Encouraging Arse Play

My successes and failures of my first week away saw me nearly losing my panties, but managing to keep them by the skin of my teeth! For my second week away A raised the stakes on my tasks. Each day I was not only to masturbate, but to also play with and penetrate my arse. He warned me that he would be fucking my arse before long and it was up to me to ensure I was ready for it.

A and I have sporadically played with my arse and I've taken a tiny bit of anal. I've enjoyed these experiences, but haven't pushed for more as I feel that I do need more anal training. I don't always feel ready to have my arse penetrated, particularly by A as his cock is much larger than the toys I can comfortably take.

I took my instruction to heart, however, and I was glad I had packed a smallish vibrator that would be suited to anal play. I noted that I would probably need to purchase a second vibrator while I was away so that I had something larger to train with in preparation for taking my Domme's cock.

My masturbation adventures became more centred on the bedroom. On a few occasions I did my nighttime front yard excursions to get myself aroused, but I would always adjourn to the bedroom after to have access to my toys and lube and the privacy I needed for my arse play. Penetrating my arse proved no problem with my small toy and I discovered that when the dildo was on the right angle it gave me the most pleasureable sensations. Many of these sessions ended with me squatting on the floor, the dildo in my arse with it's flat end resting on the ground and I would bounce up and down on the smooth hard cock as I rubbed my clit and watched myself in the mirror, imagining I was the delightful blonde from the peepshow putting on my own performance. I would always have to stifle my joyous moans as my orgasm overtook me.

Another time I used two toys. I had my smallish Lady Finger inside my arse and took my larger red vibrator to insert into my pussy. Oh it was so tight and I felt so full having both of my holes stuffed like that! It was so hot. I squirmed on the bed, rubbing my hard engorged clit with one hand while the other worked the two toys so they were pumping gently in and out of me. It was a wondrous orgasm I reached in this state! A had certainly chosen a good way to bring out a love of arse play in me. I was loving it.

I did buy a new arse toy, however I only managed to do so the night before A's imminent arrival (A was travelling interstate to meet me, then we were heading back home together). I only had one night to practice with my larger toy. I had chosen the toy carefully, it was larger than my lady finger but still not at large as A when he is fully erect. I figured it was smarter to get an "in between" size than something overly large. That night after a quick nude trip to the courtyard I headed upstairs with my new toy to try it out.

I didn't feel ready to double penetrate with the larger toy so I focussed on getting it into my arse. Well it was much easier than I expected! I didn't have much trouble at all and though the fit was noticebly tighter it did not prevent me from ending my masturbation session squatted on the floor bouncing on my new toy as I tore a sweet orgasm from my body with skilful fingers. The new toy sat much more easily on the floor than the lady finger had, as it had a large flat base to be used with a strap on. Flushed with success I sank back panting after my achievement.

Despite my efforts, I was not able to achieve a daily orgasm. There were some days when my body simply refused to cooperate. I confided this to A and he once again requested my panties be sent to him. I begged him once more to be allowed to keep them and he offered me a bargain. He would postpone my panty ban for a week (it would then only apply for a few days when I was staying with family) in exchange for 200 spanks. I agreed to the devil's deal as I believed it would be much easier to deal with the panty ban once I was living back at home again.

Finally, there was my neglect of my blog. A had of course been checking on me and had noticed I hadn't updated at all while I was away. He asked me about this one evening and instructed that I must update it before the night was out. I did update it that night, but only with a very brief post that displeased A - he felt I was being awfully cheeky, so further punishments were due. A very special punishment that would occur on the day of A's arrival. It would happen in the morning, and he would arrive in the afternoon to inspect the results. The punishment would be perpetrated by the lovely and firm Mistress Kalyss.

While You're Away

I was going to be away for 2-3 weeks on work, so A made my task both specific to the week, and to my trip. While I was away from home I was to masturbate to orgasm at least once a day. Every day. I would be staying with family and not at a hotel, so this proved to be a little tricky for me to achieve - I had to use my imagination.

To start things off for me, A put in place a special task to be performed on my day of arrival, before I laid down to sleep in my unfamiliar bed for the first time. He knew I would be the only one home on this night, and such he instructed that I should leave my clothes in the bedroom and go outside to the front courtyard of the house where I was staying and masturbate there. When he told me this such a thrill ran through me, he knows exactly how much risky encounters turn me on. I couldn't help thinking lasciviously of the task that lay before me during my long interstate journey.

Once I had arrived at the house, finding that it was indeed empty, I dumped my gear and had a nice refreshing shower. I then ventured outside, completely naked, as instructed. I had to walk carefully when coming out the front door, it is in full view of the street outside and if I stepped to far beyond I would set off the very bright security floodlight. Managing to avoid that exposure, I snuck carefully across the gravel to stand in the centre of the courtyard. The air was cool against my skin and over the fence I could see the windows of neighboring homes, if anyone looked out those windows I had nowhere to hide. It was a bright night, the moon was big and streetlights and ambient light brought a soft glow to my skin.

I caressed my breasts and feathered my fingers over my pussy. I was soaking wet already. I started to stroke myself, feeling my pussy heat up as my skin cooled in the night air. I was so very turned on. I had a thought then and before I could talk myself out of it I went back inside and grabbed my mobile phone. I carefully re-entered the courtyard and dialled A's number.

A thought I was merely calling to check in, and asked how my trip had been and othere niceties. I confessed to him early on that I was in the midst of my first task. I heard the interest pique in his voice. I described to him where I was and what I was doing, all the while caressing my throbbing pussy. I had to speak softly in case anyone was passing by, I explained to him.

"I thought you might want to bear witness to my orgasm." I suggested to A. He agreed and I sped up my ministrations, bringing myself closer and closer until I felt the spasm of orgasm and moaned my pleasure into the phone.

I think A was pleased with that.

Make Me Proud... a task

Well it's time to get the wheels turning again. Let's roll things back to where I left off...

The weekly task assigned to me by A was to do at least one sexy thing each day that would make him proud. Open-ended tasks are always so tricky for me!

For work reasons I didn't do a very good job this week, time was not something I had in endless supply and I really felt that injured my ability to fulfil my task somewhat. But no more excuses. My best successes were to do with a cute girl at work I have been working on for a while. She is a temp, travelling through Australia from England (so she has the sweetest accent). We've chatted a lot at work and I've tried to turn the conversation more personal as we went. I even gave her my phone number though we haven't managed to meet up outside of work due to clashing schedules and her working nights.

Two days of this week my task fulfilment was initiating, and then closing the deal on a "date" (or rather, getting together for a meal) with the cute English girl. I am disappointed to report this date never came to fruition as she had to cancel on me and followups with her resulted in no further success. Poo.

I have left it so long to report I can't actually remember what other things I did to make A proud... I know I did have more successes but I can't recall them right now. Maybe later.

A sexy compliment a day keeps A happy

Week 21: The Task
A really challenged me this week. My task was to make a sexy compliment to one person each day. I am terribly shy and absolutely abysmal at flirting with people I am not already very friendly with. I know A intended for me to flirt with sexy girls that I have not yet played with and it proved a real exercise for me.

Week 21: The Failure
I started out this week with a real plan to make results happen. There are at least 3 girls where I'm currently working who I've chatted to on occasion that I could try to slip a compliment to, so I resolved to try one for each.

Monday just did not happen. I resolved to try to give two compliments on Tuesday to make up for it. I gave none. I just don't know how to work a flirty comment into an otherwise above-board work related conversation! And simple "great shoes" or "nice top" compliments certainly do not qualify! To me a sexy compliment is something that will convey "I think you are sexy/attractive/hot" to the recipient. Which means at the very least it would need to be "those jeans are great, they make your bum look really good". I couldn't even work one of those in! I am really terrible at this.

I spoke with A quite early in the week about how much trouble I was having. He agreed that for each day I did not fulfil my task 20 spanks would be added to the spank bank.

Ahh... you've just checked and noticed that the Spank Bank total has not changed. No it is not because I suddenly discovered the secret to giving flirty compliment. It's because I have already worked off my debt. Read on.

A Party and a Devious Task

On Saturday evening A and I attended a party hosted by the gorgeous and wonderful Miss V. As you may have already guessed this was something of a naughty party (or at least it had the potential to be) so it offered A the irresistable opportunity to assign me some debaucherous tasks. The outcome of this night would dictate my tasks for the following Week 20. (Ah! How sharp of you to notice that I have skipped Week 19 on my blog. It will be revealed at a later time what my tasks were that week...)

My task was two-fold. Let's start with the first component. I'd been instructed to passionately kiss (with tongue) at least five male attendees (A not included). For each one I kissed I would earn a reprieve from part of the following week's task, which will be to write 5 messages per day to new contacts on AMM.

If I kissed one or less men then I would have to write 5 new messages each day. If only 2 kisses, then I'd have to write 4 messages per day, if 3 kisses then 3 messages, if 4 kisses then only 2 messages. If I managed to passionately kiss 5 or more men at the party then I only have to write one new message per day and I will be entitled to one orgasm per day to be delivered at a time and in a manner as chosen by A. If there were less than 5 men I felt comfortable kissing at the party I would be allowed to ask A for permission to substitute girls, however I would need to kiss two women to be equal to one kiss from a man. A is obviously aware of how much more often I am attracted to women over men so he was not about to make this easy for me.

The second component of the task was terribly devious. I was to keep count of every time I received a compliment that night as each compliment earned me 10 spanks. Any compliments about me paid directly to A would be worth 20 spanks. I was to keep tabs on this the whole night and if I earned more than 20 spanks by midnight then I was to gather an audience to watch me receive my due. I was to choose my implement of destruction and explain why I chose it and also thank the viewers for their attention and for the priviledge of such an attractive audience. If I chose to receive my punishment publicly the total number of spanks would be halved. If I refused a public spanking then I would receive the full amount once we were home before I was allowed to sleep in my own bed.

Decisions, decisions.

The Task: Wouldn't it be hot...

Following my xmas pledge to A, tasks have resumed with abandon.

Daily tasks resumed midweek last Thursday and this task will apply for the rest of that week and the following week to round things out. Ah, but what is the task? Well A has decided to start off the year with a creative task, so each day I must approach A and say "Wouldn't it be hot if we..." and continue the sentence to it's conclusion. My suggestion must be able to be achieved within the week.

As usual, any additional tasks or instructions can be assigned at any time by A

Week Seventeen - The Tasks

Back to the regime of tasks, and not a moment too soon. Hopefully my break from the tasks will have me more than ready to please. Week Seventeen was supposed to start last week, but I misbehaved and acted like a child and as a result my taskload is heavier this week.

Each day, I am to give A not one but two blow jobs. He has not specified that they must be to completion, but I expect he will dictate when I should finish. I'm thinking one in the morning and one in the evening would be a smart move.

In addition to this, each day I must also send A a dirty picture message via my phone. If my technology doesn't fail me, I'll also post them here for the wider viewing.

A has also informed me that he has a very special task me, as yet unspecified, as a direct punishment for my disobedience last week. We'll just have to wait and see what that shall be.

Week 14 - The Tasks

A called me last night to have a catch up and assign this weeks tasks. He's going easy on me this week, in a way. For each day this week I need to come up with an icebreaker, something I could say to a girl I find attractive in order to start up a conversation. I can either blog it, or tell A on the phone or via email, but I must do it each day.

There is also another task, well not so much a task but a rule. I'm not to wear any underwear for the entire week. This is a little annoying for me as I don't like to go without underwear for long periods, but I must do as I'm instructed.

The rule of blogging daily still stands - the blog needs to be updated each day or else it's 20 spanks. Since my tasks may not generate enough interest on their own, I must still come up with something interesting each day to blog. Whatever it is, it's up to me, but it needs to be worthwhile. We'll see how I go.

Week Thirteen - The tasks

This week it's a new spin on an old favourite. Each day this week I need to masturbate - where when and how is up to me. But in each session I need to experiment with sexual pain. Whether it's nipple torture, spanking, clit tweaking, whatever. I need to experiment enough that at the end of the week I have chosen some kind of sexual pain that I would like A to inflict on me.

Additionally, one day this week I need to masturbate three times. These three times must be spaced at least an hour apart. I shall have to select that day carefully. Oh and it must be a week day.

Lastly, for every day that I don't update my blog, 20 spanks will go into The Spank Bank.

Week Twelve - The Task

This week A has decided to make my daily task more specific. Each day my slutty/erotic act is to take a sexy photo of myself, and send it to a different person for each day!

A told me my task while we were at the reception, so I took the opportunity to grab the mobile phone number of a couple of gorgeous play friends who I somehow didn't have in my phone yet. The hard part of this task will be coming up with more creative and interesting photos I think....

Week Eleven - The tasks

This is the first of my five weeks interstate. A has given me a couple of tasks.

Daily task - each day I must do something slutty or erotic, and then blog it. I will have to be creative with this one!

Long term task - Over the five week away period, I have to give out at least 5 personal cards. That is one card per week. When I have successfully given one away, I must blog the encounter, describing the recipient and the handover. This is very challeging for me as I have only managed to give away one card and that was at a non-vanilla party where I was with A! I will have to pull my finger out.

Week Ten - The Tasks

This week A deemed that I must ask, no - BEG him to do something to me sexually at least once per day. Sounds easy enough, but you do have to make sure you have time to do it!

Week Nine - The task

Week nine's assignment is a series of photographic tasks. Each day I am to send a "smutty" photo of myself to A. I chose to take them on my camera phone and MMS them to him. A is going easy on me this week with tasks as it's a very busy week for us in "real" life.

Week Eight - The Task

Today A assigned my task for the week. I am to write an erotic story. Specifically an erotic story account of my seduction of a sexy girl. I shall have to roll out the creative juices on this one. I have until the end of the week.

If I somehow burn through the task early, there is another erotic story waiting to be written. This one is an account of an actual event from our sexual past - a night of play with a very sexy single girl.

Fingers crossed I don't get writer's block!

Week Seven - The tasks

Week Seven already! This week my brief has changed. No more tugging off in the toilets for a little while, as my new brief is that each day, at least once I day I must do something with the aim of improving A's and my sex life. That is a pretty broad brief, which makes it both hard and easy! It looks like I'll have to tap into my creative spirit a bit this week. We'll see how I go.

Week Six - The Tasks

Already Week Six! It doesn't feel like we've been doing this that long. This week's task follows along the same lines as previous weeks - I am to bring myself to orgasm once a day, the new instruction is that it must happen before 12 noon each day. I am allowed to miss this deadline only once this week.

A has also assigned me a new task, a long term task. I have one month in which to arrange and attend a play date with a person/persons of my choosing. This may be a woman, man, couple, group... whoever. However, it can't be one of our existing playfriends, or someone met through our existing playfriends. It must either be someone new who I meet over this next month, or someone I only know in a vanilla sense who I can "convert". This is a very exciting but scary task for me as I've never been any good at being the aggressor and I know I'll have to take charge.

Given that it is up to me to choose who I'll have, I've decided to try and meet a woman (I know, everyone always wants a single girl!) but I'm going to try for that first, before perhaps considering other options. A was very insistent that I'm not to do this only to fulfil the task, I must find someone I am really interested in. I don't think I could do it any other way, there must be an attraction as I'm not that good an actress.

Sunday night I put up an ad on AMM as a single girl (in an open relationship) seeking women (and possibly couples). There are other ways to meet women and I'm not dismissing them, but given my time contraints I figure what better place to start than a website created purely for this purpose? I will keep track of any contacts made on this blog and we'll see if I can even get to the point of meeting someone for coffee. Fingers crossed. Wish me luck!

Week Five - The Tasks

A has assigned my tasks for this week. He's still quite enamoured of the idea of me masturbating daily, so I am to still bring myself to orgasm once a day. This orgasm does not need to be had at work, or anywhere in particular, but it must happen daily. A is changing the focus of my tasks and my second daily task is to give him one orgasm per day also. So that's two per day, one mine, one his.

As usual, I am to perform any additional tasks as required. We'll see what mischief abounds as the week progresses.

Week Four - The Tasks

After my outburst last week, the tasks this week have changed. I will (thankfully) no longer be required to produce two orgasms per day. I will still need to supply one at work however, which should be doable.

A has also reserved the right to assign other tasks, and the evil glint in his eye when he mentioned this told me he already has some ideas in mind. Another task A mentioned was the personal cards. I am to have made a decent start on them before the week is out. No doubt once they are created there will be further tasks involving them.

Week Three - The Tasks

I checked in with A about my tasks for the week. He sees no reason to change back from the 2 orgasms per day quota, so I am still required to perform two a day. As with last week, both orgasms must be my own, and any extra tasks must be performed as assigned.

Week Two - The Tasks

A has deemed that since I have been achieving the two orgasms per day as required, that this will be my task for the coming week. He has, however, stipulated that both orgasms must be my own. Any orgasms A has will be a bonus. As usual, any extra tasks may be assigned at will by A.