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duration 21:22
The Tutors Teacher: Mom Takes Your Virginity video from PaintedRose
The Tutors Teacher: Mom Takes Your Virginity by PaintedRose How did it go tutoring that pretty, popular girl from class? It's going so good! She is so thankful for her better grades that she wants to have sex with you but you're nervous because you're a virgin. You want to make sure you impress her but are really worried about being inexperienced and express this to me. Step-Son, I understand and it's my job to prepare you for the world and that includes sex education. Go wait for me in my bedroom sweety! Do you trust Step-Mommy? Think of that pretty girl and close your eyes. Step-Mommy surprises you with some sensual kissing on the lips and it's obvious that you like it. I take out your very hard penis and start kissing it and using more dirty talk which gets you even harder. Keep pretending you're with the cheerleader and I will teach you to fuck pussy and how to please a girl sexually. This film features POV Roleplay, handjob, Blowjob, Sex Education, devirginizing excitement, close up, cum on tits. This custom made film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. ****************************************** KeyWords: Step-mom, StepMom, Step-Mom, Step-Mommy, Step-Mother, MommyDomme, Domme, Femdom, FemDomme, Blonde, Mature, Natural Tits, Pussy, Thick, Juicy, Squirting, Squirt, Female Orgasm, Sex, Step-Mommy Fetish, Romantic, Love, Drama, Story, Bundle, POV Sex, Horny, Insatiable, Depraved, Perverted, Kink, Suck, Fuck, Underboob, Curvy, Curves, Chubby, Big Lips, DSL, Rosie, MILF Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Virtual Sex, Taboo Step-Mom, Cougar, Femdom, Nurturing, Cum for Step-Mommy, Good Boy, Step-Mommys Good Boy, Blowjob, Doggy, Doggy Style, Anal, Ass, Missionary, Creampie, Cream Pie, Asshole, Pantyhose, Hosiery, Lingerie, Sensual, Lover, Loving, Sweet, Seduction, Seductive, Sin, Sinful, , Facial, Cunt, Step-Mommy Cunt, Fuckhole, Shaved, CumPlay, Spitplay, Cum, Come, Big, Tits, Titties, Tittys, Boobs, Boobies, Breasts, Nipples, Suck, Cock, Dick, Swallow, Step-Mama, Step-Momma, Panty, Panties
duration 16:44
Love Potion Transforms Hermione Granger Into An Anal Slut video from InfinityWhore
Love Potion Transforms Hermione Granger Into An Anal Slut by InfinityWhore [This was a custom request] Hermione and her friends are seeking a Polyjuice potion. She comes to you, as you're one of the top wizards in your year, for some help. You don't have a polyjuice potion but you have just finished brewing a love potion. You've always fancied Hermione but she's a bit too straight laced for your liking, so you get an ingenious idea. You lie and tell her that you have her polyjuice potion right here. You encourage her to taste it - just to make sure that it works. She admits that that's probably a good idea so sip your love potion straight from the cauldron. After a few seconds, she looks at you with lust in her eyes and begins to tell you that she's always been in love with you. She strips out of her uniform, showing you her underwear and perfect, tight little body. She begs you to make love to her right now on the desk. Your cock jumps to attention. But you want her mouth first... you instruct her to wrap her little damp panties around your cock and suck it. She happily obliges, slurping on your hard length with an enthusiasm that only a girl in love would give. Before long, you need to feel the wetness of her cunt. So she climbs on top and rides you cock on the desk until you both cum. Your seed spills into her hot womb but your cock stays hard. You want to make the most of your potion and you know, under these circumstances, that she'll even let you take her sweet, virgin arsehole. She moans with both pain and pleasure as you slip into her arse - never before stretched by a big cock. It's a tight fit and it takes a while for her to adjust to your whole length. But soon she's sat on top of you with your entire cock eaten up by her arse. She begins to move on top of you once more - riding you with her asshole. She feels incredible. Inhumanly tight and warm around your aching dick. You buck your hips into her and she matches your strokes, riding you until you cum once more into her belly. Leaking cum from both of her holes, the potion begins to wear off and she suddenly realises what has happened. She's ashamed and quickly rushes to cover up her exposed body, calling you all the names under the sun for taking advantage of her in such a way. You know she won't tell anyone of this little indiscretion though - she's far too much of a "good girl" for that. You've had your way and no one need ever find out.
duration 15:09
Bro Gives Sis Ruined Orgasm video from Fiona Dagger
Bro Gives Sis Ruined Orgasm by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) Your big sister made you a promise, and today you're reminding her of it... It's been a few days since your 19th birthday, so you shyly remind your sister that she had told you that if you had still failed to lose your virginity by the time you turned 19, she would help you! Your sister admits she'd pretty much forgotten about that promise, but says of course she'll still help you. You tell her you're nervous, so she tries to calm you down and relax you, telling you it will all be fine. She suggests that you both try and relax and get in the mood, by touching yourselves, before you try to go any further. She takes off her clothes and makes you do the same, and the two of you begin shyly masturbating until you're both frustrated and turned on. You tell your sister you think you're ready, and she lays back and allows you to slowly enter her pussy for the first time! She gives you lots of encouragment and though you start out slow, soon you're fucking her hard and fast! Your sister is amazed by how good you're doing and seems to be enjoying herself more and more! You warn your sister that you think you're about to cum, and she tells you that you'll have to pull out to be safe, but to please try and last a little longer, as she's so close! You do your best to keep going, but just as your sister is beginning to climax you realise you can't hold it any more, and you quickly pull out to safely blow your load all over the floor! Your poor sister's pussy is left twitching and pulsing as she has a ruined orgasm, with no stimulation to satisfy her! You watch as she moans and writhes, and you ask if she's okay, but she just tells you that it's fine and it's not your fault, it was your first time after all! She explains that you gave her a ruined orgasm and now she's all achey and frustrated, and says that she'll need to take care of herself now and finish herself off! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, dildo, taboo, bro sis, brother sister, ruined orgasm, dildo fucking, virgin, virginity taking, sex lesson, sex lessons, sweet, caring
duration 19:20
your curious little sister video from Squeezypeach
your curious little sister by Squeezypeach I'm just hanging out, bored, when I see my big brother's phone just laying around. "bro... I'm gonna play some games on your phone...." I unlock the screen to find a folder that's full of very interesting photos and videos. I start flicking through them and my eyes go wide! I've never seen stuff like this before. I start to wiggle around and my pussy throbs. I pull my onesie to the side and touch my wet pussy, moaning softly, eyes glued to the phone. my brother walks in on me and I smile casually, explaining what I found, still touching myself. you tell me I shouldn't be doing that but I don't understand. "what do you do with the pictures then?" but you say I should be doing it alone and I tell you I was alone until you came in, silly! I wanna try out the stuff in the video, it looks so fun! you say we can't do that together but the people in the video are brother and sister too! you get embarrassed but I ask you to show me what you do when you watch the videos. we masturbate together for a bit, I'm watching the video on your phone, you're watching me. and then I ask if I can try sucking my brother's cock, just like the video. still rubbing myself and moaning, you put your hard dick in my mouth. I drool and suck on it, trying to emulate the porn we're watching. a separate angle shows a closer view of me rubbing my plump pink pussy while giving you head. I wanna try everything they do in the video, if we can make it fit! I lay back and you rub yourself on my clit, I moan and breathe heavy, the facial expression is intense when you slide inside me, stretching me out. you fuck me missionary while I tease my nipples, moaning and giving more taboo talk throughout. I rub my clit until I cum on your cock!
duration 25:37
the virginity auction video from Squeezypeach
the virginity auction by Squeezypeach hi, I’m Abby! and I’m a virgin. I decided to auction off my virginity because I’ve always wanted my first time to be really exciting and special and this seemed like a great way to do it. plus I’ve always had a fantasy about losing it to a complete stranger. so if you’re interested, place a bid and I’ll notify the winner! good luck! once you’ve placed a bid, you’ll also receive a special video so you can get to know me (and my body) a bit better. I’m so excited and nervous to meet the lucky winner – and the idea of losing my virginity to someone I just met is turning me on so much. I start off teasing you (I’ve gotten really good at that) but feeling your hands on me sends me over the edge, I need to feel you inside me. I give you my first blowjob ever and it’s so much fun, it turns me on even more until my body is craving your cock. I lay back and tease my pussy, rubbing you against me until you slip inside. as soon as you start thrusting into my virgin pussy, I go wild for it. this stranger is inside me and i love it! I get SO creamy while you’re fucking me and I moan intensely as I cum on a cock for the very first time. this cute roleplay video is LOADED with teasing, creamy pussy, and dirty talk about fucking a stranger and how tight my innocent virgin pussy is. video is in 4 parts – part one is introducing myself and explaining the auction. part two is the video you get after submitting a bid, I show off my body and dirty talk about how you get to fuck a virgin and how bad I want it. part 3 is notifying you that you won. and part 4 is the date/winnings – pov teasing, blowjob, and fucking scene. sex scene is all in missionary
duration 26:44
Your Daughter's Lesbian GF Is Intrigued By Cock video from InfinityWhore
Your Daughter's Lesbian GF Is Intrigued By Cock by InfinityWhore [This was a custom request] You return home early one day to catch your daughter's girlfriend masturbating in her panties on the sofa. She doesn't notice you watching so you decide to let her finish as it's making you very hard. When she cums and opens her eyes, she is extremely embarrassed to see you stood before her. She profusely apologises, explaining your daughter gave her a key and begging you not to tell anyone. Your cock is achingly hard and gives you an idea. You promise not to tell anyone if she gives you her panties. She is confused and hesitant but, desperate to keep her secret, she agrees. She slides them off and hands them to you... but you've already pulled your cock out. You ask her to wrap them around your cock and jerk you off. She reasons with you about how wrong this is, and that she's obviously a lesbian but eventually comes around, deciding it's only a handjob so it's not that bad. She jerks you off with her panties wrapped around your cock, asking you intrigued questions as she does, until you cum into her panties and tell her to put them back on. She leaves with your cum pressed against her cunt. Later that night, there's a knock at your door and you're surprised to see her back. She tells you that she can't stop thinking about what happened earlier on. She's been fucking your daughter and your daughter even ate her pussy so she might have tasted your cum. It's turned her on and she wants to try more of your cock. She begins sucking your cock while you guide her but, most of all, you want to try out her wet cunt. So you instruct her to bend over and you push inside her. She is nervous as she's a virgin, other than the strap-on your daughter uses on her, but she immediately gives in to the sensation of a hard, fleshy cock and admits that it feels so much better than a toy. She lets you use her little wet pussy while telling you all about her and your daughter's sex lives, until you fill her up with a huge load of cum. But, seeing as she's so eager, you're not finished. You want to use that perfect little virgin asshole too. She is very hesitant as she's never had anything inside her arsehole before but she trusts you now, after everything else has felt amazing so far. It's a tight fit, but you manage to squeeze your adult cock inside her and she cries out with both pleasure and pain as you stretch her. She explains that your daughter is an anal slut but she's never tried it before. She talks about using your daughter's arse while you use hers, before filthily asking if you'd line her and your own daughter up and fuck both of their arses one by one, like the alpha man you are. It's all too much and you cum again, this time deep inside her bowels. She cums with you and you both lie exhausted; she's not a lesbian any more... and she finally admits it.
duration 36:04
Sex Ed From Big Sis video from Fiona Dagger
Sex Ed From Big Sis 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: Your big sis is a popular girl at your school, and tries to look out for you as much as she can! She tells you she's concerned because there's this rumour going around at school that you're still a virgin, which would obviously be super embarrasing! You sadly admit to your sister that it's true, and confess that you just have huge anxiety about anything sexual - to the point where you've only ever tried masturbating a couple of times! Your sister is shocked but assures you not to worry, she's going to help out. She kindly offers to teach you a few things and help you feel less freaked out, then she can use her status at school to find you a cute girlfriend. You admit that you've never even watched porn, and have never seen breasts (other than your mom's, of course!) Your sis pulls down her top to show you hers, patiently waiting for you to get over your nerves, and encouraging you to touch and squeeze them. She then asks you to get out your cock, and though you're very nervous, once you do show it to her she tells you it's a lovely cock and you should be very happy with it! She gets you to show her how you would stroke it, taking over after a moment and showing you a better way to touch it. She tells you that one of the things you'll probably end up doing with a girl is oral stuff, and offers to demonstrate. She slowly and gently begins sucking your cock, giggling when she can see how much you like it. After a few minutes she suggests you try returning the favour on her, and teaches you how to eat pussy! You surprise her here by how quickly you pick it up, and she begins squirming and gasping before stopping you and saying you're doing great! She suggests that you might as well go all the way, it's no big deal - even though it's technically 'the i word', it's only practice so it doesn't count really. You nervously enter your sister but soon get into it, starting to pound her hard until her pussy creams! She compliments you on how good you're doing and says that she didn't expect this to happen on your first time, but you're about to make her cum! You cum with her and fill her pussy with spunk, then shyly ask her if she wouldn't mind giving you a few more lessons... TAGS: british, english, redhead, ginger, tattooed, tattoos, solo female, roleplay, dirty talk, posh accent, pov, taboo, family affairs, siblings, bro sis, brother sister, fantasy, sex ed, education, lesson, sweet, loving, teasing, dildo fucking, dildo sucking
duration 20:33
Aunt Takes Your Virginity video from Fiona Dagger
Aunt Takes Your Virginity by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) You've gone to stay with your aunt for a couple of weeks, and you're getting the sense that things are going to be very different from when you're at home! You've always known your aunt was much more relaxed than her sister, your mother, but you're beginning to realise just how far that goes! As your aunt is welcoming you to her home and helping you settle in, you find it very distracting how she's just wearing a loosely fastened silk robe which seems constantly on the verge of falling open and exposing something! Your aunt fusses over you and tells you that she wants to make you feel as at home as possible while you're staying with her, and confesses to you that she knows she has some unsual and rather bohemian habits, but that she hopes you'll embrace her style of living. She tells you how she prefers to be comfortable in the house and so only wears silk robes or other lounge wear, and she insists that you take your uncomfortable jeans off so you can stretch out more! You shyly take off your jeans and struggle to stop yourself staring as your aunt's robe falls open even further. She notices you blushing and staring, and tells you not to be embarrassed! She pulls open her robe so one breast is exposed, encouraging you to look at it and insisting that you shouldn't feel awkward at all. She tells you how much she disapproves of your mother's strict style of raising you, with all the rules about no sex or masturbation. Your aunt tells you that if she were your mother she'd be raising you very differently indeed! She suggests that you treat your stay with her as a vacation from your mother's strict rules, and pulls her robe open even further so you can see her naked body exposed. She's pleased to see that you're growing hard, and insists that you drop your boxers and show her your erection! She begins admiring and complimenting it, telling you what a handsome young man you've turned out to be, and insisting on helping you relax. She starts slowly sucking your cock, teasing you lovingly with her tongue and showing off her expertise. She asks if anyone has ever done this for you before, and you confess that it's your first time! Your aunt is amazed; she knew your mother was strict but she was expecting that you'd still managed to sneak off and see girls sometimes, but you sadly tell her that no, you're still a virgin! Your aunt tells you that at your age that just won't do at all, but not to worry, she's here to help! She lays back and guides you gently inside of her, asking you how it feels and telling you that you're a real man now! You slowly begin fucking her as she encourages you, telling you how good looking you are and how you're going to be so popular with the ladies, once she's got you up to speed and taught you about all the things you've been missing out on! Soon you can't hold it back any longer, but your aunt gently encourages you to relax and cum inside her, saying that you've done amazing for your first time, and that you have a whole 2 weeks to get lots more practice with her! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, mom, mommy, mom son, aunt, aunty, auntie, nephew, milf, virginity taking, blowjob, missionary, sex lessons, sex lesson
duration 8:45
First Time With Your Friend's Horny Older Sister video from InfinityWhore
First Time With Your Friend's Horny Older Sister by InfinityWhore [This was a custom request] You're alone in the room that your best friend has provided you while you stay round his house. Your friend is upstairs finishing some homework while his parents make you all dinner. That's when his older sister walks in. She's acting strangely and you're all alone. You've always fancied her you've noticed your cock randomly getting hard when she's around recently. This time is no different - and she notices. She's asks if you like her but then begins to hesitate due to the fact that you're her brother's friend and you're so much younger than her. But she admits that she wants it too. She begins to flash her panties and asks if you've ever wondered what a girl's pussy would feel like around your cock. She wants to show you. She jumps onto your boner and slides her panties aside, grinding her already wet pussy up and down your cock (which feels incredible). She wraps her panties around your hard member and teases you, asking if it feels good and if you want to put it inside her properly. You can only nod. She slides down onto your hard cock and feels so warm around you. You're lucky that you don't cum there and then, but you want to see this out. It's your very first time after all with your friend's super hot older sister. She rides you, encouraging you and telling you're that you're being a good little boy for her. She refers often to your age and the fact that this is your first time experiencing real pleasure, because of her. Really, she's just using you, she says and she praises you often for letting her do so. This doesn't feel like being used to you. You're loving it. She makes you promise to be quiet when you cum as the rest of her family, including your best friend, are just upstairs. She's adamant that this stays between you two as it could get her in a lot of trouble. But her praise and encouragement for your cum are all getting too much. She cums around you and it doesn't take long for you to join her, listening to her scream for your cum - calling you a good little boy over and over again. You cum inside a woman for the first time ever... and she jumps off, immediately adjusting her outfit and reminding you that this stays a secret.
duration 17:52
The Penectomy Treatment Its For Your Own Good video from Lacey Royce
The Penectomy Treatment Its For Your Own Good by Lacey Royce After years of unsuccessfully trying to lose your virginity, you’ve decided to seek professional help. No… not that kind of help. Medical help. You’ve decided to visit a local clinic where you meet Dr. Lacey. She explains to you that her clinic offers an alternative form of therapy for virgins, or as some may say… incels. After taking some vital signs Dr. Lacey explains to you that the dramatic increase in virgins, incels, or sexually impotent men is due to a genetic phenomenon. While nature is taking its course, people like yourself, are facing extreme difficulty navigating life because they’re fixated on achieving sexual goals that the rest of us already know… are never going to happen. So how can she help you? How can she relieve the symptoms that you’re experiencing? How can she make you feel better? It’s called a penectomy. And in order to… ummm… ya know… You have to be erect first. Lucky for you, Dr. Lacey likes to provide a natural solution to get her patients very erect. That natural solution are her big, soft, natural breasts. And she’s going to show them to you, an incel virgin who will never be able to experience sexual pleasure with a woman… for the first time… breasts in real life! Then… at the moment of peak erection, Dr. Lacey uses her removal tool to remove your cock. It will make an excellent specimen and you will heal up in a few days. You may feel a little shocked and confused right now, but this is in your best medical interests. Your cock was getting in the way of you living your best life.
duration 11:53
Young and Curious video from Kat Danz
Young and Curious by Kat Danz When you're young, you're full of curiosity. And being alone in your classmate's bedroom with her is the perfect setup for sexual exploration! Even though she's 18, she hasn't had sex yet. The thought still scares her.... But you can see the way she keeps eyeing your boner. She's curious. She offers to stroke it and play with it. You know she's never touched a penis before, but her inexperienced hand feels even better. She starts getting adventurous and sucks it, gives you a footjob, all while telling you how good it feels to please a big cock like yours. It doesn't take long before she's asking for more. She's still not ready for sex, though. SO she lets your rub your cock right over her pussy lips. She's wet and horny, but she insists on finishing you another way. She's seen you staring at her petite tits this whole time. So you love the idea of her cute tits rubbing around your cock. You hump her chest until you can't take the sight of her naked tits bouncing while you fuck them, and you need to cum. She strokes your dick on her knees until you finally unload all your semen onto her face, dripping down her chest, and getting her hair messy with cum. She's shocked that a man can cum so much! But also eager to learn even more next time! **INCLUDES: students roleplay / handjob POV / blowjob POV / footjob POV / virgins exploring / cock rubbing on pussy / titjob pov / multiple cumshots on face and chest / wet and messy / 18+ / upskirt / small tits
duration 28:46
Daughter's Christmas Request video from Fiona Dagger
Daughter's Christmas Request by Fiona Dagger This year for Christmas it's just you and your daughter Fiona, since your wife moved out several months ago! On Christmas morning your daughter comforts you and tells you how happy she is to be spending this quality time with you, reassuring you that she feels so grateful to be able to hang out with her dad. She brings up how she told you that she didn't really want any presents this year, and admits that she's changed her mind, and that there is actually something she'd like... She talks about how shy and inexperienced she is, and how it's unusual for someone her age to not be dating yet. She explains to you that for a while she thought that maybe she just wasnt interested in sexual stuff, but recently she's realised that she definitely does have these desires, she's just too nervous to pursue them with anyone... The only person she's really comfortable with is you. She says she knows that this is kind of a crazy ask, but for christmas this year she'd really love it if you would help her lose her virginity. She tells you how safe she feels with you, and insists that there's nobody else she could imagine doing it with for her first time. You're taken aback and ask her if she's sure, but she insists that she's been thinking about it over and over for months, and she really wants it to be you. You take a little convincing but eventually agree, and the two of you begin shyly and gently kissing. You suggest that your daughter remove her christmas sweater, and she takes it off to reveal the lacy lingerie she purchased for this occasion. She shows off her body, asking if you like it, and you tell her how good she looks. You can see that she's growing more and more comfortable and turned on, and as she strips out of her lingerie she asks you to get naked too. Once she sees your erection she can't look away, and asks to touch it! She gently strokes it before asking if she can try using her mouth, and you let her explore all over your cock with her tongue. You encourage her and tell her how good she's doing, and watch as she gets more and more carried away. After a while she's doing so good that you have to quickly stop her, so you don't blow your load too early! You offer to return the favour and she nervously lays back to let you warm up her pussy with your mouth. She grows wetter and wetter as you lick her, then you suggest to her that she should be ready to take your cock now. You ask again if she's sure she wants to do this, and she insists she is, practically begging you to put your cock in her. You fuck her slowly at first as she gets used to it, then gradually speed up until you're pounding her tight little pussy fast and hard! You push back her legs, her christmas sock covered feet waving in the air as you fuck her, and keep pounding as she tells you she loves you and thanks you for helping her out and taking her virginity! The two of you cum together, with you flooding your daughter's pussy with your seed, and she asks if you'd be willing to give her some more practice in future! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, taboo, wincest, family fun, family affairs, daddy daughter, dad, father, christmas, holiday, cute, romantic, sweet, loving, socks, dildo sucking, blowjob, dildo fucking, missionary, creampie, pussy eating, pussy licking, pov, virgin, virginity, inexperienced, shy
duration 12:00
Friend's Mom Takes Your Virginity video from Fiona Dagger
Friend's Mom Takes Your Virginity by Fiona Dagger *Watch the first 3 minutes of this video, and all my other videos, by subscribing to my Club for as little as $2 a month!* (This was originally filmed as a custom video and the name Sam is used once) You've gone round to your friend's house to hang out and watch tv, but your friend started a wrestling match with you and then got way too aggressive with it and punched you in the balls! His mom heard the commotion and has come to check on you, after yelling at her son and sending him to his bedroom! She apologises for his behaviour and asks if you're okay, and you can't hide how much pain you're in. Your friend's mother says she'll call your mom in a moment but first she should maybe just have a look and make sure you're not seriously hurt. She pulls down your jeans and starts examining your cock and balls, touching you gently and talking soothingly to you. She's impressed by how big you are, and begins softly touching and stroking your cock, asking if it hurts. She says she has an idea for how she can make you feel a little better, and how she can say sorry for her awful son's behaviour - have you ever had sex before?? You tell her you haven't, and she asks if you'd like to try it with her now - she promises she'll guide you through it and that it will feel very nice, and that you'll be all better afterwards! You shyly agree and she quickly turns around and pulls down her leggings, bending over and guiding you inside her. She takes charge and encourages you just to relax, as she moves back and forth on your cock. She keeps talking soothingly to you as your cock slides in and out of her pussy, and after a couple of minutes you can't help but release a big load inside her! She pulls up her leggings again and tells you to be sure to not tell anyone about this, then goes to call your mom! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, taboo, virgin, milf, soothing, gentle, dildo fucking
duration 25:07
Deflower Your Daughter Daddy video from Katherine Pine
Deflower Your Daughter Daddy by Katherine Pine You asked a long long time ago for your daughter to remain a virgin. She approaches you and tells you she is ready, she wants to have sex for the first time. You aren’t sure about this, but she says she wants you to be the one to deflower her. You are apprehensive, but she begins stripping. This is so wrong, and you are still unsure. She spreads her virgin tight pink pussy open and begs you to take it. Your cock grows harder every time she calls you daddy. She isn’t going to take no for an answer, you definitely taught your little girl to be persistent. She is on her knees looking up at you, your huge cock looks so delicious to her. She tries a handjob first, before she gently kisses. She attempts to take your full length down her throat. She begs and pleads for you to slide it in her tight virgin hole. She wants it to be yours daddy. You rub your cock up and down on her clit, she begs and begs. She says please daddy over and over again, you can tell how bad she wants this. You give in, the temptation is too much. You fuck her in missionary, her wet pussy feels so good. Her tits bounce up and down and she can’t stop moaning. She rides you and has a big orgasm on your cock. You fill your daughter's pussy up with cum as she begs for it. She keeps riding to milk all of the cum out. TLDR: Daddy / Daughter roleplay. POV BJ with dildo, POV missionary with dildo, and POV Virtual sex cowgirl riding. Implied creampie. EXTREME TABOO!! This video was originally created as a custom video. I love making customs, I would be happy to bring your particular fantasy to life. Please feel free to contact me so I can create a special video for you! TAGS for this video: brunette, curvy, big tits, big ass, bouncing tits, bouncing ass, bouncing boobs, big boobs, huge tits, giant tits, body piercings, piercings, nipple piercings, tongue piercings, pussy, dirty talk, dirty talking, cute talk, Katherine Pine, katherine pine, kat pine, katherinepine19, katherineepine, body piercings, gothic, slutty, slut, whore, titty play, tits, ass, missionary, POV, point of view, Virtual sex, riding, cowgirl, blow job, BJ, HJ, handjob, daddy, daughter, dad, taboo, step dad, step daughter, family, fam,
duration 24:54
Uncle Takes My Virginity video from Fiona Dagger
Uncle Takes My Virginity by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) Your niece has come round to see you, and says she feels like you've been avoiding her recently! She says that the two of you used to be so close when she was younger, but she worries that now she's grown up you feel like you shouldn't be around her so much. She apologises if you feel weird, and says you might have picked up on the fact that she's had a crush on you for so long... She says she knows it's awkward as her father is your brother, but she can't help it! You're the only man she's ever been interested in! She tells you how she's kept herself pure so far, always hoping that you would be the one to take her virginity... And that if you don't do it, she just can't see herself giving it up to anyone else! You're very conflicted but she gradually wins you over by promising that it can just be a one time thing if you want it to be, but she just really wants to be with you, at least once... She promises that nobody will ever find out, so you finally agree! You can see she's nervous, so you gently take charge, kissing and caressing her and then laying her back and eating her pussy! She's amazed by how good your tongue feels and you soon bring her to orgasm, before slowly sliding your cock inside her as she gasps and moans! She tells you how good it feels and how she's dreamed of this moment so many times, as you start fucking her sensually. You pick up speed until she's cumming once more, then you pull out and tell her that just to be safe, you shouldn't come inside her - and instead you ask her if she's ever given a blowjob? Your niece admits she hasn't, but if you tell her what to do she's happy to try! You guide her through sucking your cock, and she picks it up quickly, admitting to you how much she's enjoying it! She gets more confident and begins quickly and sloppily going down on you, until you finally release your load down her throat! She swallows it and thanks you for making her into a woman, and asks if you'd want to do this again sometime...? TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, dildo, taboo, daddy daughter, uncle niece, virgin, shy, virginity, blowjob, pussy eating, missionary, sex lesson, sex lessons
duration 14:34
SUCCUBUS TAKES YOUR VIRGINITY video from Ellie Idol
SUCCUBUS TAKES YOUR VIRGINITY by Ellie Idol An unfamiliar voice speaks to you, waking you from your slumber. A woman before you claims to know everything about you, including that you're a virgin. She starts to ramble on about your energy and feeding on it to avoid... hunters? What is this loony lady talking about? She claims she's a succubus (yeah right), and that she's not the type to unalive her targets. She claims most succubi feed off sexual energy and that virgins taste the best! So much potential. First, she needs to work you up, though that isn't hard at all to do. You're erect and oh-so-horny at this strange half naked woman in your bedroom (even if she is a little cuckoo). Build up that desire for her, ache to feel her body on yours. There's no resisting her, not that you want to... With her tits in your face and her straddling your lap, you feel an overwhelming urge to rip off her panties and stick your dick inside her. You want to lose your virginity so bad, your skin is practically burning with lust. She wants you to BEG her to slide her panties off and you're practically tripping over your words as you do. She stands tall above you with a sexy sway... you're closer now to losing that v-card. How much longer will she make you wait?! You need it NOW, NOW, NOW. After she feels you're at peak horniness, she mounts you and slips you inside her tight wet cunt. You can't believe you're fucking this wild woman who claims to be a succubus but you're here for it. She slips up and down your shaft, gripping you tight, kissing you deeply. She wants you to hold back for as long as a first timer can, begging you for a minute more! Then, when she feels she'd had her share, she orders you to cum deep inside her. You can't get a succubus pregnant she claims so give her all you got and don't hold back!! Post-climax, she hops off while getting dressed and claims the hunters are still after her. She has the energy she needs so she must go and continue evading her capture. Not like the hunters have a chance, she's just toying with them for fun. She claims she'll be back next week so you can try out some other sexual moves with her. And as fast as she came, she's off!! Will you see her again? You sure hope so...
duration 7:25
Barely Legal and Ready To Learn! video from Krissi
Barely Legal and Ready To Learn! by Krissi ⋆ ˚。⋆୨♡ Description ♡୧⋆ ˚。⋆ Hi mister! I just turned 18, and I am so ready to explore my body and learn about sex! In this clip, I'm asking you, an older and more experienced man to show me all about intimacy. I beg you to be the one to teach me what it's like to feel a mans hands on my body, to feel the sensation of being intimate with somebody. My body is so untouched, unused. I'm barely legal, and just really wanting to have sex! I want to do it right though. I know I want it to be YOU! Will you teach me? Please? I know I'm not experienced but I know my own body at least! I've already mastered touching myself and making myself feel amazing but now I want to feel amazing with you! I make sure to let you know that I want to please you too. I know from seeing the internet that sex isn't just about me, but it's about my partner as well! I already know how to make myself feel good, but it's time to make both of us feel REALLY GOOD! Let's explore my barely legal teen body together! ⋆ ˚。⋆୨♡ Themes // Details // Notes ♡୧⋆ ˚。⋆ I can't believe I was commissioned such a fun video! There's no names or anything that make this video personal, but if you want one like this of your very own, submit that custom form! I'd LOVE to make you something special too!! This video features and mentions the following themes: BARELY LEGAL ♡ TEEN ♡ VIRGIN ♡ MASTURBATION ♡ YOUNG ♡ OLDER MAN ♡ SKINNY ♡ AGE GAP ♡ PETITE ♡ ROLEPLAY ♡ TABOO ♡ FETISH ♡ PIGTAILS ♡ COSPLAY ♡ COSTUME ♡ KRISSI POOKIE
duration 17:51
Nun Tricks Altar Boy into Fucking video from InfinityWhore
Nun Tricks Altar Boy into Fucking by InfinityWhore [This was a custom request] You're an altar boy in a Christian community and you love your religion so you're a little concerned when something starts happening to you which does not feel Holy. In fact, it feels like a sin. You've started feeling your genitals getting hard whenever you see an attractive woman - so - panicked, you visit the head Nun in your Church to ask for advice. She knows exactly what is happening to you, of course, but she uses your panic to blackmail you. She tells you that your hard cock is the work of the Devil and that you must not tell anyone else because you'll be shunned from the Christian community for having the Devil inside you. You are horrified and want to do whatever it takes to get this unholy being out of you. She tells you about the white liquid inside you and that it's where the Devil resides. She knows how to get it out of you so you agree to let her help. As you're so scared, the 'Devil' won't show himself so the attractive Nun beings to ride up her dress to show off sheer hold ups and stockings - as well as her perfect breasts. She even spanks her bare arse with her crucifix - telling you she's doing it to keep the Devil away from her soul. Right on cue, your cock gets hard. Her mouth is around your length before you know whats happening and she works your cock with an expertise that makes you feel so amazing. She tells you the pleasure that you're feeling is the Devil's work and that you must give into it for now in order to release the white liquid that he is possessing. She makes you promise that you'll never tell anyone else and only come to her with this problem in the future. She is the only one who knows how to free you. Feeling you're close, she tells you about one more trick that she has up her sleeve to release the evil from within you. She slides down onto your cock, pussy soaking wet (she tells you the Devil has started to affect her body too and that putting your bodies together will confuse him). Nothing has ever felt as good as this but, on her word, you believe that it's just the Devil putting carnal thoughts in your head. As she rides you, she reminds you that you're a disgusting Christian boy for being so weak and letting the Devil inside you. She asks how your parents would feel, or the other Altar boys? You let the pleasure take over you and release the liquid inside her body while she moans and writhes with her own pleasure. She tells you that her body is so loyal to God that she can swallow and destroy the evil inside her, unlike you. You may have to come and visit her a few times a week now to make sure the Devil never takes over your weak little body again. You belong to her.
duration 41:39
If I Wasn't Your Mother (Step) video from PaintedRose
If I Wasn't Your Mother (Step) by PaintedRose Your Step-Mom gets home from the office and takes you out to dinner and dessert and then after seeing the waitress flirt with you, she asks if you like girls. Mom doesn't really have a filter and she's very sexual around you with her body and dress and you often have to look away because of hiding erections. Tonight she tells you that if she wasn't your Mother that she'd have and devour you - she clarifies that you're handsome and sexy which leaves you with a fat hard on and a dirty dream about Mommy. Mommy is also thinking about you as she rubs her dommy cougar pussy thinking about your delicious cub meat which she admits is completely fucked up but laughs about how kinky she is. The next day, you're quiet so Mommy clears the air about erections being normal and that her body is reacting to you too - she lets you watch her change and get topless. One thing leads to another and well.. a handjob and her tasting your first cum off of her fingers. She wants all of you and she won't share - you're her precious little pervert and she's claiming your innocent young cock. She undresses sensually and literally - fucks your brains out like she promised. This film contains Stem-Mom Love-Lust First Time POV Sex and Handjob w cum spray, 2 blowjobs - 1 with facial, Missionary, cowgirl, doggy style, ass twerk, Underboob, Dirty Talk, dripping creampie in this slow burn fucked up pervy taboo film. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!
duration 16:17
I owe step-Daddy's Boss a HUGE FAVOR video from Krissi
I owe step-Daddy's Boss a HUGE FAVOR by Krissi Description I need a huge favor from my (step) daddy's boss (that's YOU!) You see, I'm still a total virgin, because my dad is always around. He never leaves me alone, I don't have any privacy! I get your number, and call you, innocently asking for a favor. Although, I didn't realize the implications of saying "I'll do anything!" You show up almost immediately. I let you know you missed Daddy, he just left! He's on that work trip we talked about. You let me know you're not here for my dad. You're here to take what I owe you! "S-sure, you can come in!" You come into my teen room and whip your cock out. I remind you that I am still a virgin, so I've never seen one before. I'm absolutely mesmerized. I ask you so nicely if I can touch it, and one thing leads to another, your big cock is in my tiny mouth! It's delicious! But, I want you to teach me about sex while you're here. Your cock is already out, you might as well! So you instruct me to take my clothes off and get ready. You fuck me doggy, then have me hop on top! It's absolutely amazing. But, you surprise me by asking to cum on my pretty little face. Of course you're going to cum on my face! You jizz all over my face, and I get so excited I just have to savor the moment. I start taking selfies, as you're trying to leave. I only notice right then that I was so caught up in the moment that it was YOUR phone I was using! Holy heck! You can't tell anybody, okay? Promise? But PLEASE come back again tomorrow so we can do this over again!! Disclaimer Background music and animated logo are not in the final purchased copy of this video
duration 20:23
Bratty Sis Blackmails You video from Fiona Dagger
Bratty Sis Blackmails You 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 generally a bit 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: Your little sister comes into your room looking rather upset, and wanting to hang out. You ask if she's still going out with her boyfriend tonight, and she tells you no, he broke up with her just now. You begin to comfort her but she tells you she's not that bummed about it, she wasn't really into him. Mostly she's just annoyed that they didn't last long enough to do anything, you know, sexually! She complains to you that she keeps dating these guys who break up with her after a few days or a couple of weeks, and she's stuck being a virgin! She's worried she's never going to lose her virginity, and the longer she waits the more stressed out and in her head she gets about it! She laments to you her lack of any male friends, saying if only she had a male best friend, he could just help her out one time, and then it would be less of an intimidating thing for her. You agree it's a shame that she only has female friends. Your sister then gets a sly look on her face, and to your horror suggests that YOU help her! You immediately try to shut her down, but she begs you to help her, saying it would only be one time, and you're supposed to want to look after her!! You tell her no, no way, she's your little sister, it would be totally wrong. It would be the i word! Besides, you have a girlfriend anyway, who you love. Your sister looks even more sly at the mention of your girlfriend, and horrifies you even more by pointedly asking what your girlfriend would think about all the messaging, and sexting, and exchanging of nudes you've been doing with girls online... You're furious at your sister for snooping and for using it against you like this, but she's got you trapped. You eventually, reluctantly, agree to help her this one time, on the condition that nobody ever finds out, and your girlfriend stays in the dark about your online activities. Your sister gleefully strips down, having a moment of doubt when she sees the size of your cock and wonders whether it will be too big for her first time; but she's extremely detirmined to lose her virginity, so she lays down and beckons you closer. You position your cock at her entrance but freak out a bit before you can put it in - this is your own sister! She's having none of it and reminds you of the awkward positition you're in, bossily demanding that you hurry up and take her virginity. You take a deep breath and slide your cock into her pussy, feeling the mix of shock and pleasure as you penetrate your sister. You try to tell her to shut up and stop talking so much, so you can concentrate (and try not to think about who it is you're fucking), but she chats away constantly, and in spite of this you're surprised to find yourself getting into it. You feel extremely guilty as you begin to enjoy yourself, but you can't deny how very intense it feels to be inside your own sister! Your sister cums hard on your cock, and you find yourself admitting to her that you didn't finish yet, but... Your sister immediately tells you to just get on with it and cum inside her, it's no big deal! You don't need any more encouragement and begin fucking her hard again, quickly flooding her pussy with cum as you wrestle with how wrong this all is! You know you shouldn't, but as you pull out you tell your sister that if she wants any more experience, you'd be happy to help out, after all... TAGS: british, english, ginger, redhead, tattoos, tattooed, roleplay, dirty talk, solo female, posh accent, taboo, bro sis, bro/sis, brother sister, family affairs, pov, dildo fucking
duration 12:24
Convincing Anal Virgin Maid into Ass To Mouth video from InfinityWhore
Convincing Anal Virgin Maid into Ass To Mouth by InfinityWhore This little French maid works for a very influential and affluent businessman, so surely he could help her out!? Otherwise, she'll be kicked out of her apartment... so she waits for him to arrive at the end of her shift and timidly explains the situation. He's happy to help, only he tells her she must do something for him first - make him cum. Realizing it's the only way out of her predicament, she agrees to suck his cock and maybe even let him fuck her pussy. She subordinately drops to her knees and works expertly on his cock, even letting him get carried away and fuck her face while she gags and drools, but then he asks for something else. He wants to fuck her arse. She explains that she's never had anal sex before and is scared but he insists - telling her it's the only way. So hesitantly, she bends over the sofa... It takes a while for her to adjust to taking his cock but eventually his thick length slides inside her tight little arsehole with a pop. She whines and moans about how painful it feels but he doesn't stop - fucking her harder until she opens up for him. Eventually, it begins to feel good and she shudders to orgasm with his cock inside her arse. Realizing he's hired her for cleaning - he decides to make her clean her arse from his cock with her mouth - until he can't handle the feeling of her lips around him anymore and pulls out of her throat - plastering her face with a huge cumshot. Glazed with his cum - she hopefully smiles up at him while he tells her she's definitely earned what she wanted.
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