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I don't have any solutions, but I just wanted to tell you that I have a similar issue.

Here's my analysis:Chafing can only occur if there is friction when the base ring moves, so we have two options:

1. Try to prevent the base ring from moving, using a belt, for example.
   
2. Allow the base ring to move freely, but reduce friction using lube.
   
   I prefer the first option, because if I allow the base ring to move I don't really feel "locked". I don't have this fully sorted out yet, but the best solution at the moment is to use this:
   
   https://www.amazon.com/ACSUSS-Underwear-Jockstrap-Lingerie-31-5-51-0/dp/B07DHF1K2H/ref=sr_1_46?dchild=1&keywords=strap+on+harness&qid=1574708454&sr=8-46
   
   The way I use it is:
   
   
3. Put the base ring for the chastity device on.
   
4. Slip this ring on top of the base ring, arranging the straps as necessary.
   
5. Place the cage on.
   
   There's no adjustment with these straps, but you can pretty easily pin it to get the fit right and then throw a stich in there permanently. You could also fashion something similar yourself out of a pair of pantyhose.
   
   If using a belt you can afford to go even larger with the base ring, since the cage no longer needs to be held up by pressure from the base ring, which may also be more comfortable.

Hello, you are so sweet to want to buy stuff for your sissies. When I started being a sissy what I was looking for was a clean guy with a clean place, lube, condoms and towel for a shower after/during sexy time. Maybe buy a jewel plug like this one: https://www.amazon.com/Akstore-Quality-Jewelry-Personal-Massager/dp/B01HOCAXDK/ref=pd_lpo_vtph_121_tr_t_2/145-5494775-2603555?_encoding=UTF8&psc=1&refRID=GDDMPT5TGEXJ7W0HQKCX if they are ok with it. My first long time daddy gave me one when we started and I was wearing whenever I could. It was the symbol that I was daddy's sissy and he loved playing with it when we were cuddling. So just maybe find a small gift your sissy will enjoy if you are planning for a long term relationship. Else for one time thing just offer them a nice place and maybe have some clothes if they are beginners/ don't have them.
Sorry for the bad English it is not my native language

It sounds like you're off to a great start!

There are a lot of different breast formers out there. https://janetscloset.com/janets-breast-forms/ here's a non-complete list of different formers. I haven't made the jump to getting breast formers because they're so expensive. This chest plate I want is $160. Which is out of my price range for the moment. In researching this for you, I found "push up enhancers" might be the way to go, which just add some padding to what I already have for $10.
Amazon has a pretty good selection too, just type in "breast silicone crossdresser"
I'm going to go ahead get these

Ultimately, this kink is what you make it, and like I said before be "Safe, Sane, and Consentual". If you don't like what the guy is doing, you should be able to say "[safeword]. stop.", and that should be the end of it. As long as you're up front and communicate what your limitations are (Condom, safeword, safe meeting place, etc.) when you're talking with them, you should be fine. It's as much as a fantasy for them as it is for you.

If you don't like them, don't do them. There are parts of this fetish that I don't like, and they're hard "No's" for me, so I don't do them. <3

I would suggest starting with a training set, like these: https://www.amazon.com/gp/product/B07BHWT1QX/ref=ox_sc_act_title_5?smid=ATVPDKIKX0DER&th=1

Made out of pure silicone so safe for long-term wear, and super comfortable due to the curved base. The largest one has been my regular daily plug for several years now.

If you're looking for something more like a jacket: https://www.amazon.com/Anself-Womens-Shaggy-Sleeve-Jacket/dp/B076ZQ51HR/ref=sr_1_2?keywords=pink+fuax+fur+coat+womans&qid=1563557858&s=gateway&sr=8-2

... And then this is something more like a "coat" coat: https://www.amazon.com/HHei_K-Autumn-Winter-Sleeve-Outwear/dp/B07KPLJ449/ref=sr_1_9?keywords=pink+fuax+fur+jacket+womans&qid=1563557800&s=gateway&sr=8-9

hope this helped. :)

I found the Raycity chastity on Amazon, its stainless steel, has an integrated lock and optional ureathral tube. Liike $26

https://www.amazon.com/gp/aw/d/B01MPX9M2A/ref=ya_aw_oh_bia_dp?ie=UTF8&psc=1

Only 2 solid steel parts, doesnt come off, descreet under clothes.

CB-6000 is also an excellent choice.

You should use an enema. There are enema kits you can hang on your wall and use it while laying on your side. There are also shower heads for cleaning your anus which is my favorite option because they're so convenient.

Here are some examples:

Enema bulb

Enema kit

Enema shower head

If you need an instruction, I found this one useful: https://howtocleanyourass.wordpress.com/

Try something like this: Nip-Xtender by Cradle Plus | Nipple Puller or Extender for Flat,Shy or Inverted Nipples | Nipple Suckers - Pack of 2 with Case | Latch Assist Nipple Enhancer for Breast Feeding Nursing Mothers https://www.amazon.com/dp/B07PZ9QY6F/ref=cm_sw_r_cp_apa_i_bg6GDbQ0847EY

They're amazing

I'm not confident I can answer this with much accuracy, but I'll try. I recall an experiment in rats that generated female sexual behavior in male rats by implanting electrodes at certain sites in the brain. This result suggests that some female brain structures exist in the male brain, and it's possible that these are being accessed by sissies. You can read about it in A Billion Wicked Thoughts by Ogi Ogas. Here is a speech by him - it's some really fascinating stuff.

a lot of the stands you see online will also come with a little bluetooth remote that can be used. like this (https://www.amazon.com/UBeesize-Portable-Adjustable-Universal-Compatible/dp/B06Y2VP3C7/ref=sr_1_6?crid=1DQMIS0H781IJ&keywords=cell+phone+tripod&qid=1557149228&s=gateway&sprefix=cellp%2Caps%2C163&sr=8-6)

https://www.amazon.com/Envy-Body-Silicone-Breast-Mastectomy/dp/B004GP05TQ

This is more or less what I have. Down side is they’ll fall out if you take your bra off but I prefer having it on anyway ;)

Pueraria Mirifica. DEFINITELY works for me (YMMV) but I never went too far. I stopped because it was getting somewhat obvious. You can get it on Amazon.

https://www.amazon.com/gp/product/B01GEUE59G/ref=ppx_yo_dt_b_asin_title_o07_s00?ie=UTF8&psc=1

OPI Nail Lacquer Top Coat, Matte, 0.5 Fl Oz https://www.amazon.com/dp/B0001435D4/ref=cm_sw_r_cp_apap_eBob4ngT89Jec

time lock safe

Put your key inside. Set the timer and it's not up to you anymore.