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?
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Elise was fantastic. I loved how she humiliated me going all dressed up like a little sissy whore!! She’s really good! I loved how she humiliated me. Thank you Elise and thank you PSK girls
Aileen rates the highest in every way!
Gemma is a Perfect 10! My calls with her get hotter and hotter every time! She is smooth, sexy, and wild! And the best part, You are free to say whatever you want to her and she never judges you! She gives you the freedom to be yourself! I love Gemma and her black girl magic! 😊❤️
In my opinion, JOEY is the best there is! It’s been over 2 years now that I’ve been calling, spanning countless hours. Worth every cent. The only reason I call here is for her, and always will be. She’s the best. A 5 star rating is far too low for her.
I can talk to her about anything. Romi can be anything I want her to be in a role-play as she goes into it seamlessly. Great experience-Thx Romi
I was so glad to see her back, because Lucy is fantastic! She’s got the perfect combination – filthy mind, amazing body, and sexy voice! Any ideas you have she’ll love, any fantasies you have she’ll make even better than you thought they could be!
Jade is hands-down my favorite operator on the site. She is smart, sexy, seductive, and open to any and all ideas I’ve had! Her creativity and sultry voice will take you to a new level, I absolutely recommend her!
I have been calling Aileen for many years. She is Awesome!!
Alyssa is fucking awesome. Any type of roleplay with her will leave your cock rock hard. She can also be dominant or submissive. Her attention to detail is top-notch. Oral skills are a 10. I highly recommend talking to her. Your cock with thank you!
I spoke to Romi several times. Not enough though. Wow!! She is really the best.
I can’t keep up. She is just Incredible!
Excellent voice, intelligent and interesting is how to sum up Aileen. Her acting skills and demeanor are relaxing and very comforting. Aileen is a gem!
I am a long-time caller to phone sex lines. I have tried other services before finding PSK. The overall quality of PSK is 100% better than others. I have tried and liked a few of the women on here. I had great calls with Jacey and Kimberly (retired). After Jacey changed her schedule, I was looking for my next favorite. I didn’t click with some, so I didn’t call them back. Then I found Maddie! Maddie and I clicked right away. She can make me feel like a long-distance lover and did that with the first call. Maddie makes me want to talk to her again and again. Our most recent call was a perfect example of how great Maddie is. She told me what she was wearing and asked me what I’d do if I were there with her. 10 minutes later, I was having an extremely powerful orgasm! She didn’t ask me what kind of role play I was in the mood for (she has and does ask sometimes). She just took over and gave me a great scenario, which Maddie can do because of how well she connects with me. She knows exactly what I like and how to get me going. If I had the stamina (I’m not a young man anymore), I would call Maddie daily! She makes me feel like a young man because of how hard I get every time I think of our most recent calls. I hope this helps you understand how much I love Maddie!