Tag: Miss Jessica Wood

Miss Jessica Wood – Merciless Hands Trampling in my Riding Boots (1080p MP4)

January 2, 2023December 24, 2023 | by Trampling Fan

Miss Jessica Wood wasnt quite happy with that particular slave and the amount of trampling he can take, so she decided to trample his hands as she missed doing that in the previous clip.This is actually a continuation from the previous clip – Miss Jessica Wood – Merciless Hogtied Trampling in Riding Boots.The slave is already in pain as you know and he didnt have a break at all. Straight after the cruel trampling, he is lying down obediently on the floor again, but this time with his hands placed on the carpet in front of him. He thought the carpet would help him, but nope. It didnt. Miss Jessica shows her sadistic style again and doesnt show him any mercy whatsoever. These heavy riding boots are so painful for the slave obviously. You can see him squirming in pain a lot. Miss Jessica just enjoys standing on his hands and fingers, walking over them and stomping them nicely. You can see clearly the red hands and fingers of the slave during the clip.By the way you can enjoy a lot of close ups this time and less full body camera angles.

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Miss Jessica Wood – Trampling and Stomping in my Riding Boots (1080p MP4)

September 20, 2022September 21, 2022 | by Trampling Fan

Miss Jessica Wood loves tormenting slaves and today it wont be any different. Shes got a slave at her mercy who will suffer beneath her heavy black leather riding boots. Wearing her beautiful brown jodhpurs she looks so hot absolutely ready to have some fun.I am sure you know her sadistic style already as shes very well known Mistress on our store. Basically the entire clip is trampling and stomping the stomach and the back of the slave absolutely mercilessly. The first 5 minutes Miss Jessica trampling and stomping the slaves stomach including some standing on his head, but just a couple of moments. Then its turn to use his back. The rest of the clip the Mistress stomping his back including a couple of stomps on his hands as well. A little bit of head standing is also taking place again. The slave is just squirming and moaning most of the time thanking Miss Jessica for the punishment hes receiving, but Miss Jessica doesnt really pay any attention whatsoever.You can enjoy nice camera angles, full body and close ups as usual.

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Beneath Her Leather Pointy Boots

August 25, 2022August 25, 2022 | by Trampling Fan

Miss Jessica Wood. She is such a cruel and merciless mistress. You know her very well. She loves inflicting pain to her slaves. This time she is wearing stunning grey leather pointy toe boots with metal high heels, black leggings and black shirt. The first 3 minutes of the clip you can enjoy really good smothering and the rest of the clip is just no compassion high heels trampling (because the slave wasnt a good sit). While Miss Jessica is smothering his face she puts the slaves hands above his head and under the heels of her boots, so the slave cant move his hands. Thats so brutal to be honest. The slave is moaning a lot in this clip as the high heels are really sharp and Miss Jessica doesnt bother herself to use them properly along his bare skin. Very nice marks as you can see. Miss Jessica also have her soles licked very well using the slaves tongue of course. And while the slave is licking her sole she is using another boot to scratch his body with her heels. And of course the slave has to suck the pointy boot. As you can see the slave is so skinny and thats why these heels are really painful for him as you can see his bones. The clip is mainly close ups of her boots, so if you really like leather pointy boots with high heels then you will love the clip.

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Little Slave for Miss Jessica Wood

August 12, 2022August 13, 2022 | by Trampling Fan

Do you know Miss Jessica Wood ? I am sure you do. Cruel and merciless mistress. She is here again to punish the slave and trample him into the ground. Miss Jessica is looking so stunning wearing a white shirt, a black leather gloves, jodhpurs and a black leather riding boots. These boots are one of her favorite boots by the way. Ouch and the slave is in trouble. She really wants to squish the pathetic slave into the floor and thats exactly what she does as she stands completely full weight on him, on his chest, on his stomach, on his head and on his back. Just to mention that Miss Jessica is standing on his head over a minute without moving and staying on the same spot on his head with her heavy boots and rough heels. At some point Miss Jessica has decided to leave the slave alone, but actually she has decided to come back and trample him again just for her amusement. No break for the slave. She doesnt feel any compassion for the slave and his suffering. And at the end Miss Jessica steps on his hand before she leaves him alone. You can see some face slaps as well and loads of close ups and some full body views. For all riding boots lovers 🙂

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Red Dress and Red Flat Shoes

March 14, 2022March 14, 2022 | by Trampling Fan

Miss Jessica Wood is coming back home dressed in red dress and red flats looking so hot as always. The slave Rusty has been told to be in position, so Miss Jessica can use him as a comfortable little sit again before she gives him some trampling. Miss Jessica likes smothering and thats exactly what the slave Rusty is getting. The first 3 minutes is smothering and the rest of the clip is full weight trampling with these flat red shoes.

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Introducing you Miss Jessica Wood

February 26, 2022February 26, 2022 | by Trampling Fan

Hello my dear customers. Let me introduce you to Miss Jessica Wood. You know her probably already as she is quite famous on the BDSM scene, but this is her first performance here. So I hope you will enjoy it. She is coming back from the stables dressed in her riding outfit (jodhpurs, black leather riding boots and white shirt) and she is a little bit tired so she wants to have a small break. And whats the best way to do that, of course by using the slaves face. The slave is waiting to be her comfortable sit. So she has started with some smothering as she really loves that. The slave is struggling for air, but Miss Jessica Wood doesnt really care. So the smothering continues approximately 2-3 minutes in the beginning of the clip. But the slave wasnt comfortable sit for the mistress and he will be trampled and stomped hard for that reason absolutely full weight. She jumps on him 2 times and basically using him as a human floor. These boots are hard by the way. Miss Jessica Wood is marching on the pity slaves body also. And of course the soles of her boots need to be cleaned so she is using his tongue as a doormat. At the end of the clip the slave does regret that he wasnt a good sit for his mistress. You can see incredibly good close ups and some boots prints on the slaves body as well.

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Beneath Her Wedges

December 4, 2021December 5, 2021 | by Trampling Fan

Miss Jessica Wood is wearing her black skirt, white long sleeved shirt and her wedges today. You can see quite good her beautiful legs by the way. Just imagine to be under these gorgeous legs. The mistress is here to trample the slave Rusty and then he will become her comfortable little sit. This is kind of a soft trampling, but as you can see slave Rusty is struggling under her weight. The first 5 minutes of the clip is trampling and the rest of the clip is smothering and face sitting. And to be honest Miss Jessica Wood is the queen of the face sitting. And when Rusty needs to breathe he has to lift her up.

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Wake Up

November 21, 2021November 22, 2021 | by Trampling Fan

Miss Jessica Wood is here again. You know her from the clip Introducing you Miss Jessica Wood. She is really merciless mistress to be honest. She is wearing her black tight leather look leggings this time and she looks awesome. You can see her beautiful legs very well. She is coming back home and she wants to use the sofa to sit down and have a small break. Slave Rusty is napping there, but she doesnt care. Miss Jessica Wood sat down on the sofa straight away once she has entered the room. She is the queen of face sitting by the way. The first 4 minutes of the clip are face sitting and the rest of the clip is trampling. This time Miss Jessica is wearing very nice shoes as you can see. So the slave Rusty has to feel the heels and the full weight of the mistress. You can enjoy full body camera angles and close ups as always. Some stomps are taking place as well. Slave Rusty looks like he doesnt show that he is in pain, but thats how he is dealing with that. He doesnt say anything. You can see some heels marks on his body at the end of the clip.

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Smothering and Trampling

October 9, 2021October 10, 2021 | by Trampling Fan

Miss Jessica Wood is here again. She looks so stunning again wearing stilettos, black leather trousers and a white shirt. What is she doing today ? Punishing her slave of course by smothering him and trampling him just for her amusement. The slaves head is trapped in a box and he can move at all. Thats so convenient for Miss Jessica. She will smother him very well. And you can see during the clip that the slave is really struggling for some air. But she is not happy with the smothering because the slave is worthless and he wasnt a comfortable sit for her. Of course he will be trampled on with no compassion from the mistress. As you can see he is very skinny and these sharp heels are extremely painful for him but really enjoyable for Miss Jessica. Of course he has to lick the sole of her shoe as well. Actually she is wiping out her soles all over his tongue. You can see some heels marks on the slaves back as well. Extremely close ups mostly in this clip.

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Obedient Doormat

September 30, 2021October 1, 2021 | by Trampling Fan

The beautiful and sadistic Miss Jessica Wood is here again dressed in white jodhpurs, white shirt, black blazer and her heavy black leather riding boots with metal spurs. She wants to have some fun again. The slave is on the floor of course and he will be trampled on absolutely full weight. But first Miss Jessica wants her soles licked clean while she is checking up on her phone. After that the trampling begins. You can enjoy some full weight head standing on both sides of the slaves head. Oh Miss Jessica is cruel. You will enjoy the moment where the slave was in absolute pain while trying to move the boots off of his head, but Miss Jessica didnt pay attention at all and just keep standing on his head. The Mistress is trampling the slave carelessly and laughing while doing that. She just loves to feel the slave suffering beneath her riding boots. You can see that the slave is gasping for air at some point but Miss Jessica doesnt care.The slave told me after the clip that these soles are extremely hard, especially the heels and his head was still in pain afterwards. So if you are familiar with riding boots in general you should know how hard and heavy they are.The clip is filmed with static camera, but we have added some close ups for the nice moments. You can see from the GIF. So basically is full body angle and close ups.

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