Doug Days Pt. 01-03

This story was requested by 'ddk7723'! I hope you all enjoy!

********

I knew I shouldn't have done it. I knew it was naughty. I knew I'd end up getting caught. But fuck, am I glad I did it.

My name is Doug. And, about a month ago, I found something I knew I wasn't supposed to.

See, one day, I was a little short on cash and I wanted to go out for a few drinks, so I snuck into my parents' room to see if I could find a couple dollars lying around. I know, I'm a 25 year-old-man, I should have enough money of my own but I'm lazy, okay?

I rummaged through my mother's drawers and her dresser... nothing. "Fuck, mom, you've always got cash lying around... except when I fucking need it!" I grumbled to myself.

My parents were out for the weekend and I had the house to myself - which I was really looking forward to. But that also meant that if I didn't find any cash now, I wasn't going to have any money for the rest of the weekend - even for food, let alone beer. So, in my desperation, I did something my mother had expressly told me never to do.

I went through my step-dad's stuff.

My mother married Carl about a year ago and he'd been living with us ever since. He seemed alright - kept to himself mostly. He did have a rather bossy side that I didn't like; we argued a couple times about him trying to be my 'new dad' and telling me what to do. But still, I thought he was alright. And he was by most standards a 'high-flyer'. He was well respected at a prestigious law firm and he was always flying from state to state, country to country, representing clients all around the world. Which is also why I knew he'd have some cash lying around somewhere, surely.

So, I went to the bottom drawer in the bedside table and started rummaging through Carl's stuff. At first, I didn't see anything too shocking. Some condoms (gross), a gun (not surprising) and a couple $20 bills. "Yes!" I rejoiced. But, honestly, I was expecting more. So I continued to rummage...

Which is when I noticed a hole in the drawer that had been covered up by a page from the newspaper. "That's weird..."

I reached in, curious as to what this was all about, and what I found there would change my life forever.

I felt a tube of some sort - like a bottle for candy or pills or something. I pulled it out and there it was. The label was huge - hard to miss. In bold, pink letters, it read: "X-CHANGE MILF! Variety pack!"

I brought the bottle closer and struggled to process what I was seeing, "What the fuck...? Why does Carl have this?"

I had heard of X-Change before. I mean, who hadn't? It seemed like half the world was experimenting with X-Change these days. I even knew a couple guys from school who were now full time X-Change girls... and proud. I'd hear stories of the sexual escapades people went on on the damn things - orgies, gangbangs, threesomes. It seemed like there was a whole world of fun out there that I was excluded from.

Honestly, I was curious. But, I was just rummaging around for a few bucks, so you can imagine I didn't really have the surplus cash to be buying expensive drugs.

And yet, here I was, stood in my parents' bedroom with a bottle of some of the highest end X-Change pills you could buy.

I put the pills down on my mother's dresser and just stared at them for a while, trying to sort out the myriad of thoughts and emotions running through me. 'This is wrong. This is weird. I mean, why the fuck does Carl have X-Change on him? Does he use it? Or does he give it to other guys and then fucks them? Either way, he's been cheating on my mother in all likelihood. And worse, I've now violated his privacy and found the pills for myself. I can't come clean about it because I'd have to explain how I found them and that'd get me in a bunch of trouble. What if my mom already knows about them? Ew, the less thought about that, the better.'

I battled myself internally for a while, trying to figure out if I should put the tube back or maybe even pop the little plastic bottle open and swallow a pill. I mean, if Carl keeps any sort of track of how many pills there are inside, he's going to find out that someone took one... and his first accusation is going to be at me.

"Fuck it. I'm doing it." I said, regardless. "Life's too short." Those words never lead to any sensible decision in the history of human kind.

I grabbed the bottle and before I could have any second thoughts, I pulled out a pill and tossed it into my mouth, feeling it travel down my throat and into my stomach.

A waited a few moments. I wasn't really sure what to expect.

Then I suddenly felt it - that singular feeling that you get when you pop an X-Change pill and your whole body transforms from inside out. I could feel my skin tingling all over and it felt like my body was reshaping itself internally. I know that sounds horrific and painful, but trust me, it's anything but.

If I had to describe it, I'd say it's like that feeling when you're on a really high rollercoaster, hurtling up and down the steep peaks and troughs. Your stomach tingles and you want to scream. You feel like something bad is going to happen... but it never does. It's just this amazing, rapid rush of euphoria... and before you know it, the ride is over, and you're left craving another round. Imagine that feeling all over your body. That's what taking X-Change is like.

When this particular ride was over, I found myself in a completely new body.

I stared into the mirror and there I was - a gorgeous brunette MILF.

I rushed to take my clothes off and inspect my new form. I was like something out of a porn site.

Suddenly, I had these gigantic, fake-looking tits that sat on top a soft, hourglass body. My ass was huge - like someone had pumped a normal set of cheeks full of air. Yet it was also firm and jiggly. My lips were naturally vibrant and luscious, as inviting as any Instagram model. I radiated pure, raw sexuality. This wasn't the kind of body built for settling down. And, perhaps most importantly, I reached between my legs and what used to be had been replaced by a pretty, pink vagina.

"Hoooly Shit!" I said, before laughing in pure excitement. I flopped back onto the bed with sheer joyful energy, thrashing my limbs against the soft sheets.

Suddenly every sensation felt heightened. Even the sheets felt softer and smoother against my skin, giving me a new sense of euphoria.

I don't know what started to come over me, but I just felt exceedingly horny. I let out a soft groan and my right hand just naturally drifted down my body and in between my legs. I started to feel and explore my fresh, new pussy - dancing my fingertips along my labia.

I could feel a sensitivity from a little higher up and my fingers found their way to my clit. Admittedly, it wasn't something I was great at finding as a guy, but as a woman exploring my own body, it was easy. And my God, it felt amazing. Every movement I made against it made me tingle and smile. I was just about to begin rubbing away at it when...

DING DONG. The doorbell rang.

I jumped up nervously. "Shit, who could that be!?" I looked around frantically for something to put on and settled for a set of bath robes hanging outside the cupboard.

I slipped them on quickly and rushed downstairs as the doorbell rang again. "I'm coming!" I shouted, then realised that my voice was now completely different and hopefully whoever was on the other side of the door wasn't expecting to hear Doug's voice.

I grabbed the doorknob and opened it. Stood outside was one of my close friends, Jimmy. 'Ah crap,' I thought to myself, 'I totally forgot I had invited Jimmy over to hang today'.

Understandably, he looked like a deer in headlights. He was staring at a busty, bimbo-esque MILF, wearing a tight, ill-fitting bathrobe and nothing else. He mumbled a little bit before finally getting out, "Uhhh is Doug home? I'm his friend, Jimmy."

I paused for a second, considering how to respond. Maybe it was the pills, maybe it was the level of arousal I had just reached starting to touch myself, but I felt incredibly naughty right now. I smirked and grabbed his arm, pulling him, "Come on in, you idiot!"

He stumbled inside, and I closed the door behind him. I turned and walked towards him with intent - all the poor guy could do was start walking backwards, retreating towards the couch. "I'm sorry, do I know you, ma'am?" he asked so nervously.

My tits felt like they were already a foot ahead of me, bulging through my robe as I continued my march forwards. Jimmy kept backing up till he fell back onto the leather couch I just burst out laughing, "Jimmy. It's me, you dumbass! It's Doug".

"... Huh?" He replied, understandably puzzled.

"I took some X-Change pills I found in... I found them. What do you think?" I spun around, giving him a full appreciation for how curvy and bodacious my new body was.

He staggered back up to his feet, looking me up and down. "I-is that really you, Doug?" I could tell that he could recognise me but he still looked sceptical.

I gave him the once over with my gaze too - seeing him in something of a new light for the first time. I don't know if it was the X-Change or just the mood I was in, but suddenly I felt an irresistible pull towards Jimmy. I mean, he wasn't an international stud by any means, but he was definitely cute. Dark brown hair, deep, hazel eyes and a nice build. He had an innocent appeal about him that I was just about ready to defile.

"Yeah, it's me. You hide your condoms in your computer's CPU case and your password is LisaAnn1972. Happy now?" I smirked, my eyes wandering down to his crotch to notice the 'effect' I was having on him as he finally felt assured of my identity. "You like what you see?"

I put my hands on my hips and stared at him and I could see the nervousness start to fade away in his body... and the lust grow. "Fuck me, it's really you then... Yeah I do... You're like the hottest MILF ever!" He said, practically drooling as he ogled me.

I could see his hands instinctively move up and towards my tits but he stopped himself halfway and was in the process of putting them back down when, in a moment of pure spontaneity, I just grabbed them and lead his hands all the way. I almost moaned out when I felt someone's fingers on my tits for the first time. But I managed to contain myself and got my words out instead,"Nice, aren't they?"

I could see his eyes visibly growing as his hands squeezed my tits, making me feel a tingling sensation through my spine. "Jeez, they're just... the fucking best..." He replied, started to get a little freer and more confident with his touch with every passing second. He was like a child with a foam ball - squeezing as hard as he could.

As his fingers brushed over my nipples through the silky fabric of my robe, I had to bite my lower lip to not let out a groan or a deep sigh at the very least. I never knew how fucking erotic that felt for a woman.

Then, he glanced up at me... and our eyes locked. In that moment, we knew what we both wanted. We both knew what we were thinking. What happened was inevitable.

He pushed the fabric of my thin apparel either side of my silicon-like tits and started to grab at the bare flesh. Meanwhile, our lips edged ever closer till our foreheads were resting against one another's. I could feel our breaths getting heavy as I whispered, "You don't mention a word about this to me or anyone else the second I go back to being a guy... Got it?"

No sooner had the words, "Deal" escaped his lips, our tongues mashed together in a hungry embrace. He pulled my robe open entirely and started running his hands all over my body and I quickly got to work undoing his dark green shirt, eagerly yanking it off his body.

He knew where my room was, naturally, having been here many times before, and we just started to walk towards it while keeping our lips locked together. No more words were needed. Our bodies - and hormones - were doing the talking now.

We stumbled our way up the steps but couldn't stop making out. I knew why Jimmy was so turned on - he was getting to fuck the kind of MILF he could only dream of fucking ordinarily. I couldn't figure out, though, why I was as horny as a rabbit during mating season. I put it all down to the pills - my burning body, my soaked pussy, my insatiable hunger for his cock - any cock - to fill my every hole. It had to be the pill.

We eventually crashed our way into my room and landed on my bed. Outside, we had left a trail of clothing leading from the living room to this spot, meaning that our bodies were free to be pressed together - skin to skin.

Jimmy had the sense to pull a condom out of his wallet before he left his pants downstairs and he quickly ripped the packaging open with his teeth. As soon as he pulled it from its wrapper, I grabbed the rubber garment and covered his cock with it, loving the way his shaft pulsed in my grip.

I had no idea what Jimmy's dick looked like before now - obviously why would I? - but it was still oddly surprising to see it. I always thought seeing a cock that wasn't mine for real would be weird and repulsive... but it was anything but. It was a decent size, nicely shaped and felt amazing to squeeze. Jimmy was nice and shaved down there too, so everything looked... frankly delicious. I had half a mind to blow him first but there was one thing my body craved right now and I was damn sure going to get it.

Once the condom was on, I lay down on my back and spread my legs. Jimmy needed no invitation to slide himself inside me.

It's hard to describe how it feels to be penetrated for the first time, especially when you're normally on the other end of the dick.

For virgin women, the experience is often uncomfortable and painful - it's something that takes getting used to. For an X-Change girl, it's absolutely the opposite. The minute you feel that first cock slide inside you, it's like a gaping need in your life becomes full. Suddenly, you realise how crap it feels to not feel this way all the time and how amazing it feels to have a pulsing, throbbing cock buried deep inside you.

I grabbed the back of Jimmy's head and pulled him in for another bout of intense kissing as he began to thrust his hips and slam his shaft in and out of my tight pussy. I could feel my walls wrapping around every inch of him... God, it felt amazing. I knew from the first second that I was going to get addicted to this feeling.

"Fucking hell, you're so fucking tight, Doug!" Jimmy grunted. From the look on his face, I could tell he was already struggling to keep himself... contained.

I don't know what came over me - it was like something inside of me took over - but I just rolled Jimmy onto his back and climbed on top. "I'm not Doug. Not right now. Call me Charlotte!" I threw my flowing, brown hair back and started to bounce on Jimmy's cock like I was riding a mechanical bull at a bar.

I used to have a crush on an older woman in our neighbourhood named Charlotte growing up, so I guess that's where the name came from. And right now, I was riding Jimmy the way I always wished she'd ride me - wild, horny and uncontained. My ass rippled and shook with every movement of my thighs and hips and my tits were like paddle-balls, bouncing wildly but always returning to their original place.

I was just starting to go wild and lose myself in the moment, when suddenly Jimmy cried out, "OH SHIT!" And, just like that, it was over. I could feel his cum shooting out of his cock and into my brand-new cunt. I stopped my bouncing and just grinded on his cock gently as he trembled and shivered.

I didn't quite get the pleasure I was hoping to but seeing him cum so hard and so quick was pleasing in its own way. The stupid grin Jimmy had on his face right now was one I'd never seen before. He was looking at me with such satisfaction and affection that I couldn't help but feel... sexy. "What?" I asked with a laugh.

"Nothing... Charlotte." He said with a cheeky grin.

"Idiot!" I replied, tapping his left cheek with my palm before I rolled off and gathered myself. I put my clothes back on and so did he.

****************

After that, Jimmy and I just hung out for a bit. We had planned to go into the city and hit up a bar and stuff but obviously, we couldn't really do that now. So, instead, we just sat on the couch and watched TV.

After a while we both got horny again (I mean, I was horny throughout, but he just got hard again) and started making out but it was pretty much the same result. We kissed, I got on top of him, slid his cock inside me and a couple minutes later it was over.

I have to admit, I was a lot more annoyed about it the second time. Here I was, hot and ready to go and this fucker couldn't even hold out from cumming for 10 minutes. And after he'd be done, he wouldn't even finger me or eat me out or anything - selfish prick.

When it got a bit later in the evening, I just told him I had a headache and that he should go home. He seemed a little miffed - not to mention disappointed that he couldn't keep fucking me - but he left anyways, thankfully.

I went upstairs and took a shower and decided to properly explore my body for myself... and my God, it was a work of art. As I stood in the mirror, admiring my busty, bimbo form, I couldn't help but feel jealous of Jimmy for getting to fuck such an unbelievable MILF. "Lucky piece of shit... He doesn't even deserve it, the limp dick motherfucker," I grumbled.

I got out the shower feeling refreshed and I pretty much spent the rest of the night relaxing...

Okay, I'm lying. I spent the rest of the night masturbating. FUCK ME it felt good. It took me a while to figure it out but once my fingers started exploring my labia and my vagina properly, I started to find little spots that just made me quiver with pleasure. And, by the end of the night, I had gotten the hang of finding my clit. That shit is really like an orgasm button. I never had to rub it for long before it sent me over the edge.

I don't even remember when I fell asleep, to be honest. I just know that I eventually exhausted my hands and my pussy till I passed out on my bed.

But, when I woke up, it was all gone. My beautiful body, my giant tits, my plump lips, my luscious ass - all gone. Only to be replaced by my normal body, which now, in comparison, seemed... inadequate. I used to be quite proud of my body - I was in-shape and nicely built. But, compared to the MILF pills, this was nothing.

Disappointed, and a little depressed, I went back to sleep. I don't know if it was the pills or the sex or the masturbating, but I really went out like a light. By the time I woke up, it was two in the afternoon.

I stumbled out of bed and reluctantly got dressed.

I sat down in the kitchen to eat some cereal... but there was only really one thing I could think of. Those damn pills.

I could practically hear them calling out to me, "Doug! Doug! Come! Use us! Be a better you again! Come be the MILF of your dreams!"

I tried to resist. I really did. I kept trying to distract myself. I sat through an entire film and I still couldn't tell you what it was about, I played video games for an hour... heck, I even went upstairs to beat my dick off, hoping it'd remind me of the good parts of having a cock.

But, it had the opposite effect. Watching one of my favourite pornstars get ploughed, I suddenly wasn't interested in her amazing body and how good she looked getting fucked. For the first time, I started to look at the other part of the picture.

I couldn't help fixate on the hunky, beefcake guy fucking her - the way his biceps bulged when he held onto her, the way his big dick slammed in and out of her, the grunting noises he was making as he came inside her. Before I knew it, I had cum thinking about how good it would feel to have my pussy fucked by him. A pussy I no longer had.