Ana's Toll Booth Dare

Hi my name is Ana and I work at a software development firm in Mumbai, India. I recently turned twenty-five and the limited dating pool is something I didn't mind at this stage, I am an introvert and like my alone time. A friend of mine, Pooja, we were school mates and good friends for a time and now got back together as we were in same city again. She works as a toll collector at an expressway, of course I wont mention which one, but it goes towards East!

Her agency that had this contract of maintaining the toll is amongst the pioneer to employee women in a area where typically you see only men, good on them. So Pooja works the 3:00pm to 11:00pm shift and is assigned to an exit not frequently used after the evening rush hour.

There are two toll booths at this exit - an unmanned for cars with Fastag and a manned one right next to it for those without Fastag or having only cash. Fastag, for people not aware, is the new digital payment system for any vehicles travelling in India, it is a prepaid mechanism. The manned booth is worked alone until 11:00pm each evening by my friend, after which cars must mandatorily have fastag as the booths aren't manned after that time.

I got into a silly argument over something I would rather not go into at this point, and I was sure my facts were right. I bet my friend and as my pitiful luck would have it I was wrong and I lost. We had previously agreed that the loser would do a dare of the winner's choosing. I had to work in her toll booth wearing only her uniform shirt from 9:00pm until closing. I was to arrive wearing a "complete" uniform a little early and work with her for awhile to get my so-called training and then work solo until 11:00pm.

A few days before, pooja lent me one of her uniforms. It wasn't too bad of a fit and the shirt did manage to cover- albeit barely - my essentials though the last button on the blouse was a bit high for me leaving the two shirt tails available to separate in a breeze or when I walked. All in all it could have been worse.

On the day of my dare I couldn't concentrate much at work. I was too filled with anticipation and dread over the risk I would be taking. I mean I'm not even a toll booth worker, for god's sake.

After I showered I tried to eat something but my stomach was interested in food. Around 7:30 I realized that I had put it off long enough and changed into my uniform blouse and skirt and off I went. Upon arriving at her exit I had to pay the toll to pass the booth and then parked in a small two-car parking area near her booth. It was about 8:15pm and it was still very light out and to my surprise there were still a lot of cars getting off the expressway at her exit. I joined pooja in the booth and she immediately started my training.

I must say her job was harder than it looked. I mean there were a lot of little details to keep track of including the handling of special passes for goods vehicles, etc. She went through it so fast as she was making change for motorists at the same time. She kept telling me how she didn't think I would go through with it and was sure I would chicken out and in the same breath threatened to beat the snot out of me if her drawer came up short because of a mistake I made! She wasn't kidding either!

By 9:00pm it had slowed down a quite a bit and the number of cars exiting was about one every 3 to 5 minutes - a much more comfortable rate I thought! pooja finally turned to me and said it was time. She held out her hand and with a huge smile asked for my skirt. I took a deep breath and reluctantly unzipped the side zipper and, after looking around to be sure no one was coming, let it drop to the floor. I stepped out of it and handed it to her. "I hope you're satisfied," I said with indignation and then said, "I just hope I can remember everything you taught me!"

Pooja put her hands on her hips like my mom used to do when I was in trouble and said, "YOU'RE not through yet. The deal was for you to work in my shirt only, NOT in my SHIRT, BRA, PANTYHOSE and PANTIES!!"

I couldn't believe it. Surely she didn't expect me just to wear only her blouse!! Her outstretched hand told me otherwise. "A bet's a bet!" she smirked. I slipped my arms out of my bra while still wearing the blouse and handed it to her and then struggled a bit with my tight pantyhose giving them to her to hold. I then removed my panties and tossed them at her rather forcefully as if to make a point that I wasn't amused!

She exited the booth with all my clothes and called out over her shoulder as she walked to her car, "Call me on my cell if you have a question. Now remember, if I come back unexpectedly and catch you wearing something else you are in big trouble! See you at eleven . . .or maybe sooner!" She laughed all the way to her car. I had a lump in my throat as she drove off leaving me almost naked in such an official place!

I didn't have time to worry much as a car came up to my booth almost startling me back to reality. I hugged my body against the half wall of the door that separated me from the car and held out my hand into which the motorist deposited his cash, and I gave him change and quite matter of factly, he drove off. Thank God!

Let me describe this booth to you. It was a rectangle about 3 by 6 feet. The front part and the right hand side were large glass windows that came down to about waist high. The side that faced the road where the cars pulled up was open except for a sliding metal door. The back part was all metal-enclosed and served as a type of very small office space. I thought about hiding back there until a car came but dismissed that idea as I thought drivers would see more of me as I took the steps to reach the front area.

So there I was, wearing only a white blouse that came about one inch below my labia. Not much room for error I thought. Every time a car came down the exit ramp I almost choked. Fortunately most had the correct change and went to the unmanned booth next to mine.

After I had made change for several cars without incident, I began to feel a bit more comfortable. I always kept change handy for a few rupees in my right hand and the coins to change a dollar in my left. That way I would have to step back and reach for the change drawer to make change giving the driver the possibility of catching a peek at something I didn't want him or her to see!

I got pretty smug about it after an hour of doing this work. I mean I was really relaxed now and getting into the sexual arousal side of myself! I was truly enjoying this! I mean cars would pull up and I was only inches away from flashing them! If they only knew!!!! When cars would speed off after paying the toll, the breeze would often lift the ends of my blouse and the cool air against my exposed pubes gave me such a thrill! The first time it happened I was scared to death but after a while I looked forward to it - my naughty little secret as it were as the wind would stimulate my already prominent little clitoris. (I still can't believe how far I have come using this sexually descriptive language! A few months ago I would have been mortified to use such words knowing somebody was going to read them!!)

A trucker came through in one of those step-vans and asked for a receipt! My mind went blank as I couldn't remember what pooja had said about receipts! I guess he needed it for business purposes. A little light went off in my head and I finally remembered that she had printed up a few dozen and laid them on the counter next to the cash drawer.

SHIT! I would have to take a step back and reach for them! I could see he was growing impatient with me so I decided just to go for it. I waited until he looked away from me and practically jumped for the receipts! I know if he was looking at me, he saw plenty of my bare ass as I could feel it exposed as I reached my right arm over the counter. When I turned around, he looked up and took the receipt, smiled and drove off. I had no idea whether his smile meant he saw my nudity and looked away as a gentleman would have done or whether he was oblivious to what had just happened. The mere thought of it though, almost made me climax right there!

Around 10:20pm I saw a car I recognized get off the ramp. I prayed that it would go into the "fastag" booth but no, damn it, it headed straight for me! Inside the car were two friends of mine that I used to party with. I won't use their real names but the driver, I'll call Sameer, recognized me immediately, "HEY, ana! What are you doing working here? I thought you had a good job working for [blank blank]?"

"Oh, I still work there," I replied, "I'm just helping a friend whom uh, had a family crisis to attend to. She'll be back soon." I said trying not to sound nervous. I just couldn't be caught by these two!! Word would be all over town and my dirty little secret side would be out in the open!! I was so nervous and began to get a little frightened almost to the point of panic as they continued to talk with me!!

He went on to say that several of his friends were heading off to a club and asked if I would meet him there after I got off work. I politely declined telling him that I had had a long day and would probably just go on home. Man, did I feel weird talking with people I knew, half-naked as wet as I was hoping like hell I wouldn't do anything to tip them off!!!

They finally left and I almost collapsed with relief! Nothing remarkable happened after that and 11:00pm was fast approaching. Pooja came by about a quarter till 11:00 and asked how it was going. She was driving a different car and had a ton of grocery bags in the back seat of her car as she sat in her vehicle in my lane chatting away. She obviously used her unexpected night off to good use! She told me she would help me close out the night and told me she was proud of me for going through with it.

Of course once she was inside the booth with me I HAD to tell her about my night. She could tell I was pretty aroused by the whole ordeal and wanted to know all the details - which was embarrassing in and of itself, telling another girl about how turned on I was by it all. She even had the nerve to ask me if I had gotten off! Of course I told her it was none of her business! That was a mistake because she just assumed that I had!!

Once she had finished her paperwork she turned the red "closed" light on the lane next to our booth, pulled the window shade down and prepared to lock up. "So, where are my clothes?" I asked, "I want to get dressed now."

A genuine look of surprise befell my friend's face. "I completely forgot! They are in my other car!" she confessed. "I am so sorry, HONESTLY, I really forgot!"

"Yeah, SURE you did!" I responded sarcastically. Pooja asked me if I wanted to wait in the booth while she went home and got them. Though I didn't relish the thought of driving home in just a blouse, it was better than being totally naked and I didn't want to push my luck in the booth in case a cop came by. She understood and apologized once again. We both waited until the coast was clear and then left the booth locking the door behind us.

Pooja walked me to my car and as I was about two steps from my car door I heard a car approaching on the ramp. Not being too concerned as we were mostly hidden by pooja's "cash" booth, I didn't run. I should have though as I heard sameer call out, "HEY, ana! Changed your mind about going clubbing?"

I was so startled that I instinctively grabbed a hold of pooja and pulled her about to shield me. I fumbled with my keys trying to open my damn car door hoping that the guys didn't notice much. Once the door opened I hopped in an immediately closed the door. I rolled down my window and yelled at sameer, "NO thanks. I've gotta go!" I started the engine as I was still talking and rudely backed my car out and took off without saying another word. I got on the entrance ramp to the expressway and headed for home. Fortunately sameer didn't follow me.

After driving a few miles I felt a bit better about everything until I realized that I had to pay a toll at the main expressway toll center. To my horror I realized my Fastag account was zero toll both and all my fucking money was in my damn skirt that pooja had in her car!!

I remembered that I usually toss my spare change and loose coins into my car's ashtray. I drove slow and desperately tried to count out the coins. I didn't want to get arrested running a toll gate without paying in my state of dress. The good news is that I found money needed. The bad news is that about 20 were single rupee coins!!

As I approached the center about 1/4 km away, I changed lanes and headed for the Fastag toll booths to try my luck if they just allow me to go as sometimes these digital things don't always work. To no surprise it didn't work and showed insufficient balance message. The guy wasn't in mood to let me go either so there was no choice, Infact he started walking towards me.

I quickly tugged at my blouse to pull it down as far as I could. It was nerve wracking waiting in line behind several cars for my turn to pay. My pubic hair wasn't showing but nothing was left to the imagination either. The pouty lips of my labia were quite visible if someone knew to look there!! Maybe it would be an older guy I thought. Nope! It was a young guy making coming very near me!

When he reached the window, I handed him all the change and he seemed really put out with all my coins. You should have seen the look I got! This guy was a real meticulous dude. He actually COUNTED my money like I wasn't trust worthy or something. Satisfied that I had paid the correct toll he turned to me and raised the gate. He must have gotten an eyeful because his expression of utter disgust with me evolved into surprise and then melded quickly into pleasure, maybe a hint of pervert smile! I didn't waste anytime finding out I just rushed away!

Well that's my toll booth dare. I have got to learn to keep my big mouth shut!!!