Sissifying Addictions

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it.

It's somewhere in between and none of it either.

It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass.

It started for me meeting Mandi.

***

I'm not a great looking guy and I've had to live with that and yeah it sucked. I was chubby, not too tall and just well one of those nerds in school. My saving grace was in school my older brother was a drug dealer and while there was a few parties here and there I got to go to and got laid a few times I never was good enough to score a girlfriend.

I was either just too ugly, plain or whatever and the rest well my family reputation did that in.

And being poor didn't help that either.

Poor lasted until my senior years of high school when I got a job pumping gas and saved money, then I worker for my brother too and his friends. Not selling but there was this guy "Chink" who looked Asian mixed but was really native and he was a really good grower of pot.

So come harvest time my brother and a few people he trusted cut, dried, picked bud and that paid really well. Enough that when I left for college that I had a nice nest egg.

After college I got work doing taxes and stuff having taken accounting and doing a few years in H&R block after I moved out west to Edmonton.

Decent money I started doing taxes for the oil patch crowd and all that stuff. My teen years drug cash went into an actual bank account after that and RRSPs and stuff over a few years.

Anyways...you get the picture. Geeky guy, homely, decently doing well.

Until I met Mandi.

We were at Jack Snowdon's bachelor party and he was a client so I got an invite.

There were lots of hired pussy there and Mandi was one of them.

She was enthralling.

Sweet, funny, with a great laugh and really good looking with great tits.

And she could suck cock...and she genuinely liked it.

No girl makes those noises or tries that hard and doesn't love sucking dick.

She sucked me off twice that night and we were outside smoking a joint when I asked her.

"Want to come back to my place?"

She did a long sucking toke and held it. "Can you afford it?"

"How much for the night?"

"A thousand dollars."

"Wow, holy shit."

She exhaled and shrugged. "It's the rate that'll beat out the other offers tonight James."

I thought about it for a few minutes and then nodded. "You take credit?"

She held up her phone and hooked in that card reader thing from her purse. "Actually I do."

I pay her and we leave the party and head to my place chatting about movies and TV shows and just general stuff and Mandi's funny, easy to like, personable too and she had a great smile and an amazing laugh.

Once inside she and I start making out heading right to the bedroom where she wasted no time getting naked.

Naked except her cock...she had a cock...and it was all locked up in this chrome and pink cage thing.

"You're a guy..."

She makes a face. "Oh fuck no, I'm not a guy."

"But you have a cock."

"Cockette, my sissy clitty."

"Sissy clitty?....What the hell?"

"Just what I said, you want me to go?"

"I...uhm..."

"Yeah, you had your nice dick in my mouth James, how about you sink that into my sweet sissy ass."

I was still deciding when she came over and kissed me and kissed me and once I was hard she pushed me onto my bed and after she took some lube from her purse she guided me there and sank down on my cock.

Pussy was good, Mandi's ass was fucking magic.

And she loved it.

Loud, sweet, vocal...it didn't take long before I was into it. Then it was doggy style and then it was Mandi on her back with her begging me to...

"Fuck me! Fuck me James, Harder! Get my legs up, higher!, higher! Fold me in half!"

It was so kinky, so erotic and so exotic.

When we were done she fed me a viagra and she got me to order take out from Kentucky fried chicken while she showered then I did. We settled in and we watched Letterkenny as we had a few joints and ate food and laughed then had a Redbull each as we just chilled for a few hours.

Caged cock or not she was fun, she was so fucking gorgeous just going around my place in just her panties those amazing tits just sort of making my night better.

All night to Mandi was a full 24 hours, she even turned off her phone.

A record for me as the viagra kicked in and I fucked her twice more until my balls were aching and really empty in a good way.

Even after I get to feel, fondle and suck on her tits as much as I want before we just chill some more snuggled.

"Best night of my life Mandi."

She laughed warmly. "Guess my little clitty isn't a deal breaker then?"

"No, it's not. It's kinda sexy actually."

"I know, that's part of it, part of the charm of being a sissy."

"What's the difference between a sissy and a trans girl?"

"I'm not really transitioning because of dysphoria like being a guy is torture or anything. That's like trans people but me, I'm a sissy, I love being a girl for being a girl and that's sexuality first. I love cock, love getting fucked, getting filled and all of that but I want my clitty, I don't want to go through surgery that doesn't really work well sometimes and is like waaay complicated after that."

"Really?" I nuzzle into her. "I didn't know it was complicated."

"Surgery means lots of deep invasive stuff right down to getting the nerve stuff right and then the urinary stuff right and then there's like all the maintenance stuff. Me...I love cumming, I get off fine as I am and everything works, my clitty isn't something I hate I love it."

"But you cage it."

"That's part kink and feeling plus training and sissy girls love having little clitties. It's part of us, we're not ashamed of them, it's part of it as much as smooth skin or titties."

"So you really love this whole deal then?"

"Oh yeah, I used to think I was some silly straight guy but that like changed."

"You thought you were straight?"

"I did until I met a girl like me and she woke me up to how amazing it is to be a sissy." "Woke you how?"

"Let me show you?"

Mandi slid herself down my body and grabbed her purse and she started sucking my cock getting me hard again thanks to the viagra and while she worked her mouth magic on my cock she rubbered up her fingers and took the lube she had in her purse and started lubing my asshole and it felt so strange and scary but Mandi's magic mouth was so distracting.

Then her fingers pushed into me slowly and she started fingering me.

It didn't hurt really but it was really weird, scary and....oh...oh...she touched something back there inside me and she kept at it.

Kept fingering and rubbing and pressing.

It felt better and better like I was going to cum but it was inside me, deeper, deeper inside under my cock...good, good better, electric.

I cried out as I came.

It wasn't like every other time.

I shot a little load out but inside...inside it felt like more like it rushed through my insides and curled up in my brain.

I wanted more, needed more.

Mandi kept going cleaning my off, drinking me down but her fingers kept going, massaging, touching my spot making more sissy magic.

And instead of being done the pleasure rebuilt and soon I was limp, limp and spent and moaning as this whole new feeling was taking my body over and ruling my brain.

Then it happened, this dry cum...this orgasm that had nothing to do with my cock.

I had a sissy orgasm.

Then another.

I was breathing hard and cum stunned while she lubed up something else and this big, much bigger thick thing entered my ass and I loved it.

Loved it so much I cried out as it felt so fucling good.

"Oh! Oh fucking god! Oh Mandi! Mandi! Ff..fuck!"

Mandi fucked me with her dildo and inch after inch hammered my sissy spot and sank in deeply into my body and made me sissy cum.

She literally fucked me until I passed out.

I remember the deep endless feelings, the really deep pleasure and then my brain not being able to process how good it was and just...just...I fainted...I had a sissy cum and I fainted.

I woke up and she was grinning sitting up and beside me watching me.

"Get it now?"

"I..."

"It's just the start James or rather Jamie."

She kissed me and we did that for awhile before she got up and showered and I called her a cab and seen her out and safely away.

After that it took me a long time to process things.

I did love it.

Loved it, loved it, loved it.

Part of me hated that I loved it too.

I even tried to ignore it too until I couldn't and looked up sissies online.

All these sissy girls like Mandi, all these sissies with little dicks some in cages and all these videos and hypno videos and all these caption memes that said that this was possible.

I wanted this.

I dreamed of getting fucked by the men on the screen.

I dreamed of being sweet and sexy.

There was so much there and for a year I ignored it but didn't until I ran into Mandi at another party for another client.

I actually avoided her for most of that until I was outside having a smoke and she lit mine for me.

"Jamie."

"It's James."

She tilted her head. "You're mad at me?"

I took a few minutes and a few drags. "Yeah, yeah I am. I felt stuff Mandi, it was great, better but look at me...I'm not you."

She lit a joint. "You think I was me when I first started?"

"Look at you now."

"You want this, you want to be like me?"

"Look at you, look at me it's not possible."

"It is, you really have to want it, really have to James."

"Easy for you to say."

Mandi reached out and she gripped my face with one hand by my jaw.

"I'm not lying, I'm not bullshitting you and it is possible but it's work, it's hard and life changing to where you are upending everything about you but it's worth it."

She stares at my eyes. "If you want help, I'll help."

I nod. "Okay...I want help."

"Okay, you're going on vacation. And let's get out of here, you're staying over at my place."

We take off and go to my place first and we pack some things mostly my computer and laptop a few clothes and taking the groceries that we didn't want to waste and garbaging the rest and closing my place up nice and clean before we head to Mandi's place.

Her place wasn't all that girly but it was at the same time as it was clean and all high end. Mandi was so definitely a girl but she was so this high end scale of girl.

It takes a while getting my things set up and while we're doing that Mandi made some drinks and we smoked a joint and gave me a viagra to take and we started making out again.

It was really good, great and we dozed for I don't know how long.

Mandi woke me up getting herself up and getting things together while running a shower.

I watch her until she notices and smiles at me. "Ready to start?"

I swallowed. "Okay."

"Great there's a drink there for you too and some Molly and a joint, this'll go better buzzed and lose."

I've never done Molly before or Ecstasy but I did LSD as a young teen with my dealer brother and working for myself well drug tests weren't an issue. Her weed was really good.

She had some music going on and we danced a little letting my booze and weed buzz hit before she had me go and shower. Showering wasn't just showering but it was using Nair and getting all the hair off my body.

Then it was getting cleaned up out there.

Freaky, scary, weird...

Then it was Mandi getting me to apply girly smelling lotion and deodorant and a little perfume.

"Smooth, sweet, smelling like a girl, like a sissy girl helps you feel like a sissy girl."

Then lipstick and a wig.

We went back out to her bedroom and she lit up another joint and passed me another tablet.

"What's this?"

"Valium."

"Why?"

"It loosens you up and takes the edge off the Molly once you start tripping."

"Oh..."

Mandi guides me to the bed and we start making out again and like last time she is with me first...this time riding and mounting me on top as she feeds me her perfect titties and we kiss and touch each other and it's different, she's treating me and touching me differently...more girl on girl...sapphic.

And I am starting to trip, my skin is so sweet smelling, so soft and so, so silky.

Then we get to her sucking my cock after that and that's when the lube gets brought out and she starts finger fucking me again.

I moan pretty much instantly my brain, my subconscious had wanted to take me back here so many times it's really played up in my head. She finger fucks me until I spurt then fingers me more until I have a sissy orgasm.

Then Mandi brings up her laptop and sets it up in front of me as she gets me to roll over onto my stomach with a pillow under my hips.

She gives me earbuds to wear.

"Just chill, chill and trip out and listen to the music as you watch the videos."

"Okay..."

The music is some kind of techno-pulse stuff and it's okay and the videos are sissy suggestion stuff and hypno videos.

... You want to be a sissy girl...

... You want to be pretty...

... You crave cock...

.... Face it you love cock...

... You love cock more than you ever liked pussy...

... You crave cock...

.... Beta's serve cock...

Then there's other things as I'm getting finger fucked like these videos that have hypno patterns in them with things like flashing neon, lots of pink, swirling patterns and the longest one is simply this guy's face morphing into a pretty girl with cum on her lips.

... The brain goes pop...

And I can't look away and don't want to because this is what I wanted and more...as I'm starting to trip out hard and I'm so stoned and loose all at the same time and getting finger fucked to one sissy orgasm after another.

Then it kinda sorta happens I have this sissy orgasm and something inside my head goes pop.

And I feel like her, like a her and I squealed as I had my sissygasm and moaned like Mandi getting cock.

Then Mandi has this strap-on dildo she put on and she moves in and she grabs my hips and sinks her dildo into my sissy ass.

Again it doesn't hurt, not even a little instead it's like my body, right down to this deep part of me loves the feeling of getting penetrated, penetrated and filled, inch after thick hard, so wonderfully hard inch sinking deep and stretching me wide.

Doesn't it just say everything that every time this has happened, that every time I'm getting filled in my ass that it never hurt, that the feeling of being filled up with something hard feels so fucking good?

I cry out... it's just sissy girly pleasure as Mandi takes me even deeper than I've ever gone and then she's fucking me.

Her gliding that thick sweet dick inside me...back and forth, moving me, making me bounce and feeling the force of it moving through me almost hypnotic in it's own right as she fucks my sissy spot with every thrust.

My hair long, sexy, in my face, in my eyes and swaying back and forth just like the other sissy girls.

More and more on the screen flashing sending those hypnotic instructions to my really stoned and tripping brain.

... Relax, Keep Watching, Be a Girl, Suck Cock, Be Happy, Be a girl, Be Happy, Lose Weight, Be Happy, Wear Panties, Be Happy, You're a Beta Male, Being filled by Cock Makes You Happy, Relax, Be Happy, Keep Watching, Be Happy...

... Relax, Keep Watching, Be a Girl, Suck Cock, Be Happy, Be a girl, Be Happy, Lose Weight, Be Happy, Wear Panties, Be Happy, You're a Beta Male, Being filled by Cock Makes You Happy, Relax, Be Happy, Keep Watching, Be Happy...

... Relax, Keep Watching, Be a Girl, Suck Cock, Be Happy, Be a girl, Be Happy, Lose Weight, Be Happy, Wear Panties, Be Happy, You're a Beta Male, Being filled by Cock Makes You Happy, Relax, Be Happy, Keep Watching, Be Happy...

... Let the cock fuck all the man out of you...

... Let the cock fuck all the man out of you...

... Let the cock fuck all the man out of you...

... Let the cock fuck all the man out of you...

... Let the cock fuck all the man out of you...

Mandi fucked me literally brainless between the drugs and tripping out and these videos flickering all these things that are so right and so just...yes, yes, yes that I'm pretty sure I was drooling a little.

Cumming is powerful, cumming is addictive too, it really can lead you to thinking differently.

Especially like this.

When she got tired she stopped and lubed me up and took out a but-plug with a cord and sank the vibing plug into my ass.

Being opened that wide and feeling my ass swallow that was so good I got hard and spurted a little.

I vibed and zoned out watching videos and having sissy orgasms until I came down and fell asleep.

***... The next day.

When I woke up I felt...different.

It was nice waking with Mandi too and I couldn't help but to smile at the feelings since me waking up with someone in bed with me was a rare thing.

I had earphones in and some kinda classical music was playing and when I moved I could feel a but-plug inside of me and I was caged in this shiny pink plastic number.

"Oh..."

Mandi rolled over yawned then smiled and I smiled back. "Yeah you wanted it Jamie. Sissies don't care about their clitties they only care about cummies and sissy orgasms and cocks."

I swallow. "Okay...I just thought that there'd be like easing into this."

"Easing into this is for monster cocks sinking into sweet sissy holes."

I was getting hard or trying to and it hurt.

"You'll get used to that, it'll hurt good."

"What about the bathroom?"

"You can still use it, you have the key but you just put it back on after."

"I have the key?"

Mandi gets up. "Duh, I've work and stuff while you're learning and training I'm not going to keep watching you every five minutes."

"Oh, okay."

"Jamie it's real life not just some porn story."

"Oh...Okay, I guess I never thought this all the way through."

She turns and looks at me. "You want to stop? It's not the life that you think if you think it's me being a walking porno or that you'll be a walking porno. It's transition and transitioning is hard and it's work."

"But it's worth it right?"

"For me it's utterly worth it."

I think before looking at her. "I still want this, ever since experiencing this it's like a spotlight got turned onto my actual life and I don't want to feel like I used to."

She smiles and I smile back. "There's you answer. C'mon breakfast and stuff."

Breakfast is a shake and some fruit as Mandi passes me more pills.

"What's these?"

"Hormone blockers, estrogen tablets."

"These are yours?"

"Yeah but I have lots, I have a guy so until I get you hooked up you can take these."

"Okay." I pop them without hesitating and she talks about dieting and what things we can't have so much of as they'll react to the hormones or the blockers in different ways.

Apparently while cock is a sissy's best friend bananas are not.

After that it's Mandi zapping my face. Electrolysis they call it and it's to get rid of facial hair for good. She's not gentle either she says. "You're not going out until I think you're ready so you can take more zaps and heal up here."

Then it's using the bathroom...and cleaning myself out afterwards and lubing and sinking the butt-plug back in my ass.

Yesssss...fuck that feels so good.

Then wearing cute panties pink boy cut panties.

Both make my cock strain against the cage and ache and hurt.

But the cage strangles my boner off pretty fast.

And then working out.

Mandi has excercise stuff in the basement. There's a treadmill and stepclimber and block things for step classes and other things.