Helping My Brother's Friend

I walked into the living room and saw my brother's friend, Jason, sitting on the couch. I was about to turn around and go back upstairs when I saw that he had his head in his hands. His posture seemed defeated.

I hesitated in the doorway, wondering if I should say something. Jason had been hanging out with my brother since they'd been in elementary school. Needless to say, while we weren't exactly close, I'd spent plenty of time around him in the past eight years. It felt weird not to say anything.

"Jason?" I called out softly.

He looked up, his dark eyebrows disappearing below the curls hanging loosely over his forehead. "Oh, Janine." He sniffed. Had he been crying? "Shit. Sorry, I..." He took a deep breath, and stood up. "Sorry," he said again, straightening up his clothes. "I was just looking for Paul. He said he'd be around."

"Ah," I said, taking a hesitant step into the living room. "He's at Marcie's place right now. Did he say he'd be back?" Usually, when he left this late, he would spend the night there.

Jason shook his head and shrugged. "He just said to feel free to come over. I guess I made the assumption that he'd be here, but now I'm thinking he was just trying to encourage me to get out of my apartment for a change of scenery." He ran a hand through his hair, pulling his curls out of his face.

"Change of scenery?" I repeated.

He rolled his eyes. "I think he thinks I spend too much time at my apartment playing video games." He paused. "Sorry, I don't know why I'm telling you this." He began walking towards the table, where I saw he'd laid his jacket. "If he's at Marcie's, he probably won't be back anytime soon. I'm sure you're enjoying having the apartment to yourself. I'll get out of your hair," he said, and though his voice sounded almost back to normal, I noticed the slight crack on the last word.

"Wait, Jason," I reached out to curl my fingers around his arm. He'd grabbed his jacket and had been walking towards me, towards the living room entrance, putting him within arms length. I hadn't moved out of the way to let him pass. "Sit down. Tell me what's wrong. I've never seen you this upset before."

Jason ran his eyes over my face disbelievingly. I registered the surprised tilt of his eyebrows. "Come on," I said. "Don't look at me like that. You and my brother are super tight. It's not like we aren't at least friends, right?" I slid my hand down his arm and grabbed his hand. As my fingers laced with his, I noticed his palm was clammy and shaking.

"Come on," I said again, dragging him by the hand back to the couch. I sat down and pulled him with me, right next to me. It wasn't like I'd forced him; he'd let me guide him. He was double my size. Literally. Jason was about six foot two, but also big around the waist. I was pretty sure he weighed at least twice what I did, so if he wasn't interested in sitting back down next to me, he could have definitely stood his ground.

"Tell me what's wrong," I ordered him gently, letting go of his hand and leaning back into the couch as I turned my body towards him. I could tell he was feeling down, and I wanted to be a good person and give him my full attention.

"It's just...I don't know. It feels weird talking to you about this. You're Paul's little sister."

"I'm eighteen now, Jason," I pointed out. "I'm not that little anymore."

"Oh yeah," he said, smiling at me. I was glad to see the break of sadness on his face. Jason wasn't the most attractive guy, but the smile definitely made him look approachable and kind. And sweet. "I don't think I told you happy birthday last month, did I?" he said sheepishly.

I let out a chuckle and waved it off. "Don't worry about it. I know you were really busy finishing up finals. Speaking of which, it's so cool that you're about to graduate. Two weeks left, right?" I said, bringing my hands together and clapping enthusiastically for him.

He nodded, but his smile slipped away as he sighed heavily. "Yeah...the last two weeks." His eyes glazed as he looked down at nothing in particular. "I just can't believe - well, it's like you said, there's two weeks left and honestly, I've been really bummed because Mary broke up with me this morning. I wanted to talk to Paul about it, to clear my head I guess. I just can't believe she would do this right before finals," he finished, shaking his head. I saw his fingers had fisted into the blanket thrown on the back of the couch.

I blinked, feeling a pang of sadness for him. "Oh shit. Mary broke up with you?" I didn't really know much about Mary except that she was a recent addition to Jason's life. They'd started dating a couple of months ago. I'd been really surprised to hear about it, because for most of my life, Jason had been single. However, I'd been really happy for him, and I'd thought it had been going really well.

"Yeah. Through a text." To my surprise, I saw a tear edge out of the corner of his eye, but he wiped it away before it could fall down his cheek. He looked away. "Sorry, this is so embarrassing."

"No, why would you think that?"

He shrugged, leaning back against the couch. "Because I feel like a loser. Because it feels weird to talk to you about this stuff."

"Aw, Jason," I crooned. "You're not a loser. You'll find someone else."

He shook his head, and his shoulders slumped further as he groaned. "Ugh, that's the thing, Janine. I'm twenty-two and I've literally never had a girlfriend longer than two months."

I paused, not really knowing what to say to that. He noticed the hesitancy on my face and let out a laugh. "See? You're eighteen and you've already had more relationship experience than me."

It was my turn to shake my head as I tried to come up with something to counter him. "Jason, you will find someone!" I said, at a loss for how to console him.

He flashed me a look that read, If you say so. "Look, you wouldn't get it. You're a girl, and you're really pretty and attractive, and I bet you have people lined up wanting to be with you."

"That's not true," I countered, opening my mouth to say more but not really having anything concrete to say.

"Janine, what's the longest you've been single for?" he said testily.

I looked away from him as I picked at the pilling on my pants. Finally, I shrugged. "I don't know, it's not like I keep track."

"Exactly! That's the thing though, I was single for four years before Mary, Janine. Four. When that much time goes by, you do keep track. And before that it was another month long relationship in high school. That's it. That's all my experience. No one wants to be with me because I'm overweight and I still have acne even though I'm twenty-two and it just feels like I'm going to die a virgin," he rambled.

My eyebrows shot up at that last part.

"Oh shit, sorry, that's awkward," he said, shaking his head and turning a deep shade of purple. "I didn't mean to dump that on you, it's weird."

My hand shot out to his again. I squeezed my fingers around his reassuringly. I said firmly, "No, it's fine. There's nothing wrong with being a virgin. I appreciate your honesty, and I'm glad that you feel comfortable talking about this with me," I told him. He caught my gaze briefly, and he gave me a small smile of appreciation.

In the back of my head, I wondered if this was the kind of conversation he'd been hoping to have with my brother. I couldn't imagine them talking about things like this; my brother was so emotionally disconnected, not to mention the fact that he was always flitting from girlfriend to girlfriend.

"So you and Mary never..." I asked, trailing off. But as soon as the words were out of my mouth, I bit my lip. I pulled my hand back from his again. "Wow, sorry, that's really none of my business." I chuckled awkwardly. I really needed to work on that filter.

"No, it's okay." He shrugged. "Mary was super conservative. We didn't do anything besides kiss. Most girls don't want to do anything with me when they hear I have no experience," he explained, sniffing again. "It's honestly just...really depressing. And lonely."

My heart broke for him and I snuggled up next to him as I laid an arm around his shoulder. "Jason, I'm so sorry. It sounds like you've been really sad about this for a while."

"Yeah, I guess. It's weird, when we were in middle school, Paul and I were both the nerdy outcasts, but then towards the end of high school he just...evolved. And I never had my glow up. I probably never will." He hesitated. "I know it's so stupid to focus on this right before exams are coming up and with me about to graduate, but I just never thought I'd finish university without having sex, you know? I was holding on to hope that Mary..." He trailed off. "I just wish I wasn't this ugly."

"Jason, you are not ugly!" I cuddled up into his side more, nudging him. He was big and warm and soft, and I hated that he thought these things of himself. Sure, he wasn't built like a model, but he was really nice and really smart. You had to be, to be about to graduate with an engineering degree.

He laughed miserably. "I know I'm throwing myself a pity party right now, but, well, let's just look at the facts. No one wants to fuck me, Janine."

I shook my head. "Honestly, Jason. You have some good features. For example, your curly hair is really cute," I said, reaching up and twisting a strand of his dark hair around my finger. I felt his breath hitch and I caught his eyes flit down my body before he looked away. A little shocked, I let the strand fall and rested my hand back to his shoulder. I suddenly became aware of the fact that I was pressed up against him in my camisole and short shorts. My breasts were pushed into the side of his arm, my clothing the only barrier between my nipples and his skin.

I swallowed thickly as I took a closer look at him. He fumbled with the frills on the couch blanket, and I realized that his hand was shaking.

"Jason, honestly, your biggest problem is probably confidence," I said slowly. "Not to be an asshole." I wanted to point out that I was sitting next to him and he was basically shaking, but I didn't want to rub salt into the wound or make things awkward between us. I leaned back slightly to give him some space; I didn't want to overwhelm him.

He looked back at me in protest, and I didn't know if it was because I'd extricated myself from my comfortable position next to him or if it was because he disagreed with what I said.

"It's really hard to have confidence when you have no experience with the opposite sex. I've never even seen a naked woman before," he added helplessly.

Again, my eyebrows shot up. Before I could help myself, I asked him, "Really? Not even in porn?"

He scoffed, shaking his head. "No, of course I watch porn. It's the only way I have to get off. Just me and the screen and my right hand." He blew out a heavy sigh.

There was a tense pause. I tried not to, but I couldn't help picturing Jason in front of his computer, pumping a couple of squirts of lotion into his hand before bringing it down to his cock. I had a hard time picturing his penis; I wondered how big it was. An image flashed across my mind of a pink dick, tucked away behind a heavy bush of curls.

Then I blinked. What the fuck. Why was I suddenly thinking of Jason's cock? I swallowed thickly.

"No seriously," I croaked out, surprised at the huskiness of my voice. I cleared my throat. "It's all about confidence. Fake it till you make it, Jason."

"Janine, maybe when you're younger it works that way. But by the time you finish college, girls expect you to know what you're doing. I turn into a shaky mess just at the thought of a girl taking off her clothes around me." He sighed again, the defeat back in his shoulders. His body tensed up, like he was about to stand. "Anyways," he started as he shifted on the couch, and I knew he was about to try to get up and leave again. But I didn't want him to go; not if I could help him feel better. He'd always been so kind to me, and he was such a good friend to Paul.

"Wait, Jason." I put my hand on his thigh to stop him. He settled momentarily back into the couch, looking up at me surprised as we waited for me to talk. I started slowly, "Do you think that...Would it help if...I mean to say..."

"What's up, Janine? Just tell me."

"Well, you've always been so nice to me, and I hate that you're struggling with all of this right now. And I do genuinely think that the problem is just that you don't...You don't really seem confident in yourself. And that's really important with girls, you know?"

He nodded slowly, like he was trying really hard to follow where I was going with this.

"So, I guess, I'm just wondering if you think that if you were to see someone naked, a girl I mean, if you thought that would help you. In the future. With other girls," I added, realizing after the words were out of my mouth that the clarification was probably not necessary.

Jason finally stopped nodding, and he bit his lip as he digested what I was saying. "I don't know, I mean, probably? It would definitely make me less anxious. But I don't see that happening anytime soon," he finished flatly.

"I'm a girl," I pointed out lamely.

His eyes shot towards me and he inhaled sharply. I felt his right knee hop up and down a couple of times - a nervous tic - as time stood still for a second. "Are you...offering?"

"I mean, yeah. It's not a big deal," I felt the need to defend myself. "If you're into it I mean. Sorry, oh god, that's probably so weird-"

"No, no," he said quickly. "I just. You're Paul's sister, and I mean, I think you're absolutely gorgeous and beautiful, but..." His knee hopped up and down again. "I'm so awkward, Janine. I'm sorry."

You're absolutely gorgeous and beautiful...

I replayed the words in my head and a soft smile covered my lips. "You think I'm beautiful?"

"You are. God, you must know you are. You probably don't need to hear this disgusting potato sack say it to know it."

"Don't speak that way about yourself. Please."

"Okay, I'm sorry," he said again.

"No, stop that, too. Stop apologizing. Do you want to see my boobs?" I asked assertively, shifting on the couch so I was facing him.

I saw his jaw tense as he swallowed. He nodded, turning purple again as he looked away.

"No, look at me, Jason. Tell me what you want. Come on, it will help you."

I saw him blink and then take a deep, shaky breath. He turned back to me, and our eyes met. I noticed for the first time that his irises were a pretty shade of blue; the color contrasted with the dark pink of his flushed face.

"I-I want to see your boobs."

"There you go," I said encouragingly. "That's not so bad, is it?"

He shook his head.

Maintaining eye contact with him, I grabbed the hem of my camisole and swiftly pulled it over my head. I discarded it somewhere on the floor. I squared my shoulders back towards Jason, daring him to look. He hesitated for a second before his eyes dropped to my cleavage. I was wearing one of my favorite push-up bras, and knew it was a pretty sight. The pained look on his face couldn't conceal the hunger in his eyes.

It honestly felt so good, so empowering to have him looking at me this way. To know that this was the first time he'd ever laid eyes on this part of a woman. To know that he wasn't comparing me to anyone else, because he couldn't. All of the other guys I'd been with had way more experience than me. I'd never been with someone where I had control and power.

"Can you undo my bra clasp?" I asked, turning around in my spot so that my back was towards him. I waited.

Just when I thought that he hadn't heard me, or he'd effectively become frozen, I felt the couch shift under me, and his cold clammy hands brushed against my back. I jumped a little, and I heard him mutter another apology as the strap from my bra tightened and then released. I sighed pleasantly as I brought my hands back up to the 32DD cups to hold them in place and turned back towards him. His eyes didn't bother meeting mine; they were glued to my chest. I bit my lip to stop the smile from spreading over my face as I shimmied and let the straps fall to either side of my shoulder. Finally, I slowly lowered my hand, the weight of my breasts pulling them down as I removed the support. As they became exposed, the cold air in the room brushed up against my nipples; they hardened into little pebbles.

Again, I saw Jason gulp and his knee bounce twice, but other than that he didn't move. His eyes flitted briefly from one breast to the other, and he groaned, a deep guttural sound from deep within his chest.

No amount of lip biting was going to stop the smile from spreading over my lips. I relaxed a little, realizing I'd also tensed. My shoulders pulled back and I stood up straighter, feeling my breasts sway with the motion. I capitalized on the movement, shaking them more, feeling them bounce side to side, the nipples pointing left and right as they jiggled.

"Do you like them?" I asked.

"Yes, oh god, yes," Jason responded without hesitation, his eyes still glued to them.

"Do you want to touch them?"

I saw him swallow again as he nodded. However, he didn't move.

I reached out slowly and grabbed his nearest hand. I brought it to my chest and pressed it against my right breast, jumping at the clamy coldness of his skin that only made my nipple harden even more. I left his hand there, and again, time stood still for a second before he brought his other hand to my left breast. He then gave them a tentative squeeze, and I bit my lip again as he began carefully pushing them up with the palm of his hand before letting them drop back down. He did this a couple of times, like he was weighing them, getting familiar with their size; they almost spilled out of his hand.

"Oh god," he moaned thickly, adjusting himself. "I can't - I can't believe this is happening."

I let out a little chuckle as I brought my hands up to cover his. "I mean, this is definitely not how I expected this evening to go," I joked, pressing my hands to his so that he tightened his grip. "You can be rougher," I added as I guided him to press my tits tight together. Then I released him and laced my fingers behind me as I thrust my chest out for him to play with. All his.

He cleared his throat a little before edging closer to me. He ran his palms lightly over my nipples, and I inhaled sharply. He noticed and did it again, and I nodded encouragingly.

"That feels really good," I told him, blushing. "I have really sensitive nipples."

He cupped my breasts, using the pad of his thumb to hover over the tips of the hardened nubs, drawing light circles over them. I whimpered. "Mmh. Jason." I was surprised at his newfound enthusiasm, and while I hadn't expected this to do anything for me, I was suddenly aware of the heat pooling between my legs.

Taking my words as encouragement, Jason lightly pinched the nipples between his thumb and point finger, rolling them and slowly tightening his grip. Harder and harder. I squirmed, feeling the pain starting, taking deep breaths along with the pleasure. I moaned again as he began pulling on my tits, using my nipples to bounce the weight of my breasts up and down. It hurt just the right amount. Just when I thought I would have to tell him to take it a little easier, he pulled his fingers back and began rolling his palms over my nipples again. I sighed from pleasure.

"Shit, Jason. You are really good at this," I told him, smiling languidly up at him from beyond my long eyelashes. He was too concentrated to respond; he was transfixed by my breasts, completely focused and zoned out to everything else. I thought distantly in the back of my mind that I wished any of my previous boyfriends would have been this focused on my body, on touching me, on my pleasure.

I began to stand up, and he tried to hold on to my breasts before his hands dropped to his sides disappointedly. He looked up at me questioningly, before understanding dawned on his face as I reached towards the button on my jean shorts. Positioning myself right in front of him on the couch, I undid the button and hooked my thumbs into my shorts and underwear. I pushed them down efficiently in one go and then kicked them away somewhere out into the depths of the room.