After his last assignment; I decided that Panty Boy needed a little more practice when it came to anal play. So this was the theme for his most recent assignment. Take a look and see how he got on...
My 4th assignment for Mistress – anal training. Mistress sent it a six day timetable starting it off gently with fingers only for the first two days and then introducing the anal plug for the next two days before introducing the dildo for the final two days. Thank You Mistress.
i followed Mistress’s instructions to the letter and for the first two days played with my ass using fingers only. Using only one finger on the first day and one then two on the second. Each day involved 15 minutes of anal play and i found the most comfortable position for this was on my side with my legs drawn up towards my chest – almost the foetal position. Whilst being more comfortable than on all fours this had the slightly unfortunate connection to being at the doctor‘s and having your prostate checked. Not nice or sexy. But i relaxed as best as i could and followed Mistress Cristal’s instructions and gently fingered my ass doing what i’m sure She intended – stretching it slightly and slowly ready for the next step.
The next day was the first day with the butt plug. Using copious amounts of lube i slid it in and out of my ass for 15 minutes and then fully inserted it for an hour. During this hour i was at home pottering about doing jobs as you do when at home. So i was taking out the rubbish, loading the washing machine, clearing away after lunch, just general stuff you do when at home. Now the problem i had was that the plug would slip out as i was walking around. It’s a slim beginners plug and, as such, there’s not a lot to grip to stop it popping back out. Relaxing or clenching didn’t help at all and i found there were only two things that would keep the plug in place for the whole hour as Mistress commanded. The first was to sit on it. In that position it wasn’t going anywhere but it was very restrictive – i wanted to be up and about doing my normal everyday things. The second way – the way that enabled it to get on with things – was to pull my panties up really tight. Effectively giving myself a mini wedgie, and the pressure of my panties would help keep the slim plug in place. So that’s what i did. And i also did the same on day four after first stretching my ass for 15 minutes with two fingers as Mistress instructed. This gentle stretching was beginning to play dividends because I was finding the process easier and easier. My “little pucker” as Mistress calls it was being slowly unpuckered. Slowly.
Days five and six involved use of the plug - keeping it in for first an hour and then two hours on day six. But i felt this was all leading up to the use of the dildo on days five and six. This was what, in my mind, Mistress really wanted it to be able to do. The whole point of this task. To be able to fuck myself up the ass. Even after all the anal play, stretching with fingers and plug, i still found this a challenge. My “little pucker” would tighten if i was not totally relaxed and make the process difficult and, if i was not careful, painful. i think part of the problem is that yes i’m kinky and open to doing this type of thing but i’m also painfully straight and the thought of cock up my ass is not one that appeals to it. But i found a solution. The sight of Mistress with a cock attached is a sight i really like to see. So i positioned my laptop in front of it displaying a picture of Mistress wearing Her strap-on and tried again. This helped no end. i relaxed and could slide the dildo fully in and out of my ass with no trouble. In fact, with my eyes closed sliding backwards and forwards on that small dildo i could imagine Mistress talking to it, calling it names; Her little slut, Her bitch. Was it not for my cock being firmly locked in it’s cage i think i might even have got hard. i definitely enjoyed it.
Thank You Mistress for this my fourth assignment. i hope i have completed it to Your satisfaction.
So to combat his little "problem" with regard to the plug slipping out; I've decided he needs a larger plug. He was instructed to order one last night...I'm sure I'll be posting more pictures when it arrives...