Dare girl goes astray!

Cindy was a sweet 24 year old when I first met her. She was the kind of fresh faced girl next door type who was easy to get along with. Her blonde hair and 38D figure gave her a Venus de Milo appearance as she skin was the soft tones of almost pure alabaster marble.

Not long after we began chatting on the internet, I discovered that she had a passion about playing true dares. She had spoken to several different Mirror Masters, over the last three years and had carried out several sexual dares by way of experimenting.


So it was that she challenged me to set her a lifetime changing dare. After much deliberation and coaxing I set her a streaking challenge. She was to dress in only a skirt, blouse, knickers and shoes, before driving 2 km from home stopping the car, get out and remove her skirt. Then run three times around the car before climbing back in to continue her journey. After a further 2 km again she was to stop the car, remove her blouse and run four times around her car before re entering the car for her last 2 km drive.

When she was 6 km from home she was to pull up remove her final item of clothing her knickers, run five times around the car before locking her clothes and the car keys in the boot of her vehicle. Then on foot she was to jog home during the hours of darkness. She set out on the task at 2.00am, eventually arriving back home at 5.30 am.

To slow her down somewhat, she had to finger her pussy as she ran, and when getting close to climax, she was to stop playing with herself and walk until she calmed down enough to recommence playing with her pussy, then and only then she could begin running again.

Once home she was to go into her back garden and using only her fingers, she was to bring herself to a climax before getting her secreted spare house key and letting herself in. I informed her that I would have spies checking on her whilst on route and if she got herself cornered for any reason she was allowed only to use her mouth to extricate a means of escape. This meant that if she could talk her way out of the situation she was to do so, if not she was to use her mouth to offer a blow job to be able to continue on her way.

The spies were coached to protect her along her path and only intervene if she was out numbered and in danger, Of Course Cindy was not aware of the safety back up.

She did the task and passed with flying colours, even delighting in telling her best friend, Mandy about her thrilling late night run. Mandy then asked if she could contact the guy who set her the task. Cindy passed on my Email address and I received an interesting email from someone calling themselves Mandy, explaining they were fully aware of the task I had set for her best friend Cindy.

It transpired that Mandy wanted me to challenge Cindy again but to get her to do something with her, like have to masturbate in front of Mandy and accept a spanking from her before reporting back to me. 

However this was to be a final part of a dare as Cindy was to run naked in a park, before lying over the bonnet of her car and masturbating herself to a climax. Then she was to make her way to her friend’s apartment and beg to be allowed to bring herself to a climax in front of her best friend as the finale of the main dare.

Mandy however had other ideas and secretively she arranged for her and a male friend to hi jack Cindy, tie her to a tree soundly spank her before the male was to fuck her and once Mandy had tortured her nipples for a while they would release her before jumping into Cindy’s car and driving off leaving Cindy 30 Km from home stark naked and with her hands tied behind her back. Some 300 yards down the long straight road, they would pull up in the car and obviously Cindy thinking her best friend had taken pity on her, she would run towards the car, only for them to speed off for another three hundred yards.

Three times this happened, before the male hauled Cindy into the back seat beside himself and on demand of a blowjob, they took Cindy to Mandy’s house. Where she was soundly spanked and not only fucked, but also had to demonstrate her ability to service another woman’s cunt as well as having her own licked while her nipples were clamped.

Thus this dare ended, again with Cindy in an exaggerated state of high sexual tension. Next thing I heard was that Mandy wanted me to dare Cindy to give six blow jobs in an adult store catching the spunk in condoms for her to drink later. Cindy accepted this dare despite the dare being changed before the night in question.

The new dare was far worse…..

Here I will allow Cindy to continue in explaining her new dare and her feelings as she undertook the dare..

Master Ray,

Now I get the Joke from Mandy, about what is the best part of a Donut. She took me into a world famous donut house and got me a cream donut. (It’s the cream inside the hole of the donut, by the way). I soon related this to the whole heap of mess I was in inside the adult store. 

Master as always you want my report from the beginning, so before I get too far ahead of myself, here it is.

Preparations began at 12 noon as I had to be in work by 2 pm, so I showered and shave my pussy, before dressing in white blouse, miniskirt and thong.

After work. Mandy met me from work and escorted me to Tim Horton’s Donut bar, where she bought me the coffee and donut filled with cream, Mandy constantly giggled as I ate the donut. She had decided to wear a combination of jeans and a tee shirt with Greek writing on it. I found out the significance of this later at the adult store.

She also advised me that the manager of the Adult store was in it and would be acting as my bodyguard and the fact that this was supposed to be a sorority pledge, hence the Greek letters on her tee shirt.

At the Adult video warehouse. I was amazed at some of the sex toys on the counter and the full array of the Magazine titles in the racks, the multitude of video’s and DVD’s the place contained was mind blowing. There were mirror on the ceiling so everyone could see what was happening on any of the aisles. So the five or six guys present got to see plenty as I got into the flashing part of my dare, stooping and bending to look for video and DVD’s on the bottom shelves as instructed by Mandy.

Andy the store manager must have been very well briefed as he had a gigantic vibrating dildo ready to show me and when I asked the price he said “You don’t need cash, honey when you look like you do, I am sure you have something you would like to trade for it” he signaled for me to come over to the sales counter and I saw he was sitting un his high stool with his penis already out of his trousers.  So I gave my first blowjob of the day behind the counter and in full view of the people in the shop. Andy insisted that his blowjob was not one of the condom ones, so I sucked his cock barebacked and swallowed his cum straight into my throat.

Whilst I was giving him his head, Mandy was talking to the remaining customers and giving them the cover story that she was a sorority sister and as her pledge I had to obtain six blowjob filled condoms to prove my worth in our sorority house. It turned out this was a complete set up as more customers entered the shop around this time and I was alter told they were all friends of Andy. Mandy enlisted the help of these guys and told them to take their time, but most of them did not as they came very quickly. I guess they were as horny as I was.

The first change to the agreed dare came when Mandy insisted I strip and spread my legs for the first guy to fuck me. Mandy insisted on helping the guys put on their condoms before they were allowed to fuck me and then she slipped the safes off their cocks afterwards and tied them off. She held them all until the sixth and final guy had fucked my soaking pussy. She then had me lie on the filthy floor on my back with my legs wide open, so everyone could see her slip the used cum bags up my pussy, then came the pussy clamp.

It was one of those cheap plastic package clamps with a four inch wide alligator jaw, it hurt like crazy when first applied but eased off after a few minutes and I hardly noticed it by the time I had adjusted to wearing it. I had to; I was made to wear it for the next four and a half hours.

I was then led through to the makeshift glory hole. It turned out to be the staff toilet facilities. But first I had my hands Fastened behind my back by Mandy and Andy attached a collar around my neck, the collar was off one of the sex toy shelves and had a large d link metal loop. They paraded me around the store so all the patrons got a real close look at me before taking me through the back.

I could not believe it, you could physically smell the facilities long before you saw it; they could not have been cleaned out in the last six months at least. They were far more obnoxious than the worst of the worst of gas station toilets. I now realized I was going to be spending the next four hours at least in this smelly fetid place and worse than that I was going to be adding to its stench.

This is how Mandy and Andy got me set, First I had to kneel in god knows what, by the open door. Right by the neat four inch circular hole cut at just about the right height in the door was an electrical staple looped into the wooden door. Through this they fastened a chain which was clipped to my collar pulling my head close to the hole in the door and preventing me from refusing any cocks pushed through that hole.

Mandy then decided, I looked much too comfortable for the pledge and promptly applied nipple clamps to my nipples. Finally I had to inch my way back into the cubicle as they closed the door. I did so until the crack of my bum felt the cold porcelain of the toilet. Then the door was bolted from the outside. It was horribly dim but not dark in the cubicle, because the walls did not reach the ceiling and some feint light came in from the narrow hallway. 

As I knelt waiting for something to happen, with all that nasty smells around me, my mind began to wander to the erotic thoughts of having no choice in swallowing what ever was pushed through the door and into my face. The ultimate humiliation of not being able to help myself, I could already feel my pussy churning its juices over and over.

Just then the first customer arrived outside the cubicle and with little ceremony promptly pushed his rather small circumcised cock through the hole, I had no where to go so I just let it slip into my mouth and using my tongue, I tried my best to give as good a blow job as possible. It seemed so different, more humiliating and not just because it was ‘right in my face’, rammed into my mouth and down my throat, no it was more the set up, and also because of the smells that invaded my nostrils as I tried to breath in that filthy hole.

I had little chance to show any finesse, at the task at hand or rather in my mouth, as the actual glory hole was less than two inches from my face and I felt that my mouth was an extension of that hole. Also the finesse went out the window because of the probing cocks bumped the back and roof of my mouth and my tongue. My mouth was filled with the pumping action of the cocks and usually rapid dumping of a load of sperm into my throat. Most of the time there was so much cum that I could not swallow it all and some escaped the corners of my mouth running down on to my chin and then dripping on to my aching nipple clamped tits.

Almost immediately as one cock disappeared another replaced it and much later Mandy had told me that Andy had arranged for all his mates to attend. So my mouth was kept well filled with cock over the next few hours.

Master, you always ask how I feel in these situations, well on this occasion I felt it was not oral sex, I became my mouth (if that makes any sense), my mouth became a receptacle for accepting rock hard cocks and my throat and stomach became a passage way for the depositing of their loads, I felt de-humanized and wickedly wanton. For the first time in my life, I realized what it was to feel like a true cum slut, to live for the taste of cum. The cock smells, tastes and touches were constant, it was the most humiliating feeling and yet I was getting off on it big time. 

Yes even when the first of seven guys used my mouth as a toilet and pissed into my open mouth, I felt always on the verge of another climax. Hew had told me to swallow his load and then keep my mouth open as he relaxed his muscles and began to urinate into my mouth, I tried my best to swallow some but most simply trickled out of my mouth and down over my stinging breasts. It was the final humiliation and yet caused my strongest cums of all. Mandy then informed me that if any customer demanded toilet time I was to repeat the process of swallowing his piss, like the good little cum slut whore I was proving to be.

And so it was for another six guys, who demanded toilet time although most preferred the traditional glory hole blow jobs and then left. How many blow jobs, I really do not know as I quickly lost count, Mandy was later to tell me, but from 10 pm it was a constant stream of various cocks fucking my open mouth, But Master Ray, the thing was that I loved every second of the humiliation and the constant thought in the back of my mind was that I was adding to the already over powering stench in the toilet. Around 3 am I was finally released and let out, there were ten guys there and they instantly burst into a round of applause. Mandy quickly quieted them down by announcing that I still had my initiation paddling to under go and promptly pulled out a ping pong paddle. Following her instructions I bent over and gripped my ankles and Mandy gave me the first ten whacks. She then Asked Andy to administer the over the knee spanking with the paddle and he duly obliged. I was un-cuffed and my pussy clamp was released and the six cum bags were forcibly removed, by Andy’s long probing fingers.

Although I still wore the nipple clamps I was draped over Andy’s lap and received ten hard spanks from his hand with the paddle, whilst still held down over his lap, Mandy invited a further two spanks from all present by their bare hands on my already crimson arse. 

I was then allowed to put on my skirt and blouse but no thong and Mandy escorted me towards the store’s door. Once outside and in her car, she announced that she would treat me to a breakfast in Tim Horton’s Do-nut bar. There were four staff and customers present for my latest public humiliation. Mandy had me hike up my skirt as I sat and waited. She ordered coffee and cream donuts but went to the loo with the donuts, she returned a few minutes later and handed me special my donut. Master was this your suggestion? For Mandy had scooped out the donut cream and replaced it with the content of two of the six condoms. Her eyes positively twinkled as she sipped her coffee as she avidly watched me chew on my cum donut.

When we had finished we drove to Mandy’s home and on her orders I took a long hot shower, brushed my teeth and gargled with mouthwash. I then returned to the living room to find Mandy wearing just black bra and black panties. Mandy then offered me a glass with the contents of the remaining four condoms in it.

When I had drunk this down she reminded me that I had a little masturbatory task to complete and produced the gigantic vibrating dildo, Andy had shown me earlier. Mandy informed me that she had exchanged this for my cum stained thong, which Andy would have stapled up in the toilet as a souvenir. She added that Andy had said “Any time I wanted, I could return to visit my thong”.

Then things got really dirty, as washed and relaxed, with the taste and smell of cum on my breath yet again, I slowly started masturbating with the vibrator, I began with it on medium speed but was soon joined by Mandy who turned it up to its max.

She cuffed my hands behind my back once more and laid me down on my back. Quickly slipping out of her panties she crouched over my head and pulled her pussy lips apart, I almost fainted as I was expecting to have to lick her juicy cunt but was now confronted with a used tampax. Mandy laughed as she ordered me to remove this with my teeth. I reluctantly did so and was rewarded with her sitting her bloody cunt over my mouth telling me to lick her clean. My nipples suddenly felt the displeasure of her wraith as I failed to lick her energetically enough.

When she raised herself my face was a mess of blood streaks but from her gasps and breathing I knew I had done a good job licking her to orgasm. She then had me kneel over the front of her sofa and said “Quick, what’s the first number that comes into your head?”

I replied “Forty”

And forty it was, she had me count out the forty whacks she laid across my buttocks with her tawse. Mandy must have adjusted the intensity of each stroke to accommodate the forty whacks because it was no more painful that any other time she had used her tawse on me with far fewer strokes.

Later as she instructed me to go home and before going to bed, I was to write this report to You, my Master and CC a copy to my new Mistress Mandy, and she stipulated that the last comment apart from my thanks to you My Lord and Master, was to inform you that I had given blowjobs to 36 Different men whilst in the glory hole in a time frame of 4 hours. 

So My Lord and Master Do you agree with my new Mistress that your Daring girl has gone astray or not… Thank you Master for arranging some of this dare with my Mistress Mandy…

I responded to Cindy…

My little slut girl Cindy,

Your new Mistress is the one responsible for all except the collection of four Condoms full of sperm which I wanted you to put in a glass along with a sparkling wine and some orange juice. I wanted you to drink a buck’s fuck fizz…    lol.

I will be having words with your new Mistress shortly…

Your lord and Master,

Ray.

