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Toby – Is a girl

1414 Words | 2 |4.33

I was so shocked when I found out my best friend was actually a girl. But then I couldn’t stop thinking about it and I just had to fuck him…her.

The following happened when I was 12 years old, my name is Luke, it was a bad thing I did but I don’t regret it. Judge me all you want but it was good, weird, but so good.

Toby, was also 12 at the time, and we had been friends for about 5 months ever since he and his family moved in to the vacant house across the street, he was the new kid in town so and we quickly became friends because we were in to the same things.

One Saturday we were helping his dad weatherproof the walls on the outside of the house and clear out the gutters, the house they’d moved in to had been empty for about a year so it needed a lot of work doing, so we spent the day doing that.

By late afternoon we’d pretty much finished and we were all dirty, while his dad packed everything away in the garage, Toby went in to the house to get a shower and cleaned up, the ladder we used to get up on the roof and clear the gutters was still up against the wall right near the upstairs bathroom window, so I thought it would be funny to climb up and scare him, we always pranked each other.

So I climbed up the ladders and got to the window, it was a bit steamed up but I managed to see inside when I pressed my face against the glass, I was going to bang on the window and scare the crap out of him but, well, that didn’t happen.

I looked through the window and I saw Toby standing under the shower, he was facing toward the window but his eyes were closed because shampoo was running all down his face, but I got the shock of my life, I saw him naked, full frontal, it was then I discovered that my new and best friend was actually a girl.

Yes, a girl, he had a pussy, no cock, in would be months afterwards that I found out Toby used to be called Sophie, SHE wanted to transition in to a boy, so became Toby and dressed and acted just like a boy, it was really convincing because if I hadn’t seen what I just saw I never would have guessed.

I quickly climbed back down the ladder and ran home to process in my mind what I just saw, I was so confused, but at the same time, as I was picturing Toby naked, I became aroused and got an erection, so I jerked myself off right quick in my bedroom.

I didn’t tell Toby what I’d seen but he did notice that I was acting a bit differently around him, I couldn’t stop staring at his crotch and thinking about the fact he had a pussy down there, I started having fantasies about it and him and me having sex, I wanted to fuck his pussy, I’d seen it now and I couldn’t get it out of my mind.

Of course they’d be no way he’d ever let me see it, and certainly not play with it, I couldn’t ask him without letting on that I knew his secret, so I came up with a different way, an evil way.

A few weeks later Toby slept over at my house, I had it all planned out, I got my hands on some pills and I slipped them in to his glass of juice while we were playing playstation in my room, I put loads in so they got to work quickly and he drifted off to sleep on my bed.

As soon as he was out I locked my bedroom door and crawled up on to my bed on my knees and looked him over, just staring up and down his body for about 10 minutes, then I got the courage to do it, I removed all his clothes until all he was wearing was his boxer shorts.

He didn’t have breasts, which I put down to him being 12 years old and probably just hadn’t started growing yet, but now that I knew he was a girl, looking at his body it kind of made sense, he was skinny and curvy, he had a girls body.

Finally the moment came and I reached over and placed my fingers under the elastic waist band of his boxers and I slowly pulled them down his legs, I smiled to myself when his bald pussy was revealed to me, it was weird seeing it on my friend who I believed was a proper boy, but also so awesome.

It was soft, warm and damp to the touch, almost sticky, while I rubbed and explored it I pushed my finger between the flaps and it went through the hole, it was boiling hot inside and very-very wet, it was strange because the inside was tight around my finger but also slippery and my finger moved very easily in and out.

A boner quickly formed in my pants and my heart was racing, I could literally feel it pounding against my chest as it pumped blood in to my cock making it hard as a rock, I quickly took off my clothes, eager to get going, I pushed Toby’s legs apart, the flaps of his pussy separated slightly, I leaned over him and I could feel the combined heat from our genitals as they got closer together.

At first I just rubbed my cock along the crack of his pussy, his juices lubricated my shaft, then my cock sank between the flaps and pushed in to his hole, it felt so good, the rim of the tight hole clung to my cock and pulled the skin on my cock back as I pushed it inside, it was a little painful but the pleasure was more intense.

I was doing it, I was fucking Toby’s secret pussy, I leaned down over him, pressing our bodies together, my head was above his and close, I was looking at his face while fucking him, it was so bizarre, he had very short hair and he did look like a boy, but as I continued to fuck him, the way I saw his face began to change, his lips were bright cherry red and he began to look more like a girl to me.

I couldn’t help myself, I pressed my lips to his and I kissed him, I heard myself quietly calling out his name, “Toby. Oh, Toby.”, fucking him felt so good, it was my first time and I was thoroughly enjoying his pussy, and then I came, my legs buckled and shook violently, and I emptied my balls completely, ejaculating all of my spunk inside him.

I was so exhausted afterwards that I just laid on top of him, but I didn’t waste this opportunity, after only a few minutes rest I got another boner and I fucked him again, I must have fucked his pussy 5 or 6 times that night, I was a horny healthy 12 year old and I could have gone all night.

When I was finished I cleaned up his pussy and the massive puddle of spunk off the bed sheets then I put his boxer shorts and t-shirt back on him and I fell asleep.

In the morning Toby complained about having stomach ache and pains down below but he never made the connection, he never figured out that I’d drugged and raped his secret pussy several times, but by doing that I got it out of my system, I wasn’t fantasizing about it anymore, it wasn’t constantly on my mind, so I was able to get back to being normal around Toby.

I didn’t care that he was really a girl, I put it out of my mind and we continued being best friends, he was just my friend Toby again.

Now that I’m a lot older I do think that I actually did a good thing, Toby may have wanted to be a boy but if I hadn’t have raped him, no one would have experienced the joys his pussy could give, the world would have been denied to pleasures of his pussy.

A pussy needs to be fucked, it wants to be fucked, that’s its purpose, I did him a favour.

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2 Comments

  • Reply CHINGATUMADRE

    Did he stay a girl or did he have the sex change

  • Reply Psiberzerker

    Transgender tweens often take hormone suppressors to prevent going through the wrong puberty. Which may explain how Toby didn’t have any breast development at 12. That’s also towards the end of the window (Roughly 9-to-13) where girls start thelarche.