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.