The Break-up
September 9th, 2006 by acrylic
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.
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Aha! The plot thickens. In one way you were too reticent in taking it to the next level, but can regret it now because perhaps with another experience later on you found out it wasn’t such a big deal. Yet at the same time you didn’t follow the social norm with your first sexual experiences. It’s good to know exactly what feels comfortable earlier in adulthood. I was too shy to do anything with ANYONE until college.
I think the main reason I held back was cause I thought it might make me gay. If it was having anal sex with a “real girl” I’m sure I wouldn’t have hesitated.
I don’t know why I thought oral sex was ok, and anal wasn’t, but you’re right. It wasn’t until later in life, that I realized I was tripping over nothing.
Did you ever have your way with the new Asian girl you were speaking of? You know, the way your LB girl was acting, she definitely wanted to be chased after. Had you humbled yourself and approached her about the way she was acting toward you, it would have delighted her. All girls that act in such a way are hungry for extra attention of some sort. Maybe she wanted you to be less discreet with her or something. Was she in your school for the rest of the time, or did her family move away? Man, I would have had to keep her for longer than 4 months. Also, what were the stunts you said that she was pulling while she was with you? Details please!!
To answer your question, no, I never did get with that other girl. She had some geezer boyfriend, and wasn’t interested in being more than friends. It’s too bad, cause that girl was super-fine!
I totally agree with you that my Ladyboy girlfriend just wanted to be chased. Maybe she felt I wasn’t serious about her, so she wanted to test me. But instead, I got a bad case of the “roving eye” and wanted to try out something different.
It’s weird, huh? I think for most straight guys it’s just the opposite. They’ve been with “real girls” all their life, but secretly want to try something different…and get down with a Shemale.
So maybe some people can understand that I wanted to try something different too.
Acrylic, how come going down on her was ok but not penetration (something every male college student would like their girlfriend to try)? How do I put it delicately, was swallowing cool with you? Can’t say I’ve gone there myself.
No need to put it delicately. I’m pretty much open to talk about anything on this site, and I always appreciate your comments!
To tell you the truth, I never swallowed her cum. She always pulled out before cumming, and jerked herself off, sometimes on my chest.
I know most male college students want their girlfriend’s to try anal sex, but I was still immature, being only in my second year of High School.
Somehow oral sex, in my mind at the time, just didn’t carry the same stigma as anal. Like I said before, I was too closed-minded, and felt that putting my dick in a Ladyboy’s ass would make me gay.
Oral sex could be considered experimentation, but there was no turning back from anal! I wasn’t ready to make that leap yet.