Cross-dressing

A fictional story.

I lived in an apartment with my father. He worked until late evening, and I came home from school early for lunch, so I had plenty of time for entertainment alone. Ever since I started masturbating, I never thought about sex with guys, but over time, this intriguing and incredibly arousing idea crept into my head.

Finding pictures online of little boys dressing up in girls' outfits and giving themselves to guys, I realized that I also wanted to look like a girl and that I wanted to please a guy, no matter his age—teenager, adult—it didn't matter.

We weren't poor, and

not even a month had passed since the desire to transform into a girl appeared before I had saved up enough money to get everything I needed. I ordered women's clothes online, more girlish than womanly, and... a small toy—a 14-centimeter dildo, exactly the same size as my own. After all, I used to want to have sex with girls, I wanted to try anal sex; now I decided to feel what anal sex is like for a girl, and not just any girl, but for my future girl, because the artificial dildo wasn't my size for no reason.

"Yes, it looks more like a stripper's outfit," I said, unpacking the costume.

The package contained several sets of lingerie; all sets consisted of panties, a bra, stockings, and a garter belt to which the stockings were attached using small clips on an elastic band that went down to the thigh.

It was three o'clock, lunchtime; I decided I had time to have fun before my father came home, and without hesitation, I began the transformation. I carefully and meticulously changed into the women's clothes to fully experience what it's like to be a girl. I managed the underwear in about ten minutes, but I decided not to put on the sent dress—a tight, dark one with light inserts, reaching only to the middle of my thigh—or rather, I decided.

"Diana," I whispered. That was the name of the girl I wanted to take in the ass. "Now I will be Diana."

I couldn't wait to finally become a real girl, and I decided to try the artificial dildo. I had read online how to prepare a girl for anal sex, and now I used that experience on myself. I pulled my panties down to my knees, took off the garter belt, and began preparing for the hot action.

There was a tube of lubricant next to the dildo; I dipped two fingers into it and began carefully lubricating my ass. Everything slid so amusingly on the outside, probably like the outside of a pussy when it's wet, but I needed to lubricate inside as well. I slowly began to insert my index finger into my ass. At first, my ass tensed a little and seemed unwilling to let anyone in, but then I calmed down, and along with me, my ass, which I so wanted to feed with a male dildo, calmed down.

With difficulty, a second finger entered my ass, and then I realized that the time to use the dildo was almost here. I began to work my ass again, taking a bit more lubricant. When my ass fully submitted and the sphincter stopped convulsively squeezing around the fingers penetrating me, I took the dildo, lubricated it, and took a deep breath, trying to transition into a state of complete calm.

I began to press the head of the lubricated dildo into my ass slowly and carefully; a dull pain appeared in my ass, but I didn't stop pressing. A moment later, the sphincter couldn't hold and opened, letting the analog of my own dildo into my own behind. After inserting the dildo to the base of the scrotum, I began to pull it back out, and when it was halfway out, I impaled my ass on the dildo again, but this time I didn't use my hand—it was just holding the dildo—now I simply impaled myself on the dildo, making thrusting movements toward it, riding it and moaning.

Such entertainment made me lose track of time, and I no longer realized what time it was and heard nothing; I just continued fucking myself in the ass, as I had once WANTED to fuck Diana.

"Come on, Diana, ride it, ride your little ass on the dildo," I said in my former voice.

"Of course, darling. Whatever you say, Andrey," I answered my own words, already diligently imitating a female voice.

After a few more minutes, my fantasies about Diana subsided, and I decided to switch to something else; I managed, though I switched to something I didn't expect. I suddenly remembered my father and thought—what if I really were a girl?

My fantasies went far. I imagined how he would bathe me, not forgetting the place between my legs; he would touch me everywhere, gently stroking my skin with his slippery hands from the shower gel.

I closed my eyes and began vigorously riding the rubber dildo, shouting my father's name with each penetration. I was already tired of riding, and my legs were buckling at the knees; I was about to fall from weakness, but I held on and continued to satisfy my father, even if only in my imagination. Feeling the approach of orgasm, I paused, not wanting to finish so soon, and suddenly I heard a creak.

The door to the room swung open, and I saw my father standing there with his pants down, holding his dildo in his hands—he was masturbating.

"Dad?" I wondered.

"Diana?" said my father.

I lowered my eyes, embarrassed, and turned to face my father so he wouldn't see that an artificial dildo was currently visible from my ass; holding it with my hand and tensing my ass, I kept the dildo inside myself, and after becoming confident that it wouldn't fall out during the conversation, I raised my eyes and looked at my father.

"Diana, I heard you calling my name when you were inserting the dildo into yourself; don't you want to help me finish?"

"I... want to..." I mumbled, barely breathing, and moved closer to him.

"Get on your knees and open your mouth."

I knelt before my father; his 17-centimeter dildo was at the level of my chin, and when I moved even closer, the dildo was already touching my face.

"Now open your mouth and wrap your lips around the dildo; be careful with your teeth."

"Okay, Dad, I'll try."

I licked my lips one last time, swallowed the flowing saliva, and slowly took the head of the dildo into my mouth; then I pushed the dildo deeper into my mouth, and when I couldn't push it any deeper, I began to suck. The soft and gentle dildo grew hotter and harder with each sucking motion; Dad began to breathe deeply and then moan.

"Come on, Diana, suck, my beloved daughter."

I couldn't answer; my mouth was stuffed with the dildo, wet from my saliva, but out of habit, I still tried, and as soon as a muffled sound escaped me, a hot, thick liquid with a slightly salty taste spurted from the head of my father's dildo into my mouth. Father held his dildo in my mouth, pressing on the back of my head with his hand. I continued to suck the dildo, slurping and gradually swallowing Dad's sperm; when he removed his hand from my head and exhaled tiredly, his dildo was already clean—I had swallowed all the sperm and cleaned the dildo.

The dildo began to shrink, but I still didn't release it from my mouth; I played with it, licking it from all sides; the smaller the erection became, the more fully I could take the now-shrunken dildo into my mouth. I finished the game when Dad's dildo shrank to minimal size, and I could completely take it into my mouth, licking it with circular motions of my tongue inside my mouth. Finally, I kissed Dad's balls several times and stood up, looking at my father.

"You have something left here," Dad said, pointing to his lower lip.

"I got a little embarrassed and licked that spot with the tip of my tongue."

"Cute," said Dad and smiled.

"Did you like it?"

"Of course, daughter; I think we'll repeat it later. And Diana?"

"Of course, Dad."

"For now, change back into Andrey; I wanted to introduce you to my woman; she might live with us, so be respectful."

"Okay, Dad."

In the end, we kissed on the lips.