It was a hot Friday to end a hot Summer. The city had rarely been hotter, and all he wanted was to put the legal briefs and affidavits behind him. The firm's rival partners had created multiple Labor Day party invitations to the Hamptons, but he had rebuffed the offers to cruise parties full of Carrie Bradshaw wannabes. Downing vodka tonics and enjoying a weekend to himself was on his mind. He ordered a 2nd, smiled as the bartender delivered it, and squeezed the juice out of the lime before stirring. He stared into the mirror behind the bar and noticed the specks of grey creeping into his sandy brown hair. As he frowned, crow's feet spread from his grey eyes. Breaking his self centered spell, the bar's door opened, and he noticed a petite brunette walk in. She sat at the bar, ran her fingers through her hair, looking a bit tired, and ordered a glass of wine.
After a few minutes, he couldn't help but find her face familiar. She would glance furtively at him. As her wine glass emptied, he ordered her a 2nd. She smiled as the bartender told her he sent it, and he figured out how he knew her. He walked over to her and said, "This may sound like a corny pick up line but are you Winnie - "
"Myerson," she finished for him, "It's Wendy now, no one outside my family calls me Winnie."
"You might not remember me, but I'm a old friend of your brothers, Ryan Landry," he answered.
"Of course I do. You and my brothers other high school friends only teased me for years," she playfully responded, "I've seen on Facebook that you get to play hot shot lawyer in the big bad city, but you waited half an hour to come over."
"Yes, yes, no one has secrets or privacy anymore. What are you doing here? Are you still in school?" he asked.
"I escaped Berkeley this spring, and now I'm working PR for a publicist in L.A. This is a business trip that I'm extending into a shopping long weekend," she answered. She proceeded to inform him of her college career, study abroad, some friendships, and other minor life details that he didn't really care about. He responded kindly to her stories and encouraged her to share. He did notice how she had grown from a gawky pre-teen into a striking young woman. Slender but shapely legs stretched out from under her skirt. Her eyes weren't the blue he had remembered. He could see the green in them, and felt them pierce his mental armor when she'd tip her glass back to sip her drink. The conversation lulled, and she glanced down at her heels. Ryan decided to move.
"We can keep this conversation going as I show you what an Associate's salary can buy in Manhattan," he offered.
"I'll do you one better. My hotel is close, and we can order room service," Wendy responded pulling him closer by his tie, "I have to warn you I play rough."
"I play rougher Winnie. You're a 22 year old who hasn't seen half of what I have," he said with a coy smile.
"Try me. I promise I play harder. One stipulation your honor: we play by my rules," Wendy answered in a stern tone, "You'd learn a thing, or three, from me." After settling the tab, walking a few blocks, and waiting for the elevator, they entered when Ryan grabbed her and forcefully kissed her. She returned his kiss, and bit his lip as she unlocked lips.
"Patience, wait until we get to my room," she whispered to him. They got to her room, and he removed his suit jacket. She told him to remove his clothes while she went to the bathroom. He waited for her on the bed, stretching his legs out a bit in preparation for sex. Wendy stopped by the closet before turning towards the bed. She had a hairbrush, some belts and his tie in her hands. Ryan must have had a quizzical look on his face.
"OK, if you want to play we can play, but I told you I play rough," Wendy said almost questioning him while declaring her intentions, "If you don't mind a bit of play, I can gladly teach you how."
"I'm game," Ryan answered, showing a tougher front than he really felt, "What are your rules?"
"You do as I say, be my sub, and whenever you want to stop, just say a safe word," Wendy instructed. Her blue-green eyes looked cold and serious as she played with the hairbrush in her hand, "anything you want will be the code for me to stop."
"OK, if I want to stop, I'll say 'teddy bear'," Ryan answered and realized he was in for a new experience. He had not been through any BDSM before besides minor spanking girlfriends' asses during lovemaking. Wendy looked amazing naked, the vodka was flowing through his veins, and he felt nervous but comfortable. He asked, "So when does it start?"
"Now. First you need to get up and remove those old man boxer shorts," Wendy said, "You think I'll let a plain white boxer short wearing pathetic loser fuck me. Get on your knees." Ryan got on his knees. He suppressed a laugh..
"You laughing at me? Apologize," Wendy demanded.
"I'm sorry," Ryan answered.
"I'm sorry Mistress," Wendy said.
"I'm sorry Mistress," Ryan complied. Wendy proceeded to berate him for 5 minutes, calling him every name he had ever heard and even a few new ones. He felt like a kid who had broken the kitchen window with a baseball, but it felt fun to have a sexy, naked woman wasting this much time yelling at him. Wendy then told him to kiss his Mistresses' feet. He complied. She laid back on the bed and ordered him to lick her pussy. Ryan eagerly started his cunnilingus routine. About five seconds into it she stopped him.
"You think you're going to eat me out the way you want to. No. Start with your Mistresses' clit, you can find that can't you idiot boy?" Wendy barked. Ryan spent what felt like ten minutes just caressing her clit with his tongue. He would reach up to fondle her tits, and she would stop him informing him that she would not allow him to. He would look up and see her pale breasts and pink nipples, and he'd instinctively reach for them. Her denials made him want to grab them more and more. Wendy next instructed him to lap at her labia while massaging her clit with his thumb. He obediently complied and enjoyed hearing her soft moans.
