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How I became a sissy femme cuckold Part 1

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By *enny_J_Jones OP   TV/TS
2 days ago

sheffield

This is a fantasy but some small parts are true. wish it all was. Tell me if you want more.

It all started when my wife bought a cheap IPL laser off ebay. She said she was fed up with shaving her legs and decided to get a laser hair remover off ebay for about £60. She said it would save her all the fuss and money she spent on veet or waxing. After a few weeks of use, her legs were permanently hair free and I commented how smooth and feminine they felt, “wouldn’t it be nice if you did elsewhere too?’ This was bold from me as my wife was so conventional sexually then and, apart from a bit of lady gardening, she never went for anything like a Hollywood or a Brazilian. “Well, I’d think about it if you did a bit too, say your hairy back and chest” she replied. As I got older, I had acquired fairly thick chest hair and even some on my back. To be honest, I didn’t like it and when I had the chance I shaved it. I told her it was because I felt it made me look younger, but really it was to make me look and feel more femme when I dressed up as Jenny. But she didn’t know that. But this offer provided me with an ideal opportunity. “You’re on I said” and for the next few months we did each other. When I finished with her 80% of my wife’s pussy hair was gone and she trimmed the stuff close to sensitive skin. She was happy to do it as I made sure she knew how much I enjoyed tonguing her newly bared sex. Meanwhile, she had a much bigger job, but eventually all my chest and back hair was gone and she conceded it made me look younger, especially as `I had lost some weight. She didn’t know then, but this was largely because as my body became more feminine I was enjoying dressing up even more and Jenny looked better as a slimmer girl. She did say, “it would be nice if you lost the moobs a bit more though.” But then she didn’t know how much time I spent when I “working from home” with my nipples being stretched by pumps and clamps.

One night, as we were dressing up for a night out, I asked her to wear stockings and suspenders like she used to. With a cheeky grin I told her, “after all, your legs look so sexy now they are bare right up to your cunt.” She blushed, but with a bit more persuasion, she was convinced to wear her red rose-buds decorated black lace suspenders and seamed stockings. “Mm, I haven’t worn these in years, they do make me feel more sexy”, she conceded as she slipped on a black cocktail dress. “Don’t wear any panties, please” I pleaded. She smiled, “do you think I am a slut?” But I noticed she didn’t dig out anything from a smalls draw. To be honest, I was envious, I’d have love to wear the same, but as my wife is so much smaller than me, I couldn’t really enjoy a sneaky fitting even if I tried.

The night out included a visit to a posh cinema where you could drink wine during the screening. As it was quiet and dark, I made sure I “casually” rested my hand on her stocking clad knee. I couldn’t believe it: my normally quite prudish wife didn’t lift my hand off, but discreetly widened her stance, so my palm could slip up her thigh to her stocking tops. Maybe the wine had made her more relaxed? She leaned over and whispered; “I am enjoying this.” Did she mean the movie, or my attention? I set out to find out by letting my hand ride up to her now smooth sex. It was warm and damp. After that I didn’t take in the movie as I wanted to get home as soon as we could and judging by my wife’s squirming bum so did she.

When we got home, my closed the door and immediately knelt in front of me undid my belt and pulled my hardening cock out. As she stroked it she said to me; “you know I would suck it a lot more if I didn’t get hairs in my mouth.” I couldn’t believe it. I had dreamt of funding reasons to shave Jenny’s pussy, but my wife Anna was too much a prude to take in such a suggestion and I knew she would wonder where and why I got the idea, but now she herself was hinting that I needed to be cleaned up. It decided to be bold. “Well you can do something about it…shave me there.” With a gleam in her eye she took up the challenge. Within minutes I was foamed up and she did a beautiful job with a fresh razer massaging bio-oil into the final smooth skin. Looking at her on her knees stroking my rapidly hardening cock I felt emboldened, “Suck it now Anna like the slut you are.” I couldn’t believe it without hestitation she licked from the shaft to the tip while stoking my balls “Oh they feel so soft and smooth,” she said “I need to suck them too.” I couldn’t believe my luck, but things took an even more surprising turn next.“ Given you made me hair free permanently, you need to be done” Anna told me. I pretend ed to put up some fuss, but quickly gave in. And before I knew it my wife was making my pubes hair free forever and I was suddenly getting more BJs.

What Anna didn’t know was how much I was enjoying wearing lingerie over my bare skin. I’d always loved a basque and stockings, but now – when I had a chance- I wore make up and some newly acquired heels. I thought I looked very sexy as a girl now. I think Anna noticed my obsession with lingerie though. Because one evening, out of the blue while she was trying on a new matching set of Rosie underwear I’d bought her in M&S, she said, “sometimes I think you like this stuff more than me”. I lowered my eyes because she was half right and mumbled something about finding lingerie sexy. I was astonished by Annas’s response, “You know what? I am going to get some for you for your birthday.” I couldn’t help blushing and although I protested feebly she could see I was excited.

[To be continued?]

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By *ircumcised PleaseMan
2 days ago

North Lancashire

Yes please.

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By *attooedJonMan
2 days ago

Gateshead

Very good start.

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By *erry55Man
2 days ago

Portlaoise

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By *lia Janine Porn FanMan
2 days ago

Birmingham

Oh yes….keep going

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By *enny_J_Jones OP   TV/TS
2 days ago

sheffield

Nothing more was said until my birthday the next week. We had arranged to go to a posh restaurant in the evening. After work, Anna popped upstairs to get dressed and made up. As I waited downstairs, I mused that the promise made last week seemed to be forgotten, but then my phone pinged. It was from Anna. “There is a special present for you in the spare room. You need to put it on before we go out.” My pulse was racing as I tried to stop myself running upstairs. When I walked into the bedroom we used as our home office, my eyes popped out of my head. Laid out on the bed was a black lacy basque, like Anna’s suspenders it was decorated with red rose on the straps. There were also expensive looking black, XL seamed fully fashioned stockings laid next to it. Next to them was a note. “Put these on under your clothes before we go out.” I couldn’t believe my luck. Quickly I stripped and put them on. As I but on my chinos and shirt and jacket I heard Anna call from downstairs; “Hurry up or we’ll be late for our date” Where would this go next?

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By *aveh1234Man
2 days ago

Christchurch

Lovely

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By *tillSissyMan
2 days ago

Bulwell

Looking forward to see where this goes!

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By *akedTradesmanMan
2 days ago

watford

Please continue

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By *issyswichTV/TS
2 days ago

Peterborough hotel PE1 area

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By *enbiCheshireMan
2 days ago

North west

Very nice

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By *vfanMan
2 days ago

swansea

More please

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By *ick1965Man
2 days ago

Bangor

Loving this. More please.

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By *enny_J_Jones OP   TV/TS
2 days ago

sheffield

At the restaurant we were shown to a discreet table for two in the corner. After ordering, we sat in silence like many long term couples do, but then Anna leaned forward and whispered in my ear; “I want to check you followed my instructions.” And with that, under the table cloth, she unzipped my flies and pushed her elegant nail polished hand onto my thighs, stroking my stockings and taught suspenders. But as she walked her hand up to my crotch her eyes widened in surprise then narrowed into suspicion; “Are you wearing little girly panties too?” she whispered. I mutely nodded.

When I saw what was laid on the bed earlier, I just couldn’t resist putting on something from Jenny’s stash of underwear. My classiest black lace front panelled pants with a sheer see-through back panel that I thought covered my plump girly arse beautifully.

Anna’s nails dug into my thighs. Gently at first but more sharply as she looked me in the eyes smiled and almost coldly said; “Did I give you permission to wear panties, dear? And yes, I do know about your little stash. I will talk about this with you later.” That sounded ominous. Although I was worried that my secret seemed to be out, I couldn’t help feeling my panties getting tighter as my cock swelled, especially as Anna continued to stroke it through the lace. “Mmm, that does feel nice doesn’t it?” she giggled “Get your coat slut we are going home.”

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By *2marcMan
2 days ago

tunstall

Please continue x

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By *erry55Man
2 days ago

Portlaoise

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By *akedTradesmanMan
2 days ago

watford

Please continue

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By *avidIanMan
1 day ago

Bolton

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By *uriousScott22Man
1 day ago

Scotland

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By *oberta99TV/TS
1 day ago

Oswestry

Eagerly awaiting the next episode

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By *ornishfetMan
1 day ago

St Ives

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By *TRAPON BOSSTV/TS
1 day ago

Waterford Ireland

MORE please

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By *ersatile-1TV/TS
1 day ago

stirlingshire

Lucky gurl

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By *elen300TV/TS
1 day ago

Telford UK

Honestly looking forward to next part

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By *preadmeMan
1 day ago

Aberdeen

Would love to be smooth

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By *orkDefenderMan
1 day ago

Wakefield

Wonderful

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By *enny_J_Jones OP   TV/TS
1 day ago

sheffield

Anna didn’t say anything more as we took the Uber home, but as soon as we stepped through the door of the house, she closed the curtains in our front room, turned to me and said one word: “Strip.” I took off my jacket, shirt, and shoes. I undid my belt and let my trousers fall. For the first time I stood before my wife in lingerie. Yes, I felt a little humiliated as she walked around and inspected me, but there was no denying my excitement - my hardening cock gave it away. Anna ran her hands over my nylon cover arse, stroking my cheeks. “I saw these in the box at the back of your wardrobe. I have to say your butt looks good in them” This is exactly what I wanted to hear, but just when I thought everything was going swimmingly Anna said something that changed our relationship for ever. “I always knew you like this really, but I ignored it because you were such a nice man, but you must admit our sex-life lacks something.” This revelation was delivered as she cupped my pantied balls in her hands and gently squeezed. “I am not going to leave you darling, but we really need to do something because I am bored. And judging by the content of that box you are too.” Oh God, she had seen the dildoes and vibrator too. Again, I blushed; “Anna I was just experimenting…” “Well, I want to experiment too. And while I do concede you actually look quite pretty like this, I want a MAN’s cock.” With that she squeezed on my balls hard. “So, what are we going to do darling?” Now, I was worried, as despite everything I desperately wanted her to stay with me, so without thinking that she still had her hand around my cock and balls, I blurted; “I think you should have a lover.” What was I thinking? I was just desperate to keep her. Anna suddenly seemed lost in thought and amazingly she didn’t seem horrified by the suggestion. “Mmm, how would this work?” she asked. “How do I get to choose someone? I mean I don’t want people close to me, neighbours, and at work knowing about our…choices.” This was so Anna; she was so prim and proper. In fact, I was astonished she was mulling over my suggestion. Of course, I was thinking of FS straight away, but fended ignorance. “I am sure there must be a website we we could find someone discreetly,” I moaned as she slid her hand under my panties gusset and began to run her nails over my hairless balls. “I’m interested but first lick my cunt babe.” She t=grabbed my long hair at the back of my head and pulled me down under her skirt. She was knickerless so I got on all fours enjoying the pull of the transparent nylon on my arse as I put my tongue to work straight away. Within a minute we were both groaning.

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By *usan 749ukTV/TS
1 day ago

Bangor

Excellent

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By *issyswichTV/TS
1 day ago

Peterborough hotel PE1 area

Brilliant

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By *akedTradesmanMan
1 day ago

watford

Great story

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By *ers_Viking_FukMan
1 day ago

Gorleston

This is so fucking hot

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By *enny_J_Jones OP   TV/TS
1 day ago

sheffield

So that was it, I introduced Anna to FS. Once she was assured that she could browse discreetly, she told me she wanted her own log-in as she wanted to do the research herself and, although I could have a say, it was her who was was going to make the choice of men in the end. I noticed, with a thrill, that she said MEN.

Over the next few weeks, she became increasingly interested in the website. One day I found her browsing sat down on our settee with a cup of tea in her hand. She smiled; “Oh, it’s like being a girl in a sweet shop, which gobstopper will I choose?”

She had always insisted that she would only look at the few entries that had headshots, even if it meant becoming friends. It was then that I found out that she had uploaded some classy B&W, fairly close-up, images of her wearing her Gossard suspenders and black stockings, or a basque and red lace topped black hold ups – those last images were from behind with her hand of her hip showing off her perfect white arse, which had filled out since her athletic youth and now looked even more tempting. She had made me take the photos using her phone and although they didn’t show her face or anything that may identify her, I really didn’t think she would post them, yet there they were. Then more seriously, she said; “I think I found a candidate for my first adventure.” I looked – a handsome older, brown-eyed man going grey at the temples. There was one close-up pic and one of him in suit looking like he was going to some sort of formal meal, but there was also a naked photo. My eyes widened, even flaccid his dick was at least 6”. Truth be told, it fascinated me, I wondered what Anna would experience and feel if, WHEN she took that cock in her hand and felt it harden and grow. Would she be fucked by him and realize what she was missing? But truth be told my main thought was I wanted it too.

I gulped; “have you contacted him yet? “oh, you know, me and Pete have had a bit of to-and-fro, but nothing has been organized yet”..PETE... I immediately responded; “Invite him round for a get-to-know you drink.” She smiled “Thank you I just wanted to check. You know what I think I will”

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By *onytechMan
1 day ago

leicester

Love it.

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By *erry55Man
1 day ago

Portlaoise

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By *ully fashioned slutMan
1 day ago

norwich

Loving this

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By *avidIanMan
1 day ago

Bolton

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By *achealtvsubtoyTV/TS
1 day ago

hoddesdon

Very,very good,,,can I request just a bit more detail on the clothing, lingerie, hosiery, shoes,,,,please xxx

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By *uriousScott22Man
1 day ago

Scotland

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By *hris106699Man
1 day ago

North hykeham

Excellent, it's got me horny

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By *elanie_welshTV/TS
24 hours ago

Newport

Great story so far! Exactly the position I’d like to be in!

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By *ature4safefunMan
16 hours ago

preston

Excellent story. More please

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By *amantha_kelTV/TS
15 hours ago

magherafelt

Hope there is more soon

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By *ric4000Man
13 hours ago

Leigh

Gf cucking me with her chubby boss and makes me dress

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By *avenMan
13 hours ago

Street

Thanks for posting.Great story.

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By *ornishfetMan
6 hours ago

St Ives

This is hotting up nicely

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By *j1xMan
6 hours ago

anywhere

Amazing

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By *i14Man
6 hours ago

Rayleigh

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By *oundleighaTV/TS
6 hours ago

Middlesbrough

Fantastic x

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By *egselevenMan
5 hours ago

burnley

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By *ibby BrownTV/TS
5 hours ago

cannock

I hope there's more soon 💋

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