Lauren the Bridesmaid

"We're getting married on St. Thomas and I would like you to be my best man." My brother was getting married for the fourth time and I was going to be best man for the third time. I knew the routine. I didn't know much about his bride, except she was like 15 years younger than he, with two weird kids. I'd met her once, and left unimpressed, but I wasn't marrying her. My soon-to-be ex-wife was anxious for me to go, probably because she wanted to fuck one of her young grad students all weekend.

I am my brother's only family, but I heard that his bride had six sisters, her Mom and step-Dad who were all coming down. They were renting a big oceanside condominium with multiple bedrooms and wanted me to stay in one of them. The condo complex was next to the Ritz. Business had been good, so rather than share a condo with a bunch of strangers I took a suite at the Ritz. It was pretty empty, so they gave me a steep discount. My room was on the top floor, with a concrete railing on the balcony overlooking their private beach. My building had almost no one registered, as I guess it was the slow season.

I took a short nap and sauntered over to the restaurant next to the condo complex where we were meeting for dinner. They had already been drinking for a while and were pretty jolly by the time I arrived. My brother's spouse-to-be was happy and cute enough. Her other sisters were as plain as the midwestern tundra they came out of. But her youngest sister Lauren, much younger than I, was truly beautiful. Keeping with the midwestern tradition, she had the girl next door beauty--blonde hair, blue eyes, a taut figure and nice tits that were bunched up into a cleavage that demanded your attention. When Lauren introduced herself, I wasn't expecting such a gleaming smile. I was quite speechless for a second, eyes glued to the deep valley between her breasts.

"Hi I'm Lauren! Your brother has told me so much about you..." she paused as she noticed what I was looking at, "...but he didn't tell me everything, it appears!"

"Ooh, sorry!" I stammered, rousting out of my trance, blushing bright red. "I mean, so nice to meet you!" Everyone at the table saw that I was busted and burst out laughing.

Lauren smiled and laughed brightly, "Oh Jimmy, we are going to get along just fine!" No one had called me Jimmy since around age five, but I wasn't about to correct her--at least she knew my name.

With that embarrassing encounter behind me, the weekend was shaping up like you would expect for a small wedding. The following afternoon we had a rehearsal on the beach, followed by a long alcohol laden rehearsal dinner. I chatted with Lauren on several occasions during the day and evening, but only like I did all of her sisters. Just guests at a wedding.

Sunday was wedding day, and now dressed up we went back to the beach for the ceremony. Lauren outshined all of her sisters; her hair drawn up into a bun with tropical flowers intertwined. Her dress lacked the bodice of the first day but clung tightly to her shapely figure. I kept stealing glances at her during the short ceremony. She smiled when she caught me looking, and even appeared to blush a bit as she looked away. But I knew in my heart that was the overactive imagination of a horny middle-aged guy. I didn't think any more about it.

The reception was held in an oceanfront restaurant, attended by the 15 or so people in the family. I happened to sit next to Lauren, and we chatted about her work as a fashion buyer, about my son (who was almost exactly the same age as Lauren) and shared funny stories about our siblings. After the reception, we were all supposed to take a boat to a nature preserve on a separate island, mostly as a concession to my new sister-in-law's son who fancied himself a nature freak. Once I heard that, I knew I was going back to the Ritz, if only to hang out at the bar.

"So, Jimmy, can I get you a drink? I am heading over to the bar." We all had taken advantage of the open bar, but I could use one more mojito.

"I need the exercise. I'll walk with you." Lauren and I went to the bar in the next room to place our orders. As we leaned on the empty bar, I sidled up shoulder-to-shoulder with Lauren, probably too close. But she didn't move away. She laid her head on my shoulder, and I could smell the sweet fragrance of the flowers in her hair.

"I'm so glad you're here Jimmy. I was dreading the thought of spending the weekend talking only with Mom and my sisters. Fights would have broken out for sure." I put my arm around her thin waist and drew her close in what I hoped was a brotherly way.

"You're glad! I would have been stuck talking only with my brother. You have made this weekend a lot more fun."

Lauren sighed, "Now we have to change clothes and go to this stupid nature reserve. Little Eddie will be happy, but the rest of us will be dying, won't we?"

"Not me!" I said brightly. "I already told my brother that I'm not going. I'm going back to my luxe hotel and hang at the bar or the beach. Or both."

"Oooh, that sounds so much nicer," Lauren cooed. "I'm jealous."

"You could come too. They won't miss you, the focus is on entertaining Eddie."

"Hmmm...no I couldn't. It is supposed to be a family event." Lauren took a long pull from her drink.

"That family you don't like spending time with? You've got your bathing suit with you; the hotel has towels and robes. You could be sailing a Hobie across the bay or tramping through a nature reserve feeding the mosquitos. But you're welcome if you change your mind."

Lauren drained her mojito. "You're right. This is the only vacation I will have this year I am going to do what I want."

I finished my drink. "I'm going to say my goodbyes. I'll meet you in the parking lot."

Now I have to confess, I totally expected that Lauren and I would change clothes, head to the bar or the beach and I would watch Lauren flirt with the ripped young men who would assume, not unreasonably, that I was Lauren's dad.

We chatted about nothing in my rental car on the way back to the Ritz. It was hard to stay on the road as the slit in the front of Lauren's long gown fell open, giving me an unobstructed view of Lauren's tanned legs and muscular thighs. Lauren must have caught me looking but did nothing to cover up. She was teasing me, and I didn't mind a bit.

"They're white." Lauren said out of nowhere.

"What?" I had no idea what she was talking about.

"They're white." I looked quizzically at my lovely passenger. She was wearing a mischievous grin. "My panties. You've been straining to see, no?" I almost swerved into oncoming traffic.

"What? No! Geez, I'm sorry. Unh-huh." I was babbling and blushing bright red. Lauren laughed hysterically.

"You are a naughty one, Jimmy! It is so much fun catching you looking, and I love how embarrassed you get. It's okay. Honestly I love the attention."

I focused on looking straight ahead the rest of the drive, even though I could see Lauren inching her gown farther up her thighs. Out of the corner of my eye, I could see Lauren staring in my direction. I remembered with some horror that, being on the island and all, I had chosen not to wear any underwear this morning. The men dressed in baggy linen pants, so I didn't think it would be an issue. Without looking down, I could tell that my stiff cock was making a tent in the linen fabric, and Lauren had noticed. I was going to make a joke of it but was too mortified. Instead I slid one hand to the bottom of the steering wheel and tried to shield my erection from view using my forearm.

We pulled into the hotel and dropped the car with the valet. The bellman driving the cart to our building checked out Lauren head to toe, then noticed the pole in my pants. He grinned at me as we slid into the seats.

"How long are you and your Dad staying with us, Miss?" He addressed Lauren. Asshole. I'd ridden with him before, he knew I was staying alone.

"Oh he's not my Dad," Lauren laughed. "We just got married." She turned and kissed my cheek. Well played Lauren, I thought. I joined in.

"Oh yeah, I always wanted a trophy wife, isn't she lovely?"

Now it was the driver's turn to be uncomfortable. "I'm so sorry, sir, I didn't mean to imply..."

We laughed, "Don't worry about it, we have to get used to it, I guess." I put my arm around Lauren and pulled her close, kissing her full on the lips. Far from resisting, she put her hand on my neck and drew me closer.

"Oooh sir, you have a long night ahead of you, no?" the driver grinned at us through the mirror. We started laughing hysterically as the cart pulled up to our building.

"I hope so!" Lauren and I bailed out of the cart and ran hand-in-hand to the elevator. Once in the elevator, we burst out laughing and didn't stop after arriving in the room.

"Nice," Lauren said as she toured the living room, veranda and bedroom of the suite. "I could live like this."

"Yeah, I splurged a bit, and I wanted a little privacy. Anyway, you can change in the bathroom. I've got to find my swimsuit here somewhere."

Lauren turned her back to me and shook her long blonde hair off of her back. "Can you unzip me Jimmy?" I gulped a bit, Lauren's gown was backless halfway down her back, and the zipper reached halfway down her tight little ass. I stepped closer, so she could feel my breath on her neck. I let the tip of my hard dick touch her ass through my pants. She didn't move away. I slowly tugged at her zipper, letting my fingers slide along the crack of her ass as I reached the bottom. I felt her hips move slightly, pushing her ass up against my cock. I decided I had little to lose, and I leaned in and kissed her neck and shoulders. Lauren sighed. I put my hands on her shoulders and slid off her gown. It fell to the floor in a silken whisper. I tilted Lauren's head back and we kissed. I pulled her closer and slid my cock into the crack of her ass. I could have cum right then. I slid one hand off her shoulder, down across her tight young abs and into the front of her tiny thong. The material was very wet as my finger slid between her labia and found her tiny clit. Lauren inhaled sharply.

"Uhhh! Mmmm...Jimmy...such a naughty boy...I've been wet since the car...I saw your boner..." She pushed back onto me, burying my still clothed cock deeper in her crack. She moved her hips a little and slid her ass along my shaft. I played with her clit with two fingers. Lauren bit my lip and pulled.

"Yesss..." Lauren inhaled sharply through her teeth, making a soft hissing sound. "Yeah...Jimmy...make me cum." I reached into her bra and played with her hard nipple while I slowly stroked and caressed her pulsating clit. Lauren's breathing became shallower and faster as her body slowly built to an orgasm. She put her hand over mine, keeping my hand on her pussy. "Ahhhh....sssss....ohhh...god..." Lauren whispered as she ground her pussy against my fingers faster. "Ayyy...yesss...!" her body tensed and then convulsed as her orgasm took over her body. She held my hand tight over her pussy, milking every sensation out of my touch. As the waves subsided, I kissed and nibble her shoulders and neck before Lauren leaned back and kissed me passionately.

As we kissed, I carefully unsnapped her bra. She dropped her arms and her bra fell to the floor, freeing a pair of young, tight C-cup tits with those very hard nipples I had just been pulling and twisting. I started kissing and licking down Lauren's spine, my hands sliding down her shapely arms and hips. As I dropped to my knees, I gently licked Lauren's beautiful ass crack as my fingers again touched the wetness between her legs.

"Ummm...what are you doing Jimmy?" Lauren whispered to no one in particular. "You are going to make me crazy."

"Good," I said. "That's the plan." I slid my fingers into the waist of her tiny thong and slipped it over her hips down her legs to where she could step out of the gauzy nothing. The crotch was very wet, and I held it to my face and inhaled deeply. Lauren's pussy smelled wonderful. Lauren was now naked except for her four-inch heels. Those shoes kept her calf muscles taut and helped her bum to flex and move. I was in heaven. I was about to play with her pussy again when Lauren turned, grabbed my arm and pulled.

"Stand up Jimmy," she commanded. I obeyed. She faced me, naked, smiling slyly. "You're still dressed, Jimmy. That won't do." She grabbed the lapels of my Hawaiian shirt (part of the wedding garb) and pulled hard. Buttons flew, fabric tore and Lauren rubbed her fingers through my chest hair. She reached up, slid what was left of the shirt off my shoulders and cast it aside. "Better," she said. She stood on her toes, wrapped her arms around my neck and slid her tongue into my mouth. My hands found her firm ass cheeks, while Lauren dropped a hand to squeeze my cock through my pants. "You like my ass, Jimmy? I put a lot of work into it."

"I love your ass. Your work has paid off." Lauren's hand had left my shaft and was massaging my balls through my pants.

"Still not good enough, Jimmy. I need to see what I am up against." Locking my gaze with her aquamarine blue eyes, she tugged hard at the drawstring of my pants. Pulling the waistband, my pants collapsed to the floor as Lauren dropped to her knees. I stepped out of my pants and kicked off my flip-flops. I too was now naked. Lauren grabbed my cock with one hand and cupped my balls with the other. She licked the bit of precum from the head of my cock and spread it lasciviously on her lips with her tongue. She stroked the length of my shaft with her hand while sucking only the head of my cock into her warm wet mouth. She coaxed some more precum out of my cock and swallowed it with a smile.

"The driver was right Jimmy..." Lauren smiled up at me.

"What do you mean?"

"You have a long night ahead of you." I pulled Lauren to her feet and kissed her and nuzzled her neck, her ass firmly in my grasp. Lauren suddenly broke away from me. "Go out on the veranda, lay down on the floor." I couldn't/didn't want to disobey any of this woman's commands. The veranda had a concrete boundary, if you will, and if you were down on the floor no one could see, and you would be quite private. I laid on the veranda tile floor, the tile cool against my back and the sun full in my eyes. Suddenly the sun was blotted out. Lauren was standing over me, naked except for her heels. About the sexiest thing ever. Without a word, Lauren stepped one foot on either side of my face and squatted down onto me, her gaping pink pussy inches from my face.

"Stick out your tongue Jimmy." I extended my tongue, just touching the outermost lips of her pussy. She lowered her pussy slowly onto my tongue and began to grind. "You're going to eat my pussy Jimmy. We are going to play Make Lauren Cum, okay?" I didn't answer, stretching my tongue as far inside her as it could reach. Lauren ground her pussy into my face, and soon her pussy juice was running down my cheeks and chin. She shifted her hips a bit, still squatting.

"Lick my clit, Jimmy. Make me cum..." My tongue found its target and I flicked my tongue quickly across her moist clit. "Ahhh...that's it Jimmy! Somebody knows how to eat pussy, no?" It was time for me to take some control back. I grabbed her hips and held her pussy in my mouth. I sucked that little nub of flesh into my mouth where I could hold it, and swirl my tongue all around it, touching every spot. "Oh my God yes!" Lauren reached behind her and grabbed my hair, holding my face in her crotch. I could barely breathe. I didn't really mind. "Yaaa...just like that Jimmy. Just like that..." Lauren was riding my face hard, her clit was completely in my mouth where I could do whatever I wanted with it. I ran my tongue around her clit, over it, and slowly massaged it until she couldn't take it anymore. "Oh! Shit! Jesus! Wha? Oh god...Oh God...Yes... Oh God! OH GOD!!!" Lauren came in my mouth with a rush of juices coating my face, her grip on my hair holding my face in her crotch so I could hardly breathe. Finally she released her grip and resumed rubbing her pussy back and forth across my face. I could finally take a breath.

"Damn Lauren, I almost passed out you had my face so far inside you."

"Sorry, that orgasm was fucking epic. You learned how to eat pussy somewhere old man."

"Nice to be appreciated..." Lauren lowered herself back onto my face, squelching my talk.

"Jimmy?" she asked tentatively, rubbing her pussy and taint across my face.

"Mmmumph?" The only sound I could make with a mouth full of cunt.

"Eat my ass, okay?" With that she rotated her hips and ground her asshole into my face. She fucked my face, running her pussy, taint and asshole back and forth across my tongue. Lauren then reached back and spread her ass wide and placed her slightly gaped asshole on my tongue and ground into it.

"Ahhhh...that's it Jimmy...tongue fuck my asshole." Lauren took one hand off of her ass and began rubbing her pussy while taking my tongue deep into her anus. With so much stimulation, it didn't take long before Lauren started to cum again.

"Oh God...Oh God...Fuck...Oh God," Lauren whimpered. She pushed her ass harder onto my tongue as she came again. "Rrrrroooowww! Ooooooh..! Fuck...Fuuuuccckkk! Yeah...Jimmy." I couldn't say anything as my tongue was still deep in her asshole. Lauren wriggled on my tongue one more time before standing up. She looked down at me, one hand pulling a nipple, another still playing with her pussy. She headed back into the bedroom.

"C'mon Jimmy, I want your cock!" She knelt on all fours on the immaculately made bed and looked back at me, wiggling her bum. "I want that cock!" I stood, letting the blood flow back to my brain while I looked at Lauren's beautiful pussy and ass. I stroked my cock to full erection and looked over the concrete railing at the people on the beach and in the water below.

"If you want this cock you have to come out here and bend over the railing," I taunted her.

"Out there where people can see?" Lauren turned and sat on the bed, leaving a big wet spot on the pristine duvet.

"Yep. All these good people need to see what a little slut you are, Lauren." Lauren bounced off the bed, came over to me and grabbed my cock while standing on her tip toes to kiss me. Still holding my cock, she led me over to the railing and bent over it. The railing only reached to a little above her waist, so her pretty tits were free for all to see. She looked back at me and smiled.

"As you wish Jimmy!" Lauren was still wearing only her heels and a smile. The heels made her beautiful ass stick out in an irresistible way. I got down on my knees behind her.

"Spread your ass for me Lauren," I said as I slipped a finger inside her dripping wet pussy. I started rimming her perfect pink butthole as my finger found her G-spot. Her hips ground on my finger and tongue.

"Damn Jimmy, you're gonna make me cum again, aren't you?" I didn't answer, as I was trying to push my tongue farther into her anal opening. While I was fingering inside her, Lauren started rubbing her clit and talking smack. "That's it you little bitch, lick my nasty asshole. You like eating my ass, don't you? Get your tongue in shape because you're gonna have to clean my pussy after your little dick drops your little load in my pussy. You love licking up cum, don't you little Jimmy? I'll bet...ohhhhhh...shiiiitttt...Jimmy!!" I could feel her orgasm radiating out from her G-spot. Her legs buckled and I had to keep her from falling with my free hand. I helped her down to her knees and helped her sit leaning against the concrete railing. She was still breathing heavily as she spoke.

"Jimmy...oh my God...Jimmy...what did you do?" Lauren wasn't making a ton of sense, but she was happy. I stood up, grabbed my cock and stroked it and waved it in Lauren's face. I don't know if my dick has ever been harder in my life. She reached up and pulled the skin of my ball sack, hard. Without a word I grabbed Lauren by the hair and pulled her away from the wall. I slapped her face hard with my stiff dick, even spattering a bit of precum on her cheeks. I just wanted to fuck her face.