Gilf Adventures: The First One

"No mom! Stay away from me!" Cherie shrieked as her mom Leslie tried to talk to her.

"Maybe you should give her some time," Cherie's husband said as they sat in the chairs.

Leslie had tried apologizing to her daughter, but Cherie took things to the extreme as usual.

It could have happened to anyone. We were going through airport security when a buzzing sound came from Leslie's carry-on, there was a mortal shock as Leslie tried to quiet it, but the security personnel took the suitcase from her.

Some people laughed others shook their heads when they found that the culprit was a huge brown dildo. The security personnel said it happens all the time when people forget to take the batteries out, and the bag moves around. They took the batteries out and handed the suitcase back to Leslie.

Of course, Cherie through one of her fits and now didn't want to talk to anyone but Hank.

Hank was a weird name for a half-Hispanic, half-white man, but that's what his parents went with, so that was his name. He was a co-worker of mine and a good friend.

His wife, though, was a complete drama queen. She blew everything out of proportion, and I mean everything.

We went to the beach once, and a dog ran across the beach, and some sand got on her from the dog running. It was a total nightmare. She claimed she had been attacked and the dog should be put down.

It was sand!

I don't know Hank puts up with her daily. I could only take Cherie in small doses; even then, she was too much.

"Sorry about that," Leslie smiled as we sat down, awaiting our plane to Jamaica.

"Like they said it happens," I shrugged.

"Hank is lucky to have a friend like you around," Leslie smiled.

Leslie was nothing like Cherie, I only met Leslie yesterday, and I could already tell she was the mellow type. She cooked dinner for us, which was terrific. Cherie could burn water if you let her.

Hank cooked, cleaned, and did everything else around the house. Cherie was only good for complaining and posting pictures of herself on social media.

The first time I met Cherie, I knew she would be a total bitch. She kept calling me Hank's friend, even though Hank kept telling her my name was Ian.

She called me Hank's friend or the black guy hanging out with Hank. It took her three months to start calling me by name, and that was because someone else told her she was being a bitch.

I knew why she was doing it. One day, I joked that she suffered from a rare disease called Noassatall, and everyone laughed.

In my defense, we played a drinking game, and I drank a lot.

Cherie didn't like it when Hank and his brother tattled on me and told her what the joke meant. She wasn't happy at all.

The truth hurts. Cherie had no ass. She had B-cup tits but was utterly flat in the back.

"She blows everything out of whack," I shook my head as I looked over at Cherie, still crying.

"Gets it from her father," Leslie nodded. "The man made a big deal out of everything."

I didn't know much about Cherie's family other than her parents divorced many years ago, and Cherie had become a real daddy's girl.

He was wealthy and gave her anything she wanted. She got a new BMW because the mileage on hers reached fifty thousand miles, and she said it was old.

"Her sister Sonya is nothing like her," Leslie said. "Neither is her older brother."

"Sonya, is that the dyke bitch?" I asked.

"Yup, that will be the one," Leslie smiled.

Cherie always went on and on about her younger sister, the lesbian. She kept saying how gross it was to be the sister of a lesbian, and she never wanted to go to her sister's house in case she caught something.

"So, how do you put up with it?" I asked as a few people shook their heads and walked away from Cherie.

She was still crying.

"What is she crying for now?" Tony asked as he joined us.

Tony was another member of our group. Which meant his sister Angela and her friend Cary were there also. The other two women went over to their friend. The rest of the group catered to Cherie's crying and antics, except for Tony, Michelle, and me. We hated it.

"You don't want to know," I said, shaking my head.

"One of my toys went off while going through security," Leslie shrugged.

I was surprised that she would come out and say it like that to a stranger that wasn't there.

"What? I am fifty-five, my give a damn is busted," Leslie shrugged.

Tony didn't know what to say as he stared at me.

The attendants told us the plane was boarding soon. I looked over at Cherie. She had finally stopped crying. The others gave us dirty looks, which I was used to as I wasn't any of their favorites.

"I better go over there," Tony shook his head.

It didn't take long for him to return with a question. Cherie didn't want to sit near her mom and wondered if I could switch.

I was happy to switch. I wouldn't have to sit near one of them.

We joked about many things along the way, and I heard stories about Cherie's young life. Leslie was great to talk to; she didn't hold anything back.

It was late at night when we finally arrived, and we all wanted to do nothing but lay down in our beds.

We all had paid our own way, and the rooms were nice and big. I lay out on my big bed and fell asleep.

~ ~ ~ ~ ~ ~ ~ ~ ~

We met downstairs for breakfast, and I saw Cherie still angry with Leslie. They were arguing in the corner of the extensive buffet room.

"Still?" I asked as I sat down.

Hank stared at me. "It was an embarrassing situation," he said to me.

"It was an accident," I shrugged. "Could have happened to anyone."

"Take the batteries out," Angela said.

"Or put it in the suitcase to be put on the plane, not your carry on!" Cary said.

"I thought it was funny," I shrugged.

"You would," Angela said.

"What does that mean?" I asked.

"You never take anything seriously, people were staring at Cherie, how do you think she felt?" Cary asked.

"Not this again," I shook my head.

People and their feelings always made my stomach turn.

Leslie came back to the table, shaking her head.

"Fourteen," she whispered to me.

"What?" I asked.

"Fourteen times, that I apologized," Leslie said, shaking her head.

"I wouldn't have," I shook my head as Cherie was all smiles now that she had gotten her way.

The more I hung out with Cherie, the more I hated her, and I knew the feeling was mutual. I smiled as an idea popped into my head.

"No," Tony said as he looked over at me.

"What?" I asked innocently.

"No, whatever you are thinking, just no," Tony shook his head.

I knew he was saying that because he didn't want to incur his sister's wrath.

"I won't do anything," I smiled.

That was a lie, and he knew it.

It didn't take long for me to put my plan into action.

I sat at the pool with Leslie and waited for it to happen.

"Here it comes," I smiled.

"Phone call for Ms. Noassatall!" one of the pool guys said.

Immediately Hank gave me a look. He got it right away. Then Tony shook his head.

"Ms. Noassatall?" the guy said repeatedly.

It finally dawned on Cherie, who got out of the pool and shot off like a rocket.

"You're so mean," Leslie laughed.

"Now both of us are in the doghouse," I smiled as we bumped glasses.

At lunch, Cherie was nowhere to be found. Hank came down and shot me a look that could kill. I shrugged back at him.

Not my fault his wife was a bitch.

"That was uncalled for," Hank said.

"No one knew it was her," I shook my head. "If she stayed in the pool and acted normally, they would have gone back and said no one is here by that name, she was the one that got up and ran out."

"That is true," Tony nodded.

"We knew," Hank said.

Angela and Cary were giving me the silent treatment.

"I am going back out in the sun," Leslie said as she got up. "Are you coming?" she said as she looked at me.

"Right behind you," I smiled.

Leslie sauntered in front of me. "Well, do I have to go by that name also?" Leslie asked.

I stared at her ass as it swayed back and forth. "Definitely not," I smiled.

For being fifty-five, Leslie had a great body. She could easily pass for someone in their early forties.

Leslie reminded me of Chandler Bing's mom on the show friends. Except she had red hair instead of blonde and had a bigger rack.

Leslie dropped her shoal and uncovered the rest of her body as she dived into the pool.

'Much bigger,' I thought as I watched as she surfaced, and her boobs bounced and swayed as she got out of the pool.

I walked over to that side of the pool.

"Got your attention?" Leslie asked as I wrapped a towel around her.

"More than that," I smiled.

"Oh really?" Leslie smiled as she leaned in close to me.

The others came out to the pool, and we branched off.

I couldn't believe Cherie's mom was flirting with me. Even now, she was staring over at me.

I was getting hit on by a certified GILF.

"Think I am going to go up to my room," I said as I couldn't hide my hard-on anymore. I rushed out of the pool area and into the hotel lobby.

I made it into my room and went out to the patio. I looked down at the pool and couldn't see Leslie.

Then there was a knock on the door.

I went to the door, and Leslie rushed inside.

"So, this is where you ran off to," Leslie said as she smiled at me.

"It wasn't exactly running," I smiled back at her.

"Well, you couldn't run in your condition," Leslie said, pushing me against the wall. "What were you thinking about?"

I stared down at her as she slowly got down to her knees. "I was thinking that a woman like you was hitting on me," I said.

"No," Leslie said, shaking her head as she grabbed the bottom of my swim trunks. "The truth."

"I was thinking about a hot GILF like you, was hitting on me," I nodded.

"Much better," Leslie said as she slowly tugged on my trunks.

"What does GILF stand for?" Leslie smiled at me.

"Grandma I would love to fuck," I said.

"The first part suits me," Leslie nodded. "I am a grandma," she said as she tugged on it more.

Leslie nearly had my pants down.

"The second part," Leslie said. "That's up to you."

My dick throbbed hard as she stared up at me.

"I take that a yes," Leslie said as she pulled my pants entirely down. "Now, this is a cock."

I watched as Cherie's mom started sucking on my dick. "Holy fuck," I said as I watched her head go back and forth on my dick.

I felt her mouth wrap around my dick as it bobbed back and forth on it.

Leslie's eyes looked up at me with my cock in her mouth, then she closed them and did it again.

'Got damn,' I thought. Leslie was a good cock sucker.

I watched as she stroked my cock while sucking and licking my balls.

"It's been a while since I had a cock," Leslie said.

"I couldn't tell," I said as Leslie held my cock in her hand and sucked on my balls.

"Thirteen years," Leslie nodded. "Practically a virgin again."

"Oh yeah?" I smiled.

"Want to find out?" Leslie smiled as she stood up.

"Definitely," I said as Leslie walked towards the bedroom.

By the time we walked into the bedroom, we were both naked.

Leslie's big tits naturally fell on her body. They were much bigger than I had thought they were, but what I wanted was much further down.

I got on top of Leslie and slid my cock into her.

"Fuck!" I said as I slowly pushed into her.

Leslie wasn't joking, it felt like I was fucking a virgin, not that I ever had, but I bet it felt the same. I looked down and saw my cock slowly going into her.

"Told you," Leslie smiled as she saw the look on my face.

I pushed deeper into her and lifted her legs onto my shoulders.

"Yes!" Leslie said as I started to fuck her.

I heard my phone going off in the living room. It was Hank's ringtone.

'Fuck him,' I thought.

I was fucking his mother-in-law. She was taking all my cock and loving it.

Leslie stared up at me as I fucked her. She was nodding her head and moaning. She looked down at my cock going in and out of her.

Her pussy gripped my cock and was coating it white.

I knew I wouldn't last much longer. "No," Leslie said as I started to pull out. "Cum inside me," she nodded.

In my thirty-two years, I only came inside once, which was my first time. Since then, I have always pulled out or used protection.

I pushed my hips forward and came inside Leslie.

"We should go back downstairs," Leslie nodded.

"As soon as I get my breath back," I nodded.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

"What!" Cherie shouted as I sat across from her at the dinner table downstairs.

'I just came in your mom,' I thought as I stared at her.

"You're being weird," Cherie said, shaking her head.

"What's your problem?" Hank asked later as we were at a club.

"What do you mean?" I asked.

"You go off for a few hours, then come back with a smile on your face bigger than this club," Hank said.

"I just had a good nap, that's all," I lied.

"Uh huh," Hank said as he walked away.

"May I have this dance?" Leslie asked.

I looked around and saw Cherie and her squad dancing in the corner.

"Relax," Leslie smiled. "If they see us, we are just dancing."

Who was I kidding? I wanted to dance with her.

"Much better," Leslie said as we danced.

It was a slow reggae song, and Leslie was pushing her ass against my crotch and moving back and forth against it.

"Now," Leslie said as I gripped her hips. "What are you thinking?"

"You know what I am thinking," I said as I gripped her tightly.

"No, I want you to say it," Leslie said.

"I want to fuck you," I said.

"That's not what you are thinking," Leslie smiled as she pushed her ass onto me harder. "The truth remember?"

I knew what I wanted to say. "Come on," Leslie said.

"I want to fuck your ass," I said.

"There we go, was that hard?" Leslie said. "Well, something is definitely hard."

Leslie smiled as she walked away. She dropped a keycard on the floor just in front of me.

"This old woman is calling it a night," Leslie said as she walked past the others.

I waited until a few others left before returning to the hotel. I acted like I was going to my floor because Tony was in the lift with me. After a few minutes, I called the elevator back. I ensured no one was on the floor or in the hallway.

I slipped the keycard into the slot and opened the door.

"About time," Leslie said as I came into the bedroom.

She was lying on the bed completely naked with the toy from her carry-on inside her.

"I had to get started all by myself," Leslie said. "Care to help finish me off?"

I couldn't strip out of my clothes fast enough.

"No," Leslie said as I tried to put my dick inside her pussy.

Leslie turned over onto all fours.

I put my cock at the entrance of her ass after using the lube on the bed beside her.

"Slowly, it's been a very long time," Leslie said.

I pushed it forward, and even though I had poured a generous amount of lube on my dick and over her ass, it didn't want to go in after several tries.

"Slow," Leslie said again as the crown of my cock went inside her ass.

Slowly I pushed further into her. The more she took, the more she began to push back onto my cock. I released my cock from my hand and gripped Leslie's waist.

"Feels good," Leslie said as she used her toy on herself. I could feel her fucking herself with the toy while I fucked her ass.

I gripped her hips hard as I started to fuck her ass.

"Yes," Leslie said as I increased my speed.

Her tight ass gripped my cock like a vice.

"Harder," Leslie said as she fucked herself.

I yanked back on her red hair as I fucked her hard and fast.

This was only my second time doing anal. The first time it didn't last long as my girlfriend at the time didn't let me finish.

I could tell Leslie was in for the long haul.

"That's it fuck my ass," Leslie said as I pounded away at her ass.

I buried my cock into her over and over. She was taking my cock like a true anal slut, and that's how I was treating her.

"Fuck," I said as I knew I was cumming.

"Cum in my ass!" Leslie shouted.

I pushed deep into her ass as I came.

We both heaved and sighed as we lay on the bed.

It was a very adventurous night for both of us.

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

"Will you stop!" Cherie said as I smiled at her as we drove to the airport.

The weekend in Jamaica was a fun one, not only because I got to fuck Cherie's mom but because we had a lot of fun on the beaches and everywhere else.

"Sorry, can't help it," I smiled.

Not only was I staring at her because I had fucked her mom multiple times, but Cherie, who was supposedly the saint, the loveable, do-nothing-wrong woman. Had sex with another guy and got caught.

Hank was pissed. He had said nothing since last night when we caught her. I knew they would be heading for divorce, and I was happy for him.

The others didn't say anything, but I laughed and laughed so hard I thought I would die from not breathing.

Cherie got caught most stupidly. It was one of the bellhops or guys that came to the room. She could have locked the door or gone into the bathroom, but no, right smack in the middle of the living room, the first room anyone saw as they opened the door, right there on the floor.

We all came into their room last night because she was going to have a movie night for our last night here. As soon as we walked inside, all of us saw the tall, skinny black guy fucking Cherie like she was a rag doll.

I couldn't stop myself from laughing. Cherie was shrieking like a banshee from hell as her legs flopped all over the place as they were on his shoulders.

We could see it all, his dick slamming in and out of her like a piston. He didn't have a condom on, and his balls slapped hard against her filling the room with a loud slapping noise.

Hank always got pissed because Cherie never let him have sex with her without one. She said it was gross and didn't want to risk losing her figure to have a baby. Not yet anyway. But here she was with a stranger, balls deep inside her without one.

Poor Hank just stood there, not moving or saying a word. It took Cherie a few moments to realize we were there as she was cursing and screaming and calling the black guy that was fucking her names that I never heard her say, well, out loud anyway.

"Adrian," Hank said as he looked at me.

"No," I shook my head. "She's always playing the higher than god role, and now, she wants all of us to ignore that it happened?"

"Let it go," Angela said. "It's between them, not you."

Leslie was still smiling with her head turned to the window.

"Okay, but you can't say anything to anyone, anymore," I nodded.

Cherie didn't say a word. She had nothing.

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

"So," Leslie said as we stood in the car park.

"Come on, let's go!" Cherie said.

I looked back at my car and saw Hank standing there. He looked defeated.

"Text or call me?" I asked.

"Definitely," Leslie said.

I walked to my car and got in. Hank sat in silence.

I wanted to tell him I had fucked her mom, maybe that would make him feel better, but I knew it would cause more problems than it was worth.

"If you say I told you so, or anything like that I swear," Hank said as he looked out the window.

"Not my place," I replied.

"You had to laugh," Hank said as he stared at me. "What was so fucking funny?"

"Are you really asking that?" I smiled.

"Yes, my wife was fucking another guy and you found it fucking funny!" Hank yelled. "What kind of friend laughs at that?"

"Oh, now we are friends?" I smiled. "What about the times, when she wouldn't call me by name or just say the black guy? What happened to being friends then?"

"You know what," Hank said as he looked at me. "Drop me off, then never talk to me."

"Sounds good," I nodded.

I did drop him off at his brother's house. "I hope she takes everything!" I yelled.