My relationship with Bella was for all intensive purposes was slowly fading away. She had settled in Atlanta with the boys and her husband. There were the nightly skype sessions and sexting, and I longed for her daily presence and companionship, but we both knew that the relationship was slowly moving towards a friendship basis. Unless, of course, things between her and her husband made a turn for the worse. Which was entirely possible.
Tiff and I were slowly blossoming into more of a business relationship rather than a physical one. We typically went to lunch several times a week to chat, get to know one another on a more personal level, and talk business. She was all that Bella had said. Smart, witty, on the ball with current events, and the girl next door. Nothing happened sexually with us after that first encounter.
Occasionally during our lunches, she would say that her husband was becoming more distant and he was not intimate anymore. But, she still tended to be all business. I could tell she wanted more from our relationship. But was, as she said, dedicated to her marriage.
I had to respect that and didn’t push the envelope further as I was dealing with my wife’s situation more. My wife was slowly failing and the doctor said she didn’t have much time left. I made sure the arrangements were made and informed the family. And, true to the doctor’s word, my wife passed three weeks after Bella left. I buried her next to my sons and began my period of mourning. I was once again devastated and began to retreat back into my shell. Working sixteen hours a day, growing the business bigger and increasing my wealth. But, there would always be something missing. Always.
*****
Four months later, I was at a conference in Vegas when I received a text from Tiff, which rarely happened.
“Hey Jay, it is Gus. You have time for lunch tomorrow?”
Knowing full well she wouldn’t come, I replied, “Hi Gus, I have time for dinner tomorrow, but you will have to come to Vegas, as I am attending a conference.”
“Where is the conference?” – Gus
“Pharoh’s Palace” – Jay
I didn’t get a response from Tiff after that and I let it pass as the conference was taking up most of my time that day.
At 7.30 a.m. the next morning, I checked my phone before heading off to breakfast. There was a message from Tiff with a picture of her standing in front of a fountain wearing that famous shop shirt with ‘Gus’ on the left side.
“In the lobby, will be waiting for you” – Gus.
I gathered my things and headed down to the lobby with a noticeable skip to my step but wondering why in the world would Tiff be here. I soon spotted her standing by the edge of the fountain. Quietly, I came up behind her, put my arm around her waist and gave her a kiss on the cheek.
“Glad you could make it, I was just kidding about dinner tonight,” I said.
Tiff turned sideways and embraced me with a hug and a deep kiss. “Oh Jay, Oh Jay…”
Tiff’s eyes were red and puffy, she was shaking slightly. I could tell she had been crying.
“Tiff, what’s wrong?”
Taking a deep breath, and fighting back the tears, Tiff let it all out, “Oh Jay, I found out Jimmy was cheating on me. We had a big fight and he started to get nasty. I left the house with a few things and stayed in a hotel for a couple of days. I didn’t go to work for three days. They fired me yesterday…”
Tiff started crying and broke down again.
I didn’t say a word. Just took her into my arms and hugged her until she stopped crying. After the tears subsided, we made our way up to my room.
“Here is my room key, it has access to the suite and also is a credit card for the hotel. You can use it for whatever you want. Anything at all.”
“Thank you, Jay, I don’t need much right now. Just some sleep and some clothes. The airport lost my bag.”
“Just get some sleep. I hate to leave you now, but I have to speak at the conference very shortly, so I need to get down there. I am going to contact my assistant here and she will be up in a few hours to get you situated. She will show you around the casino and get you some clothes for the rest of our time here in Vegas. I have a standing reservation for a cabana by the pool. Get yourself some sun, drinks, and a massage this afternoon. I should be done with the conference around 5.30. We will be going to go to dinner tonight with some of my business partners.”
With that, I gave Tiff a kiss and headed to the conference. My speech went well, and I began to lose track of time until my phone vibrated in my pocket about 11.30. I read the email as the current speaker droned on.
“Jay, I cannot thank you enough for today and the business relationship/friendship that has grown between us these past months. I knew you were the one for me the moment I made eye contact with you in the locker room at your office. I gave myself to you in the dressing room of the clothing store, something I never would do with any other man. And, after every lunch date we had, I fell for you harder and harder. I kept my distance between us because of my marriage and what was going on with your wife. But, I know now that I should have let the relationship move forward even more after that day in the dressing room. I don’t want you to think that me coming to you here in Vegas is a ruse, to get you to feel sorry for me. If you think that, I will leave on the next flight. If not…”
I closed the email and smiled. Then my phone vibrated again. This time a string of texts with pictures. “Choose what you want to see your girl wearing. That is… if I am staying. You won’t be disappointed,” Gus.
I opened each text: The first text with four pictures. Tiff posing with four different string bikinis looking very hot. Her pale white skin accentuated the see-through materials. Her nipples were erect in each top and the thin red strip above her pussy was poking out of the one-inch bottoms. I responded, “Get all of them, but you won’t need the tops at the cabana.”
The second text: Four pictures of Tiff in sexy but elegant black strapless dresses. She looked good enough to jump through the screen and take her this second.
I responded, “You are looking good enough to eat.”
The third text: Six pictures of Tiff in various everyday clothes. She looked amazing in all of them.
Again, I responded, “Get them all. Damn, Tiff, you look amazing in anything, and nothing at all.”
The fourth text almost made me fall out of my chair and I dropped the phone. One picture of Tiff naked, handcuffed with her hands behind her back, on her knees with her head tilted back looking directly into the camera. The message: “I will be waiting for you… I’m hungry?”
I smiled and looked at my watch, fifteen more minutes until lunch. After the speaker had finished, I made my way up to my room. And there, kneeling in the hallway was Tiff. Beside her was a tray of food and drinks.
“Hmm, you make this very difficult, Tiff. I need some food, but you are very tempting to eat as well. But, most of all, you teased me this afternoon.”
“I will please you whenever and wherever you want, Jay. I am yours. Always yours.”
I pulled the keys for the handcuffs out of the drawer. “Have you eaten today?”
“No, but I can wait.”
“Stand up and come over here.”
Tiff stood up with some difficulty and walked towards me. “Yes, Sir, what do you want?”
“Good, you know when to call me Jay and when to call me Sir. You learn very fast. I am going to release you. We are going to eat and you are going to tell me about your morning. And, then you can be desert.”
We began eating, or more specifically, Tiff sat on my lap and we fed each other and she told me about her day.
“I didn’t get much sleep. Your assistant came up about an hour after you left and woke me up. We grabbed some coffee and headed into the shops. You didn’t tell me Monique was going to be as sexy and nice as she was, maybe a bit too nice. But, she seemed to know what you liked and what you wanted to see on me. I knew the basic ideas, but she pointed me in the right direction.”
“So, I am to assume she took all the pictures and she came up with the idea of the handcuffs?”
“Yes, she took all the pictures. And by the way, the clothes were already bought by the time you got the pictures. But I had the idea of teasing you a bit. The cuffs were my idea since you left them by the TV along with several other, umm, rubber items this morning. The rubber items were gone after the maid cleaned the room, but she had the cuffs placed on your pillow by the time we got back here. Seems like you have a few little kinks. I told Monique to cuff me after I decided to strip naked and send you that last picture after I told her what to type in. She stayed for a bit to keep me company and let me know my schedule for the next few days. Seems like I am going to be a busy girl, per your instructions.”
“Do you remember what I said in the dressing room that day?” As I kissed her and began caressing her breasts.
“If I tease you I must please you.” And with that, Tiff slid off my lap, and knelt in front of me. I slid off my pants and boxers and stepped out of them and walked out onto the top floor balcony to enjoy the view of the city.
“Come over here, Tiff, on your knees. I want to enjoy two beautiful sights for lunch. The view of this city and mountains and my girl taking every last inch of me into her mouth. I remember the last time you gave me pleasure and I have waited long enough for this moment.”
Tiff slowly made her way to the outdoor balcony and knelt before me. The slight wind blew her hair around as she licked her lips and stared at me with longing in her eyes. I nodded and she began to work her wonderful magic on my cock. She took all ten inches of me into her mouth and slowly sucked on my cock, gradually increasing her pace until I unloaded a load of cum down her throat. It was a beautiful sight seeing her take all of me and enjoying the view of the mountains.
*****
It was 4.30 and the conference was wearing on me. I would have to remember not to schedule so many boring speakers next year and to get some excitement going. It seemed as if all the conference goers were experiencing that look of, “is this ever going to be over?” I looked down at my phone and saw that there were several texts to be viewed.
I clicked the icon and there were several pictures and a video. Apparently, Tiff was having a good time at the pool. One picture of her getting a well-needed massage and one picture of her lounging in the pool on a raft next to Monique. Both were topless with a drink in their hands. Another picture with her and Monique arm in arm, posing totally naked. The caption read, “Missing you.”
Then the video popped up, luckily I had my volume down. The private pool area was packed and the music was thumping. Tiff and Monique were dancing, swimming, and half-naked people were partying hard. I had to admit, the party looked much better than this conference. I turned up the volume a bit to hear what was going on as I saw Tiff’s face enter the screen. I heard her say in a sultry voice, “Jay, I need that hard, thick, cock of yours.”
The screen faded back a bit showing Tiff on a lounge chair. The phone screen ran down her body and down to her legs as she spread her legs. Two thin, long, tan fingers parted her pussy lips and another began to rub her clit. I knew those fingers. They were Monique’s. My mulatto assistant was beginning to pleasure Tiff. The video shut off.
My time at the conference was now over after seeing the video. I quickly left and went to my room. Changed into my swim trunks and headed down to the pool. I wanted to have some fun as well, but I knew that if Tiff continued on her path, she wouldn’t be able to go to dinner tonight. She looked a bit tipsy in the pictures and knowing how Monique loved to party, I had to curb the fun a bit. Plus, I had big plans for Tiff tonight. It was her audition. And if she did well, I would have a business partner, lover, and soon-to-be mistress.
As I entered the pool area, I grabbed a beer and took in the swath of dancing bodies and began to look for Tiff. Over in the back corner of a cabana, I noticed a screen pulled in a semi-circle, enclosing the corner. Walking up to the screen, I could hear moans above the music. I smiled, and quietly slipped inside, not hiding my appearance. After a few moments, Monique glanced up, her face covered in juices. She winked and continued her tongue and lip work on Tiff’s pussy. I stood and drank my beer and enjoyed hearing Tiff moan. Her hips were bucking every few moments while her fingers pinched her already red erect nipples. She was having multiple orgasms upon multiple orgasms. Her eyes were closed as I approached her.
Leaning down, I whispered in her ear, “Turn over on all fours, this fat, thick cock is going to fill you to the hilt.”
Her eyes opened and she smiled. I kissed her deeply. Reaching down, she removed Monique’s head and flipped over on all fours, her ass arched in the air, waiting for me. I kissed Monique, tasting Tiff’s juices as I probed her mouth with my tongue. Monique, pulled my swim trunks off and slid down my body, immediately taking my cock in her mouth and sucking on my half erect cock, making it rock hard. Once hard, she stood up and kissed me again, then took a seat in the chair next to Tiff.
I gave Tiff a hard smack on the ass and lifted her off the chair, bringing her already wet pussy higher in line with my cock. Her head fell forward onto the chair as I placed the head of my cock next to her already puffy red pussy lips. I entered her with the head of my cock and stopped. I could feel her trying to push back onto me. I held her in place for a few moments and then rammed my cock into her until my hips hit her tight ass.
Tiff squeezed the cushions of the pool chair and let out a low moan. Waiting a few moments, I pulled almost out of her again, leaving my cock head at her entrance. Again, I rammed my cock into her tight wet pussy. I could feel her pussy muscles wrapping around my cock when I hit her ass again.
Then I let loose. All of the sexual frustration of the past several months came out. For about fifteen minutes, I pounded her, my balls constantly smacking against her ass.
Her moans turned to words. “Oh Jay, fuck… me… fuck… me… Oh god, fuck me,” as I felt her body convulse and come to orgasm time after time.
I could tell Tiff was beginning to tire a bit. I stopped my pounding of her and set her back down on the chair. My cock was still hard. Tiff looked over her shoulder and licked her lips. Her hair was matted down and sweat was glistening on her back. Slowly, she turned over and stood up, getting off the lounge chair. Tiff had a glow about her now.
Wrapping her arms around my neck she pulled herself up and wrapped her legs around my waist. We kissed and embraced. Tiff slowly slid down a bit and my cock entered her once again. She was still very wet and I could feel her pussy muscles tightening around my cock.
Softly, she whispered, “Let me please you. I want your cum deep inside of me, deep inside me.”
With Tiff on my cock, I walked to a bar stool and sat down. Slowly, she began to move her hips back and forth, my hands holding her ass and helping her move. There was no sudden increase in her movements. She kept slowly moving back and forth, each time she moved her mouth opened and short gasps came out.
“My… god.. Jay… you… are… perfect.. you… hit… my… spot… every… time.”
I could feel Tiff’s pussy muscles tightening time after time I hit her spot. Her head fell forward onto my shoulder, then I felt her body tremble, her nails dug into my back and she bit down on my shoulder. She stopped moving and I could feel her juices flow over my cock. But, I couldn’t let her stop, I could feel my balls tighten up and the cum beginning to build. Grabbing her ass a bit harder, I kept up her motions. Her nails dug deeper into my back and she let go again as I came deep inside of her, her pussy muscles still massaging my cock as it went limp inside of her.
Tiff, rested her head on my shoulder for a while and hugged me all the while I ran my fingers through her hair and down her back. The moment lasted a while and she leaned back, smiled and kissed me deeply. Her lips moved down my neck and to my shoulder, kissing the area she had bit, making it feel a little better.
“I didn’t know I had a scratcher and biter on my hands,” I whispered in her ear.
Pulling her head up to face me, “I… I… I have never cum like that before. Before the dressing room with you, I had never had an orgasm. Before today, I had never experienced a woman. I… I am sorry if I hurt you… but…”
“My dear Tiff, you have just begun to explore. Don’t worry about the markings. I am used to it. Let yourself go, let me show you what is out there. Try anything once, and if you don’t like it, tell me. If you don’t object, then I will know you are enjoying yourself.”
“Now, go with Monique and get cleaned up. There is a dress on the bed for you to wear tonight. Your salon appointment is in thirty minutes. Monique knows the drill. I will see you at dinner.”
“I won’t disappoint you, Jay, never ever.”
“I know you won’t. Now go get ready. And make sure you do the assignment I gave you on the table,” as I gave her a nice firm smack on her ass.
I watched with a smile on my face as Tiff and Monique left the cabana, holding hands, their see-through body wraps barely covering their naked bodies. My dear, sweet Tiff was coming of age.
Any thoughts or words of wisdom are always appreciated. Let’s continue on with the fun of Tiff and Jay
