Jenny’s Playground

[ivanna07]

[jenniferann777777]

LOVE LOVE LOVE

wearing panties

[stac4648]

[jenniferann777777]

OMG nooooooooll

[boycdsblog]

I wouldn’t want it any other way!

💋💕

[jenniferann777777]

Sissy life

[boycdsblog]

You know you want to!

💋💕

[jenniferann777777]

Sooooo badly

[boycdsblog]

Um is that even a question!?

💋💕

[jenniferann777777]

Both please

[boycdsblog]

Yes! It feels SO right!!!

💋💕

[jenniferann777777]

Soooooo right

[boycdsblog]

Sucking cock is really fun!

💋💕

[jenniferann777777]

Every time I put them on

[sissybimbosisterhood]

What is your sissy level ? (Sissy Test)

Hello sisters. Count your points and share your level with the rest of the community. The objective is to reach the final level at one point of your life.

You wore panties - 1 points

You dressed as a girl - 1 points

You put makeup on - 1 points

You created a girl or sissy online profile - 1 points

You watched transgender porn - 1 points

You watched gay porn - 1 points

You watched sissy hypnosis - 1 points

You bought feminine clothes on internet - 1 points

You bought feminine clothes inpublic - 1 points

You crossedressed in public - 2 points

You bought sex toys in public - 1 points

You shared sexy sissy photos of you on internet - 2 points

You know the feeling of a butt plug in your ass - 1 points

You know the feeling of a sex toy in your mouth - 1 points

You know the feeling of a sex toy in your ass - 1 points

You sucked a stranger's cock - 2 points

You swallowed a stranger's sperm- 2 points

You deepthroat a stranger's cock - 2 points

You got a facial from a stranger - 2 points

You got fucked in the ass - 2 points

You got pegged by a woman - 2 points

You had a creampie ass - 3 points

You participated in a threesome with one men in each hole - 3 points

You went to a glory hole - 2 points

You were the center of a gangbang - 4 points

You received a bukkake from 3 or more men - 3 points

You got peed on - 3 points

You drunk pee - 4 points

You were penetrated by two cocks in the same hole - 4 points

Your body count is between 3 and 5 men - 2 points

Your body count is between 5 and 10 men - 3 points

Your body count is between 10 and 20 men - 4 points

Your body count is more than 20 men - 5 points

You have a sissy tattoo - 5 points

You came out as a sissy - 3 points

You took hormones - 3 points

You did plastic surgery - 5 points

Beginner in sissyhood – 0 to 15 points

A slut in progress – 15 to 30 points

Sissy bitch girl – 30 to 45 points

Experimented sissy – 45 to 60 points

Whore hole sissy – 60 to 75 points

Perfect sissy sex toy – 75 to 84 points

Sissy queen of sluts–85 points

Thank you for playing. Don't forget to leave your score in the comments.

[courtney1119-deactivated2024072]

23

[chesterdinkum]

Only 16

[favouritefemdomcaptions]

35 sissy bitch girl here

[little-closet-sissy-cuck]

Only 36 ?

[tinabtm]

So far 25 and going..

[jenniferann777777]

Sissy Bitch Girl !!!!!!

[bi-cuck-in-bermuda]

[iluvslutsnwhores]

Taste!

[jhardy]

That’s an easy one, “both” 💦💦💦

[wifefantasiesposts]

Why not both?

[jenniferann777777]

Both Please ......

[youcanownme]

[sknyssy1980]

Oh yes, it’s really nice of her. Thank you so much Mommy, I think it’s great that you will be in charge of my chastity keys. I know that having to make all the decisions about my little locked pee pee has been such a burden on you darling. I’m sure Mommy will make sure that I’m a perfect, well behaved, meek little subby hubby for you.

Mommy please no. Mommy you PROMISED that girly time would be our little secret. Well darling….sometimes, when you go out on your dates with one of your boyfriends and…and you leave Mommy to cucksit me…she…she…she makes me…she makes me put on girly panties and little dresses and be her secret sissy boy. When I’m dressed I have to act like a completely effeminate priss or she spanks me and makes me stay in panties for an additional day. Yes darling, that is why sometimes I’ve been so shy about taking my clothes off in front of you. I feel so much shame whenever I’m wearing the ultra feminine panties that Mommy insists on.

You want to see me in them? Oh darling, please…please you can’t be serious. Please darling, I’ve agreed to be your cuckold, and do all the household chores, and…and I’ve agreed to even lose access to my little pee pee and have it locked in this tiny cage so that I’d be even more obedient for you. But please, please don’t make me put on panties. The…the way they make me feel and all the girly training from Mommy, I know I’ll lose myself if you panty me.

Yes Mommy, I do think that my darling wife shouldn’t be limited to just seeing me in my panties, she should get see me in a complete outfit, flirtatiously posing and flashing my tiny panties in one of my little sundresses like you taught me. Yes Mommy, two weeks of panties, strict chastity, early bedtimes, and daily spankings is a fair punishment for my little temper tantrum. I promise to be such a well behaved prissy pansy princess for you and my darling wife. Oh you’re of course right Mommy, a..a..month does sound better. Yes, much more likely to cause permanent psychological changes.

Oh yes, it would make my first day of being a full time sissy extra special if I got to get get pretty with my darling wife. I can help her make sure she looks very sexy and tempting for her date tonight and she can help me look really girly and dainty for my first time going out in public as a sissy with my Mommy. I’m sure you’re right Mommy, while I’m out shopping for new embarrassing girly clothes with you, it will be impossible to not think about how my darling wife is posing for another man in the sexy lingerie I helped her pick out and put on. He will get to touch, hold, and have her while I’m spending quality time with my Mommy in law, doing my own cutesy poses in the dressing room with my new panties and girly looks, going to dinner, and then being put in a nightie and sent to bed incredibly horny but always soft.

I think I’m already starting to break Mommy. I’m getting excited about our special Mommy sissy son in law time together. Let’s go get ready my darling, I really want to make sure that we have time to each try multiple looks before our…hehehe…dates. And don’t worry, I’ll make sure you look SO stunning for yours that he won’t be able to control himself from absolutely ravishing you. You’re so naughty! You really think that if I look dainty and delicate enough, Mommy won’t be able to keep her hand from going under my dress? Oooooh, this is already SO exciting! Let’s hurry up and get nakie so we can start getting each other ready for our big dates!

[jenniferann777777]

OMG ..... can I please .....

[tracylynne]

[sissyswifeblog]

One happy well adjusted sissy hubby!

[jenniferann777777]

SISSY BLISS IN A GRACEFUL TWIRL ......

[sweetsubmissivegirly3-deactivat]

[jenniferann777777]

It’s sooooo hard sometimes to takeout all off and go to bed

[monicareconstructed]

[jenniferann777777]

It’s very important to not get your dress dirty when changing a tire

[steven7000-deactivated20150228]

[taccuck]

Take them off and clean up every single drop…

[jenniferann777777]

OMG

Yessssssssss

[sissymissyxo]

[jenniferann777777]

Oh she is definitely a COCK hungry slut

[doggirljennifer]

I want to be chatting up a cis girl at a bar, we get a bit flirty and then I slip a little pill in her drink. It won't be a secret though. I want her to see me do it and I want her to drink it anyway. She has no idea what it is but she'll listen to whatever command I give her. Won't you, darling?

[transclinic-hub]

Here we go…..

[gispiya]

Pink 🩷

[candicumslut]

Pink

[daniboise862]

Bright yellow satin string bikini panties I stole from my mother.

[mamarriedpantywearer]

The vintage off white girdle style from my mother’s drawer.

[pantylover925-deactivated202607]

Baby blue nylon bikini panties…

[jenniferann777777]

White with flower-ettes