A Question of Cock

It was Carla's idea. A week away. A week to spice up our dormant sex life. A week of sharing our most perverted fantasies and trying to live at least three of them out. No holds barred. No limitations. No rules. I was so excited, that as I put some books on the shelves at the local library where I work I felt a little stiffy growing in my trousers.

Finally the weekend arrived. Carla got home early from the fertility clinic where she works as a doctor and we set off to our luxurious hotel where we would be staying. On route the kinky games commenced as Carla began asking me a barrage of outrageously naughty and bawdy questions.

"The filthier your responses," she said as we got on to the motorway, "the more I'll turn into the woman of your dreams...a hot and very, very naughty wife."

To show me how serious she was Carla immediately lifted up her pinstripe jet black pencil skirt and gave me a flash of her black glossy stockings. It took all my concentration not to crash the car.

"There's plenty more where that came from hubby. Provided of course you play along and...answer every question honestly." Carla finished her instructions by pouting at me seductively.

"Agreed," I said through bated breath.

"Okay, ready hubby?" I nodded, bursting with excitement and anticipation. I was already bowled over by Carla's risque mood. Our sex life had become so predictable. In my more honest moments I knew that was mainly my fault. Heading towards sixty, I'm flabby around the middle, my cock really is small - just over four inches - and I've never been able to give Carla an orgasm without using one of her favourite vibrators to stimulate her. I genuinely don't know how she's put up with me for so long. Especially as she's still, at 51, stunningly attractive. Voluptuous body - not fat - just enthralling - think sexy vampire with big tits and a magnificent derriere, and a pussy that grips like a vice and swallows you whole. I can't help thinking, as I pass a caravan, how what Carla really needs, deserves even, is a big fat cock, preferably several of them, to satisfy her. But she'd never cheat on me. Nor I on her. We really do love each other. But she definitely has grounds for looking for sexual kicks and pleasure elsewhere. And I really couldn't blame her if she did sleep around.

"One final thing," Carla added, as she reapplied some really seductive red lip gloss. "Remember - we'll be playing EITHER/OR. So even if one of my suggestions appalls, scares or even terrifies you, you must give me your preference. Do you understand my lovely hubby?"

"Understand, loud and clear my hot sexy wife." I said, as my heart skipped several beats thrilled at the prospect of what the next 90 minutes would reveal until we arrived at our hotel for the week.

"Fabulous. Question 1: Would you rather see me kiss another woman or another guy?"

"Easy peasy," I replied, licking my lips. "Another woman."

"Question 2: Do you prefer me to wear tights or stockings?"

Another straightforward one. "Stockings every time."

But as Carla asked her next question I sensed a gear change - if you'll pardon the pun - I'd just put our vehicle into fifth gear.

"If we get the chance on our way to the hotel for me to put on a little show. In other words hubby, if your hot sexy naughty wife turns into an exhibitionist...Would you prefer me to flash my breasts at the passing truck drivers or my panties?"

Great question, I thought, And it was a question that didn't offend me at all. A perverse part of me has always loved the idea of Carla and I getting caught having sex in a lift, or in a changing room. And I've always secretly loved the idea of Carla turning other guys on knowing they can enjoy what I get to see everyday...namely, how gorgeously alluring my wife is - especially in her sexy underwear.

"That's a real tough one," I said. "I love the idea of a trucker - or any guy for that matter seeing your 34DD's, but the thought of some guy seeing your panties is ridiculously enticing."

"Really?" Carla replied, clearly more than a little surprised and obviously thrilled by my response. So much so that she leaned over and gently kissed my neck.

"Absolutely. I know other guys must find you incredibly attractive and sexy. So I don't see any harm at all in you giving them well...far more than a cheap thrill!"

"Good answer hubby. A very pleasurable answer and one that if the opportunity arises I'll definitely take advantage of."

"You don't need my permission my naughty hottie."

I could almost see Carla thinking...be careful what you wish for Dan.

"Next question: If you had to choose one...Would you rather watch me have sex with a she-male or a crossdresser?"

Fuck, what a question, I thought. I was trembling a little thinking about the scenario.

"A she-male, I think."

"Interesting. But why a she-male hubby and not a crossdresser?"

"I don't know. I guess a she-male has real breasts and wow that would be quite something to watch."

"Are you serious, Dan?"

"Yeah, deadly serious I think that would be really exciting - watching you with what looks like a woman - so therefore a bit of girl on girl action. But then, SURPRISE, he/she pulls out his big cock and gives you the ride of your life!" Fuck, where did that come from I thought. And Carla was clearly excited by the prospect. She had hitched up her skirt and two of her fingers were now massaging her clit.

"That answer has made your hot naughty wife very, very damp." Carla then took a deep breath, regained her composure somewhat and fired the next question at me. "And what about you hubby...Would you prefer to have sex with a she-male or a crossdresser?"

Shit. I didn't see that one coming. Funny thing is there's this cleaner at work...Rylan...who is a crossdresser. He wears a lovely glossy shoulder length brunette wig, always dresses immaculately...beautiful dresses, make-up and high heels and last halloween, after work, he even asked me to help him get into a pink corset and I even attached his stockings for him as the clips, according to him - and he was wearing very long false nails - were very fiddly. He was doing burlesque at some club in town, he explained, and had to look his very best as the punters would be voting for their favourite drag queen and there was a £10,000 prize for first place. He actually finished second and won half that amount. Anyway, the reason I'm telling you all this is as I was helping him get dressed I kept looking at the shape of his cock in his pink ruffled vintage panties and I got quite turned on. I'm sure he noticed, but he was too polite to say anything. I felt thoroughly ashamed afterwards. And I never told Carla of course, I didn't want her to think I was gay or even bi-curious. But thinking about Rylan now I realised I knew the answer to Carla's question.

"I think I'd choose to have sex with a crossdresser actually."

I heard Carla give a little moan of pleasure just as we left the motorway, got on the slip road and head further west along the dual carriageway.

"Oh hubby, that really does turn me on. Isolated question: Do you like crossdressers Dan? Is that one of your fetishes? Would you like to have sex with a sissy faggot?"

I didn't find any of Carla's questions disgusting. Quite the opposite in fact. I kept picturing Rylan in the changing room at work in his corset, stockings, high heels and pink ruffled panties looking like a nymphomaniac in one of those old Hammer House of Horror movies. I was beginning to feel like one myself.

"I don't dislike them," I said honestly. "There's actually one at work, Rylan, who looks amazingly convincing as a woman in his feminine attire. I'd go so far as to say he's really attractive." Carla's eyes were popping out of her head at this news. "But I don't have any desire to have sex with him."

"But you would choose Rylan over a more feminine looking she-male real breasts?"

"Oh absolutely!" I said, perhaps a little too emphatically.

Again Carla was clearly thrilled at my answer. She pulled out one of her smaller vibrators and, after kissing the tip, unbelievably put it in her mouth before asking: "And would you like Rylan's cock in your ass or in your mouth darling hubby?"

"Oh in my mouth definitely." I said, surprising myself a little, but remembering seeing Rylan's big fat cock in his pink ruffled panties and feeling this overwhelming urge to slip it out of his sexy knickers and after kissing and licking his pre-cum taking it greedily into my virgin cock sucking mouth. Oh fuck me, I thought what am I doing thinking like that? I'm straight. Straight as an arrow. Aren't I? Or has my naughty wife tapped into some sissy feminine side of me that's always been there. She clearly had, and now she started to turn the screw as her excitement mounted.

"Okay hubby. Some rapid questions now. Try not to think too much about them. Just answer me honestly again and I promise to give you the best sex you've ever had as soon as we get to our room."

"Agreed," I managed, starting to get really aroused myself. "Go!" I implored.

"Would you like to watch me have sex with one hot stud or lots of studs?"

"Lots of studs!"

"Would you wear my underwear - panties, stockings, bra, chemise - and let we watch you get fucked in the ass by some hot sissy crossdressing faggot?'

"I'd not only allow you to watch my hot sexy wife and I'd ask you to film it so I could show Rylan at work and you could show it to all the gay guys who come to the fertility clinic so they could produce a good sample!"

"Oh fuck my little sissy faggot, that's such a hot answer."

It sure is, I thought, as I felt a dollop of pre-cum splash onto my boxers. It was becoming increasingly difficult to concentrate on the driving.

"Would you like to watch me suck another man's cock darling hubby/"

"As long as it was a big fat cock." I said. Carla purred with pleasure at my response.

"Would you suck a big fat cock for me if I begged you too?"

"You wouldn't have to beg my naughty hot wife."

"Oh fuck, Dan. What an answer. You're going to have to pull over. I'm gagging for it now. How far to the next rest room?"

"Just a few miles."

"Thank fuck. Okay I'll keep going...Has Rylan got a big cock?"

"Yes...it's enormous."

"Oh Dan, how can you possibly know that?"

That's when I told Carla the halloween story. The story turned her on so much that by the time we got to the rest room we were both ready to do it in the back of the car even if everyone at the service station saw us. Problem was we both needed the loo. So we invented another game. We agreed to swap underwear and go the toilet wearing our partner's panties or boxers. We took these off as quickly as we could in the car. Carla had been wearing her lacy blue satin panties - she knows they're my favourite pair and when I slipped them on I got a visceral thrill of excitement and arousal that I'd never experienced before. They felt thrillingly kinky - especially as the gusset was soaked with Carla's pussy juices. And when Carla put my boxers on she still managed to look sensationally hot.

"Oh hubby, you definitely look better in my panties. I think you should wear them for at least the remainder of the journey and preferably for the whole week."

"Sounds like a good idea," I said relishing the prospect. More so now I was actually wearing a pair of Carla's panties for the first time. The satin lacy material was exquisite. I felt such a strong desire desire to suck cock now that I felt girly, feminine. Fuck, what was happening to me. I was aroused wearing my wife's panties and now all I could think about was what it would be like to kneel over a hot guy, preferably a guy wearing panties like me, and lick and kiss and suck his cock and swallow his yummy cum. Carla suspecting something kinky was going on in my head said:

"Oh Dan, you look so hot in my panties, sissy hubby, I think if you wore some black stockings and suspenders, a black leather skirt and a pink balcony bra all the sissy faggots would beg you to suck their cocks. After all a sissy dressed as a slut is an absolute cum whore."

Carla's words resounded in my mind like a bewitching temptress's magic cocktail. It was a hypnotic brew swirling around in my most depraved fantasies as I desperately tried to use the loo in the rest room. It was difficult, not only because I had a big erection, well a big erection for my little dicklet anyway - no more than four and a half inches, but also because I both feared some guy bursting into my cubicle to see me wearing panties and at the same time hoping one might. Eventually I succeeded in urinating. And Carla and I sped off to our hotel, both of us yearning for coitus.

As we got within 15 minutes of our destination Carla said something that I completely concurred with.

"Thing is Dan, my darling hubby, you and I both know your cock is really, really small and therefore such cocks only belong in panties. You're really a woman, not a woman like me, obviously, but a sissy. And sissies need to be trained."

"How so?' I asked increasingly aroused and intrigued.

Carla then explained that there were several levels to sissy training:

SISSY LEVEL 1: HEELS, MAKE-UP, WIG, LINGERIE

SISSY LEVEL 2: HEELS, MAKE-UP, WIG, LINGERIE...BI-CURIOUS

SISSY LEVEL 3: HEELS, MAKE-UP, WIG, LINGERIE...BI-CURIOUS, CRAVING COCK

SISSY LEVEL 4: HEELS, MAKE-UP, WIG, LINGERIE...BI-CURIOUS, CRAVING COCK, SUCKING COCK

SISSY LEVEL 5: HEELS, MAKE-UP, WIG, LINGERIE...BI-CURIOUS, CRAVING COCK, SUCKING COCK, FUCKED IN THE ASS...TOTAL CUM SLUT.

"The question is Dan. By the end of the week what level will you be? Or to put it another way...What level do you desire to be? Answer honestly and I'll make sure it happens."

"Promise?" I asked in a silly prissy sissy feminine voice.

"Absolutely darling hubby, provided I can also cuckold you so your hot wife can get royally fucked by as many horny guys as she wants."

"Of course you can my hot sexy naughty wife."

"Fabulous," purred Carla in an alluring coquettish voice. "So what level my darling sissy faggot?"

I was definitely ready to embrace LEVEL 4, but LEVEL 5...having a big fat juicy cock in my panty clad ass? Did I really want that? The truth was the more I thought about it the more I realised this was something I'd been suppressing all my life. Several movies came to mind...'Carry On Screaming', 'The Rocky Horror Picture Show', and Dr Jekyll & Sister Hyde'. I adored those movies. I found them ridiculously arousing and I realised there was a common theme that ran through them all. Hot, tight fitting dresses, men being seduced, often by strong hot women or sissy faggots. Why would I deny myself that pleasure any longer? Surely, a subconscious part of me had married Carla because I knew deep down she was a flirt, a dominatrix, a hot naughty wife who wanted to cuckold me? It all made sense now. I did want to be a sissy crossdressing faggot. I did desperately want to suck cock (lots of them) and I did want some other sissy faggot to fuck me in the ass while I was wearing a nurse's uniform or a French maid's outfit together with a pair of Carla's silkiest panties and black stockings. And I really did want to watch my hot sexy wife get fucked by lots of well hung gorgeous studs. I so wished I'd sucked Rylan's cock now. Every time I thought about it encased in those sexy ruffled panties I got really aroused.

"Carla, I want to get to LEVEL 5 ASAP and I want to watch you my hot sexy wife get fucked by lots of gorgeous guys."

"Oh Dan," Carla said, as we pulled into the car park. "do you really mean that?"

"Absolutely. 100%. You're so fucking sexy and I know now I want you to cuckold me, dress me in your lingerie and get me to suck other sissy cocks. I want to be a sissy crossdresser Carla and I want you to be a hot wife."

Carla kissed me passionately. We raced into the reception area. The guy on the front desk was about my age. Not bad looking and...clearly as gay as the day is long. Carla gave me a suggestive wink. I returned it with interest by licking my lips and nodding my head.

The guy was called Walter and he was joined by a much younger guy - not a day over 30.

"This is Ged. He's just about to start his shift, so if you need anything later I'm sure he'll be more than happy to help you."

"I certainly will." Ged said, clearly flirting with Carla who unabashed blew him a kiss.

"Hope you've got plenty of stamina Ged." Carla said outrageously.

"Oh I'm a thoroughbred." Ged said confidently. It was clear the guy had the hots for Carla and she for him. And he was so good looking. It was clear he worked out at the gym. He was built like a rugby player. And he had huge hands. And you know what they say about a guy with huge hands!

"Anyway," Walter continued interrupting all our nefarious perverted thoughts I'll show you to your room. You're booked into the junior suite I believe.

As we got into the lift Carla kissed me passionately again - right in front of Walter.

"Sorry Walter, I just can't keep my hands off him tonight."

"Well, if you don't mind me saying," Walter said in a very effeminate, but nevertheless strong voice, "I can totally understand that."

"Really?" Carla and I said in unison.

"Certainly. Your husband is a very attractive man. Definitely my type if he wasn't straight that is." The last three words were uttered in a very titillating manner. It was almost as if Walter knew I was now bi-curious. Something which shocked me as I'd only just started realising it myself.

"I think we should see if my very attractive husband Walter prefers my kisses or yours. After all if you really do think he may be your type it would be terrible of me not to let you see whether you are right. That's if you'd like to kiss him Walter?"

Walter could clearly see where this was going now. He looked like he'd won the lottery. He couldn't believe a gorgeous hot wife was basically offering her husband (ME!) on a plate to him.

He quickly opened our door and put our suitcases down.

"Walter before you leave I really must insist you get you tip - so to speak and kiss my darling husband...but before you do would you mind undressing us both?"

"Happy to oblige, though I'm not sure I'll be able to keep my hands off either of you as I do so."

"Of both of us?" Carla asked bawdily. "Are you not gay?"

"No, I'm bisexual."

"Oh Walter, that is music to my ears."

"And I'm a crossdresser."

"Seriously?" Carla and I again asked in unison. This was getting better and better.

"Are you wearing any ladies underwear now." Carla asked.

"Unfortunately not."

"Would you like to Walter? My husband is wearing a pair of my panties underneath his trousers. So it only seems fair."

"Oh yes please and can I see your husband in your panties." Walter was nearly begging now.

"Off course you can Walter. Undress my gorgeous sexy hubby first while I fish out a pair of my vintage silk panties for you."

I took my own top off in seconds. I couldn't believe how quickly this was escalating. As soon as I felt Walter's hands undoing the button of my trousers and then unzipping them I felt a huge surge of salacious lust and desire for him. It was even more thrilling because Carla was the catalyst for all of this. She was pulling all the strings and clearly loving it as much as Walter and I were. All I wanted Walter and I to do now was to dress in my hot wife's sexiest lingerie and suck each other's cocks as Carla watched and filmed the whole thing - I was desperate to show Rylan what a sissy crossdressing faggot I'd become in the space of a few hours.

Walter had removed my trousers now and both he and Carla could see my little dicklet pulsating through Carla's panties. There was a huge dollop of pre-cum visible on the silky material.

Carla now kissed Walter passionately. Then she removed all his clothes and slid on her most elegant, ruffled pink vintage panties. Seeing Walter in my wife's favourite panties sent me into a sea of perverted desire. He looked so hot in Carla's panties that I realised again that I really had longed for this most of my adult life. And it was even hotter because I'd just watched Carla kiss him, and instead of feeling jealous I felt even more turned on, especially when I noticed the effect Carla's kiss had had on Walter's cock. It was now as hard as a rock and much, much bigger than mine. And I absolutely loved the fact that my hot naughty wife had given another guy an erection right in front of me. And now I wanted that same cock in my mouth. I felt this overpowering urge to kiss it and suck it. Walter could clearly tell I was nervous and so could Carla. But Carla could also tell I was yearning to do so. And wearing her silky panties made me feel...well, girly, horny, slutty. I was turning into a sissy whore.