Miss Adventures - So You Want To Be A Crossdresser

(Please note that monthly assignments will not be shown on the front page. Always use the Archives listed on the sidebar or the Monthly Program Listings Tab at the top of the page to view assignments.)

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This program was initially posted on Patreon starting in January of 2020. It is being reposted here for free. Feel free to follow at your own pace or start from the beginning. Some months themes are specific to that month. October for instance is Halloween themed and might be considered advanced if you just started the program in August, or if you are trying to do the October lesson in April. Other lessons are cumulative based on previous months content. Breast form month follows bra month which makes sense. Just be aware if you start doing the lessons outside of their expected order.  

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Congratulations! This is an exciting time for you. Maybe you're new to crossdressing or you’ve wanted to improve on your crossdressing wardrobe or skills, maybe your wife or a friend thought dressing you up might be fun and you thought so too. Have you snuck around and secretly tried on a pair of panties and would like to do it more often or try smoother item of women's clothing. It could be that you’ve been secretly dressing up for years. Whatever the reason, don't you think it’s time you and the world accepted that you’re a crossdresser and there is nothing wrong with that.

If you’ve ever heard of a 'Couch to 5k' program, this program follows a similar concept. It slowly guides you along, each step of the way until you are a proud and confident crossdresser ready to take on the world. Speaking of couch to 5k, you really should start a workout program if you haven’t done so already. Your health is important. I'm not saying you need to be skinny to be more feminine. You just need to be healthy, for your own sake.

Like any self help program, you only get out of it what you put into it, every week and every month. There may be baby steps along the way for some or giant leaps  for others, but ultimately the goal is for you to be dressed up in women’s clothing from head to toe and out in public by the end of the program. You are either already a crossdresser, or will be when the program is over, so just (wo)man up and do what is best for you.

Each month will provide a new aspect to your feminization. Just like a couch to 5K running program, you wouldn’t be expected to run a 5K on the first day. In this program you are not expected to go grocery shopping dressed as a French Maid right away, that won’t happen for a few months yet. Just kidding! See we're having fun already. In the beginning we need to focus on the fundamentals, even if you have a box full of lingerie hidden in the attic right now, you should start at the beginning.

At this point you should look at the January entry and get started. The rest will happen in its natural progression.

Now it's easy to just read the posts and put things off until next month but in order to really benefit from the program you need to follow through on each weekly assignments. Consider having your own blog, take pictures and write down your progress and thoughts about the process and changes you are going through. If you leave a comment here and a link to your crossdressing blog, a page will be created to everyones diary/blog so we can all share in the journey.

As a show up support, Miss adventures good friend Becky has agreed to follow along with the program and do the lessons with you. It so much easier when you have a friend going through the same things that are expected of you. She will be going a write up of each lesson and sharing it on this page.

Good luck and I hope you get out of this program everything you hope for. 

Your Fourth Lesson - January 24th

 

Your Fourth Lesson - Always Wearing Panties

• Jan 24th - Jan 31st: The next lesson will be posted on February 1st.

• This week is about making wearing your panties a regular thing. You are going to wear them all week long. From the time you wake up, and then right up until next weeks lesson. You will wear them to work, while at home, when you go to bed, all of the time. 

• There are always exceptions but they are pretty limited. You don't have to shower in your panties, and you need to take off one pair to put on another pair, but that's pretty much it. And you'll want to wear a clean pair in case you get in an accident and have to go to the hospital. At least that's what mom would expect.

• This week your panties are your regular underwear you will wear them every day and every night

• Are you trying to keep this a secret from your wife or girlfriend? First off, why? You want to become more feminine, right? Maybe you get caught, maybe you don’t, maybe you just come clean and explain it to them. As a special incentive, you don’t get to masturbate until after 5pm on the 31st of January. And you only get to do that if you wear your panties every day like a good girl should. 

• Take some time to reflect back on this months lessons. You now own panties of your very own, that you bought in a store that sells lingerie. You wear your panties to bed, to work, under your boy clothes. You love them so much you masturbate just thinking about them or when you are wearing them. There is so much more to do and learn but  you wear panties now. That's something you do, wearing panties.

• You won’t have to wear panties 24x7 in the coming months, but you’ll probably want to. Just because we will be moving onto other aspects of feminization doesn’t mean you should stop wearing your panties. Be sure you are keeping them nice and clean between wearings. And if you feel like you need more panties, go ahead and buy some more. You know your size and what style you like. Go ahead, you deserve it.

Your Third Lesson - January 16th

 Your Third Lesson - More About Panties

• Jan 16th - Jan 23rd: The next lesson will be posted on January 24th.

• Last week was about getting you to fall in love with your panties. As the days progressed did you find yourself thinking about when you would be able to slip into your panties and play with yourself? That was done as a means to change your thought patterns. Hopefully now you have associated wearing panties with sexual release. Not unlike Pavlov’s Dog you may now become aroused just at the thought of wearing panties.

     

• We are going to change things up a little this week. This week you will wear your panties between 2 and 4 hours a day. Maybe it’s when you get home after work, maybe you need to bring them to work and change into and out of them in the bathroom, hoping you don’t get caught. Trying changing into your panties at various time throughout the day. This is meant to make you think about
  planning and executing when and where you will be wearing your panties.     

• This week you only get to masturbate three times…and you have to do it with your panties off. Just think about your panties while you masturbate, remember how they felt last week when you were wearing them while you masturbated. Wouldn’t you rather be wearing panties rather than just thinking about them and jerking off?

Your Second Lesson - January 9th

 Your Second Lesson - Love Your Panties

• Jan 9th - Jan 15th: The next lesson will be posted on January 16th.

• If you don’t have five pairs of panties yet, you will need them. This week you only get to wear your panties for one hour a day, but you will definitely enjoy the experience. I know you want to wear your panties, all the time but there is a reason. This week we are learning to love our panties and to do this we need to associate wearing them with pleasure. If you just wear them willy nilly the'll be just like any other underwear, albeit much prettier.

• Focus on the fabric and sensation of the silky material touching your special parts. It’s OK if you get hard wearing your panties, it’s encouraged. Don’t masturbate right away, you need to wear them for a full hour first.

• This week you are allowed to cum while wearing your panties. Enjoy it. Do this every day. You should have at least five pairs of panties if you followed last weeks lesson. By the end of this week you should realize that your panties are a treasure. Are you thinking about them when you are at work, knowing that your special panty wearing time is just around the corner. 

• Your panties also need to be cared for as well. Hand wash them at some point before you wear them again. Next month you can use a washing machine. But for now you can wash each pair before you go to bed or save them up and hand wash all five at once. If you made a mess in your panties do at least a little clean up right away afterwards. You want to keep your panties soft and clean. Nobody wants to wear crunchy or stained panties.

• Next week we'll discuss wearing your panties a little bit more often or for longer periods of time.
  

Your First Lesson - January 1st

 

Your First Lesson - January is Panty Month

• Jan 1st - Jan 8th: The next lesson will be posted on January 9th.

• Your first lesson, as you probably would suspect, is to get a pair of panties of your own. Actually, you should probably get five pairs. Now understand that we are not trying to break the bank here, if you already own four pairs you only need to buy one. The important part is that you do have to buy at least one pair and you have to go buy it in person. DO NOT order your first pair of panties online. You will be able to so in the future but for now it must be in person. Remember the goal here is to get you out in public dressed up as a girl. How can you expect to do that if you can’t go into a store, dressed as a guy and do something as simple as buying some panties. 

• You don’t have to go to Agent Provocateur or La Perla either. Victoria’s Secret or some other brick and mortar store is fine. Maybe you can find a sale somewhere. You can go to Walmart, Target, Costco, or any store of your choosing.  

• Remember this is a store and they want to sell you products. There is no shame in that. If you have a question, ask it but don't be weird about it. If you were to buy a mens shirt and couldn't find the right size you might say, "I can't find this in a Large, do you have any in stock?" It's the same thing here. And you don't need a cover story either. If they ask if it's a gift, you can say yes or no, it's up to you. If they ask if it's for your wife, you can say yes or no, it's up to you. Respect is a two way street, treat the store, the customers and the staff with respect and you will be treated with respect too.

• Try buying some different styles and colors, in the end you will want them to fit well and comfortably, this will help you determine what kind of panty you like to wear. Maybe you like several styles, that's great. Even a thong can become comfortable to wear, you just need to get used to it. Be sure to avoid boring cotton panties, they are too similar to mens underwear. Get something soft and silky, they are so much more fun to wear. 

• You can do some research ahead of time if you want to, so you can order the correct fit or get a better understanding of what type of panty you are looking to buy for yourself.

• You may try them on when you get home just to make sure they fit, but don’t wear them for any extended length of time just yet. Just think about the fact you will be wearing panties soon. This lesson is about going out and buying  panties. You have all year to wear them, but you won't start wearing them until next week.

• I know its hard, pun intended, so you can masturbate this week three times only. You can think about your panties, but you can't wear your panties, even when you masturbate. Think of it as a marathon and not a sprint, let's start with some self control right out of the gate.