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.