Catching Up: Part Four 21+ [M40/F37] [Straight Sex] [Interracial] [Cheating] [Busty] [Huge Boobs] [Playboy Bunny]

Chapter Four: Getting a little extra

“So, you fucked, a playboy model?” Alicia asked as she sat on my couch.

“Yeah,” I said as she stared at me.

I felt it necessary to tell Alicia about my encounter with Helen. Since it seemed we were getting closer than the usual friendship.

“You’re not mad?” I asked.

“I would’ve been mad if you didn’t?” Alicia smiled. “Hell, I would’ve slept with her, if given the chance. And I don’t find women attractive at all.”

“I am glad that you aren’t mad,” I said.

Alicia smiled as she leaned in close to me. “So, what does she look like?”

“Like a playboy model,” I shrugged.

“Well, I will just have to see for myself,” Alicia said as she stood up.

She went to my computer that was across the room. “Sit,” she ordered. I sat in my chair and went straight to the internet a simple search for Helen and there she was on the screen.

“A raven,” Alicia said as she leaned over me. “Your first?”

I honestly never fucked a woman with jet black hair before, at least not a white woman with black hair. “Yeah,” I said as Alicia’s hand got on top of mine as she guided the mouse towards the images tab.

“Let’s see what other pictures, she has on here,” Alicia said, almost whispering in my ear.

It showed most of the tame pictures, primarily clothed in public or at shows. “Boring,” Alicia said. “There we go,” she said as she found a few shots of her playboy days. None of them nude, mostly in lingerie. “Well, she does look good in black,” Alicia said as Helen posed in black lingerie on the back of a sports car.

“Yeah,” I said as Alicia’s other hand started rubbing on my chest.

“I bet she looked even better with your black cock inside of her,” Alicia again whispered in my ear.

My cock was rock hard, and wanted to be released from my pants. “Did she let you fuck her raw, or did you have to wear protection?”

As she talked to me, she flicked through other images of Helen on the screen. “No protection.” I said in barely a whisper as Alicia’s hand reached my belt.

“Pull out, or filled her up?” Alicia said as she spun the chair around.

“Inside,” I said as Alicia kneeled to the floor.

“Naughty girl, letting a strange black man fill her with cum,” Alicia said as she unbuckled my belt. “Did she ask for it, or did you just dump it in her?”

“She asked for it,” I replied as I watched Alicia’s tongue circle the head of my cock.

“My kind of girl,” Alicia said as she started sucking on my cock. Her head was bobbing up and down between my legs. “Did she suck on it like this,” Alicia said as she bobbed her head up and down without looking up at me. “Or like this,” she said as she stared at me.

“The first,” I said, barely able to speak.

“Oh, she doesn’t like to look up,” Alicia said, shaking her head.

“She took all of it,” I said, looking at Alicia’s blonde hair.

“All of this?” Alicia said with both hands on my dick as she looked up at me. “She took all of this in her mouth?”

“Yes,” I nodded.

Alicia looked at my dick and back up at me. “All?”

I nodded again.

Alicia tried to repeat the same thing Helen had done but stopped short; again and again, she repeated the same thing, eager and pushing herself to take all of my cock in her mouth.

Finally, she stopped with a loud gasp. “So, she is better than me at sucking this, but….”

Alicia took off her top and plunged my dick underneath her bra and between her breasts. “I am much bigger up top than she is,” she stated as she bounced her vast boobs on my dick.

That was very true. I saw the size of Helen’s bust online as we looked at her playboy stats. Helen was an E. I had no idea what size bust Alicia had, but it certainly blew an E out of the water.

“You’re wondering how big are the boobs that are wrapped around your cock are?” Alicia asked as she increased the speed of her tit fucking.

I nodded with excitement. “H,” Alicia said. “I was barely a C before I got them done, now they are a H, think she can top this?” Alicia said as she buried her head and licked the tip of my cock as it barely escaped its tit prison.

Alicia’s canary yellow bra had my cock trapped between her two large globes as they bounced up and down, faster and faster. The friction between them increased as she pushed them together.

I barely had time to say I was cumming before I shot cum from between her boobs. Some of it escaped and splashed onto the tops of her breasts. The rest of it was trapped between them.

“I bet she can’t do that, not like me anyway,” Alicia said, releasing my dick from her boobs.

“You’re too much,” I said as I bent over to kiss her.

“Remember that,” Alicia said as we kissed.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~~ ~ ~ ~

I went to work the next day, the happiest man in the building. I had a great job that I was good at, which paid me a ridiculous amount of money.

I was making more money now than I ever did in my entire life. The first time they showed me the salary for the whole year, I almost fainted on the spot. They said it was the starting salary, and depending on how I did, it would increase.

Aside from the job, I had a woman that was a bombshell. Just walking down the street with her made me feel like I was on cloud nine. Never had I been with a woman that made other guys take second or third looks or walk into things.

Sure, she was a B movie actress who showed much more skin than many other actresses. Alicia stated that most of her movies didn’t have her going topless but scantily clad and sometimes holding her breasts in her hands.

Her last movie was about space cheerleaders fighting aliens in scantily clad cheer uniforms. Of course, she mentioned there were many scenes with her big boobs bouncing up and down directly in front of the cameras, but never nude. I shrugged and fucked them again for good measure.

“Jackson,” I said as I got off the elevator.

“Rod, my man,” Jackson said as he walked toward me. “I heard you talked that Peterson kid into signing with us, good job.”

“Yeah, he should be a good linesman for any team that picks him up,” I said.

Jackson nodded. “You’re doing good work here, keep it up.”

I nodded as we went our separate methods. I loved the atmosphere here; everybody was on the same page. Sign athletes and get their names on the dotted line. That was the motto. But that wasn’t all. If they were school athletes, we ensured they had good grades and a plan after their sports career was over.

I was busy taking a phone call from an international student trying to transition from their country to the states to play in the NFL.

When I noticed a familiar face pass my office. All of our offices had glass walls so we could see and not feel trapped inside.

I hurriedly ended the conversation and then walked out of my office. “Jason?” I said as I saw the prominent figure sitting in our lounge area.

“Rod?” the tall Hispanic man said as he stood up.

“Yeah,” I nodded as we both shook hands.

“How long has it been?” Jason asked.

“Since I graduated and you went to play ball,” I said as I stood by an old school friend.

“Of course,” Jason nodded.

Jason Guerra was just like me, but instead of the gridiron, he was the star of the diamond. He had set records in our school that still hadn’t been broken.

“Last I heard you were dominating the diamond,” I said as we sat down.

“I hadn’t dominated anything,” Jason shook his head. “Played a few good games and had some good runs, even some tight playoff games, but dominated, nah, not me.”

“I hear you,” I nodded.

“Don’t get me wrong, I had some real good games, set a few team records, but getting to the big game, nah,” Jason said. “What about you?”

“Working here now,” I said. There was no need to tell my past. Everyone knew I didn’t go any further than school.

“That’s right,” Jason nodded. “Man, you should have gone. Now you would’ve dominated, that’s the truth.”

“We will never know,” I shrugged.

“True,” Jason nodded. “You should give me your number, some of the guys still hang now and then, play some light tackle football at the park, get a few drinks. They would love to see you.”

“Catching up,” I nodded. “That would be good.”

“Yeah, definitely,” Jason said. “So, what brought you out here, last I heard you were in Georgia.”

I told him about Carl and how I got away from him and was offered a job here.

“Stay away from that motherfucker, I am telling you he is bad news,” Jason said, shaking his head. “That guy is the definition of living in the past.”

“Yeah, I learned my lesson,” I nodded.

“Good,” Jason nodded.

“So, what brings you here?” I asked.

Jason told me about his second son. His first hadn’t been interested in any sports. Jason went on and on about his first son with his first wife, being lazy and not wanting to work and staying home. His second son with his second wife was different and was trailblazing his own path in Baseball.

Of course, that was when Jackson showed up. The two of them hit it off immediately, and we all went into one of the private lounges to get things settled.

“The thing is,” Jason said. “We’ve been approached by other agencies, some of them are a lot better and well known.”

Jackson nodded. “Of course, you could go with them,” he said as he sat back and stared at Jason.

“Most of them have years of experience, got number one drafts under their belt, hall of famers,” Jackson added. “None of them have what we have,” Jackson stated. “We are lifers, even when your son stops playing, we will still be there, making sure he has a life after the game. We have coaches that will be there to help with his financial situation to help him make the most of it, so he doesn’t blow it all on a car, or a flashy house.”

“Or women,” I added.

“Exactly,” Jackson nodded. “We want to make sure, what happened to you, or some of the others that didn’t have good agents, doesn’t happen to anyone under our umbrella.”

Bringing up what happened to Jason made the wheels inside Jason’s head turn. I heard rumours about trade disputes and not being happy about how he was treated. Hearing Jackson mentioning Jason’s past made me think those rumours were true.

“My wife thinks that we should go with Excell,” Jason said. “She makes some valid points.”

“They are a great agency,” Jackson nodded. “Your son will do good with them. Most of their agents are on first name basis with many owners and coaches around all the leagues.”

“They don’t have any ex-players working for them,” I said. “We have two, me included.”

“True,” Jackson nodded. “Very true, sure they could get your son onto a great team, but would it be a good fit, how many number one drafts go to a team where they aren’t a good fit, then have to spend most of their rookie contract on a bad team that doesn’t fit their talents.”

Jason nodded as he looked at his watch. “She is here now,” he said.

“We will get her in here, so we could talk things over,” Jackson said as he went out to get his wife.

Celeste walked in and took our orders for lunch. Of course, Jackson looked at her go and shook his head.

“She’s married and so are you,” I said, shaking my head.

“It’s only a ring,” Jason said with a smile. “I should know this is my third.”

“Three times,” I said, shaking my head.

“Don’t know what it is,” Jason said. “I hate being single,” he laughed.

“Yeah, I remember,” I nodded.

In school, just like Carl, he was a lady’s man. The worse thing was that the Baseball and Football teams had an in-school rivalry. It was horrible now that I wondered about it.

They used to sleep with girls we liked, and they slept with girls we wanted. I never forgot when they sent us a video, and I saw the woman I had a crush on, Linda Chan, getting fucked by Jason and one of his friends. It was the worst feeling I ever had. To this day, I still can see that image in my head.

“Linda!” Jason shouted. “All this time I have been thinking about that one girl, yeah, Linda, man you were pissed.”

“Yeah,” I said, sitting back in my chair.

“Hey, it was payback,” Jason said as he laughed. “You guys got those Auburn cheerleaders, we had been trying to get them and you guys,” he shook his head. “You guys got us good!”

“That was mainly Carl and Winslow,” I smiled. Our Quarterback was also good at getting us in trouble.

“Yeah, but you sure got yours, though,” Jason said. “Don’t play innocent.”

I nodded. I sure was to blame as well, not that said I no, or didn’t get my distribute of a few cheerleaders. If I had known the payback was that they would have run a train on the girl I was infatuated with, I might not have gone.

“Helen,” Jason said as he stood up.

‘Shit!’ I wondered as Helen walked into the room. When she saw me, the same look went over her face. She was as shocked to see me as I was to see her.

“This is my buddy from college,” Jason introduced me.

‘Yeah, I know her, I fucked her three weeks ago,’ I wondered to myself as we shook hands.

“Helen,” she said as she shook my hand.

“Roland, but most call me Rod,” I said as we sat down.

Jackson and Jason continued their talk while Helen and I stared at each other. She was stunning in every way.

It wasn’t until they had reached a stalemate that we left the lounge. I slowly walked back to my office and sat down.

Jason and Helen came into my office. “We would like you to talk to our son,” Jason said. “We were told you were good at talking to athletes that were still on the fence.”

“I could definitely do that,” I said as I stared at them both.

“Good,” Helen nodded. “He also plays Soccer and isn’t sure which one he wants to do professionally.”

“It’s not even a real sport,” Jason said, shaking his head.

“He is good at it,” Helen replied as she bore a hole through him. “He is home for a short time, before he returns, so the quicker the better, when is a good time for you?”

“If he is home, I am free today, I have a few things to wrap up and I can meet you there?” I said.

“Told you, he was the best,” Jason.

“Anything for an old college friend,” I said with a smile.

Helen nodded as she walked out of the office. “You think you can get her number?” Jason asked as he looked out at the office and at Celeste as she walked around the large lounge area.

“As I said, married, very, very happily married,” I said. As I had heard Celeste talk, everything she talked about was George this, George that, where they went, what they did, what they ate. She was still in the honeymoon stage.

“And I said, it’s just a ring,” Jason said as he looked back at me.

“I wonder if Helen thinks the same,” I said.

“If she does,” Jason shrugged. “There will be a number four.”

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Jason’s house was extreme. It made Carl’s house look like a one-car garage in comparison. After he finally walked me through the entire house, no doubt to show it off, all I could think about was the money wasted. There were too many rooms, some of which were probably never used.

Finally, we settled in the large office. Like Kevin, he had many of his medals and trophies aligned everywhere.

“I will go get him,” Jason said, leaving me in the room with Helen.

“Cloud?” I asked.

“I kept my maiden name,” Helen said. “Jason doesn’t mind, as long as… well he doesn’t mind.”

“Of course not,” I nodded.

Just talking to Jason, I knew that he was already or had many number fours lined up.

“Leon, isn’t mine,” Helen said. “Not by birth anyway, but we do have a very strong connection.”

I nodded as the door opened, and a young man stepped in. “Leave us, so we can talk in private,” I said as Leon took a seat across from me.

The talk got fast and furious from the begin. Leon had a lot on his chest that he wanted to get off. Most of it was about his father.

“So,” I said, taking it all in. “He is the one pushing you to play Baseball,” I said as I leaned back in the chair.

“I want to play Soccer,” Leon stated firmly. “But I think I will let him down.”

“Not your problem,” I shrugged. “That is something he has to deal with,” I said. “You don’t want to get into it, then realize you don’t want to play, or don’t have passion for it.”

“But what about….” Leon started to say.

“Let’s talk about you,” I said, leaning forward.

By the end of the talk, Leon decided to stay and finish school, then finally decide what he wanted to do, which would be better for him as he was still undecided.

I leaned back in the chair and looked around at all the sports trophies and medals. All of this could have been mine.

“Thanks,” Helen said as she walked in. “Leon told us what he is going to do.”

“How’s Jason taking it?” I asked.

“Not too well, but he will come around,” Helen said. “He is on the phone with Jackson now.”

“Ah, I am sure I will have to face the music when I get to work,” I nodded.

“Sorry, about the shock,” Helen said as she came closer.

“Nah, we both didn’t know, shit happens,” I shrugged.

“While, that is true, I didn’t lie about what I said,” Helen said as she walked around the table.

“About what?” I asked.

“That I was thankful,” Helen said as she sat on the desk. Just mere inches away from me.

“I have to tell you,” I said as I sat back. “I have a girlfriend; she means a lot to me.”

“Alicia, I know,” Helen said as she looked at me. “She contacted me a few days ago.”

I looked stunned as she looked at me with a smile. “You have a very committed girlfriend, and she is very thoughtful of you and your….” Helen paused as she looked down at my crotch. “Shall we say unique tool?”

“What did she say exactly?” I asked.

“Well, she said if I find myself in a position to make sure it and you gets the satisfaction that you both need, then I should take it,” Helen said.

“After all, how did she put it, if I get it up, then it’s my responsibility to get it back down.”

That sounded like something Alicia would say.

“And I can see that it is, very much in the up position.”

Before I could say another word, Helen was on her knees. “He could walk through that door any moment,” I said.

“He is on the phone,” Helen shook her head. “The boys are in their rooms playing whatever video game they are playing.”

Helen had my dick out of my pants before she finished the sentence. Immediately she started sucking on it faster than I could stop her.

Here I was in Jason’s office with his wife’s head bobbing up and down in my lap.

“Damn,” I said as Helen took me down to the base and back up again, over and over. I looked at her head go up and down while looking at all of Jason’s jerseys, bats and balls.

Helen didn’t stop like how Alicia would take periodic breaks to take a breath. She was like a dick-sucking machine, up, down, up, down.

“You still in here?” Jason said, bursting through the door.

“Yeah,” I said quickly, moving forward. Helen promptly got into the nook under the desk. “Just looking at all your stuff.”

Jason smiled as he looked around. “Yeah,” he said as he looked at all of it. “It was fun, a lot of pain now, but it was worth it.”

“I bet,” I said as I felt Helen take my cock back into her mouth. ‘Shit,’ I wondered as I tried to push her off. If she just sat there, maybe we both could get out of this situation.

“I am sorry about Leon, but I think it’s the right thing,” I said as Jason stood near the door.

It was over if he came closer or sat down in the other chair. There would be no doubt he would hear his wife sucking on my dick or notice the small tuff of black hair bouncing in my lap.

Or any of the many signs that pointed to his wife in the room. I could see her reflection in one of the large pictures on the side.

And I was sure if he looked down at the table, he would see a shadow under it.

I coughed a bit loudly, hiding the fact that Helen had my cock buried in her throat and was holding it there. Sucking on it, I could feel her mouth and throat contracting around my dick.

“I was going to take Leon out for a ride, father and son talk, away from the distractions,” Jason nodded. “I feel bad that I am doing the same thing my father did to me,” Jason said, shaking his head. “Play ball or else, you know.”

“Yeah,” I nodded. “Definitely.”

“Find Helen, when you leave so she can lock the office. She is probably around here, doing something or the other, hell knows what that woman does in a day.”

“No problem,” I nodded.

“Don’t forget you promised to meet up with the rest of the guys soon,” Jason pointed at me as he closed the door.

I waited for a few moments before I even moved or breathed. “He doesn’t know what I do?” Helen said as she got out from under the desk.

“Don’t get angry, it was just a statement,” I said as I tried to pick up my pants.

“Fine,” Helen smiled. “Fuck me, right now,” she said, turning to look at me as she hopped onto the desk.

“What?” I asked. “No!” I shook my head. “The door could open any minute, we should leave.”

Helen grabbed me by the collar of my neck and pulled me back. “Fuck me right now on his desk, in his trophy room.”

Helen took off her shorts and threw them on the floor. “Right now!” she ordered.

I stared at her. I wanted to. I wanted to fuck her as hard as I could right on his desk. Not just because she was a model, but for everything, he had done to me in the past. “Linda,” I said in barely a whisper.

I plunged deep into her as she laid back. I fucked her hard and fast with her legs wrapped around my waist. I stared at the door eager it to open and for Jason to walk in and see me fucking his precious third wife.

I buried my cock deep into her. As usual, her loud shouting started. I tried to stop her, but she pushed my hand away.

“It’s soundproof,” Helen said. “He wanted to make sure he couldn’t hear anything in this office, when he was in here, and no one could hear him. Now fuck me harder!”

I pulled her off the desk and turned her around, bending her over the desk as I fucked her hard. Helen’s wailing continued; she was like a banshee on steroids. She screamed everything that I was doing to her and even called me a few names that couldn’t be repeated in public.

I grabbed a handful of her dark black hair and yanked it back as hard as feasible as I pummeled her from behind. With each thrust, she matched it. She fucked me as much as I was fucking her.

I finally pushed deep into her and came. Helen sighed, and we both got our breath back before leaving the office.

“Told you we would do it again,” Helen said as she walked me back to my car.

“Doesn’t he have cameras? Or ….” I asked as I opened the door to my car.

“Let me worry about that,” Helen winked as she walked back to the house. “Until next time.”

“Alicia’s going to get a kick out of this,” I said as I pulled away.

***Author’s Note: The rest of this story as well as many other of my stories are on my other pages, the links to which can be found*** [***here***](

NSFW: yes


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