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To start things off, I am a male, currently 15.

So yeah, one time, it was around 1 or 2 in the morning, I had school in the morning. I was 12 years old at this time. My mom has this closet full of her gowns and heels and stuff like that. I was up at this time, and I felt the urge to sneak out wearing one of her gowns. So I decided to doll myself up, and I actually did a pretty good job, as I looked like a passable woman.

I snuck out of my house and started heading down the road. The area which I live isn’t very populated at late hours. As I was walking down the road, my neighbor randomly decides to check her mailbox, and she sees me outside. “Well, hello there, young lady,” she says. “Where are you heading to this late at night?” I try to say in my most feminine voice, “I’m just heading up the road, I went for a walk down this way.”

Then, my neighbor invites me into her home. I decline her offer, and start to head up the road further.

After 5 minutes heading up the road, I decide to head back to my house. When I opened the door, I had a surprise waiting for me.

My mom is sitting there, in the kitchen, which is right in front of the door coming in. “Well, well,” she says. “Shouldn’t my ‘daughter’ be asleep right now?”. “Mom, I can explain,” I try to say, but she stops me. “Oh no, it’s ok, my little girl doesn’t need to explain.” She then signals me to her room.

I sit there patiently in her room, straightening my dress out. My mother tells me to stand up, and she lifts up my dress. “So, you like these, huh?” She exclaims as she sees my growing erection straining on a pair of her p******. “Well,” I say, but stop. “Turn around,” she says, “and get on all fours.” I did as she commanded, and then, she yelled for my father.

My father comes into the room, seeing me on all fours in his wife’s dress. “So, looks like we need to teach you a lesson,” he says, as he grabs his belt. “NO, please dad, No,” I beg and beg. “This is what sissies like you deserve!” He yells, and starts whipping my a**.

After all the whipping, my mother sends me to bed. It turns out my mother unenrolled me from school, and re-enrolled me, but classified as a female. The rules are now:

1. I must wear skirts or dresses every day to school and in public.
2. I cannot get a girlfriend, I have to have a boyfriend.
3. I must wear a chasity belt from now on.
4. I must do the chores around the house now.
5. All of my stuff, including my phone, old clothes, and other things, were sold and I am only allowed to buy dresses and skirts.

Back to now, my neighbor passed away 2 months ago. She was big on fashion, and owned a lot of dresses from the 30s-90s. My neighbor’s husband gave them to my mom, saying he knows someone who will enjoy them.

As I’ve worn these dresses, I’ve felt like I am a woman, like I was never a man. My mother has ordered me a s** change so, I guess I’ll finally have the v***** I deserve.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.