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Chris Today Christina Tomorrow
I have never been the guy that you would see catching the touchdown pass, drinking it up with the boys on a Friday night, or even dating the cute girl from school. I was always the outcast in school, and personally, I didn't mind one bit. My parents would always to tell me "Why don't you go out with some friends tonight?" or "Do you think you are going to try out for basket ball this year?". The answers were always no. I had very little friends, and even littler interest in playing any sports. MY only friends at that time were mostly nerdy girls that only liked talking about their thoughts on the new "Harry Potter" book, and when the new "Twilight" novel would be released. I loved both of these things more than anything, because talking "man talk" always made me uncomfortable. Football was never my thing, cars were never interesting, and "checking out chicks" just always seemed sleezy. So when I graduated high school, and could finally make my own way, I took full advantage.
Starting my new life on my own was of course not simple. I wanted to go to college, but never could land on a subject that piqued my interest, and joining a trade with my small petite, almost girly frame? Give me a break. I don't think I could climb a ladder, let alone with a stack of wood. My destiny was a blank canvas, and I had forgot to buy the paint.
"You know how to stock shelves?" the local Walmart manager said, glancing over my meager resume.
"Of course I do, took three years in high school." I said, looking for a smile, laugh, anything.
"Looks like you took four years in sarcasm."
He was now not looking at my resume, but looking over the top of it at my now fading smile.
I stalled by coughing into my elbow, looking for a response.
"Sorry, just a little nervous."
"You think you could start this Friday? Start on the night shift, but if you do well in the first three months, you may be able to move to first shift."
"Yes! Uh I mean, of course sir."
"Great, here is you blue vest. Please try to be here at least fifteen minutes before your shift. None of this clocking in right before ten PM." he said, setting my personal file in his desk, then closing it with a bang.
"That wont be a problem sir,." I stood up, and shook his hand.
I walked into my first shift at Walmart around nine forty five sharp. I walked to my locked, and got ready for my shift. I put my phone on silent, and sat it in the bottom of my locker, next to my small lunch bag. I unfolded my new, blue vest, and threw it over my shoulders, and reported to my shift lead Amanda for my first assignment.
"You Chris?"
"Yes, ma'am." I said trying to be as polite as I could.
"I'm going to have you stocking the women's clothes tonight. There is quite a bit, but whatever you don't get done by lunch, I will just go ahead and pass onto the next group. You have any issues with that?"
"No ma'am."
"Great, any questions, come find me over by the electronics. I gotta finish up the CD section."
I found my pallet of boxes already staged next to the women's department, and started unboxing. My first box was filled with nothing but skinny jeans, grandma jeans, and some pajama bottoms. I gleefully hung each garment from a hanger, then hung them on the chrome shelf, displaying them towards the aisle. I opened my next box, and my heart sunk like a rock to my gut. It was filled with nothing but panties. Some were high hipped granny panties, others were boy cut shorts, then a pile of nothing but red and black see through thongs. I pulled the first pair of black satin panties from the box, and marveled at how soft they were. My mind directly went to how they would feel not just in my hands, but gliding up my thighs, cupping by pathetic cock, and my embarrassingly tiny sack. I shook myself out of it, and knew that I still had a job to do. I took the panties, and started to hang them on the appropriate shelves, but I kept the day dream of me parading around in women's panties.
I finally finished hanging up the rest of the underwear, and went to find Amanda for my next aisle to stock.
"Wow you finished the women's clothes fast. I know it's kind of awkward but everybody's gotta do it."
"Yeah, it wasn't too bad. It;'s just clothes." Trying to play it off like I wasn't interested in doing the same department again.
"This next aisle isn't too bad. Its just the towel section."
I struggled through the rest of that shift because it seemed like every department I went to stock was within sight of the rack of panties. I could not help myself from looking over at them, and even dragging my hands across them when I would walk by after my bathroom break, trying to just feel them one more time.
When I got back to my apartment the next morning, I was still trapped in the thought of those panties. I needed to feel them on my naked body. I would even trade my boxers for some granny panties, knowing that they were still soft to the touch. But what was I thinking? Do I really want to wear women's clothes I decided to take a shower to clear my mind before bed. I stripped my dirty work clothes to the floor, turned on the shower, then stood in front of the mirror waiting for the water to run hot. The man I had seen looking back at me was no man. My little frame was closer to a petite female with a cock than a man. I ran my eyes down my already mostly hairless body, and could not see a man standing here. I knew then that I needed to try the panties, I needed to see how they felt. I wanted to see what I would look like in such slutty panties like the red thongs I had seen. My cock twitched at the thought, and grew from an inch to maybe three inches, and no bigger than my index finger around. I decided not to touch it, knowing that if I were to jack off and cum, my mind might take me away from this fantasy, and I may never go back, chalking it up to me just being horny. I jumped into the shower, and decided to make sure I was truly hairless, legs, balls, and ass.
The following day, I showed up to my shift, and finished up my pre-shift routine of dropping off my stuff at my locker, and throwing on my vest. I found Amanda in the break room getting herself a coffee. I wanted to make sure where I would be working today, so I figured this might be the time to ask since she wasn't busy.
"Hey Amanda, how's it going today?" I asked, making myself a cup of coffee as well.
"Not too bad, Chris. How about you?"
"Same, little tired trying to get used to these night shifts, but I think I will get the hang of it."
"You should. Pretty soon you will be just like the rest of us, and learn to love the night."
I laughed at this, and by judging her face she seemed to be serious.
"Ha! Yeah, I guess that I might. So, where will I be working tonight?"
"Since you did such a wonderful job last night, I thought that you might head back over to the women's section again."
My heart dropped into my stomach like a rock into a pond. My mind immediately went into dumb horny mode. "Ye-yeah, of course! No Problem!" I stammered, trying to play it cool.
"Excellent, same as last night, once you are done just come find me and we will set you up with somewhere else."
"Thanks, Amanda!" letting my excited tone escape for just a moment.
When I got over to the women's section it had clearly been cleaned out again from that day's shopping. Opening the first box, I found nothing but sweaters, and blouses. I proceeded to stock all of them as I did last night. The second box though was the jackpot. This time it was full of satin panties, and cotton thongs. My heart was beating like a drum in my chest. I sifted through the piles of women's underwear, searching for the perfect pair for me to try. I decided on a just a regular pair of red satin panties for my first try on. I stuffed them into the pocket of my jeans, and looked around to see if someone was around. When I didn't see anybody, I noticed that there was a set of changing rooms across the aisle. I continued to check around for anybody, then ran to the open changing room door. Once in, I closed the door as softly as I could, making sure that no one would hear me. I pulled out my bounty, and just enjoyed the feeling of the soft satin in my hands. Then I decided that this was the moment. I unbuckled my belt, and gently dropped my jeans, and briefs to the floor in a heap. I looked at the panties one more time before slipping one foot, then the other through the leg holes of the panties, I then pulled them up, already feeling the slickness of the material drag up my legs, then the crotch hug my tiny ball sack, and perfectly hide my small cock. I looked at myself in the mirror, and realized that my feminine frame looked great in these panties. My cock being so small that I would barely have to tuck it too hide it. I rubbed the material on my skin, and the softness felt wonderful. I marveled at myself for around five minutes, then decided I better get back to work, I was sure that someone would be looking for me by now. I dropped the panties back to the floor, pulled up my original clothes, and began to feel a bit sad that I couldn't wear the sexy women's panties the rest of the night.
Back in the women's section, I pushed the box of underwear aside for now, not allowing myself to get distracted so that I could finish what I was supposed to be stocking. The next box was full of denim jeans. I pulled out the first pair, and now my mind began to race even more, was it just me, or did these pants even feel sexier. I shook my head to try and get myself back on task, then hung up the pants. I kept glancing over to the box of panties, and dreaming of trying on something else. When I couldn't take it anymore, I drug the box back over to where I was working, and started looking for the next pair. I decided on something a bit more revealing, a white, see through thong. I stuffed it into my pocket just as before, and speed walked to the fitting room again, glancing over my shoulder the entire way.
I dropped my pants, and under wear again, then like last time, looked over the thong one last time, before pulling them up. This time though, the thong brought another level of pleasure. The tight material hugged my waist, and rode high onto my already feminine hips. I leaned forward, allowing my ass to spread so the string of the thong could tuck into my ass cheeks, coming to rest over my ass hole, tickling it gently as I moved around. My cock was still barely visible in the front, and I was okay with that, because what I saw in the mirror wasn't Chris anymore.
Just then, I heard a ring of keys jingle outside changing room door, and a key slide into the knob of the door, allowing it to twist.
"Chris! What the fuck do you think you are doing?"
It was Amanda, her face was beat red, and clearly not too happy.
I didn't know much about Amanda, other than she was about thirty two. She was about 5' 8" and slim, with barely anything for tits. She had a cute face, that was neither model like, nor ugly.
"Uh, I can explain!"
"No need to Chris, looks like I found you trying on some panties, all I need to know."
Amanda turned to leave, but for some reason I grabbed her, hoping that I could talk my way out of this.
"Chris, there is nothing that you could say here."
"I will do anything, please, just don't fire me."
Or worse, tell everybody there.
"So what? Are you trying to transition or something?" Amanda said, closing the door again. "Uh, no." I said, still trying to come up with something to say.
"So you are just some sissy that likes to see himself in panties?"
"This is the first time, I swear!"
"Well you are kind cute, why don't you pull that thong to the floor so I can see what you have down there." Amanda said, nudging the tiny bulge under the fabric.
My face went immediately red, then I decided it would be the best option if it meant I wouldn't have the embarrassment of my co-workers knowing that I was caught wearing panties at work. I looped my thumbs under the elastic band, then pulled them from my hips, letting them drop to the floor.
"Jesus Christ, not much to speak about huh?" Amanda said shaking her head.
"No" was all I could say, shaking my head in shame, while looking at the floor.
Amanda unzipped her vest, then flung it to the bench behind me.
"What are you doing?" I said picking my head up after hearing the vest hit the bench.
"How about you stop asking questions, and just stand there, and do what I say." She continued to undress, starting with her shirt, which she tossed off to the side, but kept her bra on, then pulled down her tight fitting jeans, letting them pile up under her. She was now standing in front of me in boy shorts, and her bra.
"Don't look too long, I don't want you to think you get to touch anything." she then pulled down her panties, revealing a huge, monster of a cock that was growing by the second. "Well except for this." she said, grabbing the base of her cock so that it was pointing straight at me.
"But um."
"Um" she mocked me "Why don't you shut the fuck up, and get to your knees." she demanded.
I listened, and dropped down in front of Amanda, her swinging meat only inches away from my face.
"Go on, grab it."
I did. The weight of such a giant cock was so foreign to me, mine only being a fraction of hers.
"Now open that mouth, I will be gentle at first, but I expect you to swallow my entire cock." she said, using a finger on my chin to guide it open.
I opened my lips, to which she set the tip of her cock in my opening. I stuck my tongue out to meet her tip, and started by circling it, not really knowing what I was doing. I stopped the circles, and would wiggle my tongue into the hole on her head, which she would react with a shutter, so I figured I was doing something right.
"Quit teasing me, suck my fucking cock now." Amanda said. Before I could get a chance to work her shaft into my mouth, she took my head from behind with both hands, then thrust her entire length into my mouth, then down my throat. I gagged hard as she paused with her cock at the back of my throat, then released me for a breath of air, then repeated the slam again, feeling like she might pop out the back of my neck. After about five pumps, my gag reflex began to lighten up, and the sensation of gagging for the most part went away. Before I knew it, I was starting to like it. I reached down to grab my cock, and begin stroking.
"Ah, ah, ah. I didn't say you could touch yourself." Amanda said, giving my should a firm smack. I knew my cock was hard at that point, and I want badly to stroke it. "You will not touch that pathetic cock unless I tell you so."
I nodded while looking up, and making eye contact with her, her cock still thrusting to the back of my throat. She stopped the pumping, then slapped my cheeks with her slobber covered cock, before pushing it to my lips one last time, and shoving it in so that he balls were firmly planted on my chin. I reached around her waist, and grabbed her ass, pulling her into me, and holding her there.
"Starting to like this cock huh?" I released, and she pulled it from my mouth. "Why don't you go ahead and bend over that bench, and don't you dare touch that cock."
I did as she said, and turned around, planting my hands on the wooden bench in the tiny dressing room. I felt her hand grab one of my hips, then I could feel her massive member start to part my cheeks, the head of her cock searching for it's target. When it found it, what was once always an exit was about to become an entrance for one of the biggest cock I had ever seen.
"You think you can handle this?" Amanda said, starting to push harder, nearing the point of when my entrance would give way.
"I don't know, I have never..." the head popped through my virgin opening at that second. "Oh fuck." I moaned.
"Keep it down, you don't want anybody else seeing this do you?" Amanda said.
I shook my head. He member now slowly making it's way deeper and deeper into my bowels, my ass stretching past what I thought was possible.
"Stop, you are going to tear me open."
"Stop being a little pussy. You will be just fine. Now shut your mouth." she said one last time before giving her cock one last push so that it was completely buried inside of me. She paused for a moment, letting me relax a bit, but followed it with a slow pull out, then slam it back in. My body jerked hard as she began her assault. After the third hammer, a wave of pleasure ran over me, her cock was not just big at this point, but I was almost wish it had been bigger.
"Yeah, fuck me, fuck me hard."
"You little sissy slut. You like that dick don't ya." She said, slapping my ass one good time.
"I fucking love your dick, please, keep, fucking, me." I tried to say between her thrusts.
"Oh fuck, your little boy pussy feels so good. So fucking tight."
"Your cock feels so fucking good in my boy pussy."
I looked down to my cock, and noticed that it was rock hard at three inches, and had a little stream of pre-cum that was leaking from the head, down to the floor. The building of an orgasm starting, and I haven't even touched my cock.
"Don't you think about touching that cock. Not until I say you can." Amanda said after noticing I was looking at it. I knew that wasn't even going to have to, I was pretty sure that I was going to cum with just this ass fucking alone.
"Fuck, keep fucking me, I'm going to fucking cum." I screamed at the lowest volume that I could.
"You are such a little fucking sissy, cumming from just my cock." Amanda said, picking up the pace.
The first of a tingle came, then a shake, then full pulses that came from within me. I was starting to cum, and cum hard. I saw my little prick start to bounce, then shoot rope after rope of cum, pooling onto the floor beneath me. Amanda finally stopped with her cock buried inside, and pulled me up so she could say something into my ear.
"You are going back to you knees, and you are going to eat every last drop."
"Yes, I want all of it." I whispered back.
I dropped to my knees, my cum between them, and pulled Amanda towards me by her hips, thrusting her cock ,that was still wet with my juices, into my throat. She started to pump in and out, but I knew that this would not last because her knees were now shaking. She pulled her cock from my mouth, then set the head on the tip of my tongue, blowing her load that was quickly filling my mouth up with her warm, salty fluid.
"Fuck! Fuck yeah. Eat all of it." She said, stroking every last drop from her cock. After she had finished, I left my mouth open so that she could see the pool of cum before I swallowed it down.
She was now breathing hard, but started to pull her pants, and underwear back up.
"Dont think that you are done just yet. You will be cleaning all of your mess up too."
I looked down and the small puddles of cold cum that was on the floor.
"Yes, ma'am" I responded before bending down, and licking up every last drop of my cum from the floor.
"Good, since you were such a good little boy, you can go ahead and keep that thong. But next time you want to sneak away to try on some more, you better come ask me first." Amanda said before walking out of the changing room, not giving me a chance to respond.
My eyes lit up. I grabbed the white thong sitting on the floor, pulled them on, then my pants over them, hiding them from everyone I work with. No one needed to know my secret, or rather, mine and Amanda's
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