Cuckold Training
It started with a picture my wife sent me attached to a text message...
HOPE YOU'RE HAVING A RELAXING WEEKEND HUBBY. MINE JUST GOT A LOT MORE INTERESTING!
And there, bending over a bed in the hotel room Carla was staying in - she was away at a conference in North Wales - stood my wife of twenty years in only her underwear - pink panties, matching pink balcony bra, ruby red stockings and high heels, smiling at the camera. Carla looked hot as hell. I felt my four inch cock spring to life immediately, but then, when I looked closer, I noticed a 7-8 thick monster cock in the foreground, erect, clearly belonging to some hunky stud. For weeks Carla had been gently, but naughtily teasing me about how she'd like to try a bigger cock - as our anniversary approached she said it was the least she deserved after years of my little member trying to satisfy her.
Although I was a little jealous when she said such things, I indulged her fantasy by buying two enormous realistic vibrating dildos from a sex shop - a white one and a black one (Carla's eyes lit up when she saw the big monster black vibrator).
After I used it on her for the first time she'd purred with delight experiencing multiple orgasms and stating: "So it's true what they say hubby...white girls who try black never want to go back!"
Since Valentine's Day Carla had become more and more outrageous in the bedroom asking me to invent stories about young guys with big cocks fucking her in front of me while I sucked her tits. Part of me was extremely disturbed by these fantasies - Carla had always been so conservative during sex, I wondered what had gotten into her - but I was also thrilled by how excited and liberated she was becoming. And after each orgasm she would sit astride me, stroke my nipples (something that drives me wild) and use the vibrator on my small cock to give me an orgasm.
But now, looking at this picture I felt betrayed, heart-broken and yet, perversely, more than a little turned on. Nevertheless I was still hopping mad and just about to ring Carla to ask her what the fuck she thought she was playing at when another text message came through:
I HOPE YOU'RE NOT ANGRY HUBBY. I HAVE NEEDS YOU KNOW...BESIDES I FORGOT TO PACK MY VIBRATORS! I WONDER IF SECRETLY YOU'RE A LITTLE TURNED ON?! IF SO, SAY "YES I AM MY SEXY HOT WIFE," AND I'LL SEND YOU MORE PICTURES!
This was fight, flight or freeze syndrome. How the hell was I meant to respond to that? I was seething with anger, but I couldn't deny that there was a twisted, debase and deviant set of thoughts and feelings that were flowing through me, nor could I deny that my own little cock was pulsating with anticipation at what images Carla might send me next. Scarcely believing what I was doing I typed the words Carla had requested of me and only spent a moment hesitating before pressing SEND:
YES I AM MORE THAN A LITTLE TURNED ON MY SASSY, NAUGHTY WIFE, PLEASE SEND ME MORE PICTURES AND...ENJOY YOURSELF XX
I couldn't believe I'd added those last two words...ENJOY YOURSELF followed by two kisses. I felt like a voyeur appalled by the depraved images he was witnessing and yet unable, because of some degenerate addiction, to tear himself away from the scenes that were playing out in front of him.
Carla, of course, was delighted with my response. She texted back immediately:
OH MY DARLING HUBBY, THANK YOU, AM I GOING TO PUT ON A SHOW FOR YOU NOW!
Her words caused my cock to swell a little more. I sat on the edge of our bed and rubbed it gently, nervously awaiting the next picture. When it came through I nearly prematurely ejaculated.
Carla's tongue was at the base of the hunky guy's big fat cock which was glistening with pre-cum. She was smiling, clearly savouring the snack she was about to have. There were traces of her red lip-gloss on the stud's shaft and I could tell this was a guy that regularly worked out. His legs and stomach were toned and muscular. Carla is 45, but looks ten years younger. She has a fantastically rounded, big, but sexy as fuck derriere and 34DD tits. I'm 55, more than a little overweight, with a skinny body and thinning hair. I couldn't compete with this guy. I felt another wave of jealousy, Carla has never once sucked my cock, but this was quickly forgotten when my phone pinged again. The next image showed Carla on the bed naked now apart from her stockings. Her pink panties were resting on the end of her right foot which was waving in front of the camera:
WHY DON'T YOU SNIFF AND THEN WEAR A PAIR OF MY DIRTY PANTIES HUBBY. I'VE LEFT SOME IN THE LAUNDRY BIN FOR YOU XX
It was a ridiculous, but enticing, proposition. I know this sounds like it was all happening too fast, but that's the point. Ordinarily I would have dismissed such a ludicrous suggestion out of hand, but Carla was deliberately using the speed of events to prevent me from thinking straight. I felt mesmerised and hypnotised by her lasciviousness. Deranged, I jumped off the bed, opened the laundry bin and finding a pair of her vintage high-waisted purple and black satin panties (purchased from What Katie Did) sniffed the gusset (it smelt of Carla's pussy juices and I found the fragrance dangerously intoxicating), and rolled my hot wife's worn panties up my thighs. When the silken material caressed my balls and cock I had an overwhelming viscerally thrilling reaction. It was like a pleasant electrical charge surged through my body. Once more my cock swelled with pleasure. It took me by complete surprise. Instead of feeling ridiculous I felt strangely liberated. I couldn't resist going over to the full length mirror, running my hands over my chest, nipples, and then over my stiff cock. I cupped my balls through the delightful material and immediately a dollop of pre-cum became visible on my hot wife's panties. I took a selfie and without even thinking about it sent it to Carla. She was delighted by my acquiescence:
OH MY DARLING HUBBY YOU LOOK LIKE SUCH A SEXY SISSY IN MY PANTIES. I WISH YOU WERE HERE SO JAMES COULD FUCK US BOTH. I BET YOU'D LOVE TO SUCK HIS BIG JUICY COCK ONCE IT'S BEEN IN YOUR NAUGHTY HOT WIFE'S PUSSY?! XX
Now you may think Carla had jumped the gun with that comment. That she'd gone too far, way too quickly. But, by now she must have guessed I'd agree to almost anything. And the thought of sucking a cock that had pleasured my wife, was, on the one hand ridiculously stupid and indecent for a straight guy like myself, but on the other hand I felt it was mind-blowingly tempting.
Looking back now it was this salacious idea that got such a grip of me that Carla's desire to cuckold me became impossible to resist. Though I didn't really realise it at the time, my naughty hot wife had just delivered me a knockout blow. From now on she'd be able to fuck as many guys as she wanted and I would be her sissy crossdressing faggot. A part I would crave and therefore play willingly. I simply replied:
I THINK I MIGHT REALLY LIKE THAT MY NAUGHTY HOT WIFE XX
Carla's response thrilled me:
IN THAT CASE MY SISSY CROSSDRESSING HUBBY, AS A REWARD, I'M GOING TO GIVE YOU A LIVE SHOW! OPEN UP YOUR LAPTOP AND I'LL FACE TIME YOU. MY HORNY BEHAVIOUR WILL LOOK SO MUCH BETTER ON THE BIG SCREEN! XX
So I powered up my laptop and with nervous anticipation awaited Carla's call. As I was waiting however, I had a momentary pause: Where, I wondered, had I heard that name James before? My memory banks went into overdrive...but just when I thought I'd worked it out, Carla's call came through. I clicked the accept button and the first image that greeted me was Carla being fucked from behind by James the stud. She was still wearing her stockings and high heels, and in the position she was in she looked like a stunningly gorgeous porn star. Oh, and the howls of delight emanating from her as James drove his big meaty cock into her pussy while his fingers tweaked her nipples, actually made me salivate. Despite my jealousy, watching Carla in paroxysms of pleasure, stirred something primal in me and I felt my cock leak a huge dollop pf pre-cum onto my wife's silky panties. And when Carla gently moved forward, turned and faced James, pushed him on the bed, and lowered herself onto his throbbing, glistening, enormous cock - all the time staring into the camera and giving me a sultry smile - my own hand reached inside Carla's worn panties and I started rubbing my own cock. By now I was desperate for relief.
It was only recently that Carla had admitted to me during one of our role playing games how she'd dreamt of other cocks pleasuring her while I watched - now her fantasy was being lived out in front of me and a strange part of my psyche was weirdly loving every minute of it. I watched, stupefied as Carla started pirouetting and gyrating her pussy up and down the length of James's huge cock. My wife was being a total slut and there I was in our bedroom wearing a pair of her dirty panties watching her fuck another guy senseless and I was loving every minute of it!
When Carla started slamming her pussy repeatedly on James's cock I knew she was reaching the point of no return. When James reached up to meet her tongue with his own and their mouths touched I ejaculated instantly...it was then I felt Carla waking me up.
"Hey, hubby, you've just had a wet dream," she said, accusingly, but laughing at the same time, "there's cum all over the back of my black panties and on my leg. What the fuck were you dreaming about it?!"
It had only been a dream? Shit! I didn't know whether to feel relieved or disappointed.
"Wow hubby, you look really, really guilty," Carla said. "Spill the beans."
"I'm not sure I want to," I replied, rather feebly.
"If you tell me...however naughty or outrageous it was, maybe we can do it for real?" Carla said in a voice dripping with seduction and a touch of sadistic menace.
Unable to resist her coquettish witch-like charms, I finally succumbed and told her the whole lurid story, leaving out nothing. By the end Carla had inserted one of her hands inside her black lace panties and was fingering herself.
"Fuck hubby, I don't think you've ever got me so turned on. My pussy is dripping with excitement," Carla took a deep breath before continuing: "You know who James is, don't you?"
"I couldn't quite remember in my dream, though subconsciously his name rang a bell, but, obviously, when you woke me up just now, I thought he must simply be a figment of my overactive imagination."
Carla smiled and kissed me tenderly, and then more passionately.
"Not at all, hubby. James, if you remember is the hunky new d**g rep that all the nurses were fawning over when he came into my office a couple of weeks ago. The guy I said had just been added to my six guys I'm allowed to fuck list and you can't get mad. He's built like a viking and looks like one too. He does a bit of male modelling on the side and the nurses and I discovered he's actually starred in half a dozen pornos. Remember now?"
"Oh, that James!" I exclaimed swallowing hard as I recalled my dream again and imagined this Norse-like god fucking my hot naughty wife into Valhalla.
"Yes, that James! The thought of him fucking me. Oh sweet Odin! That would make me delirious. And you say, it was definitely James fucking me in your dream."
"Yes, absolutely. And he was hung like a Norse god too." I added for good measure, beginning to enjoy now how much this was clearly turning Carla on.
"How big?" Carla asked, cupping my balls. I gave a little sigh of pleasure as Carla's fingers caressed my scrotum.
"At least eight inches and a girth that would not look out of place on a stallion."
"Oh boy, fuck me! And it turned you on, hubby, watching this hunk fuck your hot naughty wife?"
I hesitated, but by now, I was too far gone to lie.
"Fuck Carla, although it sounds mental, it really did!"
Carla giggled and gave me a saucy look that said she approved of my answer.
"Maybe my dirty panties that you were wearing helped?"
"They certainly seemed to," I answered truthfully.
"So how about you try these ones I'm wearing now then? After all you have just cum all over my ass."
"I don't know Carla, I'd feel like a fool."
Carla looked momentarily crestfallen, but then her eyes brightened again and she pulled the duvet back exposing a huge damp patch on the back of her panties where my cum had fallen, and on her gusset where her own pussy juices had soaked the material, presumably because the thought of James fucking her for real had overwhelmed her with anticipation and excitement. When she was back on the bed properly she had her laptop in her hand. Without saying a word she opened it up - clicked on a tab called: CUCKOLD TRAINING and, as the first image sprang to life, she looked at me with such unbridled desire that I felt my grip on reality and sanity dissipate like dew on an unexpectantly warm spring morning.
The image showed a woman, that looked very similar to Carla, with a huge cock in her hand, her hungry tongue running across the tip of it, beside a caption that posed the question: DO YOU WANT TO LICK IT TOO? I felt my heart skip a beat, and then a surge of some primeval craving rising up from my stomach to my mouth. I even ran my tongue across my lips. I'd never felt any same sex attraction ever, but there was something deeply arousing about that picture and the caption that accompanied it. Something brazenly carnal, base, and risqué, that sent me on a train of thought that I'd never embarked on before. Still completely lost in the moment, I opened my legs willingly as Carla slid her silky black lace panties up my thighs until they nestled deliciously on my balls and cock. I felt a surprising, but potent, salacious thrill. I wasn't dreaming anymore. This was reality and I was beginning to love every perverse moment of it. Suddenly, all thoughts of resisting this journey Carla was clearly intent on taking me on, simply melted away as my cock stiffened in my hot wife's dirty panties. It was thrilling to feel her damp gusset on my ball sac, a dampness I knew was due to the thought of James the Viking fucking her into oblivion.
The cock in the image was hypnotic. I think what was so titillating about it was that the woman in the image really could have been Carla's doppelgänger - something I thought, later, my hot naughty wife had planned to perfection. And, I knew, in that moment, that if Carla offered me a cock to lick and suck, especially a cock she herself had licked and sucked, I'd probably be unable to resist such a sensual temptation.
Any lingering doubts were dispelled a few seconds later when Carla clicked on the next image. Now the same Carla lookalike was down on her knees, the same hunky guy's cock in her mouth, her red lipstick all over the shaft, and, oh, the caption, the caption was mesmeric: BET YOU WISH MY LIPS WERE YOURS, DON'T YOU SISSY?
My dream and now this. Carla was pummelling me with a type of foreplay I'd never imagined would turn me on. It was like she had simply, with ease, pressed a gay crossdressing cuckold switch in my brain and any thoughts of being straight again had vanished instantly. Seeing my prurient desire increase with every second that ticked by Carla decided to go all out and clicked the final image. It showed a middle aged guy like myself dressed in his wife's fishnet stockings, push-up bra and crotchless panties, soft red lip-gloss, mascara and false eyelashes, being fucked in his boi pussy by his wife's lover. The sissy faggot was staring into the camera, his wife was being fucked by two hunks at the same time, and the caption made me burst with longing. It read: "Oh, that feels so good my naughty wife, SO good, you making me a crossdressing sissy cuckold was the best thing you could have done for our marriage. Like you I now simply adore big cocks!"
Somewhere in the back of my mind, in some dark recess, I knew Carla was using these images as some sort of lascivious mind control to turn me into her femboi, but I was now powerless to resist her dominance over me. My own cock was now dripping with pre-cum, staining my wife's dirty black lace panties I was wearing until a small pool of liquid was protruding through the silky material. In an instant Carla ran a finger over the wondrous fabric scooping up a large teaspoonful of my salty pre-cum and spreading it on my lips and tongue. I'd never tasted my own cum before, but instead of finding it repugnant, instead of gagging on the liquid, I found myself hungering for it.
"More," I whispered hoarsely.
Carla squealed with delight and peeling the fabric of her dirty panties a little away from my fully erect four and a half inch cock, she started rubbing my little penis until another dollop of pre-cum glistened and dropped onto her hand. But this time she reached into her bedside table and pulled out her favourite dildo - it was nine inches, incredibly lifelike, and black. She placed my pre-cum onto the tip of the dildo and after saying: "open wide", inserted it into my mouth. To intensify the experience for us both she clicked on another image on her laptop. It showed a sissy crossdresser fully made up in a shiny black wig, tarty make-up, a black bodice, pink stockings, vintage cherry coloured panties and high heels about to take an enormous cock into his gaping mouth - a cock that had just exploded and was dripping with cum. The caption read: THE SISSY CUCKOLD'S MOUTH WATERED AND HE KNEW HE WAS GOING TO SWALLOW EVERY LAST DROP. Reading those words caused me to furiously lick and suck the black dildo my hot wife had just put in my mouth. I felt so gay now. I was so hungry for cock, I knew if Carla had brought some hot guy home for the weekend we'd be competing with each other to see who could give him the best orgasm. We'd certainly be passing his cock between our mouths in a game of tonsil tennis.
Carla took the dildo gently out of my mouth and started to lick and suck it herself.
"It's good to share," she said, as she passed it back to me, clicking on another picture. There was no subtlety to this image. It simply showed another sissy crossdresser (wearing a very short pleated mini skirt and balcony bra that made him look so sexy I could scarcely believe it was guy until I looked a little closer and saw an enormous bulge in his purple satin panties), kneeling down holding a lovely seven inch cock that was firing cum directly onto his awaiting tongue. The caption underscored how I was now feeling: ONCE YOU'VE TASTED CUM, THERE'S NO GOING BACK. I knew, instinctively this was true, but I also knew, as Carla had returned to caressing my cock, that as soon as I orgasmed my yearning for cock would disappear like a bad dream. But Carla was one step ahead of me yet again.
She too, suspected, that if her nefarious plan to turn me, her husband, into her sissy crossdressing cuckold was to work, she would need to prevent me from coming too soon. And if she really wanted me to suck cock she would have act fast. Unbeknown to me her planning was as good as a military campaign, her arsenal was fully equipped and she was about to launch a pre-emptive strike that would change everything.
"Well, I think that's enough for now, don't you hubby?" Carla said, teasingly.
"What do you mean, you can't leave it there?" I said imploringly.
"Why not hubby?"
"Because I'm gagging for it Carla."
"Well, so am I."
"So let's do it then."
"As I suspected Dan, you're not my sissy crossdressing cuckold just yet. You need further training."
"I don't Carla, I'm ready. Honestly."
"But you can't be."
"Why not?" I begged. Really not understanding where this was going.
"Because if you were, you'd know your tiny little cock could no longer satisfy your hot naughty wife. You'd want me to get fucked by lots of hunky, horny guys like James."
"But I do, Carla. I really do." I blurted out, totally consumed now by sissy desire for relief whatever form it took.
"You promise? You promise to not only support other hunky guys fucking your naughty wife, you will watch them doing so, and clean up the mess afterwards by eating lots and lots of cream pies?"
I knew what that would mean, but I would have agreed to anything at that moment.
"Of course I will, Carla. I'm actually looking forward to it."
"I think I'm actually starting to believe you hubby."
"It's true."
"Okay, prove it to me."
"How?"
Carla once more reached into her bedside table. She pulled out an A4 sheet of paper. On the right hand side it showed the most sexy, sultry picture of Carla I'd ever seen. It had obviously been taken in our bedroom - which begged the question: Who the fuck had taken it? But I was too far gone to care. Anyhow, Carla had never looked hotter. She was kneeling on our bed, staring directly into the camera, her shoulder length brunette hair looking glossy and lustrous. Her make-up was perfect - tarty, but stunning. Bright scarlet red lip-gloss, long false eyelashes, and smoky mascara. Think slutty, but stylish soft core porn star. And her outfit only consolidated that thought. Fuck it was mind-glowingly sexy. Spiked high heels, the finest shimmering black stockings attached, via delicate lacy suspenders, to a diaphanous black basque, and full satin sparkling black panties. A wicked thought crossed my mind: I realised it might be immoral to some couples, but my wife looked so fucking hot I knew that Carla was right - there was no way my feeble cock could fulfil her needs any longer - but, it would be a genuine pleasure to watch a load of hunky studs shagging my wife's brains out. Looking as gorgeously sexy as she did, and is, it was nothing less than she deserved. I was also struck by how much I wanted to wear that amazing slutty outfit she was wearing in the picture. And, yes, of course that included the high heels, mascara, lip gloss and false eyelashes...though it was the lingerie I truly desired. What the fuck was happening to me?
And, besides the image was a cuckold manifesto. I read it silently once. My heart pounding. My mind becoming more and more convinced by Carla's proposal.
"Now, if you honestly agree to be sissy crossdressing cock-sucking hubby say the words aloud."
Carla had played her hand perfectly. I, looked at that stunning image of my vixen of a wife again, and surrendered fully to her demands:
SIGNS THAT I AM A CROSSDRESSING SISSY CUCKOLD...
I WANT TO WEAR MY HOT WIFE'S LINGERIE, HEELS, STOCKINGS, LIPSTICK AND BASQUE.
I WANT TO WATCH AS LOTS OF HUNKY GUYS FUCK HER.
I WANT TO EAT CREAM PIES FROM MY NAUGHTY WIFE'S PUSSY AND TITS
I WANT TO LET GUYS FUCK MY BOI PUSSY..
I WANT TO SUCK LOTS AND LOTS OF COCKS.
I WANT TO SWALLOW CUM.
FROM NOW ON I WILL BE MY WIFE'S SISSY CROSSDRESSING CUCKOLD.
Carla passed me some of her expensive red lip-gloss.
"What's that for?" I asked, trembling slightly.
"To sign the agreement with, and as a reward, once you've signed I'll apply some of this gorgeous lip-gloss to your lips sissy."
I signed in a heartbeat.
When Carla put the lip-gloss on me it felt wonderfully erotic. I felt even more of a faggot. My cock was now dripping pre-cum one again. I wanted to dress like a slut and get fucked like one.
"What's happens now?" I asked Carla as she placed the agreement into a perfumed envelope and sealed it with a kiss.
"Now you ring James and if you ask him nicely he might bring over some of the sissy nurses we both work with."
The thought of ringing James and begging him to come over and fuck my hot naughty wife was humiliating, but still very exciting. And what a bonus, I was thrilled by the idea that a group of sissy trannies would come and play with me.
"What are you thinking my sexy sissy crossdressing hubby?"
"I feel ashamed telling you."
"Tell me and I'll slide this big black dildo in your man pussy...we'll call it lubrication for the real thing."
I didn't need any more convincing. The thought of that big dildo sliding into my ass as an aperitif for a real cock was insanely exciting. So I held nothing back when I told Carla..."I was wondering if James might let me suck his lovely fat cock before he fucks you with it."
Carla meowed with pleasure by my suggestion.
"I'm sure," she said handing me her phone which was now on speed dial to James, "if you ask him really, really nicely - like a good sissy faggot" Carla finished licking her lips and smearing the big black dildo with some KY jelly. This was quickly spiralling out of control, but I felt powerless to resist.
James picked up on the first ring. His voice was deep, husky, masculine. Almost the complete opposite of mine.
"Hi James," I said in a rather girly voice - Carla black panties, the ones I was now wearing, had already turned me into an effeminate sissy boy.
"You must be Carla's husband. Bet you're ringing me to come and fuck your sexy hot wife because you can no longer satisfy her." James's words didn't hurt me, they simply confirmed the dominance of Carla and James over me. I would be their sissy slave now. And therefore, I not only had to be civil and polite to James, I had to be subservient.
"Oh yes please, master James. Please fuck my hot wife in front of me. Show me how a real man satisfies a sexy woman."
"I'll be right over sissy boy and I'm going to spank your pretty ass and make you suck my cock so it's all nice and hard for your hot naughty wife."
The line went dead. My heart skipped a beat. My cock erupted with more pre-cum landing on the silky black and lace panties. James was going to spank me and let me suck his cock. I was salivating at the thought of it all.
My cuckold training was about to go to the next level...
HOPE YOU'RE HAVING A RELAXING WEEKEND HUBBY. MINE JUST GOT A LOT MORE INTERESTING!
And there, bending over a bed in the hotel room Carla was staying in - she was away at a conference in North Wales - stood my wife of twenty years in only her underwear - pink panties, matching pink balcony bra, ruby red stockings and high heels, smiling at the camera. Carla looked hot as hell. I felt my four inch cock spring to life immediately, but then, when I looked closer, I noticed a 7-8 thick monster cock in the foreground, erect, clearly belonging to some hunky stud. For weeks Carla had been gently, but naughtily teasing me about how she'd like to try a bigger cock - as our anniversary approached she said it was the least she deserved after years of my little member trying to satisfy her.
Although I was a little jealous when she said such things, I indulged her fantasy by buying two enormous realistic vibrating dildos from a sex shop - a white one and a black one (Carla's eyes lit up when she saw the big monster black vibrator).
After I used it on her for the first time she'd purred with delight experiencing multiple orgasms and stating: "So it's true what they say hubby...white girls who try black never want to go back!"
Since Valentine's Day Carla had become more and more outrageous in the bedroom asking me to invent stories about young guys with big cocks fucking her in front of me while I sucked her tits. Part of me was extremely disturbed by these fantasies - Carla had always been so conservative during sex, I wondered what had gotten into her - but I was also thrilled by how excited and liberated she was becoming. And after each orgasm she would sit astride me, stroke my nipples (something that drives me wild) and use the vibrator on my small cock to give me an orgasm.
But now, looking at this picture I felt betrayed, heart-broken and yet, perversely, more than a little turned on. Nevertheless I was still hopping mad and just about to ring Carla to ask her what the fuck she thought she was playing at when another text message came through:
I HOPE YOU'RE NOT ANGRY HUBBY. I HAVE NEEDS YOU KNOW...BESIDES I FORGOT TO PACK MY VIBRATORS! I WONDER IF SECRETLY YOU'RE A LITTLE TURNED ON?! IF SO, SAY "YES I AM MY SEXY HOT WIFE," AND I'LL SEND YOU MORE PICTURES!
This was fight, flight or freeze syndrome. How the hell was I meant to respond to that? I was seething with anger, but I couldn't deny that there was a twisted, debase and deviant set of thoughts and feelings that were flowing through me, nor could I deny that my own little cock was pulsating with anticipation at what images Carla might send me next. Scarcely believing what I was doing I typed the words Carla had requested of me and only spent a moment hesitating before pressing SEND:
YES I AM MORE THAN A LITTLE TURNED ON MY SASSY, NAUGHTY WIFE, PLEASE SEND ME MORE PICTURES AND...ENJOY YOURSELF XX
I couldn't believe I'd added those last two words...ENJOY YOURSELF followed by two kisses. I felt like a voyeur appalled by the depraved images he was witnessing and yet unable, because of some degenerate addiction, to tear himself away from the scenes that were playing out in front of him.
Carla, of course, was delighted with my response. She texted back immediately:
OH MY DARLING HUBBY, THANK YOU, AM I GOING TO PUT ON A SHOW FOR YOU NOW!
Her words caused my cock to swell a little more. I sat on the edge of our bed and rubbed it gently, nervously awaiting the next picture. When it came through I nearly prematurely ejaculated.
Carla's tongue was at the base of the hunky guy's big fat cock which was glistening with pre-cum. She was smiling, clearly savouring the snack she was about to have. There were traces of her red lip-gloss on the stud's shaft and I could tell this was a guy that regularly worked out. His legs and stomach were toned and muscular. Carla is 45, but looks ten years younger. She has a fantastically rounded, big, but sexy as fuck derriere and 34DD tits. I'm 55, more than a little overweight, with a skinny body and thinning hair. I couldn't compete with this guy. I felt another wave of jealousy, Carla has never once sucked my cock, but this was quickly forgotten when my phone pinged again. The next image showed Carla on the bed naked now apart from her stockings. Her pink panties were resting on the end of her right foot which was waving in front of the camera:
WHY DON'T YOU SNIFF AND THEN WEAR A PAIR OF MY DIRTY PANTIES HUBBY. I'VE LEFT SOME IN THE LAUNDRY BIN FOR YOU XX
It was a ridiculous, but enticing, proposition. I know this sounds like it was all happening too fast, but that's the point. Ordinarily I would have dismissed such a ludicrous suggestion out of hand, but Carla was deliberately using the speed of events to prevent me from thinking straight. I felt mesmerised and hypnotised by her lasciviousness. Deranged, I jumped off the bed, opened the laundry bin and finding a pair of her vintage high-waisted purple and black satin panties (purchased from What Katie Did) sniffed the gusset (it smelt of Carla's pussy juices and I found the fragrance dangerously intoxicating), and rolled my hot wife's worn panties up my thighs. When the silken material caressed my balls and cock I had an overwhelming viscerally thrilling reaction. It was like a pleasant electrical charge surged through my body. Once more my cock swelled with pleasure. It took me by complete surprise. Instead of feeling ridiculous I felt strangely liberated. I couldn't resist going over to the full length mirror, running my hands over my chest, nipples, and then over my stiff cock. I cupped my balls through the delightful material and immediately a dollop of pre-cum became visible on my hot wife's panties. I took a selfie and without even thinking about it sent it to Carla. She was delighted by my acquiescence:
OH MY DARLING HUBBY YOU LOOK LIKE SUCH A SEXY SISSY IN MY PANTIES. I WISH YOU WERE HERE SO JAMES COULD FUCK US BOTH. I BET YOU'D LOVE TO SUCK HIS BIG JUICY COCK ONCE IT'S BEEN IN YOUR NAUGHTY HOT WIFE'S PUSSY?! XX
Now you may think Carla had jumped the gun with that comment. That she'd gone too far, way too quickly. But, by now she must have guessed I'd agree to almost anything. And the thought of sucking a cock that had pleasured my wife, was, on the one hand ridiculously stupid and indecent for a straight guy like myself, but on the other hand I felt it was mind-blowingly tempting.
Looking back now it was this salacious idea that got such a grip of me that Carla's desire to cuckold me became impossible to resist. Though I didn't really realise it at the time, my naughty hot wife had just delivered me a knockout blow. From now on she'd be able to fuck as many guys as she wanted and I would be her sissy crossdressing faggot. A part I would crave and therefore play willingly. I simply replied:
I THINK I MIGHT REALLY LIKE THAT MY NAUGHTY HOT WIFE XX
Carla's response thrilled me:
IN THAT CASE MY SISSY CROSSDRESSING HUBBY, AS A REWARD, I'M GOING TO GIVE YOU A LIVE SHOW! OPEN UP YOUR LAPTOP AND I'LL FACE TIME YOU. MY HORNY BEHAVIOUR WILL LOOK SO MUCH BETTER ON THE BIG SCREEN! XX
So I powered up my laptop and with nervous anticipation awaited Carla's call. As I was waiting however, I had a momentary pause: Where, I wondered, had I heard that name James before? My memory banks went into overdrive...but just when I thought I'd worked it out, Carla's call came through. I clicked the accept button and the first image that greeted me was Carla being fucked from behind by James the stud. She was still wearing her stockings and high heels, and in the position she was in she looked like a stunningly gorgeous porn star. Oh, and the howls of delight emanating from her as James drove his big meaty cock into her pussy while his fingers tweaked her nipples, actually made me salivate. Despite my jealousy, watching Carla in paroxysms of pleasure, stirred something primal in me and I felt my cock leak a huge dollop pf pre-cum onto my wife's silky panties. And when Carla gently moved forward, turned and faced James, pushed him on the bed, and lowered herself onto his throbbing, glistening, enormous cock - all the time staring into the camera and giving me a sultry smile - my own hand reached inside Carla's worn panties and I started rubbing my own cock. By now I was desperate for relief.
It was only recently that Carla had admitted to me during one of our role playing games how she'd dreamt of other cocks pleasuring her while I watched - now her fantasy was being lived out in front of me and a strange part of my psyche was weirdly loving every minute of it. I watched, stupefied as Carla started pirouetting and gyrating her pussy up and down the length of James's huge cock. My wife was being a total slut and there I was in our bedroom wearing a pair of her dirty panties watching her fuck another guy senseless and I was loving every minute of it!
When Carla started slamming her pussy repeatedly on James's cock I knew she was reaching the point of no return. When James reached up to meet her tongue with his own and their mouths touched I ejaculated instantly...it was then I felt Carla waking me up.
"Hey, hubby, you've just had a wet dream," she said, accusingly, but laughing at the same time, "there's cum all over the back of my black panties and on my leg. What the fuck were you dreaming about it?!"
It had only been a dream? Shit! I didn't know whether to feel relieved or disappointed.
"Wow hubby, you look really, really guilty," Carla said. "Spill the beans."
"I'm not sure I want to," I replied, rather feebly.
"If you tell me...however naughty or outrageous it was, maybe we can do it for real?" Carla said in a voice dripping with seduction and a touch of sadistic menace.
Unable to resist her coquettish witch-like charms, I finally succumbed and told her the whole lurid story, leaving out nothing. By the end Carla had inserted one of her hands inside her black lace panties and was fingering herself.
"Fuck hubby, I don't think you've ever got me so turned on. My pussy is dripping with excitement," Carla took a deep breath before continuing: "You know who James is, don't you?"
"I couldn't quite remember in my dream, though subconsciously his name rang a bell, but, obviously, when you woke me up just now, I thought he must simply be a figment of my overactive imagination."
Carla smiled and kissed me tenderly, and then more passionately.
"Not at all, hubby. James, if you remember is the hunky new d**g rep that all the nurses were fawning over when he came into my office a couple of weeks ago. The guy I said had just been added to my six guys I'm allowed to fuck list and you can't get mad. He's built like a viking and looks like one too. He does a bit of male modelling on the side and the nurses and I discovered he's actually starred in half a dozen pornos. Remember now?"
"Oh, that James!" I exclaimed swallowing hard as I recalled my dream again and imagined this Norse-like god fucking my hot naughty wife into Valhalla.
"Yes, that James! The thought of him fucking me. Oh sweet Odin! That would make me delirious. And you say, it was definitely James fucking me in your dream."
"Yes, absolutely. And he was hung like a Norse god too." I added for good measure, beginning to enjoy now how much this was clearly turning Carla on.
"How big?" Carla asked, cupping my balls. I gave a little sigh of pleasure as Carla's fingers caressed my scrotum.
"At least eight inches and a girth that would not look out of place on a stallion."
"Oh boy, fuck me! And it turned you on, hubby, watching this hunk fuck your hot naughty wife?"
I hesitated, but by now, I was too far gone to lie.
"Fuck Carla, although it sounds mental, it really did!"
Carla giggled and gave me a saucy look that said she approved of my answer.
"Maybe my dirty panties that you were wearing helped?"
"They certainly seemed to," I answered truthfully.
"So how about you try these ones I'm wearing now then? After all you have just cum all over my ass."
"I don't know Carla, I'd feel like a fool."
Carla looked momentarily crestfallen, but then her eyes brightened again and she pulled the duvet back exposing a huge damp patch on the back of her panties where my cum had fallen, and on her gusset where her own pussy juices had soaked the material, presumably because the thought of James fucking her for real had overwhelmed her with anticipation and excitement. When she was back on the bed properly she had her laptop in her hand. Without saying a word she opened it up - clicked on a tab called: CUCKOLD TRAINING and, as the first image sprang to life, she looked at me with such unbridled desire that I felt my grip on reality and sanity dissipate like dew on an unexpectantly warm spring morning.
The image showed a woman, that looked very similar to Carla, with a huge cock in her hand, her hungry tongue running across the tip of it, beside a caption that posed the question: DO YOU WANT TO LICK IT TOO? I felt my heart skip a beat, and then a surge of some primeval craving rising up from my stomach to my mouth. I even ran my tongue across my lips. I'd never felt any same sex attraction ever, but there was something deeply arousing about that picture and the caption that accompanied it. Something brazenly carnal, base, and risqué, that sent me on a train of thought that I'd never embarked on before. Still completely lost in the moment, I opened my legs willingly as Carla slid her silky black lace panties up my thighs until they nestled deliciously on my balls and cock. I felt a surprising, but potent, salacious thrill. I wasn't dreaming anymore. This was reality and I was beginning to love every perverse moment of it. Suddenly, all thoughts of resisting this journey Carla was clearly intent on taking me on, simply melted away as my cock stiffened in my hot wife's dirty panties. It was thrilling to feel her damp gusset on my ball sac, a dampness I knew was due to the thought of James the Viking fucking her into oblivion.
The cock in the image was hypnotic. I think what was so titillating about it was that the woman in the image really could have been Carla's doppelgänger - something I thought, later, my hot naughty wife had planned to perfection. And, I knew, in that moment, that if Carla offered me a cock to lick and suck, especially a cock she herself had licked and sucked, I'd probably be unable to resist such a sensual temptation.
Any lingering doubts were dispelled a few seconds later when Carla clicked on the next image. Now the same Carla lookalike was down on her knees, the same hunky guy's cock in her mouth, her red lipstick all over the shaft, and, oh, the caption, the caption was mesmeric: BET YOU WISH MY LIPS WERE YOURS, DON'T YOU SISSY?
My dream and now this. Carla was pummelling me with a type of foreplay I'd never imagined would turn me on. It was like she had simply, with ease, pressed a gay crossdressing cuckold switch in my brain and any thoughts of being straight again had vanished instantly. Seeing my prurient desire increase with every second that ticked by Carla decided to go all out and clicked the final image. It showed a middle aged guy like myself dressed in his wife's fishnet stockings, push-up bra and crotchless panties, soft red lip-gloss, mascara and false eyelashes, being fucked in his boi pussy by his wife's lover. The sissy faggot was staring into the camera, his wife was being fucked by two hunks at the same time, and the caption made me burst with longing. It read: "Oh, that feels so good my naughty wife, SO good, you making me a crossdressing sissy cuckold was the best thing you could have done for our marriage. Like you I now simply adore big cocks!"
Somewhere in the back of my mind, in some dark recess, I knew Carla was using these images as some sort of lascivious mind control to turn me into her femboi, but I was now powerless to resist her dominance over me. My own cock was now dripping with pre-cum, staining my wife's dirty black lace panties I was wearing until a small pool of liquid was protruding through the silky material. In an instant Carla ran a finger over the wondrous fabric scooping up a large teaspoonful of my salty pre-cum and spreading it on my lips and tongue. I'd never tasted my own cum before, but instead of finding it repugnant, instead of gagging on the liquid, I found myself hungering for it.
"More," I whispered hoarsely.
Carla squealed with delight and peeling the fabric of her dirty panties a little away from my fully erect four and a half inch cock, she started rubbing my little penis until another dollop of pre-cum glistened and dropped onto her hand. But this time she reached into her bedside table and pulled out her favourite dildo - it was nine inches, incredibly lifelike, and black. She placed my pre-cum onto the tip of the dildo and after saying: "open wide", inserted it into my mouth. To intensify the experience for us both she clicked on another image on her laptop. It showed a sissy crossdresser fully made up in a shiny black wig, tarty make-up, a black bodice, pink stockings, vintage cherry coloured panties and high heels about to take an enormous cock into his gaping mouth - a cock that had just exploded and was dripping with cum. The caption read: THE SISSY CUCKOLD'S MOUTH WATERED AND HE KNEW HE WAS GOING TO SWALLOW EVERY LAST DROP. Reading those words caused me to furiously lick and suck the black dildo my hot wife had just put in my mouth. I felt so gay now. I was so hungry for cock, I knew if Carla had brought some hot guy home for the weekend we'd be competing with each other to see who could give him the best orgasm. We'd certainly be passing his cock between our mouths in a game of tonsil tennis.
Carla took the dildo gently out of my mouth and started to lick and suck it herself.
"It's good to share," she said, as she passed it back to me, clicking on another picture. There was no subtlety to this image. It simply showed another sissy crossdresser (wearing a very short pleated mini skirt and balcony bra that made him look so sexy I could scarcely believe it was guy until I looked a little closer and saw an enormous bulge in his purple satin panties), kneeling down holding a lovely seven inch cock that was firing cum directly onto his awaiting tongue. The caption underscored how I was now feeling: ONCE YOU'VE TASTED CUM, THERE'S NO GOING BACK. I knew, instinctively this was true, but I also knew, as Carla had returned to caressing my cock, that as soon as I orgasmed my yearning for cock would disappear like a bad dream. But Carla was one step ahead of me yet again.
She too, suspected, that if her nefarious plan to turn me, her husband, into her sissy crossdressing cuckold was to work, she would need to prevent me from coming too soon. And if she really wanted me to suck cock she would have act fast. Unbeknown to me her planning was as good as a military campaign, her arsenal was fully equipped and she was about to launch a pre-emptive strike that would change everything.
"Well, I think that's enough for now, don't you hubby?" Carla said, teasingly.
"What do you mean, you can't leave it there?" I said imploringly.
"Why not hubby?"
"Because I'm gagging for it Carla."
"Well, so am I."
"So let's do it then."
"As I suspected Dan, you're not my sissy crossdressing cuckold just yet. You need further training."
"I don't Carla, I'm ready. Honestly."
"But you can't be."
"Why not?" I begged. Really not understanding where this was going.
"Because if you were, you'd know your tiny little cock could no longer satisfy your hot naughty wife. You'd want me to get fucked by lots of hunky, horny guys like James."
"But I do, Carla. I really do." I blurted out, totally consumed now by sissy desire for relief whatever form it took.
"You promise? You promise to not only support other hunky guys fucking your naughty wife, you will watch them doing so, and clean up the mess afterwards by eating lots and lots of cream pies?"
I knew what that would mean, but I would have agreed to anything at that moment.
"Of course I will, Carla. I'm actually looking forward to it."
"I think I'm actually starting to believe you hubby."
"It's true."
"Okay, prove it to me."
"How?"
Carla once more reached into her bedside table. She pulled out an A4 sheet of paper. On the right hand side it showed the most sexy, sultry picture of Carla I'd ever seen. It had obviously been taken in our bedroom - which begged the question: Who the fuck had taken it? But I was too far gone to care. Anyhow, Carla had never looked hotter. She was kneeling on our bed, staring directly into the camera, her shoulder length brunette hair looking glossy and lustrous. Her make-up was perfect - tarty, but stunning. Bright scarlet red lip-gloss, long false eyelashes, and smoky mascara. Think slutty, but stylish soft core porn star. And her outfit only consolidated that thought. Fuck it was mind-glowingly sexy. Spiked high heels, the finest shimmering black stockings attached, via delicate lacy suspenders, to a diaphanous black basque, and full satin sparkling black panties. A wicked thought crossed my mind: I realised it might be immoral to some couples, but my wife looked so fucking hot I knew that Carla was right - there was no way my feeble cock could fulfil her needs any longer - but, it would be a genuine pleasure to watch a load of hunky studs shagging my wife's brains out. Looking as gorgeously sexy as she did, and is, it was nothing less than she deserved. I was also struck by how much I wanted to wear that amazing slutty outfit she was wearing in the picture. And, yes, of course that included the high heels, mascara, lip gloss and false eyelashes...though it was the lingerie I truly desired. What the fuck was happening to me?
And, besides the image was a cuckold manifesto. I read it silently once. My heart pounding. My mind becoming more and more convinced by Carla's proposal.
"Now, if you honestly agree to be sissy crossdressing cock-sucking hubby say the words aloud."
Carla had played her hand perfectly. I, looked at that stunning image of my vixen of a wife again, and surrendered fully to her demands:
SIGNS THAT I AM A CROSSDRESSING SISSY CUCKOLD...
I WANT TO WEAR MY HOT WIFE'S LINGERIE, HEELS, STOCKINGS, LIPSTICK AND BASQUE.
I WANT TO WATCH AS LOTS OF HUNKY GUYS FUCK HER.
I WANT TO EAT CREAM PIES FROM MY NAUGHTY WIFE'S PUSSY AND TITS
I WANT TO LET GUYS FUCK MY BOI PUSSY..
I WANT TO SUCK LOTS AND LOTS OF COCKS.
I WANT TO SWALLOW CUM.
FROM NOW ON I WILL BE MY WIFE'S SISSY CROSSDRESSING CUCKOLD.
Carla passed me some of her expensive red lip-gloss.
"What's that for?" I asked, trembling slightly.
"To sign the agreement with, and as a reward, once you've signed I'll apply some of this gorgeous lip-gloss to your lips sissy."
I signed in a heartbeat.
When Carla put the lip-gloss on me it felt wonderfully erotic. I felt even more of a faggot. My cock was now dripping pre-cum one again. I wanted to dress like a slut and get fucked like one.
"What's happens now?" I asked Carla as she placed the agreement into a perfumed envelope and sealed it with a kiss.
"Now you ring James and if you ask him nicely he might bring over some of the sissy nurses we both work with."
The thought of ringing James and begging him to come over and fuck my hot naughty wife was humiliating, but still very exciting. And what a bonus, I was thrilled by the idea that a group of sissy trannies would come and play with me.
"What are you thinking my sexy sissy crossdressing hubby?"
"I feel ashamed telling you."
"Tell me and I'll slide this big black dildo in your man pussy...we'll call it lubrication for the real thing."
I didn't need any more convincing. The thought of that big dildo sliding into my ass as an aperitif for a real cock was insanely exciting. So I held nothing back when I told Carla..."I was wondering if James might let me suck his lovely fat cock before he fucks you with it."
Carla meowed with pleasure by my suggestion.
"I'm sure," she said handing me her phone which was now on speed dial to James, "if you ask him really, really nicely - like a good sissy faggot" Carla finished licking her lips and smearing the big black dildo with some KY jelly. This was quickly spiralling out of control, but I felt powerless to resist.
James picked up on the first ring. His voice was deep, husky, masculine. Almost the complete opposite of mine.
"Hi James," I said in a rather girly voice - Carla black panties, the ones I was now wearing, had already turned me into an effeminate sissy boy.
"You must be Carla's husband. Bet you're ringing me to come and fuck your sexy hot wife because you can no longer satisfy her." James's words didn't hurt me, they simply confirmed the dominance of Carla and James over me. I would be their sissy slave now. And therefore, I not only had to be civil and polite to James, I had to be subservient.
"Oh yes please, master James. Please fuck my hot wife in front of me. Show me how a real man satisfies a sexy woman."
"I'll be right over sissy boy and I'm going to spank your pretty ass and make you suck my cock so it's all nice and hard for your hot naughty wife."
The line went dead. My heart skipped a beat. My cock erupted with more pre-cum landing on the silky black and lace panties. James was going to spank me and let me suck his cock. I was salivating at the thought of it all.
My cuckold training was about to go to the next level...
7 months ago
