Lived on the beach. Knew where the gay spots were. I was half high and extra horny. A good-looking woman came up and started talking to me. What the fuck, I was horny, and a pussy would be as good as dick at the time. She asked where we could get a drink, she was buying.
I took her to a local hole-in-the wall and we sat down. She ordered the strongest drinks they had available. Looking back, she was getting me drunk. Didn't take long. She then led me to her motel room. She started getting friendly. She was hugging me, squeezing my ass and kissing me. That woman had the longest tongue that ever had been in my mouth. I swear, it almost reached my throat. I was so drunk that I was having trouble standing.
She led me to the bed and undressed me. Then started kissing my whole body. Nibbling on my nipples, pulling on my nuts and caressing my ass crack. Then she rolled me over and started tonguing my asshole. That tongue felt better than anything I had ever felt. That included every dick that had been there.
I had been trying to undress her, but she kept saying in a minute. She had me so fucking worked up, if she touched my dick or asshole, I would have shot all over the bed.
She got up and told me to pay attention, she wanted me to enjoy the show. I propped up on my elbows. She started with the top. Stripped to her waist, that bitch had the flattest tits I had ever seen. Then she started on the bottoms. She told me one of my regular guys I sucked had pointed me out. Said I would love her. Then she was naked and had one of the biggest cocks I had seen until that time. I moved over and made room for my first ever cross-dresser. Needless to say, I promptly dove down on that sweet dick. I showed that bitch why I was pointed out to him.
After I got her off, I passed out.
I don't know how long, but I was awakened by that big dick easing into my asshole. He was taking it slow and easy. When I felt him bottom out, I started pushing onto him. When he pulled it almost and shoved it back end, teasing my prostate, I couldn't help slowly shooting off. After a bit. he grabbed his dick and pulled out and slammed it back in. It only took him a couple times and he bottomed out a filled my guts up.
The next morning, we showered and got dressed. He put on male clothes. Told me I saw his only female outfit. He only wore it on special occasions. Said all my regulars told him I would fall for it and then make worth his while. He told me he enjoyed himself so much, if he wasn't going home that afternoon he could spend days with me. I leaned over and gave him my you will be missed kiss and left.
That night I was asked how it went; I told them they would be lucky to have the fun he had last night.

 

I have a cuban friend 38dd tits really pretty and a thick 9in cock

 

Looks like a quite pleasurable acquaintance. While living in Alaska, I actually partied with a street walker who lived with a big tittied, big, dicked roommate. We had some really great threesomes. I was still into anal and was often getting a blow job while being fucked in my ass. I also loved giving blow jobs while being fucked. I would do so in rhythm with the cock working my asshole.

 

A favorite fantasy of mine is having a night with a passable tranny/CD.