Sissy Salon Stories: Experiences in Sissy Fashion

Sissy Salon Stories: Experiences in Sissy Fashion

Here’re 4 sissy salon stories for you:)

THE NEW HAIRDRESSER PT. 01

Carla and I have just moved house. She wanted to be closer to the clinic where she works as an IVF specialist. Although it meant a bit more of a commute for me to the library where I’ve worked most of my adult life, I was happy to make the move away from our apartment and into a much bigger, newer property.

Thing is when you move it means finding a new GP surgery, new places to socialise and it also meant finding a new hairdressers. Our old one was now more than an hour’s drive away even in light traffic. Like everything else she does Carla forensically studied the best hairdressers close to our new home. She didn’t tell me she’d found one until she came home looking like a model on a catwalk. Her new gorgeous hairstyle oozed that professional classy, hot and sexy look you associate with millionaire babes that live in L.A.’s most luxurious mansions.

Sissy Salon Stories

“Fuck Carla,” I said as she walked into our large hallway, raven coloured hair bouncing on her shoulders, gentle resting on her magnificent 34DD breasts, “you look absolutely stunning.”

“Glad you noticed hubby. Isn’t it terrific?”

“Very, very hot and glamorous.” I said, before asking: “Where did you get it done?”

“Place called Ava’s run by her and an associate named Clive. Gay as the day is long, but he washes your hair and gives you a free massage and not just on the scalp, a full body massage. He also cuts men’s hair, and Ava – super sexy hot blonde with a body to die for, she’s 45, but you could easily knock ten years off her – is so hot that if I wasn’t straight I’d desperately want her to be my lesbian lover. Actually, I wouldn’t mind a one night stand with her she’s that hot!”

Carla’s reflections were getting my tiny four and a half inch cock really excited. I’ve never heard her talk about any woman like that before. The thought of Carla becoming some kind of lipstick lesbian – if only for a night – with some sexy nubile blonde goddess was filling me with lust. Little did I realise Carla had something just as gay lined up for me.

“Sorry hubby I got quite lost and distracted there. I was coming over all Katy Perry thinking I’d kiss a girl and oh my, how I’d like it…but back to Clive. Ava told me – and this you must not share with anyone – that Clive loves wearing panties and stockings, and all kinds of other items of women’s lingerie.

He and Ava often go shopping for lingerie together, or if he’s a really good boy she’ll let him have some of her worn panties. Imagine how sexy that must be for him?! I’ve always thought guys that enjoy crossdressing prefer to wear their wife’s panties rather than a brand new pair they themselves have ordered by doing some online shopping. Anyway, Ava can arrange for Clive to give you my darling a free cut for life provided you allow him to wear ladies underwear while he’s doing so and…you must also be wearing something similar.”

“You’re joking?” But I could clearly see Carla wasn’t. The other problem was I was quite turned on by the thought of seeing another guy wearing panties – for a moment I pictured this Clive wearing some sexy lingerie of Carla’s and giving me a massage. And something snapped inside me – a yearning to be free of my masculinity – and let my curiosity for all things feminine become more dominant. None of which, of course, I was going to admit to my wife with her new sexy haircut.

“Come on hubby. Free hair cuts for life. Imagine how much money you’ll save.”

“I’m not wearing your panties and stockings while some sissy crossdresser gives me a massage. How gay is that?” I protested, but my, by now, fully engorged cock was saying the complete opposite.

“Oh, I get it.” Carla said enigmatically.

“You get what?”

“You’re just afraid that if you put on a pair of my panties and stockings and let some gorgeous gay guy give you a massage you might get turned on.”

“Don’t be ridiculous.” I objected. But the more I thought about it, the more I realised Carla was right. For most of my adult life I’ve been a little bit too interested in what it might be like to experiment with someone of the same sex. And recently Carla had really been dominating our sexual relationship. The more dominant she became, the more submissive I became. And the more I liked it.

Our sex life had grown dull and mundane. I couldn’t give Carla an orgasm anymore without using one of her large rampant rabbit vibrators. I instinctively knew she desired a bigger cock than my measly worm. Even in my better moments when I seemed to be giving her some pleasure I actually thought I couldn’t blame her if she was regularly getting fucked by some of the doctors at the clinic – or even some of the patients.

Carla is so hot and sexy with her 34DD tits and curvaceous ass, the least she deserves is some hunky guys with much bigger cocks than mine giving her a right good seeing too. Didn’t she? After all she had needs. And there’s no way I could fulfil them. I was way too small and submissive, and more and more attracted by Carla’s suggestion of dressing up in her panties and letting Clive give me a massage. After all, it would save me a lot of money.

Shit, what was happening to me? This is how Carla’s mind games over the past couple of months had got me. We’d started watching RuPaul’s Drag Race together, a couple of versions of the Rocky Horror Picture Show and other programmes and films featuring men being feminized. Afterwards, we’d have great sex together. Especially If I suggested to Carla – which I have over half a dozen times now during foreplay – deserved to have some hunky guy with a big cock, unzipping her skirt, fondling her breasts and pulling her panties down before taking her from behind in her office. It was a fantasy we were both increasingly excited by.

Thing is every time we’ve role played this fantasy Carla’s behaved like a total porn star in the bedroom and we’ve both had phenomenal orgasms. She’s usually ended up sat astride me, riding me like a bitch on heat, pinching and flicking my nipples – which always drives me insane with pleasure, and shouting expletives at me or rather at Don, or Simon, or Ben or James or a plethora of other hot guys she works with at the clinic.

I’ve met a large number of her colleagues and each one of them is far more attractive than me. They’re all well groomed and clearly work out regularly at the gym and Ben and James in particular are guys Carla is clearly attracted to.

Ben is only 30 whereas James is nearing retirement at 59 (two years older than me), but he’s one good looking guy and in my more perverse and insane moments (usually when Carla’s been licking my nipples) I’ve really started enjoying the thought of him shagging Carla in her office or even on our bed. And Ben? Well Ben is your basic nightmare.

So good looking, but someone who prefers older, more mature women, like my hot sexy wife. Carla is 45 now. She has a much fuller figure than when we first married, she’s about a size 14, but she actually looks more stunning with the extra weight. Oh and her ample ass is to die for. It’s ridiculously sexy. Think Kardashian.

All these thoughts were running through my head as I tried to take exception to Carla’s suggestion. Trouble was my complaining was falling on deaf ears.

“I think you protest too much hubby. I think you’d secretly love to wear my panties and have another guy give you a full body massage. Especially if that guy was also wearing a pair of my panties.”

Now, actually that did sound ridiculously erotic and exciting. But I wasn’t going to tell Carla that. I really feared that if we went down this road there’d be no turning back. But, eventually, as per usual, Carla won.

“Okay Dan, if you’re really against this – fair enough. But why not try it – just once – and see what happens. I’ll come with you obviously. And, who knows maybe you can watch Ava and I play at being lipstick lesbians as a warm up to the main event.”

I mean, how could I possibly say no to that?

“Okay, you win. I mean the thought of watching you kiss another woman is more than enough of an incentive.”

“I thought as much. Actually, Dan, just on that point. And this is a serious question…”

“Go on,” I said, now filled with lustful anticipation. “Ask away.”

“Well, would you prefer to see me kiss Ava or Josh or Henry or Don or Simon or Ben or James?” Carla asked the question in a coquettish, seductive voice.

Obviously I loved the thought of Carla kissing another woman, any woman. For years it had been my number one fantasy. But now I wasn’t so sure. I kept imagining her on her office desk black skirt hitched up around her waist, new white shirt tossed aside and her red satin bra clearly on view. She was still wearing her matching scarlet red panties, but the had been expertly moved aside by James and he was now giving Carla cunnilingus.

His tongue exploring every millimetre of Carla’s hot damp pussy. Ben meanwhile was kissing her lips, and Carla was now unzipping her trousers before taking his huge eight inch cock into her mouth. All of this while I watched on sat in Carla’s leather chair rubbing my little member through a pair of Carla’s vintage What Katie Did retro French Knickers.

The thought of this happening in real life was far more exciting and enticing, I mused, than watching Carla playing tonsil tennis with some sexy Aphrodite. For the first time since Carla and I had introduced such fantasies into our love life I realised Carla’s sensual eroticism was starting to really effect the way I thought about sex and it’s many pleasures.

But the thought of admitting this to Carla was terrifying. Deny these thoughts though and I knew I could spoil the moment. Carla’s dazzling blue eyes bore into me more intensely than I’d ever experienced. With her new hair do she’d never looked so hot and sexy. I felt any resistance melting away. Furthermore, I couldn’t erase those sexy images in my head of Carla servicing Ben and James at the same time as I looked on ridiculously thrilled and aroused.

“Well, it may surprise you my gorgeous hot sexy wife,” I began.

“Yes?’ Carla replied beguilingly.

“That increasingly – and despite huge spasms of jealously that frequently accompany these thoughts – but the thought of one of your hot colleagues not only kissing you, but fucking you in your office, or even in our bedroom, is far more alluring than you kissing another woman – exciting though that obviously is.” There I’d admitted it. What I never could have imagined or calculated was Carla’s thrilling and immediate response to what to my mind, was a shameful acknowledgement of how sissy and submissive I had become over the past month or so.

Carla whooped with joy, grabbed my hands and literally raced me upstairs. In no time at all she had removed all my clothes. My cock was now fully erect and didn’t look half bad considering it’s pathetic size. I watched in horror, but also in wanton anticipation as Carla went in the laundry basket and pulled out her dirty pink satin panties – she’s knows that they’re my personal favourites. She made me sniff and inhale the aroma from her gusset to begin with, the effect was intoxicating. But then she gently rubbed the soft fabric on my nipples and I’d never felt such sexual pleasure.

Until that is, she slid the panties up my legs and past my thighs before letting them rest on ass, cock and ball sac. I nearly prematurely ejaculated – the sensuality of the fabric was like nothing I could have imagined. Why had I never tried this before I wondered? It was perverse and deviant, but it was also extremely erotic and felt like an aphrodisiac.

I’d never been more turned on in my life. Carla could tell how excited I was. She could also see how aroused I was. Pre-cum was pouring out of me onto my wife’s sexy pink panties.Carla was overjoyed by how well this was going. She hadn’t taken any of her clothes off yet. But sometimes I prefer that. She always looks so hot in her outfits.

Today she was wearing a simple pink shirt – she had three buttons undone and her delicious cleavage was threatening to consume me. Beneath the shirt I could clearly see a black lacy bra.

She was also attired in a short black skirt and because she was now sat astride me her black stockings were clearly in view (Carla always wears stockings or hold-ups, never tights which she loathes). He lips were painted crimson red as usual. And her perfume was drowning me in desire. She was a hot wife already. I now knew I wanted her to become a genuine hot wife and cuckold me. After all, that was not only what she deserved, but it’s surely what we both now wanted?

Spotting the pre-cum assembling on her sexy pink panties that I was wearing Carla gave me an obscene and mischievous grin.

“Leaking pre-cum onto my sexy pink panties needs to be punished, Dan. That is so naughty. Don’t you agree?’ She said huskily.

“Yes Mistress Carla.” I said in an increasingly effeminate voice. “What do you suggest would be a suitable punishment?”

“Well I could make you eat your own cum or I could take my sheer my fully fashioned stockings off and put them on you. But then, of course, you may leak more pre-cum and then I’d have to make you lick up every drop.”

The thought of eating my own cum was both horrifying and extremely amorous. I felt caught between the devil and the deep blue sea. But I was now desperate to try on Carla’s stockings and if I leaked more pre-cum and Carla forced me to lick it up so be it.

“Oh stockings please Mistress Carla.”

“As you wish.” Carla said kissing my lips and taking her stockings off. She deliberately bent over the bed as she did so enabling me to catch a glimpse of her expensive 1950s style retro vibrant green satin with a black fishnet panel knickers. They are glorious.

When Carla pulled her stockings up my legs I knew she could now do whatever she wanted sexually. She had won our role playing fantasy game in straight sets. She was too clever, too sexy, too naughty. I couldn’t handle her anymore. More than that I wanted to submit to every whim in the bedroom however lewd, bawdy, perverse, or humiliating. The effect of wearing those retro stockings was startling. I could have sworn my diminutive cock soared to a full five inches. It certainly became more engorged. I’d never felt so utterly aroused in my life. I was captivated by the sheer softness of Carla’s nylons. As much as I was by wearing her pink panties.

The thought of wearing trousers or boxer shorts again was sickening. I felt girl. I felt like a woman. And I was starting to feel like I needed a man. A man like Clive the hairdresser who would fully understand the thrill of being a sissy crossdresser. And I desperately wanted to watch my hot sexy wife getting fucked by lots of hunky horny guys. Of course another huge dollop of pre-cum erupted onto Carla’s pink panties.

“Oh dear, ” Carla said, “looks like some sissies just can’t control themselves. Now you’re really going to have to be punished.”

Carla reached inside her underwear drawer and pulled out her eight inch black rampant rabbit. I thought she was going to make me use it on her – something I would have been more than happy to do – she was clearly more than a little aroused herself now.

But no, she took the shaft of the penis in her right hand, and placed the tip of it on the sodden panties scooping up as much of my pre-cum – there were lots of it – as she could. Kissing me passionately and again licking my nipples she then placed the huge vibrator in my mouth whispering in my ear: “Lick it all up my darling sissy husband. You need to get used to it, if you’re going to pleasure Clive tomorrow at your appointment.”

The thought of sucking another guy’s cock as Carla and Ava watched, which even half an hour earlier would have filled me with disgust, now turned me frantic with lust and perversion. I hungrily took the vibrator as deep into my mouth as possible, savouring, for the first time, the taste of cum. Yes, it was my own pre-cum, but what shocked me was how much tasting, licking and ultimately eating it aroused me still further.

“More.” I gasped, as Carla, more than a little surprised, saw how much I was enjoying it.”

“Oh my darling sissy hubby you look so slutty with a big cock in your mouth. Soon we can be girly cocksuckers together.”

“I’d love that my gorgeous hot sexy wife. I really would.”

Carla was thrilled. She removed her shirt before scooping up another teaspoonful of my pre-cum with the enormous black vibrator. Looking at her magnificent bosom, nipples hardening with every moment that passed and threatening to break free from the sexy pink balcony bra, I realised that I yearned to watch one of her colleagues fondling her breasts and licking her huge nipples. I even pictured some guy allowing me to rub his cock until he ejaculated all over Carla’s naked breasts before the two of them made me lick up every last drop. Carla really is a hot wife, I said again to myself, and she deserves to pleasure dozens of cocks and to have them pleasure her.

As she inserted the black vibrator into my mouth again, Carla made me take hold of it.

“Imagine it’s Clive’s cock,” she said. “And Ava and I are watching you both pleasure each other. Now imagine me bent over our bed like this. And Ben or Josh or James unzipping my skirt and slapping my big fat ass like this – Carla slapped her own ass, raising my arousal levels even more – before fucking me here on our marital bed in front of you my gorgeous sissy husband.”

The thought of Carla being fucked in front of was now such a potent idea that I was lost in a sea of perversion. I honestly didn’t know what was more exciting – wearing Carla’s underwear while enjoying some mutual fellatio with Clive or watching Carla get shagged by some hunk. Both thoughts were running in a wonderful picture inside my head as watched Carla swinging her ass back and forth simulating being fucked in front of whilst wearing her sexy vintage panties. I was so turned on I grabbed by own cock and started rubbing it. Carla paused her rocking motion and came and astride me, moving my hand aside and taking over.

She instinctively knew I wasn’t going to last long, so she slowed down rubbing my cock gently, in between licking my nipples. She took the vibrator from my mouth and kissed me darting her tongue inside me incessantly.

I was getting really close now. Sensing my mounting excitement Carla momentarily stopped rubbing my cock and instead tucked it back inside her pink panties. She then turned the vibrator onto it’s lowest setting and put the ears inside the skin of my cock. A wave of intense pleasure washed over me. Again this was new.

“No wonder you like this my hot, sexy, naughty wife…But what about you? You know if I come first I’m pretty much spent.”

“Don’t worry about me tonight my lovely sissy crossdresser. Tonight it’s all about you. You are such a wonderful husband embracing this new lifestyle. You deserve a mountain of pleasure.”

“Oh Carla, that’s so lovely of you. I love wearing your panties and stockings and I can’t wait to watch you get fucked by one of your hot hunky colleagues.”

“Would it intensify your orgasm this evening do you think if i describe to you what they’re going to do to me in the office when I’m working this weekend?”

“Oh, yes please Carla,” I said, “But please hurry, I don’t think I can last much longer.”

“In that case let’s turn the vibrator off again for a moment. In fact, why don’t we take up another level.”

“But how? I’m already more aroused than I ever been since we first got married.”

“Well, if you’re going to be a girly now. You’ll not only want to suck cocks, surely you’ll want to feel cocks in your boy pussy.?”

“You mean…” I swallowed, understanding what Carla wanted to do to me.

“Oh yes sissy hubby, I mean putting a load of lubricant on the vibrator and inserting it into your ass while I continue to kiss you, kiss, lick and flick your nipples and rub your cock. After all sluts like you crave cock. I know I do.”

Although I was more than a little scared I acquiesced. The thought of having a wet vibrator inside my ass far more exciting than any fear I had.

“Oh, yes please mistress. I want to feel a cock in me. A real cock.”

Again Carla looked more than a little surprised at how east this was. I was embracing this lifestyle with such eagerness that even in her wildest dreams she couldn’t have imagined how easy it would be.

I watched as she squeezed the lubricant over the shaft of the vibrator, smothering it with the liquid until she was fully satisfied I’d manage to take at least half of the eight inches into my ass. Then she moved the gusset of the pink panties aside and slowly began inserting the vibrator into my, by now, expectant ass.

The first inch went in with no problem, Carla kept glancing at me lovingly, clearly wanting me to enjoy the experience and determined not to hurt me at all. Her lovingkindness made me relax and before I knew it I had managed to take the fist three inches without any problem at all. The lubricant was working and I started to feel wave after wave after wave of pleasure. This was insane, I was loving every minute of it. There was some discomfort when the vibrator reached the half way point, but Carla compensated for this by turning the vibrator on until the shaft was pulsating. I literally screamed with pleasure.

Carla was delighted and in no time at all she had managed to insert the vibrator two thirds of the way in. I was moaning softly as the pulsations continuously pleasured me.

“Penny for them?” Carla asked.

“I was just thinking that if that is anything like what a real cock feels like inside your ass I want Clive to not only massage me tomorrow and suck my cock, I want him to fuck me.”

“Oh hubby, that’s so hot. Now relax and let me tell you a story about your hot naughty wife whilst I flick your nipples.”

“Oh Carla, that would be so exciting.”

“Oh darling hubby. Imagine there’s a camera in my office and you’re at home watching the live feed dressed in my pink panties, pink balcony bra and vintage stockings. You start rubbing your cock as Ben and James come into my office. They start to remove my clothes – my shirt comes off first. Ben tosses it aside and immediately I take his off as James fondles my breasts and unzips my skirt. As I take Ben’s trousers off you watch James and I passionately kiss.

Yes another man’s lips are on your hot wife’s and you watch, growing increasingly horny, as our tongues find each other and you hear me groan with pleasure. In no time at all Ben is naked and you look on stupefied, jealous, but more and more aroused. The jealousy is painful, but the pleasure you’re experiencing is far more powerful. Part of you what’s to stop what happening, but a larger part is desperate for the perversion to continue. I deliberately wink and smile at the camera to reassure you of my love. And suddenly you’re urging me on to more bawdiness.

“Now I’m on my knees sucking Ben’s cock as James undresses. At home you start to rub your own cock imagining what it must be like to suck another cock with me. You particularly like the look of James – maybe because he’s around the same age as yourself. Thought he’s much fitter and far more handsome. Soon both of them are naked. And I delight in taking two enormous cocks in my mouth at the same time.

“You watch as James stands up, kisses me again and moves my panties aside as he starts to take me from behind. Watching another guy put his glistening cock into your hot wife’s pussy is almost too much for you. You’re rubbing you penis furiously now – all jealousy dissipated – your porn star of a wife keeps looking into that camera lens grinning mischievously. You love me more than words can say and love me being a hot wife. And you love wearing my underwear.

Underwear that is about to be covered in your own cum. You’re so close now. I’m on my back now so you can get a really close up view. You watch with joyful lust as James thrusts harder and deeper into my pussy. I take Ben’s cock in my hand and rub it to oblivion. He erupts all over my tits just as James is about to climax.Watching another guy’s cum pour over your naughty wife’s nipples get you even hornier.

You long to be in the room with us all so Ben can tell you to lick it all up. Maybe we’d share the experience as I beg you to share Ben’s lovely cum with me. Maybe you’d have your first ever cream pie too. You know you want to and watching James not only climax but give me an enormous orgasm only makes you more eager to be a slut like your hot wife.

“The best part is looking at me satiated as James’s cum starts leaking out of my pussy…”

That was the moment I experienced my first ever “sissygasm” The pulsations in my ass and Carla’s story had sent me right over the edge. Picturing Carla covered in another guy’s cum – especially cum on her breasts and trickling down her nipples – and cum pouring out of her pussy was simply too much for me. My own orgasm was immense. I felt cum pour into Carla’s pink panties and I loved the feeling of the salty liquid soaking my wife’s panties. How I wanted it to be Clive’s or James’s or Ben’s.

How I longed to suck another guy’s cock and feel his cock inside me as we both dressed up in my hot wife’s lingerie – panties, stockings, bra, chemise. I was hooked. Carla was thrilled.

“I think you are now officially a crossdressing sissy cuckold.” Carla said, a big grin on her face.

“And you, my sexy wife, have my permission to cuckold me for life and be the hottest, naughtiest wife ever.”

“What would that look like, Dan?”

“It would mean you could suck and fuck any guy you wanted to and I could never complain.”

“Like, never complain ever?”

“Ever. I’ll even sign on the dotted line if you draw up a hot wife crossdressing sissy cuckold contract.”

“Oh, I like the sound of that…And if you break the terms of the contract?”

“Well you punish me. Why ot begin by taking some pictures of me now dressed in your pink panties and sheer stockings with this enormous vibrator sticking in my ass so you can blackmail me?” I was delirious now. “You can send them to Clive and Ava, and all your colleagues at work. While you’re at it why don’t I take some pictures of you in a variety of sexy outfits? I can then send them to all your colleagues and any other guys you wish begging them to fuck you. Telling them I’m now your sissy husband and begging them to satisfy you whenever you want.”

“Oh, that’s such a wonderful, naughty idea, hubby. You should also ask them if they no any other crossdressing sissies that would like to fuck you wearing my underwear.”

“Agreed.” I said, overwhelmed with lust and excitement despite my orgasm.

So we spent the rest of the night doing just that. As I grew more tired Carla simply gave me some different items of her underwear to wear. And she took dozens of photos of me dressed like a tart. My favourite one was where I was leaning over the bed – on all fours – dressed in a corset, stockings and suspenders, high heels and ruby red lipstick. I had my head turned the camera and I was pouting. I thought my ass looked particularly sexy in a pair of Carla’s luxurious high waisted panties.

I looked so naughty, so brazen, but also so feminine. That’s the picture you can see on my profile here on literotica that Carla made me set up to tell you all about our adventures. Stories that are true. Stories that are meant to entice other sissy crossdressers into our boudoir. I’d love to suck you cocks and feel your cocks in my pretty ass whilst you were wearing my hot wife’s panties my lovely followers. We could be so naughty together.

And afterwards Carla would you to fuck her on our marital bed. You could kiss her lips. Fondle her breasts and lick her hard nipples. Maybe I could fuck your boy pussy at the same time? Love you my fellow sissies. Carla sends her love as well. She currently on our bed with a policeman, a doctor and a builder. The builder has already exploded on her tits. The policeman has just cum on her ass. And the doctor has just given her the best orgasm – her words – she has ever experienced.

Hey, but that’s hunky James for you. He’s actually going to let me lick his lovely cock now. I’ve been begging him and Carla to let me do that for ages. He says he will as long as I’m dressed in some of Carla’s underwear. But here’s the thing he wants my followers to suggest the outfit I should wear.

So hurry up with you replies I’m desperate to suck James’s cock. Maybe, if I look slutty enough he’ll even fuck me like he’s just fucked my hot naughty gorgeous wife. While I wait for your replies I’m going to have to lick up the cum from Carla’s tits and ass. Feel free to join in my lovely sissy friends. XXX

TO BE CONTINUED

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