Kissing Crossdressers Pt. 01

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our sex life which has become predictable and less and less frequent. We've been married 10 years and I was getting more and more concerned about the lack of sex we were enjoying together, but that all changed when Carla went on that break.

I was at work the first day, and when I got home I threw some pizza in the oven, sent Carla a quick text: hope you're enjoying yourself...love you xx and then watched some wildlife documentary over dinner. Carla texted me back halfway through: I really, really am...feeling much better already...love you too xx...Her reply was a little more enthusiastic than usual, but I thought no more of it. Typical girly break, I reasoned, she's probably just having a few drinks and flirting with the barman. Carla's always been quite the flirt, but since we got married she seems to have kept it under far more control.

I rinsed the plate that I'd eaten my pizza on, got washed, did my teeth, went the loo, stripped, until I was just in my boxer shorts, and climbed into bed. The next day was Saturday and I was off all weekend and thinking I'd probably go and see a movie or two. That's when I noticed that Carla had left her laptop behind. It was sitting on the radiator next to our bed. This was extremely unusual. Carla takes her laptop with her everywhere.

If I'd been a bit more circumspect, if I'd realised this was some elaborate trap, I never would have opened the damn thing in the first place. But curiosity and a bit of boredom will make you do things that ordinarily you would never countenance.

I opened Carla's laptop and entered her password. We don't, or at least I thought we didn't, have any secrets from each other, so I knew her password, just as she knew mine. Everything looked normal, Netflix was open - Carla had been watching some French bodice ripping historical drama (she loves subtitled foreign shows); there were some work related emails and a few emails from her friends who were on the spa break with her. Her browser history for the past week displayed nothing untoward and I was just about to close the laptop, a little disappointed (and relieved) that my wife's affairs were as humdrum as mine when I noticed the bookmark tab. This was usually the place she'd record good holiday ideas (various spa hotels were listed) and clothes, make-up etcetera that she was interested in.

Sure enough, all these types of things were listed, but then I spotted half a dozen links to CDS/HW. I had no idea what that meant. I sat on the bed for a minute, puzzled, trying to figure it out - CDS? HW? Getting nowhere I clicked on the fist link and when it opened I literally dropped the laptop. Picking it back up and trembling I looked at the site it had taken me to...CDS = Crossdressing sissies and HW = Hotwife. I browsed through the images.

The hotwife section showed cuckolded husbands watching their wives get fucked by alpha males - some black, some white. The husbands, rather than being upset by what their wives were doing, were clearly aroused. One of the images showed a gorgeous brunette taking a big cock slowly in her mouth, winking at her husband and a caption stating: MY WIFE MADE SURE I JERKED OFF WHILE SHE SUCKED OFF HER BOSS. I was aghast, but undeniably turned on. I couldn't believe that Carla would be into this kind of stuff. I was also scared...what were the consequences for our marriage? And yet, the more images I looked at the more drawn in I was to Carla's secretive world.

There was no denying the sexiness of these images, nor how wildly perverted they were. And once I started clicking through them I couldn't stop. And a very small part of me started to imagine what it might be like to jerk off watching Carla get fucked by another guy or even several guys. Would I be jealous or would that jealousy be eclipsed by arousal?

I was now rubbing my cock. It had been two weeks since Carla and I had last made love. And I was desperate for relief. I clicked on another image. A blonde woman, who was similar to Carla, was staring directly at the camera - as if looking at her husband. She was being taken from behind by some handsome stud. The caption read: THE MOMENT OF TRUTH BABE! ARE YOU IN OR OUT? In, I cried, as I felt an orgasm approaching. That's when my phone rang. Startled, I picked up, it was Carla.

"Hi darling, just stepped outside, for a few minutes to give you a call. How are things going? Did you have that pizza for dinner?"

"Oh hi, yeah all's good here. Pizza was fine. I've just got into bed actually."

"Missing me?"

"Of course I am."

"Missing you too...By the way, did I leave my laptop behind."

Did she suspect something? Did she know what I was doing?

"Oh, erm. I don't know. Where will it be?"

"On the radiator in the bedroom, I think."

"Yes, yes you did. Here it is. Do you need it?"

"No, it's okay. Didn't know if I'd left it at work."

My heart was pounding at this point.

"Well, listen babes, I better go. There's a hen party here and a male stripper has just arrived. Should be fun," Carla giggled. Clearly she'd been drinking.

"Go and enjoy yourself." Then I thought, what the hell and said, jovially: "And keep your hands and your mouth to yourself!"

"Mmm honey I'll try to, but I think it's easier to ask for forgiveness than it is for permission!"

The line went dead after Carla had told me she loved me and made the sound of a lip-smacking kiss.

My cock was still erect. I looked again at the image of the blonde woman, then I closed my eyes and imagined Carla getting taken from behind by some hunky male stripper. My cock hardened.

Then, I suddenly remembered the other link CDS = Crossdressing sissies. Shaking, I clicked on this link. Looking back now it was this that changed everything. The first image completely shocked me. It showed a very, very attractive crossdresser wearing a long dark wig, polka dot basque, black stockings and matching panties kissing a naked well hung fit-looking male. The guy had his hand on the crossdresser's sexy ass and the caption read: A GOOD SISSY KNOWS THAT EVERY PAIR OF SILKY PANTIES IS AN INVITATION. AN IRRESISTIBLE INVITATION THAT SAYS - I'M BEGGING FOR COCK. I looked at that image for several minutes intoxicated by its naughtiness. I was trying to figure out if I wanted to be the guy or the crossdresser. What would it be like to feel a crossdresser's ass, to touch his false tits, to kiss his rosy red lips? What would it feel like to put a basque or a bra on? What would it feel like to slide a pair of stockings up my legs, or feel a pair of silky panties caressing my ass, ball sac and cock?

Shit! What the fuck is happening to me here? I'm losing my mind. I don't want to be a crossdressing sissy and have some guy pawing at my ass and goodness knows what else. I'm a straight, heterosexual male, married to a hot sexy wife...and yet, and yet, I couldn't tear myself away from those pictures, nor from a train of thought that the images had sent me on. A train of thought that became deeply embedded as I scrolled through a plethora of images.

The next image I clicked was a game changer. Two crossdressers were on a bed, kissing each other passionately. The one on the right was wearing a black wig, black fishnet stockings, a tartan mini skirt, a ruffled pink blouse and high heels. The one on the left was attired in a black latex basque tied with pretty pink ribbons, a vintage style suspender belt holding up ruby red stockings and dark, but transparent full panties through which I could see his lovely hard cock. He wore a fiery red wig that made him look dangerously sexy and erotic. They were both wearing classy red nail varnish and scarlet red lipstick. Their kiss was deeply sensual, their tongues clashing like powerful flamenco dancers stomping on the ballroom floor. I loved the fact that the one on the left had slid his hand up his partners' tartan skirt revealing his gorgeous fishnet stockinged thighs. And I could just make out a pair of black, frilly, lacy knickers. The whole scene was mesmerising, it had a hypnotic effect on me. I had this powerful urge to beg them to let me join in. My cock was now throbbing, crying out to be touched, to be touched and kissed by one of these sassy crossdressers.

I clicked on the next image. Again this showed a guy in panties, stockings and suspenders, a god-like hunk had just made him ejaculate. The cum was dripping down his cock and onto the stockings. It made me wonder what it would be like to make another guy ejaculate. What would it be like to pleasure a guy? To pleasure a crossdresser? Would I be brave enough to do it? And would I want to take his cock in my mouth, or in my man pussy whilst wearing my wife's underwear? Then I read the caption that accompanied the picture...ONCE YOU START WEARING YOUR WIFE'S PANTIES, STOCKINGS, BRA, HIGH HEELS AND LIPSTICK THERE'S NO GOING BACK. YOU'LL FEEL GAY. YOU'LL WANT TO START HAVING SEX WITH MEN. YOU'RE PRETTY MUCH IN FOR LIFE. I looked again at the previous picture, the two crossdressers kissing each other and I felt certain that the caption I'd just read was correct. An hour earlier I would have thought that you were insane suggesting that I, a 48 year-old, heterosexual could be attracted to the same sex or that I'd want to wear my wife's lingerie. Now that's all I could think about, and I was struggling to resist the overwhelming temptation to at least put on a pair of Carla's panties and stockings.

This desire to wear some of Carla's underwear was now reaching fever pitch. I felt like I'd been drugged. My reluctance to step over that line for fear of opening a pandora's box of sissy depravity was waning. I looked yet again at the kissing crossdressers, and my defences crumbled. I jumped off the bed, raced over to the linen bin, removed my boxer shorts, rooted through Carla's dirty panties and picked up a shiny, satin purple pair with a delicate black lace triangle on the back of them. Heart thumping, I sniffed the gusset, inhaling deeply, savouring Carla's pussy juices. Then I put them on. Instantly my cock grew harder than ever before. The sensation was incredible. I felt so horny, so naughty, so girly. I opened the drawer on Carla's side of the bed and pulled out a matching bra, and a pair of pink stockings. The bra was difficult to put on at first, but eventually, I managed it. The material was delicate, silky, but with just enough padding to make it look like I had small breasts. I slid the stockings up my legs attaching them to a pretty red suspender belt, then I admired myself in the full-sized, bedroom mirror. I flicked my nipples and rubbed my engorged cock through the satin panties. I was close to coming. Something was still missing though, lipstick. I went into the bathroom and picked up some red lip gloss. It was tricky applying it, but after several abortive attempts, I managed an okay job. I went back to admiring myself in the mirror wishing I had a wig to complete the picture. Another time, I thought. What I really desired, more than anything, was to be kissing one of those crossdressers in the picture, maybe even sucking their cocks. That's when I really went over to the dark side.

Carla has three vibrators - a big thick black one, a huge pinkish rampant rabbit and a slender, six-inch, realistic dildo. I went back into her bedside drawer and pulled out the rampant rabbit and the dildo. Looking at the picture of the crossdressers I imagined we were all in a hotel together with Carla filming us. I took the rampant rabbit, turned the vibrating mechanism on and after kissing it, placed it in my mouth. Then I placed the soft slender dildo on the floor, moved Carla's panties aside, and gently lowered myself onto what I wanted to be the guy on the left of the picture, glistening cock. The first couple of inches went in fine, the next two were painful and I winced and wiggled my ass. Eventually, the pain eased and I was able to take the full six inches in my man pussy.

I felt like a slut, sucking one cock, while another one rammed my ass. The sensation was so tremendous my cock leaked some precum. I stroked my stockinged legs, cupped my balls through Carla's panties and then knelt over the mattress. I grabbed the dildo and started thrusting it in and out of my panty clad ass. I took the rampant rabbit out of my mouth, put some of my precum onto the shaft and started licking it. I was reaching the point of no return. I realised even a gentle tug on my cock would send me over the edge. I looked at the kissing crossdressers one more time longing to have a menage a trois with them; then I gently rubbed my cock once, twice, three times. On the fourth occasion, my cum fired like a missile landing not only on the bed, but spattering Carla's bra and even my chin. It was the best orgasm I'd ever given myself. I took the rampant rabbit out of my mouth and removed the dildo from my ass. Then I collapsed on the bed, exhausted, but incredibly satisfied. I was asleep in seconds.