Simone

I'm so sick and tired of my life.

It was like I'm cursed.

I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor.

My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out.

So everything was tight and for the most part people in school looked down on me except for the other kids like me.

Geek into tech and D&D and heavy metal it was that and partying with my friends since ninth grade.

Honestly I was lucky to graduate.

But no college for this guy.

Nope, straight to Walmart.

Dad died of a massive heart attack and there was no insurance so mom had to sell the house and she moved out east to someplace in Maine with my oldest sister.

Judy's not a nice person and she's all churchy and republican and stuff. But she took mom in and that was okay.

Jack's in prison, so is Eric and Nicole got away the best having married some guy while she was in the army and they live in Australia.

Me I'm left here just moved a little bit from my hometown to the big city of Amherst.

That's a joke.

Pretty much since Amherst is the closest city of like...maybe sixteen, twenty thousand people.

My job was here so it was a no brainer.

But yeah it's just getting super frustrating.

Half my friends are gone and moved, others are in jail or other stuff and the few still around are like me and working.

I'm renting a crappy trailer for way too much and trying to keep my car running and yeah.

Hand to mouth and nothing to show for it.

And girlfriends?

LOL I've never had one.

Never been with a girl.

Not a date.

Never even been kissed.

Girls don't want guys that are geeks in school or they didn't, they want nice dates, nice cars, they want a guy with a future. That wasn't me in high school it's not me now six years later.

And honestly I think part of me has just given up on all of that.

I had been just going through the motions in a slow spiral.

Three twenty AM and I'm pumping what gas I can afford into my old Camry when I see this nice and literally shiny new mustang pull in and Mike Summers gets out of it.

Mike Summers...

Tall, blonde haired, good looking, was the entire high school stereotype with him the quarterback of our football team and he even went in for a year in varsity wrestling. He had a strong family from everything I had ever seen all upper middle classed and stuff. And always had the girls, any of the girls and dated like every hot one there was in school.

The one thing that threw people was he didn't go to college he went into the airforce.

So not just perfect but patriotic and perfect.

I'm not going to gripe on service people, there's too many kids from my end of things that went in to get the hell out of here.

Me I was way too stoned back then.

I just sort of stared at him.

I was working up to some of that pity mad when he smiled at me.

"Hey Simon, what's up!?"

"You know who I am?"

"Yeah sure we went to school together."

"Yeh but we never really spoke Mike."

He shrugged. "High school was busy, sorry."

"Uhm... no problem? So what are you doing back here and out this late?"

"I just moved back with a new job, and I'm still stuck on Korean time so I'm awake."

"Korean time?"

"I got a job working for an oil rig company after I got out of the air force."

"Wow that had to be rough."

"Not really great pay."

"I heard that about the rigs."

"Oh no I was working for the company I'm an aircraft mechanic so I was keeping their stuff in the air. That's actually even better money."

"Shit...good for you."

Mike looks at me. "So why are you up?"

"Just got off work, we're short so I pulled a twelve from three until three."

"Ouch, you eat yet?"

"No, going to do that when I get home."

"Waffle house?"

"Sorry broke."

"Dude my treat."

"I can't let you do that Mike, we barely know each other."

"No time like the present to start. C'mon."

I was hungry.

"I'm not a cheap date."

"Fine by me."

"Okay then let's go."

We both pay for our gas and leave going to The Waffle House and it's sort of busy and sort of not but we get a booth and order. Mike gets a big load of food and that fits because up close he's a damned tank.

I get bacon and a double stack and some scrambled eggs and we eat and we talk.

He knows some actual things about me or remembers stuff like me being a metal head and into the drugs and being one of the low key pot dealers.

"Not really, I knew people through my brother and I was able to buy for me and my friends but it was really dealing."

"In our small town and school you were as close as we got dude."

He shows me some pictures on his phone of some of the places and it's weird he's as much this tech geek with engines as he is a skin hound. Lots of pictures and lots of babes and lots of places too. Like all the touristy stuff and there's some military pictures too. Like nothing he couldn't have but like some cool shit like from being on ships to aircraft carriers.

"Man I've never really been anywhere. I kind of feel like a loser."

"Simon we graduated six years ago I went home, home and while it was nice to visit there's a ton of the girls with kids and just not doing a thing and half the guys on the teams never finished college and shit they just fucked the dog and are still going around in their varsity jackets living in the past."

"Okay that makes me feel better, so why didn't you go to college?"

"All I had was a football scholarship which was fine but I knew that I wasn't going to be a big deal at a big school and there would be too much stuff going on to get a good degree. I'd have ended up fucking around so my grandfather suggested going into the forces and getting a paid for by them high end trade. So I did and the military stuff opens a lot of doors afterwards with resumes."

"Wow man you have your shit together so what about the homefront, the wife pissed you're out?"

"No wife, no girlfriend right now."

"Why not?"

He shrugged. "Lots of women here, around here not my type."

"What about Jeannie?"

"No thanks."

Jeannie was our waitress and a kind of hot looking black girl that was definitely feeling it for Mike.

"Not your type?"

"Nope, not really and she's looking for the hook up and I'm not looking for that, I've had that."

"Fair enough."

We ended up talking a bunch and aside from him moving back from work Mike was looking to do stuff that he missed out on in high school and the air force.

Which I get but a lot of it was geek stuff that I'd always been into.

So I invited him over and we ended up playing videogames until dawn.

And that kinda started our weird friendship.

Mike didn't try and flaunt his cash. A real jeans and t-shirts kinda guy and he did end up paying a lot of the times that we hung out.

And as much as that bothered me there was some trade off.

Like teaching him about videogames and when he wanted to see Black Panther he hadn't seen any of the other Marvel Movies so we got food and snacks and booze and we marathoned them.

He even smoked a few joints with me to get in the zone of oh wow shit that was cool.

He also couldn't cook worth shit, like typical rich kid sort of unable.

He was a good bartender and made loads of mixed drinks I've never had and introduced me to some booze I've never had.

Slowly he started to date but it didn't work out and a few times he hooked up with them it fizzled.

Which kinda had me pissed not pissed?

On one hand I'd give a lot to date some of those girls.

On the other hand I ended up meeting some of them and most of them didn't like me his dirtbag friend.

A few times he managed to score me dates that were her friends doing her a favor to hook up with Mike.

Those were utter disasters, most thought I was a poor slacker dirt bag. Only one worked sort of out and her name was Jill. And she kinda told me she wasn't into guys that much and was a chick leaning bisexual girl and this was literally a favor.

Shitty? Maybe but she was kind of embarrassed enough by telling me and super uncomfortable that I cut her some slack.

We smoked a joint outside the movies and we had a blast just as friends.

So that was a first, having an actual female friend.

But yeah it was frustrating having my usual dating life and it's results but not just that but seeing Mike fumble all the time too.

And honestly I wasn't mad at him.

Especially after I heard stuff from him on these dates and how some of the ones that fell apart fast were like horror stories of gold digger kind of stuff.

It was like eight months we'd been tight friends when I asked him. "Mike seriously you're not getting anywhere dating maybe you should just be good with someone?"

We were drinking and watching pay per view and he sighs. "Honestly, they're not my type. Simon none of them are."

"Well what's your type?"

"Honestly?"

"Yeah, honestly."

"You."

"Me, dude are you gay?"

"No, nor really but I like trans women, I like sissies."

"Sissies?"

He looked at me pretty openly but intensely. "When I was out east I met some Ladyboys, trans girls and they were sexy, hot, sweet, kind and so not like all the other women I'd been with."

"I'm not one of those."

"Neither were some of them at first, seriously Simon if I had a girl that I liked as much as you everything would be different."

I just stared at him confused a bit.

Mike looked at me and said. "Come here, I'll show you."

We got up and moved to his computer in his office and her brought up this tranny stuff, sissy stuff. "Look for yourself, I'm going to go and get another drink."

I looked.

Mostly porn and stuff but there were sites with actual like talking or just posts and one thing hit me.

Several of these girls with lives like mine.

And then getting this.... "If you cannot have a girlfriend then be the girlfriend."

I read more of that and more and there were pictures of all these shemales and trannys and they all started as guys but they were all doing this, all getting laid but there were so fucking many of them online that this was a legit thing.

And sissies? Okay there was this whole bimbo thing going on and that seemed part of the fetish and porn stuff but still.

I left to get a drink and Mike looked at me.

I asked him. "You still serious about this?"

"Yeah...you don't hate me or think I'm a freak?"

"No, not really, the stuff I seen well there's people legit doing this and there's obviously guys like you into it. I need to think some more."

I took another drink and fuck it I kissed him lightly on the lips.

Okay...that wasn't so bad.

Mike honestly looked shocked as fuck which was kind of cool and not mad shocked either.

I took my drink outside and smoked a joint and a cigarette and then making my mind up I went back inside.

"Okay, deal, I'm willing to try."

He looked shocked.

"Well what's first?"

He looked at me. "I don't know."

I went back into his office and he followed me and I clicked on one of the videos and one of these trans girls was sucking cock.

So with a breath I reached out undid his jeans and pulled out his cock.

It was getting hard and I stroked it and as soon as it started getting really hard I took the head in my mouth.

It wasn't bad.

It wasn't good either it was hard getting my mouth even over his cockhead and I stroked him more than blew him but I kinda did both.

Mike has a big dick too eight inches and circumcised and thick and just big.

When he came I knew when and was buzzed enough that I did an open mouthed cum shot and swallowed.

That was fucking just strange.

Thick, hot, actually creamy in a weird way and there's bits that my brain doesn't want to process.

Mike shuddered and sighed.

I tucked him back in his shorts.

And honestly this wasn't the end of the world sucking dick.

Though I'm pretty sure my first time sucked.

No pun intended.

Mike looks at me. "Are you sure?"

"Not a bit, but I...I want more out of my life, you and me could be that?"

"I'd like to think so."

"We're not there yet, you said you're not gay and I'm way too much guy for this."

"So what now? He asks."

"Shopping? I think I need things before we try this further."

"Shopping?"

"Shopping I think if we're going to do this we need to do this right."

"So?"

"We get a cab and we get started."

Mike's definitely sort of shocked by me doing this and honestly so am I.

But...

"If you can't get a girlfriend be the girlfriend" is echoing through my head like nothing ever has,

No one knows Mike like I do.

And holy fuck I sucked his dick.

And really because,,, because I actually like him that much.

I get some paper and write a list and yeah, my heart is pumping crazy and my head is where... well I don't know but we leave and we meet the cab and get a lift to the mall before it closes.

And as much as I want to go wild tonight I'm not.

Tonight is the acid test, the test run of all of this.

Mike goes to the cash machine and takes out a large sum of money.

I go straight for Victoria Secrets in the mall and the girl there looks at me as I go right up to her.

"I need measured for a bra and panties."

"Excuse me?"

"I need the right fitting bra and panties so I can look sexy for my boyfriend."

"Oh sorry I thought you were a guy?"

"I am right now, so can you help me out?"

She looked me up and down. "Hell why not it's a slow night and sales are sales."

We're actually not in there a long time. I get measured and she sells me the flesh toned gel inserts and I get three sets of lacy black bras and cheeky cut panties and head out paying her cash and then I head to Shoppers Drug Mart.

Veet hair removal gel for sensitive skin, shea butter lotion because I like that anyways, nail polish, fake nails, lipstick, and a make-up kit that they're selling that's like this bulk deal thing from Maybelline, Secret body spray, a little thing of recommended perfume that was still pretty expensive and a curling iron and a crimper.

And I stop by and I get some condoms and some lube a couple of varieties of each as well as an emema kit.

The look on the clerks face was kind of both embarrassing and funny both.

And no.

I really have no idea of what I'm doing.

The next stop is at this out of the way sex shop.

I didn't even know this was here but Mike did and once inside I'm a little stunned at the stuff that's there.

There's a lot of sex toys, a lot of tranny stuff there too.

We don't get much there some more lube and some ribbed condoms and a medium sized vibe and a butt plug.

Those are going to be inside me.

My head's going through stages of excited to curious to oh fuck.

We get a cab back to Mike's place and once we're inside I roll another joint to chill me the hell out and he makes more drinks.

I get my buzz picked back up and I head into Mike's master bedroom.

The enema was the freakiest thing, kinda gross and I'm paranoid so I cleaned myself out three times and then it was in the shower with the hair remover.

That stung honestly and it's a good thing that I had the buzz that I did so it kept me from freaking out.

Though being smooth, fuck that's way nicer than I thought it would feel.

And the lotion I used felt good and made me smell nice too.

It wasn't until I pulled those lace trimmed cheeky panties until it really started to feel girly.

That satin encased me so softly, so tightly too and I tucked my cock away as best as I knew how to.

But it was the way they framed and clung to my ass that did it, the feeling and the way that I looked in the mirror.

It made me excited for more.

The bra was next and getting it on was easy fasten it in front of me, then turn it around and then slide it up and settle the bands over my shoulders and when I filled the cups with the gel inserts it gave me this shape.

I looked hard in the mirror and said to myself. "Can't get a girlfriend, be the girlfriend."

I said it three times.

Meaning it more and more.

I'm tired of being lonely, I'm tired of being a virgin, I like Mike, He's my best friend, I've sucked his big cock, I've kissed Mike, he's handsome, he's smart...I want him.

I get determined as I do my hair using the crimper and the curling iron to make my hair looking as girly as I can get it. I've had long hair since junior high and started as a metalhead and some of this isn't too hard to do or the make-up either as I've worn both but just in that metalhead sort of way.

Getting girly is a different approach but I go with the way the girls in the clubs and concerts looked.

I was still nervous when I came out and looked at Mike.

I wasn't really prepared for him to stare and say "Wow, Simone, you're beautiful."

Simone.

Okay.

Then as my brain is dealing with everything Mike comes over and he kisses me.

Like a real kiss, like romance movie style I mean something kiss.

This never happens to me.

And we kissed over and over and I'm not good at this. I have zero experience in kissing or being kissed or kissing back but slowly as we're doing this it's kind of sinking in that Mike's doing this to me...with me and he's into it and into kissing me.

That really feels good on this emotional level I didn't think I had or really get how starved it was.

And wow.

The way Mike's touching me, the way his fingers trace over my skin.

The reverence there?

I'm getting turned on.

It gets better as we kiss to his bed,

He has a sleeping bag undone there so it's... we're not going to make a mess I think.

And there's more kissing, his hands touching me, feeling my ass, playing with my panties.

He's hard, he's so fucking hard.

Mike lays me down and there's more kissing and more kissing as he reaches my panties and pulls them down.

"Roll over Simone."

I roll over and then Mike has the lube and he's applying it to my asshole and he slips his fingertip in a little a few times and I gasp and whine.

"You okay?"

"I'm good just this feels so strange, good but strange."

"It'll get better, just trust me."

Mike kisses me and sinks his finger into my ass and I gasp around the kiss.

It does feel different, does feel strange and kinky but it doesn't really hurt with all the lube and Mike starts to finger me and then his finger hits something inside of me and there's this surprising jolt of pleasure.

It feels like that twinge of good that happens as I jerk off that jolt that runs through me as I'd start getting close to cumming.

Mike touches that again, and again, and again making me shiver as it's happening faster than ever when I'd jerk off and it's deeper too. Like inside me deeper than my cock or the base of it.

I cry out as my cock fires off a load of cum into the sleeping bag suddenly and without warning and I moan and gasp around his mouth and Mike's finger keeps going and keeps giving me these jolts over and over and his hand is moving faster and he sends me over the edge of cumming again.

Only I just came so it doesn't spurt it sort of explodes inside of me like I came inside of myself.

I moan. "Mike, Mike oh fuck Mike what was that?"

"You just had your first sissygasm babe."

"I...."

He kisses me harder and he fingers me to another one making me shiver and my eyes roll in the back of my head.

He moves and I'm trying to recover but it feels like my insides are melting along with any reservations about this.

He lubes me more and then he sinks the vibe into my ass.

My very rapidly accepting sissy ass.

It was bigger and harder inside of me which was this definite awareness shift of something in my ass and at the same time right now I didn't care.