I had a very interesting day.....with the prospect of a pretty 'real' punishment looming on the near horizon. And it all started with a playful dare between me and my Monster who I have been missing terribly, Ana. I have been pretty good about not bothering her too much at Dental School, since it's serious stuff she's doing.....but we both miss each other and agreed early on that we would try to keep her "junior boss" status somewhat alive via texts.
Yesterday I was "in a mood". No question about it! I was a little lonely and a little bored....and feeling like stirring the pot. And along those lines I had an idea: I would text my Monster when she wasn't busy and suggest a sort of one-sided dare that would fall very much in line with how we all interact here. It was simplicity itself: I dared Ana to text her Mom, my Rosa, sometime before the weekend and tell her that since it was obvious I was missing her being around as my 'other boss', that she would recommend that Rosa give me a spanking 'from Ana' as a playful reminder that she was still a force to be reckoned with even if she wasn't around the house. I told Ana that all I was really looking for was to feel like once the dare was agreed to, I was going to be obligated to go through with whatever she and her Mom decided upon, and that from her end she could decide whatever fate amused her....including a treated lunch to wherever she wanted when she was finally home on break.
Truth be told, with her being away and so absorbed in her studies, I would not have been surprised if she demurred, but......here is a screen shot of her reply:
However, early this morning Ana sent me a text asking to postpone the dare until next weekend because she feels too swamped right now......except that Rosa and I will be away with people that weekend. So we tried to figure something out and she suggested a 2 week postponement:
I fully understood her reason for waiting two weeks, but I also somewhat selfishly wanted something to deal with now.......and naturally something my Ana would not have to spend any real time on. Which led to me making a very simple interim add-on request, so that I could have some sort of action while I was still in the mood I am in. I suggested that since I dared her to request a spanking from Rosa, how would she like to simply dare me to do the same today? Her perk would be to decide what I was going to ask for in terms of seriousness, severity, and number, but other than that she would have nothing to do and could go about her business. The texting request would be all on me.
At first Ana went with a 100 swat playful romp......except she wanted the spanking to be harder than usual....a real roaster.....but for fun! Had she said she wanted the smacks to be average, I would have just gone along with that and the story would be done, but knowing my Rosa I knew that even if I ask for something hard like a punishment, if it's for fun, she will very likely go easy on me. And since I kind of had something 'real' but not overly serious at the ready, I suggested an alternative:
So Ana pretty much dared me to go with that option since it seemed the most likely to get the result she (and I suppose I also ) wanted.
Rosa had already teased me via text this morning calling me a bad boy over something else, and I used that as my opening to agree that I was. She immediately wanted to know what I meant and I went on to confess to the neglected bed-making and wondered if she had noticed. She said she had but didn't mention it, and then I formally asked to be spanked for it with Ana's suggested number of 100 swats. Rosa replied with her typical mix of personal glee and warning, and even included a spanking meme:
And I thought, "well, that's that. I guess I'm going to definitely get a hard spanking I won't be able to back out of" when about 20 minutes later Rosa sent me this:
And with that simple text, and some follow-ups on the nature of the plug I should wear, my day went from from playful dares to clean-up duty! All while knowing that a hard spanking was still coming my way.......and then another, two weeks from now, when Ana texts her Mom her dared request!
For those with a prurient bent, here are a few 'selfies' I took as I went about my chores:
Rosa wanted the plug today to be appropriately challenging rather than fun, and so here is a nice view of the "squid" keeping me motivated while bending to dust the bed frame.
Dusting the bureau.....with an as yet unspanked bottom on display. I wonder what it will look like after a dose of Rosa's paddle?
And vacuuming...... as my penis does its usual "mushroom retreat" under the dominating
influence of the large, nasty squid-plug.