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I used plug trainers with my gf. It took awhile but with a lot of lube she started to enjoy it.
You should start with something that feels good but that you can work your way up from. My very first toy (aside from stuff around the house like pencils) was a butt plug training kit. This isn't the exact set but it's close, and it's not very expensive.
Once you work your way up to the biggest one, you can move on to other toys like dildos or rimming plugs.
Here you go, slut 😘
Real Vibes Butt Plug & Anal Plug Prostate Massager Enema Kit with Suction Cup & Anal Lube for Anal Dildo | 4 Pack Anal Toy (Kit with 4.5g Lube) https://www.amazon.com/dp/B015TLFTNM/ref=cm_sw_r_cp_api_glc_fabc_4hu2FbQEJES27
I got this exact set from Amazon and I have been very pleased with them. The size increase seems very reasonable, they are nice silicone, and they have a very wide base so you'll never worry about them getting sucked in, so to speak. That wide base is also a downside though. I have a huge ass, so the wide base really pushes into my cheeks, so it's not comfy for long-term wear. I think they've definitely helped. I am more relaxed when I insert anything anally, and I feel comfortable enough looking to upgrade to other toys.
Lube, lube, lube and warming yourself (and the plugs!) up are key.
I couldn’t find the exact one I bought but this one looks the same. I think I probably jinxed myself by typing up how well I’ve been doing the other day, I’ve been having problems since 😢
Haven’t been taking any supplements or doing anything else since though yet so I guess it’s time to start some sort of strict routine again..
Then I'd suggest starting first with a set of butt plugs in a few different sizes like this. Start with the smallest and work your way up. After you get that hole nice and stretched I'd go with a nice 6" x 1.5" dildo. You'll eventually get used to that and crave something bigger. The most important thing is to take your time and use plenty of lube. Good luck!
Looking at this. Seems ideal. Quality soft and flexible medical silicone. But no loop.
http://www.amazon.com/Anal-Trainer-Kit-Beginner-Silicone/dp/B015TLFTNM
How hard would it be to screw in an eye-screw? Would that work? Would I need any special glue to keep it from falling out?
First, read this infographic:
Now, consider investing in a butt plug trainer kit. I recommend Real Vibes 4 piece Starter kit. It's under $20 on Amazon. Here
Once you've gotten comfortable with the biggest size, invest in a silicone, rubber, or glass dildo:
Silicone:
Pros: - Durable - Can be hypoallergenic - Very flexible/feels real
Cons: - cannot be used with Silicone lube - not very rigid
Rubber:
Pros: - economical - firm - feels somewhat real
Cons: - rubber odor and chemical taste - deteriorates quicker - difficult to clean
Glass:
Pros: - easy to clean - odorless/tasteless - durable
Cons: - rigid/inflexible
You can find them on ebay and amazon for around $15. Most kits dilate from 3/4 inch to around 1.5 inch diameters. Good for getting started with BD toys unless you get an ika or winston's tougue to stretch.