A pegging punishment to train my boyfriend’s tight little ass. My boyfriend loves submitting to his Goddess and pleasing me in any way that he can. And sometimes, he is rewarded in kind with fun experiences like a girl-on-girl threesome that I invited him to. But other times, the kinky roleplay takes a dark and twisted turn, and I let out my mean streak. William was being too much of a little brat lately and asking for a punishment. One day, I walked into the room to find him looking through my laptop, and suddenly some things made sense… He’d been intentionally affecting the porn that pops up in my suggestions! What a little weasel!
And you wanna know what he was secretly sneaking into my recommended list? Pegging punishment and strap-on videos. He was such a little brat that he’d been dropping hints and breadcrumbs about wanting to be pegged. So one night, I really made things sexy and exciting for him. I invited him over, and he walked into my room to find the set of that night’s peginng punishment… unbeknownst to him, at least. Red lights. Handcuffs on the bed. Thigh-high boots, fishnet stockings, and a little black thing. He took a moment to take in the scenery. And finally, I walked in behind him and pushed him along with a little police baton.
As he reached the bed, I cuffed his hands down to it in the most compromising position. He lay on his stomach, with his ass in the air as I circled him. Click, click, click. The sound of my boot heels followed as I played with his excitement. Then, I harshly gripped his pants and yanked them off. He gasped and froze in excitement as I rubbed my baton between his cheeks, rubbing through his boxers. Finally, I yanked those off, too, and he jolted. “Mistress…” He begged, which almost sounded like a little moan. “Are you ready for your pegging punishment?” I asked, applying a dollop of lube between his cheeks and on the head of a bigger, thicker 8″ black strap-on.
He groaned and squealed like a slut as the lube helped me pump that big toy in. He was spread open further than he’d ever been before, and I didn’t even warn him up with a butt plug this time. “Oh my god, it’s so big, oh my god—please Mistress!” He cried, and I could see that he was getting even more excited. His cock was starting to get hard. To make things even meaner and sexier, I took another pair of handcuffs and tightly fastened them around his cock and balls. I gave it a good squeeze, making the metal dig into him like a cruel cock ring. Oh, this was going to be so much fucking fun. The pegging punishment was only just beginning.
He had one inch of my big black cock in his ass, and there was much more to come. Finally, I pressed my strap-on deeper. Inch by inch, I slid into him, making his legs shake with pleasure. And when I finally bottomed out in him, I pulled it all out… To ram it into him all at once. His squeaks and surprised moans were like music to my ears.
Are you ready for your pegging punishment? Call me.
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Aileen~ Awesome as Usual!
Aileen is the best! We have had quite a few date nights now and she drives me crazy each time. She knows me and what I like now and plays until I can’t take it anymore…in a good way of course. It’s also fun to laugh with her during “pillow talk”. The time always goes too fast! As always, looking forward to next time.
On our latest call Aileen deemed me to be Her sickest disciple, after previously telling me I am the most pathetic. I am so honored to be Her sickest most pathetic disciple. Aileen has brought me so far. I love ❤️ and worship Her and pray that our journey continues forever. Aileen rules!
Michelle’s voice and ideas were very exciting!! I can’t wait until our next adventure!! Everyone should give her a call she won’t disappoint you. When you call her, I’m sure you’ll be feeling the same way!!
Simply put, Vicky is and always has been amazing. She is so much fun to play with and talk to!
Zoey was amazing. The minute our call started, she knew what I needed and delivered like no other has. She is Spectacular!
This red-headed vixen blew more than my fantasy away! Talk about knowing what to do and how to do it…. This was by far the best I have had in a long time.
I feel Mistress Megan is in charge even when not online. I’m her slave.
Megan is extremely open minded. Plays along with even the most taboo fantasies. Close your eyes and enjoy!
Jamie has gotten insanely popular, so she is often “busy” or “offline,” but a call with her is well worth the wait. Sweet, attentive, and often funny as well as dirty, she has raised my fantasy role-play into something hotter than I ever imagined it could be.
Paris is incredible! She has such a sexy voice and an open mind.
My first call with Dixie was so fantastic! Unbelievable voice! So soft, so sweet, so nurturing, so Southern! Dixie is everything I ever wanted in a Southern lady. Her voice will leave you shaking and breathless as she weaves her Southern charm and teasing into your mind. Dixie is the one I have waited for my whole life! Five big stars for this sweet, classy Southern lady who touched something very deep within me. I LOVE Miss Dixie! The Southern Belle of my dreams!
