A long time ago (back in the mid 80's), I was between girlfriends and needed some release. I picked up a local adult newspaper (the Spectator for those of you who remember it in the S.F. Bay area) and checked out the escort ads. I found a girl who was local and I called her number from a pay phone (this was before cell phones in every pocket).  She told me she could see me right away if I wanted and told me to call her again when I got to a certain street corner. I told her I'd be there in about 10 minutes and I'd call her from there. 
When I got to the pay phone, I gave her a ring. She told me her apartment was right across the street and which apartment was hers'. I walked across the street and went up a flight of stairs. I knocked on the door and when the door opened, I saw the hottest Latina you could imagine. She was barely 5' tall and couldn't have weighted 100 lbs soaking wet even with clothes on. She ushered me in and we got down to business. 1 hour "massage" was $45. I gave her $45 and made sure she saw I did have more money in my wallet. The massages sucked, but she kept rubbing my ass and my cock was getting rock hard. She told me to roll over and when I did, she just stood there and stared at my big thick cock. 
My 8" cock was so hard, it was throbbing. Even a bit of pre-cum was oozing out the tip. It would have lain against my stomach if it wasn't so damn hard.  She asked if I was "up" for something extra. I told her I really wanted to fuck her. She said she couldn't because it was "that time of the month". I asked her what she could do for me; she told me she'd love to suck me (for $40). I told her to strip to her panties and I'd give her $50. I gave her the money and she went to work.
Her mouth felt like velvet. She gave the softest blow job I have ever had. She gently sucked me and I closed my eyes. I was in heaven. My hand was on her ass; then it was on her pussy. I felt the sanitary pad there, so I figured, she was on her period like she said. She sucked my cock for over 30 minutes and I could tell from her breathing, I was having an effect on her with my touching. She told me she wanted to do something, but I would have to be careful. I said I'd do anything as long as I could cum. 
She lay on her stomach and told me to climb on top of her. She pulled her panties down and positioned my cock along the crack of her ass. She handed me some massage oil to pour on her ass crack and I poured a whole bunch. I slowly fucked my cock back and forth, up and down her wonderful crack. She pushed her ass back to me and was moaning into the pillow. I kept going faster and faster, taking long strokes as I went. On one upward thrust, I slipped down a bit because her hips were moving up and my cock slide right up her ass. I stopped dead in my tracks. I was about to tell her I was sorry, but she just told me to hold still for a moment. 
I felt her ass relax and she told me to fuck her ass real slow. I rose up and down ever so slow. It was so fucking tight. At that point in time, I'd only fucked a few asses and this one was the tightest out of all of them. She encouraged me to go faster and I did. Now, my hips were slamming hard against hers and I knew I wanted to bring her up to doggy position to get a better angle. I reached under her to bring her hips up and I felt something.
In my hand was a 5" uncut rock hard cock. I was ass fucking a tranny. She was about to freak out, but I told her it was okay, I was bisexual and I loved fucking trannies. With that was a sigh of relief and her ass actually opened up even more. I grabbed her hips and really started to fuck her. I fucked her ass as hard as I could. The sounds of her moans and groans of ecstasy were driving me insane. I wanted it to last for ever, but I also wanted to blast a huge load up her ass. 
My cock was right on the edge and I felt her ass contract around my cock as she came. I reached under her and felt her cock shooting streams of cum as I pumped my cock in and out. I put my hand in front of her cock head and caught some of her cum. I brought it to my mouth and drank down the thin liquid. As I drank her cum down; I shot three thick shots of cum deep in her ass. 
I slowly lowered her to the bed and turned us to our sides. I spooned her with my rock hard cock still deep in her. I asked her how she was doing; she told me she was feeling real good. I asked her if I could fuck her ass some more since I was still rock hard. She told me sure, but to go slow. I fucked her ass in the spoon position for another 30 minutes and she told me her ass was getting kind sore. I told her give me just a few more minutes and I'd cum again. She said sure and I continued to fuck her. I reached around and played with her cock. It was hard again and it felt real good in my hand. 
I came inside her again, but this time it was a bit on the weak side. It still felt real good, but I wasn't done. I pulled out and rolled her over onto her back. I went down on her cock and sucked her real hard. After a few good sucks, she shot a load into my mouth. I brought her legs up high and looked at her gaping asshole. My cum poured out of her all over the bedspread. I tried to ask her what I owed her, but she shushed me. She told me she loved what I did for her and that she hadn't came in over 3 years since she started hormones. She gave me her private number and told me I could fuck her ass anytime I wanted, as many times as I wanted. 
I meet her every few weeks, fucking her for hours at a time. I always came deep inside her and she would cum at least once, if not twice. A few times I had her fuck me, but that wasn't really her thing, although she did cum in my ass so much one time, it leaked out of me for hours. She moved around the bay area a few times, but we always kept in touch. Two times she brought her "boyfriend" along to let me fuck also. I know it really wasn't her boyfriend, but just a client of hers that needed to have his ass fucked, but I never let them know that I knew. She never charged me to fuck her, but I always gave her some money so she could make ends meet. Then one day I called and her phone was disconnected. I'm not sure what happened to my "hot Latina", but I would do anything to fuck that ass one last time.


