Walking Fingers and Talking Anus

I was a habitual masturbator and somewhere in the process discovered the joys and pains of anal. I always fantasized about a woman enjoying the pleasure of invading my back door and delighting in the sight of me gyrating and masturbating as she worked on that dark hole between my cheeks. I started visiting massage parlours thinking that ladies who work there would be more open minded to a guy like me. I live in a Caribbean island where the subject is taboo and any guy who engage in such behaviour is queer or gay. I just love the booty; giving and receiving. Added to all of this, I am a black guy, so you can fully understand how complicated my situation was. I was still determined to get some, so I visited various parlours hoping to enjoy my fetish in secret.

On this fateful day, I called and arranged to visit a parlor in the central vicinity of the island, which was a good distance away from my home. As I got to the Central area, rain showers started falling lightly and I had to skip across the street to enter a taxi quickly that would take me to a location that I never visited before. I paid the fare and dropped off at the location full of anxiety knowing exactly what behavior I wanted to engage in. I called the number to let the lady know I was at the location and she advised me to cross the street and walk up to the front door of the house right ahead. A middle aged lady opened the door to the downstairs apartment and beckoned me in. My mind went into a state of confusion as she sounded nothing like the person on the phone and I requested someone thick and this lady was slim...very slim. As I walked in it seemed to be a regular home with a living room set, dining room set, television and other normal household items.

She asked me to sit and told me "she is coming soon." I sat waiting to see who the she was and after a couple minutes she appeared with a beautiful smile and said "hi." She was an ebony beauty. Tanned and smooth, a fair mix of chocolate and cream she was thick and sexy. She beckoned me into a room on my right and as she walked I was staring at the voluptuous ass she moved behind her gracefully. She asked me what I desired and when I told her body to body, she immediately started to step out of her dress and the black underwear she was wearing underneath. I also got nude and she took a peep at my dark slim body and started smiling when she saw my private saluting her wonderful ranks. She advised me to lie on my back and she asked me if to use baby oil or cream. I requested the baby oil and she began.

As she massaged my body, I started to small talk about her name and how she got into the industry. She instructed me to lay on my stomach and as she worked up the legs I asked her what is the weirdest request she ever got. She advised me that she could not say as it was to be kept between her and the client, but she really never had any strange requests. Just about this time she started on my butt. It was my cue to ask what she would do if during a massage, a guy requested or show signs of wanting anal play. The rain was no pouring outside. The room was dimly lit. My body covered in baby oil and her hands massaging my booty as it glistened in the soft light. A "hmmm" escape her lips, giving away the fact that she gave it a couple seconds of consideration and then she said softly "I might fuck him." With that response I exposed myself "what if I asked for it?"

"You" she asked.

"You want that?"

"Yes" I replied...".I enjoy fingering my booty and sometimes trying an object or two."

"Hmmmmm" she replied.

Then the massage changed. She was still on my butt but a finger was trailing between my cheeks with every rub. I started pushing up as her finger got to the hole and she started letting the finger linger longer on my hole.

She asked "oil or cream?"

This time I opted for the cream as I myself enjoyed using it to penetrate during masturbation. She went for the cream but returned with cream and a large towel that she laid on the floor. She sat on it and instructed me to come and lay on it on my back so she could get full access to the booty. I raised my legs and she applied some cream to my ass and her middle finger. She then started massaging the hole and pushing in the cream into my ass as got more hungry for the fingering. I took my hand off my dick as I felt the finger press against my black hole and I tried moving to get more of it. Seeing this, she slowly pushed it all the way in and my ass swallowed it up.

She slowly started moving back and forth giving me the full length of it and started pushing harder and faster when she saw how my ass took it. She had a smile on her face like she could not believe she was finger fucking a guy ass and he was enjoying it. After some time of the one finger, she upgraded to two fingers that my greedy bitch ass took willingly as i started groaning and stroking my dick. She did not say a word but kept fucking my ass with the two middle fingers as I whimpered like a bitch in heat and rubbed on my dick. After a couple minutes well of this, I could not resist anymore and groaned loudly as I shot my load all over my chest. I heard the "hmmm" again as she saw how hard and thick my cum was.

She asked if I enjoyed myself and my only reply was "what do you think."

My ass now satisfied and slightly sore, I needed a couple minutes to recover before I got up to shower and leave.

When I tried to make contact with her two months later, the number went unanswered like it never existed. It took me twenty years before I got back in touch with her and we chat almost daily now. We recall the fun of that day and I have now learned I was the first in a line of bootys she had the pleasure of pleasing. She is retired from that life, but I am desperately trying to get one last booty play session with her...