In the Pursuit of Pleasure

Lisa was not an outgoing person, at least not until she got to know someone. She was shy, quiet and kept to herself. Her life was mundane at best. She was a born giver, taking care of those she loved. It was a gift she was honored to have and made her proud that she so easily gave of herself unselfishly. The only problem was, she was left in a pile of tears more than she was smiling. These experiences gave her a lot of insecurities.

Lisa could never understand why her love and devotion never seemed to be good enough. No matter how hard she tried, there always seemed to be someone better, someone more desirable. Why was it so difficult to find someone who could appreciate her heart, someone who didn't use her or abuse her? Too often she was left with the feeling of just inadequacy. She had just accepted the fact she would never find anyone to be as devoted to her as she were to him.

One day, while over at a friend's house, she was feeling down about life. Of course, she always turned it inward. What could she do differently? How could she change to be a better person for another person? Her friend could see on Lisa's face that something was troubling her. She saw the usual sparkle gone from Lisa's beautiful eyes.

"What's wrong Lisa?" Mary asked.

Lisa, looking up at her, smiled faintly and simply said, "Oh, nothing. Sorry, I'm not much company. Maybe I should just go."

Lisa stood up and Mary quickly, in a slightly stern voice, "No. You're not going anywhere. I can SEE there is something troubling you, now spill it." Lisa looked at her, took a deep breath and let it all out.

She told Mary how depressed she was because it felt like no one loved her, how often she felt insignificant. Other times she felt invisible. She was convinced she was only around to cater to the needs of others. And as much as she loved helping, nurturing, and loving others, it was draining her. "I don't even want to leave my house. I mean, I know I don't like to leave my house anyway, but it's worse. I just want to lay in bed. I must force myself to even shower. I cry constantly...I just don't know what to do," she stopped. The tears were burning her eyes and soon, they were flowing over her cheeks.

Mary sat down right in front of her. She wrapped her arms around her best friend and let her cry. And Lisa did. Her body shook and the emotion poured from her heart. It was almost violent. Mary could feel her own tears sting her eyes. The pain she was receiving from Lisa was powerful. She just held on. They stayed like that for a bit. Eventually, the tears and shaking began to subside. Lisa slowly pulled back and looked at Mary. Lisa noticed she had left Mary's shirt soaked with her tears. "Oh my gosh," She put her face in her palm, "I am so sorry Mary, I..."

Mary quickly interrupted, "Nonsense. Don't you dare apologize to me. I hugged YOU. It's a shirt. You're my friend. The shirt is replaceable, but you my dear friend, you most certainly are not." Lisa smiled. She was so thankful for Mary.

They had been friends since high school. They met freshman year and became inseparable. Mary was strong, confident, she was everything Lisa wished she could be. But most importantly, she valued Lisa. Mary never once took advantage of Lisa and was always there for her. It was a beautiful friendship, a perfect example of give and take.

"Lisa, you need to stop beating yourself up. You do this so much and I pray one day you can see yourself the way I do. The way a lot of people do." Mary paused, she had said this so many times before, but was determined to say it until Lisa listened. "You are this rare combination of inner and outer beauty. People are literally drawn to you because your light is like a beacon. Yeah, it draws in the assholes too, but that is to be expected. But the one thing you should never, absolutely never do, is doubt yourself. You have so much to give and offer. Any man should be on his knees daily worshipping you!"

Lisa laughed at this idea. "A man, on his knees, worshipping me?! Riiight! I could never see that happening."

Mary's eyes narrowed and she got serious for a moment. "It's because you don't demand it. Any man I am with will always worship me if he wants to be with me in any capacity. I will accept nothing less than a man giving himself over to me completely."

Lisa just looked at her. All these years they had been friends, and she still didn't understand how Mary did it. She was a Dominatrix and damn good at it from what Lisa could see. Men didn't dump her, she dumped them. They looked to her for everything and worshipped her completely. Whatever she wanted, she got. But Mary wasn't like some of the Domme's Lisa had seen before, Mary didn't take advantage of it. She took care of her subs. She would say, "A well taken care of sub is a loyal sub."

"Oh Mary, you know how I feel about that." Lisa's cheeks flushed red, "It's really not my thing. It's not natural for me to demand anything from anyone. I just want them to want to do things for me."

Mary giggled at this, she said, "In my experience, you get further with demanding what you want than waiting for them to think of it on their own." She winked at Lisa, "Just remember, if you ever want to try your hand at it, let me know."

Lisa laughed and with wide eyes and a silly smirk she said, "SURE!"

They had the best night. They ordered pizza, played card games, then just sat up late into the night talking about old times, present times and the future. Lisa was a widow, with a daughter and Mary was divorced with a son. Their kids were more like siblings. Mary had been there to force Lisa back to the land of the living when Lisa's husband passed away. Even though secretly, Mary rejoiced that he was gone. As horrible as it is, the fact was, he was a horrible husband. In their short 5 year marriage, he constantly and consistently cheated on Lisa. He took advantage of the love she had for him and their daughter. Mary hated every minute of it. She never told Lisa this, but the night he died, she went out and partied. Hadn't been to a bar in years, but that night, she celebrated the fact her best friend was free from the slavery of that man. Mary worked overtime to get Lisa over his death. She's pretty sure that the process was sped up when Lisa also finally realized she was free from the torture of that marriage.

Likewise, Lisa was there when Mary felt destroyed after finding her husband with another woman. In their bed no less, while their son napped in another room. Mary had been careful all these years not to fall in love with her subs, it was a no no. But he was different. He won her over, then almost destroyed her. But Lisa was there, she was there to remind her about the badass she was. She'd never looked back.

The next morning the women slept in. Lisa was the first to wake. She got up and made coffee. They weren't as young as they use to be. Being in their 40's, 'Rise and Shine' took a bit longer than it used to. Lisa was in the kitchen making two cups of coffee when Mary came stumbling in. She looked at Lisa as she took the cup and smiled. The two women sat in a comfortable silence on the couch watching the news. Lisa in her shorts and t-shirt, bundled in a blanket while Mary had on a thick cotton robe. No one spoke until the second cup was in hand. Mary, a serious look on her face, "Let me teach you about the ways of being a Domme. I mean it Lisa. There are different levels and styles. We can find one you're comfortable with. I know a lot of subs you could practice with."

Lisa looked at her sideways, she wanted to believe this was a joke, but she saw the seriousness on Mary's face. "I don't know Mary" she said, slowly shaking her head. "I couldn't degrade someone. I've seen and read about this stuff. And the..." her voice dropped "the whips and spankings and such, I just don't know."

Mary burst out laughing. "Do you think this is 50 Shades of Grey or something?!?!" she continued to laugh as Lisa's look turned from embarrassment to frustration.

Lisa rolled her eyes, "Ok fine, what's it like then?" Mary decided they needed food and more coffee for this discussion, so they moved into the kitchen. Lisa refilled their coffee cups while Mary began gathering all the ingredients for breakfast. Lisa positioned herself at the table while Mary began cooking and explaining the Domme/sub life.

"Yes, there are parts of this lifestyle that include the stereotypical things you read about or see in movies, but that isn't the norm. Believe it or not, there are men who want to be ridiculed, spat on, even harmed. But, there are also men who just want to please a woman. Like, your wish is their command. Men who love a strong woman."

"Wait" Lisa interrupted, "There are men who WANT to please a woman? Like, more than they want their own pleasure?"

Mary got a little grin on her face, "Absolutely. Their whole purpose is to fulfill your needs. They want, more than anything, to make you happy. Believe it or not, doing those things make them happy. For example, if you're a woman who enjoys anal play" Lisa scrunched her nose at that, "IF, it's an example Lisa. Then that's what he will want to do for you. It's the same if you prefer oral, the sub will want to do that. All the time. But there are rules. The biggest problem is sometimes you meet someone so wonderful; you break all those rules. The best advice I can give you is to talk with your sub right up front. Make it clear to each other what you want, what you don't want, as well as what you are willing to try. Set the boundaries very clear. This will ensure you both enjoy your roles."

Lisa thought on this for a moment, unsure she could take control of the bedroom. It's intriguing, the thought of a man wanting to please you blew her mind. Lisa had never experienced anything like that. Most of her sexual experiences were completely one sided, leaving her to take care of things herself.

"There is no way I could hurt or belittle someone. It's just not in me to do something like that." Lisa said.

Mary looked at her, shrugged a bit and said, "Then don't do that. If you have a sub who tells you that is what they're into, tell them 'No thanks' and let it end with that. Most Dommes never even have intercourse with their sub."

Lisa looked her completely perplexed, "Excuse me? Then how does everything, um, happen?"

Mary giggled, "Masturbation silly. Now, I'm not saying there is NEVER any intercourse. But there are some Dommes who won't do it. They feel it takes away their power. Now, penetrating him is a different story."

Lisa looked at her horrified, "Um, penetrate him? You don't mean..."

Mary quickly said, "Oh yeah, that's exactly what I mean. From both a Domme and a sub's perspective, it's the ultimate exchange of power." Lisa just sat there, completely confused. She was trying to process everything, and it made her head hurt. She wasn't completely sold on all of this, but she would soak up all of Mary's knowledge and go from there.

Over the next several weeks, Mary and Lisa spoke constantly. Everything seemed to be a teaching moment on how to be the best Domme possible. Mary encouraged Lisa to make lists of things she knew she liked and things she knew she didn't, then a list of things she wouldn't mind trying and things she had no desire to try. Mary said be thorough. Research the internet if needed. Ha, Lisa thought, I don't need to search the internet. I may not be a 'Domme' but I do know sexual positions.

About a week or so after the assignment, they met back up so Mary could look over Lisa's list. Mary confused, "Um, where's the rest of it?"

Lisa looked at her, equally confused and said, "What do you mean, that's everything. I even included anal and feet stuff. What more could there be?"

Mary looked at her, looked down and closed her eyes chuckling a bit. Then she looked up at Lisa and said, "Oh honey...what about threesomes or even more? Male, Male and female or female, female, and male? Are you into golden showers? What about porn as a mood booster? Exhibitionism?" she paused noticing the look on Lisa's face, "Ok, I see there is a lot you don't know about. Honey, there is sooo much more than just normal stuff. Before I became a Domme, I was with a man who absolutely got off on watching me with other men. Yeah." Mary took a deep breath, "You may have to just wing it. My suggestion is if a sub asks you if you enjoy something you've never done or considered or heard of, tell him you will need a few days to consider his request. Then, do some homework on it and really think about what you would feel comfortable with. And hey," she said coyly, "he might just request something that sounds really appealing to ya." Then she winked at me.

Lisa's head was spinning out of control with all this information. She didn't know what to do. If this would even be something she enjoyed. Lisa didn't have 'kinks', she just wanted someone who would be just as happy to show her pleasure as she was to show him. Her only kink was simply passion. She really didn't know if she was going to be cut out for all this. Finally, she thought, what the hell, at least maybe she will have a really good orgasm that she didn't have to give herself. That would be pretty awesome. So, she called Mary.

Mary had a perfect sub in mind, he was actually one of her favorites and she thought he would be a great starter for Lisa. He really didn't have any weird fetishes and was up for whatever. He had always been a sub, so he's been through the world of BDSM and has experienced most of what it has to offer. A good confident sub is what Lisa needed to help her get going. Someone who will help guide her to discover what kind of Domme she would be. Mary was still completely convinced she would make a perfect domme. Lisa was loving and kind, and would never make someone do anything they didn't like, but at the same time, if they could build her confidence, Lisa could definitely offer a guiding hand to a sub.

She sent Ted a text message:

Hey stranger! I have something I want to run by you,

You're the perfect man for the job. Call me when you can

So, we can go over all the details. Thx, Miss Mary

Ted was in the middle of a presentation when he felt the buzz in his pocket. Not expecting it, he almost jumped. He ignored it for the moment; he was trying to land this client he'd been working on for a while now. As soon as the meeting ended, he gathered his things and began walking back to his office. Remembering the text, he pulled out his phone and noticed it was from Miss Mary. His heartbeat quickened and he felt a tingle in his pants. Not knowing what she could've sent, it had been almost a year since the last time they were together, he wanted privacy to open it. He quickly closed the distance between him and his office. He threw the stuff from the meeting, including his laptop in the chair, closed the door, and positioned himself at his desk. His breathing became slightly heavy in anticipation.

Reading the text, he wondered what she wanted to chat with him about. I mean, they ended their arrangement in a nice manner. She was a really nice woman and knew how to get him going, but she was a rougher domme than he preferred. But they had a lot of fun together. With a deep breath, he hit the button on his phone to dial her number.

"Hello." Her smooth, sultry voice flooded his ears and he closed his eyes too drink in the sound of it. "Hi Miss Mary. It's Ted. I got your text." He was so nervous; he was speaking way to fast. Control your breathing Ted and calm down.

"Awww, Teddy! I'm so glad you called me back. I have something I'd like to discuss with you. Do you have any free time to meet up and maybe talk about it over a cup of coffee?" Was that playfulness he detected in her voice? He wasn't sure if he hoped it was or wasn't. But he could never say no to Miss Mary.

"Su-sure, I'd love to Miss Mary. I have an open schedule; you just tell me when and where. Please." He stammered. Her light giggle made him blush and that tingle in his pants was getting stronger.

"Well, how about tonight? We could meet at the Diner. Would you like that Teddy?"

He was fully erect now. "Y-yes Miss Mary, I would like that very much."

There was a pause and then her smooth voice, "Wonderful Teddy. That makes me very pleased. I'll see you later. Don't be late."

He gulped, "I would never disappoint you like that. Ever."

She responded, "I know Teddy. See you soon." Click.

His mind was racing trying to figure out what she wanted from him. The next several hours were going to be torturous. His cock was fully erect and was making it very difficult for him to focus. He kept seeing flashes of her in his mind: her body, her smile, her smell. She didn't tell him not to, so he slipped off to the toilet to have a quick rub.

Nobody in the restroom, so he locked himself in the stall. It took him no time to unzip and start rubbing. Picturing her in front of him, he cupped his balls as he stroked like she enjoyed. From tip to the bottom of his shaft was what she wanted to see. Full tugs like she enjoyed from him. He wanted to go slow for her, like she liked it, but he couldn't. Before long, his hand was squeezing and tugging fast. Precum began to leak out. He had balled up his tie like a gag and put it in his mouth to muffle his moans. If he were at home, he had no doubt he would be loud. He felt the tingle in his toes and the warmth spread through his body as his cock pulsed in his hand and his load shot all over the stall door.

He sat there for a moment, trying to get his bearings and let the blood rush back to his head. Holy fuck that felt good. It had been a long time since he masturbated so good. It was her, just her. She was a really good Domme. So much so that just a mere conversation got him that worked up. He was both excited and nervous for their coffee date tonight. He would think of nothing else nor accomplish much for the rest of the afternoon.

Ted arrived at the Diner early, he liked to always be prompt and never keep someone waiting, especially someone like Miss Mary. For him to be tardy was unacceptable. He decided to wait on ordering anything, he didn't want to be presumptuous. Had they met at an upscale restaurant, he would've ordered her favorite wine, but at the Diner, sometimes she had coffee and sometimes a soda. He fidgeted as he waited for her: straightening the salt and pepper shakers and messing with the napkins. He had read the menu so many times he probably had it memorized. She wasn't late, he was just nervous.

He looked up and saw Miss Mary walking toward him, right on time. He felt the tingle in his pants but was determined to keep it under control. The woman was simply breathtaking: long dark hair, she had added a little curl to it, which softened her look, Mary had big brown eyes, perfect lips and pale milky skin. She was dressed simply in a pair of jeans, t-shirt and flip flops. Her finger- and toenails were painted the perfect shade of red. He stood to greet her. She leaned in, "Teddy!" They hugged and he kissed her cheek. They sat across from each other as the waitress came and took their drink orders. She had a coffee, so Ted ordered the same.

"Teddy" she said in that sultry voice, "I need to confess why I brought you here."

Anything you want Miss Mary." Ted said eagerly.

She smiled; her whole face lit up. She reached out and patted his hand, "Teddy, dear, I am no longer your Domme, you do not need to call me 'Miss'. The reason I reached out to you is I need a favor."

He always had to concentrate on her words; there was a quality about her voice that soothed him. "Whatever you need Mis-uh...Mary. You know I would do anything for you." Ted said with a smile.

She looked at him: his eyes wide in anticipation, eagerly awaiting her instructions, and his uncontrollable desire to please her. He had been a lot of fun, unfortunately, it just hadn't worked out and she had no choice but to end it. He had agreed that their fetishes were too opposite to continue. But they had a lot of fun. "I have a friend; who's curious about the lifestyle. I have been coaching her and educating her on it. She is very hesitant as she has always been the giver. I want her to find her voice. She needs to find her way. Now, she may not like it. She will probably make mistakes and I can guarantee you she will be unsure of herself." He listened to every word with curiosity, understanding and willingness to help. "Now Teddy," she continued, "you are the only man I could think of for this; I trust you and I know you would be patient with her. She needs a gentle hand. Are you interested?"