Sissy Jennifer
Last update
2021-12-15 22:36:32

    Mother said to me, ““Sweetheart, I am going to make you look just like you feel.” She gave me a bra, and put ribbons in my hair, and put makeup on me. She was right, I looked just like I felt - like a pretty girl. ““Honey, you look so pretty, why aren’t you smiling?”  Trying to hold back tears, I said, ““Because I want to look like this all the time, Mama.” She hugged me and smiled and said, ““And you you shall, Princess. So you shall.” 

    Auntie Wants To Play A Game - 2

    Well, I am so pleased to say I’ve been getting a few messages.  I am quite flattered.


    So, let’s talk a little about dressing up. I’m sure you love to do it, and so do I. I love to wear nice bra’s, panties and girdles. Sometimes I’ll wear a corset, and most of all I like to wear things that make it easy to look at me.

    I think you like to look at Auntie don’t you? I think you wonder what it might be like to touch Auntie and feel her close to you.

    I know you’d like me to dress you up, too. So, for a moment I’d like you to think about me putting a little make up on you. You’d like that wouldn’t you. You could look just like Auntie if you tried. You really could.

    SO, to continue our little game, I’d like you to reblog this if you’d like Auntie to dress you up and get you ready to be a little girl. Think of it. And all the girlie things I might get you to do.

    Sometimes those things might be fun and sometimes they may be things you just have to do because you’re a girl. And some of Aunties friends might even want to play with you!

    So, be sure to reblog this and message me and tell me how  much you like to play with Auntie.


    The Proposition Part 2

    See Part 1

    Graham was trembling so much he was struggling to place the key in the lock of Mr Briggs’ front door. He tried to calm himself with a deep breath, steadying his hand by putting down his bucket of cleaning supplies and holding onto his own wrist. He felt relief when he was finally inside, the door firmly closed behind him. The house was laid-out differently than his own. The developers had varied the sizes and styles to encourage a mixture of residents, and this house was very large compared to Graham’s.

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    Ask Any Cocksucker.

    It’s simple. There are guys born to suck cock, and guys born to dominate them and use them.  It’s just the way it is, and it’s a good and natural thing.  But a good cocksucker doesn’t just suck your dick and get your rocks off.  It’s a symbiotic relationship where both find peace, and their true purpose.

    A good cocksucker does so much more than just get a guy off.

    He also worships your masculinity. A cocksucker understands the immense privilege he is given when you allow him to suck your dick. The more you give it to him the hungrier he gets and the better he will perform, devoting himself exclusively to your total pleasure. So indulge him, teach him, and make him thank you for that privilege, every time.

    A good cocksucker makes your penis the center of the world while he’s on his knees for you. That’s a big turn-on for most men. Encourage that by being verbal with him as he is using his mouth to pleasure you. Talk about your penis.  Let him know how hard it is and how good it feels.  Let it echo in his ears as he worships your cock.  Ask him if it tastes good and how it feels sliding in and out of his mouth.  Make him tell you how beautiful it is and how much he wants it.  

    Talk down to him.  Let him know that what he is doing is low and degrading, but if he’s doing a good job of it let him know that too.  If not, then direct him on EXACTLY how you like to be serviced. Give him verbal instructions and feedback. Tell him how to use his lips, his tongue his cheeks his throat.  Tell him how to care for your cock. Sometimes a tiny slap in the face is all it takes to refocus his attention.  Let him practice and get good at it. Or just grab his head and move it the way you want it; fast or slow, just the head, or all the way down to your nut sack.  Any way you want.    Don’t worry, he’ll fall in line.  He really wants to please you. You can be nice about it if you want to, but whatever. He’d be there anyway, nice or not. You’re not friends.  You’re a man.  He’s a cocksucker.  You both have your jobs to do.  So do whatever is most effective. Be gentle or firm, but keep him focused on your cock and your pleasure. Bathe in the glow of your power as he bathes in the glory of your manhood.

    Don’t worry about straight up using a cocksucker rather than having ‘mutual’ sex with him.  Cocksuckers don’t expect or want reciprocation, even if they think they do. It only disturbs their focus, which is YOUR pleasure. I.  A cocksucker is getting exactly what he wants when he’s worshiping you, and so are you. A cocksucker WANTS to be used, wants to make it all about you and your pleasure, your cock, your masculinity. He’s on his knees ready to serve YOU, his feeder, and his leader. So let him what he craves to do. He is happiest pleasuring you alone, concentrating on you and serving you well.

    Having your cock worshiped by a cocksucker, on his knees, and seeing the hunger and gratitude in his eyes, hearing him pathetically moan and whimper, lost in blind adulation and submission, amplifies your power and reinforces your dominance over him. Every now and then you should demonstrate your dominance, just to remind him of his place. So pull your cock out of his mouth and let him crawl to it on his knees.  Laugh at him, hell it’s funny! Make him tell you who’s in charge. Look him straight in the eye when he tells you it’s you. Make him use your name or a respectful term like ‘Sir’. Over time you become more superior as the cocksucker necessarily submits more to you. Most men love to dominate, and you can’t get much more dominant than by using a guy for sexual gratification with your dick in his mouth.

    You should take your time with your cocksucker, and extract every bit of pleasure from his service. It should be an adventure.  Try every conceivable position! Go for a cocksucking marathon!  I’ve had guys worship my cock for literally hours straight.  It’s fucking awesome!

    As you approach orgasm, you should let it build up in your body as long as you possibly can before you cum.  Most men get a little aggro when this happens.  So flex your powerful muscles, grunt and pant, feel your heart racing and go primal!  When you do finally cum, make it the best, most powerful orgasm ever!  And pump out every single last drop of your seed. Make it last. When you think your balls are completely drained, then cum some more! Give it everything you got!  You should be totally utterly spent when you’re through.  Your cocksucker should be in absolute awe of your masculine splendor by now.  Your semen should be symbolic and precious to him, and he should be greedy for it.  Make sure that your cocksucker wears some your cum on his face with pride (to mark him as your inferior), and then swallows every single drop.  He should clean you with his mouth (or his hair, whatevs). If he doesn’t do it automatically then teach him.  If any of your cum should hit the floor or your body or clothes, make him lick it up. Don’t ever let him waste any. It’s common courtesy.

    A cocksucker will instinctively allow your superiority to inform and guide his worship. In turn you will realize, if you didn’t already, that you can get a cocksucker to serve you any way you want and you don’t need to hold back. Cocksuckers expect to be used this way.  They WANT to make your life better for you.  They may protest at first, but trust me, you’re doing them a huge favor. Its how they are wired and what they need in order to be fulfilled. This is why men use cocksuckers. It’s your duty to use them well.  It’s simply the natural order of things.


    🎀💋💕❤️Pretty Pink Sissy!❤️💕💋💄🎀


    so true. Be a worthy cocksucker.


    Whether or not it is something a sissy wants, in time it will be something she needs to affirm her place in the world and to validate her femme, unmanly nature.

    Letter from a sissy to Master


    Thank you for the most wonderful of notes .. your words, and attention, do thrill me. 

    I do want you to understand what I feel .. both the exquisite pleasure and the profound shame. The growing awareness that I make a far better sissy-girl than I ever did a boy .. and the implications that understanding entail. 

    I never intended it would go this far .. but as time passes I realize this is more than just a 'hobby', a sexual 'kink' .. that it arose not specifically to be a girl but from a deep-seated uncertainty about myself as a boy. The evolution has taken time .. each immersion strengthening the association between being girlie and with pleasure and comfort and self .. each surrender to my weakness and addiction strengthening that uncertainty that I have any right to live or love or be perceived as anything but the most effeminate and submissive of sissy-girls. It is an evolution I seem incapable of stopping .. many do, but for reasons of personality I seem unable to. Perhaps it is a need for emotional clarity, an inability to live with the confusion of two worlds .. 

    And yes, I .. who once felt I had no sexual leanings of this sort .. find myself  thrilled and validated that I am capable of arousing you as your sissy-girl, that I am able to satisfy you in a way that I felt deep inside I was incapable of satisfying a woman. A soft, submissive receptacle for you .. each act of submission a reminder of everything you are .. and I am not. 

    The desire for shame .. which so few understand and overlie with tones of negativity .. is such a part of that.  I crave it, hunger for it .. lingering in the background .. never allowing me to escape fully into imagining I am a real girl, always a reminder that I am a feminized boy, a sissy .. that what I've become I fully deserve to have become. 

    I want you to appreciate how every aspect of being a girl excites me in a way no real man would be excited .. how it thrills and shames me to gaze on my soft, hairless effeminate body .. how my clitty helplessly responds to the simple act of rolling sheer hose over my soft legs, how I adore the sight and feel of the lace-trimmed straps of my bra biting into my soft shoulders, the staccato click of my heels as I walk, the hem of my skirt swaying about my knees, the floral scent that envelops me, the texture and taste of the ruby red lipstick .. how I am helpless to avoid the narcissistic masochism that has become my world .. how my sense of validation and fulfillment has become totally dependent on you .. that kneeling to serve you is  more than a sexual act but a confirmation of our respective roles in the world, that I have value and am valued even if for this.

    I miss you too so very much .. and hope to see you so very soon.