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From Regret to Sissy - Part 3

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By *histime911 OP   Man
1 week ago

southend

I’ve previously posted about my formative experiences - check out ‘From Regret to serving as a sissy’ and ‘from regret to sissy - part two).

I thought it was about time to confess more!

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By *histime911 OP   Man
1 week ago

southend

Did you enjoy that” asked master. “Yes sir” is all I could say as I basked in the glow of one of the most powerful orgasms I’d ever had.

He eased me up and undid the handcuffs, finally freeing my hands . They were sore where the metal had dug in but it didn’t seem to matter. “Clean yourself up, you dirty fucking whore” said the old man. I slowly got off the mattress, tottering in the heels and walked back to the bathroom, where earlier I had been naked and urinated on by these old men.

I looked at myself in the mirror. My softening cock still exposed as the thong was pushed to the side. Basque and stockings covered in sticky semen. I felt behind and could feel cum still trickling out of my arse. I lingered over my face in the reflection - again covered in sticky semen deposited by an old man. What had I become. Was I disgusted? Or had I enjoyed it……?

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By *histime911 OP   Man
1 week ago

southend

As the days passed I still couldn’t reconcile in my mind if I had enjoyed the experience. University had certainly not started as I expected.

I threw myself in to normal ‘guy’ stuff, flirting with the girls on my course, playing sports. But in quiet moments I couldn’t stop thinking about how turned on I had been being used and humiliated by older men. I knew the urge and desire was creeping back, no matter how much I fought it…

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By *histime911 OP   Man
1 week ago

southend

My master had messaged me, but I was trying to fight the urges and get back on the path of being a good ‘straight’ boy.

However, I knew I couldn’t ignore him for long. In one boring lecture my phone vibrated - I surreptitiously checked and there was a message from Master with a picture. I knew what the pictures were of, even from the small preview image. I clicked on them- it was photos taken at our last meet - me in stockings and heels- with a message simply saying ‘I own you’….

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By *histime911 OP   Man
1 week ago

southend

I couldn’t suppress my feelings. My cock twitched and I counted down the minutes to the end of the lecture so I could respond (and look at the photo of me looking like a slut!).

Soon as we were told to pack away our things I need my stuff and headed to the nearest loo so I could compose myself in the cubicle. I replied to Master simply saying ‘yes I am sir’. He promptly responded saying ‘Friday 5pm-i will collect you in the car park’. No questions on my availability or willingness - just a clear direction….

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By *oxy4youTV/TS
1 week ago

Henfield

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By *histime911 OP   Man
1 week ago

southend

I had a few days to pass during which I wondered what master would have in store for me this time. I’d made it clear (braver in writing than reality) what my limits were and he had pushed them. It took great efffort not wanking myself off at the thought of what would come…. But I resisted as I knew my balls full would make me more compliant to whatever he had planned….

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By *histime911 OP   Man
5 days ago

southend

The Friday came about and I washed and prepared for whatever master had in store for me. I suspected I wouldn’t be in my clothes for long so wore loose fitting joggers and jumper and went to the car park. Always a strange feeling walking through halls with people going about their daily business whilst I was on my way to do something that was likely to be quite sordid.

Masters van was there, and after a quick glance to check no one I knew saw me getting in, I got in to the passenger seat. I was met with a gruff ‘evening slut’ which instantly reminded me who was in control.

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By *usan 749ukTV/TS
5 days ago

Bangor

Excellent

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By *histime911 OP   Man
2 days ago

southend

We drive off and it was clear there was not going to be any small talk. I still didn’t know the area that well, but rather than the dingy council estate he has taken me to last time, this time the houses seemed to be getting nicer as we went.

After only about 10 minutes of driving he took a few junctions and slowed down along an unremarkable middle class cul-de-sac, with semi and detached houses. At the end he turned his van in to a driveway of a neat looking detached house and parked up. As he got out he said ‘come with me’ and I got out and was led to the front door. My heart was pounding - the buzz of the unknown. What was in store for me this time….

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By *aypee46Man
2 days ago

Nuneaton

Mmmmmmm sounds fun x

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By *mooth FuntimeMan
2 days ago

Oxford

Go on….

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By *histime911 OP   Man
2 days ago

southend

Master knocked on the door the door and stepped back so that as the door opened I was standing in front of the host.

I was pleased with what I saw- a smart looking man, in his mid-60s at a guess. Thin, with grey hair, but healthy looking-like a professor I thought (given I was at university I did think it a possibility). He looked me up and down and smiled, liking what he saw. ‘Come in’ he said and stepped aside. I felt masters hand at the small of my back push me gentle towards the door - but he need not have bothered- my cock was stirring and I was excited to see what unfolded….

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By *histime911 OP   Man
2 days ago

southend

We stepped in and he directed me through a door in your what was his lounge. Warm, nice carpet and sofas. ‘I’m Graham, and I hear you are a fucking slut’ he said to me. His abruptness caught me off guard and I could only stammer back a ‘yes’. He grinned. ‘Good. Then remove your fucking clothes’ he ordered. I’m not sure why but I looked at master for approval and he just nodded. The room was bright and I felt a bit shy getting undressed. I took my socks off, then top, then joggers, then slowly pulled down my boxers. I was extremely self conscious of my cock growing hard.

Graham leered and walked round me, like he was inspecting me. ‘Not bad’ he said to my master rather than me. ‘But she needs to lose this’ he said, tugging at some wispy chest hair. ‘I hear you like being treated like a girl…. So you should look like one… don’t you agree?’. I could only nod…..

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By *histime911 OP   Man
2 days ago

southend

‘Come with me’ he ordered and he led me upstairs and into a lovely large bathroom with full length mirror, bath and shower. He went in to a cabinet and came out with some shaving gel and blades. He started to squirt the gel on his hand and massage it in to my chest. He then shaved that area with delicate precision. It felt so intimate and my cock grew harder. He then proceeded to shave my legs and arms and back with a concentrated look - occasionally complimenting me as he looked at his handiwork. My mind was thinking ahead and the time came when he worked up the gel around my cock and balls, taking my cock in his hand as he shaved around the base and then held my balls and worked on them as I did all I could to avoid squiring. It was terrifying but intimate.

He told me to get in the shower, which he turned on and washed me, then after turning it massaged some cream in to me. It felt good. He had removed all hair from me and told me what a good girl I was.

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By *histime911 OP   Man
2 days ago

southend

He then me in to the bedroom. On his soft looking double bed was laid black stockings, black basque, black lacy thong, black skirt and a glittery top. The lingerie looked expensive compared to what I had been made to wear before. He saw me looking and asked if I liked it. I nodded and he grinned and barked - ‘put it on and come down’.

As he left I started to put the clothes on - it felt expensive and felt amazing as I slid it over my bare body. I wriggled in to the skirt and top which fitted perfectly. At the foot of the bed were some black high heels which I put on and noticed how the made my stockinged legs look even more feminine. There was also a blonde short bob wig which I put on. I looked in the mirror and could barely recognise myself. I felt so feminine.

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By *h22cdTV/TS
2 days ago

BH22

Very nice. Keep going x

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By *aimeSmithTV/TS
2 days ago

Hoo

Sounds amazing xxxx

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By *histime911 OP   Man
14 hours ago

southend

I slowly made my way back downstairs as instructed - holding the handrail tight as I was still not used to walking in heels.

When I got in to the lounge master and Graham were sat there in just boxers. They both stood up, revealing nice bulges. Graham was skinny, but healthy looking. Light tan showed off his white wispy chest hair. I could see them both inspecting me. My cock excited but well concealed in the luxurious lacy thing and skirt.

They both stood near me and Master said ‘well, get to work slut’. Pushing me down to my knees. I was level with their boxers. Graham pushed his crotch in to my face and held the back of my head. I could feel his hardening cock through the material. He took my hands and put them in to his waistband - I knew what to do… I pulled down his boxers and enjoyed that moment when his cock sprung out and found its natural position. It was very long and meatier than you would have thought given his lean frame. Nice neat white pubic hair framed it. Without being asked I licked the length, then moved down to lick his very low hanging large balls. I hadn’t even been asked. ‘Good slut’ he said. He then proceeded to take his cock in his hand and wipe it over my face and slap it on my lips. ‘Open up’ he said and before I knew it his cock was driving in to my mouth and to the back of my throat. He held my head and drove forcible, causing me to gag. I could tell he liked that.

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By *harlotte39cdTV/TS
6 hours ago

rochester

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