tagTransgender & CrossdressersKissing Crossdressers Pt. 02

Kissing Crossdressers Pt. 02


I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do.

I felt a sense of shame, guilt and disgust with myself. I took a long hot shower and made a firm resolution never to do anything so perverse again. I hadn't counted on Carla's ability to wrap me round her finger, or rather her curvaceous ass.

I stepped out of the shower just as my phone pinged. I picked it up and saw a message from Carla...MORNING HUBBY LOOK WHAT I GOT UP TO LAST NIGHT! I tapped the screen to download an image. When it opened I dropped the towel that was wrapped around my waist. Carla was lying on a bed in her gorgeous, slinky knee-length black dress with her curvaceous panty-clad ass waving at the camera. Her dress was covered with cum. In the frame of the picture, a bulging cock was dribbling with cum. I swallowed hard and shaking, replied: Carla WTF?! Carla replied immediately...OH DON'T BE UPSET HUBBY, THE HEN PARTY GOT A LITTLE BIT OUT OF HAND. I DID NOTHING WRONG...WELL, ALMOST NOTHING! ALL THE GIRLS CAME BACK TO MY ROOM WITH THE STRIPPER AND, WELL, ONE THING LED TO ANOTHER, AND ONE OF THE BRIDESMAIDS STARTED RUBBING THE STRIPPER'S COCK AND IN NO TIME AT ALL HE'S SPURTING CUM ALL OVER YOUR NAUGHTY WIFE.

I was still angry, but Carla's response made me feel a little better. Besides my cock had suddenly sprung back to life. The image of my sexy wife with some other guy's cum all over her dress was sordidly arousing. And looking at her sexy ass in those gorgeous panties made me yearn to be in her position.





We both laughed, told each other how much we loved one another and then put the phone down.

I looked at the picture of Carla again covered in the stripper's cum. She looked outrageously hot and naughty. Her mouth was agape, but her eyes were sparkling. She looked like she was saying...OH FEED ME, BIG BOY! Then I realised, I'd actually love to watch my wife suck another man's cock, in fact, I'd love us both to be wearing a strappy black dress, high heels, stockings, panties, a push-up bra and scarlet red lipstick whilst we sucked a couple of hunks or at least shared one enormous cock. I felt hypnotized by that picture, drugged and delirious.

My resolution to be a good boy from now on and not descend into perversity again melted instantly. I picked up Carla's purple panties and slid them on once more. Immediately I felt that wonderful sensual pleasure I'd experienced for the first time the previous evening. Something primitive in me was stirring. Something truly life-changing. I went to the wardrobe and picked out a slutty looking basque that Carla had worn to a Halloween party last year. It's funny, if I remember rightly, she wanted me to wear it and a pair of her panties and stockings. The party was fancy dress and the theme was the Rocky Horror Show. Carla had said we could go as a couple of sweet transvestites. I point blank refused, genuinely scared of what people might think of me, so I dressed as

a vampire instead. I wonder whether that was the catalyst for something? Anyway the basque is ivory, and trimmed with light blue lace and delicate pink ribbons. It was a struggle to put it on, but after I did I noticed the suspender clips that went with it. I picked out a pair of vintage blue stockings with a line down the back of them from Carla's drawer and rolled them up my thighs attaching them to the suspender clips. The effect was electrifying. My cock went into spasm, thrilled to new heights by the sensuous feeling the lingerie was having on my male body.

I opened Carla's laptop and clicked on another of the bookmarks: SEXY CROSSDRESSING SISSIES...the first set of images revealed a gorgeous crossdresser wearing a silky, and very realistic, dark wig. He was encased in black stockings, suspenders, panties and a stunning red balcony bra that was barely covering some delicious silicone breasts. Fuck he looked amazing.

In the first image he was kneeling up on a bed, the false nipples protruding through the silky balcony bra. The caption read: IF YOU ARE DRESSING LIKE A GIRL...I breathlessly moved to the next image. The gorgeous crossdresser was now on all fours being fucked in the ass by a beautiful male model...YOU HAVE TO FUCK LIKE A GIRL, the caption stated. In the next picture the crossdresser was waving his sexy ass in the air, the male model's big cock spearing him...the caption said: YOUR ASS...IS YOUR PUSSY. Fuck, I thought, this is so fucking naughty and horny. I love it! The next image had me grabbing for the rampant rabbit I'd pleasured last night...the male model's cock was on the lips of the crossdresser, cum was dribbling from his mouth and had trickled onto his titties...the caption stated: AND YOU TAKE CUM, IN YOUR MOUTH, LIKE A GIRL. The final image showed cum all over the crossdresser's ass, face and tits, and the caption read: THIS IS YOUR FUTURE SISSY...CARE TO JOIN US? Yes! Yes, fucking yes! You fucking bet I want to join you. I started rubbing my cock again overcome with depraved excitement. I was desperate now to be a gay crossdressing sissy. Wearing Carla's lingerie had been a good start, but I realised it would never be enough.

I realised if I was going to be a convincing sissy I would have to shave or at least trim my pubic hair. I went into the bathroom, picked up one of Carla's pink razors and hesitantly, at first, began to trim some of the bigger hairs. But then something possessed me and I couldn't stop. I shaved every last little hair off my balls and pubic mound. I looked at myself in the mirror and actually started laughing uncontrollably and saying over and over again...I shaved my balls, I shaved my balls, I shaved my fucking balls. I'm a little sissy gurl. I rolled Carla's panties back up my crotch and squealed with pleasure. Already I looked and felt more girly.

I spent the rest of the morning and much of the afternoon, looking at pictures of sexy crossdressers. By the time evening arrived I realised I wanted some live action. Carla and I live in a city centre apartment a ten minute walk from the city's gay village with its numerous bars, restaurants and nightclubs. I was hardly ready to go there dressed fully as a sissy, but I felt this urge to at least put on a pair of Carla's panties, stockings and bra under some male attire and have a drink or two in one of the bars.

By 9.30pm after having had a huge internal struggle with myself for several hours I decided it was a bad idea. I looked at myself in the bedroom mirror. I was dressed in a pair of high-waisted cobalt blue panties and matching bra that Carla had puchased only a couple of weeks ago from Boux Avenue. The elastene gusset liner satin material had kept my cock fully aroused ever since I'd put them on an hour earlier. The bra, with its pretty lace trim was gently caressing my nipples which was driving me insane. I still had on the blue stockings with the line down the back of them. I was gagging for sex, desperate to just kiss another crossdresser simply to know what the reality felt like, but fear was preventing me from following through. I had just resigned myself to another night in with Carla's vibrators when my phone rang. It was Carla wanting to Facetime. Shit!

I quickly scrambled under the duvet and pressed: ACCEPT. Carla was lying on her hotel bed dressed in some white lacy panties and bra that I'd never seen before. She looked incredibly sexy.

"Hi hubby, just thought I'd Facetime you before I head out tonight. How's your day been? Did you go to the cinema? Are you in bed already?!"

"Erm, yeah it was good. Very relaxing. Just chilled at home. Weather's been awful here. And yeah, a bit tired." I was very conscious that I was wearing Carla's underwear and I was desperately trying to curtail this conversation as quickly as possible. At the same time it was thrilling to be speaking to my wife while we were both wearing her sexy underwear. My cock was throbbing with pleasure inside the sexy panties.

"So what you up to tonight my sexy wife? You look so fucking hot in that outfit."


"Absolutely. You're going to turn a few heads looking like that."

"Do you really think so?"

"I really do."

"I mean I'll have to put a dress on as well."

"Why bother? You're already dressed to thrill." We were both really enjoying this.

"Well how about if I put on a daring pair of black fishnet stockings I picked up from Ann Summers recently...wait there a moment."

I watched enthralled, rubbing my cock through Carla's panties under the duvet as my very naughty hot wife glided the black fishnet stockings up her legs. She stood up when she'd finished and gave me a little twirl.

"So what do you think hubby?"

"I think there's going to be a plethora of men in the bar who, given half a chance, will want to fuck my naughty wife tonight." Carla's underwear was turning me into a proper little sissy cuckold. I couldn't believe the things I was saying to her.

"Oh fuck, now that kind of talk coming out of my husband's mouth is really turning me on. How do you think the men in the bar will respond if I bring a couple of them back to my room and bend over the bed like this with my tits hanging out?"

Carla then removed her breasts from the lacy bra, put on a pair of black spiked high heels and bent over the bed. She gyrated her curvaceous ass in concentric circles and put a finger in her mouth. I was now rubbing my cock furiously.

"So what do you think those guys will want to do to me hubby?"

"I think they'll want to roll your sexy white lacy knickers down, spank your big curvaceous ass and fuck you all night, filling you over and over again with their manly cum."

"But hubby that's terribly naughty. How would you feel about other guys spanking and fucking your sexy hot wife?"

"Oh Carla, it turns me on so much. I want you to fuck any guy you want from now on, anytime you want."

Carla's eyes lit up at this news like a firework on the fourth of July.

"But wouldn't you be angry, sad, and jealous my lovely hubby?"

"No, not at all. I'd be massively turned on. So turned on in fact that I'd want to eat their cum from your pussy afterward, whilst wearing your underwear!" And with that, and by now completely overcome with wanton desire, I threw the duvet cover back.

Carla barely looked surprised. "Oh hubby, my little crossdressing sissy don't you look hot in my underwear. And what you just suggested is so fucking hot I think we should try it."

"When?" I gasped.

"This very night."

"How are we going to do that?"

"I'm only in Chester. It'll take you an hour to get here in the car...There's a crossdressing party going on here this evening. You'll feel right at home...you look so sexy by the way. How does it feel wearing my underwear?"

"Sensational...please don't be mad...but I'm desperate to kiss another crossdresser."

"Oh sissy hubby, why would I be mad? It's a massive turn on. From now on we can be not just husband and wife, but girlfriends sucking cock together. Would you like that?"

"I really would Carla. I'd like nothing more."

"Fucking amazing. Now get in the car, keep that underwear on and get here as quickly as you can. We're going to have one helluva party in my room when you arrive."

I kept not only the underwear on, but also applied some lipstick and even a bit of mascara. Over this I simply threw on pair of trousers and a jacket. I hated the feel of the male clothes, but thought it best not to frighten the neighbours.

I made it to Chester in 45 minutes, I was lucky not to get pulled over by the police I was driving that fast. I turned into the hotel car park and raced inside. A cacophony of music and voices greeted me. I went up to the reception desk and asked them where the crossdressing party once. The girl behind my desk asked: "Are you, David? Or should that be Davina, now? Carla's husband?"

"Yes," I stammered. The receptionist was very pretty, blonde hair, deep, husky voice. "How did you know?"

"I can always tell the first-timers...You look fabulous, though, so don't be nervous. I'll be taking care of you, my name's Ruby...Josh, can you take over on the front desk please," Carla continued addressing a big hunky guy who looked like a male model. Ruby then invited me to join her in a large cloakroom.

"Your wife has left a lovely black cocktail dress and a pair of high heels for you," she pointed to a rack filled with alf a dozen dresses. "Come on, I'll show you."

She could tell I was still apprehensive, so she took hold of my hand, helped me remove my jacket and trousers, and put the cocktail dress on that Carla had left for me.

"As I said, Davina, there really is no need to be nervous, we're all here for the same thing this weekend. And you're in very safe and experienced hands."

That's when it dawned on me. This stunningly attractive blonde haired receptionist was actually a crossdresser. I felt my cock stir with lust and longing. And when Ruby slipped on my dress and high heels there's was no disguising my desire for him/her.

"Looks like someone's pleased to meet me."

"Ruby, I hope you don't mind me asking, but are you male or female?"

"I don't mind at all. In fact, it's quite the compliment that you're asking. Here let me show you..." Ruby was wearing a dazzling cheerleader outfit, pleated pink skirt, matching stockings bra and, I gasped, ruffled pink panties. When he/she lifted up the skirt I spotted an enormous erection.

"Wow, that's impressive!" It was a monster size cock and I could feel the room spinning. All I could think about was wrapping my tongue around Ruby's cock and then bending over and letting him fuck my man pussy. I felt so slutty and tarty, like a bitch on heat.

"Why thank you, kind sir. I know most sissies only have small cocks - Carla told me yours is about five inches?" I nodded, I wasn't even upset that Carla would tell complete strangers how tiny my cock was. because although it was humiliating it also turned me on.

"Can I see your little sissy cock?" Ruby asked, very politely.

"Please help yourself."

"You don't mind me touching it, handling it, maybe even rubbing and kissing it?" Ruby asked seductively. I was falling under his girly spell. I was aching for him to play with me.

"It would be an honour, you're so sexy and gorgeous, Ruby and you have a cock to die for."

"I love these compliments your giving me Davina, maybe we should take this upstairs? Your wife gave me a spare key earlier."

"Oh Ruby, I'd love that. But, can I kiss you first? I've never kissed another man, sorry, another crossdressing sissy before, and your lips look so enticing in that sky blue lip gloss."

Ruby smiled, licked her lips and said..."These sultry things you mean? You want to feel my girly man lips on yours?"

"Oh fuck, yes, yes, Ruby I really do." We were standing only a few feet apart now. My heart was pounding like a snare drum. The beating intense and overwhelming. When Ruby's hands interlocked with mine and I could breathe in her heady perfume and feel the faintest touch of her pleated skirt against my stockinged thighs I felt drunk with desire. And when he pulled me close and I could feel our hardened cocks pressing into each other through our silky feminine panties I felt a ton of precum ejeculate onto my wife's cobalt blue knickers.

Then Ruby's lips met mine, gently at first, soft as kissing any other woman, yet more exotic, more naughty, more wildly thrilling. When Debbie's tongue found mine, and our lingerie clad bodies moved even closer together, I knew i could never go back to just being a boring straight male again. I'd never felt such a thrill, such lust - even for my very hot naughty wife. My wife's panties were now soaked with precum and I needed to go upstairs with Ruby before I suffered premature ejaculation.

"So, sissy David, how was your first kiss with a crossdresser."

"Fucking amazing," I said.

"You really are sensational for a first timer," Ruby said, which made my confidence soar. "Come on, let's go upstairs."

Shaking with excitement I followed Ruby out into the lobby and into the lift. There were party-goers and revellers everywhere. It was hard to distinguish real females from crossdressers. Everyone looked stunning. I felt I'd entered a new world, a world where your deepest fantasies could be lived out in the safety and security of being accepted as a crossdressing sissy.

Once we were in the elevator Ruby said: "You know, even though you're not wearing a wig or false tits many of the men down there were ogling you."

I felt thrilled. "Seriously?"

"Absolutely. You could see some of them thinking - I'd like to fuck him."

"But I'm not even gay."

"Oh, really?" And with that Debbie leaned in and kissed me again.

"Okay, maybe I am a bit." We both giggled and exited the lift.

At room 669 Debbie paused, inserted the key and opened the door. Immediately, I could hear voices, but couldn't tell where they were coming from. Room 669 turned out to be the bridal suite. It was enormous. We walked through the main room which had spectacular view over the old Roman city walls of Chester, turned a corner and...there was my hot sexy naughty wife, wearing only her fishnet stockings and spiked high heels, on the bed with two hot young studs that were naked. The sexual tension and atmosphere in the room rose considerably when Carla introduced me to them as her sissy husband and his new friend, Ruby.

"Wow hubby don't you look pretty in my underwear."

"Yes, your husband looks really hot," said the young studs in unison.

There was a long silence, as everyone wondered how I was going to respond. The funny thing was I didn't feel the slightest bit of jealousy. The silence was due to fantasy becoming reality. I was trying to take this in. To be honest, it was all a bit much for me. And I thought I was going to faint. But then Ruby squeezed my panty clad ass, kissed my neck and even tickled my nipples through the silky material of my wife's blue balcony bra and suddenly the reality was so incredibly naughty that I wanted to live in it all night long.

"Not as hot as the two studs who are about to fuck my naughty wife," I said, finally.

Everybody cheered, Carla jumped off the bed, kissed both me and Ruby passionately, felt our cocks and then said: "Enjoy each other sissies, welcome to the party." She jumped back on the bed and immediately the two guys, who I later discovered were called Keith (blonde hair, blue eyes, looked like a Norse god) and Topaz (a gorgeous looking black guy), started kissing my wife's tits and stroking her thighs. This drove me crazy with desire for Ruby and instantly I went down on my knees, rolled his ruffled panties down and tasted my first cock.

My wife seeing how much of a sissy I'd already become squealed with delight, as did Ruby.

"Go on you sissy little cocksucker, take all of Ruby's big cock in your pretty little mouth," Carla said.

Being called a sissy little cocksucker by your wife is amazing. I loved her calling me that in front of the two hot studs, one of whom, Topaz, was now inserting his lovely black cock in my wife's pussy. This just made me greedier still for Ruby. And when Keith started kissing my wife and fondling her tits, I become even hungrier.

I led Ruby over to the bed, climbed on top of him, and right there with my wife next to me, I started going down on Ruby over and over again.

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byCandyboi© 6 comments/ 30227 views/ 28 favorites

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