Double anal training

He smiled as he looked at their shaking butts as Jake retracted his fingers.

"All right both of you did well, now it's time to continue. Jennifer come here for a bit."

Kayla kept in the same position, with her hands at the wall, while sticking out her ass. Jennifer turned around and awkwardly walked towards Jake.

Having just felt her butt toyed with it still felt weird right now and she knew Jake was far from finished.

Jake turned to Jennifer and gave her some small anal beads: "Lube them up."

Jennifer didn't ask why and got to it, while Jake lubed up the other anal beads.

After both of them finished Jake said to Jennifer: "You get behind Kayla. Because she's been causing you trouble for a year, you may be the one to toy with her asshole. At the same time though, I'll be playing with yours."

Jennifer looked at Jake and nodded.

Meanwhile, Kayla had also heard Jake's words and had a wry smile on her face not knowing if Jennifer wanted to get back at her. Kayla knew she had caused her quite some trouble in class, never listening to her.

When she turned her head she already saw Jennifer arriving behind her with a smug smile on her face. Kayla realized she wouldn't let her off nicely. She begged with her eyes to go easy on her.

Jake got behind Jennifer and grabbed both of her tits. While squeezing them nicely he whispered in her ear: "You can play with her as you wish, but don't hurt her."

He then gently sucked on her earlobe for a bit after which he let go of her breasts.

Jake took the anal beads and without wait he gently inserted the first one in Jennifer's ass, causing her to let out a cute shriek as something foreign once again made its way inside her ass.

"Don't just enjoy it yourself, I'm sure Kayla is begging to feel it as well," Jake joked.

Jennifer regained her composure for a bit and as Jake did to her she gently inserted the first of the anal beads inside her ass, which in turn caused Kayla to shriek.

Jake smiled and continued playing with the meaty ass in front of him inserting anal beads and pulling them out as he pleased. All the while the only things he heard were Jennifer as well as Kayla's moans.

And judging from the sounds of it, it didn't seem like Jennifer was going easy on her at all.

Jake smiled as he could see both women were slowly opening up to anal stuff and before long they would start to like it as well. The anal beads he used right now were small, but they were still plenty enough for both of them to feel it.

And while his dick was already hard from seeing two beauties being played with their asses, he didn't fuck any of them, after all, he was planning on giving it hard to someone else.

He kept playing for over 15 minutes and both women were already moaning nicely. Then suddenly the door opened and the other two in the house came out. Both had red blushes on their faces.

Jake smiled and said to Stefanie: "Give me those two anal plugs over there."

Stefanie quickly handed them to Jake, who in turn pulled out all the anal beads lodged inside Jennifer's ass.

Naturally, she moaned nicely feeling them all suddenly leave her butt. Still, she knew what Jake wanted to do next and thus she too pulled them out of Kayla's, causing yet another nice moan.

Jake smiled and pressed the butt plug inside Jennifer, making sure it couldn't pop out on its own. After that, he got behind Kayla and put a slightly different plug inside her ass.

It was a little bigger, but the biggest difference was its ability to vibrate. Still, Kayla didn't know this.

Jake smiled and said: "Well then it's time for Kayla to repent for her past mistakes. Get on the bed and spread your legs wide, while holding your arms behind your back. And you girls," Jake said turning to the other three, "tie her up."

Jake then went and got a bag, filled with all kinds of vibrators and other toys.

Kayla got nervous and swallowed her saliva, knowing the moment had arrived. Still, she obediently got on top of the bed and moved in position, after which the other three tied her up, making sure she couldn't move and her legs were spread wide.

Especially Julia was eager to tie her up nicely, even though it was her own daughter and she fully knew what was gonna happen next. She couldn't wait for Kayla to drown in pleasure.

Jake smiled as he looked at his beautiful slave all tied up and nervously looking at him. He then continued and pressed egg vibrators on her nipple as well as clit, using some tape to make sure they stayed there. Then a long dildo was shoved inside her pussy and was being kept in place by some rope, so it wouldn't slide out.

Jake smiled as he got some more items out of the bag. he then held a ball gag in front of her mouth without saying anything. Naturally, Kayla knew what this meant and nervously opened up wide.

Jake smiled and was satisfied with her obedience. He then placed the ball gag inside her cute mouth. He finished it up with a blindfold over her beautiful eyes.

Looking at his creation he smiled and said to Kayla: "All right enjoy this Kayla."

Jake then placed earplugs inside her ears, making sure Kayla couldn't hear anything at all.

He smiled seeing at her tied up body. She couldn't see, speak, move nor hear, and in a minute endless pleasure would assault her body.

Jake then got a remote and put it to 1, causing all the vibrators on Kayla's body to start vibrating. Immediately moans kept coming out of her gagged mouth, as her body squirmed in vain as she was tied up well.

Jake looked at her for a while, causing his dick to get even harder.

He then turned to Jennifer and handed her a remote.

"Have fun with her, but make sure nothing happens to her."

Jennifer was now fully in control of the vibrations that assaulted Kayla's body.

"Julia come with me, it's time for us to have some fun as well. As for the two of you play with each other as well. After all, you'll be sharing a bed for a long while to come."

Jennifer and Stefanie looked at each other and gulped nervously. None of them had any experience in lesbian sex. Stefanie had only lost her virginity a day before as well.

Not to mention the fact they were student and teacher. Still, they had to obey Jake and so they said simultaneously: "Yes master."

"Oh naturally don't forget who your master is. You can please each other for now, but once I'm done with Julia you'll be soon moaning in under me as well."

Jake didn't care if his women did lesbian stuff with each other as long as they remembered who's boss."

Jake smiled and turned to Julia as he took a hold of her amazing ass, "Well then let's go. It's time to pop that anal cherry."

Julia nodded nervously and together they left the room, walking towards Julia's room.

Jake along with Julia entered the master bedroom and Jake closed the door behind them. He could see Julia was nervous.

He got behind her and hugged her closely, "don't worry, it won't hurt," Jake said to her.

Julia responded, not really reassured, "Y-yes master."

Jake then got on top of the bed and signaled Julia to lie down next to him. He lied on his back while Julia rested her head on top of his chest. Naturally Jake was already groping her meaty ass.

Before we start how about I tell you the reason I want to fuck your ass so badly.

Julia looked at Jake not saying anything.

Jake smiled as he said: "Since the time you became my woman, you've taken everything. My first kiss, first blowjob, first boobjob, and even my first time having sex. Now it's finally time for me to get one of your firsts."

Julia looked at Jake with a loving gaze, not having thought Jake would have cared about any of that, but it seems she was wrong about that.

She smiled as she rested on his comfortable chest as she said happily: "I'm happy to give master my first-time anal sex."

All the worry in Julia's eyes disappeared. She was very nervous about receiving something as big as Jake's dick inside her asshole. But now hearing Jake's words she actually couldn't wait for it to happen.

As a middle-aged housewife, she had already done a lot of stuff, unlike a young teenager like Jake. She had already fallen fully in love with her master Jake, but she wasn't able to give him any of her first, which had all been taken by somebody else.

And at first, she thought Jake wasn't that bothered by it, so now hearing Jake wanted to fuck her in the ass so badly, was because it would basically be his private hole, where no man had gone before, Julia got insanely happy and all her worries disappeared without a trace.

Jake moved on top of her and looked at her beautiful face.

Julia smiled happily as she said: "Master, please fuck this slave's asshole as much as you like. From this moment on my asshole will belong only to master."

Jake gently rubbed her cheek as he moved in for a sweet kiss with her.

After making out for a bit he said to her: "Don't worry, I'll make sure you'll soon love it up the ass, but first let's make some sweet love."

Jake then thrusted his erect dick inside Julia's soaking pussy, causing her to moan loudly.

She wrapped her legs around him, making sure his dick wouldn't be able to leave her pussy, and like that Jake continued to pound her pussy while looking Julia in the eyes.

Julia never shied away and kept looking at Jake while she moaned loudly as his dick fucked her pussy.

"AH! Master, yes, master more fuck me mooooreee," Julia's words got lewder and lewder as she sunk into pleasure.

Naturally, Jake didn't back down as he swung his hips making sure his dick reached nice and deep inside her.

After a bit passed Jake came deep inside her pussy, causing her womb to once again fill up with his semen.

Naturally, Julia climaxed hard as well as she felt Jake's hot semen fill her up.

After both orgasmed Jake got off of Julia and lied down next to her.

He then said: "Lie on your side, your back facing me."

Naturally, Julia immediately moved in position. Jake then got behind her as he spooned her he then whispered in her ear: "Now stick out that meaty butt of yours and enjoy as I finally take one of your firsts."

Different from before Julia didn't get nervous. Now she couldn't be happier giving Jake her first-time anal sex.