My former male classmate became a female teacher - a cross-dressing story

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Last summer, during a weekend getaway, my classmates and I, who had graduated eight years prior, held a reunion in Taichung. When I entered the venue, I noticed many classmates had changed; they had lost their student naiveté and gained a more mature, working-class air.

Then I saw Yu-ching. Wait, wasn't Yu-ching a boy? How come she looked like a woman? Her hair was longer, she wore some makeup, and she was wearing a fitted skirt and a suit. While she was still petite, it seemed she had breast augmentation. Honestly, Yu-ching had become incredibly beautiful; none of the female classmates could compare to her.

We ate and chatted. Our classmates came from all walks of life. Yu-ching sat next to me. Surprisingly, Yu-ching, as a woman, had passed the entrance exam and become a primary school teacher. This wasn't surprising, as Yu-ching's grades were always among the top three, unlike those of us who were in the bottom three.

Although Yuqing was dressed in women's clothing, she was still the same as everyone else. However, the suit she wore that day had a really low-cut collar, and I could occasionally glimpse her cleavage through her light blue strapless bra, which made me feel a little guilty, but also strangely excited. It

was already past 3 PM when we parted ways. I thought, although it's still early, I'll just drive back to Taipei.

As I opened the car door, Yuqing walked towards me, smiling and saying, "So early, already in a hurry to go home?"

Perhaps it was from the beer, but Yuqing's cheeks were flushed, making her look very beautiful, which made me look at her a little longer. "No, nothing urgent, just going home. Why, do you want to come home with me?" Just like in our student days, I teased Yuqing.

"Sure, I've got nothing else to do anyway, might as well go shopping in Taipei. I'll lock the car, wait for me!" Before I could even process what was happening, Yuqing had already locked her white Civic 6, quickly walked over, and jumped into the front seat.

"Come on, what are you daydreaming about!" Yuqing smiled at me, as if it were the most natural thing in the world, while I felt completely lost, utterly oblivious to the situation. This continued until we reached the highway, exited at the Muzha Interchange, and arrived at the East District that Yuqing had suggested we visit. Before we knew it, it was late at night.

"My legs are so sore from all the walking, let's go home!" she said, hooking her arm around mine. This scene reminded me of a couple deeply in love.

"Sir, your girlfriend is very pretty! Want to take a look?" A clothing vendor by the roadside looked at us, his eyes full of smiles.

"Hey, seriously, where are you staying tonight?" I asked as I drove.

"Isn't this your house? I don't think we need to look anymore!" Even though I knew Yuqing would give this answer, I still felt she would definitely change her mind at the last minute. Yuqing's personality had been so unpredictable since their student days.

But when Yuqing carried her small bag and followed me up to the fourth floor, I realized she was determined not to leave.

"Let me tell you, if my parents ask later, don't say anything nonsense. I don't want them asking all sorts of questions after you leave." I said as I opened the door. A note was floating on the French windows, with large characters that read: Uncle Nanbu is moving into his new house tomorrow. We're going to help. Remember to come down tomorrow morning.

"Looks like I can skip the greeting!" Looking at Yuqing's mischievous face, I wondered if she was really a teacher! After welcoming Yuqing inside, I let her sleep in my sister's room. Since I had a long drive tomorrow, I wanted to go to bed early after taking a shower.

"I'm not going to entertain you anymore. You'll have to fend for yourself! Help yourself to the fridge, watch TV, listen to the stereo. I'm going to sleep now!" Lying in bed, I couldn't fall asleep no matter what. Hundreds of questions were swirling in my mind, forming a big question mark: Why did Yuqing insist on coming back with me?

My thoughts were interrupted by the sound of a door opening. Yuqing walked into my room wearing an oversized t-shirt. "Can you chat with me for a bit? I can't sleep!" she said, sitting down next to me. This caught me off guard because I only wear underwear to bed. I quickly pulled up the light blanket.

We chatted about this and that, when suddenly Yuqing fell silent. After a while, she suddenly said, "You're such a blockhead!" I was still confused when Yuqing slowly crawled into my blanket and said, "You know, I've liked you since our school days, and I still have. I thought you'd be interested if I dressed up as a woman, but you still ignore me. Am I really that unattractive to you?"

Actually, God knows, when Yuqing dressed up, although she wasn't stunningly beautiful, she was definitely a beauty among beauties, more womanly than most women. I think Yuqing wouldn't even look at someone like us.

"Actually, when I saw you dressed up, I was completely captivated by you, but it seems you're not so easy to win over..." Before she could finish speaking, Yuqing rolled into my arms, her faint perfume filling my nostrils.

I gently embraced Yuqing from behind, carefully. I looked at the skin on Yuqing's neck, so smooth, so delicate, and couldn't resist giving it a light peck.

On one hand, Yuqing was a male classmate, and we had studied together for several years. On the other hand, Yuqing wasn't just any cross-dressing beauty; she was a primary school teacher. This made me even more apprehensive, like a child afraid of doing something wrong.

Unexpectedly, Yuqing turned her head to one side, making it easier for me to taste her skin. She raised her hand and wrapped it around my head, seemingly enjoying it.

At this moment, I boldly pressed my body against hers, my hands moving from behind, roaming over her body, starting from her waist and slowly caressing her ribs. My hands stopped below her breasts, and I was considering whether to move upwards when Yuqing shifted her body, and my left hand covered her breast.

To my surprise, despite her small stature, Yuqing had a considerable bust. Even more surprising, she wasn't wearing a bra. Once I confirmed this, I felt it was a waste to leave it through her clothes, so I simply slipped my hand under the hem of her t-shirt and cupped her breasts in my hands. I gently pinched and kneaded Yuqing's breasts. They didn't look like they'd been surgically enhanced; they were incredibly soft and elastic to the touch. The soft feel in my palms was irresistible. Then I found Yuqing's nipples, teasing them and tracing circles on her areolas with my fingers.

By this time, I was already aroused, so I pressed my already hard penis against Yuqing's inner thighs, letting her directly feel my burgeoning desire.

At this point, I wasn't thinking about anything else. Experience told me that Yuqing was a special woman, and a cross-dressing beauty who could drive a man wild.

My right hand kneaded Yuqing's full breasts, my thumb and middle finger playing with her nipples, while my left hand slipped down into Yuqing's panties. My hands were met with a lush meadow, which almost made my fingers lose themselves in the thick pubic hair.

"Wow, so thick! It's been treated!" I whispered in Yuqing's ear, rubbing his soft, small penis. Soon, my fingers pulled back his foreskin. As my fingers circled and gently stroked his glans, Yuqing let out a soft "Mmm..." Before I could speak, he spread his thighs apart, allowing my fingers more freedom to move up and down.

I had decided to enjoy this lovemaking experience properly and give Yuqing the best possible experience. This couldn't be rushed. So, I first used my middle three fingers to massage Yuqing's soft penis, initially making gentle circles, then increasing the pressure. I felt Yuqing's penis go from soft and drooping to hard and stiff, until finally, even the glans turned red and released a trickle of semen.

At this moment, my hands and mouth were certainly not idle. My right hand focused its firepower on attacking her nipples and areolas, while my tongue roamed over Yuqing's pink neck and delicate earlobes. Under this multi-pronged attack, Yuqing's legs spread even wider, and her anus happily exposed itself to me.

"Oh... um... where did you learn that... um... um... it makes me want it so... so much... oh... um..." At this moment, I bent my middle finger and rubbed Yuqing's already hard glans, which caused Yuqing to release more semen. Her buttocks arched back, and her slender waist twisted from time to time.

Clearly, Yuqing's desire was already high, but I still pressed on with one last strike, sliding the first and second knuckles of my middle finger into her anus, teasing her inside and igniting an even more intense lust within her.

"Hmm... Teacher, is this alright? What do you want?" I boldly teased Yuqing's ear, while simultaneously intensifying my attacks with both hands.

Yuqing gasped repeatedly, "You... this... this bad... bad student, I... I'm going to punish... punish you by making you copy the text... oh... hmm..."

"Teacher's going to punish you by making you copy the text, then I'll have to flatter you!" With that, I quickly pulled down Yuqing's panties, and Yuqing arched her buttocks back, writhing impatiently.

I aimed my already engorged and hard penis at Yuqing's anus, inserting the glans a little, and then, as Yuqing writhed, my hands tightly covered and kneaded Yuqing's full breasts.

"Okay...okay, I really want it...no...don't do this...please..." Seeing that the time was right, I thrust my hips forward and pushed hard, instantly plunging my entire penis into Yuqing's anus.

At this moment, I held still, allowing Yuqing to fully experience the sensation of my penis filling her anus—and I felt the same way about Yuqing.

As expected of a cross-dressing teacher, it was slippery, hot, and tight. Clearly, Yuqing hadn't had her anus penetrated in a long time. Once again, I felt incredibly lucky.

Slowly, I began to thrust back and forth, and Yuqing gently swayed her waist with my movements. My desire grew stronger and stronger until it was uncontrollable. I flipped Yuqing over onto her stomach and began to attack her from behind. Yuqing didn't lower her upper body yet, but instead arched her back to meet me. I held Yuqing's 24-inch waist and thrust violently. This position allowed me to clearly see my penis going in and out of Yuqing's anus, and Yuqing's hard penis swayed up and down, giving me a great deal of sensory stimulation.

"You...bad student, bullying...bullying the teacher, you should...you should be punished...um...um...oh..."

I smiled after hearing this and said, "You should be punished, stand up!" So I first pulled out my penis, turned Yuqing over and picked her up. Yuqing's legs naturally wrapped around my waist, so I held Yuqing's buttocks with both hands, aimed my penis at Yuqing's anus, and pushed it forward, and started doing it while standing.

Yuqing seemed to derive immense pleasure from this, and I, because Yuqing was petite, didn't need to exert much effort, so I naturally enjoyed it immensely as well. After playing like this for about fifteen minutes, I felt Yuqing's glans twitching in waves, and a large amount of semen gushed out. Her whole body became hot, and she hugged me tightly, shouting passionately, "Oh...oh...ah...ah...um...oh..."

I knew Yuqing had ejaculated, so I placed Yuqing on the edge of the bed, while I stood on the floor, lifted Yuqing's buttocks, and began with the deepest thrusts. Then, twisting my waist, I pressed the tip of my glans against Yuqing's rectum, grinding it powerfully. After a while, I felt a suction force from Yuqing's anus, as if it wanted to suck my penis in, while Yuqing's prostate gushed out scalding prostatic fluid, as if it wanted to drown me.

"Oh...give it to me...give it to me quickly...I want it...I want it..." At this moment, Yuqing was a woman completely overwhelmed by desire, waiting for the response of her extreme pleasure. And I, no longer wanting to torment Yuqing, let her enjoy it!

Feeling a numbness in my lower back, I pressed down, allowing Yuqing's rectum to suck my penis in, and then poured a large amount of hot semen deep into Yuqing's rectum.

Yuqing closed her eyes, seemingly enjoying this extreme pleasure with abandon. I lay on top of Yuqing, gently stroking her glans with my tongue, then kissing her testicles and her anus.

"Passable, right?" I said with a soft smile.

"If this isn't good, I don't know how to give a perfect score!" Yuqing's eyes were languid, her cheeks flushed, truly incomparably beautiful.

Suddenly, I thought of something that seemed quite important, and my face stiffened for a moment.

"Hehehe, it's okay. I've been cross-dressing to regulate my hormones and because I love beauty, so I haven't slept with any men since I started cross-dressing. Don't worry! I'm not sick!" To be honest, Yuqing's words made me feel ashamed. Facing the generous Yuqing, I seemed to have lost my manly magnanimity and was truly outshone by her!

"Yuqing, let's go to Taichung tomorrow. I'll drive back when you're at work, okay?"

I got excited thinking about going out with Yuqing tomorrow. And now that I have a beautiful cross-dressing teacher in my arms, I think I'll probably get very little sleep tonight!

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My former male classmate became a female teacher - a cross-dressing story

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