A good story...
All this reminds me of an episode that happened to me when in Halifax a few years ago. I had met my cousin for dinner and was ambling back to my room at the Casino Hotel when this obviously inebriated but attractive black woman came stumbling downm the hallway. She asked if it was possible to call a friend of hers from my room as she had no change for the pay phone (I know - I also thought "Yeah, right!" but she was pretty and if it was true, I thought I should do her a favour). So she literally trips into my room and on to the bed. I come in, close the door and direct her to the phone on the side of the bed. She asks for a glass of water and I oblige. She's still pretty incoherent, but she does say she needs money and found me attractive (I know - that's "Yeah, right!" number two...) I asked her if she would be willing to make me feel good in exchange for some money. We play the verbal back and forth for a few minutes and she states that she would LOVE to give me a BJ but that it would cost $75.
At that point I was a little worked up after the talk, so I said OK. She immediately (and a little roughly, which was a bit of a turn-on) whipped off my pants and started making Sounthstreet Junior very happy. Her technique was pretty good, but then, as she continued sucking, she started some anal digit play on me. I was a little uncomfortable with this (probably the gay-paranoia thing) but I relaxed a little with a few minutes.
Then she surprised the crap out of me with two moves: she inserted her finger in my ass and started a prostate massage, while suddenly deep throating Southstreet Junior at the same time. I had never had a prostate massage before (and rarely had the dt experience) so the two together were pretty intense. Just as the pressure was mounting, she looked up at me and said "Come on A**hole, shoot your load right down my throat!" Well, that did it, and my swimmers were released from their holding cell before you could say "Lickety Spit" (which she didn't) I'm here to tell you, I still dream of the intensity of that particular orgasm, which I assume was largely a result of the prostate massage.
I don't partake much in the prostate massage,even now, probably because of my own phobia, and while a finger is OK, I am always a bit worried that an SP might assume something or worse, suggest something larger if I OK'd even just a finger.
...oh, and to finish the story, after I was spent, she had her money and was walking out the door (a lot less drunk than she had been 15 minutes before), just before she closed the door, she turned back and said "By the way, I'm a guy!"
(a true story, I swear)