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The School Superintendent

The winter of 2015 was quite a memorable one for me, I had just met a woman who was intrigued by the whole BDSM scene but had never tried anything other than plain old sex with her high school sweetheart turned husband who she was in the process of divorcing. She was the administrator of a charter school system, she said here, I have a book I think you should read. It was her copy of 50 Shades of Grey with highlighted chapters and underlined sentences, the next to last page she wrote,” I want to try it, I want to try it all.” I read the book to just see what she was expecting, it was kind of lame for the most part, I texted her that yeah, I’d be more than willing to tie her up, spank her etc.....but she had to sign a contract first (pulled that part from the book, lol) she responded with OMG! When? So we set a date and we met at a local winery and sat down to discuss terms. I had printed up a very basic letter that she happily agreed to everything and anything in it, signing her name and said, we’re doing this tonight right?....I cleared my throat, leaned over and whispered into her ear “you meant we’re doing this tonight, Sir”.....her eyes popped open and she kind of sat there quiet for a second and said “I’m sorry, it won’t happen again”.....and I added Sir once more. Before she spoke I said we need to leave before she got herself in deeper. Once outside in my car she said this is hot.....I said not another word until I say you may speak. I pulled out a nice, new 1.5” black leather collar that I placed around her neck, as I tightened it up I said nod your head if it’s too tight, she did so I loosened it a notch, better? to which she nodded again. I drove to the hotel I had rented playing a couple of songs that were featured in the recently released 50 Shades movie....the smile said it all, but also the wide eyed looks I was getting told me she was nervous.

Once at the hotel I opened up the door to the room, it was a nicer room with a large sitting area that I put a chair in the middle of the room with a black towel on it. I told her take your clothes off and sit, to which she did immediately. I said you may now speak when spoken to, do you understand...”Yes Sir” she replied, “good girl, but you slipped up almost as you were signing your willingness to be used by me, what should I do with you for that indiscretion?” She said I should spank her, which I did. 10 firm slaps on her ass, the last one much harder than the first nine. I then proceeded to put wrist restraints on her and I paused, I said did you really read the contract? She stifled a laugh and said no, not really, thinking it cute. Well, I had read her book the last thing she could have done was read my contract.....the look I shot her made her realize I wasn’t being cute. I said well, basically you agreed to anything I want to do to you, signed and dated....this is your last chance if you want out.

After about 5 seconds she said “Sir, please use me for your pleasure in any way that pleases you” ....”Good girl” is all I said as I unzipped my pants and put my cock in her mouth. Her cock sucking skills were in need of a refresher course, I said her let me help you as I grabbed her by the hair and fucked her face for a brief period. She gagged slightly and said I’ll do better next time....Sir.

I helped her stand up and led her to the bedroom area of the suite, I had turned the bedding down when I checked in earlier and had more restraints ready, she said “oh wow” which got her a firm slap on her ass. I told her to get on the bed and she laid down on her back with a very soft come hither look, no I said. Face down, ass up slut. She looked surprised I said “you know, why are you looking surprised?”

Placing connecting links to her wrist restraint & collar I rolled her face down. Stroking her pussy which was by now soaking wet I then lifted her ass up. I started rubbing her dripping wet clit, she moaned slightly at first, then a bit louder which earned her a correctional slap on her ass. I said we need to keep it down as I slipped a breathable ball gag in her mouth and fastened it snuggly. I said feel free to moan or squeal now my slut. A few mild protests came forth but they soon turned to muffled moans and other noises I started rubbing her clit once more. Starting to now work a couple of fingers in her she ground herself into my palm, with a mmmmm sound as she pushed backwards. Working her pussy for a few minutes with a bit of lube really relaxed her, I was 4 fingers into her and she was moaning in ecstasy, I got the feeling she wanted more. Could she want to be really stretched? Could she handle it? I decided what the hell, she’s been a gamer so far, so taking liberties with this slut I decided I was going to fist her. A bit of manipulating and twisting, turning and pushing and a whole lot of lube got my hand firmly into her hot, hungry pussy. She was loudly making a mmmm mmmm mmmm sound while also grinding intermittently. She had cum at least once, possibly twice, the sheets were soaked and I thought I heard a muffled “more” come from her gagged mouth. I pulled the gag aside for a moment to confirm what she said and she repeated “more, Sir”. Yes my slut, I replied as I slid my cock into her mouth, she happily sucked it like a pro now.

I decided to go to working that pussy again after replacing her gag, I said you love that don’t you to a muffled yyysss sssrrr. Fast learner apparently, maybe that’s why she’s the school district superintendent! So after a few more minutes of working her pussy with my hands it was time to fuck her a bit. My cock slid right in and out of her pussy, like a soft, slippery & velvety glove it was so smooth. I thought, damn this slut is stretched so much! So I decided to change things up once again.

With her ass now up in the air I squeezed a bit of lube on her it as I started working her ass which was a bit tight at first. In a slow circular motion I massaged her ass and putting one finger in and working it for a minute or two I felt her muscles slowly loosen up, next adding another finger and massaging it once more for a few minutes she was getting ready. I reached around her and pulled her gag out, and with a slow but forceful motion slid the tip of my cock in her. Hearing her oooohhhh, and mmmmm I was encouraged to work the head of my cock in and out, feeling her stretch as it passed in and out, when I heard her say “deeper Sir”. I started to go a bit deeper but still at a slow pace, and I heard her breathing get faster and heavier, she was really enjoying getting her ass fucked! She started saying “fuck me Sir, fuck me”....I said no, repeat after me....”fuck me like a whore, that’s what I am” she said “fuck me like a whore, that’s what I am “....again, again, again....I was now fucking her ass deep and hard, she was repeating the line I told her too. Thrusting now as deep and as hard as I could I was about to cum, I let it go deep inside her ass, I stayed there for a what seemed like a few minutes listening to her breathing going from an intense panting to a more controlled rhythm. She very quietly said “thank you Sir” as I pulled my cock out of her and as I released the restraints I told her it was time to get in the whirlpool tub.

I opened the bottle of wine I bought at the winery earlier that evening and poured us a glass,....something about a good Merlot after sex. So we sat in the tub for a bit, and I asked her did she like what we just did and she said yes and was hoping to maybe we could do this on a semi-regular basis! She commented that after 20 years+ of vanilla sex this was just what she needed. I asked if she was sore and she replied no, she had one of those huge toys with the suction cup bases she liked to get off on. She did say though that was the first anal sex she had ever enjoyed, she had considered trying to stop me but she signed a contract after all! So as we finished the bottle of wine I stood up in the tub, and said now you need to fulfil the last clause in the contract.

Telling her to get on her knees I said it’s time for blowjob, it had better be good or I’ll spank you hard and make it hurt this time! She said “yes Sir” with great conviction in her voice, hungrily taking my cock in and licking it with great delight. She was massaging my balls while pumping my cock, it was surprising how ast I had to cum, and when I did she deep throated my cock taking the first few squirts of cum right down her throat. She then proceeded to pump my cock and get the last few drops of cum out, licking her fingers as she finished. “Good girl” I said helping her out of the tub. We dressed and parted for the night, I met with her a few more times and there are other stories to be told, but those....are other stories!

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