A sissy strap-on punishment can never be too easy. I love letting my wicked, creative streak out when it comes to punishing my little submissive toy. See, sometimes I wonder how he’d react if I gave him a very LIGHT punishment. I think he’d be even more paranoid, looking around every corner and wondering when the actual punishment is coming. Maybe I’ll try that next with him and barely give him a spanking. I’m sure the paranoia will riddle him. He’ll be looking over his shoulder and expecting a room full of toys I could use to fuck him with!
But usually, he gets exactly what he’s aching for. I’m always willing to supply the matching pain for his actions. In fact, he expects it and yearns for it. My little subbie is a bit of a masochist, a total pain slut that wants a hard, rough fuck every time he “breaks a rule.” And trust me, he’s had me set up plenty of easy rules for him to break. For example, when he comes over, he’s supposed to dress up like a sissy within five minutes of entering my house. Otherwise, he gets a sissy strap-on punishment.
My little sissy toy always wants whatever I can give him. So when he comes over, sometimes he talks and talks, knowing I’m keeping time on my phone. Sometimes he talks so much as he goes to my room to change that he purposely exceeds his time limit. And then, of course, he’s guaranteed to get what he wants. He craves a sissy strap-on pegging punishment, and I give it to him. Once he’s earned his punishment, it’s all up to me. I could be kind, or I could be cruel. I could make him stick a little butt plug covered in ginger paste in his ass. Or even better, I could fuck him for a certain amount of strokes and have him count out each one.
All our games are so wicked and fun. The last time I got to fuck his ass was an improvisation of that second punishment. I had him pick a random number from one to five hundred. The poor soul picked three-fifty-two! Now, he clearly didn’t know what he was choosing, or maybe he was hoping for a spanking instead. Because his eyes went wide the second I told him to bend over and spread his cheeks. And this time, I gagged him too. I slipped a little ball-gag over his mouth, so he was a mumbling and moaning mess during his sissy strap-on punishment.
He couldn’t really move, and he couldn’t yell or whine. I secured his hands to the headrest and had him put his tight little ass in the air. Then, he was entirely under my control. All his days of strap-on anal training didn’t prepare him for such a high number of strokes. He tried to count them out one by one, but I quieted him with the gag. He couldn’t look back at me either; all he could do was twitch and squirm. With every stroke, I made him take the toy from the base of the balls to the head. I could feel his struggle every time I got it in, almost down to the balls. Poor little subbie was getting SORE from this sissy strap-on punishment.
The pegging was too much for him, but it was delicious! He came twice for me through the whole ordeal. I wonder how you would feel, bent over the bed, tied up, and at my mercy. Could you handle my strap-on fucking?
What started with trying on some women’s panties has become much... Read More
Panty Wearing Secret Sissy Fuck Boy Jacob was your class... Read More
MEET YOUR NEW MISTRESS: Pesky Neighbor Made to Submit When you... Read More
Pink lacy panties Joshua likes to wear pink lacy panties... Read More
Shopping For His First Pair of Panties Once upon a time, in a s... Read More
I love a sexy Tranny. Hell, I love tranny JOI and edging just as much... Read More
Sissy Bitch Boy in Waiting “Blow out the candles... Read More
I love a good holiday party, especially when it is adults only left at... Read More
I laugh when men say they’re straight closeted cock lovers. &nbs... Read More
Calling All Panty Sissy Boys!!! Panty sissy boys, let’s g... Read More
Change or Not to Change – A Sissy Boy Crossdressing Dilema  ... Read More
Girlfriend experience phone sex is a must! Girlfriend experienc... Read More
Loved the naughty nurse angle. Ramona made it feel real. I explained what I wanted and we went right to it. Would definitely call her again.
Megan is very personable and friendly and we hit off. She heard what I was looking for and was able to craft a great call that we both enjoyed. I’ll definitely call her again.
Jamie is so dedicated to providing the utmost experience. Whether you have a role play picked out or just have Jamie run wild, the experience is top notch. Jamie is super special and a PSK rockstar. Don’t miss out on this tantalizing experience.
Roxy is simply Amazing!! She does any roleplay. Her oral skills are fucking fantastic. I highly recommend talking to her! You will not be disappointed. She really is Amazing!
Megan was fantastic! She was unbelievable! What a sweetheart ❤️
Wow, Sloane is the operator that can keep a caller on the line longer than requested. She has the sexiest voice, laugh and imagination. We have both clicked together when we get going. Wow oh wow, completely amazing!!
Just simply a great call! Sloane is real & fun. Thank you!
I had the best time last night talking to Alyssa. She is fantastic! She is great no matter what role play. I highly recommend talking to her you and your cock will feel fantastic.
Eden has a sexy voice, tone and presentation!
Jamie read my mind and knew exactly what I needed! And her voice…oh fuck!
I cannot get enough of Romi! She is a special sex goddess. Oh my, after who knows how many calls, I am always very horny and I can truly say she loves to make me happy and most certainly sexually satisfied. There is no doubt in my mind she gets as horny and hot as I do. Love my Romi! Call her for a completely sexually satisfied time, for sure.
Sloane is a gifted conversationalist, with a really unique way of drawing you in and making you feel special. She’s sexy and, if needed to be, highly intellectual. She’s the best!