Seeking advice for sexual intimacy

I've never been one to seek advice or take anything anyone has to say with more than a grain of salt, especially coming from a gaming forum so general rule of thumb has always been to take all things into moderation.

for starters, this guy i've been seeing for 9 months now is Bisexual and a tad overweight (i'm a chubbychaser and I pretty much just walk out the door the moment the guy says he's trying to get skinny) he is 8 years older than me and definitly a butch with a smartass/sassy personality (S-M-R-T YAY!).

I'm just going to say right off the bat, feet and his face being anywhere near feet or feet on his lap or touching feet is a big NONO for him. Not a fan of ear/nipple play and RP/talking dirty is not his thing.

I've been in 3 (including this one) LTR and probably 5 sexual encounters (including LTR's).

Anal in my experience has always been P A I NFULL! (I am always the bottom since I go for the masc top guys,go figure). First experience I waited till 3 months into the relationship before I let the guy anywhere near my private parts.
Lube has always been used, intercourse usually ends roughly in a 10 minute window since they like to get it over and done with, foreplay usually irritates me to the point I need to get it over and done with myself HA! But over the course of the years since I began adult relationships I have grown curious/interested in methods but not sure where to turn.

This guy i've been seeing will be coming to help house sit my parents house (only way my mother is letting me stay home since I flooded the house recently) in December for about 2 weeks and i'm ready to go all out to make this the most satisfying experience for both of us.
Sadly our intimacy has been....not so intimate since July of 2013 the last time we house sitted together for my parents (had our first fight which some pretty harsh things were said from both sides).

Anyway we have begun to rekindle our way back to a lovey love love place but a main issue in Anal sex has always been as the following
1) I cum before he does which makes anal more painful without the building up of pleasure
2) It hurts WAYYYYYYY more than usual when he insert their longjohns and the sex ends there when I have to say "it hurts!" (we use ALOT of lube, and I take it in really slow)
3)he cums before I do

Things i'm not so eager to try but willing to think over
-trying toys (start with dildos)

As a Gaymer (personality wise), not really having a rough idea of how to make anal sex more pleasurable is a bit......frustrating especially as a elitist (kinda makes me feel incompetent) if that makes any sense?

At this point I just want to have a firm grasp of tips/sex advice that will make sexual encounters and future sexual encounters more pleasureable. And if I have to spend my 21st birthday in Feb. in a gay bar in Portland not having any sexual knowledge and still having that irk face when thinking of anal intercourse....I may as well become a permanent recluse hahaha
(of course I dramatize but it is what it is in the end)

 

There is no way that any web-based diagnosis of your problem here will really ever work.

For what it is worth, you may want to do the following:

One
Stop focusing your thoughts on the anal part of sex. Don't think of something that is very special or reserved for some sort of exclusive elite. This is like learning how to ride your bike. Some kids do it sooner. Some do it later, but every kid gets there if they want to. You have not been too successful, and you are occasionally trying to repeat the experience with equally dissatisfying results. Sure, you need to change the scenario somewhere for the game to work out for you.

Two
Every magic has its price. If you happen to be keen on getting there sooner rather than later, and believe that you are too tight, and fear that the size of your top's cock may be an issue, re-consider playing around with reasonably sized dildos. A dude is only so big, and won't get any bigger, no matter what he tries or says. If you already know that you can take those dimensions anyway, your worst enemy, fear IS defeated.

Three
There is always a chance that the anal sex may NOT be your thing. I have come across a few guys who have discovered that. No matter what or how, this is just not working for them. I would not worry too much about that either. There are things that you cannot change. You may as well have the maturity to accept that, should this be the case.

KD