Chasing Me Chasing You

An uncollared submissive struggling through depression, motherhood, and the constant craving of her next orgasm.

It Always Works Out in the End

The package had arrived two days ago but I was instructed not to open it until I had time to complete the task. So there it sat, tempting me until today when I finally found sufficient time alone to open it, examine the contents and follow the instructions that he had included in the package. I knew roughly what to expect but not the specifics of the challenge.

You see, he’s finally arranged to come and visit me. We’ve been talking for a couple of years now but we just haven’t ever found the time to be together in the same place. We have missed each other by a few hundred miles or a couple of hours on a few occasions which has been frustrating to say the least. He will be finally arriving in a little over two weeks and be staying for around three days. I can’t wait, we have so much to catch up on and so much sex to have to make up for the times we haven’t been together.

Over the years we’ve exchanged a lot intimate thoughts and fantasies, the occasional video, stories and even collaborated on writing erotica. I know that he has one unfilled sexual desire and that is to have anal sex. Not judging, but his partner has steadfastly refused to even consider trying it which has caused him a lot of angst and frustration over the years I have known him. My recent attempts at anal sex have been less than stellar as well due to my lack of preparation, a fact he is aware of so I have a fair idea what the focus of the task will be and what the likely  contents of the package.

Opening the box I find an envelope which I assume contains the instructions, a tube of Wet Platinum Premium Lube, a small anal vibrator, a medium size butt plug and a longish rectangular box. I’m very curious about what’s in the box so I open it up to find a very life like silicon dildo which can have a vibrator inserted into the base if desired. The resemblance to a real cock is amazing. Even the colur is close to pale pink skin. There is also a suction mount that I assume helps secure the dildo to a wall or floor.

So now I have the contents spread out on the bed I decide it’s time to open the envelope and see what he wants me to do with all of this. Tearing open the envelope I find a couple of A4 pages of typed instruction.

The first instruction is that he wants me to video the session and send him a copy once I’m done. He has been specific around the camera angle he wants so that he can see my ass being penetrated close up. He insists that I do a short test video to make sure the positioning is as he has asked.

It turns out that the life like cock dildo is in fact ‘a clone a willy’ silicon replica of his cock. He says that once I’m comfortable taking his cock up my ass he will know that we are both ready for the real thing. How amazing is that. Only he would have been that thoughtful.

The rest of the instructions are more about ensuring I’m clean and that I warm up properly so that I have the best chance of taking his cock in my ass first time. Looking at his cock I think that this will be doable. He has often said that he has the perfect cock for anal sex, long and thin. I think the girth his  fine, but I’ve seen some that are bigger. I think I’m in agreement to his assessment. Time will tell.

Okay, I’ve got myself prepared. A little clean out and lots of lube liberally applied. Test video done.

Now let’s get into position and get on with taking his cock in my ass.. He wants me positioned on my knees so that I can place my ass back onto the cock and allow me to rock back and forth.

I am finally start the recording and get on with it. I’m already wet with anticipation. Maybe I’ll get him to fuck my pussy after the anal preparation. He never said I couldn’t.

Using my fingers first. I reach back and rub my finger around my anus and slowly slip the tip of my finger inside my ass. Moving in in and out I slowly increase the depth of penetration. Once I’m feeling aroused and relaxed I next add a second, then a third finger. I’m may have also missed my ass a few times and ended up fingering my pussy. Oops.

After a few minutes I feel I’m ready to use the butt plug to further open up my ass. His instructions said that I have  to continue with inserting and removing the plug until my ass gapes and remains open for two seconds before closing. Following his instructions I slowly insert the plug. I know from a previous video exchange that he loves seeing the plug slowly disappearing up my ass. So to give him some added viewing pleasure I make sure I do this a few times. I also push back trying to expel the plug creating a bulge which looks amazing and hot. After about five minutes the plug has done its job and my ass is staying open. I do enjoy sticking my fingers into my open ass. Such an anal slut.

I’m ready for the last part of the task. Taking his cock I secure it to the floor using the suction cup he supplied. Next I grab the lube and apply a liberal amount to his cock  and slowly jack the cock smearing the lube over its length. Another squirt and I lube up my ass. Ok, so here goes. Squatting down as directed I slowly lower my ass towards the tip of his cock. I feel it start to push against my anal opening. With a bit more pressure I feel the head slip past my sphincter and into my ass. Pausing to get used to the cock in my ass, I take a few deep breathes. I pull back off his cock and slowly impale myself on his cock again. This time a little deeper. The next time I pull his cock out I leave the head inside. The next down stroke takes him deeper into my ass. It’s a little uncomfortable but I think I can do this.

Moving slowly and deliberately I take my time getting used to his cock in my ass. As my excitement increases, so does the speed of my movements,  lowering myself further onto his cock. With one last push I manage to bury his cock balls deep in my ass. There is some slight pain and some uncomfortable twinges, but it’s not too bad. I’ll do better next time, and the time after that. I then raise myself up and off his cock and turn off the video. That completes his challenge for the day. Now I’ve just got to clean up and send him the video for him to review my progress. I hope he is pleased.

I love that he sent me his cock to practice on. I know that when he gets here I’ll be ready. Hmmm, maybe I need to practice my deep throating skills as well.

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