Family Obsession

This story focuses on the theme of incest. If this doesn't interest you, please do not read further. Thanks for your time.

MIKE

Mike sat at the computer in his office. He was casually surfing porn, pants around his ankles and had his hard dick in his hand. He didn't have to worry about IT or getting caught since it was his CPA firm, his server, and his office door was locked. He contemplated how he had gotten to this point in his life. He was 42 years old with two great kids and a stunning wife. He had been chasing his tail for the last 20 or so years, building his career, then a business, and raising his kids. Now that his son was in his first year of college and his business basically ran itself, he found his mind wandering.

His life had revolved around his son's sporting events and work. He had almost no hobbies and very few close friends. Since his son went away to school seven months ago, he had begun spending a lot of time on the internet, mostly watching porn. He knew he was addicted but found that he just couldn't stop. Every day at work he would find himself watching porn, almost exclusively videos with two guys double penetrating a woman. He fantasized it was his wife getting fucked and he was the man fucking her ass while she straddled a stranger.

Mike had blonde hair, stood a little over six feet tall, and was thin but athletic. He had always felt his penis was below average and not in proportion to his body. His dick was almost but not quite five inches long and thin but his wife had always seemed to enjoy it. They had been high school sweethearts and were married when she got pregnant while he was in college. She had never mentioned his cock being small but he felt the only time he had really made his wife squirm and feel like she was being truly fucked was when he took her virginity the first time they had sex and a few days after their wedding when she had let him try anal. Afterwards she said anal sex hurt too much and they had never done it again. Now it was all he could think about.

He had slowly started letting his wife know his feelings over the past few months. He brought up the one time he had fucked her ass almost every time they had sex, which was at least twice a week now. At first she seemed hesitant but she warmed up to the dirty talk after she realized how horny it made him and how quickly he came.

He surfed around the net until he found a suitable two guys on one girl video to watch. He thought back to his first conversation with his wife about double penetration two months ago.

"Do you wish you were fucking my tight ass?", she whispered in his ear.

"God yes, but what about your little pussy, it would be a shame to leave such a

beautiful little pussy without a dick in it."

"You can fuck both holes, right after another. Would you like that?"

"Hell yes, but don't you want both holes filled at the same time?"

"Would you like that honey? We could put a dildo in my tight pussy while you fuck me in the ass." She purred.

"Wouldn't you rather have a real dick?", he asked hesitantly.

After a long pause, his wife played along and said, "If you want that honey, I'll do anything for you."

"What kind of man would you want?"

"Whatever you want honey, I want a clone of you inside me if I could. That would be hot."

Thinking of that conversation and watching the video had brought him to climax and he quickly jumped up and caught his cum in the tissues he had prepared. He always felt bad immediately after jerking off at work but he knew he would be looking on sex message boards the rest of the day trying to fulfill his ultimate fantasy. He wanted to bring in another man to fuck his wife while he was inside her ass. He wanted to see his wife moan and writhe in pleasure. He wanted to feel in control, manly, and make his wife feel filled like the women in the videos he watched every day.

He had been looking at sex message boards for weeks. There were plenty of men willing to join in with a couple. Lots of them had pics of their dicks, usually very large dicks, and most didn't show their faces. He didn't want a man with a giant cock fucking his wife and he certainly didn't want anyone who could possibly know him, which would be difficult since they lived in a small town. He wasn't sure his wife would even go for it. Sure, she had gone along with the dirty talk but he was pretty confident she would never allow another man into their bedroom.

Nevertheless, he persisted in his daily search to fulfill his fantasy but it seemed futile and he was continually frustrated. He did have a crazy idea that had been bouncing around in his head lately. He was heading up to visit his son at college this weekend to watch a spring football game and he thought about acting on his risky idea, if he could only summon the courage.

JEN

Jen stood in front of her bedroom mirror fully naked. She turned left and right looking at her body and smiled.

"Not too bad", Jen said out loud to herself.

Jen was 42 years old, her C cup breasts were still full and had a little bit of a hang to them. Years of yoga, pilates, squats, and spinning classes had created a toned abdomen, thin strong legs, and thick firm ass. Her auburn blonde hair hung about a foot past her shoulder. Older folks often said she looked like Suzanne Somers and she had heard friends of her son say she was a MILF.

Life was good. Jen was happily married to her high school sweetheart. He owned a successful CPA firm that enabled her to be a stay at home mom. Her 19 year old son, Billy, was away in his first year of college. He was a jock, an inch or two taller than his father but with more muscle. Her 18 year old daughter, Kim, was a senior in High School, she was a bit on the nerdy side. Kim looked like her mother but had gained weight over the last year. Her daughter would be going to college in the fall and her and Mike were beginning to plan for all the free time they would have with the kids away at college.

If the past 6 months was any indication, their free time would include lots of sex. She wasn't sure what had gotten into her husband but he wanted sex multiple times a week. He had become focused on discussing anal sex, although they had only done it once a long time ago. His latest obsession involved her having anal sex with Mike while she fucked another man. Just mentioning it during sex usually brought Mike to climax within moments. She didn't mind it though, she enjoyed the dirty talk and the way her husband still lusted for her after all these years.

Mike had been mentioning for weeks that he had a surprise planned for her and they needed to talk but every time she brought it up, he would say maybe next week. Oh well, she thought, he would let her know when the time was right. She dressed in her usual attire of yoga pants, sports bra, and loose t-shirt. She liked to get her workouts done in the morning then take care of the house chores in the afternoon. She put her blonde hair in a ponytail and headed out for the day.

BILLY

Billy was waiting outside the dorm for his dad to pick him up to watch the spring football game together. Life at college this year has been fun but challenging. He had acquiesced to his parents demands that he would focus on academics his first year, and would pursue athletics in his sophomore year if his grades were up to snuff. So far, he had lived up to his part. He expected he would finish the year with mostly B's and a couple C's. He spent most of his free time lifting weights and training for next year. He had made a few friends and had a girl he was seeing but he really missed playing sports.

His dad picked him up and they went to the stadium. Instead of heading straight in, his dad pulled a cooler out of the trunk and asked if he wanted to tailgate a little. Billy was a little taken aback since his father had only offered him beer twice and both times his father had been a little tipsy. It was a beautiful day and there were plenty of other people in the lot tailgating. Mike poured some beers in plastic cups and they talked about school and other mundane things until the conversation took a strange turn.

"Are you having a lot of sex up here?" Dad asked.

"Ummm...a little," Billy said hesitantly.

"Oh good for you, son. Just make sure you use protection. I have been having a lot of sex with your mother lately," his Dad said awkwardly.

"Aww c'mon Dad, I don't need to hear this," Billy laughed.

"You are a man now, son. You can have these conversations. I only bring it up because I think I need your help," his dad said without looking Billy in the eyes.

"Help how?"

"Well, your mother has a particular fantasy..."

Billy was in a daze for the next few minutes as his father laid out a plan for him to fuck his own mother.

"She can never know it was you, but you are the only person I can trust, what do you think?" His dad asked pensively.

"I...I...I don't know, It all sounds so crazy. Mom would kill me if she found out."

"That's why she can never, ever, ever, find out. If we do it like I laid out, she will never know. You will be helping out your Dad and her fantasy will be fulfilled. I would rather it was you than a stranger. Look at it like good practice for all the girls you will be meeting at college," his dad said, giving Billy a playful punch on the shoulder.

JEN

"This is your surprise? Are you serious?" She asked incredulously

"It is what we have been talking about for months. We will go to the city, in a hotel room, we will wear masks, it will be anonymous. Don't you think it would be exciting to live out a fantasy like that before we are too old?" He asked.

"It was just pillow talk, I don't know about this. It would just be weird."

"You said before it would be hot," Mike responded.

"Yes, I admit it would probably be hot. Aren't you reluctant to let another man see me naked, touch me, not to mention actually fuck me? Wouldn't that make you jealous?"

"A little, but I will be fucking you as well. Seeing another man enjoy your beautiful body while you are filled with pleasure, well I think it would be exciting."

"Where did you even find this man? Are you plotting with one of the other Dad's? I would be embarrassed to death walking around town with one of them knowing they had fucked me." she said angrily.

"Anonymously on the internet, like I said. Completely anonymous, a guy from the city. I have no idea who he is and he will never know who we are."

"Right, because of the masks," Jen said sarcastically.

Jen thought in silence for a minute. Mike stared at her expectantly but sheepishly. She had only known one lover in her life, she wouldn't have this body forever, in a decade or two she would probably not even care about sex anymore. She had to admit that it would be hot to feel what it would be like having another man and it wouldn't be cheating since her husband was with her.

"Fine, we can do it but I swear I will kill you if anyone ever finds out. This is a one time deal, and I want that Hawaii vacation I have been dreaming about."

Mike smiled and said, "Done!"

BILLY

Billy sat in his car in the parking lot two blocks away from the hotel. He couldn't believe he was actually here, following through on his dad's insane plan. He legitimately thought his dad was going through some kind of mid-life crisis when he brought up this crazy plan and that it would pass. Shockingly, two weeks later his Dad had called with the date and details of the plan. Was it really going to happen? Was he really going to fuck his mom? He couldn't imagine actually doing it. He had jerked off almost every day since the call thinking about it. His Mom was beautiful, his friends had always raved about her and how hot she was. He had even gotten into a fistfight with one friend who kept calling his mom a MILF in his presence.

Now he was sitting in a car waiting for a text from his dad to go fuck her. It was surreal. Could he even do it? Yes. How could he not? His Mom was the hottest woman he had ever known. The phone beeped. Billy read the message and headed towards the hotel.

As he approached the door, his hands were shaking. He stood there for 30 seconds trying to hear if there were any sounds coming from the room but it was silent. He pulled out the mask that he had bought, it was a masquerade mask that only covered his eyes and forehead. He didn't need more because the plan was for his Mom to be fully masked and blindfolded. He reminded himself of the number one rule; no talking. He slipped the mask over his head and knocked.

His dad answered the door wearing shorts and a t-shirt, and sporting a similar mask. The room was on the larger side but was simple and dimly lit. A couch and writing desk sat along one wall. The king bed was in the middle of the room. Billy's mother sat on the edge of the bed wearing the same mask as his father but with the eyeholes taped over. She wore a black sheer nightgown, he could see she was wearing a matching black bra and underwear along with black thigh highs. Billy stood slack jawed looking at his mother, she was amazing. This was the sexiest woman on earth to him, she put the college girls to shame.

"Honey, we have a guest here to see you, I will put the additional blindfold on now to make sure the mask doesn't slip off."

Billy watched as his dad wrapped a blindfold over the mask and tied it. Billy stood there awkwardly not knowing what to do. Billy's dad took his mother by the hand and led her over to her son and helped her kneel.

"Honey, please make our guest welcome," his dad said.

MIKE

Mike couldn't believe it, this was finally happening. He felt bad for Billy, he looked so nervous. Billy kicked off his shoes and stood directly in front of his mother wearing gym shorts and a t-shirt. Jen reached out blindly till she found Billy's leg. She was slowly rubbing his crotch and hips with her hands. His wife had downed almost two glasses of wine before Billy arrived, it seemed that it had cooled her nerves and put her in the mood.

"Oh, is this big thing all for me," she cooed.

Jen grabbed the top of Billy's shorts and underwear and pulled them down around his ankles. Mike let out a small gasp when he saw his son's cock spring out and nearly hit Jen in the face. How was this his son? He had expected that his son, who was similar to him in almost every way, to have inherited his cock. Billy was not fully erect yet but it was already far bigger than his father's. Jen grabbed Billy's cock and began stroking his shaft with her right hand while the left hand explored his plum sized balls. Billy didn't notice his father at all, he was staring in disbelief at his masked mother pulling on his dick.

The effect was almost immediate, Billy's dick was now fully erect and Mike watched his wife pull on her son's shaft with both hands. Mike's shock deepened. His son's cock had to be almost three inches longer than his and twice as thick. His son's balls were almost double the size. His wife seemed just as amazed.

"Wow, I never. I wish I could see it. It's just so big," she said breathlessly.

Then his wife put the mushroom head of her son's cock into her mouth. Mike watched with jaw wide as Billy moaned then seemed to catch himself remembering the no talking rule. Mike was starting to feel a little sick, maybe he had made a mistake. He had meticulously planned for everything except for his son having a huge dick. He didn't think he would have cared if it was a little bigger but there was no comparison. It was massive. Well, he thought to himself, there was no going back now.

"Let's have our guest lay on the bed honey like we planned," Mike said as he motioned his son towards the bed. Billy looked like he wanted to continue with the blow job but he pulled his cock from his mother's mouth and she released her firm grip from his cock reluctantly as Billy removed his shirt and laid naked on the bed.

JEN

Jen was blown away by the size of the cock she was sucking and was a little upset when he pulled it out of her mouth and moved to the bed. She longed to see what it looked like. Jen was shocked that her husband would invite a man with a such a large cock to fuck her. She wasn't going to complain though. If she was going to do it this one time, she may as well get the full experience. This man's cock was so much bigger, longer, and thicker than her husband's that she could hardly believe it. Jen reached out looking for her husband's hand so he could guide her to the bed. The plan was for her to ride him and her husband would join in from behind. Jen's heart fluttered at the thought of sitting on this stranger's huge cock.

Mike took Jen's hand and led her to the bed. She got her bearings once she reached out and felt the strangers muscular chest and abs. Jen winced as Mike pulled the blindfold covering her mask tight again so it wouldn't slip off. Jen took off her underwear, dropped it on the floor, and slowly straddled the stranger's stomach on the bed. She could feel his rock hard cock resting between her legs and she positioned her already wet pussy over his shaft. Jen felt like a virgin again. This man with this big cock was going to be much deeper inside her than her husband had ever been.

The stranger sat completely still and hadn't moved or touched her yet. Jen ground her pussy lips along his shaft a few times to make sure she was nice and wet and lifted herself forward and up on one leg to position his mushroom head between her lips. Jen let out a gasp as she managed to slide his large cock head into her pussy while she was still gripping his shaft. She knew it would take some time to work her way down on this cock as she was already being stretched wide by his bulbous head.

It was an odd feeling not being able to see, as she awkwardly balanced above the stranger while gripping his cock, she noticed that if she looked straight down with her left eye she could just see a little bit of this man's hairless muscular chest, he was definitely younger than her. The mask had lifted slightly on the bottom when her husband pulled the blindfold tight. Jen moved her head down and around a bit more trying to see if she could see his dick out of the bottom of the mask and she froze. Her heart stopped, she felt her body flush, and her mouth went dry. This man had the same mole on his right hip that her son had. Not similar, exactly the same mole. She had seen it a million times. The chest, the abs, and the mole. It was him. This was her son lying beneath her with the head of his cock inside her pussy, stretching her wide. She realized she had also just sucked her son's dick.

Jen had never been so angry in her life, she would kill her husband. What the hell was he thinking? She sat there, perched above her naked son with his firm cock inside her. If she stopped this now, the embarrassment and shame would be unbearable. Her pride would force her to divorce her husband. How could she ever look at Billy again if they both knew what had happened? How could her loving son agree to this? Her brain worked feverishly. Jen thought of the alternative, she could continue through with the plan. It was crazy but her son would never know that she knew it was him. She could just act like nothing happened, and she would vow to make her husband's life miserable for the foreseeable future. Jen made her decision, sighed, and sunk further onto her son's dick.

Billy

Billy was in heaven. The head of his dick was inside his mother's tight pussy. Billy could see her little hand tightly gripping his cock, her rings sparkled in the dim light, her blonde pubic hair was trimmed and framed a perfect pussy that was now spread around his cock. He thanked god he had jerked off earlier or he would have cum already. His mother's large tits strained against the black lacy bra and her ample cleavage hung deliciously above him, begging to be squeezed. Billy felt as if it had to be a dream. Suddenly he felt his mother tense and she stopped, barely moving, and just stayed in that position. He yearned to be deeper inside her but she didn't move. Was something wrong? Did he do something? He hadn't even moved yet really. He started to become concerned but then breathed a sigh of relief as his mother continued sliding down his dick.