Staying Close to My Sister Ch. 05

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This guy fucks.
48.7k words
4.81
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46

Part 5 of the 5 part series

Updated 06/08/2023
Created 10/04/2016
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Huge thanks to chiefhal for proofreading this for me!

Part 5

I slowly faded into consciousness to the feeling of lips running along my member. From the soft, steady breathing surrounding me, I could tell that most everyone was still sleeping. I kept my eyes closed and stayed still so I would not wake anyone. Based on the technique, I could tell it was not Elizabeth or Mom, so I assumed it was Gwen. That said, her ministrations were much more reserved than she had been when she sucked me at the restaurant. I chalked it up to her trying not to wake me.

I laid back and enjoyed the soft fingertips tracing along my shaft, which then slipped to my testicles for some gentle tickling. Her tongue circled my tip for a time, but soon she switched to giving me adorable little kisses up and down, saving a few for my balls too. She eventually took me into her mouth, but did not go down very far, presumably to avoid making too much noise. Drool leaked down my shaft, which she used as lubricant to stroke me with both hands as her tongue fixated on my sensitive crown. After a few minutes I felt the pressure rising inside me.

I needed to warn Gwen about my imminent eruption, so I peeped my eyes open to catch her gaze. To my surprise, Gwen was still sleeping to my side, and a very naked Brianna was the one loving my manhood. She froze when she noticed my eyes on her, so I gave her a soft smile and breathily whispered, "Thank you, you're doing so good."

She nodded and slowly returned to her ministrations, timidly now that she knew I was conscious. Her eyes stayed locked with mine, so I made sure my face reflected the pleasure she gave me. Her confidence seemed to grow as she redoubled her efforts, trying to swallow me deeper and deeper as her hands moved faster and faster. I allowed myself to examine her naked form. She was similar to Gwen, save the pregnant belly, and her breasts were smaller of course. Her body was fit, toned in all the right places without having bulging muscle. Her fitness came in handy as she energetically pumped away. Her movements were fairly clumsy, but her enthusiasm had me on the edge sooner than I expected.

"Watch out." I whispered. "I'm about to blow."

She slipped her mouth from me, reaching one hand behind her to grab something as her other hand continued working my shaft. She produced a pair of panties, which she draped over my tip to catch my load. I tried to warn her that a single pair of panties would not suffice, but it was too late.

My first couple shots fired straight through the thin fabric, prompting her to ball her panties right around my tip, adding more layers to soak in the torrent. Cum deflected to the sides, spraying over her hands and face, and some landing on the bed. Panicked, Brianna discarded the panties and tried to use her mouth to catch my load and avoid making the mess even bigger. Since her mouth filled up quickly, and she was unable to swallow fast enough, she was forced to remove her lips from my member to avoid choking. Cum spilled from her mouth and poured over her smallish breasts as I continued to blast thick ropes into her face and hair. Once her mouth was cleared, she used it to desperately catch the final remnants of the deluge.

"Wow." She mouthed; her expression of surprise and awe concealed behind her cum-painted face.

"Sorry." I mouthed back. She just smiled and slipped out of bed, returning with a towel to clean what she could, then gave me a little wave and retreated to her bathroom.

Soft morning light was streaming through the window, so I decided not to return to sleep. I put my swimsuit on and headed downstairs to chill in the hotel pool. I sent Elizabeth a text message so she would know where I was when she woke up.

The morning sun warmed me up as I went for a swim in the large hotel pool, which was mostly vacant, as it had just opened. The only other person around was the lifeguard, a woman with sandy-blonde hair topping her slender and fit body, and adorned with a red one-piece swimsuit. She sat in her stand at the side of the pool, her eyes scanning my body as I stepped into the water.

I lazily drifted around the pool, enjoying the clean and cool water rippling around my skin. Sometimes, I could feel the eyes of the lifeguard sweep over me. At first, I figured it was because I was the only person in the pool, but then I remembered the bulge protruding from my tight swimsuit and suddenly felt self-conscious.

"Hey," the lifeguard said, "how's it going?"

"I'm alright, how are you?" I answered, dipping my legs under the water to hide my bulge.

"Honestly, I'm kinda bored." She huffed. "Do you mind if I join you in the pool?"

"Sure." I replied. She climbed down from her seat and dipped into the water. I swam to the edge of the pool and leaned against it. "I'm a strong swimmer, but I always feel better with a lifeguard around."

She drifted next to me. "You better not drown on me. I don't think I could drag you out of the pool. You're pretty big."

"You think so? I bet you could handle it, just don't get mad if you have to give me mouth-to-mouth."

"I wouldn't mind." she wheedled, pressing herself against me.

We brought our lips together, and kissed for a few seconds before I gently pulled away. "I don't want to get you in trouble at work."

"Nobody's around right now." She whispered as she squeezed my bulge.

"Somebody could come by."

She started grinding her crotch against mine, "Then I'll get in trouble. You'll have to make it worth it." She dipped underwater and pulled me free of my shorts, pausing for a moment to take in the sight. She started planting kisses up and down its length as it grew to its full size.

I was starting to enjoy it, but soon she surfaced, panting, "It's fucking huge! I knew it was big from when I saw your bulge, but I didn't expect a fucking hammer!" She produced her phone from a waterproof pouch on her swimsuit. "You have to take a picture for me. My friends will never believe I got one this big."

"Uh, sure..." I said as she pushed the phone into my hands. I aimed the phone down towards my underwater member.

"Not yet!" she exclaimed, then she plunged back underwater and posed with my dick over her face. I snapped a couple of shots as she shot a sexy smile for the camera, then she surfaced again.

"I hope they're good enough, the water caused a bit of a glare."

She reviewed the photos. "They're perfect! God, it looks so huge over my face! My friends are going to be so jealous!"

She moved to the side of the pool with her arms resting on the ledge and her thumbs tapping on her phone. She wiggled her butt and said, "Go ahead and get started."

I moved behind her, rubbing my cock against her covered slit as I asked, "Are all of your friends as slutty as you?"

"You bet, but they've never had your fucking T-Rex cock. They're already texting me back! So fucking jealous!" She boasted as I pulled the fabric covering her slit to the side and lined up against her, ready to rail her underwater pussy.

She let out a deep moan as I slid inside her pulsing honey pot. "Fuck yessssss! I bet you can tell I've never had anyone as big as you before! I don't think I'm even going to be able to feel other guys anymore. So fucking good!"

"How many times do you think I can make you cum?"

Her pussy quivered on my cock as she groaned and ground against me. "Apparently at least once, but I'm willing to bet that I'll lose count before we're done."

"Maybe so, but I don't want to take too long. If someone comes along, you'll get in trouble."

"Fuck them," she groaned, "they can eat a dick. They can eat your dick. I don't care if I get fired for this. Make me cum my brains out!"

"If you say so." I said as I started drilling harder.

Her phone started buzzing in her hand, signaling an incoming call. "Keep going, don't stop for anything." she breathed as she accepted the call and brought the phone to her ear. "Hey girl!"

I heard a voice from the other side but I could not make out any words. I only heard the lifeguard's side of the conversation. "Yeah, I know it's massive. He's... ah... he's fucking me right now if you couldn't tell. I know, but it's not like I could leave work. Hell no, I'm not waiting 'til after work for this fucking slab. They can fire me for all I care, he's pounding me... mmm fuck... he's pounding me so fucking hard."

I moved my hand around her front and pressed my fingers against her clit, causing her to spasm around my shaft.

"Mmmmm he's pushing all the right buttons." The lifeguard continued. "God he's got me so fucking stretched. I'm ruined for all those shrimp-dicked assholes that usually hook up with me. I'm gonna... fuck yes... fuck me fuck me fuuuuck me! Fuck I'm cumming so much! At this point we'd be in a pool either way! Fuck yes it's so good!" Her pussy went wild around me, then she panted, "Sure, let me ask him."

She tilted the phone away from her mouth and looked back towards me, "Hey, my friend wants to know if it's okay if she jills herself while looking at the picture I sent her of your cock."

"Uh yeah, I don't mind."

"Thanks! Hey girl, he says he doesn't mind. I bet he actually wants you to. I bet he wants you to cum while drooling over his fat cock. Fuck! I'm cumming again! Yeah, I bet he wants you to imagine his big fucking dick splitting you open like it's splitting me open right now. Mmmmm pumping a bunch of dirty sperm deep inside... ooo fuck... because you forgot to bring a condom. No, he doesn't have a condom on right now. You can't get pregnant if it's underwater."

Maybe I did fuck her brains out. Whatever.

"Fuck I can't wait! I feel him twitching inside me! I bet he's going to dump a big batch of baby-batter for me! Fuck yes! I'm cumming so much! Mmm how close are you?"

I almost answered before I realized she was still talking to her friend.

"Sooo close, huh? Keep going girl! Keep it up! Tell me what you want him to do to you!"

I heard the voice on the phone slowly crescendo into frantic squeals as the lifeguard backchanneled with moans. The phone finally went silent as the lifeguard said, "She came so fucking hard just now, and she said some really fucked up shit. She told me she wanted you to wreck her pussy, hold her down, and bloat her with your stud seed. I'll leave the rest to your imagination."

"Heh, well I'm feeling ready to blow."

"Mmm good, give it to me. Shoot it up inside me! You're the best I've ever had by a longshot! I've cum soooo many times around your fucking cock! It's about time I returned the favor, so blow your spunk up my poor little cunt! Fuck you're making me cum again! My pussy is falling in love with your cock! It's taking your shape! I've never felt like this! I've never felt this good! FUUUUUCK!"

She screamed as I released my load inside her. I could hear the voice on the phone cheering her on, and I also heard an unexpected voice from behind me.

"What a show!" Elizabeth exclaimed, almost causing me to jump out of my skin. Did pool guests arrive while we were distracted? My eyes darted around the area as she continued. "Relax, nobody but me got anywhere near the pool. You two were really into it, so good thing I kept watch for you."

My sister sat on the opposite side of the pool from us, slightly out of line so she could get a view of the underwater penetration.

"Thanks." I panted.

"I should be thanking you. That was fun to watch." She replied. "But if you're done then we need to head back to the room. Everyone's going to the mall and you need to change."

"Gotcha."

I pulled myself out of the lifeguard's snatch, eliciting a whimper. She seemed dazed, wracked with post-orgasmic bliss. Her eyes fell on Elizabeth as she asked, "I'm sorry. You're not his girlfriend, are you?"

Elizabeth giggled, "No, don't be sorry. I'm his sister." She threw a towel over me as I stepped out of the water, then rubbed it over me to help me dry off. "It feels amazing though, doesn't it?" She asked, winking at the life guard.

After a pause, the shocked lifeguard breathed, "Yeah." as she watched my sister lace her fingers with mine, then we headed back to the hotel room.

We arrived in the bustling hotel room, everyone getting ready to head out. I noticed Brianna did not seem to mind so much about being in a partial state of undress while I was around. The other girls had absolutely no qualms, allowing me to enjoy quite the skin show as we prepared to head out.

"You don't mind going to the mall with us, right baby?" Mom asked. "I know you hate shopping."

"Yeah, I don't mind." I responded.

"I bet you're just going to hang out in the food court and play games on your phone. And maybe listen to your weird ass music." Elizabeth quipped.

I was about to defend my refined musical taste when I remembered that Gwen and Brianna were supposed to go to a concert.

"I almost forgot, when's your concert?" I asked. Both girls looked disappointed.

"We couldn't get tickets. Dripping Dream has been getting really popular lately." Gwen said.

"They have a show tonight, but it sold out weeks ago." Brianna added.

"Oh, I'm sorry to hear that." I said. Mom changed the subject as the girls finished dressing, then we walked out the door. Because I had been distracted, I forgot to change out of my tight swimsuit.

The mall looked pretty much exactly like I expected, a bunch of shops appealing to tourists and a few attractions, while a rotund mall cop waddled past. I saw a sign for indoor minigolf which looked interesting, and we passed a movie theater too, much to my sister's excitement when a sign for some romance movie came into view.

"I forgot the new Moonlight movie came out!" Elizabeth exclaimed. "I've been wanting to see it!"

"I'm going to get a massage." Mom said.

"I'm going to look for some clothes. I don't have enough cute pregnant stuff." Gwen said.

"I'll go with you if you don't mind." Elizabeth said. "I'll need some new pregnant clothes soon."

"I'm getting a pedicure, want to join me?" Martha asked Brianna, who quickly agreed.

I remained silent, allowing the women to disperse as I made my way to the food court and started playing games on my phone. I tapped away on the little screen, eager to grind out some experience on PoonScrape.

Before long Gwen returned, grinning. "Lizzy told me you'd be here." She teased.

"She knows me too well." I replied. "What are you doing back so soon?"

"I'm a little tired. Lizzy's still shopping but I think I'm going to head back to the hotel room and take a nap. Pregnancy stuff I guess."

"I'll walk you back."

"Don't worry about it. I'm sure the others will drag you along somewhere later. You should stay."

"I'd rather hang out at the hotel than go shopping."

"If you're going to sit in the food court, you might as well get some food." Gwen gestured towards one of the stands. "Look, they have snow cones over there! We should share one before I go."

"I can't say no to that." I said.

I let her pick the flavor, raspberry, and we returned to the table. I realized that we only got a single spoon, so I started back towards the stand.

Gwen stopped me, pulling me down to sit next to her as she said, "It's okay, we can share this one. Here, I'll feed it to you."

I was a little embarrassed as she scooped up some flavored ice shavings and brought them to her mouth. To my surprise, she leaned in for a kiss, slipping her tongue into my mouth and literally snowballed the snow cone to me. We shared a few kisses before we both recoiled, suddenly wracked with brain freeze.

"We should have seen that coming." Gwen giggled.

"Yeah." I responded, rubbing my forehead.

"I almost forgot! I was going to give you something!" Gwen said as she reached into her pocket. She produced a small heart-shaped paperclip.

"Thanks..." I said, trying to hide how underwhelmed I was. "I like it! Where did you get it?"

"I found it on the floor and thought it looked cute. It made me think of you so I thought you'd like it."

"Yep, it's almost as cute as you are! Thanks so much!" I lied. I mean what the fuck? The floor is gross! Naturally, I did not allow my face to reflect my true feelings.

"I knew you'd love it! I'm going to get going. Have fun today!" Gwen trilled, leaving me the rest of the snow cone.

I finished the snow cone over the next few minutes, then moved to the trash can to throw it away. I almost threw away the dirty heart-shaped paperclip too, but I felt bad about throwing away a gift so I slipped it into my pocket.

As I returned to my table, I nearly bumped into a greasy man wearing a poorly fitted suit as he stomped past me. He did not seem to notice me as he barked into his phone and flopped into a chair at the table adjacent to mine. I sat back in my seat and returned to my game. I did not mean to eavesdrop, but he talked so loudly that I could not help it.

"I mean it's fuckin' bullshit!" he ranted. "They fuckin' bailed on me! Me! Do they even know how big of a deal I am? They ought to be grateful that I even considered going with them in the first place."

I could not imagine why they would not want to go with a person like him. I wondered what he was talking about, and thankfully it seemed the person on the phone asked the same question.

"I don't know, some stupid band called Cream Drippers or something." the man continued. "It was front row seats and everything, and they bailed on me the day of the show! Fuckin' stupid dip shits! No, I'm not going anymore, I'll probably just burn the tickets. No, I'm not giving them to you, fuckin' charity case."

The person on the other line talked for a few moments, then the man growled, "Fine, bye." He hung up and put his phone down, pulling out a laptop and booting it up.

"Hey, I wasn't trying to listen, but I overheard that you have some tickets to a concert tonight. If you're not going, I would be willing to buy them from you." I offered, figuring that I could give them to Gwen and Brianna as a gift. I was pretty sure Brianna liked a band with a similar name in the area, and I was betting that these tickets were for their sold-out concert tonight.

"Heh, you want to buy some tickets from me? I don't need your money. Get lost dumb kid."

"Fair enough, I'll pay you even more than you spent in the first place."

The man rose to his feet, bloodshot eyes glaring at me out of his seething face. "Maybe you couldn't hear me with that thick skull of yours, but I'm not giving you a fuckin' thing you little runt." He spat, despite the fact that I stood a little taller than him. "I'm a big fuckin' deal kid. You couldn't pay me a grand to even look at your ugly mug, so I sure as hell ain't about to sell you my tickets."

"Sounds good man." I said and started walking away.

"Don't you fuckin' blow me off you fuckin' piece of... AHHH!" He grabbed the small of his back and hunched over, face wincing with pain. It seemed he got worked up and pulled a muscle or something.

"Are you okay?" I rushed to his side.

"Get back!" he grunted, pushing me away as he gingerly eased into his seat. I kept my distance, but waited around for a bit to make sure he was fine. He took some deep breaths, then sighed, "God dammit I need a massage."

"Uh, you know there's a massage parlor in this mall, right?"

"Fuck off, I'm not a dip shit. I used to go there all the time, but the owner won't let me in anymore."

"Damn, that sucks. Welp, I guess there's no solution to that problem."

"I'll tell you what kid. If you convince her to let me in again, I'll give you these tickets. Sometimes women listen to little shrimps like you."

"I guess I'll go ask her, I'm not doing anything else after all." I strode away towards the massage parlor.

"Hello!" A sweet Asian lady chimed as I walked in. "Would you like a massage?"