Hey Everyone!
So basically I am a sissy (man who dresses and acts like a woman). I’ve done anal loads but my new friends with benefits is massive and I am really struggling with him.
Any advice or help would be greatly appreciated
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Hi, welcome to the forum 
Have you considered anal training up to his size with but plugs and/or dildos?
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Hello
As above.
Hi @a.lyons94 welcome to the forum 
As @Green_Eyed_Girl suggested, anal training using butt plugs or dildos (probably dildos if you are wanting to work towards sex with your FWB). What size do you need to get to? Think about the size that you can take easily and buy something slightly larger and work up in small increments until you get to where you want to be.
The only other thing that I can think of is an inflatable butt plug (just make sure that whatever you get has a flared base!) - something like these (other sizes available, I just picked a couple that I thought looked good):
Do you do use any toys with your FWB? If you don’t, then using a butt plug or smaller dildo together before penetration would help you to relax a bit first. Or even wearing a butt plug before meeting up if he’s not interested in playing with toys.
I’m assuming if you do a lot of anal play already that you know the importance of a good anal / thick lube?
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Thank you so much for all the responses already, wasn’t expecting it!
I’ve taken men before who are 6/7 inches and they knew how to use them as well. But this one is on a whole other planet! He is about 9.5/10 inches which is a struggle in itself but its mainly the girth which is difficult to handle. It is so so thick
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Might be a good idea to ask him to whip the tape measure out and measure his circumference when hard so you know what your aiming for.
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I have to admit that I was thinking the same thing!
Wow! That is quite large, at least it would be for me. 
I agreed with @Green_Eyed_Girl, it would be helpful for you to know his girth. All the toys on the LH website state the maximum circumference of a toy so if you measure the circumference of him at the widest point you can get a better idea of what toy to buy.
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The toys on the uk site are measured in inches. If your elsewhere you may need to check in the specs of the individual toys.
The sizes in the names dont usually reference the circumference by the way (they tend to refer to insertable length), so do make sure to check.
If your struggling with the length too, sizing up with dildos as @Kitty-Cat01 says, may be the better plan
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At the minute I could probably take about 7/8 inches in my ass…I’ve never measured his girth I just know its very thick. Because of his thickness I think I can only take about 5 inches of him and I feel physically full
And yea it is large, biggest I’ve ever tried to take. The first time I took it out of his boxers I thought there is no way I can handle this. Now its just made me determined to be able too
Sounds like a fun challenge 
Theres lots of people on here who like big toys anally, so having a wade through the forums (search bar is top right) may also net you some good tips. I know i often see advice to stretch anally with other toys before taking something big.
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I’d probably enjoy someone who was 7/8 inches more and a little less thick. He’s told me he is treating me to a weekend away at valentines so I want to be able to really treat him for the 2 nights as well 
some new lingerie and hopefully able to take all of him!!
edited by mod
My wife pegs me with a 10" long 7" girth dildo. I had to work up to it using a series of plugs but when the time came it went in without a problem. At first I couldn’t take the whole length but now I can.
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He is almost 10 inches, which with normal thickness men I could nearly manage all of that. But because he is also really thick I can only take about 5/6inches of him. Because I can’t take him properly pounding me yet he lasts so long. I had to take the next day off work to recover last time lol
Hey, so for this I’d defo recommend warming up before trying to take his big package… have you tried using a dildo or even an inflatable buttplug to loosen things up?
He just uses tongue and fingers to relax me before he puts it in
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Hmm yes sometimes i find another guys fingers only makes me tighten up. I’d defo consider trying a dildo or plug before going to see him and it will help already get you loosened up and able to handle his size better… also try out some anal relaxing lubes too which can help
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My advice is based on what some women do when they struggle to take a large cock, I cant see why it wouldn’t work with you. Firstly invest in a Come Close protector ring worn outside the body that limits how far he can thrust his cock in you during sex, Its safe, comfortable, reliable and easy to use!
Secondly experiment with different positions to find one that’s most comfortable for you (doggy style isn’t usually the first choice for big cocks), make sure you lube up well too and maybe swap over as much as you can to give yourself a rest. 
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