Top products from r/MenWithToys

Happy to help!

The secret of wearing plugs for a long time is twofold: you want to have a plug made of a softer material so when you move around and change your position it doesn't bump and poke around your rectum so much and cause discomfort, and you want to make sure you manage your lube properly. What I mean by "managing" lube is that most soft plugs will require that you use water-based lube, which your body with absorb over time. Before you pull out a plug you've had in for a while, you need to "touch up" the lube around your anus so that it'll come out more easily.

I have a favorite medium-sized plug that I love to use for stretching out before sex(my boyfriend is pretty thick), but it's fairly firm, tapers a good bit for tip to bulb, and it's about 5" long, making it very uncomfortable if it gets jostled around inside me at weird angles(I wore it while riding a bus once. never again.). I have another plug that much shorter, softer, and I can easily wear for extended period without any discomfort even in a variety of positions and angles: Doc Johnson Raging Hard-on Butt plug

I know finding that exact plug may be tough, but in general you want to look for four things in an extended-wear plug:

• Short insertable length
  
• Blunt end instead of a pointy taper
  
• The stem should be much narrower than the "bulb" of the plug, so it stays in very well until you're ready to remove it
  
• Soft material (pure silicone being ideal)
  
  Other than Doc Johnson's softer stuff, a really good brand to look for is Tantus, which makes all their toys from 100% silicone. Once again, if you can see/feel it in person, all the better!
  
  I hope that helps! I'll also note that as you get more into anal play, you may want to look even more towards prostate simulation toys like the Aneros and Rudeboy, since finding your prostate and getting it revved up can be a time consuming, and very rewarding, process that's well suited to just lounging around the house with a toy inside you and just flexing it back and forth across your p-spot.
  
  Let me know if you have any more questions! I know this is a lot of information. :P

Some of my favorites include:

• The Icon Brands Velvet Plush Silicone Fulfiller. This is my favorite plug because it's the perfect size to make you feel full, yet it's not uncomfortable to wear and is easy to insert if you warm up properly. This is the plug I used in this post.
  
  
• The Lovehoney 7 Inch Curved Silicone Dildo. I use this dildo if I'm craving something on the larger scale for continuous penetration. The suction cup base acts as a safety to stop you losing it and is very useful for sticking to flat surfaces for hands free enjoyment. This is the toy I used in this post.
  
  
• The LELO Billy. Although a little pricey, the quality is worth it and it is a great first vibrator for beginners. It is quite slim, so if you like being stretched, this product might not be for you. That being said, vibrators aren't usually very girthy. Despite this, it is specifically designed to reach your P-spot and has extra sensitive motors in the bulbous end to stimulate the area.
  

If you want the benefit of a fleshlight stamina trainer without the cost, this pocket pussy comes close. being mini and closed ended guarantees snug fit, and once fully sheathed, focusing on just moving the sleeve over the head causes (for me any way) knee shaking pleasure. the cock rings also come in handy.

I love the Njoy 2.0!!!

https://www.amazon.com/Pure-Plug-2-0-Pleasure-Object/dp/B0097RR3FW

The Njoy would be alot better out n about for sure. It's heavy but it has girth so it doesn't fall out. It's stainless steel so it's easy to clean and it doesn't absorb smells. The cons are for one they are expensive. The second con it would have to be that the handle is kinda of sharp so it will irritate.

And then there is glass.

https://www.amazon.com/gp/aw/d/B003YIHXZK/ref=pd_aw_sim_121_of_12?ie=UTF8&psc=1&refRID=S74CM850ZCFFJ955E93N

I use this one. It's really good.

http://www.amazon.com/BOSS-Silicone-Stopper-Butt-Plug/dp/B006TQLMFQ/

http://www.amazon.com/NS-Novelties-NS1104-13-RENEGADE-PLUG/dp/B00A0VVFSA/

Pocket 3D Pôckët-Pûssë`ýs Men Toys https://www.amazon.com/dp/B07V6B2RNN?ref=ppx_pop_mob_ap_share

It was this but I took the outside layer off because it made it just slightly too much.

https://www.amazon.com/dp/B007GFR8KW/ref=cm_sw_r_other_awd_7x5DwbKCBD30J

This kind.

My Doc Johnson Sasha Grey Glass Plug (Large) and Triad cock ring.

http://www.amazon.com/California-Exotic-Novelties-Smooth-Lubricant/dp/B000BUPHYS

it's nothing special really, i'd prefer something thicker.

These toys, from left to right, are as follows:

Bad Dragon Elden Med size/Firm
https://bad-dragon.com/products/elden

Three Bumps for your Rump https://www.amazon.com/gp/product/B008OJ7KDY/ref=oh_aui_detailpage_o07_s00?ie=UTF8&th=1

Bad Dragon Rex Med size/Med
https://bad-dragon.com/products/rex

Lifelikes 9"
https://www.adameve.com/adult-sex-toys/dildo-sex-toys/realistic-dildos/sp-lifelikes-dildo-12866.aspx

Comfywand 10.25"
https://www.amazon.com/gp/product/B017SAB7W4/ref=oh_aui_detailpage_o02_s00?ie=UTF8&psc=1

All American Ultra Whopper 11"
https://www.adameve.com/adult-sex-toys/dildo-sex-toys/realistic-dildos/sp-all-american-ultra-inch-curved-whopper-98872.aspx

Goose Probe Small
https://www.amazon.com/gp/product/B010KN03UI/ref=oh_aui_detailpage_o05_s00?ie=UTF8&psc=1

Rex, the 9", and the 11" whopper are my favorite. :D

These are the ones I want to be able fuck. I can barely insert the screw and the dick now. The last one i can push till the depth hurts.

https://www.amazon.com/AnE-Toys-Controlled-Vibrating-Realistic/dp/B00Z8SWV7Y/ref=pd_sim_121_3?_encoding=UTF8&pd_rd_i=B00Z8SWV7Y&pd_rd_r=ASC9V7P2J2T62MEGMVD9&pd_rd_w=70Igr&pd_rd_wg=r5t7Z&refRID=ASC9V7P2J2T62MEGMVD9&th=1

https://www.amazon.com/Master-Cock-Screw-Giant-Dildo/dp/B01KYHNI0W/ref=pd_sim_121_24?_encoding=UTF8&pd_rd_i=B01KYHNI0W&pd_rd_r=ASC9V7P2J2T62MEGMVD9&pd_rd_w=70Igr&pd_rd_wg=r5t7Z&psc=1&refRID=ASC9V7P2J2T62MEGMVD9

https://www.amazon.com/Doc-Johnson-TitanMen-Intimidator-Vac-U-Lock/dp/B002NU68GA/ref=pd_sim_121_68?_encoding=UTF8&pd_rd_i=B002NU68GA&pd_rd_r=ASC9V7P2J2T62MEGMVD9&pd_rd_w=70Igr&pd_rd_wg=r5t7Z&refRID=ASC9V7P2J2T62MEGMVD9&th=1