The Checklist

The Checklist

Mark was not sure why he had agreed to what she had ordered of him, but that didn't really matter now. He had agreed to it and knew he would be driven to try and please her regardless of what she demanded of him now. Not that she would really care at all, I mean she had a partner and she had other playmates. It was very clear that he was just being toyed with for her amusement and he was positive that he would be cast aside when he had worn out his value as entertainment.

They had met on and online dating site and chatted and she had expressed a desire to be in charge and have a guy do anything she wanted. He had told her that his biggest pleasure came from fulfilling a ladies desires, even when they were a bit kinky and wild and even when they were things that he did not actually want to do. They started exchanging texts and emails more regularly and after a few days she told him that she wanted to be there the next time he came, and that he should stop any form of self pleasure until that time. Mark agreed to this as he guessed it would be a few days at the worst and he was sure he could hang out that long.

So cut to a week later and thy are still yet to meet. Driven by his desire to please, he has denied himself orgasm at all for that whole time, which is unusual as he generally got himself off a couple of times a day when he was not getting any action. Although he had not cum in that time, he had played with himself, but on her orders. It seemed like at least once a day she had ordered him to go and jerk off until he was about to cum and then stop and get back to whatever he was doing. This made things much worse for him. She also added to his torture in this regard by telling him to surf the net for porn, read and even write kinky stories. All of this stimulation with no relief was making him desperate, but he had promised she would be there the next tim he orgasmed and he was going to make sure that happened. Even sitting at work he had to check messages from her regularly online or on his phone in case he missed something and keep reading stories.

Mark was not someone who anyone would think was desperate, in fact he had no trouble finding someone to play with or picking up in a bar or anything. He was tall, a bit over 6 feet or so, slim with an attractive face. His hair was closely cropped but this look suited him as well. He was clean shaven and had a very infectious smile. He was 38 but looked younger and could easily pass for early 30's. Even knowing he could go and get someone else if he wanted didn't help, he had promised this to a lady he had never met and he would do his best to do this for her, because that is what she wanted.

His phone beeped and it was a message from her that simply said “check your email”. He logged back onto the dating site and there was a fairly lengthy email from her, well more than the usual two liners that people sent back and forth.

Hey Mark,

I am very glad you seem to be holding up your end of the bargain but you might not like what is coming next. I think I might be able to really take advantage of you and plan on doing just that. I really like the idea of making you jump through hoops and seeing how far I can push you with this game. So you will continue on with what you are doing, you are not to cum until you are with me and even then you will have to earn it and will be doing it in whatever way I direct at the time.

Before you get to meet me though you will need to bring several things with you and you will probably no enjoy collecting them. They are as follows:

1. A letter from a female that you have pleasured orally with no sex or returned pleasure for you (obviously). You will find a girl who is willing to let you pleasure her orally and who will then write a note for you. The note is to be addressed to me and explain that you got her off and got nothing in return. I do not care what age she is or what she looks like. I do not care if you have to pay her or anything like that. Just get the note after you have done the deed.
2. Now I know you are straight, but next is a letter from a male you have pleasured orally with no sex or pleasure for you (again, obviously) and you will swallow his cum. Same as above, the note is to be addressed to me and I don't care about their age, looks or whether you have to pay them or not. Just get the note after you have done the deed.
3. A note from anyone, male or female, who watched you jerk off until you were about to cum and then stopped. I don't care how you get them to agree to it, but they have to watch you play with yourself and then write a note addressed to me saying you almost came but stopped before you did.
4. Another note addressed to me, but this time from someone who pissed on you. It can be male or female, paid or unpaid. Just get them to piss on you and get me a note to prove you did it.
5. Surprise, surprise, another note but this time from someone who pissed in your mouth but it cannot be the same person who pissed on you. Same rules, don't care who or how bitch (heh I might call you that from now on too) just get me the note as proof they pissed in your mouth. This will be good practise for you anyway.
6. Note number six is to be from a lady who punched you in the balls. You will obviously have to ask her to do it and explain you need a note saying she has done so.
7. I would like to know you have been fucked in the ass so the next note is to be from a lady who has done this to you with a strap on or dildo or vibrator or whatever. Do whatever you need to do to make it happen.
8. Same as number seven, getting fucked in the ass, but this time from a guy. Any guy you can, just get a note saying you did it for me.

Now that will do for now. I have a few other things I would like to see but I will save them for when we meet as I would like to see them. I will also enjoy seeing the replay of several of the things on the above list over time as well. So now you better get cracking bitch, you have eight notes to get for me. I know you are straight and don't want to be playing with guys, but to be honest that makes it even more of a turn on to me. Make sure you don't accidentally cum as you do these things either, I want to see your next orgasm for myself. I would like an update email from you each time you cross one of them off the list telling me what happened. And it has to be eight different people, no doubling up!

Have fun bitch!

Maz

Mark sat back at his desk and stared into space for a few minutes then read over her email again. Surely she could not be serious? Why would she want him to do all this when she would not be able to see it? Enough is enough he thought, deleted the email and went back to work.

Several hours later, towards the end of the day, he went into his deleted items and printed the email off. Everyone else had gone so there was no worry about someone seeing it. He read it again and started surfing through a few profiles on a couple of the dating sites online. He didn't want to do it but was starting to check into it anyway. Mark shook his head, knowing he would at least try and see if he could do it. He couldn't help himself.

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Hi Maz

I really don't know why I am doing this, but I got one thing done off the list today and got the note you wanted. I went with number six first because I know a lady who is into that sort of thing. We met for a coffee and just chatted a bit. When there was no-one close by or looking she got me to stand up, put my hands on my head and then she punched me square in the balls. It hurt like hell, as I am sure you would expect. She told me to stand there so she could enjoy the look of pain on my face, then she reached out and grabbed them in her hand and squeezed them until I begged her to stop. I asked to write the note for me then, which she did and then she went back to chatting as normal, as if nothing happened.

I hope this is what you wanted to hear and I will update you when I get more done. My balls hurt a lot after that today but I am still desperate to cum.

Mark

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Hi Bitch

I am very glad to hear it, thats fantastic. I wish I could have seen that, although I am sure I will get to at some stage. Keep up the good work.

Maz

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Hiya Maz,

OK, I got number one done and yes it was probably the easiest one. It was a lady I have been speaking to for a while on  dating site and she isn't into things kinky but knows I have dabbled with kinky things so it was easy enough to explain to her that I needed a note and why. She was pretty good about it and loved being licked, she came twice. She said she felt bad about not getting me off in return and even said she would do it and still say in the note that nothing had happened but I did what you wanted and made sure nothing did.

Mark

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Hi Bitch,

I knew you would take the easy ones first. Looks like the next choice isn't going to be too easy for you. I look forward to your next email.

Maz

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Hi Maz,

I actually got two done today, and yes from two different ladies.

The first one was a lady who I have been chatting to for a few months and she is a little bit curious about a lot of things and I asked if she would mind pissing on me and doing the note bit and told her exactly why. She felt a bit weird about it but agreed to it as long as it was not just that. So I went to see her this morning and she wanted me to go down on her first but to get in the mood for that she wanted to watch me wank. I know this won't count for the number 3 on the list because it has to be a different person, but I did wank for her for a bit and then went down on her until she came and then she pissed on me in the shower. It was warm and made me feel very dirty, but also aroused. Then I washed up, got dressed and left.

When I got back to work I noticed a friend of mine online. She is a Mistress who lives well north of the city who I have chatted to on and off for several years now. She is very much into pissing games and stuff like that and has told me many times she wanted to piss into my mouth. I told her about you and the list and she loved it and asked if anyone had pissed in my mouth yet, which of course they have not. She told me to come on over. Thankfully I was able to get away from work. You will be pleased to know that she was a bitch about it. She had me naked and teased the crap out of me. She cuffed my hands behind my back once I was naked and then played with my cock, giving me a hand job for ages and telling me she was going to make me cum and I would then have to tell you I failed you. I begged her to please not and she just kept going. I don't know how I managed to hold off from cumming but I managed somehow.

Then she told me she didn't need to piss so I should make myself useful while we waited by going down on her. I lapped away at her pussy for about half an hour, she came twice in that time, and then she said she needed to piss. She made me lay down on the back lawn and stood over me. She was pissing on my chest and then leant back and told me to open my mouth which I did. The first bit went straight to the back of my throat and made me choke and gag. Some got swallowed and some came out my nose, I can still smell it now. She laughed a lot at that and then started again and told me to catch and swallow as much as I could. It was very bitter and salty and I swallowed a lot. She had me clean her up with my tongue and then asked me what else was on the list. She might know some people who can help with some of the other things but wants to be there to watch and told me to check with you, so I am. She will write the note when I come back to her with an answer from you.

Mark

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Thanks bitch,

You have made my day with that email. Pissed on by two ladies in one day and only one note to show for it. What if she doesn't do the note? You would have to find someone else. Hahhahahhah. Of course she can watch you doing any of the other ones, in fact feel free to give her my phone number and she can send me pictures of you doing it. That would be wonderful.

Have fun bitch,

Maz

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Hi Maz

I went to the pub after work last night and had a few drinks and ended up chatting a lady there. She was a bit rough around the edges, mid forties, and worked in the mines so was in town for her week off. She was pretty smashed and we ended up flirting and stuff a bit. I told her about this little “game” and that I needed to have someone fuck my ass with a dildo or toy and she said she liked that idea.

We went back to her place, had a few more drinks and started kissing and undressing and I went down on her for a while then we got down to business. She got her vibrator out, lubed it up and fucked my ass with it for a while. She left it in there and had me go down on her again. I didn't like how it felt, but she did it. Then she basically passed out so I went to sleep.

The next morning I asked her to write me a note for you and she said she didn't remember doing what we did so would have to do it again to be able to write the note. She got me bent over the table and fucked my ass with it again, at the same time stroking my cock and I had to beg her to stop before I came. She stopped and then wrote the note for you.

Mark

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Hey bitch,

Thats funny as fuck, you had to get it done twice. I am sure she did remember and just wanted to go again. You must be so horny now, I bet its driving you crazy.

Have you heard back from the other Mistress lady yet?

Maz

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Hi Maz,

Yes, she emailed me this morning and told me to come and see her to collect the note and to meet a friend of hers tomorrow at noon. 

You said you didn't care how I did it so I told a fuck buddy of mine that I needed to have her watch me jerk off without cumming and then get a note to prove it as a bet with someone. She laughed and was quite happy to watch and do me a note so that one is crossed off.

And yes I am extremely horny and need to cum so badly. I still can't believe I am putting myself through all this when I don't even know you and have not even met you. There must be something wrong with me.

Mark

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Hi bitch,

There is something wrong with you, you are a pathetic loser. I can't believe you are doing this either, but you are!

The really funny thing is that you are going to be at your horniest now after almost 2 weeks of not wanking and the only things left on your list involve guys. This will possibly be the most turned on you have ever been in your life and it is going to be you and lots of cock.

Have fun on your lunch date tomorrow, I look forward to hearing all about it and don't forget she can send me pictures.

Maz

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Hi Maz,

Well you would have seen the pictures by now and I am pretty sure she took some video of things too.

I got to her house and she introduced me to a guy in his 40's that was there. He is bi and was happy to go along with the deal and write me a note after I sucked him off. She made me undress and then I had to get on my knees and ask permission to blow him. He let me after making me beg for it and you would have seen that first picture or video of me taking a cock in my mouth for the first time. It did not take him long to cum and I managed to swallow it all, even though it was foul and make me want to vomit.

Then he said I had not put enough effort into it and would not write a note until I did a good job, until I did it to his satisfaction.

In the end I had to blow him four times before he would write the note and the last time took forever.

Anyway, thats done. He has a bi friend who is going to get the final thing crossed off the list for more tomorrow so I have to go back again.

Mark

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Good bitch,

I loved the pictures and videos she sent, you look like you were almost crying but I did notice your cock was hard at the time so it can't have been all bad.

It is much better to have her there so I can not only get picture evidence but I also know she is making it difficult for you plus she gets to enjoy it too! Everyone wins.

I bet your jaw is sore from that, too funny.

Have fun tomorrow!

Maz

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Hi Maz

The last one is done and again you would know this already.

The guy from yesterday was there again with the Mistress and also his bi friend. The friend made me go down on him once I was undressed to get him ready to fuck me. Then he asked me if I had been fucked in the ass before, and I said only with a vibrator. He said he didn't like breaking in a newbie so would only do me after the guy from yesterday had broken me in.

So then I had to suck the guy from yesterday again so he was nice and hard so he could fuck my ass. Thankfully he used a condom and slid in with the help of a little lube. It still fucking hurt. While he was fucking me his friend decided to use my mouth again so he was ready when it was his turn. I am sure you liked the pics of me with a cock in each hole.

The guy fucking my ass came at last and pulled out so his friend could fuck me. He then came round and lifted my head up so he could empty the condom into my mouth and then made me lick his cock clean while the friend was fucking me. I told him I didn't want to but he said there would be no note if I didn't do it, so I had no choice.

So I had a cock in my ass and one being cleaned in my mouth when the Mistress started to stroke my cock. After all this time it was not going to take much to make me cum. She was laughing and said it would be hilarious if I blew the deal right at the end here by having an orgasm after I had done all the things on the list and wondered what punishment would follow from you.

I was very lucky that he came and she stopped before I crossed that line. He also made me lick him clean and swallow the cum from the condom which was really foul.

The note was written and I left, although I have been told to ask you if they can have fun with me again.

So anyway, I have done all that you asked and have 8 notes for you from 8 different people. Can I please cum now?

Mark

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Hi bitch,

No way! You haven't earned the right to cum yet bitch. What made you think it would be that easy.

I am pleased you have the notes though and will let you meet me now so you can present them to me. And yes, they can play with you again anytime, the more cock for you the better although I would like to be there at some stage and watch too.

I will text you my address, be there at 4.15 today, you will need about an hour and you will be drinking my piss when you arrive.

Oh, and be wearing frilly or lacy knickers. You will need to go and buy some and you have to tell the lady they are for you to wear. 

Can't wait to see you tonight!

Maz

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