I agree with "tswhisperer." Oftentimes, a first timer is simply too tight to enter. A little stretching helps.
Although using dildoes on oneself isn't much fun in my opinion. To me that's the whole point of playing with a partner. Having someone do things you wouldn't ordinarily do yourself.
Like fisting - which I guess would be the ultimate stretching exercise. There you definately need a partner, and you have to work up to it. But some people get a great deal of pleasure from it.
TS's are generally on hormones so while we get errect it's not usually rock hard like a guys toy. So if you are really tight it's hard to enter and maintian an errection. But for the "top," tightness is part of the attraction to ass fucking over vagina fucking. Also please remember guys, T's are like anyone else. If we aren't turned on by our partner things don't work and no amount of stretchig will help you.
My partner and I tend to tag team things successfully. She is smaller and usually starts things off, then I can usually come in afterwards and finish the job. Sometimes we add various toys before or after.
I also think it's important let your partner know of your experience. A first time shouldn't be painfull if there's pain things are ripping and you are going to fast.
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