Mistress had said she wanted to try something new, something different that I had never thought about until now! My first anal training! Of course, she suggested that we should film this first-time experience for you all. What you’ll see is our real D/s dynamic with me getting my first-ever anal training from my Mistress. She starts by warming me up with some spanking on my bare round bottom. Next, she spanks my cute little bum-hole with her hand and a crop while I am fully exposed for you in the humiliating diaper position. It would seem that I love having my sensitive little hole spanked as I can’t hide the growing wetness from my princess parts. Mistress uses a small jeweled butt plug to start with. We have done butt plug play before but never one that vibrates. She enjoys pushing the jewel which creates different vibration speeds as well as strapping my bottom at the same time. This feeling is quite new to me, and at this point, I am unsure if I like it or not but my naughty puss-puss clearly says otherwise as it glistens even more. I am told to get on all fours and crawl around on the bed to show off the cute jeweled plug, pink ass, and dripping pussy. Now it is time for part two: The fingers. She slowly pulls out the butt plug and then lubes up my bum hole some more to prepare me for her invasive fingers. Mistress puts in one finger to start with, massaging and slowly penetrating my cute, quivering anus before delving deeper inside, moving the digit around slowly, stretching my hole further. My reactions are all 100% natural as I get used to this interesting new sensation that she promises I will learn to enjoy as this is just my first time. She ups the ante soon after by inserting a second intrusive finger to continue the stretching process. Now she is starting to slowly finger fuck my ass with both fingers moving in and out as the rhythm increases… oh my! I get turned on even more as Mistress tells me to imagine her behind me with her strap-on, fucking her little ass slut. At the end of this anal training, I’m told I must cum with her fingers still inside filling up my ass. I lay on my back holding a powerful, throbbing vibrator to my dripping cunt as she fucks my ass with her fingers as they fill and stretch my insides even more! I can feel my lubed ass tightly gripping her, powerfully clenching onto her fingers inside as I cum hard for her. Fully satiated from this new experience, I hold my Mistress as we embrace in each other’s arms. Phew… That was hot!

miss Bernadette, Sarah Gregory

Resolution : 1920×1080
Duration : 00:33:33

https://way4share.com/98P2/Sarahs_First_Anal_Training_-_MP4.mp4

Ridel Reform school is a school for Wayward Young women with a strict Corporal Punishment Policy. Sierra is a past student at the school and currently works as a maid at the institution. When she is arrested she calls the Principal who is able to first bond her out of jail, then get the charges against her dropped. It was for bringing contraband into the school. Needless to say the principal is quite upset with Sierra. For his help he promised her a very strict punishment. Sierra is brought down to the punishment room for a whole night of spanking and anal punishment. It starts out with hand spanking but progresses to strap, ruler, and then the cane. He then fucks her with a large dildo and then uses the fucking machine on her sore and swollen ass. She is crying all though her punishment and by the time it is over this girl has learned a very important lesson.

Sierra

Resolution : 1280×720
Duration : 01:04:02

Download Sierra’s Contraband Punishment

Sierra was fired from her teaching position at the Ridel Reform School because she was a bad influence on the girls. She’d been a maid at the school for the past several months. However she kept her nose clean and even completed classes at the local Junior College. She talks Dr. Bridgewater into letting her enter the Student Nursing program that the school runs. As a condition of her education she required to attend a Rehab program and go through regular UA testing. Sierra amazes everyone and for the first 6 months she holds it together with flying colors, however after the 6 months cracks start to appear. She doesn’t complete Rehab under questionable circumstances but Dr. Bridgewater tells she’d better be perfect for the next 6 months. That very evening the good doctor catches her on her phone and ignoring a patient. He promises her the spanking of her life. Like all naughty girls Sierra is crying uncontrollably by the time he is finished and she gets her tiny little butthole fucked as well.

Sierra

Resolution : 2560×1440
Duration : 00:52:51

Download Here Come The Tears

Sierra just doesn’t seem to be able to learn her lesson. This time it is Drinking & Driving and then shoplifting. She is given a serious Spanking with cane paddle strap. She is crying right from the beginning and begging for anything else. But her punishment continues and the Principal gets out the enema bag and gives her an enema before he fucks her ass with the fucking machine. She keeps right on crying and begging but it does no good. The punishment continues.

Sierra

Resolution : 1920×1080
Duration : 00:24:13

Download Sierra’s Punishment Room Enema

Ridel School For Wayward Young Ladies was established in 1904 as a means to put errant young women and girls on the right path, the girls 18-21 are all women who have gotten in trouble with the law. Upon sentencing the Judge gives them a choice between prison and Ridel. Sierra is has been at the school since the first day she turned 18. She has been punished numerous times and for the most part it has improved her behavior. She is a trustee of the school and allowed to take care of the which are used in equestrian sports. Today is not Sierra’s day. Principle Outlaw is in a meeting with the board of directors of the school and his boss the Superintendent, when he looks out his window and sees the outside the fence and in danger of being hit by cars on the highway. Imagine his embarrassment when he has to cancel the meeting to deal with the (and Sierra). To make matters worse for Sierra when confronted she denies the deed trying to blame it on the other girls. Unfortunately for her the school’s security cameras show her clearly leaving the barn door and gate open. Sierra is to wait until bedtime when Outlaw takes her down to the punishment room, a room that she knows and dreads. Outlaw makes puts handcuffs on her and makes her go over his knee, keep a paddle nearby telling her if she puts her hands back she will be paddled. He then gives her a no mercy spanking with his hand showing no mercy until she admits to the misdeed. She thinks her punishment is over but Outlaw bends her over the punishment bench and uses the fuck machine on her tender pussy. Spanking her with the cane, paddle and bath brush while she is machine fucked. This is just the beginning though. He uses the fuck machine on her tender asshole, fucking the tight little hole until there is tears in her eyes. The Journey to the truth is a painful one. I am pretty sure that this young lady with be more careful about safety in the future.

File Name : BarnHD.mp4
File Size : 1155.04 MB
Resolution : 1920×1080
Duration : 00:32:57

https://way4share.com/0d79b9a46884c29d/BarnHD.mp4

Parker’s previous record with the ginger root is 3 minutes. She blows that out of the water with this one of a kind figging and spanking video, given by Miss Sephie! The ginger stays in for a whole TEN minutes while Miss Sephie spanks Parker’s naughty bottom with a brush and her hand, plays with the ginger, and even drips hot wax onto her sore bottom! Watch the beautiful bottom jiggle as Parker whines, whimpers, and writhes in this unforgettable video! After the ginger comes out, she gets her big metal plug complete with warming lube to keep her feeling the burn!

File Name : The BEST FF Figging Video by Miss Sephie.mp4
File Size : 1534.44 MB
Resolution : 1920×1080
Duration : 00:13:51

https://way4share.com/960k/The_BEST_FF_Figging_Video_by_Miss_Sephie.mp4

At least 1 in 6 college students experience the roommate that just doesn’t know how to keep their hormones in check. They bring back all sorts of company to their room, and the sexual escapades never seize. This happens to Chris, whose roommate Annie, just can’t seem to keep quiet while she’s studying. Chris also finds out that Annie has been fooling around with some of the other girls’ boyfriends. She finally confronts Annie about and they get into a cat fight. Chris rips Annie’s clothes off and decides what this girl needs is a good old-fashioned spanking.

Afterwards, Chris notifies the Dorm Mother Miss Payne. When she shows up, the two of them really teach Annie a lesson. They tie her to the bed and give her a good strapping and paddling. They untie her and make her hold a butt plug in her bottom. Then a vibrator finishes the job. Annie is taught a lesson she will never forget.

File Name : The_Campus_Cooze.mp4
File Size : 17.05 MB
Resolution : 352×240
Duration : 00:03:01

https://way4share.com/66733efead7cecf6/The_Campus_Cooze.mp4