Teddy cuddles

I’m underdressed today again. This time a white silk teddy with ribbon straps which don’t show through my hoodie.


Except there are no poppers. Every woman will know this pain. Now I too sympathise. No poppers means a trip to the loo involved striping down to your birthday suit to take the teddy off. 

Camisole and knickers tomorrow. 

DTG xxx

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Underdressed at last

After much planning and trying various items of lingerie on under male clothes to see how much of a strap can be seen, I have managed to find something that is easily hidden and today, at work, I’m underdressed.

It’s a fairly simple concept. One that The Recovering Crossdresser gave me in one of her blog entries. Basically put, you wear your femme lingerie under your work clothes but hide it with strategic pieces of male attire. So today for example, ivory silk French knickers, matching cross over swing set ivory silk camisole and black opaque lace top holdups. All hidden under a pair of loose trousers, a t-shirt and a jumper with verticals stripes on it. You would never know what I was wearing under my male clothes unless you either saw it or felt for the spaghetti straps under my jumper.

I have a new person sitting behind me but other than that the desks here are quite sparsely used. Mind you she is gorgeous are loves to talk about clothes, makeup, shoes and going to the gym. I love to listen in sometimes. She’s the type of person I’d love to be caught by.

Perhaps it is just a fantasy of mine? Or do most crossdressers have the same fantasy? Mine has evolved over the years. I used to want to be caught by my favourite female teacher at school, wearing some silky lingerie and for her to fore feminise me before using me to her own end. She would reveal her own sexy lingerie and force me to wear more before forcing me to go down on here then have sex with her. She would use her position of power over me to have me when ever she wanted. That fantasy grew as I did, the teacher was replaced by one of my sisters friends, then by girls I went to university with and now it is co-workers. Specifically the type of co-workers who wear the type of clothes I love to wear myself. Skirts and dresses, heels, black opaque, sheer blouses etc. Whileswt trying not to be too shallow, only the ones I find attractive really. It wouldn’t be a great fantasy otherwise. Do others have the same ideas?

I’m tempted to flash her but then that would open up a can of worms. The world does not work the way it does in my fantasy. She wouldn’t want to whisk me outside for a walk in the woods to see my lingerie, to show me hers, to have quick and dirty sex in the bushes. Life is a lot more complex than that.

In the mean time, I’m underdressed and enjoying the feeling.

Dirty tranny girl xxx

Down

I’ve been feeling pretty down recently, my wife is having a rough time at work, I’ve changed jobs and there have been a few screw ups with my new salary meaning I’ve been paid too little and the tax man has been paid too much. Time seem to be flying by as well and I never seem to have time to myself now. When I worked from home I seemed to have loads of time and I’m starting to have pangs of regret leaving my old job. Perhaps once my pay has been sorted out and the money starts rolling in as it should be, I’ll feel better, but currently, I feel down.
I sometimes turn to dressing as a means of escaping real life. Slip on a dress and heels and suddenly I’m not me anymore, I’m somebody else. Soon however, the realisation that my problems are not left at the wardrobe door catches up with me and I feel silly and angry. I usually end up pulling the dress off and chucking the high heels to the back of the cupboard. Angry at myself for either letting my problems get the better of me or angry that I thought putting a dress on will solve them.

On a positive note, my weight loss is going well. Nearly 20lbs dropped, the weight of a car tyre apparently. This has allowed me to fit back into a lot of clothes, not only in my male wardrobe, but my femme wardrobe as well. I had been thinking of selling a few things on eBay that I’ll never be able to wear again because they are too small (read, I’m too big), however wearing them again feels like it could be a possibility soon. I might end up having to sell the clothes that are too big instead.

I’ve now also booked my waxing appointments for the Christmas and new year fortnight. I’m not getting a whole body wax this time, just everything from the waist down, back and eye brows. The rest will be trimmed right back. This is mainly due to financial constraints but also the pain of a chest wax when your hair is as dark and thick as mine can be unbearable. I fully intend to dress at new year, wig, makeup, dress, lingerie and heels. Mind you I had that intention last year too and my wife and I ended up wearing our silk nightdresses and cuddling up on the sofa watching rubbish tv before retiring up the stairs. We watched some fireworks from the back window and hugged for a while, with the gorgeous silk nightwear we had on, we got quite horny and we ended up making love at the window, our nightdresses pulled up out the way. Even though I want to dress this NYE, I know something will either get in the way or I’ll end up not being bothered. At least I have a fall back in wearing a gorgeous full length silk nightdress again.

I’m in between waxing just now, the hair is growing again slightly but not enough to warrant another wax soon. I do hope it has grown enough in 4 weeks to make it worth spending the money I don’t really have on something that is to make me feel more femme at a time that I might not have the conviction to dress. I did notice at my last couple of waxes that the girl I go to has been using girly talk to get my skin taught. Regulars will know that I get all hair, and I do mean all hair, removed from the waist down. Waxing a flaccid penis is apparently not easy so something you will never ever be told, is that your waxer will have an easier time waxing you if your penis is erect, because the skin becomes taught. Regular readers will know that the girl at the salon I use knows about my dressing but I’ve noticed that when it comes to waxing that area she starts talking about dresses, high heels, makeup, lingerie etc. Of course the the subject gets me aroused as she asks about the lingerie I like to wear, do I prefer hold ups or stockings. How she wears hold ups sometimes under a dress to make herself feel really feminine and sexy. Even now I feel aroused thinking about it. It works for her, I become erect, she gets a easier life waxing me and I get a smoother finish so to speak. A win win all round. I just hope I don’t get too aroused. I once was so aroused that a bead of cum leaked out and rolled down my penis over a girls (gloved) hand once. That was a bit embarrassing.

Hopefully I’ll feel more of myself again soon. Christmas decorations will be up, although sometimes that just masks the sadness some are feeling underneath. I know I’m not depressed or anything, just sad and down in the dumps. I hope it lifts soon.

In the mean time, I may try out a new thing I’ve read about recently over on The Recovering Crossdressers blog. Underdressing at work. Basically it involves wearing your lingerie under your work clothes and hopefully not being caught. Feeling sexy and femme all day. At the most, I only ever wear knickers under my male clothes to work. In a job years ago, I used to wear knickers and hold ups. At my new job I don’t have to wear a shirt and trousers. Jeans and t-shirts are ok so I can fully under dress in hold ups, French knickers and a camisole, or a teddy and cover the strap lines easily with a striped jumper. Easier to do now we are into winter here in the U.K.

Dirty tranny girl xxx

Caught again…

The weather has taken a turn in recent days, the frosts have arrived and my home town is very cold. The big coats are out of the wardrobe and scarves and gloves are out in force.
One thing in the arsenal of a cross dresser that I love to wear in the winter months is a camisole or indeed a teddy. Especially silk ones, so sensual to wear and also very comfortable and warm! This weekend was the first time this season the camisoles were out. On Sunday I wore an ivory silk set from M&S, a swing camisole and matching French knickers. The swing part refers to the straps of the camisole which come together at the back, through a small clasp and back over the shoulders, giving a cross over effect without the straps actually crossing over.

So wondering around town I was nice and cosy, enjoying the feeling of the silk against my skin, knowing that the lingerie I was wearing was probably sexier than most of the women walking past me. I was warm and felt really sexy.

We decided to go for dinner in a shopping mall which was on the way home and ended up in Nando’s. It was round about now that it hit me that i was wearing just a t shirt over my camisole and the straps and adjustment clasps would be quite visible when my coat came off. I made sure to be sitting in a booth with a high back so nobody would see the straps through my t shirt and it seemed to work ok. We enjoyed a lovely dinner and we’re about half way through when I noticed one of the girls in the booth next to us looking quizzically at what I thought was my crotch area. Confused, I looked down to see the ivory silk of my camisole was hanging lower that my t shirt and she was close enough to see it was silk and close enough no doubt to see the metal “label” sewn onto the hem of the camisole. I was rumbled, it seemed to dawn on her what I was wearing under my t shirt.

I was slightly surprised then that given her age, she simply smiled at me and got on with her chat with her pal. I was expecting giggles and hushed talk. I was expecting her friend to be turning to look at the cross dresser next to them. I was expecting a scene. But no. Nothing happened. She looked over occasionally and I must admit it was a thrill to have her see the bottom of the camisole peeking out. Eventually they got up to leave and she smiled again as I pulled my t shirt down to cover my cami.

We left and headed home. I slept well that night, keeping my knickers and camisole on, for warmth. Honest 😉

Dirty Tranny Girl xxx

Work

I recently started working in an office again which is a bit of a drag after working from home for so many years.

As a cross dresser, working from home offers a lot of opportunity to dress up. I’d get up in the morning, shower, shave and dress for the office. It may be a nice dress, or skirt and blouse combination. Sometimes I’d simply sit at my desk in my nightdress or teddy.

I seem to recall doing this a lot, but to be honest I don’t think it happened very often at all. I always thought I’d have more time to dress during the day, but sometimes, just sometimes, it gets in the way and I had to dress in drab.

Working in an office though has many advantages, esp with our graduate programme which is full of young women who seem to think the office is a place to parade themselves, dressing in as little as possible. I’ve seen girls on a night out wearing more. Short skirts, dresses, lots of opaque tights, high heels, silks tops, satin blouses, chiffon dresses, you name it… For me, paradise.

I can’t help but fantasise about some of these girls, how I would take them over their desk, their dress round their waist, kickers round their ankles… Hmmmmmm how sexy.

In reality, none of them would look at me twice. Some dirty old man perving at them. Which brings me to one of the very few cons of working from home for me. I was too close to my kitchen. Since 2010 I’ve put on 34lbs and now it is having an effect on my life. To combat it I’ve joined a slimming class and I’m doing quite well. I’ve already lost 14lbs and my own clothes are starting to fit better. The next step is to make sure my dresses and skirts fit me better. I know I’ll never have the figure these girls in the office have but I can dream. I’d love to just faint into the clothes that I see in the shops, most of which seems to stop at a size 16. I saw a gorgeous black lace playsuit recently in Quizz but their 16 says a 33″ waist! What? That’s more like a size 12!

I should stop thinking about these things though. They just get me down. After proof reading this, I feel down on myself and in need of cheering up. That usually meant a chocolate bar which completed the vicious circle, but today, it’s an apple.

I’m not really sure where this blog post was meant to go or the point of it other than to have a blether.

Dirty Tranny Girl xxx

Neighbours…

About 10 years ago, I used to live alone, in my 3 bed house. I had my own garden front and back and life was pretty sweet. The only thing missing was an understanding woman in my life who would embrace my dressing and perhaps even help me.

In the mean time, I had a very good neighbour who lived through the wall from me, next door. She was married, although I don’t think it was a happy marriage. He was away most of the time working abroad and she didn’t seem to have any friends. None who I saw anyway.

She was a really lovely person and quite attractive too, although the big baggy jumpers and horrible jeans she wore tended to hide that fact. I think she was attracted to me as well and when I came home from work I usually found her in the front garden on nice days, mowing the lawn or cleaning her car. She would make a bee line and we would chat for ages.

In hind sight I wish I’d invited her over a few times for dinner etc, just for the company when her husband was away.

When he was home, she seemed to make a lot of noise, esp. when she was having sex. her moans and screams would penetrate my walls and turn me on. I’ve no idea if that was her intention. I used to do that same on the rare occasion I’d bring home a girl.

I eventually met somebody and we bought a house together. I was moving out soon when she caught me partially dressed, just hold ups, high heels and a camisole. She was mowing the lawn and I was in my living room. She looked in the window, mouth ajar as I lay on my sofa watching some light porn. one of the 900 channels on Sky TV. It was not a deliberate act, in fact I thought she was out.

I made out that I didn’t see me and she pretended she didn’t see me. I was hard as a rock, touching my self and slowly masturbating in front of her. She continued mowing the law, barley taking her eyes off me. I started to move faster, sitting more upright and moaning in pleasure. She had managed to stop near the window to empty the lawn mower. I was rubbing the silk of my camisole on my chest as I pumped away at my rock hard cock. Getting ready to cum I sat up right and grabbed a few tissues and held them ready to catch my load. As i came I moaned out very loudly and looked up at her deliberately. She was staring back with a sly grin on her face as she saw my hot spunk, spurt from my cock.

I hurried away to clean up and cover up and she, I presume went back to mowing the lawn.

Later than night I heard her moans and screams of pleasure through the wall as she shouted “I love to masturbate”. I guess that was her way of telling me she enjoyed the show.

I soon moved out and regret never speaking to her about that day.

Dirty Tranny Girl xxx

 

Holiday

I love a good holiday.

I especially love watching the girls in their bikinis with pants that barely fit, with boobs heaving out of the top and every girl parading it like they are in a fashion show.

I love to look, but I’d never dare to wear. It just wouldn’t suit me or fit me.

A bikini is the one item of female attire I will never try on when dressing.

Dirty Tranny Girl xxx

Fuel Crisis

So as mentioned before, I planned on heading out on Friday night for a drive dressed as Becky.

After dropping off my other half friend at 2am, we got ready head to my usual secluded country lane, but then disaster. My low fuel warning light came on. I knew I would not have enough fuel to get to where I wanted to go and back again. And of course, there are no 24 hour garages to fill up at where I live.

So whats a girl to do?!

Well, I headed to a business park where I used to work which was on the way home from where the other halfs freind lives.

I slipped my t-shirt off and put on my dress which was an over the head affair, no zips or anything like that. I put on my lace beloro and sorted my self out. All I had to do was take off my trainers, jeans and put on my high heels. Simple and quick enough to do. I had parked the car in an area next to a car park so it would not look out of place and being familiar with the area, I knew which businesses had CCTV and which would have staff on that night. I avoided both and went for a lovely walk round the area. My heels were clicking and my dress was swishing and it was lovely.

Of course I was rock hard by now and my other half felt me though my dress. We kissed gently and she slowly lifted my dress and underskirt. Taking me in hand and stroking me. I was getting rather excited and she bent in front of me to take me in her mouth, sucking me gently. It was so sensual and lovely that it didn’t take long for me to climax and cum in her mouth. She swallowed the lot.

We headed home, undressed and chatted rubish for a while before falling asleep for hours!

Dirty Tranny Girl xxx

After party outing

A good friend of my other half is coming over this weekend for a boozy evening and catchup before holiday season kicks off. She is quite young, very pretty, if a little boring to talk to. She tends to wear skinny jeans and horrid t-shirts along with gastley flat sandals. She looks lovely in a dress or skirt and top but that is a rare event.

I will of course offer to take her home in the car at the end of the night but this is usually to allow me to go for a drive dressed as Becky afterwards. She normally goes home at 2am-ish.

This time I intend to have my dress on under my jacket and joggies and some makeup ready to go. Once I’ve dropped her off, me and the other half will head to a local car park, get my makeup on, change to my dressy jacket and go for a walk. During my walk I’ll change shoes and slip on my high heels. As I continue along the road I’ll slip out of my joggies to reveal my dress.

Soon after its back to the car, drive to a country lane, headlights on and head out infront of the car. I don’t wear knickers on these drives so hopefully just lift my dress and underskirt before releaving my hard cock of its hot sticky cum.

Maybe one day I’ll be joined by somebody else? I’d love to suck her cock til she cums in my mouth.

Becky Boo xxx

Music to my lips

I was always infatuated with older women when I was going through puberty. The girls in my year at school didn’t really do anything for me. There were two or three who liked to wear underskirts under their school skirts which were visible through the kick flap at the back of the skirt and those girls always intrigued me, but I never really fancied them.

Some of my teachers on the other hand were stunning.

One in particular who was somebody you would describe as “mumsy” was my favourite. She was very kind and gentle. Always wore a dress or skirt and top with high heels. At Christmas she always wore gorgeous long dresses which were quite thin so she usually wore an underskirt with them. I recall one day in class she wore an orange flowery dress, matchin heels and he underskirt or “slip” as some call them just showed a tiny bit below the hem of her dress. The white lace was an instant attraction to me and when she bent over you could see the satin of the underskirt against the dress.

I was hard for almost all of that lesson. It was lunch time when it ended and we all trooped back to the main building of the school which was being renovated and the class room I had been in was a 5 min walk from the school building.

I had “accidently” left a pen behind and had to go back for it. The teacher was still in the class and was surprised to see me back. I had of course planned this next bit.

I explained I’d left my pen and she helped me find it. All the time I was watching her underskirt and the way her dress swished as she moved. Once found I put it in my school bag and pulled out a christmas card for her which she thanked me for.

I then said “oh and a very merry Christmas” as I pulled out some mistletoe. She giggle as I held it up and she stepped closer to me. I recall the event in slow motion as if it were earlier today. The smell of her perfume, the smell of her hair, the swish of her dress. I rested my hand on her waist working it round to the small of her back. Gently pulling her in as she moved closer. I kiseed her on the lips with a slightly open mouth and it lingered as my cock grew rigid against her thigh. I so wanted to kiss her again and slip my toungue onto her mouth but I was so nervous and she was afterall my treacher. Insread she gave me a little hug and a kiss on the nose and forehead. There is no way she could not have felt my cock straining against her. I wanted her so much.

“Merry Christmas” she said as we parted and the moment was over. I headed to lunch. It was the source material for many boyhood pleasure sessions I can tell you.

Dirty tranny girl xxx