Written by Boundary Explorer

17 Jan 2012

I was out at a local club watching a band and I noticed my school friend’s daughter behind the bar. Like her mother, she is a gorgeous, head turning, fit brunette with a body for sin.

She is twenty, sexy and a bit wild. I remember DJ’ing at a party at their house where she was innocently flirting with me all night having discovered the power of her assets. She is defiantly a very hot young woman now.

She noticed me and said Hi. I asked how her studies were going and she had deferred for a year to travel overseas and she was working to save the money. “And how’s that working out for you?” “It’s hard; I have to work my ass off a hundred dollars a night”. “Your so gorgeous I would like to work your ass off for a thousand a night”. She was shocked to hear me say that and somewhat taken aback. “I bet you would”. “What type of girl do you think I am?” “Well I think you’re a beautiful sexy woman who needs money and some sexual education”. “What makes you think I need educating”? She said cheekily looking at me with her sultry green eyes. “Because you have only slept with immature boys who don’t know what they are doing’. You need an experienced man who can show you the rapture of total pleasure. There was an uncomfortable pause…“Hey I’m sorry for being forward please accept my apologies”, fearing I was pushing my luck. She just looked at me, blushed with a cheeky smile on her face and kept about her work.

Just before I left she followed me to say goodbye by the bar and slipped a note into my hand and said “ You’re a bad man, I’m not saying yes but call me and don’t tell a soul” I got home and sent her a text saying that my comments were inappropriate and I am sorry and just wanted her to know she is a gorgeous woman, I did not mean anything by it and I am completely discrete. She text back, “I am flattered, it was hot; what could I teach her?” Quick thinking was called for as I asked her if she had ever come more than once in her life? She texted back she had only ever had one orgasm when her girlfriend went down on her. She had never climaxed with a boy before and I was right, they didn’t know what they were doing.

Wow! I thought that was unexpectedly out of left field. I text back, asking her where she was and she wrote she was in bed. What are you wearing? “Nothing, I am lying here naked”. Are you touching yourself? I wrote. “Yes” she replied. “Is your pussy wet?” “Yes” she replied. “Stick two fingers in your pussy and put them in your mouth” I text back. She did not reply so I thought I had spooked her and crossed the line.

Three days later she completely shocked me out of the blue. She sent me a sexy photo of herself with a text that said, “Does your offer still stand?” I was blown away that she even considered the idea. Worried her parents may find out, I texted back “Of course do you think you can handle what I have in mind because it involves total submission and doing exactly what I say obediently”. “What did you have in mind?’ $1500 for Saturday to Sunday afternoon ½ on arrival and half when your done, how does that sound? That sounds very generous but what do I have to do for the money, “prostitute myself”. This arrangement is in the strictest of confidence and you don’t do anything you don’t want to. The only condition’s I ask is to give in to pleasure, allow yourself to be subordinate as an object of sexual gratification and learn how to fuck and be fucked.

“Give in to pleasure and do whatever I say obediently and that’s all I will say”. I promised her if you concentrate upon nothing but pleasure and do as you are told you will have the best sexual experience of you life. Don’t for a second consider it prostitution, more like a generous benefactor contributing to your sexual education. I will not put you in any danger. She texted back, “OK we have a deal as long as it’s our secret but it makes me very nervous”. Do I have to sleep with you? I text back, “ you don’t do anything you don’t want to with the utmost discretion is assured”.

I booked a room in a nice hotel, champagne the whole nine yards to impress her. I texted her details and told her to meet me at a coffee shop in the city. I told her to wear a short skirt and top that showed off her cleavage. She turned up a few minutes late looking very hot, a little nervous and I reminded her she was late.

I told her I am going to buy her some nice lingerie at a shop nearby. We went into the shop and she started looking through the rack for a couple of minutes. An attractive middle aged shop owner approached us. I whispered in her ear to pick out some provocative undies and a black corset with suspenders. I explained that my little princess would be wearing them now. I asked if she could help us with the fitting in private as we were going somewhere special and slipped her a fifty dollar tip. My young protégée looked somewhat embarrassed as I told her to do as she is told as we proceeded to a stock room out the back.

The shop assistant told her to remove her clothes and she reluctantly complied standing completely naked before us. The assistant helped her dress, “Someone is very lucky tonight, you look very sexy”. The lady was twice her age and looked hot. My young lovely let out a sigh as the lady, the same age as her mother run her fingers lightly all over her body as she fit the corset. I asked her “Does she look fuckable?” She replied, “extremely so”. “Feel her Pussy,” I said. The older woman placed a finger in the young girls pussy pulled it out and licked her finger. “She tastes very nice”. She helped her dress and I paid. I told the woman that she was very inexperienced and I was taking her to a nice lady who would teach her some discipline. “I would love to watch that” she replied.

This girl was a spoiled brat who, no one ever said no too. I had booked a session with a top dominatrix mistress who worked out of a large mansion in the city. We pulled up in the cab and she asked, “Where are we going?” I told her if she wants to earn her pay and learn she does not get to ask questions. We made our way to reception and were directed into a waiting room. She had no idea what was happening and was a little nervous. After a few minutes we were greeted by the mistress, a stunning woman dressed in full dominatrix attire that looked like Betty Page. “Is this the girl? “Yes” I replied”. She’s a young and pretty one isn’t she, I shall enjoy this. I told her to be gentle with her as it’s her first time and she is very inexperienced. We need to explore her boundaries and push her as far as she felt she could go. “Don’t worry by the time I am finished she will do anything we say, enjoy it and ask for more”. This made her apprehensive yet inquisitive like waiting for a spanking after being a naughty girl. She enjoyed being the center of attention. None of the clumsy young boys who had fondled her were so forward or sophisticated. The dominatrix oozed authority as she led us into her dungeon. This young girl had seen nothing like this, her eyes were wide open, as she was both shocked and excited.

I told her that you must do exactly what the mistress says as this is a big part of her education in subordination. The mistress told her to take off her skirt and top, put it on the chair and kneel before her and kiss her feet. She let out a cautious laugh and the mistress pulled her into line telling her she was not allowed to speak unless she was ordered or she would be punished. The mistress ordered her to answer only with “Yes Mistress” and nothing else would be tolerated. She reluctantly complied playing along kind of what was going to happen. “She kissed the dominatrix feet adored in six inch black stiletto heels compliantly and was told to stand. Our young flower stood adorned in the sexy black corset, suspenders and French lace undies. “Don’t you look nice, did your sugar daddy buy those for you?” “Yes Mistress”. She led her to a large wooden brace removed her undies and restrained her hands and feet, which freaked her out. To her credit she did not say a word as the mistress laid out a series of toys she had never seen before, little own experienced. The mistress selected a vibrator for her clit and turned it on. The mistress then blindfolded her teasing and lightly scratching her long fingernails down her young slaves milky inner thighs.

She was very excited as the mistress placed a vibrator on her clit telling her she was not allowed to come until she was instructed to. If she did she would receive 10 strokes of the cane. She moaned with desire and was told not to come or she would feel the sting of the cane. The dominatrix removed the vibe from her clit and squirted a generous dose of some lube into her young eager pussy. “I feel you need to be broken, would you like me to break you?” “Yes Mistress” she whimpered. Her dominant mistress placed a high leather collar and chain around her neck and unhitched her from the frame. She then placed a long heavy metal bar that spread her legs wide apart that shackled her ankles at each end. She was bent forward over another frame that her exposed and spread her firm ass with wrist restraints. The mistress then instructed her slave that the nurse was going to ‘clean her’ and she retired to a large armchair in front of her and lit a cigarette.

A pretty blonde entered the room dressed as a nurse. The woman had a large silver tray with champagne, glasses a small silver bucket and a doctor’s bag. The nurse popped a bottle of champagne and proceeded to pour mistress and myself a glass. The nurse opened the bag and took out a large ball gag large strapping it to her subject’s mouth. Our restrained beauty felt completely helpless as the nurse produced a large glass enema from the bag, filling it with champagne liberally lubricating the long rubber stem. Our blonde nurse walked behind her lightly touching and spreading her firm ass cheeks touching her wet pussy lightly circling her virginal asshole. The nurse then inserted two fingers deep into her virginal asshole for the first time. Our young sub was shocked, bucking as it took her by surprise. No one had ever touched or penetrated her ass before. Her screams and protests were muffled through the gag. “Did I tell you to speak”, exclaimed the mistress as our young sub sobbed at her treatment. The Nurse then held the silver bucket beneath her inserting the six inch rubber stem deep into her ass and proceeded to slowly empty the fizzy champagne deep into her asshole. Our little slave girl moaned in pleasure as one third of a bottle of bubbly rushed into her ass. The mistress then ordered her to hold the champagne in her ass till she commanded her to let it go as the nurse rubbed her pussy till she come. The mistress then commanded her to push it out as hard as she could as the nurse caught the liquid in a small silver pail. The nurse cleaned up our slave and disappeared as the mistress walked removed her gag. “Did you enjoy that?” “Yes Mistress”.

The mistress then produced a cane and told our young sub to count off ten strokes “Yes Mistress” she replied. She rubbed the cane over her thighs and ass before delivering four vicious stokes of the crop that burned ass.

This girl was now in dire anticipation of what was going to happen. The mistress exclaimed, “I will now mark your ass and you will feel the sting of my cane am I clear” “Yes Mistress” she and she delivered six more hard strokes that broke her milky white skin. The mistress then positioned a mechanical fucking machine with a large silver dildo behind her and positioned it to penetrate her ass. Her asshole was relaxed from the champagne as the mistress squired lubrication into her asshole. The mistress stretched her slave’s ass wide open by placing two finger’s each side and pulling her hole wide open. She then pushed an ecstasy tablet deep in her ass. Our slave girl started to cry, “Does that hurt?” “Yes Mistress” she said through her tears. The dominatrix turned the machine on and it penetrated her ass deep and hard on a slow speed. Her mistress left her alone for ten minutes with the machine slowly fucked her virginal ass in an unrelenting mechanical fashion. She had never experienced anal sex so she felt quite violated as the pain had subsided, she had now surrendered subordinately to the extreme pleasure of her rough treatment. Mistress returned to the room and inserted a large vibrator in her pussy and placed one on her clit as she positioned the machine to pound deeper into her ass. She moaned lost in the experience of double penetration as she was allowed her to come. She screamed, shaking as she came violently. Mistress then removed the contraption and blindfolded her. Mistress unhitched her and instructed her to kneel before her. She told her to lick her mistress’s pussy then turned around and instructed her to lick her mistress ass, she complied “Yes Mistress”. “I want your tongue inside my ass is that clear?” “Yes Mistress” I could see she felt dirty but was extremely horny and obeyed without question.

Mistress donned a large strap on dildo and proceeded to fuck her doggie style as she she screamed climaxing in a deep orgasm. Her Dominatrix made her lick the dildo clean and thank her. Her mistress told her that she must obey her master and not to question anything that was asked of her. She agreed, “Yes Mistress”. Whatever is asked of you, you must comply. “Yes Mistress”. “I have inserted something in your ass that will release any inhibitions you have and its completely safe is that clear” “Yes Mistress” “Are you broken”, “Yes Mistress”. This girl was well on her way.

We were ordered a cab and made our way to our next port of call, sex club with a glory hole. She was still tingling from her last adventure as the ecstasy was kicking in. She told that she had enjoyed the experience as I explained that we had only just got started reminding her that she must do all that is asked of her. We arrived at the sex club and browsed at the toys for a little while. She had never been in a sex shop so I picked her out a nice vibrator. Guys checked her out as I paid to enter the cruise bar. We entered an area with metal bench seats where men were watching porn. The men were shocked to see this hot girl and a few milled outside the room not believing their luck. The four men inside were transfixed as I made her take off her panties and hold them in her hand. I hitched up her skirt exposing her pussy. She was watching the gang bang porn glancing at the men masturbating while I placed the vibrator on her pussy. She was moaning loudly as I was penetrating her with the vibrator in full sight. A crowd gathered so we got up and went to the area outside the private booths. Men were cruising outside scoping her out as we went inside a private booth closing the door behind us. She had no idea what was happening until a stiff 8’ cock appeared through the wall. I told her to do as she is told as she reluctantly dropped to her knees on the stained floor, wanking then taking the strangers cock in her mouth.

She looked so hot with that cock in her mouth and after a few minutes the guy started to come. I grabbed her by the hair holding her head against the hole as the guy fucked her mouth. She gagged as he his come spilled from her mouth over her chin. I told her to remove her clothes, she complied and I put them in a plastic carry bag. Almost strait away another cock came though the wall and she was told suck it. She was now naked in the booth sucking stranger’s cocks.

My cock was as hard as a rock. The guy came all over her hair, tits and chest as another cock appeared which she took in her mouth exploding come over her. I opened the door and there was at least seven men standing in the area outside the booths who were shocked to see her naked covered in come. I led to the metal bench outside the booths. As quick as we sat down a guy walked up, dropped his pants and starts stroking his cock. He puts his huge hard cock up to her mouth and come all over her face. Soon there are a bunch of guys with their cocks out masturbating. As each man was ready to come, they took turns coming in her mouth and over her face. I fucked her doggie style and when I had finished another took my place while at least seven men come in her mouth drenching her hair and face. At one point she was laying on the bench with a line of guys wanking over her face and tits while guys took turns fucking her. This went on for at least an hour till she was sweaty, spent and had the sperm of at least twenty men all over her. She put her clothes on, soaked in come and we left.

We hailed a cab and went back to the hotel. She wanted to have a shower and clean up; I grabbed her cellphone and took a picture of her covered in strangers come before she showered to remind her of her exploits. She showered and slept soundly. We woke up, ordered breakfast and discussed her adventure. She said it was wild and she enjoyed every minute of it. “I lost count of how many times I came”. I paid her as agreed and I commented that she had earned every cent. “Thank you for my education master, I now know how to fuck”.

I have managed to have some very interesting adventures with her including an excursion with the middle aged lingerie sales woman who it turns out was very kinky indeed. But that is another story for another time.