https://www.freepornflix.com/categories/age-regression/ Thu, 16 Apr 2026 23:02:27 UTC https://www.freepornflix.com/video/616840/your-step-mommie-new-nanny-diapers-and-jerks-you-off-in-the-back-of-the-car-wmv-720p2/
Click for hd mp4 versiongoing on roadtrips with step-mommie are so much fun.  today your cute & shy new nanny, miss layla is coming along.   you are so excited!    right as you all get to the shore of the lake, you have an accident in your diaper.  step-mommy always knows so she sweetly uses the opportunity to show the new nanny how to take care of you as you lay comfortable in your diapee, enjoying the rustle of the wind and the waves.. with the threat of passers by.   step-mommy praises you for using your diaper as miss layla intently watches on and helps out.    unfazed by your embarrassment, step-mommy calmly keeps the windows down and car doors open as you lay there blissfully exposed as she shows miss layla how to jerk your wee wee and get the stickies out, making you so happy.  you are such a good boy!   step-mommy and miss layla knows how to make you feel good, don't they? *editor's note:  slight discount due to minimal wind noise, but still an amazing video    ]]> Mon, 08 Dec 2025 09:37:19 UTC https://www.freepornflix.com/video/616840/your-step-mommie-new-nanny-diapers-and-jerks-you-off-in-the-back-of-the-car-wmv-720p2/ https://www.freepornflix.com/video/597792/neighbour-shrinks-and-regresses-you/
Your neighbour has noticed your submissive side and invites you over for a “no distractions” weekend of pampered control. in this pov fantasy she lays out clear rules, soft but unyielding: you relax, follow directions, and let her take charge. she teases, comforts, and corrects with that addictive mix of warmth and authority, marking you with glossy lipstick kisses and promising she can put you right back under her spell anytime she likes. she makes sure that you are fully regressed so that you need to rely on her for everything.. she even breastfeeds you. sensual caretaking meets playful dominance. ]]> Sun, 30 Nov 2025 09:45:43 UTC https://www.freepornflix.com/video/597792/neighbour-shrinks-and-regresses-you/ https://www.freepornflix.com/video/594766/la-trasformazione-sbagliata-the-wrong-transformation/
Io sono un imprenditore di una grande azienda, un uomo tutto di un pezzo che non ha paura di nulla e di nessuno ma durante la solita visita annuale di routine dopo aver fatto vari esami clinici etc la dottoressa scarlet mi convoca nel suo studio per una cosa abbastanza grave. lei mi accoglie con un’aria molto preoccupata, dopo avermi ascoltato il cuore con lo stetoscopio gonfia un palloncino davanti a me fino a farlo scoppiare. a me non suscita nessuna reazione, la dottoressa scarlet mi chiede “sicuro che il palloncino non le abbia provocato alcuna reazione? strano perché nella sua condizione dovrebbe aver pianto a dirotto dallo spavento” poi mi dice “dottor matteo, lei è un grande imprenditore che non ha paura di nulla e di nessuno quindi glielo dico così brutalmente sul viso: lei tra 3 mesi tornerà un bambino! si, i suoi organi e il suo cervello stanno subendo una regressione. ma a mio avviso conviene psicologicamente accelerare i tempi. la mando da una collega” vado dalla dottoressa eleonore, mi accoglie festosa, mi da del tu, mi tratta come un bambino e mi fa tante coccole. mi dice “prima di tutto dobbiamo imparare a perdere il controllo degli sfinteri” mi fa indossare un pannolone e con un esercizio di respirazione mi fa pisciare sotto poi mi dice “mai più telegiornale, per essere un vero bambino solo cartoni animati! guarda che bello questo” e sul tablet vediamo questo cartone animato alla fine dell’addestramento mi dice “sarai stanco dopo questo addestramento, fai la nanna con me? e con questa ninna nanna  mi addormento vicino a lei e mi dice accarezzandomi “vedrai sarai un bambino perfetto” alcuni giorni dopo mi convoca d’urgenza la dottoressa scarlet e mi dice: “c’è stato uno scambio di esami clinici, lei non diventerà mai un bambino, lei tra 3 mesi diventerà un transessuale! ma a mio avviso conviene psicologicamente accelerare i tempi. la mando da un mio collega che le farà una specie di addestramento così il cambio di sesso sarà più sereno per lei” io comincio a piangere e lei mi dice “ma dottoressa mattea cosa le succede? suvvia una signorina che piange?” e il video finisce così. i am an entrepreneur of a large company, a one-piece man who is not afraid of anything or anyone but during the usual annual routine visit after having done various clinical exams etc. dr. scarlet summons me to her office for one thing quite serious. she welcomes me and seems to be very worried, after listening to my heart with a stethoscope, she inflates a balloon in front of me until it burst. it doesn't provoke any reaction to me, dr. scarlet asks me “are you sure the balloon hasn't caused you any reaction? strange because in her condition she should have been crying bitterly with fright "then she tells me" dr. matteo, you are a great entrepreneur who is not afraid of anything or anyone so i tell her so brutally on her face: in 3 months he will be a baby again! yes, his organs and his brain are undergoing a regression. but in my opinion it is worthwhile psychologically to speed up the times. i'm sending you to a colleague ”i go to doctor eleonore, she welcomes me joyfully, she speaks to me, treats me like a stepchild and gives me lots of cuddles. she tells me "first of all we have to learn to lose control of the sphincters" makes me wear a diaper and with a breathing exercise makes me piss underneath then tells me "no more news, to be a real stepchild only cartoons! look how beautiful this is "and on the tablet we see this cartoon at the end of the training she tells me" you will be tired after this training, are you going to rest with me? and with this lullaby i fall rest next to her and she says caressing me "you'll see you will be a perfect baby" a few days later dr. scarlet urgently summons me and tells me: "there has been an exchange of clinical exams, she will not become never a baby, she will become a transsexual in 3 months! but in my opinion it is worthwhile psychologically to speed up the times. i send her to a colleague of mine who will give her a kind of training so the change of sex will be more peaceful for her "i begin to cry and she says to me" but doctor mattea what happens to her? come on a young lady crying? " and the video ends like this. full hd italian ]]> Fri, 28 Nov 2025 10:11:14 UTC https://www.freepornflix.com/video/594766/la-trasformazione-sbagliata-the-wrong-transformation/ https://www.freepornflix.com/video/571808/step-mommy-punishes-you-for-peeing-in-the-pool-wmv2/
Click for mp4 versionyou are excited for a fun day of swimming and bring me your swim trunks. i let you know you can swim as long as you follow two rules: no creamies in the pool and no peeing in the pool. if you break my rules, you lose your pool privileges, get spanked, and have to go into a diaper and plastic pants.after you get in to swim, you end up disobeying me, playing with yourself and peeing in the pool. it was not a good idea to test step-mommy and be disobedient. i grab you out of the pool, pull down your pants, scold you, and proceed to issue you swift spanks to your tender behind with my sandal. then to further make my point, i put you in a diaper and plastic pants. one way or the other,step-mommy has to get your attention and you need to learn! a great vintage miss katherine flashback!  enjoy!  xo ]]> Wed, 19 Nov 2025 09:23:52 UTC https://www.freepornflix.com/video/571808/step-mommy-punishes-you-for-peeing-in-the-pool-wmv2/ https://www.freepornflix.com/video/570970/girlfriend-shrinks-and-regresses-you/
You’ve been messy one too many times… so your bossy girlfriend reaches for her secret weapon: a shrink-ray. in this pov, you’re reduced to pocket-size while she towers above you smirking, scolding, and setting strict “tidy up” rules with deliciously casual dominance. she mocks your tiny protests, taps a fingernail against you, and lets you know you’ll earn your way back to full size only when you obey. she regresses you, lots of ‘little’ talk. finally, breast feeding you.   expect towering visuals, playful humiliation, and indulgent, sensual control, micro size play and strict girlfriend energy. ]]> Tue, 18 Nov 2025 10:31:09 UTC https://www.freepornflix.com/video/570970/girlfriend-shrinks-and-regresses-you/ https://www.freepornflix.com/video/567345/never-disappoint-step-mama-age-regression-wmv-mobile-version/
The usual disobedient step-son! laura knows what awaits you, always late, despite the recommendations, a good spanking lesson with hands and slippers on your bottom, you need it!  english this video is for mobile version hd format 854x480 to buy full hd format version 1920x1080 click here ]]> Mon, 17 Nov 2025 09:47:28 UTC https://www.freepornflix.com/video/567345/never-disappoint-step-mama-age-regression-wmv-mobile-version/ https://www.freepornflix.com/video/560142/un-bambino-capriccioso-e-tante-ciabatte-comode-a-naughty-kild-and-many-comfortable-slippers-3-age-regression-wmv-mobile-version/
Sei appena rientrata dal lavoro, apri la dispensa in cerca di qualcosa da mangiare, prendi un biscotto, nel mentre fai un po’ di shoeplay con le scarpe, sei al limite della sopportazione, non vedi l’ora di infilarti nel ciabatte, perciò ti cambi e subito dopo torni indossando un pigiama e delle comode ciabatte.  prendi un altro biscotto e come provi a masticarlo senti uno strano rumore, hai scheggiato un dente, preoccupata decidi di sentire eleonore, la tua amica dentista. fortunatamente oggi non è in studio, perciò ti risponde e ti rassicura: passerà da te entro sera.   nell’attesa ricevi una mail sul telefono dalla scuola di tommy, una comunicazione riguardo una nota presa . chiami la scuola e la professoressa ti dice che tommy è stato sorpreso a masturbarsi in classe. la notizia ti sconvolge e ti monta una rabbia incredibile verso il ragazzo. ecco che arriva eleonore, ma tu sei ancora scioccata da quanto successo a scuola, cosi decidi di raccontarlo alla tua amica.   ele non sa cosa pensare, ma è concorde con te del fatto di punirlo in maniera esemplare. poi visto che ti sei calmata un po’ ele ti dice se per caso hai delle ciabattine da prestarle, le rispondi che non ci sono problemi e può scegliere lei il modello che preferisce.   ele torna  e tu apprezzi le ciabattine che si è scelta.  ora è pronta a guardare la tua bocca e vedere cosa è successo di preciso. ti metti seduta e lei ti esamina ,ti fa i complimenti per la bellissima bocca che hai anche e soprattutto per merito dell’apparecchio fisso che hai portato fino a qualche mese prima. nota la  scheggiatura, ma sembra meno grave di quanto pensava ,ti rincuora dicendo che è una cosa facilmente riparabile. ele guarda la sua agenda e vede che c’è un posto all’indomani nel primo pomeriggio. ele ti consiglia anche una visita per tommy per vedere se c’è la possibilità di fargli mettere l’apparecchio per i denti vista l’età. tu le dici che visto quello che è successo a scuola potrebbe essere anche una giusta punizione! magari anche il baffo. ele dice che potrebbe andare bene, che adora prescrivere quel tipo di apparecchio ai ragazzini come tommy. prima che se ne vada però vuoi far vedere le nuove ciabatte che un ammiratore ti ha regalato, cosi indossi le ugg e gliele mostri.      you just got back from work, you open the pantry looking for something to eat, you grab a biscuit, while you do some shoeplay with your shoes, you are at the limit of endurance, you can't wait to slip into your slippers, so you change your clothes and immediately come back wearing a pajamas and comfortable slippers. take another biscuit and as you try to chew it you hear a strange noise, you have chipped a tooth, worried you decide to hear eleonore, your dentist friend. fortunately, she is not in the studio today, so she answers and reassures you: she will come by you by evening. while you wait, you receive an email on the phone from tommy's school, a communication about a note taken. you call the school and the teacher tells you that tommy was caught masturbating in class. the news upsets you and mounts an incredible anger towards the boy. here comes eleonore, but you are still shocked by what happened at school, so you decide to tell your friend about it. ele doesn't know what to think, but she agrees with you about punishing him in an exemplary way. then, seeing that you have calmed down a bit, ele tells you if by chance you have some slippers to give her, you answer that there are no problems and she can choose the model she prefers. ele comes back and you appreciate the slippers she has chosen. now she is ready to look at your mouth and see what exactly happened. you sit up and she examines you, compliments you about your mouth and teeth you have thanks to the fixed braces you wore up to when you were younger. she notices the chipping, but it looks less severe than she thought, heartening that it is easily repaired. ele looks at her agenda and sees that there is a place for the next day in the early afternoon. ele also recommends a visit for tommy to see if there is the possibility of having him wear braces at his age. you tell her that given what happened at school it could also be a just punishment! maybe even the headgear. ele says it might be fine, that she loves prescribing that kind of braces for boys like tommy. before she leaves, however, you want to show the new slippers that an admirer gave you, so you wear the uggs and show them to her. italian this video is for mobile version hd format 854x480 to buy full hd format version 1920x1080 click here ]]> Fri, 14 Nov 2025 09:39:45 UTC https://www.freepornflix.com/video/560142/un-bambino-capriccioso-e-tante-ciabatte-comode-a-naughty-kild-and-many-comfortable-slippers-3-age-regression-wmv-mobile-version/ https://www.freepornflix.com/video/555798/babytime-regression/
Some days it’s just too much. too many thoughts, too many things to hold together, too many ways the world asks you to be strong. its okay though; this is a soft place to put all that down.my voice drifts around you, slow and steady, coaxing your body and mind to rest. every breath feels lighter than the one before. the tension in your shoulders, the tightness behind your eyes, it all starts to melt. you don’t have to do anything here. you can just be small. safe. held.imagine warmth wrapping around you, like a blanket that knows exactly how to hold you. feel it settle in your chest, your arms, your legs. your thoughts start to slow. the world fades back until only calm remains. you don’t need to plan, or fix, or carry anymore. nothing is expected. nothing is demanded. just this moment, and the quiet, steady comfort of being cared for.let yourself sink deeper. my voice guides you softly, reassuringly, as if i know everything you’ve been holding onto. you can feel me pulling you into a place where it’s okay to let go completely — where all you need to do is breathe, to trust, to be small. the day’s worries slip away, replaced with gentle care and a quiet, steady warmth.here, you are safe. here, you are allowed to rest. here, someone else carries the weight for a while. close your eyes fully, and let yourself be wrapped in that comfort. let go. just be. ]]> Wed, 12 Nov 2025 09:51:36 UTC https://www.freepornflix.com/video/555798/babytime-regression/ https://www.freepornflix.com/video/545450/diaper-your-wife/
Your wife doesn't have the capacity for adulting. throwing temper tantrums, overwhelmed, dramatic- it's always some display. here's a fun way to test your wife and see if your marriage will stand the test of time. ]]> Sat, 08 Nov 2025 09:29:56 UTC https://www.freepornflix.com/video/545450/diaper-your-wife/ https://www.freepornflix.com/video/525259/lil-punkin-s-halloween-hazing/
The party was supposed to be fun; just a silly halloween initiation, some harmless hazing to prove you could handle your new organization's traditions. but then the older members cornered you. then the *drink* they handed you started tasting… strangely sweet. then the room got fuzzy at the edges… and now? you’re kneeling on the floor in nothing but an oversized "little pumpkin" onesie, your head swimming as the senior members laugh and coo down at you. and the head sorority sister, the one they all call "big sis" is kneeling in front of you with a fresh diaper in her hands and a smile that says: "you’re not leaving this party as an adult."lots of playful humiliation, covert trance work, teasing, wetting encouragement and diaper changes! ]]> Thu, 30 Oct 2025 09:55:53 UTC https://www.freepornflix.com/video/525259/lil-punkin-s-halloween-hazing/ https://www.freepornflix.com/video/512709/blowing-up-your-buttplug-in-a-diaper-hd-mp4/
Starring josie jo hd (1280 x 7280) mp4   *custom video*   you never saw it coming - now you're completely under josie’s spell, with no choice but to surrender to her every desire. as you watch her blow up a balloon, her words weave a spell around you, coaxing you into regressing to a helpless, innocent guy. the more you give in, the more you crave her tlc!   with the balloon in hand, josie commands you to let go of your adult responsibilities and embrace the freedom of being carefree again. as she blows up the balloon with exaggerated puffs, you feel your mind slipping away, replaced by a sense of vulnerability. it's both exhilarating and terrifying, but josie's soothing voice keeps you grounded, guiding you through this transformation. as you become more and more carefree, josie takes care of you in the most intimate way possible. she cleans you up, changes your diaper, and the fun part - she inserts a buttplug into your tight little hole. the pressure in your rectum intensifies, causing your prostate to swell and your arousal to skyrocket, making it nearly impossible to resist the urge to cum in your diaper.   with each balloon she blows up, josie challenges your body and your mind. and as the balloons get bigger and bigger, you feel your arousal growing, even as your buttplug-filled ass protests in pain. you're on the edge, desperate for release, but josie keeps you teetering on the brink, refusing to let you cum until she's ready!     order a custom video through akirashellxxx ( at ) gmail . com ]]> Sat, 25 Oct 2025 09:40:30 UTC https://www.freepornflix.com/video/512709/blowing-up-your-buttplug-in-a-diaper-hd-mp4/ https://www.freepornflix.com/video/511538/breast-is-best-especially-after-getting-your-face-slapped-from-step-mommy-weirdest-fantasy-breastfeeding-and-face-slapping-large-file/
Mommy weirdest came back from her trip, dressed up in leather skirt, coat and gloves, looking so scary in her high heels and she caught you lazing about instead of attending to your work. next thing you know, her gloved hands are slapping your face! luckily, it is your feeding time, and she will never neglect her duties. reluctantly, she asked for her slippers and orders you to take her shoes off and put her fluffy slippers on her pretty little feet. she makes you kiss her toes and feet before allowing you to get on the bed and offering her lovely nipples to you. it was all worth it as they are sweet and juicy as always. most importantly it really calms her down and by the time you are finished, she forgives you for now. her heavy breasts are resting on your face and you are her sweet lil boy again. ]]> Fri, 24 Oct 2025 10:23:17 UTC https://www.freepornflix.com/video/511538/breast-is-best-especially-after-getting-your-face-slapped-from-step-mommy-weirdest-fantasy-breastfeeding-and-face-slapping-large-file/