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The Sweetshop

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By *tephanie Somtimes OP   TV/TS
5 weeks ago

South Derbyshire

It was great when I was a lad to have a sweetshop on the corner of my road. Mum worked there part time with the owner Harry.

Harry was a big jovial man, sometimes when I was off on holiday he would take me to pick up the papers and magazines from the wholesalers. We didn't have a car and he had a posh one that I loved going for rides in.

When I was about 15 mum got me a job as a paperboy. Harry was always flirting with my mum, squeezing past her behind the counter and grabbing her thighs. Making rude suggestions. Mum enjoyed all the naughty banter but she always told my dad.

One man on my paper round always had a girly magazine delivered called Mayfair. It was a fairly tame magazine but for a lad of 15 it was very exciting.

I carefully looked through it before posting it and the rest of the newspapers through the door.

The years went by and I got good grades at school and moved onto 6th form college.

I was a naïve lad of 18 now and looking for work. Mum still worked with Harry in the sweetshop and asked if I would like to take over from her until I found a proper job. I agreed and so took over mum's part time job.

Harry was obviously disappointed that mum had left. He told me he missed all the naughty banter, but still flirted with the ladies that came into the shop.

It was the fashion at the time for lads like me to have long hair and mine was almost shoulder length. At puberty I developed breasts and pert nipples, wide hips and a big bottom.

Boys jeans didn't fit me so I would secretly buy girls jeans that fitted perfectly. It was the fashion to wear them tight and mine really hugged my peachy bottom. I wasn't very big in other areas and struggled to either get or keep a girlfriend.

Harry on the other hand was well endowed. It certainly hadn't escaped my notice that he was well hung. He didn't wear tight trousers but he wore braces that pulled his trousers up around his crutch. Whatever he wore you could always see his fat cock sticking down his leg.

A new magazine came out called Whitehouse. It caused quite a stir not only with the public but between my legs too. It was the first magazine to feature erect men and they were big too.

Harry and I both thumbed through the magazine. I'd never seen such a big cock before. It gave me butterflies in my stomach. It was a strange feeling, it looked so powerful and made me feel quite weak. Even Harry blushed.

One day I was bending over unpacking the cigarettes when Harry slapped me on the ass really hard.

"Fucking hell Harry", I said, "What are you doing"?

He went bright red and apologised. He said he'd forgotten himself and for a split second thought I was my mum.

I have to admit I was smiling from ear to ear and rather enjoyed it. So much that I got an instant hard-on which I'm sure Harry noticed.

Harry carried on trying to explain why he did it.

He said, "It's your fault with your girly hair and those boy boobs and pert nipples poking through your t-shirts.

I couldn’t help but blush. No one had ever commented on them before and it was embarrassing.

I subconsciously ran my thumbs over them.

"There you go again", he said, "You are always touching them and it's distracting".

I didn't realise that I was doing it and apologised but they were incredibly sensitive.

After this encounter Harry started teasing me about my girly attributes.

He would do what he did with mum and pretend there was not enough room for him to squeeze past because of my bottom.

It was like he was flirting with me and I enjoyed it. He began grabbing my waist like he did with mum. Then one day I pushed back on him and gyrated my bum against his groin. I could feel his hard cock and it excited me.

He pulled me against him and immediately reached around and pinched both of my nipples really hard.

I gasped in excitement and felt something wet in my briefs. I reached between my legs and Harry asked what was wrong. I said I think I'd pissed in my pants.

We both went into the back and I undid my jeans and checked my briefs. To my astonishment it wasn't piss but cum. I'd had an orgasm without even touching myself and flooded my briefs with cum.

I asked Harry if he had a tissue and he said he had something better than that.

He dropped to his knees and and straight away took my cock into his warm mouth. My knees were like jelly and my legs trembling I held onto the counter for fear of crumbling to the floor.

I tried to push him away it was all to exciting but he wrapped his arms around my legs and made me cum again and again.

Then we heard the bell ding on the door and we knew we had a customer.

Harry told me to stay put and I collapsed onto the chair still trembling not quite sure what had happened.

Harry came back in as white as a sheet.

"I'm sorry, I don't know what came over me", he said, "I've not done anything like that since my 20's".

I said I felt guilty and a bit dirty. He was worried I would tell my mum but I assured him I would not be telling anyone.

That night I went to see my girlfriend. I promised myself I would never flirt or do anything with Harry again.

The next day at work I couldn't bring myself to look at Harry. I don't think we actually spoke to one another.

Another week went by, we did talk but there was no naughty banter.

The following week Harry went to the wholesalers. When he got back he handed me a glossy magazine called He-She - When Boy Becomes Girl.

On the cover was a young man about my age and then next to that photo was a picture of him dressed like a glamorous woman. I thumbed through the magazine getting very aroused.

Harry asked if I knew Sid one of the men who worked in the office opposite. I said that I thought I did. He was the man who gave me 50p coming up to firework night a few years ago when I had the guy outside Harry's shop.

Harry said Sid had seen me dressed in women's clothes in my bedroom.

I was so embarrassed but it was true. I did dress in my bedroom and never closed the curtains. I couldn't see into the offices opposite and thought they couldn't see me.

Harry asked me what I wore. I told him about a girly magazine that my dad owned. It featured a woman in a mink coat wearing just a lingerie underneath.

"Go on", Harry said with a wry smile.

I told him that I wore mums fake mink coat her bra and stockings and suspenders. He asked if I enjoyed being girly and I said I did.

He then asked if I would dress like a girl for him and Sid one night after work.

The thought of dressing for two older men made me rock hard but I was such a wussy I didn't know if I could do it.

Harry said that Sid could get one of the office girls uniforms that consisted of a white flouncy blouse with puffy sleeves and lace trim and a black mini or pencil skirt. Harry suggested I could wear mums panties and the stockings and suspenders.

Harry described a scenario where I could play the helpless office girl or an innocent shop assistant. Either at the office over the road or here in the shop.

I was taken aback with his suggestion but very curious to try something like that but I would need to mull it over.

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By *hris1954Man
5 weeks ago

Beverley

More please

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By *issykissyMan
5 weeks ago

York

amazing story, please continue

xx

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By *imale999Man
5 weeks ago

dudley

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By *uffolkbi7Man
5 weeks ago

aldeburgh

Now this I like xxx

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By *ikki1970Man
5 weeks ago

leicester

Excellent start, looking forward to more

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By *iss WednesdayTV/TS
5 weeks ago

Stortford

Wow, I'm very excited reading this

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By *urious85ukMan
5 weeks ago

Newcastle

Nice

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By *ackiex32TV/TS
5 weeks ago

Wick

Please keep going x

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By *ashtoolMan
5 weeks ago

belfast

More of this great read

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By *jsucksTV/TS
5 weeks ago

Chesham

Oh god this is so hot please don't stop

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By *otwillyMan
5 weeks ago

Scunthorpe

Interesting story

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By *lackmini2TV/TS
5 weeks ago

solihull

great start

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By *ax_glasscotMan
5 weeks ago

glasgow

Looking forward to hearing how big Harry is.

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By *rianishardMan
5 weeks ago

Cambridge

This is so horny, more please. This is too good to leave it hanging!!!!

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By *onmar01Couple (MM)
5 weeks ago

Bargoed

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By *atinbloodMan
5 weeks ago

Birkenhead

Oh please do not stop now

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By *egselevenMan
5 weeks ago

burnley

mmm keep going xx

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By *vsrTV/TS
5 weeks ago

Sunderland

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By *aninnylonsTV/TS
5 weeks ago

Ipswich

loving this

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By *ature boyMan
5 weeks ago

Erdington

Good start

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By *usan 749ukTV/TS
5 weeks ago

Bangor

Great job

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By *outhdub50Man
5 weeks ago

D18

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By *entleoneMan
5 weeks ago

near heathrow

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By *ub guy 68Man
5 weeks ago

Keith

Great story fella

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By *harliesfunMan
5 weeks ago

North Tyneside

Excellent start

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By *dinthewoods69TV/TS
5 weeks ago

travelling around GB

Great story luv it very well written and cannot wait for more x

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By *aypee46Man
5 weeks ago

Nuneaton

This is great 👍👍

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By *esley 60TV/TS
5 weeks ago

PERTH

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By *unfollowerMan
5 weeks ago

Peterborough

Wow….very nice beginning..

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By *otusTV/TS
5 weeks ago

Aylesbury

Mmmmmm, love this, very hot, looking forward to the next instalment!!

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By *at2121Man
5 weeks ago

Swindon /Algarve

Hot

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By *ich65Man
5 weeks ago

Chorley

Oh wow, this is hot

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By *ountyGuy18Man
5 weeks ago

Leicester Groby Road

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By *lifunTV/TS
5 weeks ago

derbyshire

This is great set imagination going I love to be doing this fantasy we need more now Hun xxx

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By *erry55Man
5 weeks ago

Portlaoise

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By *rbyTV/TS
5 weeks ago

SUNDERLAND

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By *osportNewbieMan
5 weeks ago

Gosport

Great story, very hot

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By *seableMan
5 weeks ago

Halesowen

This is excellent. I would have loved this at 18.

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By *eil B4UMan
5 weeks ago

winchester

Very nice story. A little more detail please, on those moments of ‘no return’.

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By *endeepMan
5 weeks ago

Gt Yarmouth

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By *awkeye13Man
5 weeks ago

sunnieside

Omg this is so hot 🔥

More please

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By *ohnny 51Man
5 weeks ago

Middlewich

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By *ice Bi BoyMan
5 weeks ago

Prenton, Wirral

Oh yes!!!! More please.

I love being spitroasted in my tiny nix.

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By *ibblerMan
5 weeks ago

Dublin

Very good

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By *tephanie Somtimes OP   TV/TS
5 weeks ago

South Derbyshire

The next few days at work I was like a bitch on heat. I asked myself, did young men like me have a menstrual cycle or was it my biorhythms? Maybe hormones, after all I had developed puffy breasts and big nipples not to mention my rounded bottom and hips.

Whenever Harry came near me I got so hot and sweaty. I was loving all the attention he was giving me, the little touches, groping my bottom.

We became more daring with him standing beside me fondling my bottom while serving a customer. Sometimes I would reach behind me and squeeze his cock through his trousers.

I so wanted to feel his cock in the flesh maybe even drop to my knees and suck it but he wouldn't let me. He wanted me dressed in the shop but I just couldn't see how I could do that.

He suggested I wear a skirt and stockings and suspenders and if I stood behind the sweet counter no one would see me.

The idea excited me but could I do it. Could I smuggle mums clothes out of the house? I'd worn them for about 15 minutes before but Harry wanted me dressed all day.

I was so desperate to be girly and even more desperate to experience what it was like to be a girl. Fully a girl, with a man's cock inside me, kissing, feeling a man's rough stubble against my face. Legs open, a man between them or on all fours with my bum in the air feeling deliciously vulnerable. I wanted it all.

To encourage me Harry got me another magazine called LadyLike. It had a section inside entitled, Mirror Mirror. It was for young men like me to show how they transitioned to girls. The girls looked very glamorous but they were all wearing nice wigs and strappy heels and I didn't have either.

I mentioned this to Harry and also asked about Sid and the office girls uniform.

He said Sid hadn't got it yet but he was working overtime on Saturday and would be able to get the items then.

He then picked up the Exchange & Mart, and asked if I'd seen it, I said of course. He then asked if I'd looked in the pages towards the back, I hadn't.

He turned to the back pages and showed me some adverts for theatrical supplies which included wigs and heels in larger sizes.

He said if he bought me a wig and some heels would I fully dress for him in the shop. I replied yes but to be honest I wasn't sure if I had the nerve.

The next day I arrived at work early, Harry was beaming from ear to ear. He pointed to an old battered suitcase and said take a look in there.

I opened the suitcase and my eyes lit up it was full of pretty clothes. Blouses and skirts, dresses, panties a couple of bras, a corset and even a bag of makeup.

I asked where it came from and he said his wife June was having a clear out and asked him to take it all down the tip.

I asked if I could try some of it on and he suggested I put on a fashion show for him. I said I would but that I wouldn't be venturing out in the shop.

Then the bell rang and Harry had to go and serve a customer.

Mum didn't have a corset so that was the first thing I tried on. June, Harry's wife was a lot bigger than me so I got it on quite easily. Luckily being young I was quite supple and managed to slowly tighten the laces at the back.

The corset was white satin with powder blue accents on the suspenders. It didn't pull me in much but it certainly pushed up my puffy titties and made them more defined. The cups were a bit loose but this just showed off my cherry red nipples that were as hard as rock.

Harry walked in and said, "Wow, you look hot"

I did a twirl for him and wiggled my bare bottom at him.

"Oh my", he said, "Look at your little titties, they look so suckable"

"Thank you kind Sir", I replied in my best girly voice.

He grabbed me by the ass and pulled me against him.

He gently ran his fingers down the crack of my ass and asked if I'd ever kissed a man before. I shook my head.

"Would you like to"? He asked.

"I'm not sure", I replied

"Shall we try", he asked and I nodded.

He kissed me gently on the lips. His lips felt surprisingly soft not unlike a woman’s.

I could feel that we were both getting hard.

Then his kissed became more passionate and I could feel his rough stubble against my smooth face. Oh my there was no doubt now that I was kissing a man.

I started to tremble.

In between his kisses I whispered that I was going to cum and he held me closer to him.

For the second time I just exploded without touching myself.

Harry held me tight but I wanted to run.

He kissed my neck and told me how beautiful I was.

I stepped back and saw a big wet patch on Harry's trousers. I asked him if he'd cum but he said no it was my cum.

This made me feel even more guilty and I told him I was so sorry. He reassured me that it was fine, it was lovely and that I was so sweet.

There was a ding and Harry had to go and serve another customer.

I undid the corset being careful not to get it covered in cum and put it back in the suitcase.

I cleaned myself up in the toilet and put on my male clothes although as usual my jeans were ladies.

Harry came back and asked me how I was.

I felt a little sheepish and guilty but it wasn’t as bad as last time. At least I could look him in the eye.

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By *otwillyMan
5 weeks ago

Scunthorpe

Good story

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By *ature boyMan
5 weeks ago

Erdington

Lovely moment

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By *iss WednesdayTV/TS
5 weeks ago

Stortford

I wish someone had a suitcase like that for me x

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By *egselevenMan
5 weeks ago

burnley

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By *umlover71Man
5 weeks ago

Lowestoft

Fantastic. X

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By *aney RopesTV/TS
5 weeks ago

Gourock

More please

Jane x

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By *ikki1970Man
5 weeks ago

leicester

Loving this

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By *ynetteTV/TS
5 weeks ago

BOLTON

more please x

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By *enbiCheshireMan
5 weeks ago

North west

Excellent

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By *illmecreviceMan
5 weeks ago

Reading

Lovin it

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By *edro208Man
5 weeks ago

sheffield

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By *erry55Man
5 weeks ago

Portlaoise

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By *onmaccTV/TS
5 weeks ago

glasgow

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By *edigree69Man
5 weeks ago

Broughton Astley

I remember the Whitehouse magazine. It was really advanced for its time but today’s internet porn makes all those old mags look tame.

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By *orkDefenderMan
5 weeks ago

Wakefield

This is a good story

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By *rbyTV/TS
5 weeks ago

SUNDERLAND

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By *ohnny 51Man
5 weeks ago

Middlewich

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By *orth yorks guyMan
5 weeks ago

Castleford

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By *ac6969Man
5 weeks ago

leeds

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By *obbi_sutherlandTV/TS
5 weeks ago

Ardgay

The suitcase sounds fun

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By *isherman70Man
5 weeks ago

Bexley

Great story more please xx

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By *ibblerMan
5 weeks ago

Dublin

So nice

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By *atnat54TV/TS
5 weeks ago

Bexhill-on-Sea

Loving this

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By *issykissyMan
5 weeks ago

York

got very wet and hard reading the newest upadate

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By *esliebTV/TS
5 weeks ago

Scunthorpe

My first porn magazine was "Parade"

It was more or less a step up from page 3

Just tits, the pussies were airbrush out.

I had many 30 seconds wank in the early days

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By *ackotoolMan
5 weeks ago

Edinburgh - fountainbridge

I am loving this story

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By *ard8onMan
5 weeks ago

Darwen

Loving this

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By *alpalMan
5 weeks ago

Scartho, Grimsby

Interesting to see this story developing

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By *ritney LingerieTV/TS
5 weeks ago

Rotherham

I remember the he to she adverts in the exchange and mart.

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By *tephanie Somtimes OP   TV/TS
5 weeks ago

South Derbyshire

I went home that evening feeling more accepting of what I'd done with Harry. I loved his kisses, especially when his tongue was in my mouth it felt so naughty.

I still kissed my dad goodnight but only ever on the cheek but I have to admit that his rough stubble aroused me. Not that I had any interest in my dad in that way. I would never think of Harry as a dad he was more of a naughty uncle.

The next morning at work I noticed the suitcase had gone. I asked Harry and he said he'd hidden it, just in case June his wife popped in.

I told him it would turn me on if June caught us in a compromising position. Harry coughed and spluttered on his breakfast and said it would mean divorce and bankruptcy.

I told him that I'd fantasised about my girlfriends mother catching me with a much older man's cock in my mouth.

He laughed and said, "You're brave this morning".

He was right, I'd had a very naughty dream and I was feeling so horny.

I dropped onto my hands and knees and crawled over to Harry.

"Fuck, where has this come from Stuart"? he asked incredulously.

I didn't know where it had come from but I felt incredibly naughty.

I looked up at Harry and ran my hand up the inside of his thigh. As usual his thick cock was hanging down his leg. I kissed it gently through his trousers. Then mouthed it up and down, he soon got rock hard.

I looked up at him with my big doe eyes, his beg belly hanging over his trousers and undid his belt and fly.

I pulled his trousers down around his ankles and began kissing his bulge through his Y fronts. His pants were wet with a mixture of my saliva and his pre-cum. I was pleased to see for an old man he could still get rock hard. I was about to take his cock into my mouth when there was a ding.

It was a customer, the first of many that morning. Harry straightened himself up and I went in search of the suitcase.

I don't know what was the matter with me but I felt so horny and so naughty. Again I wondered if guys like me had menstrual cycles. I was obviously different to other lads my age.

When my boobs started growing mum took me to the doctors. He was quite an old guy who muttered something about a hormone imbalance but basically told us it was just a bit of puppy fat. The trouble was I wasn't fat, I just had tits. At school the other lads teased me and I hated PE.

Anyway I was so horny not for girls but for men, older men like Harry. It felt taboo with me being 18 almost 19 and Harry in his 50's but that was part of the attraction.

Eventually I found the suitcase with June's clothes in and searched through it.

I found a black lacy bra, size 38C. I put it on, it fitted fine but the cups were way too big. It was a full cup underwired bra with lots of side support. June was a big woman and needed it I guess.

Harry called me to help in the shop but I was having fun and ignored him.

I got a pair of scissors from the kitchen and carefully cut out the cups. I put the bra back on. This was better the wide sides of the bra helped gather up my boobs and push them out. My mate called bras like this cowboy bras because they headed them up and moved them out, lol.

I got the impression that June liked warm colours whereas I preferred cooler colours. She was also quite conservative there was nothing sexy here apart from the corset.

I did find a black top with a lace trim that was nice so I slipped that on. I loved the way the open cup bra allowed my nipples to poke through the thin material.

The panties I found were simple burgundy cotton ones but I slipped them on. Most of the skirts were long and I wanted something short but I found a flowery summer skirt with an elasticated waist band. I was able to roll it up to make the skirt shorter so I slipped that on.

I found some stockings but no suspender belt apart from on the corset. There was some sheer laddered tights so I slipped those on instead.

They reminded me of the time I played one of the seven dwarfs in a school play and had to wear my sisters green tights.

Mum said I had more shapely legs than my sister. That comment really made her cross.

Then I opened the make-up bag. Dare I wear some make-up and go into the shop?

Although I had long shoulder length hair it wasn't cut in a girls style. Harry had mentioned a wig in the back of Exchange & Mart but I didn't really want to wear and wig and how would I hide all my own hair anyway?

In the make-up bag was a few lipsticks, two tubes of mascara, some eyeshadow, a compact with foundation and an eyebrow pencil.

I was well aware that to remove some makeup you needed makeup remover. However I wanted to try some mascara.

Harry was getting really annoyed in the shop I could hear the bell dinging but I couldn't go in and help as I was dressed like a girl.

I went into the toilets and stood in front of the mirror. The mascara had almost dried out but I managed to put some on my eyelashes. The transformation was immediate. I wouldn't say I looked like a girl but I did look like a nancy boy. I found a lipstick I liked called 'Rock on Plum' and applied that rather haphazardly to my lips.

I thought I'd looked quite sweet but my hair didn't look quite right.

Then I remembered some pink ribbon left over from Christmas. I gathered my hair together into ringlets and tied it together using the ribbon.

I stood on a chair to see how I looked in the mirror. What I was wearing was all a bit of a miss-match but I felt girly and quite cute.

I walked through the back to the shop and stood in the alcove. From here I knew that Harry could see me but the customers couldn't.

I stood there holding the hem of my skirt with one hand and sucking my thumb with the other gently swinging from side to side. I wanted to give Harry the impression I was an innocent young girl. This wasn't really that far from the truth.

Harry's eyes nearly popped out of his head.

"Where have you been you naughty young lady", he asked, going along with my ruse. "Come here".

I shook my head and in my best girly voice said, "Come and get me".

There was another ding and another customer came into the shop.

I stepped back a bit just in case but carried on acting the girl. Gingerly lifting the hem of the skirt up to show Harry my panties.

Harry kept looking over and then I ran my fingers gently over my nipples while licking my lips.

I could see he was rock hard with his thick cock sticking half way down his leg.

The customer left and he started walking towards me.

"I'm going to fuck you", he growled.

I put my finger to my lips and went, "Ooohhh".

I was loving flirting with him and when he got close I ran into the storage room.

We were either side of some boxes and he couldn't get to me but I so wanted him to.

Then there was another ding and Harry went back into the shop.

I went back and stood in the alcove teasing him as he served the customer.

Then he disappeared onto the other side of the counter.

He'd gone for over a minute so I edged into the shop. Then I noticed he'd pulled the window blind down. I looked over the sweet counter. Harry had put the CLOSED sign up at the door and I knew I was in trouble

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By *obobMan
5 weeks ago

Harold’s Cross

Fantastic story

More please

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By *aypee46Man
5 weeks ago

Nuneaton

Big trouble 😛😛😛😛

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By *ameulTV/TS
5 weeks ago

norwich - ish

Please keep going

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By *atinbloodMan
5 weeks ago

Birkenhead

Tell us more

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By *eeking smooth sissiesMan
5 weeks ago

Bournemouth

Beautiful story and very horny !!

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By *merald toyTV/TS
5 weeks ago

bicester

Lovely story

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By *otusTV/TS
5 weeks ago

Aylesbury

Such a horny read and so well written, looking forward to the next part - now Harry has shut the shop!

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By *otwillyMan
5 weeks ago

Scunthorpe

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By *ich65Man
5 weeks ago

Chorley

Mmm... this is going to be fun

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By *rianishardMan
5 weeks ago

Cambridge

Wow so good, glad it's back x

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By *onmaccTV/TS
5 weeks ago

glasgow

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By *ibblerMan
5 weeks ago

Dublin

O can't wait

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By *ocklover50100Man
5 weeks ago

Gloucester

More please. Lovely story

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By *rbyTV/TS
5 weeks ago

SUNDERLAND

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By *lderoneMan
5 weeks ago

Cheadle Hulme

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By *ashtoolMan
5 weeks ago

belfast

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By *ardsoloMan
5 weeks ago

Harlow

So good

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By *agerforbothMan
5 weeks ago

perth

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By *ei7Man
5 weeks ago

Wembley

Sensational!

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By *ac6969Man
5 weeks ago

leeds

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By *atietv1TV/TS
5 weeks ago

co. Durham

Wow x this so hot

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By *rdiscreet327Man
5 weeks ago

notts

You’re in trouble now the shop has closed!

Incredible writing op.

Loving every minute of this!

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By *ohnny 51Man
5 weeks ago

Middlewich

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By *ikki1970Man
5 weeks ago

leicester

Loving this

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By *illgossardTV/TS
5 weeks ago

Walton on Thames

Oh this is good. Keep going please

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By *iss WednesdayTV/TS
5 weeks ago

Stortford

can't wait for what happens next

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By *aney RopesTV/TS
5 weeks ago

Gourock

More please

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By *ictor36Man
5 weeks ago

Essex

The voyeur in me is hoping he didnt lock the door!

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By *ake64Man
5 weeks ago

Aberdeen

Amazing more please

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By *honabicdTV/TS
5 weeks ago

Cornwall


"The next few days at work I was like a bitch on heat. I asked myself, did young men like me have a menstrual cycle or was it my biorhythms? Maybe hormones, after all I had developed puffy breasts and big nipples not to mention my rounded bottom and hips.

Whenever Harry came near me I got so hot and sweaty. I was loving all the attention he was giving me, the little touches, groping my bottom.

We became more daring with him standing beside me fondling my bottom while serving a customer. Sometimes I would reach behind me and squeeze his cock through his trousers.

I so wanted to feel his cock in the flesh maybe even drop to my knees and suck it but he wouldn't let me. He wanted me dressed in the shop but I just couldn't see how I could do that.

He suggested I wear a skirt and stockings and suspenders and if I stood behind the sweet counter no one would see me.

The idea excited me but could I do it. Could I smuggle mums clothes out of the house? I'd worn them for about 15 minutes before but Harry wanted me dressed all day.

I was so desperate to be girly and even more desperate to experience what it was like to be a girl. Fully a girl, with a man's cock inside me, kissing, feeling a man's rough stubble against my face. Legs open, a man between them or on all fours with my bum in the air feeling deliciously vulnerable. I wanted it all.

To encourage me Harry got me another magazine called LadyLike. It had a section inside entitled, Mirror Mirror. It was for young men like me to show how they transitioned to girls. The girls looked very glamorous but they were all wearing nice wigs and strappy heels and I didn't have either.

I mentioned this to Harry and also asked about Sid and the office girls uniform.

He said Sid hadn't got it yet but he was working overtime on Saturday and would be able to get the items then.

He then picked up the Exchange & Mart, and asked if I'd seen it, I said of course. He then asked if I'd looked in the pages towards the back, I hadn't.

He turned to the back pages and showed me some adverts for theatrical supplies which included wigs and heels in larger sizes.

He said if he bought me a wig and some heels would I fully dress for him in the shop. I replied yes but to be honest I wasn't sure if I had the nerve.

The next day I arrived at work early, Harry was beaming from ear to ear. He pointed to an old battered suitcase and said take a look in there.

I opened the suitcase and my eyes lit up it was full of pretty clothes. Blouses and skirts, dresses, panties a couple of bras, a corset and even a bag of makeup.

I asked where it came from and he said his wife June was having a clear out and asked him to take it all down the tip.

I asked if I could try some of it on and he suggested I put on a fashion show for him. I said I would but that I wouldn't be venturing out in the shop.

Then the bell rang and Harry had to go and serve a customer.

Mum didn't have a corset so that was the first thing I tried on. June, Harry's wife was a lot bigger than me so I got it on quite easily. Luckily being young I was quite supple and managed to slowly tighten the laces at the back.

The corset was white satin with powder blue accents on the suspenders. It didn't pull me in much but it certainly pushed up my puffy titties and made them more defined. The cups were a bit loose but this just showed off my cherry red nipples that were as hard as rock.

Harry walked in and said, "Wow, you look hot"

I did a twirl for him and wiggled my bare bottom at him.

"Oh my", he said, "Look at your little titties, they look so suckable"

"Thank you kind Sir", I replied in my best girly voice.

He grabbed me by the ass and pulled me against him.

He gently ran his fingers down the crack of my ass and asked if I'd ever kissed a man before. I shook my head.

"Would you like to"? He asked.

"I'm not sure", I replied

"Shall we try", he asked and I nodded.

He kissed me gently on the lips. His lips felt surprisingly soft not unlike a woman’s.

I could feel that we were both getting hard.

Then his kissed became more passionate and I could feel his rough stubble against my smooth face. Oh my there was no doubt now that I was kissing a man.

I started to tremble.

In between his kisses I whispered that I was going to cum and he held me closer to him.

For the second time I just exploded without touching myself.

Harry held me tight but I wanted to run.

He kissed my neck and told me how beautiful I was.

I stepped back and saw a big wet patch on Harry's trousers. I asked him if he'd cum but he said no it was my cum.

This made me feel even more guilty and I told him I was so sorry. He reassured me that it was fine, it was lovely and that I was so sweet.

There was a ding and Harry had to go and serve another customer.

I undid the corset being careful not to get it covered in cum and put it back in the suitcase.

I cleaned myself up in the toilet and put on my male clothes although as usual my jeans were ladies.

Harry came back and asked me how I was.

I felt a little sheepish and guilty but it wasn’t as bad as last time. At least I could look him in the eye."

fabulous story that I can relate 2 x

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By *asher72Man
5 weeks ago

Newton Abbot

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By *alpalMan
5 weeks ago

Scartho, Grimsby

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By *ully fashioned slutMan
5 weeks ago

norwich

Loving it

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By *lasgowlatexMan
5 weeks ago

Glasgow

Mmmm very nice story

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By *ustjanMan
5 weeks ago

bristol

Love This storey

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By *ature boyMan
5 weeks ago

Erdington

Getting interesting

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By *seableMan
5 weeks ago

Halesowen

So annoying when people repost a long post from the OP and just add a line at the bottom saying they like it

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By *ibblerMan
5 weeks ago

Dublin

O please finish

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By *illyoneMan
5 weeks ago

Hailsham

Mmmm very good writing. Made my cock hard. Please write more.

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By *ndrews642Man
5 weeks ago

exeter

Great story and would love to be dressed for someone like this to use me

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By *iredmodemMan
5 weeks ago

Westhoughton

Correct,so annoying

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By *usan 749ukTV/TS
5 weeks ago

Bangor

Excellent

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By *orth yorks guyMan
5 weeks ago

Castleford

You are a naughty gurl

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By *erry55Man
5 weeks ago

Portlaoise

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By *egselevenMan
5 weeks ago

burnley

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By *um lover111Man
5 weeks ago

Biggleswade

Bloody brilliant

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By *ip73Man
5 weeks ago

Stanwell

I think you're going over Harry's knee with your knickers down

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By *ubsteffTV/TS
5 weeks ago

Portsmouth

This is very good!!

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By *lutty Sara2020Man
5 weeks ago

stratford

I’m loving this your going to get exactly what you deserve

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By *rickyWire1Man
5 weeks ago

Warrington

Looking forward to reading what Harry did with the Teasing little Slut

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By *ammtMan
5 weeks ago

newcastle under lyme

Love this so horny

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By *issychrissyMan
5 weeks ago

Greenhithe

Oh Stephanie, more pleeas xx

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By *carf57Man
4 weeks ago

arctic

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By *avenMan
4 weeks ago

Yeovil


"So annoying when people repost a long post from the OP and just add a line at the bottom saying they like it "

Agree totally.Whats the point?

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By *seableMan
4 weeks ago

Halesowen


"So annoying when people repost a long post from the OP and just add a line at the bottom saying they like it

Agree totally.Whats the point?"

Perhaps some people have an overwhelming need to display their stupidity in public?

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By *tewartfoster1Man
4 weeks ago

Wolverhampton

Mmm

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By *ibblerMan
4 weeks ago

Dublin

You must finish

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By *avidIanMan
4 weeks ago

Bolton

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By *imale999Man
4 weeks ago

dudley

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By (user no longer on site)
4 weeks ago

So horney need to see the rest please, loved the days of being mollested by older men when i was a lad.

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By *olflord07TV/TS
4 weeks ago

exeter

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By *harliesfunMan
4 weeks ago

North Tyneside

Great

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By (user no longer on site)
4 weeks ago

Hey op can we have some more please

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By *egselevenMan
4 weeks ago

burnley

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By *ovemynipsMan
4 weeks ago

Aldershot

Please don’t keep us waiting this is so hot I need more

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By *ardsoloMan
4 weeks ago

Harlow

Definitely need more

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By *ceerMan
4 weeks ago

Hadleigh

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By *lifunTV/TS
4 weeks ago

derbyshire

Nice gentle story that keeps you hooked loving this hope there's more soon well written beautiful more please xxx

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By *avidIanMan
3 weeks ago

Bolton

Yes more please

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By *avidIanMan
3 weeks ago

Bolton

[Removed by poster at 15/08/25 10:04:58]

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By *um lover111Man
3 weeks ago

Biggleswade

Take it this isn't coming back as it's been 2 weeks now

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By *samtv1TV/TS
3 weeks ago

Northampton

So hot x

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By *imon_hydeMan
3 weeks ago

Bredbury, Stockport

Great thread, such a turn on

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By *ay_WP9Man
3 weeks ago

cheam

Just found this thread. Very interesting and beautifully written (which makes all the difference)

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By *ashtoolMan
3 weeks ago

belfast

Steff hope there is more to cum

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By *annasuckcockMan
3 weeks ago

ibstock

Loving this

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By *v-simoneTV/TS
3 weeks ago

Brislington, Bristol

Great story

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By *awtyboy71Man
3 weeks ago

Bradford

Hope there is more cumming x

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By *nigmameMan
3 weeks ago

Aylesbury

Great story and well written, can’t wait for more x

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By *ovesuckingcock39Man
3 weeks ago

aberchirder

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By *ibblerMan
3 weeks ago

Dublin

Is there more

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By *reenockboyMan
3 weeks ago

greenock

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By *rbyTV/TS
3 weeks ago

SUNDERLAND

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By *ick682024Man
3 weeks ago

swindon

Would live to hear more

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By *acyboyTV/TS
3 weeks ago

Southampton

Shame this has dried up

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By *usan 749ukTV/TS
3 weeks ago

Bangor

I was thinking the same thing

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By *eenet1Man
3 weeks ago

Chester

Mine was Fiesta.

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By *lder bi guyMan
2 weeks ago

telford

wish there was more alas not

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By *lf123Man
2 weeks ago

near you

Mmm liking this

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By *ust_havin_funMan
2 weeks ago

mine

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By *tephanie Somtimes OP   TV/TS
2 weeks ago

South Derbyshire

There is more to come but I've been away

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By *egselevenMan
2 weeks ago

burnley

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By *ottomnewbridgeMan
2 weeks ago

Newbridge

Loving this

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By *tephanie Somtimes OP   TV/TS
2 weeks ago

South Derbyshire

Harry came walking towards me like John Wayne in a cowboy film, his fat cock sticking down his leg. I knew I was in trouble. I enjoyed flirting but now I had to come up with the goods.

For a split second I thought about running but when Harry pinned me to the wall with both arms under mine I knew there was nowhere to hide.

Although I had tits and a rounded bottom I was still slim. Harry on the other hand was big and broad. I don't know what it was about men's bellies but I loved them.

Harry held me against the wall and gently teased my nipples with his thumbs. I closed my eyes and sighed, it felt so good. Then he cupped my breasts while kissing my neck.

"There's quite a handful here", he whispered.

"There is here", I whispered back, reaching between his legs.

Harry slipped his hand up my blouse.

He looked at me I opened my mouth slightly and he brushed his lips against mine. His lips were full and soft like plump pillows but his stubble was rough and that really turned me on.

As we kissed I undid his overall and ran my hands over his broad chest and down his strong arms. Harry had defined chest and hard nipples. There were wisps of dark hair showing around the open neck of his shirt.

I whispered in his ear, "I want to feel your weight on top of me. I want to open my legs and feel you inside me".

He slipped both hands down the back of my skirt and pulled me towards him grinding his groin against mine. I could feel his hardness and I wanted him to make me his girl, fully and in every way possible.

I could feel his finger against the crack of my ass. Then a ripping sound as he tore off my laddered tights.

With one hand he pulled my panties to one side and with the other he explored my bottom.

I was squirming on his hand desperate to be fingered like a girl.

He circled my rosebud with his finger. I was holding onto him as little electric shocks of pleasure ran through my body my legs trembling with excitement.

I knew I was tight. I had started playing with mums vibrator but it was a solid plastic one that dad had bought her from a novelty shop while on holiday.

Harry spun me around against the wall and I naturally arched my back and pushed my bum out.

He dragged my panties down to my ankles over what was left of my tights.

He pushed my legs further apart with his feet, my panties stretched between my legs like I was tied. I felt so deliciously vulnerable in this position,

He hitched up my skirt and buried his head between my ass cheeks. His tongue was warm and wet and his stubble rough against my smooth ass cheeks.

I loved this position. I quickly realised that vulnerability was key to being a sissy. Men were not supposed to enjoy it but I loved it. It excited me and made me feel so girly.

I reached around and held my ass cheeks open. I felt so exposed with the cool air on my rosebud. Harry was licking, slurping and probing my ass literally feasting on it like a man that hadn't eaten for days.

Then he started fingering me, oh my it felt so good.

I could feel myself getting wetter, I reached around and fingered myself. I was beginning to open up.

Harry ordered me to lick my fingers and I did as I was told. Then he grabbed my arm placing my hand on my ass and told me to do it again. I did as I was told fingering myself then licking my sticky fingers.

Harry pulled me down into the shop and bent me over the counter. I lay over the newspapers on tiptoes with my ass in the air.

"I always wanted you mother like this", he laughed. "I never imagined it would be you I would be fucking over my counter".

I held onto the far side of the counter my ass in the air and watched as Harry got out his fat cock.

I'd never really seen it in the flesh before I'd only kissed it through his briefs. It was fat with a very fleshy foreskin. Tt was hard but his glans were only just poking out. It looked so suckable and I wanted to run my tongue around his foreskin.

Harry grabbed my waist and pulled me towards him rubbing his cock up and down my ass crack. I wiggled and rolled my wet bottom up and down his cock eager to experience what it was like to be a girl.

Harry took hold of his cock and guided it towards my little hole. We both pushed but I was still to tight to take his fat cock inside me.

I reached around and pulled my ass cheeks open, I could feel my hole being stretched but I was still too tight.

Then Harry got a tin of shaving foam from the shelf and sprayed it over my ass. It smelt so fresh and masculine but it did the treat and loosened me up for Harry to enter me.

His fat cock popped inside me and straight away I started to cum. I didn't know about my prostate back then but every time his cock grazed against it cum dripped from my cock onto the floor.

It wasn't like cumming from having a wank it was like the cum was being pushed out from inside. There was no loss of desire or a climax but I was cumming with each thrust.

He worked my ass quite slowly, I could feel myself getting fuller and fuller my legs trembling as I was on tip toes leaning over the counter.

I started pushing back on him to meet his thrusts. It took a few seconds for us to get into sync but when we were it was fantastic.

Soon he was pounding my ass so hard I could feel his balls slapping against me. The feelings were intense sometimes it felt like too much excitement too much pleasure if that was such a thing.

I was whimpering and moaning with each thrust I felt sure people outside the shop could hear me but at that point I didn't care.

Harry kept calling me his little slut his dirty bitch which made me wiggle and jiggle my bottom even more.

I joined in telling him what a naughty man he was fucking an innocent girl like me. How I was such a dirty bitch with a man's cock up my ass.

Then we heard something neither of us expected to hear. The ding of the bell over the door.

We both looked up, time seemed to slow to a crawl. I watched as the door slowly opened.

Harry muttered the words, "Fuck, I didn't lock it"

I thought I heard my mums voice but it was like we were frozen unable to move.

The door opened further....

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By *ikki1970Man
2 weeks ago

leicester

So glad this has resumed, loving it

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By *rucker for tvMan
2 weeks ago

Banffshire area tonight

Brilliant story thanks.

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By *ashtoolMan
2 weeks ago

belfast

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By *ich65Man
2 weeks ago

Chorley

So glad your back with this great story 😈🥒💦

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By *erry55Man
2 weeks ago

Portlaoise

Glad you are back Stephany, great story.

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By *orkDefenderMan
2 weeks ago

Wakefield

Wonderful

Will they get caught?

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