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Discovered at work - part 2

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

Part 2

Recap (see Discovered at work) –

Jack and his work colleague Jan are on a business trip during which Jan discovers Jack’s secret life as a cross dresser . Jan is now enjoying using and abusing jacky for her entertainment and pleasure..

Part 2- ONE

I felt deflated, her cold self centred desire to use me with no sentiment, or concern as to my feelings and take her pleasure in my abuse was clearly driving her and exciting her more and more…. It was ironic that I was becoming more and more addicted to her, attracted and needy of her attention, her femininity and I really wanted to see her naked, and especially would have liked to see her taking of her bra and getting her tits out.

Each time I tried think about the reality of my situation, a wave of panic flooded my senses, she could ruin my life with one deliberate, or more worrying a careless email or throwaway comment to a colleague. I had to make sure I kept her happy at all costs, The strange thing was, I was enjoying the excitement and the thrill of it all…

"oh please Jan, let me see, please" ,, "NO" she said, " YOU WILL DO AS I FUCKING SAY" – and with that she put a make shift blind fold on me (she had used a pillow case from the room” , and ordered me to get my knickers of and to rub some lube inside my ass so I would be ready.

I did as she said, and then she had me get on all 4’s , my ass at the end of the bed, and she strapped my hands together with my belt and placed condom on my back. "there, that’s as much bondage as we can do at the moment, your all ready for a good seeing to, this is going to be good, I can't wait to watch you get a good fucking, and I am getting 50 quid as well, this is good times"....

The guy came in, Paul he was called, and she greeted him and took his coat. Jan took his money, and whilst I could not see what was happening, I could hear them chatting, and I guess from what I could hear, he was a mature businessman type.

He asked Jan to sit on the bed legs apart in front of me “I want to see you whilst I am fucking this faggot” he said with an annoying tone,,,, She surprised me by doing exactly as he said. All the time I could not see, but I could hear him take of his trousers, and walk towards me, placing his hands against my bare exposed ass.

She got into position, and I was so frustrated that I could not see, but I could smell her sex in front of me, inches from my face… . she slapped my face “just don’t get any ideas” she said to me…..

“take your blouse of now ”, he said to Jan …" yes that’s good" he said, "yes they are big, come on let me see them"... , Jan was obviously enjoying teasing him, and I can only imagine her hands inside her bra squeezing her tits and rubbing her nipples.

Then I felt a hard slap across my naked ass….”time to fuck this slut”,,, he said taking the condom of my back, “is it lubed” he asked “yes the slut is all ready for you” said Jan.

I could feel him pushing into my hole…."you have a fantastic pair of tits, let's see you squeeze them nipples,... Yes there nice," and he pushed his cock deeper inside me "a nice tight ass hole as well".... Mmmmmmmmm he groaned as he went deeper inside me and stared to fuck me hard as he watched Jan play with her tits in front of him. – all the time I could not see Jan, and she was inches form me, my cock was straining in the cage hanging between my legs ….

He built up a steady rhythm, and after the initial pain of the first deep penetration subsided, the heat was replaced with an amazing smooth rubbing sensation, it felt so good, his warm firm cock seemed to be hitting all the spots for me, my cock was jangling in unison to his thrusts and he just started to chat with Jan as he fucked me…

" whats this all about" he said, " you two an item, is he your hubby?,, is this a fantasy of yours… I can never resist a cuck and you are one hell of a… ….. ,.... "

Jan interrupted - .."fuck No" she said," he is my boss at work"...

and he laughed, " wow, that’s a new one on me, cuck boss fantasies" …

“No this is real, he is my whore " , and they both laughed, and he continued to fuck me harder. " so, he is your boss at work, and you wanted to get him shafted eh ??” he laughed “but you are the real boss, how, why – would love to know more – but I suppose its none of my business,. But I can see your enjoying it, go on, finger your pussy” …

Jan was enjoying it, and she started to play with her self I could hear her - she was clearly very wet , but then she got up … “I need to see this” she said, as she got of the bed and looked closer at him fucking me, “pull out let me see your cock go in him,, yes, wow that’s good, let me take a few pictures” she said,,

Then she got closer to him and I guess he was now playing with her tits and kissing her as he fucked me, her hands were on my ass, touching his cock as it went in me, her fingers pushing towards my hole squeezing slightly between his cock and my ass…

He pushed one last time, and I could feel him cum inside the condom. “Oh god that was good” he said, holding his cock deep inside me,,, yes it was amazing,,,,,

"OK" he said, "now I want to punish his sissy fucking ass, it was what we agreed, and its going to fucking hurt him……. " he pulled out and took the condom of and placed it on the table. "Stay there" , said Jan, and she repositioned herself back on the bed, pulling my head down int the bed sheets…. , and held my back, and he started to slap my ass. Jan pushed my head harder into the bed, as she could see what was coming next. I had no idea, but he had took his belt of, and was obviously indicating to Jan that he was going to give me 6 with his belt.

The pain was intense, 6 really hard belts, and I was in agony, I tried to move, but Jan had all her weight on my back, and he was quick. 6 hard whacks across my exposed ass, I could feel the pain rip through me….. I tried to move away but it was all done so quickly,,,,

"OK all done" he said," get your boss up, and he can clean my cock" he laughed… and lets take of his blindfold, I want to see this pathetic excuse of a boss you have…..

I was pulled up and onto my knees on the floor, my hands were still tied, and he told Jan to open my mouth. Jan pulled of the blind fold, and I looked up to see him looking down at me and his cock hanging down before me…… “what a pathetic slut you are” he said laughing….

Jan took her hand to my chin, and said "open wide, tongue out" , and he squeezed his condom onto my tongue, “that’s it, drink it al down” she said squeezing the last drops into my open mouth….

Then he stuffed his semi erect cock into my mouth… "suck on this you pathetic fucking faggot" he shouted, pushing his cock in my mouth and gripping my head tight.. His cock was getting hard again "see you could have had this in your pussy, I can sometimes cum 3 times in a session,”...... he said as he started to face fuck me hard, and soon deposited his second load down my throat.

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By *rouble 50Man
over a year ago

turriff

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By *cotFit4funMan
over a year ago

Kettering

Wow how intense!

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By *iving for todayMan
over a year ago

stirling

Just gers better

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

Brill story

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By *imale38Man
over a year ago

Barnsley

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By *r and Mrs BlackCouple
over a year ago

Chesterfield

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

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By *aulaxd500TV/TS
over a year ago

Wigan

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By *eanasmustardMan
over a year ago

corby

Excellent

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By *onsi69Man
over a year ago

llanfairpg

Fantastic

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By *hager777Man
over a year ago

Hereford

More please

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By *d funMan
over a year ago

Telford

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

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By *ane08TV/TS
over a year ago

redruth/ camborne

Very nice getting me hard again

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2 – 2

After Jan had finished getting herself ready, I was allowed to shower and clean myself up. She took delight in re fitting my cock cage, and it felt embarrassing stood naked in front of her whilst she was dressed so casually, in her Jeans and blouse, “need to get my sissy locked away for the night” she laughed as she slapped my ass …

It had been a hell of a day, lost count of how many cocks I had sucked, and my ass was sore from the belting - but I still felt high on adrenaline after the excitement of the day. I was starting to get used my new relationship with Jan but still on edge, as she seemed to be very un-predictable. Jan

“you get this room tidy, get my cloths unpacked ironed and hung up in the wardrobe and get your-self cleaned up - put on that pretty pink sissy chemise that we got today and get yourself an early night, - you will be having a busy day tomorrow you can sleep on the floor near the window” she said as she went out to the hotel bar shouting “don’t wait up ”.

I have to be honest, I could have done with a few pints after the events of the day, and on a normal business trip, even when I dress in the hotel rooms on my own, I would always finish the night in male mode at the bar, having a drink, chatting / making conversation with others - – and hearing Jan order me tidy the room, iron her cloths and to go to bed early as she headed out to the bar really hit home, reinforcing my new role and total humiliation.

I took the opportunity to check my emails and phone messages whilst Jan was out , sent a few texts home – usual stuff – busy day, hope you’re ok etc etc - remembering the reality of my situation, and the fact that I had a real life, and needed to keep things as normal as possible – but then thinking about what was going to happen over the next few days… I took the opportunity to shave again, making sure I was as smooth as possible, and put on the pink chemise, remembering back to the events earlier with Amber and Claire – god I look such a sissy in this, and it feels so good- as I looked at myself in the mirror, posing…. then I got on with the tidying. I hung up my cloths , then started to unpack Jan’s bag, picking up what she had left on the floor in the bathroom, ironed her cloths and hung them up as she instructed. I felt good, but with my cock caged, it was a constant reminder of my new found role in Jan’s life,

I made myself as comfortable as possible with the spare duvet and pillows and eventually fell asleep.

I felt a sharp kick to my side, and looked up, struggling to open my eyes – I must have dropped of quickly, despite the fact that it was so uncomfortable on the floor.

Jan was looking down at me, her heels pushing against me, pulling at the duvet …

She had obviously had a few drinks, “come on SISSY, help me get ready for bed, chop chop and get me a cup of tea” she said…

I jumped up and it took mem a few moments to regain full awareness and then it hit home – shit this is real…..

I put the kettle on and as she laid on the bed still in her heels, jeans and blouse. “pass me the tv controls slut” … “put your heels on sissy, I like to see you mincing round the room” …. “how’s your ass, is it still sore, come here let me see… lift up your nighty, shall I rub some cream on it ”… I quickly put my heels on, and took the tv control to her and stood by the side of the bed, as she lifted my nighty and pulled down my pink panties and laughed - She placed her cold hands against my bare skin, running her fingers over the raised red welts from the belting earlier “OH poor love….. that must have hurt like hell Jacky, It made me squirm”…… “I think I wil l have to have a go at you later, I could get into the BDSM stuff”,, she laughed.. I could smell the mixture of alcohol and perfume on her breath, she must have had a few gins, as she seemed to be slurring her words a lot.

I brought over her tea and she motioned me to the end of the bed… “my feet”,,,, “massage my feet”,,,

I sat on the edge of the bed and I took of her shoes and placed them on the floor, her feet felt warm and clammy - she had nice feet, a deep red varnish on her toe nails.. I started to massage them rubbing the soles of her feet with my hands, trying my best – reacting to her moans of pleasure “oh I could get used to this, I do love my feet played with OOOOHHH yes that’s nice jacky” she moaned as I continued to massage her feet “suck my toes jacky” she said,,, and I bent down and took her big toe in my mouth and sucked it in, and used my tongue to lick between her toes … This continued for a while, as I sucked each toe in turn licking carefully between them as she stretched out enjoying the pampering………… Then she told me to look at the TV screen, and she had managed to cast her phone to the TV screen and I could see – “look at you sissy, all the pictures I have of you from today” she was laughing as she scrolled through them,,, then a clip of me sucking cock at the garage, one of me trying to dance round the pole at the transformation shop and then the last one this evening - me getting fucked - and a close up of his cock diving deep into my ass…..

“pull of my jeans sissy” shouted jan, “I need to sleep”…

I reached up and pulled down jan’s jeans, pulling them over her smooth white tones legs, she was wearing a white thong, and I looked up between her legs, catching her eye as she stretched out.

“what you looking at sissy,,, you looking at my snatch,,,,,,, “,,,”sorry ma’am” I said, remembering that she liked me to call her ma’am… “yes, that’s right, its ma’am, and I am not your fucking mam, I am your owner, your pimp, your mistress now and forever” she said “get my nighty , the black one – I hope you hung it up so its not creased”,,,”yes ma’am” I replied, and I quickly brought it over …

“take of my blouse then” she said, “come on slave, you do everything for me now, I am your queen, and you are going to learn how your queen likes to be worshipped”..

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By *rouble 50Man
over a year ago

turriff

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By *mfao88Man
over a year ago

north yorkshire

Absolutely love this. Cant wait to.hear more

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By *ppetiteforsexMan
over a year ago

Isle of Man

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By *ndrea54TV/TS
over a year ago

cambridge

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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 *cotFit4funMan
over a year ago

Kettering

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By *ane08TV/TS
over a year ago

redruth/ camborne

It's so horny I want to be jacky

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By *orwillieMan
over a year ago

Melrose

Pathetic...

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By *angerineMan
over a year ago

somewhere inbetween the right and wrong

Loving Jackie's story

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By *tockton GentMan
over a year ago

Middlesbrough

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-3

I leaned over and started to unbutton Jan’s blouse; my fingers were shaking I was so excited. Whilst I rejected her advances in the past, I was always obsessed with looking at her cleavage at work, and could not help myself, and now, I was actually going to get the chance to see her breasts. I guess the drink had relaxed her, and as I pulled open the final button, she let me pull her blouse apart to expose her black bra, barley covering her amazing breasts. Jan had her head back and eyes closed ,, her hair resting over her shoulders, “you like” she said quietly, “oh god yes ma’am , please can I take of your bra”,,, “go on then”,,,,,, I had to stretch my hands behind her warm naked back to unclip the clasp and let her bra drop forward, pulling the straps down over her arms, releasing her glorious breasts, falling forward, and resting on her chest, huge full pink nipples, already hard, her white skin with light dusting of pink freckles, I could not help myself, and I moved down to suck on her nipples, expecting a rebut , but nothing, she just lay back and let me gently suckle on her nipples, groaning quietly under her breath. I moved over to sit on the side of the bed so I could get better access, and started to suck harder on her nipples, licking and kissing – it felt good, my cock was now straining inside the cock cage, and I dearly wished she would let it out ….I placed my hands on her breasts and squeezed them softly, pulling them together and licking between them – oh how I wish I had real breasts like these, they were amazing, - I suppose I was taking advantage of her now, she was clearly starting to fall asleep on the bed, as I started and lick her belly, moving down kissing and licking until I got close to her pussy. I got up, and moved to get myself between her legs, lay on the bed, my cock cage pressed against the bed and I pushed my face up against her trimmed ginger pussy, pulling aside her thong and placed my lips against her glistening warm moist vagina, and started to kiss and lick her, pushing my tongue against her clit, - her reaction was instant as she stretched her legs around me - my face now hard against her pussy as she started to groan louder,,,,, “suck me bitch” she said, “worship you mistress… oh yes ,,,,ahhhhhhh mmmmmmmmm yes, yes , yes ,,,, I licked and sucked burying my head between her legs, breathing in her musky sweet scent, my face soaked with her juices…,,, she then started to buck her pussy against me, groaning louder “oh god, yes, YES , YES OHHHHH YES…. I licked her clit, rubbing my face against her harder now sensing her climax approaching, feeling good that I was able to satisfy my mistress, feeling so good that she was allowing me to do this for her… and then she climaxed, and to my surprise she started to spurt her juices into my open mouth “drink it all bitch, don’t spill any, AGHHHHHHHH YES YES YES YES”…

“I hope you enjoyed that ma’am” I said meekly, “can you lease let me take this cage of now so I can…..”

“CAN WHAT” she shouted….. … “You will keep yourself locked up , now I am going to turn over and I want you to get that tongue of yours inside my ass, and you can lick my ass as I fall asleep, because that’s what you are now, you are my ass licking sissy slave”

I buried my head between her ass cheeks, breathing in her aroma, and pushed my tongue between her cheeks, pulling them aside and licking deep, as she pushed back against me moaning. “Yes, this is good sissy” she said, “keep going, oh yes, deeper..mmmmmm I could get used to this”, I continued licking her , pushing inside her hole, kissing and licking her…….

“I need to pee”, she said

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

Still so good

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By *tockton GentMan
over a year ago

Middlesbrough

This is fantastic

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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

Great story

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By *cotty99Man
over a year ago

tranent

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By *d funMan
over a year ago

Telford

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

So horny ??

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By *agical HandsTV/TS
over a year ago

wellingborough

Love this so much

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By *cotFit4funMan
over a year ago

Kettering

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-3

Pulling away and I sat on the bed as she got up , “crawl by my side slave, time to prove yourself.. ”, and she told me to get into the shower cubicle “have always wanted to try this,,, on your knees”… guessing what was to cum, I quickly pulled my chemise of.. “on your knees for your queen” she said laughing,,,,,,,, I knelt before her on the floor of the shower and braced myself, looking up at her exposed pussy, her breasts, - yes she looked amazing and she was my goddess now, and I wanted to prove myself even more, and after her spurting display earlier, I was even more excited, but also apprehensive - I had never done anything like this before “lick me now , hurry up, get your head between my fucking legs bitch, your my fucking slave now so you can learn to drink from me”,,, she squeezed her pussy against me, pushing my head against the side of the shower, grinding against my face as she released floods of warm pee that spurted over my face…, It seemed to on for ever, initially in my mouth, but the taste and smell made me gag and I tried to move away, - she just pushed against me harder “drink me bitch” ,, holding me in position covering my face her piss streaming down over my body……

The next day was a lazy start for Jan – but not for me,,, - After she pissed over me last night, she showered then went to bed, allowing me to shower and do the same. I managed to get some sleep, as she allowed me to sleep at the bottom of the bed. The morning was full of her ordering me about, The first thing she made me do was suck her toes as and lick her feet she scrolled through her phone …. “you got a treat last night I let me guard down allowing you to suck my tits,,,, you took advantage” she seemed annoyed but I could not tell if she was serious or not. She lectured and continued to chastise me - “my ass is itchy slut, you know what to do” she shouted as she turned over and I buried my head between her cheeks and licked her , she pushed her head back against my face “yes - this is a good way to start the day with my manager licking my ass” she laughed

Later she made me order room service for breakfast, and she sat in her bed, issuing orders, as I had to wait on her like a slave, holding her food for her, getting her drinks, changing the tv channel, running her a bath… I was allowed to eat her leftovers sat on the floor next to the bed … “you are my slave now” she said, so you will have to learn to act like one…

“We will be going shopping later, and you better be prepared to spend some money on me, your credit card is going to get a hammering – today is all about me”

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By *agical HandsTV/TS
over a year ago

wellingborough

Mmm what a dream this would be.

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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 *asmin999jm OP   TV/TS
over a year ago

wakefield

2-4

Jan made me dress in my male cloths for the shopping trip, but I had to keep my black hold ups, and pink panties on as well as the cock cage. She seemed to settle down and her anger subsided as we walked round so many shops – I was carrying the bags as she bought herself a new dress, shoes, bag, perfume, make up – all the time she was talking at me, ordering me around, and taking every opportunity to embarrass me in front of the till attendants when she made me pay each time. She had no filter, and seem to revel in my embarrassment.

As we walked round the make-up counters, I stood, holding her bags as she talked to the attendant, explaining that she wanted to find a decent foundation that matches my skin tone. The lady looked over to me smiling, “that’s ok, come on and sit down whilst we try some” she said… I felt so embarrassed in the busy shop, but had no choice but to sit down as she tried a few different tones, settling on one that matched perfectly. I tried not to look as people walked past, I suppose If I was a good-looking young fem guy I don’t think people would have been that bothered, but I was not … so people were looking twice at me sat at the chair as she tried the foundation. That said, I had always wanted to do this, so in a way, I was pleased, and just had to go with it, and try and relax.

I still had my nails done from yesterday but that did not stop Jan calling in at a nail bar to get hers done, and insist on having mine done, this time with the words sissy and slut on my nails, the woman who did them did not seem that bothered as they chatted and I could hear her tell her that I was in chastity and was going to be getting a good spanking when we got back to the hotel.

I was starting to get used to the embarrassment now, but that just hit a new level when we got to the pub. It looked like a rough and ready kind of bar, just on the edge of the shopping centre

She wanted a drink and called over to the bar man.

"I will have a large glass of white wine, and my sissy here will just have tap water", she said smacking my ass as she walked to a seat and sat down. The barman smiled at me, and I paid for the drinks and took them over to her.

"massage my feet slave" she said, kicking of her heels, and placing her warm feet on my lap. There were not many in the pub, and I just started to massage her feet. There was a guy sat opposite reading a paper, he looked over and caught Jan's eye. "you have him well trained" he said with a smile. "Oh yes, my sissy here is very obedient" she said and he just looked and went back to his paper.

"You can take the bags to the car and then drive it here, there no way I am walking back to the car park"

When I returned, I walked into the pub and Jan looked like she was enjoying herself. She was sat with the the man who was reading the paper earlier and they had had a few drinks.. She noticed me and called me over "this is John, say hello to John sissy". My face went red., John interrupted "hello sissy, your mistress has told me all about you, why don't you get us a few more drinks and pay the bar bill while your on" he said, , I thought, what the hell has Jan been telling him… But I just nodded and played along, paid the bar bill and brought them more drinks.. "now fuck of and wait in the car" Jan said as she placed her hand on John's leg, rubbing her hand towards his cock, moving over and kissing him….

I did feel a pang of jealousy, I guess I was starting to get used to the intensity of Jan's attention to me, but I did as instructed and went back to the car and waited.

About 30 minutes later they were both in the back seat of the car and I was driving them back to our hotel. John and Jan were kissing and groping each other, her hand was wanking his hard cock and he had her tits out and was busy suckling on them, "if I catch you looking again I will stop this car and give you a fucking good hiding" shouted Jan… I Looked away, and concentrated on the driving as we parked back at the hotel.

I walked behind them with the bags as we went to the room, and as soon as we got in, they were on the bed, pulling there cloths of like two love struck newlyweds.

I was ignored throughout, they were fucking on the bed, and I had to sit and look away.

Then John sat up, "so shall we we let your sissy join us" he said to Jan looking at me. .

Jan laughed, "strip sissy and why don't you show John what a good ass licker you are"...

I striped down to my hold ups, and stood waiting for my instruction, cock still locked in the cage and waited for John to mount Jan and start fucking her.. "dive in sissy, lick my ass" shouted John, so I moved over on the bed as he pushed his cock inside Jan i pushed my face against his ass and started to lick him, pulling his cheeks apart and pushing my tongue against his hole, trying my best to keep it against him as Jan squealed as he fucked her…I think its time you fucked the sissy" said Jan and with that I was laid on the bed, as Jan sat on my face, John pulled my legs up and jan held them as she squashed down on my face, and John fed his cock inside my hole using Jan's juices that covered his cock as lube he pushed deep into me, and started to fuck me. I tried to lick and suck on Jan's wet pussy as they both used me, and John ramped up the pace pushing his cock deep into me…

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

Great story. X

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By *ilks123Man
over a year ago

wf1

Excellent

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

Keeps getting better

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

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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

2-5

Jan seemed to be letting John take control, and he had her on all 4's with me lying underneath.

"I am going to fuck all the holes available" grunting as he pushed his cock in deep in my mouth, then pulled out and found Jan's willing , dripping pussy, - and after a few sloppy strokes inside her he moved it up and found Jan’s ass hole, and squeezed it inside her making her squeal and squirm as she gripped my legs tight laying over me, her wet pussy dripping over my face looking up all I could see was Johns balls bouncing above my face as he rode Jan’s ass. –then with a loud farting noise, his cock pulled out of Jan’s ass and went back right into my mouth …. "make sure you suck all your mistress’s juices of my cock" he shouted…. Pushing it deep down my throat and holding it, pushing against my throat making me gag. Jan was loving it, - then back inside her ass and back into my mouth, driving it in deep, making me gag even more as Jan sighed with pleasure as he continued to enjoy all 3 holes….. . "which hole is going to get my seed" he shouted as he went back into Jan's pussy then her ass then back into my mouth. This seemed to go on for ages, and my cock was seriously strained now and Jan kept teasing it slapping it back and forth as John finally emptied his huge load in Jan's ass…. Jan was rubbing her clit frantically as he groaned loudly, I could see his balls jumping and tensing as he dumped his seed inside her ass, pulling out only to fill my mouth again as he spilled more of his cum over my face and unloaded his last drops of cum down my throat..

"that's good, clean me up"... He said as he got up and pointed as Jan's ass. " there plenty more in there for you, looks like you have a job to do sissy boy, I want to see you clean your mistress, get your face onto her ass now and clean her up, suck it out her dirty slutty as ".

I spent the next 10 minutes licking John's cum out of Jan's ass, tasting his seed, eating it from my mistresses hot sticky hole,... Jan was fingering her pussy and as this went on, John started to slap my ass with his hand, and then Jan told him that there was a leather paddle on the side and that he could use that,.. John got carried away slapping my ass hard with the paddle, “clean her ass” he shouted, “that’s all you are good for, you’re a dirty ass licking sissy” it stung so much but I just kept my head buried between Jan's ass cheeks lapping up his seed…. as Jan frigged herself with her fingers occasionally pushing them back into my mouth…

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By *agical HandsTV/TS
over a year ago

wellingborough

Fuck I need to be him. Such a dream come true

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By *es for funMan
over a year ago

port talbot

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-6

John took he first shower, and I had to wait on him, and I dried him as Jan lay on the bed watching, and they were chatting as though I was not there, I did not matter, I was just the slave, and now it seemed that I had a master and a mistress to serve.

I knelt down towelling his legs, between them, round his ass and between, gently round his cock and balls. "look, I think this slave of yours can't keep his hands of my meat"... Jan laughed, "yes he is a fucking cock whore, aren't you sissy, a fucking cock sucking sissy fag".... John kicked me away, "fuck of now slave, you best help your mistress shower now". “yes”, shouted Jan, “I am training it to become a toilet slave,,,, maybe I will piss on you again, or better still, why don’t you beg master John , beg to be his toilet slave, and take a drink from his cock”, …

I just tried to ignore Jan, hoping to god that they would not make me do that,, as john looked over… “yes, come here slave, I could do with a piss”,,,,

“please no, I beg you, please I cant do that” I felt like crying “oh dear listen to it, begging ,, whats wrong don’t you think masters piss is good enough for you, how dare you insult your new master, you are happy to eat his cum, but your too good to drink his piss”,,, “no, sorry please, Its” just, I”,,,,, but John grabbed me by the ear and walked me into the bathroom, slapping my face as he dragged me into the room, “on your knees cunt” he shouted as I staggered into the shower cubicle and he pushed me down, and then took hold of his semi erect cock – pointing it at my face … “open wide slag” he said, “get ready for your masters piss”…….Jan rushed over to watch, and as expected she had her mobile and she started to video us, “here master, let me hold it for you”, and Jan took hold of his cock as his warm wet piss started to spurt over my face “open wide” and I tried to move away as the hot stream covered my face and body.. thankfully it stopped soon, and they left me to clean myself up, laughing as they went back in the room.

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By *d funMan
over a year ago

Telford

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By *angerineMan
over a year ago

somewhere inbetween the right and wrong

OMG I'm LOVING this.

Thanks Jasmin

Xx

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

This is so sexy and hot. Wondering how cd slut dream about this when in a hotel

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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

2-7

I showered and cleaned myself up as John and Jan talked in the room.

I stood by the door, listening to their conversation, John was about to leave, but was telling Jan about a club that he goes to, and suggested that we all go along to night. "bring the slave, if it scrubs up well I am sure it will be very useful I have a few friends that will enjoy using it"...

……

Later ,,,

Jan was ready for the night out. She looked amazing in her new red dress, , open back, and crossover front showing plenty of her cleavage, with her bare legs, and new heels, she looked amazing…

Finally, I got chance to dress, and Jan, was in a much more relaxed mood - she helped me with my make-up, and sharing her perfume, "by the time I am finished with you, your going to look amazing" she said. She took her time with my make up and even styled my wig for me. I felt amazing, much more relaxed, and starting to get excited about going out dressed, feeling much more confident. She helped me into my lingerie, black fishnet stockings, black bra, and pink panties, placed my breast forms perfectly, as I stood feeling so good as she helped me on with the new white and pink flowered ring necked skater dress, puffed out the hem, - and then I put my black low heeled dolly shoes and stood before her feeling cute, sexy, submissive, feminine and so amazingly excited - as she arranged my mousey brown wig perfectly, with a nice pink allice band.

Then she handed me a box.. “a present from Jan” she smiled… I opened it. It was a neckless, sliver roped, with the word’s sissy in pink and silver letters – need to make sure you remember what you are my dear she said as she fastened it round my neck, letting it hang down over the black fabric of my dress. When I looked in the mirror I could not believe what I could see, - yes the words sissy was very apt, I looked so cute, sexy, and far from blending in, I was going to stand out so much, - and a wave of mixed terror and excitement rushed over me.

She had me pose for some pictures, and I have to admit I felt good, and for a few moments Jan was talking to me as an equal, as a friend, helping my pose, brushing my hair to one side, straightening my hem, “I have to say jack, you do look very convincing, just walk slowly, don’t talk too much, I am sure you are going to enjoy tonight”…

“lift up your skirt darling”, she said, sitting on the side of the bed, she pulled down my panties and unlocked my cock cage, pulling it away, finally releasing me from this chastity , and my cock pointed straight up, I had never seen it so hard as she started to slowly wank my cock… “do you want Jan to make you cum before we go out”,,, she said looking up at me….. “oh god yes please” I begged, “yes, Yes, yes”.. she wanked me slowly and then to my surprise she took my cock in her mouth and started to suck me gently, her tongue tracing a line round the tip of my cock, her soft red lips kissing down my shaft…”who owns you” she said….. “you own me, I am yours Jan, Yours, You own me, “… she pulled away from my cock, held my balls in her hand and squeezed them gently, holding the grip she looked up at me,,,,,,, “Yes, I do, don’t I, and yes, you will do anything I say, absolutely anything, because you know what will happen if you don’t, don’t you sissy jack” “yes ma’am” I replied, sensing that now familiar swing in her attitude and mood, how quick she changes from that caring friendly familiar warmth, the Jan I used to know so well, to that hard, brutal dominance of Jan the mistress, …..

She took 3 or 4 hair bands and wrapped them double and tight round my balls, making my cock stand out even more …”really they need to come off don’t they” she laughed, smacking my cock from side to side …

She then reached over taking one of the coffee mugs from the desk, “come on Jack, wank that cock for me, let’s get you empty and see you cum, but don’t you dare get any mess on my dress, get it all in the mug…. “NOW”.. We don’t want you walking round tonight with that thing poking up between your legs, it’s been hard enough to make you look half convincing, that will just spoil the illusion….. like a slap in the face, she brought me back to reality, and I had no choice but to wank myself and it did not take me very long before I was spurting a lot of my own thick gooey cum into the mug …”drain it sissy, that’s it get all the last drops out”….

She reached over and took hold of one of my but plugs dipping it in the mug and covering it with my cum. “open wide” she said, and she pushed the plug inside my mouth “that’s it get enjoy the taste, as you are going to be getting to taste a lot more by the end of the night” she said,,, then she took it back, covered it again in some of my cum, turned me round, and pushed the plug inside my ass, right in, until it locked in position… “make sure it stays in all night, or at least until we get the chance to get a big fat cock inside you”,,, she laughed.

She handed me the mug and a spoon… “you know what you have to do, eat up” what is left………NOW … as to my frustration, she re attached my cock cage… “did you really think I was going to let you go out without this locked away” ……..

I stood there, as she took a picture of me spooning my cum from the mug into my mouth, drained, cock caged, ass stuffed with a but plug, and now feeling very uneasy about what was to come and when I looked again at myself in the mirror, I could not see a cute sexy female me, just a drained, mature man, dressed up like a sissy, looking clearly ridiculous, humiliated and afraid.

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

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By *ppetiteforsexMan
over a year ago

Isle of Man

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By *d funMan
over a year ago

Telford

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By *agical HandsTV/TS
over a year ago

wellingborough

Omg yes

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-8

The taxi picked us up at the hotel, and took us straight into town, we sat together in the back seat and Jan spent most of the time on her mobile.

The walk from the room to the taxi was my first challenge, and I felt eyes burning into me as we waited for the taxi. We clearly stood out, short skirts, Jan's low cut top, ample cleavage and my fishnets, and I was sure everyone could see my sissy knecklace. "relax hun", you look great, Jan said, reassuring me, this is what you want isn't it, you should be greatful, I am giving you the chance to experience what you crave so much,... She was right, I had dreamt of doing this so many times, and now the reality was just so exciting and scary….

……

The first bar was alredy crouded, and reasonably dark, and it felt so strange brushing against men and women as I had to get the drinks and wait on my mistress, Mistress Jan, Ma’am, and all through the night she insisted I address her as ma’am. She made me accompmany her to the toiltes, and I dreaded some d*unk woman challanging me, “you’re a fucking bloke” I was expecting to hear but I guess with all the noise, dull lights and alcohol, no one was really seeing past my dress, hair, and as I was not wearing high heels, so my height was just below jans, so I did not stand out that much, , and I did start to relax, but when men joined us wanting to buy us drinks, I clamed up, I did not know what to say, but after a few gins, I started to relax even more, despite the fact that my cock was caged and I had a but plug firmly inside my hole…

Jan caught sight of John, and I felt a wave of embarrasment as he approached and walked straight up to us.. He kissed Jan and then looked at me. "your sissy scrubs up well, can't belive its the same slut that was drinking my piss earlier" he said, so loud I thought that everyone in the place would hear him. His friend approached and he looked much older than John. John introduced Greg who looked at me, "wow, yes, I want a piece if that", he said…..

The music was loud and the place was reasonably busy, and I was doing my best to smile and keep his hands of my ass. He must have been in his 60’s, and was intent on getting his hands up my skirt, as I stood, holding Jan’s bag and drink as she was now otherwise occupied with John and 2 more of his friends who were falling all over her. I was stuck with John's older friend, Greg. “so how long you been dressing babe” he said,, “are those real”,,, "John told me all about you, can't wait to fuck you, said you are a right dirty whore, I have fucked loads of men like you, don't care who I fuck, any hole will do... ".... His hand was now on my ass as he tried to kiss me, and I pulled back, trying to play hard to get, sort of enjoying the attention, but I did not fancy him, he was a short ugly old bloke…..

“you gona suck my cock for me….John told me your a right dirty slag"... He had obviously had a few drinks was repeating himself a lot and was very insistent...

Jan returned and could see I was not enjoying things and she smiled, "seems you have pulled already babe" she said, laughing.. I did not reply. Jan looked over to Greg who was now focusing his attention on Jan. "fuck me, you look amazing, your not".. Jan interrupted. "before you go any further, no, I am all woman, but if you want to get in her pants just give me £20, and she is all yours". I looked at Jan, and she smiled, "smile babe, you have pulled".... Jan took his £20, and she looked to me, "your bought and paid for now darling, so do whatever he says, else you know what will happen, would hate to have to put you over my knee in this busy club and spank you in front of everyone".... Jan paused... "what do you say".. "thank you ma'am" I replied.. "kiss Greg, and thank him and tell him now that you are his property for the next hour and he can do anything he wants".

I turned to Greg who was smiling, I kissed him and he responded pushing his tongue deep inside my mouth... Then he just grabbed my arm as Jan took back her bag waving at me "have fun, dont do anything I wouldn't", she said as I was almost dragged outside round to the alley between the bar and the car park opposite.

"on your knees slag, and get sucking", and within seconds I was sucking on his semi erect cock,squatting down as the floor was wet as it had been raining, and I did not want to get my knees wet, this position also made my butt plug release and I tried to push it back in as he pushed his cock down my throat..

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By *rouble 50Man
over a year ago

turriff

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

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By *iM4kinkMan
over a year ago

San Antonio

i luv this story it's great thank you.... please continue

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By *d funMan
over a year ago

Telford

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By *hager777Man
over a year ago

Hereford

More please

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By *ippa 63TV/TS
over a year ago

St Helens

Yes more please

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-9

He was banging away at me, pulling my head into his groin, pushing hard as he face fucked me…. His cock was getting harder now, and he wanted to fuck me, and he was looking round for somewhere to do me. I could hear the noise from the club in the background, and there was a distinct chill on the air, as he pulled me up, "get over there, cunt, near those bins where you belong, will do you over the bin, come on, and bend over the bin,...".. I got up and discreetly removed my butt plug and put it in my bag and took out a condom… "all prepared eh", he said taking it from me, and I positioned myself over the bin, feeling even more degraded, as I was about to get fucked, over a smelly old bin down a back alley….he hoisted my dress up and pulled aside my panties,.. He pushed his finger inside my mouth "suck bitch," then pushed it inside my hole, frigged me a few times and then rammed his cock inside me,... So much for the lube I thought, but as he entered me, it was like he had inserted a magic wand, It felf bloody amazing, so good as his hard cock drove straight into me, and I let out a whimper… My hole was already stretched enough, and it slipped straight in and he got to work quick banging me over and over, as I held onto the bin…. "oh oh ahgh wow yes yes yes oh god yes, YES, YES, FUCK ME OH FOD YES, I AM YOUR DIRTY SLUT GREG, FUCK ME… " I shouted, letting go and I thought I was going to have to pretend to do this, but his cock was just the perfect size for me and was hitting all the right places, it was amazing, had to be the best fuck I had ever had, despite the fact that I was hanging on to a bin down a back alley, now oblivious to my surroundings, the alcohol kicking in, I just did not care now, I was Jan's whore, and I was lost in the sheer extasy of this fucking, ….. Greg was loving this, my screams of delight were making him go even harder, my panties now ripped and hanging of one of my legs, his hands griping my waist, slapping my bare ass and occasionally griping my breasts, as he pushed deep in and out, in and out making the bin rattle against the wall….

…….

Then breaking the moment I heard voices shouting

"there they are, look at the dirty old git go, you not finished yet Greg, "....

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By *MBER KENTCouple
over a year ago

folkestone

Great read

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

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By *ppetiteforsexMan
over a year ago

Isle of Man

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By *d funMan
over a year ago

Telford

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By *aulaxd500TV/TS
over a year ago

Wigan

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

Keep up the good work, hot story.

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2-10..

I tried to look round, the voices bringinng me back to reality, a wave of panic, .. it was dark and drizzling rain, but it was clear that two men who were also talking to Jan earlier were now watching Greg fuck me,... "go on you dirty old git, , fuck the bitch, but hurry up, your time is nearly up and we have paid to go next, we got a cheaper deal to do both holes at once,..."

"hold on lads, nearly done, just about there, let me seed this whore first and then it's all yours… … AGh AGHHHHHHH YES FUCK Yes, aghh YES YES ARGHHH " as he released his seed inside me, and I felt it shoot deep up me, ,, and that's when i realised that he had not put on the condom, as his cum started to leak down my legs." fucking hell,.. I bet that hole is too fucking slack now "one of them shouted as he pulled away and walked over leaving me draped over the bin, desperate for my own release, but before I could do anything the two men, were upon me ,

" it's all yours lads, your welcome to very sloppy seconds, well lubed now… … enjoy, and just dump it in the bin after where it belongs, dirty cock sucking faggot" … .... Shouted Greg, finding further ways to take me total degregation.

The gin had caught up with me now, and my head was spinning as they just lifted me up onto the bin and lay me over, sort of half on, belly resting on the top as one of them found a crate to stand on and the other was up my hole pumping me, no small talk, just two cocks straight inside me, mouth and ass full as they roasted me holding my legs as I did my best to balance …Two younger and much larger cocks destroyed my throat and ass, deep and hard, as I gagged and strugled to breath.

"what a sight to behold", shouted Jan, who was now stood near us, just as I felt a jet of thick gooey cum hit the back of my throat. He pulled out his cock as I gasped for breath, and he wanked the last jets of cum over my face, but the guy in my ass was still pumping away, "AGHHH JUST ABOUT THERE,...." and then he pushed deep inside and released his seed which was soon dripping down my legs, which were sore now as he had his jeans on and they rubbed against my legs ripping my stocking tops,....

"well, well, jacky, you have sunk to new depths tonight darling spit roasted over a bin in a back alley",.... "don't move, I want a picture of this for the memories," she laughed.

Jan could see that I was well and truly fucked, and she took pity on me and helped in into a taxi. "been an exhillerating night for you".... Her new friend John looked impatient "ditch the fucking sissy and let's head back to my place Jan, no one in thee right mind would be interested in touching it now, and for fucks sake his fucking wigs falling off" . Jan straightened my wig and helped me into the taxi.. "You get yourself back to the hotel room jacky, clean yousellf up, you look like you need a rest" .

I was grateful for her help and felt for a moment that she was almost caring for me, and then when the taxi was about to pull away she looked over to the driver,.. "look mate, she has no cash, and if you take her back to the hotel, she will give you a blow job, is that OK?"..

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By *rouble 50Man
over a year ago

turriff

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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

2-11

The driver, a young shy looking Asian lad looked back, smiled, "no problem love, why don't you hop in as well, let me at those gorgeous tits"... Jan smiled at him shaking her head and tapped the top of the taxi with her hand and I was back down to earth with a bump. So much for the caring Jan I thought.

"so love, what is your name, let us find somewhere well quiet to park up, my knob is desperate for a good suck… me balls are well full"

All I wanted to do was get a nice long shower clean up and try and rescue myself, as I was well and truly knackered, my ass was sore now and I needed a good sleep.

But, no, another cheesy cock to suck, and this lad sounded so desperate, he would not stop talking,.... He parked up in a laybye and was quickly out by the side of my door stroking his cock,.... "come on then, my knobs ready for your hot lips babe"...

. I opened the door and tried my best to get out the car with some dignity, "what about a kiss first babe" he said pulling me against him, pushing his hard cock into my groin, his hands on my ass, and over to my breasts, well my false breasts, but he did not seem to care as he squeezed them and pushed his tongue down my throat.. I was too tired for this, and wanted it over with, so I knelt down and got on with the job in hand.

It was a quick job as well, I wanted it first, a nice big hard cock as well, thick black hairy balls and he smelt very sweaty, on another day I would have enjoyed this and made it last longer, but I soon had my lips round his shaft, looking up as him, pulling his cock out and kissing his bell end, smiling, kissing it then taking it deep into my throat, gagaing and back for more…...He lasted about 2 minutes before I had what seemed like a litre of cum, and for some reason as he cum he pulled out, and it squirted over my face, in eyes, on my dress and when I took it back in my mouth even more his cream seeped out and I had a full mouth of his watery seed, and I had to spit it out "oh dear, good girls don't spit" he said, and he wanked a last jet over my face, grunting as he pulled his cock back into his trousers.

As we drove to the hotel he was such a gentlemen,, he passed me some Wipes, and apologised for cuming on my dress saying it was such a lovely dress…. He old me that he found older women sexy, and he obviously thought I was a woman,....I felt so good that despite the situation he thought I was a woman…. . He said that this was the first time he ever did this as not been doing the taxis long , and all his friends think it must happen all the time,, and that it never happens to him,.... and it was the best blow job he had ever had…. He wanted my number and kept asking to see me again,...he was so sweet,. And he was asking about Jan, .. I just kept nodding and smiling, I was knackered and just wanted to sleep….

I had to be insistent when he pulled up at the hotel lobby, "do you don't want me to walk you up to your room, I am done for the night,"... "no darling, your so sweet, but I need to sleep, maybe another time"... I let him kiss me once more and I gave his cock a nice squeeze, and made my escape….

I just did not care about who could see me as I headed back through the hotel lobby and up to my room, the old guy on reception must have seen some sorry sights in his time, as he just smiled and did not seem phased by my appearance as I hobbled past him, God knows what my face must have looked like, and my dress was wet, sodden with cum stains, and my stockings ripped.

Soon I was showered and in bed, in my nice satin nighty, my ass still felt full and stretched, and I drifted of to sleep, half expecting Jan to burst in demanding attention, with more tasks, men, who knows,.... But I just closed my eyes and hoped that she would be true to her word and let me have some rest. I tried to count how many cocks I had sucked, how many times I had been fucked, and imagined the amount of incriminating pictures and video Jan had of me, knowing that there was a full day and night to go, God knows what she had in store for me,...... and worse still soon we would be back at work, and that was going to be strange after this, how would she treat me, what if she let slip to someone about me,.... I was restless, fighting back the anxiety of my situation, but soon, thankfully my exhaustion took over and I was asleep……..

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By *ubsteffTV/TS
over a year ago

Portsmouth

A quality tale, this

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

Such an amazing story

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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

2 12

I slept till 11am, and considering it was at lest 4am when I got back to my room, 7 hrs was good for me, and no sign of Jan. I took another shower, and ordered some room service, then took some time to get myself ready. I decided to dress down, I had a blue skater dress, black opaque tights, and I had to get my aubrun wig out as the one from last night was covered in cum….

I applied my make up and then decided to tidy up the room, then I found a spare key to my chastity cage, so I unlocked myself and felt such a relief as my cock was finally allowed some freedom…if Jan did not like it then I did not care, I was ready for home to be honest was just pleased of the rest. I checked my emails, made a few calls, checked in with my wife, and relaxed…

Then, without warning Jan more or less fell into them room. She looked as bad as I did, and she just stumbled in, kicked of her heel, flung down her bag and lay on the bed.

"I am fucked Jaky, I need to sleep, get me ready for bed, and clean me up I cannot be arsed to go in the shower"...

Jan lay on the bed, and she was more or less asleep as I undressed her. She stunk of alcohol, fags, and that all familiar stale smell of sex, cum,.. I guess she had been shagging all night….

It felt strange undressing her.. I had to lift her up slightly to get her top of, then I reached round her back unclipped her bra and let those huge breasts spill out over her chest. I was so tempted to touch them, kiss her huge nipples, but I resisted, and went to pull her skirt down. Jan mubled "good girl, my snatch feels like it's been fucked by a rugby team, get tour tongue in and clean me up, must be a gallon of cum up there for you"..,"maybe more in my ass".... I did not need asking twice, my cock was hard, and the smell of her sweet body odour and perfume mixed was like an aphrodisiac and I wanted to taste her.

Her panties were seriously stained, and I pulled them down over her bare legs, as she strecehd out, arched her back "come to mummy" she mumbled, as I crawled up the bed, toward her red, glistening cum stained pussy, and pushed my face between her legs and started to clean her, licking and sucking around her pussy and deep inside, tasting her juices……

"Don't touch my clit, it's sore" she said, as I averted my tongue, and focused on licking between her legs and round the fleshy glands of her vagina, as she mumbked again, farted and turned over, "ups, sorry about that, but better out than in," as I knew what she wanted me to do next,.. Her ass was red, and I could see snail trails of cum round her ass cheeks, as I parted her flesh, and pushed my face between her cheeks and started to clean her cum stained ass hole, licking again round the crevice if her ass, up and down, then down and inside her hole, as she farted again, the smell was horrible, and I was just thankful that it was just a fart, as I worked on, licking and rimming her ass….

She pushed me away and turned onto her side, and soon I could hear her snoring, and I took my chance and moved close and nestled my face between her huge breasts, breathing in her body odour, and suckled gently on her nipples, her hand moved, I flinched but continued as she groaned slightly then pulled my head into her bossom, "good boy Jack, you suck on mommies breasts, your mine now, I own you, your mine, suck me, mmmmmm" her hand reached between my legs and she gripped my cock that was so hard now, and she gently pulled on it, wanking it, as I sucked on her nipple".. "cum for mommy, cum for mommy, your mine now, mine, I knew one day it would happen, soon it will be official… ", and then she was asleep, and her grip released, and I was so close, so close to cumming, I pushed my cock against her leg, and finally exploded, releasing warm wet cum all over Jan's leg, as I suckled hard on her nipples lost in my climax, ,.. As I thought about that last statement, official, what the hell did that mean… …

I cleaned up my mess from her legs, without having to be asked, using my tongue, then nestled back into her warm body.

I lay with Jan for the rest of that day, she slept and I just held her, feeling so good wrapped in her arms, my head burried in her bosom, and I knew that something inside me had changed and I knew then that just did not want this to end.

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

Still so good. Always look forward to this.

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

Thanks all for the messeges and posts on here. I write for my own enjoyment, so it's always a bonus when others enjoy. This one was based on a partially real event, but 90% is fantasy. Last part coming next... And going to make it a happy ending for poor Jack xx

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By *d funMan
over a year ago

Telford

thank you

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By *hager777Man
over a year ago

Hereford

Can't wait

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By *agical HandsTV/TS
over a year ago

wellingborough

Love this

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By *ppetiteforsexMan
over a year ago

Isle of Man

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By *asmin999jm OP   TV/TS
over a year ago

wakefield

2 12

When we returned to normality after the business trip, Jan backed right of, it was as though nothing had happened, and I found myself feeling very deflated. If I tried to mention it, to make time to be close to her in private at work, and every time I mentioned it, she just smiled, our little secret.

As the weeks went by, I found myself thinking of Jan all the time, and when we next finally got chance to go on a sales trip together, she back out last minute, said she was not well.

That's when I knew I had to find a way to be with her, and I knew I wanted to spend the rest of my life serving her and did not want to lose her.

Life at home with my wife was just so mundane, and all I could think about was Jan, and it was clearly not working.

To cut a long story short, I left my wife, my feelings for Jan left me with no choice. It was an amicable split, and I just needed to come to terms with my feelings for Jan and my deep routed desire to dress and be feminine.

I moved out, got myself my own flat and within 6 months I was formally separated and just waiting for the divorce to come through, and I was free.

That's when I decided to approach Jan. It was all or nothing..

I had it all planned, but it ended up been a sort of spur of the moment thing one night late at work.

She came into my office, I remember it well, she was wearing a tight fitting business suit, black stockings, heels, white blouse and a black jacket.

I stripped naked, got on my knees, looked up at her and said that I was in love with her, since that time at the hotel I had thought of nothing else but her, and wanted to devote the rest of my life to serving her as her slave. "ma'am, I beg you with all my heart, can I be your slave for real"...

She smiled, stood back and looked down at me…..

"you took your fucking time jack ", she said, looking down at me smiling…..

Then she knelt down and kissed me, "I said official".... She smiled and slapped my face so hard, I fell over… I regained my composure, almost in tears, “ma’am, will you marry me, please, I beg, own me, control me, make me yours forever”….

She stood up and walked out, leaving me on my knees, in tears.….

Then, a few days later, Jan emailed me a contract. I took it home, read it, read it again, and I signed it. This was everything I wanted and more, however, one of the conditions was going to seriously test me.

I moved in with her, and within a few days my life had changed completely and I was happy, so happy. I had to sign everything I owned over to her, she took control of my bank account, and my phone. I was allowed 2 days of every month so I could continue some contact with my family, but that was all. Every other moment of my life had to be devoted to Jan.

I was in love with her, she allowed me to be true to myself.

At home, I did everything, I was the house wife / slave, and had to dress in my fem cloths all the time. Over the next few months, my wardrobe developed, and apart from when I was at work I spent most of my time as Jacky.

Jan continued her life as it was, and she continued to have many lovers, sex with men whenever she wanted, they were told about me, and if they didn’t like it they left, else they would use me as Jan directed. I was always there to clean up and be used sexually by the men depending on Jan's mood. We had many amazing times at the various clubs she frequented, many whereby I was dressed, and displayed as her slave. She had me tattooed, "Jan's Sissy Slave" across my lower back. I was punished regularly, sometimes it was fun, sometimes it was just, well, punishment and it hurt like hell. I had a cage with a blanket in a shed outside, and sometimes I would spend the night tethered like a dog in the cage, but many, many times, I would be lying next to Jan, in her warm loving arms, sucking her beautiful breasts.

Jan had me in permanent chastity with a specially made cage, so I could wear it all the time. It had two keys, and she let me have one of them, on a chain round my neck.

She had many new ideas of ways to push my limits, pain and humiliation. I would be whored out regularly for real, and my body shape and dressing skills improved, she started to increase my price.

It became a common joke round the office. "Since Jack moved in with Jan, he is so under the thumb", and the fact that Jan domineered me at work, was more obvious now, but accepted, as she took a promotion, and I ended working for her, (this was part of the contract)

But it was the wedding day that would test me most. The wedding day was a big step for me, and I had to make that final statement in front of an audience and come out as Jan’s slave.

“I promise love honour and obey” ,

“ I give myself to you and will devote my life to serving you”

“I pledge my devotion, and everything I have is yours”

Jan was going to wear the trousers, and I was going to wear the Wedding Dress.

She insisted, knowing full well that this would expose my secret, but she said it was necessary, to prove myself as her devoted slave, I had to do it willingly, not under pressure.

Many of our work colleagues would be at the ceremony and my family would find out.

But there was no going back, and I had 6 months of diets, skin treatment, body shaping exercises and hormone treatment. She made me grow my hair, and had it styled on the day, Jan wanted me to be her bride, and she wanted everyone to know I was her slave and her sissy… I was so happy.

I remember that moment, as I stepped into the small hall, full of people I recognised sat patiently looking towards the front of the room, waiting as I took Jan’s hand and walked slowly past everyone in my amazing dress, it was short at the front, wrapping round with a long back, just trailing the floor, It was white with a hint of pink, with bows and flowers, I had silky white stockings and pink and white heels. My own hair had been styled and waved, flowing softly over my shoulders, my make up was perfect, I looked so convincing, and never felt so excited and scarred in all my life.

As I came into view, the gasps of surprise from the audience was evident, the ceremony concluded and instead of exchanging rings, Jan took my necklace with my chastity key and placed it round her neck as that final symbolic exchange of power and control from me to her, and she replaced my necklace with a stainless steel collar, locked into position engraved with the words, Owned Slave, Property of Jan.

As I we kissed, I looked out to see everyone as the photographer took some pictures, Jan in control, lifting my leg slightly to expose my pink garter, such a traditional image, but also demonstrating Jan’s ownership of me, displaying me publicly on my wedding day, but Jan went further, holding it up longer, brushing her hand up my stocking clad leg, pulling on the garter, displaying my panties and the outline of my cock cage underneath, , . ,,,,,,,

I tried not to look into the eyes of the faces looking back at me, some looked happy, many looked surprised and shocked, but I did not care anymore – I was happy, and now I was Jan’s owned slave.

When we went into the side room to sign the marriage certificate, I had to sign my new name, taking Jan’s surname, and then the photographer took a few more pictures of us together , me on my knees looking up to Jan, and Jan holding the key with my cock cage on view.

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By *d funMan
over a year ago

Telford

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By *atsWoman
over a year ago

wexford

Fantastic story as usual,Jaz. xxx

Can't wait for the next one.

Cats xxxxxx

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By *angerineMan
over a year ago

somewhere inbetween the right and wrong

Beautiful ending

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