Fiona Dagger

Fiona Dagger – Losing Your Virginity To Mommy

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Fiona Dagger - Losing Your Virginity To Mommy

Fiona Dagger – Losing Your Virginity To Mommy

Your mother is very concerned about how unhappy you’ve been recently, and after you had confessed to her that still being a virgin was stressing you out so much that you were considering seeing an escort to get it over with – well, she’s decided that just won’t do! She sits you down and tells you that you’re such a handsome and lovely young man, and that she knows if you just give it some more time then the right girl will come along for you – but if you really can’t stand to wait any longer, then you should just use her, rather than going and spending your money on a sexworker! She promises that she’s serious about the offer, and tells you she just wants to help you feel better, and that if this will help raise your confidence a bit then she’s happy to be your first time. You’re very grateful to your mother and agree immediately, dropping your trousers and surprising your mother with how quickly you got hard! She strips naked and lays back on the bed, talking soothingly to you about what’s going to happen, and promising not to judge you if it’s all over rather quickly! You climb on top of your mother and nervously slide your cock inside her, taking it slow at first but quickly relaxing once you realize it’s not as difficult or scary as you thought! In fact you seem to be something of a natural, picking up speed until you’re pounding your mother hard and fast while she moans with surprised pleasure underneath you! You even manage to last long enough to make her cum, which she praises you for and tells you how great that is for your first time – then tells you to go ahead and ejaculate inside her, saying that you’ve done so good and she’s so proud! You let go and unleash your load into your mother’s pussy as she keeps praising you, then she even offers to do this again sometime so you can have even more practice, since she enjoyed it so much!

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Fiona Dagger – Happy New Year Brother

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Fiona Dagger - Happy New Year Brother

Fiona Dagger – Happy New Year Brother

It’s New Years Eve, and while you’re settling in for a quiet night on the couch, your sister is getting ready to go out and party! She does her best to convince you to join her and her friends, but you tell her you’d rather stay in and chill, but that she should go have fun. Unfortunately, your sister’s friends all bail on her when she’s in the taxi, and she returns home feeling dejected! You commiserate with her over her flakey friends, and tell her not to worry – the two of you can celebrate together. Your sister cheers up and grabs a bottle of bubbly from your parents’ stash, saying it’s a good thing that they’re away tonight, so the two of you can have a bit of a party without mum and dad watching! The two of you get gradually sillier and gigglier as you enjoy the bubbly, talking about how you’re both chronically single, and how maybe next year you’ll finally get lucky… As midnight approaches, your sister jokes about how you’ll have to kiss each other, since kissing someone at new years seems to be a bit of a rule! As you both countdown to 2025, your sister leans in and plants one on you, laughing at your shocked face. A strange moment passes between you as you stare at each other, then suddenly you’re kissing again! You can’t believe what’s happening as the two of you breathlessly make out, and after a moment you both pull away, half laughing and half apologising to each other. You try to change the subject, toasting each other and the new year, but the tension in the air is too much now, and it’s not long before you’re drawn back together – this time giving in and passionately kissing each other as you run your hands all over your sister’s body. The two of you murmur to each other in between kisses, questioning if this is a good idea but not wanting to stop – and soon you find yourself pulling off your sister’s dress and admiring her body in her underwear as she sits shyly before you. You push her back onto the couch, laying on top of her and kissing her intensely, before pulling up her bra and moving her panties to the side… Your stare into your sister’s eyes, watching her expression change as you slide your fingers between her slit, feeling how soaking wet she is… You push your fingers inside her as you kiss her, slowly pumping them in and out as she moans and tells you that it feels so wrong – but begging you not to stop! You pull her up onto the couch and help her remove her panties, before bending down to apply your tongue between her legs… Your sister gasps and writhes in pleasure, taking your unfinished glass of bubbly and pouring it over her pussy for you to lap up with your tongue… You tell her to turn around, and she bends over on the couch to allow you to continue eating her pussy from behind – as she tells you she had no idea her brother was such a freak! You eat her out until she cums, twitching and moaning, and as she’s still bent over she groans that you should just go ahead and do it – she’s desperate to feel your cock inside her… You stand up and slide your cock into her tight, gripping hole, as she tells you how crazily wrong and dirty it feels to have her own brother’s cock stretching her out… You start fucking her hard, feeling her round ass slap against you, until she stops you – but only because she wants to suck your dick! She kneels down and licks all her juices off your cock, telling you that this isn’t how she thought the night was going to go, but she’s not complaining… She sensually sucks you off until you’re almost ready to explode, then begs for you to fuck her once more! You lay her back on the couch and plough her pussy hard until you cum explosively together, flooding your sister’s pussy with spunk… Afterwards, the two of you snuggle up on the couch under a blanket, stealing some more of mum and dad’s bubbly and telling each other how this is the craziest new years you’ve ever had, and that maybe you can do it again sometime, when mum and dad are next out of the house…

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Fiona Dagger – Hiring Your Escort Daughter

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Fiona Dagger - Hiring Your Escort Daughter

Fiona Dagger – Hiring Your Escort Daughter

Your daughter is getting ready for an appointment with a new client, and as she sensuously gets dressed and does her makeup she reminisces about her estranged father and how she looks for similar qualities in all the men she dates. She thinks about how she misses him, and how much she resents her mother for pushing you away from her and saying that your relationship was inappropriate. Once she’s ready, she makes her way to the hotel, and is stunned into silence when you open the door. At first she assumes she must have got the wrong room, and tries to leave, feeling embarrassed about her attire and what you must think, but you calm her down and invite her into the room to talk. Once inside, you explain to her that you hadn’t realised it was your daughter you were booking – you just thought it was someone who looked a lot like her, it’s been years since you two have seen each other, after all! This reassures her a little, but she questions you about why you would hire someone who looked like her – isn’t that a bit strange? You admit to her that you tend to favour girls who look like her, and that you’ve always found her beautiful. She begins to relax and warm up, and tentatively asks you more questions, trying to seek out your true feelings. She mentions how her mother was always suspicious of your intentions towards her, and when you admit that perhaps there was some truth in that, she seems relieved and excited; confessing to you that she always felt drawn towards you, probably more so than a daughter should. As you catch up she moves closer and closer to you, until you’re both confessing your desire for each other. She shyly suggests that since you hired her to do a job, she could go ahead and do so… If you’d still be okay with that. She tells you how much she wants you, and how she’s felt guilty about it for years, but she doesn’t want to feel bad about it any more. She peels off her dress and kneels down to show you how much she’s missed you, worshipping your cock and asking if she’s better than her mother, and than the other girls you’ve hired. She then begs to be able to sit on your face, confessing that it’s been a fantasy for years, and climbs atop you so that you can lick her soaking wet pussy. Soon she can’t hold back any more and simply must have you inside her, and she rides your cock in cowgirl, telling you how much she’s missed you and how amazing it feels to have you inside her at last. You then bend her over the bed and pound her pussy, and she gets wilder and wilder as you do so, begging you to use her like a slut and do whatever you want to her – and after you’ve made her cum hard, you surprise her by sliding your cock into her asshole without warning! She loves it and tells you to use her holes however you’d like, only asking that she can look into your face as you cum, so you flip her onto her back and keep pounding her tight ass. As you get close she admits that she’s not on birth control but she doesn’t care, she’s desperate to feel you filling her pussy with cum, so you pull out of her ass and slide back into her wet pussy, pounding until both of you cum together!

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Fiona Dagger – Mom Sucks Your Cock At A Party

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Fiona Dagger - Mom Sucks Your Cock At A Party

Fiona Dagger – Mom Sucks Your Cock At A Party

Your mom is hosting a party and has asked you to stay upstairs and out of the way for a few hours, but you keep annoying her and demanding her attention!
She comes up to your room to ask you to stop calling for her, and begs you for a few hours of peace! You tell you’re mom that you’re horny and you need her to take care of it, and your mother is amazed, as she made sure to drain you 3 times before the party started!
At first she asks if you would do her a favour and just take care of it yourself this one time, but you keep complaining and eventually she feels your swollen balls and tells you she’ll take care of it. She warns you that it will have to be very quick and quiet, and starts taking down your jeans to stroke your hard cock for you. You ask if she can take her top off and she sighs but quickly pulls up her top and bra so you can watch her tits while she jacks you off.
After a couple of minutes you whine and beg for her to use her mouth on you instead, and she huffs but agrees since it will probably make you cum faster! She kneels down and begin rapidly sucking your cock, encouraging you to try and cum quickly – when suddenly there’s a knock at the door!
Your mom calls out to find out who it is, and when she realises it’s her friend Ashley, she quickly calls her inside and tells her to shut the door behind her! You start to hide but your mom reassures you that it’s fine, Ashley has the same kind of special relationship with her sons, all 4 of them! Your mom absently strokes your cock as she chats with her friend about how much work it is to have sons, and how other people just don’t understand the special kind of love that they need; then your mother asks Ashley to keep the ret of the guests away from the upstairs until she can finish taking care of you!
When Ashley is gone, your mom tells you to hurry up and cum now, and to focus on really getting every last drop out, as she won’t be draining you again until after the party! She passionately sucks and strokes your cock until you release a huge load of cum down her throat, which she struggles to swallow; then she tells you she loves you and she’ll pay you lots of attention after the party, but to please stay quietly up here for a few more hours!!

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Fiona Dagger – Sisters Oral Fixation

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Fiona Dagger - Sisters Oral Fixation

Fiona Dagger – Sisters Oral Fixation

You’re gaming on your PC when you feel something moving by your legs, and spot your annoying little sister crouched under your desk, trying to gain access to your boxers! You ask her what the hell she’s doing and she whines and begs for you to just let her suck your cock, she won’t bother you and she’ll stay quiet so you can keep gaming with your friends! You tell her no and accuse her of being a little slut, but she insists that it’s a real medical issue – mum and dad took her to see a doctor who says she has an oral fixation, so it’s not her fault, she really needs it! You tell her to go find someone else’s cock to suck but she reminds you that she can’t, she’s grounded for exactly that reason – your parents caught her sneaking out and sucking random boys’ cocks, so now she’s not allowed out any more! She begs you to just be a nice brother and let her do it, and besides, it’s not like you won’t enjoy it! You finally give in, reminding her to stay quiet so your friends don’t hear her over your mic, and she gleefully thanks you and takes out your cock! She begins happily licking and sucking it as you try to concentrate on gaming, but she stuggles to contain her noises of enjoyment and you keep having to remind her to keep it down! After a while you warn her that you need to cum, which makes her mad! She tells you that she’s not had nearly enough time sucking your cock yet, and tells you to hold it in! You try to hold off your cum for a few more minutes but then have to tell her that you really can’t hold it anymore; if she keeps sucking it, you’re gonna cum. Your sister is annoyed but you sigh and promise her that you’ll be ready to go again after like half an hour’s rest, which cheers her up slightly! She sucks you fast until you cum down her throat, then insists that she’ll just stay her under the desk playing with your cock until it can cum again!

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Fiona Dagger – Son Needs Help Masturbating

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Fiona Dagger - Son Needs Help Masturbating

Fiona Dagger – Son Needs Help Masturbating

A few weeks ago you had a nasty accident and broke both your arms, and your recovery has been going very slowly… Your sweet mother has been waiting on you hand and foot, checking on you often and getting you whatever you want, but still, you can’t help but get grumpy after weeks of being unable to masturbate! Today you’re feeling extra frustrated and backed up, and your mom can tell something’s wrong. She tries to soothe and calm you, and insists that you tell her what’s on your mind… So you eventually, reluctantly, tell her that you’re fed up because you really need to cum, and you can’t do anything about it… Your mother is a bit taken aback at first but quickly rallies herself and tells you she totally understands, it’s a normal human need, and you must be so frustrated! She worries for a while about what to do, saying you have so many more weeks to go until your casts come off, and it’s not like she would know where to hire an escort for you, even if the family could afford that… You’re getting more and more disheartened until finally she steels herself and offers to help you out herself – just a quick handjob, to give you some relief! You’re surprised and ask her won’t that be weird for both of you, and she says yes she expects it will be rather uncomfortable for the two of you, but that she doesn’t know what else to suggest! You nervously agree and your mother takes a deep breath and starts pulling down your pyjama bottoms, telling you to just relax and close your eyes, and you can imagine that it’s someone else doing this to you… She slowly and nervously starts stroking your cock, barely able to look at it at first, and unable to stop nattering about how weird this is… She keeps telling you not to look at her and to not think about your mother, but then won’t stop talking to you and distracting you from thinking about anyone else! Eventually you give up on closing your eyes and just watch in fascination as your mother’s hand glides up and down your throbbing cock, feeling so wrong but so incredible at the same time! Your mother slowly starts to relax and even compliments you on how lovely and big your cock is, and then catching herself and trying to stop thinking about how nice it is… You begin to suspect that she’s starting to enjoy herself as she gets more and more breathy and begins staring you in the eyes and talking softly to you as she jacks you off, even eventually offering to do this for you every day, so that you feel more comfortable while you’re receovering…. You warn your mother that you’re getting close and she grabs a tissue for you to cum into, encouraging you softly and gasping as she sees you flood the tissue with your huge, backed up load… She then tells you not to feel weird or ashamed about what just happened; it’s her job to look after you and she’s totally happy to come up and help you like this every afternoon, if you want…

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Fiona Dagger – Son Needs Help Masturbating 2

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Fiona Dagger - Son Needs Help Masturbating 2

Fiona Dagger – Son Needs Help Masturbating 2

It’s been a week or so since the prequel, and your mother has been dutifully ‘taking care of you’ every afternoon! Today she comes up as usual to help drain your balls, since both your arms are still in casts, and as she strokes your cock she chats away to you about how nice it is to have this new way of bonding with you, and how at first she found it awkward but now she just thinks it’s so nice to spend this extra time with you, and to help you out! She tells you what a lovely cock you have and says she wishes she could tell all her friends about it, and says how silly it is that society wouldn’t approve! You can see her eyeing up your cock wistfully, and you’re surprised when she shyly suggests you might be getting bored with handjobs… perhaps she could try using her mouth instead? She seems to expect you to say no, that’s too weird, but in fact you jump at the chance and tell your mom to go ahead! She eagerly begins slowly licking and sucking the head of your cock, taking her time and savouring this new experience before taking you deep into her mouth and sucking strongly. The sensations are so much more intense than just her hand, and you gasp and lay back as your mother goes to town on your dick! She seems to really be enjoying herself, and she tells you that when you’re ready to cum you should just go ahead and do it in her mouth, so she can get rid of the mess. It’s not long before you oblige her, and flood her mouth with a massive load of spunk that she dutifully swallows down and licks up every drop off your cock!

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Fiona Dagger-Bro/Sis Anal FuckFest

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Fiona Dagger-Bro/Sis Anal FuckFest

Fiona Dagger-Bro/Sis Anal FuckFest

(This was originally filmed as a custom video and the name Michael is used a couple of times) Your big sister storms into your room, saying that you need to talk about how she just caught you spying on her getting changed. She’s angry with you but you try and get her to understand; you’re really horny and frustrated being stuck indoors during the pandemic, and as she’s the only girl around you’ve developed a bit of an obsession with her. You suggest that maybe it would help you get over your fixation if your sister showed you her body a bit… She reluctantly agrees to this, saying she’ll let you have a look so you can get over her, but that’s it. You can’t keep your hands to yourself though and end up touching her boobs and ass, then pulling out your cock to stroke it in front of your sister. She’s exasperated but then says fine, just have a cum and get it over with. She watches you stroke for a couple of minutes, then asks if it would speed things up if she touched herself too… You masturbate together, each getting more and more turned on and frustrated, until you manage to convince your sister to help you out and use her hands on you. As she strokes you she’s clearly getting very aroused, and soon she ends up straddling you and rubbing her soaking pussy on your hard cock, whilst reminding you that your cock can’t go inside of her… She gets onto her back to let you continue rubbing and slapping your hard cock on her pussy, but then you can’t hold back any more and you suddenly thrust inside of her! She’s shocked but says the line has been crossed now, so you fuck her harder and harder. She asks if you’d like to be the first person in her ass, and of course you agree, so she lets you pound her asshole, stopping you frequently so she can suck your cock and clean her ass off it with her mouth and tongue! She becomes obsessed with making you fuck her ass and then sucking your cock afterwards, making you do it over and over again in different positions until she can’t wait any longer and begs you to cum into her mouth so she can taste your cum!

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Fiona Dagger – Mom’s Sex Test

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Fiona Dagger - Mom's Sex Test Fiona Dagger - Mom's Sex Test

Fiona Dagger – Mom’s Sex Test

Your family is preparing for their monthly sex party, where they host lots of relatives and friends for a big orgy, and you’re annoyed because you’ve never been allowed to go. You pester your mother to allow you to attend the party this evening, complaining that it’s not fair that your sister gets to go – but your mother tells you that your sister has proved she can handle everything that goes on at these parties, and that she’ll be a vaulable asset to the orgy. Your mother just isn’t sure that you’re ready yet! You beg her to reconsider and ask her to test you right now, and she finally agrees. She strips off quickly and drops to her knees to stroke and suck your cock, softly nagging you about keeping up the family reputation and not embarrassing them in front of their friends. She impresses upon you the importance of not cumming too quickly at the party, and warns you off following your sister around the whole night as she’ll be very busy with lots of other men. She lies back and encourages you to slide your cock into her pussy, reminding you to concentrate and not cum too soon, but you surprise her by fucking her hard and long, until she’s telling you how pleased she is with you and that after you drain your balls into her pussy you can come to the party after all, she’s sure you’ll do wonderfully!

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Fiona Dagger – Sharing A Hotel With Sis

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Fiona Dagger - Sharing A Hotel With Sis

Fiona Dagger – Sharing A Hotel With Sis

Your sister was in charge of booking the hotel room for the night, and it seems she fucked up! She swears she asked for a twin room, but they’ve only given you the one bed. It’s fine though, it will be like a cute little slepover like you guys used to have! She asks if you want to hang out or watch a movie or something, but you grumpily tell her you’d rather go straight to bed. Your sister shrugs and starts to get ready for bed, provocatively getting undressed just in your line of sight, and daring you to comment on it. You try not to watch but gradually find yourself staring as she gets changed, before sitting down on the bed in her short little nightdress. She bothers you for a bit and you can’t help but notice how short her dress is! She laughs at you complaining about it, and tells you it’s not like she’s making you look – but you can if you want to! You’re going to be sharing a bed together, so you might as well get comfy with each other, right? She pulls up her skirt to flash her pussy at you and at first you look away, horrified, but you soon find yourself staring at it. You manage to get a hold of yourself and tell your sister that she’s being super weird, and you want to go to bed now. She sighs and huffs but lays down, pushing her ass closer and closer to you on the bed. After a while of wrestling with yourself you just can’t help it, and you reach out to touch her ass and pussy, but quickly get freaked out and pull away. She sits up and demands to know why you stopped; telling you that she wanted you to do it, and she knows you want to as well! You try to protest, telling her it’s wrong to do that stuff with your sibling, but she tells you she doesn’t care. In fact, that’s what makes it so hot. It’s dirty and wrong, and that’s why it feels so good. She takes your hand and puts it back on her pussy, taking your cock out of your pants to stroke it. You can resist less and less as she plays with your hard cock, and when she asks if you want more, you say yes… She begins sucking your cock, giggling and telling you how long she’s been fantasising about this, and how filthy it feels to have her brother’s dick in her mouth… She then rides your cock before you pound her in doggy until she cums hard on your cock, then begs you to cum on her face!

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