Subliminal Obsessions

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A lonely, loner guy meets a sissy that changes everything.
6.4k words
4.61
73.5k
102

Part 1 of the 7 part series

Updated 06/08/2023
Created 05/24/2017
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Sissyhalo
Sissyhalo
667 Followers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room.

And my luck turned around after I won money.

Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not big cash but you know it was enough to move, first and lasts plus getting back my deposit from the other place and I moved to 200 Timber lane.

It's one of those places that was amalgamated into the city so it's in town but it's kind of off in the boonies for the city in a kind of older neighborhood with a lot of older buildings.

The apartment building is just two stories and it used to actually be some kind of bakery I guess according to Jack the super who showed me the place and the shipping dock room was converted into a pretty big laundry room.

And my place was one of the basement apartments.

It was actually pretty spacious and the floors were all tiled or oilcloth and there was new carpet in the bedroom and while there was lots of space and heat included in the rent since it had a hot water pipe and boiler system it was still out of the way and my drive to work went from fifteen minutes to about forty.

There was a corner store at the end of the street and a few blocks away there was a big gas station that had one of the built in stores and liquor stores and they had a Pizza-pizza place across the street from them.

But everything like the banks and the malls well they were as far away as work was.

But the rent was reasonable, actually it was pretty good for the city.

And the neighbors as I was moving in were both nosey and friendly.

Oh yeah the usual ones in to check out what I had as I was moving in which wasn't a whole lot being a single guy.

Okay a sort of geeky and very single guy.

I'm not even that much of a geek just I like movies and I like cartoons yes at my age still and I've never really had a big social life. I dated a few other desperate souls in high school but that was a lot along the idea of it would have been so utter shit to be alone.

But I never went to college, smoked a lot of dope with my friends and barely graduated and I just ended up going out and getting a job.

Oh yeah I work at a window plant making those vinyl windows. That turned out to be one of those high turnover jobs because the work was sort of hard and it was kinda dangerous too with getting plastic burns sometimes or getting cut.

It didn't take a rocket scientist to pay attention enough not to get hurt. And that one little bit of common sense got me there long enough for full time and off shift work.

So I had things with an okay income.

Some things I just bought cheap and new. Like those cheap twenty buck blenders and mixers and things. I had some of those and my big extravagance was getting a new box spring and mattress at the liquidation place.

But the neighbors were pretty okay and there was mostly a bunch of single guys here and everything so it wasn't that bad.

Shawn this guy about my age from across the hall actually brought me over a pint of Crown Royal as a housewarming gift.

He was well...pretty like guy pretty and kind of effeminate looking and soft spoken and all not that I have a problem with folks like that, each to their own you know.

He extended his hand to shake. "I'm Shawn I live next door."

"I'm Mark, thanks for this you want a drink?"

"Sure, I won't turn down a drink."

"How do you like it?"

"Ice is fine."

I laughed. "Well I haven't gone for groceries yet so ice is all I have."

I found two glasses that are actually for drinking whisky from and poured us a decent drink each and added some ice from the fridge door and we talked a little while and he asked what I did and I asked what he did which was website design and management which seemed to fit as he didn't look like a remotely hands on guy.

He stayed for a bit longer letting me know some things about the neighborhood and then left and went back across the hall for his place.

Life settled in after that, work, chilling out, watching movies or TV a lot of online TV stuff too. I'm kind of a homebody since most of the friends I had either live in other places and are online only or they work and other stuff that just has us occasionally seeing each other.

Especially the folks with kids, honestly I'm not a fan of kids a lot but some friends have them and well that's about it. Yeah I'm the person pissed at kids being jackasses in a nice restaurant.

Anyways life was pretty much life until I was doing laundry and it was just there...this basket of underwear and not just underwear or panties but hot girl panties, like the Victoria's secret kind of stuff, stretch lace and satin or something lots of bright colors.

I still don't know why but I stole two.

Well yeah I know why, because the shape, the look the girl must have been hot.

So they became stroke material.

Then each time I stole another and another pair until I found an envelope on the washer one day when I looked for more.

There was a note inside.

(If you're going to steal them Mark at least wear them.)

She knew my name.

And for two days after that I was honestly freaked out and limp too just it messed with my head.

The third day I slid a pair on.

I only wore them at home and the boner was incredible. So was jacking off to them.

And I had enough that I wasn't taking any more of hers.

But like three weeks later there was another note in an envelope on my clothes basket.

(You're wearing those all the time now aren't you Mark? Here, use this, it'll look so much better when you stand in front of the mirror.)

There was a coupon for a dollar of hair remover, the stuff women use in the shower.

Fuck me didn't I go buy it.

I showered and used the stuff which kind of stinks and it kind of stung some too especially on my balls. Yeah I know they don't advise that but I figured what the hell right?

And suddenly I was smooth.

And I never really checked myself out in the mirror either, not like this, not like over and over.

The hard-ons were incredible and just honestly it looked better, looked right.

When the weekend rolled around I was determined to find and meet panty chick so I sort of stuck around did an extended wash with all the stuff like towels and bedding, couch covers and things I usually don't do.

She came in.

She was Shawn.

Yeah I know part of my brain had sort of guessed that but she was either Shawn or his twin sister.

In fuck me heels and a robe with stockings and her hair done and nice make up he...she had some curves. A nice waist, tiny breasts, no bra from what I could tell and wow, what an ass.

"Shawn?"

"Sometimes, when I'm in drab, when I'm just being me though it's Sarah."

"Oh...I..."

"Were waiting?"

I blushed. "Yeah I wanted to meet you?"

"Me too, I was waiting for things to be more awkward."

I look at her. "More awkward?"

She smiles and she's fucking pretty. "Yeah well if I was going to ask you over so we could fuck it's a lot easier to ask that when you're hard and wearing my panties."

I blushed again. "I..."

"They're sexy and fun, I get it heck I'm wearing something even better so I get it. Here how about you come back to my place and I'll pay you two hundred dollars so I can suck your cock and so you can fuck me."

"What?...wait what?"

"You heard me, I'm going live shortly and you're invited."

"Live?"

"I do cam porn Mark."

"Oh..."

In the end my aching cock decided for me.

"Okay but can you blur my face?"

"No, trust me Mark no one watching this cares about your face they'll be watching other things."

"Okay...okay are you serious about the two hundred bucks?"

"Absolutely, everyone needs money right?"

"Yeah things are okay but still."

Sarah smiled and took my hand and took me to her apartment.

It was girly and not, I actually liked it with some actual real paintings on the wall mixed in with photos some of Shawn some of her in places they've been to. She or they put down hardwood flooring instead of the tile and there was a nice entertainment unit, big tv on the wall and a really cozy and fairly expensive living room set.

She had shelves of plants set up at her main window of her kitchen and I could smell them a little.

Sarah took me to her bedroom which was girly, Thick carpeting and more art, there were several faceless black and whites of her body that looked professional and she had an exercise corner with a ski-stepper machine. and really nice too like not too over the top and there was another big screen TV on a night stand where she had the camera's set up and her computer.

The TV kept cycling through these pictures of porn all she males too and guys with them but with captions in pink and saying stuff like. "You brain is just too fagged out, grow tits, date guys, suck cock and have fun."

And more and more all saying things like "Feminize yourself." or "Start being popular, stop being boring, be a bimbo, give in and suck cock all day long, live for cock, find a daddy."

Lots more, lots more stuff about being a sissy or wanting or knowing that you are a sissy.

"What the heck is this stuff?"

"Self training, things that are just me."

"What?"

"I'm Sarah and Sarah is a cock loving sissy slut."

She dropped her robes and she was braless with pale skin and these really tiny titties and she was wearing crotchless panties and garters and her cock was smooth and tiny, her balls were tiny which was hot and scary and fascinating.

I was going to ask questions but she came right over and took me buy the hand and led me out in front of the camera and undid my pants and dropped to a squat and pulled my raging cock from her panties.

"Oh fucking yum, I love dick."

I've had three blowjobs in my life but Sarah was a thousand percent better as her lips wrapped around the head of my cock and she made love to the tip turning her lips back and forth over the head, behind the head making me moan, moan more as she played with my balls and then deepthroated me.

That was my first and she didn't gag or anything but she sucked my cock hard, sweetly, but so insistent and she made my cum and she opened her mouth to show me and the camera her mouth full of my spunk and even let some run out over her lips then she sucked it off her fingers as she swallowed it all.

"Mmm...fucking yummy."

"Glad you liked it."

"I love cock, I love all cock, I love the taste, the smell the feeling of hard, hard dick under my lips making them tingle with friction."

She was getting me hard with the talk and her stroking me. "And I love cock in my ass, stretching me, filling me with heat and hardness and making me cum like the sissy that I am."

I'm hard and she rubbers my up and passes my lube and turns from me and goes low with her ass up.

"Fuck me Mark, fuck me, fill me, sink deep into my ass."

Sarah's voice is soft and sort of mixed between breathy and high and late night radio chick.

Her ass was so hot, and she was clean inside as I lubed her and then sank in.

I've never had anal before and she was tight and hot and perfect.

Demanding too in her "Harder!, Grip my hips, There, there, there!"

Vocal as fuck when she squirts cum and I never touched her cock, cocklette?

And when she did that her muscles gripped, pulsed and flexed around my dick and I shot a load that felt like a testicle imploded from the rush of cum blasting out.

I almost lost my balance with my legs going shaky and hold on for dear life as Sarah flexed her ass muscles milking my cock before she pulls herself off of her.

I sank to my knees and she turned herself around and kissed me then pulled off my condom then she sucked my cock again rolling me flat on the carpet. I didn't think there was anything left in the tank for me to get hard anymore but Sarah was the most amazing cocksucker.

The big screen TV still cycling messages about how much sucking cock is fun, how much sissies crave cock, how girls look so beautiful with cum on their faces, with their lips wrapped around a hard cock.

She definitely took all this stuff to heart.

Sarah sucked then pumped a facial out all over herself and let it run and drip down before rubbing it into her small starter titties and off her face with her fingers and ate it.

She got up and she went and did something on the computer and sighed.

"That was good thanks."

"I should be thanking you, gods Sarah sex has been never like this, you're amazing."

Sarah smiled. "Well I should say so. I love cock, I love sucking, feeling, tasting it Mark."

"Like the stuff on the screen?"

"Just like, I mean I knew I was something I just needed little pushes to be me."

"With this stuff?"

"And others." She tapped out on her computer and it started playing this flashing strobe of all this stuff but more with all these words like sissy, swallow, cock, worship cock, you're not a man, you are a sissy, you are a sissy, you are a sissy, suck cock, be happy, suck cock, empty your mind, keep watching, suck cock, be happy, drink cum, be happy, swallow semen be proud, suck cock, be happy...

I blinked it out of my eyes and looked away because it's very flashy stuff and there's a lot of neon.

"And that works?"

Sarah nods and gets money from her purse and pays me which gets me sitting up. "It does, still more of a push really but you have to use it right."

"Use it right?"

"Well yeah first you got to be open to it, then a little resistance softener helps?"

"Okay that sounds ominous."

She laughed. "Okay basically stuff to get your mellow on."

She walked to a mini bar as I slid my boxers back on and she made two drinks and drank some of hers as she passed me mine. Mmm...vodka with lime and club soda on ice pretty much just what the doctor ordered.

"Drinks..." She passed me a tin of...oh...Molly...Ecstasy...I took one and smiled popped it in and washed it down. Like fuck it right it was the weekend and I had no plans and she did the same "My friend Molly." and I got up with my drink and sat in her bedroom chair and drank some more while she took a tray and sat on her bed and a bag of weed and rolled a joint. "And some good toke."

"Okay..."

I mean I wasn't going to dissuade Sarah sharing her stuff and that might lead to more sex after you know.

She had some really good weed.

We got high and sarah sat beside me in the chair and we kissed and she talked about chilling out and relaxing and letting the drift happen.

And she talked about having cock inside her and how she loved it in all these ways from the little ow not ow pleasure feeling of getting entered and how it feels like this addicts prick and knowing it's going to bring pleasure that will take her out of her everyday, how the cock massaging her insides feels so amazing, the hardness, the heat of it, then there's the feeling that come bubbling up from feeling sexy, wanted, desired.

I wasn't trying to not watch the video but I was watching it and other ones as they rotated in sequence and pretty high as I was it was all eye catching and stuff.

Hours later we had enough and were coming down and got dressed and walked ourselves down to the pizza place before they closed.

It was one of those cool out with a girl and a friend both plus that drunk/stoned walking around with someone at night with no real aim.

There was this really great three AM moment when we were eating pizza in the local playground park sitting on the swings.

Then we went home and I crashed hard and was lightly tripping.

Not being able to go to sleep because of that I went online with my laptop and looked up sissy...sissification...and cruised and watched things, found some of those hypno flashers too.

Sarah was like Sarah so into this stuff but this was kind of stroking stuff, kind of.

I watched until I fell asleep.

I watched it again when I woke up, my cock raging hard and full of dreams and came hard, hard, hard.

I debated it over and over then scooped it from my hand with my tongue.

It wasn't bad, wasn't scary or horrible other than the things in my head from society saying that.

And the girls on those videos did it all the time.

I thought, no I knew that fresh from the pipe would be better, it cooled so fast.

I went and got up and showered thinking a lot about the line I crossed.

Used my Nair and got hairless again and slid myself into Sarah's panties, my panties.

My panties, I was doing this, heading here wasn't I?

I went next door after getting dressed and knocked and Sarah wasn't home so without that option or sounding board I grabbed my jacket and my money and went shopping.

I mostly went up to the malls and wandered around and found myself more than once staring at guys that looked built or looked like they might be having good sized cocks.

I was really going there.

I mean part of me was struggling with it for sure it was gayer than fuck, and while gay people never bothered me it wasn't ever part of my sexuality before.

Part of me though led me to Shoppers Drug Mart and I bought things, lotions, and some new razors and some girly body wash with the puff kit and powder and things to dip my toes in the feminizing pool, at Bed, Bath and Beyond I bought new bedding some of those faux satin sheets and just a new bed set package my first actually never having thought to have all that matching stuff before.

Then I headed to get a few groceries going for the girly stereotypes of the healthy things like salads and fruit that sort of stuff and with that some booze.

I headed home after that and sat and watched more trying to think, trying to decide if I was going down that rabbit hole and drank my first bottle of wine that wasn't cheap high school hooch.

They seemed so happy, so willing to be girls.

Dicks and all they seemed to revel in sucking cock and getting fucked and I knew it was staged and it was porn stuff but still there were so many and then there were all these transgender blogs out there and some of them were just sissy blogs as well and then there were all the stories people wrote.

We were out there and we were real people.

I half dozed buzzed after clicking on one of those feminizing hypovideos and napped half watching through sleepy eyes on my couch watching the screen on my coffee table.

What if I'm like Sarah? What if I want this? What if I wanted this all my life and just needed the push?

It's not like I've ever developed anyone close ever that'd object to it.

Well there'd always be bigots but, no one close like lovers and family.

My family would hate it but then again Dad was an asshole that thought he owned us and one of the reasons I moved was he thought entitled to everyone's free time and labor and not even a thanks. Mom...I hated her because she was the queen of guilt trips and passive aggressive head games. My brother Tom was a druggie and yeah while I use his life is solely about his highs and I literally have zero contact because he had ripped me off of things all my teenaged life to help feed his habit. And Mary my sister left early because she wanted out too and for the same sort of reasons but she was like mom too and pissed off all the time because she never grew up as one of the rich kids.

So, no no family. We don't write, call, e-mail... no cards of birthdays or holidays...not for a few years,

I couldn't, still can't. Every trip home was a fight and horror, guilt and manipulation.

I just moved, changed my phone, left and never looked back really.

And those thoughts led to feeling alone and upset for the first time in a long time over that.

I got up and turned on some tunes fairly loud but stuff I never listened to too much a chick rock playlist from Youtube and went and cleaned my apartment. I mean it wasn't bad or anything but I went into that fussy cleaning and washed my new bedding and dried it and made my bed.

Sissyhalo
Sissyhalo
667 Followers
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