"I know this is a bit odd, but you are the only one that can do this..."

Dildo

Tara’s Sissy Anal Training: Advanced Level

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 read to take on the Advanced Level?? Get out your fattest dildos or cucumbers of your choice. Utilize four Read more...

Anal Play Instruction, Challenges, Cleavage, Dildo, Eye Glasses, Female Domination, Masturbation Instruction, Orgasm Control, Sex Ed, sissy slut, Sissy Training, tara's sissy anal, Toys, video series

My Big Plans for My Little Girl

My little girl-boy is growing up... you're turning 16 - sweet 16 - and I'm so very proud of what you've become. No, no, no... it's too late for you to ever be a boy. I might as well share with you Read more...

Anal Play Instruction, bi encouragement, Cleavage, Corset, Dildo, Dirty Talk, Female Domination, Forced Bi, Forced Fem, Lingerie, Milf, sissy slut, Sissy Training, Toys

Let’s Change Gender Roles and Spice Up Our Play

I've got an idea... wanna hear it?? Let's try something different tonight! I know how you love my sexy clothes... wanna watch me strip out of them? And then YOU can put them on! Oh, come on. Just play Read more...

Big Breasts, Dildo, Female Domination, Forced Crossdressing, Forced Fem, Lingerie, Masturbation Instruction, Nipples, Silk & Satin, Strap-On, Striptease, Topless, Virtual Anal Play, Virtual Sex

Coercing You into Turning Both of Us on More than Ever Before

You know I love you. I REALLY love how you eat your own cum for me on occasion. It really gets me hot! I've never come harder than when your head is between my legs, lapping at that fresh hot cum Read more...

Anal Play Instruction, Big Breasts, Costume, Cum Eating Instruction, Dildo, Forced Fem, Garter & Stockings, Humiliation, Lingerie, Masturbation Instruction, Nipples, Role Play, Tease, Topless, Toys

You Love It When I Gently Coax You

As IF you don't know how to make yourself FEEL amazing... how to stroke your cock... how to edge yourself... how to make your cock head bulge and pulse... how to get yourself so close to orgasm that nothing else matters in the world. Read more...

Cleavage, Corset, cum countdown, Cum Eating Instruction, Cum Play, cum swallowing, Dildo, edging, Masturbation Instruction

Tara’s Sissy Anal Training: Mid-Level

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 Read more...

Anal Play Instruction, Cleavage, Dildo, Female Domination, leg spreading, Masturbation Instruction, Panties, Sex Ed, tara's sissy anal, Toys, upskirt, Vibrator, video series

Growing Stronger, Taller, and Bustier with Every Touch and Taste of Your Mighty Cock

Oh, so you're going to "let" me suck your cock? You're so lucky I've always had the biggest crush on you... and I've been dying to see what's in your pants... and just how BIG it is. Oh, yes. That's what Read more...

Naughty Girl’s Revenge

Santa, Santa, Santa. I'm disappointed in you. If it wasn't for your famous taste for milk, I never could've managed to take advantage of you. Did you like your little nap? Oh, no, don't worry about every other house on Read more...

Big Breasts, Christmas, Cleavage, Costume, Cum Eating Instruction, Dildo, Female Domination, Masturbation Instruction, Nipples, Strap-On, Topless, Toys

Your First Critical Lessons in Pleasing a Woman, Courtesy of Your Unorthodox Nanny

You've spent your prepubescent years mostly alone with your beloved nanny to supervise and teach you. You've naturally grown enamored of her: the most beautiful woman ever... in your eyes. During intimate conversations and your innocent confessions, she's come to realize your Read more...

Cfnm, Cleavage, Dildo, Female Domination, Legs, Masturbation Instruction, Milf, nanny, Older Woman, Panties, Pantyhose, Pussy Eating Instruction, Sex Ed, Strap-On, Toys, upskirt, Virtual Pussy Eating

You Know What Would REALLY Turn Me On…

Before we go to bed... well, I wanted to share something with you. You know, I saw something on the internet the other day when I was just browsing around. You might find it funny or... well, I saw this video of Read more...