InAnotherLife

I would love to join you! We could share whatever came through the hole, as well as whatever came out of it! LOL

Very nice! Great penetration!

Challenge accepted! I will make it my new sissy goal to get that monster cock balls-deep in my ass! I may need a collection of larger buttplugs to make it a reality, though! I’ll just channel my inner Natalie Mars and resize my sissy hole!

🥰 Thank you, hon! 😊

From the files of “Don’t write Checks Your Ass Can’t Cash” . . . . I think this sissy has done just that! The top is my big chocolate dildo; the same one in my most-recent video that I was riding when I had my first ever sissygasm. So what does this ambitious sissy do? That’s right, order a longer, wider, blacker dildo with a better-defined head, all the better to hit my sissy’s sweet spot. OMFG!! I’ll say that again. OMFG!! I can only imagine — even balls-deep on that beautiful chocolate stick that I’ll be gasping and moaning like a little bitch in heat trying to stretch my sissy cunt wide enough to take even the head of that BBC inside.

Believe me, if I ever get that beast even remotely up my ass there WILL be pictures! Just for sizing purposes I tried having a quick suck on it before I stashed it away. I COULDN’T EVEN GET THE HEAD IN MY MOUTH!!! My jaw simply won’t open wide enough! begs the question: what chance does my poor sissy cunt have? 😈 😮🍆

From the files of “Don’t write Checks Your Ass Can’t Cash” . . . . I think this sissy has done just that! The top is my big chocolate dildo; the same one in my most-recent video that I was riding when I had my first ever sissygasm. So what does this ambitious sissy do? That’s right, order a longer, wider, blacker dildo with a better-defined head, all the better to hit my sissy’s sweet spot (from right here on TooTimid)! OMFG!! I’ll say that again. OMFG!! I can only imagine — even balls-deep on that beautiful chocolate stick that I’ll be gasping and moaning like a little bitch in heat trying to stretch my sissy cunt wide enough to take even the head of that BBC inside.

Definitely one of my favorite pairs! I may have to make them part of my next ass-fucking dildo sessions!

And the last of this series . . . Enjoy, my lovelies!

And still more . . .

More from my “crotchless collection” parade!

Thank you, hon!

Thanks, hon! 💋 Plenty more pics where those came from!

Here’s the view from the side . . . IMG_5714.MOV

Or perhaps in sissy-pink wearing my chastity cage while riding the big chocolate stick? IMG_5715.MOV

We allowed to post that kind of stuff here? Seems off-topic since I ditched the panties before hopping on thedildos! 😉 IMG_5883.MOV

Just how big is big?? Big enough to fill this sissy ass nicely!

How about in my crotchless lace teddy? 😈

Or maybe you prefer doggy style? 😉💋

Or maybe you’d like to see me balls-deep on the big chocolate stick?

Like this? Am I going to be banned for posting these here?

I love panty fun, too! 😉💋

Just waking up after creating my account here a few years ago. I am a 55 yr old CD/TV who is into crossdressing, sissy fantasies, anal play, chastity, mild S&M, and sharing my pictures and videos I do while enjoying those “hobbies.” I am married to a woman who once approved/enjoyed my “little habit” of wearing lingerie; but have since had to go back into the closet.

Let me know if you’d like to see more of me!

And some of me playing in chastity (pink cage, of course!).