College Crossdressers in Pittsburgh

Pittsburgh, PA (IB) – The Steel City has more to offer than Steelers, Penguins, Pirates and Iron City Beer. When I was little and traveling with my parents on vacation, my father told me that you can always pick out the airport gate where the plane to Pittsburgh was boarding just by looking at the people sitting there. Like it or not, Pittsburghers have a distinct look; it’s a stuck in the 1980′s look with big hair and fashion that comes from the back of most people’s closets. Although, I can’t say that I didn’t have my share of fun in the 80′s when I was in high school and the start of college. I always had good stories to tell after weekend trips to party in Pittsburgh.

I remember going out bar hopping in the Oakland near the University of Pittsbrugh main campus. The city offered less inhibition than my private college, and mixed with alcohol and weed, Pittsburgh provided plenty of dimly lit encounters and perversions each trip that I made. On one trip, I stumbled upon an ‘alternative’ club with music and patrons spilling out into the street. It was the first time that I saw college aged crossdressers, and I had to find out what else was in the club. I was out with friends from my school, and managed to separate myself and get lost from my friends so I could explore the club with the crossdressers. The short skirts, heels and tight boy butts were too strong of an allure for me to pass up.

Primed with beer and weed, my new surrounding offered little inhibition with house music and bass pounding and bodies pressed against one another on a packed dance floor. You couldn’ve move in the club without becoming intimate with at least three other people. Turning around, I found myself face to face with a fully crossdressed brunette who was hotter than any girl at my school. Without exchanging a word, I found her tongue in my mouth, and I was sucking her tongue as my cock started to grow in my pants. She turned around and started rubbing her tight ass against my cock trough my jeans as my hands felt up her entire body. Even though she had her penis tucked away in a tight pair of bikini panties, her bulge was growing too. As I rubbed her cock through her panties, her head went back and I started kissing her long neck. I couldn’t believe the experience that I was having.

We didn’t talk until we got outside. She was having a smoke, and I was unsure of how to approach the subject of going back to her place and going down on her. She solved that problem by taking me by the hand and leading me the three blocks to her apartment. Her roommate was still out for the night, and all I could think about was getting her cock out of her panties. Tasting her precum almost made me cum in my pants. I loved every second that her thick cock was in my mouth, and feeling her hand on the back of my head, I knew that I was where I was supposed to be – between the legs of a hot, sexy T-girl sucking every drop of cum from her cock.

Boston Shemale Hospitality & Early Morning Cab Ride

Boston, MA (IB) – I love Boston. I love the accents, the “T”, that red line on the sidewalk that prevents you from getting lost on the Freedom Trail, and most especially, I love the local shemale atmosphere. I have had more than my share of good times across the country as I travel on business, but Boston never fails to disappoint.

My first shemale encounter in Boston was a brief but memorable one. I flew into Boston from Columbus, Ohio for a brother-in-law’s bachelor party. We started out at a brew pub and pool hall near the old Fenway Park, and then moved the party downtown to do some bar hopping in the general vicinity of Faneuil Hall. When it was time to head back to the hotel in the early morning, the “T” had stopped running and it seemed that every taxi in Boston were already filled with drunks heading home to pass out. I and another guy got separated from out main group when we stopped off in a closed pizza shop to talk our way into using their bathroom so we could avoid publicly uriniating out in the parking lot with the group of bikers who were hanging out in their leather vests.

I thought this was an intesting sight until my new bachelor party friend and I started walking back to the hotel. We were a couple of blocks off of Boston Commons when we saw a couple of ladies getting into a cab. Desperately in need of a ride, we yelled to them to hold up and asked if we could share their cab. They were more than willing to help out a couple of drunk out-of-towners. My friend jumped in the front seat, and I climbed into the back of the cab with the two ladies to find out that they were two transexual ladies who had been out having their own good time in Boston that night. Now, this was at a time in my life when I was just beginning to appreciate transexuals, so I quickly decided to make the most of this opportunity.

When we reached the hotel, I walked in with my friend and then told him that I had left my wallet in the cab and that he should head up and pass out. The girls had kept the cab waiting for me, and I went with them back to their apartment. I ended up having the night of my life up to that point in time with Christina. Christina was a tall and lovely brunette with 36C tits and curves that I couldn’t believe, plus an eight inch package tucked away in her panties. Her girlfriend Maria went to bed while Christina and I stayed up all night as I enjoyed every inch of her beautiful cock and body, and she enjoyed taking my shemale cherry in Boston that early morning. I didn’t get any sleep that night because I was a greedy horny married man who didn’t know when I would have an opportunity like this again. Before I had to leave in the morning to catch my flight out of Logan International Airport, I gave Christina my best blowjob and swallowed every drop of her cum.

After leaving Christina, I was cheering my cabbie to ‘go, go, go’ to get me to my hotel so I could collect my golf clubs and luggage and get to the airport without missing my flight. I made it, and I even managed to catch about 90 minutes of sleep on my flight back to Columbus, Ohio. I remember kissing my wife when I got home without having brushed my teeth following the blowjob that I had given Christina that morning in Boston. I still enjoy that to this day, espcially following the divorce that I went through a couple of months later. It was definitely worth it.

Road Trip for Football Season

With college football season getting ready to kick off, that means that I’ll be making several trips to Columbus, Ohio to watch the Buckeyes play this season. Heading to Columbus affords me the opportunity to take in some post-game activities with a couple of my favorite T-girls. Cindy and Samantha have been showing me a good time whenever I’m in Columbus for a couple of years now. These two shemales are real beauties, and definite girlfriend experiences when we head out. … Continue Reading