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From regret to serving as a sissy….a 100% true story

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By *histime911 OP   Man
20 weeks ago

southend

I stirred from my alcohol fuelled slumber completely oblivious to the time. Low winter sun was streaming through the gap between the poorly drawn curtains giving me an indication that it was morning at least.

I’m sure we have all had that feeling sometimes when waking up after a night out? A feeling of regret or shame. That thought that you have perhaps done something you shouldn’t have and wouldn’t have but for the alcohol. Head pounding and somewhere between still being d*unk and an impending hangover I try to recall why I have this feeling.

I knew it had been a normal night out. I was away at uni at the start of the second term. For boring reasons, I was back earlier than most and had arranged a typical night out with friends involving lots of alcohol and an aim to pull some local hottie.

But this feeling of regret was strong. I opened my eyes and looked around my room. Typical student campus accommodation. Immediately I was struck by items out of place. At the side of my bed was the vibrator I had bought myself which I would use occasionally when watching porn and fantasising about being used by older men. It was glistening with lube so I know that I must have got home, no doubt frustrated, and used it on myself.

Next to the vibrator was my phone. The memory then came cascading back to me and answered the question of the feeling of regret.

Being away from home and in a new town I had started chatting to men from various sites. My preference was dominant older men. I would message them and get off on the thought that they were getting turned on at the thought of using me. There was one in the area who had been keen to meet but I had always chickened out. He had seemed perfect to me - he went by the name ‘Jhndom’ and the dom part was what attracted me to him. He was 30 years older than me and we had messaged over the previous weeks about what he would do to me.

This has all seemed like a bit of harmless fun-but as I reached for my phone to check the messages, I knew everything was about to change. The last message showed up “I’ll be there in 45 minutes”. My heart pounded (and I admit, my cock twitched). I checked the previous exchanges and it all fell in to place. In my d*unken state I had messaged and told him all the things he could do to me. This time though id given him my address! And he was going to be here shortly. With him having my details there was no chickening out of this one……..I was terrified but excited….

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By *omiley49Man
20 weeks ago

London

Nice. Please keep going!

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By *histime911 OP   Man
20 weeks ago

southend

I was a mixture of terrified, nervous and disgusted. I was a ‘straight’ guy who generally managed to keep my real desires secret. He now had my address and messages from me telling him what he could do to me. He would be turning up and there was no backing out. But first and foremost I had that post alcohol horn and was excited about what would happen.

I tidied the place up, though kept the vibrator out. Then I showered and cleaned my teeth - washing myself thoroughly (inside and out) so I could please my visitor. I have to admit to having a little play with my semi-hard cock at the thought of the messages we had exchanged, but was careful not to go too far - I had been told to save my load.

I dressed as instructed - loose joggers and t shirt and nothing else. I knew from our messages I wouldn’t be in them for long. And then shortly after I was ready the message arrived. “I’m outside, slut”…..

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By *ackiex32TV/TS
20 weeks ago

Wick

Sounding good

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By *icky13Man
20 weeks ago

Didcot

Sounding good

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By *ony 529Man
20 weeks ago

Coventry

Oh sounds good to me for some unknown reason

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By *eddyfMan
20 weeks ago

Chatham

Great stuff

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By *kitsmeMan
20 weeks ago

St Helens

Good start

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By *egselevenMan
20 weeks ago

burnley

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By *ita99TV/TS
20 weeks ago

bognor

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By (user no longer on site)
20 weeks ago

Hope there is more to come

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By *argassMan
20 weeks ago

Brough

Yes done this in prem inns a few times

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By *lderoneMan
20 weeks ago

Cheadle Hulme

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By *ony 529Man
20 weeks ago

Coventry

It was just getting me to attention I want to look for another story

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By *tephens11Man
19 weeks ago

Leeds

Great start !!

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By *el1234Man
19 weeks ago

Santry

Good start

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By *ornysuckerMan
19 weeks ago

Portsmouth

Good start keep going

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By *im12Man
19 weeks ago

West Lothian

Good so far

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By *histime911 OP   Man
19 weeks ago

southend

I nervously headed to the door of the communal building to meet him. As I mentioned, I had returned to halls early but there was still the odd caretaker, groundsman or foreign student around.

Heart pounding. I could see a man holding a carrier bag through the glass panel as I approached down the corridor and knew this was the man who would soon be using me. I opened the door and sheepishly asked “John?”. He looked me up and down and a wicked grin spread across his face. It conveyed that he liked what he saw and he liked what he was going to do to me. “Call me Sir, or Master” he said, instantly conveying who was in charge.

He was over 30 years my senior. Much bigger than me, he was burly from years of manual work (I knew he was a builder of some sort). Grey hair, wearing a fleece splattered with with paint and plaster and work boots. He was a real man.

“Sorry Sir” I mumbled. “Pardon?” He barked back. “I’m sorry Sir” I said more clearly. He nodded and said “That’s better, now let’s go and see if you are the sissy you said you are”.

I lead him through the corridor in silence. There was no small talk as we both knew what we were there for. I was grateful that we didn’t pass anyone as it was clear he was not a student and most in halls would know he was not my dad.

We got to my room and we entered. He stood right in front of me, close enough that I could smell that he was a smoker. Grabbed my crotch through my joggers feeling my semi hard cock and said “pathetic”. Again, no question who was in charge. He gave me the bag and said “go and get ready”. I knew what this meant as we had discussed it in our d*unken exchanges. “Yes sir” I said meekly.

I left the room and walked to the communal bathroom clutching the carrier bag. My heart was racing and I was buzzing as I locked the bathroom door to inspect the contents of the bag. I laid it out and it was exactly as described in the text exchange. A black lacy paid of knickers, black bra, black nylon stockings, black pvc mini dress, a pair of platform stripper heels and a blonde wig.

My joggers and t shirt were off quickly. I had a great urge to play with my now rigid cock but resisted as I didn’t want to disappoint my new master. The knickers went on first, feeling amazing against my straining cock. Then the bra which fit well around my young frame. I rolled up the stockings that had a lovely lace hold up. I then put on the heels that really accentuated my toned stocking clad legs. I wriggled in to the pvc mini dress. It was a perfect tight fit. The dress barely covered the stocking tops and the shape made me look like I had lovely feminine hips. Lastly, the short blonde bob wig-a perfect contrast to my normal brown hair. I looked in the mirror - I was transformed - not convincing but looking like the slutty whore I wanted to be. I was ready.

The final part was designed to show my compliance. He was now in my room showing his control and I had to walk along this corridor to my room dressed like a slut. I knew no one was about really but being seen would change the rest of my year at uni. But I looked at myself in the mirror again. I was no longer the ‘straight’ guy who chatted up girls and played football. I was a sissy tart.

I opened the bathroom door and walked deliberately and tentatively in the heels to my room. No one was around and I enjoyed the exhilaration of walking in public like a whore. I finally got to my room and knocked. “Who is it” barked my master, enjoying the control. “It is your slut” I said back.

The door opened and we were ready to play…….

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By *ita99TV/TS
19 weeks ago

bognor

More please

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By *lutty Sara2020Man
19 weeks ago

Stratford on avon

Can’t wait to hear more

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By *antsubbiladMan
19 weeks ago

milford Haven

Very horny!

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By *addyBottomMan
19 weeks ago

Blaby

Mmm nice start

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By *perm bank69Man
19 weeks ago

Hythe

Love it

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By *irmingham_BoyMan
19 weeks ago

sutton

Excellent start!

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By *agerforbothMan
19 weeks ago

perth

Excellent stuff

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By *ony 529Man
19 weeks ago

Coventry

Well I’m excited at least

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By *histime911 OP   Man
19 weeks ago

southend

I walked in and stood in the middle of the room. He leered at me as he slowly walked around me looking me up and down like he was inspecting and appraising me. In my stripper heels we were now similar height, though he was the much larger man.

As he walked behind me there was a ‘thwack’ as his strong masculine palm smacked my pvc covered bottom. It was more shock than pain. “Did you like that, slut?” He asked. “Yes sir” I replied. ‘Thwack’ another spank on my bottom, almost making me unbalance on my platform heels. He merely grinned and said “good girl”. I’d never been called a girl before, but here I was, in stockings, knickers, bra, heels and mini dress at the mercy of a stronger man.

He walked back in front of me. Only inches between our faces as he continued to ogle me. I felt so desired. I could smell the aroma of tobacco around him. As a non-smoker who normally hated the smell of cigarettes, this contrast turned me on even more. He then held the back of my head and unexpectedly, and roughly, kissed me. I’d snogged plenty of girls before but this was different. It was aggressive and animalistic as his strong tongue pushed in to my mouth. It was electric and erotic and my cock was absolutely straining in my knickers and against the tight minidress.

He then pulled away and said “right, get on your knees where a slut belongs”. I duly complied and I was now level with his crotch which was only inches away. He slowly pulled down his joggers and pulled them off over his boots so he was now stood in his boots, socks, grey boxers and t shirt. I could see the outline of his cock through his boxers. I’d seen pictures from when we were texting but this was now real and I couldn’t wait to see it. Instinctively I reached out a hand to touch it. “Oh you are an eager slut aren’t you” he asked. The truthful answer was “yes I am, Sir”. As I touched his cock through his boxers. It felt solid and much bigger than mine. “Good little whore” he said, and I actually felt pleased with the praise. He let out some soft gasps to let me know he was enjoying it and I was enjoying the feeling of his cock getting absolutely rock hard at my touch.

“Right, slut, it’s time to take these boxers off” and following his instructions, and trying to be as seductive as possible, I slowly stopped rubbing him and moved my hands to the waist band of his boxers, slowly pulling them down, eager for the moment his cock would spring out…..

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By *hinySecretsTV/TS
19 weeks ago

Leeds

I'm so turned on right now!!

Please continue?

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By *ilkyphoebeTV/TS
19 weeks ago

Biggleswade

Mmm building nicely... Shame not silky panties hehe

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By (user no longer on site)
19 weeks ago

Mmmm nice xx

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By *histime911 OP   Man
19 weeks ago

southend

I slowly lowered Master’s boxers. Revealing his black and grey pubic hair before the moment I had desired - his cock sprung out and stood rigid. 8 inches and thick, far bigger than mine.

I continued to pull down his boxers, releasing his low hanging large balls. He shuffled the boxers over his boots to take them off and he parted his legs a little to fully expose his gorgeous cock and balls. It was inches from my face and I could smell the manliness. I started to move my hand up towards it but he batted it away. “You have to beg for it, slut. And a real whore doesn’t use their hands” he commanded. Again, I was not the ‘straight’ lad everyone thought I was- I was a pathetic sissy wearing stockings and heels. “Without thought I asked “please Sir, can I have master’s cock”. “Of course you can you good whore” he replied and he arched his back a little so his cock moved towards my face. I opened my mouth and slowly enclosed it around his meat. It was so thick and tasted amazing. I started to suck and move my mouth up and down the shaft and he also started to rythmically push back and forward letting out low groans of pleasure.

He started thrusting harder, holding the back of my head and pushing his cock right in to my throat. Occasional he would just keep it there, hands clamped round my head so I had no where to go. I gagged and spluttered a few times. He would remove his cock so I could get my breath back but the respite was fleeting as he would soon thrust it back in to my throat. All the while telling me I was a good slut, or asking if I liked Master’s cock. I could only attempt a nod in confirmation.

“Lick master’s balls” he demanded as he let go of my head and removed his cock from my throat. Relieved for the air I gratefully ran my tongue along his sack, occasionally kissing or gently sucking his balls as he told me I was a good girl. Whilst working on his sack he took his meaty, glistening cock and slapped it across my face. Covering my cheeks and forehead in my own salvia as he laughed and called me a perverted bitch. I guess I was.

Then he abruptly stopped and asked “are you ready to give Master your hole?”…….

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By *entletouchMan
19 weeks ago

Edinburgh

Arousing story

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By *ssassinMan
19 weeks ago

Kirkcaldy

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By *ony 529Man
19 weeks ago

Coventry

Ohhhhh fuck ……… yes

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By *atin9999Man
19 weeks ago

mallow

Mmm of course you do

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By *hris106699Man
19 weeks ago

North hykeham

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By *histime911 OP   Man
19 weeks ago

southend

“Yes sir” I replied hesitantly. Although in our text exchanges I had told Master how much I wanted him to use me, the reality was a different proposition. He was larger than my vibrator, both in length and thickness and I had no idea how it would feel to take him. Almost sensing my concern he took control as a Master should and said “don’t worry slut, it’s what you want and you will enjoy it. Or at least, I will”.

I stood from my kneeling position and he kissed me again. Whilst doing so he hitched my mini dress up over my bottom and pulled down the top so it exposed my bra. I was now in the stripper heels, stockings, knickers and bra with the pvc mini dress bunches around my waist. My cock still not touched by straining and leaking a little in anticipation.

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By *oodtimebiboyMan
19 weeks ago

Bristol

So enjoyable

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By *aidclaireTV/TS
19 weeks ago

bideford

Great story. X

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By *umslut7Man
19 weeks ago

dunfermline

Superb

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By *hinySecretsTV/TS
19 weeks ago

Leeds

Following this story avidly! So hot... X

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By *histime911 OP   Man
19 weeks ago

southend


"Following this story avidly! So hot... X "

Thank you! It is an encounter I look back in fondly!

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By *histime911 OP   Man
19 weeks ago

southend

He ordered me to get on to the bed on all 4s. The bed was a single bed against a wall with a window along it. I got on to the bed on all 4s as instructed. My bottom no exposed to the centre of the room other than the small lacy material covering my crack. My face was directly in front of the window.

I sensed him move behind me. ‘Thwack’. This time his firm hand made direct contact with my bare arse Cheeks. It stung but felt great. ‘Thwack’ again followed by a little laugh from Master. “You are a good slut”. Again the praise made me swell with pride that I was pleasing this older man.

I could then hear something that sounded like a kid being taken off and him squirting something on to his fingers. The knicker material covering my hole was moved to the side and a cold wet finger slowly rubbed my opening before parting and a finger slipped in, then 2. It felt amazing and I couldn’t help but wriggle on to his fingers. “Oooh you like that slut so you?” He asked. “Yes sir” came my reply without thinking.

He then withdrew his fingers and allied some more liquid - he told me Master was now going to own my hole so I knew he must have been lubing his manly cock. One hand was placed on my waist and I felt his meat up against my hole-pausing at the entrance before pushing past and in. I’d never felt anything like it. He now put the other hand on my hip too and held them right as I felt his cock push further and further. It took my breath away. It hurt and I screwed my face up but tried to relax. I had no idea how much he’d put in until I felt his crotch against my arse and realised he was now all the way in to the hilt. My cock twitched and I had the urge to touch it but I was using my hands to balance on all fours. “Oh you so take it like a good girl” he told me. And with that he started to slowly move back and forth, bringing his cock almost out and then powerfully pushing it back in all the way. Here I was, in front of the window, on my hands and knees, heels, stockings and bra, dress bunches up and knickers pulled to the side, and a meaty cock pumping in and out of my tight hole….

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By *imale999Man
19 weeks ago

dudley

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By *hinySecretsTV/TS
19 weeks ago

Leeds

🤤

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By *histime911 OP   Man
19 weeks ago

southend

As he built his rhythm I got use to the feeling of being stretch and pushed back when he pushed forward so there was a lovely slapping sound of his balls and crotch on my arse as he pumped away. I felt like a true sissy enjoying being used by a stranger.

He then pulled out. I felt empty not having him inside me. “Lay on your back” he ordered. I duly obliged. He hooked my stocking clad legs up and over his shoulders as he guided his cock in to me from this new position. He again pushed all the way in and I could feel his heaviness on me. I could now see masters face, with my stockinged legs and heeled feet over his shoulder. He pumped hard and fast. He looked me in the eye and I tried to hold his gaze as he told me what a good girl I was.

The bed was rocking and that lovely slapping sound kept coming as he ploughed away.

Then he asked if I wanted Master’s cum. I looked him in the eye and said ‘yes please’. His grunts got louder and he started to tense and shouted ‘here it is, take master’s cum you little slut’ as he pushes his cock as deep as he could go in to my tight hole, his full body weight on me and I could feel him spasm as he sent his warm seed in to me.

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By *histime911 OP   Man
19 weeks ago

southend

Eventually, after what seemed like an age he slowly pulled out his softening cock.

He told me to get off the bed and stand up in front of the room’s full length mirror. What a sight I was. Dishevelled after being throughly used, my cock rigid and leaking constrained in the black lace knickers.

He took my vibrator from the side table, bent me over a little and slipped it in my now stretched and wet hole. “That will plug my seed in you, you little slut. Now wank’. I remember noticing how easy the vibrator now fitted having being stretched by him.

I had obviously wanked many times before but now it front of someone. Watching myself in front of the mirror looking like a slut I slid my cock out of the knickers. It felt so good to touch. With pre-cum I started stroking myself whilst he watched with a leer. It didn’t take long before I could feel that build up in my balls and then shot the biggest stream of spunk id ever released. It hit the mirror and went over the carpet. “Good slut” my master said.

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By *hinySecretsTV/TS
19 weeks ago

Leeds

I'm leaking so much reading this!

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By *histime911 OP   Man
19 weeks ago

southend


"I'm leaking so much reading this! "

That you. Had messaged you but not in your age range.

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By *reed maid carley cumdumpTV/TS
19 weeks ago

exeter

Am loving this story, so wish it was me being used xx

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By *histime911 OP   Man
19 weeks ago

southend

Now we both had got what we wanted and I was in heaven. Master started to dress and told me to walk back to the bathroom to get changed. He removed the vibrator. It glistened with his spunk and lube and I felt his seed trickle out my hole.

This seemed more daunting - I didn’t have that pre-orgasm horniness where you would do anything. But I was a good slut. So I left the room and did a walk of shame to the bathroom in the heels, stockings, kickers and bra with the dress still round my waist. And a strangers spunk dribbling down my leg. I made it with out being seen and slowly undressed in front of the mirror. I touched my hole to marvel at how it had been stretched. I put the clothes back in the bag and put my joggers and t shirt back on.

I returned to my room but Master had gone.

I checked my phone and there was a message “thank you slut. Keep the clothes. You will need them again. You are mine now”.

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By *sh1966Man
19 weeks ago

Exeter

Wonderful

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By *histime911 OP   Man
19 weeks ago

southend


"Wonderful "

Thank you!

I still enjoy these type of meets if any older men liked the sound of it….

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By *ystevoMan
19 weeks ago

Pensarn

Wow love it

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By *ssassinMan
19 weeks ago

Kirkcaldy

Great story

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By *issychrissyMan
19 weeks ago

Greenhithe


"I'm leaking so much reading this! "
Me too, this is so hot x

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By *el1234Man
19 weeks ago

Santry

Love it

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By *amantha_kelTV/TS
19 weeks ago

magherafelt

Lucky girl fabulous

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By *ohnny 51Man
19 weeks ago

Middlewich

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By *imale999Man
19 weeks ago

dudley

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By *egselevenMan
19 weeks ago

burnley

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By *ogwhammerMan
19 weeks ago

Rainham KENT

Brilliant

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By *histime911 OP   Man
19 weeks ago

southend

Story seems popular with the fellow submissives! Any tops like what they read and want to message me?

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By (user no longer on site)
19 weeks ago

I would love a Master like that

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By *parks2020Man
19 weeks ago

East Kilbride

Would love a master to control me

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By *uffolkmale54TV/TS
18 weeks ago

lowestoft

this is fantastic

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By *histime911 OP   Man
18 weeks ago

southend


"this is fantastic "

Thank you x

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By *aniBttmBoiMan
18 weeks ago

Doncaster

Very hot, love this story. Well down for walking down the halls haha x

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By *ilkyphoebeTV/TS
18 weeks ago

Biggleswade

Ooh wow

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By *perm bank69Man
17 weeks ago

Hythe

Mmmmm

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By *ubBikerBtmMan
17 weeks ago

Swansea Valley

Amazing story, did he keep using you? Would love to meet a guy like that

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By *aney RopesTV/TS
17 weeks ago

Gourock

More please

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By *ndstorm45Man
17 weeks ago

Wakefield

Mmmmmmmmmm. Awesome.

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By (user no longer on site)
17 weeks ago

We have a lot in common ..

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By *ia2TV/TS
17 weeks ago

Near

oooo I’ll have to come back and read this when I have more time to sit with a little glass of wine (or two ) and enjoy it, hehe, xxx, Tia

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By *moothtouch55Man
17 weeks ago

Chandlers Ford

I love the feeling of seed leaking from my pussy afterbeing fucked hard and deep.

So loving re recall the experience you have had.

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By *seableMan
17 weeks ago

Halesowen

This is a perfect read, thank you so much.

I would have loved this when I was young.

I'd love it now od course but not the kind of slut studs want these days sadly.

Tha ks again.

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By *heekyheadMan
17 weeks ago

Doncaster

Great story. Made me so horny

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By *histime911 OP   Man
13 weeks ago

southend

Thanks for all the feedback guys. Any tops who like what they here-get in touch x

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By *ia2TV/TS
13 weeks ago

Near

oooo sweetie having found a little bit of time I’ve just finished reading. What a horny little minx you’re turning out to be hun You've made my skimp little thong so wet I got so excited hehe. Loved reading it. It’s a good job us girls are quick learning how to take cock properly isn’t it and it’s sooo enjoyable as well xxx Tia

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By *heffBiBtmMan
3 weeks ago

Sheffield

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By *rains78Man
3 weeks ago

all over

This is good

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By *azmin999jmMan
3 weeks ago

Wakefield

Wow

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By *histime911 OP   Man
3 weeks ago

southend


"This is good"

Thank you - happy memories!

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By *ckieroyMan
3 weeks ago

Shrewsbury

I hope there is a sequel.

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By *hris106699Man
2 weeks ago

North hykeham

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By *ub slave whore jessieTV/TS
2 weeks ago

Grimsby

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