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duration 21:43
Naive Mom Condom Education video from Miss Ellie
Naive Mom Condom Education by Miss Ellie My son approaches me and wants to talk. I try and shrug him off, talk to dad about those kinds of things! But he's always been more comfortable and open with me, so I eventually oblige and have the uncomfortable condom talk with him. You (my son) say that your gf is ready for the next step but you've got no clue how to put the condom on. I'm in disbelief and try every avenue to consider before eventually caving and showing you how to put it on. With a condom on, your uncomfortable mom hardly able to look at you, you take your perverse plan a step further and exclaim that you won't be able to feel anything with the condom on. I touch your hard, condom wrapped cock and say "see? yes you can." but you consistently tell you you cannot feel anything. Infuriated, I jack you off and eventually shove your cock down my throat to prove you can feel it. You still say you don't. Dad calls and I answer, needing to walk away for a moment, you seize your opportunity and remove the condom so when mom comes back and starts sucking you off again, she's got no clue it's her sons bare cock in her mouth. Once she notices, it's time to hang up with dad. He cannot know about this! You shoot a load all over my face, unexpectedly and I sit in shock. You just nutted on your mom. A few hours later, I thought you'd left and instead, I find you watching me masturbate on my bed while licking your cum off my fingers. I try and try to deny it but you pull my legs to you and show that big hard cock again, this time, I submit and tell you to shove that cock in your mom. The ending of this video is a dirty surprise :)
duration 18:34
Revealing Your GFs Sissy Chastity Demands video from MissFreudianSlit
Revealing Your GFs Sissy Chastity Demands by MissFreudianSlit Part two in a series of customs, it's time to move forward with your girlfriends demands. She told me she's been enjoying you becoming her sissy cuckold, but you're touching your little clitty a little too much.... are you focused on her needs during sex? Are you anticipating her wants and desires and her need for water and more lube while she's getting fucked?  It's time to introduce chastity into the mix! I brought you more underwear- two cute little pairs of panties for your sissy training. And now to introduce you to your next step - wearing a cage on that little thing. First, I show you a very large cage... you can't fit that even at full capacity so this definitely isn't the right cage for you. The next cage is a small cage, perfect for tiny dicks to get a little bit hard in, but it's very snug. The last cage is your future - small, almost flat. Don't worry, I'm teaching your girlfriend how to ease you into it.... it's up to her how long you wear the cage for or how often you're allowed to cum! Before I lock you up after breaking the news to you, I think we should let you cum one last time before I send you back to your girlfriend. Start associating this feeling of restriction and denial, because it's all part of training your brain to enjoy being caged. Fetishize this feeling. Give in to the fear and excitement. Cum for me, after I count you down. Then, I'm going to put this cage on your little dicklet and call your girlfriend to come pick you up and take you back home. Are you ready to be her little caged sissy cuck?
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