Family Videos

Forgot to add this. I'm not putting it back on lit tho. Don't really like it anymore.

Later on, Heather got the family together so they could reminisce over old family videos. Heather **** me into joining them and enthusiastically went over all the videos she’d gotten, unsure which she wanted to play first. I was resigned to sitting through boring family videos by the time she chose one and hit play. I should have know better than to think the Sim would let a boring story thread take point because a few minutes in, things started to get interesting.

A younger looking Daniel complained to Reese. “Dad I’m tired, I don’t really want to do this.”

“Too bad, I know you had a get together with your friends and those girls at school, but we’re your family and we celebrate birthdays together, with each other. I don’t care if you think that’s lame, that’s how we do it.”

Reese filmed Daniel walk into the house and there’s a stereotypical birthday party set up, a banner saying ‘Happy 18th Birthday Daniel!’, cake, drinks and so on, the shocking thing about the scene is an almost naked woman’s ass staring at the camera.

The girl is on her elbows and knees on the floor with her ass up in the air. I watched as she turned around at the sound of the two coming in, revealing a younger faced Heather. “Surprise! Happy birthday Daniel!” the younger Heather said with delight and a heart meltingly warm look. Heather’s almost completely nude except for the bright pink ribbon on the small of her back, with matching lacey lingerie. The camera lingered on Heather’s ass, showing off all the details; the garters clipping her stockings to her panties, panties which had a neat hole and slit cut out, and the little crystal base of a buttplug resting snugly in Heathers ass, it was the most appetizing present I’d ever seen.

Daniel seemed frozen but Reese nudged him. “Go on son, it’s alright now.”

That seemed to break the spell because Daniel rushed over to his mom and whipped out his cock. He wasted no time at all before pulling the buttplug out and immediately trying to work his dick into her ass with just spit, ignoring or not noticing the little tube of lube that was sitting next to his mom. It took a moment but he **** his cock inside her. As soon as he was in, the whole family watched as he started assfucking Heather in an absolute frenzy. Reese scolded Daniel. “Daniel! That’s your mother there, not some stranger on the street, don’t be so rude.”

Daniel slowed a fraction, as if regretting how inconsiderate he was being but Heather quickly cuts in. “Oh it’s his first time with me, he’s just excited. If he wants to ruin the hole let him.” Then turned to address Daniel. “Ignore him honey, have fun, that’s your present and you can treat it any way you want today.”

Daniel murmured a quick thanks. And with his moms blessing, resumed assfucking her manically, completely losing himself in her ass, with every little detail captured thanks to the attentions of Reese. The hottest thing to me about the scene is while Daniel is rutting away, Heather was giggling and laughing almost uncontrollably during the sodomy.

“Well, like father like son I guess, hahaha,” Heather said between peals of laughter. “He went straight for the ass Reese, didn’t I tell you he would?”

“I never disagreed. Damn, the boy’s eager like a jackrabbit, just look at him go, like a man dying of thirst.”

“He’s so precious. Reese, make sure you get good footage, this’ll make such a cute wedding video,” Heather turned to the camera and waves. “Hi everyone!”

I heard someone giggle as I watched. Turning around I saw Heather laughing even now at the memory.

“Oh boys at that age. It was so cute. After that he followed me around like a puppy, never leaving me or my asshole alone. Every day, any chance he got, he’d pump my ass like he was afraid I’d take it away from him or something,” she turned to look at Daniel wistfully. “I don’t think any man’s been up my ass as much as my boy. Thought my poor hole would never recover.”

Daniel looked abashed at that and tried to hide it. He covered it up by reaching for his mom and pulling her over, onto his lap. She accepts the handling routinely and hiked up her dress to let Daniel have his way with her as usual.

I turned back to the video to watch Daniel hammering his moms ass, trying to get it to gape. He was trying to spread open her asshole with his thumbs but it was refusing to cooperate. Heather giggled. “Sorry Daniel, going to have to work at it longer than that if you want her to open up.”

Flipping her over onto her back, Daniel assfucked her while spreading her legs apart and holding them down at the thighs. Heather giggled again loudly and purred out, “that’s my boy.”

As the video goes on, I noticed neither Daniel nor Heather pay any attention to the pussy. Daniel leaves it empty and Heather never touches it. Instead, Daniel carelessly fucks Heathers ass missionary, treating her like a woman that was only ever made to be assfucked. Eventually Daniel stiffens and everyone sees the telltale signs of spasmodic, jerking release. Eventually, he slowly pulled a softening cock out of his mother’s ass and waddles up to her face on his knees. She expectantly opened up her mouth immediately and accepted his filthy, cum covered cock, eagerly devouring every bit of cum still on it and leaving it clean.

I watched Daniel collapse on his mother, burying his face in her tits. “How was that honey? Was mom’s asshole as nice as the girls from school?” Heather asked sweetly.

“It was better than any of the girls at school, thanks mom,” he deliriously replied.

“You’re welcome sweetie. Remember, these holes are yours to play with from now on. So you don’t have to run around the neighborhood looking for an ass to split open. Just bend mommy over and put it in hers whenever you like alright dear?”

“I will mom,” Daniel said sleepily before nodding off.

The video cut off there. I turned to see Heather looking quite nostalgic while Daniel casually pumped away at her ass. “Time passes so fast, it feels like that was just yesterday,” Heather said wistfully.

“Everyone grows up mom,” Daniel said evenly.

“I know, but doesn’t mean I have to like it.” Heather quickly changed the subject, “By the way, how is Melissa treating you down there? Are you getting enough of her ass?”

“Yes mom, I assfuck her plenty.”

“Well, even so, be sure to get as much use out mine as you can before you head back honey.”

“I will mom, I will, you don’t have to worry about that.”

~

Over the next few days, Daniel stayed true to his word and seemed to be on a personal mission to keep his moms ass occupied for as much of each day as humanly possible. But he wasn’t the only one to give it any attention, Reese and I had our fair share of fun as well. It got to the point where Heather just completely gave up wearing underwear or pants and just went around bottomless the whole day so the house could have easier access to her asshole.

She got so used to going around bottomless that she even forgot to put on pants when going out, telling us about the story at dinner. “The funniest thing happened today. You know how I’ve stopped wearing anything below the waist these days at home right? Well when I went out to run some errands, I had forgotten to put anything on before I left and didn’t even notice until I was at the bank. There I was, waiting in line when all of a sudden I feel someone sliding straight into my ass, and no wonder it went straight in, living with the three of you,” she said playfully, sweeping a fork in our direction accusingly before continuing.

“I must have been acting on reflex or maybe I thought it was you Daniel, because I started backing up into the guy to meet his thrusts before I knew what I was doing. I think he really liked that because he finished up pretty soon. But then the next thing you know, every darn man in the line wants a turn; by the time I get to the counter, half a dozen of them have had a go in my ass. Fine by me, but that wasn’t the worst of it. The employee at the counter kept running into all these issues with their system. I spent half an hour waiting there at the counter before they cleared it all up, with every man there killing time by pounding out my bum; the poor thing, I don’t know if she’ll ever be the same again,” Heather said with a sigh.

“Sounds like you had quite the day mom,” Daniel said.

Heather gave a dramatic look. “Oh that’s just the start of it. It’d be rude to give the first man special treatment and then deny it to everyone after. So obviously I had to back my ass up on any cock that came my way. But don’t you see how it looks?”

Those around the table gave her blank looks, prompting her to go on. “I show up at the bank bottomless, with an ass so stretched out people were sliding in with no trouble immediately, and then help everyone that had a turn to fuck out my ass even more. People are going to talk and everyone’s going to assume I’m some kind of anal addict now.”

“But, you are, aren’t you?” Daniel blithely asked.

Heather rolled her eyes. “That’s beside the point Daniel, I don’t want that kind of reputation, I’m not some uni girl anymore.”

Daniel shrugged. “Well there’s no helping it now, you can’t exactly undo the day. And maybe it’s a good thing, you might get it up the ass enough now.”

Heather hummed thoughtfully and conceded. “I do like the sound of that. You might be right,” she said before shifting the conversation to the garden.

~

As the days went by, I noticed even with another woman in the house, the twins and Maria started getting used less and less. For some reason, Daniel, Reese and I all coincidentally seemed to decide to spend all our time with Heather. With the three of us giving Heather’s poor ass so much attention, Heather ended up spending pretty much half of every day with cock constantly ramming into her asshole, which she somehow managed to find funny.

Heather got fucked open so badly that by the fifth day, she was walking around with almost a permanently gaping asshole that yawned open wide if she so much as bent over or spread her cheeks. It might have been fun to look at but not so much to fuck, loose as she was at that point. Still, I got kick out of it that wasn’t a purely physical thing and didn’t intend on stopping any time soon.

I walked into Heather’s room to check to see if she was free, and unsurprisingly she wasn’t. Heather was on her elbows and knees with Daniel crouched above her ass, demolishing what was left of it with rabid thrusts.

Heather saw me and smiled, greeting me warmly. “Afternoon James, I figured you’d be by soon. Bit stuffed at the moment, but Daniel will probably be done soon. Come by in, say, another half hour?” she said, looking to Daniel for confirmation, who grunted in reply.

I nodded and headed back out the way I came but just before I left the room, I heard Heather call out. “Actually, you know what James, you could join us if you wanted. There’s more than enough space these days for the two of you to share.”

“You can do that? Take the two of us at the same time?” I asked with barely suppressed surprise.

“I don’t see why not. So that’s a yes then?”

“I’ve never tried that before, but I’m up for it,” I said shrugging.

Heather smiled brightly. “Oh that’s wonderful to hear dear. Dan, make some space for James would you and come under here.”

Daniel reluctantly left Heathers ass and repositioned himself below her, he seemed a lot chipper though once his face was buried in her tits.

I stripped off my pants and took Daniels place, crouched above Heathers ass. Using my fingers, I pried her ass open further to make space for my cock. It was a struggle to fit the tip in with another cock already inside but I eventually manage it and **** my way down to the balls. It wasn’t exactly nice with another man there but I managed to ignore it for the most part. Heather certainly couldn’t though, she gasped deeply as I slowly bottomed out in her. “My, that’s certainly new, I don’t think I’ve ever felt quite so full,” she said breathlessly.

Dan and I took that as our cue to start hammering into her. With the two of us in her ass, it stretched her open obscenely, perilously wide. We were stretching her out so badly that I didn’t think she’d ever feel tight again with anything less than more double anal, which was fine by me; I liked the idea of her only ever getting two cocks in the ass.

It was strange seeing the usually calm Heather writhing and groaning beneath me, but the combined 15” of cock in the ass was no joke.

Almost an hour of the two of us ruining Heathers asshole went by before we finally finished with her. By the time it was over, her ass was a stretched out mess that didn’t look like it’d be fun for anyone to use anymore. We took turns getting our cocks cleaned in Heathers mouth, having her absentmindedly eat the cum we’d deposited in her ass before we left her to recover.