Start of an amazing day (2)

Jake along with the three women headed into the kitchen and together they ate breakfast.

Jack relaxedly ate his meal as he looked at the three beauties. Naturally, they were still fully undressed and their breasts moved nicely with every movement they made.

Just after finishing his food, he heard the doorbell ring.

Jake smiled as he said: "All right it's time to start."

He then headed to the front door and opened the door. As he was still naked as well he made sure no-one from outside was able to see it.

After the door was opened Stefanie quickly got inside and Jake closed the door behind her. She was wearing a cute dress, which made her look all the more beautiful.

Naturally, the dress would be taken off almost immediately.

"H-hi master," Stefanie said with a shy face, knowing what kinds of things she would do hereafter, especially seeing his dick was already out.

Jake smiled as he looked at her cute face, he then lifted her chin with his fingers and kissed her deeply.

Stefanie feeling Jake's lips pressing on top of hers gladly accepted it and kissed him back as well.

Meanwhile, Jake's hands had already found their way to Stefanie's small tight butt and groped it nicely.

After kissing her for a bit Jake broke off the kiss and said to her: "All right take off that dress and let's go into the kitchen, there's someone I want you to meet."

Stefanie immediately took off her dress and as she wore nothing underneath she was immediately naked.

Jake chuckled seeing she still wore no underwear.

"Seems like going commando is becoming more and more normal for you."

Stefanie pouted and kept quiet, knowing that she actually started to like the feeling of not wearing any underwear under her clothes, especially as she knew it turned Jake on, which was all she wanted. Still, she didn't know when Jake would finally let her wear some underwear again.

Jake along with Stefanie then moved towards the kitchen.

When Stefanie entered the room all three women looked at her, which caused Stefanie to lock eyes with Jennifer.

"M-m-ms. Harper?!" Stefanie yelled out in surprise.

She never expected her usually so serious and strict teacher was here eating breakfast, completely nude.

Seeing those big tits usually packed away, move so freely Stefanie got even more jealous of her.

Jake stood beside Stefanie as he said: "It's not Ms. Harper anymore in private, you can call her sister slave Jennifer."

Stefanie looked at Jake with a dumbfounded gaze. Never had she thought this guy was capable of conquering a woman like Jennifer, but nothing was less true.

After all, the woman in question was here naked and it was easy to guess she had already been pounded a lot by his amazing dick.

Jennifer was blushing red fiercely as well as she had been seen by yet another one of her students. She couldn't bring herself to say something as she was very embarrassed.

She was supposed to guide the youngsters into a good life, instead, she had happily become the slave of one, now living to satisfy him. And from now on some of her students would look at her lewd actions, as Jake would do whatever he wanted with her.

Jake looking at the embarrassed Jennifer and he said: "All right everyone of you finished eating breakfast?"

"Yes master," the three of them replied in unison.

"Great then line up in front of me," Jake then got a fun idea as he smiled and said: "By breast size."

Naturally, it was quickly decided with Julia at the front, followed by Jennifer, Kayla, and lastly Stefanie.

Julia had a smug smile on her face as she pressed her chest out, even more, showing the other slaves they didn't even come close.

At the same time, Stefanie was embarrassed as she looked down on her own two small bumps and then to her right where three women stood each with bigger and bigger tits. After all, even if Kayla was the third-biggest, she still was way bigger than she.

Jake chuckled as he looked at the four of them.

"All right before we begin having an amazing day filled with pleasure some announcements. Firstly Kayla will receive punishment for being a bad big sister, a bad student, and nearly running her mouth off yesterday. Any of you a suggestion?" Jake said looking at Julia, Jennifer, and Stefanie.

Where Jennifer and Stefanie didn't really want to have any say in this regard, Julia had no problem speaking up.

"Master, I have an idea. Just like master did to me, put a lot of vibrators at all sensitive places and have Kayla cum non-stop."

Julia still remembered vividly when she had to go through this ordeal and especially Kayla's smile knowing she didn't have to do this.

After Julia finished she stuck her tongue out at Kayla, as if telling her this is revenge for laughing at me before.

Jake enjoyed himself seeing Julia act so childish. She was 37 with a bombshell body, which made it all the more erotic when she acted like a kid. Now she wanted revenge on Kayla for laughing at her previously when she got lost in pleasure.

Naturally Jake had no qualms with what Julia said as he was quite interested in seeing how long Kayla could hold out.

"Very well, let's do that then."

Julia was happy whereas Kayla felt shivers go through her body as she remembered her mother's face when she was finished.

"Well then continuing, today will also be the day Jennifer as well as Kayla will start anal training."

Jennifer as well as Kayla looked at Jake with a stunned gaze. Naturally, both of them didn't talk back at Jake and just accepted the fact.

Julia instead got even happier. She was the only one who's ass was constantly tormented and had to live with a plug up her ass. While she knew lately she had enjoyed it more and more, coming to a point where Jake could make her cum only toying with her ass, she still was glad more women would now join the anal training sessions.

But Jake's last announcement made her gulp down her saliva hard.

"And finally today will also be the day, I will take Julia's anal virginity."

Julia looked at Jake with a wry smile but accepted her fate.

Jake smiled seeing the women's expressions. Everyone but Stefanie would now experience anal pleasures and he couldn't wait to insert his dick in Julia's tight asshole.

"Good then Julia you go cleanse your insides with an enema make sure it's fully clean, Stefanie you help her with that. As for the two of you," Jake said turning to Kayla and Jennifer, "Let's go to my bedroom to have some fun."

Julia gulped knowing Jake was set on taking her inside her asshole and went towards the bathroom. Stefanie followed behind her not really knowing what to do, but as Jake had told her to help Julia she did so without asking.

Jake along with Jennifer and Kayla went towards his own bedroom where he planned to have some fun and start their anal training before it was time to dig in the real thing.

Before starting, Jake took out all the things he would need to start their first-ever anal session. Naturally, a lot of lube was present as well as small anal beads and finishing it up with a small butt plug.

He would do it just like he did with Julia, first, he would finger their asses while lubing them up, after which anal beads were used to make them get used to it more and he would finish it up by placing the butt plugs inside them.

Just like Julia, they would only come out for anal training or if they needed to go to the toilet.

"All right put your hands on the wall and stick out those amazing asses of yours."

Both women gulped as this was something they had never experienced before and thus they were incredibly nervous. Still, they moved as Jake said as they didn't want to disobey him.

Jake stood behind the women in between them, looking at both meaty asses. Jennifer had some wider hips and her ass was a bit fuller than Kayla's, but that didn't mean Kayla's ass wasn't nice. Rather Jake knew for a 17-year-old girl, Kayla's behind was looking incredible.

He groped both women's butt gently as he said: "You two ready to start?"

Both replied nervously: "Y-yes master."

Jake smiled as he put lube on his index finger on both hands and then simultaneously used these fingers to start poking at their buttholes. Both women tensed up from feeling Jake's finger in that place.

"Relax, I won't hurt you. The more you relax the better It'll feel."

"Yes, master."

Jake saw both of them did seem to relax a bit, yet they were still tense.

After gently poking their holes for a bit and drawing some circles around them it was finally time. Putting a huge amount of lube on his fingers he put some force behind them and entered both Kayla's as well as Jennifer's asshole.

"Eehhh!"

"Oohhhh"

Both women shrieked as something entered them in a place that wasn't meant for it.

Jake gently started to finger their assholes, making sure not to enter too deep at the beginning at lube everything up.

Like that he fingered them for a few minutes trying to get them a bit used to it. At first, they tightened their assholes very hard, yet after he had continued fingering them, they relaxed more and more.

Seeing they were getting used to it, he entered them even deeper with his fingers. He could even hear some small moans coming from their mouths as well.

Jake smiled as he continued playing with them. After another few minutes passed he guessed it was about time to start with the anal beads.