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Back to Stories and Fantasies

Caught by the Bosses Wife - Part Two.

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

Training begins.

More to follow shortly. Thanks for all the lovely messages and comments.

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By *-allthewayMan
over a year ago

Claydon

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By *tockings12369TV/TS
over a year ago

Oxford

Looking forward to more

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

Woohoo

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By *ragsterMan
over a year ago

Blackburn

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

I did as instructed in the text messages, and booked a taxi to a suburb of the town that I had never been to before. The houses were all detached with large walls surrounding them.

I payed the taxi and walked up to gate and pressed the intercom announcing my arrival.

The gate buzzed open and I entered the property and up the driveway to the front door. Before I could knock on the door it opened. The woman who stood in the doorway was not who I expected at all. She was definitely not the bosses wife, but a woman in her early thirties, wearing a bright red latex catsuit and boots.

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By *j and c 2Couple
over a year ago

mullingar

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By *orkiepud_69Couple
over a year ago

Scarborough

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By *eterpervisMan
over a year ago

back where i came from

Love a red latex catsuit….

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By *igbbackagainMan
over a year ago

Tallaght

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By *i015Man
over a year ago

Millbrook, Southampton

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By *ragsterMan
over a year ago

Blackburn

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By *hil911Man
over a year ago

Solihull

Ooo nice

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By *kpiercedCouple
over a year ago

walsall

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

The woman turned her back om me and walked back into the house. I followed, my eyes focusing on the way her arse moved in the tight latex.

I followed her in to one of the reception room, and was stunned when she turned and slapped me hard across the face. I went to speak,but was silenced by another slap.

"On your knees slut, head touching the floor. Don't speak again until you are permitted to do so. I am Mistress Devine, and you pathetic sissy are here to be trained as the cock sucking slut that you desire to be."

I could hear her heels on the parque flooring as she walked around me. She then tossed something on the floor in front of me.

"Strip off all your clothes and place them in the bag. You will not need them again while you are here. When I come back I want you with your hands behind your back, kneeling upright, eyes firmly shut. Don't think I didn't know that you were staring at my arse as you followed me in here.

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By *ornybarMan
over a year ago

clonmel

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By *ragsterMan
over a year ago

Blackburn

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

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By *lderWiserNowMan
over a year ago

Kettrin

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By *usie pTV/TS
over a year ago

taunton

Thank goodness there is more to come

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By *oth0712Man
over a year ago

cambridge

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By *ubforfandcoupleMan
over a year ago

pontardawe

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By *ornynhappy23Man
over a year ago

renfrewshireish

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By *ac6969Man
over a year ago

leeds

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By *oyntzMan
over a year ago

all over Ireland

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By *ipper truckMan
over a year ago

near by

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By *umblebiMan
over a year ago

ayles

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By *atthew78Man
over a year ago

Winsford

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By *axixxxMan
over a year ago

Bathgate

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By *avey997TV/TS
over a year ago

East London

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By *arried-bi-guyMan
over a year ago

Lanarkshire

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By *idLTMan
over a year ago

Leeds

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By *orkiepud_69Couple
over a year ago

Scarborough

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

I am not sure how long I had been kneeling for before I heard the distinct tap tapping of heels approach.

"Knees apart, sissy."

That was the bosses wife's voice. So where was the younger woman I wondered.

"Good, you followed my instructions. There is hope for you yet."

As instructed I had completely removed all of my body hair, though previously I had shaved my legs, and what little chest hair I had. Now I was completely smooth.

"Now this is what is going to happen over the next week. You are going to be transformed into a bimbo sissy slut. You will learn how to suck cock, and you will learn what it is like to be f*cked. On a daily basis you will be given hormones to help the transition from a pathetic male specimum into what you have always craved to be. From now on you will walk, talk, suck and be f*cked like the sissy you are." I was horrified, though a part of me was also excited.

"Once your training is complete you will return to work as my husband's PA. When he wants a blow job in future, or wants to f*ck his secretary it will be you that will be prividing those services."

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By *eanasmustardMan
over a year ago

corby

Mmmmmm v nice

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By *ragsterMan
over a year ago

Blackburn

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By *umalotagainMan
over a year ago

a town called malice

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

While my training progressed Simon (my boss) was suffering his own punishment. When he and his wife had returned home from the party he was ready to ask her if she enjoyed her f*ck, but he never got the chance. As soon as they had closed the door behind them she told him to get upstairs and get undressed. He thought to himself that she must be really turned on, it was not like her to initiate sex. He rushed up the stairs and did as asked. He then propped himself up in what he thought was a sexy pose and waited for her to join him.

When she entered the room she had stripped down to green and black lace bra and knickers with sheer black stockings and spike heels. His semi erect cock twitched as he looked at his curvacious wife.

"Oh you think this is for you do you." She laughed at him. "No, I have invited a friend over, and she is going to f*ck me like you never can. But first we have to take care of that cock of yours. You see while I appreciate you have urges that I will not satisfy, I don't like you going behind my back to satisfy them. So in future when you need release, I will be the one who decides who with." She then climbed on to the bed straddled her husbands face and told him to lick her through her knickers while she attended to his cock.

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By *Sweet94Couple
over a year ago

dunfermline

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By *hil911Man
over a year ago

Solihull

Oooo

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By *ragsterMan
over a year ago

Blackburn

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By *usie pTV/TS
over a year ago

taunton

Lol excellent

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By *ig daddy 1969Man
over a year ago

manchester

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By *ecker30Man
over a year ago

Northwich

??

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By *ndrea54TV/TS
over a year ago

cambridge

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By *onmacMan
over a year ago

glasgow

More please

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By *ac6969Man
over a year ago

leeds

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By *addy and the TrampCouple
over a year ago

Gamlingay

Awesome

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By *ipper truckMan
over a year ago

near by

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By *uddle4uMan
over a year ago

Purbeck

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

She could feel herself getting close as she ground down on her husband's face, but she was not going to allow him the pleasure of knowing how close. She quickened her actions, wanking his cock, seeing his muscles tighten and his hands clench as he too got closer to orgasm. Then just as she sensed he could not hold back any longer, she squeezed his cock, so that rather than squirting all over his naked stomach and chest, he dribbled cum down the length of his rapidly deflating cock. At the same time she pushed down hard on his face, imobilising him, allowing her lover to enter the room, grab his ankles and enclose them in cuffs that she then attached to the bottom of the bed. Simon's wife then cuffed his wrists, and as she got up off his face attached these to the iron headboard.

Once he was completely restrained, she encased his now deflated cock, still sticky with his ruined orgasm, in a metal cage.

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By *oyntzMan
over a year ago

all over Ireland

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By *ounggent01Man
over a year ago

N yorks

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By *uckjayMan
over a year ago

ripon

Loving this and cannot wait for more

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By *ndrea54TV/TS
over a year ago

cambridge

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

Once they had ensured that Simon was secured the two women knelt each side of him and began to kiss and caress eachother's bodies. The younger woman moved her mouth down to Rita's (The bosses wife) neck, nipping at the skin as her hands tweaked Rita's nipples through the lace of her bra, making her moan.

They momentarily climbed off the bed, Rita removing her bra and knickers before climbing back on the bed. She placed her knees each side of Simon's waist, as if she was about to ride him, then she leant forward so that her hands were holding his upper arms. Simon was not sure what was happening, though he could feel the effect on his caged cock.

"Remember sweetie I said you would not be fucking me anymore. Now I want you to look at my lover's cock. It might not be real, but she knows how to use it to satisfy me. And unlike your pathetic specimen it does not go soft after a few minutes." As Rita spoke the younger woman came round the side of the bed, climbed on and straddled Simon's face. A large black rubber phallus sticking out from between her thighs.

"Now gag on that lovely cock sweetie, make it lovely and wet ready for my pussy."

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By *ndrea54TV/TS
over a year ago

cambridge

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By *ragsterMan
over a year ago

Blackburn

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By *ac6969Man
over a year ago

leeds

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By *harlottes ChurchTV/TS
over a year ago

Toy me town

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By *he-ProfessorMan
over a year ago

cheltenham

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

On the Monday when I reported for training, Simon was on the way to his conference, his cock now caged.

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

The first day of my training consisted of me demonstrating my walking skills, though the shoes that I was made to wear had far higher heels than I was used to. It did not help in that all I was permitted to wear was a very tight corset and my own cock cage.

When Mistress Cathrynn (Ms Rita's lover) was satisfied that I could walk without breaking my ankles she moved on to the next phase of my training. I was led into another room which had one wall made up of mirrored glass from floor to ceiling. Attached to the glass by suction alone about waist height was a row of realistic looking phalluses in varying length and girth. I was told to get on my knees and start with the smallest and start sucking. When I was comfortable that I could take one fully in my mouth without gagging I was to move on to the next.

Three days later I had progressed to wearing holdups, corset and stilettos. I had been fed on a strange cocktail which was causing a change in my physical appearance already. Though Ms Rita had indicated that they would have to improvise until my body was ready. What this meant I had no idea. I had also managed to take nearly six inches of phallus in my mouth without gagging. I was also now having my arse stretched as each phallus I moved on from was then used to fill my arse for hours on end.

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By *ragsterMan
over a year ago

Blackburn

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By *avidking73Man
over a year ago

Barnet

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By *hil911Man
over a year ago

Solihull

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

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By *avey997TV/TS
over a year ago

East London

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By *umalotagainMan
over a year ago

a town called malice

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

At the end of the week I was sent home, though if any of my neighbours saw me, I was not quite sure how I would react. Having left the flat Monday morning in male attire, at least outwardly, I was returning in full girl costume, including wig and silicone breastforms.

I did manage to get in to my flat undetected, and spent the whole weekend enfemme. I continued with the hormone replacement cocktails and enjoyed the fact that I no longer had to shave my face every day.

Monday morning came around and as with the previous week I took a taxi to Mistress Cathrynn's Academy. I was greeted at the door once more by the vision that was Mistress Cathrynn. This time I knew my place and immediately went down on my knees to allow her to place my collar around my neck and attach a lead to it. On all fours I was led through to one of the training rooms.

In the middle of the room was a large office desk, behind which sat Ms Rita.

"This week we are going to test your secretarial skills. Firstly oral dicktaking I think." She said. She then instructed me to walk around the desk to where she was sitting. I did as instructed, swinging my hips from side to side as provocatively as I could. When I got round to where she was sitting I noticed that her wrap around skirt was parted to reveal a very large phallus between her thighs.

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By *uckjayMan
over a year ago

ripon

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By *he-ProfessorMan
over a year ago

cheltenham

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By *ohnny 51TV/TS
over a year ago

Middlewich

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By *ragsterMan
over a year ago

Blackburn

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By *rgasmdonorMan
over a year ago

millstreet

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By *arks173Man
over a year ago

doncastet

So hot this xxx

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By *rt1976Man
over a year ago

redcar

Really enjoy this

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By *-allthewayMan
over a year ago

Claydon

Been really good, how’s it going to end I wonder.

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By *kpiercedCouple
over a year ago

walsall

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By *ac6969Man
over a year ago

leeds

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By *axixxxMan
over a year ago

Bathgate

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By *j and c 2Couple
over a year ago

mullingar

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By *atthew78Man
over a year ago

Winsford

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

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By *oyntzMan
over a year ago

all over Ireland

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By *addy and the TrampCouple
over a year ago

Gamlingay

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By *umalotagainMan
over a year ago

a town called malice

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By *eeker of pleasureMan
over a year ago

manchester

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By *ounggent01Man
over a year ago

N yorks

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

Like any good sissy secretary I got down on my knees between Ms Rita's thighs, took the base of the phallus in one hand and lowered my painted lips over the massive head until it filled my mouth. Then with a combination of finger strokes and sucking, I began to pleasure the phallus as if it was a real cock.

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By *he-ProfessorMan
over a year ago

cheltenham

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By *ragsterMan
over a year ago

Blackburn

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By *onred1221Man
over a year ago

.

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By *ndrea54TV/TS
over a year ago

cambridge

Oh wow this is a dream come true

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By *un guy 2020Man
over a year ago

near you

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By *axixxxMan
over a year ago

Bathgate

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By *ark_sentinelCouple
over a year ago

Andover

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By *lare_thomas38TV/TS
over a year ago

my town

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By *umalotagainMan
over a year ago

a town called malice

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By *ricky09Man
over a year ago

Gloucester/Cyprus

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By *elly loveTV/TS
over a year ago

kilmarnock

Loving this x

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By *r MacmullyMan
over a year ago

Tarbert

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By *ag165Man
over a year ago

Greenock

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By *eeker of pleasureMan
over a year ago

manchester

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By *ike231251Man
over a year ago

Heckmondwike

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

Mmm yes

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By *arks173Man
over a year ago

doncastet

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By *ignbeardyMan
over a year ago

Leeds

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By *ovingmyknickersgTV/TS
over a year ago

cheshire

Need more please

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By *oyntzMan
over a year ago

all over Ireland

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By *athytvsubTV/TS
over a year ago

Bulwell, Nottingham

Can't wait for more even tho I am caged and getting uncomfortable x

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

Ms Rita grabbed the back of my head and pulled me down to her cock, laughing as I gagged as it hit the back of my throat. She then squeezed her thighs together holding my head in place.

"That's a good sissy, take my full length in your mouth..."

I was gasping for breath when she finally allowed me to lift my face from between her thighs, though she continued to face f*ck me for a further ten minutes or so.

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By *ohnny 51TV/TS
over a year ago

Middlewich

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By *ark_sentinelCouple
over a year ago

Andover

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By *ragsterMan
over a year ago

Blackburn

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By *eeker of pleasureMan
over a year ago

manchester

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By *axixxxMan
over a year ago

Bathgate

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By *rgasmdonorMan
over a year ago

millstreet

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By *oole20Man
over a year ago

everywhere

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By *af105Man
over a year ago

newtownards

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By *ove2pleaseseukMan
over a year ago

Hastings

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By *ac6969Man
over a year ago

leeds

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By *he-ProfessorMan
over a year ago

cheltenham

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By *ton_maleMan
over a year ago

Shoreham

nice

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By *avem30Man
over a year ago

barnsley

Nice story

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

What came next was a complete surprise. As the large dildo filled my mouth I felt a jet of warm liquid hit the back of my throat. Not once, but three times until I was choking. Ms Rita withdrew her cock, and then squirted me in the face. The dildo's realistic looking ball sack had been full of warm milk.

"Good sissy. Next time I will allow you a taste of the real thing. Now crawl over to the corner and await further instruction."

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By *ragsterMan
over a year ago

Blackburn

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By *umalotagainMan
over a year ago

a town called malice

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By *af105Man
over a year ago

newtownards

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By *ark_sentinelCouple
over a year ago

Andover

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By *rent100Man
over a year ago

Warwick

Omg! Perhaps reading this whilst dressed in one of my skimpy bras, thongs, holdups and one of my pairs of 5” heels wasn’t such a good idea. My thong appears to be a little damp now , but I still want more please , xxx Tia

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By *ohnny 51TV/TS
over a year ago

Middlewich

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By *he-ProfessorMan
over a year ago

cheltenham

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By *ac6969Man
over a year ago

leeds

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By *oyntzMan
over a year ago

all over Ireland

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

About an hour later Ms Rita appeared to notice I was still kneeling in the corner of the room.

"Come here sissy, my cock needs servicing."

Three more times during that day I was called upon to crawl between her thighs and suck her strapon until she decided to fill my mouth with milk.

"You see my husband is very demanding and has a high sex drive. Well he will have once I release his cock from its cage. And you will need to satisfy his every need. Now go and clean yourself up. Tomorrow we will seeing how good you are at taking cock in your slut hole."

I was dismissed from the room.

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By *oyntzMan
over a year ago

all over Ireland

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By *j and c 2Couple
over a year ago

mullingar

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By *r ed300Man
over a year ago

bradford

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By *he-ProfessorMan
over a year ago

cheltenham

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By *rgasmdonorMan
over a year ago

millstreet

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By *umalotagainMan
over a year ago

a town called malice

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By *ragsterMan
over a year ago

Blackburn

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By *atthew78Man
over a year ago

Winsford

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By *icurious69jockMan
over a year ago

north east lincs

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By *ounggent01Man
over a year ago

N yorks

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By *lli_sissyTV/TS
over a year ago

Cambridge

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By *igbbackagainMan
over a year ago

Tallaght

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By *ike231251Man
over a year ago

Heckmondwike

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over a year ago

Warwick

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over a year ago

Middlewich

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over a year ago

newtownards

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over a year ago

Tarbert

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over a year ago

Telford

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over a year ago

Andover

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By *ricky09Man
over a year ago

Gloucester/Cyprus

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By *ubsteffTV/TS
over a year ago

Portsmouth

Wow!

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over a year ago

Bathgate

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By *ac6969Man
over a year ago

leeds

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

Over the next couple of days my training continued. Sometimes it was Ms Rita, sometimes Mistress Cathrynn who wore the strapon. All the time I had a plug in arse as I took their cocks in my mouth.

Then on the fourth day I was ordered to attend Mistress Cathrynn in the office. As with every other training session she was dressed in a power suit. This session though she stood up and walked towards me.

"Now sissy your boss is going to want to f*ck you like the slut you are. So get over to my desk and bend over."

I did as I was told, and my skirt was pulled up, my knickers pulled down, and the plug removed from arse. I felt empty, the first time in four days, but it was not going to be empty for long I knew.

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By *igbbackagainMan
over a year ago

Tallaght

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By *ark_sentinelCouple
over a year ago

Andover

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By *onmacMan
over a year ago

glasgow

Oh more please

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By *atthew78Man
over a year ago

Winsford

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By *ragsterMan
over a year ago

Blackburn

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By *ohnny 51TV/TS
over a year ago

Middlewich

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By *avingabreakMan
over a year ago

Near the Border

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By *oneysmithcdTV/TS
over a year ago

Glenrothes

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over a year ago

bradford

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By *0nderMan
over a year ago

wolverhampton

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By *ike231251Man
over a year ago

Heckmondwike

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over a year ago

Bathgate

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over a year ago

doncastet

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

Brilliant story

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By *ac6969Man
over a year ago

leeds

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By *hirk999Man
over a year ago

oswestry

wow

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