Helping My Brother's Friend

A cold shiver ran through my body as I cupped my breasts in my hand and took a deep breath to ground myself. I raised my knee and placed my foot on the edge of the couch to his right, spread myself apart for him to look at. I could feel that I was soaking wet from his earlier ministrations, and the air in the room felt extra cold against my throbbing labia.

I stood like that for a second, waiting for him to do something, anything, and I wondered if I'd have to give him directions again. However, he brought his hand up to my foot and began slowly tracing the length of my leg. His palm followed the curve of my calf, my knee, and then my thigh before he used his middle finger to trace the crease of my groin. So close to my pussy. I shivered as goosebumps broke out over my skin, and he looked up at me, our eyes meeting briefly.

I saw the question there, and I nodded.

He stroked his middle finger gently down my slit, lightly tracing my labia. I took a deep breath, trying to ignore the aching pleasure that simple touch had generated in my lower half. He went back in, using his middle finger to trace from my vulva down over my clit, spreading my labia and stroking slightly deeper in my slit. This time, when his finger pulled away, a strand of wetness stuck to it, and he looked at it marvelingly. The strand broke and hung from my pussy, glistening in the light of the living room.

"Shit," he hissed. "You're so fucking wet." He looked back up at me, his face pleading. "Can I - Can I taste you?"

I blinked, unprepared for the question and his sudden bravery. I hadn't expected this to go past me showing him my body. Hell, I hadn't expected to let him touch me. Regardless, the anticipation of his tongue on my clit had me shaking, and I gave him another small nod. He inched to the edge of the couch and leaned forward as both of his hands crawled up my backside and cupped my butt. Before I knew what he was doing, he'd used his grip on me to pull me forward towards his mouth.

I'd expected him to go straight for it, but instead he laid his cheek on my vulva and dipped his nose into the neatly trimmed strip of hair lounging above my clit. And I felt him inhale, deeply, and growl another animalistic noise that was dripping with want and lust. It was one of the hottest sounds I'd ever heard, of pure desperation, of near insanity. I couldn't believe that someone was reacting this way to my body. It was so fucking hot.

After another deep sniff, his tongue finally lashed out, a quick and tentative lick over my labia. Using the tip of his tongue, he spread me apart and pressed directly against my clit. I let out a sigh of pleasure - and honestly relief, because virgin or not, here was a man that knew what a clit actually was. He licked around it, gently at first, and I felt his light touch trembling on my buttcheeks. Slowly, he began to use more fervor, kneading my backside harder and harder, pushing me more and more into his face until he was buried in my slit and dining hungrily on my pussy. I was whimpering, my legs shaking, and I reached forward and fisted my hands into his soft black curls, pushing him deeper into my pussy as I began to thrust into his face.

"Oh shit, Jason, oh shit," I moaned, and the pleasure building as he went faster and harder. I wasn't sure how he was breathing down there, but I didn't have time to ponder. All of a sudden, my legs began to give out, but he caught me as I half slumped over him. He looked up at me excitedly, a tingle in his eyes as he grabbed a nipple in mouth - his lips and chin glistening from my wedness.

He began sucking eagerly as he tried to pull me back into him, but I pushed him away.

That look of sheer disappointment and sadness flashed across his face again before he bit his lip and leaned back. "I'm so sorry, I don't know what came over me -" he started.

"Let's go to my room, Jason," I said at the same time. I paused and smiled at his words, my stomach fluttering at his kindness and consideration. I reached out a hand and he linked his fingers with mine without hesitation. I began leading him towards the entrance to the living room, sashaying my hips and hoping his eyes were admiring my ass. I was about to have so much fun with him...

"What is that?" he said, pointing to the teardrop-shaped toy on the right. I picked it up and offered it to him.

"It's called a Womanizer," I explained. I was sitting naked next to him on my bed. I'd never been a shy person, so I didn't mind being exposed even though he was fully clothed. Anyways, some of the urgency of our downstairs endeveaors had eased as the reality of what we were doing had set in, so I'd decided to switch gears in his "confidence training" by showing him my collection of sex toys. I was sure that would be useful for him in the future, with other women.

"How does it work?"

"It's a clitoral stimulator, but it like...doesn't actually touch the clit. I'm honestly not exactly sure how it works." I gave out a nervous laugh. "Here, turn it on and put it on your finger," I offered, taking it from him, turning the machine on and then grabbing his thumb. I pressed the hole against the pad of his finger as the toy vibrated loudly.

"Wow, that feels weird," he said with wonder.

"Would you wanna try it on me?" I asked him, holding my breath.

"I would love to," he said. But then he hesitated. "I'm not sure what to do, though."

"Don't worry, I'll walk you through it," I told him, thinking he looked really cute as he blushed. A tingle of excitement fluttered through my body. It was so nice being able to guide him and tell him exactly what I wanted.

I laid back down on the bed and eased my hips to the edge. I didn't have to guide him as he crouched down in front of me, and I gently put my feet on his shoulder as he stared straight into my pussy.

"Your v-vagina is so pretty," he commented as I felt around the bedsheets for where I'd left the Womanizer. I didn't think I had it in me, but I felt a little blush creep up my chest. I'd always been insecure about my large labia, and it definitely eased some anxiety I hadn't realized I'd been feeling.

"Thanks, Jason." I took a deep breath and then rached a hand down between my legs. Using my fingers, I spread apart my hot, swollen lips. With my other hand, I brought the Womanizer to my clit and slid it up and down the top of my slit to get it into position. When it finally landed on the highly sensitive nub, my whole body convulsed with pleasure, and I closed my eyes and curled my toes into his shoulders. "Here, like this. If you hold it here," I told him and I felt him grab the machine from my fingers. My hands relaxed on either side of my vulva and I pulled back, helping to give him as much access as possible. "And if you want to - to make it real good," I hissed, trying to hold back from bucking again, "You can use your tongue to lick at my pussy hole while you do it. That would make me come really fast," I explained, distracted. I hoped what I was saying was making sense.

It did, because while he was holding the womanizer of my clit, I felt his hot, wet tongue lapping up at the wetness that had accumulated at my slit again.

He groaned loudly. "Fuck, Janine, you taste so fucking good," he spoke against my pussy, the deep vibrations from his voice adding even more sensation. I only whimpered as he dove his tongue deeper and deeper inside me. Meanwhile, the Womanizer throbbed over my clit, bringing wave after wave of pleasure. The feeling intensified quickly, and I brought my hands up to pinch my nipples as Jason used his free hand to pin my hips down to the mattress.

"Make little circles with the-" My breath hitched. "Oh god, yes," I moaned as my whole pussy felt like it was on fire. "I'm cumming," I told him, bearing down and clenching my muscles. I let out a low, sustained groan, and he lapped faster around my spasming pussy lips. My groan turned into a whimper as I felt liquid trickling out of me. It had been so long since I'd squirted, but I immediately recognized the feeling. A brief moment of panic hit me and I wondered if I should hold back - I didn't wanna make a mess, didn't wanna scare him, didn't want to be gross.

But all of a sudden, I heard him moan, and I decided to not give a shit. "Fuck, fuck, fuck, fuck," I chanted and sobbed at the same time as wave after wave of pleasure ran through me. The liquid trickled out of me fast, hotter, and I felt him press his whole face into it, drinking straight from the source. I forgot where I was, who I was with as my body shattered around his hands and mouth, nothing existing except for the intense, explosive heat at my core.

And what felt like an eternity later, my brain finally swooped back down into my body and I pulled away from him quickly, breathless. Pleasure could only go on for so long before it became overwhelming. A sheen of sweat was covering my forehead after the intense full body shudders that had overtaken me.

"Shit, shit, shit," I said again, and in the back of my mind, I registered that he'd turned off the toy and sank next to me on the bed to hold me.

"Are you okay?" he whispered into my ear, his hand draped across my stomach. He sounded worried, so I turned to look at him in amazement.

"Am I okay?" I repeated incredulously, my eyes meeting his. He was holding his breath, concerned, almost scared. "Jason, I just came harder than I ever have with anyone else," I told him honestly. "Like, thank you so much. That was incredible."

I heard him let out a relieved laugh, and felt the bed shift as he relaxed next to me. "You're a good teacher," he said, and I could hear the smile in his voice.

I turned towards him, adjusting the hand he'd draped over me as I put one on his chest. I felt his heart beating; his pulse was fast. "What are you thinking?" I whispered next to his face. His lips were a couple of inches away from mine. He looked down at me as he pulled me into him.

"I'm thinking I'm so fucking lucky to be able to do this with you. I'm thinking I'm so grateful to you for letting me touch you and pleasure your amazing body. And..." He paused, then let out a chuckle. "I'm thinking that my cock feels like it's going to explode in my pants. I've never been this turned on in my life."

I raised my eyebrows. "Never?"

"No. You're fucking incredible. Your pussy...your smile...your tits..." His hand slid to my front, and he ran his thumb over the tip of my nipple again. It hardened immediately, and my body shuddered at the pleasure. It felt so good to be in his arms, under his adoring gaze, his worshiping hands.

My breath had finally calmed, along with my body. And I knew for sure that I didn't want this to be over. I bit my lip to stop the smile from spreading on my face; I was so excited to see his face and how he'd react to this. I pulled out from under him, ignoring his small noise of protest, and I grabbed his hand to pull him into standing position. Again, he obeyed, standing up next to me, over a foot taller than me. God, he was so much bigger than me. I felt so petite and feminine next to him.

Taking his hand, I led him to the lazyboy in the corner of my room. Before he was able to sit down, my fingers went to the button of his jeans.

He wrapped his hand around mine, freezing.

I looked up at him, confused, but he refused to meet my gaze. "What's wrong?"

There was no response for a moment as he examined the pattern on my carpet. Then, "I'm nervous."

I nodded, understanding. "Trust me," I said, as I began to move my hands again, but his grip only tightened. I paused again, wondering if I should give up. I didn't want to cross any boundaries and make him uncomfortable, especially after he had been so good to me. "Do you wanna sit down together?" I asked him, and he laid back in the chair. "Do you mind if I sit in your lap?"

He gave a short shake of his head, and I climbed into his arms. My body fit perfectly into his warm and soft embrace. He wrapped his hands around me and pulled me to him. I rested my head on his chest, and he laid his head on top of mine. It was a very intimate embrace, but I'd always been a cuddler and I knew that all of this must have been hitting him really intensely. I remembered when I'd lost my virginity; even though the guy hadn't been that close to me, I'd still felt very vulnerable. I wanted to be sensitive to Jason and his desires, insecurities, and fears.

"I'm sorry," he started again, and I opened my mouth to fight him about the apologizing, but he continued before I could get a word out. "I'm honestly really insecure about my penis."

The comments about his sorries immediately disappeared from my brain, and I nodded slowly, taking his words in. "I hear you, and I think I get it. I'm insecure about some things with my body as well. I don't want to push you into anything before you feel ready. I just wanted to give you pleasure like you gave me pleasure," I explained, running my hand across his broad chest. I felt a shiver run through him at my words.

"You're perfect," he interjected. "What do you have to be insecure about?"

I shrugged, biting my lip. "Everyone has things they're insecure about, Jason. Some people just hide it better than others. Me? I hate my pussy lips. I think they're enormous, and they get in the way when I wear jeggings, and-"

"That's bullshit. I love your pussy lips. They're beautiful...and delicious. And they feel so good against my tongue."

I blushed and nestled further into his chest, closing my eyes. "I appreciate you saying that. I really do. It's one of those things though that I have to work on accepting about myself, you know? It doesn't matter who says what to me, because I should be able to love myself without caring about what other people think."

"Mmh," he said, thinking. He rubbed his cheek against the top of my head, tenderly. "I know it's not a competition, but if you feel this way about your body, how are the rest of us mortals supposed to have any confidence?"

I let out a little laugh, hearing the compliment in his words juxtaposed with his feelings of insecurity. "You think you're ugly but you're not. Literally everyone has insecurities. Your confidence is your biggest barrier, Jason."

He shrugged. "I guess. I don't know. I just...I'm really scared."

"Oh what?" I asked gently, peering up at his face.

He looked down at me briefly, but still couldn't hold my gaze. "Like...so much. You looking at my little dick and laughing. You being instantly turned off by my body and not wanting to do anything anymore. You secretly thinking I'm disgusting the entire time we're doing stuff. You going and telling everyone including your brother what a tiny, disgusting penis I have. To name a few." He let out a bitter chuckle.

"I get that. I've definitely felt some of those fears before. I think part of getting more experience is knowing that everyone has imperfections that they're ashamed about. Learning to love ourselves is a life-long process. And it comes down to who you choose to share that with and whether or not they are people worthy of you trusting them with your body. Like, I made that mistake already once, when I was sixteen. My boyfriend took pictures of my body and then showed them to his friends, talking about my beef curtains and stuff. Honestly, I thought I was going to die. It was so embarrassing."

I felt Jason tense under me. "I had no idea. Fuck. I'm so sorry that happened to you, Janine. God, that fucking pisses me off that some assholes would do that to you," he said. "That's so messed up."

I shrugged. "It was a really shitty experience. But I think it also helped me face some truths early on about insecurities and trusting people. Like, I know you're a good person. In all the time that I've known you, I've never heard you say anything mean about anyone else. I trust you, and I wanted to help you. I hope that maybe, given our past, you feel safe with me, too. And honestly, I think you're really cute and...you turned me on so much with your touch. I just wanted to return the favor," I said, trailing off.

He inhaled sharply, and finally our eyes met. "That's so hot. God, you're so hot. I do, I want it so bad, I just - can we go slow? I'm scared," he said.

I nodded, excited at the go ahead. "You can stop me at any point," I told him, shifting in his arms so that I was straddling him. His hands rested on my hips, gliding up and down my thighs.

"Shit, you're beautiful," he said for the millionth time, and I laughed as his eyes raked over me.

"Can I kiss you?" I asked him, and when he nodded, I learned forward until our lips met. His mouth was warm and wet and he didn't try to suck my stomach out of my mouth immediately like most guys did. We kissed gently, our lips sliding against each other, taking in the sensation of the new contact as our breath intermingled. Lips pressed firmly against mine, and then his hands wrapped around my back and pulled me down onto him. I moaned and gyrated my hips against his lap, sure I was leaving a wet spot on the front of his pants. His hands reached back to my ass, gripping it on either side tightly and using his strength to push me further down into crotch. I opened my mouth into our kiss and our tongues met sweetly, a quick flick, sending another tingle of pleasure throughout my core.

My hands slowly slid down his chest and over his stomach. I gave him plenty of time to pull back or change his mind. My fingers reached the button of his jeans again, this time he didn't stop me, just slowed down and returned to light kissing. I undid the button and then gently pulled down the zipper. I gently reached under the hemline of his pants, sliding my hand down past his curls until my fingers found his shaft. He was hot and hard as a rock. I pumped my hand up and down his length and he pulled his mouth away from me, leaning his head back into the couch and moaning loudly. "Holy fuck," he said as his breath hitched and his eyes rolled back. I smiled again, enjoying the complete submission.

I slid my body down his while I kept my hand on his cock. Finally, I was leaning in front of him, and I paused to pull down his pants and underwear. He lifted his hips, helping me pull them down while he looked straight into my eyes. His gaze was a whole nother level of intense as I grabbed the base of his cock in one hand and leaned forward until my mouth was right next to the small slit at the top of his mushroom head.

Maintaining eye contact, I reached out my tongue and slowly licked that hole, once, twice, going farther down his frenulum, licking the underside of the cockhead, running my tongue all over his tip before finally putting my lips against him and slowly taking him into my mouth. He wasn't big, maybe four inches, the perfect size for giving blowjobs. I took the entirety of his cock into my mouth, swallowing him until my nose pressed against his pelvis and his whole body shivered.

I pulled my mouth back all the way to the tip before I went back down, and all of a sudden, I heard him say, "Oh shit, I'm cum-" His body shuddered under my mouth, pumping his length into me. I hadn't been expecting him to come so soon, let alone at the back of my throat, so I struggled a little to swallow the massive load as my head bobbed over him.

"Shit, Janine, oh fuck, that feels so good, please don't stop, I'm coming so hard," he said as he continued to fuck my throat. I managed to swallow the spurts of jizz he sent down my throat, barely getting a taste of sweet cum as he fisted his hands in my hair and pushed my head down onto his cock. I pushed back against him, surprised again and not ready for the motion, but he kept me there as he humped my face. Tears sprung to my eyes and I debated tapping him to bring his focus back down to earth, but I didn't want to ruin his orgasm.