seemed particularly apt in this situation.

"Oh, I think I have a pretty good idea. See you tomorrow."

I rushed back to my room and closed the door.

God, how could I be so stupid! Jess was clearly coming onto me. It was all that I wanted in the world right now. How could I have frozen? I swore to myself that if the situation ever presented itself again, I was going to act.

I climbed into bed and took Jess' panties out. The aroma of her sweet juices filled my nostrils. Well, at the very least, I established that Jess was in the same boat as me. Now we both just had to navigate to the same shore.

***

Tomorrow came, and to my dismay, nothing more happened. Jess seemed a little distant, and I was worried that I had put her off by not fully responding to her advances.

Her butt was apparently feeling much better though, and she espoused the greatness of my massage services to Mom.

"Well, maybe you'll have to give me one too!" Mom said to me.

I doubted she wanted the same kind of massage I had given to Jess.

The day of Christmas Eve arrived, and we were busy the whole day putting the tree up (as a stout follower of holiday traditions, Dad refused to put the tree up earlier) and preparing a large meal for dinner. We always opened presents and celebrated on Christmas Eve, and overeating on glazed ham, mashed potatoes, and an assortment of other foods was part of that as well.

Dinner ended, and we opened the few presents under the tree. Dad had gotten a new pair of golf clubs, which he was super stoked about. Mom got a coupon for a free spa day (so she could get a massage from someone with more experience than me) and some new cooking appliances. Jess and I both got the customary socks and pajamas. She got her next semester's books paid for, and I got a big Playstation gift card. It wasn't a huge Christmas, but we spent it together as a family, and that was what's important.

The night was winding down. Mom and Dad were tipsy on champagne and cognac, respectively, while all of us had partaken in some spiked eggnog for some extra Christmas buzz.

We were all gathered in the living room. Jess stood up and set the bottle of champagne she had been unceremoniously drinking from down.

"Alright, so I do have a bit of an announcement to make. I've been wanting to say it for a while, but haven't worked up the courage, and I wanted all of you guys here."

Uh oh. I think I knew where this was going.

"So I figured this would be best if you heard it from me, and not having to find out on your own." Mom and Dad looked understandably puzzled. "So college is obviously very tough with books and tuition and groceries and rent now that I'm living off campus. I really do appreciate how much you have helped me out."

Jess paused and took a deep breath. "With that said, I know we aren't exactly Rockefellers, so I wanted to try to reduce some of the stress for you by getting a job. It would allow me to pay my own rent, so one less thing you would be paying for me."

Dad chimed in. "Well that's great honey! I'm glad to see you being proactive and already thinking of this stuff while you're still in school."

"Aren't you too busy for a full-time job?" Mom asked.

"Well, not really. This job isn't full-time, it only requires a little bit of time and effort. And it pays really well."

"Even better. Why didn't you tell us before?" Dad asked. "What are you doing?"

"That's the kicker. Guys, please, please, don't freak out at me, but... I started doing porn."

The cat was officially out of the bag. This wasn't my concern, so I sat back and let the three of them talk.

"You what!?" Mom screamed as she shot out of her chair. "Jess, how could you? We raised you better than being a common whore!"

"Mom, please."

"Please what? Accept that you've officially ruined your career? What happens when you're out of school applying for jobs? This is permanent!"

"Honey, just calm down," Dad said, trying to comfort her. I wasn't particularly surprised that he was more cool with it than Mom. He was less uptight than her. Plus, it was his money, so he probably didn't care too much how Jess was helping him save it.

"Calm down? Calm down? Our daughter is whoring herself out on camera! Like any common slut!"

Tears started to form in Jess' eyes. "Listen, Mom, this was the best way to help you guys out. I have enough time to focus fully on school and still provide a living for myself."

"With your body? God, Jessica, we gave you everything! A nice home, a good childhood. We raised you right. We even paid for you to go to college! And this is how you give back? Oh God, what will happen when everyone else finds out? We're going to be ruined."

The argument waged on, and got even nastier. Mom basically disowned Jess and she was firing back about Mom's prudishness and inability to think about anyone besides herself. Dad was trying his best to defuse the situation, but it wasn't working. Eventually Mom stormed off to her bedroom, slamming the door hard enough to make the walls shake a little.

"Listen, Jess, I fully support you in your decisions," Dad said. "I hope you know that. I will always love you."

He opened his arms, and Jess gave him a tearful hug. "Thanks, Dad. I love you too."

"It'll be okay. I'll talk to your mother tomorrow after she's had a night to sleep on it. You know how she can get when she's confronted with something unexpected. Everything will be fine."

Jess wiped away her runny nose. "Thanks. I sure hope so."

Dad left the living room and joined Mom in the bedroom.

Jess turned and collapsed down on the couch. She looked over at me.

"Why the fuck were you so quiet?"

"It wasn't my fight. I didn't want to get in the way."

"Well, how do you feel?" Her tears had stopped, and she looked better now.

"About what?"

"Me doing porn, dumbass."

"I'm with Dad. I support your decision."

"Well, you don't seem very rattled or surprised." A look of realization crossed her face. "You already knew, didn't you?"

I paused, not sure how best to answer the question. "Uh, well... yeah. I've known for the past little while."

"How long?"

"Um... Six weeks."

"Why didn't you tell me?" Her tone wasn't angry or accusatory. More curious.

"I figured you'd let us know when you were ready. I didn't want to intrude on your right to tell us. Just didn't realize it'd be on Christmas."

"Yeah, I might have fucked that one up."

"Well, maybe."

We sat in silence as Jess took a long swig from the champagne bottle. It couldn't be all that bubbly by now.

"So did you jerk off to me?"

I looked right at her. She was dead serious.

"Yes."

I answered without hesitation. This wasn't the time to be coy.

"Which video?" she asked.

"You were on your knees blowing some dude before he came on your face."

"Well, that doesn't narrow it down much," she joked.

Her words hung in the air for a few seconds. "Listen, Zach. I've already fucked up Christmas for everybody, and I didn't contribute to your gift this year." Jess got up off the couch and walked over to me. "I feel like I need to give back. So how would you like it if my gift to you this year was taking your virginity?"

I gulped, my Adam's apple bobbing. My heart was racing, pumping blood rapidly down to my hardening cock.

"Uh-"

"Shhh," she interrupted. "Don't say anything. I already know you want to." Jess dropped down to her knees in front of my chair. "Stand up."

I obeyed immediately.

My eyes looked down at Jess. She was wearing a red wool turtleneck, with green Christmas-themed pajamas that had little snowmen on them. No makeup, her hair wasn't styled, she had just been crying, and she was pretty drunk. And somehow, this was the most beautiful Jess had ever looked to me.

Her hands moved to my own pajama pants. She grabbed them and pulled them down. I remained frozen, like a statue, captivated by my sister.

Something else made of rock popped free. My fully erect cock stood at attention, pointing right at Jess. She gasped a little when she saw it, admiring the more than seven inch-long shaft.

Jess reached out with a hand and gently wrapped her fingers around my shaft. My cock surged against the touch. It was the first hand besides my own that had ever touched my cock.

She slowly moved her hand further down my shaft and then back. Her hand gently stroked my shaft, bringing me to a fully erect state. My dick throbbed with each movement of her hand.

"You know Mom and Dad could walk out at any moment and catch us, right?" I asked.

Jess got up off her knees and stood in front of me, maintaining the slow stroking of her hand on my rod. She was about half a foot shorter than me, so she had to look up.

"That's part of the fun, isn't it?"

Jess put her free hand on the back of my neck and pulled me in for a kiss. Our lips met, and I felt like I could melt right into her. Her lips were so soft and warm. It was an extremely romantic and sensual kiss. Neither of us were being aggressive or hurrying. It was pure, unadulterated, taboo lust.

She pulled away after a few seconds.

"I'm sure you'll like what else my mouth can do," she seductively purred.

I stripped off my shirt, leaving me fully naked. It was rather odd, seeing as how she was still completely clothed.

Jess dropped back down to her knees. Her hand stopped its constant motion, and steadied the base of my dick. Jess shifted her head closer to it. My eyes were glued to her.

She opened her mouth, craned her neck forward, and took my cock into her mouth.

It rested on her tongue for a split second, before she pushed forward and took a few inches into her mouth. Jess wrapped her lips around my cock and created a perfect seal with her mouth. I was in heaven. Her mouth felt so warm and amazing.

Her tongue flicked out over the engorged head of my cock, making me shudder. She did it again, and began licking long strokes with her tongue over my sensitive helmet. Her hand started up again as well, stroking the bottom half of my shaft up to where her lips were locked.

Jess drew in her cheeks, putting additional pressure on my cock. She really knew what she was doing. I briefly tore my eyes away from her and looked to our parent's bedroom door down the hallway off the room we were in. I had to admit, the bonus factor of how vulnerable we were was making me even harder.

Jess' mouth began to move on my cock. She pulled back, leaving just the head in her mouth. Her tongue tickled the tip of my cock before she plunged back in. As she did so, her tongue trailed along the underside of my shaft, making my cock throb and pulse.

She continued the movement with her head, cresting a steady bobbing motion that I had seen many times before from her in porn. Her hand jerked at the same speed her mouth was moving, ensuring that my whole shaft was being pleasured equally.

I felt pre-cum leaking out of my dick. I couldn't last much longer, not with Jess' mouth working its oh-so-wonderful magic.

She seemed to sense that too. Her eyes were beaming, looking right up at me. It felt oddly romantic that we maintained eye contact the entire time her head was bobbing up and down my cock.

Jess removed her hand from the base of my cock, freeing her mouth up to take more of me in. With each subsequent bob of her head, she was taking more and more of me in her mouth. I knew she could deepthroat a lot, and I wondered how far she would go.

That answer wouldn't escape me for long. I felt the tip of my cock brushing against the back of her throat. Jess had evidently mastered her gag reflex, because she soldiered on without hesitation. She had most of my cock already in her mouth. She made one last push and buried her nose in my torso. My cock was pushing against her throat, but she had swallowed the entire length.

Saliva had begun to drip onto her chin from her now-opened mouth. I shuddered, knowing I was about to blow. Jess' tongue flicked out and tickled my balls. I was so close...

To my dismay, Jess pulled away off my cock. She took a few short breaths to regain her composure. Other than the saliva on her chin and flushed cheeks, she certainly didn't look like she had just been blowing someone.

"Not yet," she said, responding to the look in my eyes. "I'm having too much fun," she continued with a giggle.

Jess returned back to her original position. Her mouth sealed around my shaft and her tongue worked its way over my head. Her lips ran back and forth over the first few inches of my rod, while one hand jerked on the rest of my now-slippery length.

More pre-cum spilled onto her tongue. She licked it up eagerly. Her pace began to quicken. I was about to cum again. Jess kept going for half a minute, slowly going faster with each bob of her head.