Saturday Night is Date Night Ch. 02

Leaning forward, I press my lips together then pout to admire their glistening red fullness in the bathroom mirror. I step back, make a slight adjustment to the blonde bangs of my wig, and assess the figure in front of me.

My blue eyes sparkle, huge circles against the dark ring of shadow I'd penned around them. I always loved how dark make-up contrasted with my porcelain pale skin. Blonde waves frame my pretty face, the hair falling lightly on my shoulders and down my back. The upper half of my body is squeezed inside a tight black t-shirt several sizes too small, showing off my flat tummy and belly button. The lower half is covered only in a tiny, light blue denim skirt that barely stretches over the plump round cheeks of my ass. My legs are bare, save for the black straps of my heels around my ankles.

I pull out my phone and pose, hand on hip, for a few selfies in the mirror, trying to look as sexy as possible. I pout again, blowing myself kisses, before I realise I've gone full-on duckface and start laughing at myself.

I tap record on camera app and hold it up while I test out a few lines.

"Hi... thanks for picking me up." I say, reaching for my most feminine voice.

"Hiiiii!" I try again, going for a higher pitch and holding it for longer.

I flutter my eyelashes, and summon all my inner girl to say, "Can you take me to... uh..."

I laugh again. Just where AM I going tonight?

It's Saturday night and, like every Saturday night, it is what I call Date Night. Every Saturday night I meet with a different man, or sometimes the same man, for a date. Normally, I don't leave the house; the dates all take place in my apartment. But tonight was going to be different. Tonight's date was going to pick me up.

He'd responded to my ad with a suggestion that caught my attention. Date Night is always role-play night. And I like my dates to bring their own ideas. Last Saturday, my date role-played as my Daddy, getting home from work to find his bratty teen daughter about to go out dressed like a whore. He forbid me from leaving, spanked me, and showed me what happens to teen girls who dress like whores. The Saturday before that my date had wanted me to role-play as a masseuse, and I gave him the happy ending he sought.

Tonight's date wasn't only going to be the first such date to require me to leave my apartment, it also promised to not include very much role-playing.

His name was Amir. He had explained in his message that he was a taxi driver who wanted to fulfil a fantasy of picking up "a sexy girl like you," as he put it, and having sex in his car. He also attached a photo of himself, clearly taken as he sat in the driver's seat of his cab, showing his dark, fat cock sticking straight up out of his pants.

Just because something is a cliche, doesn't mean it can't be exciting. Almost all of the date night scenarios I've role-played with men have resorted to cliche, playing upon very traditional stereotypes of masculinity and femininity, and often very obviously cribbed straight from the guy's favourite porno. But at the same time, it's never stopped me from feeling incredibly turned on. Reading Amir's message and drooling over the attached photo instantly had me tingling in all the right places. I had replied on the spot and made all the necessary arrangements.

In the bathroom, I tuck my phone in my handbag after seeing Amir's text that he was downstairs, and take one last look in the mirror. A nervous thrill wriggles its way through my body. I pinch the hem of my denim skirt and lift it up at the front. Underneath, the head of my now stiff little cock pokes out above its black lace pouch, while below the thong strap splits my smooth, tiny sack in two before disappearing into my ass crack behind. I bite my lower lip coquetteishly and moan ever so softly.

"You look fucking hot, Amy," I say aloud to myself. And I'm right.

Sneaking from my 4th floor apartment to the street only heightens my nerves. My neighbours have no idea about Amy, and while I feel confident that I pass as pretty feminine - especially at this time of night - I have no desire to explain to someone why exactly their 23-year-old male neighbour is all dolled up in skirt and heels.

Role-playing getting caught is really hot. I'd done it a few times now. The sense of embarrassment and humiliation I'm able to summon for these sessions is always arousing, and it's a buzz to discover which way my date would play it. Sometimes he'd be caring and understanding; he'd still end up fucking me, of course, but he'd do so in a tender, supportive way. Mostly, though, he'd choose the opposite approach, holding it over me, blackmailing me to consent to whatever depraved sex act he desired; he'd fuck me hard and rough, almost sadistically using it as an opportunity to abuse me. However much I enjoyed role-playing either approach, my preference is to avoid such an encounter with my actual neighbour.

Fortunately, no one is there to surprise me as I gingerly descend four flights of stairs in my two-inch heels. The lights are on in the foyer, however, and I can hear someone hammering a door buzzer at the main entrance, but I manage to slip out through the fire door at the side just in time. It's dark in the lane that runs alongside the building and it takes me a few moments to realise that the cab I'm searching for is parked right in front of me. Amir must have switched off his sign to indicate he wasn't accepting passengers. My tummy is fluttering. I suck in a deep breath and open the car door.

"Hiiiii!" Thanks to my nerves, I end up half-squealing my greeting as I slip into the front passenger seat. My skirt's so short I can feel the slightly rough polyester of the seat rubbing against the bare skin of my thighs and ass. Keen to leave something to the imagination, at least for the moment, I keep my handbag in my lap as a small gesture towards modesty. Finally, I look over at the man seated next to me.

"Good evening," he says, in a thick foreign accent. "I am Amir. It is nice to meet you... Amy."

I smile and study him as closely as I can in the poor light. Broad shouldered, and sitting tall in the seat, he's bigger than I expected. He's carrying more weight than his photo suggested, too, with an obvious belly silhouetted next to the steering wheel. His face is dark, but I can make out a short beard, possibly strewn with grey, and the whites of his eyes staring back at me. Even though we're both seated, I have to look up at him to meet his gaze.

Suddenly, I feel extremely vulnerable. In the space of a few seconds, dozens of desperate thoughts race through my panicked mind. What am I doing, sitting here in a strange man's car in the middle of the night? Why on earth did I agree to meet someone outside my apartment? If this takes a turn for the worse, there's no way I'm going to be able to fight him off, let alone get away? He's so much bigger than me. He's got a car and I'm wearing this stupid heels. What have I done?

Amir lifts his hand off the wheel and I flinch, briefly. He places his large, thick-fingered hand on my trembling knee and, as if sensing my anxiety, speaks gently. "You are very pretty, Amy. Beautiful, in fact. I am honoured you would allow me to live out this fantasy."

"Thank you..." I whisper in response, gasping as his rough fingers trace delicate rings around my knee, soothing my nerves. "I'm happy to... help." I finish, lamely.

Amir flashes his white teeth in a smile that breaks through the shadow of his face. "Now, you are my passenger. Where do you wish to go?"

"Um..." I knew I should have thought of a destination earlier. "How about you just drive? You know, like they say in movies."

"Of course. As you wish, beautiful Amy. We will just drive." Amir somehow manages to start the car and pull out from the kerb without removing his hand from my knee.

"I have finished my shift," he says. I can feel his hand still stroking my leg, though he's no longer limited himself to my knee. Much of my thigh, at least the part that's exposed and not covered by my handbag, is now fair game. I'm delighting at the touch, my pale skin now pimpled with goosebumps. I can feel my little cock stiffening to press against the weight of my handbag.

"So we have all the time we want," Amir finishes. As the city lights flash through the cabin, I'm getting a better look at him. His face is rough like his hands, and he has a large, slightly disfigured nose, as if he's had it broken in the past. His greying beard is well-groomed while his head is covered in thick black hair, with some salt and pepper at the sides. Lower down, his belly is quite large and rests on his lap, denying me much of a view of any bulge in his crotch. I'm pretty sure he must have been sucking it in when I first got into the car. Now he's relaxed and letting it hang out. I smile to myself at the thought that he might also have been a bundle of nerves before our meeting.

"I have been a taxi driver for 20 years. I have driven many beautiful women. Many times. Very, very beautiful women," Amir tells me. "I notice them, of course! I am a man, how could I not notice all these beautiful women? But I am also a gentleman, Amy." He took this moment to squeeze my thigh, as if he wanted to emphasise the point. "A real gentleman, always. And so I admire these beautiful women, but I never... how do you say? Make a move? Yes, that's it. I never make a move."

Amir glances at me and sees me nodding in acknowledgment. "You understand me, Amy? I am a gentleman."

"Yes, I think so." Though I wasn't sure I did. Was he suggesting that this time he was going to make a move on the beautiful woman in his cab? Or was he encouraging me to make the move because a gentleman is, of course, too polite to do so? And, hang on, hadn't he already made a move when he put his hand on my leg?

Suddenly I thought I knew how I was going to play this. I placed my tiny hand on his and slipped my thin fingers through his much thicker ones. Ahead of us, I spotted a side street I knew well. "Amir, I know where you can take me now. Just take the next right."

Turning into the street, I was relieved to see it was an empty as I had expected. The warehouses that lined most of its length would be closed and, given it was also a dead-end, it was unlikely anyone would enter behind us. I indicated to Amir to pull over in the shadow of the tallest building.

"It's actually my fantasy to be picked up in a cab on a dark street like this out in the middle of nowhere," I say, turning to face Amir, both my hands now clasped around his. "And I'm so relieved that someone, anyone, has found me that I'm willing to, well... do anything to show them how grateful I am."

Amir's eyes lit up as he understood what I meant. I let go of his hand and moved my handbag to the floor. Immediately, his gaze dropped to my skirt as he hungrily anticipated what lay beneath. I turned further sideways in the seat, running my hands up his hairy, muscular arm and feeling his hand slide up my thigh, closer to its prize.

"I can be very... very... grateful," I purred in to his ear as I leaned in close. I ran my fingers through his thick beard and kissed his ear. I bit his lobe and flicked my tongue inside his ear, tickling the hair sprouting inside it. One of his hands still explored my bare thigh while the other slipped in behind my neck and pulled my head around to face him.

"You are very beautiful, Amy." Right up close, I could smell his sweat mixed with his cologne. I could taste the heat on his breath. I could see his expression was one of pure lust. He pulled me onto his mouth, immediately filling me with his tongue. I could barely keep up. The bristles of his beard left light scratches on my smooth skin. I knew my whole mouth was going to be red by morning, but right now I didn't care. I wanted him to eat me alive.

As I sucked on Amir's forceful tongue, I felt his big hand slip under my skirt and take a tight grip on my ass. Roughly, he dragged me over to his side of the car and onto his lap, my hip bumping painfully into the steering wheel. I let out a muffled cry, but he didn't seem to notice. With my head pinned in place by his strong hand on the back of my neck, he simply continued to devour me, his tongue never leaving my mouth.

Now that I was straddling the large man, I could feel his very obvious erection pressing against my ass. I started to grind my hips against him, revelling not only in the aggressive feel of his apparently sizable cock but also the exquisite sensation of my own cock rubbing against his belly.

Amir broke off our kiss by yanking my head away. He looked different now. Hungrier. "You are grateful?" I nodded while he held me by the back of the neck. "Show me." He shoved me back onto the passenger seat. I yelped as I banged my knee on the gearstick. I couldn't believe how strong he was, the way he was able to drag and throw me around like a doll. The only thing I could think of was how much I wanted him to do it again.

Amir had eased his seat back to create more room and was now unzipping his fly. He tugged down his jeans and let them fall to the floor. Reclining in his seat, he proudly showed off the giant tent in his boxer shorts. They were loose and crumpled, the once-sharp lines of the pattern now faded. His large belly still crept down over the waistband of his underwear, despite his best efforts to hold it in. I licked at my chafed lips and gathered myself to kneel on the passenger seat.

Inching forward, I leaned in over the tent of his shorts. It twitched as I did so, and I heard Amir grunt quietly. I could feel the heat and smell the sweaty funk emanating from his crotch. My mouth was salivating at the prospect of what delicious, manly treat awaited me on the other side of the thin cotton. I couldn't wait any longer. I slipped my fingers under the waistband and glanced up at Amir. His eyes met mine in the dim light and I paused, waiting for his instruction to continue.

"You will be very... very... grateful," he said, smiling as he mimicked my earlier suggestion. He lifted up my chin and studied me, as if he had just worked something out. "This is what a beautiful girl like you needs, isn't it?" I moaned in affirmation, and nodded for extra emphasis.

"You need a man's cock, is that right, Amy?"

I nodded again, more desperate this time.

"And you are very grateful for any man's cock, aren't you?"

"Y-y-yes." It emerged almost as a whimper.

"Good." He inclined his head in a gesture that said I now had permission to claim my prize.

I tugged down his shorts, letting his cock spring free. He raised himself from the seat so I could pull them all the way down, leaving them with his jeans around his ankles. Even in the dark I could tell he was huge, as thick as my wrist and perhaps as long as my forearm. It protruded at a slight angle, curving up towards his belly and a little to his right, from a thick mound of coarse dark hair. The thick shaft ended in a fat mushroom head where a large drop of his pre-cum glistened as it briefly caught the light.

In the dark below his cock, I could just make out lighter patches where the skin of his balls was visible amongst his pubic hair. I reached out and felt them, running my fingers through his hair and gently tickling his large droopy sack.

"Yes, baby, show me how grateful you are," Amir groaned at the touch.

Leaning further forward, my face now right above his erect cock, I tucked my hair behind my ear so as not to block his view, and kissed the head. Slowly and softly, I brushed my mouth across the slit and let his pre-cum paint my lips. Then I opened them and slid them down around the fat head until I held the delicious mushroom entirely in my mouth.

"Mmm... that's it, my beautiful baby girl..." Amir's groans of pleasure were increasing in both volume and frequency.

Still moving slowly, I glided my lips back and forth across the ridge of the head and flicked my tongue up and down just below the slit, lapping at his pre-cum and savouring its sticky sweetness. While I continued to caress his hairy sack with one hand, I wrapped the other around his thick shaft as best I could and began to stroke his heavy cock up and down in time with the motion of my mouth.

At first I felt Amir's hand on the back of my neck again. He'd slid it up under my hair and wrapped his fingers around my neck. Then I felt his other hand on top of my head, applying pressure. "That's it, baby girl." He pushed down on the back of my head, forcing more of his fat cock into my mouth, the head pressing at my throat. "You are grateful for all this cock, yes?"

I tried to reply, in the affirmative or not I wasn't sure, but I couldn't get the words out. I had started to gag as his huge mushroom head filled my throat. Releasing his shaft, I pushed at his belly as I struggled for breath. But he held firm, his grip on my neck and weight on my head were too much. His strength, even in this position, overwhelmed me. He started to lift his hips in an effort to force his cock deeper into my throat, quickly settling into a rhythm of short, sharp thrusts.

Over the sound of my own choking, I could still hear him groaning. His breathing was louder now. The groaning transforming into shouts. "You want this cock, yes?! You want Amir's cock inside your pretty little throat! You want it, you beautiful whore!"

Amir let out a roar and squeezed my head like he was going to crush it in his hands. His cum flew into my throat in waves, most of it passing straight through on it way to my stomach while some oozed back into my mouth. I was on the verge of passing out when he released me and let me suck in air instead of his cock. Coughing and spluttering, I slumped back into the passenger seat and stared awestruck at the glistening pillar I'd somehow just deep-throated.

Amir was stroking himself, squeezing any last drops of semen out of that huge and still very hard cock. Now recovered, I leaned back over and, in a trance-like state, slid my pale hand around his dark piece of meat and eagerly took him back into my mouth. Ravenously, I licked the fat head, slurping up any leftover cum and relishing the soft, velvety feel of his incredible cock.

Amir's heavy breathing filled the air. His belly and massive chest were heaving from the exertion. His cock between my full, red lips, I tilted my head to look at him. I was loving the fact that I could have this sort of effect on a man.

"Amy, look at you..." he started. "Still so grateful, I see."

"And still beautiful?" I pouted before returning my lips to the slick head of his cock.

"Yes, still a very beautiful... whore," he grinned. He reached out and ran his fingers through the blonde hair draped over my shoulder. "You see, Amir is a gentleman. And I would never do this with a beautiful woman. It is too... cheap."

Clouds passed in front of the moon, casting a darker shadow over the street. I was still holding his cock, but I'd stopped licking the head. I suddenly felt very vulnerable again.

"You are beautiful, yes. But you are nothing but a cheap whore." He grabbed me under the chin and sat up. There was a ferocity in his eyes this time. Suddenly he spat in my face. A large ball of saliva striking me on the cheek, spattering into my eye and mouth. I gasped and recoiled in shock, but I felt his large hand grab me by the neck, his fingers wrapping around my throat. I started to scream, but he clamped his other hand over my mouth. Even in the dark, I've no doubt he could see the terror in my eyes.

"Don't scream, whore." Amir said, with restrained anger. "If you scream again, I will hit you. If you try to escape, I will stop you. If you behave like a good little girl, then I will take you home. You understand?"

Shaking with fear, I responded the only way that I felt I could. I nodded, meekly.