Sibling Love

I gasped when his fingers suddenly reached virgin ground. Probing, flicking across my clit. Still he didn't penetrate me, even with his fingers, and I wondered what he was waiting for. Groaning, I closed my eyes firmly shut and balled my fists into the sheets. "Jasmine..." the warning note carried in his voice, and I wondered what I had done to displease him. Shit, I thought. My eyes. "Good girl." James mused. "Right, I wasn't even going to consider this, until I took your virginity...but you need to learn that you being sassy just isn't going to wash with me. I'm going to cum in your ass. Now its going to hurt, but, if you listen to me, I will make this as pleasurable for you as it is going to be for me."

I frowned. My head wasn't processing what James had actually said. "Why would you cumming on my ass hurt James? I don't understand, does your sperm sting or something?"

He laughed, a real deep chuckle that sent pulses racing to my pussy. James leaned down and kissed my furrowed brow. "No Jasmine. My cum does not sting. And you misheard me. I'm not cumming on your ass... I'm cumming IN your ass. Inside it. Deep deep inside it."

He let me digest what he was saying, and when my brain finally registered what he was actually saying and suggesting, I flinched and started to protest. James placed his finger against my mouth, and I hushed instantly, afraid of the outcome if I misbehaved. I must have paled, as once again he kissed and nipped at my earlobe, "Trust me Sis. I promise you it'll only hurt more if you actively fight it. The more relaxed you are, the better it will be for both of us."

I swallowed hard and licked my lips nervously. "Okay." I said, barely even a whisper. But he heard me.

James smiled, kissed me hard on the lips and moved out of view. I felt myself tense up and tried to stop. Luckily his hands were on me instantly, and it went a long way to relax me.

"I'm going to use my tongue Jasmine, see if that will get you to calm down a little."

I sighed, happily, safe in the knowledge that he was about to do something I had already experienced with him during the course of the evening.

James, however, threw me another curve ball that not only shocked me, it blew my mind.

His hands slid down my hips, kneading and stroking. Until he finally settled on a spot he was happy with, and he pulled my ass cheeks apart. I gasped at the sudden cold on my backside, but still not actually realising what James had got planned.

I felt him, breathing against my asshole, and I tried to keep relaxed. His arm was across the bottom of my back, and it was comforting. It was also there for a specific reason. James being James, knew that the second his tongue touched me, I would almost bolt off the bed. Because it wasn't my clit he was intending on tonguing. It was my ass. My fucking ass.

I shrieked and snapped my legs shut. James was patient. He continued to rub my backside, gently at first, then a little more forcefully, easing my cheeks open once again. "Shall we try that again little Sis?" He asked.

I tried to get my breathing under control, and when he had soothed me, I gave a tiny, squeaked "Yes."

I felt him settle back down into position, and the whole process began again. Each time his tongue pressed against my tight little rosebud, and each time I let him go a little bit further, until eventually he was stroking and probing my hole with his tongue.

He spent what seemed like forever lavishing attention on me, completely relaxing me till I was moaning and writhing beneath his arms in a very different manner. His arm slipped under me, and gently touched against my clit and he groaned when he found how wet I actually was. There was a movement behind me, and I was shocked when his tongue was replaced with, what I soon realised, was a finger.

James didn't insert it inside me, just lay there gently putting pressure on my tightest of holes.

He rubbed the bottom of my back in small circles, and I felt something cold, dribbling down between my butt cheeks.

"What's that...?"I whispered, not sure if I was frightened of the answer.

"Lube sweetie. Lubrication. Its going to stop this from hurting so much. I'm going to use my fingers first, to stretch you out a little bit. And we'll see how you do with that first okay?"

"Okay James," I held my breath, and a small swat on my ass jolted me out of my own mind.

"Breathe Jasmine. You need to relax, so just breathe deeply for me." I nodded, but was certain he could feel I had started taking deep breaths. I felt his finger slide gently inside me, and was shocked at the sensation. It didn't hurt much at all, just made me feel full. That and very very naughty.

James slowly worked one, then two fingers into me and I couldn't help moaning into the sheets. He chuckled behind me and it made me relax even further, helped a lot by the fact I could tell he was enjoying himself immensely.

I lay, writhing under his arm, enjoying the sensations he was making me feel. And for the first time since he mentioned it, I was actually looking forward to his attempt at fucking my ass.

I groaned loudly when I felt his fingers leave my butt, and braced myself for the pain that I knew was about to come.

His weight took my air away momentarily. I just hadn't been expecting it. James landed a kiss on the back of my neck and I shivered. "You ready baby Sis?" I tensed ever so slightly when I felt the head of his cock nudging my tight rosebud. "I'll go really slow, but like I said earlier, the more you relax and open up for me, the easier it's going to be. I'm going to try a couple of things to help, but this is down to you now."

He slipped his hand between our bodies, and lined up the huge head of his cock. His teeth grazed my shoulder, and his other hand slid down the front of my body. James found my clit, and started dancing circles around it, completely successful in his aim, I was now fully focussed on his fingers, and not what his penis was doing.

He must have read the subtle change in my breathing and tension, as James decided at that moment to drive himself home, without much prior warning. I gasped, and cried out loudly feeling myself stretch around him. It was painful, yes. But actually not unbearably so. I found that with his fingers on my clit I could enjoy the low burn of the stretch.

"Is...is it in James?" I grunted, and flinched at a tender spot. He nuzzled into my cheek, and moved towards my neck, sighing contently.

"Oh god baby yes. Yes it's in." He kissed me again and I felt his cock twitch inside me. "You did so well..." James brushed the hair out of my face and landed another kiss on my brow. I could hear the strain in his voice, desperately trying to stay as still for me as he could, to allow me time to get used to my first ever anal intrusion.

I could feel my whole body ripple in waves under James. His arm holding me steady, whilst his other hand stoked and caressed. His teeth nipped at my shoulder, the back of my neck and my ear. The whole while he kept his bottom half statue still. Helping me adjust.

I was almost positive he could feel my body loosen under his weight, around his cock. I moaned into the bed, eager for him to move. I wriggled my bum, just a fraction. Letting him know I was ready. James read my cue easily. He kissed my ear and whispered things I really needed to hear.

James braced himself, and pulled out of me, almost to the tip. In one fell swoop he drove his throbbing cock deep into my ass. I cried out, loud and wanton. Pain hit me, as he started his infinitely slow torturous fuck, stealing my anal cherry from me with such ease.

My head was filled with pain messages. But holy hell, they were a good sort of pain. They mingled with the most amazing sensations I had ever felt. The tight burn, the friction. I could feel every inch of him, I couldn't stop the vocal cacophony that spilled from my mouth. Every time he thrust back inside me I cried out loudly, unable to keep even a modicum of my inhibitions. My dissonance seemed to spur him on. The louder I became, the harder he fucked me. The pain was exquisite. It blended in with pleasure, and I could feel my orgasm building. It surreptitiously rode up inside me, and my whole body flushed pink.

James was now fucking me with wild abandon. No longer having the ability to be concerned for my pain level. He was in such a trance of feelings and sensations, his fingers briefly stopped circling my clit.

"James!!" I cried out, unable to hold back any longer. He slowed briefly, concern evident, but unable to completely stop. I was glad he didn't. "James, I need to orgasm. I really, really need to."

He moaned against my neck and sped up once again. The feeling of tension rose again within me, and I knew my orgasm was only seconds away, especially when his fingers started up again.

"Cum for me Jas. I want to feel your ass constrict around my cock when you do. I want to take your anal cherry and have you cum all around me because of that. Fucking hell Sis, I want you so badly."

His motions became fast and jerky, and I felt him swell ever so slightly inside me. I rode wave after wave as my orgasm hit. Rolling over me, shooting down my limbs, making me shudder. My breathing hitched in my throat, and as it hit, I screamed. All the pain was out of the window. It didn't matter any more. There was no pain. Just the two of us.

James yelled out as his orgasm started to hit. Furiously fucking me. He flexed, kissed my neck and cried out into my ear.

"I'm going to cum inside your ass baby."

"Oh god yes, please." I begged.

"You are so hot. You ass is so incredibly tight and I am going to spurt my load deep inside you sis..."

James thrust hard, all pretence of gentleness disappeared, and he cried out his release into my ear. Both catching our breath, we lay in silence for a few moments, and I moaned as he pulled out of me. Extremely gentle once again, he kissed my neck with such tenderness. His weight shifted off me, and he lay on his side next to me, tracing patterns across my back.

James looked at me, pupils huge and dilated, a huge stupid grin on his face.

"You are fucking amazing baby Sis. I've never...that...just, yeah..." He sighed and kissed my forehead. "I can't believe we just did that! I've always wanted to, but...and the fact I took your anal cherry before your pussy is unbelievable."

I flushed under his gaze, and wriggled a little. I grimaced when I felt some of his cum leaking out of my ass and dribble down between my pussy lips. It was totally gross, but so hot.

James' hand was stroking my cheek, running his fingers through my hair. I sighed contently and closed my eyes, happy with his tender touch.

"Do you think I'm ready?" I asked. He knew right away what I was inquiring about.

"Only you can make that call." James smiled at me gently.

"I'm ready...I know I am. I want you inside me. Please?"

He nodded. "If you are sure?" It was my turn to nod and he smiled with such tenderness it made my heart flutter a little bit. His hand snaked down and pushed my legs open ever so slightly. "I need to open you up a little with my fingers first. It will make it a little easier for me to...well, you know, like I did for your ass."

This was it, I thought. "Okay, I want you to...but just go slowly. Please?"

"I will go slowly, trust me Sis."

"I trust you, I really do. You are my big brother for goodees sake. I trust no one else more. Doesn't stop me being scared though. What are you going to do to me?" He grinned secretively at me.

"Tell me if you want me to stop, okay?"

I bit my lip, thinking for a second and nodded. James slid his hand further down my front, over my breast, down my stomach till he reached the lips of my pussy. Parting them slightly, his fingers brushed my clit and I cried out loudly, his mouth was on mine in an instant silencing my moans. I thought he was going to bring me to orgasm again, but I was confused when his fingers dipped lower, away from my clit, and I groaned in frustration.

He chuckled and nibbled on my lip. "Easy there little Sis..." James admonished.

I could feel his fingers at the entrance to my pussy, and I jerked away a little out of instinct. He was patient though, and continued gently yet firmly, slowly sliding his fingers over my labia. I squeaked when James brushed past my clitoris again, and my back arched upwards when his fingers entered me.

The kisses he was peppering on my neck combined with his fingers penetrating me made my moans louder than before. He paused briefly.

"I'll stop if you need me to okay?"

I moaned again. "No! No, don't...stop...Jesus Christ, do not fucking stop!"

I felt James slide another finger inside me, and the feeling of being stretched was phenomenal.

"How many fingers do you have inside me James?! It feels truly amazing...like nothing I had ever felt before...Oh god, and when you kiss my neck." I groaned his name out loud again and started to writhe underneath him.

He chuckled and dropped a kiss on my neck. "Just the two for now Jas...I'm glad you like that. I can actually feel you grinding against my hand, you are such a naughty girl! And fucking hell, you are absolutely soaking wet!"

I flushed bright red and let out a little squeal when I felt James' thumb brush against my ever sensitive clit.

"Just two? But I feel so full. I can feel the wetness on the inside of my thighs! How...why does it...oh my god James, I can't handle this...It's happening again. Fuck. I can feel it building up and up...Is that normal??? This many times? Should I..."

I felt him smile against my shoulder as he kissed my collar bone. "Mmm yes, Yes Jasmine. Cum for me hard."

James' hand movements seemed to speed up with every twitch and moan that he wrenched out of me. I couldn't stop it, I didn't want to.

"Mmmm Oh my god James!" I was screaming out his name, his fingers deep inside me. I was certain he could feel my pussy clenching and contracting around his digits. My legs stiffened, I was moaning loudly now, grateful our parents weren't in the house. I could feel the explosion, shuddering under him. My juices and cum splashing out all over his hand.

God, I can't breathe...I literally could not catch my breath.

"You make me so damn wet James... how do you do that to me? All you had to do was touch me down there and, well, bam..."

He laughed at the bemused look on my face. "It's one of the most sensitive parts of your body, and you did good Jasmine. You came...like, a lot! It was amazing!" James pulled his hand from between my legs, and licked one of his fingers. I was shocked, and baffled frowning slightly.

"Wanna see what you taste like?" he asked.

"Really? Oh god...erm, well. I've tasted you, so sure why not?" He smiled and held a finger to my mouth. Before he had chance to stuff it in I spoke. "Did I really do good?" I asked blushing yet again.

"You did really good!" He said kissing me on the end of my nose. "Anyway, watch out for this...the taste is slightly addictive."

James touched one of his fingers to my mouth, and lightly brushed my lips. I opened up, letting him enter. Reaching up, I grasped the hand he was offering, I could feel straight away how slick it was. I wondered if that was all me. Slowly I took one of his fingers, then two, into my mouth and sucked them in deep. Flicking my tongue around tasting myself, smirking as his eyes rolled back a little and he moaned.

"I taste different to you James." I noted. "You tasted salty and biter. I taste...Musky. Its good!" I was surprised. Pleasantly so. I looked up at him coyly. "Do you...Do you think I'm ready now?"

"It's your choice Jasmine honey. I'm not going to push you though."

I nodded. "I'm ready, I know I am...I want you inside me. If it feels anything like your fingers...then...well, just wow! But you'll have to go slow."

James laughed. "If you thought my fingers were good then...well, prepare to have your mind blown!"

He pushed my bra strap off my shoulder and dropped a kiss where it had previously been. "Let's get this off you shall we?" He asked.

When he had removed my bra, he tugged me towards him closer and my breasts squished up against his naked chest. I sighed content.

"God Sis, you are so fucking sexy."

"I'm glad you think so." I giggled.

James kissed me lightly on my mouth, my body pressed tightly up against him. I could feel his hard cock pressing against my soft belly. His tongue slipped past my lips and massaged my own, making me relax...open up for him. James pushed me onto my back, leaning over me. I could feel my whole body trembling.

"You sure you're ready for this? I can feel you shaking honey. You nervous?"

"Very." I nodded. "I'm actually terrified big brother! But I don't want you to stop." I smiled up at him. "Please James. Don't stop. Whatever you do, don't stop."

He nodded. "At any time if it's too much for you, you have to promise to tell me, okay?"

"Okay." I whispered. "I will...I promise. Please James, show me what I've been missing all this time."

He kissed me gently and slowly slid his hard thick cock between my legs, and guided it towards my soaking wet labia. I gasped, trying desperately to stay as still as I could under his weight. I could feel James' cock nudging at the entrance to my pussy.

"I'm ready...I'm yours!" I gasped out.

Ever so slowly he started to edge into my aching pussy, a short sharp gasp escaping his mouth as he did so. My breath caught in my throat, as I felt him inch into me. James held still...really still. He was letting me become accustomed to the feeling once again I realised. The stretch. I winced a little at the pain, the burn. He reminded me to breathe and I took a deep, shaky breath in.

He was looking down on me, tenderness written all over his face. "Brace yourself..." He whispered.

Even I knew what was coming next. Well, I think I did anyway. James kissed me gently, asked if I was okay to continue...if I was sure. It was literally only the tip of his penis situated inside me, he was waiting patiently for me to give the go ahead. I gasped as he pulled back a little, the sudden emptiness was so stark. I can do this I tell myself...I know I can. I just have to be brave.

I give James a slight nod and feel him grip my chin, pulling my face round to look into his eyes. I search them for any sign of insecurity, and find none, which makes me feel much better. I nod again, this time a bit more forcefully.

"You are going to break my hymen aren't you? Is it going to hut really badly?" I ask in a small voice.

"Yes I am." He nods. "I honestly don't know how much it is going to hurt, But it shouldn't hurt anymore than me fucking your ass." I flushed and James smiled fondly down on me, his eyes locking with mine. "I'll try not to hurt you too much though, I promise." James slowly started to push his cock inside me, feeling, more than hearing me take a huge deep breath. "God Jas, you are so fucking wet!" He grunted.

I could feel him push deeper and deeper into me. Then he suddenly stopped, hitting resistance. I knew it was coming and I took a deep breath, holding it in, nervous for what seemed the hundredth time that evening. James grasped my face again, making me look him in the eyes. Those grey eyes that are so like my own we could be twins. There is no denying whatsoever we are siblings. I brace myself, and cannot tear my gaze away from his.

He kissed me lightly on the lips and an adoring smile lit up his face, relaxing me further.

When he could feel I had finally let go a little, and I'm no longer tense underneath him, he pulled out a little. Without warning he gave a short, sharp thrust forwards, burying himself right up to the hilt.

I could feel the skin tearing, the sharp clarity of searing pain shooting through me. I cry out loudly. It hurts. Holy shit it hurts. Then there is still the feeling of James deep inside me though, and that overrides any pain I am feeling.