Fulfilling all My Fantasies Ch. 01

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... "

I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smile, even though my heart was racing. Jalen was right though. Thinking back on what I've done in the past year, this was probably the most dangerous and exciting fantasy I've ever planned. It all started with simple fantasies like walking in public followed by going to nightclubs. But it was after meeting Jalen, when I felt safer venturing out with someone I trusted, that I started with more challenging fantasies, even some that I never knew I had. Every time I fulfilled a fantasy, I would start thinking of something up something more sexual, and more depraved.

My latest project - I was finally going to fulfil my drug-induced gang-rape fantasy!

But before I go into that, let me tell you how it all began, and how I became addicted to fulfilling my sexual fantasies as crossdressing slut:-

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I am a petite East Asian crossdresser, normal build in Asian standards, Caucasian teenage girl frame by UK standards. I had always wanted to crossdress since I was a teenager. I used to envy my older sisters whenever they dressed up for clubs. Back then, I was not sexually aroused by men - it was the power that beautiful female clothes bestowed to women, to garner control over men, that I wanted.

So, the moment I was sent to study in the UK, I was liberated. I began to collect a fair bit of women's clothing, wigs, makeup, etc. through university, and when I graduated, I had to get a place of my own, not only to house and expand my wardrobe, but to gain the full freedom to dress up any other time outside work.

Financially I was set - I landed a job paying nearly twice my graduating peers were getting - my reward for being the top student of my class.

I rented a corner terrace about three streets away from the clubbing scene in Bournemouth, in a nice part of town. It was nicely located - a quiet and sparsely populated street that my neighbours would never notice my alter-ego leaving the house at night, yet close enough to walk back after a late night in the nearby clubs.

Most nights, I would just dress up as soon as I got home - nothing fancy, a simple dress, a wig, very light makeup, and then go about with chores like making dinner, watching shows, doing dishes - you know the drill. I was an introvert, so not socialising after work gave me a lot more time perfecting my make-up skills, my voice and my feminine demeanour.

Some nights, I would go for a walk, just to enjoy the thrill of getting found out. I eventually knew I was very convincing though, as I had walked past neighbours who did not recognise me. I did not dress to draw attention back then, so I easily disappeared into the background. In those days, I was satisfied with just daily crossdressing and the occasional night time adventure.

Before bed though, I would revert to my male persona (who wears lipstick to bed anyway?) and I would indulge in some crossdressing videos and some Asian porn. Mind you, crossdressing videos because I loved learning more about dressing up, but I was still straight back then, and I loved watching Asian girls being used by big white cocks. It was a bit of penis envy in some sense, but it was more the domination that those men had over the girls that got me off.

One evening, I was still in Cristina mode, when I decided to jerk off before changing back. I had just finished practicing a makeup tutorial I saw the night before, and I wanted to see how it looks on Cristina, fully dressed. In my usual routine, I switched to the other tab, and scrolled down.

To my surprise, on one video was an Asian girl dressed very similarly to me. Short yellow dress, long hair, with black heels. We even looked alike - the makeup was sharp eyeliners with pink smokey eyes. It was an interracial video, a category which I normally didn't watch. I clicked the video anyway and watched it.

I was never so entranced by a porn scene. She was in a club, drinking some cocktails, when a black guy approached her, danced with, invited her to a booth, and then fucked her. Throughout the whole video, I kept imagining what it would be like to be her, roughly taken by a stranger in the club. As she climaxed, I felt released my load into my hands, and felt disgusted with myself. It was a dirty fantasy, and I was confused by how I was drawn by the cock she was sucking, rather than the Asian girl herself. Probably because I was Cristina, I told myself.

It did not matter much though, as that video made me fantasise for the first time about being the girl herself. That door was unlocked, and I was staring through it. What I didn't know was the second figurative door that unlatched itself quietly.

I returned to regular Asian porn, but I began to fantasise regularly on being the girl in the video.

On future Friday nights, I would dress up (conservatively, I might add), leave through the side door of my house into the adjacent alley, then make my way to one of the clubs. I would be one of those wallflowers, watching the crowd while sipping a few Bacardis, before heading home.

Back then it was still more about crossdressing with little sexual context - I really enjoyed dressing up in public just for the fun of it, and to see if I was convincing. But as I spent more time in those clubs, the more I wanted to be those slutty vixens, with men crowding around them, desperate for a feel as they loosened up on drinks. The men would dance with them, hands running over bare skin, 'accidental' brushing against their body and hips in the midst of the dance floor...

A couple of months later, my wardrobe expanded from mostly knee-long dresses and turtleneck tops to tight miniskirts, body-con dresses, stay-up stockings of various material, colour and types (fishnet, sheer, suspenders), more bare-shoulder tops and low-cut dresses, especially sexy clubwear.

Around the same time, I invested in a lovely silicone breastform vest. It matched my skin tone and it went from neck all the way to the base of my breasts. One problem that arose during that impulse buy was that only D-cups were available for my size. On second thought, it was not so much of a problem than a boon after all! It blended quite nicely along the shoulders, and I was now more confident of wearing sleeveless dresses, and especially clothes that revealed cleavage.

That purchase also changed my daily routine a bit. I used to wear sleeved clothes, so I did not need to shave my armpits. As the vest allowed me to show off my shoulders, I started shaving not just my armpits, but my legs. Not long after, the routine included my pubes.

Even after my wardrobe upgrade, I would still cling to the walls, but I was drawing more attention. I must have been quite convincing, as men began approaching me and offering to buy me drinks, to which I initially refused. By the fifth week though, I was happily accepting drinks and confidently dancing with them. I loved the attention the men were giving me, and how arousing I was to them. I enjoyed watching them as adjust their crotches, as I did some dance moves I learnt from K-pop music videos.

And that's when I met Jalen.

Usually, I would always leave after feeling tipsy. One night, I probably had more drinks than I could handle. I was getting very drunk, and it must have been obvious to some, because as I continued dancing in the crowd, I could feel hands caressing my hips, feeling up my legs. At one point, a hand started tugging my black miniskirt up, exposing the laces of the fishnet stockings and touching my bare thighs. I started to panic, worried that my true self would be found out if they went any higher. I tried pushing the hands away, but somehow they always came back. All of a sudden, a tall, black man pulled me aside and asked me if I was feeling alright.

It suddenly felt too real. I was being groped and nearly exposed. A stranger was checking whether I was alright. I mumbled that I was OK, and that I wanted to go home now.

"Let me call you a cab," he said. I nodded in confusion, and he guided me out of the club. "Did you bring a coat, anything else?"

I felt for my sling purse and felt relieved. I shook my head.

"Wear mine." He put his suit around my shoulder. I was wearing a see-through white long-sleeve blouse, and the material must have looked cold in the autumn breeze.

The fresh air cleared my head a bit. I turned and looked at the stranger. He had gone to the taxi stand to queue. He was about a head taller than me, clean-shaven with a short crop of hair. He was dressed in business attire sans the coat and a tie. Quite handsome, I thought, like a young Will Smith.

"Hey," I called out. "I actually live nearby, so I'll just walk."

He walked over, "Are you sure? You don't look too well."

I nodded again, "Yea, I'm sure. Don't worry. I'm only five minutes away, and my mind's clearer now."

"Let me walk you home, at least." He put his arm out. A little chivalry, I thought to myself. I grabbed it, pulled myself up, and started walking, while leaning on him, a smile on my face.

After a while, he asked, "My name's Jalen. What's yours?"

"Cristina, you can call me Cristi, for short." I looked up and stared into his dark black eyes.

"Well Cristi, you weren't too careful tonight, were you?" Jalen said. "I'm not too sure, but I think you may have been slipped something."

"What do you mean?"

"You may have been drugged, I think. Do you feel like your mind is hazy?"

"No.. I don't normally get drunk, just tipsy. Then again, I don't normally go for so many drinks in a night. I think it was the alcohol. I'm actually feeling much better now, thanks."

Jalen sighed in relief. "That's good to know. I was worried that you were, you know, roofied!"

"Well, it's a good thing you were there then," I replied.

We walked in silence for a bit.

"So what brings you to Bournemouth? I haven't seen you before, I would have remembered," I asked, shyly.

"Well, I work in London, but I just started a project here. I'll be here every Thursday and Friday. I didn't feel like returning to London, so I decided to stay the night and explore the club scene."

"Oh, does that mean you'll be coming to the club more often then?"

"Only if you'll be there," Jalen smiled. "By the way, you're gorgeous, if you don't mind me saying!"

I blushed. "I don't mind at all. By the way, so are you! You're quite attractive, tall and dark, the way I like it." I guess the alcohol was still in my system after all, as I braved myself, and touched his abs, "Wow, you're muscular underneath these clothes as well! How old are you?"

It was Jalen's turn to blush. "I'm 22, I just graduated actually."

I continued, "Me too! So Jalen, what do you like about me?"

"Well," said Jalen. "Your legs, for one. They're so long and perfect, and I love how they end in those cute heels. And your lips... so red and luscious..." He suddenly took a step back, and said, "Was that too creepy? I swear, I'm not usually like this!"

I started laughing, and Jalen must have felt relieved. "I guess I had a drink too many too!"

Just then we arrived at my home. "Well Jalen, here's home. Thanks for walking me, and for being my knight in shining armour back there."

"Well, you're not my first cross-dressing friend who got in trouble, you know."

A moment of silence.

"Wait a minute, you - you know?" I stammered.

"Well... yeah. The signs are there you know."

"What signs?" I asked.

Jalen smiled, and replied, "Well, you still have your apple, and, your wig's a little off-centre now, since we left the club."

I pulled away from Jalen, a little embarrassed. I started correcting my wig. "Please don't tell anyone, I didn't mean to mislead you when I flirted earlier. I only crossdress for fun..."

"Don't worry, Cristi, your secret's safe with me. Also, my friend would never forgive me if I didn't stand up for you back then. And I really meant it when I said how gorgeous you were. You're very convincing!"

At that moment, I felt how genuine Jalen was. I gave him a hug, and said, "Thanks. Jalen. You're a great guy!"

He hugged back, and said, "Well, since you're safe and sound, I guess I'll be heading back to the club now."

"Emm... would you like to come in and a drink?" I quickly offered. "I would like to get to know you a bit more, if only as a friend. You're the first person who knows I crossdress. Plus, the club will be closing soon, it's already 1am."

Jalen looked uncertain. "We just met, I don't think you would want a stranger in your..."

"I do! Oh, please say yes!" I pleaded. "I would love to hear about your friend too!"

Jalen agreed.

We sat on the couch, had a lot more beer and talked for a while, me sharing my experience crossdressing, and Jalen sharing stories he had with his female crossdressing friend. She was his best friend, and found out accidentally about her habits during university. Since then, he was her confidante, and wingman at times, as she discovered her sexuality.

As we spoke, I noticed how hard he was trying not to steal glances at my thighs. I did not realise it, but as I got more comfortable on the couch, my skirt hiked up ever so slightly each time I moved, that eventually my bare, inner thighs were exposed. He was also shifting in his seat, a clear sign that he was getting an erection and trying to hide it. We were both getting drunk, but he was still being such a gentleman!

Jalen was really a nice guy, and I suddenly felt bad that he could not enjoy the club. A good guy like that, he deserved a good ending to the night. I decided there and then to do something I thought I would never do - give a black man a blowjob.

I started to recall the video I saw months ago, and realised at that moment how badly I wanted to see Jalen's cock. I had always thought my first would be a white one, but I guess the video was always in the back of my mind.

I downed the remaining half pint of beer, got up, and kneeled in front of Jalen. I looked up to him, and saw his shocked face, eyes wide open.

"I know I said I crossdress for fun, and not for sex. I'm definitely straight, or at least I think I am. But I like you a lot as Cristi, and I'm sure Cristi would do this. Please, Jalen, would you let me suck you off?"

Jalen stared back at me like a deer in the headlights. He gulped and nodded.

I unbuckled his belt, unbuttoned his trousers and pulled them down. His boxers came down next, and exposed a monster of a cock! It was at least 7 inches long semi-erect, and my own was only 4 inches fully erect. Mind you, I did not used to watch interracial porn, except for that one video, and it was on screen.

I asked, quickly, "Do I need a condom? Any STDs?" One could never be too careful.

Jalen blushed ever so slightly and shook his head. "I'm actually still a virgin." That was too embarrassing to be a lie, so I took my chances.

While I never thought I would be in this position, I knew what to do. A blowjob as much as I could do, followed by a handjob to finish. I just did not have the experience to do anything else, and I was not going to ruin the night for Jalen.

I started by licking his shaft up and down, then playing with the tip with my tongue. I unbuttoned the blouse, exposing more of the silicone breasts, for his viewing pleasure, of course. The diamond necklace adorning my chest hung from my neck, and the black bra was now in his full view. I knew I dressed like a high-class escort when going to the club that night, and I wanted to play that part fully now. I kept staring into his eyes, letting know I was giving him my all. He sat up straight now, and moved forward. It gave me better access to his beautiful pole. It was getting erect, and was probably close to 9 inches now. My fingers were struggling to meet its girth, but my mouth had no issues fitting it in.

I put my arms over his thighs, and grabbed the base of his cock, and started sucking and bobbing my head. After enough salivating and lubricating it, I grabbed his muscular ass, and thrusted my head down, taking it as deep as I could.

For the first time in my life, and to my surprise, I realised that I did not have any gag reflex. Jalen must have realised this too, and stared at me with awe as I took in his entire cock to the base. I stared back and buried my nose into his pubic hair, and tried to hold it there as long as I could. I could feel his cock pulsating, throbbing in my throat, expanding into the full space.

"That's amazing!" he praised. "Oh my god, it feels so good!"

After a while, I pulled back for air. As I gasped, Jalen leaned forward and kissed me. "If you don't feel comfortable, you can stop. Please don't force yourself to do this for me."

Just then, I recalled one of my favourite porn videos, where the woman was being face-fucked lying on her back, and how the cock was visibly sliding down the throat. I was not sure if I could pull it off, but I sure as hell would try.

I shook my head, and said, "Jalen, don't worry about me. I'll let you know if I can't take it. For now, just enjoy the moment. I'm going to do everything to please you tonight. Just use me for your pleasure."

I pulled Jalen to a standing position, and then I laid down on the couch, head over the armrest. He instinctively stood in front of my face. He had a full view of my body now, miniskirt pulled up, my black g-string pulled aside, my tiny dick released from the tuck. With alcohol, I did not usually get erect, and was also the reason I did a simple tuck with tape when I went to the club that night. My semi-erect dick was probably only the size of his thumb. My midriff was now showing, the skirt was now bunched up around my waist, and the blouse were now pulled up.

He started by placing his cock in my mouth, and started leaning forward, pushing it deeper. My hands were squeezing my silicone boobs and I raised and lowered my legs as seductively as I could. I was still wearing my high heels, and I knew I was giving him a show.

All I could see was his balls, as smooth as it was tense. It was beautiful, and it came closer to my face as he inched deeper.

Already, he was gaining his rhythm, using my throat as his sex toy, thrusting in and out. He put his left hand on my throat, and with the other, grabbed my dick. He started twisting it with his thumb and index fingers, and gently massaging my balls with the others. With his other hand, he started squeezing my throat a bit tighter.

I was a good swimmer, and I could hold my breath for quite some time. As his squeeze on my neck intensified, I knew he was close to cumming. The next time he pulled out, I took a deep breath. As he plunged back in, I moved my hands to grab his buttocks, and pulled it close. His big black cock plunged into my throat, his balls smacked my face. As he pulled out slightly, I pulled him in deep again, letting him know he should try to finish up. I felt his hands let go of my neck and dick, and he grabbed the sides of my head.

He started thrusting deep into my throat repeatedly, my red lipstick staining his pubes. His cock was already well-lubricated from my saliva, and each thrust was a little harder. I let go of his muscular ass, and started running my hands along my entire body, giving Jalen a good show. To my surprise I was fully erect despite the alcohol - I must have been really enjoying this subconsciously.

My body shook with each thrust, and towards the end, as he increased speed, I kicked off my heels, and put my feet against the other armrest to steady myself. I stopped playing with my dick and grabbed hold of the coach with both hands. I was also nearing my limit of holding my breath, and I hoped he would finish soon.