Tag: crossdressing

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Alone with Will again

Will takes control…

If you’ve read previous instalments, you may remember that Will had agreed to meet Colin and I to cuckold Colin. However, before the three of us met, Will had asked for an evening alone with me so that he could finally have me bareback. I was at Coli…

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Blackpool Pt3

My beatification and my later surprise emasculation begins, but first.. Simon was to make the most of me…

Well I can honestly say that I didn't get much sleep last night, Simon, so lovingly and masterfully made love to  me with a gentleness I'd not often experienced with other men, or women, I'd always been that cum dump  men loved to fill.Ive …

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Moving forwards with Colin

Planning the next adventure…

After ‘Colin’s surprise’ there were a few loose ends to tie up. I was chatting to Will to arrange a session with him where Colin could be cuckolded. I also still had Mark, the original lover, waiting in the wings. I had to tidy things up.Mark was a g…

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Colin’s surprise - Part 2

New rules are agreed…

Continued from ‘Colin’s surprise - Part 1’I’d returned to Colin’s sitting room, as ordered by David.Colin was sat in an armchair looking totally dejected, but still managed to give me a fleeting smile. David, however, was in the middle of the so…

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Blackpool Pt1

Simon knew I'd use that voucher, however I wasn't ready for what he had in mind…

Recap from previous story >>Simon was just as mysterious as he'd always been, I'd got this wonderful once in a lifetime offer, I'd be stupid not to take it, wouldn't I?<<That one thought would keep me awake, thinking , should I, shou…

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How it all began part two

How I progressed form simple sex acts to crossdressing…

At first when I had a greed to be Simons girlfriend I had not given it much thought, but as I lay in bed that night it struck me that all though I was letting him do sexual things to me it was kind of hard for me to be his girl seeing as I was male.I…

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How it all began

A little raunchy about my first time with a guy and becoming a crossdresser, names changed due to privacy…

I had known Simon for as long as I remembered, he was same age as my brother 3 years older than me, that's how I met him he was my brothers friend first but as they got older they went different ways but I still used see Simon at school and around th…

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A Twist of Lemon Pt2

Part 1 was a dream, Pt 2 is me wondering what happened next…

She noticed that the call she made had distracted me and pushed my head back down to her moist mound and opened her legs wider, "more tongue" she said coolly. I continued to lap at her juicy clit and probed her hole ( I knew she liked that )."So" she…

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When David contacted me again - Part 3

Everything has changed…

Continued from ‘When David contacted me again - Part 2’I awoke later and instantly remembered what the caring guy who was lying next to me had said. I felt a warm glow inside as I thought about future encounters with him. This was immediately crushed…

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When David contacted me again - Part 2

Used all night by David’s friend…

Continued from ‘When David contacted me again - Part 1’I ended the first part after being spitroasted by David’s friend Al and his unexpected guest, Colin. I’d gone to freshen up and then go and slip on another outfit.I came back to Al and Colin in a…

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After Dee Steven and Gary

Steven fulfils his fantasy…

Part 2 Lying on the bed, Steven carefully put the pegs on my nipples, they had quite strong springs as they crushed my nipples almost flat , some pain as they did so but manageable, suddenly Stevens caring side  disappeared as he now pulled…

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When David contacted me again - Part 1

Not what I expected…

I’ve previously written about David, who was one of the guys I met at the toilet block.In my last report, I described another experience with the other guy, Mark, who I was really falling for. He was caring, respectful and keen to see me and experien…

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Being with Mark again

Another encounter with my gentle lover…

Following on from the encounter with David, I was keen to meet my more sensual lover, Mark. My last encounter with Mark took place during a lovely afternoon in a hotel room. Mark had enjoyed free rein with me, getting me to dress the way he wanted an…

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Meeting for the first time in 10 years

Meeting a guy and unleashing my inner slut…

So after 10 years of being good, the urge to dress got too much. I finally bought myself some fake boons, some sexy lingerie, make up, wig...I was set.Last night I decided to go for it, showered, shaved everywhere and got dressed, the started lookin…

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A twist of Lemon

An early morning dream, pieced together.…

So this morning I woke from a dream horny and hard but at the same time confused and feeling a bit vulnerable. I shall attempt to piece it together.Rewind 20 years to when things were going south between me and my ex. She was working as a barmaid at …

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Meeting David again

David likes to make me his gurl…

If you’ve read previous instalments, you’d have seen that I met David at a toilet block and then followed up by messaging him to arrange a further meet. This is the story from the third time I met him.A few days after our session in the car park of a…

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My first time Pt7 The next level

Ann decides to test me to see just how far she could go…

I'd always told myself that the last gang bang would be my last now that I'd been claimed by Ann, my future wife who was also now my mistress so I was in heaven. By now things had quietened down and for a while Ann had me all to herself, our sex life…

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Impromptu Fun

There’s a lot of fun on offer, if you look in the right places…

I used to think it was really difficult to stumble on some fun when you're seeking action. I've read the stories about fun in toilets, but felt I must have only visited straight guy loos, as there was never any action.I was ready to give up on it whe…

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Open To Offers

How I would like a outdoor meeting to go…

Hi all, I hope that this out-line of a story/fantasy is not out of order here.Well over the last couple of weeks, I have been reading all the 'Crossdressing' stories (Yes all 70 pages. But I was mostly interested in the Outdoor/Wooded area and Adult …

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My Sister’s Ex Pt1 - My Favourite Blue Dress

My sister’s bully ex notices me dressed and I can't resist…

My name is Sophia and I’m a twenty-one-year-old sissy girl who loves to dress femme all the time. Over the past few years, I have got more and more daring with my feminine side, going out in public dressed. It was on one of those adventures I discove…

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Always the bridesmaid

A change to dress up at a wedding goes slightly wrong…

My wife, Hannah, and I drove from the North West to Reading for a wedding. My wife was going to be one of three bridesmaids for her best friend Claire. The wedding was on Saturday but we got down to the Motel, a  coach house on London Road, mid-…

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Adventures of a married man 2

Gay Bi sexual adventures…

I am writing my adventures in no chronological order, just memories coming back to me, I have written before about my wife having her fling with a young colleague from her work which still turns us on when fucking, I am still reluctant to tell her my…

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Crossdressing Journey: Tentative Steps - The Next Day

Finally, the follow up to my encounter with a new friend in a hotel…

The next morning I woke with a pleasing memory of the previous evening. The thoughts of being played with whilst dressed as a girl were amazing and now a new day had dawned with the promise of more adventure.I got up and showered and douched in case …

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My partner introduces me to cuckolding

An evening with Ann's friends opens my eyes to the pleasure of cuckolding…

I always told myself that the last gang bang would be my last now that I'd been claimed by Ann my future wife who also was my mistress so I was in heaven. By now things had quietened down and for a while Ann had me all to herself, our sex life was am…

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8 into 1 dies go

Steven invites me to meet his friends with a surprising outcome…

Part 6 After another explosive meeting with Paul,the man who had expertly made me cum hard at a previous party,  I was lost within myself, reliving that moment in my head where he made me shoot my  spunk literally everywhere , I tried …

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Crossdressing Journey - Tentative Steps

The first taste of fun, whilst wearing nylons…

After indulging my fantasies of nylons, lingerie and heels on my own for some time, I decided to be brave and see if I could be ‘used’ whilst dressed in my girly clothes. I’m not a convincing CD, so I wasn’t going to hit the streets looking for atten…

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Totally dominated

My friend invited his dominant friend round and it changed my life forever.…

Part 3After that momentous and memorable night, my friend and I met up often for him to continue to use me as his submissive sissy for his and now my pleasure.My girlfriend had now moved away to university so I had ample time to be Christine which my…

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My Journey in Crossdressing

This is not a raunchy story. I just wanted to share my journey to crossdressing and, once shared, it may encourage me to share some other stories relating to my obsession with nylons.I’ve always been into nylons and high heeled shoes or knee high boo…

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On holiday down south

Crossdresser taken…

I was on my own having a day pottering around a seaside resort and noticed a toilet in the car park, the thought of having an accidental meet crossed my mind as I was wearing a green and white gingham bra and matching panties with black hold-ups unde…

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