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Well, I'm going to assume that you have already talked about it and that it's something he's interested in too.

From there it's what you both want out of him being in chastity during it. Is it just because you really want to focus on his prostate and want to remove the temptation to touch, or is it more of a control femdom thing? If it's about the temptation and really focusing on his ass, maybe don't have the chastity device at first. In fact I'd recommend giving him a nice long and slow prostate massage to really awaken his prostate. Then go to slow pegging that isn't putting too much pressure on his prostate.

Taking off the cage for me hasn't really made it more sensitive or painful, my penis is actually much less sensitive because I just spend the last 20 minutes only focusing inside me.

If this is about the femdom stuff, just talk about it before hand. Play up the aspects that you both like. If you're experienced in this then feel free to ignore my advice, but I'd read both the gentle femdom sub and the femdom community sub and see what aspects you like.


From there it's about sizing. If your man is more than 1.5 inches in diameter for girth, don't get the holy trainer knock off. I'm 4" long flaccid and 1.4" flaccid, and those things are a bitch to get on if you're uncircumcised. If he is, then it might be easier. I got the "large" size here

Resin Chastity Cage https://www.amazon.com/dp/B01M9FE42B/ref=cm_sw_r_cp_apa_i_we-KDbWG5ZM2T

and if it was just a bit thicker it'd have been fun, but getting it on was so hard it's not worth it.

Right now I'm trying out this one

https://www.amazon.com/dp/B075MCMM6N/ref=cm_sw_r_cp_apa_i_zf-KDbPXYCB3Z

and it's much better for my size. It's a lot easier to get on for me.

If your bf is more than 6 inches flaccid, I might get this one.

https://www.amazon.com/dp/B01I155M94/ref=cm_sw_r_cp_apa_i_Wg-KDbYATWPFX

And if he's more than 2 inches thick, you're going to need a custom. Maybe Cherry Keeper https://www.shapeways.com/shops/josielynn-s-body-jewellery


But /r/chastitytraining is going to know better for that one.


So good luck! Have fun, be safe. And remember, if the cage hurts, it's not a good cage.

For the best beginner experience, the dildo needs to have an adequate insertable length and a comfortable diameter. I advise strongly against pegging kits I've seen from otherwise great brands; they are a waste of money and can provide a bad first time pegging experience. Why? Dildo is too short at 4-inches and harness is flimsy (straps don't provide a snug fit low enough on her pubis bone which you need for control). I've been pegging for 15 years and have taken many pegging v-cards. My number one recommendation for a dildo is the Vixen Creations Mistress Dildo. You can find it on Amazon for $42. The best reasonably priced harness I have used as of late is the U Strap Avalon Jock Style Strap on Harness also available on Amazon for around $30. I have suggestions on how to improve the harness out of the box if you go with this one. DM for those. I suggest water-based for pegging because silicone lube ruins silicone toys and lube gets all over the giver's hands making them very slick. The giver needs her hands free and clear to guide the dildo. I keep a damp black washcloth by me at all times when pegging to deal with excess lube on my hands. I use Wet Light Liquid Water-Based (also available from Amazon at about $8) All USD. I can give you reasons why all of the above are my tried and trues for budget friendly pegging but this would make the post long. Wishing you and your pegging princess happy pegging. Welcome to the #peggingrevolution. :)

Lube: https://www.amazon.com/gp/product/B00CPQUP3E/ref=ppx_yo_dt_b_asin_image_o01_s00?ie=UTF8&th=1

Didlo (link is to a glitter dildo, but they come in black too): https://www.amazon.com/gp/product/B00L06BDYK/ref=ppx_yo_dt_b_asin_title_o03_s00?ie=UTF8&psc=1

Harness: https://www.amazon.com/gp/product/B00R6WVV2Q/ref=ppx_yo_dt_b_asin_title_o01_s01?ie=UTF8&psc=1

Thank you! ☺️ I’m pretty fond of the way it looks myself! It’s a Sportsheets! They’ve got a version that has the bullet vibe pocket, but lots of reviews I read say the pocket doesn’t put the vibe in the right place. It didn’t seem like a necessity for me at this point, so I couldn’t see paying almost double for something that may be useless. I also considered a brief style harness since they look great for beginners, but I wanted the sexiness factor a jock style harness has. They just look sexier to me.

I will! When we talked he asked what about it exactly turned me on, if it was a dominance thing. I didn’t really have the right words to express it then, but I knew it wasn’t that hardcore femdom type of stuff most people automatically pull up in their minds. Now I realize it’s about the sensuality, vulnerability, and trust. Often we don’t see the vulnerability from men. And if I’m being honest, it’s just him I want to peg. I’ve never ever thought about it with any of the other partners I’ve had.

I’ve got a video I want us to watch together that I think really conveys that level of sensuality and vulnerability I’ve got in my mind. We just haven’t had time to watch in recent weeks. I think I’ll start with that versus just popping out of the closet all geared up. 😆

Thanks for the birthday wishes! I never dreamed I’d be buying myself gear for my 30 something birthday!

Wife wears an 18-20



We have this one. it is her current favorite.

We have the Tomboi which is comfy for her, I don’t find it as sexy, but she has good control.

We also have this one. I find this one very sexy, but it’s not as soft and comfortable.

And we have this one I do not recommend this one however, as my wife said it felt too much like wearing hiking gear.

just go to the Pegging Gear Wiki for a good list of quality gear.

You say you don't want a tiny dildo... How much experience do you have at anal play? Don't make the mistake of thinking that you can handle larger if you don't have a lot of experience. Plus even if you do have experience using plugs, it's a completely different feel when it's being stroked in/out of your ass, it's more intense and needs to be smaller than a plug. 1.25" diameter is a good beginner size. If you have experience, then 1.5" would be a good start. Highly recommend Vixskin dildos- they are expensive, but the dual density just feels amazing during pegging. Don't be like us and spend tons of money buying cheaper dildos, always looking for the best feeling. We wasted hundreds of dollars doing that, when we could've bought one Vixskin for much less and been happy with that.

As for prep... I have found this to be the easiest. About an hour before pegging, fill the bottle, 15 pumps of water in the butt, expel, repeat 4 or 5 times. Then go about daily activities for a while- there will usually be some water still up inside, and after a while it wants to come out, so you need time before pegging for that to happen.

But even with the most thorough prep, sometimes shit happens. So it's good thing to keep a pouch of baby wipes handy. So that if it does happen, it can be quickly cleaned up, and return back to pegging without much loss.

Firmness is fine, but width on a soft dildo beats a thinner hard dildo any day of the week.


I recommend the Outlaw by Vixen, its large, yes, but it is also deliciously soft and fills me up as it pounds my prostate just right. Plus she can slip in in DEEEEP and that's a whole nother amazing feeling once you build up to it.


https://www.amazon.com/Vixen-Creations-Outlaw-Vixskin-Caramel/dp/B0026CN4OY/ref=cm_cr_arp_d_product_top?ie=UTF8&th=1

Sure man - I'll even do a follow-up comment when I have a chance to talk to him about it (he's out with the kid right now).

I know that he did a workbook, here's the link to the one he chose, I think per recommendation from the counselor: https://www.amazon.com/Mindful-Way-Workbook-Depression-Emotional/dp/1462508146/ref=sr_1_5?keywords=cbt+workbook+for+anxiety+8+weeks&qid=1567360748&s=gateway&sr=8-5

He not only went through and did every exercise in order, he went through it a second time with a good friend. Per him, this one was most effective.

Here's another book he read, to directly deal with panic attacks (to be fair, he gave this one mixed reviews): https://www.amazon.com/Worry-Trick-Brain-Tricks-Expecting/dp/1626253188/ref=sr_1_5?keywords=the+worry+cure&qid=1567360943&s=gateway&sr=8-5

He used meditation a LOT - mostly apps on his phone, the usual ones that you've probably heard of - and for a while did meditation every single day. He still does meditation from time to time when things get overwhelming.

Lastly but not leastly, he went on a very low dose of Lexapro. He's calm enough now that I wonder sometimes if he still needs the meds, but frankly, it's his body his business and for all I know the meds are what is making the calmness happen! ^^; I do think it's important to note that he's never had to use a higher dose, and I think the techniques he learned which halted the spiral.

Last, CBD... do you mean cannabis, or controlled behavioral therapy? We have not done marijuana since The Incident and likely never will again ^^; I think some of what he worked through was controlled behavioral therapy.... but I'll ask him tonight :)

Make some time for yourself. Plenty of time. Get a bottle of lube and a smaller size dildo. (Not a hard vibrator) cover your bed with towels. Slowly start to play with yourself. Find what feels good. Keep a slow pace. Remember that your exploring. After sometime, your going to feel a warm comfort come over you. Your going to want to speed up. Go into the shower and continue picking up the pace. It might get messy. (I suggest buying bidet)you can use it before, during and after. You will feel an orgasm build. It will be like no other. Don't force it. If you get there, congratulations. If you don't, try again in a couple of days. Once you get more comfortable with your body, start involving your wife again.

We have had the spareparts Joque for 10 years now, and it has held up well.

As for positioning:

• Get a foam wedge pillow, which can prop his ass up in the air for easier missionary. IMO the wedges provide much better support than a pile of squishy pillows.
  
• For doggie style: if he is tall or has long legs, the height differences can be tricky. Try having him get in an "army-crawl" position: on his stomach, with one leg extended behind him, and the other leg pulled up towards his chest at an angle (as if he were about to start an army crawl). Then get behind him and straddle across his extended leg. It helps a lot if he can put a wedge pillow under his torso for support.
  
• I think the Joque has pockets for a bullet vibe- though my S.O. never had much luck with them. She would be too focused on what she was doing, to try and fuss with the dildo and get any sensations going. Now we just alternate pleasuring one another, or else I will give her oral as a 'warm-up' to her pegging me. You might get more sensation if you get a tighter, leather harness that rides low.
  
  
  

So much fun! Impressed with the vibrant quality as well. We used a lot and probably could get another 1 or 2 uses for each of us.


https://www.amazon.com/dp/B00BUPN6UA?ref=yo_pop_ma_swf

Cheaper than lube!

That’s the same one my wife uses. It looks amazing on her. Amazon has them on prime.


https://www.amazon.com/Sportsheets-Ss69103-Lace-Corsette-Strap/dp/B003MKKWVW/ref=pd_aw_sim_sbs_121_1?_encoding=UTF8&psc=1&refRID=8YXYA3RPXVBM28GFSJSY&th=1