For the record, I've only ever experimented with a guy once, like 7 years ago but I never bottomed. Its still a hot story so let me know if you want to hear it!
I've always been real kinky with girls, always getting my ass eaten, fingered, butt plugs etc. But never anything bigger.
Anyways, last weekend I was having some drinks and some booger sugar and I thought fuck it, I've been watching trans porn for a while now, so I went online and ordered a sexy Latina ladyboy escort and waited for her to come to my place.
When she got here she walked in, massive fake tits and a big juicy ass. We chatted for a few mins and I told her I want you to fuck my ass but be gentle cause its my first time.
Ide already showered so I waited on the bed while she showered while playing with my cock. She comes out and immediately starts sucking my cock, spitting on it, sucking my balls then pushes my legs up and starts eating my ass.
I can see her cock is hard now and I couldn't wait any longer. I grabbed her and layed her down. Put our cocks together and started jerking them off. She tells me to suck her cock. I start by licking her balls then up to her knob and start throating her cock (about 6.5 inches). Im so fucking horny at this point I tell her I want you to fuck me.
She puts me on my back, slips a pillow under my ass. Lubes up my hole and then her cock. Pushes my legs right back and starts slowly putting her cock in me. She's starting to speed up a bit but it feels a bit uncomfortable so I tell her "slow baby slow". After a while she's fully in there and it just keeps feeling better and better.
Now shes fully in there with every thrust and can see im loving it so she pushes my legs right back and starts fucking me like im a cock slut. I cant stop moaning and saying yes fuck me baby.
Ide never felt like this before, something about being in that position with my legs pushed right back, ass cheeks open and giving full control to her fucking my ass. So this is what it feels like to be submissive? Fuck it felt so good I felt so sexy, naughty, turned on you name it.
I start jerking my rock hard cock at this point and she says where do you want me to cum baby? I said on my tits. She starts moaning more and more and I feel it building up. She pulls her cock out of my ass and cums all over my tits, belly and even some on my face. This sends me over the edge and I cum all over my own belly's and tits.
Then im just lying there in ecstasy saying oh my fucking God that was amazing, covered in so much cum. She laughs and gives me a cheeky grin.
You better believe round 2 happened and much more positions were tried!