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.

Losing My Virginity

I grew up in a very religious house; my mom was pretty easy going, but my father was a hardcore Christian. Like, I believed that when my parents had sex, it had to be the missionary position and that was it. At birth, my parents were given a choice – did they want a girl or a boy, and my father of course wanted a boy. They ended up with a very feminine boy, and according to my dad, it was a sin to be anything but straight.

So when I hit the age of eighteen, I was out of there. I packed my bags, kissed my mom farewell, and hit the road with one hundred bucks in my pocket. It took me about five days to make it from Maine down to New York, and I tried to save every cent I had for when I got there. So basically, I starved for those five days until I got into New York safely. I got there and gave my parents a quick call to let them know I had arrived safely. My dad hung up in my ear.

I found a run down place to stay; it was a real dive but I had no choice. I only had a hundred bucks in my pocket. I needed to find a job quick if I was going to survive in this city. It was going to be tough being on my own. It felt good though to be on my own and able to be myself. It was the first time I could dress as the woman I felt I was, and I was beautiful.

Quickly I realized that I wasn’t going to get a job. I needed money though; I was already two days late with my rent, and if I didn’t have something by tomorrow, I was going to have to head back to my parents house. That just wasn’t going to happen. That’s when I made the choice to becoming a working girl. My only problem with that was that I was still a virgin. I would just have to suck it all in and make some cash.

We all do things we are not proud of, and at this point I knew this was going to be one of those things. Nothing was going to send me home begging though. So that night I dressed myself up, packed on the make up, and headed out the door. I stood outside realizing I had no idea where to go, so I just started walking. Half an hour later, my feet were getting tired in the heels I had put on; I couldn’t walk any farther. I was about to turn my ass around and head back to the slum of a room I had when a car pulled up beside me and asked me to get in.

He was a big bear of a man, not very attractive and kind of stinky but I had no choice … I needed cash. He parked in a dark, empty parking lot and started pulling at my clothes and groping at my body. I got nervous because this man had no idea I had a penis, and I don’t think I wanted him finding out. I pushed him back against his seat and ran my hand over his leg to his zipper. I thought I was going to gag at the thought of putting my mouth anywhere on this man. I closed my eyes and just did it. The most disgusting part of the experience was the humiliation of this man spilling his juice all over my face. He paid me forty dollars, then asked me if he could get more if he paid me more.

As he drove into me I kept my panties on to hold my hidden surprise from this guy. I exposed my bung hole to him and he was happy with that. Although he was kind of turned off by the hair on my butt. Opps, I forgot about there when I shaved.

I got my rent paid for another week with just that one nights experience. Luckily by the end of the week, I had landed a job waitressing at a local bar. I had to venture out for one more night to make another weeks income but never did it again. It certainly wasn’t the most romantic way to lose my virginity, but I’ll never forget how it all happened.

Shemale Thrills on a Football Afternoon

What purpose do shemales serve? They weren’t created by nature … they are medical marvels of genetics, hormones and surgical art. A male to female transexual is easy to understand; a woman trapped in a man’s body. But a shemale is in a class by herself. Beautiful, soft, chesty, and hung better than the average straight guy … shemales are eye candy for men and women.

The thought of sucking off a shemale cock is much more appealing to the average straight guy than it is to suck off another guy. Straight guys masturbate to thoughts of sucking cock, but a cock attached to a female body makes it easier to pop into a hertosexual mouth and some hairy bear’s penis. Plus, you get a female bi0tch attitude times 10 with a hot shemale who has a cock the size of your forearm. She knows she’s hot, and she knows that you want to be bent over or down on your knees taking cock.