This is a tale from quite a while back.
In the early 80s I had got into music and was into lots of rock and hippy music. My hair was long and had a good slim build. In the summertime I went to a few festivals - mainly rock, but a friend from Bristol invited me to her place, we had wanted to go to Glastonbury but missed it and ended up at Orchard fest. A small event with just local bands and much booze.
My fiends - Susan D though got fed up and left early - she was tired and just not into it. She lived about 15 miles away. After it ended I decided to go back to London but madly after talking to two girls decided to hitch it. Well after waiting four hours and it's now late afternoon Sunday...festival had finished late sat and I'm tired. I decided to walk to a main road and wait. It was a long walk and I was very hot ..another hour passes and no one is stopping - not surprising really. A long haired guy with a ruck sack looking wild..
I just sat down and and started to consider changing my route, maybe Bristol?
Then a car stops, a Ford estate. One guy early forties. He leaned out and said "hiya sexy girl.." then as I stood he realised.."oh, sorry...".
I'm desperate now it is getting toward 7pm and I need a ride.

"it's ok no worries - any chance of a lift to London?" me being so cheeky. He looked at me and smiled. Dark brown hair, nice face, he said ok - but I have driven from Bodmin, I need to stop for a rest. But hop in.

I was so pleased and soon we were off heading east. We chatted, he is Paul, he is on the road selling shower parts to hotels. I tell him that I was at a concert. He apologised again about thinking I was a girl, it's your hair!

My hair is long - shoulder length with a wave to it. While he's driving I check my bag for some mints, I'm starting to feel sleepy and hope that by sucking them I will stay awake, while im searching my bag I suddenly realise that Sue has left some clothes in it, two panties!! A summer cotton dress and small bag, I peered in and see make-up. I hope Paul has not noticed!!!

Despite my best intentions I fell asleep. When I wake it is about 10:30. Paul is still driving but then pulls into a layby.

He stops and turns off the his engine. " I'm tired, feel tense.."
"ok" I replied.
He looked over and said can you pay for the ride?

I responded that I had about £3 hence my need for a hitch!!

He looked again and said not cash. I was puzzled then he said get my cock out and wank me off...

I said erm, I'm not gay..which is true as I was bi. He looked again and said come on, I have driven, I need this. Please?

I felt horny, scared but wanted to help, so I reached over to his groin and gently squeezed between his legs. He felt semi hard and it felt good, I stroked and I heard him sigh, then he said get it out.

I gingerly undid his button, then I slowly pulled down the zip, parted his flies and reached into his pants...I felt warm, smooth soft flesh stretched over a hard shaft, I pulled him out and gently stroked his cock, carefully rolling his foreskin. He was a good size, about 7, nice width, largish head and a gorgeous strawberry colour. A bead of per cum appeared and rolled down.

Arghhhhhhh - he monaned.

And then lick it....

I froze, unsure, knowing I like cock, but feeling shy.

Go on!

I tentatively flicked out my tongue and licked his precum. I love it's taste. His cock is in my hand and mouth is inches from his cock..

Suck it, go on cocksucker...

I lick again around the head, then forming my lips into a tight O I took the head in, he groaned, I moaned.

He tasted sweaty, slightly of piss, but as I suck the taste recedes, he feels great in my mouth

I knew you were a cocksucker, he said - you are a great cocksucker. I keep going my head bobbing up and down, as I swallow more and more of his hard cock...

Then he tensed and I reached for a box of Kleenex,

No ! Cocksucker, swallow

Then I feel him cumming and hot liquid is in my mouth. I swallow...hot salty cum and love it

Paul stayed still, I just stayed still his cock growing limp in my mouth, I love a cum tasting cock. I slowly let it out of my mouth

Paul smiled and said wow! That was hot. He closed his eyes and fell asleep in seconds.

I soon dropped off too, I awake and it's around midnight.

Paul is driving and the roads are empty. He looked over and smiled.
I wanted some mints to wake me up he said but I'm sorry I saw your gear, I apologise.

I was puzzled gear??? The girls stuff - so your a transvestite?

No I responded, it's my friends, even as I said it I realised how lame and so totally untrue it sounded - my friends....

Hey he says, ok with me, I like it, boys who dress as girls, it's hot and wow you probably look great. You are kinda girly, your hair and hips.

I looked at him - I'm bi but I'm not into that, but inside I'm excited....

But does anyone like this?

I was feeling very excited and turned on, my stomach had butterflies and I was tingling.

I tried to pretend to be uninterested but I now wanted to try on the panties and the dress.

Paul looked at me and said I'm tired, we are staying here. He stopped outside a small guesthouse.

I looked at him and said I cannot afford this, I'm really not able to...

He smiled again and said no worries I am sure you can pay me back in kind..

We went in and Paul paid explaining that he was working with me. The room was small, two single beds and cupboard, plus small toilet and shower. I threw my bag on the bed and sat down.

Paul smiled again and then said - I'm horny. Turn round on your knees.

I was stunned he had only come about two hours back!! I turned nervously, and got on all fours, I felt his hands grip my jeans and pull them and my undersea down to my knees.
Wow! He said, nice bottom!
he stroked my cheeks, gently and ran his finger along the slit.

"Ok I need to fuck you.."

I was shocked but equally turned on , next thing I know is a wet liquid is gently wiped down my slit, and onto my bum hole,

" oh yes! Looks good"

Then I felt hs cock on my arse cheek and then slid between, I loved the feel of it between my cheeks, the head resting against my anus. Then he gently pushed and it felt huge, I was thinking it cannot fit, but I knew it would I could feel his head stretching my bottom open, it hurt
I clenched my teeth, and gripped the bed, but still he pushed and then the head was in, he pushed harder and then with a feeling of pure wicked pleasure he sank his cock home , I moaned, full of hard cock.. He started to fuck, gently sliding in and out but building

"so tight" he said " lovely soft bum... You sissy take my cock..."

I felt so full and with each stroke a wave of pleasure hit me, I felt his tight balls slap against me, the only sound was the slap of flesh and our breathing...
Then Paul groaned and made one last thrust before just stopping buried deep.
I knew he was coming, he pulled out slowly but said
"do not move, I want see my cum "

I could feel myself blushing and I felt warm, wet liquid run out and down my legs.

Paul said lovely arse - so enjoyed that... You have a pretty bottom.
He moved away and went into the toilet, I grabbed some tissue and reached back, wiping the sticky cum of my legs and bottom.

I then stripped and waited - Paul came out and smiled - shower is yours, make sure you clean I want to fuck again soon..

I showered and then using the shower nozzle I fully douched myself.

Leaving the bathroom, I found Paul had gone. But on the bed laid out was the summer dress, black panties, stay-ups, and - where he got them I do not know but some heels, black, medium height...and the make- up bag. Plus a note

Get dressed and be ready, I want you girly and ready

My own clothes apart from my pants were gone, but part of me wanted to try the stuff on, wanted to be feminine.

I was alone in the room... I took off my pants. Picked up the black panties, they were smooth, with a lace edge and a semi-transparent back panel. I took a breath and stepped into them, sliding them up. I loved the feel of the material as they went over my bum. Looking in the mirror I bent over, checking out my own bum! I looked good, although my hips don't flare, my bottom looked great, only issue was the growing size of my covk was never going to fit in the panties, unless it stopped getting hard. I tried to ignore it. Sat down and tried on the stay ups. This was so sensous and lovely, the way my legs transformed to looking slim, shapely and sexy. The smooth feel and then at the top, the flesh between the stocking top and the panties. Feeling very sexy now, I picked up the cotton dress, it was cream, finished just above the knee, light and clinging - I pulled it over my head and was stunned at how comfortable it was to wear and how liberating, a dress!! It made my legs feel so free and I felt turned on again. The only issue was my chest, I have no size to my chest and the dress was button front but only up to a low collar.

Now the tricky bit..I opened the make up bag, and was lost ,, what did all this do? Luckily I had shaved and being fair and young I had smooth skin with no shadow.
Ok I thought these ones
Lipstick
Eye shadow
Eye-liner
Mascara
Blush

First and with my botches I used eye-liner, with eye-shadow it transformed my eyes, wow! So different, made me feel attractive and confident..
Mascara - was hard but again my lashes suddenly appeared! Such an impact, I used the blush on my cheeks and then pouting my mouth I put on lipstick, not bright Red but red, oh my god, I could not believe how sexy it made me feel and how much I wanted to kiss...

Looking in the mirror I could not believe how different I looked, I knew I was a boy or rather a sissy, but looking femme and feeling so liberated. I put on the shoes, tight and tried walking, not easy but again the feeling of power, confidence and sexiness was amazing...
I was loving it, being a sissy was so hot!!

Like this theme??

I had just finished dressing and applying make-up, when I heard a knock and then Paul's voice.
" Hey are you ready?"

I felt so nervous and scared and shy...

" yes ...come in"

Paul came in closed the door and just stared at me - "wow you look so sexy - can I call you Suzy?"

He walked up and put his arms round my waist...
I was unsure, I felt self-conscious and at the same time so horny...
I turned put my arms on his shoulders and kissed him, feeling his lips thru the lipstick..
He responded eagerly kissing me, his hand slid into the small of my back, then over my bottom...
We moved to the bed and sat still kissing, his hand slid up my dress , feeling the inside of my thigh...

Then further to the flesh above my stocking, my hand moved to his groin and I started stroking his hard cock through his clothes, we kissed more with passion, then I quickly undid his trousers and slipped my hand in, searching for his hard shaft, I pulled his pants down and took his cock into my hand, gently releasing it...

I broke the kiss to look at it, it felt warm, soft skin, but hard erect cock...
I pushed Paul back lowered my head and slowly flicked my tongue around his head, down the back of the shaft, smelling his aroma, my tongue went up to the head, licked a trail of precum in a sticky trail, then pursing my lips I took the head into my mouth, just to the glans, my on glue swirling across the top, he groaned and I pulled him in deeper, until he hit he back of my mouth, as I pulled back I tightened my mouth around the head and again as I went back down, I old taste his precum more, I love the taste of precum.. I felt like a slut, but I felt good too, mouthful of hard cock, I raised my head releasing his cock and stared at it, it was huge, shinning with saliva, hard and throbbing, I held it gently and then firmly - quickly taking it back into my mouth, sucking had and bobbing up and down...

He pulled me off his cock, and said "I want to fuck your tight hole"

I obediently flipped over on all fours, I felt him move between my legs and raised my bum, he pulled my dress up and gently pulled the panties down to just below my bum. He parted my cheeks and carefully lubed my tight hole. I felt his cock touch my arse, then he pulled it down my arse crack to rest against my tight hole
"ready for cock Suzy?"

"Please , please fuck me, fill me with hard cum...fuck my tight sissy hole"

I felt him push, his huge cock head against my small tight hole, then he pushed harder and the head stretched me, uk pending my hole and then he slid into the hilt...

He gently fucked me, with each thrust a wave of pleasure ran through me, I was tingling all over. His cock felt delicious inside my tight hole, I felt so turned on, on all fours dressed as a girl, panties down..

Suddenly he pulled out,

"Suzy turn over, and spread your legs.."

I turned over looking up at him, seeing his hard cock, he gripped my stocking covered legs by the ankles so my feet were in the air, the heels pointing up at the sky, my legs looked so great clad in black nylon, so long and sexy, he pushed me up higher revealing my bum, then deftly he slid his covk back in filling me. I felt so weird, I loved being a sissy, loved being fucked, filled with hard cock, he leant over, still buried to the hilt, the panties were still on me, covering my straining cock, he kissed me and started a strong slow fucking of my tight boi-pussy, I realised that I was moaning in pleasure..
After a few more long hard thrusts, he pulled out, pulled me up and turned me round, lifted my skirt and pulled the panties down around my ankles, and once again lid his cock back in...then he thruster harder into my bum, then with one deep thrust I felt him clench, and just hold me around the waist , he groaned and I knew he had come, he pulled out and pulled the panties back up. I could feel cum dripping out into my gusset,,
I felt so girly, pumped full of hot cum, feeling soaking my panties...

Is this working for anyone?

Paul layed back and went to sleep, leaving me standing with cum oozing into my panties, my slit felt deliciously wet. I loved the feeling of cum in my panties, the feeling of just being fucked...
I sat down and drifted to sleep. I woke two hours or so later, and then realised I was still dressed as a girl, and I had no other clothes.

Paul was awake reading - ok he said I will return your clothes, but first I need a blowjob, I want to come over your face. Then we will go out.

I walked over feeling hot, confident in my heels, I knelt and my dress rode up, revealing my stocking tops. I undid his trousers, pulled down the zipper, his cock was hard in his pants, I stroked the outline. A small damp patch appeared where the tip of his cock was straining at the cotton material. I kissed it through the material, tasting precum, nuzzling its hardening shaft.
I reached up to the waistband, pulled it down, his hard cock sprang out, pointing at my face. Precum dripped out. I put out my tongue, licked the tip, and drew a string of silvery precum into my mouth. I opened my mouth and took his cock deep into my mouth, pulling its hard hard shaft in, feeling the head hit the roof of my mouth. Keeping my mouth tight around the head as it moved in and out. My lower lip pushed down, my cheeks sucked in tight. I gripped his bum and pulled him closer, taking his cock far into my mouth, almost gagging, tasting that musky cock taste, feeling his pubes against my face. I held him like that constricting my mouth, tongue caught under his hot hard cock.

I released him, holding the shaft, stroking his foreskin, then taking him back in, not wanting him out for a second.
My tongue flicked his frenum. My lips tight on the glans, then I feel sim squirt, shooting cum into my mouth, I pull away to watch his cock twitch and fire over my mouth and cheeks, feeling the hot sticky liquid run down my face, my tongue catching it and swallowing his hot salty load...

Ok said Paul don't wipe it, I love seeing the cum on your face.i froze feeling self-conscious, but loving the totally slutty look and feel.

He pulled me up and said lets go out

Now? I said? I can't! Not like this!

Paul smiled and said you sissy. Last one. He took my hand and led me out, luckily reception was empty, I felt weird in high heels, dress, makeup, cum on my face, we walked to his car. I got in smoothing my dress, crossed my legs, and then he drove, he his hand wandering to my legs, under my skirt, caressing my thighs, my legs opened, I wanted his touch. I reached over and felt him, he was hard again, I undid him and pulled him out, he was massive and rock hard, straining. He stopped at a layby, we got out and his arm went around my waist.

We walked through trees until we came to a small fence. He positioned me facing away and told me to bend over. My dress was raised, and then my panties pulled down, they fell around my ankles, I felt his hard cock against me again and once again he penetrated me, pushing in to the hilt. Your bum looks great he whispered and process to ram in and out. Take it sissy!

I love it I responded, I love being your sissy cum slut...

He slowed the pace, kissed my neck, his hands roving over my chest, my bottom, then he started again, a slow relentless pounding, his head hitting deep inside me, I felt a wave of pleasure, my anus felt so tight, so tingling, then a huge orgasm hit me, and I felt my semi-erect cock cum, my bum clenched him, Paul moaned and shot a third load into my bottom..holding my hips.

Your bum is so soft he murmured, so tight. Love it.

He pulled out slowly and carefully, then pulled my panties back up. Let's o back for dinner and we walked to his car, I could feel cum in my panties, they were soaking, and then it trickled down my legs in sticky warm trails. In the car I sat and could feel how much cum was now soaking my panties...

Paul smiled and said - good? Nice sticky panties? Full of cum?

I smiled back and kissed him. Thank you I whispered. You made this girls day.

If you want more, of how I discovered I was still into dressing later in life please leave a message.

A

We stayed one more night at the guest house, but strangely on retuning Paul collapsed. I guess four loads in about one day sated and exhausted him.

I took the opportunity to bath, shave my legs, armpits, chest and bum. I wanted to be smooth, then I moisturised my legs, chest and bum. Finally I shaved my face, then just wearing a tshirt and panties I fell asleep.

Next morning I woke and Paul had returned my clothes. He was smiley and happy he thanked me for being brilliant and sexy. Seeing his clear joy meme reel moved and I offered him a morning snog and blow job but he declined. He did ask if I could stay dressed for the journey ome, he would stop somewhere saw for me to dress down. I was worried about being dressed as a girl in daylight - while I'm thin and have long hair, I think most people would realise quick that I was a guy dressed up. Especially if I spoke!!! I cannot do a femme, camp voice!!

Paul though said he would not risk exposing me, and we could have a last fling, did I not want cum soaked panties? One last time?

I agreed and dressed up again, after a quick face shave, I used foundation, powder, shadow, liner and mascara. Then lipstick, which turned me on huge and made me want to suck him...I didn't but heck I wanted to so much. I realised how erotic my mouth had become and my bottom, I cared not or being erect or cumming as a man, I just wanted cock.....

After a careful plan I left first and got into the car, and waited for Paul, I was shocked to see that when I sat down my stoking tops showed!!

Paul quickly joined me and with a quick caress of my inner thigh we left and headed east. Paul kept on saying how pretty I looked and he was so mad to have sex.

So I'm dressed in

Black lace panties
Black bra - though I'm flat chested
Black stay-ups,
Dress -cotton, short.
Black heels,

I loved sitting legs crossed and just feeling so relaxed and calm. A few time I caress his knee, and once or twice a quick fondle of the bulge in his lap....