Hot Summer S&M

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.

In the midst of going down on her, she grabbed him by the hair and told him he needed to receive his punishment for upsetting his Mistress. He was a bit surprised as he had done all she had asked, but he went with it. She grabbed the hairbrush and ordered him to bend over her knee. She yanked at his erection and stuck it between her thighs as he bent over.

"You will never call your Mistress 'Winnie' ever again. Promise?" Wendy said as she swatted him on the ass. His rear stung as the back of the wooden hairbrush made contact.

"Ok, I promise," Ryan pledged. A few more quick smacks, and Wendy asked again, "Will you ever say Winnie again?"

"NO," he cried as she really laid into him.

"Wrong. You will only say 'Winnie' if I order you to, correct?" Wendy explained. Ryan agreed and shook his bent head. Ryan noticed his hard on had become firmer, and Wendy must have noticed as she ordered him to the bed on his back. She grabbed the belts and tied his right arm to the bed frame. As she went for his left arm Ryan said, "Teddy Bear."

"Ok, what's up? You seem ready to go," Wendy said glancing at his dick. Ryan explained he wanted one arm loosely tied in case something went wrong. Something out of a Stephen King novel stuck in his head. Wendy agreed, and then went back into Mistress mode. She removed the lamp shade from one of the nightstand lamps and turned the light on. With his swimmer's build stretched across the bed, he was at her mercy. She turned to him and mocked his cross, his grooming, his 5 o'clock shadow, and anything else she could think of. Despite his engorged member, she told him he needed a cleaning before she'd mount him. She started to blow him and removed her ornate ring. Ryan closed his eyes and enjoyed her work. She used her tongue and flecked at his head, teasing him. He hadn't noticed her slow down, and he opened his eyes to see her stretching her arm to place her ring on the light bulb. He watched her as she went back to a steady pace and realized why she had placed her ring on the bulb. She had sped up the fellatio as she placed the hot ring against his right thigh. The pain was quick and intense. Combined with her oral skills, he felt lightheaded and nearly came. She would remove the ring and reapply ever so often. The hot ring combined with her oral prowess sent adrenaline rushes to his head. Wendy stopped, and squatted over his chest. Looking down on him she asked,

"Are you ready to be used you piece of shit?" At this point, Ryan did not care at all, and just wanted to fuck her. She slapped his face.

"Yes."

"That's not right, scumbag. Will a pathetic chump like you bring me pleasure?" Wendy asked followed by another slap.

"I will. I'll fuck you any way you want," Ryan answered a bit impatient.

"No, I will fuck you and use you so that I get off. If you aren't an good, I'll kick your ass out of here to finish yourself off in your little apartment all by your lonesome," Wendy retorted. She was good. He now really wanted to give it to her. Before she slid down to his dick, Ryan asked, "Please, can you tie that left arm tighter?" She smiled and made the belt loop a tight cinch. She grabbed his tie and stuffed it in his mouth.

"How much did this cost?" she inquired.

"$85," he answered.

"Even better," she smiled and then glided down on his dick. She started with a bounce to her riding, finding a rhythm. Her pear shaped breasts gently moving and peeking out whenever her long, black hair swayed. She cursed him as she rode, calling him the worst fuck she had ever had, which only made him tilt his body more or thrust harder with her bobs. She shifted a bit as she got wetter and started to grind in a circular motion, leaning down to place their faces inches from one another. She threatened him, "I'll kill you if I don't come; I'll call a queer here to finish you; I'll stomp on your balls if I don't get off," as she dug her nails into his ribs.

He could feel the heat from her pussy and she started to quickly grind down on his pubic bone with her clit. He tilted his waist for a better angle, and she dipped her mouth to his ears. She bit his earlobe, and Ryan grimaced in pain. She stopped her biting and let the mask of mistress slip short enough to whisper, "I'm coming little bitch," into his ear. He smiled as she pulled her body back, but she furrowed her brows, and said, "I'm not done."

Wrapping her hands around his throat, she rode him for another orgasm. The gentle choking combined with the tie stuffed in his mouth had caused him to go light-headed, but had amplified his senses. Ryan could feel a bit of warmth on his ear. Wendy looked down, removed the tie and untied his arms quickly. He asked what was the matter, and she explained that she bit a little too hard during her climax. She started to resume her grinding and told him they could switch to doggie style by the desk so she could watch him come. They got up in front of the mirror and he started to pound her. She gave him instructions as to how to hit her spots. Freed of the restraints, he felt a bit out of focus. Ryan was missing something and told her he needed her closer. He needed her to order him, not just give suggestions. They laid on the bed with Wendy on top of Ryan in reverse. He could feel the sweat on her back and ass on his body.

"I knew you'd love it. I knew your pathetic little ass would love this," Wendy cooed at him. Ryan moved her mass of dark hair out of his face and begged her to talk him up. It was thrilling to be with a woman who was so active and engaged.

"Of course you need me. You need your Mistress to let you come. You haven't felt this way before have you, fuckface," Wendy whispered up to him. She was right. He hadn't been this hard in years. He could feel his orgasm coming and breathed a bit shallower.

"Come now. I want you to come, come now you fucking twit." Wendy demanded, and in that moment he felt his groin spasm. His cock flexed several times, and he felt himself slowly pump Wendy. Time slowed a bit as he felt that muscle at the base of his cock squeeze itself sore. He moved his arm across her body and grabbed her left breast. As his body shut down, she slid off him, gave him a kiss, and walked to the bathroom as if nothing happened. Ryan saw her saunter back and slide up to him. After a few minutes of silence, Ryan felt his thoughts come together and recalled a promise for room service.

"So your parents sent you to Europe to study, and French men taught you this?" Ryan playfully asked.

"I never said anything about a man teaching me this. It is amazing what you find you are capable of with just a little guidance," she answered as she turned her head to chat, "A different partner can pull something new out of you."

"So do we order food now or do we go for round 2," he asked trying to appear suave. His exhaustion must have betrayed him as Wendy cracked a smile.

"Well big shot, I think we should order up some food and take a breather," she answered as she reached over for the room service menu. Reading the menu, she shot him a glance and said, "Plus, if you want to touch me again tonight, you're going to have to wash your Mistress first."