My first experience with a transgendered woman (M/T)

It was a late night, I was 18 and very horny in my parent's house, and I was on craigslist looking to experiment a little. I've known for a while that I'm bisexual, but at the time I had only been with cisgender women before. I was trying to find a transwoman to mess around with and get to know, as I had developed a bit of a fetish for them.

I posted an ad, and after sifting through a lot of scammers and old guys, I connected with a very beautiful woman with an enormous cock. I was nervous because I assumed that her pictures were fake, but she agreed to come pick me up as she lived in the next town over. When she arrived, she was just as sexy as in the pictures, and she was very dominant. She was tall, with an hour glass frame, and long, straight blonde hair.

"Nice to meet you boy," she said in a very feminine voice, as she grabbed my ass and rubbed my cock in her car.
She then proceeded to guide my hand towards her cock, and I was amazed to feel that it was quite big even soft. As I started rubbing it, she began to get hard and it was evident that she was much larger than my modest 6.5 inches.

Once she was fully hard, she pushed my head into her thick cock and I began to suck the first dick I had ever seen in person other than my own. Not only was it the first, but it was also one of the biggest and smoothest cocks I have ever seen to this day 7 year later. I sucked her the whole 15 minute drive there and she took me into her apartment where she stripped me down and went to town on my cock.

She had a gorgeous, feminine face, covered in intricate makeup, and her big, thick lips got my cock hard immediately. She sucked me so well that I had to focus on not blowing an early load. Eventually, we started 69ing with her on top, and it was incredibly pleasing to grab her round ass, while sucking her huge cock while having my own cock serviced as well.

I then ate her asshole and lubed it up, getting ready to go to town on her doggystyle. Once I got some momentum going, I began to feel her elephant trunk cock and balls slapping up against my legs which only made me harder. After I finished, she grabbed my ass, pushed me into the center of the bed, and said "you're next."

I had toyed with my asshole at this point of my life, but I had never taken anything like her cock before. She had to have been at least 8 inches long, and 6 around. I told her to be gentle at first, and she began with a small buttplug before moving up to a bigger toy. Once I was ready, she inserted her enormous cock into my ass very slowly before moving faster and faster. I began to feel my own cock grow rock hard as she fucked me. She then started jerking me off rapidly while fucking me doggystyle on her bed. I started to feel such intense pleasure from a mixture of prostate and cock stimulation, that I immediately came, but she kept going. Eventually she pulled out and blew a load on my face.To this day, this experience is probably one of the sexiest hookups I have ever had.

When we put our clothes back on, and got back in the car, I tried to make some casual conversation with her, and she kept replying with one word answers. After driving about 1000 feet down the road from her home, she slammed on the breaks, and yelled: "Get out of my car!" I stopped and looked at her for a second, and she repeated: "Get the fuck out of my car!" Awestruck, I got out, and she sped away back towards her apartment. Considering that she lived a solid 5 miles from my house, and I didn't bring my wallet or phone, I was in for a long walk. It took me until the sun began to rise before I got home, and I spend the whole walk wondering why she chose to do that.

Source: reddit.com/r/gonewildstories/comments/3uigob/my_first_experience_with_a_transgendered_woman_mt

5 comments

  1. Yeah it was a real bummer. The worst part is that I never got a chance to do it again!

  2. Yeah pretty much but she was so hot that I still get hard thinking about her massive cock.

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