1. My Evolving Transition – Ch. 01


    Date: 4/10/2024, Categories: Fiction Pegging, Author: Luvagobfull 

    01. The Beginning:

I was not long out of school at eighteen, and my girlfriend for the past few months, was almost twenty-one. I was athletically built from the school sporting program, and rather good-looking, most girls flirted with me at school, but I didn’t take the hint and finished school alone as a virgin. Then you have my Tiffany, a girl every red-blooded dude with a cock would stare at if she walked by them. She had reddish-blonde dreadlocks, a seductive smile, blue eyes, and reasonably sized breasts. Tiffany also had secrets, that I was yet to find out about. I thought I won the lottery when I first hooked up with her.

There was a downside, to our relationship. She knew I was timid and if she told me to do something, I would do it. Little did I know, she was patiently grooming me for something else.

What began with a whirlwind romance where we had sex at least every day or whenever we could. In the beginning, we fucked like rabbits but then after three months, Tiffany started to feel stale. It was around that time I’d started thinking I was a girl trapped in a man’s body, and questioning myself, was I like Dr Jekyll and Mr Hyde, in a non-violent but sexual way?

It looked like it was over, between us. Although I was straight by nature, I started to stroke my cock while watching bisexual, or tranny porn, in secret. I also suspected that I wasn’t the only guy she was screwing, at the time. Little did I know, she had a girlfriend tucked away ...
    ... elsewhere.

We both held secrets.

Once Tiffany suspected I knew or suspected her secret, she hunted my computer and found mine. This is when she started to hatch her plan. She used the opportunity to try and spice our life before I called her out.

In the past, she had never denied the fact, that she plays the field and left it up to me if we were to continue. So, after some research, she dropped the idea, about pegging. She thought she’d spice up our love life, by pegging me with a strap-on. My cock twitched at the thought. I froze for a minute, as I thought about it.

“That’s gay, I’m not gay,”

I then responded.

At first, I was cold to the idea and in denial.

“Yeah right, I’ve seen your secret of websites, you may not be gay, but you’ve fantasized about it,”

She snapped at me with a smirk. I didn’t know that she knew until she mentioned it,

We then debated it before I started to give it some thought.

“I’ve heard from my friends, that it feels amazing, just think about it before closing the door on it, pretty please,”

she said compassionately. I was still weighing up the pros and cons.

“It’s not gay, it’s just what couples do in straight relationships and relieve guys of prostate pressure,”

She sounded convincing. I didn’t know why I was fighting against the idea when I was curious about it anyway.

“I will go shopping tomorrow and Friday night, we’ll then have some fun,”

she said with a smile. She seemed more into it than I was.

The next day ...
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