Why fight it any longer? The need, the desire, the unexplainable itch in the middle of your back which you can never reach. Just give in and taste what it's like on The Femme Side.

 

After The Prom: It’s better to give and receive than to simple give and make a run for it.

After The Prom: It’s better to give and receive than to simple give and make a run for it.

First Date Traditions: There’s the dressing up, the picture, the picture with the boyfriend, the groping in the car, the blow job, swallowing your first load of cum, and the fumbling kiss at the door while your mom watches. It’s going to be a great night for firsts!

First Date Traditions: There’s the dressing up, the picture, the picture with the boyfriend, the groping in the car, the blow job, swallowing your first load of cum, and the fumbling kiss at the door while your mom watches. It’s going to be a great night for firsts!

Home Economics: Where was this final exam when I was in high school?

Home Economics: Where was this final exam when I was in high school?

0pentoanything asked
So I have been acclimating my self to my new chastity cage steps at a time but I tried sleeping in it tonight and I woke up in pain three times and I had to eventually take it off to give myself a rest. Any tips to help me get through the night and accomplish my sissy dream?

Depends on the type of pain it was. You naturally have several reoccurring erections during the night. If that’s all it is then guess what, sissy. That’s the price you pay for being caged. It’s supposed to wake you up that way. It will only get worse the more you go without an orgasm.

You might try milking your prostate a little more. It’ll help somewhat, but not much.

If it’s pinching you then that’s a different matter entirely. Try a little more baby oil to allow things to slide around easier and acclimate to the confines of the cage. Whatever you do, don’t use any sleep aids (over the counter crap, or behind the counter crap for that matter,) that might make you sleep through an injury.

Alternately, you can always go see a phchyatrist specializing in gender issues and an Endocrinologist and see about starting on feminine hormones. After a certain point you won’t have to worry about erections anymore. I certainly don’t miss them.

Your Very Own Breasts: What sissy in his right mind wouldn’t want a pair?

Your Very Own Breasts: What sissy in his right mind wouldn’t want a pair?

Anonymous asked
is it dangerous to use a dildo in the anus?

In general I say no, it’s not dangerous. However, you must exercise common sense as well. I wouldn’t just shove something the size of a large cucumber up there at the drop of a hat. Start small, and use plenty of lube at the beginning until you get the hang of things. Then you can go larger in incremental stages.

Listen to your body when doing this. If it hurts, stop. Use more lube, get a smaller dildo, go slower. If it hurts then you are doing it wrong. Pain during anal sex is an old wives tale that is perpetuated by porn and pain fetishists.

It should not hurt if you are doing things right.

Threesomes: It’s always the guy that cums on your face that wants to take the blackmail pictures. What is that?

Threesomes: It’s always the guy that cums on your face that wants to take the blackmail pictures. What is that?

Piano Lessons: Sometimes playing with the teacher is more exciting than playing scales.

Piano Lessons: Sometimes playing with the teacher is more exciting than playing scales.

Embarrassing Erections: It’s best just to keep it locked up until it’s made into something more useful.

Embarrassing Erections: It’s best just to keep it locked up until it’s made into something more useful.

A Mirror For Your Bed: Your new sissy cuckold should always have the chance to see what she looks like when she pleasure’s your bull. It can only increase the humiliation she feels at being made to take another man’s cock inside her body.

A Mirror For Your Bed: Your new sissy cuckold should always have the chance to see what she looks like when she pleasure’s your bull. It can only increase the humiliation she feels at being made to take another man’s cock inside her body.

Proper Training: It’s paramount to practice all the time in order to be the best femme-boi you can be. This is your future. Don’t slack off.

Proper Training: It’s paramount to practice all the time in order to be the best femme-boi you can be. This is your future. Don’t slack off.

Anonymous asked
Any advice for a sissy who isn't quite an adult yet?

Grooming should be your number one piece of advice that I can legally tell anyone regardless of age.

Always make sure you separate and pluck your eyebrows so they are neat.

Make sure to always use a good conditioner in your hair, not the cheap stuff. Don’t use a hair dryer if you can get away with it. Instead, brush your hair dry in long even strokes from root to ends. If your hair is longer (past the shoulders) start carefully at the middle first to work out the tangles and then brush from root to the ends.

Everyone can use lotion or baby oil after their shower to keep their skin moisturized.

Everyone should use an emery board to file their nails and not cut them.

Lip moisturizer or at the very least lip balm for soft supple lips. 

Everyone should do these basic things sissy or not. it keeps you fresh and ready for when you want to do something more. That way there won’t be a large change in your personality and/or your appearance.

0pentoanything asked
I love your challenges you've given me and excited to do them... but I'm severely in the closet how do I explain shaved legs to people who ask? Especially my family. (I still live with them.)

Someone asked me this in a an earlier message, but it’s been a while so I’ll cover the subject again.

Using excuses to shave your body is not that hard. Do not use the lame “I swim” excuse. It’s lame and unless you have a history of competitive swimming then they’ll know you’re a closet trans.

Chaetophobia is the fear of hair. It is a legitimate phobia, and like all phobias are strange and often irrational. That’s why they’re called phobias. 

I suggest starting off small, like overreacting a little when you find hair in your food, or in your mouth, etc. It happens to everyone, and you can “plant” the evidence when people ask what you’re freaking out about. Just remember the words, “disgusting, gross, and GAH!” If you can manage it, fake vomit (cover your mouth and make a run to the bathroom to fake dry heave. Don’t try to fake vomit because it always sounds fake.)

Get a general unhappy look on your face all the time and start rubbing at your arms and legs on occasion. This will enforce the image in their mind.

Then shave your body and remember to act relieved and happy once it’s done.

If someone makes fun of you then get offended and make sure you can point at their phobia (everyone has one) and make fun of it in return. Remind them that, “It’s irrational and I understand that. Why do you think it’s a phobia! I’m not hurting anyone, so fuck off!”

I did this when I went through my skittish phase and it worked like a charm. Only one person acted like they didn’t believe me. And… well, fuck him. He was an asshole anyway.

0pentoanything asked
So I recently bought myself a CB-3000 and I was wondering if you could give me any challenges or kinky guidelines that I could follow? I'm a huge fan btw!!!!!!

Congratulations! The first chastity cage can be such a joy.

A word of warning. The CB series has been known to split apart at the plastic seams at times. They’ve mostly worked the problem out, but it still does happen. I tell you this to warn you not to store your key away where you can’t get at it in case of an emergency. Being pinched can seriously hurt. This usually happens when the wearer is larger than normal and a large amount of pressure is being placed upon the device. So if you’re a tiny sissy like most of us then you probably won’t have anything to worry about.

Guidelines: Follow the instructions. They are there for a reason. Deviating will cause nothing but pain, and not the good kind.

Challenges: A big reason to wear a chastity cage is to get you to do the things that you wouldn’t normally do in order to get a reward at the end of the challenge or goal. 

My goals were always to feminize myself further and further until I had to come out of the closet and announce my feminine self to the world. So that would be my challenge to you.

The first challenge is to shave your entire body below your eyebrows. You’re not allowed to take off the cage until that goal is reached and maintained, except for proper cleaning or another reason labeled in the instructions you received with the cage.

The times it is off you are not allowed to pleasure yourself in any way other than anally. That’s another reason to wear a cage, to train yourself to orgasm anally, which will be another goal later, when you’re so horny and frustrated that it’ll be a much easier task.

When you’ve reached your goal you may take off the device and masturbate in any way that you want (once and only once). Then place yourself back in chastity until the next goal is reached.

Goals are to be maintained at all times. That means you when you’ve completed the shaving goal you must shave all the time, alternately you may have yourself waxed or wax yourself. Any method of depilatory is fine.

BTW it’s always a wonderful feeling to know that my blog is appreciated. Thanks!