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duration 10:43
Pegging My Sissy Boyfriend video from Fiona Dagger
Pegging My Sissy Boyfriend by Fiona Dagger (This was originally filmed as a custom video) Your girlfriend catches you trying to remove your cock cage, and she's not happy about it! She reminds you that she's the only one allowed to uncage you, and says she's going to have to punish you now to teach you a lesson. She makes you lay back on the bed and spread your cheeks so she can remove your butt plug, then puts on her strap on harness to pound your sissy hole! As she starts fucking you she teases you about what a slutty little sissy you are, telling you how she's not going to let you wear boy clothes at all any more, just skirts, dresses and little thongs for you from now on! She fucks you harder and harder in your tight little sissy pussy, describing to you about how she's going to tell all her friends that you're a sissy, and that they're all going to share you together! You're going to be passed around and used, of course with your little cock cage on the whole time, so you can only ever have a sissygasm! Your girlfriends makes you call her daddy as she fucks you, and gets you to moan as girlishly as you can as she pounds your sissy hole, until finally you can't take it any more and you have a sissygasm on her cock! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, femdom, british domme, female domination, sissy, sissies, sissyboy, humiliation, pegging pov, strap on, strapon, strap-on, butt plug, gender play, gender swapping, feminization, submission
duration 15:34
Sweet Mommy Pegs You video from Fiona Dagger
Sweet Mommy Pegs You by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) Mommy can tell you've had a hard day, and she wants to make you feel better. She kisses you and tells you she's here to look after you, and says that she knows what will help relax you - her strap-on! You perk up immediately at the prospect of mommy fucking your ass for you, and she smiles and tells you to go ahead and start warming up your asshole with your fingers as she gets ready. You start fingering your hole as you watch her strip down to her lingerie and put on the harness, offering you a selection of toys and smiling when you pick the largest one! She lubes it up, getting you to match her strokes as she jacks it off for a minute, until she feels you're good and ready for her. You pull your legs back and she leans over you, kissing you sweetly as she starts to slide the toy inside you. She fucks you slowly at first but builds up the pace until she's pounding you hard and fast, encouraging you to stroke your cock for her and to watch her tits swinging above you. She gets you to hold your cum as long as you can, then finally allows you to spill it everywhere before kissing you again and telling you to go take a shower and then to join her on the couch for cuddles! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, mom son, mommy son, mother son, gentle domme, mommy domme, gentle femdom, pegging, strap on, strap-on, loving, sweet
duration 19:54
Pegged By Mommy video from Fiona Dagger
Pegged By Mommy by Fiona Dagger (This video is taken from my Just For Fans, and is perfect to watch on your phone! It's a good example of the kind of taboo content I post on my JFF - I make videos like this which are filmed on my phone, and generally a little shorter and simpler than my full length roleplay videos; plus I also post photo sets and GIFs, all with explicit taboo story captions. There's also NO pay-to-view content once you're subscribed, $7.99 gets you access to everything, including this very video! :) Subscribe to JustFor.Fans/FionaDagger for just $7.99 a month to see all the taboo content you've been missing out on!) In this video: You and your mom are catching up over a cup of tea, when she asks you how things have been going with your girlfriend recently. She asks if you guys are experimenting sexually, and impresses upon you the importance of being safe. She asks if you felt more confident with your girlfriend after trying out a few things with your mom first, and you thank her and say yes it was very helpful! You confess to your mom that your girlfriend wants to try pegging you, and you're feeling a little nervous about it! Your mom reassures you that it will be fine, in fact she suspects that you'll love it! She offers to do some practice with you so that you'll feel ready for seeing your girlfriend, and you gratefully agree. Your mom gets you to start fingering your asshole and warming it up, while she goes to get her old strap-on out of the attic. When she gets back she takes over from you, using her fingers to stretch you out and get you nice and ready. She then straps herself in and gets you to pull your legs back, talking soothingly to you and encouraging you to stroke your cock as she slowly and gently begins to fuck you. She takes her time warming you up and making sure you're feeling happy and relaxed before she speeds up and starts fucking you more vigorously. She makes you edge yourself, not letting you cum straight away, even though you really want to! Finally she allows you to orgasm and you make a mess all over your stomach as she pounds your asshole. She then tells you she's got a butt plug you can use to keep your ass nice and relaxed until your date with your girlfriend tomorrow, and makes you promise to tell her all about how it goes! TAGS: british, english, ginger, redhead, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, taboo, family affairs, mom, mother, mommy, son, sweet, loving, gentle, pegging, strap on, strap-on, anal play, pov, anal fingering, anal masturbation, joi, jerk off instructions, jerk off encouragment
duration 21:44
Big Sis Teaches You Pegging video from Fiona Dagger
Big Sis Teaches You Pegging by Fiona Dagger You come to your big sister with an embarrasing request; explaining to her that the lastest craze amoungst your friends is pegging, and that all the boys are bragging that they've done it; you have to admit that you've never done it and you have no idea what it's like! You beg your big sister to help you out so you can hold your own in your friend group, as right now they're all making fun of you for being inexperienced! Your sister is very surprised and suggests just showing you some videos and talking you through it, but you beg and beg until she eventually agrees to just show you. She finds her strap on and tells you how to warm yourself up, alternately between being sweetly encouraging and giggling at how weird it is to be doing this with her own little brother, then slowly begins inserting the dildo into your ass. You surprise her by how well you're taking it and she soon begins speeding up the tempo until she's pounding your ass hard and fast! As she keeps encouraging you and telling you how well you're taking it, she also admits that she's missed doing this! She teaches you how to stroke your cock at the same time as getting fucked, and talks you gently through it as you get closer and closer to cumming! After you've exploded all over your tummy she offers to keep practicing with you, saying how she had forgotten how much she enjoyed fucking boys in the ass! TAGS: british, english, redhead, ginger, tattoos, tattooed, pov, solo female, roleplay, dirty talk, posh accent, taboo, wincest, family fun, family affairs, siblings, bro sis, brother sister, older sister, loving, sweet, caring, femdom, pegging, strap on, strapon, ass fucking, anal play, sex lessons, cute, genlte, cfnm, clothed female nude male
duration 25:38
Pegged By Your Auntie video from Fiona Dagger
Pegged By Your Auntie by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) Your mother suggested you go spend the evening with your aunt, and when you get there your aunt starts immediately fussing over you and quizzing you about your love life, saying what a handsome young man you've turned out to be, and how she's not surprised at all to hear from your mother that you've had plenty of girlfriends! She says that if you have any questions or worries about sexual stuff, that you should tell her and she'll be more than happy to help out. You say you're not sure that your mom would want you talking to her sister about things like that, but your aunt tells you that's where you're wrong - your mother actually sent you to see her for the express purpose of expanding your sexual knowledge! Your aunt explains that although your mother has always been more of the reserved and shy type of woman, whereas your aunt is much more bohemian and adventurous, they understand each other very well - and your mother knows that she'd be too awkward to teach you about these things, so she's handed the responsibility to your aunt instead! Your aunt promises that your mother is absolutely fine with her 'coaching' you, and says that she even has permission to physically show you new tricks! She launches back into questioning you about all the sexual experiences you've had so far, and when she gets to asking about anal play, you admit that you've performed anal on a girlfriend, but never recieved it. Your aunt tells you not to worry, she can absolutely guide you through your first time, and in fact it's one of her favourite things to do! She lifts up her kaftan to show you that she always wears a strap on harness as she loves the feeling and the reminder of it, then tells you to sit and relax while she goes and finds a toy for it! When she gets back the harness is now fitted with a dildo, and your aunt soothingly talks you through what's going to happen next. She removes her kaftan, telling you not to be embarrassed by her breasts, and encouraging you to admire them. She lovingly strokes her dildo as she walks you through what's going to happen, then tells you to go ahead and get naked! As you strip off in front of her she admires and compliments your body and cock, saying that your mother will be so pleased to hear that you have a lovely big dick - she told your aunt that she was wondering about it, but she'd been too shy to ask you directly! She gets you to lay back and start stroking your cock, then massages your asshole gently until you feel less nervous. She uses her fingers on you at first until your asshole relaxes, then slowly begins to fuck you with her strap on while she lovingly encourages you to jerk yourself off. She slowly picks up the pace until she's fucking you hard and fast, giving you lots of compliments and telling you that your mother is going to be so proud when she hears how well you've done - until you can't hold it any more and you spurt huge ropes of cum all over your stomach! Your aunt tells you that you did amazing, and if you feel like you need any more practice or advice for anything sexual, you can come to her any time - then suggests that the two of you have a nice warm shower together to clean up before you go home to your mom! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, mom son, mommy, mother, aunt, auntie, aunt nephew, strap on, strapon, strap-on, pegging, anal, pegging pov, gentle femdom, mommy domme, sweet, loving, sex lessons
duration 29:03
Making Molly My Good Little Slut video from Fiona Dagger
Making Molly My Good Little Slut by Fiona Dagger I sensually domme the beautiful Molly Darling - gagging her cute little mouth with a ballgag and pulling her around on a leash before bending her over my sofa and having some fun with her big round ass. I insert an anal hook into her asshole and attach it to her hands behind her back, leaving her squirming and powerless against me. Next, I get a vibrating toy and push it into her tight wet pussy, making her wriggle and moan even more as both her holes are filled. I then take my time getting her ass all nice and pink, spanking her with my hands and then a paddle! Then, I inform her it's time for her to eat my pussy, and she does so beautifully, kneeling on the floor between my legs and sucking and licking my clit until I cum. I then decide that she's earned some attention and I put on my strap-on for her to suck, commanding her to impress me with her skills and show me how much of a greedy little slut she can be. She deepthroats and gags on my cock, getting all messy and dribbly, and when I'm satisfied I bend her over again and fill her pussy with my cock, fucking her tight hole until she's moaning and trembling! Before she can cum I pull out of her and make her sit down on the sofa with her legs spread, and inform her that she's been a very good little slut and I'm going to use some toys on her now until she cums for me. I use a wand vibrator on her clit and a glass dildo in her pussy, pleasuring her until her creamy pussy is making a huge mess all over my sofa and she finally cums! ~~This is Molly Darling's first Girl/Girl video! Make sure to go check her other videos out :)
duration 17:55
you were meant to be a girl: loving feminization and pov bj video from Veggiebabyy
you were meant to be a girl: loving feminization and pov bj by Veggiebabyy This is a custom video! Contact me if you’d like your own! You’re one of my boyfriend’s friends, and I’ve noticed they always pick on you and make fun of you, and I don’t like it. I decide to take matters into my own hands and start by sitting you down for a talk. I want you to have good friends. Friends shouldn’t bully you like that. Friends should take care of you and treat you well, and why not start by befriending the person taking care of you right now? Be my best friend! Become one of the girls! You’ll fit in much better with us. Becoming one of the girls just seems right for you, and I think you’re going to love it. If you’re going to be one of the girls, well, you’ll need to be one of the girls! I’ll help you pick out new outfits and do your hair. I even picked out an outfit for you that matches mine so we can be twins! One last thing before you get changed: I have a chastity cage for you. It’s not a punishment. Girls just don’t have penises. We’re going to lock yours up so it shrinks away, and I’ll hold the key so you aren’t tempted to unlock it. After you’re all changed and looking sexy in your new girl clothes, we take things one step farther. If you’re going to be a girl, you’ll need to take dick like a girl. Don’t worry, I’ll teach you. I unzip my pants and slide my cock into your mouth, gently facefucking you while I praise you and give you tips for sucking cock. I get a bit carried away and hold your head to fuck you a bit harder, but you take it like a champ. We’ll get your throat trained up to take any pace of facefucking in no time! You already seem so much happier being a girl! I knew this was the right life for you.
duration 33:01
Pleasure Puppets: Trix and Kayleth aroused and controlled on Sinister's mental strings video from Mesmerotic
Pleasure Puppets: Trix and Kayleth aroused and controlled on Sinister's mental strings by Mesmerotic Trix and Kayleth love to play together, but deep in Sinister's hypnotic control their normal closeness is twisted into a fevered desire to kiss, touch, and pleasure each other. After an induction staring deep into each others eyes their emotions become just strings for him to pull, and his puppets just can't keep their hands to themselves. Even when Sinister holds them apart, they pull desperately towards each other, desperate to touch. The desperation intensifies when he starts to play with their minds even more, his words forcing Trix and Kayleth alternately into dominant and submissive mindsets. Each melting under the other's touch before suddenly needing to control in turn. And when they're both set to be on top, sparks fly as they wrestle to be the one making the decisions. Kayleth then spends some time as Trix's blank doll, with Trix feeling and mirroring every touch and sensation that's inflicted on her helpless plaything. Before long the hypnotic pleasure becomes too much for them both and they cum in unison, the arousal amplified as it echoes between them. Finally it's time for Kayleth to taste Trix's strapon, with the added bonus of Trix feeling every touch to it as if it were a part of her body. For his amusement, Sinister mentally tugs them between needing and hating the act, so the two take it in turns to push the other to take the pleasure they're determined to give. Models: Sinister topping, Imaginatrix & Kayleth bottoming. More of Kayleth can be found at: onlyfans.com/kayleth ✧༝┉┉┉┉┉˚❋ ❋ ❋˚┉┉┉┉┉༝✧ Mesmerotic is a small hypnosmut production company run by Imaginatrix and Sinister. We are available for sessions, customs and tuition. Imaginatrix: http://HypnoHedonista.com Sinister: http://SinisterDenial.com
duration 11:14
the third attack: therapist destroys your sore asshole with strap on video from Veggiebabyy
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