Family Tutor

"Can we borrow one of mom's strap-on's?"

His father barely looked away from the news. From the glimpse Rob had gotten it appeared there were more riots in one of the Reservations for the Incurably Religious. He didn't get it. They had everything Rob had, including the right to believe whatever Stone Age nonsense they chose to believe. After years of trying and bending over backwards, it was clear they were not and never would be content to live and let live, so they had been quarantined. It wasn't like back in the dark times where those who didn't fit in were shoved into corners no one else wanted. He'd heard there were parts of Texas and Alabama that you couldn't tell from Farmington or Greenwich, not until you notice everyone was wearing clothes, even when the weather was gorgeous.

His dad pointed to one of the drawers without saying a word. Rob pulled it open and examined his choices. He was intrigued by the idea of either his sister or Ms. Banard shoving one of the dildos lying there up his ass.

"Hey, pop?"

"Huh?" his father replied, looking away from the HoloVid, which promptly faded to near transparency. "What's up, Rob?" His father appreciated his son's need to move beyond his childhood. He was careful not to call him Robbie, though he sometimes failed.

"Do you enjoy pegging?"

His father nodded. "Sometimes, yes, it can be very pleasurable. It's not something we do every day. It's more of a treat for me, or sometimes it's a treat for your mom when she is feeling especially horny."

"Right on. So, if I wanted to try it with Car and Ms. B, which of these would be the most appropriate?"

"Use the red one, it's a nice medium, small enough for a beginner but big enough you know you're being fucked. Take the small butt plug as well. Put that in during the prelims then you'll be nice and relaxed for the real thing. I don't want to wake your mother, are you streaming it?"

"Of course," Rob answered as he collected the toys his father had recommended. He added a pair of nipple clamps connected by a silver chain and slid the drawer closed.

"Excellent. Have fun. Your mother and I'll watch it later and offer you some critiques." The latter was said with a smile as he turned back to his news.

"Sure, pops. That's what Ms. B said we keep you old farts around for, education."

"Hmm, I'll have a little talk with her about that later. Probably while I'm fucking her mouth so I can get a word in edgewise. Have fun, son."

When Rob re-entered the sex quarters, his sister and neighbor were laying side-by-side, head-to-toe, eating each other's pussies. Ms. B had her hand been his sister's legs, keeping her ass nice and loose with the ebony dildo.

"Sis, lube this up for me, huh?"

His sister lifted her face from the woman's cunt and took the butt plug from her brother's hand.

"This for you, baby brother?"

"Yup," he answered as he turned and bent at the waist. He trusted his sister. He used his hands to spread his cheeks. A wet finger, Caroline's or Ms. B's was unclear, massaged his pucker. He slowed his breathing and relaxed, reminding himself he'd had his own finger in his ass before. This part was no big deal. The pressure on his ass increased and he felt his sphincter relax and let the finger enter him. The finger penetrated far enough to press on the firm mound of his prostate. He felt the fullness in the head of his cock that was the whole point of the exercise. The finger continued to loosen him for a moment and then withdrew.

"Relax, baby brother, don't hold your breath. Bear down, don't squeeze," his sister instructed.

He felt the tip of the plug pressing against his anus. He did as he was told. The pressure began to build. It was starting to become a little uncomfortable. He bore

down and the tip of the plug penetrated his ass.

"Okay Robbie, that's the tip. This is a fairly small plug but. You're gonna feel a little pressure and it might hurt a little but it shouldn't hurt a lot. If it does, say so, we'll stop and go back to the finger or find a smaller plug. Understand?"

"Yeah, feels okay. Go on, Car."

She pushed slowly, giving his ass muscles time to stretch and accept the plug. It did hurt a little but never enough that he felt he needed to pull away. Soon, he felt his ass close around the neck of the plug and felt the silicone flange nestle between his ass cheeks.

"How's that feel, dear?"

He straightened and turned to look at his neighbor. "Nice. It feels nice, Ms. B. I'm surprised."

"Life is full of surprises, you darling boy. A great number, in my experience, are pleasant ones, if one keeps an open mind." She reached for the strap-on. "I think it will be simpler if I use this to get inside Caroline's sweet little ass first, then you can position yourself more comfortably to get into mine." She spotted the nipple clamps dangling from Robert's hand. "Excellent idea, dear, excellent. I have an idea for those later."

Robert wondered what the woman had in mind and decided she was so far beyond him when it came to sexuality it was silly to wonder.

"Ms. B, I'm gonna fuck you but I was thinking this whole scenario is a bit awkward, lots of wide spread legs and squatting.," "What if I watch you fuck Car while I get used to this butt plug? When you've finish with Car I'd be honored to fuck you however you wish. If it all falls into place, maybe I'll let Car use the strap-on on me. I'd rather watch Car on her knees with you over her, fucking her ass as I did last night."

Ms. B glanced at Caroline, who shrugged.

"Okay, dear. Caroline slip that old dildo of mine out of your ass, child, and get back on your knees." As Caroline positioned herself, the older woman looked at Robert. "Don't you dare blow your nut anywhere but inside me young man, understand?"

"Yes, ma'am."

Ms. B nodded at the strap-on with approval. It had a small dong she could put in her pussy and soft nubs that would stimulate her clit as she fucked Caroline's ass. She slipped into the contraption without hesitation. She was not new to such sexual accoutrements.

Robert watched, impressed by the strength in the older woman's legs, as she squatted above his sister's upturned ass. He watched as she rubbed the head of the strap-on over his sister's anus. The woman lowered herself and the silicone cock disappeared inside Caroline's ass. The woman began to move up and down. Her speed was surprising. Her legs were thin but there was no quiver or shake in them that Robert could see.

Caroline began to moan her pleasure, rubbing her tits over the sheet. Robert sat down near her head, letting his own weight press the butt plug into his ass. He rocked back and forth on the mattress, loving the way the feel of the plug in his ass changed as he moved. He moved back up in the bed and rested his head against the wall. He pulled his knees to his chest, reached between his legs, and removed the butt plug. He pushed it back in. There was no pain. He popped the plug in and out of his sphincter as both women watched.

His sister reached between her legs and he could see her fingers begin to circle her clit. Ms. B continued her assault on his sister's ass. Both women's cheeks glowed.

"You like that dear? You like the way I'm fucking your ass? I know a few tricks. That's what us old dogs are good at, old tricks. Your brother will learn. I'm not just moving up and down, I'm alternating the angle of my hips, the angle of my fake cock. One way presses against your G spot and the other against your colon. Back and forth, up and down, switch now, twice one way, twice the other, or twice one way and once the other. There is more to fucking, youngsters, than simply moving your cock in and out of an orifice."

"God, yes," Caroline panted. "This is. Totally. Different. Ass fucking. Fuck me. I'm going to cum."

His sister grabbed the sheet between her teeth. A high keening wail filled the room. She thrust her ass upward, seeking the pounding dildo.

"That's right, dear. You go ahead and cum like a good girl. Ms. Banard is showing you what it's like to be well and truly fucked isn't she? Cum like you mean it, girl, or I'll fuck you again. That's right."

Caroline collapsed onto the bed. Ms. Banard was left crouching above the panting girl with a glistening, bouncy rubber cock jutting away from the black harness around her waist.

"Kneel down there beside your sister, young man," she ordered, shifting her gaze from Caroline to her brother. "Quickly, don't make me ask twice. You can leave that," she added when he rolled to his knees still clutching the butt plug.

He moved past Caroline and knelt beside her. Their shoulders touched. She turned her head and though she was still panting, he started to kiss her. With no warning, he felt pressure on his asshole and then she was burying the strap-on deep inside his ass. The feeling was overwhelming, nothing like he expected. There was very little pain. He felt as if the dildo were driving the essence of his being into his cock. He felt his cock swell and then felt a gush of precum. He looked between his legs as a large drop of clear fluid detached itself from his cockhead and fell to the sheet.

The randy woman, a woman he had grown up next door to, began to fuck him as she had his sister. He resisted the urge to reach down and jerk his cock. She had instructed him to save his cum for her pussy or ass. Orders were orders.

"Girl, on your back," she ordered Caroline. "Eat her cunt," she said to Robert. "I'm going to let you fuck me in a few minutes. I want your face to shine with your sister's pussy juice. Eat her fucking pussy like a good boy."

Caroline rolled onto her back, scooting up on the bed as she did so. She threw one leg over the top of her brother's shoulders so that she lay, pussy agape in front of her baby brother's mouth. She whimpered when his lips touched her still sensitized clit. She would not be able to take much of this. Ms. B was a pro. She read their bodies as easily as she read her own. She stood, freeing Robert's ass from the pounding of the dildo.

"Catch your breath, dear. Robert, let her be for a moment. Let her catch her breath so she can finish what I've started."

Robert remained on his knees. He tightened and relaxed the muscles around his cock and his ass. He wondered how he felt about this. He'd jerked off with other guys at times but he was not attracted to dudes. If some guy wanted to suck him off, he supposed he wouldn't care. Fuck, a blow job was a blow job. Did he want a real cock up his ass? He wondered.

"Young man if you're wondering if you're gay, you're not. Trust me on that one. You're as straight as any straight man I've ever met. Straight men have prostates and having their prostate massaged feels as good to them as it does to a gay man. Now, I suspect if you were horny enough you might let a man fuck you but it wouldn't be because you wanted to be fucked by a man it would be because you wanted to feel what you just felt and a real cock happened to be the easiest way to do it. That's all. Itch. Scratch. Nothing more than that."

She turned her attention to his sister.

"Have you ever worn a strap-on, dear?"

Caroline nodded.

"You got your second wind?"

Caroline nodded again, albeit a tad more slowly. She reached for the strap-on.

Their neighbor plopped down onto her back. She reached forward and touched Robert's cheek.

"Eat my cunt." It was an order.

Her cunt looked nothing like his sister's. There was a small landing patch of gray hair. The lips were much thinner than his sister's, which made her clit look huge. He didn't want to be rude by hesitating. He stretched his neck and pushed his tongue into Ms. B's pussy. It tasted like pussy. That was reassuring. He began to tongue her slit as he wiggled forward on his elbows to get closer.

He took her clit between his lips and began to flick it. He ran his tongue around the tiny head, then up and down the sides of the shaft.

"You eat pussy like I do, young man," the older woman chuckled. "You should. Your sister taught you and I taught her – and your mother. Um, that's good. Eat my snatch."

Beside him, Caroline finished with the harness. He could see the cock out of the corner of his eye. It looked much bigger than it had when he selected it. He was amazed it had been in his ass.

Ms. B pushed his head away.

"Ass or cunt, Robert?"

"Whatever you'd prefer, Ms. Banard," Robert replied as he rose up on his knees. His cock throbbed. The sheet beneath him was wet.

"What I want is be fucked and fucked hard. Everyone is afraid they'll hurt me. I'm old but I'm not made of glass. Do you remember how I showed Caroline how it felt if she was fucked at a steep angle? Were you already awake then?" He nodded. "Excellent. I'll take care of my clit. I know what it likes. You, you concentrate on fucking the shit out of my cunt. Understand?" He nodded again. She turned to his sister. "Dear, he can't fuck me like an animal with you on top of him. When I'm close, when your dear brother is close, we'll slow down. Then you can get behind him and fuck his pretty boy ass and help him fill my cunt." Caroline nodded.

The woman rested her head back on the bed, pulled her legs to her chest and used one hand to spread her pussy open.

Robert guided his cock with one hand and speared her with his erection.

"Oh my dear, that feels lovely, just lovely."

Mindful of her instructions, Robert pulled out and immediately slammed his cock back into her cunt. He fucked her. Fucked as she had requested. The room rang with the sounds of flesh on flesh and the soft grunts his thrusts forced from her lungs.

"That's right, that's how to fuck. Keep it up. Fuck me. Damn, it's been years since someone plowed my cunt like this. Harder, damn it, harder. Fuck me."

Robert did his best. He did as he was told. He was a good student.

---------

"My goodness, Robbie. What is Mable doing to you there?"

His mother had finally gotten up. She was sipping a cup of tea as they watched a playback of the morning's sessions. She was referring to a point when Ms. Banard had instructed Robert to slow down and finally to simply lie with his cock as deep in her cunt as it would go.

On the HoloVid, it was clear something was happening both by the look on Robert's face and the way Ms. Banard's stomach was tightening.

"She was doing that pussy ripple maneuver wasn't she Rob?" his father asked, clearly pleased he'd identified what was happening.

"You've felt her do it, too? It's fucking crazy awesome. Does mom know how to do it?

"No," his father answered truthfully, unhesitatingly and without a trace of disappointment. He was not worried that Martha would be upset. We all have different talents. No one is without something unique. Humanity had finally reached a point where no one felt bad for not being the best at everything.

"What's he talking about, George?"

His father paused the HoloVid and turned to his wife.

"I've told you about it before. Mabel has such fine control of her cunt she actually makes it, I don't know the way to describe it, ripple is as close as I can come. It's a wave of contractions that feels like her cunt is trying to pull you in."

"That's exactly right, dad." Robert turned to his sister. "You need to see if she'll teach you that. It felt like my cock was a small animal being swallowed by a boa constrictor. That's a terrible analogy. There was nothing painful about it. It was bizarre but intense. Very intense. As good as she is, she almost made me cum before she was ready. That's why I pulled out of her so abruptly. Watch."

He motioned with his hand and the HoloVid resumed. The blissful look on his holographic face was replaced in an instant by a look of concern. He jerked his hips back and squeezed the head of his cock between two fingers. A trick his dad had taught him to delay orgasm.

"Forgive me, dear," the holographic and entirely real appearing Ms. B could be heard saying. "I allowed myself to get carried away."

"Holy fuck don't apologize. That was the most amazing thing I've felt on my cock in my entire life."

Beside them, Caroline was stroking the rubber cock strapped to her waist as if it were real. "What, Robbie? What felt so amazing?"

"Later, sis. Right now I need to cum. I need to cum and then I need to piss."

"You heard the man, young lady. Get over here and fuck your brother. Fuck him hard enough and he'll barely need to move. You pounding his ass will move him in and out of my ass enough to get him off." Her gaze moved to Robert's face. "And if you've never cum with a bladder that's about to burst, you have another treat in store. This is your lucky morning, young man."

Four pairs of eyes watched the action unfold. Robert and his father were both stroking their cocks. Martha and Caroline sat side-by-side, one leg draped over the other's. Their arms were crossed, their hands diddling each other's clit.

Martha sighed at the sight of her holographic daughter burying her own strap-on in her son's ass. The virtual image of her son already had his holographic cock inside Ms. B's holographic ass.

"A moment, dear," the image of their neighbor requested. She reached to one side and retrieved the nipple clamps. "Hold still," she instructed. Robert watched and the ache in his left nipple re-awoke. He watched, remembering the feel of Ms. B's fingers pinching just behind his nipple and the sharp bite as she allowed the clamp to close on his nipple. He heard his moan and for a moment wasn't sure if it came from his mouth or the playback. Ms. B attached the other clamp to her right nipple. The silver chain dangled between their bodies.

"Now, sweet girl. Now you may fuck your handsome brother as hard as you wish."

She did. Caroline did herself proud. She fucked her brother's ass with speed and strength. The older woman had been correct once again. Caroline's thrusts moved Robert's cock in and out of the woman's ass. Ms. B tugged at the chain with one hand, pulling at his trapped nipple. Her other hand was busy working her clit.

On the holographic, Robert moaned, "Fuck, I'm going to cum," at the exact moment his father said the very same thing.

Caroline was closer than her mother. Without taking her fingers from her mother's clit, she twisted and leaned over her father's cock. She had her head turned so she could watch herself on the screen. She took the head of her father's cock between her lips. She did not try to suck him off. She ran her tongue over his cock while he jerked himself off.

"Give me your cum, daddy," she whispered and he did. Robert paused the HoloVid as he and his mother watched as George's hip twitched, Caroline's cheeks puffed out, and a stream of white leaked from her lips and ran down the length of her father's cock. When the line of cum reached his balls, his nut sack shrank and grew taut. Caroline swallowed, bobbed her head over her father's cock a few times, and then sat back up.

"Go ahead," she said, licking her lips and speaking to her brother, "let it play, finish it."

Robert motioned his hand and the ass cheeks of his virtual twin began to contract. He threw his head back when Ms. B reached up and jerked the nipple clamps off their nipples. Using well-practiced gestures of his hands, Robert zoomed the HoloVid in on Ms. B's ass. His cock worked in and out with small motions as his sister continued to fuck him. Soon enough, white trails of jizz began to ooze from around his cock.

Ms. B came quietly but the intensity of her orgasm was apparent in the lines of her face and the brightness of her eyes. Caroline pulled the dildo out her brother's ass and laid down beside Ms. B. Robert remained kneeling, gently fucking her ass while his cock relaxed. When his cock left her ass, a stream of white followed, running down the crack of her ass.