Slutty Task For Experienced Sissies

Are you struggling in chastity? Whether you are new to having your cock locked away or a seasoned cage slave, you may struggle at times throughout your chastity sentence. The urges to remove your cage and masturbate regularly may be strong, and become more intense over time. However, instant gratification is rarely rewarding in the long term. I am here today to remind you why you are doing this in the first place, and why it will benefit you in many ways. Watch this clip to reinforce your devotion to denial during chastity.

Today is going to hurt. You are going to jerk off for me, but on my terms. I have decided that if you want to feel the pleasure of stroking your cock and ejaculating for me, you are going to feel some pain along with it. Today you will feel as though your cock and balls are on fire, and being frozen, to be precise. You will need a tube of IcyHot, Bengay, or any other similar pain relief cream. Follow my instructions, and enjoy the combined agony and bliss of this fun JOI challenge.

You have spent plenty of time browsing vanilla webcam sites, and are well aware of the types of shows that many mainstream models perform. Cum shows. Toys shows, Hardcore, explicit shows. All for the entertainment of horny men. Your specialty! You love dressing up in pretty lingerie, fucking yourself, sucking cock, playing with your toys, and obeying every depraved demand of your observer. I have trained you well as my sissy whore, and I think you have the potential to be an incredible webcam model. Today, you are going to put on a show for me. A private show, on webcam! I will direct the show, of course. You will need ALL of your toys: dildos, plugs, and anal beads, if you have them. Dress up in your sexiest outfit for me-I want to make you marketable, pretty, and eye catching on cam. I need you to be good at this, so I can potentially sell you to other men in the future. You are going to perform a VERY sexy blowjob show, and then play with and fuck your ass until you cum. I want a very steamy, hardcore cum show. You are always horny and eager to please, so this all should not be much of a stretch for you. Just be yourself, and follow my instructions.

A new year has just begun, and you are still the same closet fag. You constantly fantasize about sex with a real man, but are too much of a pussy to actually do it. You may have even had opportunities or plans to hook up with men in the past, but ultimately never followed through. Today, in my presence, you will resolve to suck and/or fuck a REAL penis in 2021. Not a dildo or a fuck machine. We both know those do not replace a throbbing, rock hard penis, and fleshy balls filled with hot cum. No more excuses. We both know how badly you need this. Make me proud, and complete this task.

You are going to jerk off for me today, but not in the way that you expect to. I present you with a fun little exercise to test how GAY you really are. Spoiler alert: it involves stroking yourself to something truly humiliating. I know that you crave more than just female domination-you need COCK to get you really excited. Relax, follow my commands, and prepare to masturbate and cum to some deeply degrading porn.

****Custom clip, no names used***
Why is your wife always hanging out at the next door neighbor's pool, and why does she insist on wearing the tiniest bikinis to do so? She tells you that they are just friends, but one day, you find yourself peeping on them over your fence, and you are alarmed at what you see. He has his hands all over her! He is tickling her, and she is playfully telling him to "behave". If you see this upon a random glance, who knows what else is going on over there. You have caught your wife cheating one time in the past, two years ago, and suspect she has been unfaithful since then. She stays out late regularly, is constantly texting and sending selfies on her phone, and wears extra sexy outfits on any possible occasion. Recently, you saw her outside chatting with a tall, muscular guy. You asked her to come inside, and he threatened to bConsume you up! You feel humiliated and in need of answers. You have no control over your wife, and know nothing about her male "friends".
Today, you walk in on your wife taking selfies in a bikini. She has her flip flops on, and is ready to head over to the neighbor's house for their usual pool parties that you are never invited to. To your surprise, instead of brushing off your questions, your wife has an honest talk with you. She spills the entire truth about what she has been up to. She is not cruel, but does not hold back, and is completely transStep-Parent. Do you think you can handle it?

I know you have been dreading this conversation, but it is about time we sat down and talked honestly about our relationship. The truth is, I am way out of your league, and your smaller than average cock has never satisfied me. We both know I have just been using you for money, and cheating on you the entire time we have been together. At this point, I am bored of you, and no longer want to pretend to care about you. In this important discussion, I break up with you, but since you are so desperate to keep me in your life, I offer a few alternative solutions that you may find appealing.

I am goddess, a true earth angel, and the definition of perfection. My big natural tits, beautiful face, long pretty hair, and curvy figure make me irresistible to all men. But those traits are not the first thing that you notice when you look at me. You notice my mouth. My soft, plump lips, which I regularly paint bright red. You cannot look away from my shiny, slick lips, and when I lick them, you melt. I love to tease you with my lips and mouth, making your cock rock hard, and your mind melt. You love my mouth so much that you are constantly fixated on it. You would do anything to get inside it, and live there forever.

You always beg to see me in blue denim jeans. Other men get hard seeing me in lingerie and fetish wear, but nothing makes you weaker than my tiny waist, round ass, and sexy legs in tight, fitted denim. It's your lucky day. These durable, high quality Madewell jeans hug every curve of my perfect lower half. I catch you staring at me for a little too long, and decide to indulge what you have been begging for. But, of course, there is a catch. If I am going to let you worship and jerk off to me in my sexy denim jeans, you are going to do it exactly how I tell you to.

Another boring, stressful week in quarantine. You have been jerking off nonstop. You are somehow more horny than ever, seeking out all the femdom porn you can get your hands on. You stroke your cock to my live cam, my clips, and my photos. My beautiful perfection turns you on so much that you cannot get enough. Your favorite way to jerk off to me is by edging -your obsession. You pump your cock until you are ready to cum, stop, and then keep going. A never ending cycle. You eventually work up to a satisfying orgasm, and end your session for a while. Until now. I dreamed up a fun challenge for you to complete for my pleasure while in quarantine. It will be difficult, but ultimately deeply rewarding. You will get to cum, eventually, but that may not be for a long while. How long, no one knows for certain at this time, ha! And yes, you can fuck up, but it will cost you. Have fun, and happy edging.

Stay at home orders in your state are being lifted in just a few days, and your hot wife can not wait to get out. No, not to get her nails or hair done-she has more important priorities. She has been stuck in quarantine with your average cock for months, and has been craving the touch and rough fucking of a REAL man. Today, you catch your wife taking sexy selfies. Who are they for? She never sends you photos of herself. And who has she been texting so often lately? It is time for a confrontation, and she decides to lay it all out and be completely honest with you. Your wife has had the neighbor's number for quite some time, as he kindly collects your packages when they are left outside on the porch for too long. Well, during quarantine, he and your wife have become closer, and recently, he sent a picture of his big, thick cock. It is SO much bigger and sexier than yours! Plus, he is exciting, funny, and adventurous, unlike you. Ever since the cock photo, wifey has been obsessed with fucking him. They are currently planning an elaborate, romantic night including a homemade dinner (he cooks, too!), movies, and lots, and lots of sex. Maybe if you are lucky, you will get some live video footage of the evening. You should be thrilled-your unsatisfied wife is finally getting some REAL dick!

You have already been edging for a while to my clips, photos, and live stream, and you cannot hold back any longer. You are aching to release, to finally cum for goddess. Buying this clip will grant you permission. I give you a quick, painless countdown. Well, not completely painless-I have to tease you for just a bit longer before we finish what you've been working toward.