Sissy For A Day

Summary:

With his wife's help and support, a man becomes a sissy for black cock.

Note 1: This is a

Halloween 2018 Contest Story

. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further.

Note 2:

This is dedicated to the real

Paul

who requested this story.

Note 3:

Thanks to:

Tex Beethoven, Robert, and Wayne for editing.

*

Some would call it a mid-life crisis... although I'm only thirty-five and hopefully I haven't reached the midpoint of my life yet.

Some would call me a faggot... although I love eating pussy and fucking my wife.

Some would call it curiosity... although I did some of this in my younger days.

I didn't know what

I

wanted to call it other than a growing obsession... but I'll get to that in a bit.

In most ways I'm a stereotypical male in my mid-thirties. I'm five foot nine, brown hair, blue eyes and a bit chubby... but not fat. I work an interesting nine to five job as an analyst, which gives me lots of time for thinking. I'm great at math and would be considered a geek by most who know me: I love board games, computer games, comics and anything sci-fi. Yet I counter that geek list with a love of sports... just as a spectator; I'm not a jock.

Like I said, I'm a pretty typical man in love with a beautiful woman who's years younger than I, who has long red hair, green eyes and an amazing body in her five foot six frame. She's a spitfire in the bedroom and willing to try most things... and is also quite submissive.

Although I'm dominant in the bedroom with her, and I relish that role, there's another side of me I'd kept squashed for the past dozen years... a side of me I'd been completely ashamed of... my submissive side combined with my attraction to cock, kind of a package deal.

Now unlike some stories of mid-life crises where a guy watches porn and suddenly becomes intrigued by cock... or someone who's watched hypno videos and is subconsciously coerced into becoming a cock sucker... I'd

always

been intrigued by cock. I mean I'm also intrigued by tits, pussy, shapely legs and a curvy ass... but cock had always intrigued me as well.

I mean there are so many unique qualities to a cock... I suppose there are as well for a pussy, but a cock is the ultimate sexual organ... at least it is to me. It is simplicity itself to understand its psychology: arouse it and it gets hard. It's great to look at: a long hard shaft just begs for attention. A tasty treat: male cum is a lot heartier and tastier than the watery female variety.

And although I had no interest in men, no sexual attraction at all, I was drawn to their cocks. In my early twenties I experimented with a few. Got sucked by some, men definitely being better cock suckers than woman (just like I imagine women would have to be better pussy lickers... it's just common sense that the same sex would understand the pleasures of their own unique private parts)... and I'd sucked a few. I never fucked a guy, nor did I ever get fucked. Although I was curious what it would feel like, back when I'd been experimenting I had been too nervous to try it out.

The first time I sucked cock I'd been chatting online in a sex chat room. I used the name BiGuy4Fun at the time. I got talking to someone who called himself BigUKC or sometimes BigCUK. I never learned his real name or why he'd picked those handles. It turned out he was inexperienced and curious too, and he didn't live far away. We agreed I would pick him up in my car and we'd experiment.

Twenty minutes later I was parked on a dark street a block away from his house waiting for him. Suddenly he appeared, knocked on my window and got in the passenger seat. It was nighttime and we drove around aimlessly until we found a car park at a restaurant that had closed for the night. I parked behind the building.

We both took out our cocks and started to stroke ourselves to hardness. The nighttime light was dim but we could see each other reasonably well. I was as nervous and excited as I'd been the first time I was with a girl: the anticipation was enthralling, the taboo of it stimulating, and yet the fact I was possibly about to have gay sex made me question myself... my dad was old school (a euphemism for fucking bigoted) and thought fags should burn in Hell... which was why I had resisted the curiosity that had been bugging me from when I was in high school until I was twenty-three.

So when my unidentified new friend eventually asked if he could touch mine and I said yes, he started to stroke me.

It felt nice and after a minute I asked if I could stroke him too. His cock felt so hard. It was about seven inches and I soon wanted to try and suck it. Reality was I had been curious about this for years and it was really now or never, but I still couldn't make myself ask. As I was struggling with this immobility, without asking permission he leaned down and just took mine in his mouth. (I'm not complaining.) I groaned as he bobbed on my cock.

Now that he'd broken the ice, after a couple more minutes I was able to summon enough courage to ask if I could suck him and then I leaned across the seat awkwardly, almost tangling myself in the steering wheel, and took him in my mouth. I had watched a lot of oral porn, I had read a lot of written porn, and yet nothing can possibly prepare you for your first time having a real flesh and blood, pulsing, warm, and eventually spurting cock in your mouth.

It was a strange feeling, partly because it felt so natural when I wasn't expecting it to. I wrapped my lips around it and bobbed, only taking two or three inches in my mouth.

For a good ten minutes we took turns sucking each other, yet each time he sucked me all I could think about was how long before I could take his cock back in my mouth.

I just loved the feeling of his cock in my mouth, and now of course, I wanted to taste his cum. The fourth time it was my turn to suck him we were going faster and I was taking more of him in my mouth, he warned me if I kept it up he was going to come. That's what I wanted so I bobbed faster, dying to taste that first load.

I wanted his cum more than I could recall wanting anything in a long time!

A good thirty seconds later I got what I wanted as he groaned and spewed his load in my mouth. I was no longer a virgin cock sucker!

I kept bobbing, swallowing his whole load like a good cock sucker, enjoying taking it all and only wishing I could have savoured the taste more... most of it had shot down my throat rather quickly.

Once done, he finished me off too, also swallowing my load, and I dropped him back off near his home. We met a few more times, both of us swallowing each time.

I hooked up with two more guys, both of them tops who wouldn't suck me off, which oddly I preferred. I knelt before them and sucked their cocks. Although I had enjoyed the car sex and felt satisfied afterwards and considered it a perfectly good introduction to cock sucking, I found I preferred just being a cock sucker. I even got my first facial at a guy's house. I felt so dirty taking a hot load of cum on my face, and also a little ashamed, yet my cock raged and the memory of the exultation I'd felt outlived the shame.

One of the tops said he would fuck me in the ass one day, but it never happened, and then I met Susan and I quit cold turkey. I'm not going to lie, it's been twelve years or so, and I still crave cock.

Lately when I watch porn it's always oral porn where I imagine I'm the girl.

When I browse Tumblr it's almost exclusively sissy pictures or gifs.

When I read porn it's usually about straight guys sucking cock or guys crossdressing.

And because of Tumblr, which I have been obsessed with the past few months, checking it regularly every couple of hours even at work, I've recently become intrigued by black cock. I should note it isn't about the race thing, it's just that most blacks seem to be tops (although I'm sure some must be bottoms too) and there is just something about a black cock, something majestic, something captivating.

The sissy gifs and captions also led me to revisiting something else I had done often in the past but not for years: crossdressing. As a teenager I'd often worn my mom's recently used panties, feeling her wetness on my cock and balls a major turn-on, the fantasy of being with my mother something I never got to live out, God rest her soul.

In college I often wore panties, always pink ones, and pantyhose under my jeans (never openly of course), getting a kick out of my secret sissy attire, but I stopped doing that as well once I met my wife.

My wife knows of my gay-ish past, and I know of her wild past (she fucked a black guy once and loved it, for example), but we both let our wild youth go when we got married. We haven't really hidden anything from each other, but our reveals have always tended more towards generalities than specifics. Yet I wonder if like me, my wife ever fantasizes about her past. She is naturally submissive to me in the bedroom and we have a good sex life, albeit less frequently than we used to, but I sometimes wonder what it would be like if we could get our teen and college selves together and go a bit crazy.

So there! That's all the background you need, and likely even more than you wanted. Long story short, I have recently become addicted to Tumblr porn, hypno sissy videos and have now begun wearing panties and pantyhose under my clothes again at work (then changing out of them in the garage before going into the house). I've also recently begun on occasion wearing a butt plug to work too... a recommendation from a sissy video I felt compelled to obey (yeah, I get the irony, but it turns me on, so I'm going with it).

Then Susan found my pantyhose and panties hidden in the garage.

"What is this?" she asked angrily, storming into my home office.

"What?" I asked, before turning around from facing the wall and seeing the bag of feminine items I'd hidden behind my toolbox.

How had she found it?

"This collection of panties and pantyhose and whatever the hell this is," she said, displaying the butt plug in her hand.

My face burned red as I said, "It's not what you think."

"My first thought was that you're cheating on me, and this evidence strongly suggests that you are; are you telling me you're not?" she demanded.

"No, never."

"Then what is it?" she demanded again, "and it'd better be good!"

"Those are panties, pantyhose, and the thing in your hand is a butt plug," I answered, before adding, shame coursing through me, "They're not for someone else, they're for me."

"Oh!" she said, looking at me with a mixture of

thank God

and something else I couldn't read. After a silence that seemed to last an eternity and yet was likely fifteen seconds as I tried to find words to explain further but came up empty, she asked, "So you're gay?"

She asked it as a question, but it was more like wanting a confirmation to her own assumption.

I protested, "No, no, no. I love

you

, I don't find guys attractive at all."

"I'm confused," she said, looking confused.

"I don't like guys, it's just I..." I began and paused, worried my next words would sound maybe worse than being gay.

"What?" she asked. "Tell me, I want to understand."

I just blurted out the truth, throwing the words out there, not knowing how they would be taken or the consequences that might follow, "I just like dicks. I'm obsessed by them."

She said a single word, "Oh!"

She again remained silent for an eternity.

She then said, it being her turn to surprise me, "Well, I guess that explains the porn I found on your computer."

"Oh, God," I sighed, my laptop full of hypno sissy videos, sissy and gay erotica, and literally thousands of Tumblr gifs about how to become a sissy.

"So you want to be a girl?" she finally asked after another long pause to process this new avenue of thought.

Deciding there was no reason to lie, it was all out there already, "Sometimes."

"You want to

dress

as a girl?" she asked.

"Sometimes."

"You think a lot about sucking cock?" she asked, using a naughtier word than she usually did.

"Sometimes," I answered, feeling smaller and smaller with each question and repetitive answer as I watched my manly image fading in her eyes.

"How often?"

"I don't know," I lied.

"Don't give me that, answer me!" she demanded in a tone I'd only heard her use twice, both times during fights, which happened extremely rarely, thank God.

"Often."

"How often?" she repeated the question, more gently.

"Daily," I finally admitted, figuring this was likely the end of our marriage.

"Do you wear these panties and pantyhose out in public?"

"Lately I have," I nodded, struggling to read my wife. She was still showing hints of anger, but she seemed more to be curious, as if trying to process all she was learning about me, which I guess she was.

"Do you want to be fucked in the ass?" she asked.

"Mostly I fantasize about sucking cock or crossdressing, but on occasion the idea of getting ass fucked pops up," I admitted then added, deciding to be a hundred percent honest, "lately it's been more often."

"Any cock, or black cock?" she asked.

This surprised me until she explained her thought, "Most of your hypno porn is about black cock."

"Oh," it was my turn to say, wondering how much she had watched and read on my laptop.

She added, "I never knew such videos or even the concepts existed, but one you bookmarked has over 300,000 views, so you can't be the only one." She then added joking for the first time in this... confrontation? discussion? soul-baring?... or at least she seemed to be joking, "Unless

you've

watched it that many times."

"No," I said, before admitting with an awkward, shameful smile, "a couple hundred, tops."

She then repeated the question, "So do you want just any cock, or black cock?"

"I can't believe we're having this conversation," I said, happy she was still here with me.

"Me neither," she said, but added, "yet, here we are. Don't worry, if you were lying about the cheating and this sissy stuff and all the rest were just a smoke screen, you couldn't have made up all this detail on the spot, and I wouldn't have found what you weren't expecting me to find in your computer. So I'm over my mad and there's no way I'm leaving you, I just love you and want to know." After a pause, she asked again, "So?"

"I mostly crave black cock," I admitted.

"Why?"

"It's just..." I paused, this again making me sound really gay.

"Go on," she said and reminded me, "remember I'm no stranger to sucking and being fucked by big black cock. Not recently, but still."

I couldn't believe she'd used those words to describe it. I'd never felt insecure about her sexual past until this moment. Suddenly I wondered if I'd ever been enough for her. I didn't ask her though, this was still about my kinks not hers, so I just admitted my truth, "Black cocks just seem more visually appealing. I can't explain it, but I'm drawn to them."

"Oh, I understand," she said, her tone full of meaning, but she didn't elaborate.

"You do?" I asked; she was taking this way better than I could have ever imagined.

"Black cock is almost irresistible," Susan said, as if reminiscing about 'the good old days' when she'd been fucked by them.

There was a lengthy pause, as I wasn't sure how to respond to that.

"Do you want to be pegged?" she asked suddenly, a term I didn't even fathom she knew existed.

"You'd peg me?" I asked.

"I don't know," she said. "I love you and I want you to be sexually happy, but..."

"I know," I said, although I really didn't know since I didn't know what else she was going to say.

"I'm not sure I can do that," she said.

"It's okay," I said. "Fantasy is sometimes just that."

"But I can do this," she said brightly, dropping to her knees and fishing out my cock.

I couldn't believe this encounter had started with my wife discovering my contraband bag of feminine toys and was finishing with a blow job.

That night ended up being our most amazing sex in a long time. She sucked me; I went down on her; I fucked her to multiple orgasms before coming on her face.

As she lay there wiping my load from her eyes so she could open them she asked, "So do you want facials like this one?"

I shrugged, "I had one years ago."

"Want another one?" she asked.

"In a perfect world," I said.

"Well, how about this?" she asked, scooping a big wad off her cheek and carrying it to my mouth.

I opened and without any hesitation sucked my own cum off her fingers.

"Wow!" she said.

"What?" I asked, when she pulled her fingers out of my mouth.

"I never thought you'd eat your own cum," she said.

I leaned forward and licked my cum off her chin.

"That tickles."

"Sorry," I said, scooping some cum from under her eye and eating it.

"No worries," she said, as she got off the bed.

Things went back to normal for the next few days... until Halloween. I arrived home after work and was surprised to find her already in her costume: she was a super-hot Daphne from Scooby Doo with the purple one-piece blouse and skirt, and pink thigh high stockings... which were completely in view because she was wearing the sluttiest Daphne outfit ever. She didn't even have to wear a wig, as her red hair and green eyes made her a Daphne ringer.

Every year we did couple costumes, and every year she choose them and surprised me on Halloween evening. Last year we were Wilma and Fred; another year it was Snow White and her Prince; another year we were Marge and Homer Simpson. She was always very creative, and I was dying to know what she had in mind for this year.

I asked, "Am I Fred?"

"Nope," she said, with a mischievous smile.

"Shaggy?"

"Nope," she repeated.

"Scooby?"

"Nope," she said, taking my hand and leading me to our bedroom.

I seriously had no idea who I could be until she led me into the bedroom and I saw a Velma costume laid out on the bed. "Oh!" I said.

"You wanted to cross dress," she pointed out.

"True," I nodded.

"Get undressed, then," she ordered.

"I love those words," I joked.

"I'm going to make you into the sexiest Velma ever," she said.

"Hotter than Linda Cardellini?" I questioned, thinking she'd been so hot as Velma.

"Hopefully," she said, "now get naked."

"Yes, ma'am, hopping right to it," I hopped, getting naked.

I soon learned the costume wasn't the only surprise. She handed me a padded bra and said, "Put this on."

"I'll have bigger tits than you," I joked.

"Tonight I'm going to slut you up," she smiled, as I pulled it into place over my head.

"Oh my," I said, as my cock flinched.

She put the orange shirt on me... and it was tight, making it look like I had huge tits.

I looked in the mirror and saw myself with big tits and my cock still showing and joked, "I'm a shemale!"

She laughed, "No, you're a drag queen and you're

my

drag queen. Come into the bathroom."

"Okay," I said, as I followed her into our bathroom.

There was a razor and shaving cream set out and waiting for us.

"You're going to shave me?" I asked unnecessarily; why else would she have a razor and shaving cream set out? She was already dressed.

"I'm making you look as feminine as possible," she said.

"Oh," I said, excited on the one hand, feeling very unmanly on the other, still shocked that my wife wasn't put off by my fantasy to cross dress.

"Now sit down on the toilet and lift a leg up," she ordered.

"Okay," I obeyed.

"And don't move if you don't want to see blood," she warned.

"I won't," I said, as she knelt down beside me.