What is best for relaxing a tight bottom

[Laspalmas]

Hi, so I am in a relationship and my boyfriend is bottom. We have been together for over a year and later on we only have oral sex. I have a big dick and the only way we can have anal sex is with a lot of lube and poppers, and still it gets painful to him.

For guys in similar situation. What position works better? for him is lying on one side but i don´t like that position that much. I would love to be able to fuck him for long and without poppers and I know he wants too. Any recommendations?

Thanks

 

[winesthel945]

Different angles may help, also don't forget lots of warming up. Tongue, finger, two fingers, etc. Consider getting some different sizes of dildos to help regularly work on stretching a bit. But it may take a while and in the end you may not be able to ever really pound away if his butt just doesn't have the flexibility to handle you. Just go easy and let him control it as well, that will let him keep it in his comfort range. You don't want to do damage and take his ass out of commission for months while a fissure heals. So go easy and practice.

 

[winesthel945]

Sorry, hit send too soon. Also make sure to try different lubes. Some lubes can cause irritation, burning, etc., and that can make pain more likely. A good water-based lube with no additives (flavors, desensitizers, etc.) is a good place to start, silicone lubes last longer but might cause more irritation. Be prepared to experiment and find something that works.

Finally, Tristan Taormino’s Ultimate Guide to Anal Sex for Women is a great resource. The tips are just as useful for men.

 

[colm84]

Alcohol if you have not tried it. A good bit of alcohol but not so much he is wasted. Trust me it will work.

 

[Brodie888]

He needs to get himself a series of gradually larger dildos to get himself used to taking your size.

The key is foreplay. I'd dedicate at least 10 mins working his hole with your tongue, then introducing one finger at a time. Lots of lube. Then a medium plug or dildo. After that, he should be good to go.

Once you've been fucking him on a regular basis, you can speed the process up or keep it as part of your routine.

Best position is for him to be on top so he can control the depth until he feels himself relax enough to take more. After that you can swap to whatever you like.

 

[Brodie888]

If his issue is depth and hitting the back of his colon, the best thing to do is buy a thin double ended flexible jelly dildo and work with it to stretch his colon wider. Don't force anything or cause pain. He just needs to aim it towards his left shoulder and gradually stretch the kink of his sigmoid colon to accommodate the length deeper.

 

[gayhunglover]

Everything you guys have said is so true and exactly what I would have recommended. When I first started bottoming it took a long time to prepare my ass for a good fucking but after 30 mins or so of foreplay of rimming, fingers, dildos and lots of lube I was ready for a good hard fucking.

 

[winesthel945]

If his issue is depth and hitting the back of his colon, the best thing to do is buy a thin double ended flexible jelly dildo and work with it to stretch his colon wider. Don't force anything or cause pain. He just needs to aim it towards his left shoulder and gradually stretch the kink of his sigmoid colon to accommodate the length deeper.

Most jelly toys have dangerous levels of pthalates in them, a chemical plasticizer that makes them soft but leaches out and can cause skin irritation because they are mildly poisonous. This is why most of those toys actually have little disclaimers that say, "not for insertion" or "for external use only"... That crap shouldn't be on the market, but sex toys are a largely unregulated market unfortunately.

Steer away from jelly and look for pthalate-free toys that will do the same for you. They cost a little more, but if you're trying to avoid pain and discomfort, the poisonous toys are not the way to go.

 

[Nectarseeker69]

The second guy that I bottomed for was 6" (15cm) in C. Way too much for me to take for any amount of time. So I bought one of those 2" wide tapered butt plugs and over the course of 10 days I finally could take the whole thing. Next time with him all went well. Slow, but he finally came. It got better and better as we keep seeing each other. Good luck.

 

[Brodie888]

Most jelly toys have dangerous levels of pthalates in them, a chemical plasticizer that makes them soft but leaches out and can cause skin irritation because they are mildly poisonous. This is why most of those toys actually have little disclaimers that say, "not for insertion" or "for external use only"... That crap shouldn't be on the market, but sex toys are a largely unregulated market unfortunately.

Steer away from jelly and look for pthalate-free toys that will do the same for you. They cost a little more, but if you're trying to avoid pain and discomfort, the poisonous toys are not the way to go.

If someone is worried about chemicals they can put a condom over their toys.

 

[Nectarseeker69]

If someone is worried about chemicals they can put a condom over their toys.

Great idea.

 

[gayhunglover]

Did anyone find it a struggle to bottom? I seemed to have taken it quite naturally.

 

[illinigradman]

I taught my guy by using a lot of the foreplay already mentioned and techniques to relax him but I found the best position at first is for me on my back and him straddling me and going down on me. That way he can take a little at a time at his own pace and know he is in control. A key to do it is to take a little and then back off and then take some more and pretty soon you can tell him he has half of you and then a little more and a little more. Plus you get to enjoy watching him and coaching him. The big tip though is once he gets all of you to have him pull off and do it over again. You will both be surprised how well he can take it the second time. I would suggest different lubes. I find the thicker creamier ones are best at first.

 

[gayhunglover]

Great tip, riding allowed me to take my biggest dick ever from me building up to taking the full length inside me

 

[swimmersox]

What is best for relaxing a tight bottom?
Give him a fifth of bourbon and a few Xanax.

 

[GeorgeSpokane]

I have been reading and try the doggy style position. Get him up on his hands a knees then inser slowly. That position straightens out the s curve in the colon. It worked for me today when I had a nice 7" really thick screw me. Didn't strain or hurt at all. Don't forget to cleanse. Have fun.

 

[henry777]

I think preparation is key. Whether it's rimming him, putting a small dildo then use bigger ones or anything else that turns him on.

 

[Samantha Hopkins]

Lubrication is everything ! The rule of thumb is that too much is almost enough.

I use a total of four lubricants and with some rare exceptions, Its great for me and the guys love it.

First go buy a device called a lube shooter. or a syringe so you can inject lubricant above the anal sphincters. By having lube above the sphincters, your cock actually becomes more lubricated as you penetrate him. I personally use a 20cc syringe.

Start by having him insert 3 KY liquibeads, These are little eggs of Lubricants which will dissolve over 20 or 30 minutes or so, giving you long term lubrication.

Secondly, I insert two lubes internally. One which is ID platinum which is a liquid silicone. The second one is called Albolene and can be bought in any pharmacy. The albolene melts at body temperature but has a different feel that the silicone liquid. The mixture of the two is awesome.

Lastly I coat his dick with Astroglide Diamond Lube. Which lasts well.

You sphincter will ultimately relax and can accept any size cock. Any pain after the initial insertion is probably lubricant problems.

One last thought. When you finally get all the way inside him, who starts pumping, him or you? If the answer is you, that may be the problem too. As a smaller size cross-dresser, 5'4" all cocks seem big. It is painful to get a guy inside me, especially if I haven't had sex in a while. Once he is inside me, I need a few minutes to get used to him being inside of my body. If he immediately starts thrusting, its painful and miserable for me, though I would never let on until I got older and wiser.

Now when I take a man inside me, I ask him to be very still for a few minutes. Sometimes we kiss or cuddle, but mostly I like to just "be there" for a few minutes as my body adjust to being taken by a man. After a while the pain goes away, I can start pushing onto him a bit. After a few minutes of this, I Start pumping slowly and then a few minutes later, I am totally good to go. He can do whatever he wants after that.

 

[gayhunglover]

Lubrication is everything ! The rule of thumb is that too much is almost enough.

I use a total of four lubricants and with some rare exceptions, Its great for me and the guys love it.

First go buy a device called a lube shooter. or a syringe so you can inject lubricant above the anal sphincters. By having lube above the sphincters, your cock actually becomes more lubricated as you penetrate him. I personally use a 20cc syringe.

Start by having him insert 3 KY liquibeads, These are little eggs of Lubricants which will dissolve over 20 or 30 minutes or so, giving you long term lubrication.

Secondly, I insert two lubes internally. One which is ID platinum which is a liquid silicone. The second one is called Albolene and can be bought in any pharmacy. The albolene melts at body temperature but has a different feel that the silicone liquid. The mixture of the two is awesome.

Lastly I coat his dick with Astroglide Diamond Lube. Which lasts well.

You sphincter will ultimately relax and can accept any size cock. Any pain after the initial insertion is probably lubricant problems.

One last thought. When you finally get all the way inside him, who starts pumping, him or you? If the answer is you, that may be the problem too. As a smaller size cross-dresser, 5'4" all cocks seem big. It is painful to get a guy inside me, especially if I haven't had sex in a while. Once he is inside me, I need a few minutes to get used to him being inside of my body. If he immediately starts thrusting, its painful and miserable for me, though I would never let on until I got older and wiser.

Now when I take a man inside me, I ask him to be very still for a few minutes. Sometimes we kiss or cuddle, but mostly I like to just "be there" for a few minutes as my body adjust to being taken by a man. After a while the pain goes away, I can start pushing onto him a bit. After a few minutes of this, I Start pumping slowly and then a few minutes later, I am totally good to go. He can do whatever he wants after that.

Really good advice since lube is so important and it can allow me to be fucked for hours on end when it's properly applied. I always wait for a few minutes with him deep inside me so my body can adjust to his length and girth. I'm a 5'11 hairy cub so lots of guys automatically feel like I'm ready to be fucked hard and deep as soon as he's inside me. I like to take my time at the start to ease him in then I start bouncing up and down for a bit before I let him loose on my ass.

 

[951321]

As a bottom myself there's nothing more relaxing than a bit of foreplay, being given a massage and then some patience when the top decides to try entering my hole.

I've had tops just try to go straight into penetration and my hole just would not relax and any form of penetration became unbearable. On the other hand I've had guys take their time and help me relax beforehand and sex had been amazing