Kissing Crossdressers Pt. 02

"Oh that's so fucking hot my sissy cocksucker," my wife said, as Keith now sucked on her tits.

Carla was now bucking her hips as Topaz increased his rhythm clearly close to filling my naughty wife with his gorgeous cum. I couldn't see a condom anywhere and this excited me further. As Carla's bucking grew stronger and she started to moan with pleasure, Ruby harmonized. He was now getting close to ejaculating. That's when the game changed. He held my head and with deep desire in his eyes said: "I want to fuck you; right here, right now in front of your naughty wife.."

"Oh Ruby, I want you to as well. Please fuck my man pussy."

This sent Topaz and my wife into overdrive. And as I knelt over the bed Topaz roared with desire and emptied his cum into my wife's pussy, he kept going until Carla, with Keith's cock now in her mouth, screamed as an enormous orgasm swept over her. Watching my wife writhe with pleasure after another man had fucked her sent me insane. And as soon as Topaz disengaged I feasted on my wife's cum-filled pussy savoring my first cream pie. I think, if I'd already cum I never would have done that, but my cock was aflame with desire and this only intensified when Ruby pulled down the blue panties I was wearing and, after applying a bit of KY lubricant to my virgin ass, started easing his giant cock into me.

There were moments of agony after the initial couple of inches, but Ruby was gentle and we would kiss again and again and again. I loved the feel of his lips on mine and his hand on my stockinged thighs. He'd also rolled his ruffled panties back up and I loved the feeling of the delicate material on my ass. There was one horrible moment when the pain became severe, but Ruby once more halted, kissed me and gently rubbed my cock. Then there was a popping sound as the final few inches were inserted into my ass and pain turned to exquisite pleasure. Was this what it felt like for a woman I thought? If so, I wanted more of it. Any remaining inhibitions dissolved as soon as Ruby started pounding my ass with his cock. The pleasure sweeping over me was earth-shattering. It literally felt as good as fucking my naughty wife. With every new thrust Ruby turned me sissier.

"How gay do you feel now?" Ruby asked.

"I feel like a 100% sissy gay faggot and I love it." It couldn't be denied. I felt like a gurl, a crossdressing sissy girl. And as Ruby's thrusting accelerated I realised I loved watching my wife get fucked by hot guys while I was dressed in her panties, stockings and bra. I wanted to be her crossdressing sissy cuckold forever. I wanted us to dress up in vintage panties, girdles, bullet bras, basques, high heels and slutty dresses and go out on the town and pick hot guys up and bring them back to our apartment where they could fuck us all night. I wanted to feel like a real woman. I wanted some silicone breasts, I wanted to shave my legs, armpits and the bit of hair I had on my chest. I never wanted to go back to being a proper man ever again.

"Oh David, I'm coming in your virgin ass."

"Fuck me Ruby, fuck me hard. Fuck me with your delicious cock. Rub my nipples through my wife's bra. Move closer so I feel can our stockinged legs entwined and please kiss me again. Debbie's tongue danced with mine. I watched in pure ecstasy as my naughty wife took all of Keith's cum in her mouth; Topaz was now licking Carla's clitoris and she was close to yet another orgasm.

I felt Ruby's cock pulsating in my ass, he was nearing oblivion, and so was I. It was so weird. There was no way I thought I could climax without someone rubbing my cock, but Ruby was so deep inside me it felt like our cocks were rubbing against each other. When Ruby's hand gently touched my cock and he accelerated even more, we both cried out more or less simultaneously. I was a few seconds behind Ruby. It was the feeling of his hot cum filling my ass that sent me over the edge. My cum landed on my stockings, well my wife's stockings and on the balcony bra I was wearing. Some even landed on Topaz's ball sac and he made me lick it off.

I'd never had such a fulfilling sexual experience. The feeling of my wife's underwear on my body was sensational. I knew I could never fuck anyone again unless I was wearing lingerie.

The five of us collapsed on the bed.

The next morning only Carla and I remained. My wife was still wearing her fishnet stockings and spiked high heels. I was still wearing her blue panties, matching balcony bra and seamed stockings. We looked at each other and we're both overcome with lust. The scent of sexual fragrances still hung heavy in the air. The smell of cum and pussy juices was everywhere. Carla grabbed my panty clad ass - I felt a surge of sexual debauchery run through me. I wanted to fuck my wife whilst I was wearing her underwear. Carla saw the hunger in my eyes. She reached over to the bedside table and grabbed some scarlet red lipstick which she applied to both of us. Then we fucked liked rabbits all morning.

After brunch we headed into Chester, underneath my male clothes I was still wearing her underwear.

"Are we going the pub now?" I asked.

"No, my darling sissy hubby. We're going lingerie shopping for us both. Then we're going to get our nails done together. And after that, we're going to buy you a wig."

I leaked some precum once more onto my wife's panties.

"And then?"

"Then we're going to go back to the hotel and get ready together. I think Ruby's going to help us both. I hope that's okay sissy hubby?"

"I can't wait," I replied, as my cock stirred in the gorgeous silky panties I was wearing.