Mary, Tim & Mike Ch. 08

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Mike's introduction to anal sex.
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Part 4 of the 4 part series

Updated 11/02/2022
Created 05/29/2003
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MCJRM
MCJRM
45 Followers

Tim picked up the pizza and wings and handed them to Mike. "If you and your mom can get the plates and drinks and stuff, I will be right back. I think we should eat in the dining room and we will need lights so you might want to pull the shades." Mary and Mike nodded in assent and set about their tasks.

Mike took care of the shades and Mary got the plates and stuff. Mike could not believe it but he felt his cock trembling as he watched his mom walk around in her "pizza" outfit. He had cum more today than he had in his entire life and his cock was still wanting more. As she set the table she told Mike to get some more beer. In the kitchen, Mike discovered she had freshened her and his dad's drink. Mike got another Bass Ale from the fridge, opened it, scooped up the two drinks and carried them to the table. As he was setting them down, Tim walked into the room holding a large box. He placed the box on the table and then sat down. The three of them suddenly discovered they were ravenous and began eating the pizza and wings. As they ate, they were quiet, just enjoying the food at hand.

After eating their fill, Mary got up and brought out wet towels from the kitchen so they could wipe their hands clean. Mike stood up, noticed that his cock was not hard, and gathered up the remnants of the food. He took them into the kitchen. "Hey, is it okay if I have another beer?"

His parents answered with a chorus of "Yes's."

He took his beer from the fridge and then walked into the dining room. The box was open and pictures were spread out on the table.

Tim looked at him, "Now we kind of have these categorized so let's try not to get them all mixed up. You can look at any of them you want, Mike."

Mike sat down and started to sort through the pictures. Some of them were of his mom, some of his dad, and some of the two of them together.

One set of pictures of his mom showed her sucking a variety of cocks, some where she had been given facials, and some of her kneeling between two guys sucking both cocks at the same time. Others showed her on her hands and knees with a cock in her mouth and another in her pussy. Still others showed her with black men, in one of them she was being three holed – a black dick in her ass, another in her cunt and a third in her mouth. There was another group of pictures of her with other women, some of her eating a woman, others with her going 69 with a woman, and some of her eating one woman while another woman at her. In one, she was sitting on one woman's face while two others were sucking Mary's tits. Looking at the pictures was having the desired effect on Mike and he felt his cock starting to harden on him.

He shifted to another set and they were of his dad, sucking cock and fucking other men. In one, he was on his back sucking one cock while another guy was holding Tim's legs up and fucking him in the ass. Tim had also, based on the pictures, been fucked by black men and had even fucked a couple of black women. In a series with the same black woman, he was stuffing his cock into her face, the next his dick was in her ass, and the third showed him fucking the woman's pussy. Mike's cock continued to get hard.

The final group of pictures was of his two parents together with others. In one, Mary was on her hands and knees with Tim underneath apparently eating her pussy while another guy was fucking her pussy. Mike looked at his parents and set that picture aside since he wanted to ask a question. In others, his parents were simply fucking each other or going 69 with each other. One picture showed Mary with a large strap on dildo, fucking Tim in the ass. Mike unconsciously reached down and began stroking his hardened cock.

It has taken about 30 minutes for him to look at all the pictures and during that time, no one had said a word.

He took the picture of Tim eating his mom's pussy while another guy fucked her pussy. "I would love to try this, but I was wondering, did he cum in mom's pussy or in your mouth?" he asked.

"Actually, he came in her asshole. Shortly after this picture was taken, he pulled out of your mom's cunt and asked me to help him get into her asshole. I guided him in, went back to eating your mom and then the guy came. As I recall it, your mom came at that time – although I don't know if it was from me eating her or the guy doing her in the ass."

Mary piped up and said, "It was a combination of both, you goose!"

Mike was still stroking his dick and could feel pre-cum on the head of his dick. He looked at his dad, "Can I ask you a question?"

"Sure, go ahead," his dad replied.

"Does it hurt to get fucked in the ass?"

"Well, to be honest, yes and know. Let me explain. If it is the first time you are fucked in the ass and the guy doesn't go slowly and help you stretch, it does hurt. But after a few moments, if the guy is being slow and gentle, the pain goes away. If he is not going slow, then the pain can last for quite a while and it would probably make you not want to try anal again. Now, if you like it and do it pretty regularly, each time a cock slips into your asshole, there is a twinge of pain but that is nothing like the first time and it disappears right away. Wouldn't you say that is accurate, dear?" he asked as he looked at Mary.

Mary looked from father to son, "Yes, that is pretty much it. The first time I got it in the ass, your grand dad took it really slow. Before he ever put his cock in my ass, he slipped a number of things into my asshole and helped me get used to feeling things inside my ass. Even still, the first time I took his cock in my ass, it hurt. He pushed the head of his dick into my ass and then immediately pulled it back out. He knelt down and kissed my ass which seemed to help the pain subside quite quickly. A minute later, he was standing behind me, held his greased up cock and then eased it into my asshole. There was no pain that time and he was soon slowly fucking my butt and I was loving it. So, your dad's assessment is accurate."

"Hmmmmm," was all Mike said.

"Why did you ask?" Tim asked.

"Well," Mike said as he sorted through other pictures, "you both seem to really enjoy it and I think I want to try it. Like you said dad, "…sex is for pleasure…"

"Would you like to try it right now?" his dad asked.

Mike nodded his head in the affirmative.

"Well, lets retire to the bed room then."

All three of them stood up, Mary noticed that both her husband and son were starting to get hard. The sight amazed her considering how many times that day the two men had cum. "You two guys are holding up well, considering!"

Mike and Tim smiled at her. Then Tim led the way into the bedroom. When they got to the bedroom, Tim told Mike to kneel on the bed and rest his head on a pillow. Mike did as instructed and felt somewhat self-conscious about kneeling in front of his parents with his ass high in the air. Mary had pulled out a tube of lubricant.

"Let me know how this feels," she said.

Mike felt the tip of something pressing against his asshole. There was pressure and he tried to resist. "No honey, you have to try to relax. Mike willed his asshole to relax. The he felt something slide past his sphincter muscle. He knew instantly that it was a finger. There was a little pain but Mike had to admit, it felt good. The finger slipped in and out of his asshole several times. Then Mike felt the finger slip from his asshole only to be replaced by something a little larger.

"How does that feel?" his mom asked.

Mike admitted, "That feels good, but what is it?"

"The handle of my hairbrush. A little larger than my finger but not as thick as your dad's cock," she replied.

She began to ease the hairbrush in and out of his asshole and at the same time, she reached between his legs and fondled his balls and cock.

The bed moved as his dad sat on the bed. "You doing okay, so far?"

"Yeah dad, it feels good, I have to admit it really feels good," Mike replied.

"Well I would love to suck your cock but that might distract you. Getting butt fucked and your cock sucked at the same time will come later on."

Mary slipped the brush from his ass, "Now here is something larger still."

Mike felt some pressure on his asshole, it stretched, and he experienced a spike of pain. "Unnnhuh," he said, "that hurts some."

"If it gets to bad," his mom said, "let me know but try to relax your asshole more."

Mike focused his thoughts on his asshole and it seemed to work. He felt his asshole stretch and then seemed to close back up. He knew he had something in his ass but was not sure what it was.

As if reading his mind, Mary said, "That is a smallish butt plug. Show him one Tim."

Tim sat up, stretched over, and got a larger butt plug. Mike could see it was shaped like an ice cream cone, thin at the top then fattening out and then thinning out at the bottom with a flat end. "This part," Tim said while he was pointing to the flat end, "keeps the plug from going all the way inside you."

Mike nodded.

"Are you still okay?" his mom asked.

Mike nodded and then felt her draw the butt plug out of his asshole. He was surprised that it didn't hurt a great deal when she took it out. "Now," she said, "I am going to ease a dildo into your ass."

Mike looked between his legs and she showed him a dildo that was a little more than an inch in diameter and about eight inches long. "Will all of that go inside?" he asked.

"It can," she said, "but we will only ease in four or five inches.

Mike again willed his asshole to relax and when his mom pushed the dildo into his asshole there was no pain to speak of. He felt it going in and in and in. Then his mom drew it out and began to fuck his asshole with the dildo. Mike felt his cock stiffening in response to what was happening to his asshole.

After several minutes, Mary said, "Okay, now I am going to use one that is just about the size of your dad's dick." Mike felt the pressure but didn't feel any pain only pleasure. "How are you doing?" his dad asked.

"Good, good, it feels good," was Mikes reply.

"Do you think you are ready for the real thing?"

Mike nodded and watched his dad stand up and then move behind him. As he looked back between his legs, he saw his mom squirt some lubricant on his dad's dick and then rub the lube all over his dick. His dad then moved up behind him, grasped his cock and then Mike felt the pressure on his asshole. The head of his dad's dick pushed into his ass and, much to Mike's surprise, there was no pain. Tim then pushed forward until the entire length of his own cock was buried in his son's ass.

"How does that feel," Tim asked his son.

"God, it feels great. Fuck me in the ass dad, fuck me."

With that, Tim began thrusting his cock in and out of his son's asshole. Tim gripped Mike's hips and set up a rhythm that Mike found very pleasurable. For a long time, Tim just kept up a slow but steady pace. After several minutes, Tim leaned forward a little and said, "Mike here comes your first load of cum into your asshole."

Tim began shoving his cock faster and faster into Mike's asshole. Mike felt his cock bobbing back and forth in sync with his dad's thrusts. Mike looked to his side and his mom was sitting on the bed, frigging her pussy and rubbing it with a dildo that was humming. Tim's thrust took on an urgency and Mike sensed that he was about ready to cum. Suddenly, his dad pulled Mikes hips back, shoved his cock deep into Mike's ass, and then held still. Mike could feel his dad's cock pulsing and knew that his dad's cum was filling his ass. After a moment or two, his dad pulled back slightly and Mike felt his asshole squeeze his dad's cock out.

Tim flopped on the bed, spent from his exertions. Mike remained on his hands and knees enjoying the lingering sensations. Mary started to moan from her self-ministrations and both men watched her cum.

As the three of them rested, Mike was thinking to himself, "What a wonderful family I have, and a sexy one at that. I hope next weekend with grand dad and grandma is just as exciting. But I wonder what is going to happen now."

MCJRM
MCJRM
45 Followers
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