My Brother's Dilemma

It was an ordinary Friday evening. I was twenty-two years old, still living at home with my mother and eighteen-year-old brother Leon. In my bedroom, deciding what outfit I was going to wear on Saturday night, there was suddenly a knock on my door.

"Come in!"

"Hey, Pippa." It was my brother. "Do you ... ur ... have a few minutes for a chat please?"

My brother looked very nervous and unsure of himself. "Of course. What's up?"

Leon stepped quietly into my bedroom and closed the door, checking mum wasn't around first.

"Is everything ok?" I asked, dropping what I was doing. My brother look anxious.

"Yeah, listen, I'm sorry to come to you with this, Pippa. I just don't know who else to turn to."

"Ok, sit down and relax. I can see you look stressed about something."

"Thanks," he huffed, taking a seat on the end of my bed beside me. "Well, there's this girl in school ..."

I giggled. "Arrrr, I see."

Leon smiled, slightly embarrassed. "The thing is, I really like her, and I know she likes me too."

"So, what's the problem?"

"We've been seeing each other for a couple of weeks now. Nothing serious yet. But she's invited me round her house this Sunday. Her parents are going out for lunch. Netflix and chill were her words. It's going to be the first time we've been alone together, properly alone I mean."

"Are you thinking she wants to have sex with you?" I cut to the chase.

"Maybe?" my brother shrugged.

"Leon, answer me honestly. I won't judge you, okay?"

"Ok," he nodded and sat up straight.

"Are you still a virgin?"

"I know it's pathetic at my age, but yeah."

Suddenly dejected, my brother slumped and looked down at my bedroom floor, fiddling with his hands together. He looked sad, as if he thought of himself as a loser.

In all honesty, I was surprised. My brother is a good looking, sweet, genuine guy. He stands five nine with a slim body and a gentle personality. He never displays arrogance and I've never heard him talking down about girls either. Probably due to the fact he was raised by a woman, and he had me, a slightly older sister who actually looked out for him. We hadn't had a serious sibling rivalry fight since I was twelve.

Leon looked up to me because I was always there for him. I'd given him dating advice before, when he was sixteen, about to go on his first date to the cinema. I advised him on the appropriate behaviour etc. and the signals to look out for from his date.

Fast forward two years, to this very moment, I was surprised my brother was still a virgin, but also proud he wasn't one of those typical high school guys who couldn't wait to stick it inside every girl prepared to spread her legs.

"Leon, it's fine. Don't ever be ashamed or embarrassed about it. So, what if you're still a virgin. Be proud. I wish I was still a virgin," I joked. We both laughed.

"The thing is, Pippa. The guys in school are always talking about sex and blowjobs. I haven't even touched a girl. I've kissed girls for sure, but that's it!"

"You mean to say you haven't even put your hands on a girls' breasts yet?"

"Only over her top, never had the balls to go under it, let alone get them out and play with them."

"Why not?"

"Too worried about scaring her off."

"Oh, Leon," I sympathised. My brother really was an innocent sweetheart. Too innocent.

"Sad, I know," he grumbled.

"Ok, wow! Where to start?" I stood up, trying to think of a way to help my brother before he went to his girlfriend's house and made a complete fool of himself.

"I just want your advice on how to approach Sunday."

"What's your girlfriends name? Is she a virgin?"

"Donna, and yeah, she says she's a virgin. I believe her."

"Ok, and has Donna actually indicated she wants anything to happen on Sunday? What kind of girl is she?"

"She's amazing. I think she's intelligent and beautiful, but some of the boys say she's frigid and I have no chance of shagging her. I really like her, Pippa. It's not about sex."

"You're so sweet, Leon, but even girls don't want a guy to be too sweet. What vibes are you getting about Sunday? You're both eighteen and virgins, going to be home alone chilling in front of Netflix."

I cast my brother a dubious look. Surely, he wasn't this naïve?"

"I don't know if she wants to have sex. I doubt it. We've only been seeing each other for a few weeks. We've kissed so I'm expecting we'll be doing that, but I'm worried that if I try to touch her, I'll ruin everything."

"Do you want more than kissing? Does she? You know what I'm talking about, right?"

"Yeah, I know what you're talking about. I think we both want more. I know I do. I get hard every time we kiss."

I laughed and sat back down. "Trust me brother, Donna definitely wants you to touch her. You have to be mindful though, move too fast and you might trespass on her boundaries."

"That's exactly why I've come to you. I'm a guy who hasn't even felt a pair of tits before. I want to do it right and not get carried away. I want her to enjoy it. If that's all that happens then I'm fine with that."

I thought for a few moments, unsure of the best advice to give my little brother. Not knowing this Donna girl at all, and not knowing how reliable my brothers knowledge of her intimate past was, I had to think carefully.

"Ok, it's really quite simple. The first thing you need to do is to be confident. If she's as frigid as your friends say she is, then chances are she's either rejected all of their advances, or she's had a bad experience. Guys can be right arseholes when they have a girl in their hands. You think with your dicks all the time. Which sometimes is a good thing," I laughed. "But not when the girl is looking for genuine affection."

"So, what do you suggest?" Leon sighed, totally lost.

"I suggest you follow your heart. You're a good guy. You're sweet and loving. You'll know the signs. It's natural. When you're kissing Donna simply recognise her responses."

"I was hoping you'd give me a bit more than that?" my brother frowned.

"Donna is creating the perfect setting for you both. No interruptions and you've already kissed. Make sure you have protection, but keep it hidden just in case sex isn't on her agenda. Go there with no expectations. Then, when you get close and inevitably start kissing, gauge her responses. You'll know if she wants more. Kiss her nice and slow. Don't rush it. Hold her and don't get too excited with your hands unless she starts getting excited, signalling she wants more."

"That's pretty much what happens. Except Donna doesn't take the lead. So, we end up just kissing."

"She's waiting for you, Leon. Inexperienced girls rarely take the lead in fear of messing it up or leading you on too far. You know what guys are like. How many of your friends shoot their mouths off about girls who don't put out? And the girls who do? You already said they brag about having sex and blowjobs."

"I know, but I'm not like that. It's the same for guys to, you know. I've seen guys reputations get destroyed by girls because he shot his load too early, or because his dick was too small. Anyway, I'm not even worried about that. I just don't want to start groping her and then fuck it up."

"First of all, don't grope her!" I laughed. "This is not happening whilst drunk in an upstairs bedroom at a house party. If she's not taking the lead then you have to. Consent is the key ingredient. Ask her softly what she likes and wants while you're kissing. If she's enjoying the kiss, move across her face. Kiss her cheek, neck and ear lobe. If she doesn't like something she'll tell you. She's won't panic and kick you out because you kissed an area she doesn't like."

"The kissing isn't a concern, Pippa. I'm happy kissing all those areas. But when I want to bring my hands in on the action, I get doubts in my head. I know it's not normal for a guy my age, but that's how I feel. Then the anxiety creeps in and my head is fucked."

"Trust me, Leon, with your attitude you're going to be fine. You're already putting Donna's feelings before your own. I'm starting to doubt if you're actually a guy!" I joked, it was poor timing, very poor timing indeed.

"Thanks, sis, I came to you for help, not to have my masculinity questioned."

I quickly put my hand on my brothers thigh and smoothed it back and forth. "I didn't mean it like that. I'm sorry."

"I know you didn't," he sighed again. "I'll leave you to enjoy the rest of your evening."

"Leon," I sulked. "Don't leave like this."

"It's fine, Pippa, honestly. "I just need to man up. Get over these dumb nerves and go with the flow."

"You'll be fine. You have a gentleman's heart."

My brother left and closed my bedroom door. I reflected on what I'd told him and wondered if I'd been any help at all. But what else could I say or do? I knew he would be fine. But somehow, I felt he left just as nervous as when he first opened up to me, possibly worse.

I returned to my wardrobe and spent the next hour trying on different outfits. When I finally decided what I was going to wear on Saturday night, I went for a shower.

As always, when I'm under the pleasant feelings of hot water, I became aroused. Over nothing in particular, I simply became turned on as I soaped and washed my large breasts. My nipples became hard and my clit began to throb.

Standing beneath the main shower head, I picked up the smaller hand shower and began to rinse the soap from my body. Taking my time to caress each breast with my free hand, I then smoothed my hand down my tummy and over my shaven pubic mound.

My body was already tingling when I reached my pussy and slid my index and middle fingers either side of my clitoral hood. I spread them to reveal my throbbing bud, then directed the hand shower a few inches in front of my clit.

As the jets sprayed against my pussy and and clit, pounding it with hot pressurised water, I leaned my back into the corner of the tiled wall and let the water do all the work.

Moaning and panting in no time, my mind began to wander. Visions of my brother and his girlfriend Donna entered my thoughts. She was blurry because I didn't know what she looked like, but I could see my brother clearly, expertly caressing his girlfriend just the way I liked it done to me.

In my fantasy my brother wasn't aggressive or too grabby, he was gentle and attentive. In no rush to unclothe me.

Wait! What? I was suddenly the blurry girl in my fantasy. I could see myself kissing my brother as he touched my breasts through my clothing. He was rubbing them over my t-shirt. Leon then confidently put his hand up my t-shirt and played with my breasts over my bra.

The next thing I saw in my mind was my brother removing my t-shirt. Once it was off he started touching all the exposed fleshy parts of my breasts which weren't covered by the bra. His fingertips gently grazed along the top edge of the black lace bra I imagined myself wearing.

Leon grew in confidence, kissing my neck and throat before he moved down into my cleavage. Touching and kissing the sides of my breasts, he slid his hands round my back. I helped him by raising my body off the bed. I visualised myself gasping just as hard in my fantasy as I was in the shower, because I imagined my virgin brother unclasping my bra as if he'd done it a million times before.

"Oh my God! Yes! I'm gonna cum!" I panted inside the bathroom.

But my brother was only getting started. Unlike the boys before him, but like the men I've been with, Leon oozed confidence and delight at seeing my breasts for the first time. He didn't dive in and grab them as if they were big balls of dough, needing to be flattened and slapped about. No, he delicately touched the areas around the sides of my breasts. Very gently tracing a fingertip along the sides of my sensitive curves, downwards and across my underboob.

My brothers soft lips then gently kissed my breasts for a few moments. His tongue licked around each nipple in turn. He tasted my dark areolas, turning my already hard nipples sensitive. They were crying out in agony. Then my brother suckled on one teat and then the other. Back and forth he teased every inch of my breasts.

A question suddenly popped into my head. Do you want him to fuck you? Do you want your brother to slide his cock into your pussy, Pippa?"

"Oooooooh, fuck! Yes! Fuck, yes! I'm cumming, Leon. I'm cumming!"

My orgasm was so intense I dropped the shower head into the bath tub and it sprayed water straight up at the ceiling. I didn't care. I started rubbing my clit and shoved a finger into my wet, aching hole. I fucked myself hard until my clit became too sensitive and my orgasm subsided.

"Shit, Pippa!" I gasped too myself, quickly picking the shower head up. Where the hell did that come from? What if he heard you?"

I finished showering and anxiously stepped out of the bathroom. Relieved to see my brothers door closed, and hearing his screams and shouts, I exhaled a huge sigh of relief. He was busy online playing video games with his friends.

Mortified that I'd just wandered into an incestual fantasy involving my brother, I shivered and closed my bedroom door.

Sitting at my vanity unit, I dried my hair with my bath towel wrapped around my body. I tried to concentrate but thoughts of what I'd done in the shower, the thoughts I had, kept returning. No matter how hard I tried to ignore them, they just kept coming back.

There was another knock on my door. It startled me and I panicked. "Hang on! I've just gotten out of the shower! I'm still in my towel!"

"It's only me, love!" It was my mother.

"Come in!" I sighed in relief again, turning off my hairdryer.

Only popping her head inside, my mother said to order a takeaway for ourselves. She was going out for drinks with her boyfriend, and she wasn't going to be back home until the morning.

"Enjoy your night, mum."

"You too, love. I'll just let your brother know."

For the next ten minutes I sat motionless. With the towel wrapped tightly around my body, I clutched the hairdryer in my hand and stared into space. I listened as my mother said goodbye to Leon and left the house.

Those ten minutes of contemplation were the longest ten minutes of my life. But I made my mind up, convinced what I had thought about in that time would work.

I stood up and put a matching black lace bra and panty set on, then slipped into my loungewear blouse and shorts. With a few deep breaths, I walked out of my bedroom and knocked on my brothers door.

"Yeah!"

"Mum said to order a takeaway. What do you fancy?"

Busy on his Xbox, Leon barely glanced in my direction. "Pizza's always a winner."

"Double Pepperoni?"

"Yes please. Give me a shout when it arrives. I'll come down and eat with you."

I closed the door and went into the kitchen. I ordered the pizza and immediately poured myself a large glass of wine. By the time the pizza arrived, I was half way through my second glass.

"Leon! Pizza's here!" I shouted up the stairs.

"I'll be down in five!"

The tension as we sat watching an episode of Friends and eating pizza was exaggerated for me. Leon was chuckling away, munching on his double pepperoni while I sat across from him, one eye on the sitcom, one eye on my brother, biding my time to bring up his dilemma again.

"I'm sorry about earlier, Leon." Now was a good a time as any, I decided, pausing the TV. "I don't think I was much help."

"Forget about it, Pippa," he shrugged nonchalantly. "It wasn't exactly something a brother should ask his sister."

"Come on, Leon, you know that's not an issue. I want to help you."

"You already did. You're right. I just need to be myself and let everything happen naturally."

"No, Leon. I want to help you."

"Huh? What do you mean."

"Let's say Donna wants you to do more than just kissing. You obviously want this too, but do you know how to remove a girls clothing and touch her body? Touch her in a way that will arouse her and not kill the fun and excitement you're both experiencing?"

"You know I haven't done any of that," Leon frowned. "That's why I asked you for advice."

"I can only tell you what I like. Most girls will be similar, depending on their mood."

"Will you tell me what you like? I mean, not in a weird way. Just tell me how a girl likes to be touched. I don't want to grab or hurt Donna by being too rough."

"You're more in danger of being overexcited. Donna will get a buzz out of you being excited about her body. But she won't just want a kissing, groping session. She might, but I doubt it."

"So will you tell me how to do it, please?"

"I can do better than that. Finish your pizza and come meet me in my bedroom."

"Pippa? What are you saying?" Leon looked shell shocked.

"I'm going to let you practice while I tell you what to do."

"Practice how?"

"On me you dummy," I giggled. "How else are you going to learn. By the time Sunday comes you'll be able to control your emotions, be ready to seduce the clothes right off your girlfriend. Who knows, you might even lose your cherries together."

"Fuck! Are you serious? Your tits are massive compared to Donna's."

"Been peeking have you?" I laughed.

"No!" Leon instantly shot back. "But they're hardly missable are they? You and mum have both got big tits. I get plenty of stick from all my mates about it too."

"What kind of stick?" I wondered.

"My mates follow your social media. They all say they'd fuck you. The ones who have met mum say she's a MILF. It's annoying to be honest."

"Well, let's not get side tracked. Finish your pizza and meet me in my room."

"Forget the pizza, I'm ready now."

"Calm down. Now your showing your adolescent side. The side that will put Donna off in an instant."

"Sorry."

"Give me a few minutes to get ready. You can wait outside my door until I call you into my room."

Inside my bedroom, I stood with my back against the door, shocked to my very core. I couldn't believe what I just offered my brother. I couldn't believe he accepted so readily.

Inhaling several deep breaths, I paced my bedroom knowing my brother was standing outside.

"Are you ok, Pippa? We can forget about it if you want?"

I didn't answer him. Instead, I collected my sleep mask and a scarf and put them on my bed before finally opening the door.

"Are you ok?" Leon asked once more.

"I'm fine. Come in and sit down on the bed."

"Are you sure? It's a bit weird, isn't it?" My brother moved awkwardly, taking his seat on my bed again.

"That's why you're going to be blindfolded," I told him. You need to concentrate on what you're doing, not who you're doing it to."

"I'm cool with that." Leon's voice was shaky.

"Put my sleep mask on and then I'll gently tie the scarf around your head."

"I can't stop shaking," he chuckled nervously, staring at my chest. "I never imagined my first pair of tits being my ..."

"Shhhhh!" I giggled, placing my finger against his lips. "Just close your eyes and relax."

Leon took a couple of deep breaths before he slipped my sleep mask over his eyes. I then wrapped my scarf around his head, covering the sleep mask.

"Can you see anything?" I smiled.

"Pitch black," he replied.

"Ok," I sighed nervously. "Now pretend I'm Donna. Imagine we're on her bed when I kiss you."

"We're going to kiss?" Leon gasped. "I thought I was only going to feel your tits?"

"Relax. Stop talking and pretend I'm Donna." I was so nervous my brothers understandable hesitance was quickly getting on my nerves. I sat down beside him, but face on.

"Ok, ok, no more talking," Leon agreed as we settled on my bed together.

It was a very strange and surreal feeling sitting beside my blindfolded brother. I closed my eyes and turned his face towards mine. We were both breathing heavily, from nerves more than excitement.