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How I became a sissy femme cuckold Part 1

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By *enny_J_Jones OP   TV/TS
19 weeks 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
19 weeks ago

North Lancashire

Yes please.

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By *attooedJonMan
19 weeks ago

Gateshead

Very good start.

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By *erry55Man
19 weeks ago

Portlaoise

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By *lia Janine Porn FanMan
19 weeks ago

Birmingham

Oh yes….keep going

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By *enny_J_Jones OP   TV/TS
19 weeks 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
19 weeks ago

Christchurch

Lovely

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By *tillSissyMan
19 weeks ago

Bulwell

Looking forward to see where this goes!

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By *akedTradesmanMan
19 weeks ago

watford

Please continue

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By *issyswichTV/TS
19 weeks ago

Gateshead

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By *enbiCheshireMan
19 weeks ago

North west

Very nice

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By *vfanMan
19 weeks ago

swansea

More please

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By *ick1965Man
19 weeks ago

Bangor

Loving this. More please.

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By *enny_J_Jones OP   TV/TS
19 weeks 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
19 weeks ago

tunstall

Please continue x

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By *erry55Man
19 weeks ago

Portlaoise

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By *akedTradesmanMan
19 weeks ago

watford

Please continue

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By *avidIanMan
19 weeks ago

Bolton

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By *uriousScott22Man
19 weeks ago

Scotland

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By *oberta99TV/TS
19 weeks ago

Carmarthen

Eagerly awaiting the next episode

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By *ornishfetMan
19 weeks ago

St Ives

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By *TRAPON BOSSTV/TS
19 weeks ago

Waterford Ireland

MORE please

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By *ersatile-1TV/TS
19 weeks ago

stirlingshire

Lucky gurl

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By *elen300TV/TS
19 weeks ago

Telford UK

Honestly looking forward to next part

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By *preadmeMan
19 weeks ago

Aberdeen

Would love to be smooth

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By *orkDefenderMan
19 weeks ago

Wakefield

Wonderful

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By *enny_J_Jones OP   TV/TS
19 weeks 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
19 weeks ago

Bangor

Excellent

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By *issyswichTV/TS
19 weeks ago

Gateshead

Brilliant

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By *akedTradesmanMan
19 weeks ago

watford

Great story

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By *ers_Viking_FukMan
19 weeks ago

Gorleston

This is so fucking hot

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By *enny_J_Jones OP   TV/TS
19 weeks 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
19 weeks ago

leicester

Love it.

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By *erry55Man
19 weeks ago

Portlaoise

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By *ully fashioned slutMan
19 weeks ago

norwich

Loving this

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By *avidIanMan
19 weeks ago

Bolton

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By *achealtvsubtoyTV/TS
19 weeks 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
19 weeks ago

Scotland

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By *hris106699Man
19 weeks ago

North hykeham

Excellent, it's got me horny

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By *elanie_welshTV/TS
19 weeks ago

Newport

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

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By *ature4safefunMan
19 weeks ago

preston

Excellent story. More please

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By *amantha_kelTV/TS
19 weeks ago

magherafelt

Hope there is more soon

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By *ric4000Man
19 weeks ago

Leigh

Gf cucking me with her chubby boss and makes me dress

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By *avenMan
19 weeks ago

Street

Thanks for posting.Great story.

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By *ornishfetMan
19 weeks ago

St Ives

This is hotting up nicely

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By *j1xMan
19 weeks ago

anywhere

Amazing

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By *i14Man
19 weeks ago

Rayleigh

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By *oundleighaTV/TS
19 weeks ago

Middlesbrough

Fantastic x

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By *egselevenMan
19 weeks ago

burnley

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By *ibby BrownTV/TS
19 weeks ago

cannock

I hope there's more soon 💋

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By *obt71Man
18 weeks ago

bradford

We need more

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By (user no longer on site)
18 weeks ago

mmmm this is really hot and sexy x

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By *oreiMan
18 weeks ago

Chester Le Street

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By *enny_J_Jones OP   TV/TS
18 weeks ago

sheffield

A week later a black fancy German car pulled up outside our house and a Peter knocked on our door. Trim, wiry, with a full head of hair and an easy grin, clutch a very decent bottle of red. He was dressed in a crisp white shirt, Hugo Boss jeans, and very polished brogues. My first thought was he was ex-military, a notion cemented when he told us he ran a private security firm.

He was curt and polite with me seemingly showing interest in my work. But, once the wine was poured, he was soon – literally - charming the pants off Anna as he flirted with her saying she looked 10-15 years younger than her profile age and complimenting her on her, ”striking looks and figure.” Slowly their talk moved to the bedroom as they outlined the rules they would follow. Anna insisted I should know when they met and that they should keep this arrangement separate from real life. Peter immediately agreed, but told her he wanted a regular timetabled meet as he had “needs both professionally and…romantically” as he put it. Although this all took place as if I wasn’t in the room, Peter was polite enough to check whether I was okay with this. Oh yes, I was, I assured him. Although I felt a knot in my stomach, I was already dreaming of somehow getting my hands on that hard body and cock, preferably with Anna’s permission.

Suddenly, Peter brought the conversation to a close: “When does this arrangement start then?” Anna turned to me, “Would you be okay if Pete and I go upstairs now? I know he has some time now…” I looked them both in the eye and, because my voice was in danger of catching (anxiety? desire? I wan’t sure), I just nodded. Pete took Anna’s hand, their first contact, and told her to lead the way to the bedroom. “You okay here?” Anna half whispered. Again, I nodded and immediately planned to wait until they were in our bedroom so I could sneak into the spare room next door and listen in the forthcoming events.

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By *erriTV/TS
18 weeks ago

Hastings St Leonards

Just started to read your story and I think it's really interesting

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By *avidIanMan
18 weeks ago

Bolton

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By *ilkyphoebeTV/TS
18 weeks ago

Biggleswade

Mmm perfect

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By *orkiebar51Man
18 weeks ago

Keighley

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By *iss WednesdayTV/TS
18 weeks ago

Stortford

I love your fantasy x

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By *erry55Man
18 weeks ago

Portlaoise

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By *hris106699Man
18 weeks ago

North hykeham

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By *enny_J_Jones OP   TV/TS
18 weeks ago

sheffield

Five minutes later, I had my ear pushed against the dividing wall. It was quite thin as we had split a very large original bedroom to create the office/spare room in which I now stood with my trousers dropped to my ankles to reveal my black denier 10 sheer stockings held up by a matching black lace, Janet Reger deep suspender belt which attached through a front silver metal clasp. The knot in my stomach was still there, but when I looked down, I could see my lingerie framed cocklet was dribbling precum. I listened carefully and after some mumbling I couldn’t catch I heard Anna say, “Oh God, Pete you are sooo big. After what I’m used to I am going to be very tight.” Well, that was true we had hardly fucked in the last few years. I assumed it was because Anna was postmenopausal and off sex. The next few minutes changed by view.

Peter mumbled something I couldn’t hear and then I heard Anna let out a low moan followed by a sigh and a long drawn out “Oh yes”. I could hear the bedhead hitting the wall in a slow steady thump as gradually Anna became increasingly vocal. At first it was more sighs and whispers I couldn’t hear. Then louder “Give it to me I want it hard” was followed by a load groan of pleasure and “Fuck me harder” then I heard Peter saying, “Say you desperately want my cock” and immediately Anna answered, “I want your hard cock in me, please Pete, please”. By now I was hard too and like the sissy I was becoming I didn’t stroke my cock but rubbed my nipple and dreamed I was being fucked by Peter. I found a dildo from my draw pushed in my arse. My wife was being fucked by a stranger hours after she had met him and I felt wonderful as I bounced on the dildo in the same rhythm as Anna’s fucking until I came hands-free the jism spilling over my stockings. Then I heard Anna voice which was now low and guttural begging, “Yes give it me. Please, please give it to me, I am coming” I scooped up my cum, licked the lovely sticky juice of my hands, swallowed it, quickly pulled up my trousers and snuck back downstairs. Ten minutes later the two now lovers came downstairs dressed but slightly dishevelled to a find cup of tea waiting for both of them. Anna was only a little bit shy when eventually spoke - It was clear from the glow on her skin she had enjoyed a good fucking that had released a lot of tension. She asked me; “was I loud babe?”. I decided to be honest “Yes, you were but it was incredibly exciting.” Peter immediately butted in, “So you liked hearing your wife being properly fucked?” Before I could answer, Anna said; “Oh Pete don’t tease the poor darling.” But Peter continued to look at me with amused, (knowing?), eyes. Abruptly he said, “I have to go to a business commitment now.” Then turning to Anna with a smile he said “Keep in touch now you have my number. Maybe you can send some thoughts by text? Is it okay to visit next week?” In unison, we both said “Oh Yes!” And with that he was gone.

As soon as Peter had left, before anything was said, I immediately began kissing Anna. I think she was going to say “not now.” But maybe a little guilt restrained her from stopping me, as I peeled off her white silk blouse and unzipped her black leather mini. Silently she stepped out of the skirt as I gently pushed her onto our huge leather couch, knelt in front of her hot wet pussy and began to greedily lap up another man’s spunk mixed with her juices. Within a minute or two she grabbed my hair and pushed her cunt into my willing face as I inhaled the heady scent of cunt juice and sperm, until I came spontaneously again over her stockings. When she saw the cum on her thighs, Anna sighed and in her low husky voice said, “Oh dear darling what have you done? Lick it up.” This may have been the first time I tasted another man’s spunk, but it wouldn’t be the last.

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By *dinthewoods69TV/TS
18 weeks ago

travelling around GB

Fantastic sexy story x

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By *achealtvsubtoyTV/TS
18 weeks ago

hoddesdon

Owwww,,,BRAVO !

EXCELLENT

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By (user no longer on site)
18 weeks ago

Oh yesss, that was hot 🔥

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By *avidIanMan
18 weeks ago

Bolton

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By *erry55Man
18 weeks ago

Portlaoise

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By *enny_J_Jones OP   TV/TS
18 weeks ago

sheffield

Thanks for the feedback everyone. I will add more soon.

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By *ornishfetMan
18 weeks ago

St Ives

Very hot indeed

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By *aney RopesTV/TS
18 weeks ago

Gourock

Brilliant story, carry on please

Jane x

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By *uriousScott22Man
18 weeks ago

Scotland

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By *ers_Viking_FukMan
18 weeks ago

Gorleston

Please continue

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By *issyswichTV/TS
18 weeks ago

Gateshead

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By *harliesfunMan
18 weeks ago

Brighton

Great story so far

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By *ully fashioned slutMan
18 weeks ago

norwich

Wow

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By *he WormMan
18 weeks ago

all over

Love this!!!!!

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By *enny_J_Jones OP   TV/TS
18 weeks ago

sheffield

more soon

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By *athyTV/TS
18 weeks ago

Nottingham

Beautiful and so lucky xx

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By *enny_J_Jones OP   TV/TS
17 weeks ago

sheffield

After a few weeks my life settled into a new routine. My newly sexualised MILF wife was regularly getting fucked by her alpha-male lover and, as they relaxed into their relationship, they were happy to show their affection – and lust- for each other in front of me. Peter began to French kiss Anna on his arrival and departure, squeezing her arse while he did. In return, Anna began wearing shorter and tighter skirts mostly in black and red and often grabbed Peter’s crotch urgently while they kissed. But still, they fucked in our marital bedroom with the door shut.

What they didn’t yet realize was that I was nearly always in the next room, dressed in lingerie, fucking myself as I listened to Anna’s increasingly vocal and confident demands. I could never imagine the old Anna even thinking about some of the things I heard her demanding and begging for from Peter. Clearly, she was enjoying sex much more with him than with me and that was making her more adventurous. One day, as I heard her moaning breathily; ”I love your tongue in my arse like that, I want it deeper,” I was lost in lust holding onto a chair as I used a suction-cupped dildo to fuck myself. I wanted so much to be in there watching and more. So, maybe it was my subconscious that made me slip and noisily knock over the chair against the dividing wall between the two bedrooms.

Within seconds Peter was opening the door to the room, butt naked and exclaimed; “What the fuck?” when he saw me still on all fours. I was wearing a black satin teddy with an elasticated waist and white lace trim and black stay-ups with lace tops that matched the trim of my teddy. The spaghetti straps of my teddy were off my shoulders exposing my pert nipples which – after so much playing with them – were too thick and long to be anything but feminine looking, especially as I had paited them with red lipstick. From his vantage point at the door, I knew Peter could see the dildo thrust between my rounded arse cheeks. There was nothing I could do but blush and stare at his beautiful cock shaft, especially when Peter started laughing; “well what do we have here, but a little sissy voyeur?” I try to mutter some sort of excuse but my mouth was completely dry. He grabbed me firmly my the wrist and pulled me up. As I got up, the lifelike, thick pink dildo fell to the floor. “Pick it up,” commanded Peter, “Anna needs to see you like this.” With that he pulled me into what used to be our marital bedroom, but was now I realised their domain, and my new role there was soon to be defined.

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By *iguy_wbroMan
17 weeks ago

Hungary

Hot

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By *ohnny 52TV/TS
17 weeks ago

Middlewich

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By *umslut7Man
17 weeks ago

dunfermline

Superb 😉

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By *avidIanMan
17 weeks ago

Bolton

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By *aney RopesTV/TS
17 weeks ago

Gourock

More please.

Jane x

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By *issyswichTV/TS
17 weeks ago

Gateshead

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By *azmin999jmMan
17 weeks ago

wakefield

Lovely

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By *enny_J_Jones OP   TV/TS
16 weeks ago

sheffield

I was led in, looking down to the floor with a blush blooming on my cheeks. When I looked up, I was astonished at the sight before me. Anna was grinning wickedly at me, dressed in a tight red wet-look PVC corset, tightly laced to emphasize her waist, and matching tight thigh high boots with unbelievably high spiked heels. just peeking over the tops on the boots I could see black stocking tops. Her red hair was piled on top of her head, so I immediately noticed her long sparkling earrings, her dark batwing eyeshadow and thickly applied crimson lipstick. She looked so fierce and fantastically sexy, but why was she dressed like that? I had never imagined she could dress up for sex like that. I would find out that there was a reason for this later

“Look what I found,” laughed Peter. Almost laughing Anna asked; “Poor darling, are you a little frustrated?’ I looked at Anna then at Peter’s taut body. He was lightly tanned, and although I noticed a military tattoo on his left muscled shoulder, I was mesmerized by his manhood. Even with only a semi, it was at least seven inches, with a long smooth relatively slim shaft, but a massive purple head. I desperately wanted to have it in my mouth and feel it pulse and swell as I sucked on it and cupped Peter’s low hanging huge hairless balls. Again, he laughed; “look at her Anna, we both know what this slut is thinking. I told you were married to a sissy. Do you believe me now?”

Despite my deepening blush and the humiliation of being paraded in front of my wife and lover while he called me “her”, I could feel my cock hardening because there was no denying I felt hugely excited. Anna noticed and was quite brutal; “Oh Pete, look at that dick - I haven’t seen him with a proper little hardon like that for ages.” Yet despite these comments, my now rock hard “little hardon” began to twitch. “How cute” said Anna as she ran her painted nails over my balls and scratched along the underside of my shaft. “Finish her off Anna,’ said Peter and then looking me straight in the eyes he added, “Make it enjoyable for her as I think we all know this is the last time a girl like this gets her enjoyment that way.” Anna knelt down and, in front of Peter’s gaze, took my whole shaft into her hot wet mouth. The thought that it would be easy after servicing Pete the same way only minutes ago brought me to an instant climax. Anna swallowed, patted her lips with a tissue at the side of the bed and smiling asked; “What are we going to do with you now darling?” Peter was decisive; “Well if they dress like a girl, from now on when I visit, I am treating her like a girl. What do you think she should be called?” Without missing a beat in a low whisper and my eyes lowered I said, “Call me Jenny, Sir.”

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By *issyswichTV/TS
16 weeks ago

Gateshead

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By *ohnny 52TV/TS
16 weeks ago

Middlewich

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By *avidIanMan
16 weeks ago

Bolton

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By *uriousScott22Man
16 weeks ago

Scotland

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By (user no longer on site)
16 weeks ago

Definitely following this

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By *azmin999jmMan
16 weeks ago

wakefield

This is excellent xxx

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By *esley 60TV/TS
16 weeks ago

PERTH

Loving this

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By *ewwomen259Man
16 weeks ago

kegworth

Love it.

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By *enny_J_Jones OP   TV/TS
16 weeks ago

sheffield

Both Peter and Anna agreed that the name Jenny suited me and that was what they called me from then on. Peter also told me that that from on I was to address him as Master Peter or Sir and Anna would be Mistress Anna or Miss. Between them, they also agreed that Mistress would teach me how to wear make-up and chose what I would wear for Master’s visits. When he found out that I was working from home on my own next day, Master Peter also told me he would send me a little gift that I would be wearing from now on. And, sure enough, early in the afternoon a courier knocked on our door with a “package for Jenny - no second name?” I nodded and not without a slight blush, signed for it as Jenny. As soon as the door was closed, I ripped open the package to find a little pink nub cock cage. Within seconds my phone pinged with a message. It was Master Peter; Mistress must have given him my number. “I have notification that my package has been delivered. From now on you wear my gift all the time. I hope I am clear here; you wear it ALL the time.” “Yes Sir” I said to myself and there and then I stripped down and put it on. It was a squeeze to get the ring over my balls and dick, but it was a nice snug fit. When I locked in the pink cage, I couldn’t help admiring myself in the full-sized mirror in Master and Mistress’s bedroom, but then my phone pinged again. “Leave the key on our bedside table. I have told Anna to pick it up when she comes back from her office.” So, after following the instructions I went back to working on my laptop, occasionally stopping to enjoy the feeling of the cage tugging on my balls as I squirmed in my chair.

When Mistress Anna came back, she immediately asked if I had followed Master’s orders. I nodded and told her the key was in their bedroom. She went upstairs immediately and 5 minutes later I heard a call; “Jenny come here now, darling.” When I came into her room, I noticed the key had disappeared. Mistress Anna was sitting in front of her make-up mirror with make-up laid out in front of it and an empty chair next to her. “Pete is coming to visit tomorrow to give me a special treat. So, It’s time for you first lesson, sweetie,” she said patting the seat next to her. And with Mistress’s help, I learnt how to put on lipstick and lip-liner, eyeliner, eye-shadow, long feathery eyelashes and even stick-on nails. When we had finished, we were both gazed into the mirror admiring the transformation we had made. “My gosh you do look cute” said Mistress Anna, “Pete is going to just love playing with you.”

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By *ohnny 52TV/TS
16 weeks ago

Middlewich

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By *avidIanMan
16 weeks ago

Bolton

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By *acyboyTV/TS
16 weeks ago

Southampton

Fantastic story telling

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By *ndrews642Man
16 weeks ago

exeter

Oh yes , so hot and would love to be treated like this

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By *aidclaireTV/TS
16 weeks ago

bideford

Love this story. X

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By *ndstorm45Man
16 weeks ago

Wakefield

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By *ers_Viking_FukMan
16 weeks ago

Gorleston

So fucking hot

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By *enny_J_Jones OP   TV/TS
15 weeks ago

sheffield

After wiping off my make-up, we went off to bed, but I couldn’t sleep. Two things kept running through my mind. I was mystified what Mistress’s treat from Sir would be, but I was also excited that I would be dressed as Jenny and, maybe, be let into their room and get a peek of Master servicing Mistress Anna; would she be dressed as sexily as the last time?

Next day, after a unproductive day at the office, where I just couldn’t concentrate, I rushed home to find that my Mistress was already upstairs. As their bedroom door was locked, I knocked on the door and waited. “Oh, is that Jenny? If you go into your room, you will find everything you need” “Thank you Miss,” I replied. I almost floated into my room with excitement, where I found the makeup that we had practiced with last night on the compact dressing table and some clothes selected for me laid out on the bed. I put on my eyelashes and eyeliner and after looking at the clothes, chose a deep pink lipstick, and little bit of matching blusher. Then I put on the white lace bralette, matching French knickers, and white lace topped polka dot hold-up stockings. The white satin blouse and navy-blue short pencil skirt fitted perfectly. Peeking out from under the bed I found some patent Mary-Jane shoes in the same colour as the skirt. At that moment, Mistress Anna walked in, “Oh good, you found the shoes. I chose them as they are not too high, only 2 or 3”. You’ll need some more practice before we get you in 6” spike heels.” She giggled, “Besides you are quite tall in those already, aren’t you?” While she was talking, I finished off my look by putting on false nails that matched my lipstick. After looking me over with a nod, Mistress said; “I think you need some jewellery too. Let me see what I can find you.” She came back in with a little crucifix on a fine gold chain and matching sleepers. When I we first met when we were younger, I used to wear earing in both ears, as was the trend at the time. “I am sure your ears won’t have closed up” Sure enough, without any effort she put the sleepers in and made me turn around so she could put on the chain. Finally, we decided to keep my hair down. I was proud of my hair, I had always worn it long – down to my shoulders- but usually in a ponytail and, although it had gone grey, it was still thick and in shiny. After some brushing, With the way I was dressed and made up, when I looked in the mirror I thought it looked like I had had a trendy ash blonde tint. “Well, you are certainly ready for our visitor,” said Mistress, “I just have one last thing to do.” She went to our bathroom with a clutch bag I hadn’t seen before. I thought it might be make up, but then heard the loo flush a couple of times before Mistress came out and said, “Now I am pure in mind and body I am ready for anything.” At that moment, the doorbell rang. I was a little confused, normally Master Peter let himself in, why was he waiting there? Mistress obviously caught my thoughts, “Oh you are a silly girl, Jenny. He wants you to let him in like a good maid.” “Sorry Mistress, I will do it right away. Miss” I went as quick as I could but I had to deal with the unfamiliar sensation of walking in heels and the fact that if my stride was too big my tight pencil skirt began to ride over my stocking tops revealing my little pink cock cage and are white bum. After Master had rung the bell twice more impatiently, I finally got to the door. Straightening my blouse and skirt I opened the door and Master Peter strode in. Without a word, he started looking me over with a wolfish look in his eye. He lifted his index finger and waved it round. I followed his unspoken command and slowly spun round so he could inspect me. “Very nice, very nice,” was his only comment, but it was accompanied by a squeeze of my bum. I couldn’t help but squirm a little under his firm grip. With that he said, “Right my little sissy, you have a treat in store. I am going to show you what a slut I am making of your wife.” He took my hand and led me upstairs.

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By *ohnny 52TV/TS
15 weeks ago

Middlewich

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By *iss WednesdayTV/TS
15 weeks ago

Stortford

Really good x

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By *erry55Man
15 weeks ago

Portlaoise

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By *ndstorm45Man
15 weeks ago

Wakefield

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By (user no longer on site)
15 weeks ago

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By *amieforfun1973TV/TS
15 weeks ago

bognor regis

Fantastic, can’t wait to hear the next installment and when Jenny gets 6 inch platform stilettos!

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By *aybee1TV/TS
15 weeks ago

Slough

This is sooooooo good

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By *ersatile-1TV/TS
14 weeks ago

stirlingshire

Thank you. So well written

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By *enny_J_Jones OP   TV/TS
14 weeks ago

sheffield

When we walked into the bedroom, we found Mistress Anna waiting for us, wearing her short fluffy white towelling dressing gown. Looking down I saw she was wearing new sheer black fitted stockings and spiked high-heel patent court shoes with a diamante decorated buckle. Her hair was scrapped back in a tight, high ponytail, her lips were painted deep ruby, her eyes were made up in a smudged panda eye style with her long lashes thickly mascaraed. She let her gown slip off her alabaster white shoulders to reveal she was wearing a very tightly laced, black brocade corset, her beautiful tits with their hard pink nipples sitting sexily on top of the corset. Without a word, she turned around, bent over from her waist, reached round and pulled the cheeks of her tight arse apart to reveal a red-jewelled butt-plug.

My feelings were all over the place: Mistress looked so fierce and sexy as hell, but at the same time I knew that someone else had lit this hunger within her and I was going to be forced to watch. I felt a weight in the pit of my stomach turning over, but at the same time my caged cocklet was positively dripping with precum. I was in a trance staring in wonder at the Goddess that used to be my timid wife. Master Peter broke the spell; “Tell Jenny what you want, Anna” “I want Peter to take my virginity. I want him to fuck my arse while you watch Jenny” My jaw dropped. “Oh, she isn’t going to just watch, she is going to help it happen” replied Master Peter.

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By *umslut7Man
14 weeks ago

dunfermline

Superb

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By *vsindyTV/TS
14 weeks ago

A place where sheep are warm, or Burnley.

Oh wow.....loving this.

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By *ane195854TV/TS
14 weeks ago

cornwall

This is very horny xx

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By *ane195854TV/TS
14 weeks ago

cornwall

Please I want more xx

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By *enny_J_Jones OP   TV/TS
14 weeks ago

sheffield

As he began to undress his jockey shorts were tented by his enormous cock, which flopped out as he pulled them down. Staring at his unreleased manhood I didn’t really hear him tell Mistress Anna to get on all fours at the end of the bed and for me to kneel behind her. I was fully woken from my trance when he sharply slapped my arse. even through my mini-skirt I felt the sting. “Are you paying attention to me or is your mind filled with my cock?” I was startled, how did he know? “Get on your knees, take out that plug and give it to me and then get on with worshipping your Mistress’s arse, you little cock-obsessed airhead”

I knelt down and with one hand I pulled Mistress’s cheek open and with the other I gave the plug a gentle tug and it popped out. It was clear to me that Mistress Anna had douched herself ready for her servicing. I handed Master the plug and immediately kissed my mistress pink rosebud, gently working my tongue into it more and more deeply. On the infrequent previous times I was allowed to, I always loved rimming her. So, I was soon lost in my task, happy to hear her let out a soft “Mmmm,” but then I realized Master was working my tight skirt over my hips to reveal my French knickers. He pulled them down roughly, slapped my bare arse again and then began - with surprising gentleness- to push the butt-plug into me, saying “Don’t stop Jenny, by the sound of it Anna is ready to be serviced” Promptly Mistress groaned and pleaded, “Oh yes, please Pete put your cock in my arse now…pleeese??” He replied, “Jenny, you are going to guide it in, aren’t you?” I got up, turned around and with eyes lowered nodded “Yes, sir” “Go on, hold it” said Master Peter, “and put it right between the cheeks of that nice wet tight arse” At last I was going to get my hands on that wonderful cock! I reached forward and grasped it, it felt like a soft velvet, covered warm steel-hard piston. I couldn’t resist stroking it and squeezing as I led him to Mistress. Silently, she raised her arse and lowered her face into the pillow as I gently positioned Master’s throbbing cock between her cheeks, pulling his foreskin back to reveal a head like a big plum. I was reluctant to let go, but I could see Mistress Anna pushing back to take it. Master took hold of her hips and with slow but ever deepening thrusts began to penetrate her. She let out an involuntary groan, “Oh, you are so big!” But at the same time, she reached back and pulled her cheeks apart to offer him easier entry. Standing by Master Peter side I was again slipping into a trance watching his cock progressively slip into my wife. She was too gone to realize that Master had leaned over and whispered in my ear; “Are you watching this Jenny, don’t you wish it was you who had my cock in your arse?” All I could do was again silently nod. Then louder he said, “I think you need to help your mistress enjoy this even more, don’t you?” He pulled his cock out despite Mistress Anna begging him to continue. “No you’ll enjoy this more” he replied, pushing me toward the bed. “Get on your back Jenny and let Anna crawl over you. You are going to lick her cunt while I fuck her.” Without another word being spoken I took up the position and Mistress Anna lowered her now dripping cunt to my eagerly waiting tongue. Greedily I set to work on her hard clit and wet hole, while above me I saw Master’s cock slip into her now stretched arse again. I reached round her thighs and pulled her cheeks apart as far as they would go. As his cock pistoned into her bumhole his low hand balls slapped into her cheeks. Then he pushed his shaft in all the way and paused. While Mistress Anna enjoy being impaled on his manhood, I raised my head and began to lap at his balls, feeling so happy when I heard him grown too. It made me feel I was doing my job well. But then he began to thrust into her again and I went back to serve my Mistress’s clit and cunt. Eventually, he began to pick up the pace of his thrusts and with that and my attention Mistress began to orgasm. With her voice catching she started begging for him to cum, almost babbling; “Fill my arse Pete I want your spunk in me. I want in me now, give it me” He groaned, and he arse clenched as he came. Anna almost shouted; “Oh you own me now Pete. You’ve marked me as your bitch. You OWN ME.” With that - face drenched in my Mistress’s cumjuice –I came hands-free in my cage.

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By *umslut7Man
14 weeks ago

dunfermline

Brilliant

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By *entleoneMan
14 weeks ago

near heathrow

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By *teve1867Man
14 weeks ago

wirral

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By *enny_J_Jones OP   TV/TS
14 weeks ago

sheffield

Sorry for all the typos and mistakes in the last entry. TBH, I was too excited to notice them while i was writing it!

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By *ohnny 52TV/TS
14 weeks ago

Middlewich

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By *earing stockingsMan
14 weeks ago

Liphook

Lovely story, looking forward to the next instalment

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By *harliesfunMan
14 weeks ago

Brighton

More

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By *achealtvsubtoyTV/TS
14 weeks ago

hoddesdon

Absolutely superb

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By *uriousScott22Man
14 weeks ago

Scotland

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By *ndrews642Man
14 weeks ago

exeter

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By *issybitchjoMan
14 weeks ago

moving around the river

Love it

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By *parks2020Man
14 weeks ago

Glasgow

Fantastic

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By *ature4safefunMan
14 weeks ago

preston

Typos? I was too engrossed to notice. Mmmmm

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By *enny_J_Jones OP   TV/TS
12 weeks ago

sheffield

We stayed that way for a while with Mistress Anna’s cunt pushed against my face. I inhaled the heady scent of her juices mixed with Master’s cock and cum. But Master wasn’t finished with me yet. He got up, rolled Mistress Anna off me and then demanded; “Clean your Mistress up, Jenny. I want to see you lick all my cum out of her arse, just so I know you are good maid.” “Mmm, that would be nice,” agreed Mistress Anna as she knelt at the foot of the bed, face pushed down onto the bed. With my lipstick smeared by cunt juice, I got behind on all fours and pushed my tongue into her relaxed arsehole licking away as daintily as I could, hoping to look like a cat who got the cream - which is what I truly felt like. I became more engrossed in the task when I thought that, if only a few months ago, anyone had told I would be in my own house licking another man’s spunk out of my lovely wife’s fucked arse while dressed as Jenny I wouldn’t have believed him (although I would have been hugely excited). Judging from her reaction - her bum wiggled in my face, Mistress was enjoying it too. As I began to push my face between her cheeks, so I could push my tongue as deep as possible, I felt Master Peter’s hand on my butt. “Good Girl, Jenny lap it all up,” he said, and he slapped my arse. I could feel the cheeks warming and I couldn’t help letting out a little gasp. “Oh, she likes this, Anna,” said Master. “Did you know your little slut liked a little bit of a spanking?” With that he slapped me harder and I let out an involuntary groan confirming to both of them how much I enjoyed being a sub – and being called a slut.

I was lost in my task when Master grabbed hold of my hair and roughly pulled me away. “That’s enough Jenny. I think you have swallowed all my cum. Good girl, but stand up now, we have something to tell you.” I got up. I must have looked a sight: my face was smeared in makeup and love juices. But I stood with head bowed mystified, waiting for the announcement. Master Peter spoke, “I know we said that we would only meet here, but I have arranged something for later this week. Anna has told me she had a little ambition that I realized I could help her fulfil – which would also be very useful for a business deal I am making. So, we are going to spend the afternoon on Thursday at the XXX Hotel.” The city-centre hotel he mentioned was luxurious and very expensive. “Don’t worry though you won’t be forgotten. I have arranged a treat for you, so you will have to book the afternoon off too. Seeing your behaviour today, I am sure you’ll love it.” Master Peter went on to tell me that Mistress Anna would pick out some “nice sexy” clothes for me before she went and that I’d should be excited because, “I was going to do some entertainment myself” What did this all mean? I wondered, but couldn’t help feeling more and more excited, especially as Mistress Anna told me, that as I “obviously enjoyed it so much” she thought I should now wear lingerie and my cockcage every day, even to work. I was beginning to feel like a proper sissy, but as the next few days taught me, this was only the start of my journey.

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By *ature4safefunMan
12 weeks ago

preston

So glad this is back

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By *ohnny 52TV/TS
12 weeks ago

Middlewich

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By *achealtvsubtoyTV/TS
12 weeks ago

hoddesdon

Mmmmm,,,,multiple partners and brown bottle time ?

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By *xstockingsTV/TS
12 weeks ago

north

Great story

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By *aywardsHeathSubMan
12 weeks ago

Haywards Heath

[Removed by poster at 20/10/25 16:53:20]

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By *umslut7Man
12 weeks ago

dunfermline

Superb

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By *amantha_kelTV/TS
12 weeks ago

magherafelt

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By *harliesfunMan
12 weeks ago

Brighton

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By *j1xMan
10 weeks ago

anywhere

Would love to see what happens next

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By *erry55Man
10 weeks ago

Portlaoise

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By *enny_J_Jones OP   TV/TS
9 weeks ago

sheffield

I will the start of Part II soon

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By *athyTV/TS
9 weeks ago

Nottingham

Loving this, making me full my cage xxx

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By *ocklover50100Man
9 weeks ago

Holsworthy

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By *ld joe69Man
9 weeks ago

Farnborough

Loving this

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By *reed maid carley cumdumpTV/TS
9 weeks ago

exeter

Really loving this storyline, time for a little brown bottle and lose yourself in sissy land xxx

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By (user no longer on site)
9 weeks ago

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By *harliesfunMan
9 weeks ago

Brighton

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By *ornishfetMan
9 weeks ago

St Ives

I do hope there is going to be more to this fantastic story

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By *hris106699Man
3 weeks ago

North hykeham

Awesome, looking forward to more

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By *usan 749ukTV/TS
3 weeks ago

Bangor

Good

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By *ew_bi_guy1984Man
2 weeks ago

ng19

love dominant men talking filth while I drain their balls and they taste wifes soggy thong

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By *ully fashioned slutMan
2 days ago

norwich

Wow

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By *perm bank69Man
1 day ago

Hythe

Mmm hot

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