Cross-dressing Confessions:

True Story of a Self Tormented Man

by Stacy

 

Aged 10 i remember having to use a girl's bathrobe and thought nothing of it.

From Aged 8 to12 id been fascinated by girls and had thought nothing of it.

After reading around this story site (which is very erotic at times) I thought id tell a true story, my story

May even provide some insight into why the urge is within me (and maybe you) to do what I/We do

Now aged (mid 30's) I still seam to daydream at pretty women

And even though I have access to the World Wide Web and all the porn under the sun,

I still prefer to look at women dressed, don't ask me why, I don't know why… But clothes are sexy, erotic, and they stir something within me.

Were does my ride begin you may ask, and ile tell you…

When I was 13, I went to stay with a relation for 2 weeks (family problems & school holidays)

She lived alone and was fairly old, id often help around her flat, one day while she was out, I was tidying up for her

When I found this white underskirt style thing, was like a lacy bodice but plastic style under skirt

(Was really weird like a costume style wedding dress) just made me feel so calm & relaxed touching it.

The under skirt part felt like plastic bed sheets, was so cold to the touch and the bodice felt so smooth and warm

Like rippled silk and cotton, I stood their for what felt like a life time looking at the bodice pattern

When the door opened and she came back into the flat.

I stuffed it back in the cupboard and said all tidy now, she made us both a cup of tea then she went to bed.

I lay there for hours thinking about wearing it then I fell asleep.

I used to play in the forest over the way from were she lived and one day I took the underskirt from the cupboard

And went out to play, I had no idea what I was doing but the thoughts in my head were so vivid

Alls I wanted to do was feel it more & more and not just the material; I loved the butterflies in my stomach.

The feeling of being caught and the urge to feel it against my skin

Hiding deep in the woods I took of my coat and pulled the underskirt from my coat sleeve and looked at it,

I could hear noises everywhere and was so scared of being caught by someone,

I quickly took of my t-shirt and pulled it on over my head, adjusted the shoulder straps and did the zip up under my arm,

I was shaking like a leaf as I put my t-shirt back on over it. Weird place for a zip, and shoulder straps were a nice sensation

Out in the open made it more exiting for some odd reason. Like why wear ladies pants if they do not zip up at the side.

If its NOT feminine theirs no point

I undid my jeans and pulled them down and felt the cold plastic of the underskirt touch my semi erect penis

(Which hadn't seen any hand action at all EVER) I suddenly felt the urge to stand up "which I did"

I twirled like an idiot then realized were I was so I quickly tucked the under skirt into my jeans and fastened them,

It felt great but at 13, I had no real idea what I was doing or what was driving me.

Probably a good job I had no idea, if id of known and wanked were I was, chances are id of been found

By some dirty old man walking his dog, part of me now wishes I had been,

Or found by a woman who new what to do with a little grille like me

As I walked through the woods I felt so relaxed (no family stress or problems just pure relaxation)

I waited until I got back before I took it off, standing there in the bathroom I noticed some sort of gunk on it

When I realized id been dribbling something from my penis (pre cum) and I franticly rubbed at the skirt till I cleaned it

Sticking it back in the cupboard all's I could think about was wearing that again.

That night when she went to bed, I started going through a bag of clothes (she did jumble sales)

I found all kinds as my hand dug deeper feeling all the new textures of clothes my hand stopped on soft silk

When I pulled it from the bag, it was a pair of sky blue silky pyjama pants with a small split up the side

Of each leg with lace around it. I found the matching top and I put them on, I must of lay there wearing them for hours then I changed back & went to sleep.

Next day she went out "taking the bag" which Ide planned to explore more of its contents

I was so gutted when I suddenly remembered the cupboard & the underskirt

And that overwhelming warm feeling of contentment hit me again, more butterflies in the tummy,

I rushed to the cupboard heart pounding, when my hands touched it, I remembered the last time

I couldn't work out what to do about (pre cum) which I had no idea what it was at the time

I was in a right state dying to wear it and stand proud and feel it and twirl

When I decided to grab a small clear food bag from the kitchen and place it over my penis

Then I put on the under dress and lay on the bed

Then I got up and did a twirl (I felt so great and nothing on my mind) I went back to the cupboard

found a sort of large red & black can can style rar rar skirt, long gypsy style, So I put it on, I was in heaven as I skipped around the room like a little girl.

I was jumping up and down on the bed I could just start to feel it rubbing against my nipples

When I started to get the shakes and felt light headed

The more I moved the more friction I felt on my penis and as I was really starting to swet

The food bag would slide around brushing against me and the material held heavier by the skirt over the underskirt

It felt so good and my mind was just going into a blur, as I collapsed on the bed

I lay face down waving my legs around and was really starting to wriggle

My heart was pounding, I can't even remember what was going through my mind but I was so happy

When I felt this uncontrollable urge to pee, i panicked,

I bit into the pillow, face down like a bitch, and I had my first ever orgasm, (not the last ill have face down neither)

Not that I new what had happened to me back then, but it was the most earth moving thing in my childhood.

I lay their totally stunned for a moment I thought I was going to die

As I tried to move, it just felt so tickly, my limp penis now sitting in a bag of what I later learnt to be cum,

I lay there for over an hour and then I minced to the end of the bed

I tried to stand then cum ran down my legs my legs just went to jelly

And I hit the floor clinging to the end of the bed like a frightened little girl during a storm,

I got up some courage & I stripped off and disposed of the bag and cleaned up, my heart was still racing,

When she got home she asked if id been out and was I ok, you looked very flushed she said

I just giggled and said id been climbing trees hoping she didn't understand what id done.

Hell at that point even I wasn't sure what Ide done but I sure liked it and I wanted more but was so scared.

Next day I went back home and 2 days later, I was back to school, starting new term.

Girls in my first school just wore basic uniforms and those nasty little blue and white dresses,

Which did not really interest me, for some reason I liked cold smooth or rough warm to the touch clothes

(Probably a perversion to friction some would say)

However, personally, I think I just gave my dick more sensitivity to touch than clothes Ide normally wear.

St.Trinnians movies are also torture for us poor guys

One night I grabbed a bag off a door step of a charity shop and ran off

At home I opened the bag and found a denim dress and that was it just a big boring dress

I guess line dancers would love it now but back then it was the late 80's early 90's and I liked foxy chicks

Nevertheless, I wore it then I actually binned it (after doing a wriggly using a food bag again)

Took me ages to build up the guts to hit a charity shop

Ide never wear my moms clothes and had no urge to, I liked Barbie style grille clothes

After that, I never did it again until I hit my high school then things started to change faster for me

I started to realize what I was doing and finding ways to do it with ought being caught.

In a new class just looking at the girls with the navy blue pleated skirts and white silky blouses

I was in heaven (or so I thought) I always wondered what it was that captivated me And how it could just make me reacted the way it did.

One day I was to ill to do P.E and the gym teacher let me stay in the locker room and read a magazine,

I sneaked into the girls changing rooms and was about to take a complete set of clothes,

Underskirt, tie, jumper, blazer, skirt shoes, bra, socks even knickers, I was in a hormonal frenzy

When I realized what about pre cum oozing and what if I oozed fully (Which I new by now was cum im like15 and in secondary school)

I still hadn't wanked neither, id always done the wriggle of ecstasy

Sometimes I even spat in a carrier bag or used lots of spit

Then basically lay face down on a folded pillow and the friction of the bag would send me into heaven

Then trying to move would be torture as it tickled as I lay wallowing in my own cum

But I guess that's the same urge, as wanking only id not done that besides this still feels better than wanking to this day

Anyways, this then became more like torture to me, sitting in class looking over at them

And the most bizarre thing is, I did not want sex with them, nor did I want to see them naked

I just wanted to look in the mirror and see my self dressed like that I wanted to feel the breeze against my legs I wanted to feel the bra straps under my silky white blouse I wanted to feel the skirt pleats on my knees.

I wanted to sit with them talk about girlie things.

You girls have no idea how cruel school is for a guy who just melts when he wears knickers

You all claim to have it so bad yet us guys end up having to fight just to stop being bullied

And you lot sit there in the most sensual sexy teenage clothes and complain about periods,

Trust me Ide put up with a period to be able to play with my own breasts and pussy,

And be able to have multiple orgasms 1 after the other over and over

You're all so frigid now adays and a Lot more men are turning bi

Because a lot more girls are closed of to their sexuality and are scared to explore

(In later life, I had no complaints taking it off a man while giving it to a woman, it was amazing)

I was the filling in a sexual sandwich

In school, it all got too much for me so i start skipping school and hung around just outside my home area,

Was really lonely for me but then id had a fairly lonely childhood and to pass the time id hang around

The usual places lads should not hang out, like empty buildings, hiding from 9am till 3:30pm

Id always travel to places either by the railway lines or back alleys,

A few times neighbours had seen me and told my parents I was not in school,

So alleyways were a must have way of travel

One day walking down an alleyway pushing my bike I snagged the peddle on a bin bag,

And clothes were hanging out, like a kid about to steal, a candy bar I felt that churning feeling

I grabbed the bag, ran all the way down the ally shoving the bike

And scrambled up onto the old railway lines and down into the bushes

I had a 40ft building one side and a 20ft crevice the other; anyone looking down I was invisible

Id snuck right down way off the tracks and into the shrubs, my heart was racing

Alls i wanted to do was wear something

I tore away at the bag and to my pleasure I found a school skirt, quickly I pulled at my zipper

Off with the pants and tried to get this skirt on and it was to small,

I was heart broken, I dug back into the bag and pulled out a bra I laughed to my self,

Thought well that's something ive not tried yet so I put it to one side and looked back in the bag

In addition, pulled out a black jumper and size 10 jeans, this was not looking good

I then pulled out a green skirt really ugly but defiantly girly and size 12 so I threw it to one side

Then as I reached in the bag I pulled out a bunch of sports socks some boys boxers "eww"

And some girly socks and knickers mmm, and although I said eww at boxers back then,

Today id probably put them on my head and positioned the crotch around my mouth and nose

In the hopes of smelling their penis and maybe sucking some juices from the material (OMG I am a pure dirty slut)

I put the skirt and everything else back in the bag besides the knickers and bra

As I looked through the knickers they were stained {some of you girls really are unhygienic}

I found a pair that were ok and slipped them on, they were tight, when my erection finally died down

I managed to fit my dick rather snugly in the gusset tucked back then I sat back to examine the bra,

I looked at it, id seen them in magazines id seen them in porno videos and now sitting in knickers hiding in a bush

I had one in my hand. After about twenty seconds, I had it on under my school shirt, so tight and sensual.

Feeling vulnerable I headed back up to the old train tracks and followed it back down the direction id came from

Riding through the same alley with my First ever pair of knickers riding up my crack,

I started kicking the bags like a tramp looking for food or a drug addict looking for a fix,

I must have kicked at least 30 bags when I kicked me a winner then another then another,

With my heart pounding I grabbed the 3 bags and ran for it as fast as I could,

Stumbling everywhere dogs barking heart racing, knickers riding up bra clinging to my swety chest.

I went back to were id left the first bag and sat down, my hart was pounding,

My nipples were itching in this bra and my dick felt like it was on fire, semi hard

But trapped within the confines of little cotton panties

I ripped open the first new bag and it was blanket's I could have screamed I opened the second and it was clothes I ripped at the third and that was cloths to.

Most of it was boring adult male cloths and the old lady style blouses

When I came across a pink and white shell suite in the bag

(I miss late 80's Girly fashions) I stripped down to my, well someone's bra and panties

And slipped on the shell suite, it felt very smooth on my skin and tight around my crotch,

I rolled up the bottoms a bit and slipped on some of the pink socks {put the rest in my bra}

Then I tucked in the top and pulled the waste cord of the pants tight and tied them,

Then I laid out one of the blankets and lay on it looking at the other clothes

I pulled out a black skirt and put it on over the shell suite pants and fastened it

Then put on one of the blouses, as I lay down on the blanket and started to wriggle,

I got closer and closer to the pile of dirty panties and I could smell them

As I got closer my mind was a whirl of emotion, just like back in that flat aged 13 I was a wash of emotion

Id not been dressed like this for a long time and god was I horny and shaking like a leaf

Alls I was imagining was what if someone found me what if the girl had followed me & im wearing her clothes

And she was punishing me and as I wriggled I started to totally loose it, absolute uncontrollable pleasure

I got closer to the pile of knickers as I was wriggling, like I was drawn to them

I put my toung out and at that moment I was about to lick the dirty crotch, I cum in a world wind of pleasure

At that moment I stopped wriggling and felt sick, even though id not touched the knickers I still started to Bork

I wasn't sick but I felt so ill, I wondered would I of actually licked them if Ide not cum so soon

Or even took the whole crotch into my mouth.

I quickly got changed and went home.

A few days later I got the urge again and as im walking through the alleyways

With my heart pounding, I started looking for clothes when I came across an empty house with no back gate,

The entire front was boarded in the street but one of the back window boards was ripped off

And I sneaked in, with most people in work or school I figured its empty and you never no

So I sneak in to look around, it was dark and I was scared,

There was clothes & rubbish everywhere, not that I could see much the place was a mess

Typical council house all messed up and people moved to a new home to destroy.

I held clothes up to the light, it was like id been dropped into Aladdin's cave,

I grabbed some tights, bras, knickers, shoes, skirts, dresses, and other odd bits

Most were dirty or slightly damp but I didn't care, I had an urge and I needed something

I hopped out the window and down the ally up onto the railway, lines and this time headed the other way

Down to an abandoned sub station and sneaked in (most my area was abandoned buildings it was great)

I went through everything id got and picked out exactly what I was going to wear

1, g string which went right up my crack then a pair of baggy silky knickers, Black tights,

4 & half inch heals blue, a really tight bra which I padded then it started to rip under my arm

So, I put on three others over it and the Restriction of wearing so many really turned me on,

I then put on a mini denim skirt and didn't like it; the way it rubbed wasn't feminine enough

Then I found a short lined black pencil skirt was a bit to small but I managed to squeeze into it

As I tried to walk, I minced like a fairy as the skirt kept my legs close together

The underlining of the skirt glided against the Tights it was the most erotic thing id ever felt

I slipped on a long sleeved white silky blouse with weird shoulder pads then I just

Stood there in the corner of an abandoned power station thinking what the hell am I doing here,

I must look such a dork but I felt so good and the butterflies were back, and the wriggly…

Well that was the last thing on my mind; the longer I hung out there the more a realized if I did the wriggly

Id stain them and besides the stain, once id cum, id not wear them anymore and being dressed meant feeling contented.

See once ive cum I just strip off, it's like once ive released sexuall tension I have to change my clothes back

Or I feel so weird, but when im Horney ile wear anything, its like that part of me wants to dress up and be shagged

And afterwards, im the one who feels used and dirty, between around the 8^th of febuary and 30^th April

Im like a dog on heat, I can cum 3 times a day, normally in the space of an hour

mid febuary ive even been known to eat my own sperm from the first time, as I cum for the second time

Maybe it's the moon the stars who knows but its like a cycle every year were I take a holiday and she minds the store

I must have sat there for ages in that building when I remembered the time and I was meant to be home from school

I felt somewhat sad getting undressed and I hadn't cum neither, so I stripped, hid the clothes and went home

Next day as I left for school I headed back to the power station and checked a few alley bags on the way

Found a bag of clothes and got my self a black belt with gold style rings,

Handbag, lipstick & powder case with mirror and some naffy perfume and a busted up jewellery box

Heading up to the building, I sneaked in then waited,

Making sure none of my mates followed me from home

So I got dressed added the belt to my outfit and sprayed the clothes with perfume

Then I started thinking about the lipstick, so I used it (wouldn't risk the powder though)

My lips felt so soft and tasted strange but really nice

After about an hour I decide I want to do the wriggly thing, im really horny all dressed up

And there's no were to lay down in there, so I struggle with my tights and knickers

And I flip my dick out and start playing with my self when I feel dirty and somewhat sick

So I stop and put it away, this continues for ages,

Im so horny yet ashamed of what im doing and really worried ile be seen or caught

And it don't feel as nice playing with it compared to when I wiggle face down

Then that's it I finally snap and I yank and yank till ive got my dick back out and I wank until I exploded

This then happens during school hours for years, different places & different clothes,

Until I hit 17, I was always out looking for clothes even looking in places were people just fly tip their crap

Then I meet a woman (much older than me and I finally loose my so called virginity to a woman)

All seams normal for a long time (5 months) and I don't even think about dressing again

Then after about 2 months after I split with her, I start wearing clothes again.

Saw a bag "same charity shop" I used to dream she would catch me and make me her Female shop assistant

Aged 18 in my own flat im then wearing more and im now keeping more in my wardrobe,

One night while out looking for more clothes, I find a vibrator and my eyes light up

I rush home and get dressed, black suspenders, rough ass teasing thong

Flairy black mini skirt black bra and really tight black top

I wash the dildo over and over till I just can't take it no more and in my mouth it went, no hesitation

I watched my self in the mirror as I jerked my self

I guess I liked watching my self as a woman sucking cock

I lay on the bed and started to put it near my ass as I played with my self

And as I opened my legs more to take it in my ass, I cum all over my self

Ide finally used my own hand to cum, my first proper wank

Next night I got all dressed up and got the dildo again; I thought this time im going to put it in my pussy

No teasing the hole and coming before hand so I leaned forward and rubbed Vaseline

On my crack and rubbed the head up and down I felt so relaxed and comfortable with my sexuality

I do not fancy men although ile give you head so intense you will think I was a cock hungry woman,

{That actually goes ALL the way & Swallows, as I later learnt in life)

I took that dildo all the way, I couldn't move, it stung so much

I just lay their rock hard for about 4 hours until I fell asleep

I woke up later in agony like my balls were going to explode,

I was about to take the dildo out when I thought; the more I do this the less it will probably hurt,

So I slid to the end of the bed and sat there thinking will it hurt as much coming out as it did going in

As I jerked my now hard cock through my thong

I rocked back and forth on the dildo and wriggled as I sat on it

Until I finally cum then I started to Bork again and felt really sick

To this day, I still do this stuff and have NO idea why

I wouldn't say im possessed, id say it's Hormonal

I can have sex with a woman and fuck 2 hours solid non-stop

Put your wet knickers on me and ill last about 2 minutes

My new girlfriend and me (then aged 25 and still never really walked out dressed)

We put an advert in the paper for couple (us) looking for Bi male (him)

And we got one; I took great pleasure in eating his cum from my girlfriend

As he put his second load into my ass,

I get so driven to look feminine and act it until I cum then I feel ashamed but I wanted it

I felt so embarrassed all dressed up he was rock hard, I couldn't take him, he hurt way too much

Therefore, I gave my lips & throat a taste of the real thing then after sucking him like a kid with a new toy I then lay back

And watched as he fucked her like a real man fucks, I felt sad as I watched her orgasm after orgasm

He kept looking at me and smiling as he fucked my girlfriend into a frenzy, I felt more jealous she was getting cock

And I wasn't then he collapsed on top of her and she called me over to the bed and

Then I ate his and her cum from deep within her and then sucked and cleaned him off

I wonder if I could never cum would, I dress more as a woman as well as outside

I certainly stay dressed longer, but the moment I cum I change back to male clothes

Even though my fantasy is to be tied to a bed wearing cum soaked knickers (his and hers) not mine

But ive noticed once ive cum I don't want to and 99.9% of the time I really wish she'd make me

We only used him twice and since then, my girlfriend has a strap on

Which she uses from time to time, but I still get the urge for a real one in my ass and one in my mouth

Buy this time I was thinking, Ide love to take a burst while deep throating but he was short & wide

Strappon is long and medium but empty

Am I a pervert ? Am I a slut ? Am i a woman trapped in a mans body ?

I no a few thing's about my self,

Being able to cum stopped me eating on the crotches of seven pairs of crusty knickers on that life-defining bin bag day

Being able to make my self cum probably stopped me begging for a dick at the age of 15

Being able to make my self cum probably stopped me walking the streets of a day dressed as a girl

And when im tied up on the bed in her damp knickers with no hands free, ile take any kind of sex offered

I wish she would abuse me more, but she wont, and I yearn to take it while she stands watching

Knowing its her who has despunked me and is still making me take him, just turns me on even more

But I want her as well as him

I could say,

Im sexually driven by an extra Chromosome and I love it; just don't let me cum or the fantasy's over

But id be thinking

MAKE ME CUM, Then make me take him anyway, im sure I will get used to it

Im certainly dressed for the part, so why not share my self with that

Poor lonely undecided Chromosome, besides why should the male genes in me

Get all the fun when the one feminine gene knows what i really want deep down, and up….

Yours truly

Stacy

 

Ps

That Misplaced Hormone makes this whore moan

  

  

  

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