Life: An update

It's been a while since I last posted so thought it was about time I updated everyone. In looking at that post I realised that it's been about 3 weeks since I posted it and in that time, I've worn lingerie nearly all day, every day. There were about 3 or 4 days were I wore man-pants, but apart from that, it's been panties all the way :)

At one point, I thought I was about to be outed by my own carelessness as I found a pair of my panties trying to 'escape'. Firstly they seemed to have fallen out of a drawer and into a box containing a new kitchen appliance owned by my flatmate, which she nearly picked up, and then when they turned up in the dryer after being washed with a load of her washing that I was helping her with. I certainly didn't put them in there, so can only guess that I'd left them lying around as she picked them up and put them in the wash without realising she'd never seen them before! Nothing has been said and she's been acting normally around me, so maybe she doesn't know. But then again, maybe she does and has decided not to say anything in the worry that it would ruin our friendship. I've tried to be a bit more careful since then, but maybe I'm sub-consciously either trying to out myself into the life of a sissy or shame myself into putting those feelings aside. I believe I know why I cross-dress - given I'm a 40 year old virgin, it's not rocket-science. I want to feel sexy and desirable, but being short, extremely shy and ugly, I believe I'll never have a woman that's attracted to me. Maybe the cross-dressing habit would go away if I was to feel that someone was attracted to me, but then again, if that hypothetical woman was really special, maybe it would be something we could enjoy together.

Oh I don't know how I'm feeling at the moment. I feel like I'm trapped at times. There's so much I'd like to try and like to experience when it comes to sex and relationships, but the reality is that it's not going to happen for me and I need to find some way of coming to terms with that.

Some thoughts

So I was thinking yesterday about the somewhat unusual situation I find myself in and what it means to be a man in todays society and how it reflects on me.

Firstly, though I should probably give a bit of background. I share a house with a single mother and we have shared for the last 17 years. Our relationship has never been, or ever will be, anything but platonic, but we are close and have helped each other through some very rough times. Strangely though, we have two very different personalities. She is outgoing, bubbly and loves socialising and I am introverted, shy and avoid groups of people and socialising. Despite these differences  we have formed a partnership over the years and I have helped bring up her daughter (now a teenager), hopefully guiding and teaching her to be able to get all from her life that she can. Neither of them are aware of my cross-dressing habits.

Yesterday, we were having a lazy day. For most of the day, she watched some films and I was sitting in the same room on the computer. She thought I was playing a game, but I was really reading "My Fall to Grace". It's an excellent story by Leeanne over at http://leeannessissymusings.blogspot.com and I would really recommend it to anyone. I've been wearing Lingerie all week, so had some stockings and panties on under my clothes. Once the film had finished, she asked if I would dye her hair for her. So there I am, in lingerie, dying the hair of a very good friend whilst she's checking out a dating site and talking about a bloke she's met who sounds promising. It sounds like something a girl would normally do with her girlfriends :) She has met talked to plenty of men on these sites in her search, but has been unable to find "The One" so far. Most have turned out to be complete idiots who are looking for a fuckbuddy rather than a partner. A number of years ago, she met one and fell in love. Unfortunately, he turned out to be a user who almost destroyed her, literally, with his lies, deceit and downright nastiness.

So what is it that women want in a man? It seems to me that to be a man in today's society you need to treat women as objects. If you're nasty, sleep around, or simply ignore them to go watch football, then you'll get the girl, even if you're not stunningly attractive. If you care and support them, then they don't want to know, unless you look like a Greek God. Don't get me wrong here, I'm not trying to suggest that I want to get together with my housemate, but I've tried the dating sites and had a few nibbles, until I post a picture and then I never hear from them again! I'm not angry, after all I know I'm not Hercules, but I am slightly disappointed in the emphasis that today's society puts on looks. I would never, ever treat someone the way that some men seem to want to treat their girlfriends/lovers. Yet they seem to think that's how it's done and have had relationships that suggest it's working for them.

Having said all that, I'm aware of the irony that this is being said by a person that has pictures of attractive women in his other posts!

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Sorry for being away

Firstly I'd like to thank all those people who tried to contact me whilst I was away. Thank you very much for your messages. I'm sorry I wasn't around to read them.

It's been a while since I've posted, although I'm afraid to say not much has changed in my life. I still have had no luck in love and I'm having the urges to be a sissy again - they're never far away. How I wish for a mistress to take me and control me. Since last weekend, I've been wearing lingerie to work. It's exciting to think/hope that no-one around me has a clue of what I'm wearing or how I'm feeling. In a room full of male engineers though, it's a shame there are no attractive females - mind you, I'd dread to think of the consequences to my little Weiner if there were.


I've found I've been reading a lot of stories on the web that have had a consistent theme - lesbian domination. I can't decide if I wish if I was the dominant in the story or the submissive. Both ideas turn me on, big time. I have an idea for a story I'd like to write based on the fantasies I've been reading about. Unfortunately, real-life and not finding writing easy mean it hasn't made it into 'print' yet.

Anyway, that's enough idle musings for now. I thought I'd leave you with a couple of pictures of my two fantasy sides. In one, I'm the maid undressing my mistress with love and devotion in my eyes. In the other I'm tied and awaiting my mistresses pleasure.

Big kisses to you all

Not going very well

A few days ago, I set myself some targets for this week and they're not going very well. The first failure was my attempt to give up pleasure for a week (if you know what I mean). That target got blown a few hours after I made it - just like a New Years Resolution :) I'm too much of a perve for porn!

The second target was get more exercise. I weighed myself on Monday and found I was 2 lbs lighter than when I last weighed myself a few weeks ago. Unfortunately, I think the run I had on Saturday has taken too much out of me. I tried to go for a run this afternoon, but really didn't get very far at all before I had to give up. Unfortunately I don't think I can blame everything on the fact I had a big bag on my back full with my work gear and coat. Maybe trying to run 3 times a week was too much of an ambition at first.

At this point, I'm feeling pretty down, so I probably need to remind myself of my goal. So here's a pic of one of my favourite girls in the world - Sarina Valentine

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.

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

Preparation

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 :)

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. :)

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 :)

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 (http://pennymaid.blogspot.co.uk/). 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 (http://thesissyschool.blogspot.co.uk).

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 bubblepopmei 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