How I Turned Myself Into A Perfect Sissy Part II [MF] [Anal]

*I really advice you to read the first part first.* [*It is over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwfq0/how_i_turned_myself_into_a_perfect_sissy/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

After being locked up for about a week, horny was in full swing. I was desperate for some relief. I wanted to jerk my rock hard dick, I wanted to fuck some hole. Any hole. But both

of it was just a no go. So I got creative. I asked the Internet. I researched other ways to cure horny.
The first thing that popped up was exercising. Exercising and even more exercising. So I go myself the first gym membership of my life. And I bought myself some nice running shoes and some nice, tight fitting sports clothes.

When I hit the gym, I trained mostly my ass, to turn my body more female. To get a nice big and round booty. And it worked out. But I wasn’t a skinny dip back then. I had some pounds on me. That was where the running came in. I went on runs nearly every day. To cure horny, to loose weight.

I combined it all with some diet, not a too harsh one, because not having the right food, the food I like turns me into a total unlike able bitch. And no one likes bitches. Men love nice woman. And well, I wanted to impress a men. Finding someone to fuck with, finding someone to suck off, yes, my mindset was already transitioning.

During it all my roommate was next to always with me. She took pictures, she filmed me, we posted that stuff online. Besides a ton of encouraging comments that kept me going more and more people were following. Some were even willing to financially support me and my transition a little bit. Not that I, not that my roommate and I got rich back then, but some expanses were covered.

But horny wasn’t cured forever. It came back a few exhausting weeks later. But it changed. The urge to fuck something wasn’t as big as it used to be. I wanted to get fucked now. I wanted a big dick up my ass, I wanted a dick sliding in and out of my mouth and then dumping a load down my greedy throat.

I told my roommate, and my best friend since back then, about my urges. A pleased smile appeared on her face: “So it really works. I think it is time for the next step.”

Then she took me by my hand and we went into her room. Then she turned on her computer, opened a web browser and then we went on a web page that was selling sex toys.

I blushed a little bit, giggle escaped my throat when I saw all the beautiful plastic dicks. I naturally wanted to buy the biggest one, but my roommate stopped me: “Stay reasonable. Start small, get bigger. You don’t want to destroy your fuck holes before the first real dick was sliding in and out of them.”

She was totally right. So we ordered some smaller toys, plenty of lube and something to clean out my dirty hole. To prevent nasty accidents. To feel save while playing with myself. My first supporters paid for my first toys. I thanked them with some special, individual and exclusive content later on.

A week went buy until the order arrived. I was more than just exited. My roommate was next to me, filming it all. Filming the exited, happy expression on my face when I sucked on one of the dildos for the first time. Not to train myself, not on intention, it just happened, because a cock sucking urge overcame me.

About an hour later my dirty hole was clean. I was ready to train my asshole. So I lubed up my dirty hole, took the smallest dildo we had ordered, lubed it up too, and then I slid the toy up my ass. It was my first time. It was the first time that I got fucked, or that I fucked myself up the ass. My roommate filmed it all.

After some time to get used to the feeling of something inside my ass, I began to slid the toy in and out. In and out. Then I applied more lube. And kept on going. Moaning was escaping my throat. It felt good. It felt awesome. And it relaxed me, horny left, well it never really left, it just got less. It got easier to bear.

I was in heaven. I was riding my new toy, I was toying myself in various positions, I was hitting different spots, but that was all. I wasn’t able to have an orgasm. Not back then. But the first step was done. I lost my anal virginity, unfortunately only to a toy, but well, better than nothing.

And I really needed the practice. I needed to train to ride a cook. To built up some stamina. To built up the needed muscles. To really be able to please a man. To be able to rid him long enough until he was willing to dump his sticky, tasty juices inside my ass. And yes, I was so looking forward to some real cock back then.

But it was to early. My body, my mind wasn’t fully ready back then. My roommate knew that. So she made me suck on some dildos for the rest of the day. She was taking pictures, she was shooting videos, she was encouraging me to take them deeper and deeper, but also took care that I stopped before I began to hurt myself. Yes she really took care of me back then.

Now that my anal and blow job training had begun, now that my body got sexier, slimmer with every week, it was time to buy some new panties, some new stockings and my first piece of sexy lingerie. A very kind supporter was willing to pay for it. He just wanted a few of my worn old panties in exchange. I sent him three pairs, sealed in a plastic bag, as soon as his money arrived.

To get the lingerie my roommate and I went in the biggest woman underwear store in town. At first the didn’t wanted to let me in, but when we told them what was going on with me, the were so nice and allowed me to enter their store.

In the store, I was overwhelmed. Nothing but good looking, good feeling and nice lingerie everywhere. And to my surprise, looking at it didn’t made me horny like it did in my past, it just wanted to have them. To wear them. To show them to someone else.

It took a while until we found something that really fit, luckily a saleswoman helped us out a lot. I tried on countless pieces. My roommate took pictures of me in nearly every piece. In the ended we decided for a classic, black one.

I wore that thing all the time when I was training my dirty hole. The viewers loved it. More and more tuned in with every training video we posted. My holes got used to the penetration. I fucked both of them every day. My toys got bigger and bigger. It felt better and better with every time. I was barely ever thinking about woman in a sexual way anymore: Sure, I adored them, because I wanted to be like them. And I was on my way to reach that goal of mine.

Source: reddit.com/r/Erotica/comments/xvf25w/how_i_turned_myself_into_a_perfect_sissy_part_ii