Lets face it, not all shemales asses are the same. Now we all much prefer a tight ass to fuck but on occasion we are just too big to comfortably fit. This has happened to me a couple of times, and after a quite a bit of fingering and lube I always got it in, but at the expense of the poor tranny I was fucking.
Now you could just take it out and let them suck your dick, and I have done that a few times. But honestly for the tranny your fucking its better to finish the job so the next time it won’t hurt as much.
Now not being heartless I do feel sorry for them sometimes particularly if they are reduced to tears. This indeed happened to me once or twice, with an Asian tranny or two. (they seem to have the tightest assholes). But eventually they got though it like a trooper and complemented me on the size of my dick.
So I guess the moral of the story when fucking younger Shemales be gentle.
From Shemale Ambush 
Tags: Ladyboy gets fucked · Painful Anal Shemale Sex · Shemale · Teen Shemale · Tranny fucking4 Comments
4 responses so far ↓
hey i was just wondering where you find these gorgeous shemales. im living in Kentucky and i havent found any! so if u could give me some tips id appreciate it
im Alessandro Riposi im a gay Italian man im 37 years old and i work for Italtel Spa as an IT engineer and i love to fuck ladyboys and shemales and suck shemale cocks and i enjoy watching shemale hardcore porn.
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Wishing I was on the bottom of the dog pile