Saturday, 28 April 2012

Challenges for the week ahead

In my last blog, I talked about my achievements last week. This blog aims to list the challenges for the week ahead.

The first objective this week is to get into the habit of exercising. I'm never going to have the sissy body I desire (or that anyone else will desire) with my big belly. I'm not hugely overweight, but I do need to lose a couple of stone, so the task is to go for a jog at least 3 times a week. The first attempt was this morning and I managed to walk/run about 2.5 miles with the first 0.8 mile jogging and the rest alternating between walking and jogging. By next weekend, I hope to be able to jog that first whole mile. The weight will not drop off overnight (unfortunately), but I have to keep in mind the body that I want.

The second objective is to follow some more for the sissy training whilst keeping up with everything I've learned so far. Rule number one for this week is no wanking :( This is going to be hard (no pun intended). After making my new purchases yesterday, I spent the evening catching up on all the 'educational' sites. I got so turned on by a LezDom that I just can't help myself at times. I imagine myself being the victim, being stripped of my clothing, my lingerie and being restrained and then used like a piece of meat.

I'm also going to start ex-foliating to get my skin nice and soft and smooth. I've bought some ex-foliating gloves and some lotion.

That should be enough challenges for the week. I'll let you know how it's going.

Friday, 27 April 2012

A review of the week

It's now been about a week since I started my journey so I thought I'd summarise my week and look forward to my next challenges (see next blog). Firstly, my Sissy's Anonymous declaration: It's been a week since I last wore man pants.

My tasks this week were:
- To wear panties for at least an hour a day. This has been passed easily as I've been wearing them 24 hrs a day.
- To buy a flavoured lip balm and apply it like a lipstick. This was bought today and has had its first application.
- To sleep with it all tucked back. This has also been achieved this week. It's also been tucked back whenever it got excited - which is quite a lot given I've been wearing panties.

What else has happened this week?

Well, I bought my first school uniform and some new undies and have added pictures of the uniform to my imagefap page. Here's a preview of the uniform if you want to look further

Wednesday, 25 April 2012


I'm hoping to buy myself a nice little school uniform in a couple of days time (see the pic) so thought I'd prepare myself by shaving my chest. I've never done this before and it definitely feels a bit strange. I was surprised that my little clit was getting hard as I was rubbing lotion into my chest. It's not quite complete yet though so I'll have to catch all those bits I missed tomorrow. I'm hoping that my Bras and Basques I wear wont itch either now, but will have to get back to you on if that's the case next time. I hope to take some pics of me in the uniform for everyone's enjoyment when I have it.

P.S. In a Sissys Anonymous type moment, it has been 5 days since I've worn man pants :)

Monday, 23 April 2012

The first day at work

Today was a bit of a milestone. I wore my panties to work. I've worn them before, but always underneath man pants so no-one would know. I've had this job for 18 yrs and have known some of my colleagues for almost as long. I've always chickened out from only wearing my panties under my trousers before. The trousers are quite thin and I've been worried it would be obvious that I was wearing a g-string under them.

Today I took the plunge and have been wearing panties all day. No-one noticed - or if they did, nothing was said.

I've now not worn man pants since Friday. :)

Sunday, 22 April 2012

A Close Call

Like a good little sissy, I decided to wear a nice pair of panties and a pair of hold-up stockings today underneath my jeans so no-one would know. This was very nearly a big mistake that could have outed me before I am anywhere near ready.

I had to go to the shops which are about a 20-25 minute walk away. I need to lose a few pounds, so rather than drive, I chose to walk. Getting there was fine, I picked up what was needed and started to head home. It was at this point that I realised the hold-ups had started to slip down. They'd never done this before and I've no idea if the slip was caused by the moisturiser I rubbed into my legs after shaving this morning, or by the sweat from the walk. Either way, I was close to walking down the road with stockings appearing from under my trouser leg.

Fortunately, there's a public toilet about half-way home, so I thought I'd pop in and sort the stockings out. With my usual luck, they turned out to be closed on a Sunday. Damn! Then it hit me. I'll pop into the department store on the high street. It was on my way and by this time, the stockings were closer to my knees that my thighs. I managed to get to the department store without them falling further. Disaster! That was closed as well.

What was I going to do? I had about another 10 minute walk and the stockings were on my knees and felt like they wanted to fall further. I continued home, hoping that they wouldn't fall further. If they did, I was screwed. I share a house with a woman and her daughter and if any of the neighbours saw me, it would get back and cause me a world of problems.

Fortunately, they didn't fall any further than my shins and I made it home without my secret getting out. That was a bit close!

Note to self. Next time I want to go for a walk, make sure the stockings are attached to a garter belt :)

Saturday, 21 April 2012

My Goal 1

I also thought I'd include some pictures in my Blog that show my goals, or where I wish to be in the future. To that end, here is a picture of Amy Daly, a gorgeous shemale that I wish I could be. I'll add more photos over time which I also hope will remind me of what I'm aiming for

The next day

Well it's the day after starting the blog and here I am again :) The urge to make a transformation hasn't yet diminished and I'm sitting here in the lingerie I slept in, like a good little sissy.

The next two lessons in sissy school are firstly to taste every orgasms and to sleep with it all tucked back. I've been tasting myself occasionally for a while now, in fact, I did it yesterday whilst reading the exploits of Maid Penny ( The lesson is now to do that every time, so that is what I shall do.

I think I tend to sleep with it all tucked back already when I'm wearing panties to bed. Unfortunately it can prove difficult to keep it there and when I lose the erection over night it moves round to the front again so when I gain size in the morning it's all uncomfortably out in front and needs tucking back again. There's not a lot I can do about that though so will just keep tucking it back.

I've considered getting myself a cock cage in the past to stop the erection from getting too big and forcing it into a good position. As I sleep on my front though, I'm not sure if the cage will dig into me. I've not plucked up the courage to buy one yet either.

First Lesson

Well I started my training today at the sissy school (

Fortunately today's lesson was easy. The first part of the lesson was to wear panties for at least an hour a day. Before starting the lesson, I'd actually changed from the panties I wore under my PJs overnight into a nice white stocking and panty set I'd bought from Ann Summers a few weeks ago. So that was the first part of the lesson sorted without having to do anything.

The second part of the lesson was to buy a flavoured lip balm to use on my lips. Unfortunately, a lack of finances until payday in a week means that wont be possible, but I do have some vaseline I've been using to keep my lips from drying up. That will have to do for now.

I'd also like to give a big hello to  whose blog I encountered first and which inspired me to chart my journey here.

The first post

In this blog I hope to diary my transformation from a middle aged bloke with no sexual experiences to a fully trained sissy slave  for both men and women. I've no idea how successful this will be but hope you'll join me on my journey.

Any training tips, suggestions, advice or any other help would be gratefully received