4 comments/ 50393 views/ 41 favorites Pool Party Surprise By: DPWestley Like they say; it's good work if you can get it. I had scored another housesitting job for another couple who were off to the Caribbean for a couple weeks. I had earned a reputation in my upscale neighborhood starting years ago when I was babysitting for couples when they would go out to their galas and benefits and dinner parties. I had been prompt, clean, responsible, good with their kids, no boyfriends over; the perfect babysitter. Word of mouth had been good for my extra-income career, and I transitioned into housesitting after graduating high school. I was still prompt, clean, and responsible. I didn't have to worry about their kids - except the furry ones - and now I could bring over a boyfriend if I wanted. These homes were beautiful and most were designed for entertaining. Custom built pools, hot tubs for ten, grills, gazebos and shaded decks, all with privacy from prying neighbors. I was out to lunch with my high school besties, Dawn and Gracie, telling them the good news. "The Millers are leaving tomorrow for Bermuda," I said as we waited for our food. "Their place is to die for. We should totally plan a pool party for this weekend." "Oh, Steph, that would be perfect," said Gracie. She was a pretty brunette who I'd met in 6thth grade, and we had been good friends ever since. "I'm done with finals and I just need a nice relaxing weekend." "Totally," agreed Dawn. She was a sexy red-head, always the vixen and the one the guys went for first when we went out. "On top of finals, one of the girls at work quit three weeks ago and I've been working extra hours ever since. I practically live in those awful orange shorts, and the smell of wings is starting to make me sick." She wiggled her giant rack back and forth, pantomiming. "Welcome to Hooters! Gag." "Dawn, you look great in that outfit," I told her. "I'll bet the tips are rockin'." She gave us a 'no-shit' kind of grin. "And I still get damp seeing you in those shorts, Babygirl," said Gracie. They were both Bi, and had been on and off during high school whenever they got tired of boys. Dawn leaned over and gave her a peck. "Thanks," she said. "Ooh, maybe we should all ditch the guys and have it be just us girls," she said excitedly. "So I can watch you two sneak off and scissor every five minutes," I protested. "I get you're into that, but I need dick; no way. Besides, Brad already knows, and I'll bet he's telling those lucky fuckers as we speak." The waiter came by and filled our tea glasses, his eyes locked on Dawn's 32F tits spilling out of her push-up bra. She smiled and winked at him, leaning over to grab a sugar packet and giving him a nice view down her cramped cleavage. The poor guy lost track of time and overfilled her glass, spilling some tea on the table. "Oh, man," he said, sheepishly. "I'm so sorry, ladies. Let me clean that up." "You got me all wet," Dawn pouted in her most alluring, breathy voice, torturing the poor guy. He tried to ignore her and toweled up the spill, running away before his boner would really embarrass him. "You're such a slut," I told her in our familiar, teasing manner. "Now he's gonna have to go rub one out so he can get back to work." "Shit," said Gracie, looking back at his retreating form. "I hope not. I've got to eat and get out of here. I'm supposed to meet Jack in about an hour." "What the fuck," I said. "I thought we were supposed to hang this afternoon. We don't get to see each other as much anymore." "I know, Stephie," she said. "But we're supposed to go look at apartments." "That's right," said Dawn. "You two are moving in together. So grown up," she teased. "God, don't remind me," Gracie whined. "I don't know if this is what I want. Jack's totally amazing and everything, but it seems like we're going too fast." "At least he's mature," I told her. "Most times I think Brad would rather play with Xbox than my box." They both giggled. "Seriously, you guys! The other night he gave me that, 'Five more minutes' crap, so I snuck my head in his lap and started blowing him." "Oh my God, Stephie," Gracie said. "What happened?" "He tried to keep playing for a few minutes, but I'm no slouch, so he lost his concentration and fucked up his level, or whatever. I still sucked him off, but I swear, I think he was pissed. Not to mention that I had to wait for him to go to sleep so I could get the toys out and take care of myself. Again." "I swear, Steph," said Dawn. "I fuck guys and girls, but I've never seen anybody as horny as you." She turned to Gracie and pointed at me. "This one loves the cock." "She certainly looks insatiable," Gracie responded, right on queue. The food showed up at that moment, delivered by a different guy, and we ate so Gracie could run off to meet Jack. I covered her tab and Dawn and I headed for the doors. Outside, we hugged and started toward our vehicles in opposite directions. "Hey," she shouted back at me. "Try not to suck any dick on the way through the parking lot!" I smiled and kept walking, flipping her the bird over my shoulder. Three sluts raised by fucking Jay and Silent Bob. What a world. I picked the keys up from the Millers the next morning and waved at them as they drove off. I made a circuit of the house, making sure I knew where stuff was supposed to be in case we got a little rowdy this weekend. As was fairly usual in this neighborhood, the bar was stocked but not locked. It's not like I was a big drinker or anything, but most of the people I sat for didn't mind if I had a couple drinks. I was in college and they knew booze was everywhere. I was, after all, the 'Responsible Stephanie', and they trusted me. I spent the following day on my cell, coordinating with the girls and Brad for the party, and was really looking forward to letting go of the semester and spending some time with friends. Jack, as well as Dawn's new boyfriend Bryce were joining their girlfriends, so it would be the three couples like we often did. I bought a bunch of food we could grill, and the girls went with me for mani-pedis and bikini waxes. I didn't know about Dawn and Gracie, but Brad wouldn't have his Xbox, and I was getting fucked a lot this weekend. I brought over my clothes and other personal items for my stay and slept there for the first time. I woke up Saturday morning at the Millers' excited and a little apprehensive. Dawn went through guys like underwires, and I hadn't even met Bryce yet. She was always up front with her boyfriends about wanting to fuck girls as well, and they were all in at the beginning. What guy wouldn't be? But eventually they would freak out. Either the girls Dawn brought home were straight up dykes and wanted nothing to do with the boyfriend, or even if the guy was getting the occasional three-way, they would start to get jealous or something. But I knew her type; he'd be a hottie, for sure. I felt a tingle of excitement at the thought of spending all day watching three good-looking guys around the pool, all of us flirting and making out with our men. I was getting wet. I jumped out of bed and went into the bathroom. No sense having to pee the whole time I was playing with myself. After I peed, I started the shower to let the water warm up. I admired my body in the mirror while I waited. I cupped and lifted my 34Cs and turned side to side, checking the profile. Good to go. I let go and they bounced nicely. Check. I spun around and stood tippy-toe, looking at my ass over my shoulder. Nice apple shape and I could still see daylight between my things. Freshman Fifteen, my ass. I smacked one cheek and my whole ass jiggled nicely. The water was getting, warm, and so was I. My nipples were hard, and running my hands over my body and watching in the mirror was definitely working. I ran my hands down over my flat tummy down to caress the fresh smoothness of my pussy lips. I worked them up and down, opening and closing my slit until my clit began to grow out from its pink little hood. Images of Dawn's various boyfriends flittered through my mind as I got my juices flowing. They had usually been the cutest and best athletes during high school, but after graduation she had branched out, getting hot bikers and bouncers, the occasional smokin' lawyer or club owner. I remembered that she had said Bryce was in film. Maybe he was a stuntman or an actor. I let my imagination run wild. Some of my toys were on the sink, cleaned from last night's fun. The Miller's walk-in shower has a bench and one of those removable, massaging shower heads, so I needed one hand free. I grabbed my trusty acrylic butt plug and got in the shower. I luxuriated in the feel of the warm water running over my skin, stimulating my already tingling skin. I love the indulgence of masturbation. I made sure I was all wet, then lifted one leg up on the bench and worked the butt plug into my pussy, getting it nice and juicy. The tapered length slid in and out, filling me nicely. I pulled it out and placed the tip against my puckered little ass hole. I relaxed and slowly worked it in, finally popping its largest point past my sphincter muscle. I love the full feeling in my ass; it's strange and arousing all at once. I grabbed the massaging shower head and sat down on the bench with one leg up. Ladies, if you haven't got one of these, get one. I rotated the dial until the pulsating water was coming out at a firm, but not brutal, pressure. I leaned back a little and aimed the spray at my pussy. Nothing any man has done to me has ever come close. "Oh, yeah," I moaned. "That's the ticket." I reached down and spread my lips apart, letting the thumping jets of water thrum against my pussy hole and my clit. Having my ass full and my cunt empty always got me hornier fast, and the pulsating water on and around my clit was electric. I clenched and relaxed my pussy muscles, wiggling the butt plug a little with each contraction. I was thinking about the mysterious Bryce being the missing cock my pussy wanted when my first orgasm crested through me. A surge of warm velvet heat rose up in my crotch and ran back down my legs. My tits seemed to burn with new heat, and my clit throbbed. My pussy muscles began to spasm, and the intensity on my clit was almost too much, but I had performed this routine before. "Oh, fuck," I yelled. "Fuck, fuck, fuck, yes!" Another wave crashed and I was past it now, I lay back, keeping the water pounding on my clit and found the butt plug with my groping hand. I slid the fat part of the butt plug in and out of my ass as orgasm after orgasm washed through me. My pussy clenched agonizingly, having nothing in it while I climaxed, but the sensations between my ass hole and my clit were like a live wire and I came again and again. The shower head eventually slipped from my weak fingers and broke the spell. I jammed the butt plug in one more time and clenched down for one last little spasm of pleasure. I lay panting for a while, just enjoying the warmth in the room and the warmth in my pussy. I relaxed and slipped the butt plug out of my ass and sat up, a little dizzy still. I thought that would hold me over for a while, at least until later that night when Brad and I were alone in the house. I got out, dried off, and cleaned my toy for the next time. I went back into the bedroom and got out my favorite bikini; a black and white horizontal stripes pair I'd picked up on vacation a few years back. The bottom had ties at the sides, and the top had ties behind the neck as well as in the back. I wrapped a sarong around my hips and then dried my hair. The really light blonde was showing up in streaks as I spent more time in the sun. I pulled it back and put it in a ponytail up high so it hung down just to my neckline. The gang was supposed to come over around 11:00, so I had plenty of time to prep. I made a light breakfast and opened up the back of the house. The forecast was for 74 degrees with scattered clouds and a slight breeze; Perfect pool weather. I made sure all the meat was thawed, seasoned, and marinated. I put ice and water bottles in a big cooler and placed it out on the patio in a shady spot. I made sure the condiments were ready and cut up a bunch of veggies for snacks and for hamburgers. I finished with twenty minutes to spare, so I found the stereo and dialed in a satellite station with the alternative and grunge we had listened to throughout our school years. I went out back and checked the pool and hot tub, making sure everything was good to go. The Miller's had speakers out on the deck, so the music was playing out here as well. It was already warm out, and the sun felt great on my shoulders. That and several orgasms this morning were wiping the stress of finals right out of mind. A chime broke me out of my reverie, and I went to the front door. Brad had arrived, so I let him in. "Hey, Steph," he said coming in. "You look great!" "Thanks," I said. "You, too, Baby." He had a Hawaiian shirt over board shorts and had actually made an effort with his hair today. I took his overnight bag and told him to check out the deck while I ran it into the bedroom. I stowed my toys before he had a chance to see the arsenal. Brad knew I had toys, but he didn't need to know the wide variety or that I took them everywhere. He was still checking out the place when I came back. "Nice place," he said. "You get to stay here for two weeks?" "I'll bounce back and forth to my place, but, yeah," I told him. "You want something to drink?" "Ooh, yeah," he said excitedly. "Whadda they got?" He saw the bar and made his way over like a kid on Christmas morning. "Don't go ape shit," I warned him. "The Millers were cool enough to have it stocked, but they'll be pissed if it's all gone when they get back." "Chill," he said, trying to ease my concerns. "I'm cool, I'm cool. Can I get you one?" I could hear ice clinking into glasses and he was checking the inventory when the bell rang again. "Hold on," I said. I went to the door and opened it to see Gracie and Jack. "Hey, you guys! Come on in." Jack had a case of beer in each strong hand, and I told him where to find the cooler. Jack looked great as usual, his nice arms flexing with the weight. He was the tallest of the two guys, at 6'2", and was wearing a tank top and a swim suit that showed off his fit frame. Jack was a bit older than Gracie and I. He was a roofer, so he always looked lean and fit. They had been together for almost two years now, and he didn't seem to mind that Gracie sometimes hooked up with other girls. Hell, he had even asked her to live together. He was a good guy and I was happy that she was with him. I hugged my girlfriend as Jack headed for the deck. We complimented each other's outfits and she came in. Gracie had tight capris and a halter top over her one-piece. It was almost like seeing her underwear sticking out of clothes that were supposed to hide them. I doubted she would stay in her top layer for long. Brad greeted them, took drink orders, and came over to us as Jack made his way out back. "Here you go, Steph," he said. "And one for you, Gracie." He handed us highball glasses full of clear liquor and ice. "Rum Rocks." I took a nice long draw, and was watching Jack unload the beer when the doorbell rang again. "Brad, Honey" I said. "Go help Jack while I let them in, okay?" "Sure." He grabbed the other drink from the bar and headed to the deck. Before I could get to the door to open it, Dawn was coming in. "What's up, Bitches," she yelled. She rushed towards me, arms extended for a hug and I could see the mysterious Bryce coming through the door as I hugged her. Huh. At first impression, I thought maybe Dawn was losing it. He was about 5'8" and had close-cropped hair. He wasn't gorgeous, but he had a nice smile. Dawn was still squeezing me so he shook hands with Gracie. He was wearing loose jeans and a dress shirt. The sleeves were rolled up a bit, exposing a lot of ink on his forearms. He looked like he was in pretty good shape, but not Dawn's usual eye candy. Dawn broke our hug and repeated the hug routine with Gracie, leaving me to get another eyeful of Bryce. He stepped toward me and that's when I saw it. There was an anaconda in his pants. My pussy twitched and I swallowed, trying to find his face and not stare at his crotch. "You must be Stephanie," he said in a smooth, masculine voice, his hand extended. "I'm Bryce. It's nice to finally meet you. Dawn can't stop talking about you three." I shook his hand and tried to think of something witty. His hands were very smooth, but strong. Oh, my. "Hi. Yeah," I sputtered, still a little flustered. "Yeah, we've been friends forever." I finally managed to let his hand go. "Come on in. Do you want a drink?" "Water would be great," he said. "Um, sure," I said, a little confused. Was Dawn dating a recovering alcoholic or something? "There's water in the cooler out on the deck. C'mon, I'll show you." Dawn and Gracie were still exchanging pleasantries and I led Bryce out to the deck. Brad and Jack had managed to get all the beer in the cooler finally, and were sipping their drinks and chatting when we arrived. I made introductions all around, and I couldn't help staring at the swinging meat in Bryce's trousers whenever he wasn't looking at me. God, it was huge. His pants were very relaxed and I could still make out the shape now and then, running down one thigh. I excused myself before anything embarrassing happened. I made it back to the girls, still in shock. "Dawn," I said. "What the fuck is in his pants!" They broke into a raucous round of laughter, waving at their eyes and trying to keep it straight. Dawn was the first to recover. "Oh, Stephie," she said. "It's marvelous." She held out her arm, bent at the elbow, and made a fist. "It's fucking huge, you have no idea." She pointed out at the guys, drawing a glance from Gracie and I. "That? That right there? He's not even hard yet." She broke into another fit of giggles as Gracie and I looked at each other in disbelief. "Where did you meet that guy," I asked her, "at a porn convention?" Now Dawn was hysterical with laughter; she was hopping up and down and laughing, her giant rack bouncing up and down. It was infectious. Gracie and I were smiling and watching her. She managed to stop long enough to spin around and face me, pointing at me with one hand and touching her nose with her other index finger. "Bingo," she sputtered between giggles. "Got it in one, Bitches." "Are you fucking serious," Gracie asked her in disbelief. "He's a fucking porn star?" She looked back at Bryce and the guys. I was still watching Dawn get her shit together, waiting for an explanation. "Well," Dawn answered, "not a star." She was trying so hard to keep from laughing that tears were streaming down her cheeks. "But he's up and coming," she managed to barely get the joke out before she completely lost it. She retreated to a comfy chair in the den and covered her face, bent over in laughter. I looked back at the guys. They were watching us, but were still talking and staying out on the deck. I downed my drink, trying to ease my irritation at Dawn's little inside joke, or whatever it was that had her in giggles. Gracie was smiling easily at her old girlfriend. Her glass was almost empty as well. "Gracie, you want another?" Gracie slammed hers and nodded, grimacing, and handed me the glass. I went to the bar and poured three just like it. By the time I had finished, Dawn seemed to have regained her composure. I handed them each a drink, still a little confused by Dawn's behavior. I waited for her to take a sip and made sure there wouldn't be a relapse. "Well," I said, "you want to let us in on the joke?" Dawn smiled up at both of us and took a last calming breath and another drink. "It's just," she began, struggling for words. "The looks on your faces when you finally noticed his cock; fucking priceless." She smiled at us, trying the old Dawn charm to get us to lighten up. Gracie finally giggled, looking at me. Pool Party Surprise "It was kinda funny, Steph," Gracie admitted. "I guess I probably looked the same, but your eyes almost fell out of your head." That image, along with a dozen like it from all the cartoons I had watched growing up, finally got me. I laughed along with my friends at the absurdity of it all. We settled down and I raised my glass in a toast. "Ladies," I said as they raised their glasses along with me, "and I use the term loosely; to big dicks." They echoed the toast and we downed what was left of our drinks. It was starting to feel more like a party as the burning warmth of the rum spread in my stomach. "What's he like in bed," I asked Dawn. "I mean, how does a cock that big feel?" Dawn rolled her eyes and fanned herself like a southern belle. "My stars and garters," she said with a drawl. "At first, it was like, 'no fuckin' way,' but then for a couple of days I couldn't get enough." She looked wistful as she recalled the memory. "And now," asked Gracie. Dawn looked up at her with a sly grin. "Now I think I'm ready for a break." Gracie held out her hand and helped Dawn up from the chair. They kissed innocently, but the old chemistry was there. "Good," said Gracie with a strange finality. "Fuck it. Let's go swimming!" We all spent the next few hours grilling and getting to know each other. Once I had some food in me and my earlier buzz had settled into a nice holding pattern, I felt more comfortable drinking beer. I noticed Bryce never drank at all. I asked Dawn about it, but she played coy with me and wouldn't give me a straight answer. As I had guessed, Gracie had stripped off her clothes down to her swimsuit immediately. It was a salmon one-piece that really accentuated her tall, lean figure. It was French cut, showing off her heart-shaped ass and long, tanned legs. I had always envied her height, since I was only 5'5" compared to her 5'9", but at least I had bigger tits. She wore a 34B, but they looked right on her; not too small, not too big, like Dawn. Dawn had worn her usual black string bikini, with barely enough fabric covering her nipples and pussy to qualify as clothing. The color stood out against her ginger skin, and the guys were definitely noticing those giant, freckled tits. There were, of course, the requisite number of wardrobe malfunctions, like she didn't know how to deal with her two unruly children. She would dive in the pool and her top would come off. She would bend over to get a beer from the cooler, and her tits would fall out. I was used to it. Gracie was watching with an intense look of desire. I was used to that too. Everybody seemed to be watching Dawn except me. I kept sneaking looks at Bryce. He and the other guys had finally lost their shirts, and that was a good thing. Bryce wasn't super muscular, but he was cut. He must have had, like, two percent body fat or something. I could see every little muscle writhe under his tattooed skin with any subtle movement. The ink I had seen on his arms continued up for full sleeves. He had nice work done on his back and his pecs, as well. Lots of tribal work, Celtic knotwork, suns and moons and the like; nothing offensive or vulgar. He had an easygoing manner to him, and I was getting a little horny wondering what his cock looked like. After a few hours and a few more drinks, the subtle shape of it under his pants wasn't as jarring, but it was still there if I looked. Brad and Jack had gone into the water with Dawn and Gracie, and they were choosing up teams for chicken fights. Bryce was looking on and smiling. I went over to join him in the peanut gallery. "No way, Dude," he was yelling. "She's used to having you between her thighs, man." He must have been talking to Jack. Everybody laughed and the four in the pool were splashing each other and talking shit. "I don't know," Jack was saying, trying to defend his position. "I might throw out my back trying to lift up Dawn's massive tits, man." There was more laughter. "Those are no longer flotation devices when they're in the air." "Here, fucker," Dawn said. "I'll lighten the load for you." She pulled the little triangles up off of her nipples and took the whole thing off over her head. Catcalls and whistles rained down on her as she chucked her top onto the deck. "Better?" Jack raised his hands in defeat and made his way over to Dawn's side, leaving Brad with Gracie. He looked over at her and back at Dawn. "No fair," he said. "I have to get distracted by the twins? Gracie has to go topless, too." More catcalls and a chant of, 'take it off,' erupted from the other three. Gracie blushed, but she had never been afraid to keep up with Dawn and her exhibitionism. She peeled the shoulder straps down and exposed her tits, tucking the extra fabric into the bottom half around her waist. "Better," she asked Brad, and I could tell he approved. Bryce and I were clapping, and that seemed to settle the debate over sides. They went about getting set, with the guys submerging under the girls legs and lifting them up on their shoulders. I snuck a glance at Bryce's jeans, thinking he might be more interested in the water games. He was sitting on a barstool with one leg - that leg - propped up on a lower rung. Bryce's pose had slightly tightened his pants and I could see the length of his cock running down his thigh. Even limp, I don't think I had ever seen one so long. Girth was a little hard to determine, but it had to have been ten or eleven inches as it was, and the ridge of its head was clearly visible near the tip. I realized he was looking at me, and I turned away, trying to cover, but I knew he'd busted me. "It's okay, Stephanie," he said as the chicken fight was getting raucous. "I had to get used to that a long time ago." I turned back to him, and he had a kind look on his face. "Hell, I got so used to it, now most people have to pay to see it," he said with a chuckle. That eased my embarrassment a little. "Sorry," I said. "It's just...I don't think I've ever seen one that big." "Probably not," he said rationally. "I'm in the business, and it's one of the bigger cocks out there." That surprised me. "Jesus," I exclaimed and looked back down at it for a second. "You mean, there are bigger cocks than yours?" He laughed at my disbelief. "Yeah, a handful," he said. "No pun intended." He smiled and I felt myself finally relaxing around him. I had spent time chatting with everybody during the day, but I hadn't spent any time one-on-one with Bryce, and my curiosity about his cock had mingled with my attraction to him and my perpetual horniness. I had been uncomfortable around him for hours, but now, he was putting me at ease with his casual confidence. Don't get me wrong, I was still attracted; I just wasn't nervous anymore. "You want a drink," I asked him again, thinking I might get a different answer. "I really can't," he said. "It's a business thing." He seemed reluctant to say any more. I excused myself and went into the house to hit the bar. I kept thinking about Bryce's cock, and imagining how much bigger it might get, how it might feel stretching out my pussy or my ass, what he might taste like, and how much I could get in my mouth. I poured a double, upended it and tried putting it out of my mind, but it was in vain. I was getting wet again. More yelling and clapping and catcalls erupted from the deck, so I went back out to see what was happening. The chicken fights must have ended, as Brad was climbing out of the pool. He really was a good-looking guy and I was glad to be with him. The water ran off his smooth chest and back as he emerged. He turned to go to his towel hanging over a deck chair, and his wet trunks were plastered to his nice, firm ass. Oh, yeah. He was definitely getting fucked later, that's for sure. Jack had sat on the edge of the pool looking back at Gracie and Dawn. They were still only topless but it didn't look like it would last for long. They were face to face, close, their hands running over each other's faces, arms, and tits. Gracie's nipples stood out long and hard as Dawn traced little circles around them. Dawn leaned in and kissed her, pressing her huge melons over Gracie's chest. They embraced, kissing deeply and their hands explored each other's backs and ass as their passion grew. I made my way over to Brad who was drying off and hadn't seemed to notice the action in the water. "There they go again," I said to him. He turned around to me and then caught my eye to see the girls making out in the pool. "Every time they get drunk," he confirmed. He looked at Bryce who was just watching. He leaned in to whisper in my ear. "At least Bryce doesn't seem to mind, like so many of the other ones." "C'mon," I said to him. I was a little drunk, and a lot horny, and I didn't want to sit here watching my friends make out. I pulled Brad off toward the chaise lounges. The girls were climbing out of the pool, stripping off their suits and looked to be headed off to the shady confines of the gazebo. They gave us a glance and a wink and were sending fetching looks toward their boyfriends. I didn't care; I wanted some cock pretty soon, and having Brad oil me up would go a long way toward that end. "I want you to put those great hands to some good use," I told Brad. I grabbed a bottle of tanning oil from my beach bag and tossed it to him before lying down on my stomach on one of the lounge chairs. I couldn't see what had happened with the other four, and I began to care even less as Brad trickled the warm oil on my back and legs. Brad's deft hands began to work the oil into my shoulders, spreading the slick oil around and massaging my muscles. His hands really were amazing. They were one of the first things I had come to appreciate about him when we started dating. He moved down my back and worked the sore spots in my lower back. I was getting wet and was fantasizing about Brad fucking me as his hands worked me over. I moaned softly with the relaxation and pleasure. He started working my legs, slicking the oil from the back down each side, working from my thighs down past my knees. He massaged my calves a little, and rubbed the oil into my feet. In my fantasy, Brad's cock was growing, and growing, and pretty soon it was this massive slab of meat pounding into my cunt. I realized he had transformed into Bryce, but I just went with it. Brad's hands were working back up my legs, paying a little extra attention to my inner thighs and getting closer to my bikini. I spread my legs a little to give him access and he obliged, rubbing even higher and tracing random fingers over my pussy and ass. He pulled the ties on the sides of my bottom and pulled the fabric down, exposing my ass cheeks. He poured more oil over my ass and began to rub and squeeze my ass. "Mmmm, yeah." I moaned. "That feels great, Baby." I clenched and relaxed my ass and pussy muscles along with his movements, anticipating his cock thrusting into me. "Your ass looks great, Steph," he said, his voice heavy with lust. He dribbled more oil down my ass crack and began working his fingers up and down my crack. He spread my cheeks open and was running his thumbs up and down from my pussy lips to my ass hole. Brad had never really showed any interest in ass play, and I had never pushed him. "That feels really good," I said when his focus was on my little rosebud. "Ooh, yeah." "Oh, you like that, huh," he asked. I moaned my pleasure and wiggled around appreciatively. "You want something in there?" I snuck a look back at him. His greedy eyes were focused on my oily ass. He didn't seem disturbed at all with this new development. "Mm, hmm," I purred. "I want all my holes filled today, Baby." He worked a finger down, now intent on getting in my ass. I relaxed and his finger slipped in easily. He had a thumb down my slit and was massaging my pussy as he wiggled his finger around, exploring my ass. "Oh, fuck yeah." Both his hands were working my ass and pussy, and I was getting close to an orgasm when I felt my top being untied. I opened my eyes and saw a pair of jeans near my head; Bryce. I looked up and he was smiling down at me while he untied my bikini top. I looked back at Brad with a questioning look, and he just gave me a smile and a little nod. My heightened senses, alcohol buzz, and wet pussy were keeping me from comprehending exactly what was happening, but I knew this felt good, and I really wanted to see Bryce's cock. Once my ties were undone, I flipped over on my back and spread my legs. Brad tossed my bottoms away, and Bryce tossed my top as I moved my hands tentatively toward his pants. Brad moved down and started licking my dripping snatch, slipping two fingers into my ass. I ran my hands along the length of Bryce's cock, feeling its warmth and size under his pants. It twitched and throbbed a little with each touch, and was starting to grow. Bryce undid his belt and unbuttoned his pants, letting them slowly slide down. I marveled as he revealed first his tight abs that ran smoothly down to a small, manicured tuft of pubes above the root of his cock. The jeans slipped down and I began to see it emerge, inch by inch. It was smooth and thick, tanned like the rest of him, and it just kept going. I moved my fingernails up to the exposed portion as his pants slipped further down, tracing a light touch along the shaft. It twitched and moved like nothing I'd ever seen. Brad was lapping away and fingering deep in my ass as the last of Bryce's massive cock came free. I had a soft orgasm as I finally saw the whole thing spring toward me. No amount of blood was ever going to make that thing stand straight out, but it was already bigger and thicker than it had been just a minute ago. Its girth was catching up to the width of the uncircumcised head, giving it a sleek, eel-like appearance. It throbbed and swelled with each heartbeat, dangling over my face. I propped myself up on my elbows and took the head in my mouth. Bryce hummed his pleasure as my warm mouth stretched around his head. God it was big. Bryce grabbed the shaft and guided his slick, thick cock in and out of my mouth, rocking his hips gently as I worked my tongue around the head, rolling back his foreskin and teasing the crown. I tried to take a little more, but the angle was bad. Bryce must have noticed so he moved around to stand behind my head so I was lying down with my head thrown back and his cock sliding into my mouth from above. I reached my hands up to caress his smooth, strong thighs as he rocked in and out of my stretched out mouth. I cupped his balls and gently pulled on his hairless sack, feeling his cock throb in my mouth as he moaned. Brad pulled his face away from my soaked pussy and I vaguely heard him ditch his swimsuit before he climbed back onto the lounge chair. Bryce was stroking one hand up and down the length of his cock, one hand on his hip, moaning and coaxing me on. "Yeah, Steph," he said. "Suck my cock, Baby. You know you like that, don't you?" I mumbled my pleasure around his massive organ, slobbering and running my tongue out along the top of his cock. Bryce lifted my knees up and spread my legs. He slapped the head of his cock a few times against my pussy, sending shivers through me. Bryce pushed a little deeper, testing my limits, and then Brad was suddenly in my ass. My eyes bulged as I was filled from both ends. Brad buried his firm cock in my ass until his balls slapped my ass crack. He held there, and I clenched around him, feeling his hard, warm cock filling me like he never had. Bryce relented on his thrust into my throat and I caught my breath, fighting a gag and swallowed all the spit in my mouth, sucking hard on him. I was so wet that my juices were running down onto Brad's cock in my ass. Brad began pumping into my ass, holding my ankles up and driving deep into me. He was breathing heavy and moaning, and I knew he was close. This had to be pretty erotic for him, having his girlfriend banged and getting his first anal at the same time. I closed my eyes and reveled in the sensations as two cocks drove into me. My empty cunt was aching for cock, and it was getting me that much hotter. "Oh, shit," Brad cried out. "I'm gonna cum, Baby!" He thrust twice more, balls deep in my ass, before I felt his load surge up his shaft and erupt in me. The hot seed sprayed deep in my ass and I came hard. I tried to yell out, but my mouth was too full. Bryce pulled out his massive cock and my grunts and groans escaped as Brad and I climaxed together. "Fuck, yeah, Baby," I yelled at him. "Oh, fill my ass. God, that feels good!" Bryce reached down and tweaked my nipples as the waves crashed over me. His monster cock throbbed, glistening on the end from my spit. I could see I hadn't even gotten a third of it my mouth. My orgasms subsided and Brad pulled out of my dripping ass, letting my legs down, and climbing off the lounge chair. Bryce grabbed my hand and pulled me up. I stood, and he lay down on the chair, pulling me onto him. I noticed Jack was sitting nearby, stroking his cock and watching everything. Bryce's cock had ended up trapped between our bellies. I could feel the solid length of it from my pussy almost to my ribs. There was no way all of that would fit in my cunt, but I wanted as much as I could get. I sat up and straddled him, sliding my pussy lips along the thick shaft. His hands found my tits and squeezed and massaged them while I lubed his cock. I went to lift it into position, but had to almost stand up to get it to my hungry little pussy. Somehow we managed, and I felt the hot, swollen head pushing its way into my tight, wet hole. I worked and wiggled and the thick meat slowly worked its way in. I remembered how it had felt the first time with my first boyfriend. I had fingered away my hymen years before, but the feeling of Tommy's dick expanding my virgin hole had been an exciting mixture of pain and pleasure. I never thought I would feel that kind of new sensation again. Bryce's cock was bigger than any toy I owned, and he was stretching me in a delicious mixture of pain and ecstasy. I had seen the monster dildos in the adult store, but I figured they must have been gag gifts for bridal showers, or something. Who would ever want something like that in their pussy? But now I did. I moaned and squeaked as I worked up and down bit by bit, my pussy sore but aching to be filled. I looked down between my legs and marveled as his monster cock was slowly inching deeper and deeper until I finally felt him against my cervix. I shuddered as I finally had as much in me as I could get. I could still see at least six inches of his cock outside of me. I tried to squeeze him, but it seemed pathetic against the solid thickness of his massive erection. My walls stretched to their limit, I began to move slowly up and down along the shaft. I was sopping wet, so it was becoming easier as the pleasure began to override the discomfort. Bryce had his hands on my hips, helping me up and down. I found my clit and began rubbing as my heat rose again. Soon I was moving at a steady pace, bucking against his cock, and slamming it into my depths. My eyes were closed tight as my fingers rubbed furiously on my hard clit. I felt a new presence near me and opened my eyes to see Jack's cock in my face. I didn't even think, instinctively taking his cock in one hand and cramming my mouth down on it. Bryce held me still so I could work on Jack, and he started thrusting his hips up into me. Bryce doing all the work was somehow more invasive than before, and I shuddered with a strong orgasm, moaning around Jack's cock as he thrust into my mouth. I worked my clit furiously and willed the waves to keep coming. My humming and stroking were getting Jack near the edge. "Oh, yeah, Stephie," he groaned. "Fuckin' suck it hard. Yeah." I sucked furiously and stroked him as my mouth moved along his slippery shaft, all the while cumming and cumming around Bryce's huge hard-on. "Oh, shit," Jack said. "I'm gonna cum." Before he could make the choice, I grabbed on tight to his cock and held the head in my mouth, feeling his cum spurt into me again and again. It was salty and bitter as usual, but I loved it. Pool Party Surprise I sucked and drained and cleaned Jack's cock before he finally stepped away, leaving me atop Bryce. He was still slamming his python against my cervix. I looked down again and saw a coating of frothy juices dribbling down his exposed cock. I'd never worked up a lather before, and, God, it was hot to see. Bryce continued like that for minutes before finally lifting me off of his cock and bending me over on the deck chair. Facing this way, I could see Gracie and Dawn emerging from behind the wispy curtains on the gazebo. They were naked and walking together, arms around each other's waists, watching as Bryce guided his cock back into my pussy from behind. He gripped my hips and slammed every possible inch back into me again. "Oh, fuck," I yelled, my eyes rolling back. "Fuck me, Bryce. Slam my tight little cunt." I had already finished Brad and Jack, and now it was Bryce's turn. He seemed capable of going forever, and I wondered how long he had been pumping me. "I want you to cum all over me, Baby. Gimme that fucking load!" He began punishing my pussy again, ramming in and out in long, forceful strokes. I felt hands on me and opened my eyes to see Gracie fondling my tits. She lay down beneath me and started sucking my nipples as she squeezed and massaged me. "Ooh, yeah, Baby," Dawn was saying from behind me somewhere. "Fuck that tight little pussy." I felt her hair tickling my ass and then she was licking my ass hole as Bryce pounded me. "That's fuckin' hot," he said. "Oh, yeah" he was groaning and his cock was swelling in me. The feel of Gracie sucking my nipples while Dawn licked my ass pushed me over the edge and I came yet again, screaming incoherently as the waves crashed over me. "You ladies ready? I'm gonna cum." "Stephie," Dawn said, "you're gonna find out why he doesn't drink. Trust me, girl, you wanna taste his cum." Bryce thrust into me another minute or two as my orgasms subsided. When he felt me relax, he pulled out and spun me around. I sat on the edge of the chair and opened my mouth, waiting for his load. Gracie was behind me, her arms around and still working my tits as she watched over one shoulder. Dawn was on her knees, both hands stroking up and down on Bryce's massive cock as he worked a hand over the swollen head. He was licking his lips and grunting as he worked to get off. "C'mon, Baby," I coaxed him on. "I wanna taste your hot cum." "Yes. Yes. Oh, yeah," he yelled, and the first sticky rope of cum erupted from the tip. Most of it made it right in my gaping mouth and it was hot and sweet. I had no time to marvel at the wonderful flavor before another shot hit my face. Bryce aimed a shot at Gracie and she flinched as he splattered her. Dawn grabbed his hand and directed the rest into her mouth, making yummy noises as she savored his tasty seed. I have never tasted cum that good. I love giving head, and had tasted my fair share of guys. It was always the bitter, salty taste that I had gotten used to, and eventually grew to like, but this was nothing like that. I swallowed the load in my mouth and started wiping the semen off of my face with a finger and licking up as much as I could. It was so good. "Oh, wow," Gracie was saying. "It's sweet!" She was doing the same as I was, wiping her face and licking her fingers. Dawn was still sucking on Bryce, and I could understand why. He was glistening with sweat and smiling down at us. "No booze, no smoking, no junk food," Bryce said, explaining his secret. "I rarely eat meat. And the girls keep coming back for more. Right, Baby?" Dawn gave a satisfied murmur around his cock. Gracie and I finished cleaning up as Dawn drained the last of his load. She let his deflated cock slip from her mouth and stood, facing me. "Well, well, well," she said. "I knew you had it in you, but I really doubted I would win." I looked at her, confused by her statement. "Win what," I asked her. "Brad," she queried over her shoulder at my boyfriend. "I fucked her in the ass," he replied, "and she let me cum in her ass while Bryce was in her mouth. She got off on it." "Jack," she asked, again, keeping her eyes on me the whole time. "Yup," he replied. "She sucked my cock while riding him; Swallowed my load like there was nothing to it. I'm pretty sure she was cumming the whole time." By now I was really confused, and starting to smell a rat. "What the fuck, Dawn," I said, a little annoyed at her. "Win what?" "I bet these fuckers a hundred dollars each that Bryce's cock would get you so horny that you'd do all three of 'em." I gaped at her in shock. She had set this whole thing up to test me. And I had fallen right into her little trap. But I had never cum so hard, so many times. I shook my head and smiled at Dawn, realizing that she had opened a new chapter for me. "You're such a slut," I told her for the thousandth time. She smiled in victory. "Pay up, Bitches!"