Teddy bears picnic

With the last bank holiday of the year before Christmas approaching, I’m planning, and fantasising about a walk in the nearby woods dressed up.

I’m not sure what to wear but the fantasy involves my knickers round my ankles and a strangers cock pounding me from behind. His hot cum dripping down my legs and my chin.

Soon followed by my own hot cum spurting all over my dress and stockings.

It gets me hard just thinking about it. I know I’d never arrange anything but I used to love looking through the personals on Craigslist. Alas that has now been removed and I’m left with just my dirty thoughts of being fucked hard, in the woods.

DTG xxx


Tonight Mathew…

I’ll be a slut.

I’ll be heading out tonight in what can only be described as a micro mini belt. Not even a skirt. It doesn’t cover my bum and it does not cover the bulge in my silk knickers. Maybe it is supposed to be worn over leggings, I don’t know…

I’ll add shear black holdups, black silk diamontè shoes, and a white satin cami with diamontè encrusted neck line.

Auburn wig and lots and lots of makeup. Nothing but the best slut look for me.

I’ll then pleasure myself in public (where I can’t bee seen or arrested for public indecency)

DTG xxx

The dreaded purge

I know what you’re thinking, but no. I’m not about to throw out a lot of good clothes. I am however about to sell a ton on clothes on eBay. There are so many lovely clothes I have but never time to wear them. And I could do with the money!

I started to clear out my wardrobes and wasn’t just of clothes. Shoes and general junk were also targeted. So far 5 bin bags of rubbish have been cleared. It’s amazing how much just gets hoarded. Boxes of useless cables, an empty guitar gig bag with a rusted shut buckle, you get the idea.

The thing I dread looking at now are my dresses. My femme wardrobe is split in two. One side has a rail high enough for maxi dresses etc to hang and the other side has two tails where tops and skirts sit above my male overflow wardrobe. That too needs cleared out.

I dread looking because I know none of the dresses will fit me currently. An all inclusive holiday helped me to gain 6lbs. So what I really needed to do it to get exercising and cut out lol that rubbish I’m eating. Easier said than done.

In the room is some gym equipment. Cross trainer, spin bike etc. I’m going to hang my favourite dresses up where I can see them to give me motivation to fit back into them again. Just a glance at the silk or satin should be enough to get me going.

As for shoes though, if they don’t fit, they don’t fit. I’m not about to cut my feet short to get into them. Some are even broken. Time for them to go.

DTG xxx

Brush with tar

To the majority of people I know, men who dress in women’s clothes are all the same. Weirdos. Perverts. Nutters. Odd. Funny or to be laughed at.

Their ignorance can not comprehend the differences between transsexual people, transvestites, drag queens, etc. To understand would probably destroy their perception of the weirdos in wigs, so there is generally a push back against being educated. I see this everyday at work when messages of “inclusion” are emailed out. They don’t want their fragile world of black and white broken.

This frustrates me somewhat but has got me questioning my own existence which is even worse!

I’m not transsexual but I often fantasise about taking anti-androgens to become less masculine. I lovingly touch my dresses and skirts as they hang in the wardrobe. I often slip into my high heels and wonder round the house to enjoy the feeling of them. But recent office talk has hit it home harder than usual that I will never be close to being female. I’ll never actually pull off the look some of the women I admire can put on. I have no option but to accept this. I can’t even emulate the looks I want anymore.

This is going to go one of three ways I think. Either I carry on as before and battle to accept what I am, I do something about it and try to get to the point where I can pull off a feminine look again, or I throw a hissy fit and dump the whole concept of what I am and what I would love to achieve. I deliberately chose the words “what I am” because right night I have a bit of an identity crisis.

I’ve managed to track back to where this shift started to occur. Right now I don’t have anyone I can talk to about my inner self. I used to have a few female friends who were sympathetic to what I was going through. One in particular used to give me makeup tips and we would chat for hours about dresses, makeup, shoes and all things girly. For me my crossdressing started to shift away from pure sexual expression and satisfaction when I had these friends. Sadly life gets in the way and I no longer have that girly release. I can’t have those discussions with my other half although we still go shopping for clothes and makeup together, it is hard to explain that I want to slip into a skirt and fluffy jumper on a cold evening and be my girly side. She still expects me to be the man. Even though a lot of the time I don’t.

So I find my self at a three way crossing. What to do. I don’t have any face to face female friends to myself any more and finding some would be hard. Talking to anonymous women online is helpful but not what I want.

If only could find a lamp and get three wishes…

DTG xxx


It’s not often these days I get to work from home. Today however I’m in my home office wearing a blue silk teddy, nude holdups, a very short skirt, black silk high heels and a white silk blouse. Very secretarial.

Love it. Its difficult to keep my hands off myself.

I may have to use my anal dildo later.

DTG xxx

Last day walks

Since changing my job I’ve not had a chance to “under dress”. I’m back to shirts and trousers where under dressing would be too obvious and visible. Of course I still wear knickers and hold ups under trousers but camisoles or teddy’s are out sadly.

In my old job I under dressed almost every day. It was great. Silk teddy’s, camisole sets, hold ups, thongs, it was marvellous. I sat near the back corner of a huge open plan office that was shedding staff daily. By the time I was leaving (my own decision) there were 4 people left in my area. One of whom was a test specialist. She was gorgeous. Tall blonde, early 30s and always dressed impeccably. At first I didn’t like her. She was arrogant and pushy, but as most of her team left and she was pretty much left to do everything, she started chatting to me. We started to have a good laugh and would go for coffees and we would even flirt occasionally. Neither of us were single but that didn’t seem to matter.

The warmer weather rolled in she of course dressed appropriately. I admired her dress sense. Gazing at her when I thought she wasn’t looking, a hint of stockings or hold ups through her spring midi length dresses? I was caught quite a few times looking, but I bet she never dreamed I was wearing sexy silk lingerie to rival her own.

The campus was massive and there was a mile long woodland patch that went round the buildings. On occasion after lunch the two of us would go for a wonder. The flirting was getting crazy. She once said that two people could easily have a quickie in the woods and never be seen or caught. Sex in the woods up against a tree or even with her leg wrapped round somebody’s head with her knickers round her ankles. I just laughed, stupidly, wishing I had flirted back saying we should try it and see if you can do it without being seen.

My last week in the office rolled round and we were the last two left in the bank of desks. She had now also handed in her notice. So we basically talked and told stories which became rather intimate. Flirted lots and joked about how bad a place to work the office was. She was wearing a white flower pattern dress one day with buttons down the front and she happened to let it sit open as she crossed her legs one fateful morning. I could clearly see the lace top of her nude hold ups. She was also clearly wearing a short basque like bra which was visible though her dress, being as it was unbuttoned to her cleavage.

My cock was stirring all day. We went for a coffee at about 11 and she was touching my hand,squeezing my leg and becoming quite hands on. I was hesitant at first but soon relaxed in to her holding my hand. At about 2pm-ish. She declared she was bored and asked if I wanted to go for a walk round the campus. The sun was out and nobody was about. We walked talking and giggling to the woodland path.

She turned to me and said how wonderful the past few weeks had been, how she had enjoyed my company and how she would miss our flirtatious chats. I told her how I’d miss them too. She blushed and stammered how if she didn’t do this now, she never would, and kissed me. I was taken a back but gently kissed her back. Our kiss evolved into a deep embrace, our tongues exploring each other. I held her tight and her hands were all over my back. She stepped back, took my hand and led me deeper into the woods. She stopped and turned toward me, slowly unbuttoning her dress. I stood in awe as she exposed her lingerie and hold ups. I was desperate for this, but I was under dressed. I couldn’t possibly get away with a quickie with her and for her not to see my lingerie.

she pulled me closer and my hands caressed her soft skin. She gently pushed my hand towards her panties. I pulled them down a bit and she gasped as my fingers brushed past her soft mound. As we kissed more, my finger traced her line before I gently opened her and pressed a finger to her clit. She moaned out in pleasure as I slowly circled her clit and slid first one, then two fingers easily inside her. I finger fucked her as I rubbed her clit with my thumb. I’m going to cum too soon she gasped as she stopped me. She took off her panties and told me to lick. I was in front of her in a flash, her leg wrapped round my neck as I continued to finger her and to lick her clit. It didn’t take long at all for her to gasp and moan as her orgasm shot through her body. She held my head and pushed her wet pussy against my face as the last of her orgasm ran through her.

We’d better get back I stammered backing away. Now wasn’t the time to be revealing my white silk teddy and white holdups under my male attire.

I don’t think so, she said pulling me in and kissing me. She rubbed the front of my trousers feeling my hard cock. We need to take care of this.

I stuttered and stammered about the need to go back to my desk as she pulled at my hoody and tried to unzip it. I looked down to see a sliver of white lace getting revealed and quickly pulled the zip back up.

Do you just not want me to see your lingerie she asked. I was scrambling in my head for an excuse or even a denial. None came to mind. It ok she said. I know you wear it. I noticed a while ago that wear hold ups occasionally. I’ve seen the lace top through your trousers when you sit down. I’ve seen the strap marks when you hunch over your desk and I’ve felt the strap under your hoody of whatever you have on today. I find it really sexy.

I let her unzip my hoody. She undid my trousers letting them fall to the ground. I was stood in white hold ups and my white silk teddy. She pulled me in and kissed me again. I could have cum there and then.

She quickly sprung my cock from its silk prison and went down on me. Licking and sucking me while maintaining eye contact. It was one of if not the best blow job id ever had. I slipped a condom on and she put one leg up on a tree stump as I slid inside her. It really didn’t last long and I grunted and moaned as I came inside her.

We got cleaned up and she offered a baby wipe to mop up the last of the cum dribbling from me. She put her knickers on and buttoned up her dress as I pulled up my trousers and zipped my hoodie back up.

We continued our walk and headed back to the office.

My last day arrived and we said our goodbyes. We didn’t hook up on Facebook or twitter. We don’t see each other at all now or keep contact. It was a great end to a piss poor job.

DTG xxx

Wax on wax off

Freshly waxed again. I think however that my beautician is taking a strange liking to me. Not something I really want to encourage though. I was getting my eyebrows waxed and she kept stroking my hair which is quite short and was certainly not in the way. If it happens again I’ll sweep my hair and say “is my hair ok? Is there wax in it?”

I have a few plans for next weekend now. I’ll be selecting a nice outfit for a wee drive. I want to wear a silk teddy, hold ups and a dress. Not sure what shoes yet.

Looking forward to it.

DTG xxx

New Year, New Me…. sure.

I’d like to say that in the new year I’ll be a new person, trying to put behind me all the bad bits and concentrating on the goodness.

I know that won’t happen, so I won’t even pretend.

I want something from this year, life is rushing away from me, when I was young,  had it all before me but now it seems I’m heading straight into a life of responsibility and planning. I want the spontaneity back. I was to get out dressed again. Go to a club as my femme self. Lose weight to fit back into my sexy get up again.

2018 is the year it’s going to happen.

If I have to live a life of planning and such, I’m planning on getting fit, sorting my health, my wealth and love my life as a trans-person.

I’ve dabbled in the thought of anti-androgens to block my hormones in the hope that it may stop me bring too masculine, but I think instead I’ll speak to a counselor about it and hopefully live more of a life as a woman.

Happy New Year to us all!

DTG xxx



Most of this story is true, some of it isn’t. I’ll let you imagine which is which. 
I don’t often get to spend a day on my own, my other half is a teacher so is always off, or so it seems. It means a day off for me to spend by myself is a rarity.

The last bank holiday before Christmas was fast approaching and it was one of those rare events when I would have the day to myself. The schools were back and most places would be quite quiet. I decided to plan a few activities while at dressed up. I wanted to head to the woods nearby wearing a dress and lingerie under my male clothes, strip down to my dress and put on my heels. I would wonder about a bit then pleasure myself before heading home. 

Things didn’t quite work that way.

I was freshly waxed and excited for my adventure. Monday morning came and I was up early, a good scrub in the shower and a very close shave, then time to get dressed. I carefully slipped into my nude hold ups, making sure that the lace tops were even and in place. Next was a black silk thong, a very short black satin half slip and my green satin dress. I figured that wearing green would help hide me in the forest. I applied as much makeup as I could get away with in public, hoping to add more when I got to the woods. I packed my wig in my rucksack and slipped my heels in there too. I carefully put my male clothes on over my dress and headed out. It was still before 9am but I didn’t see anyone during the short walk to my destination. I spotted 1 dog walker in the woods but he wouldn’t be anywhere near the secluded area I was going to. I stumbled through the overgrown woods following an unused path until I got to the place I wanted. It was secluded and protected by trees on all sides with a solid grounding. I slowly checked out the whole area as best as I could before undressing out of my male clothes and putting on my heels. I put on my lipgloss and fitted my wig. I was so hard by now that I had to touch my cock through the thin satin of my dress. My hands wandered all over my body and under my dress. I was soon masturbating myself, my dress around my waist, my knickers round my knees and my slip pulled up. I was so engrossed in my pleasure that the noise I was making no longer bothered me. I didn’t care who saw, but knowing full well nobody was anywhere near. 

That was until I heard “hello there!” behind me. 

I spun round, pulling my dress down and trying to pull my thong up. It was the dog walker. ” no need to do that honey” he said. I sorted myself quickly and looked for an escape route. “Can I help you?” he said, slowly unzipping his jeans. The look of confusion on my face must have been clear for him to see. “Maybe we can have some fun?” He said. 

Curiosity had gotten the better of me and I let him approach. ” you are so sexy” he said touching the front of my dress. “Thank you” I replied. “I’m Becky”. 


I helped him pull his jeans down a bit and he eased his cock out of his underwear. He was wearing a par of black lace knickers and a big grin on his face. I smiled and he guided my hand to it. He hardened quickly and I slowly masturbated him. I could tell he wanted to kiss me but I wasn’t sure so I avoided that and instead concentrated on his cock. It was much bigger than mine. “I want you to suck me” he said and I willingly crouched down in front of him. I took as much of his hot meat in my mouth as I could. Sucking on him and licking him. He he groaned in pleasure and I felt his cock pulse in my mouth. I made a lot of noise, moaning as he fucked my mouth. His salty pre-cum leaking from the tip of his huge manhood. “I want you” he murmured pulling his very wet cock from my mouth. My pink lipgloss down his shaft. He lifted my dress and pulled my thong down. He moved my slip up and turned me around. I could feel him proding my entrance, I was willing him inside me. “I need lube”. He seemed well prepared as he covered his penis and my virgin opening in lots of lube and started to push inside me. It was sore at first but I wanted him inside me. I pushed back “good girl” he said as his full length forced its way into me.

He fucked me gently. Sliding in and out of me as I held on to a tree for support but his enthusiasm soon built. He was speeding up and I loved it. My own cock was rock hard as I masturbated. The feeling of my prostate being massaged from within by a monster cock was bliss. He was holding my hips now as I bucked against him. “Oh god” he kept repeating as he fucked me harder and harder. “I’m going to cum” he grunted as he pulled his cock out of me and finished himself off. He came. Hard. So much cum. It shot up the back of my dress, covering me. I heard it’s splatter as it hit my bum and felt the hot cream hit the tops of my legs. It was dripping off me in to my holdups. Spots were dropping onto my knickers now round my ankles. I was still masturbating and turned to face him. He dropped to his knees and licked my hair free balls. My cock erupted in orgasm. More hot creamy man cum jetted from my own cock onto the front of my dress. My mouth instinctively opened as some spunk hit my lips and chin. The rest spreading over my dress in thin arcs. My dress dropped over my cock as I stood up, a fresh stain of cum spreading on the inside of the hem of my dress.

I was soaked in cum, front and back. I loved it. He smiled and gently kissed me. It was lovely. I parted my lips as our tongues gently met. As we parted  he smiled again and pulled up his knickers and jeans before turning on his heels and making a quick exit.

There was too much cum on me to dress over my female clothes so I had to strip off. I carefully put away my heels and wig and got redressed before balling up my cum soaked dress, holdups and knickers. 

Everything washed up well. I’m tempted to take another days leave to see what happens next time. 

DTG xxx

Powered by WordPress.com.

Up ↑