Emmy's New Kinks Ch. 10

Chapter 10

Flight Down and Day 1

I tried calling and sending messages to Lydia, but got no response. At first I was sad and worried, but after a few days of being ignored I only felt angry. She was the one who came on to me! I thought about going to her house and finding her, but decided I should do my best to give her some space. I was a little worried since we were signed up to be roommates at college in the coming year.

My trip with Nick's family was rapidly approaching, but I tried to keep some space from him. I wasn't sure how I felt about his admission that I could sleep around. The night he told me I cried myself to sleep, although I wasn't sure why. I'd liked all the sex, with Nick and with others, but I was worried about what it meant for me and my relationship with Nick.

The next day I called Jill and talked things out with her.

"He said that?!" she exclaimed after I told her what Nick said.

"Yeah..."

"Holy shit that's awesome!" Jill seemed really happy for me. "The more I hear about Nick the more I like him. He has an older brother doesn't he?"

"Yes..." I said. I wasn't quite as enthusiastic about the situation as her. She seemed to sense my mood.

"Hey Emmy, I know it's scary and different and, well a little odd honestly. But seriously, sounds like you have a good deal here. He promised not to fuck around if you didn't want him to. Honestly one of the main reasons I broke up with Jack my freshman year is because I wasn't ready to just have sex with one person. Seriously, you have the best of everything: rich devoted boyfriend and you get sex with whomever. I am totally jealous!" She did sound jealous, which made me feel a bit better.

"Oh, when you put it that way it does seem like a good deal." I started giggling. "I wish he had told me privately though, I'm pretty sure mom or dad was around the corner of the house."

"Ha! Well I'm not getting involved in that one. Frankly I doubt you have anything to worry about. When I warned them about my implants mom just said 'that's nice honey' and dad cracked some joke about me being safer in a car wreck. Anyways, tell me more about this vacation you get to go on! I saw the bikini pictures online! That white monokini is really hot and your friends really seemed to like you in it!"

"Wait what pict-," I began then cut short. "Yo-you looked atthosepictures...?" I realized she was referring to pictures and video Jenny had given to Nick.

"I just can't help it! I always try to stay away, but it seems like everytime I end up drunk and alone I end up checking in on you. God Emmy, your life is like a fantasy. It's not fair you get the better looks and the best boyfriend!"

I didn't know what to say so I just stayed quiet.

Jenny seemed suddenly unsure of herself. "I'm sorry Emmy. I didn't mean to intrude on you like this... If you want I will stop. I just wanted to be a part of your life."

"It's okay..." I found myself saying. WTF?! Why the hell would I say it's okay if my sister watches me fuck around?! I decided to turn it back on her. "I don't see what you get out of watching though. I mean, I'm your sister for Christ's sake!"

"Just making sure my baby sister is okay," she said and laughed. "Well, I'd love to talk but I'm supposed to meet some friends so I gotta go. Love you and talk to you later!"

"Bye Jill!"

The rest of the time leading up to the trip I couldn't get the fact that my sister watched my videos out of my head. Fortunately the excitement of the trip and pacing became a welcome distraction. When the day to leave finally came my mom took me to Nick's house and dropped me off. As we pulled into the driveway Nick's brother Andy came out of the house carrying luggage.

"Whoa, who is that!" my mom exclaimed.

"That's Andy, he's Nick's brother," I responded. My mom had a flushed look to her cheeks, although I couldn't blame her. Nick was an attractive guy, but Andy was taller, stronger, and had the jawline of a superhero. Add in his piercing blue eyes and he was pretty much any red blooded female's fantasy.

When we parked the car he quickly approached. "Hello there! Emmy it's always nice to see you, and you must be Mrs. Rosin. I'm Andy, Nick's older brother." He pulled each of us in for a hug and my mom's cheeks flushed as she felt his muscled body. "Let me grab your things for you Emmy." He easily hefted my large suitcase and put it in the back of Nick's car.

My mom hugged me goodbye, took one last look at Andy then left.

"Nick should be down shortly, he just had a few more things to pack" Andy said. His eyes roved up and down my body, taking me in. I'd chosen a comfortable sundress that fell to my mid thighs. I wasn't wearing a bra, and I felt my nipples harden as he inspected me. I wasn't sure if I wanted him to notice or not!

We caught up a bit and Nick soon joined us. It was time to leave for the airport, so we headed to the car.

"I'll drive," Andys said. I got the sense he was the kind of guy who was always taking the lead. Nick handed his keys over and I headed for the back seat.

"I think the lady always gets to sit up front," Andy said and used his hand on my hip to steer me to the front. Nick didn't protest, so I let myself be guided. Andy opened the door and I slid into the car. Andy's eyes flicked down, and I blushed as I realized he probably saw my yellow panties.

Nick and Andy happily talked on the drive to the airport, and soon I was joining in. Andy was a really funny guy and he seemed to have a lot of wisdom about the world to share. Security at the airport was quick, and in just a few hours we were airborne. I took the middle seat between Andy and Nick and settled in for the uneventful flight.

When the captain announced we would begin our descent soon, Andy offered his window seat to me.

"Here Emmy, trade seats with me. You should really see how beautiful the islands are!" I happily traded and was peering out at the blue water and sandy beaches. Suddenly I tensed as I felt Andy lean against me.

"That big one over there is where we're going to land, but we'll take a boat over to the one our resort is at," he said pointing out the window. He dropped his hand it rested on my thigh. My nipples hardened at the contact from the attractive man, but I tried my best to ignore it.

He pointed out a few other things, each time lifting his hand pointing, then replacing it slightly higher on my thigh. By the time we landed my dress was pushed up nearly to my crotch and his hand was gently rubbing my exposed thigh. I felt like I should say something, but when I looked at Nick I noticed his pants bulging. I decided we both might enjoy a little harmless flirting so I let him rub my legs.

We landed and quickly found representatives from our resort. They helped with our luggage and soon we were on a boat headed to the island. We hung out on the bow, enjoying the warm wind and sea spray. I was careful to keep my hands down so my dress wouldn't blow up, but at one point we cut through some wake and I stumbled. My arms shot out as I fell backwards, but Andy quickly caught me around the waist.

"Whoa! Careful there. You'd better hold on the rail Emmy," he said. I realized that my dress had flapped up and he had his arm around my bare waist! When he pulled me close my dress had pinned up between us and my ass and yellow panties were exposed to everyone! I decided it was best to pretend nothing was wrong so Nick wouldn't realize what was going on. Hell, Andy probably didn't even realize what was happening.

We stood there chatting, but after a few minutes Andy's hand slid down to my ass! I'm really glad there was so much wind, because otherwise my moan would have been audible! I decided I needed to extricate myself.

"Is there a bathroom on board?" I asked.

"Yeah, it's in the back behind the cabin," Nick replied. I pulled away and smoothed my dress down and turned towards the cabin. I was shocked to see the captain giving me a smile and a thumbs up from the cabin and blushed. I quickly headed to the bathroom.

When I got back I tried to get Nick to scoot down, but he again made room between him and Andy! I stood there holding my dress down nervously.

"Careful Emmy, you already fell once," Andy said. He resumed discussion of sports with Nick and took my hands and placed them on the rail. Fortunately the wind seemed to be coming from a different direction and my dress didn't fly up. This didn't seem to perturb Andy, who calmly lifted my dress over my ass and resumed his fondling!

When I turned to Nick he seemed engaged in the conversation with Andy. Fortunately I could see our destination coming up. A short cart ride later and we arrived at our house. It was small but luxurious and just off the beach in the shade of trees.

There was an outdoor shower and hot tub. The inside had a small kitchen area adjacent to the sleeping and living area. I was shocked to see that the only private room was the bathroom! I'd been looking forward to some sex with Nick, and needed it pretty badly after his brother's aggressive groping, but now it seemed we'd have to sneak off somewhere.

Nick's parents would arrive tomorrow morning, so we had the evening to ourselves. Meals were delivered by room service and that night we had fish served over rice with fruit on the side. They also left us wine and a large supply of beer for some tradition of Nick and Andy's. I didn't have to wait long to find out what this was.

"Ready for the game little guy?" Andy asked soon after dinner.

"You're going down this time!" Nick said laughing. "I'll clear some space. You brought the cups right?" Nick was pulling the table into the center of the room and moving chairs from either end. I watched curiously until Andy started setting cups down in a triangle on the table.

"Are you guys playing beer pong?" I asked.

"Hell yeah we are!" Andy responded enthusiastically. "Little man here thought he was something special a few years back and challenged me. Seems he enjoys getting beat because we play every year now."

Both guys took beers and began filling cups. I went and poured myself a glass of wine and settled in to watch. Turns out it wasn't just one game they played, but a first to 9, win by two system. I was bored at first, but Andy and Nick made sure my wine glass was full and soon I was cheering along with them.

A few games later Andy cursed as Nick sank his last cup, "Shit Nick, you been practicing?" The score was now tied at 2-2.

"Nah, you're just getting old!" Nick teased, a grin on his face. Andy returned the smile.

"How about we make it interesting then? Winner gets the bed," Andy suggested. The room had two beds, a king sized one near the back, but the other was a couch-lounge combo.

"What? I thought you said Emmy and I could have that one?"

"She can still use the bed! Besides, all you have to do is win. Shouldn't be so hard for a young guy such as yourself!"

For some reason I chimed in at that point. "This lounge is pretty comfortable honestly."

"Come on pussy, even you girl has more balls than you," Andy taunted.

Nick set his jaw and quickly agreed. Just as we were about to start up the games again a resort staff member showed up and dropped something off for Andy. He set it on his bags and the game resumed. Everyone seemed surprised, even Nick, at how quickly he won, taking the lead 3-2. The games and teasing went back and forth. They seemed evenly matched and we stopped to take a break when the score reached 6-6.

I went to the bathroom, and when I was back I found Andy opening the package that was dropped off. Inside was a plastic bag of pot! I'd seen kids smoke it at parties, but I'd never done it before. He rolled a joint and lit up then passed it to Nick. My eyes went wide.

"You don't smoke Nick!" I exclaimed as he brought it to his mouth.

"Wha? I don't during the school year, but that's just because of the drug testing for sports," he replied before taking a hit. He held the joint out to me and I found myself taking it. I inhaled deeply. When exhaled my throat burned and I coughed hard. Andy offered me a glass of water which I gratefully accepted.

"First time?" he asked. I nodded in reply, still coughing. A few minutes later I took a second hit, and soon I was feeling very relaxed.

Andy won the next two games, giving him an 8-6 lead. He looked confident. Nick won the next two games, but just barely and I could swear Andy was throwing them on purpose. Between shots he stared at me and I felt myself shiver in desire. It was tied up 8-8 now, and Nick seemed confident. We took another smoke break and I was pretty fucked up.

Nick was trash talking a lot now, and was obviously very drunk. "Scared Andy? Sure that the lounge has enough for your dick and your ego?" Nick taunted. At the mention of Andy's dick my mind wandered, imagining what such a masculine figure was packing. I came back into the conversation and got a shock.

"There's no way she will agree to that!" Nick was saying.

"Just ask her," Andy instructed and Nick turned to me.

"How about it babe?" I just gave him a confused look. "The lounge is probably too small for two, so are you okay with sharing the bed with the winner?"

"I don't know Nick," was my blunt reply. I knew where this was probably heading. Nick looked shocked and a bit worried and Andy's face took on the look of a predator.

"What?! No, just share the bed. You don't even have to get naked if I don't win," he explained quickly. "It's a huge bed and you won't even have to touch!"

"I don't know, her ass was feeling pretty nice earlier." Andy interrupted us and my face reddened. I suddenly realized how messed up I was and reigned myself in.

"Andy!" I was blushing furiously. "I-I'm not getting naked..."

"Just panties then," Andy said. I tried to figure his game out, but his expression was blank. I couldn't believe he was pushing so openly in front of his younger brother. The wine and weed and teasing had me on edge and I nodded slightly.

"Well, it's agreed then. The big bed and Emmy in her panties. Let's settle this," Andy said and moved to the table. Andy won in ten minutes. He didn't miss a single shot, and his gaze rarely left mine. When he sank the last cup he winked at me. Nick cursed in frustration.

"I'm not sure I can do this," I said, my throat tight and my heart hammering. I was still looking at Andy as Nick spoke. Andy raised his eyebrow at me.

"A bet's a bet, Emmy," Nick said, "Besides, if you back out now he'll never let us live this down."

"Yes it is, now it's time to pay up!" Andy moved towards me. "Let's see those yellow panties again." I didn't resist as he reached behind me and unzipped my dress and pushed it off my shoulders. I was surprised when he moved back after exposing me.

"Damn Nick! Emmy is fucking hot!" Andy exclaimed. "Let's see that ass!"

I turned around and looked at Nick so his older brother could see my ass. Nick was smiling, and his shorts were definitely looking a bit fuller than usual. I felt a small thrill run up my spine.

I hung out mostly naked for about thirty minutes, but soon we decided to call it a night. I brushed my teeth and joined Andy in bed. I lifted the sheet and quickly dropped it when I saw he was naked.

"I'm not sleeping with you," I hissed.

"Relax, I always sleep naked. Besides, we will definately be sleeping together, that's what beds are for." Andy reached out and pulled me onto the bed and under the covers. I rolled over so my back was to him and he nestled up behind me.

From my brief peek and the feel against my butt, he was huge. He hadn't been fully hard, but he was already bigger than Nick. His chest hair against my back felt nice and it made me wish Nick had a bit more hair.

Nick came out of the bathroom and saw us, Andy's arm around my naked torso causing Nick's eyes to widen. "Goodnight Emmy, love you," he said nervously before turning the light out. Andy's hand immediately started rubbing my breast.

"Aaahhh, what are you doing?!" I hissed. I didn't want Nick to hear, but Andy didn't seem to have any such qualms.

"Playing with your perky tits, can't you tell?" Andy spoke at a normal volume and I heard Nick shift. My eyes were starting to shift to the darkness and I could make out a lump on his bed. I grabbed Andy's hand with the intention of removing it, but found myself just holding it as he massaged my breasts.

This wasn't enough for him, and soon his hand moved down and I felt him pulling my panties to the side.

"What the fuck are you doing?!" I said, a bit louder than I wanted to, but I needed to get my anger across.

"Well, you said you weren't taking your panties off, so I was just going to fuck you in them. Don't pretend like you don't need this, I saw how wet your panties were earlier," my boyfriend's older brother smugly said. I thought I heard a moan from across the room but it had to be my imagination. I tried to struggle away, but Andry grabbed me and I felt his cock rubbing across my pussy and ass. He took my hand and guided it to his cock.

"Shit, you're huge," I whispered. I knew he had to be smirking as my hand was running up and down his veiny manhood. I could probably fit both my hands on his cock and still not fit the rest in my mouth.

"Stick it in," he ordered. My hands froze on his cock. When I didn't move he grasped my arms and used them to angle himself. He started to move his hips forward. All I had to do was let go and he would slide across rather into my pussy, but I didn't.

"MMMMmmm," I moaned as he slid the first inch into me. I let go of his cock and panted. I wanted him to stick it the rest of the way in, but he wasn't pushing forwards anymore. I groaned in frustration.

"Fuck Andy, you're already in, just fuck me," I begged. At this point I had forgotten my boyfriend was just across the room and could probably hear everything.

"I knew you were a slut. You want my cock, you're gonna have to agree to a few things first." He seemed to be talking a bit louder, and I realized it was probably so Nick was sure to hear.

"Fuck you!" I hissed and shoved my hips backwards, trying to impale myself on his dick. He was ready for it though and caught me after I only got another inch or so in me. I hissed in frustration.

"Damn girl, you want my cock bad!" He laughed and started to pull out.

"What! No! Please..." my voice sounded desperate. "Just...Just fuck me please... I need it." I was whispering, ashamed of what my body wanted.

"Don't worry, I'llfuckyou after you say yes to my terms." His hips thrust forward slightly when he said "fuck" and I moaned again. "First, you sleep here all trip. I'll let you keep your panties on if that makes you feel better, but don't think for even a second that is going to stop me from getting what I want. Second, I have to approve any outfit you wear this week. How do those two sound?"

I heard what he said, but didn't really care about it. I needed to fuck and Nick wasn't stopping us so I figured once Andy had me once it would be fine if he had me a few more times. "Fine, just fuck me you ass!"

"Well there is one more thing. For this trip you're my girlfriend."

"What the fuck?! You can't expect me to go on vacation with my boyfriend and not have sex with him!" In my shock at this demand my voice was loud, and I knew Nick had to be listening in.

"Don't worry, he likes to watch. Besides, you're gonna be too busy with me, your new boyfriend, for him." He started moving the tip of his cock around. It was only an inch or so, but it felt amazing. I hadn't seen Andy hard yet, but from feeling his cock I figured it was a couple of inches longer than Nick, and significantly thicker.

"MMMmmmm, fuuuuucckkk. Fine, whatever. I'll do what you want, just fuck me." I could feel my wetness dripping down my leg. I had to be as wet as the time Nick tied me up, belted, and ass fucked me.