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cross dressing in my uncles shed

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

It’s difficult for us cross dressers who still that deep desire and need to dress, but are stuck at home and financially dependent on their wives and dare not admit our secret. I did have a job that allowed me to travel and that’s when I took the opportunity to dress (and I had a lot of fun), but for the last 12 years, I have been the “house husband”, as the wife’s career took off (she is a GP) . When we first moved here it was ok, as soon as I got the kids off to school, and the “house work” done I would shut the curtains and dress and relax (hiding my fem cloths in the loft).. but now the kids make their own way to school and the eldest has left and spends a lot of time at home. Yes there is still some opportunity to dress during the day, but it’s risky to do anything outside my bedroom, and I have to be so careful not to leave anything out by accident. Also, we now have many friends who live near, and our neighbours are very close, so arranging for men to visit me is out the question, as is walking round the house dressed. My wife does not go for anything other than jeans our trousers, she very rarely wears make up and does not own a pair of shoes with any size of heel “not practical” she says,,,- so I can’t even get excited wearing her stuff.. and what I want to wear would simply repulse her (short skirts and heels , stockings and lots of makeup). I tried to go out in the car during the day and dress, and visit men at their houses – but so many time wasters and not enough time to get out the area as to avoid risk of been seen. So, 2 years ago I gave up…… But this was all about to change thanks to my uncle. Let me explain…….

The allotment had been my Uncles, and I took it on without having really much interest in gardening. It had a large shed, and that would be the ideal place for me to hide my female cloths and spend some time dressed. My wife has no interest whatsoever in gardening – so this was the ideal opportunity.

No doubt for many readers this does not sound very glamourous, but for me it was the perfect opportunity to rekindle my age-old hobby as a trannie…

The allotment was not very big, but the shed was amazing. It was at the end of a row of about 30 plots, so not overlooked, and very private. My uncle was very handy, and he had managed to tap into the communal water supply, so it had a sink, solar panels, a small wind turbine, and a generator he had even made an outdoor compositing toilet.

From the outside it looked like a typical garden shed, albeit a very big one, - but inside it was much more. As you went in it looked like a potting shed, but it was fixed against a large shipping container which had been transformed - it was something else. Very secure with a steel door and heavy duty locking system, and inside he had fitted out with quality wooden flooring, all fully insulated, sofa, sat TV, and a bar across the back wall. Large windows with amazing views over the field to the woods at the back.

I had to do a little bit of gardening, just to tend to already well-pre pared beds left by my uncle, so to be honest, an hour in the garden was all I needed to keep on top of things with plenty of time to dress.

I managed to acquire a large double wardrobe and a dressing table and over the next few months built back up my collection of dresses, wigs, shoes, make up and a few toys - and even fitted a couple of security video cameras so I could keep an eye on things from an app on my phone, and also record me dressed, which I liked to do occasionally.

For the first few months, I would just dress, sit and watch TV, have a drink, go online on fab and chat with friends and sometimes get the toys out and play with myself, or go on cam.

My wife was so pre occupied with her career, she was just pleased that I had found a hobby and was enjoying it. She would almost push me out the house when she wanted to watch her favourite tv program on an evening (that I hated) - “why don’t you go and do something at the allotment” she would say – so me being at the allotment was never an issue.

This was perfect, don’t get me wrong, my wife and I are close, and have a great life, she has always felt guilt about me having to give up my career, and never complains about my new found love of gardening…..

As time went on, my desire to do more grew. Maybe find another local cross dresser to play with, or arrange to meet men at the shed… but my paranoia about being outed in the village prevented this.

I wanted so much to try going for a walk outside dressed, and had worked out that after 7pm, most of the people would have left, and there was a short, private pathway leading from the back of my allotment to the woods. I wanted to see what it would be like to go for a walk in my short black dress, stockings, wig and heels. I often fantasied about doing this, bumping into a man walking his dog, and letting him chat me up and taking me into the woods and letting me give him a blow job. The only problem with this fantasy was my paranoia about someone local recognising me and this getting back to my wife (who as a GP is known to nearly everyone in the village).

Anyway, one particularly dry, cool night in march, I decided to go for it, and take a chance with a walk. I had planned the walk and even practised it before hand in male mode to make sure it would work, as in heels, I did not want to end up stuck in mud .. It was dusk, and I remember how excited I felt, stepping out of the shed for the first time, locking the door and heading out down the pathway. The adrenaline rush was amazing as the cool evening breeze rushed round my stocking clad legs, and I walked out in my heels, full make up, my new long auburn wig – I felt amazing,,,,,

“Are you ok Love” ……….. the words sent a shiver down my spine. I looked round, and nearly died it was Colin. Colin was the chair of the allotment society; he managed the place and had his own patch at the other end of the plot. He was at the top of the list of people I did not want to bump into, and the only reason why I decided to go for the walk this night was that he was supposed to be away. When he told me a few weeks back, that’s what made me decide on this night. I had convinced myself he was away, and did not bother to check.

Colin was a tall guy, thick set, very confident, and had that outdoor rugged look. The total opposite to me….. I had seen him many times over the years when visited my uncle, and tried to keep away from him since he died, exchanging the odd hello here and there, he had tried to call round a few times, but I ignored him.

“yes thanks” I said, “you a friend of Jack’s ” Colin said, “lucky jack” he smiled…. “He is probably in his shed watching tv, he has the best shed here, it was his uncles you know, Joe, he was …..” Colin liked to talk, so I jumped in to stop him..” no its ok, I am Jack’s sister, Jill“ as I turned to head back to the shed, thinking why the fuck did I say that – and Jill- for fucks sake, all I wanted to do was get back inside quick. Colin followed me, and as I tried to unlock the door of the potting shed I dropped the keys,,,, Colin jumped to me rescue, picking up the keys … “”jack and Jill eh” he laughed,,, “you have your own keys” …. “here let me open the door for you, you must be bloody freezing out here dressed like that , he pushed his way in, still talking, telling me all about Joe, and this amazing shed, and how the shoes I was wearing were not very practical for an allotment……… “A drink would be nice Jill, do you still have the bar”, he went on, I used to spend a lot of time here with Joe watching the football on his telly, he had the best shed on the allotment, we used to all come round for drinks.. Joe was great crack, but Jack , we never see much of him”… he went on as he found the key to the steel door and opened it up and walked into the room – which was as I had left it minutes ago, make up on the dressing table, my pink dildo in the middle of the table, my dresses hung against the wardrobe, and my male cloths folded up on a chair in the corner next to my Wellys.

“I will just wait for jack to get back” I said, ,,, but Colin was not listening, and had already walked round to the bar and pulled a bottle of bud from the shelf, opened it, sat on the sofa and was smiling , looking at me…… “for fucks sake jack, I am not stupid”,,,, he said…. “I have known your family for years, and never a mention of a sister…….don’t worry mate, your secrets safe with me,,, I have been watching you on and off for a few weeks now, knew you were up to something in here, often seen you bringing stuff in… now this explains it – you’re a trany…. And I have to say, you look fucking amazing……. Wait till the lads find out……… and what would the Doc say ”

The colour drained from my cheeks, and I felt weak at the knees, panic hit me… , shit shit…. What am I going to do.

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By (user no longer on site)
over a year ago

Please keep going

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By *unboy69888ABCMan
over a year ago

fleetwood

Good start

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By *eckycd41TV/TS
over a year ago

Navan

Keep going xx

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By *r 007Man
over a year ago

harrogate

Fun times

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By *ony 529Man
over a year ago

coventry

Mmm. Loving the story so far please continue

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By (user no longer on site)
over a year ago

So much detail please keep going

I can't wait to read what Colin will do

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By *cotFit4funMan
over a year ago

Kettering

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By (user no longer on site)
over a year ago

Great start

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By *idethesausage2Man
over a year ago

Trowbridge

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By *imale38Man
over a year ago

Barnsley

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By *ardsoloMan
over a year ago

Harlow

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By *ecretpantyTV/TS
over a year ago

lisburn

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By (user no longer on site)
over a year ago

Looking forward to more of this one.

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By (user no longer on site)
over a year ago

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By (user no longer on site)
over a year ago

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By *aria_tiaTV/TS
over a year ago

Bolton

Cracking start

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By *ed01Man
over a year ago

happy ville

Wow

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By (user no longer on site)
over a year ago

Love it

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By *oventry4biTV/TS
over a year ago

coventry

Enjoying this

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By *af105Man
over a year ago

Newtownards

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By *tockton GentMan
over a year ago

Great Ayton

Great story

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By (user no longer on site)
over a year ago

More please

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By *titch69Man
over a year ago

Torbaydos

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By *atexpvcTV/TS
over a year ago

chester/Merseyside

More please...

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By *urabriteMan
over a year ago

stafford

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By (user no longer on site)
over a year ago

“It’s difficult for those of us who are stuck at home and financially dependent on their wives”” OMG!!! Do you know how disgustingly self-centred that sounds?

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By (user no longer on site)
over a year ago

Very hot. More please!

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By *usie pTV/TS
over a year ago

taunton

Lol allotment sheds have an awful lot to answer for.

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By *es for funMan
over a year ago

port talbot

You got to keep this going

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By *icoleSheffieldTV/TS
over a year ago

Sheffield

Loving this story, hopefully plenty of stories to share out of this shed... x

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By (user no longer on site)
over a year ago

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By *r 007Man
over a year ago

harrogate

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By *ubsteffTV/TS
over a year ago

Portsmouth

No other option. Colin must be killed.

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

TWO

I turned to look at him, and was taken a back, as he had his mobile phone and took a picture of me. I tried to hide my face, but not quick enough “that will do for now” he said, as he started to unzip his jeans and pull out his huge thick cock. “I know this is what you want, I bet your gagging for it, don’t worry, you just do as I say and we will keep this as our little secret”….

His cock was fully out of his jeans, and he was stroking it slowly with his big hands…. A mixture of dread and excitement filled me…

“sorry colin, I cannot, can you please leave” I said weakly… “ok, if that’s what you want, and if you don’t mind me showing this picture to your wife next time I am at the surgery”…… “no please, no” I begged him… It was clear I had no choice, and my mixed emotions were getting the better of me now… It had been a long time since I had sucked a cock, and deep down I knew I wanted to…..

I walked towards him, crouched down between his leg’s , his muddy boots either side of my stocking clad legs, he smelt damp and foisty as I placed my hands on his thighs to steady myself and moved my face closer to his cock. “good girl” he said,,,, “smell it Jill, your going to be doing this many more times after today, now open wide” .. He slipped his warm musky cock between my lips, and I took it all in slowly till I gagged, he pushed my head down , gripped me and started to face fuck me, pulling my head up and down over his cock as I gagged, almost throwing up as salvia dripped from my mouth , his huge thick cock slamming against the back of my throat… OGGG,UGGHH OGHH ,, he slammed his cock harder down my throat “gona have some fun with you” he said… as I tried to keep my composure…

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By (user no longer on site)
over a year ago

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By *ecretpantyTV/TS
over a year ago

lisburn

I bet you where hard in your panties when he was making u suck him.

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By *akeyjohnMan
over a year ago

ossett

Hmmmmmm more plz

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By (user no longer on site)
over a year ago

Can't wait for more!

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By (user no longer on site)
over a year ago

This story is fantastic, please carry on, I used to see a guy who used me in very similar circumstances.

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By *tephbicdTV/TS
over a year ago

Northamptonshire

Love it x

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By *un Bi couple yorkshireCouple
over a year ago

york thorganby

Excellent start xxx

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By *reedyannaTV/TS
over a year ago

Swaffham

Mmmm yummy

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By *aughty grease monkeyMan
over a year ago

Coventry

Do tell more fantastic horny hot story xx

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By *.A.MGUY55Man
over a year ago

littleborough

omg just what i want an allotment to play in an meet dom guys

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By *un couple 2Couple
over a year ago

Tynemouth.

We have loads of fun at our allotment

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By *cubasexMan
over a year ago

Dudley

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By (user no longer on site)
over a year ago

Great story

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By *mrmarkMan
over a year ago

tavistock

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By *es for funMan
over a year ago

port talbot

Love it

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By *cotFit4funMan
over a year ago

Kettering

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By *iving for todayMan
over a year ago

stirling

Good story

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By *r 007Man
over a year ago

harrogate

good girl

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By *titch69Man
over a year ago

Torbaydos

I also need to get a allotment lol

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By *unboy69888ABCMan
over a year ago

fleetwood

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By (user no longer on site)
over a year ago

Great story

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By *dam5805Man
over a year ago

Bristol

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By *hantelle-La-SlutTV/TS
over a year ago

South Birmingham

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By *ed01Man
over a year ago

happy ville

Ohh you lucky

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By (user no longer on site)
over a year ago

Excellent horny start looking forward to the next installment baby oil at the. Ready

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By *af105Man
over a year ago

Newtownards

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

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By *usie4uTV/TS
over a year ago

Havant


" "

More please xx

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By *ohncukMan
over a year ago

london

Loving this, more please

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By *imale38Man
over a year ago

Barnsley

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

Three

He continued to face fuck me for a long time, pushing hard and the gagging was starting to hurt my throat… His release was welcomed as he pulled back and sprayed a hot jet of thick gooey cum over my face, …. “clean it up jack” he said, “lick my cock clean”,,,, I did as he said, licking round the tip of his cock, suckling the strings of cum into my mouth as he took another picture of me as I sucked the last bits of cum from his cock, catching the drips down his shaft with my tongue …

I sat back on the floor below him as he finished his drink… “going to have some fun with you jack” he said, “or should I say Jill” ,,,, “just do as I say and your secret will be safe”,,,,,,, he went on as he looked at the pictures he had taken of me on his phone….. “I have to say, you look good considering you are a bloke, I could quite fancy you”, he said,,, “that was a good blow job as well, best I have had for some time now”….. Thankyou I replied, ,,,,, “good girl” …… “did you enjoy it” he asked, “err,,, yes , but it was a bit rough “ I replied meekly ……………

“Good, don’t fucking care if you enjoyed it or not, in fact I don’t want you to fucking enjoy it, I want you to be my fucking slut ,,,,, so let’s have a better look at you all dressed up, get up”….

I stood up in front of him, wiping some of his cum from my face.. He was scaring me now, confusing me…. “that’s a good girl, like to see my cum on your face,,, what a slut you are” he said,,, “yes, make up as well, he touched my face with his fingers, tracing the outline of my yes, round my cheeks, and to my lips, rubbing some of my lipstick onto his finger … then he pushed his finger against my lips, and inside my mouth ……. “suck my finger “ he said,,,, I sucked as instructed , “not bad for a bloke, you look a hell of a lot sexier than your missis ” he laughed….

“But ya falsie tits are too small, you need to get bigger ones .” he mocked… “lets see what you are like to kiss”,, he moved close and pushed his lips against mine, hard, his tongue pushing into my mouth… his face was rough, unshaven and his breath smelt of stale cigarettes and beer. He pulled away… “nice” he said….

“the only complaint I have so far is these” he said pointing to my chest “I like my women to have bigger tits than that.. … the docs tits are big, but she always wears them baggy jumpers doesn’t she, what they like to suck”, he went on and on ,,, It felt embarrassing him knowing my wife in a professional context and asking such intimate questions about her…. I thought that I had better say something,,,,, “yes there very nice ” I said.. “do you ave any pictures of her … you must have, maybe on holiday, topless …..

”NO” I replied sternly…. I did not want to think about Ann now, here, with him…. It felt wrong, despite the madness of my situation talking about my wife to him like this was just not right…… , and it felt like he invading far too much into my personal life now…”shame, would love to see her tits” he said… “what’s her first name, I only know her as Doc Green…. “Ann” I relplied….. “well, maybe you can get a picture of her for me, next time your banging her , or do you not , maybe you prefer men, .. I get it, yes,…. That’s why you dress… I get it now --- is she a lesbian then – maybe she’s the man in your house EH… she wears the trousers – is that how it works…. “no” I said,,, “well, er,, yes she wears trousers … look I don’t know,,, we don’t talk much about that” I stumbled on hesitating to say more “what, you don’t sleep together … so you would prefer it if she had a cock then” he went on……..

“Anyway, enough for now about that,,,, , let’s see what ye back end is like shall we…”

His comments about Anne and my breasts annoyed me as I was lucky enough to have a small pair of real breasts, so did not bother with false ones that much. For whatever reason I had always had man boobs, which was embarrassing when I was younger, but as a cross dresser I considered myself lucky to have them, I always felt so good about them when I was dressing, and I kept them smooth and they filled out my A cup bra nicely… “these are my real breasts” I said sounding hurt …

“Oh,,, that touched a nerve ,,,,, ok, ok, calm down, she is getting annoyed , might have to spank you” he said,,, “Let’s have a look then, come on then, prove it, let’s get your tits out and see”,,, and he grabbed edges of the V of my dress and pulled it aside, ripping the front and exposing my pink bra. He then walked behind and placed his arms round me pulling my dress right down exposing my shoulders and back and slipped his hands inside the delicate fabric of my bra and squeezed my tits roughly…. “yes, I suppose for a bloke they are big, fucking hell, they look like a real pair of girly tits, not bad at all, and big nipples too …. and he kissed the back of my neck, nuzzling against me, “your my girl now Jill, jacky Jilly jacky jilly….. mmm you smell nice as well, I suppose this is a wig is it”,,,,, as he brushed my hair to one side….

Then he started to get angry again,,,,,, “but for a woman they are still fucking tiny tits” he laughed,,, and he nipped my nipples tight between his fingers … “owwww “ I said,, “that hurts”,,,, my knees buckled with the pain … “owwww” he pulled down my bra straps and exposed my little man boobs , and they both popped out of the cups as he moved round to face me his face close to mine, he squeezed my nipples tight again and looked at me “DON’T YOU DARE BACK ANSWER ME AGAIN SLUT UNDERSTOOD, I WILL DO AND SAY WHAT EVER I WANT, AND IF I WANT TO KNOW THINGS ABOUT YOU, YOUR MISSUS, OR MAYBE YOUR DAUGHTER OR YOUR FUCKING SON I WILL ASK AND YOU WILL TELL ME ”,,,, “yes , owww,,, sorry,,, yes understood”… the mention of my son and daughter made me feel totally ashamed,, …Then he pulled my wig of and started to laugh at me….. “get the dress of “ he shouted,,,,, “LETS SEE WHAT A FUCKING PATHETIC EXCUSE FOR MAN YOU REALLY ARE, NOTHING LIKE YOUR UNCLE ARE YOU, IN FACT YOUR WIFE IS MORE OF A MAN THAN YOU ” I pulled it down over my hips and stepped out of it, ,,,,,,

“don’t fucking look much like a woman now do you” he laughed as he took another picture of me………. I felt ridiculous stood Infront of him now, no wig, lipstick smudged, boobs exposed, my little cock poking out the side of my pink panties in my hold ups and heels……..”not much you can do about that though eh” he said pointing to my cock…. I felt totally humiliated now, unable to hide, exposed…..

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By *r 007Man
over a year ago

harrogate

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By *unboy69888ABCMan
over a year ago

fleetwood

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By (user no longer on site)
over a year ago

I love tidying up my garage dressed in my sissi gear..

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By (user no longer on site)
over a year ago

Great story

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By *oddneyMan
over a year ago

east linton

Really good story

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

FOUR

“turn round sweet cheeks and bend over , ” he said, “let’s see what the back ends like , legs apart,,,,, wider,,, that’s better ,,,” I could not believe how easily he had taken control of me, and how weak and pathetic I was, just letting him degrade me like this, talking to me as if I was a cheap whore, a piece of meat…. But I could not help that feeling of excitement inside.

I was oblivious to the fact that he was taking more pictures of me …. he placed his rough hands on my knickers and started to feel me up, squeezing my ass cheeks and slapping them gently…. Then he pulled my knickers down and placed his thumb between my cheeks, pressing slightly against my exposed hole, My cock was hanging down “fucking hell your cock is so small, I bet the doc gets frustrated with that” he said,,,, “get it out the way” ………so I grabbed my cock and pulled it away as he continued ….. “lets have a look here, see how tight this little hole is ,,, how many men have fucked you” he asked….. “not many” I replied… He slapped my ass hard with this hand “I SAID HOW MANY SLUT” … “two” I replied, “two eh” .. “lets see how this feels then”… and he took his bottle of bud into his mouth wetting the neck with his salvia and then tipped a little against the crack of my ass , I felt the cool liquid spill between my cheeks then he pushed the smooth neck of the bottle against the entrance to my hole…. “two cocks and a bottle of bud” he laughed as he pushed the neck of the bottle slowly inside my hole…. “owww, no please “ I begged…..

“don’t fucking move, if it breaks it will do some serious damage, and I will have to call the doctor – or your wife ANN eh” he laughed, my legs were shaking as I stood in my heels, bent over as he frigged my ass with the neck of the bottle …….. “how will you explain this to the missis eh …..just fucking relax and take it like a man ” he was in hysterics now as he pushed the bottle gently in and out of my hole ……“does ANN know you dress as a slut in your shed ” … “no, please don’t tell her” ,,, “I thought not…. ..don’t worry, just teasing you,,, and he pulled the neck out and slapped my ass… “Next time it will be my cock”….

He sat back down on the chair and made me stand in front of him.

“ OK slut, I have a few things on next week, but I expect I will see you about, I will let you know when I want to see you dressed up like this again. We are going to have some fun… you belong to me now, and as long as you do as you are told, these pictures will stay safe - understood ”… “UNDERSTOOD” he shouted …. “yes colin, understood” I replied… “you can call me SIR” he said, even in public, call me sir – if you don’t I will punish you……… “UNDERSTOOD” “ yes sir” I replied…..

“Good Girl”… “oh, and you can clean all the rubbish that’s accumulated down the side of the allotments, … I have had a number of complaints from the members, and to be honest whilst the council pay me to look after this place, it’s one of them jobs I keep putting off… but now I have my assistant, that is YOU …, I want YOU to clear it all away tomorrow, and make sure its spotless…. , I will check, and if there is anything left I will take my belt to that sissy ass of yours, maybe tie you up and give you a good hiding” ….. he went on…. “Maybe you can clear it all up dressed in a short skirt and stockings” he laughed,,,,,, “No please,” I begged,,, “just joking, “ he laughed …. “But remember, if you do not obey me, I will make sure everyone in the village knows what a pathetic little cock sucking slut you are”

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By (user no longer on site)
over a year ago

Great story

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By (user no longer on site)
over a year ago

Fantastic, more soon please

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By *r 007Man
over a year ago

harrogate

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By *unboy69888ABCMan
over a year ago

fleetwood

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By *es for funMan
over a year ago

port talbot

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By (user no longer on site)
over a year ago

Great story

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By (user no longer on site)
over a year ago

cant wait to read more of this

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

FIVE

I cleaned myself up after he had left with mixed emotions. The bottle he had used on me was just left on the bar in the shed, I could not believe I had let him do it, how I just gave in him - But then I knew deep down it was what I craved - just not with him. Of all the people in the world to have discovered my secret Colin would be right at the bottom of the list …. However, he had a reputation to keep, and I guess he would not want everyone to know he wasnfucking men dressed as women in the allotmants he managed… - so maybe he would keep my secret safe -

I arrived home just as Ann was still watching some film and we chatted for a bit but it was clear she was engrossed in the film, so I went for a shower and then to bed.

The next day, I got up early, sorted the regular jobs out round the house and headed straight to the allotment. Colin was noy about and I did not want to be seen clearing up, so I just grabbed a few bin liners and a pair of gloves and started to clean up the rubbish as per Colins instructions.

It was not that bad and after a few hours, I had collected 6 bags of rubbish and loaded it into the skip by the side of the allotment entrance.

I then went to my shed , locked the door and sat in the back on the sofa and tried to collect my thoughts….

I stayed away from the allotment for the next few days. I felt sure he would be waiting for me, and I did not feel ready for him. I liked to dress, and I enjoyed the fantasy of being used by men, but in a fantasy I am in control, I was not comfortable with having to obey him, and not sure what he would make me do next. I was in a state of panic for the next few days…. Maybe if I kept a low profile he would just leave me alone , a one off…..

3 days later over tea Ann asked me why I had not been to the allotment…and then she said that she had bumped into Colin at the surgery, and said that he wanted to ask me to ask you to call over, he said he has something to show you in his shed… he sounded very insistent… Said that he would be disappointed if you did not call over, said that you too were getting on really well ….

Ann was smiling, she knew what Colin was like, "maybe he wants to show you his prize carrots he grows for the village show" she said mockingly …. "does he have a big one" she went on, laughing now…. I laughed along, sharing the joke, but inside relief that he had not said anything else about the other night…… Colin had a reputation in the village, a bit of a loud mouth, Know it all – and we had joked about him in the past -

I knew I had no choice now, Colin was serious, playing with me, testing me… So the next day I went back to the allotment to find him.

"agh Jack, about fucking time where you been hiding" he said,... Come here I have something to show you…

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By (user no longer on site)
over a year ago

Brilliant please do continue soon

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By *af105Man
over a year ago

Newtownards

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By *cotFit4funMan
over a year ago

Kettering

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By *everlyandersonTV/TS
over a year ago

newcastle

mmmm id love this

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By *es for funMan
over a year ago

port talbot

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By *r 007Man
over a year ago

harrogate

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By *unboy69888ABCMan
over a year ago

fleetwood

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By (user no longer on site)
over a year ago

Good story

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By *v shaunaTV/TS
over a year ago

doncaster

Dont stop

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By (user no longer on site)
over a year ago

more plz

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Nice story so far!

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By (user no longer on site)
over a year ago

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

SIX

Colin took me to his shed and showed me inside. He had a lot of wood working tools, as I knew he made stuff for village shows as well as displaying his pirze veg but he also had another room. and when I stepped in, it was a damp with wood shavings on the floor - to the side was a bench with an assortment of tools lying about, there was a steel chair in the corner and chains hanging from a pulley attached to the roof beams… “I want you to test out my new toys” he said,,, “I love all that medieval torture stuff, always wanted to have a willing volunteer to play with”,, he went on….

“This is what I am working on at the moment,” he said pointing to what looked like a medieval stock. It was about 3 foot of the ground with 2 small gaps for arms, and a larger one for a head to go through.

“I have been dying to try it out, why don’t you pop back to your place get yourself all dressed up nice for me, and I want you to put on your make up, make sure those lips are nice and red for me … then you can come back and let me test his out. ”

I did not know what to say, but my instinct was to run, run as far away as possible. “don’t worry I won’t hurt you, … much “ he laughed …. “its just a bit of fun, relax, look I don’t want to cause you any harm, but, I do want you to remember that your mine now and that means you do what I say,,, else,, well you know what I will do….”

So, just under an hour later I am dressed, I have my short skirt, fishnet stockings, black zip up ankle boots, a crop top t shirt, and my tight Wonderbra that pushed my little boobs together so show a hint of cleavage. I put on my blond shoulder length wig, and as instructed full make up with thick red lipstick… I looked a total slut, and felt like one,,,, Expecting the worst, I applied some lube to the inside of my hole, and popped that with some condoms and lippy into my small clutch bag.

It was still light outside, early afternoon, and there were a few people around the allotments. That meant I had to risk a short walk from my shed to Colins place right at the entrance to the site. There was a back path that was relatively private, so I put on my long raincoat, and went for it.

The adrenaline rush was amazing, I could not believe I was doing this, and when I could see Colin at the entrance to his shed, I relaxed as he ushered me inside, closing and locking the door behind me. He slapped my ass as I walked in, took ,my rain coat from me and gave me a big kiss…. “you do look amazing Jill” he said,,, which made me feel so good… “just to make it a little more fun and exciting for you, let me put on this eye mask,” he said, as he placed it over my eyes and guided me into his play room.

“ok, Jill, if you bend down slightly, arms out and rest your neck here”… I hesitated, but then knew that there was not much point me resisting, the worst he could do was fuck me, and I suppose deep down I quite fancied the thrill of been fucked whilst tied down,,, It was making me feel so excited to be honest,, so I positioned myself inside the stocks as he clamped the top beam down, locking me inside his stocks…

“there now, that is perfect, just as I had imagined” he walked round me admiring the view. “now, let me clamp your lovely sexy ankles, just a spreader bar to make sure your totally helpless and cannot move .. let’s get your legs apart, yes that’s perfect…”

“Now, I need to do something with that cock of yours… “ he said … Then he knelt down and proceeded to wrap some form of clear tape round my balls and cock taping them up tight so my cock was pushing up towards my belly button. He wrapped the tape tight than placed a black stretchy corset around me, under and over me, pulling it tight and securing it with what must have been hooks– as if he was hiding it away… “there, that’s better – they won’t even notice that you have one now…” he said to himself … My cock felt tight and I guessed that taking the tape of would be painful…

He then switched on a light above me, and took some pictures of me strapped down. "you won't mind if I video this, just for my wank bank of course" he said smiling….

My legs were fastened inside ankle clamps and stretched apart slightly, I felt totally and utterly helpless now… It was not as uncomfortable as I expected. “this will help you relax Jill” as he opened a bottle under my nose. “ big sniff,,, yes that’s it” ,, my head started to spin a bit and colin walked round and stood behind me.. “just trying you out for size,,,, mmm perfect position – just the right height for me” as he lifted up my skirt and started to run his hands over my ass,,,, oh god it felt good. He spanked me lightly and then pulled aside my panties and started to rim my ass… wow it felt good as his tongue darted inside and round my hole… My cock was straining now getting hard but constrained within the tape and corset. Whist uncomfortable, the amazing sensation of Colins mouth and tongue against my exposed hole was making me relax and feel even hornier…… this was nice…

Then he came round to face me.. His had removed his trousers now, and his cock was already hard and I knew what he wanted, so I opened my willing mouth lifting my head up to suck him…. He thrust his cock right down my throat and I gagged hard “you need get used to this Jill,,, Relax your throat, just let it go in by itself, I want to feel my cock at the back of your throat” he said,, as he continued to slowly face fuck me , pushing on against my retching and gagging … I was totally helpless and dizzy with the adrenaline, fear and pleasure of what he was putting me through.

As he face fucked me he started to talk about my wife, Ann. "I bet the doc is a good ride, does she let you fuck her in the ass", obviously as his cock was in my mouth I could not awnser,.... But he went on… "I want to fuck her in here, I bet she is a dirty slut like you in the bedroom"... I could not believe that this was turning me on.. This brought back memories of when Ann was younge, before the kids, and she liked a bit of kinky role play and we did fantasies about me watching her get fucked by other men with bigger cocks than me, but more recently our sex life was very mundane…

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By *MBER KENTCouple
over a year ago

folkestone

Great story

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By *oeKelly2003TV/TS
over a year ago

City

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By *umblebiMan
over a year ago

ayles

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By (user no longer on site)
over a year ago

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By *unboy69888ABCMan
over a year ago

fleetwood

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By (user no longer on site)
over a year ago

Wonderful story, more please. I have various tie points set up in my garage..

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By *akeyjohnMan
over a year ago

ossett

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By *ammyTV/TS
over a year ago

manchester

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By *cubasexMan
over a year ago

Dudley

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By *ichelleanddaveCouple
over a year ago

blanchardstown

Loving this story

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By *atexpvcTV/TS
over a year ago

chester/Merseyside

Love the story wish it was me in the shed

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By (user no longer on site)
over a year ago

Great story

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

SEVEN

Colin continued to ask questions of Ann, as he face fuxked me, and after a while he pulled the blindfold from my eyes and told me to look up at him as he placed his hard wet cock just in front of my mouth. "I will have your wife in here very soon, and you are going to help make that happen, and I will have you both as my sex slaves"... " I bet you would like to watch me fuck her". I just nodded.. "tell me you want me to fuck your wife".. He demanded…. As he pointed his phone at me….." yes Colin, I want you to fuck my wife" I said… and at that moment I did, in fact I wanted him to do anything he wanted to me……

He walked back round to my bum, and pushed his wet cock against my already wet hole … “you don’t mind if I fuck you bare Jill” he said… "does the doc ride you with a strap on" he laughed…. … “ER no, but I would prefer if you wear a condom, please Colin,,,” I tried to say but it was too late ……”it doesn’t look like I have any choice” I went on to reply and then just squealed “owwweee” as he pushed his hard fat cock inside me, and I felt a sharp burning sensation rip through my ass as he went in deeper, deeper inside my tight bum hole . “aggggggg that’s fucking good ,, so tight,,, so fucking tight,,”….. he said as he started to pull back, then push inside me again this time further, and I could feel his balls slap against me .. He rested his body weight over my back as he squeezed his cock in deeper, as deep as he could go, gripping my shoulders pushing them hard against the wood of the stocks…..”aghhhhohhhhhhhhh that’s good” he said,,, and then he pulled back out and stared to fuck me at a steady pace,,,, in ,, out,, in ,, out… each time pushing me forward against the stocks… I could not see him, I was helpless,,, as he took his pleasure and fucked me, … Soon the burning sensation was replaced by pleasure, as I could feel ever inch of him inside me, rubbing against the inside of my bum, tickling and itching those parts of me that have needed a cock for so long – the feeling was so good, and I felt so alive, aroused, wanton – I was his slut now, he owned me, and I wanted this so badly .. it was my turn to express myself now, “oh yes sir, fuck me, please , fuck me, I am your slut colin, you own me, I will do anything you say anything, please fuck me,, fill me with your cum,” “good girl” he said,,,” that’s what I want to hear, just imagine when I am fucking Ann and you are watching, maybe make you lick my cum out of her pussy when I am done" he said….. ,,, “my slut now,, your going to be my whore, my slave”….. “yes sir, I will be your slave, your whore , I will do anything to please you, please fuck me harder, please ”…… I was beyond help now,,, in extasy ……. This was amazing,, but I only wish I could have touched my cock, it was so hard now but I could nod do anything to get near it,,, I was trying to move myself so the end of my cock would rub against the corset as he pushed down, but it was so hard and frustrating….

He went on for a long time , and his moans and grunts got louder and louder,, He was now gripping the side of my waist pushing myself upwards as he fucked me,,,”oggggg yes yes YES EYES YES YES

EHMM EHMMM EHMM YES OH FUCKING YESSSSSSS” And he released his seed deep inside me,,,, I was screaming in pleasure as I fekt his seed pump inside me,,, He pushed one last time so hard and deep, holding himself hard against me as hic cock spasmed inside me “FUCKING HELL THAT WAS SO GOOS JILL” he said,,,

I was released from the stock and allowed to rest a while. His cum was dripping down my legs and my cock was aching for release….

"OK my slut, that's enough for today, you can go back to your shed now and clean up, same time tomorrow

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By *imale38Man
over a year ago

Barnsley

Love this story.

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By *ubsteffTV/TS
over a year ago

Portsmouth

This is excellent!

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By *es for funMan
over a year ago

port talbot

Love it

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By *exy sal002Woman
over a year ago

.

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By *oeKelly2003TV/TS
over a year ago

City

Can't wait for Colin to fuck your wife ??

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By *oredcouple1TV/TS
over a year ago

kirkcaldy

Getting hard reading this,

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By *rdiscreet327Man
over a year ago

Nottinghamshire

Great story, very well written. Got me so hard!

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By (user no longer on site)
over a year ago

Great story

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By *lli_sissyTV/TS
over a year ago

Cambridge

loving the story

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By *unboy69888ABCMan
over a year ago

fleetwood

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By *ritter1Man
over a year ago

Dundee

Great story

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By *apomanMan
over a year ago

st hel3ns

Amazing story and so fucking horny.

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By *r 007Man
over a year ago

harrogate

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By *usie pTV/TS
over a year ago

taunton

Love it, I did experience allotment shed fun with some dirty old guys many years ago.

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By *iderryMan
over a year ago

Derry

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By *cubasexMan
over a year ago

Dudley

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By *oventry4biTV/TS
over a year ago

coventry

Love this

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By (user no longer on site)
over a year ago

I love cross dressing as i tidy up my garage at the bottom of the garden..

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By (user no longer on site)
over a year ago

Brilliant

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By (user no longer on site)
over a year ago

more plz

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By *everlyandersonTV/TS
over a year ago

newcastle

mmmm would be a dream come true

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By *ed01Man
over a year ago

happy ville

Wow

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

EIGHT.

I got back to my shed and it took me ages to slowly unwrap the sticky tape that he had used to bind my cock and balls up out the way… Thankfully as I kept myself smooth it was not too painful.

That night whilst I was sat at home with Ann, I could not help thinking about what Colin had said and what he wanted to do to Ann.

When we were younger, Ann was much more adventurous in bed, and we had an exciting sex life. She did like me dressing as a woman on occasions and sometimes encouraged me, but when I last suggested it almost 20 years ago now, she laughed, and told me that it was a ridiculous idea at our age…

After the kids, things were much more mundane and whilst we had a regular monthly fuck, and the odd fumble when we were in the mood, my obsession with dressing and men and her focus on her career and her activities in the village ( she is chair of the local WI, School governor and various other things in the community, as well as involved with running the village General Practise ) suited us both and sex was never really an issue to discuss..

That said, if anyone in the village found out about my life as a cross dresser, the shame would be very difficult for her to deal with. I had never really given that much thought until now. Ann enjoyed her social position in the village, she was very focused on how we looked as a couple and extremely politically correct in her manner and ways - I just had to tow the line at functions and events…

So I just decided to dismiss it out right and said nothing at all to Ann.

The next day I was back in Collins shed, he did not seem bothered about Ann, and just said that he was teasing… and not to worry… Colin was in a great mood, and was showing me a lot of attention, the sort of attention from men I enjoyed, telling me how sexy I looked, and that he could not wait to fuck me again….. We kissed and his hands caressed my body, as he unzipped my dress and let me step out in my bra, hold ups and my wig and makeup and heels.

We kissed again, and it felt so good been nearly naked as he held me tight, his hands roaming free over my body, as I reached down to feel the bulge in his jeans, --- I wanted it so badly……

“Jill, before we go on I want you to sign this document … Its just a typed letter from you to me, saying that you consent to everything we are doing together ,, that you have asked me to take pictures of you dressed as a woman and with me having sex with you as part of a consensual agreement….”… “why do I need to do this” I asked…. “look, we are having fun, and I don’t want you to go to the police and tell them that I am making you do anything against your will… If you do not agree, I will let you go now and we can end our fun – it’s up to you….”…

I was torn now … confused…., Clearly the best thing to do now was to leave.., but I was horny as hell, I was so lucking forward to Colin fucking me again, I had already felt his hardness against me and I wanted more….

I hesitated… Colin had the paper and pen on a small table in front of me.. I could reach out, pick up the pen and sign the document, or I could leave ….

Needless to say, I signed the letter, not only did I sign the letter, but I wrote at the bottom of the letter … I will obey colin and do anything he says to please him …. I looked at him and told him that I was his, and repeated again that I wanted to do anything to please him …. within a few minutes I was secured to the stocks, and enjoying the feeling of his tongue deep inside my ass…..

Then………

The first strike of the cane stung so bad I thought I would pass out… The thick bamboo he had chosen, made a loud crack as it bit into my bare exposed buttocks….

"WHAT DID SHE SAY WHEN YOU ASKED HER" he shouted, whacking me again… "OWWWWW please stop this hurts, what do you mean,,,, please… “WHEN YOU ASKED ANN TO JOIN US, TO COME AND LET ME FUCK HER, WHAT DID SHE SAY,,”….. “ERR,, owwww OWWWW PLEASE,,, ShE, s ER owww she just said that she was not interested in that sort of thing Owwww please stop oowwww"....

"WHAT DID YOU SAY TO HER , HOW DID YOU INTRODUCE THE IDEA YOU FUCKING PATHETIC TWAT"... I did not know how to respond, “err,,, I … just ,,, well,,, no I knew she wouldn’t be interested,,, OWWWW sorry, please stop…..” as I guess he knew I clearly didn't even dare mention it to her… he went on caning me, and after the 12th strike he stopped…

"Well, you were warned, you say you will do anything to please me, but you ignored my instructions ……. Your weak,,,,,,, it looks like I am going to have to take matters into my own hands and do this the hard way…" .. "you had your chance and you did not have the balls to even ask her"....

"I want you to phone her now, tell her to come here, say it’s an emergency"....

“NO, PLEASE NO,, I CANT DO THIS” I said, panicking… I could handle Colins attention on me, but involving Ann is just not something I can get my head around.

“OK, I will phone her, and explain that you have had an accident and that she needs to come right away….”

“what will you do when she comes” , I asked…

“That’s easy, , I will tell her to get naked and fuck her in every hole, take lots of pictures of her and have you both as my fucking slaves, I won’t need to fuck your sissy ass anymore, and I will whore you out to my friends to fuck,,, I will keep the lovely Ann to myself…..…..” and if she refuses, I will make sure that pictures of you dressed, with my cock in your ass, and mouth are displayed on every notice board in the village, on every social media post and if you were to go to the police I will just show them the letter you just signed”………

“I was in an incredible panic now, helpless

Colin took my phone from my handbag, walked round to face me, took out his cock and pushed it deep into my mouth…. “ This will keep you quite whilst I chat with your wife “ he said laughing..

Then he scrolled down to Ann’s number and called her….

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By (user no longer on site)
over a year ago

Omg, fantastic, more soon please..

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Story just gets better! Hehe

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By *everlyandersonTV/TS
over a year ago

newcastle

love it

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By *ritter1Man
over a year ago

Dundee

Nice

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By (user no longer on site)
over a year ago

Great story love to hear more as this has got me turned on so far

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By (user no longer on site)
over a year ago

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By *unboy69888ABCMan
over a year ago

fleetwood

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By *es for funMan
over a year ago

port talbot

Cant wait for this phone call

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

Great storey

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By *oeKelly2003TV/TS
over a year ago

City

Wow can't Wait

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By *.A.MGUY55Man
over a year ago

littleborough

more plz

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By *az1941Man
over a year ago

Nr Llanrhaedr

Wow, this is amazing ??

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By (user no longer on site)
over a year ago

Great story

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

This is a great story

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By *usie pTV/TS
over a year ago

taunton

getting real good

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By (user no longer on site)
over a year ago

Gagging for the next episode

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By *atsWoman
over a year ago

wexford

Fantastic. Really and truly your best work to date.

Can't wait for the next part!

Xxx Cats

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By *af105Man
over a year ago

Newtownards

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By *imale38Man
over a year ago

Barnsley

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By *issyShellyTV/TS
over a year ago

lytham

Very horny story ..... xx

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

NINE

It was so surreal listening to colin talk to my wife, as he pushed his cock inside my mouth, slowly face fucking me as he explained to Ann that she had best come and collect me from the allotment. I could hear the conversation, and I assume Ann must have been asking many questions, but Colin was good, he would not go into detail … “listen Ann, it’s a bit embarrassing, I am afraid your husband has had an accident, however, well, it’s a bit awkward, you see he was wearing women’s cloths, and whilst I could phone an ambulance, it may be a bit embarrassing for you both if anyone was to find out, so I think it’s best if you come and collect him and have a look at him to make sure he is ok…”

Colin gave me a few more strikes of the cane and then gagged me , and left me in the stocks, now I a complete state of panic as Colin went outside to the entrance of the allotments to wait for Ann to arrive. What would she say, what would Colin do………

The door opened and Ann, walked in. I could see that she was dressed as usual in a trouser suit, flat shoes and her face was in shock as I met her gaze,... What must I have looked like, looking up from the stocks with my ball gag in place.

"OH MY GOD WHAT THE HELL IS GOING ON IN. HERE" she yeled. Colin had walked in behind her and shut the door.

"Nothing to worry about, and I suggest you sir down and let me explain your situation" said Colin in a calm but authorative tone.

Suprisingly Ann did as he said, and Colin went on to explain, dispite my attempts at shouting against the gag, which only resulted in Colin taking the bamboo and striking my ass hard to shut me up…

Ann looked on in shock as colin told her everything that had happened but not exactly the truth, as the way he had describes it was that I had approached Colin and asked, in fact begged to be his slave… Colin showed Ann my signed letter and then went on to let her scroll through many pictures and video he had taken of me over the last few days

Then he presented Ann her options..

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By *ornycouple44Couple
over a year ago

St austell

Great

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By *ritter1Man
over a year ago

Dundee

Keep going, just getting better

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By *itom18Man
over a year ago

Wigan

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By (user no longer on site)
over a year ago

Wow! So horny

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Can’t wait until the next part!!

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By *everlyandersonTV/TS
over a year ago

newcastle

mmmmm brilliant love it

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By *vanabeusedTV/TS
over a year ago

somewhere

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By (user no longer on site)
over a year ago

When is the next instalment

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By (user no longer on site)
over a year ago

This is killing me, waiting on the next installment hurry up before I explode xXx

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By *b1976Man
over a year ago

North East

Absolutely brilliant story

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By *unboy69888ABCMan
over a year ago

fleetwood

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By *imale38Man
over a year ago

Barnsley

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By *es for funMan
over a year ago

port talbot

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By *DFriendly FolkCouple
over a year ago

Redditch

[Removed by poster at 19/02/20 07:13:00]

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By *r 007Man
over a year ago

harrogate

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By *everlyandersonTV/TS
over a year ago

newcastle

i love this story thinking of it happening to me thought of it makes me horny

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By *cubasexMan
over a year ago

Dudley

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By *akeyjohnMan
over a year ago

ossett

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By *oeKelly2003TV/TS
over a year ago

City

Love it

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By *aye tvTV/TS
over a year ago

stoke on trent

will anne be going in the stocks will jill take pics of her been used

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By *ansymanMan
over a year ago

Kidderminster

Loving this story

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By (user no longer on site)
over a year ago

Great story

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By (user no longer on site)
over a year ago

more pls

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By *ed01Man
over a year ago

happy ville

Mabey colin has been fucking ann all the time and she has set up jill

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By *uckinsMan
over a year ago

edinburgh

More

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