The Lady Executive Returns

As I finished my makeup and hair I decided how I would start breaking Bailey in. I know Reggie told me to stay offline but Bailey needs some training if she is going to keep up with me. Besides, what could possibly happen? It's time she faced the facts that her divorce is coming to a close and her children are growing up. With everything getting out of my control with Randall, Reggie, Lance, and whoever else they have in the wings, I could use the comfort that Bailey provides me.

As I went through my closet trying to decide what to wear to the airport, a random memory popped into my head. It was from many years ago, during a cross country road trip a friend of mine and I had taken as part of a photography project he'd been hired to do. The end result was to be an extremely limited run of erotic photographs taken at some of the more popular and significant landmarks across the nation. My friend, Jake, was the photographer and I was his muse. The gentleman who had hired Jake had a list of the landmarks he wanted in the photos. Some of them had very specific requirements as to time of day, arrangements, poses, props, bystanders or not, etc.

I sat down on the bed as I remembered doing the shoot at the Golden Gate Bridge. We had found an overlook that gave a great view of the bridge and the bay early in the morning when there weren't any other people around. I wore a ruby red wrap around silk blouse with a matching skirt. The skirt had a slit up the side. Jake had positioned himself so that the bridge was in the background and I just started slowly walking toward him, smiling seductively and flirting with the camera. I licked my lips and caressed my braless breasts and looked around to make sure no one else was there. I blew the camera a kiss and smiled as I slowly untied the blouse straps around my waist and let it hang there for a few moments, the sides of the blouse caught on my hard nipples, hiding most of my tits but leaving no doubt as to the treasures beneath. I let Jake take a bunch of pictures before shrugging my shoulders and acting shocked as the blouse slipped off my nipples and opened wide, exposing my tits to the world. I took my nipples in my fingers and pulled and twisted, letting the passion and arousal show on my face.

Lost in the memory, I pinched and pulled on my nipples as I had at the bridge and I felt my pussy begin to flow. I looked at myself in the mirror and saw the flush in my face and chest. I chewed my lip as I checked the clock and verified that I had plenty of time before leaving to get Bailey so I gave in to the urge and laid back on the bed as I spread my legs wide and slid my fingers between my lips, into my pussy, and gently stroked in and out as I lost myself in memory once more.

Jake encouraged me as only he could do. No man I had ever met could induce me to the behavior that Jake could, yet he was one of very few men I ever trusted fully and truly loved.

He was saying, "Oh my god, Joanie, keep that up. Run with it, Baby. You are so incredible, so beautiful, so erotic that you just blow my mind. Give it to me, give me that passion, that heat!"

His words just fanned the flames that had already been building in me. I grabbed handfuls of my tits and squeezed before letting go and taking the ties of my skirt in my hands and tugging on them.

"I'll tell you what, Stud. You show me yours and I'll show you mine." I said seductively as I slowly opened the skirt to reveal my left leg up to my hip.

"You're on. I'll go first." Jake exclaimed and laughed as he set the camera on the trunk of our rental car. Without taking his eyes off me, he unbuttoned and unzipped his jeans and kicked off his shoes. He slid his jeans down his legs, exposing his hard cock to me. I licked my lips and stared hungrily at it. With his jeans on the ground, he stroked his cock a few times before picking up the camera and telling me, "It's your turn."

I smiled at him as I very slowly opened my skirt while he took a rapid series of pictures. I gave him different expressions as my skirt slowly exposed my ever smooth pussy. With the skirt completely removed and a blouse hanging loosely on my shoulders, I laughed as I quickly threw the skirt at the camera. To my horror, a strong breeze came along at that same moment and took my skirt to places unknown. I remembered laughing at the facial expressions Jake had captured at that moment when we looked at the pictures later that day. I watched as the skirt just floated away, knowing there was nothing I could do about it. When it disappeared, I just looked back at the camera and shrugged and then smiled as I took off the blouse and threw it up in the air. I laughed as the wind took it too. When it was gone, I looked at Jake and gave him my best sultry look.

"Jake, put that camera down." I said as I walked toward him.

Jake, being the smart man that he was, did just what the horny, naked woman in front of him told him to do. He set the camera down on the roof of the car.

By the time he turned around, I was standing in front of him, close enough to let my nipples brush his shirt. I looked him in the eye as I put my arms around his neck. I jumped and wrapped my legs around his waist. He caught me and slowly lowered my pussy onto his rock solid cock. We made love standing up with him leaning back against the car and holding my ass in his hands as I did the rest, thrusting my hips forward and back, repeatedly taking his cock deep into my pussy.

I thrust my fingers into my pussy in sync with the action I remembered. I came all over my fingers and the bed at the same moment we came in my memory. As I lay there on the bed, breathing heavily from an intense orgasm, I finished the memory.

As we stood there next to the car, relaxing from the lust charged encounter we'd just enjoyed, Jake chuckled.

"What's so funny?" I asked.

"I don't suppose you brought another outfit with you this morning?" he said, smiling.

I just smiled. "Nope."

"Well, I guess there is going to be a bonus chapter in the book. We'll call it, 'Naked Woman On The Streets Of San Francisco.' How's that sound?" he asked.

"It sounds like I am going to be very horny all day long and you are in big trouble back at the hotel." I said, seductively as I walked to my side of the car and got in.

Feeling my pussy getting wet again, I checked the time and decided I'd better get a move on. So I hurried to set up my bed, laptop, webcam, toys, and lingerie for both me and Bailey. I went back to my closet and pulled out an outfit similar to the one I wore that day in San Francisco, except this one was a royal blue blouse and a black skirt. I chose matching blue heels with a sexy ankle strap to complete the ensemble. I decided to forgo the underwear and went commando, planning to tease Bailey a bit on the way home. I took one last look in the mirror and then I headed out the door to pick Bailey up from the airport.

As I got in my car, I thought "It's time she goes online with me, has fun and learns the ropes there for starters. She has watched me do it so it won't be such a shock to her. We can perform in the chat room and after she is all warmed up, I can talk to her about Cory."

I parked my car at the airport and went inside to meet Bailey. Wilmington has a small airport but it was very busy being so close to the 4th of July weekend. All the families going on beach vacations were arriving making it difficult for me to see Bailey in the crowd. It made me thankful of the quiet and secluded beach house I was in.

"And there she is." I said out loud as soon as I saw Bailey. I realized just how much we looked alike at that moment, we could pass for sisters! Many people had commented on it, but I had never noticed until I saw here beaming with excitement walking quickly towards me.

I couldn't believe it but Bailey had worn almost the same outfit I had on. She wore a pale blue silk button down blouse with a short loose darker blue skirt and matching black flats. I knew at glance that she, too, had gone commando. I openly watched her breasts bounce as she walked across the concourse toward me. I thought I detected a little more hip action than usual, causing her breasts to bounce quite nicely as I watched. When she reached me, we embraced holding each other tightly. She had no idea how happy I was to see her and get her out of Houston for good even though she had no idea that she would never be returning.

I kissed her as we headed for baggage claim to get her things but the belts weren't moving yet. "Bailey, let's go outside for a smoke while we wait. I have a surprise for you."

"A surprise?" she squealed.

"Yes babe, a fun surprise." I answered as I found us a bench to sit on. I reached in my handbag for my cigarettes while Bailey moved in to sneak a kiss on my cheek. I loved how playful she was and knew this would work out just great. I lit my cigarette and told her, "I have the day off and the bed all ready for some fun."

"But I thought we had urgent business at the office. What's going on? Did you just miss me that bad?" she smiled with confidence.

"Oh, we have business. Trust me on that one." I told her, smiling seductively.

Bailey took a drag off my cigarette as she pondered what I had in store for her, put out the cigarette and said, "Well, let's get the show on the road."

I hugged her to my side as we strolled in to find her bags knowing she had no idea what was in store for her. I patted her ass as she stepped away to pick up her bag from the conveyor belt. She acted shocked, then looked over her shoulder and blew me a kiss.

With the car loaded down with her bags and the sun shining brightly, we headed to the beach house. As I drove, Bailey slid her hand up my skirt to find my wet pussy waiting for her and asked, "Now what's the surprise?"

"You might as well know now so you have some time to get in the mood." I said.

"I'm already in the mood." She whispered as she leaned in and gently licked my earlobe, sending shivers down my spine straight to my pussy.

I sighed as I reached over and placed my hand on her thigh. Her breath caught as I slowly and gently dragged my nails back and forth across her thigh, ever closer to her pussy. She spread her legs and whispered in my ear, "I have a surprise for you too." She took my hand and pulled it straight to her pussy, growing impatient with my teasing. I smiled as my fingers encountered bare skin. I knew she'd gone commando but was slightly surprised that she'd had her pussy waxed since I'd been gone. As I slid my fingers deeper, I received a big shock. I encountered jewelry on her clit!

"Oh my God! Sit back and show me!"I said excitedly.

Bailey laughed and sat back in her seat and turned her hips toward me. She pulled up her skirt and spread her legs as wide as she could. "It's a clip, not a piercing. It wraps around my clit and dangles between my lips. It is absolutely incredible when I walk. Last night I had I don't even know how many orgasms just walking around the house with this thing on. You have got to get one, Joanie. It will rock your world." she exclaimed as she sat there and played with it, flicking it back and forth. It didn't take long before she was in the throes of an orgasm. I let her enjoy herself for a bit.

"Girl you are lucky the windows are tinted. Do you know a cop pulled up next to us just now while you were cumming all over your seat?" I asked, chuckling.

"I am so horny right now that I wouldn't have cared had I known. I can't wait to get to the house. I want you so bad I can taste it." she purred, reaching over and caressing my leg, pushing my skirt higher again. As she moved her hand up my thigh to my pussy, I sighed and chewed my lip as she worked my clit making it difficult to concentrate on the road.

"Good, I'm glad you want me. The bed is made, toys are ready, and lingerie is set out for your first performance online with me. Your online name will be Brandy."

Removing her hand from my pussy quickly, she exclaimed, "What? You expect me to go online and play games with men I don't know?"

"Bailey, settle down. You won't be playing any games with men, you will be playing with me. The men will be watching and paying to watch us. Maybe we will find a special one to send over to my private site for an in person threesome. You know you have wanted to do this ever since you watched me do it. Now, admit it. It's exciting and you used to always enjoy being watched while we were in college. You were quite an exhibitionist. We can revive those days starting now." I said gently.

Bailey looked out the window as we crossed over the intra coastal waterway then back at me batting her eyes she said, "So Brandy is the best name you could come up with?" We were laughing together as we pulled into the driveway at my beach house.

We carried her bags upstairs to the bedroom that Reggie and I had shared on our first encounter and left them there for her to unpack later. We had some fun waiting for us in my room. I showed Bailey to my room and she quickly noticed the balcony and the sliding doors overlooking the ocean and opened them right away. She stepped out onto the deck and, with the ocean breeze meeting her body she began to undress in full view of anyone who happened to look her way. I just smiled.

"That's my girl, let go and have fun while I do a sound check on the equipment set up. I want to make sure we can be not only seen perfectly but heard just as well." I said.

"Joanie, I am so happy you brought me here. I don't think either of us knew how much I needed this." she said excitedly as she came back in, leaving her clothes in a pile on the balcony.

"Honey the fun is just beginning. Now on the bed we have matching black lace teddies with red trim, red thongs with black lace, and black stockings. There are also red chokers that should clasp firmly around our necks. I find the chokers a much sexier touch than necklaces that get in the way. Start getting dressed so we can touch up our makeup and hair."

Bailey did as instructed and while I finished the sound checks I went over the rules with her and began dressing. As I watched her getting dressed, I couldn't help but wonder at the changes that we were both going through.

"You will go by Brandy and you must always refer to me as Joanie which shouldn't be a problem. My online name is Joanie Starr. Some men will call me Miss Starr because I do a lot of dominating. Ignore the assholes that are rude, if they get to arguing in chat, I will remind them to focus on us and they will obey. They can hear and see us perfectly but we cannot hear them so we have to watch the computer screen for their typing. As soon as we go online, my regulars will get a text message sent to their cell phone that I am online and since it is lunch time, we will draw a good crowd for a few hours. Many men get online and jerk off in their offices during this time. If someone takes us to paid private chat, a bell will ring alerting us and if we think he is a candidate for a threesome, I will refer him to the site after we have given him a trial run in paid private chat. Also, the person taking us to private paid chat has the option of showing his webcam to us. If the tipping is good, I will turn off private chat options and turn on party mode. In party mode, they can only tip for what they want, no privates. If we have a large crowd, party chat will be best. A different sound 'cha ching' will alert us when we are tipped. Pay attention to the screen when we hear that noise so we can thank them. I like to play games in party chat so just follow my lead if it goes that way. Last but not least, do not refer anyone to my site in public chat. Don't even mention it."

Bailey was dressed and looking sexy as hell. "Got it Miss Starr. Any other orders?" She giggled.

"No, now come help me with my choker. I can't get it hooked in the back."I said, smiling.

We positioned ourselves on the bed after I logged in, grabbed my remote for the webcam, and hit broadcast. "Smile, Brandy, we are online. Watch on the right side of the screen. When you see people's online handles coming in, you know we are being watched. I never call anyone out. If they like what they see, they will type." And just like that, the chat room was filling up.

I smiled and said, "Hi everyone, we have a treat today. My friend Brandy is joining me. I hope you guys are ready for some girl on girl fun." I reached to Brandy and pulled her to me, grabbed her hair tilting her head back and kissed her long and passionately, just as I had wanted to do all day.

Cory was driving to Wilmington when his phone beeped. When he picked it up and looked at it, he was surprised to see that it was a 'Showtime' announcement from Joanie's Miss Starr website.

He looked around and found a McDonald's just down the street. He pulled into the parking lot and opened his laptop and turned it on. While he waited for that, he sent a text to his brother, Reggie.

"Hate to bother you, but she's on." he said.

"I know. I just got the chime. See you there?" Reggie answered.

"Yeah. Why can't she just do as we ask? LOL" Cory said.

"Because she wouldn't be any fun if she did. LOL." Reggie sent back.

Cory logged into 'Miss Starr's Party' and within moments he saw that Reggie was there too. Together they watched and enjoyed the show, even though they were over 1000 miles apart.

The sound of tips started pouring in and Brandy chimed right in, "Thank you John Doe and Dollar Bill. By the way, I love that handle Dollar Bill."

I smiled at Bailey and said, "I think it's time for party mode Brandy what do you think?"

"Sure Miss Starr." she answered, licking her lips seductively.

"Ok boys, this is Miss Starr's Party Auction. The biggest tipper within the next 3 minutes gets to direct a 5 minute show with me and Brandy, so get started because the clock is ticking now!"

The tips poured in with one exception, a man with the handle Starrman kept typing, "Go away Brandy, I only want Joanie."

Bailey thanked and encouraged the men as I did. I watched the clock and the three minutes were up. "Ok guys, your time's up, the biggest tipper was Dollar Bill. You have five minutes to direct your own show so start typing what you want.

He typed, "I want you to remove each other's teddies. Once you have done that, I want to see tits, kissing and rubbing and pinching nipples for starters."

I started by removing Brandy's teddy and sucked her nipples as soon as the teddy hit the floor. As I sucked her nipples she moaned and removed my teddy and threw it in the floor with hers. She took my nipples and pinched them as she kissed me, pulled my head back by my hair and licked my neck and then back down to my tits where she sucked them as I massaged her perky breasts.

I moaned and asked, "Oh, Dollar Bill, I want more of Brandy please. What do you want next? Your time is almost up and my pussy is dripping wet babe."

He typed, "Remove the stockings."

I pushed Brandy down on the bed, sucked her tits, and licked her from her stomach to the top of her thong while she begged, "Eat me Joanie please!"

I rose up and lifted one leg at a time kissing her legs as I removed the stockings one by one. "Do you like that, Brandy?" I purred.

"Oh hell yes!" she moaned.

I looked at the screen and the clock and said, "Wow that 5 minutes went fast! Let's go again. We want more of each other. Brandy is begging for me to eat her and fuck her with my toys. Highest tipper in the next three minutes directs the next show."

Brandy got on top of me and sucked my tits some more while I watched the screen as the tips poured in again. I noticed Starrman was getting more and more forceful.

He typed, "Hey slut, get off my Joanie." I ignored him immediately as Brandy started licking my inner thigh ever so close to my puss as she removed my stockings one by one.