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Cross dressing in a charity shop

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

One

The shop seemed quiet, just of the main street, and I could see that it was a large shop, and seemed to have plenty of racks of female clothes. It was already getting dark outside, and it was about 4;30pm so I expected that the shop would close at 5pm. I am always hopeless at buying female clothes, and as cash is tight, it’s easy to waste a lot of money on stuff that just does not fit me, so I have to search the second hand shops.

As I opened the door, that musky charity shop smell hit me, along with the ring of the loudest doorbell I had ever heard in my life. The lady in the shop turned towards me, smiled and went back to her chair at the till. She looked to be in her early 60’s, a tall buxom blond lady, and she was just walking back to a chair where I assumed she was reading a magazine. That look from her knocked my confidence so I headed to the men’s selection, and started idly browsing the rails. As I settled myself, I headed for the ladies racks and started pulling a few out, looking at the styles, and the colours. I wanted a skirt and a top, something that i could try and wear outside, something that would not bring to much attention to my male form, but was clearly feminine and would show of my legs, and disguise the rest. I also wanted something sexy and revealing for the evening in my hotel room. Many times in the past I had bought 5 or 6 items in one go, and i would be so excited getting to my hotel room, striping of and trying them on. Usually to find that they either did not fit, or I just did not get the right feeling looking at myself in the mirror, - and as i did not have a wardrobe - only a small bag, they usually all ended up in the bin the next day.

Anyway, I picked up a nice black satin slip dress, oh it was gorgeous… very strapy, but obviously not for my shape - if only !!.... then another, a wrap sequin maxi dress, long and flowing , oh my god i wanted it … but it was only a 14.. Then another,,, this had a satin feel, black and white print, and it felt good, loose slit skirt and it looked to be just over knee length with a wrap round V cut into the chest. It was size 16 which was probably going to be too small for me, and as I looked, I was oblivious the female attendant who was now stood behind me, “ that's a lovely dress, is it a treat for you” she said… I was dumbstruck, and my usual response in this situation would have been … its for a fancy dress, or for my wife left me and I just said,, “sorry, err,, yes…. Is that ok”... “dont worry” she said placing a hand on my shoulder, “I don’t think it’s illegal you know, I have to say we get many men in buying dresses for themselves … each to their own I say luv… ” she took the dress from me and held it against me… “16”, she said, “are you sure “... “not really” i said, I tend to get away with 18, but have managed a few 16’s in the past .. it’s just a lovely dress,,, “ you have the height for it, but not sure about your stomach.” she smiled… “maybe with a corset, black tights, … what colours your hair” she asked…”I assume you wear a wig”...she added .. “ it’s a sort of plumb / purple, i said,”... “do you have it with you”.. “It’s in my car”, ,then she surprised me - “do you want to try it on”....”can I”, i said, “yes please,, if thats ok”.... “Look, its getting late, I generally shut shop at 5pm anyway, so why don’t you get your wig, and your underwear and you can try it on, as long as you promise to buy something …” she said..

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

Very interesting start

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By *uetv2TV/TS
over a year ago

Poole

Carry on please I've been in this situation

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By *dsindyTV/TS
over a year ago

East Lancashire

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By *avey997TV/TS
over a year ago

East London

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By *idethesausage2Man
over a year ago

Trowbridge

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By *isterfoxxxMan
over a year ago

nottingham

Fuck just getting I to that's as well

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

TWO

Excited, I went to my car which was parked about 5 minutes away. I collected my bag, from the boot of my car.. It had a few things inside, some lingerie, make up, heels and wig.

I returned about 15 minutes later, and the lights were out and the door closed. I had to knock a few times, and I thought that she had changed her mind… then she appeared from a side door…

“you will have to come round the back now”, she said,,, “I have locked up”...

I followed her and could not help feeling excited about the chance to actually try on a dress before I bought it… She took me to a small room at the back of the shop. It was a sort of storeroom, hangers on the walls, a small oil filled electric radiator and two freshly brewed mugs of tea a kettle with a half-finished pack of digestives …

She had a few things hung up, “I keep these in the back, ,,” she smiled, pointing at a selection of dresses, skirts, tops… even a bag, some heels, and some costume jewellery...,

She must be going for the hard sell I thought,... but I did not mind at all… the opportunity to finally get to try out some clothes and maybe even get an opinion was worth splashing out a few quid for…. She was already taking control, and she introduced herself as Helen, and asked my name, which I replied as John, then she laughed … “no what’s your female name” she said,,, … “Jasmin” I replied, or “Jaz” for short… “OK Jaz” she said, let’s have a look at what you have in here… took my bag from me and started to open it…

I suddenly remembered that I had a large cock shaped dildo and a few but plugs and vibrator in the bottom of my bag.. And a few other items I would prefer her not to see… including a set of handcuffs and a leather strap - something I liked to do with any potential willing dominant males - loved nothing more than getting a good spanking whilst dressed...

I moved across to stop her opening the bag ,,, then she said “oh sorry,,, I can be so nosy”,,, and just as I was about to take the bag from her my phone buzzed …. I mumbled something along the lines of “it’s ok” and I quickly ended the call and swiched of my phone , but it was too late,,,, she had already opened the bag thinking I was saying it’s ok to her ….

She had obviously spotted a few of those items, as she laughed to herself but did not say anything, and just pulled out my wig, and my bra, panties and a pair of black hold ups…then placed them back inside the bag.... “Why don’t you get out of those clothes and I can quickly measure you - “ and she sat down to drink her tea ….I was not sure whether I was to start undressing in front of her, or go and find a cubicle…. “Where should I change” ... I asked….

She was sat down, her black stocking clad legs were crossed, and I am sure there was a extra button open, as her huge cleavage was pushing hard against the white satin of her blouse.

“You’re not shy are you… I am sure there is nothing you have down there that I have not seen before…. “ she smiled……

I felt slightly embarrassed now, but also very excited…

I took of my jacket and hung it on a hook behind the door, then my shoes… socks… and then my shirt.. The room was cold, and she asked me if i was ok with the temperature…. She placed her hand on my bare back, “oh your cold darling” she said, … My nipples were already pointing at her, and I could feel something else growing between my legs… the whole situation was turning me on,, I said I was ok, and I continued and removed my trousers, stepping out of them awkwardly, and then just stood there on the cold floor in my underpants….

Then the door opened, and to my horror, a young woman walked in on us. She must have been in her early 20’s , she was dressed in black leggings, and a loose fitting t shirt, brown blond hair -

“Don’t panic its only Jen, she works with me, I asked her to join us, - Jen this is Jasmin” …

OMG OMG i thought......

So there I was stood in my underpants, in the back room of a dusty old charity shop with this sexy 60 year old milf and her young sexy assistant….

This was all my CFNM fantasies at once….

“Unbelievable”. Jen laughed, “not another one Helen, that’s 3 this month”, she said…. . She settled down on the seat next to Helen, taking out a digestive, and started to drink the tea…

“come on then sweetie, drop em,, and lets get you all dolled up,”

So I removed my pants, placed them on my pile of clothes on the table and stood naked in front of them, feeling so excited, I could not believe my luck..

I hope you have brought your credit card” said Jen… as Helen collected my clothes and placed them in a locker on the other side of the room. She locked it and popped the key in her bag… “you wont be needing these for a while” she said,,,

I hesitated… “err,, well yes, I have a card,,,”… well, said Helen, this is a bit of a side line for us as we don’t get paid from the charity shop, so why don’t you relax and lets us transform you into the woman you so desperately want to be, and shall we say, £100 for me and Jen, and whatever you want to buy from the shop goes to the charity… how’s that sound….”…

“or shall we cuff you up and give you a good spanking, I see you like that judging by what I could see in your bag”,,, she handed the bag to Jen… “have a look at that dildo Jen, and the handcuffs and, a whip and a paddle”, “Let’s have a look” giggled Jen, and she took the bag and started to pull everything out onto the table, as I just stood there naked, covering myself with my hands, starting to feel slightly concerned, as I got the feeling that this was something they had done before..

Helen was obviously clever, and she had played me nicely and now she had hooked me in, sensing I would be an easy catch,,,, she had my clothes locked away, and It was clear I was going to do anything these ladies wanted....

“I agreed with the fee, and told her that my card was in my wallet in my jacket which was hung up on the door…

As I did this, Jen and Helen approached me, walking round me.. Helen was stroking her fingers over my chest, tweaking my nipples. ,

It felt so good, she smelled so nice, and looked so sexy,,, I could not help look down her cleavage…

“do you like what you see” she said, “yes” I replied, “they look amazing…

My hands where covering my cock, and Jen went to move them. “dont be shy”

she said, “lets have a look, we are all girls together…… is it a big one”…

“er not really” I said, as she took me by surprise and quickly pulled my hands behind my back and cuffed me.

“there, that’s better” she said,,,,, “ yes its very small isn’t it” she said, pointing between my legs,,,,

Helen was laughing,…..”OMG,, its tiny”,,, “is that as big as it gets” she said… “your poor wife darling”,,,,

They left me stood in front of them, Helen went into my jacket and took out my wallet.. “lets see, driving licence, ,mmmm guessed your real name was not John” she laughed, and cash card, credit card.. oh, £80 as well,, I best take that now as a deposit….. let me take a swipe of your card, and I will photo copy the driving licence as well… don’t worry, just a precaution in case you decide to not to pay your bill at the end” she said…

This was getting a bit to uncomfortable now, and I was starting to feel worried… but deep down, I just did not care – this was all my fantasies and more ……..

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By *ubsteffTV/TS
over a year ago

Portsmouth

Lol, see this barrel, best get over it x

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

Hook , line and sinker . Keep going

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

Love it keep going

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By *issy vickiTV/TS
over a year ago

lisburn


"Carry on please I've been in this situation "
would love too hear bout your situation

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By *hona tvTV/TS
over a year ago

Bathgate

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By *ebbie360TV/TS
over a year ago

huntingdon

I'm sure lots of us girls have had risky conversations with the assistants in charity shops. For my part, i had a fit looking late 60s/70s woman saying that she bets the tiny teenage style skirt i was buying would look good on and that she was thinking about it for herself. For my part, i said that i would return with some photos and said that she probably saw lots of old men buying inappropriate clothes for their (cough, cough) niece. The conversation continued without either actually saying it was for me but both knowing the truth.

Nothing as dark as this story is turning though. Loving it so far. X

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By *ussgbrMan
over a year ago

Burton

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By *d funMan
over a year ago

Telford

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By *ree guyMan
over a year ago

Fleetwood

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By *hil911Man
over a year ago

Solihull

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By *d funMan
over a year ago

Telford

I so need buy some clothes

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

I would love this shop

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By *ony 529Man
over a year ago

coventry

Wow it's certainly got me hard that's for sure

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

THREE

Can we stop this, I asked, feeling very nervous about the situation… .

“Don't worry” smiled Helen, “we are not going to try and rob you, or do anything to harm you, we will all have some fun, you get an experience that you clearly desire, and we will get a paid very well for providing the service…. As long as you do as you are told”

Helen kissed me gently on my lips, put her arms round me and hugged me… .she sensed my nervousness, and Jen came closer, and put her lips to mine and kissed me as well… …… “your not bad looking for a bloke, so let's see how gorgeous you look as a woman”....

“OK, let’s get Jasmin ready”, said Helen. She got up ……”I can see your nice and smooth, I guess you shaved to day”… I nodded, as my plan was to pick up some clothes from a shop, head to my hotel, dress and hopefully get a meet from the swinging site. I had shaved my chest and legs this morning to save time.

“Have you ever been measured for a bra” she asked…. I replied telling her that I never fully understood how it worked.

“First we measure loosely around the fullest part of your bust, with the tape straight across and around your back, bringing it to the front. Then subtract your band measurement from this bust measurement. The difference calculates your bra size- each inch represents a cup size” she said …. so many words but I was lost now in this sureal situation, still trying to make sense if it, but also starting to relax.....

Jen was tracing her hands over her chest, “jaz, you do not need big tits to look femanine “ said Helen, Jens are small, they are so sexy"....

"I know, let's show jaz our boobs, said Helen… .and I will measure Jen, then we will measure you".

My cock pulsed inside it's little cage.. My eyes lit up as I watched

Jen, pulled of her t shirt up without hesitation, exposing her many tattoo's and a black sports bra. She pushed them together, squeezing them as she went on talking. , I could not take my eyes of them….

Helen simply spooned her massive boob's out of her blouse and they hung down, over her top. They were in very good shape, and she had huge nipples, that I was desperate to suck on..

Jen pulled her bra over her head and displayed a beautiful, bouncy pair of small perky tits… almost cone shaped pointing perfectly towards me… she flicked each of her nipples rubbing the ends between her fingers, and shook her self as the wobbled about, ..... Amazing....

They both stood together, and touched each others breasts. …”well, do you like what you see Jaz”.... “Oh god yes, yes , yes yes …” I said , ........

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

More

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By *eathersarahTV/TS
over a year ago

warrington

Keep going. It. Amazing. X

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By *ndrea54TV/TS
over a year ago

cambridge

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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

FOUR

I just starred at them both, a confusing mixture of envy, excitement , and sheer lust at these two extremes of pure feminine beauty… yes I have always had an obsession with breasts, never stop dreaming of having my own, and this was just a dream come true for me… .

I had a nice smooth small pair of man boobs… I was very very proud of them, I had tried all the exercises and took many different herbs, including fenugreek, on a regular basis.. I knew deep down that unless I went for surgery or hormone treatment they would never get any bigger… and. … as a closet cross dresser living a lie, so as not to risk loosing my wife, and my job, I knew I would never be able to have them… .

Helen was going through the motions of measuring Jen, and telling me all the details , occasionally touching Jens nipples, and playful caresses , shaping her boob's in her hands…

I just watched in awe… . Taking it all in, and learning at the same time… this was amazing..

Then Helen snapped be back to reality… ..

, , “Now it's your turn my dear“ as she replaced her enormous beasts back into the confines of her bra and blouse, but leaving most of the buttons open, and she pulled the tape round me, her hair brushing against my face, and her deep cleavage pushing against my bare skin…. She was a very sexy confident lady, and her perfume was so strong… Then she placed the tape round and over my chest (my small moobs sticking out not making much difference) ... the tape was cold, and my nipples which I do delight in seeing when cold, were sticking out and she pinched one with her fingers,” . Then she took a 4 inch wide strip of clear plastic, it was slightly thicker than cling film and also sticky.. “Jen , help me with this, lets get it nice and tight round Jasmin’s chest, this should help with her shape.. They wrapped it round, pulling so tight, and it pushed my little man boobs up and tight together..

“oh, look at these little puppies“ she said, ,, that’s much better…. And then she took a measurement around my stomach, then asked me to breath in, and took another measurement, each time I felt so excited being naked in front of these women as they measured me…

.Jen had just put her t shirt back on, no bra, and the shape of her breasts underneath the loose fabric looked so sexy.

Then she bent down and did my inside leg, pushing her fingers, up to get the end of the tape between my legs, her hands brushing against my balls “Jen, can you get this out the way whilst I measure” said Helen, and Jen stood behind me, reached her hands between my legs and pulled my cock and balls tightly between my legs..

“get that silly cage of Jen” said Helen, “it's only a little cock, I am sure we can hide that between his legs with some tape, and a few hair bobbles” she said.

Jen was fumbling with my cheap pink cock cage and when she released it, my cock sprung up, and Jen laughed… .

Then I felt a tightness round my cock and balls, as she pulled something round them. “That’s better, I know it’s only small, but we don’t want to see it hanging about do we” she said firmly, slapping my bare ass with her hand as she finished the measurements.

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By *ince163Man
over a year ago

Birmingham

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

Getting better all the time

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By *oannacd67TV/TS
over a year ago

worcester

Mm what a sexy story

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By *.A.MGUY55Man
over a year ago

Rochdale

Horny story sat here throbbing

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By *d funMan
over a year ago

Telford

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By *ina_blackTV/TS
over a year ago

newcastle

Bought lots of things but this has never happened to me

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By *om1962Man
over a year ago

Brighton

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

Im going in a charity shop fololr some heels this week

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By *ymrocruMan
over a year ago

penygroes

This is such a horny story. Keep going.

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

Great stuff

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By *vanabeusedTV/TS
over a year ago

somewhere

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By *ack Seat LoverTV/TS
over a year ago

Woking

Great story!!

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

FIVE.

Helen opened a door at the back of the room, and took me down some steps. Must have been a cellar. My feet were bare on the cold stone steps, and Jen flicked on a light switch, and opened another door into a large room. It had a few tables, chairs, and benches… in one corner there was what looked like a photography studio, lights, nice carpet area, and it was set out like a bedroom, pictures on the wall , and a small kitchen area…

On the other side of the room there was a few chains hanging from an A frame , and lots of floggers, whips, .. It looked like a medieval torture chamber..

Then over in the other corner, again, more lights and cameras, and what looked like a doctors surgery, with various medical implements, another bench with stirrups and cuffs, and various things on the table…

What a place… ...i thought… .

,”Well, jaz, welcome to my workshop.” She said. You have probably realised by now that Jen and I have done this before… the thing is, the shop is for real, and I do donate a lot to the charity, but its just a front for my other business. I have a few web sites, manly cfnm and she male porn and a bit of BDSM. You would be surprised how many men are into this…and you would probably not be suprsed at how many men, experimenting in the art of cross dressing are lured into this shop, notice how I had the plus size shoes and all the tarty dresses close to the window. Those shoes are not seconds my dear, I order them especially for men like you… Never fails… .

Your just the fly that fell into my web.. I suppose you could say it's your lucky day darling… …

This made more sense now, and to be honest I felt relived, and even more excited… .

This is where I make a lot of my content for the web site, and occasionally entertain men and sometimes women who pay me a lot of money for a very exclusslive service.

Whilst I had paid to see escorts before, it was expensive, and getting someone who understands and is able to fullfill my fantasies and needs is generally very difficult. Plenty of dominant women, but I was not into extreme BDSM and they were expensive… ..

There are plenty of men who just want to fuck, get sucked and go, which suited me, and generally it only cost me the price of a hotel room… ..

Helen went on talking and Jen escorted me over to one of the benches and she sat infornt of me, and I was told to stand with my hands in my head..

Helen walked over

…”You have lovely long legs” she said… … “I blushed”, and she looked at me,,, “looks like you are enjoying this”, as she walked closer, bent down and gently teased my cock that was now hanging between my legs, bobbing up and down with my excitement… my face now red with embarrassment...

My cock was getting bigger now almost hard, , but at 4.5 inch it's not that impressive… …

Jen said “maybe best if we milk this little man clit then we can tape it up out the way”.....

Helen smiled, “good idea Jen, get rid of all that tension, and then we can concentrate on getting this gurl ready… .”.

“what do you think jaz, Will you feel better after a quick wank, then you will possibly stop looking down my cleavage and concentrate on getting transformed into the woman you want to be.”

It had been a long time since a woman had touched me never mined wanked me, ..for the last 10 years or so I had been the one on my knees , doing my best to please men… .. I would generally wank myself after the guy had finished with me…

I wanted to be touched and it felt exciting but part of me would have prefered to keep the climax to the end, …. But, at this point I did not know what these ladies had planned for me, and as was obviously paying for there time, I would have preferred some say…. “can you leave it till later” I asked sheepishly”

Helen glared at me… “we are not your fucking whores” she said…. “WHO THE HELL SO YOU THINK YOU ARE”.. I was shocked at Helen's outburst… . “S sssorry” I stuttered,

“Jen, this pathetic excuse for a man, thinks we are whores, he thinks he can decide what we do and when we do it… ., we are helping you become the woman you so want to be, and all you are worked about is cumming to soon and feeling spent and embarrassed after”.....

Helen went on scolding me… .. This was now getting very strange, I was confused after her speech earlier, she was playing games with me..

Helen instructed Jen to take out the paddle that was in my bag and give me 10 hard slaps accord my ass… .

As Jen moved round I flinched not knowing how painful this was going to be.

Jen took the paddle, reached ronlund and grabbed by cock in her hand then began to whack my bare ass hard… WHACK. WHACK. WHACK…

I just nodded, “yes, yes, whatever you think is best,”and my cock was not well and truly hard, well as hard as it gets”

Jen knelt down in front of me. She held the end of my cock between her thumb and forefinger, examining it like a piece of meat… .

“bloody hell Helen, how the hell would you even know it was inside you, maybe you just rub it against your wife clit do you jaz”... She was looking up at me smiling, and she started to wank me exaggerating her thumb and forefinger holding my thin shaft,, her little finger sticking out to the side… .. ..”come on then jaz, let's see you cum for Jen” she said, holding her other hand with a tissue at the ready to catch my cum… pointing my cock away from her…. “any of your mess gets on me, you will be spanked ” she said sternly, as she continued with quick jerky motions to bring me of… Helen looked over, “ is she done yet”.... “no” said jen, “and my hands getting tired…, Will have to charge him extra”

.

“let's speed this up a bit” Helen said as she walked over to me, took out one of her breasts and offered her nipple to my eager mouth… … “I sucked like i have never sucked before, as she cradled my head and squashed her soft fleshy mound of breast against me, and that was enough to make me squirt …”ughhhhhhhhhhh” I groaned as I shot all me sticky goo into Jens waiting tissue… my knees buckled as I cum, it was so amazing, such a warm, fantastic orgasm, nuzzled into Helen's warm soft mammary, …… wowowowowowow I was in heaven… ..

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By *hil911Man
over a year ago

Solihull

Awesome

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

Well written and interesting story

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By *vanabeusedTV/TS
over a year ago

somewhere

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By *d funMan
over a year ago

Telford

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By *acktar74Man
over a year ago

leeds

Very good

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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

Nice very nice

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By *rtmarshMan
over a year ago

Stewarton

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

Great story

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By *atsWoman
over a year ago

wexford

Fantastic !!

Can't wait for more xxx

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

Getting more interesting as we go along . Keep up the good work

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By *ippa 63TV/TS
over a year ago

St Helens

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By *ymrocruMan
over a year ago

penygroes

More. Mmm

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By *ylonLexiTV/TS
over a year ago

Blackpool

This is such a kinky tale xx

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

Very kinky indeed, almost makes me want to try cross dressing

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By *vanabeusedTV/TS
over a year ago

somewhere

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

SIX

Jen handed me a tissue to clean my limp cock, as Helen handed her a pair of dark red lacy panties, and she helped me step into them “It's smaller than my clit now” laughed Jen as I tucked myself into the panties…

Then they both helped to fasten me into a tight a black bra, this hid the tape, and with a couple of small fillets which she fitted perfectly against my already visible mounds, this rounded of the illusion perfectly… I could not believe it when I looked down to see my cleavage… She stood in front of me and adjusted the fillets and the strap, until she was happy with the fit…

Helen then handed me an unopened pair of black 15d gloss hold ups, and I sat down on the chair and put them on. She knelt in front of me, showing even more of her ample cleavage as she adjusted the stockings round my toes, and then she made me stand up and got behind me to straighten the tops of my hold ups, pulling them up just below my panties, brushing her hands gently against my limp cock which had dribbled a wet patch of cum visible now against my red panties. “you are going to have to pay for these as well now, messy girl… ., we won't be having those back” she said pushing her red fingernail against the wet patch and gently teasing the end of my cock, …..

Then she took out a black and red corset. “This will be ideal for you luv, does a great job of hiding all this”, as she pointed a finger and prodded at my stomach, which was hanging slightly over my panties.

She pulled out the cords and held it open as i stepped into it, and positioned it round my waist and started to pull it tight and click the lower hooks together, Then Helen and Jan started to strap me in, “breath in” they said, and they both pulled me in tightly, taking turns to pull on the cords as they strapped me in…..

“Right, over to you Jen,,, Time for the makeup”..

Jen had me sat in the bedroom area in front of a lovey dressing table with a n amazing array of makeup, brushes, and for the next 30 minutes she worked a miracle with my face whilst Helen did my nails, a sort of mini manicure, and finished them with a lovely deep pink varnish.

Helen took a black shift dress, out of the wardrobe in the pretend bedroom….. “this will be perfect for you Jaz” she said, as she helped me in to it.

She fastened the back of the dress, and adjusted the hem which sat just above my knees… “not to tarty, she said, I am sure Greg will love this. “....

Who the hell is Greg I thought, …..

then on cue, Helen went on to say

“Greg, in case you are wondering, is one of my regular clients. He is a lovely old guy who has a thing for gurls like you. He likes a bit of role play, and he loves guesting in my short films.

He will be over in about half an hour, and your now going to be his leading lady”

I did not know whether to laugh or cry,,,, yes the thought of having a nice gent have his way with me was very appealing, but to have the resulting video uploaded for all to see filled me with horror….

.................

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

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By *istresskaty1981TV/TS
over a year ago

brigg

Interesting xx

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

South Birmingham

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By *usie4uTV/TS
over a year ago

Havant

More please xxx

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

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By *anessa_xdTV/TS
over a year ago

Larkhall

Loving this...??

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

Would love this to happen to me, though not surrendering my wallet.

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By *imale38Man
over a year ago

Barnsley

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By *.A.MGUY55Man
over a year ago

Rochdale

More an more this is great very horny

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By *d funMan
over a year ago

Telford

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By *ommy littleMan
over a year ago

Coventry

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By *vanabeusedTV/TS
over a year ago

somewhere

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By *hloe_swallowzTV/TS
over a year ago

stafford

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

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By *oe774Man
over a year ago

Stowmarket

Amazing

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By *rtmarshMan
over a year ago

Stewarton

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By *iss_Nikki_xTV/TS
over a year ago

and around

Keep going...

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

Loving this story xx

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By *ndrea54TV/TS
over a year ago

cambridge

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By *ymrocruMan
over a year ago

penygroes

Mmmm keep going. Xx

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By *r.ringMan
over a year ago

totton

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By *acabiscuitsMan
over a year ago

exeter

Wow sexy post

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By *d funMan
over a year ago

Telford

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

Seven

Jen had some costume Jewellery on the table and was selecting a few bangles and an ankle bracelet and some earrings. She also had a silver and black collar for me to wear, with the words Cum Slut hanging on a large tag..

“Greg likes his sluts in a collar,, , this has a clip for a lead or a chain on it, so he can play his games with them. you will see soon enough Jaz”….

I was panicking now, I just asked them to let me go, I offered to pay the £100 and whatever the cost for the dresses and stockings were, and asked if we could just leave it at that… I started to walk out the room, - then remembering that Helen had locked my cloths away, and had could have lifted my wallet and car keys from my jacket pocket I hesitated.

Jen and Helen soon had me convinced to stay. Jen came up so close to me, “Look Jaz, what have you got to worry about, I will keep your face of shot, and will take a few pictures of you as well that you can keep, - relax, enjoy it.. You have come this far, and you have obviously enjoyed it and you look amazing, one of the best we have had”,,, Helen was telling me how good I looked, and how luck they were to have me walk in the shop, and was suggesting that pose for a few pictures to take home with me, and that its worth paying that little bit extra to get an experience that I would enjoy.

I felt more at ease, especially when they started the mini photo shoot…

I had my wig on that I brought with me, and Jen made sure it looked tidy, straightening it up and brushing it. That felt so good, all this attention was doing wonders for my feminine ego.

“I am jealous of your legs jaz, you look amazing” said Jen as she took me over to where she had a camera set up, and switched on the lights, and soon had me even more relaxed, feeling very girly and feminine as she directed me posing for some pictures.

“Lovely,,, Lovely,,, to the side Jaz,,, look over your shoulder,,, head up, push your bum out a little…. Lovely… a bit more leg, that's right babe, don’t be shy, lift up your skirt, let's see the tops of your hold ups,.... Wow. ….… wow those legs look amazing….. SMILE jaz,,,, come on Jaz, SMILE…. Wow…” she went on, as she took more pictures.

Jen was tracing her hands over my dress, and she kissed me gently on the cheek. ,”I like to be in Helens films as well, and maybe she will let you and me do something after– you would like that”…… “I know I have been teasing you, but I guess you like that, and look, you’re a woman, , you don’t need to use your cock, but I bet you want to feel a nice hard cock inside you… ..… AM I RIGHT JAZ”…. “oh god yes, Jen”,,, I giggled...

,,, bloody hell, I was actually giggling like the cock hungry slut I so wanted to be..

– she knew just what to say to make me feel so fucking slutty and horny….

I was so excited now, and did not even notice that Greg had arrived and was busy chatting to Helen.

Jen kept me talking, distracting me from Greg and Helen and then after a few minutes Helen walked over.

“OK Jaz, Greg is very much up for this, and he is keen to have his evil way with you, but he does not want to meet you first. He just wants us to film it so its fresh for him, and more exciting… I have told him to take it easy with you, and that you are a game gurl, up for most things, love a nice spanking and desperate for a good seeing too” – she was smiling as she said this, “are you excited” she went on,,, “he is a big boy, and he likes it rough”.. Helen was clearly excited, “I can’t wait to watch, it’s getting me wet thinking about it” she went on… …. .

“We will just film everything and we can edit what we have at the end…… is that OK darling” she said, “sure it is” she went on, “I bet your gagging for a nice bit of cock” ,,,,,, she did not give me chance to get a word in, I just stood there nodding , it's too late now for second thoughts, I just had to get on with it… ..

Jen had a dog lead attached to my collar, and walked me over to Greg. I was on all 4’s, as she handed the lead to Greg. “a new toy for you Greg” she said and he took the lead and started to walk me round the room for a bit, calling me to heel as he made me crawl by his side as he told me what he intended to do sluts like me….He had a riding crop and gave me the occasional slap across my ass as he walked me like a dog, before making me getting me up onto the table.

I was secured with my face squashed against it, dress pulled up over my back wrists tied tight and knickers off, stuffed inside my mouth.

Then he started to spank me. He was calling me all the names under the sun, whilst he abused me with an assortment of floggers, paddles and a slipper…. As for taking it easy, my bum and the tops of my legs were red and sore I had never had such a hard spanking before in my life… . The more I screamed the more he spanked me… , and then he stuffed my panties in my mouth to shut me up…. Jen and Helen were both stood by filming the action, and despite Jens earlier reassuring words, they did nothing to discourage his excited and frantic actions…for his age, he was very fit, and obviously enjoyed the attention, almost providing a running commentary to Jen and Helen , talking to the camera as he tormented me..

I had not seen his cock yet, but was about to feel it, as he wasted no time, and started to guide it into my hole. I was very tense, not knowing how bug his cock was and expecting the worst. Jen kept making him stop as she got in close to take pictures but he got impatient and just impaled me. His hard, big cock ripping up my hole, pushing hard, and my insides felt so hot as he pumped in and out of me, fucking me hard and deep. Helen was filming my face, and she pulled out the panties so she could record my squeals and pants as he fucked me.

“ahhhhh,,, owwww,, owwww ahhggggggggggg” I was squealing as he fucked me….. “looks like she is enjoying it now” whispered Jen to Helen, “oh yes, my goodness,,,,, I think we have a new star here” , replied Helen

The fucking continued, as Greg continued his commentary “this is how a man deals with sluts who can’t pay their rent, spending your money on dresses and wigs so you look like a woman, - but your just a facking sisisy faaaagg with two holes to fill with my big cock” he said in his southern accent - I guess he was trying to keep to the very loose role play scenario for the context of the video –

The filming paused as Greg pulled his cock out of my ass, and went to get a drink…”thirsty work fucking slags” he said, ……. Charming I thought ……. As I was unclipped from the ties round my wrists and Helen and Jen helped me up.. “Now for some oral shots, and he wants to finish of with a nice facial for you” said Jen… so on your knees like a good girl” she went on..

I struggled to get up, but as the pain from the fucking subsided, I have to admit that I did feel very excited, and the last 5 minutes of the fucking was very nice….. My ass was stinging, but it felt good, and I was soon on my knees, looking up as Greg took hold of my chin with his large hands “your ladies ready to roll” he said,,, “this slut is keen, mouths open and she is gagging for it” ,,, you’re a pretty thing for a tranny” he said,,, “are you ready to taste my cock” “yes sir,” I said, getting into character,,,,, Jen and Helen were in position filming as Greg laughed than slapped my face, “open bitch” he said,,,, and I opened my mouth, looking up at him, ,,,,,, He slapped his cock across my face,,, it was at least 8 inches, and that certainly explained the pain from the fucking….. he had pulled the condom off “we don’t need this” he said, and then he spat on my face… “suck my cock ye faaag slut” he said, and within seconds, he was feeding his cock down my throat, and I was soon gagging hard as he face fucked me, making me dribble salvia down my dress…….. Oggggg, Ughhh Ugggg , UGGG,, aggg Ahgg uuuu aghhh I was gaging as his cock pushed in and out my throat,,,,,,,He would pause every now and then, ordering me to suck and lick his balls, and then spiting at me again, he seemed to like the mess it was making all over my face, which was wet through with my own saliva and his spit….

When he came, it was amazing, I felt the first glug of cum on the back of my throat, as he rammed his cock deep and held it in position till he sensed my panic, and then he pulled out and pumped his cock with his hand to empty the remaining spurts of his thick gooey cream over my face , and it seemed to cum for ages……. Then he made me suck it again, “there more where that came from he said”, and he looked over to Jen “did you get thatm or would you like a replay” he said laughing,,, “come on girls, whos next” he said,,,,, “not to day sweetie” sad Helen, I am sure Jaz is ready for more…….

He had me on my back next, laid on the table, my dress was removed now, and I just had my hold ups and corset on, he held my legs up as he fed his cock inside my ass for another fucking,,,,,, Jen and Helen continued to film it, and Jen made sure she got her camera in position as he pulled of his condom and emptied his load of cum over my ass. “that ell do for today “ he said,,,,,, “would fack this slut every week”,, he said…

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By *ony 529Man
over a year ago

coventry


"Seven

Jen had some costume Jewellery on the table and was selecting a few bangles and an ankle bracelet and some earrings. She also had a silver and black collar for me to wear, with the words Cum Slut hanging on a large tag..

“Greg likes his sluts in a collar,, , this has a clip for a lead or a chain on it, so he can play his games with them. you will see soon enough Jaz”….

I was panicking now, I just asked them to let me go, I offered to pay the £100 and whatever the cost for the dresses and stockings were, and asked if we could just leave it at that… I started to walk out the room, - then remembering that Helen had locked my cloths away, and had could have lifted my wallet and car keys from my jacket pocket I hesitated.

Jen and Helen soon had me convinced to stay. Jen came up so close to me, “Look Jaz, what have you got to worry about, I will keep your face of shot, and will take a few pictures of you as well that you can keep, - relax, enjoy it.. You have come this far, and you have obviously enjoyed it and you look amazing, one of the best we have had”,,, Helen was telling me how good I looked, and how luck they were to have me walk in the shop, and was suggesting that pose for a few pictures to take home with me, and that its worth paying that little bit extra to get an experience that I would enjoy.

I felt more at ease, especially when they started the mini photo shoot…

I had my wig on that I brought with me, and Jen made sure it looked tidy, straightening it up and brushing it. That felt so good, all this attention was doing wonders for my feminine ego.

“I am jealous of your legs jaz, you look amazing” said Jen as she took me over to where she had a camera set up, and switched on the lights, and soon had me even more relaxed, feeling very girly and feminine as she directed me posing for some pictures.

“Lovely,,, Lovely,,, to the side Jaz,,, look over your shoulder,,, head up, push your bum out a little…. Lovely… a bit more leg, that's right babe, don’t be shy, lift up your skirt, let's see the tops of your hold ups,.... Wow. ….… wow those legs look amazing….. SMILE jaz,,,, come on Jaz, SMILE…. Wow…” she went on, as she took more pictures.

Jen was tracing her hands over my dress, and she kissed me gently on the cheek. ,”I like to be in Helens films as well, and maybe she will let you and me do something after– you would like that”…… “I know I have been teasing you, but I guess you like that, and look, you’re a woman, , you don’t need to use your cock, but I bet you want to feel a nice hard cock inside you… ..… AM I RIGHT JAZ”…. “oh god yes, Jen”,,, I giggled...

,,, bloody hell, I was actually giggling like the cock hungry slut I so wanted to be..

– she knew just what to say to make me feel so fucking slutty and horny….

I was so excited now, and did not even notice that Greg had arrived and was busy chatting to Helen.

Jen kept me talking, distracting me from Greg and Helen and then after a few minutes Helen walked over.

“OK Jaz, Greg is very much up for this, and he is keen to have his evil way with you, but he does not want to meet you first. He just wants us to film it so its fresh for him, and more exciting… I have told him to take it easy with you, and that you are a game gurl, up for most things, love a nice spanking and desperate for a good seeing too” – she was smiling as she said this, “are you excited” she went on,,, “he is a big boy, and he likes it rough”.. Helen was clearly excited, “I can’t wait to watch, it’s getting me wet thinking about it” she went on… …. .

“We will just film everything and we can edit what we have at the end…… is that OK darling” she said, “sure it is” she went on, “I bet your gagging for a nice bit of cock” ,,,,,, she did not give me chance to get a word in, I just stood there nodding , it's too late now for second thoughts, I just had to get on with it… ..

Jen had a dog lead attached to my collar, and walked me over to Greg. I was on all 4’s, as she handed the lead to Greg. “a new toy for you Greg” she said and he took the lead and started to walk me round the room for a bit, calling me to heel as he made me crawl by his side as he told me what he intended to do sluts like me….He had a riding crop and gave me the occasional slap across my ass as he walked me like a dog, before making me getting me up onto the table.

I was secured with my face squashed against it, dress pulled up over my back wrists tied tight and knickers off, stuffed inside my mouth.

Then he started to spank me. He was calling me all the names under the sun, whilst he abused me with an assortment of floggers, paddles and a slipper…. As for taking it easy, my bum and the tops of my legs were red and sore I had never had such a hard spanking before in my life… . The more I screamed the more he spanked me… , and then he stuffed my panties in my mouth to shut me up…. Jen and Helen were both stood by filming the action, and despite Jens earlier reassuring words, they did nothing to discourage his excited and frantic actions…for his age, he was very fit, and obviously enjoyed the attention, almost providing a running commentary to Jen and Helen , talking to the camera as he tormented me..

I had not seen his cock yet, but was about to feel it, as he wasted no time, and started to guide it into my hole. I was very tense, not knowing how bug his cock was and expecting the worst. Jen kept making him stop as she got in close to take pictures but he got impatient and just impaled me. His hard, big cock ripping up my hole, pushing hard, and my insides felt so hot as he pumped in and out of me, fucking me hard and deep. Helen was filming my face, and she pulled out the panties so she could record my squeals and pants as he fucked me.

“ahhhhh,,, owwww,, owwww ahhggggggggggg” I was squealing as he fucked me….. “looks like she is enjoying it now” whispered Jen to Helen, “oh yes, my goodness,,,,, I think we have a new star here” , replied Helen

The fucking continued, as Greg continued his commentary “this is how a man deals with sluts who can’t pay their rent, spending your money on dresses and wigs so you look like a woman, - but your just a facking sisisy faaaagg with two holes to fill with my big cock” he said in his southern accent - I guess he was trying to keep to the very loose role play scenario for the context of the video –

The filming paused as Greg pulled his cock out of my ass, and went to get a drink…”thirsty work fucking slags” he said, ……. Charming I thought ……. As I was unclipped from the ties round my wrists and Helen and Jen helped me up.. “Now for some oral shots, and he wants to finish of with a nice facial for you” said Jen… so on your knees like a good girl” she went on..

I struggled to get up, but as the pain from the fucking subsided, I have to admit that I did feel very excited, and the last 5 minutes of the fucking was very nice….. My ass was stinging, but it felt good, and I was soon on my knees, looking up as Greg took hold of my chin with his large hands “your ladies ready to roll” he said,,, “this slut is keen, mouths open and she is gagging for it” ,,, you’re a pretty thing for a tranny” he said,,, “are you ready to taste my cock” “yes sir,” I said, getting into character,,,,, Jen and Helen were in position filming as Greg laughed than slapped my face, “open bitch” he said,,,, and I opened my mouth, looking up at him, ,,,,,, He slapped his cock across my face,,, it was at least 8 inches, and that certainly explained the pain from the fucking….. he had pulled the condom off “we don’t need this” he said, and then he spat on my face… “suck my cock ye faaag slut” he said, and within seconds, he was feeding his cock down my throat, and I was soon gagging hard as he face fucked me, making me dribble salvia down my dress…….. Oggggg, Ughhh Ugggg , UGGG,, aggg Ahgg uuuu aghhh I was gaging as his cock pushed in and out my throat,,,,,,,He would pause every now and then, ordering me to suck and lick his balls, and then spiting at me again, he seemed to like the mess it was making all over my face, which was wet through with my own saliva and his spit….

When he came, it was amazing, I felt the first glug of cum on the back of my throat, as he rammed his cock deep and held it in position till he sensed my panic, and then he pulled out and pumped his cock with his hand to empty the remaining spurts of his thick gooey cream over my face , and it seemed to cum for ages……. Then he made me suck it again, “there more where that came from he said”, and he looked over to Jen “did you get thatm or would you like a replay” he said laughing,,, “come on girls, whos next” he said,,,,, “not to day sweetie” sad Helen, I am sure Jaz is ready for more…….

He had me on my back next, laid on the table, my dress was removed now, and I just had my hold ups and corset on, he held my legs up as he fed his cock inside my ass for another fucking,,,,,, Jen and Helen continued to film it, and Jen made sure she got her camera in position as he pulled of his condom and emptied his load of cum over my ass. “that ell do for today “ he said,,,,,, “would fack this slut every week”,, he said…

"

. Wow this is what dreams are made of very very sexy it's only as got me hard reading this I just need a helping hand now

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

Your not the only one, wheres the nearest charity shop

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

Loving it

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By *imale38Man
over a year ago

Barnsley

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

Loving this, where is this shop?

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By *d funMan
over a year ago

Telford

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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

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By *vanabeusedTV/TS
over a year ago

somewhere

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By *d funMan
over a year ago

Telford

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

South Birmingham

what a lucky sissy fag.

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By *d funMan
over a year ago

Telford

Please more

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By *mmacdheelsTV/TS
over a year ago

France, Not in

Going into a charity shop will never be the same any more. Will always wonder if !!

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By *ames WhyteMan
over a year ago

Near Manchester Airport

Bookmarked

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

I'm getting worried for Jasmin now, stuck in that basement for a week

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

Great story

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By *imerickboyMan
over a year ago

city

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By *ammyTV/TS
over a year ago

manchester

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

It's here

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