I’m [M27] bi, So there is this Ladyboy [M26]. He’s a prostitute and I have been seeing for about a year. He is about my height and body size. He is soft and feminine from all the hormones he’s on. He gives the best blow jobs, better than all girls I’ve been with.
So I was horny and I texted him, I went to his place expecting the usual to happen. I arrived, we took our clothes off and started making out. He laid on his back and I proceeded to kiss and lick his soft chest. After a while I moved my hip to his head and put my dick in his mouth, he took it all, deep throat. (I came once before in his mouth and it was the best experience).
After a short while, I told to turn on his stomach, he said no and made me lay on my back. He proceeded to suck my dick and moved his hip near my face. I started playing with his ass and slightly fingering him. I noticed his dick was hard, for the first time ever, he’s probably on Viagra. I started playing with it. I spread my legs while he was sucking, he understood what I want and started licking my balls and getting closer to my anus. When I noticed he was up for it, I spread my legs even more, giving more access to my anus, he did not hesitate and started licking my asshole.
I was so excited by then, I asked him to sit on my face, I started licking his asshole while playing with his hard dick. We continued for a while, then he told me to lay on my stomach.
He started licking and sucking my asshole, I was moaning with pleasure, I lift my hip a bit to give him better access. I thought this was going to continue for a while then I would fuck him as usual but I was wrong.
After a while of him giving me the best rimming ever. He moved his hip to mine and started putting oil on his dick. This was not why I went there, and it is certainly the first time he’s hard with me. He put oil on his dick and thrust it into my ass, it was the perfect size for me. He started pounding me hard, going fast then going slow, all while he’s kiss me and licking my ear.
I moaning load, I was enjoying every second. After few minutes, he told he’s already came, twice, and still hard and going, probably from the bills he’s on.
The pain was growing because the oil was drying up. I stopped him, even though he wanted to continue. But it was my turn.
I was horny and hard, he laid on his back and I put oil on my dick and started to fuck him. After all the excitement, I came in less than 20 seconds. This happens when my prostate is excited either by fucking or fingering. He was not disappointed since he got to fuck and cum in me twice.
Anyway this is it. I’m definitely going to see him again.
Source: reddit.com/r/gonewildstories/comments/xy3mi1/mm_my_appointment_with_a_shemale_took_unexpected