Fail using my first toy.

[quiubo]

This is quite a long story, but I want to paint the whole picture for you guys. TLDR at the end.
So, I loved watching dildo play or anal related videos, and I thought that I would be able to take one myslef, after all... how could I be different from the people in the videos? Oh boy.
I bought a nice 8.7'' clear rubber dildo off of Amazon, thinking it would be a piece of cake (I even thought of looking for a bigger size, as I believed it would not satiate me.) It arrived, and after unboxing it, I started doubting, but I thought I was just getting scared for nothing.
I jumped into the shower, cleaned myslef (did not actually douched, just showered and fingered a little with water to cleane myself because even though I somewhat know how-to, I don't have the toold to do it safely, and I am a scared pussy) and jumped straight to watching porn to get in the mood. Once I felt horny enough, I decided to watch a nice video and just do it.
Next to me, I had my water-based lube, toilet paper roll, and wet-wipes, just in case, as I didn't know what woudl actually happen. I was laying on top of an old shirt, just in case, and started massaging my hole using the lube. I put a finger in, but I might've done it too quickly, as I felt a slight burning sensation. I kept going until my whole middle finger (about 8cm long or 3.14 in freedom units) was in. Then, I slide my index finger as well, and I felt that burning again, so I used even more lube. I went in and out with my own fingers for a short while (I'm very impatient), so I decided to finally use the toy.
I put a condom on it, and lots of lube. First, I tried to sit on it, which might have not been the best, but I thought that forcing it in would just work. Nope, my hole just didn't budge. I swear I was trying to relax, but I just couldn't, I guess.
Then I tried to lay on my side, and push it in with my hand. This worked, but not quite. If you open the amazon link (that hopefully works for you) and can see the whole thing, you get an idea of what I'm describing. Not even the tip went in.
After what felt like minutes, but was more than an hour of "playing", the tip started to penetrate, but it wouldn't go further.
I really did what I think was my best to play with it, but I just couldn't get it in.

After reading this whole thing, what do you think went wrong?
I really wanna get into it and use it more. I would love to slide the whole thing in, but I just can't stretch my hole it seems.

TLDR; I bought a dildo and couldn't get past the tip. Help?
I really wanna hear advice in here.
For a little bit more context; this is my second time trying one, I tried another (about an inch smaller) one back in 2021, same thing, but I didn't have lube, so I used lotion.

Help?

 

[jamiegorgous]

Was this your first time playing with your hole? like fingering etc.

 

[tyler19872]

I know this is your first time using a dildo but is it also your first time playing with your ass? If it is, please know that patience is key

An 8.7in dildo is an absolutely huge unit to start with; if you can, I would first get a smaller toy (say 5 inches with less girth) to train with.

Before you even start playing with the toy it is really really important that you relax. It can be really exciting (and scary) exploring your ass but these feelings of excitement and fear have the habit of tensing us up; you need to take some time (when you have nowhere to be and no rush) to lie down and focus on your breathing, really allow yourself to feel fully relaxed.

Make sure your finger nails are trimmed and smooth.

Start by lubricating a finger and rim your hole, slowly massaging the sphincter applying small amounts of pressure so you get used to the sensation. Give this plenty of time, you will want to rush it but it is so important that the feeling of something there no longer engages a tense response.

When you feel comfortable, slowly insert a finger an inch and hold it there, allow your hole to relax again before repeating this over and over. This will take time, your body is wired to tense up and you will probably need to keep applying lube - you never want to feel skin directly on skin at this stage.

With your finger you can explore going deeper; you will notice how your hole resists you pushing deeper. To counteract this, you must push out (as if you’re doing a poo). This action will release the sphincter muscles and allow you to push deeper. The ability to push out and hold it from tensing is a real skill - this will take you time and lots of practice to achieve - don’t expect to get this right away!

I would put some time aside and repeat this process above for a few weeks before even thinking of using the toy. The more you practice the more you can experiment using more fingers, a butt plug etc. I would ensure you’re comfortable doing this before attempting a dildo, otherwise you are very likely to injure yourself.

Now you’re comfortable with relaxing and controlling those sphincter muscles you are ready to use a dildo.

Start with a small dildo (and you can work your way up). Using plenty of lube, warm up your hole as normal and lie in a comfortable position. If this is your first time with a dildo lie on your side with your knees tucked up under your chest (this will open your anal cavity up). Using the push out method you have practiced, push out and simultaneously present the dildo to your lubricated hole. Slowly insert an inch of the dildo and hold it there. Ensure that you are still in control of those sphincter muscles before proceeding any further. If you’re not, wait there and focus on breathing, relaxing and pushing out.

Push the dildo as deep as feels comfortable, controlling those muscles as you go and slowly remove the dildo from your ass. You will probably have to apply lube multiple times.

Repeat the above and when you feel fully relaxed and the dildo is inserted, use a small rocking motion to simulate being fucked. Don’t do any big moves at this point, just a small rock forward and back - if you’re relaxed enough this will feel amazing if you can line it up with your prostate it will feel even better.

Again, I would get comfortable for a few weeks with this smaller dildo and slowly build your way up to a bigger more girthy dildo. You will get there but patience is very important to pain free play.

If you have any questions don’t hesitate to ask!

T
X

 

[louparis10]

You need some asshole training, self-training!
Starting with fingering and a small dildo. With lube, lot of lube. Practice every day, at shower time. And you will see that your asshole will get accustomed to your toy and will slowly accept bigger toys...

 

[jamesonjon]

Can only echo the advice above , start small, 8 in is way too big. Honestly took a long time using finger size vibrators and dildos before i managed larger ones and of course having patient and loving partner to help is also a benefit and in truth i know i am one of the lucky ones in that regard, she is very sexually open and understanding.

Hope all the advice helps and of course make you ready for the real thing

 

[goldscorpguy]

I think all the good advice has already been said. Lifelike monster dildos look fun and exciting, but if you're not used to ass play, they can also make you tense up in expectation. I highly recommend using a smooth butt plug before any ass play (toys or the real thing). They are easier on your hole and help that inner sphincter to open and relax. You also mentioned that you didn't douche, and sometimes doing that with warm water a few times can also help with the relaxation process. Maybe just try a few sessions using just a butt plug, just to build up your confidence, then progress to trying the dildo again.

 

[quiubo]

Wow, thank you guys. You really opened my eyes. I will follow your advice to the best extent possible and report back once I’ve broken through.

Wish y’all the best.

 

[WilliamG]

Wow, thank you guys. You really opened my eyes. I will follow your advice to the best extent possible and report back once I’ve broken through.

Wish y’all the best.

Baby steps. I did the same starting out. Picking out dildos when you're horny...
It's like ordering food when you're hungry!

Check out something like this Tantus.

 

[chrissal480]

Anal plugs can help..