Sex with a new buddy

[DenBoy]

Hey guys, I've been having great almost mindblowing sex with a new fuckbuddy for about 2 weeks now, at least for me. The problem is he wants to take my rather large cock up his ass really bad but only seems to be able to take it for a couple of minutes at the most. I've had both guys and girls take a look at me and back out or attempt it once, but never again, but have never had anyone keep trying to take me but couldn't.

His ass has always been lubed and feels slightly open to me when we start. We have been doing lots of making out getting really hot for each other before we even start the heavy forplay. I have been really working his hole with my tongue and lubed fingers getting it as open and relaxed as I possibly can, and he is always eager to take it, and I have gone as slowly into him as possible, but he never gets past the point of being able to take a few gentle strokes. We have tried every position we can think of, but still no luck. I've talked him into fucking me the last couple times, but he claims to be more of a bottom, and is unable to cum from topping. Any advice would be appreciated.

 

[Pappy]

More foreplay and lube, lube, lube ....well you get the idea. If that doesn't work, get a toy that is about your size and use it to open him up first. Then insert your big self and see how it goes.

 

[carter2006]

Sounds like he may be a bit too keen to the point where he's getting worked up about it and therefore not relaxing enough. Maybe he needs to chill out a little bit and try not to worry so much. I had a similar problem with a seriously hung top once - the biggest I had ever taken. I wanted it so badly that when I couldn't take it first couple of times I got really stressed out and it just made the problem escalate. Eventually I took after much de-stressing, relaxation, foreplay and above all LOTS of lube (like nearly a whole bottle by the time we finished!) It was all worth the effort in the end though...
Another tip... My current partner who I've been with 2 years now had problems taking me at first and still has difficulty in many positions. Let him take control of how much is going in a how slow/fast. Get him to sit on your cock while you lie back and enjoy the ride! It gives him complete control to go at his own pace, and all you need to do is stay hard and reassure him. But do try not to touch his cock while he's getting used to having you inside him. Stimulating the cock during anal sex could cause his muscles to contract and make it more uncomfortable for him...
Good luck!

 

[spl98006]

Let him take control of how much is going in a how slow/fast. Get him to sit on your cock while you lie back and enjoy the ride!

Good advice - that has helped me in the past.

But do try not to touch his cock while he's getting used to having you inside him. Stimulating the cock during anal sex could cause his muscles to contract and make it more uncomfortable for him...

Possibly true, but on the other hand, make sure you have lots and lots of foreplay before trying to insert. Get him REALLY horny. Make him not ejaculate for a few days before you have sex, then build him up for an hour before taking the plunge.

Again, this has helped me and my partners in the past. ymmv.

 

[carter2006]

spl98006 is right - lots of foreplay and getting him SERIOUSLY horny will help a lot too, I think. But I still say that when you first enter him, try not to stimulate him too much as he needs to be relaxed...

 

[spl98006]

I've had both guys and girls take a look at me and back out or attempt it once, but never again, but have never had anyone keep trying to take me but couldn't.

Noticed that your profile says 70% straight, so I'm assuming most of your experience has been with women.

One thing you'll find with guys much more so than girls in my experience is that a lot of guys totally dig the challenge of taking on a really big dick. Like it's a test of their manhood to see how much cock they can take.

There have been threads about this on LPSG if you search for them.

Anyway, just be sensitive to the fact that for your buddy, this may be an ego thing. Let him know that you find with sex with him really hot even if you don't get to fuck him, but then make a point of telling him in explicit detail how hard you're going to plow his ass as soon as you can open him up. "Yeah dude, you're gonna like bragging to your buds that you got ripped apart by a [fill in the blank]-inch cock, aren't ya?" Without knowing your buddy, I bet talking to him like this will get him VERY turned on. He just sounds like that type, from your description.

I wish the two of you best of luck!