Help inserting a butt-plug

[DerbySubMale]

I'm currently under training to insert my medium sized butt-plug up my ass but I'm having difficulty getting it all the way in.

I'm 5 feet 8 inches tall and the medium butt-plug in question is 5.5 inches high and 5.5 inches in circumference at its widest point. I've done three training sessions so far on different days (two of 45 minutes and one of 30 minutes). At the end of each session I feel I've made progress and have inserted the butt-plug further than previous sessions but I still can't get it all the way in.

The problem is the pain. The further in I push the butt-plug the more it hurts. At first I thought the pain was around my ass hole as I try to push the bulbous part of the butt-plug through my sphincter, but in my last two sessions I've thought its actually at the top of the butt-plug as I push it deeper inside me.

I've been told that "it's not meant to be comfortable the first time" and "I need to block out the pain and keep pushing until it goes all the way in".

And with my last session I pushed harder and longer from the start - no more easing it in gently - and when I started to feel the pain at the top end of the butt-plug inside me I continued to push as hard as I could. I know from the feel of the base and hands against the underside of my bottom cheeks that I'd pushed the butt-plug in further than in the previous two sessions but, still, not quite all the way in.

But it's so frustrating because with every session, I'm sure, the butt-plug's going in further than the time before and needs just one more good push to go in ... but I still haven't been able to get it all the way in.

I'm using lots of lube and there is no sign of any blood. I do have a smaller butt-plug (4.5 inches tall x 3 inches circumference at its widest) that I can insert easily without lube. In fact, since I've been training with the medium sized butt-plug, the smaller butt-plug goes in easier than ever now.

Any advice, comments or suggestions would be greatly appreciated.

[Under your control]

Hi

The pain is probably the butt plug hitting the bladder. There are a couple of things you can try. You can try adjusting the angle of insertion a bit more towards the back. Also, when you are inserting it, make sure you have been to the toilet first and push against it, as if you were trying to do the toilet and actually expel the plug.. As long as its well lubed up, squeezing the muscles and trying to expel the plug should help everything line up and will also help you get past the widest part of the plug.

Hope that helps.

[DerbySubMale]

Originally Posted by Under your control

Hi

The pain is probably the butt plug hitting the bladder. There are a couple of things you can try. You can try adjusting the angle of insertion a bit more towards the back. Also, when you are inserting it, make sure you have been to the toilet first and push against it, as if you were trying to do the toilet and actually expel the plug.. As long as its well lubed up, squeezing the muscles and trying to expel the plug should help everything line up and will also help you get past the widest part of the plug.

Hope that helps.

Thank you. I'll try that next time.

[DerbySubMale]

Originally Posted by Under your control

You can try adjusting the angle of insertion a bit more towards the back.

I'm not sure I quite get how I would do that. My ass hole is very tight, and it seems to me that the butt-plug only goes in one way, so I'm not sure I fully understand how I can adjust the angle of insertion.

Apologies for being thick.

[Under your control]

Best way to describe the rectum is as a cavity rather than a tube. Altering the angle will make a difference as it will be creating pressure in a different place if it hits the walls or hopefully go in without the tip creating pressure on the walls of the anus at all. Anyone who has had anal sex will know that if it goes in at the wrong angle it can be very painful.

[Mr.Slave]

Hi,

It's good to see that you already have some experience with plugs and have lube But I think you 'lack' of real experience, there are a certain things you should know before you attempt to insert a 'bigger' plug.

A: Make it yourself comfortable, don't force anything! RELAX
B: Lube (Helps a lot)
C: More practice

Before you can insert the bigger plug, you need to practice with your smaller one first. Slowly 'fuck' your ass with the plug and remember what I said; Make it yourself as comfortable as possible. When you think it's right, try to insert one finger in as well. And slowly use your finger to slightly put pressure to the outside (Stretch your anus) and keep going till you can add 2-3 fingers, keep stretching.

Now, it will be much easier and less painful than when you use your big plug right away.

Don't rush things If you have any more question, just send me a pm ;-) or add it here.. I'll try to keep an eye on this thread.

Mr.Slave

[DerbySubMale]

I received this advice by PM. I won't disclose who sent it but will post it here in case it helps anyone else:

Some things to keep in mind when stretching: -

• NEVER RUSH THINGS WHEN YOU'RE STRETCHING. You can hurt yourself and no one wants that. Not you and not your master.
• Five minutes stretching seems like for-fucking-ever. Put in the time, though, if you are planning on taking larger insertions.
• ALWAYS be relaxed when trying to stretch. There is no need to rush and there is no need to tear the muscles in your rectum. It serves no purpose and reduces the enjoyment you will have from that activity later.
• Try stretching using the middle or "bird" fingers of each hand and pull in opposite directions. Move the fingers *and your hands" so that you can stretch right-left and top-bottom. Stretch all the way around the anus this way. It helps.
• You are stretching a muscle that runs in a circle; stretch the whole circle. Take the smaller plug, as Mr. Slave said, and "fuck" yourself with it. When that is comfortable move the plug inside yourself from one side to the other and up and down. When it feels comfortable, insert a finger and continue to stretch in opposite directions: up with the plug and down with a finger; right with the plug and left with a finger. Continue to do that until you can feel a noticeable difference.

Depending on the size of the "larger plug," you may need several sessions before you can accept it. Remember the last piece of advice about stretching when trying to insert the larger plug: you stretch in a circle. Keep making the same types of motions with the larger plug that you made with the smaller one even when it doesn't yet fit: stretch to the top, bottom, right and left.

It's not uncommon for it to take quite a while to accommodate a large object. Be patient. Don't force it. Keep up a gentle fucking motion and twist gently when inserting. A more substantial lube may also help. If you're using a silicone plug (the best kind INHO), then NOTHING BEATS CRISCO as a lube. It's a vegetable shortening that you can buy in a can at the grocery store.

[Star Shadows]

first thing, take it slow, try not to get frustrated, that it takes a while, if you do it too fast or too hard too soon you could cause yourself damage. It isn't a race, it takes as long as it takes, keep practising and you'll get there.*

Also i cannot emphasise the importance of lube. get a good quality of lube and use it generously and it makes it so much easier and try to stay relaxed while you do it, when you get stressed your muscles clench and create more resistance, try and relax.

*Additionally the person who gave you the advice of it's not meant to be comfortable the first time" and "I need to block out the pain and keep pushing until it goes all the way in" should kindly shut his mouth as that is the biggest load of rubbish going, we experience pain from stimuli for a REASON, blocking it out helps no one, it is a sign that you need to slow down and ease up not some form of nuisance to be ignored. Blocking it out will likely just get you hurt the flesh in the anus is quite delicate and can be torn if you aren't careful with how you interact with it. Please DO NOT listen to any more of their advice, anal takes time. lots of it when you give it time and patience it can be practically painless. but it takes time.

[Counterfeit_Fantasy]

I'll make it short.
Lube.

Rather than pushing it in, proceed to sit on it.

[DerbySubMale]

Originally Posted by Counterfeit_Fantasy

I'll make it short.
Lube.

Rather than pushing it in, proceed to sit on it.

Thank you. I've tried sitting on it but it tends to bend rather than going in. Perhaps I'm doing it wrong?

[DerbySubMale]

Thank you everybody for your kind advice.

I'm quite looking forward to my next butt-plug session now.

[DerbySubMale]

Thank you everybody for your advice. I did my next butt-plug training session tonight and it went a lot better. The butt-plug still didn't go in all the way but I feel I got a lot closer with far less pain.

I've posted a full report on my punishment thread Page 7, Post #98.

If you have any more advice based on this update please let me know.

Many thanks again ... I really appreciate the advice.

[collared4cuties]

Definitely start with the smaller one. Lots and lots of lube. After that move on to the bigger one. Push it in a little then take it out and apply more lube. Keep repeating that process, going a little deeper each time you relube. If it hurts real bad, you're not quite ready. You might have to find one thats a tiny bit smaller. Just my opinion.

[marslv]

you already received a lot of good advices. i just wanted to emphasize again that pain is big NO. If you feel pain, stop, especially if the pain is coming from the inside.
Of course there might be discomfort. i mostly feel discomfort every time at the beginning altough i use buttplugs and dildoes for more than 10 years. But do not mix discomfort with pain. Pain is almost always a sign you are not doing something right. Even if in most cases you are probably not doing any damage if you feel pain, it might as well be that you could.

my suggestion would be to use a well lubed small buttplug for 30 min to 1 hour, maybe even under clothes doing whatever and then when it feels completely comfortable step up to the medium buttplug. That's what i do.

[DerbySubMale]

Thanks to everybody who has so far responded with advice and suggestions on this thread.

Since starting this thread i have had two sessions (one of 90 minutes and one of an hour) and have still been unable to fully insert my medium sized butt-plug when it is well lubed.

In total, i've now had five sessions (the first three before starting this thread) and each time i think i'm getting closer but i experience pain inside me at the end of the butt-plug. There has been no blood and the pain stops as soon as i pull back on the butt-plug. My small butt-plug inserts easily dry and there is no pain.

i'm 5 feet 8 inches tall and the medium butt-plug in question is 5.5 inches high and 5.5 inches in circumference at its widest point; my smaller butt-plug (which I can insert easily without lube) is 4.5 inches tall x 3 inches circumference at its widest. [See photo at the bottom of this post].

i'm on an ongoing training punishment to not only insert the medium sized butt-plug when well lubed but to continue until i can insert it dry. My Master has requested i ask those of you more experienced with anal insertions than me whether you think this is doable and if you have any further advice to help me?

i received the following advice today, after my last update on my punishment thread: "I think your problem is definitely length, I have the same issue with longer dildos if the head isn't very soft. Try on all fours and arch your back backwards, so your pushing your stomach to the floor and your shoulder blades up, this can help line things up."

My Master and i would welcome your thoughts.

More detailed reports on the two sessions since starting this thread can be found at the links below:

Fourth session (90 minutes)

Fifth session (one hour)