Cherry Takes On The NFL Ch. 02

Story Info
Cherry is surprised and the orgasms keep cumming.
13.6k words
4.7
47.5k
26

Part 2 of the 8 part series

Updated 11/02/2022
Created 06/19/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Liquor69
Liquor69
312 Followers

"Not a word to her, okay? Mark asked. "See if Jamal and Chris are on board with this little scheme of mine and call me back and let me know."

"You got it boss. I can already tell you they will be but I will check. How long are you planning to be there? Rashad asked.

"I'm planning on a ten day vacation. I'm hoping you guys can stay for most of it. I don't want you guys bringing dates because you'll be getting all you can handle and more once you get there. It would really blow her mind though if you could arrange for a mind blowing party while you are there. She really would lose her mind and your rewards would be beyond belief. Trust me on that. I know her that well. Do you think you could arrange that?"

Rashad laughed, "Oh there is no doubt in my mind that could and will be arranged. Now who are you bringing to this shindig?"

"I'm bringing her as far as appearances go. Once she gets there, I'll be on my own. She will be with me, in the box for the game but with you guys afterward. I've got a few other pleasant things lined up that I'd really like us all to do but as for me, I just want to unwind and relax."

"Are you alright? Seriously Mark, we are worried about you. First, you feed us a line of crap that you don't find Cherry attractive and none of us believe that for a fucking second. Now, you are telling me that you are coming to Hawaii, with her, for us. I mean this is our Mark, the man who dates actresses and models and gets more pussy in a month than the average guy gets in a year. Are you sick?"

"No, I am quite well. I'm sure if I want some female company while I am there that I can find some. As you say, I do know how. As for Cherry, she is not just a friend and you know it. I love that woman with all my heart but what she wants, I can't provide. That is a fact of life and I accept it. If I looked like you three, I'd shoot you before I ever let you lay eyes on her. So, having said that, I have given her the best three guys I know and I am happy that you have treated her so well. Now, call the guys and let me know."

"Question boss, where are you staying?

"Oh shit, I have taken the top floor of the Honolulu Palms. It is actually two four bedroom suites. I have one side and you guys have the other side. There will be plenty of room to party and all the privacy anyone could ask for. Diane in my office made those arrangements. I just forgot to tell you. My bad."

"I'll call you back," Rashad said.

Rashad placed a conference call to his two buddies and caught them before they went to practice. They all played for different teams and all three had been selected for the Pro Bowl again. He liked the fact that they were going to see Cherry again. Mark was right about her. She was not only gorgeous. She was sexy, loving, caring and adorable. She also had the strongest sex drive any of them had ever encountered. Rashad filled them in on Mark's plans and they loved what they were hearing. He told them to plan a ten day stay and not to bail after the game. They didn't mind spending New Years Eve in Hawaii one bit.

Jamal burst out laughing, "We have to find three of the hottest women we know for Mark. I mean, seriously, these women have to be the sexiest black women on the planet. If that muthafucker thinks for one minute that he is going to be alone, he's outta his honky head."

I know who I am going to get but she isn't black. She was Miss Hawaii a few years ago and she is the second hottest woman I know. All she has to know is that she will at least once get to be with Cherry and she will definitely be a go for this. Plus, she knows Mark, only by reputation. She asked me if I thought he could represent her in her movie career. Now, she can ask him herself."

"Preferably while she has his dick in her mouth," Rashad giggled. "As for me, I'm going to ask my friend Diane. Mark will love her to death. She fucks like a mink. She loves white men and she too, wants to meet Mark. She is one of the top lingerie models in the country. It's funny because she asked me the same thing about him representing her. She earns millions a year. She is on so many covers and ads. Mark should consider this actually."

"I don't even have to think about this," Chris stated. "Remember that lawyer I dated a while ago? Lori is so hot. She is exactly what Cherry said Mark loved. She and I are good friends but she won't fuck me anymore. She says I am too big for her. She is a wild, fantastic fuck, gorgeous face and she lives to suck cock. I talked to her just the other day. She just left the firm she was with. She had some differences with the partners and she was tired of playing politics. She also knows Mark by reputation. I'm betting she would love the chance to meet him."

Rashad said, "OK, call them and call me right back. Tell them where and with whom they will be staying. Also, Mark wants us to arrange a special party for Cherry. I mean he wants us to get the guys together and give her so much cock that she begs us to stop. Think we can arrange that?"

"Fucking right we can! Damn, can you imagine what she will be like with us after that?" Chris exclaimed.

"Call me back."

Within a half hour, they had their answers. Everything was a go. They were like kids again, plotting Mark's surprise. They were also wanting to see their dear Cherry once again.

Early the next morning, Mark logged onto his favorite site and sat in a room waiting. It didn't take long until Cherry signed in.

When he saw her screen name, he didn't say hello. He just typed three words, "Answer your phone."

He hit speed dial and the phone rang once.

"Hello darling, is everything alright? You don't usually call unless you're in town or something has happened."

"I need you to accompany me on a business trip. It is very important and you'll be gone for ten days. I'll cover all the money you would lose so that is not a problem for you. I really, really, need you with me."

"When is this trip. Where are we going?"

He gave her the dates and then told her they were going to Honolulu.

"Hawaii? Did you say we were going to Hawaii? Are you fucking kidding me? Hawaii? You know damned well how much I want to go to Hawaii. I've never been there. It is so beautiful. I hope we get to see a few things. I want to go. Can we leave tonight? Oh Mark, I would love to go."

"Well, let me tell you that the first three days, I have to work but I want you with me. I want you to look your usual gorgeous self. It is Hawaii so you'll be dressed "casual gorgeous". We do have a dinner to go to and that will be "really gorgeous" but not formal. Oh yeah, there is a really big thing we have to attend but you can be as casual as you want. After that, it is bikini's or less for the next week. So, to wrap it up, it is 3 days of fun work and a week of pure luxurious vacation. Still interested?"

"Oh wow, I can't believe you. You always make me so happy. Damned right I am going. Nothing could stop me from this. Oh wow, I have to go shopping. Fuck, I am so excited I just came."

"That is too funny. It must not have you too excited. I've heard you have bigger orgasms ONLINE," Mark laughed.

"Oh hush you or I'll..."

"Or you'll what?"

"I love you Mark. When do we leave?"

"Well, this is what I was thinking. If you want to extend it one day, I can pick you up on Wednesday morning, after the club closes. We can fly to Vegas so I can pack and get what I need together and then we can fly to Hawaii. We would get into Vegas about 4 AM Vegas time, grab a bite to eat and then some sleep. Thursday morning, I have to go into the office for an hour. You can lay out by the pool or go gamble or whatever. When I get back, it is off to the airport and on to Hawaii."

"Oh I am so excited. I really am. I can't wait."

"Well, you won't have to wait long. I am so glad you said yes. I will be so proud to have you on my arm Cherry. You know I really do care about you."

"I know you do my dear, I know you do."

The week flew by and they talked every night. With each passing day, Cherry got more excited.

"I have to tell you something," she said one night. "I've completely changed my hairstyle and color."

"You change your hair color all the time. That doesn't surprise me one bit. In fact, you have many fetishes but hair color and shoes top the list and it is a very long list."

"Well, my hair is much longer than the last time you saw me and it is jet black." I really hope you like it.

"Sounds perfect to me. Just as long as it does not cover the most perfect ass God ever created, I'll love it," I quipped.

"You like my ass? You have never once commented on my body other than to say that I looked amazing. That is one hell of a compliment coming from you."

"Cherry, there is absolutely nothing about you that I don't like. You are, seriously, the sexiest woman I know. From your eyes, to your nose, your face and your killer smile. You have the most gorgeous breasts, ass and pussy I've ever seen. I really love your voice. There is nothing I would change."

"Wow, I never knew that. Thanks."

"You're welcomed. I need to tell you something. Tomorrow night when you get off work, I want you to drive to the executive side of the airport. My assistant arranged for your car to be in the executive garage while you are gone. It is more secure. Do you know where that is?"

"Yes, what do I do, just pull in? Who will I ask for?" she inquired.

"I'll meet you there and it will be taken care of."

"Great. I can't wait. Hawaii, we're going to Hawaii. This is unreal."

"I'm tired hon. I've been tired now for a long time. I really need this vacation. I'm going to bed. G'Nite." I said

"G'Nite, get some rest. You're going to need it."

"No I'm not. All I need is rest. Luv ya. See you tomorrow."

Mark laughed as he signed off. He really did care for her. Giving her this gift was going to be the best one he had ever done. He really loved to make her happy even though he would never touch her.

Mark left New York at midnight and flew to pick up Cherry. He sat and enjoyed his rum and coke. He lit a cigarette and watched the news. His pilot Jack informed him they were approaching the airport. He finished his drink and put out the cigarette as his assistant Michelle took the glass and stowed it. Another perfect landing. Mark was so happy with his flight crew. Jack and Tom were retired Navy fighter pilots and he stole Michelle away from a top law firm a number of years ago. Mark and Michelle had shared many a night in various cities and they had a very special relationship. She was a blonde with a great body, a hunger for both sexes and a drive that was hard to quell. She was the perfect traveling companion when Mark was not otherwise occupied. On a trip like this, she was a total professional.

They taxied the G5 to the terminal and Mark was pleased that they were there fifteen minutes ahead of schedule. Mark deplaned and walked into the terminal. It was empty at this time of the morning. Tom came in and filed the new flight plan as Cherry arrived. He walked out and she ran into his arms and kissed him passionately. He took her bags from the car and Tom took them to the plane. Mark made the valet arrangements and they walked from the terminal to the plane. Cherry stopped dead in her tracks and looked at the plane.

"What is this? I thought we were taking a regular plane. Whose plane is this?"

"This is my plane hon. My job requires me to be all over the globe. You know that. I can't wait on commercial carriers anymore."

"This trip is getting better by the minute."

They boarded and Mark introduced Michelle and took Cherry up to meet Tom and Jack. Cherry was awestruck and kept looking at the plane. Her hands were running over the softest leather she had ever felt. She kept looking as they reached altitude. Michelle served them drinks and Cherry was speechless.

"You never told me we would be riding in style. Holy crap Mark. I mean, I never knew you lived like this. I know you travel all over all the time but I just thought you took the same kind of plane we all do. This is impressive. What kind of plane is this? It is so pretty."

"This is a Gulfstream G5 hon. Yes, it is a nice plane. It gets the job done."

Another couple of drinks were served. Cherry sat beside Mark with her head on his shoulder.

Michelle winked approval at Mark after appraising Cherry critically. Mark laughed to himself. He wasn't quite sure if she was approving her for him or for her. What she didn't know was she would probably have her before this vacation was over. He knew he wouldn't.

Tom announced that they were on final approach to McCarran and they buckled up. Cherry was looking out the window at the lights of the strip. She loved the view. It was a view that Mark could never get enough of himself. He loved this city. The plane landed and taxied to the terminal. The valet was gone only a couple of minutes and pulled up to the front door. Cherry just starred as the red Ferrari idled at the curb. She was seated in and Mark turned onto Koval and headed home. He turned on Tropicana and headed to the strip and turned right at the MGM Grand. Cherry sat speechless once again. She had been to Vegas before but she had never arrived in a private jet nor had she cruised the strip in a Ferrari. So much had changed since she was last there. Mark drove north on the strip and pulled into Trump Tower.

He pulled into the parking garage and into his private garage. There was parking for four vehicles. In addition to the Ferrari, there was a Maybach, a pickup truck and a Candy Apple Red 32 Deuce Coupe. If there was one thing she knew, it was cars. Mark helped her out of the car and walked to the elevator inside his private garage. She entered the elevator and saw there were only three buttons. They were labeled P1, P2 and P3. This confused her until the elevator stopped. She stepped out into the most beautiful apartment she had ever been in.

"Welcome home sir," a strong male voice boomed.

"Hello Jackson, This is my friend Cherry. She is accompanying me to Hawaii tomorrow."

"It is a pleasure to meet you Jackson," Cherry stated as she looked at one of the largest black men she had ever seen.

"Are you hungry sir?"

"I don't know, are we?" Mark asked Cherry. "I know I could eat something."

"A sandwich perhaps," Cherry suggested.

"We have fresh Pastrami, would that suit you miss?"

"Jackson, that would be delicious. Thank you."

Jackson walked away to the kitchen and Mark started laughing loudly.

"What? What did I say that was so damned funny?" Cherry demanded.

"It is not what you said but what you didn't say that got me laughing."

"What didn't I say?"

"Jackson, put your dick on a hoagie and I'll be the happiest woman on earth!"

Cherry looked at him and burst out laughing. "You fucking know me too well. That is exactly what I was thinking. Where did you find him?"

"Jackson was one of my players and he was very badly injured. His career was over and he could not get a job because of the medical issues and health insurance so I hired him. I am gone so much and I am glad he is here taking care of the place and the staff."

"Staff? How many people are here."

"Jackson and Michelle live here and Tom and Jack live two floors down. They are on call 24/7 as am I. There are 3 maids that come in every day. One per floor."

"One per floor? Come on Mark, seriously? This place is 3 floors?"

"When were finished eating, I'll take you on a tour."

Mark showed Cherry the place and she was blown away. The top floor was Mark's private quarters. It took up the entire top floor of the building. His living room was huge and the view of the strip was amazing. His office was elegantly constructed of dark cherry wood. It certainly was something to see. He had his own private gym with every piece of equipment you could ever imagine. Cherry lost her mind when she walked into his bedroom. It was literally half of the top floor. The furniture was so tasteful. The bed was a fantastic four poster unlike anything she had seen before. Whoever the decorator was, they had only one thing on their mind when they created this look. SEX. SEX and ORGASMS!

"Hey, What the fuck? You have a stripper pole in your bedroom?"

"Yeah and two more in the playroom on the lower level."

"I can't even describe this to anyone."

He took her into the master bath and her jaw dropped. She walked into his closet and looked at him in disbelief. He had the smaller of the two closets. The larger one was empty.

"Why don't you use the larger closet?"

"Well, someday, if I find the right woman, she will need it. That is why it is empty."

They went down to the middle floor where they had eaten. He showed her where Jackson had his two bedroom apartment and then he showed her where Michelle had her two bedroom apartment. He showed her the kitchen and she started to laugh.

"You could just live in the kitchen. It is fantastic. Now I know why you love to cook."

Mark took her downstairs and showed her the party floor. He wasn't kidding. There was a bar that belonged in the Bellagio, a dance floor that was huge. There were slot machines and pinball machines too. Mark took her hand and walked into a double door room and Cherry was simply stunned. This was a twenty four seat theater. It was amazing. Mark walked in and sat down. As Cherry walked, she looked down at the floor. It was very soft. She sat next to him, looking at the floor again.

"Why is the floor so soft?"

"Get on your knees dear."

"Oh my God. Holy fuck me flying! This floor is this way so whoever is sucking a cock won't hurt their knees. You've thought of everything."

"Honey, lots of pussy gets eaten in here too you know. There is more to see. Come, it gets better."

They left the theater and walked into the next room. Mark hit a switch and turned on the lights. The floor was tiled for the first three feet of the room. After that, the floor was mattresses. This is part of the orgy rooms. He hit another switch and the lighting dimmed and the music came on and Cherry smiled broadly.

"Oh this is great. I love it."

"Come see this." They walked into the next room. It was long and narrow. A padded bench ran the length of the room and glory holes dotted the wall.

"You've got to be kidding me?"

"Nope, my friends like to party." Follow me. He took her hand and walked out of this room and past the next. That was the other side of the glory holes. The last room was interesting to get into. It was a maze and the farther you went in, the darker it got. After the last turn, the floor was mattresses again but the room was pitch black.

"This is the grope room. When you are in here, you don't have any idea who is touching you, sucking you or fucking you. This is a very popular part of the party. I enjoy being in here myself."

They walked out onto the balcony which ran the entire length of the building. There were three hot tubs and lots of chaise lounges and mattresses. People liked to fuck in Vegas and this was a great place to do it.

They went back in and up to the second floor. This spectacular level was elegant in the extreme. Mark walked into the living room area which was so expansive. There was seating for at least 50 people. Big screen TV's, large lounging sofas, perfect for fucking. There was a large area of hardwood floor set into the carpeted area. Cherry asked Mark why he had two dance floors when the one downstairs was so huge. Mark laughed and walked over to the wall and flipped a switch. The dance floor began to rise. As it lifted, a gorgeous swimming pool was revealed. It was lit with LED lighting that gave the pool very sensuous look and feel.

"Mark, I am beyond amazed. This is simply the sexiest home I have ever seen."

"There you are," Michelle said as she walked into the living room. "I've been trying to find you. Cherry, come with me dear."

Liquor69
Liquor69
312 Followers