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Lady boss
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100% fantasy but based on real events about a real person.
In my 20s I worked for a hot woman twice my age who often had nylon clad legs, she wore very tight pencil skirts. The outine of her lingerie was often noticable.
Ater her dipstick husband left her she started to go out some nights straight from work.
One day she was going out after work so she changed in her office, leaving her bag of clothes there.
I told her I would cash up and lock up so she could get going, soon as she had gone I was in that bag.
I was right about what i thought i saw she had very sexy lingerie stockings, suspenders, sexy silky satin knickers.
I had to wank and ended up shooting the biggest load of my life into her knickers.
A few days later she questioned me and asked if I had been in her bag, I said no but I think we both knew I was lying.
It became a regular once a week thing where she would go out after work and the same would happen quite often.
I was called into her office once more asking why id left so late, I made an excuse about tidying up and she laughed and said I hadnt done a very good job.
As the weeks passed I got more daring and started trying them on, at first the panties then the stockings and suspenders.
Id always have the doors locked and lock myself in the office so figured i was quite safe until one day I heard the footsteps of her coming back.
With very little time to sort myself out I pulled my work trousers up over her lingerie and stuffed my boxers in my pocket.
I unlocked the door and she was stood behind it her eye to the peep hole. I said id just been cashing up but id no idea what she had seen or not seen.
She went straight into the office and picked her bag up and went through it. she took her purse from the bottom of it and said that she had forgotten it.
Peering back into her bag she said to me that her underwear was missing and asked me where it was, I shrugged and she told me to empty my pockets, i protested but she put her hand in my pocket pulling out my boxers.
Then the penny dropped and she looked me straight in the eye and said are you wearing my underwear. I tried to avoid an answer and said im sorry it wont happen again.
She looked at me sternly and said take them off now. I asked if I could go into the toilet and she just stood in front of the door shaking her head.
I undid my trousers slipped off my shoes and stepped out of my trousers. I went to unclip the suspender strap and she said wait.
She walked past me and sat on her desk, she got me to turn around and do a little twirl for her then she asked me if they feel nice. I nodded and she said ok, lets make it part of your work uniform. I made a half arsed protest, I even said what about my girlfriend. She just grinned and said get rid of her.
She told me to get dressed but to keep them on til I get home but to put them back on for work tomorrow.
As I was getting dressed she said she will sort out some extra shifts for me and that I may have to stay behind to help with stock taking.
No problem I said and once dressed I went to pick my boxers up of her desk and she snatched them from me and said no, you wont be needing these again. |
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The next day I arrived for work and was having a coffee prior to the start of my shift.
My boss stuck her head in the kitchen and said we were short staffed again and it was just me and her tonight.
The shift went quite normally, always customers about but im sure she caught me looking at her more than once.
At the end of the evening she was cashing off the til and she gave me the keys to empty the floor safe. She was stood directly over me then she reached over to get some bags and she ended up with a heel either side of my head, every time I looked up I could see straight up her skirt.
She got me to take the money onto the office ready to be cashed up. We locked ourselves in and she gave me a bag and said, this weeks uniform. I looked inside and it was bursting with lingerie.
She then told me to take it into the loo and come back with something on.
To be continued tomorrow |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Excellent so far. Please continue mmmm |
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By (user no longer on site)
over a year ago
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Great start...can't wait for more. |
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By *avid1234555Man
over a year ago
Dfs and Galloway/Ayrshire. |
Excellent start, I’ll be following this story!! |
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By (user no longer on site)
over a year ago
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Oh wow |
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I went into the toilet and opened the bag, there was about half a dozen sets in there, all with matching bras or basques.
I chose a white set with matching white stockings, it had a matching basque with hearts on it.
I put it all on and slipped my sirt and trousers over it and returned to her office.
She was sat at her desk doing some work. I walked in and closed the door. Without looking up she said show me what you chose then. I stripped off til I was stood in front of her in just her underwear.
She got up from her chair and walked over to me. She picked her bag up from the floor and said she needed to get changed now.
I was expecting her to go into the loo too but she turned around in front of me and said unzip me then.
I undid her skirt and it dropped to the floor. She had black stockings and suspenders and blue satin panties.
She turned around and I undid her blouse to reveal a matching blue satin bra that her big tits were bulging out of.
She pulled a black leather look skirt and sheer wwite blouse from her bag and handed them to me, I held the skirt and she stepped into it, then I slid it up her legs and zipped it up. She put the blouse on and buttoned it up.
She then walked back to her desk and sat down. Then she slid her chair back and said get in there bitch and pointed to under her desk. |
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By (user no longer on site)
over a year ago
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Great start. |
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I got under the desk and she sat back in the chair, she opened her legs and said you like looking up my skirt dont you?
I said yes and she kicked me with her heels on and said your a naughty little sissy and im going to have to train you.
She gave me a few more kicks then pressed her heel into my panties and looked down at me and said you are enjoying this to much, get up and bend over my desk |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Hot  |
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I bent over the desk and she took my belt from my work trousers and whipped me straight across the arse with it.
I screamed in pain and she slid her knickers off and stuffed them in my mouth.
She said if i could take 10 more I would get a reward.
I leant back over the desk and took my thrashing, she didnt hold back and it really hurt but I had no choice but to take it |
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She then took a pair of stockings from her bag and tied my hands behind my back.
She got me to lay on the floor my hands trapped behind me.
She freed my cock from the panties, it was rock hard, she smiled then slapped it telling me I had a naughty cock.
She then squeezed it really hard and looked straight at me and said this is mine now.
Then still with her clothes on but knickerless she climbed on top of me and slid my cock straight inside her pussy, she dug her nails into me as she bounced on my cock. I couldnt hold back for long and emptied my load inside her. |
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By *vbiker2TV/TS
over a year ago
morpeth |
Worth ten strokes of the belt any day |
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By (user no longer on site)
over a year ago
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Loving the start to this |
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She lifted herself off my cock turned around and lowered her pussy onto my face, I licked her as she squeezed and teased my softening cock, As I licked at her cum soaked pussy my cock started to stiffen again, she leand forward and started to suck it. Her bum had lined up perfectly with my face and before I knew it I was licking that too, the noises she made told me she liked it.
She then stood up and bent over her desk, I wriggled to my feet as my hands were still tied behind my back. She untied them and I got behind her, pushing the tip of my cock against her bum hole, she held her cheeks apart and I pushed my cock inside her, she was moaning and it was tight but inch by inch she took the lot, after a couple of mins I exploded my second load deep inside her ass. |
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She wriggled forward as I pulled my cock from her ass. With no words I knelt behind her and licked her arse as my cum dribbled out of it. I started to slip my fingers in her at 1st a couple but with ease went to 3 then 4.
She shuddered as she came, holding my head and pushing her bum back against my face.
Then she moved away and said we better get cleaned up. I went into the loo and washed my bits and returned to her in the office where she was now fully dressed.
I picked up my trousers and shirt and as I was putting them on she went in her bag pulling out a small metal chastity device. She told me to come over to her. She expertly put it on my cock and clicked the padlock shut.
I asked how long I had to keep it on for and she said that she hadnt decided, maybe a day, maybe a week, maybe forever.
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By (user no longer on site)
over a year ago
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Loving this!!! |
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I got myself dressed and she handed me the bag of lingerie and said dont forget this and as I walked out the door she said wear pink tomorrow.
I showered and dressed for work the next morning in the pink set. Was all bright barbie pink, the stockings had black seams and the whole outfit was quite see through.
I looked at myself in the mirror and couldnt believe what had become of me in a 24 hour period.
When I got to work, I noticed my bosses skirt was a bit shorter than usual, her make up a bit sluttier and her top even lower cut.
After the other staff had left she stood chatting to me about work stuff before brushing past me and giving my cage a squeeze and going back into her office to do her work.
At the end of the day I locked the doors and stuck my head in the office to say we were all done.
She looked up at me and said show me then. I slipped out of my trousers and stood in front of her, head to toe in lingerie and cock locked.
She stroked it with her finger and said does he want to get out? as she pointed to the key attached to her necklace. Not yet she said as she let go of the key.
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She asked me what size shoe I was and I said about a 7 she said she might have some shoes that will fit.
She said she has got lots of clothes that will fit me too and said she will get me a wig and make me pretty for her.
She said I was to meet her at her house at 7pm on the saturday coming.
I pointed at the chastity device and said what about this, she squeezed it through my knickers and says that stays on! |
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That was my dream when I was 20 . Wish that had happened to me xxx |
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I was told to arrive at hers for 7, I was also told to shave off all of my body hair which was quite easy as id never been a hairy person anyway.
I got to hers for 7 on the dot, she invited me in telling me to remove my shoes at the door, as I did so she looked down at my stockinged feet and smiled.
She was wearing a red silky satin type dress, low cut as ever with a buttons up the front and nylon clad legs as ever.
She poured herself a large glass of wine and handed me a beer. Then as we stood in the kitchen she told me to show her what I had on today.
I pulled off my trousers and t shirt to show her the black and red basque, suspenders, g string and sheer seamed black stockings.
She walked over to me and squeezed my caged cock through my knickers and asked if I was getting used to it yet. I shook my head and said not really and she leant in and kissed me and said you will.
As she pressed against me I felt something under her dress and it didnt take me many seconds to realise she was wearing a strap on. She said oops thats spoilt the surprise a bit but 1st we have to get you ready, come on upstairs, ive got a treat for you. |
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I walked up the stairs she followed behind me, smacking my bum a couple of times on the way up.
She directed me into her room where there was lots of clothes lay on the bed and a blonde wig and a couple of pairs of heels on the floor.
She took me to her dressing table and told me to sit then started applying make up to me, looking at myself in the mirror I thought I looked stupid but when she put the blonde wig in my head I though wow not bad.
She then slipped a black leather look skater style dress, it was short and my stocking tops could be seen. She sat me down and helped me on with the heels and the final touch bright red lipstick.
She then adjusted the neck of the dress and I heard a click, I felt the back of my neck and it was padlocked on! |
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She stood me in front of the mirror quite proud of her creation.
She then lifted the bottom of my dress as she hitched hers up to reveal a reasonably sized strap on cock.
She put it against my locked up cock and it was obviously bigger.
She whispered to me, on your knees, hands behind your back. Without question I did as I was told and she slipped her fake cock into my mouth, her hand on the back of my head as she said I was a good girl.
I tried to back off from it to get my breath but each time i did she thrust forward and pushed on the back of my head. Then she pulled out and told be to get on the bed. I got up and sat on the bed, not like that she said and turned me round so my arse was in the air.
I said im not sure about this, she said that she let me do it to her so it was only fair, then she put cold lube around my hole she pressed the tip against my hole. She pushed the tip in and said just push back on it when you are ready. After a few seconds I pushed back a little feeling it fill and stretch my virgin hole.
About half way there she said, want me to help you? I nodded and she pushed forward pinning me against the bed, then she gently withdrew and did it again a little quicker, after a few strokes she got to a regular pace.
In less than a week id gone from jacking off over my sexy boss to being dressed up by her and her taking my anal virginity.
After a couple more thrusts I started to cum in my cock cage all in my knickers and over her bed.
We both collapsed for a rest, her cock still inside me. |
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By (user no longer on site)
over a year ago
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Brilliant story |
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As I lay there getting my energy back she got up taking off her strap on then going to a draw and pulling out one twice the size and saying reckon you can take this one?
I shake my head and say can you? She winks at me and says come here. I get up and she fastens it around my waist, it almost completly shadowing my locked cock.
She then lays on the bed and slides off her knickers leaving them dangling from one ankle, she spreads her legs and I climb on top of her, pushing the monster strap on inside her as I do, she lets out a sexy squeal and rips open her dress and frees her boobs from her bra and pulls my head into them, Im sucking her nipples as she takes every inch of this cock, her wanting it harder and faster with each stroke.
Then she grabs me round the neck and snogs me as she orgasms with her hands tight round my throat.
As we were getting our breath once more she lifted the monster strap on and stroked my locked up cock.
I asked if I had earned release now and she laughed with a hand around each one and what do you think?
Not being in a position to argue, I agreed and got between her legs and ate her well stretched pussy, she rolled over offering me her ass to do the same to.
I picked up the lube and slipped a finger in her ass as I licked her, I got my other hand under her and pushed it into her pussy with ease.
I had somehow turned the tables and now I had her where I wanted her, I took my hands from inside her and kneeled behind her with the monster strap on pressed against her arse.
Dont you dare she said as i put lube on her ass and the strap on. I lined it up with her bum and said push back on it then, to my surprise she did and the tip slipped inside her. I held onto the back of her hair and pushed against her as she pushed back. She rode it til she could take no more and we both fell into an exhausted heap once again. |
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By *mfao88Man
over a year ago
north yorkshire |
Absolutely love this story x |
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We nodded off for a bit and when we woke up we took a shower together to freshen up, she unlocked the dress and we both stripped.
As we showered I asked if the cage could come off for a little wash, she knelt down and unlocked it with the key from her necklace, then washed it with shower gel, then she started to play with it, next thing her mouth is round it.
She gets back up and snogs me as she lifts her leg and guides my cock inside her pussy.
As we are fucking she says I better make the most of it, after a few mins I fire my load in her pussy.
She gets out of the shower and goes into her room returning with a smaller pink silicone chastity device.
She easily slides in on to my now limp dick with only shower gel as lube and clicks the padlock shut. |
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By (user no longer on site)
over a year ago
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Very hot  |
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I walked back from the shower into her room, my little pink cage rattling against the padlock, there was also a little pendant on it with the word sissy on it.
She passed me some black fishnet stockings, lace and statin panties and a black lacy suspender belt with a matching timy little bra.
She watched me as I put them on in front of her.
Lay on the bed face down she instructed and I complied. She then tied both of my hands to the bed and left the room, returning a few mins later wearing a pvc dress and holding a whip.
She sat next to me and asked if I liked using that big strap on on her, I laughed and told her she loved it. She whipped me straight across my bum and said that I needed teaching a lesson. It stung and I yelped a little, but she took no pity whipping me across the top of the legs, bum and back.
Then she untied me, passed me my clothes plus another bag of stuff and said get dressed and dont be late for work on Monday!
To be continued |
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I went to work monday after spending the weekend with my cock locked away, Black stockings suspenders and panties under my work clothes.
To my surprise my boss wasnt there, her boss the area manager was covering for her.
The two of them were good friends and often went out together on an evening.
As I was talking to her I noticed she had a key on her necklace too! Had my boss told her? The area manager was a readhead, tall and slim with small tits but pretty and a nice arse.
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The working day went as normal, and once everything was locked up I stuck my head in the office to tell her everything was locked up.
She smiled and said yes it is, even you!
I asked her what my boss had told her and she said everything!
She stood up from her desk walked over to me and undid my belt letting my trousers fall to the ground. She rubbed the front of my knickers and said get it out.
She held it in her hand inspecting it, saying how great she thinks it is, and that she wanted to get her husband in one and that she wants me to help her do it!
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By (user no longer on site)
over a year ago
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Very hot |
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I asked how could I help her do that she says that he loves looking at sissy porn and that she would like to doll me up and give me to him as a gift.
She says after hes fucked me and goes soft I am to lock his cock up.
I tell her that im happy to do anything she says and she says thats good cos its not like ive got any choice.
She then tells me to get on my knees |
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Great story. Looking forward to hearing more! |
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She stood in front of me and hitched her skirt up, she had nude hold ups on and blue silky knickers on.
She pulled my face to between her legs and was grinding herself on my face. I had my hands on her arse as she slid her knickers to the side and I licked her pussy as she held her pussy lips open.
I slid my hands to between her arse cheeks to find that the dirty bitch had a butt plug in. I started to wiggle it and she moaned with pleasure.
She turned around and spread her cheeks as i licked around the plug, then she pulled it out so i could lick her ass.
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By (user no longer on site)
over a year ago
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As licked her bumhole I started to finger her pussy and it long before I had most of my hand inside her.
She was pushing her arse back on me so I could lick deep inside her ass.
My caged cock was pressed up against her nylon clad legs and she squuezed them together around my caged cock.
I started to dry hump her legs whist in chastity, that proved to be a big misstake.
She pushed me away asking who said you could touch me with that thing! |
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She tells me to put my hands behind my back. Without question I obey then without warning she kicks me hard between the legs with her heel.
I collapse onto all 4s but she just walks behind me and kicks me again from behind making me fall to the floor on my stomoch.
She digs her heel into my arse cheek saying get back up bitch, i get back onto all 4s only to be kicked again, this time I stay up. She kicks me again and I fall to the floor once more.
I get back on all 4s without being told. She says I have to take 5 in a row without falling.
I put my head on the floor and stick my ass up and she kicks me 5 times in quick sucession.
She then tells me I can fall on this one and kicks me one final time harder than ever. |
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I fall to the floor, tears streaming down my face.
She pulls me to my feet by my hair, and wipes the tears from my face. She looks me in the face and says want me to stop?
I shake my head, knowing that im totally powerless against this woman.
She then stood behind me and scratched down my back with her nails leaving marks from my shoulders to my bum cheeks.
She then stood in front of me and told me to look at her. She started to undo her top, I glanced down at her boobs and she slapped me hard in the face.
She slapped me again and again calling me a dirty little sissy perv. |
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By (user no longer on site)
over a year ago
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Has this run out of steam? |
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By (user no longer on site)
over a year ago
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Dream boss |
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She then told me to get dressed as it was home time, but said dont make any plans for tomorrow night as I was going home with her.
I agreed and she handed me her butt plug, sleep in this tonight and have it in tomorrow for work too.
I got myself and dressed and went home, knowing tomorrow was going to be a very testing day. |
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So the next day I went to work plugged, caged and in pretty lingerie. The area manager came in toward the end of the day.
She told me I was coming home with her tonight as she had a couple of little surprises for me.
After work I followed her to her house. As we went inside I could hear talking, we walked into the lounge and her hubby and my boss were sat there.
My boss was dressed like a cheap hooker, tiny leather skirt, stocking tops on show see through top with her big tits busting over the top of her bra.
My area manager looked at me and said upstairs you, lets get you ready. We went upstairs and she pulled out a similar outfit to what my boss was wearing.
She put it on me along with blonde wig and did my make up, she gave me some heels to put on and I was sent downstairs to wait for her.
Her hubby went upstairs leaving me and my boss alone together.
She apologised and said she was sorry she told her boss but she had seen us together on the security cameras.
Just do as they say and we will be ok, I asked her what she meant and she replied they are in control of this not us.
She gave me a hug and the door opened, area boss was in a pvc catsuit wearing a large strap on and her hubby was naked and his cock wasnt far off the size of the strap on! |
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They both saw is hugging on the sofa, area boss lady said aah thats cute, you two should have a little kiss and make out in front of us.
We started to snog as she rubbed my locked up cock my hand went up her skirt and inside her panties but was met with a steel plate. My are boss laughed as it dawned on me that my boss had a female chastity belt on.
Area boss and her hubby walked up to us, she said that we both needed to earn our release, she placed her strap on to my mouth and her fella did the same to my boss, we both got face fucked. Then they swapped and I got my 1st real dick in my mouth. I had no choice but to take it, there was a hand on the back of my head.
We were then ordered onto all 4s facing eachother and told to kiss again. Her chastity belt had an opening at the back by her bum and her fella thrust his cock inside her, next thing I felt the strap on against my plug, she pulled it out and pushed her stap on up inside me.
Me and my boss kissed as we moaned as we got stretched and used. |
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By (user no longer on site)
over a year ago
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After about 5 mins they both pulled out and swapped places, i felt her hubby rubbing his cock on my stretched and weaken bum.
Area boss thrust her big strap on straight up inside my bosses arse and she let out a scream as she did so, area boss pulled her hair to keep her in place.
Then I felt her fellas warm cock sliding up inside me, sissy instinct kicked in and I felt myself pushing back on it as my bosses big tits were pushed against my face. Her fella quickened up the pace and fired his spunk inside me.
They both withdrew and me and my boss collapsed in a heap on the floor as we cuddled. |
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By (user no longer on site)
over a year ago
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Very hot |
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. Fabulous 
