CHALLENGE NUMBER 4, plugged at work

So last week I was set anew challenge (it was late last week and been away) and it is a great one! Its not shopping or dressing as such but its still physical. I have to wear my butt plug at work and spend some time wriggling about on it. Not only is this to show that I want to be a sissy but also that I want to have things in my bum, and when I say things what I am really saying is a cock in my bum which makes me a fag (hope that does not offend anyone I just like the word). I do have to wear panties as well and take pictures but it will be very, very exciting I am sure!

This is my plug, its stainless and heavy (medium size) I have some ky jelly to use and must wear it for at least 2 hours.

Here is a video of what I will be doing (this is not mine!)

Inserting a butt plug

SISSY CHALLENGE 3, HOLD-UPS REPORT part 1

On paper this might seem like an easy task and for some of you I am sure it is, probably not a challenge at all. For me it was quite the opposite. First I would like to say that being married and keeping my sissy side a secret can be a real obstacle as well as organising to go out. I want to go out more so that when I want some sissy time it will seem more normal to my wife that I am just going out to see friends, music or whatever.

To complete  the task I would have to go shopping, I work in the town next to the town where I live and I know lots of people in both towns so even shopping can be fraught with danger. I decided that shopping at lunchtime would be easiest and I have visited Primark a few times and knew they had a great lingerie section. I skipped my lunch with my colleagues (told them I had a couple of errands to do) and headed into town, first stop was Primark and I went straight up the stairs and into the fabulous girly underwear section. There were a few ladies browsing the clothes and I walked up the knicker isle and down the tops isle but no tights, stockings or hold-ups to be seen. I ventured all the way into the ladies clothes (saw a few nice items) and into the kids section. Still no hold-ups!

Back down the stairs I went and then noticed that the ground floor had the hosiery section, silly me I missed it!  From a distance I could see the plastic model legs displaying the various stocking material, fish-net, glossy, high denier etc so I knew I had found my section. There were 2 whole racks of tights, stockings, pop socks, shaper and all manner of things, I browsed it all, my heart was beating fast, I felt hot and bothered but I wanted to be a good girl and complete my mission.

I checked the hold-ups section and no white at all, I flicked through all the hanging boxes to make sure, so what next? The natural ones looked just normal, they had fashion ones with 3 rings at the top but I thought the glossy lace topped ones were by far the sexiest. I read the back of the box to check the size, 6 foot tall, size 14, makes me XL, well there were no XL so I went L. I took my purchase up to the desk (I did not have a basket) and within a minute I was handing over my cash. Then I was asked by a nice young man if I want a bag? Now why did I not think of that before, I would need a bag so I accepted a small paper bag with Primark printed on it.

After that excitement I decided to go back up the stairs to the lingerie and take a couple of pictures to show my boyfriend (not sure I am allowed to call him that yet but for the sake of my report I will!) what it was like and where I had been.

Then I was back into the town centre with my gay little Primark bag swinging in my hand. After buying some fuses for the car (boring) I went back to work safe in the knowledge that part one was done and now just needed to wear them and show them.

2nd Sissy Challenge

I was still coming to terms with (and erotically enjoying) my first challenge and then another is thrust upon me. At first it was just a question, sort of hypothetical and we talked around the subject for a while, I guess Mark was working out the boundaries and trying to set the level of my un-ease just enough so that I would still be compelled to accomplish the feat. Well I said I would do my very best to please Mark so I had to accept. Although the second time of asking was more of a command which certainly got my full attention!

So what was the challenge you are all thinking, well its to wear a pair of panties to work and send photographic evidence. Mark gets to choose the panties and I get to choose the day but it has to be within a week.

I sent Mark a selection of pictures of me in panties and after some deliberation he choose a pair. The problem is I have them hidden away in the loft so now need an excuse to extricate them. Putting them on in the morning should be no problem but I will be so conscious of them all day and probably be in a state of excitement as well. Hopefully I can get a picture during a quiet moment even if its a visit to powder my nose.

I am confident I can achieve this so not worried about the consequences which have been vague but I am sure over time all will be revealed! I am trying not to think what the next challenge will be, please post any ideas for Mark as he is an avid reader of my blog (which is why I have to write so much!) maybe it will be a sissy assignment, sort of girly home work, I had to do some years ago which meant posting pictures on certain subjects and writing comments on them and going to other websites and putting myself about for some exposure. Who knows!

These are the panties of choice!

and these are a pair he wants me to buy, they are very cute and sexy!

Janine xx

SISSY ASSIGNMENT 5: Making my own titties

I cant believe its been so long since I last posted but I was set the assignment and it did take me a few weeks to sort out and then I still had the photos to take that I was happy with. So the assignment was to make myself a pair of boobs and get some pic's of me in my various bras, blouses and dresses. I did get them made using rice and an old pair of stockings (note to self I must get some more stockings as running low). Total weight was about 800g but felt fantastic in my favorite bra and moved nice. At first they were a bit large for my C cup but I reduced them so they fitted snug. They are still a little large for one of my tops but mostly ok.

My camera failed on me when I tried to take pics of them the first time and it was quite tricky getting pictures while hiding up in my workshop. Then I had a great day session with lots of chat and cam action and even got a date and invited another CD round who did not turn up so I was relieved as well as dissapointed. I ran out of time for a photo shoot so never got the appropriate pics done. Since then its all work and no play so have not managed to complete the task or receive another one. Now i am on hols and kids off so no dressing fun for a while (boo, hoo)

SISSY ASSIGNMENT 2: POP PRINCESS

Choose 5 pop stars that you would like to be and say why.

This took some research and I enjoyed watching lots of videos on youtube, love to make my own pop video enfemme.

First up is Megan Trainor, she is fun and I want all her outfits! Some are very girly which I adore.

Next is the Queen of pop who has the most sexy lips, I'd love to be the tall version of this girl, she always looks fit and has a great fashion sense. This picture makes me think of a hotel corridor rendezvous.

My third choice (and these are in no particular order) is Taylor Swift who has the most amazing eyes and just about a perfect body. I'd love boobs like hers.

This lady was always bound to star in my list, I sing along to most of her songs especially that one (you know!) Always seems so happy. The beautiful Shania Twain.

and finally the gorgeous Katy Perry, she loves PVC and showing her tits off and with her body who wouldn't? I think she is cute and sexy and love to have a play date with her and her wardrobe.

Thats my selection let me know what you think and feel free to reblog!

SISSY ASSIGNMENT 1: choose 5 skirts

Dear Readers,

My mistress has emailed me to say that she is disappointed with  the lack of time spent dressed and acting like the sissy that she thinks I could be (and I totally agree with her). She understands that my home life makes certain restrictions on my sissy life but also that I don't take or make my opportunities as best I could.

To prove to her my dedication to be a better sissy she is setting me assignments that will work on my inner sissy so that even when not dressed my mind will be occupied with sissy thoughts and thus make sure I am ready when the time comes to take steps towards being my true sissy self.

She would like me to do my best to please her with my responses, post them using all my various accounts (twitter, BP, pinterest, polyvore) and to interact with as many other girls, boys, sissy's, CD's and doms. So in reading this you are actually helping me out! She will be monitoring all communications and will use my responses to tailor her training schedule (as well as my wardrobe!)

Please let me know if you have done anything like this before or would like to be more involved.

Sissy in training,

Janine xx

So on with the first assignment: Choose 5 skirts you like the look of, excite you or think you could wear...comment on your choices.

This is a pin in my pinterst page. Its cute and schoolie and short and I like showing my legs.

I had to have a leather/pvc skirt in my list. Always says super sexy to me and maybe a bit slutty too but you have to get the right size to look this hot.

I wore a skirt like this and it was gorgeous, it feels tight but you can still move and it just contours to your body. Colour is a bit bland but goes with lots of things.

 Its plain, simple and girly. Love the colour and its the right length.

For my last skirt it would have to be satin, this is smart looking, ideal for a secretary who offers a little bit more. Must be so good to feel the suspender clips through the satin, mmmmm.

So how did I do?