Pizza Dare: The Beginning

Disclaimer: This is a work of fiction.

We have all heard the term experimenting in college, though not in the indian context. Well for me it was was totally accidental. But it changed my life forever.

It was during my 1st summer internship. My friend Alex and i had been accepted at an IT firm in Gurgaon. Alex in gurgaon? You must be thinking. Well he was from goa. I hope that sorts that out.

Aleks sister had a flat there. As his jijaji had got to go on site to the US, the apartment was empty and we were welcome to use it. The work wasnt very hectic and we had a lot of free time. Neddless to say it was pretty much a drinking binge and movies almost every evening.

On weekends we would start a bit early. It was probably the 2nd weekend we had and by about 3 in the afternoon we had gone through a six pack and one movie and had the entire evening in front of us.

“Mall chale kya?”, i asked tossing my empty beer can to the garbage bin and missing. With a sigh i got up to put in its place.

“Nahi yaar, kya karenge jaa kar. Waise bhi apne paas urane ke liye paise to hai nahi. Aur sali yahan ke mini skirt wale larkiyon ko dekh ke aur bhi frustration ho jati hai. Wo sirf gym wale body wolon ke saath ghumte hai. Hume to ghaas bhi nahi degi.”

“To aur beer piye?”

Now to give bit of background info, neighter of us had gym wale bodies. Far from it we were both quite the opposite. I stood at just 54″ and 45 kg. Alex was probably an inch taller and a shade heavier. We were both quite fair and wore our hair long, being rock and roll fans. It was the rock n roll that had been the bedrock of our frienship. We have been told more than once that we looked like brothers. And even some that we looked like sisters a few more times than we would have liked. To summarise we looked quite effemine. We had tried our luck with girls but forever seem to get immidiately typecasted into the cute brother they always wanted. It seemed that the girls of our age couldnt look beyond six pack abs.

“Ab kaun sa movie lagayr?” Alex asked. “Ya phir Friends dekhe?”

“Abe porn lagate hai.” I said, not knowing that i had stared a chain of events. I was actually thinking about a girl i had seen in the mall yesterday. She was wearing a very short summer dress that barely covered her hips. And the memory of milky white thighs and the bare hint of panties i had glimpsed while following her up the escalator was causing my cock to harden.

“I second that” Alex said enthusiastically.

We logged on to pornhub and i immidiately searched for candid upskirt. After a few videos i was rick hard and was pretty sure that Alex was too. We would just click on one of the suggestions that would appear at the end of each video for the next one.

Then Alex clicked on one that said “upskirt pizza dare”. It was home video. A pretty young girl wearing the most ridiculous of skirts answers the door. After taking the pizza she bent down with her back to the guy, apparently looking for change. She wasnt wearing any panties and gave the guy quite an eyefull. The guy was bending down trying to get a better look while at the same time adjusting his cock. After he went she flipped up her skirt at the camera confirming that she had shown her bare shave pussy to the pizza delivery guy.

One video led to another. With dropped towels, bare bottom in just a top, short nighty with no panties. Some even went further. One girl asked the guy to put on a sticker tatto on her butt. Another said that she wanted a pic wirh the guy as a dare, then completely undressing and taking a couple of selfies. She the said that she needed another with her holding his cock. The guy agreed. She then rubbed him to make him hard and took the pic. Then another with her mouth on his cock. She went on to give him a bj which ended with him cumming in her mouth.

These videos were so naughty that we were hooked. Also the fact that they genuinely seemed like the real deal and not scripted made them even better.

The porn and the beer was going to our head which led to the next fatefull point.

“Abe mere dimag mein eak bet a idea aya hai.” Alex said.

Now this was something we did. We made bets and the loser would have to complete an embarrassing dare. It started about a year ago. We were playing a mutilplayer video game and we bet that the loser will have to propose to this girl in our class. I lost and the next week i cornered her after class and did it. She said no and immidiately friendzoned me. Or rather brother zoned with a load of crap that i was a nice guy but she was concentrating on studies now and what not. And that was it.

But our bets did not end. And they went on becoming more and more embarrassing . Luckily for me, Alex lost most of the ones that were somewhat sexual in nature. Like masturbating in class to the hot Shilpa madam or walking through our hostel corridor wearing bra and panty. The last one was late at night and luckily nobody saw him but me.

But that last dare had made an impression on me. I had made him shave off his entire body hair for it, not that he had much. The bra and panties we had ordered online were lacy, somewhat see through, ones brought online. And i had to admit that he looked really sexy. I was no stranger to crossdresser porn and i could see the liytle bulge of his cock snug in the panties. From behind, with his shoulder length hair, a slight flare of the hips and the panty providing only half coverage, his white butts were practically bare. I was thinking that with makeup he would look more than passable. That night as i went to bed, my thoughts went to his jiggling bottom and panty bulge and i ended up jerking off to my best friend. Needless to say, i was extremely embarrassed and a bit confused when i woke up the next morning and the alcohol had worn off. I did ended up telling him that with some makeup i wouldnt have been able to tell that he was a girl. And he surprised me by saying that i too can easily pass as one. We didnt talk about it again but the thought stuck in my mind.

And apparently it did in his mind too coz he said “challaenge hai ki kaun eak can beer pehle khatam kar sakta hai aur harne wale ko…” dramatic pause ” eak pizza dare karna parega”

“Pagal ho gaya kya, eah dare to ladkiyan karte hai, male delivery boy ke saath. Agar delivery girl ayegi, jo india mein nahi hota, to kar sakte hai. Lekin woh jaroor police ko bata degi”

“Puri baath sun to le.” He interjected. “Yaad hai woh hostel corridor wala dare”

I immidiately got what he meant. “Abe nahi, wo kahne ki baat thi, we cant actually pass a girl. Pata chalte hi woh bhag jayega”

“No we can. Acha use pata chal gaya to dare yehi hai ki ladki ban ke slutty dress mein delivery lena hai aur jhuk ke use panty dikhani hai.”

My heart was pounding. If i lost then it will be the most sexual dare that i would have to perform. But i was pretty sure that i could outdrink him. And the i would get to see alex dressed again. And this time in makeup, fully dolled up. The alochol and the porn was working again. I do enjoy crossdresser porn from time to time and i was sure that alex would make a sexy little cd.

“Ok then” i said trying to make it sound as if i was reluctant.

“Ruk, poora sun le.” He said. “Agar use pata nahi chalta to use bolna hai ki dare ke liye tumhe uske saath photo lena hai, pehla uska lauda haath mein leke aur doosra muh mein leke”

“WHAT!!! PAGAL HO GAYA KYA?” i was shocked at the extent of the dare.

“Just eak baar leke eak still photo lena hai”

My heart was thudding. I knew exactly which video he was getting his inspiration from. But i wasnt one to back down. Besides i was pretty confidant that i will win.

“Ok then, chal beer la”

Alex got two fresh cans from the fridge. We set the clock. Opened the cans and took our stances like duelers from the old wild west.

“And START.”

“And END”….. said alex.

I HAD LOST. The unthinkable had happened. I snatched up the can to check and it was empty. I checked his clothes to see if he had spilled any, but again no luck.

I sat back, sipping the last dregs in my can as the enormity of what i had to do hit me. I lit a cigarette, took a long drag and accepted my fate. “Ok. So how do i do it. I dont know how to apply makeup. And what clothes to wear.” I knew we had plenty of his sisters stuff to do it.

” tu chinta mat kar. Maine didi ko kai baar makeup mein help kiya hai. Aur kapre main pick karta hu. Tu bathroom mein ja aur shave kar. And i mean shave everthing.”

“So thats how its gonna be?” I asked.

“Yep. Its payback time.” He smirked. ” go to tje master barhroom. You will find appropiate razor under the sink”

I dragged my feet into the bathroom. Sure, there were a couple of gillette female razors there. I took a new one. Well i had to do what was to be done. I undressed, showered and lathered shower gel all over my body and went to town. Luckily i did not have too much body hair. The most difficult part was doing my butt. But i was determined to do a good job. I even shave the crack of my butt. I dont know why, but i did. The most delicate was my cock and balls. It took utmost concentration but i did it. When i finished, there wasnt a single hair on me below my eyelases. I did not have much facial hair, i only had to shave one a week or so. But that meant when i had gotten it off, my face was absolutely smooth. No 5 oclock shadow at all, as i had seen on some crossdressers.

As i rinsed off, i realised that my body feet so smooth. I ran my hand over cock and it was smooth as a babys ass. My smooth thighs rubbing against each other send an electric current thru my body. I instanly got an erection. I looked myself over in the mirror and was shocked to see how gud i looked. Any i realized that i had a feminine body. My hand were slim. So was my waist. But i had been chubby as a chipd and had only recently lost weight. The result was that i had sime remaining fat in my hips and my chest. I was looking at what coupd easily pass a teen female body with a-cup breasts, if not not for the little cockp1 between my legs. If i had any complaints with god, it was only that my cock was barely 5 inches when erect. I stood under the cold shower waiting for the erection to calm down. It somehow felt wrong to jerk off then. It slowly went down. Now limp it was barely an inch long handing uselessly between my legs.

I patted myself down and wrapped the towel around myself. I suddenly realised that i had wrapped it around my chest as a girl would do. And in the mirror i saw a cute wet girl staring back at me. Alex was right. Even without makeup i loooked passable. What was i getting myself into. I shrugged off the scandalous thoughts and retied the towel at my waist and stepped out.

Alex was waiting for me and on the bed were laid out my dress. I saw he had laid out the same lingerie that he had worn. And what looked a tiny yellow summer dress that belongs to his sister.

“Time to get dressed.” He was positively beaming, enjoying my apparent embarrassment. “Then we do the makeup”

Not to give any more ammo, i casually picked up the bra. To be honest it was more of a camisole. See through, lacy with small cups and ending a couple of inches above the navel. It was supposed to be slipped over the head.

“Dont worry, its washed.” He said reassuringly. I outwardly shrugged, but was relieved that i did not have to wear his dirty lingerie. I pulled it on. My man breasts nicely filled the cups. Lucky that they were padded. But it definitely gave me some clevalge. I pushed my boobs together, ok i am going to call them my boobs now coz they looked like boobs, to get some more clevage and we both shared a laugh.

Then i slipped the dress over my head. It actually fit quite snugly. There was a ribbon at the waist that was to be tied begind. As i struggeled with it, alex came up.

“Lao, main banhd deta hu.” I stood still and let him do it. He was strangely quite gentle about it. What was he feeling. I remember my own feelings when i saw him in that dare. But again i pushed the thoughts aside.

“Done, chal ab panty pehen le, phir chair pe baith ja, tera makeup karna hai.” The work pany rolling off his tounge sounded so naughty. I dropped my towel. My modesty protected by the dress, but barely. Christina didi stood barely 5 feet tall, and the dress was a short one, even for her. On me it barely came an inch below my butts.

As the cool breeze of the ac, hit my privates i realized how exposed i was. One wrong movement and i would end up giving alex an eyefull. I regretted that i had dropped the towel but there was nothing to be done now. I picked up the panty and turned away from him towards the dressing table mirror. Trying my best to make only the most economical of movements i bent down to slip my legs into the panty. I was looking at alex in the mirror out of the corner of my eyes. And as i bent down i say his eyes widen. My butt had just peeked out of the bottom of the dress. But he didnt look away. He was starering intenetly as i pulled it up and around my hips. At the last step i realized that i couldnt wear the panties without my dress riding up and i will be exposing my behind. But i went through it, feeling very exposed but also a little excited. Alex was looking at me with what was definitely some lust. It felt strangely empowing. I was strating to feel like a pretty girl who had a boy wrapped around her little finger.

“Ok. Done. Chal ab makeup kar de.”

He made me sit in a chair and made me promise not to peek till he is done. I sat down and relaxed. There was a lot of combing of hair and stuff being dabbed on my face. But i did peek. And i realised that there was definitely some tenting in alexs pants. I was getting my friend hot. At first it felt disgusting, but tjen i realised that he probably saw just a pretty girl just as i had some 6 months ago. I was feeling very naughty and i opened up my legs a bit. Just so that at tje right angle he can see a glimpse of my panty covered bulge, tiny one that it was. The panties felt amazing around by little cock and i had to do my best not to get an ertection. I was willing to tease him with some knicker show but an erection would spoil the illusion.

But for the most part i was a good girl a d kept my eyes closed.

“Ok done.” He said.

I opened my eyes and my mouth just hung open. While previously i was a passably pretty girl, i now saw a stunning beauty staring back at me. Damm, i would definitely want to fuck me.

“Wow Alex, tumhare hathon bein jadu hai. Agar engineer nahi bane to beauty saloon jaroor khol sakte ho.”

“Nonsence, model achi ho to kaam kuch rahta hi nahi hai.”

I blushed a little realising that he said achi and not acha. What the fuck was happening to me

“Aur awaz pe kaam karna hai. Woh ghost call wala voice use karo.”

The ghost call was another of our dares. We used a unknown number to call up random boys in our class pretending to be girls. Our voices were naturally high and with a little practice we did very well. The goal was to get them to send dick pics and we had both succeded in that. Boys are so guillable when thay are or think are with pretty girls.

“Ok. Is this good. Kaisi lag rahi hai meri voice.” I said switching into my alter ego voice. It actually seemed easier now that i was dressed for the part.

“Perfect, ab order place kare.”

I had actually become quite comfortable infront of alex, i felt sure that my secret was safe with him, but now it hit me that i was going to be infront of a stranger and i even had to get sexual with him. A pit was forming in my stomach. I was never so nervous in my like. But the thrill of tje dare was also there.

“Theek hai, lekin agar eak buddha bihari nikla to main dare poora nahi karoongi.” I was staying in chatacter embracing my female alter ego. ” meri bhi standards hai.”

“Hmmm… thoda thoda kar ke order karte hai. Pehli baar nahi hua to 2nd try kar lenge. Chalo order place karo” he said tossing me the phone.

I dialed pizza hut.

“Hello gud evening and thank you for calling pizza hut. May i have your name and telephone number.”

Name! I hadnt thought of one but it just rolled off. “Shalini, 980”.

I ordered a solo pizza and a coke. All in a female voice. As i put down the phone alex said… “shalini, cute name.”

I just smirked at him and open a beer and lit a cigarette. The waiting was the worst part.

On his part, Alex set up the camera discreetly. I forgot to mention it, but wasnt it obvious, a pizza dare without a hidden camera was unthinkable. Also for the pics that i would take on the dare he set up a mobile on a selfie stick. We were going to pretty much stick to the script of the video which inspired us.

I was trying to stay cool and was going though different versions of what i was going to say when the intercom buzzed. The guard called from the apartment gate, it was showtime.

“Eak minute idhar ana” alex said.

“Kya hua”

“Dress thoda adjust karne nai”

He then proceeded to shorten the shoulder straps an inch so the my dress rode even higher. I looked at the mirror over the washbasin. From the behind, a sliver of the bottom of my butt was now visible even when standing straight. I was looking positively slutty now.

“I will be in the next room, if you need me.” He said and disappeared.

Ding-dong… the bell rang. Taking a deep breath i opened the door.

“Madam, aapne pizza order kiya hai?.”

It was a young guy. One of the gym body types. Easily towering over me. He looked young enough to be a student. My last hope disappered, there was no backing out now.

“Haan, andar aao, table pe rakh do.”

He walked over to the dining table and i closed the door after him. I saw that he was finding difficult to take his eyes off me. I guess he never had to deliver to a sluttily girl before.

As he put down the pizza and coke on the table, i asked “kitna hua?”

“328 rupees.”

It was time to execute phase one. I had kept one of didis bag on the floor near the sofa with the money. I turned and walked towards it, trying to sway my hips as much as i could. I was really getting into it. I was no longer a boy. I was a naughty, slutty seductress. And i was getting excited about it all. My little cock was stiffening in my panties. I knew that even now i was giving him glimpses of my ass.

I slightly spread my legs and bent over to reach the purse. I could feel the draft of the fan through the thin translucent materials of my panties as my the hem of the dress rode over as i bent. I was now totally exposed. I had looked in the bathroom and i really did have a gorgeous white ass. The guy had been undressing me with his eyes as i was speaking to him and even though i could not see, i could feel his stare on my ass. I made a show of rummaging through the bag to find change prolonging the moment. I just hoped that he did not see my bulge. But then it was tucked to the front and was anyway so small that there was hardly any danger.

Finally i stood up, walked back to him and handed him the money. I was blushing like anything and just hope my makeup was hiding it. Now to the hard part….. pun intended.

“Tumhe jaldi to nahi hai.”

“Jyada jaldi nahi hai, kyu madam.”

“Wo kya hai na, maine apne friend ke saath eak dare liya hai. Usko complete karne ke liye tumrahi madat chahiye.”

“Kya madat?” He looked confused.

“Wo kya hai na…. wo…..”. Cmon Shalini, i told myself. Its like pulling a band aid. Just say it and be done with it.

Taking a deep breath i let it out in one go. “Mujhe eak selfie leni hai….. tumhare laude to chooste hue… lekin agar tum comfortable nahi ho to koi baat nahi.”

His mouth fell open. I guess he went into a shock.

I quickly tried to reassure him. “Tumhara chehra nahi ayega, sirf meri ayegi, kisi ko pata nahi chalega ki tum ho.”

He kept staring at me, too shocked to speak. I could see the bulge in his jeans. I had already turned him on with my earlier display. Now it was a struggle between his mind and penis.

“Please meri help karo na.” I said putting on my best pouty face.

Finally he spoke. I was almost a whisper. “Madam darwaja mandh kar le.”

I got him. I thrill ran through me. What was happening to me, i was begging to suck a strangers cock and i was thrilled that he agreed. Was i secretly gay. But i was too caught up. I practically skipped as i went and locked the door.

“Main baithu ki khara rahu..” he asked. The poor guy was sweating in the ac.

I did a quick mental calculation. He was standing perfectly for the camera to catch our profile.

“Wahi theek nai.” I came and knelt down before him. “Main chuwu?” I asked. It was pretty obvious what since my hand was already halfway to his crotch.

“Haan theek hai.” He said

I placed my hand on his cock over his jeans. It felt so big and it wasnt evem fully hard yet.

“Nervous ho kya?” I asked him

“Haan thoda sa.”

“Main isse upar se sahla du. Tumhe poora hard karne ke liye. Selfie achha ayega”

“Ji, please”

I stood up and started to rub my hands over his jeans. It was working. I could feel him growing. But was taking too long. I had to do something to speed it up.

” Tum chaho to meri boobs choo sakte ho, aur meri gaand bhi, lekin panty ke oopar se. Aur tango ko beech haath mat lagana.”

Instantly his right hand clamped on my left boob and his left hand sneaked up under my dress to grab my ass.

It was working, he got really hard. And he was not the only one. My tiny cock was stiff as well. He was also getting adventurous. His right was now down the front of my dress and was massaging my bare boobs while his left hand was making its way into my panties. His finger pressed my butthole and it sent a current through me. I almost came then and there. I never knew that my butt was so sensitive. I was loving it but i had to stop him before we secret was revealed.

“Nikalu bahar?” I asked coyly.

“Kya?” He seemed surprised.

“Tumhara land, aur kya.” I said with a shy smile.

He reluctantly took his hands away and started to unbutton. I grabbed his hands.

” main karti hoon.”

He just nodded. I knelt down before him. I could see the outline of his hard cock thru his jeans and it looked huge. I wondered what alex was doing. He had hooked up the camera to the laptop thru the wifi and was seeing a live telecast in the next room.

He was already unbuttoned. I just pulled down the zipper. I took a deep breath and with a jerk pulled down his jeans and underwear in one go. It was huge, at least 8 inches, and shaven, although the hair had started to grow back a little. It sprang out and hit me on the cheek.


“Sorry madam.” He blurted out.

“Sorry kyu, tumhara sahi mein bahut bara hai. Aur tumne shave kar rakha hai… thank you.”

“Wo.. mere girlfriend ko shaved pasand hai.”

“Aur tumhari girlfriend ne tumhe aise dekh liya to, mere saath.” I teased

“Maar dalegi mujhe.”

“To use nahin batayenge, infact kisi ko nahi.”

“Yes madam kisi ko nahi.”

The guy was just a putty in my hand. I haf never felt so powerful before.

” ruko mein camera lati hu. Mere challange ke liye.”

I grabbed the ready camera on the selfie stick and took my position in front of his cock. I counld smell the strong musky odour, but it did not turn me off. In fact it was turning me on.

I gently placed my hand on his cock. It was rock hard and throbbing. It jerked a little as i grasped it. I first put on my pouty face and …. click.

Only one such pic was needed. But i was in the zone and was feeling so slitty. I clicked 4 or 5 pics with increasingly horny faces. At the same time i started jerking him off slowly. Rubbing my hand gently over his long shaft.

Now it was time for the money shot. I opened my mouth and slowly leaned forward. I saw a drop of precum forming on the tip of his cock. Just hanging there, about to drop off any moment. My own cock was oozing precum and a wet spot had formed on the front of my panty.

I stuck out my tounge positioning it just below the drop of precum as if i was trying to catch it…. and click.

I was mesmerized by the drop of precum. I flicked it off with my tounge. Thr pizza guy moaned as my tounge touched the tip of his cock. It tasted salty. And now i was on fire. My own tiny cock was the hardest it ever had been. I leaned forward and took him in. I cannot explain the sensation of have a hard throbbing cock in my mouth. It gently moved my head forward and back, gripping the base with my left hand and i clicked off a few more pics.

Dare done. I leaned back wiping a dribble of saliva off my chin.

“Thank you very much.”

He looked so dissapointed realizing that itbwas over. In fact it was probably very cruel leading gim on and letting go at the last moment.

“Madam, main aise wapas nahin ja sakta. Aap bura to nahin manoge agar main muth maar lu.” The poor guy said shyly.

I felt bad for him. “Main madat kar du. Main tumhe mooh mein le sakti hu thodi aur der. Bas bata dena kab tumhara nikalne wala hoga.” I was so horny and had an irresistible urge to suck him off.

“Please madam, thank you.”

I resumed my position took him back in. I had seen plenty of porn and i took lessons from that. I possible couldnt take him all in. I could only do about half. So i used my hands tohether with my mouth.

I picked u a rhythm. The room was filled with the sound of my slurping and his moans. I myself was getting dangerously close. As i rocked forth and back, my cock was rubbing adainst the lacy of the panties sending little shocks through my body.

“Madam, nikalne wala hai.” He barely croaked.

I realized that i didnt want him to make a mess in the room. If he came on my face, it could dribble down and spoil my borrowed dress. And i didnt mind the taste of his precum.

“Tum mere muuh main cum karna chahole?”

He couldnt believe his luck… he just nodded. I took him back in and renewed sucking and jerking with my hands. He did not last even 30 seconds. I could feel it before it came. His cock started to twitch and knees shake. Then his hips buckled and with a mighty groan, he came. Shooting jet after jet of cum into my mouth. I struggled to keep it all in but i managed most of it.

As he slumped against the wall i opened my mouth to show it filled with his cum. I then shocked even myself by swallowing it all in one gulp. Some of it had dribbled down my chin. I scooped it up with my fingers and in the most seductive way i could manage sucked it up. The pizza guy reached down to pull his pants up, but was still some cum on his cock. I dont know what came over me, but i had been transformed into this cum hungry whore.

“Ruko, tumhare land pe cum laga huwa hai. Tumhara undie ganda ho jayega.”

I took his cock back into my mouth and proceeded to lick it all up.

“Lo ab saaf ho gaya hai.” I said with a wink.” Ab chalo, tumhe late ho raha hoga.” I just dismissed him.

The guy quickly pulled up his pants and left muttering various forms of thanks. As i locked the door behind him i realized that i, a till then straight guy had just dressed up in drag and given a blowjob to a total stranger and i didnt even know his name.

“Wow, that was well beyond the call of duty. ”

I turned and say Alex standing across the room. He had taken off his pants and was standing in just his boxers. I could see his erection tenting his boxers and i myself still had a raging hardon and was aching for release.

…. to be continued.