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Cassandra May Videos

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9:32
Confessing My Love For Younger Boys Custom- Church Taboo AP video from Cassandra May
Confessing My Love For Younger Boys Custom- Church Taboo AP On the phone with one of my close girl friends, I tell her how I'm just waiting to go into a church. Why? Because I'm meeting my boy toy there- it was his idea to hook up in one of the confession booths. I'm so excited to suck his cock in there, he's been such a good boy for me recently. I hang up and walk in the booth, titillated and ready to go, but as I hear the voice answer me from the other side, I realize that I went into the wrong booth... and I'm talking to a priest instead! I hurriedly try to leave, telling the priest that I'm not there to confess my sins, sorry... But wait... You aren't allowed to respond to anything I say, right? Or tell anyone what I tell you? Well, in that case... I actually came here to fuck one of the boys in your congregation. He's not the only one I've slept with, but he's my current favorite. I've slept with soooo many younger boys, I just love it! I tell you in detail the ages and things I've done with other younger boys. I realize I'm running late to meet my boy actually, and you beg me to reconsider and not to do this. I scoff at you, telling you that I'm going to hell anyways, I might as well have fun with it and have sex with my boy toy in church! This video features taboo roleplay themes at the request of the customer. No actual taboo is featured or depicted. Again, heavy warning for intense content in this video. This is a custom video. Want your own? Email or DM me! This video features captions due to background noise that impairs some of the dialogue. Keywords: church, confessional, ap, taboo, kink, fetish, non-nude, story time, older woman / younger man, dirty talk, religious, public, tattooed, brunette
15:00
CLASSMATE RIDES YOU Custom - For David video from Cassandra May
CLASSMATE RIDES YOU Custom - For David You come over to help me study for our upcoming test. I start snacking on a blowpop while we study, running my tongue all over it and sucking it as I take notes, and complain about the class and the teacher. You ask to see the book we're studying; and oops! I accidentally spill my beverage on your lap as I lean over to hand you the book. I quickly grab a towel to dry you off, and then cheekily smile as I feel what's in your lap. "....What's in your pocket?", I ask. I make several silly, joking guesses as to what it is, but you won't tell me. I keep teasing you with my tongue. "C'monnnn," I say, "It felt really big.. and very hard... I think I want to play with it, David." I tell you to take your dick out, and I'm shocked and delighted by how big it is. "Can I have it?", I ask, as I take off my panties from under my skirt; and slowly slide on top of you. I start slowly, but pick up speed as I ride your huge cock, trying (and failing) my best to stay quiet so my step-mom doesn't hear us. As I get close, tits bouncing up and down, I tell you I want you to cum in me, but that I want us to do it at the same time. After we both finish, I breathlessly say, "Let's do that again... I'm not quite finished with you yet." This video features the name "David" throughout. This is a custom video. Want your own? Email or DM me! Keywords: white outfit, skirt, sports bra, redhead, brunette, ponytail, innocent, schoolgirl, study, book, class, schoolmate, seduction, tease, tongue, fetish, kink, riding, cowgirl, straddle, boob bouncing, small tits, petite, tattoos, first time, risky, POV, name saying, names, personal, close up, eye contact, oral fixation, mouth, teeth
14:47
Making You Fuck 3 Younger Girls Custom - Taboo CuckQueen AP video from Cassandra May
Making You Fuck 3 Younger Girls Custom - Taboo CuckQueen AP I discover your open computer to see your porn tabs all left open for me the find. I curiously start watching what you've left open, but to my surprise they're videos you've made yourself... with other, much younger girls! I'm a little pissed, but I quickly come up with an exciting way to get back at you. Once you get home, I tell you I have an amazing surprise for you. I tell you I found your videos, confronting you on how old the other girl was and calling you names. Then I call in three girls, each one younger than the last. I found them outside, and I want to watch you fuck each of them, since you're a disgusting sick fuck that likes fucking younger girls, and I'm going to film the whole time... I direct you take the clothes off of the oldest of the girls, and slide your big cock into her tight pussy. It's so hot watching you fuck her as she cries from your cock. I say to let her cry for now; she'll eventually get used to your pervert dick pounding into her. I strip down and play with my pussy as I watch you fuck her, calling you a nasty pervert for doing this. I pull out my vibrator as I tell you to move on to the middle girl. She looks so scared after watching you split the other girls pussy open, she barely knows her ABC's and you're going to shove your cock into her tiny little body. I mock you for being so hard while fucking this younger girl, you must be a sick fuck for liking this so much. Her body can barely handle your fat, grown up cock. I wonder if this is going to turn her into a nymphomaniac, and she'll get addicted to taking Daddy's cock from now on because you're a monster who fucked her. I tell you to stop fucking her and hold her legs open so I can see her gaping destroyed little pussy. Now I tell you to fuck the youngest girl, but you'll have to go really slow with this one. I can see your cock bulging through her belly.. I wonder if I came over there and stroked it from the outside if you would come faster... which by the way you need to hurry and cum in her; before their parents start to come looking for them. Yeah that's right, bounce her tiny body on your cock like a little pocket pussy. I bet your cum would explode out of her little pussy since her body isn't big enough to hold all of your load. Or would you rather I made all three of these girls line up so you can bust all over their little faces and tongues? Oh, that did the trick, you disgusting monster. You lasted so much longer than I thought you would, you fucking monster. This will teach you not to make porn with other girls behind my back again. I can't wait to see how many you get through next time! This is a fantasy roleplay video. This video features taboo fetish content that some may find disturbing. Everyone involved in this content is at least 18 years of age, and no actual youth are featured or depicted. Again, heavy warning for intense taboo roleplay themes at the request at the custom video buyer. This is a custom video. Want your own? Email or DM me! Keywords: taboo, AP, roleplay, masturbation, cuck, cuckqueen, mean girlfriend, mean gfe, younger girls older man, humiliation, degradation, name calling, brunette, tatted, dress, demanding, challenge, dirty talk, roleplay
15:45
Watching Taboo Porn Chat Site Masturbation Custom - AP video from Cassandra May
Watching Taboo Porn Chat Site Masturbation Custom - AP I'm bored and kinda horny, so I decide to hop on a chatting site to see if I can find someone to help me out. I skip through a few people before I find a cute guy with a nice dick. He says he wants to show me something; but I'm shocked and horrified when I see the video he shows me. "What the fuck is wrong with you? Why would you show me this? You're a sick individual.", I disgustedly say. I decide to just focus on your cock so I can hurry up and cum, and then block you. But I quickly become morbidly fascinated with the type of porn you're showing me. I start playing with my tits as I comment on the videos, sickly amazed at the smooth, small bodies, and the scenarios. You keep showing me more videos; and I start rubbing myself through my PJ bottoms, despite my own disgust. It's so wrong, but I'm getting a little wet from watching. You tell me you'll only show me more if I get completely naked. I don't want to, but I finally agree. "Fine," I say, "it just makes it easier to finger myself." The videos continue, and it's so fucked up that I'm getting off to this while you watch me. "Look at the way her tiny cunt stretches around her daddy's cock." I'm fingering myself harder as I get closer and closer to cumming, and I beg you to show me more as I admit I'm loving watching these videos of younger people get used by grown ups. I beg you to cum at the same time as me, and I cum super hard fingering myself. "Well... thanks, I guess. That was a super good cum; I really needed that. But uhmm, I'm gonna go now... Maybe I'll see you on here again some day." I close my computer, both satisfied and repulsed that I just came so hard to the things you showed me. This is a fantasy roleplay video. This video features taboo fetish content that some may find disturbing. Everyone involved in this content is at least 18 years of age, and no actual youth are featured or depicted. Again, heavy warning for intense taboo roleplay themes at the request at the custom video buyer. This is a custom video. Want your own? Email or DM me! Keywords: taboo, AP, roleplay, chatting site sex, phone sex, video call sex, masturbation, encouragement, brunette, solo female, trimmed bush, long hair, reluctant, disgust, dirty talk, watching porn
67:47
LIVESHOW: Panties, Degradation, and Subbing video from Cassandra May
LIVESHOW: Panties, Degradation, and Subbing My private show customer commands me to bark like a dog, and to put on a pink o-ring collar, making me call myself a dumb little puppy slut, and hang my tongue out and slap myself several times while moaning and barking. He tells me to slap myself in the face ten times, before telling me to grab one black high heeled shoe and to lick it and deepthroat the heel, spitting and slobbering all over the place, and to slap myself on my tiny tits and pinch and twist my nipples while I do. He tells me to go and put on the pair of black panties he's buying from me, and I say "Yes, daddy." as I show them off. Then he instructs me to take the pink pair I was just wearing and suck off my own juices from them, while he reminds me that I'm just a dumb little bitch and to keep barking and panting as I suck on my panties. Then I grab my baseball bat and beat my ass with it until it's nice and red and daddy is satisfied. He then makes me hump the bat and then the high heel in my underwear like a desperate stupid fuck cow. I moo and slap my tits as I hump the shoe, before leashing myself up, slapping my small tits, and calling myself David's dumb pathetic cow, a stupid POS, and a bunch of other names. He tells me to pull on my leash and moo like a cow as I keep humping the shoe, before making my slap my tits, thighs, and pussy with my paddle. He then decides I've been good enough to grind on my stuffed pillow pet and use my vibrator until I cum, and I do so as I keep calling myself "David's stupid fucking bitch" and "Daddy's dumb ugly slut". Once I've cum, I suck the head of the vibrator like an obedient slut. Then I take off the black panties that I just came in and suck and lick the juices out. He then wants me to try on all of the other panties he's buying from me. I degrade myself as I try each one on, keeping my collar and leash on, and intermingled with calling myself a cow, pig, fat, and bitch. I pull my nose up and oink, shake my ass, spank myself, hit myself on my pussy with the high heel shoe, hump the bat some more, cover my ugly fucking face with one of the worn panties, give myself a wedgie with the leash, mooing and oinking the whole time. Once we get to the last pair, he makes me poke and stab my nipples with the pointy end of the high heel, call myself horrible degrading names like "worthless", "pathetic", "whore, and "slut", and hump my stuffed pillow pet again. With the pair of panties still on my head, I beg David to cum all over his dumb painslut, hitting my ass as I hump the pillow. Then I get close to the camera and Hit my udders as I beg him to cum on my stupid ugly cow face. Video ends with a little bit of conversation between us before the show ends. This is a recording of a private show, so the video quality is lower than my usual videos; the price point reflects this. The customer typed to me the actions he wanted, but they are not featured in the video, so it may be confusing at times when I respond the conversation that no one else can see. This video is full of highly degrading things, s&m, humiliation, lots of panties, and use of the name "David" and "Daddy" throughout the video. Email me about scheduling your own private cam show!
7:54
Brad Big Dick Impreg Smoking Suck + Fuck video from Cassandra May
Brad Big Dick Impreg Smoking Suck + Fuck start the video by thanking you for coming over. I know that you've had a bad day at work, Brad, but I'm going to make you feel better. I tease you by stripping out of my little black dress into my lingerie, then take off my lacy bra and panties as well. I knew this would make you feel better! But I've got something to tell you- I went through your phone history and I know what your biggest turn on is. I pull out a pack of cigarettes, and light one, saying that I know your secret kink is women smoking. Then I tell you to pull your big dick out. I start giving you a handjob and say how I've been wanting your big dick all day. I know that you love it when I blow my smoke in your face and on your dick; and tell you that your dick belongs to me. I tell you that I need your big dick in my mouth, and then start sucking you off. I've always wanted to suck your big dick while smoking. Sucking your big dick is making me really horny and wet. I say how I need to fuck you, and that I'm going to fuck you raw. I start riding your fat cock, saying how from now on I'm going to smoke a cigarette every time I fuck you, and that I'm going to ride your big dick every day, since your dick belongs to me. I love being your dirty little slut, and I'm going to smoke and fuck you raw whenever and wherever I want. I need you to cum inside of my tight wet pussy, I'm so horny and I'm going to breed you from now on. As I keep smoking I tell you how badly I want you to get me pregnant. We both cum as I'm riding you cowgirl style, and once we're done I tell you that was great and that I'm going to do that every single day, because your dick belongs to me forever now. Keywords: Brad, name calling, using a name, smoking, shaved, cigarettes, riding, big dick, impregnation, begging for cum, cum inside, breed, breeding, dominant women, cock worship, handjob, blowjob, cowgirl, doggy, reverse cowgirl, cock control, smoke, red lipstick, petite, tattoo, strip, lingerie, bdsm, kink, female domination This video features the use of the name "Brad" throughout the video. This is a custom video. Want your own? Email or DM me!
13:49
TEACHER ACCIDENTALLY FLASHES HER PANTIES Custom video from Cassandra May
TEACHER ACCIDENTALLY FLASHES HER PANTIES Custom In a white button down shirt that just barely shows my black bra underneath, a short tight skirt, glasses, and black heels, I admonish you as soon as you walk into the room. You're late for your makeup quiz. Don't you realize that this is 25% of your final grade? Well, now you only have 5 minutes to finish it, so you better get to it!! I stand up to hand you the paper, unknowingly flashing my panties as I sit back down. I'm grading papers while you complete your test, crossing and uncrossing my legs, revealing my rainbow striped panties again and again. I notice you staring at me, and ask if you have a question. No? Okay, well then focus on your test, please. You don't have that much time left. I see you staring again a little bit later, and embarrassed at being caught a second time, you say you do need help, so I stand up and walk over to help you out with one of your problems. I tell you not to be so nervous, and next time you should be on time, because you stressed yourself out by being late. I sit back down, flashing you again. You still seem nervous and I check on you in between grading. You finally finish up, and I tell you that since you seem so worried, I'll go ahead and grade it right now. And you aced it! I'm impressed- but why were you nervously staring at me the whole time? What.. omg my god. Could you see my underwear this whole time? Oh no, I didn't even realize I was sitting like that, I shouldn't have worn this skirt. Can we just... keep this between us? It would look really really bad for my career if parents found out I was flashing my panties at a student. I can't believe this. If we can keep this a secret I promise you will ace this class for the rest of the year. Okay? Okay, great, thank you. I tell you awkwardly that I'll see you in class next week, before nervously gathering my things and walking out, but not before accidentally flashing you one last time as I go. This is a custom video. Want your own? Email or DM me! This clip features both landscape and portrait angles of the camera, at the customers request. Keywords: student, teacher, roleplay, heels, black heels, high heels, classroom, school, test, skirt, upskirt, panty, panties, flashing, exposed, accidental, unknowing, white shirt, glasses, brunette, long hair, nervous, awkward, embarrass, embarrassment, humiliation, humiliated, candid, POV
11:33
I WANT TO BE CUCKED BY YOUNGER GIRLS Custom- Taboo AP Cheating Fantasy video from Cassandra May
I WANT TO BE CUCKED BY YOUNGER GIRLS Custom- Taboo AP Cheating Fantasy Your wife calls you into our bedroom to tell you something that's been on my mind. Our sex life is great, but there's one fantasy I really want to try. I want you to cheat on me. With younger girls. And get them pregnant. Please don't think I'm weird! I tell you how hot I think it would be to watch as you touched their smaller bodies with your big hands, stretched out their tight virgin pussies with your huge cock, before blowing your load in their little pussies and getting them pregnant. I touch myself as I describe what I'd want you to do to the younger girls, and confess that I fantasize about the two daughters who live on our streets. I finger myself as I tell you in details how I want to watch you fuck them, how I want to see your cum drip out of their cunts, how I want you to shove your dick down on of their throats as the other sucks on your balls. I cum as I beg you to cheat on me with these girls, I want to cuckquean as you impregnate these teenagers. Once I finish, I suggest we invite the girls over someday and play with them for real. This is a fantasy roleplay video. This video features taboo fetish content that some may find disturbing. Everyone involved in this content is at least 18 years of age, and no actual youth are featured or depicted. Again, heavy warning for intense taboo roleplay themes at the request at the custom video buyer. This is a custom video. Want your own? Email or DM me! Keywords: cuck, cuckqueen, cuckquean, cheated on, begging, solo female, masturbation, gfe, taboo, kink, fetish, AP, cheating, impreg, impregnation, younger girls, dress, lingerie, dirty talk, fantasy, extreme, edgeplay, roleplay, redhead, tattoos, wife, girlfriend, natural, masturbation
9:56
Tricked Into Being Dinner Vore POV Custom video from Cassandra May
Tricked Into Being Dinner Vore POV Custom I invite you over to my house, with the expectation of filming a fun food-play and vore dinner party video - with you! Once you arrive, I tell you that you have to follow everything I say exactly for this to work properly; then instruct you to undress and get into my baking pan. I'm delightedly fattening you up and covering you with a variety of cheeses, and oil and season you up so you'll be extra delicious! Then, my demeanor changes completely and I reveal to you that this isn't just a play-pretend, kinky fantasy... I'm actually going to cook you up and serve you to all of my friends at dinner! But since you're all tied up, you can't escape! I tell you how I plan on cooking you, but as I do I notice your huge hard-on. It looks so tasty I say that I think I'm going to save it for myself. I lick and suck it to give it a taste, then decide to jerk you off and make you cum all over the cheese to add more flavor! I keep stroking and sucking your cock, encouraging you to explode your load until you finally do. Now that you and all of the ingredients are covered in cum and everything is fully prepared, I throw you into my oven and close the door. This is a custom video. Want your own? Email or DM me! Keywords: bondage, bdsm, fetish, kink, vore, femdom, female domination, food porn, food play, eating, cheese, cann, canni, POV, cum, jerk off, redhead, CFNM, dinner party, cooking, kitchen, executrix, blowjob, meal prep, female, petite, seasoning, carnivore
9:55
PUBLIC DATE SMOKING HANDJOB Custom video from Cassandra May
PUBLIC DATE SMOKING HANDJOB Custom We've just come from our dinner, and I'm telling you how much I'm enjoying our date, and this cute bar, and spending time with you! I ask if you're okay with me having a quick, after-dinner cigarette; and you tell me you're more than okay with it. In fact, as I light my cig, you tell me it's actually one of your kinks! I'm intrigued, and I ask if you mind if I blow my smoke at you. As I do, I notice that you instantly got hard. I'm so excited and shocked! I keep teasing you and turning you on with my smoke, until I put out my first cig and tell you to come beside me. The bartender isn't paying attention and everyone else in the bar is busy. So I tell you to put out your cock, and as I start my second cigarette I start to jerk you off. I'm dirty talking and smoking at you, while trying not to get caught stroking your dick. As you get closer and closer from me giving you a handjob in public and smoking, I lean down to catch you load in my mouth, swallowing every last drop down into my smoky mouth so we don't leave a mess. I can't believe we just did that in here without getting caught! I tell you that we should close out our tab and head back to my place for the rest of the night. This is a custom video. Want your own? Email or DM me! Keywords: public bar date girlfriend gfe girl net door nice girl smoke smoking smoky cig ciggie cigarette red lips lip gloss lipstick red hair redhead alt girl sweet handjob handy jerk off jerk-off stroke cock tease teasing exhibitionist
9:26
First Date Accidental Flashing Custom - Upskirt Embarrassed video from Cassandra May
First Date Accidental Flashing Custom - Upskirt Embarrassed I greet you as you come in- we've got some time to kill before our dinner reservation. Wearing glasses, a short tight skirt, a tight dark shirt, heels, and white thong panties with pink flowers on them, I sit down, not realizing that you can see my underwear at all! I'm a bit nervous, but bubbly and excited as I chitchat about my outfit, and offer you a glass of wine. I cross and uncross my legs as I tell you how excited I am to try this place out, and that I'm really happy you asked me out because I've been crushing on you for awhile. I continue to ask you questions about yourself, playing with my hair and adjusting my glasses as I cluelessly show off my panties every time I uncross my legs or stand up to grab something. As I check my phone for traffic, I suddenly realize I've been flashing you this whole time! I'm so embarrassed! I apologize profusely and awkwardly, I just didn't realize my short was so short! I can't believe I flashed you on our very first date! Maybe you can just forget this even happened and we can start over fresh when we get to dinner. I get up to grab my purse so we can leave, and flash you one last time without realizing it, tugging my skirt down as I walk away. This is a custom video. Want your own? Email or DM me! Keywords: flashing, upskirt, panty flash, accidental, unknowing, short skirt, underwear, thong, white panties, glasses, ditzy, embarrassed, humiliation, humiliated, awkward, heels, black heels, date, gfe, girlfriend experience, first date, dinner date, apology, apologetic, nervous
16:01
Bareback Cheating W Your Barefoot Ex Custom - Risky Ex GF Impreg video from Cassandra May
Bareback Cheating W Your Barefoot Ex Custom - Risky Ex GF Impreg You come over to drop off my shoes for me, my favorite pairs of heels that got lost in packing when we broke up. I thank you, and mention how much you used to love when I wore them for you, back when we were still together. You get up to leave and I invite you to stay for a bit to catch up, after all, we haven't seen each other in ages. You look between my legs and notice I'm not wearing any panties- oops! I must have forgotten to put some on before you came over. You'd get into a lot of trouble with your new prudish girlfriend if she knew you were looking at your ex girlfriend's pussy. But c'mon- don't you miss this pussy? Don't you miss the taste? I strip out of my dress and lay back, inviting you to ignore how wrong it is, and give into true pleasure. You eat my pussy as I moan with my bare feet in your face. I bet your new gf doesn't moan and dirty talk like this. After you make me cum, I tell you there's no going back now; we might as well go all the way. I climb on top of you cowgirl style, and as I rub my warm, wet pussy against your bare cock, I wonder aloud... "are you still scared to fuck me without a condom on? You were always too scared to before.Too worried about knocking me up." But I start riding your bare dick, saying how much better it is raw, and how the risk makes it so much hotter. Your new girlfriend would never fuck you like this, she's too boring. We keep going, harder and faster, me begging you to go deeper and bust inside of me. After we cum, I'm delighted. "I can't believe you actually lost control and came in me!" What would your girlfriend think if she walked in right now and caught us... if she saw your cum dripping out of your ex's pussy? And what if I got pregnant? But don't worry- I won't tell her.. because I want to do this again. We can sneak around behind her back and you can fuck me raw any time you want to. The risk of getting caught cheating and the risk of me getting pregnant makes it soooo much hotter. And could you imagine how cute I'd be if I did get knocked up? Walking around, barefoot, big belly... Well, anyways, you'd better run home to your boring girlfriend before she gets suspicious. But before you go; I think I left one of my jackets at your place too. Could you drop it off to me sometime next week? Maybe we could do this again... And next time you fuck your new girlfriend, I hope you think about me. This is a custom video. Want your own? Email or DM me! Keywords: cheating, infidelity, cheater, ex, exes, ex girlfriend, feet, foot, soles, barefoot, pussy eating, shaved pussy, dirty talk, pov, riding, tits bouncing, cowgirl, bare feet, heels, little black dress, risk, caught, risky, pregnancy, impreg, cum inside, cum talk, tease, seduce, unprotected sex, tattooed, petite, bareback
16:40
MEAN WIFE MAKES YOU FUCK YOUR SISTER Custom - Taboo video from Cassandra May
MEAN WIFE MAKES YOU FUCK YOUR SISTER Custom - Taboo Your controlling, bitchy, jealous wife is mad that you paid more attention to your sister during dinner than her. Now that you've pissed her off, she's going to make both you AND your sister pay for your indiscretion. You're so afraid to not listen to her, you'll accept whatever she says, not wanting to upset her even more. She calls your sister back to the house under the false pretense that she left something over. When your sister returns, your wife's plan is set into motion. She berates both of you, and commands that you strip naked and then undress your sister. She tells you to play with your sister's tits that you must loooove so much more than hers. Then tells you to eat your sister's pussy. You're both too scared to disobey her when she's already mad. She admonishes and mocks both of you while you go down on your sister, before demanding that you fuck her. You reluctantly shove your cock into your own sister, while your wife directs you two and doesn't let you forget that you're related. Your wife plays with her pussy while calling you both sick perverted fucks for what you're doing at her command- committing the ultimate taboo just because you're told to. She tells your sister to start riding you, commenting about how her ass bounces on her brothers cock. "Is that going to make you cum? Are you going to cum in your own sister's pussy? You must like fucking each other." Your wife says, before saying that neither of you are allowed to cum until she says so, because SHE'S the one in charge here. Once you're told to bust in your sister, your wife calls you disgusting and as a final punishment makes you eat your own jizz from your sister's pussy. You're helpless to obey your mean dominant wife, and this will serve as a reminder not to ignore your wife, and she says the next time you disrespect her the punishment will be so much worse; before finally demanding that you both get the fuck out of her sight. This video features taboo roleplay themes at the request of the customer. No actual taboo is featured or depicted. Again, heavy warning for intense content in this video. This is a custom video. Want your own? Email or DM me! Keywords: dirty talk, taboo, roleplay, brother-sister, family, wife, bro-sis, cuckquean, mean, dominant, controlling, bitchy, mocking, degrading, perverted, fantasy, kink, fetish, little black dress, encouraged cheating, encouraged taboo, shaved pussy, petite, tattooed, punish, orgasm control, solo female, POV, masturbating, cuck wife, extreme
7:39
INTERVIEW UPSKIRT PANTY FLASHING Custom video from Cassandra May
INTERVIEW UPSKIRT PANTY FLASHING Custom Hello, I'm Cassandra May! I'm here to interview for the marketing position? I sit down, my short, tight skirt hiking up as I take a seat in your office. We go over why I want to work for the company, what I think I could bring to the table, and my educational experience- but I'm unconsciously crossing and uncrossing my legs as we chat through the interview, not realizing that I'm giving you a full frontal view of my white, strawberry print covered panties. You ask me about my resume, I forgot to give it to you when I first came in! I reach to grab it out of my purse, spreading my legs wide as I turn around in my chair. I stand up and hand it to you, and you ask if I filled out the application as well. "I'm so sorry," I say, "No one said anything about an application, I didn't know I needed to do that." Luckily, you have an extra one for me to fill out, and I sit back down to complete it. As I'm filling out the application form, I'm wiggling my high heels, swinging my legs open and closed, and crossing and uncrossing my legs; still not realizing that I'm showing my panties. As I finish the application, I accidentally give another long flash before I stand and hand it over to you. Before I go, I ask how long I should expect to wait before I hear back about this role. Okay wonderful! Thank you so much for your time and considering me for this position. I walk out, still having no idea you were getting glimpses of my underwear the entire time. This is a custom video. Want your own? Email or DM me! Keywords: short skirt, underwear, panties, panty, high heels, professional, job interview, roleplay, non-nude, upskirt, bare legs, long hair
11:40
Watching You Fuck a Younger Girl Custom - Taboo GFE Voyeur video from Cassandra May
Watching You Fuck a Younger Girl Custom - Taboo GFE Voyeur We get home from date night, and while everything was going fine; I did notice that your eye was wandering tonight. Specifically at the young, pretty hostess who was working tonight. So; I decided to surprise you, since you like ogling other younger, girls in front of me. I brought home another girl, one who looks just like the hostess but even younger. Since you're a nasty old pervert, I figured you'd enjoy fucking her young, tight pussy - and I want to watch. I instruct you to take her clothes off, and gently start playing with her pussy. I mock you for hard you are and how fucked up this is, then tell you to slide your cock into her. I'm touching myself as I watch you fuck this young girl, griping and complaining the whole time about how sick it all is and how perverted it is, but how I still love watching you fuck her young tiny body. I tell you to cum in her little pussy, then say that it's a good thing she can't get pregnant; because I have so much more planned for us and this is just the beginning. This is a fantasy roleplay video. This video features taboo fetish content that some may find disturbing. Everyone involved in this content is at least 18 years of age, and no actual youth are featured or depicted. Again, heavy warning for intense taboo roleplay themes at the request at the custom video buyer. This is a custom video. Want your own? Email or DM me! Keywords: masturbating, solo female, redhead, gfe, girlfriend, mean girlfriend, bossy girlfriend, voyeur, taboo, roleplay, cuck, fucking encouragement, AP, cum encouragement, fetish, kink, tattoo, petite, roleplay, perversion, older man / younger girl
19:45
Evil Alt Girl Makes you Her Gooner Bitch Custom - Taboo Twincest video from Cassandra May
Evil Alt Girl Makes you Her Gooner Bitch Custom - Taboo Twincest I invite you over to confront you about my identical twin sister, Meg. I know you've been sending her perverse messages + pictures, and that it's developed into full blown sexual harassment. It started subtly, but it's been going on for months now and you're completely obsessed with her and her sexy, alternative look. You first told her that you're a sadomasochistic, pussy-free, porn addicted pervert, a loser virgin who's never had sex with a woman. You worship porn like a religion, and routinely jerk off to pictures of her with religious devotion. You want a Goddess to guide your depravity. And you want Meg to be the one to do it. You want to call her Mommy, and you want Mommy to own you and feminize you, turning you into a perfect little cocksucking latex fuckdoll. But, she wants nothing to do with you. You repulse her, and she's tried to avoid you. So now you've told her that since she won't control you, you want to destroy her. Because she refused your advances, you went even darker with your fantasies, trying to dehumanize her. You want to steal her away, and turn her into porn. Disturbing, extreme porn of you torturing and hurting her. Make videos of her and post her online so that everyone else can worship her alt girl perfection. But then I tell you that everything you love about Meg, she learned from me. I'm the slightly older twin, and my sister has always idolized + admired me, much in the same way you idolize her. But how could you not? I show off my perfect tits, my Goddess ass... my body was made to be worshiped by little loser bitches like you. I saw the shock, + the lust, on your face the first time you saw me. You knew that Meg had a sister, but not an identical twin sister. Perverts like you always fetishize twins like my sister + I, putting us on pedestals. As you should. You should always worship women like us, and I believe you should be made to suffer while you do. I go on to tell you that because of your constant harassment of Meg, she and her boyfriend broke up. I know he tried to scare you off at first, but your disgusting messages made my sister feel so dehumanized that it emotionally destabilized her and they split. She was completely broken when she came crawling back to me.... I see this is turning you on. Why don't you pull your sad cock out and stroke it for me? I guess I should really be thanking you. Now that Meg's boyfriend is out of the picture, there's no one left to protect her... from Me. You're not the only one who wants to completely control and hurt Meg. I start rubbing my pussy as I tell you all about how ever since we were younger, I've been stronger than my sister, so I groomed her into being the perfect playtoy- a fucked up, submissive version of myself. I tell you how, when she came to me crying, I made her sit and read out every single message you've sent her, over + over until she'd memorized them. Then I fucked the hell out of her with the biggest cock I have, still making her repeat your creepy, pervy, fantasies; then made her lie down in the bathtub and pissed all over her to remind her who really owns her. That's always been my favorite game to play, degrading her and pissing all over her while making her thank me for my abuse. Meg is my property. I love fucking my twin slave sister in perverted and fucked up ways, because it's almost like I'm doing it to myself. I can play Domme and sub at the same time. I thought I had already destroyed Meg, until you came along and fucked her up some more. I have a proposal for you...I want you to keep harassing my sister, and other women that I select. You're going to wear them down and make them vulnerable for me to swoop in and take advantage. I'll let you watch as I play with them, as I fuck them and degrade and control them. I'll let you record it all. We'll make our own porn with these women that you'll watch on repeat to goon to. All of the sick, twisted porn you could ever want to melt your brain to. I might even let you play with some of them if you're very good and do exactly as I say. Because Mommy owns you now. I have since the second you laid eyes on me. And I will gradually feminize you and make you into another version of myself, like I did with Meg. You'll be a constantly horny, always obedient little fuckdoll and help me act out my own perverted fantasies. You'll be Mommy's little creep, helping me dominate other women. Think of all the dark, twisted things we can do together. I'm so close to cumming, I tell you to keep stroking as I cum; but command you not to cum yourself. You don't ever get to cum. Only Mommy gets to cum. After I cum, I tell you my net plan. I'm going to invite my twin sister over, and you're going to watch and film us. Keep stroking and think about all of the nasty, depraved porn we're going to make of Mommy doing her evil stuff. This video features taboo themes and dialogue. It is a fantasy, but viewer discretion is advised. This is a custom video. Want your own? Email or DM me!
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