Games and 'Games'.

An excellent game of Scrabble with Miss last night.  She came very close to another win but thanks to an 81pointer from me with the third last lay of tiles i managed to hold Her off.  It's a great bonding time for us when we play Scrabble and i do enjoy it immensely. 

 

 

 

As the game concluded i cheekily asked Miss if She required me for anything else and was even more cheeky, after hearing Her say 'no', to ask if She might not mind helping me to achieve a sissy cum?  Miss knows that She could simply order me to satisfy myself but it is so much more intimate and meaningful with Her there.  It's all 3 parts of the jigsaw i wrote about in an earlier blog post.  Miss decided that She would retire upstairs, slip into a pretty gown and then 'help me' play.

 

She looked so gorgeous when She came down wearing a dark blue vintage full length Olga gown.  i was also dressed in an Olga, mine being red.  Under that i had on a pretty set of red lace bra and panties with black lace topped hold up stockings.  i love the way my Olgas allow the lace of my bra cups with forms in to thrust forward and display themselves.  It really does make me feel oh so feminine and girly.  As Miss sat down next to me She casually tossed a condom onto my lap 'see if you can get your sissy clit hard enough for that and then cum into it'.

 

When She's good....She's very very good.......

 

 

What followed however was a quite surreal experience where somehow again the subject of the Ashley Maddison site came up.  'Have you found any lovers for me sissy?' asked Miss.  In the context that we were being intimate this sort of comment would, in the past, be part of the mind games and teasing Miss employs to bring me to orgasm.  i feel things are different now and i sensed Miss actually meant it.  Or at least She meant She wanted to know if i thought anybody of the replies i had so far might be of interest to Her - in my opinion. 

 

As i sheathed my tiny cock with the rubber of the condom and with Miss delightfully mocking it's (lack of) size we then had a very interesting conversation about AM and somehow we kept dipping back and forth between how an actual date for Miss might end up playing out.  i was certainly not expecting this and yes, my sissy cock was certainly responding but my mind was trying to work out what it was Miss was working towards.

 

 

 

We talked about a typical first date...a meeting only....very likely to be no sex and then Miss saying 'on a second date there definitely would be sex!'  We talked about me buying new clothes and lingerie for Miss 'I might even let you dress me sissy'.  We talked about transport, 'I can use taxis for that sissy'.  We talked about safety.  'Stop trying to control it all sissy!'.  i hope Miss realises that i'm not.  Miss joked about what if Her lover had a small cock or even wore panties...oh the irony!  This very easy, casual conversation was pinging back and forth between us and i think it helped us imagine what the reality could be like.

 

What i was glad of however was the chance to let Miss know that any date She does choose to go on is not about me...it's all about Her.  i told Her how i would make sure that everything would be taken care of domestically, that She'd have only one thing to think about and that being having a good time, in relaxation and with no worries.  It would be all about Her enjoyment, the excitement, the thrill, the attention She'd get from a Real Man...the wining....the dining, the flirting. 

 

 

 

Miss does seem to think Her enjoying Real Men is weighted towards my excitement and my pleasure.  i can't deny that i will get enjoyment as well but Hers is the main factor and the priority. i assured Her that i would not be demanding to know everything, that i would not be expecting to be there, that i would not be expecting recordings or even to be revealed to a lover as the cuckold sissy in Her life.  All of that would be up to Her to decide if She chose to. 'Well, I might make some secret recordings for you sissy' She said.  A lovely thought but not essential Miss.   

 

 

(An aspiration not an expectation)

 

i am now of the belief that Miss won't actually create 'Her own profile' on AM but instead may be much more favourable to me continuing 'the experiment' and 'looking out' for potential playmates.  i am happy to do that for Her. After all, it can be quite a time consuming activity - and i certainly have the time!  i think Miss is subtly trying to let me know that, for now, this is the way She prefers it to develop. This is still 'the process' stage.

 

So my plan is to keep 'my profile' up there and visit it daily.  i will 'keep' the contacts of Men who are both good looking and articulate and who come across well.  There are a couple of those already.  i'll then find a way to let Miss know that they might be worth Her looking at. 

 

 

 

How do i further encourage Miss from here?  i simply don't.  i can only try to imagine what it is like for Her now.  Perhaps if i were in Her place, i'd try to split this down into two further parts. The first being the experience of the date and the second being the experience of the potential lover on that date.  At this moment in time i think that the actual 'experience' of going on a date and all the things that entails from nerves, to wanting to look good, to feeling good and perhaps many more are what i would be thinking most about.  How would it make me feel??  x