My wife Cindy had a sexual past before we met. I'd only been with a couple of girls before her but her sexual history was epic. I overheard her talking about me to one of her friends once and she said that I was the sensible choice. I was safe, I had a job, I wasn't going to treat her bad or cheat on her. Everyone has to settle down sometime.

What hurt the most, though, was how little affection she gave me. We rarely ever had sex, even on our honeymoon, and when we did it was just missionary with her laying there, waiting for me to finish. 

About a year after we wed, she got a job working nights at a restaurant and by this time I'd found myself in a sexless marriage. I would normally just sit at home most evenings and jerk off to porn, my way of coping with the lack of sex.

I had heard some things about my wife's past. Her friend got drunk once and told me how Cindy used to be a bit of a slut, that she had dated a lot of guys and had a thing for black guys. My wife tried to reassure me saying it was never anything serious, just sex, but being a skinny white guy I always found myself feeling insecure, thinking about them fucking her.

As time went on my jealousy seemed to overwhelm me as I found myself searching through her Facebook galleries looking at old pictures of her dressed all slutty, always hugging and kissing different guys. Each picture had comments saying things like, 'thanks for last night baby,' or 'let's do it again sometime'.

Whenever she left herself logged in I would torture myself by reading old messages and viewing the profile pages of guys she'd fucked. My jealous subconscious tookover and I began watching interracial porn, jerking off to white girls being fucked by big black cock.

I also became obsessed with hypnotic videos of white sissies; anything with the title bbc sissy or white sissyboi made me hard like never before. This is what led me to start dressing like one. 

At first it was just a few items, slipping on some of Cindy's panties and bras, but then I started going through her wardrobe trying on all her old dresses. I loved loading pictures of her past sex partners and jerking off to interracial porn, imagining I was her.

This soon escalated and I found myself ordering high heels in my size, wigs, lingerie, and a black vibrating dildo. I spent my nights pretending to be a girl, sucking and riding my black cock while obsessing at the thought of how much of a slut my wife used to be, dreaming that I was one too.

It didn't take long for me to make a profile online and start looking for the real thing. I'd been video chatting with this one guy, Andre, and had introduced myself as Cindy. He enjoyed watching me dance and strip for him, sucking on my black dildo while he jerked off his black cock, talking dirty to me. 

A few weeks before my wife's birthday, I started to feel guilty so I stopped everything I was doing and tried to purge my sissy feelings. She said she wanted to invite all her girl friends over for some birthday drinks and would I mind making cocktails and nibbles in the kitchen for them.

I of course obliged, and that night they got really drunk and loud. I was sitting in the kitchen when they started talking about sex, specifically how many guys Cindy had slept with. I always knew it was more than ten but her answer enraged me.

"Fifty-seven!" she shouted, bragging further, "and that's just the white guys!" Her friends all laughed and asked her how many black guys she'd fucked.

"262!" she yelled. My heart pumped rage through every artery, thinking of how many men had fucked my dirty wife, and worse still, the fact she had barely given me any pussy!

My mind exploded; that was it! I thought. I'm gonna get this bitch of a wife back. Fuck you for fucking everyone except me! For only marrying me because I was 'the sensible choice'.

I was determined to fuck a guy just to spite her, quickly loading up my sissy profile on my phone and texting Andre.

'Hey sweetie, what you up to tomorrow night, wanna see me in person?'

He replied within minutes. 'Yes! Where?'

I texted back, 'I'll book a hotel and send you the address, 8 pm ok?'

'Can't wait!' he replied.

A little smirk grew on my face at the thought of the revenge plan formulating in my head. 

The next day Cindy left for work and I quickly grabbed a bag. I packed one of her sluttiest dresses, my high heels, wig, some makeup and of course the sexiest lingerie and stockings I owned before heading off to the hotel. I checked in and almost ran to my room, eager to dress up like a sexy girl.

I ran a shower first, shaved myself smooth all over and began to dress. Slowly I rolled up the stockings one by one, feeling my legs as I did before clipping on my suspenders, slipping on my new bra and my matching thong, ensuring my cock was tucked back underneath my ass.

I went to the bathroom mirror and began carefully applying my makeup, admiring how feminine I looked as I donned my wig. I walked back into the bedroom put on my high heels and picked up Cindy's sluttiest dress.

It was a wet-look, sleeveless bodycon that stretched against me as I pulled it over my lingerie. I had purposefully picked this dress as I'd seen her wearing it in lots of photos with different guys, and remembered thinking how hard they must have been when they saw her in it.

After dressing up I stood in front of the mirror, moving my body and acting effeminately, rubbing myself all over. I was busy enjoying the feel of the stockings rubbing against my dress when I heard a knock at the door.

I looked through the peephole and saw Andre. Opening the door I watched his eyes widen as I stood provocatively enticing him in.

"Oh, Cindy, you look amazing!"

I blushed and replied in my best female voice, "Thank you, sweetie, come inside."

As soon as the door shut, I dropped to my knees, unzipping his trousers, pulling them down and grabbing his cock out of his boxer shorts. I'd never actually sucked a cock before, other than a dildo, and couldn't wait to get my first taste.

His cock looked delicious. Big, black, and smooth. I grabbed it with my hand, feeling it harden between my fingers as I sucked on the tip. It tasted so good and I tried to get the whole thing into my mouth.

I must have sucked his dick for a least ten or fifteen minutes, feeling his precum ooze onto my tongue, listening to him moan with pleasure.

Finally he couldn't take it anymore and asked if he could fuck me. I stood up, pushed him to the bed and pulled off his trousers, jumping on top of him and lifting my bodycon dress over my ass.

I'd rubbed Vaseline on my ass while I was getting ready so my boipussy was nice and slippery. I grabbed his cock and guided him inside me as he grabbed hold of my ass cheeks.

His cock felt amazing as it entered my hole and pushed deep inside me, stimulating my g-spot. I suddenly realized what my wife must have felt fucking all those guys and let out a girly scream.

"Oh, Andre, fuck me with your big black cock!"

He started thrusting up into me as I bounced on top of him, making loud girly moans. "Fuck me! Yes! Fuck my tight ass. I want you to use me like a slut."

As he fucked my virgin ass, my limp dick flapped up and down, making a soft slapping sound. He held onto my ass and groaned in ecstasy, talking dirty to me as I continued to bounce up and down on his cock.

I could tell he was almost ready to cum so I started riding him faster, moaning like a girl.

"Are you almost ready, baby? I want you to fill my ass with your load. Come on, fuck my white ass, fuck me with your big black cock!"

He shuddered and rampantly fucked me, grunting and shooting his load deep into my anal pussy, his cum filling my ass and tickling my g-spot. Now I knew how Cindy must have felt all those times. She used to be a slut, but now I was a slut and I loved it!

He grabbed my ass and squeezed it tight as he emptied his balls into me. As he moaned I felt a juicy load of my precum dribble out of my limp dick. His face said it all. I'd fucked him good and made him cum all in my sissy ass.

Afterwards we talked for a while. He told me he had always wanted to fuck a sissy, but had never had the chance before. It was quite romantic, but I knew he was just the first of many cocks I would fuck now that I had become a true sissy.