My Crossdressing Life

I'm an ordinary office worker. After graduating from university, I landed a good job at a foreign company. Thinking back on the hardships and lack of freedom I experienced during my school years, I decided to enjoy a few years of work. If there's one thing that sets me apart from others, it's that I like to be a woman, even though I'm a man. As a child, I often felt ashamed of this idea, but later I realized many people shared the same sentiment. Because of this unique preference, I've always paid special attention to my appearance. I'd rather eat less to maintain my figure. I often stretch my legs, hoping they'll look longer. My only regret is not being able to actually dress as a woman. But that regret will disappear as I start working. I've gradually started buying wigs, stockings, women's clothing, lipsticks, and other cosmetics online. I'm going to fill that void. I've been planning for a long time to fulfill this long-held dream.

After graduation, I specifically applied for a job in another city, not living with my family. Due to financial reasons, I rented a room in a private residential area. The landlord is a very refined middle-aged man. The apartment had three bedrooms and a living room. He rented one bedroom, one study, and the extra room to me. The price wasn't expensive; he said living alone was too lonely, and he wanted someone to talk to.

I didn't know how to do makeup, so I often spent weekends searching online. After several weeks, I finally got the hang of it. One day, I finally put on a makeup look I was quite satisfied with, wore tight jeans, a tight top, a wig, and high heels. I looked at myself in the mirror for a long time, took many photos, and admired them for a while before changing.

I posted some of the selected photos online, on cross-dressing forums, asking for feedback. That's how my dressing skills gradually improved. I started thinking about going out in women's clothing and showing myself off to everyone. But the landlord was there every day, so there was no opportunity.

"I have a social engagement tonight, so don't buy me dinner; I'll be home late," the landlord told me as I went to work in the morning.

"Oh, okay," I replied casually, but my mind immediately turned to going out in women's clothing.

On Friday, I deliberately didn't work overtime and took a taxi home after work. I didn't eat dinner, took a shower, and carefully put on makeup. I finally went out. I was a little nervous. But, after walking for a long time, no one paid much attention to me. Was it a success? Or was no one noticing? I gritted my teeth and hailed a taxi.

"Miss, where to?" the driver asked loudly.

Huh? It was the first time someone had called me "Miss," and I panicked a little. "I'm going to xxx." I immediately said the name of a shopping mall, trying to sound as feminine as possible.

"Oh, a date, it's the weekend..." the driver said casually.

"Mmm..." I replied softly. Then I regretted it a little; there were too many people there, what if they recognized me?

"We're here, just give me ten yuan, don't worry about the change..."

"Oh, thank you..." I quickly paid and got out of the car.

I walked with my head down for a long time, but still, no one paid much attention to me. I slowly raised my head. I looked at a few more shops. Finally, I gained confidence.

"Miss, do you like this dress?" a saleswoman asked enthusiastically as she approached me.

"Ah!?" I panicked again. "Yes...yes..."

"It suits you, really, you have long legs, this dress is perfect for you. Look at the mannequins outside, you have a great figure, almost like them." The salesperson continued to promote it.

"I'm afraid it won't fit..." I wanted to find an excuse to leave.

"Try it on, come on, it's not expensive..."

So I went into the fitting room. I took a few deep breaths. I changed into the dress and thought it looked good. The salesperson was so sweet-talking. So I bought it. Is this the fun of shopping for girls?
Not daring to linger in the mall, I went home wearing my new dress...

My life of cross-dressing continued like this. Occasionally I would go out for a cup of tea and go shopping. I also often chatted online. I knew in my heart that people I met online were unreliable. We chatted and that was it, never meeting in person. I don't know when, I added a friend named Xunmi. We got along very well. I knew he was divorced, the reason was unclear. But he didn't know that I was actually a man. I think he's a gentleman. We've known each other for a long time, and he never asks to meet up or makes unreasonable demands. He also often helps me solve work-related problems.

Occasionally, I fantasize that if I were a girl, he would be my boyfriend…

The turning point came last year during the Spring Festival. I was considering whether to choose a plane or a train for the Spring Festival travel rush. My parents had already agreed to my older brother's suggestion that we spend the New Year in Singapore. Due to work, I declined. I talked to my mother on the phone for a long time. Although she nagged a lot, she couldn't hide the allure of Singapore.

I chatted with him online…

“When are you coming home?”

“No, my parents went to Singapore.”

“That's great! Why don't we spend the New Year together?”

“No… it's inconvenient for me to go alone.” Actually, I had a little longing in my heart, but after all, I'm not a girl.

"I'm just looking for a companion."

"Uh... I rent a place..."

"I have an apartment, come on over."

"No, I'm just getting ready for the Spring Festival travel rush, it's too late."

"Seriously? We're just chatting in the same city, you seem to be making excuses. Something's wrong?"

Sigh, I really didn't know what to say, so I just made up an excuse and ended the call.

I forced myself to watch a few movies, and it was already late at night. I was still a little uneasy about suddenly hanging up. Unable to resist, I logged onto QQ again. His profile picture was still online. Before I logged off, he started the call again.

"Are you still there?" I said casually.

"You're acting weird..."

Sigh, anyway, it's just a computer network, we don't really know each other, so I steeled myself and decided to tell the truth.

"I... I'm actually a guy... I'm sorry..."

"Really? We've video chatted before. You're not exactly stunning, but you're still got a certain charm."

"Sigh... I really am a guy, I like cross-dressing..."

There was a long silence, no reply. He'd probably think I was a pervert, maybe he'd already turned off his computer? Suddenly, the penguin hopped, "What if I liked it?"

This was an answer I'd never considered. He must have thought I was playing him, or he was playing me.

"Stop it, I'm a bit of a pervert who likes to dress up as a woman... I really don't want to talk anymore."

"I know... but I've been looking for you for a long time. Listen to me..."

He typed slowly, but told his story in the most concise language. He had a neighbor from a family of Peking Opera performers since childhood. He never understood why boys could be prettier than girls. He was particularly interested in cross-dressing. Later, after encountering Thai ladyboys, he found it even more unbelievable.

Once, on a business trip to Thailand, he couldn't resist meeting a ladyboy, only to be seen by a colleague. That's how he got divorced and quit his job.

"I really want to meet you, and I admit, I'm interested in you. Since you like to dress up as a girl, you need someone to pursue you to be considered successful."

I've always had feelings for him and didn't want to reject him, but there had to be a way out.

"Well, I've come to find you..."

"Huh!? You don't even know where I live..."

"So I came to find you, huh? I found you, you've lost to me this Spring Festival."

I felt a little dizzy...

The door to my room suddenly opened. I was startled too. Why didn't the landlord knock before coming in? I was still wearing a short skirt. My face turned red. How embarrassing. What she said next made me even more dizzy.

The landlord said softly, "I've found you."

He'd been talking to me all along... landlord?

"Listen to me," he said. "One day I had a business dinner and came home late. When I got upstairs, I found my house key in the car. I took the key, but then I saw a voluptuous girl open my door... and go inside." He licked his lips. "I thought she was your girlfriend, but I never saw her come out again."

"I started to have suspicions. At first, I suspected you were letting a girl stay overnight. But soon, I knew something was wrong. I'm sorry, I later secretly opened your computer and confirmed your online chat nickname. Later, we video chatted, and I was certain of my suspicions. I rented the apartment to you because you were so clean and tidy."

He continued, "I've found you."

I was still dressed in my carefully chosen women's clothing. Someone was confessing their feelings to me, and I felt happy, but I was at a loss.

He suddenly hugged me tightly, his thick lips sealing mine. I tried to break free, not because I disliked him, but because it was so sudden, so overwhelming. He still held me tightly: "You lost, now you belong to me, help your brother... your brother is so pent up... so pent up."

In that instant, I thought of the transgender protagonists in those pornographic films. They sucked and licked my penis, their buttocks raised, their anuses welcoming the thrusts. Some moaned, some furrowed their brows, letting the thrusts continue. My face flushed red to my neck.

The landlord's kissing technique was excellent; he kept kissing me, making my heart flutter. "Let's go to my room, the bed is big," he whispered in my ear, picking me up in his arms. I wrapped my arms around his neck. I thought to myself, this is tacit consent, isn't it? I wondered how I would serve him later. He

kept kissing me, his tongue constantly teasing me in my mouth. I truly enjoyed it, truly felt aroused. He stopped, then kissed my neck again, sucking on my earlobe. Gently biting and sucking on my nipples. He occasionally stroked my penis. I felt a slight electric current running through my body, arching my back from time to time. I've never felt this good before. His teasing had completely aroused me, but my erect penis made me incredibly embarrassed.

He seemed to read my mind. He gently held me, whispering in my ear, "It's okay, I'll teach you..."

I blushed and nodded.

He went from gently sucking my nipple to sucking harder, one hand lightly stroking my penis, the other roaming around my anus. This continuous, electric sensation was driving me crazy. "Brother... I can't take it..."

"Is it good?"

"It's good... but I can't take it... anymore..." I blushed, convulsing and writhing.

He suddenly increased the speed of his stroking, then took the opportunity to give me a deep kiss. I almost felt like I was about to ejaculate (I'd masturbated). He stopped stroking and whispered in my ear, "We're already like this, don't be shy. You can't be shy about this. Shout if you want to, scream if you want to, play however you feel good."

I looked at him breathlessly and nodded. “Brother, you really played with me so hard just now…”

“There’s something even better, my beauty.”

He turned around, grabbed a bottle, poured some oil into his hand, and gently applied it to the outside of my anus. Lubricant… I’d seen it in porn. He’s putting in oil first, so he’s going to fuck me now…

“Brother, you want to…” I blushed and couldn’t speak, then thought about what he’d just said, “You want to fuck me??”

“Yes!” Hearing such a frank answer, I blushed even more.

“I have no experience.” I whispered…

“Ah… you’re shy again…” He hugged me and gave me another deep kiss, “I’ll try my best not to hurt you, but it depends on the person; some people just can’t handle it. Also, once I’m done, I won’t care about anything else, but I’ll take care of you at the beginning.”

I was dizzy from the kiss; my female instincts were particularly strong, like a girl’s first time. It’s rare for someone to like me, so what’s a little pain? I wrapped my arms around his neck and said, “If you enjoy it, I don’t care how much it hurts.” After saying that, I lowered my head, not daring to look at him. He laughed… his fingers gently tracing the outside of my anus. Suddenly, his index finger slipped in, and I sighed softly. It didn't hurt. He thrust in and out a few times, then his middle finger went in, thrusting faster. I felt a swelling in my anus, a strange pleasure slowly, gradually appearing. The pleasure wasn't strong, but I could still feel it, and it increased with each thrust.

“Brother, go harder!” I groaned. I couldn't be shy anymore.

“You like it?”

“Mmm! It feels good, the harder the better, the faster the better…”

“You're really born to be fucked, you're enjoying it so quickly.”

“Mmm…”

I casually touched his penis, bigger and thicker than mine… about seven inches long. I played with it with my hand. I wondered if I should give him oral sex? Could my anus handle it? He took his penis, quickly put on a condom, and applied lubricant.

It's about to begin, I thought to myself.

His thick cock pressed against my anus, and with a thrust, the glans went in. The glans was large, and even the full insertion made me gasp. He then pushed further in. His cock was thick, and it really hurt at first; my anus felt like it was being torn open. I gasped several times. Seeing his expression of enjoyment, I couldn't bear to interrupt him. Besides, I had said that I didn't care how much it hurt, as long as my brother was enjoying himself. So I tried my best to spread my legs wide. My brother was on top, and I lay between his legs, my legs spread wide. I finally saw this lewd scene. I closed my eyes in shame.

He thrust all the way in before remembering me. "Baby, can you take it?"

"It hurts, brother, don't move, let me adjust," I pleaded, panting.

"I'm sorry, I was so focused on my own pleasure, I've been holding back..."

"Brother... I did it willingly, I'm not afraid of pain," I quickly said. Then I kissed his lips.

Another long, sweet kiss.

“Brother, move…”

“I’m afraid it will hurt you…”

“Brother, how can it be fun if I don’t move? Don’t worry about me. I like being fucked by you.” I really felt a burning desire.

“Okay, then I won’t be polite…” he replied excitedly.

I spread my legs wider, “Come on…”

The thrusting started slowly, but as his breathing became heavier, the speed of the thrusting increased. That inexplicable pleasure from before gradually reappeared. With the high-speed thrusting, he would occasionally stop to kiss me and suck on my nipples. I wrapped my arms around his neck, plunging into his crotch. The thrusting reached its maximum speed, and the sound of flesh colliding filled my ears. At first, I could still clench my anus, but later, I couldn’t feel anything. I only felt the pain from deep in my rectum accompanied by inexplicable pleasure. And the satisfaction of being conquered. At this moment, I knew that I would serve this man wholeheartedly from now on.

He was satisfied, just as he said, he couldn’t care less, no more kissing, no more caressing, just relentlessly fucking. I arched my back to receive each of his thrusts. "Good sister, you're so good..."

"Brother, are you enjoying it? You're so rough."

"Sister, can you take it? Does it hurt? Brother will fuck you to death, brother loves seeing you in pain, you look so beautiful in pain."

"Brother...loves you..."

With a shout, I felt him ejaculate inside me. His penis trembled incessantly, for a very long time. He must have ejaculated a lot. I hugged him tightly, my legs naturally wrapped around his waist. I squeezed my anus tightly, hoping he would enjoy it even more.

"Hoo..." He exhaled. "So good..."

Then he gently pulled out his penis. I immediately felt my anus empty... I understood, I would never be able to live without a man again.

He hugged me tightly and gave me a kiss naturally. "You were only thinking about yourself, and you still..." He looked at my penis shyly.

My face flushed again. "I'm fine, I feel great." Girls don't ejaculate, I thought to myself. I was already satisfied.

"It's okay, there's plenty of time in the night, I'll make you feel even better later..." he said mischievously.

Later... I felt a surge of excitement. I nestled in his arms, cuddling in the blankets for a long time, whispering sweet nothings. The happiness in my heart was indescribable.

"I'm going to wash up first." He suddenly pulled back the covers. I immediately hugged him and pulled the covers back up. "Don't go, it's cold."

"Wash up, just a little while... hehe, I'm not

done yet." "What if you get cold?" My anus was also a mess, so I used a tissue as a temporary measure.

"I still have to wash. It's sticky and weird."

A thought struck me, and I gently pressed him down on the bed. "I'll do it."

I crawled under the covers, my face next to his penis, my hand involuntarily reaching for it. "Do I really have to do something so degrading? How could I have such thoughts?" The question was immediately interrupted by instinct. I opened my mouth and started licking his penis. I licked it clean.

"Oh..." he exclaimed outside the covers? Was it pleasure? Or was he surprised by my boldness?

His penis was sticky and had a fishy smell. It tasted salty in my mouth. I imitated the transvestites in porn movies, licking his penis desperately. He moaned repeatedly outside the covers. After enjoying it for a while, he suddenly pulled out his penis, pressed me back onto the bed, and said, "Good sister, you have no experience, licking like this is itchy and comfortable, but you can't come."

He stuck my head out of the bed, held my head with both hands, and then sandwiched my head between his crotch. "Sister, brother will fuck your mouth." After saying that, he inserted his penis into my mouth. In an instant, my heart was filled with happiness. I was willing to use my mouth to welcome his penis. Just like in my anus, his penis began to piston-like.

"Sister, it's so good to have you...so good..."

His penis went in faster and faster, deep into my throat, making me feel a little nauseous. His two testicles rubbed against my face, tickling me. Would he ejaculate in my mouth? If he did, would I have to drink it? These thoughts excited me. I hoped he would ejaculate in my mouth.

"Ah...ah..." His penis moved in and out faster, each time reaching my throat. I knew he was about to ejaculate again. His penis suddenly started trembling, and he suddenly hugged my head tightly. He sat on my chest. Thick streams of semen shot into my throat.

After he finished, he stood up satisfied. "Mmm..." He let out a long breath. "Sorry, I was too excited, I ejaculated all of it inside..." He was a little embarrassed.

"It's okay, I like it..."

"You like it???"

I looked at him: "Yes, I like drinking your semen..." After saying that, I licked the remaining semen from his penis. Men must all like their sex partners to be both slutty and wanton.

"You're so slutty." He touched my whole body with his hands. "Drink this too?" He mischievously held up the semen that had just shot into my anus, filling the condom halfway. I blushed and nodded; I really wanted to taste it. He poured it into my mouth. I slowly savored it—it was fishy and a little salty. Very sticky. Then I swallowed it.

He looked at me, clearly moved. He hugged me tightly and kissed me repeatedly. "Don't tease me yet. Let me rest for a bit, then I'll make you feel good."

"You teased me first," I said unwillingly.

"Hehe... but when you licked my dick just now, I got all hot again." I buried my face in his chest.

"Does your back hurt?" he asked with concern. I shook my head.

"Let me see," he continued.

"Ah?" I exclaimed, thinking, after all this time, it's not enough, he wants to see too. How embarrassing to show someone my anus.

"Come on, let me see if you're hurt. Besides, we're practically husband and wife, what are you afraid to see?"

I nodded. I spread my legs again. He pried my legs open and gently removed the tissue stuffed inside.

"A little bleeding, does it hurt?" I shook my head, blushing. He inserted his finger.

"Ah..." I wasn't prepared at all.

"Doesn't it hurt?"

"No." I shook my head again. He took out the tissue and carefully cleaned my anus.

Suddenly I felt a warm, tingling sensation enveloping my anus. It turned out he was licking my anus.

"How dirty, don't do this."

"I don't mind you being dirty, don't you like licking my dick too..."

He licked diligently, his tongue reaching inside my anus. I was intoxicated, happiness overflowing my whole body.

After he finished licking my anus seriously, he straddled me, his penis pressed against my lips: "Come on, give your brother a blowjob." I took his penis into my mouth. I licked it lightly, moving it in and out. Soon, his penis proudly stood up again.

"Turn over and lie face down."

Doggy style, I knew what to do. I rolled over, raising my buttocks high. My asshole was already being fucked, so there was no shame. This position was even more stimulating, a feeling of being conquered. He applied some more lubricant to my anus.

"Put it in like this, deep in. I'll help you masturbate, but I won't let you ejaculate. Just lie there and enjoy it."

He thrust all the way in. "Ah...! Ah!... Ah!..." I screamed. It felt good, but it hurt too. No mercy whatsoever. It went all the way in. At the same time, his rough, large hand grabbed his penis from behind.

The slapping sounds of him fucking my anus and hitting my buttocks were incessant. With each thrust deeper, he would vigorously stroke my penis, and I quickly felt like I was about to ejaculate. He suddenly went crazy and fucked me dozens of times.

"Ah... ah... brother... ah... I really can't take it anymore. Be gentle..." My anus was burning, and it was stretched very wide.

"Brother, are you trying to fuck me to death... Ah!!! Okay, fuck me to death, I'll do it willingly..." The storm of thrusting into my ass made me dizzy. He still didn't speak, then suddenly, he leaned back and lay on the bed. With his movement, and with him holding my slender waist tightly, I went from lying down to sitting up. Due to my weight, his penis went further into my ass. I was sitting on his penis, and waves of numbness, pain, and the feeling of being torn apart all came together in my ass. I took two deep breaths, adjusted to the depth, and started moving up and down on my own. He increased the intensity of his masturbation. As the stimulation in front intensified, my buttocks moved faster and faster.

"Brother, ah... brother... I'm going to cum... It feels so good..."

As soon as he heard that I was going to cum, he grabbed the base of my penis with one hand, and moved his other hand even faster. Suddenly, I couldn't cum.

"It's all about your asshole. Get me out, and I'll let you cum freely."

My backside was burning, swelling with every thrust, while my urethra was blocked, preventing me from ejaculating.

"Ah...ah..." I desperately twisted my hips, lifting myself up and slamming down, no longer caring about the pain in my anus; it seemed this was the feeling I was after. His penis thrust upwards, matching my movements.

"Brother's getting it, so good..." Hearing he was about to ejaculate, I moved even harder. Suddenly, that inexplicable pleasure intensified.

"Brother, ah...ah...my asshole's going to burst...ah...ah..."

*Slap slap*... With my weight, I recklessly sat down, letting his penis penetrate my anus, reaching deep into my rectum. After dozens of thrusts, I truly reached my limit. "Brother, aren't you going to ejaculate? I can't take it anymore..." My voice was clearly trembling with tears.

"Oh...oh..." His penis suddenly trembled violently. He ejaculated again. In the instant he ejaculated, he tightened his grip on the base of my penis, and then his other hand forcefully stroked my penis. "Don't stop, keep moving, faster...faster..." He seemed to be begging me. I endured the swelling in my anus and quickened my movements. His penis trembled even more violently. At the same time, that inexplicable pleasure spread throughout my body. With this pleasure, I quickly sat up several more times.

"Aww...ah!!!!!" He suddenly let out an almost terrifying scream, his hand gripping the base of my penis loosened, and his other hand quickly stroked it. I ejaculated instantly, the pleasure from the previous ejaculation combined with the pleasure from the aftermath...

"Brother!!...Brother!!...Brother!!..." I called for a long time. Finally, I collapsed on top of him.

We were panting heavily. We rested for a while. "Come on, lick it." He put his steaming penis to my mouth. I held it in my mouth for a while, then licked it clean.

"Look..." He held up the semen he'd ejaculated; there was half a packet in the condom. "So much..."

I exclaimed. "It's been so long since I've done it, I saved it up... haha."

"You want me to drink it, don't you..." I folded a tissue and placed it outside my anus. "You feed me..."

He slowly poured the semen into my mouth; this was the second time I'd drunk his semen tonight...

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