Pittsburgh Shemale Encounter

When I was on the road for my former law firm, I found myself stuck in Pittsburgh for a week for a mind-numbing labor arbitration hearing. I usually got into trouble when I was away from home and stuck in a hotel room all by myself. Pittsburgh was no exception.

The week started out harmlessly enough. I stopped in at the local adult bookstore and picked up a copy of the magazine ‘Transformation’ and a copy of the western Pennsylvania swingers magazine. This got me through my first night on the road with visions of shemales dancing in my head, and a couple of cumshots landing on the headboard of my bed. The second night, I ventured through the swingers magazine looking for crossdressers and shemales local to the Pittsburgh area. I ended up calling one of the phone sex numbers in the back of the magazine and talked to who I hope was a real shemale for over an hour while wishing that her cock was really in my mouth.

By the third night, I had to do something. I had been fantasizing of being with a shemale for weeks prior to this road trip. I needed to see a beautiful shemale wrapped up in a pretty package - heels, pantyhose, panties, lace bra, and short skirt - in my room. I needed to feel her hair against my face, and taste her cock in my mouth. I was even ready to bury my face in her ass and eat her out for as long as she wanted. I needed to be a total bitch boy for a shemale.

I got up the courage to call one of the telephone numbers in the Pittsburgh Yellow Pages, and arranged to have a Brazillian shemale visit my room around midnight. My heart was ready to beat out of my chest when I made the appointment with the escort agency. When she did arrive at my room, it was more that I had ever expected. She was flat out gorgeous and dressed in a black cocktail dress with slingback pumps and sheer black pantyhose. She could tell right away what I needed. She came close to me and put her hand on the back of my head. I thought that I was going to be tasting her lips and tongue, but she just smiled, grabbed a handfull of my hair, and led me across the room, practically dragging me behind her.

She took a seat on the couch, and I found myself down on my knees before this goddess while she called her agency on her cellphone to let them know that she had arrived. When she got off of the phone, she stood up, lifted her dress, pulled down her pantyhose, and told me to lick. I buried my face between her perfect ass cheeks and licked around her asshole before she told me to “put my tonge inside.” My cock was ready to cum while my tongue was in her ass, and I could tell that her 8 inch cock was getting hard. When she turned around, she didn’t need to tell me to put her cock in my mouth. I sucked down her cock all the way to her smooth balls.