Series: Tara's Sissy Anal Training

Tara Tainton has released this Series back in 2015. It is a training program from beginner level to Pro level.

 Tara's Sissy Anal Training for Beginners

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This is a masturbation marathon for my sissy sluts: a tribute to your fem ways, your cock desires, and your insatiable appetite for serious ass play. You know you want it. We'll start gently, and I'll introduce you to warming up your hole for anal receptivity. Get our your tiniest butt toy and a standard vibrator... I'm going to bring you to the brink over and over and build up one, beautiful orgasm as my sluttiest whore-slaves deserve! Submit, spread, and suck it right in...

Tara's Sissy Anal Training: Mid-Level

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It's time to take your training to the next level. You've been practicing so hard on your own, giving your tight ass a good probing, I'm sure. Now, I want you groomed to be a true sissy slut. Your ass is going to learn to accommodate real girth and serious length. Get your LONGEST vibrator or dildo lubed up and your THICKEST dildo within reach. We're going in, going deep, and going HARD! Don't worry. I'll take you through every step gently and slowly. I'm going to make an expert out of you, bringing you to the edge over and over again. Your asshole will be hungering for those dildos by the time I'm through with you!

Tara's Sissy Anal Training: Advanced Level

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You've been begging for it, but you must've learned by now that you should be careful what you wish for... Are you REALLY ready to take on the Advanced Level?? Get out your fattest dildos or cucumbers of your choice. Utilize four fresh ones to switch out during your training or just use two... if you're just that dirty. Now, get ready to be tested, trained, and all-together tempted as your every position, orgasm, technique, and speed are dictated for you. You're going to be driven to the edge and beyond several times, in several ways, and just as you think you can't possibly handle anymore. Oh, and YES, my devious little metronome is going to really challenge you. Keep up with the ass pounding it dictates for you, and you'll graduate to my Advanced Sissy.

Tara's Sissy Anal Training: Master Level

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This is it: the moment we've both been waiting for. Are you ready to graduate? Well, then, your ASS needs to graduate. I'm ready to school you... are you ready to take on the biggest anal-stretching challenge yet?? (Master my BIGGEST dildo yourself... for the most expansive experience.)

Quarterly Milking by Balls with Star Nine

Mistress Star Nine released these two clips back in 2020. I believe they came part of an old Big sister themed clips, where your Big sister edges you or even locks you up in chastity (I will save that for another post). You come to the first one based on that idea. You have been locked by your Big sister and now it is time for your quarterly milking. Star Nine did not just use this term "quarterly milking" which is alone a hot topic and worth of a post but she also made it even it better. Star Nine will milk you by squeezing your balls only, no jerking off at all. 

Quarterly Milking

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you eagerly await your quarterly milking, the short window where Big sister lets you out of your cage to drain your swollen balls. Usually she gets you off effectively with her feet, wearing the sexy socks that have always made you so weak. This time, she intends to milk you without any gratification, she's just going to squeeze the built up cum right out of your balls. you struggle and flinch, trying to close your legs as her arm muscles visibly pop, her hand around your balls like a vice. you're desperate for release, aching to expel three months worth of cum, but your balls are bursting in her tight grip. Eventually Big sister gets bored and crams your aching balls through the tight metal ring, locking you up again with no relief.

Interested in commissioning your own custom fetish fantasy video? They're my specialty - see my store header for more information ;)

Category: TABOO, BALLBUSTING , CHASTITY MALE , ORGASM CONTROL , SOCKS , CHASTITY

Price: $21.99 USD

Length: 21 minutes

Size: 1527 MB

Format: MP4

Resolution: 1920x1080

Added: 7/24/20 12:00AM

Milked By Your Sister Star Nine

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you trot in eager for your quarterly milking, you've obviously been counting the days, swelling in your cage as you draw on all those old memories of the fun you used to have with Big sister. Of course this is going to be nothing like the old days when it amused Me to let you jerk it to my socks. your attraction to Me has only gotten more and more painful & today it will get even worse. I've decided that this milking will solely be administered via the balls. you'd better hope that you can cum from My hands applied tightly around your weakest bits, because if you don't you're just going right back in that cage for another three

Interested in commissioning your own custom fetish fantasy video? They're my specialty - see my store header for more information ;)

Category: ORGASM CONTROL, BALLBUSTING , ORGASM DENIAL , CHASTITY , FEMDOM POV , TABOO

Price: $13.99 USD

Length: 13 minutes

Size: 989 MB

Format: MP4

Resolution: 1920x1080

Added: 8/20/20 12:00AM

Spotlight: Prolonged tease effects

The Matriarch, Ezada Sinn tweeted: 

"Prolonged tease and denial with make you cum in your sleep like a teenager. Hubby wet his bed last night, in his sleep."