Gay for a dare
I went to a friends stag do and they got the groom a tranny stripper. This girl was hot so none of us knew until she was down to her underwear and pulled it out. It was massive! Never seen a d*** like it except in p***.
Anyway, after the fun had died down we were betting him money saying he wouldn't put it in his mouth. Anyway the money got up so high that I say 'f***, for that money I'd let her c** in my ass.' We all laughed and then they turned round and said, go on then.
Well I'm a straight guy and have a girlfriend but they were offering £800 and what they didn't know is that I've always found trannies super hot. So...
I took off my trousers lubed up my ass hole and stood over this girl, her d*** was hard and standing up ready for me and I squatted until I felt the tip touch my hole. And then with the eyes of all my mates on me I dropped on to her member and slide down as far as I could. Don't get me wrong the first 5 minutes hurt like f*** while I got used to it but then I slowly bounced on that D***. 15 minutes passed and I was bouncing pretty fast now and the tranny, sits up, roles over so she is on top between my legs pumping away. She leans forward, grabs my head and kisses me right as I feel her swell and explode in my ass.
Best dare I've ever taken part in. I'll probably use the money to do it again but this time in paying.