Awakening With Jacky

Ironically, my first time publishing a story here was in the "First Time" category. This is really my first ever story so please don't bash me haha :) Admittedly, I didn't use an editor because I don't really know how to source for one here but I promise that the story is coherent and there would be no grammar mistakes that compromise the clarity and readability of it. On that note, I wrote this in Microsoft Word to use the basic proofreading so I hope that it is not excessively long because I initially intended for this to be much shorter but the story really took a life of its own. Enough of rambling, I hope you enjoy reading this and please leave any feedback in the comments!

***

*ting*

My phone screen lit up and the Tinder logo caught my eye.

Instinctively, I glanced at my phone.

I received a match!

I was overjoyed -- I had been using all my swipes with barely any matches and I was determined to give this a shot. Opening the app, I went to check the profile of my match and my heart skipped a beat when I saw a voluptuous brunette with a heart-melting smile. Hopefully her personality matched her looks, I thought as my fingers started trembling in excitement.

Wow, now what do I say?

Hi?

or

Hello?

or

Please give me a chance because I'm super shy and have never had a girlfriend?

Nah, that might scare her away. Ok never mind, I'll reply later when I'm calmer.

***

Here I was in the subway feeling so nervous, my heart thumping in my chest trying to escape. Wearing a navy blue formal shirt and black pants, I'm hoping I'm not overdressed. The Irish Tavern? I've never even heard of this place before but my date suggested it so whatever, I'm not about to argue with Jacky.

Oh yes, I forgot to tell you about her!

Since Jacqueline matched with me 3 days ago, it has been amazing! We flirted with each other so much and she even gave me her number. Just last night we were texting till late, just chatting about all sorts of random topics from food to family, and by the end of it she even let me use her nickname 'Jacky'. I'm a sucker for someone with confidence -- and she really had me hooked. Enough about her personality, she just turned twenty but seemed mature for her age, both mentally and physically. By that I mean she had a perfectly rounded ass and generous breasts that were just the right size -- at least that's what I could gather from the racy pictures she teased me with. This really was like a dream, no, a fantasy come true, even though she was just a date.

As I was daydreaming about this, the train stopped at the next station and a crowd of people got on. A young couple were all over each other, grossly kissing and making out in the stuffy train, much to the dismay of those around -- although it turned me on by reminding me of Jacky. As I was about to look back at my phone, I saw a beautiful lady looking like she was headed to a club. Clad in a wine red figure-hugging dress and black heels, she had a killer body although her back faced me and I could not see her face. I smiled a little to myself, thinking about Jacky and how tonight was going to pan out.

*ting*

Jacky: heyyy um I'm 1 stop away what about you?

Jacky: do you wanna just meet at the station first?

Me: Sure thing!

I couldn't help smiling to myself as I stepped out the next station among the crowds pouring out headed to the city centre. She should be here soon I pondered as I sat down to text her.

Wait didn't she say she was 1 station away just now? That means we must have been on the same train!

Quickly, I glanced around but there were just too many young women who were, unfortunately, not my date. Amongst the crowd I saw the red dress lady rush towards the exit too. Just then, my phone buzzed.

Jacky: Hey, I'm at exit B wru?

Me: I'm just sitting at the platform chilling. Somewhere in the middle, around door 16 :)

Jacky: oh ok good, I was just about to exit. One sec, I'm coming over.

As I looked up, I saw several girls walking around, including the red dress lady. Hmm, she was pretty hot but that couldn't be her ri— Just then she turned and I saw the unmistakable face of Jacky!

Woah.

She was stunning, even hotter in real life than in her photos! Ok, she was a bit shorter than she looked in photos but with her high heels it was barely noticeable. The front of the wine-red dress caught me by surprise, with a plunging neckline and side cuts that exposed her tanned skin and showed off her ample breasts. Wow, how was I to keep my composure for the rest of the night? I was already enthralled by her at first sight and completely forgot I had been staring at her, rather indecently too.

"I'm sorry is everything alright? Am I dressed inappropriately?" she asked, breaking me out of my trance.

"No, no you're really fine -- I mean your dress is fine, sorry," I blurted out, a sheepish look on my face.

"Oh ok haha," she giggled cutely knowing I had just checked her out, "You're looking fine too. I love it when guys dress well because it shows they really care."

Phew

. Overall a good first impression?

"If I'm not wrong the restaurant should be near the river front. Let's walk by the river as the view is really nice", she chirped.

"

Mmm sure," was all I could manage, captivated by this beauty. She walked ahead and led the way, her shapely ass swaying as though she was catwalking.

Finally, we reached the Irish Tavern -- a cosy dimly-lit bar playing 80s music in the background. Hmmm, this seemed perfect for our date I thought to myself as we picked a table at a quiet corner, away from the rowdy groups of men having their Friday night beers. As we were browsing through the menu, the aroma of grilled meat tickled my nose so we decided on a sirloin steak and pork ribs to fill our spirits. While waiting for the food, we began talking and although I was really nervous when I met her, her laughter made it melt away and put me at ease as we talked and laughed the night away.

As we were talking about relationships, Jacky suddenly asked me, "So what's your ideal type?"

"Well, I do like brunettes but more importantly, I love a girl who smiles and makes me laugh because I feel comfortable too..." I rambled, caught off guard by her question.

"Hmmm, what about when it comes to sex?" She said seductively, winking at the end, "Do you want a girl to satisfy your kinks?"

"Errrr..." I stalled, before adding, "Yeah I guess." My heart started beating rapidly, worried that I would embarrass her with my inexperience.

As she probed further she began rubbing her foot up and down my legs using her heels to stroke my inner thigh, making me more uncomfortable. I couldn't even focus on what she was saying -- my mind was racing. What was she trying to signal? Somehow she was just talking normally as though nothing was happening but for me I could barely concentrate.

After five minutes of painful conversation, she said, "Could you pay the bill first, I'll go to the toilet."

"Ok sure", I said as I watched her head off towards the toilet, heaving a sigh of relief as I signalled to the waiter to arrange the bill.

Damn she really was such a vixen

, I mused, captivated by her swaying ass. As I awaited the bill, my phone screen lit up, with a message from Jacky.

*ting*

Jacky: Hey I need your help

Before I could even pick up my phone to respond, she rang me.

"Hey don't be alarmed. I'm actually fine but I wanna tell you a secret."

"Umm ok what is it?"

"Come to the toilet and see!"

"What?! Now?"

"Yeah, if not when haha?"

"I'm still waiting for the bill actually..."

"Zzz whatever hurry up and come here. I'm waiting!"

What the heck? Is she really ok or is she in trouble? Oh gosh I better check. Maybe she hurt herself and didn't want me to be alarmed? But why did she have such a sultry tone... Perhaps it's something totally different. Maybe she's horny after all that talk about sex... Ok no way. Stop being ridiculous I'm not that hot to make her feel horny so fast.

*ting*

Jacky: I'll be in the last cubicle

Jacky: waiting for you babe ;)

Damn

.

Ok she's probably not in trouble -- maybe just maybe she's horny and wants me? Wow this is beyond amazing and I can't believe it! As soon as the bill arrived, I quickly took out several notes and tried doing the math but my brain just wasn't working.

"Nervous about your first date, eh?" the waiter teased as he helped me out.

I forced a laugh, before rushing towards the toilet. Wait was it the female or male toilet? Ok let me just check the male one first just in case -- never mind, it's empty. Ok now I've never stepped into the female toilet since I was like 3 years old. How do I do this without getting caught?

*ting*

Jacky: are you coming? :<

Ok, fuck it!

I'm just going to walk in and not give a damn. Fortunately, the restaurant was dimly lit and mostly full of drunk people singing and cheering loudly to themselves, much to the bemusement of the waiters. Seeing all the waiters' backs turned, I spotted my chance and darted into the female toilet, hoping I wouldn't bump into anyone. PHEW! I was really lucky -- I stepped in just as a lady in the second cubicle closed her door.

Gulping the spit in my mouth, I walked over to the last cubicle, the large handicapped cubicle, and knocked twice. My hands were trembling as I waited in agonising silence, glancing back over my shoulder multiple times to make sure no one else saw me.

*ting*

Jacky: is that you?

Jacky: Don't speak just text me back :)

I texted back frantically, nearly dropping my phone in excitement.

Me: yeah of course who else???

Slowly, the doorknob turned and the door creaked open as Jacky peered out with a wicked smile on her face. Immediately, I rushed in and heaved a sigh of relief. Gosh, that was terrifying.

"Wow I didn't think you'd actually come" she laughed.

"Why not?" I asked, confused. "You literally called me here."

"Well, you seem quite shy about sex stuff so I thought you wouldn't want to do it," she shrugged

"True, but... I'm pretty horny and you're so beautiful. And also I've actually never done it before," I blurted out. Shucks maybe I shouldn't have said that but luckily she was understanding.

"Aww it's fine, everyone starts somewhere", she said in a soothing tone.

Suddenly, she reached out and caressed my face.

"You're so sweet and I'd love to be your first," she said excitedly, dropping to a squat position and kissing my crotch.

Before I could react, she stood up again. "Actually, we should take this slow since it's your first time. Let's start right from the beginning."

Looking me in the eye, she clasped my hands with hers and pulled me close. I held my breath as she tilted her head slightly and pressed forward, moving her lips to meet mine. Unfortunately, my nervous self tilted my head in the same direction, smacking our noses together instead.

"Let's try again!" she said, laughing. This time, she placed her hand around my neck and guided me towards her for a kiss. As our lips met, it felt like static and I pulled away in shock before putting my arms around her and kissing her deeply. The kiss felt magical, almost as if we were connecting on a spiritual level as time froze around us.

As we came up for breath, she pushed me against the wall and looked at me with lusty eyes. Before I could say anything, she leaned forward and kissed me hard on the lips again, before retracting slightly to soften her kiss.

Slowly, I felt her parting her lips as her wet tongue traced a circle around the soft inner part of my lips. As she did this, her hands found their way down to my hips and moved in circles around my back. Feeling the warmth of her kiss, I closed my eyes, taking in her lovely scent.

As I closed my eyes, she thrusted her tongue further into my mouth while grabbing my butt cheeks with her hands. As our tongues met, I felt her warm saliva exchange with mine and we licked each other's tongues grossly, slapping them around each other's mouths until we were out of breath.

Meanwhile, her hands worked wonder on my back while I just squeezed her toned body aimlessly with my hands. As we paused to catch our breath, I smiled and ran my thumbs along her cheeks. She let out her signature cute giggle and I felt compelled to kiss her. I pulled her close to my side and gave her a little peck on the cheek.

"Oooh," she cooed, "Kiss me all over pleeease!"

"Mmm," I hummed as I kissed her cheek again, the softness of her skin tantalizing me. Wow she really was a goddess, I thought as I traced a finger from her cheek, down the side of her neck to her collarbone and around her breast towards her cleavage. As I used the tip of my tongue to trace the same path, she giggled, running her fingers through my hair. Seeing how much she enjoyed this teasing, I retraced and planted sloppy kisses along this trail. Blowing gently to make my saliva evaporate for a cool slight burning sensation, I caused her to shiver a little.

"Ohhhh, that's so nice," she moaned, "Do that all over me please!"

"I'll try to... but you're so sexy I might not last," I said in amazement as she pulled the straps of her dress over her shoulder and slid her dress down to reveal her luscious breasts and pink panties. Straddling a black lacy bra, her tanned breasts were full and perfectly rounded, with perky nipples that stuck out through the lace. Seeing my astonishment, she tilted her head down and licked the top of her breasts, smiling coyly.

"Wow these are so beautiful," I said, bending down and burying my head in between her meaty mounds. As she caressed my head, I resumed my kisses. Starting from her clavicle just below her neck, I showered her soft skin with kisses, venturing down her cleavage past her navel till her waist. As I reached her panty line, I stood up and pulled her close, wrapping my arms around her. Kissing her lips hard, I began massaging her back. My hands caressed her flat torso and hers traced my back and neck while we kissed intensely, making gross noises as we exchanged saliva and our tongues trashed about in each other's mouths.

As we came up for breath, my hands moved to her plump breasts and I began squeezing them like I was milking them. This time as we kissed, her hands too found their way down to my butt crack and she began massaging my butt which felt oddly pleasurable, making me groan softly. Midway through the kiss, I tried to slip my fingers into her panties but she caught my hand, saying, "Not yet."

We continued to moan and groan noisily as we made out for another ten minutes, switching positions and kissing each other all over while our hands explored every nook and cranny of each other's body. Panting, I stopped to look at Jacky, admiring her body. Noticing me staring at her juicy breasts, she beckoned at me with her finger and turned around for me to unbuckle her bra. With shaky hands, I reached forward and tried to unbuckle the multiple clasps of her fancy bra but my fingers were too clumsy and were trembling uncontrollably.

"Hey. Take a deep breath and relax first" she offered, laughing.

Doing as she suggested, I unclasped her bra rather smoothly and let it fall to the ground. Even in the dim light of the toilet, her breasts stood out like monuments, hanging freely as they came loose from her bra. Reaching forward, I squeezed her breasts tightly, squishing them with my fingers repeatedly while grinning stupidly at her. I was lost for words as I had never done this before and playing with her breasts was so therapeutic. Again, I buried my head in between her breasts, this time letting the soft tissue of her bare breasts engulf me, unrestricted by her bra.

"Suck and lick them baby," she coaxed, guiding my head to her cleavage.

Licking her cleavage a few times, I opened my mouth as wide as possible and pushed her left breast in as far as possible. Applying pressure with my lips, I sucked her breast while licking her nipple lightly, grasping her other breast with my hand and flicking her nipple. I switched over and did this for her other breast, making her purr with pleasure as she bit her thumb, unable to contain herself.

"Oooh, now it's my turn," she chirped, signalling for me to stand up straight.

Arching her head forward, she kissed me on the neck, nibbling softly as I groaned. Undoing my shirt button by button, her head slowly made her way down my torso, paralyzing me with her kisses. As she neared my crotch, she undid the button of my pants before kissing my crotch, using her lips to feel my bulge through the pants material, making me close my eyes and groan loudly.

"Shhh someone might hear us" she giggled softly, bringing me to my senses.

Straightening up, she planted kisses all over my chest and tummy, making me tingle as she traced the outline of my abs with her tongue.

"Mmm, take off your pants and show me what you're made of," she commanded in a sexy tone.

Quickly, I unzipped my pants and pulled them to the ground, my raging boner strangled by my boxers as a small wet spot covered the head of my penis.

"Wow you're really horny aren't you?" She teased, "Let me see what's underneath there."

As she winked, I gulped, knowing this was the real deal. My first blowjob. I couldn't believe my eyes.

I took a deep breath, putting my thumb on the waistband and slowly pulling down my boxers when suddenly...

*KNOCK* *KNOCK*

"Hey could I use the handicapped toilet after you're done?" a girl's voice sounded.

I froze with my boxers halfway pulled down. We stared at each other, mortified. After a good ten seconds of shock, Jacky answered, "Uh sure," as I held my breath hoping she wasn't someone who saw me sneak into the female toilet.

"

Let's get out of here!" Jacky whispered, breaking my trance.

I frantically pulled up my pants without even zipping them and she haphazardly slipped into her dress, clutching her bra in her hand as we pushed the cubicle door open, knocking the door against a wheelchair.

"Shit!" Jacky cursed as we rushed out, taking a glance at the poor girl who we knocked into. The young lady, sitting in a wheelchair with a cast on her left leg, looked at us in confusion before laughing, "Had a good time, eh?"

Without turning again, we hurried out of the toilet, pausing to catch our breaths as I looked around to check if anyone noticed. Fortunately, there were fewer people around and the only waiter in sight was busy attending to some other guests. Taking this chance, I covered my face and ran out of the restaurant, with Jacky following suit soon after.

After we exited the Irish Tavern, I heaved a huge sigh of relief, putting an arm around Jacky and holding her close to me. I zipped up my pants, and saw her still clutching her bra in her fist. That was a very close call, a bit too close for comfort.

"Now what shall we do?" I asked, hurt that I blew my chance to get blown for the first time.

"Let's take a walk first to cool off," Jacky chirped, pushing her bra into my pants pocket. I glanced at her but she was beaming for some reason. How was she not shaken by this?

"Sorry about that embarrassment," I muttered, my face burning red.

"It's fine, I like the thrill of doing it in public places," she laughed, "And when you take risks you have to bear the consequences right?"

"Yeah, I guess," I shrugged. Wow she was really chill about this!

As we walked down the riverfront, admiring the view of the starry night, Jacky suggested "Let's walk down past the Orchid Gardens into the forest area." Although the view was really nice, my heart was on the edge after the earlier incident and my mind was distracted with thoughts of what could have been if not for the girl in the wheelchair.