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duration 10:55
PENIS ENVY video from Ellie Idol
PENIS ENVY by Ellie Idol Recently you've had an experience that has changed you. It's been on your mind nonstop since it happened. You and your best friend went to a party and met a cute babe. One thing led to another and you were tag-teaming that hottie with your BFF. Even thinking of it now it has you beating off a little bit, doesn't it? But there's more to this story than just a hookup. A little something called "penis envy" perhaps? While this girl tried to treat you both as equals, it was clear which dick she had a preference for, and it wasn't your small-ish average one. She loved your best bud's monster cock!! You're left feeling conflicted with jealousy but also horniness. Ellie is going to help you tame those feelings and turn them into pure desire as she describes those events back to you. Embrace the envy and use it to jerk that lil pecker!! Ellie wants you to think about your best friend's titanic tool and all the pussy he must get with it. Stroke yourself as you think about all those stretched cunts gripping his shaft and dripping wet. Have you ever truly pleasured a woman compared to him? You wish you were blessed with his physique and talents but you must work with what you have. Sure you're a great guy but so is he, and if a woman had to pick between two great guys, she'd pick the one with the bigger dick every time! That hookup hottie could be fucking your best friend right at this moment. She did get his number after all, and yours but you never did get the call, hmm? He's probably bending her over doggy style plowing her deeply while you sit here and enviously jerk your peen. You wish it could be you getting some action...but that's not in the cards. Not with any lady who has seen both your cocks. His will always be the preference, the VERY BEST. Everything has changed since that night, you can't get his handsome hung dong out of your brain!! So use it as masturbation fodder and crank one out in front of Ellie!! Let that penis envy turn to lust!!
duration 11:50
The Church Counsellor Goes Rogue video from InfinityWhore
The Church Counsellor Goes Rogue by InfinityWhore [This was a custom request] There's a new church counsellor and you're nervous to meet her because you know she will have been told about your antics. She politely introduces herself and checks through your file, mentioning that you have a clear problem with masturbation. She reminds you that this is a sin and asks what God would think of such acts - but suspiciously seems to be showing off her nylons pantyhose underneath her tight skirt. She continues ready and gasps. You were caught in the church after hours using a crucifix to fuck your arsehole... and it seems she's just learnt this information. She is so shocked that she begins to laugh. She tells you she's never come across one of her clients committing such a sinful act before and, because she's so surprised, she's going to let you into a little secret of her own. She leans in and whispers that she likes to sin and masturbate too. Before you know it, her legs are spread and she's touch herself through her nylons. She begins to unbutton her shirt, encouraging you to stroke in the name of Satan. Sinning is fun and she wants to share it with you. She instructs you on how to stroke while blaspheming and stripping out of her business wear. She shows off her perfect arse in her nylons and laughs, telling you each stroke of your cock is like a hammer slamming into a nail on the cross. Her hand slides underneath her nylons and you can hear how wet she is. She loves that she's turning you away from God, rather than 'fixing you' as she should be doing. The session is almost over but she has one more idea before you have to go. She passes you her personal crucifix and asks you to repeat the lustful act that she'd read about. You slip the cross inside your arse and begin fucking yourself while still stroking your cock. She is close to orgasm and can tell that you are too, so she counts down from 10 to 0 asking you to repeat each blasphemous phrase that she moans in between each number. You cum at the same time and she makes sure that you lick your filthy arse off her crucifix before you leave. You think you're actually going to enjoy these counselling sessions...
duration 12:19
Sis Helps You Get Experience video from Fiona Dagger
Sis Helps You Get Experience by Fiona Dagger (This was originally filmed as a custom video and the name Luke is used throughout) You're hanging out with your big sister and have something you want to talk to her about, but you feel nervous... She tells you whatever it is she won't make fun of you, you can tell her anything! You work up the courage to tell her that you hooked up with another guy at school today for the first time... She's very excited and supportive of you, and asks if this means you think you're gay? You tell her no, you're bisexual, you fancy girls as well, it's just that you haven't had the chance to get any experience with them. You tell your sister how you feel awkward around girls and unsure of what to do with them, but you feel like you need to do stuff with them so you know for sure that you're a proper bisexual. Your sister offers to help you out - if you're scared of doing stuff with girls, she can get you used to that! You're not sure, it seems a bit weird doing that stuff with your sister, but she reassures you that it's fine, she just wants to help. She says that first she needs to test your stamina, and makes you get your cock out and start wanking it. You're feeling embarrassed though and having trouble getting hard, so she gets her tits out for you to look at, and that helps a bit. You stroke your cock while your sister encourages you, but she can tell you're still feeling a little awkward, so she offers to touch herself as well so it's more fair. You both masturbate together as she tells you she'll be in charge of educating you about girls from now on, and she doesn't let you cum until she's ready to cum too!
duration 11:27
Tinder Date Transforms You Into A Sissy video from InfinityWhore
Tinder Date Transforms You Into A Sissy by InfinityWhore [This was a custom request] You've just got back from a successful Tinder date, at least, she invited you back to her place so you assume it went well. However, when you get there you quickly realize that something is wrong. She immediately tells you that it's not going to work out between you because she's after a real alpha man. She noticed your stuttering when you spoke to her and your sweaty palms while trying to eat and quickly realized that she intimidated you. You're not a real man - you're a beta male who doesn't deserve pussy. She humiliates you for thinking that you had a chance with a woman like her. While you try to process this information, she's already pulled out some pink frilly underwear and encourages you to put it on. You have always known your place deep down... but you're hesitant. So she teases you with the chance of seeing her tits. Put the bra on and you might be allowed a peak. You're such a simp and she is so hot so you slip out of your male clothes and into the pretty frilly bra. She laughs at you - you look ridiculous - but she keeps up her end of the deal and shows off her perfect tits. You could never have a chance with her. She even suggests that she might invite a real man over to fuck her while you're on clean-up duty. She teases you again with her pussy and you are so hard. She notices your hard cock and tells you that it would look better clad in matching frilly panties. She throws them at you with an evil smirk and sits back to tell you what a pretty girl you are becoming. You truly feel like the beta male you are now as you watch her show off her pussy and tell you that only real men get to see how perfect and wet it feels. You could never get her wet looking as pathetic as you do right now. One final touch... some pink sheer holds up to finalize the look. All sissied up - you watch the Goddess before you bend over and tease you with her holes. She reminds you again and again of your place until you truly realize how pathetic and beta you are. You were meant to be her sissy pet. She wants to collar and own you while you clean up after her and real men. She slips a buttplug into her arse but then quickly removes it and spins around to make you clean her arse off the glass toy with your mouth. You savor the small taste of her but she wants to stick the plug somewhere else. If you're to be a true sissy bitch, you must learn to take cock in your virgin hole and to cum without touching your pathetic cock. She encourages you through the process of the plug sliding into you for the first time. You're so tight but it feels good to be filled... especially knowing it's been inside a Goddesses arsehole too. She instructs you to very gently stroke your cock while the plug is in your arse - but to remember that over time she will train you to never touch that pathetic little worm again. Anal only for sissy bitches! As you near orgasm, she pushes the glass plug into your arse with her fingers and tells you to imagine it's another man fucking you because you have clearly never deserved pussy and will never get pussy ever again. You're her little sissy pet now.
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