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November 2020
Sunday November 1
Monday November 2
Humiliated by Your Jilted Lover

Hello my darling. What a beautiful rose you sent me. It’s so delicate and fragrant. Did it make you think of me? Do you think that I am a delicate flower, so easily torn to pieces? Apparently you also think that I’m weak. I read your letter… darling. I read every last desperate word out of your lying mouth. You do have a way with words. I’ve saved all of your letters. They were precious to me. And this last one is precious to me because it’s a reminder to never allow another man to take advantage of me or insult me. Oh yes, so good with words. “If you would accept my proposal, I would be the happiest man who ever did live.” It’s sad that you’ll never know what true happiness with me is. In tearing up this letter, I show you what I think of your words: flowery and meaningless… just like this rose. You thought you could spend a few dollars and all would be right? You’re so arrogant. “I think of the way the light played across your hair, highlighting the copper as precious shiny pennies. And, if I may be so bold, I think about your ample breasts and pink nipples moving ever so slightly against my gentle touch. I cannot erase you from my mind.” How interesting. My darling, I owe you nothing. One day I will wrap these milky breasts another man’s cock, but you… you will never feel them again. You think that I am fragile. I am not fragile at all. I will heal and move on, and the next man I allow to touch me will be so much better than you. Now you will spend the rest of your days thinking of me, pining over me, wishing you had not been so arrogant and foolish. You think that I will come crawling back to you, but I never will. You will dre.am of me for the next 50 years.
Humiliated by Your Jilted Lover

Tuesday November 3
Wednesday November 4
Thursday November 5
StepMom and StepSisters Teach You How to Fuck

Thursday Throwback (2016): You know your stepMother has something serious to say, but you really didn't see this coming. Apparently your girlfriend told your stepMom that you had sex & you came really fast. You're so embarrassed, and you can't believe your girlfriend told her, but your stepMom says it's completely normal & you just need some training. Your cheeks burn bright red as your stepMother says she told your stepSisters & they've agreed to help you. StepSisters know?!? Aw man. But then your stepSisters come into your room, and you start to realize what this "help" and "training" is. Your stepSisters are dressed so hot, and they sit down on the bed with your stepMom. StepSisters Raquel & Taurus say that since they're your older stepSisters they have to help you. The fam has a reputation to uphold after all, and we can't have you coming from a household of all women & not knowing how to please a woman. StepMom starts to suck your cock, and you can't believe this is happening. Then Raquel & Taurus join in, and they take turns deep throating you. You've seen this before in a porn, but you never thought it would happen to you... let alone with three women... let alone with your stepMom & stepSisters. They each fuck you cowgirl style, then reverse cowgirl, and each rides you in a different way. Each time your young cock feels like it's going to explode in an intense orgasm, they switch speed, technique, or they take turns. StepMom explains that each has her own technique, and by varying that & the speed, they're edging you & helping you learn not to cum too fast. She tells you that she & each of your stepSisters must cum on your cock, pleasuring themselves with your body, before you're allowed to cum. It's torment but it's amazing. Finally, when they've all orgasmed, stepMom gives you permission to cum. StepSister Raquel helps get you there with her skilled mouth, but you just can't help yourself... you cum right into her mouth. She's a little upset about it because you didn't warn her. Taurus tells you that's not polite. But stepMom says it's just proof that you need another lesson. You hope for many more lessons from your hot stepSisters & stepMom.
StepMom and StepSisters Teach You How to Fuck

Friday November 6
Saturday November 7
Sunday November 8
Monday November 9
Tuesday November 10
Wednesday November 11
Thursday November 12
Friday November 13
Saturday November 14
Sunday November 15
Sexy Doctor Milks Your Cock

I’m your doctor and you’ve come to see me for a check-up. As I go through the usual questions, you mention that you’ve been having trouble getting an erection. I need to take a closer look, so I carefully inspect your penis, checking it over and moving it from side to side as I inspect your balls. I “accidentally” give your penis a little stroke now and then. I notice that you’re getting an erection, and I say that I think things are fine (wink) but it would be best if I empty your balls, and as a professional, I will of course help you.... with a handjob, and then with sex.
Sexy Doctor Milks Your Cock

Monday November 16
Tuesday November 17
Wednesday November 18
Thursday November 19
Friday November 20
Saturday November 21
Sunday November 22
Monday November 23
Lady Fyre's School for Sissies: Orientation

Welcome to Lady Fyre's School for Sissies. This is quite a big step for you, but I know that you can do it. My office staff and I reviewed your application, and it seems like you're smart enough and dedicated enough to be successful. Let's start with some basics like your pronouns and the words you'll use to refer to parts of your body. Language informs thought, and it's very important sissy for your thoughts to be aligned with your vision for your future. I know you have goals, and I'm going to help mold you into the sissy that you were always meant to be. We have some very strict rules at this establishment, one of which is that at first you will not be allowed to touch your clitty or pussy at all. If you're caught, it means immediate expulsion from the program, and you will never be allowed to return. The greater the temptation, the harsher the punishment for giving in. Over time, as I see your behavior aligning with your true nature, you will earn privileges, such as new exciting clothing appearing in your closet. Tonight, while you're removing all of your body hair, an assistant will place a new negligee in your closet. Once the assistant has deemed you sufficiently hairless, you will be allowed to put on the first outfit of your new life. Make sure to do a good job sissy, and don't disappoint me on your first day.
Lady Fyre's School for Sissies: Orientation

Tuesday November 24
Wednesday November 25
Thursday November 26
Friday November 27
Saturday November 28
Sunday November 29
Monday November 30
Tuesday November 1
Wednesday November 2
Thursday November 3
Friday November 4
Saturday November 5