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Not Just Another Gradual Change Story – PART ONE

As I write this I am sitting at the computer wearing a summer dress that’s pretty damn short. I’m about to go out again because yesterday was so fun…

As we all know, certain unnamed stores in the not too distant past (stores that were already very LGBT friendly) decided to start allowing people to choose the bathroom they want to go to regardless of what their birth gender happens to be. As a closeted bi guy who loves to dress up on occasion, I realized that this must also mean that the store policy is not to harass people simply based on them wearing clothes that may not match their birth gender.

I have been going to a particular location of this store for years. I love it. There is a big university close to here, so you always see lots of young hotties shopping for clothes, makeup, groceries, and housewares. The staff also includes quite a few sexy women from age eighteen on up. For instance, they have this one tall milf that wears glasses and has an amazing body that she tries to hide all the time. She has curly hair. She sees me check her out a lot and I can tell it makes her uneasy. If I had to guess, it would be that she feels uneasy not because she is unattracted to me but because seeing me look at her makes her ask herself if she looks weird or ugly. A lot of women, especially ones that you can tell do not think of themselves as attractive, have this sort of initial reaction to this sort of attention.

There are also a lot of hot young girls that work there. After about a year of shopping there, I found out that they recruit strippers from halfway house type programs. It sucks so bad to be a Target cashier that they have to try to vulture strippers away from the noble profession of showing their asses.

You’re like how the fuck does this dude know this? He is full of shit, etc. I am sure many of you right now. Well, this one chick used to come in the gas station all the time and we had become acquaintances. Fat tits and ass, lots of tattoos babygerl face and blonde hair. She’d come in dressed like a complete slut 9 out of 10 visits, and the rest of the time it was slumpy sweats cuz she was so stoned she didn’t give a fuck.

Body wise, I’d fuck a chick like this in a heart beat. Lifestyle wise, I’d only spray my jizz on her but there’s no way I’d let her nasty ass touch me. Also, if I am gonna spray her over I would definitely have to be filming it to show you guys. That’s another story, not too worried about her. The point is what she told me.

Stripping is legal here like it is in most places, but that’s not what these little whorebags get popped for. It’s usually a combo of minor d**g offenses and of course prostitution. Again, where prostitution is already i*****l but stripping is not, the overlap of the two professions is pretty huge. If anything there are way more whores that don’t dance for money in a club but will do just about anything you want in a room for the right amount of dough. I could go on and on about some of the legit chicks in ads I’ve seen. I actually paid for an oil massage once, this chick was new to the scene and super clean. Not nasty like the last chick I was talking about. Yeah, you never know what she might have had, but unlike the stripper chick that was doing private parties with her friends at fat old dudes’s trailers, this chick had her own total studio with a shower, full length wall mirror, and massage table.

If you read many of my stories, you’ll find they wander and go off on tons of tangents. To that I say, I hope you enjoy them. There’s a reason my sex life is strewn about all sorts of weird ways of perking up my perverted cock. Shit, last night I was so close to fucking this amazingly hot and super thin tall blonde 27 year old. She was pretty buzzed and came in to my work right after close dishing on her whole life as a mistress to an ungrateful married man named Tyrone (now this Tyrone could be a white dude, very possible… but at this point in the context I think we can probably agree the cock she told me she has been getting pounded by for a year and a half is big and black on that dude… there ain’t many more stereotypical names for darker skinned dudes than that). I hooked her up with a rice crispy bar which I enjoyed watching her stretch her small, sweet, unmakeupped lips over repeatedly while talking about how frustrated she was with this dude. Her work is right by mine, and I already knew her, and I have been growing some huge balls lately, so I was talking mad shit to her. I was trying to game her horny young pussy, hard.

I am in my mid 30’s and have always been super shy around opposite sex. I am told that I’m not bad looking, but I pretty much have to fall into pussy most of the time. If it requires much effort or even noticing interest, I am usually out to lunch on it in one way or another. But last night I was really laying it on her like I ain’t never laid it on a chick that has shown no interest.

I have always told myself if I talk this way to a chick that she will almost definitely slap me or at least disappear immediately. Here I am, telling her she would remember my name no problem after one session of me bangin her while she screamed it. Normally I’d imagine saying that to a chick out of the blue would almost certainly get a super angry reaction.

Instead of freakin out, she chuckled hard as she jammed another chunk of her crispy bar in her mouth, a piece of M and M falling toward the floor and missing her suddenly upturned hand that tried to catch it. The visual reminded me of so many nasty porn cumshot scenes I’ve seen where it starts spilling out of the chicks mouth all over and she does her best to try to catch some.

After her chuckling she just started pretending to scream my name. Anyway I said a bunch of other shit to her like that I could cum in her repeatedly no problem without stopping, and could her married dick do that, etc. She said no cuz she was not on B.C., and when I told her that’s cool I got vasectomy, she laughed a bunch more.

Told her I’d imagine her in all sorts of positions, legs in every direction, she just goes yeah most guys probably would, but seems totally unoffended. She’s heard all this shit before.

Anyway, there were a few more lines that did okay but in the end she was all about getting the fuck home so I told her have a good night and she dipped.

Back to the stripper chick at the department store now, I saw her again where I worked after she had rang me up at dept store and I commented on it. She explained that she had been in a halfway program type thing and that the store hires people out of it to run cash registers.

So there is a few more wandering paragraphs just to explain one lil thing. Learn to scan over the boring parts if you just want the sex. Don’t worry because it is cumming.

I do want to tell you about one other cashier really quick. I wouldn’t be surprised if she was a stripper too, but one day recently I was showing her my tap and pay working and said lemmeshow ya somethin really off the cuff and not even trying to hit on her hot lil ass. I almost shit when shorty looked up and innocently smiled while saying “You can show me anything you want!”

Where’s my time machine so I can backup to that? I have been back a few times hoping to see her but no luck yet.

Anyway, this particular location of this particular store may have had something to do with the decision to allow crossdressing all over in the store because there are at least two girls with penises that have been working there for years. Obviously there could be more penises in those khaki pants that I don’t know about, and the revolving door at this place has different young chicks in there EVERY time I go in. Anyway these two were long time workers here, and I loved to watch them whenever I’d see them. Can you imagine how badly I wanted to take either one to the closest potential fuck location to do just that? I wondered how much or little they wanted to have such an effect. I wondered what their threshhold was for agreeing to begin engaging with sex with a strange customer. Well, I guess I still do. One of them is quite tall, an inch taller than me even and I am a good deal above average. His/her body is fuckin amazing. She used to be a lil more chubby in less fortunate areas, but yeah… as she has taken her hormones she has shaped out so nicely.

It is obvious, so obvious that this is a hormone therapy man, now… I must say. But she is one of those that while still obvious is so close to being pretty fuckin passable (and would definitely be in LOTS of situations with the right getup on, especially if people around were under the influence)… but in broad daylight or under those bright florescents there was no doubt to anyone that cared to see that it was someone born with a penis.

Her tits didn’t get giant, either. They got just the slightest bulge to them from all her hard work. Her ass went from flat and square over the past few years, starting out like a man’s, to become rounder and rounder every time I have seen her. The last few times I have seen her, she has not been working but shopping there with another female looking person. Now this person, if a penis, hides it so well that I simply cannot tell. That kind of ambiguity drives me wild with sexual anticipation and lust also, by the way. How hot is it to wonder what is down there, this chick wearing nothing but a sun dress and all? The one I know was born with a penis I have only seen in a skirt one time, it was like a tight dark green military looking rig with cargo pockets. I wanted so bad to be at the right angle to be checking out what was hidden there, and actually that time she caught me staring.

To add to my anguish, tall chick in the tiny green mini didn’t seem freaked out or turned off by the fact I had stared but also showed no apparent interest in idea that I was either. I always hope a chick will catch me staring and start to show off. It has happened a few times. Actually a few days ago at the wading pool this milf with huge legs, ass, and tits was wearing a cottony white and navy sun dress. When I got to pool I made it a point to sit on bench directly opposite to where she was at edge of pool with her legs spread.

This chunky milf’s panties were obviously that. How can you tell? When their sun dress set up is obviously cotton AND the panties don’t match it at all.

Okay, maybe they weren’t obviously that because maybe they were swimsuit bottoms or part of a uni or something.

You know why it doesn’t really matter that much to me? (Paying attention, ladies? I hope so, god you guys are so naive when it comes to the fact bathing suits are basically two layered underwear it’s not even funny and boy do I fucking LOVE it! Nothing better than a milf or teeny chick in a bikini that you know good and well would be screamin with hands tryin to hide every possible inch if you saw her, bending over the way they love to do in those wet spandex setups, wearing underwear instead of spandex.

Okay so yeah it could have been a bathing suit bottom thing but the point is that she noticed me looking and right there with her hubby she casually opened her knees while watching me and reached down to start scratching her leg. The fabric stretched lewdly across her sex for me while she looked down to scratch her ankle, but she was repeatedly peering up with her head still down to see me.

I was wearing some thin spandex shorts and was nicely medicated so my already arching dick went ahead and stood straight up.

When this happened I went into the pool right away so that at least I could try to ‘hide’ the 90 degree boner maybe by leaning forward some. I can tell it had the intended effect of actually showing it off a lot more and getting it a lot closer to her eyes, because at this point I was putting on the show for her. My shorts already shine like crazy with their thin spandexness when dry, and after getting splashed all over I can’t imagine what the show was like for her horny mind. Her husband was right there and she would occasionally look over at him to see what he was up to while this whole thing was going on. My guess is that he is probably not the type to want to share and that she was trying to be as careful as she could not to tip him off in the process of what she was doing.

Anyway, yesterday I didn’t get to see either of the two shemales that work at the store yesterday, as I had hoped when I went in at first.

I can’t really afford to be seen wearing women’s clothes because my wife would definitely freak. She knows I like panties only, and I never bring that up because she is obviously a lil freaked out and grossed at idea I would get off on it.

Funny thing is she has this super dirty mind, my wife. She has talked about that I probably sniff and wear her panties while she is at work, shit like that… but the fucked up part is that she SEEMS like it is NOTHING but a joke, so I have to treat it as such. (I am pretty sure she knows I am a big time crossdresser by a lot of hints she has dropped, but I am mortified at telling her and us having a breakup just because of that and yes she has definitely indicated that things ass off the wall as that should be considered deal breakers without being super specific. I’m just assuming a lot, definitely… like I said, it is definitely possible she is only joking about the dressing up thing. That dark green dress in the pics on my page, she couldn’t find it one day and was like ‘ya probably been wearing it all over the house and got it stuck away somewhere’ all nonchalantly. I play along for a second like ‘yeah I get my wig on and go online to shop for tampons…’ with a chuckle to indicate the sarcasm and she gives me this look, only in jest, but this look of YOU WHAT GET OUT MY HOUSE type of shit lol.

Anyway, I honestly would say there is probably like only 15% chance in my mind that I could be like baby I like to wear womens dresses sometimes and she not dump me for it. I am so super scared of us breakin up over something stupid, and have been with her like 20 times longer than anyone else in my life. We fight all the time but in the end are so very compatible in the most important ways other than sex. Yes, I was about to just put a period but her sexual attitudes are way different than mine. Oh, besides telling her about panties I did tell her I have sucked dicks and let guys suck mine for fun. She does not like that idea at all either, has teased me over that occasionally (like we’ll be talking about some gay guy we see just cuz of how funny he is, and before the convo is over she’ll be like you know you want him).

I asked her before if she would fuck a girl, and she said she didn’t really want to. I asked if she had fantasized about it and she said sure, I asked if more than once and she said yeah. She explained to me that she does find females attractive and all, but that she just doesn’t see herself being that type of chick. (I think it’s cuz she thinks she is too overweight and ugly to be attractive, same reason she barely ever feels loose enough to let me fuck her anymore, but I don’t press these issues).

Anyway, now that I’ve told you a little about how that is playing out, you’ll understand why I might have some hesitancy at trying to be crossdressed at my local store to see how it would feel to do so. If you are a guy testing these sorts of waters, what better place to go than a store that promises, ‘Hey, its cool’ and on top of that is full of young female workers?

I know most people probably think crossdresser and instantly think (homooo!) but the fact is that most guys who want to look sexy and feminine feel exactly that way about females, that they are sexy and super fuckable.

Anyway I went in there yesterday to buy my dick hard pills and decided I would wear a sun dress and some heely things and my wig and sunglasses and red lipstick that I have. The wig is this cheap party store wig, but it is better than nothing.

Whoa the looks I got. Major distraction, major head turning. All sorts of hot looking dudes were catching glimpses and suddenly looking away a bit with a quick smirk. I wonder how many were thinking o yeah lets fuuuuck you slutty crossdresser.

So yeah I am bi, I love suckin dick and trading cum swallowings, but dig chicks more in the end. That’s why I really like shemales and agree with the best of both worlds sort of thinking.

Anyway, there was a dude and a chick pharm tec working. The chick had waited on me many times, about mid 20’s, blonde with a really dumpy ugly shaped face but super nice complexion and some serious dick suckin lips. Chick never smiles, has super curly dirty blonde hair and again a dumpy body the way she dresses but is young, normal weight, and I guarantee any dude with a prostate full of jizz and the right opportunity would fuck the shit out of if he saw her naked.

I made it a point to hover around until the dude was away from counter so I could try to get the chick. As soon as she looked most available I moved into position since no one else was waiting, but damn all the luck she took one more look at me (she had been giving me odd glances the whole time) and went back behind counter to say something to him.

He nodded and took her place. Doh! Fuck that, I pretended to ‘realize’ something and mutter to myself and left the spot for next person. Peeping over my shoulder with my sunglasses I could see not only the two pharmacy cashiers staring at me, but the pharmacists were peeking as well in the middle of trying to fill prescriptions. Don’t get distracted now, I thought, slowly bending over to ‘adjust’ my shoe strap while making it a huge point to keep my legs straight so that the pouch at the rear of my genitals and the fabric stretching up between my shaved ass cheeks (my legs were totally hairy from thigh high level down, by the way, still hairy as fuck.) would DEFINITELY be exposed by the rising fabric. I looked over my shoulder again, sunglasses still on, as I messed with the shoe, and saw five sets of eyes staring. Four were behind the counter and the other was a tall brown haired milf with a cross necklace that had just rounded the end of the aisle. Her eyes were like saucers man, and then she furrowed her brow and yanked her head back on her neck a bit like what the hell??? and shook her head visibly and ducked away from her initial path down my aisle.

The whole time she was doing this I was continuing my show, pretending to drop my shoe and saying ‘fuck’ all high pitched suddenly and gay sounding. I ‘dropped’ the shoe on the floor in front of me. The milf had taken off from disgust, and one of the pharm tecs was staring straight down and trying not to see me, but the two cashiers and the younger, blonde, freckled, thin, amazingly hot to a guy who likes plain blue eyed freckled chicks that never wear makeup pharmacist apprentice were staring big time as I went down to my hands and knees and shoved the small of my back towards the floor, stretching out with my hand for the shoe.

I knew it was obvious at this point to them what I was doing. The pharm apprentist was sneakin little smiles and glances as I stood up and straightened the sun dress, the female cashier was now trying not to look just like the other pharmacist, and the male cashier who tried very hard to let me know he was secretly gay when he talked to me whenever I have talked to him was smiling with his mouth a little open in obvious, delighted surprise.

Anyway, I camped out until the pharmacist apprentist, the freckled one, got in the right spot to be the one to wait on me, and I stepped up again. At this point I tried to go ahead and make it obvious I was waiting for a chick. I could tell the dude had seen this before and was actually trying to facilitate my desire wordlessly, because when I stepped back in position he almost came over to ask if I needed help but when seeing her close to counter also grinned a little and backed away.

Thank GOD. I love this lil bitch. Tiny tits, tiny everything… I bet she is 21 or 22. Hot as fuck, any guy’d fuck her as far as looks go. Anyway, I won’t go on and on but she was super friendly and polite and made me feel comfortable enough to ask for her number.

When I did, she bit her lip, looked down, glanced in both directions, and showing obvious hesitancy said ‘… well, okay… I never do this but if you are as chill as you seem I guess we can talk, just talk!…”


Updated: October 21, 2016 — 1:29 pm

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