Well, it’s been awhile, since I continued with my story about the first Ladyboy I was with, and maybe I was putting this off cause the memories are still a little bit painful.
It’s about how we broke up. We were only together around four months, but it was a great four months. In that short time, I received my first blowjob, experienced my first 69, and sucked a dick for the first time too. All with my beautiful, genuine, Asian-American, Ladyboy girlfriend.
We would meet up almost everyday after school, go over to her house, get naked and roll around, sometimes masturbating each other with our cocks pressed up against one another. Some of the things we did, surprised me, as I always considered myself to be totally straight.
But my Ladyboy girlfriend was more feminine, and hotter, than lots of the girls at our school…so how could I resist? Alas, as I said before, I was a total fool, and never took it to the next level…anal sex. It’s something I still regret today, and think it was from that point that things started going downhill between us.
She began acting a little cold to me, and sometimes after school, would just go straight home without waiting. I was a stubborn bastard, and didn’t want to bow down by asking what was the matter. Instead, I just played along, and gave her the cold shoulder as well.
This went on for like a month, and during that time, I started hanging out with this cute Asian girl from one of my classes. We were just friends, but I thought she was fine, and hoped she felt the same. Things with my Ladyboy girlfriend were on the rocks, plus I’d never been with a “real girl” yet. I was curious…and I have to admit, I wanted to taste her pussy, and go inside.
At this point my T-Girlfriend and I hadn’t broken up yet, but we weren’t even talking anymore. I started to feel that it may be over. One day, at lunch, when I was alone she walked up out of the blue and asked,
“Do you like her?” (referring to my new friend)
“Yeah.” I said.
“As more than a friend?!” She asked, more forcefully this time.
I could see the hurt in her eyes. ‘What should I do?’ I thought. Should I lie, and protect her feelings, or should I tell the truth, so we can both move on. I chose the latter option, and answered,
“Yes, as more than a friend.”
She started to cry, then pushed me hard, and walked away. I felt lower-than-low. But hey, I never cheated or anything. We hadn’t talked for a month, so I thought she wouldn’t even care. But she did, and gave me a serious guilt trip about it.
I felt pretty damn bad about breaking her heart…until I learned about the stunts she’d been secretly pulling behind my back when we were still together. Truly scandalous!
That story next time…
Click here to read about my scandalous Ladyboy Girlfriend.