Pool Party Surprise

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.