Changing My Rommate free porn video

It started last Halloween. My roommate Jordan thought it would be funny to dress as a schoolgirl for our house party. Jordan was 18, and had been on his own since moving out of his parent's place at 15. I was 25, and had randomly been paired with him through some of our friends. He needed a cheaper place to stay, I needed a roommate -- we got along better than I think we both expected. Jordan never talked much about his family life before the move, but other than being a little immature on occasion, which I attributed to his age, he was a pretty upbeat dude for someone who had been working and living on his own since 15. He generally kept to himself, but always tried to make light of any situation, which I realized was his way of contributing to any conversation, seeing as I knew he was self conscious about his lack of schooling. He wasn't dumb by any means, just simple. Having a knack for always being able to take a joke, he was often constantly razzed by our group of friends for being half Japanese and half Russian -- a heritage which ultimately gave him a very pretty boy look to his facial features and made him quite slight and small in stature. I was often jealous of his good looks, when he was around, most women bypassed me and often focused their attention on the attractive young man with the slightly exotic features. Which is generally why we all seemed to like razing him in our group of friends, because on some level we were all just a little jealous -- and the amount of anime or drunk Russian jokes directed at him were always good natured, since he often just played into them. ---------------------------------- Which brought us to Halloween of last year. A week before Halloween, our buddy Tom had cracked a joke about how Jordan was growing out his hair, and asked if he was letting it grow out for his Japanese school girl costume for Halloween. We had all gotten a laugh at the comment, but the joke quickly slipped from all our minds... except Jordan's. Who couldn't resist poking a little fun at himself. I was a pharmacist, so I often worked odd hours at the local grocery/everything under the sun store, which is why the night of our party I was at work, eagerly watching the clock, as I sat alone, having no customers on a holiday weekend. About an hour into scheduled start of the party I got a text from my friend Jessica. I felt my heart skip, I had been looking forward to seeing her at the party, maybe she was missing me already? I hoped. But she had simply wrote, "Jordan is a riot, have you seen his costume?" I responded back with: "Nope. What are you dressed as?" Trying my best to steer the conversation away from my woman stealing roommate. I got a pic message shortly after and opened it. Jessica was dressed as a german beer maid, and she looked incredible, but my eyes quickly went elsewhere, to the other person in the picture. It was Jordan, dressed in a simple Japanese school girl costume that looked like he had bought it from the first place he could find. But what was weird wasn't how badly it looked on him, but how good it did. My brain kind of stalled. What was going on in there? I stared some more. He was in a simple blue pleated skirt, and a white school girl top that showed a little midriff. On his legs were a pair of knee high socks And clunky black heels. But he had put a little effort into his face, wearing makeup and styling his longish hair and bangs on either side of his face. Other than missing a few curves, he looked good... And that's when I realized, him dressed and looking like he did was turning me on. I actually said "What?" to myself out loud at this realization. Where had this come from? I'd never had thoughts like this before. I quickly rationalized in my head that any true male mind would be attracted to what appeared to be a lady in a school girl costume. I left it at that, texted "haha" back to Jessica and set down my phone. I tried to busy myself around the pharmacy.... I tried... My brain kept thinking about that picture, and even worse, I was eagerly anticipating heading to the party now to see him in person like that. I shook my head violently, I must just be bored, I decided. An hour later, I opened the door to our apartment and was greeted by the loud music, dark atmosphere, and smell of booze and sweat that accompanied any good party. Several people happily greeted me and poked fun at my "great costume" which was simply the lab coat I wore everyday. I quickly grabbed some alcohol and began to mingle, trying to keep myself from darting my eyes around the crowded room looking for a particular someone. Thankfully, Jessica took care of that for me and found me in the crowd, quickly erasing my mind of Jordan as I admired and began chatting her up. Jordan slipped almost entirely out of my mind until a couple hours later as the party began to thin. We all started to collect from the recesses of the rather spacious apartment and a group of about 25 gathered into our living room. I wasn't one to brag, but I was quite proud of my job and the extra chunk of rent change from Jordan that allowed me get such a nice living space. Soon we were all dancing, and I finally spotted Jordan out of the corner of my eye. Jessica was all over me, but despite this, I found my eyes wandering towards him. He was clearly shitfaced, and having a hell of a time. His small frame never really could handle booze. I almost shook my head at the sight. Of course, even when dressed as the opposite sex -- Jordan was dancing with several sorority girls Tom had invited over. Jordan's inebriated and humorous state, along with his funny costume, had obviously gotten their attention and they were lapping him up. I continued to watch, and as the girls continued to dance around him in a little pack, I noticed him watching them, smiling. And then, very slowly, as the song kept on, he began to gyrate and dance like them, mirroring their sexy style of dancing. This only made the girls laugh and applaud him more, so Jordan continued. Soon he was gyrating and bouncing just like any one of them. If you didn't know it was him, he would have seemed like any other drunken sorority girl in the pack. "Are you enjoying this?" I heard Jessica whisper sexily to me, I snapped out of it, worrying she had caught me. But she hadn't, she was still rubbing up on me to the music, backing her ass into my crotch and seemingly ignorant of my staring. Then I realized why she had asked. I had an erection -- but even worse, I couldn't tell if it was from her rubbing up on me, or watching Jordan dance... Though, I had a pretty good idea which it was... ---------------------------------- The party eventually began to die down about an hour later, and people began to leave. I had done some heavy petting and made out with Jessica in the "coat room" before she left, and I was quite proud of myself. I headed back to the living room to mingle with the last 10 or so stragglers left behind. Jordan and his sorority sisters were sitting on our long couch, but they had finally been separated from the herd a little. Some bros I figured Tom had invited had found a way to weasel in between them. Jordan had done something similar, placing himself near the cute short blonde next to an arm rest, and then cutting her off from the bro who was sitting next to him. I just stood in the doorway, sipping on a beer, and watching all the remaining party patrons. I was starting to feel all the booze of the night flow through my system. After a while I noticed something. The bro sitting next to Jordan was trying to hit on him. But Jordan was so drunk and focused on the blonde, he had no idea it was going on. I chuckled to myself. Poor bro didn't know he was barking up the wrong tree. He kept trying to insert himself into Jordan's convo, but Jordan just kept nodding, then going back to the girl. I couldn't blame the guy really. Jordan was sitting just like the rest of the girls, legs crossed, and with his skirt showing his smooth thighs. Had he shaved his legs? He had. I felt the stirring again, so I quickly retreated, and headed for the kitchen for food. By 3:30am, the party was over, I was eating in the kitchen, and laughing at the drunk texts Jessica was sending me. I heard the final closing of our door and the click of heels. Jordan strolled into the kitchen, teetering and smiling, and quite drunk. I tried not to look at him. He pulled out a bag of rolls from the cupboard and began to eat them plain. "That was a hell of a party," he stated, and hiccuped. I looked up, this was the first time I had heard him all night. He was talking in a female voice. He must have been doing it all night and was now too drunk to stop. "Sure was buddy," I said. "You get any digits?" He nodded happily, which almost threw him off balance, he grabbed the countertop for support. "I think I got everybody's digits. Even those I didn't want." He giggled. Why was he giggling? "I am so god damn drunk," he stated and giggled again. I laughed, I had never seen him this far gone before. "I... I got laid off at work today," he said, chewing on another roll, "didn't give me an excuse to drink this much though." "Oh shit," I said, genuinely feeling bad. "Sorry man." "Yeah... Sucks... I'll figure it out... Always do." He smiled, but behind his eyes, I could see the pain. He was exhausted. He was sad. Probably explained the costume, anything to get his mind as far from being out of a job as possible. "I'm..." he slurred, laughed and continued, "I'm gonna pass out... Maybe even literally." He took a couple steps forward, and stumbled a little, he grabbed the countertop and looked down at his heeled shoes. He laughed, "God I look silly," he slurred in almost inaudible English. "I think you look great --" I said without a thought. Fuck! I continued quickly, attempting to cover my tracks, "As great as one can look as a drunk Russian dude in a school girl costume." "Shut up!" he laughed, smiling, and seemingly missing my compliment. He started to walk but stumbled again, I laughed and finally stood to help him, grabbing him by the arm. "My hero!" he joked, grabbing onto me fiercely for support. He looked like he might pass out at any minute. I slowly helped him to his room, guiding him past all the empty cans and plates strewn about the place. I got him to his bed and lowered him down onto it, where he sat -- swaying back and forth a little. "You want some water buddy?" I asked. "Probably." He nodded, and instantly regretted moving his head so much. I headed back to the kitchen and filled up a glass, taking a couple extra minutes to finish up my texting with Jessica. ---------------------------------- I returned to his room with the water and paused. He had passed out of top of his covers, but not before taking off the school girl outfit. But that wasn't why I paused -- I paused because I didn't realize he had completed the costume by also wearing lingerie under it. He was lying back in his bed decked out in a sexy bra and panty set, with the heels and knee high socks still on. The lingerie was dark blue and black, and very sexy. There was lace edging and satin adorning it. Again, I assumed it was less of a style choice and more that he just grabbed whatever he came across first.... And if that was the case, I appreciated his choice. I was going to set the water on the bedside table but instead continued to stare. I could blame my fascination on being drunk, but I couldn't help also realizing how attracted I was to him like this... I mean, he looked like a sexy woman, minus some of the curves... But shit, if he had the curves he would be cute as hell... I began to get aroused as I imagined him with those curves, and fully embracing his femininity... I scanned him as he slept. His cute face was still made up and his soft facial curves and small nose really helped the illusion. Even his eyes were big and cute, and hell, how had I never noticed the light freckles. And if his hair were even just a little longer... My eyes traced down his long neck to his chest, which was slowly rising and falling with each breath. The bra around his chest looked like it should always be there, and despite no real breasts, the bra cups were pushing up something, even just his small pecs. His stomach was tight and slim, and his waist was thinner than most boys his size, which made his hips look bigger. The sexy panties he was wearing held his package tightly, almost making it appear smooth down there. And his long smooth legs looked great in heels. I imagined them in stockings. Then I went back and imagined the rest of his body, and how it would look with real curves. How hot would he be with real breasts? I don't know why but the idea of him having the body of a sexy young woman, but also knowing who he really was, was what was turning me on so much. I wondered what he looked like from behind, and at that thought I finally caught back up to reality. "Shit," I whispered, taking my eyes away. I stumbled quickly out of the room while cursing myself. Jordan didn't notice in the slightest. I went back to the kitchen and quickly took a couple shots that burned my throat, trying to calm my thoughts and wrap my head around what was going on in my mind. After another shot that I shouldn't have taken, I noticed the glass of water I had forgotten to drop off for him. I sighed angrily to myself and headed back, but was glad for the drinks I had taken, I felt much more at ease now. I reentered the space and averted my eyes, quickly planting the drink on the table next to him. But before I left, I looked one last time, and made a decision... I had to put him on his side. It was no good leaving someone on their back like that when they're that drunk. I cautiously stepped forward and raised my hands. Hesitant on where to grab and turn him. I lowered my hands slowly, placing one on his hip, and the other on his stomach. He had definitely shaved. Then I caught a whiff of the perfume he had obviously put on, God he even smelled good... I couldn't help myself. I watched almost in autopilot as my right hand slowly slide over his stomach and up to his bra. I gently cupped the satin and lace and the breast it was covering.... Just calling it his breast even turned me on. My other hand ran to his hip, gently fingering the sexy lace of his panties. I squeezed his breast gently, letting my fingers play where I knew the nipple was. I was shocked to hear a small moan of pleasure escape his lips. I froze. But Jordan was not waking up, he was out cold. I continued, rationally I was just convincing myself I was rolling him over, so as I leaned over to get a better grip, I found self leaning closer to his bra covered chest and slowly after one more gently squeeze of his breast, my hand traced down his bra band, until I had my hand under his side. My other hand slowly moved down his thigh. It was so smooth. I was breathing heavily now and felt like a fucking pervert, so I forced myself to finish the job and I gently rolled him over. He followed my lead, but remained passed out. God, from the back, with just his hair, and in his sexy lingerie, he looked just like a woman. And his ass was fantastic. He was wearing cheeky panties and his cute little bubble butt fit perfectly into them. It would make any girl jealous... I made an irrational decision. He deserved those real curves, I decided. At this point, I was drunk as fuck, and there was no real conscious brain activity. I left him as he was and grabbed my work keys. ---------------------------------- The pharmacy was only a couple blacks away, and I was walking with so much drunken determination, I was there in less than 10 minutes. I came in through the back door and quickly moved through the shelves, I knew everyone had gone home for the day long, long ago. I quickly grabbed what I came for from the pharmacy and made a mental note to fudge the numbers the next day. I also headed out to the main sales floor and picked up a couple other items for my plan. My heart was racing, but I got them despite the sweat now pouring off me. Thank god we never installed cameras. And thank god I hadn't made any drunken mistakes in grabbing all this stuff. Within minutes I was back to quickly walking, now with a bag of items I would have to deal with in the morning. Somehow I was still convinced this was an incredible idea. I entered the apartment entirely out of breath minutes later, and forced myself to calm down. I was shaking a little and my gasping might wake him. After cooling down a bit, and taking one more shot for confidence, I returned to the bedroom. Jordan was as I left him, and still very much passed out. I thought for sure I would chicken out by now, but seeing him as he was, only made me want to do it even more. I crumbled up two of the pills in my hand from the box I had stollen from the pharmacy, and carefully let the remains fall into his water glass. The rest of the box would take some time to get through, but this was a good start. I gently stirred the mixture and watched as the pills disappeared entirely from view. I set the glass back down... I was so turned on by this. What was I doing? But as I pulled out the other items, I decided I was evil. I was definitely evil. It didn't shock me as much as it should have... But on the other hand, he shouldn't be cold there in bed... And he would look so amazing by the end of all this. I set the stockings and garter belt set on the table I had taken from the store, along with the nighty I had found that was an exact match to his bra and panty set. I had been right in my assumption that he had simply grabbed things from the nearest store. I gently prodded and shook his shoulder, half waking him, he was so out of it, he barely even opened his eyes. "Huhh?" he groaned, trying to fall back asleep. "I'm going to help you into your Pj's Jordan," I whispered. I could hear the nervousness in my voice, but he couldn't. "Uhhhh? Yeah... Yeah... Ok... Thanks Stacy... You're the best...." His hangover was definitely going to be awful. I assumed the blonde sorority chick had been Stacy. I brought the garter and stockings to the end of the bed and slowly reached up and grabbed his long slender legs, pulling off his knee high socks, I had left the lights intentionally dim and dark in the room. He squirmed a little as I did so, but was giggling drunkenly to himself. "Shaved legs actually... are good... feel good. I mean," he muttered. I crawled up on the bed a little holding the garter belt and wrapped my hands around his waist. He arched his back, letting me do whatever -- he had no idea what was happening. He looked cute arching his back and pushing his breasts out like that. I put the garter in place and straightened it out and couldn't stop my hands as they slide down to slide the garter straps under and out of the panties he was wearing. Only a naughty girl wore their panties over their garters like that. I felt my erection stiffen, I loved calling him a girl like that. What was I doing?? Next I slid on the sheer stockings, it was heaven as I ran my hands over his smooth legs, and I heard Jordan moan in pleasure too. "Mmm Stacy," he called out sexily. I noticed he was still using his girl voice. I clasped the garters to the stockings quickly. I was getting way too turned on by this, and I needed to finish setting the trap before I did something really stupid. I ran my hands up his sides and he squirmed at the touch. Eventually my hands curved down around to his back, he sat up gently. By now I was over him, with my knees on either side of his hips. He rested his head on my shoulder as I found the clasp to his bra. I gently removed it, he giggled in a half sleep daze as I did. I then raise his hands over his head and gently let the nighty float down over his head and let the straps fall into place. Somehow on luck I had guessed the right band and cup size. I adjusted the bra built into the nighty to him and played with the hooks. Jordan remained blissfully unaware I was dressing him this way. I clasped the bra, then gently ran my hands over the silky dark material, letting it fall into place over the rest of his body until it reached his thighs. He moaned again. "This is... great..." he muttered. I agreed. I stepped back to admire my handy work. God he looked sexy all dolled up, even in the low light. And soon he'd look even sexier. I eyed the water glass next to him that was swirling with female hormones. He deserved the real female body he belonged in, and my trap had been set to get him that body. ---------------------------------- I couldn't hold back. I practically sprinted back to my room, and immediate relieved myself. I had never felt such pleasure. After gasping for air for several minutes, I eventually passed out. I awoke in terrible pain the next day and forced myself up to get food in me. Amongst all the dirty party dishes and empty bottles, I eventually started making some eggs... The previous night's activities hadn't even crossed my hungover brain yet... until... I heard a gently stirring of Jordan waking up in the next room. The events of last night finally came crashing back. I simply stated, "Fuck," to nobody and felt my blood run cold as ice. What had I done? I almost rushed to grab the water from his table and dump it, but knew if I burst in on him as he was, it would only make matters worse and make me look more suspicious. What if he remembered anything of last night? Good god... I was fucked... I had basically sexually assaulted him! What was I doing??? I heard more stirring from his room and forced myself to keep cooking, grinding and scrambling the eggs until they were basically dust. I was sweating. I heard his door open, and with as casual a look as I could give, I looked up. Jordan had changed out of everything I had left on him the night before, and put on a pair of shorts and a tank top. With his face still made up and his hair still slightly styled though, he didn't look much more masculine than I had left him. He was drinking from the water glass... It was half empty. He stumbled forward, not even looking up at me yet. He sat on the bench in front of me and put his head on the cool countertop. "Jesus..." he groaned. "What even happened last night?" There was a glimmer of hope. I tried to chuckle but it felt fake to me. "I know man... You ah... You had a couple drinks." Jordan groaned again. "So it would seem," he sputtered, "All remember last was chatting up that Stacy chick on the couch. She kept complimenting my legs." he laughed to himself and coughed. He finally looked up at me and took a drink from his glass. I stared... God he was cute.... Well -- "she" I rationalized. All I kept seeing was a cute girl in my kitchen. Was I insane? "Was fun though..." he continued after a long drink. "Things may have been too fun... Did I..." he glanced back at his bedroom, "uh... Did you see me go to bed?" Here was my chance to come clean. To let this all drop and not start in on this ludicrous plan I had devised... But I wanted to see female Jordan in lingerie again. "Yeah..." I offered, feeling my nervousness start to fade. Jordan sighed in embarrassment. "You uh... See what I was wearing?" "I did." I smiled and laughed a little, trying to lighten the mood. It seemed to work a little on him. "God dammit. I don't remember any of that... So why was I dressed like that?" he asked. "Well... Because you said you felt like you were supposed to dress like that. That you felt like you should be dressed like that." I was evil... So evil. Mine own words felt like they had ben spoken by someone else. I could see the confusion in his eyes. "Nah..." he started... "I didn't... I didn't say that did I? I mean..." He looked down at himself. "I don't feel like that at all right now. Like not the least bit. It was just a silly joke." "Well..." I offered, playing this carefully. "You seemed pretty adamant about it last night." Jordan began to blush furiously, he started to avoid eye contact. "There's just... There's no way... Right? I couldn't be... That's just weird..." "It's not weird Jordan," I stated. Was this going to work? "Look buddy, you're one of my best friends, you be comfortable with whoever you are, you wear and do whatever you want. Especially here, in our apartment. I'm not one to judge." Jordan looked back at me, he was so confused, trying to wrap his head around everything. "I just don't... I woke up in it this morning and just started laughing, like, I had no desire to keep wearing it, at all." "Well," I offered, "you are still wearing makeup." Jordan quickly touched his face, he had forgotten he was obviously. It made sense, he was a dude after all. Normally didn't have to deal with that crap. "Are you sure I said I liked it?" he pushed. "And that I should be dressed like that?" he pleaded, looking up at me, and hoping I would say I was just joking... I didn't give him what he wanted. "Jordan, you made me run out and buy lingerie for you at like 3 in the morning, I would say you were pretty passionate about how you felt." I just smiled, being "supportive." I saw his face fall. This was all too much for him. "I... I don't know what to say..." He stared down at his body in confusion. "I just... It was a joke. Had to be a drunken joke. That's all." I was not going to lose this yet! -- "Look Jordan, can I suggest something?" "Yeah, I certainly don't know what I'm thinking." He laughed a little at himself "I took a couple psychiatric classes in college." Where was I going with this? I certainly hadn't done that... But I continued, "And I did a section on gender studies, I even had a paper published on it." Whoah, really needed to reel this back. But the college thing was good, Jordan's shame at not going to school often drove him to cling to whatever bit of schooling education he could and just run with it, it often made him post stupid shit on facebook as an attempt to seem like he was smarter than he was. "And I can tell you this -- when you discover this kind of thing about yourself, you don't run from it, and you don't try to ignore it, you look into it, and you see where it goes. A lot of the time, the answer is simple, or even what you expected, but either way, ignoring it will only make things worse." Jordan stared nodding like he knew what I was saying... He still looked entirely confused. I think this was working... I couldn't believe this was working. "So..." he started, "what... Uh, what do I do? What does that mean?" "You told me you got laid off," I offered and he nodded in shame, obviously having forgotten he told me. "Take some time off then. You have time, and hell, this entire apartment to figure this out. Try it. Figure it out." "You mean..." He paused. "Like... What do you mean? Dress... Like I did last night?" "Yeah," I smiled warmly, "Jordan, you were so happy last night, so try it when you're not drunk. Set a goal, from now until the end of the month, dress like a girl. And by the end of this month, you will absolutely know what you feel." "That seems crazy..." He was still in shock. "I just... Would that make me crazy?" "No Jordan, you're not crazy at all, okay? And hell, what harm is there buddy? It's just me, and if you can't tell, I don't have a problem with it. I just want you to be happy." I smiled genuinely. He continued to stare... Had it worked? "But... I can't be out of work for a month... What about rent? And I mean... Clothes?" Holy fuck... His hungover mind was actually starting to consider this. "Come on Jordan, what are friends for? You think I won't be here for you? I don't care about rent or some clothes. I care about you." The confusion, emotion, and hangover finally got to him. He began to say something but stopped, his mouth just opening and closing silently. I made my move, I was overwhelming him! This was working! I came around the counter and reached out, he still just stared in confusion. I wrapped my arms around him and gave him a big hug. Jordan wasn't much of as hugger, but I could tell, as someone who had been there for him over the years, and who had just played the part perfectly the last couple minutes, it was all just too much for him. He hugged me back, and began to cry a little, not too much, just some silent tears. "Alex..." he muttered into my shoulder, "you're the best. I just... You're right. If that's really how I felt last night, I need to figure this thing out for myself." I continued to hug him, but couldn't help thinking how his chest would feel against my body like this, once he had breasts.... I was truly evil. I pulled back and looked at him in the eyes. He wiped away some tears, and seemed to be shocked to see them. "Jesus," he laughed a little, "I'm already crying like a girl." He chuckled and I did too. "I'll buy you some stuff today, okay?" "To... Today?" His eyes went wide. "I... I don't know, maybe I need to think about---" "No, no, no," I teased, "if we're doing this, we're doing it right. I don't mind spending some cash on stuff for you." "It's not that, it's just maybe it was a fluke or something, maybe if my head is cleared by the end of the day--" I was losing him, I had to steer him back. "Don't be nervous Jordan, be happy! I don't mind at all okay? Trust me, like I said I have experience in this. Now, stop second guessing yourself okay? You're too smart for that." He smiled at my compliment. When had I gotten so good at manipulating him? "You're right." He nodded. "You're right. I shouldn't." He swallowed the remaining water in his glass. I could feel an erection stirring as soon as he took the last drop. I went back to the eggs quickly to hide it. "You go get changed, have some eggs, and I'll go get what you need," I stated. "Get changed?" he asked nervously. "Yeah, start the clock. No looking back now. You woke up dressed like that, don't second guess yourself." "I don't... You know... you're here." I smiled. "Look, I'll head to the store okay? I'll be gone for a while, you stay here and get used to it a little. I can do that for you." Jordan seemed to relax. "You're... Thanks Alex." "Of course." He slowly turned and headed for his room, closing the door behind him. Just the thought of him changing back into that lingerie behind the door was making me ache. I had to get out of here for now. I had done my part. ---------------------------------- An hour later, I had left Jordan behind and was at the mall, headed for the first store on my list. Jordan had made this too easy. With me in control of this, he had no say in what he was going to wear. I definitely had some ideas. The saleswoman smiled at me. "Hello, welcome to Victoria's Secret! How can I help you today?" I smiled back. "I'm here to completely replace my girlfriend's wardrobe." I returned that afternoon, about the same time my hangover finally died off. I hauled the many, many bags of clothing I had purchased and set them down in the living room. Jordan had probably heard me enter but hadn't left his room yet. He had called me a couple times while I was out shopping, I ignored the calls. I couldn't let him try and back out now. I heard the door open and he slunk out shyly. He was back in the previous night's lingerie and already blushing. In the day light he looked even better, and his face looked more made up. "You redid your makeup," I pointed out. He blushed even more somehow. "Yeah I figured... As long as I was... Holy shit, that's a lot of bags." He stopped and stared at them all, eyes wide. "Yeah, well I get a massive employee discount at the store, this was like nothing. And I didn't know what to get so I just grabbed whatever I could." Both of those were lies, but he didn't know that. This has taken a good chunk out of my savings. I was officially insane. "I... I don't know what to say..." "Don't mention it." I spread my arms towards the bags. "Just enjoy!" "Yeah..." He stared at them all still. "I just... I don't know, I feel more clear minded now, I think this is just, going too far. I don't think I even like what I'm wearing now." He looked down at himself in his nighty and stockings. "So..." I tried to sound disappointed. "I should just... Take all this back? I thought I was helping..." "Oh no! No, Alex... You're the best... Not many roommates would do this for another roommate." "Come on Jordan, you're not just a roommate. You're my friend." here it came, "Look," I said, taking an empathetic tone, "At least do this for me okay? I was there last night, I'm just trying to help you see what you saw when you aren't drunk." He still looked skeptical and somewhat annoyed with all of this. But I was swaying him, I just had to keep this up. I couldn't believe it was working. He was so easy to manipulate, I should have done this year's ago to get him to do dishes more often... "I mean come on, it's not everyday your roommate goes out and buys you a whole new wardrobe... I got way more stares buying this than you can imagine," I joked. Jordan laughed. There we go, laughing always got him back. He shrugged. "Okay..." he sighed. "Okay. I'll try this." He came forward and began picking up bags, carrying the first couple back to his room. I watched him from behind, admiring his booty in the sexy panties and nighty. I was changing my roommate into a girl. And I was loving every minute of it. ---------------------------------- Jordan began dressing for the rest of the month. He had his qualms initially after discovering all the sexy lingerie, and mostly skirts and dresses I had gotten him, but any real argument was squashed with me playing dumb, or just assuring him nothing was wrong with it. As the end of November neared, I could tell he was eagerly awaiting the end of the month, as he was still trying to fight about what he was doing. But as the end of that month neared, I could sense other changes in him too. His arguments with me soon became a little more emotional, and I had noticed him tearing up over a film we had watched the other night. This was understandable -- I had been sneaking the hormones into his morning breakfast still. As hard as this was on Jordan, it had been very hard on me, not only did I have to get into a routine of waking up early enough to sneak him his hormones, but him prancing around the house had taken it's toll on me. He had limited his wardrobe to a couple simple outfits that were borderline androgynous, but it didn't matter to me, everything I saw him in turned me on, and even more so, every time I caught a peek of a bra cup, strap, or panty line, I nearly had to run to my own room to take care of myself. He stayed in basically house arrest, never daring to go outside, and spending most of his time looking for new work on his computer. I refused get togethers with our friends to spare him having to meet them and be thrown off track, I blamed us avoiding them on apartment renovations and job searching for Jordan. The end of November drew near, and Jordan's qualms with dressing, mixed with his very understandable case of house arrest boredom, meant I knew I had to convince him to keep up the charade. I either had to take action, or let all this work slip away. I had come too far now. But I had a plan. I came home one evening with a bottle of whiskey, and a fake smile on my face. ---------------------------------- "I got a raise!" I said to Jordan, who was on the couch in a simple tank top and short shorts. God his legs drove me wild. He looked up from his magazine. His hair had gotten longer, and he was wearing minimal makeup, but still a cutie. I handed him a shot of whiskey, and he toasted me. "Cheers!" he shouted, genuinely happy for me. He took the shot. "Congrats Alex! Was it a big raise?" "You have no idea, I am getting drunk tonight! We are definitely going to celebrate! I know you've been kinda stuck around the house and without much access to anything, so I picked up Saren's on the way home." Saren's was an expensive restaurant in town, Jordan loved it, he had worked there as a first job years before. "Oh sweet! That's awesome man, thanks!" "No problem, we're also gonna eat it on the balcony, because you need some damn air." "Even better!" he exclaimed, but he looked out at our second story covered porch a bit hesitantly. I poured him another shot, and he took it. I stood and headed for the kitchen and the take out. "So dress in your best, it's a white tie event, I'mma throw on my suit and get this all on a plate!" "Sweet!" Jordan stood, then seemed to register what I'd said. "Best? Oh... Like... I mean it's just out on the balcony right?" "Yeah," I said as nonchalantly as possible, "but what's the point of celebrating if you don't dress up?" "Yeah... I just..." "Didn't I buy you something nice? I can't remember, I don't think I've seen most the stuff I bought you," I said, trying to lay on a little guilt. "Yeah... well I mean, I've just been stuck around the house, there hasn't been a reason to--" "Well perfect then, I don't want all that to go to waste." I poured him another shot before he could tell me not to and headed for the food. Jordan seemed hesitant. I watched him stealthily from the kitchen. He just stood, unsure where to step toward. He seemed to finally give in, took the shot and shrugged. "You're right, okay, yeah..." He started heading for his room. The whiskey was going to do its trick. I started pulling out plates and glasses, anything to keep busy as I watched him head to his room. He did what I expected, I hadn't been lucky enough to get at the right angle yet for this. From the kitchen I could see right into his room, and he had always been so used to not giving a shit about privacy, he usually left it open. I tried not to stare, but it was impossible... I wanted to see if the excessive amount of pills I'd been giving him were doing anything... With his back to me, he headed for his closet and then gently pulled his tank top up and over his head and let it fall to the floor. The sight of his pale back covered in a bra was already a turn on. I was changing my roommate into a hot, sexy little woman. He was wearing a bra, for me! He unbuckled his belt and then slid out of his short jean shorts, bending over a little to slide out of them, and revealing a sexy pair of panties hugging his cute little bubble butt. He would thank me for this later, his body was destined to be this sexy, and so much more so, with my help. I cursed the tingling feeling in my pants. I had to hold it together. ---------------------------------- About half an hour later I finished setting the table and sat down, laying more whiskey in front of both of our plates. I heard the gentle clicking of heels and tried my best not to whip my head towards him as he walked out onto the porch. He paused briefly, he was stunning. He was wearing a skin tight little satin dress, in a bright red. It landed about halfway down his thighs and had an off the shoulder style to it. The neckline plunged to accentuate his surprisingly present cleavage. Nothing huge, but a little of something. He had finished off the look with some smoky makeup and nylons that led to some sexy strappy heels. His hair had been curled a little, resting just above his shoulders. I had caught him watching makeup tutorials in confusion in the past month, he must have been practicing when I wasn't there. His nervousness only made him that much cuter. "You look great," I said a little too honestly. "Don't... Come on..." He became red with embarrassment. "Don't say that man... I feel silly enough as it is." He absentmindedly tugged at the short hem of his dress. "Don't feel silly Jordan," I reassured, "there's nothing silly about it." I waved my hand at his seat. He took a couple timid steps forward, darting his eyes around as if in fear that someone may see him. He reluctantly sat down, and instinctively ran his hands over his butt to let his dress lay flat. It was such a feminine move, and when he crossed his legs properly I had to make sure my jaw was closed properly, less it was hanging. He gently picked up the whiskey in front of him and started drinking to calm his nerves. I started eating, pretending everything was natural. After a strong sip he seemed to relax a bit, but he still seemed unsure of his own body, he tried to sit back then changed his mind and sat up straighter. It only accentuated what I was now officially calling his perky little breasts. I started asking about the TV shows he'd been watching in the apartment on his own, and it seemed to get his mind of himself. Soon he was chatting like we used to back in the day, and he seemed to become unaware of what he was dressed in as he ate and drank along with me. By the time I was filling up his sixth glass at the table, he was starting to show the signs of drunkenness I so desperately wanted, and even I was feeling buzzed as hell, which upset me, I had to play this right, I could take no backward steps. I set down my fork and focused on my whiskey. "Hey Jordan, I hope I'm not being out of line, but I was just wondering... Do your... You know... Pecs seem bigger? Have you been working out while I'm at work?" He looked down at his subtle cleavage. "I wish... It's kinda the opposite, I feel like I've been gaining weight, even though I've been on the treadmill every morning. Especially in my butt, I mean, my panties actually kind of form fit to me now." He blushed after saying panties. He looked so cute like that... With his hair framing his freckled face, his lashes covering his big, almond shaped eyes. "That's... Huh... I wonder..." I started, then stopped, pretending to lose interest. "Never mind. It's probably nothing. How was the food?" "Huh? What is nothing?" He was worried, and blinking slowly, he was getting to that stage. "Oh, nothing. I just, you know, I remember some things from when I took that class... Just about how the body reacts to certain stimuli." "You know why I might be gaining weight?" "Well... Not just that... But, well, let me ask, have you been feeling more emotional at all lately? Kinda mood swings and stuff?" He thought for a second, then his eyes went wide. "Holy shit... I kinda have... I didn't really realize until I thought back on it." "Oh... Well... Jordan, your body is reacting to how you've been dressing this last month." "What... What do you mean? How can wearing clothes make me gain weight?" "It's not the clothes Jordan, it's what your subconscious is doing... Your subconscious is changing your body to how you really feel." He stared at me... Trying to wrap his head around it. "What... What are you saying?" But I could tell he was picking up on what I was saying.... Or... At least falling for the massive lies I was spinning... I had no idea someone could be so manipulated with just a little bit of fake science to back shit up. "I mean, that's not even a push up bra Jordan." That was a lie. That's all I had bought for him. Just some pushing up slightly less than others. "What... What?" He gently grabbed his breasts, trying to measure them. "It's not?" "No Jordan I mean... It just means you almost fill out a woman's bra now... After only a month." "Holy shit you're right... I should be taking these off of women, not be capable of wearing them! Oh my god Alex, am I growing breasts?" he pulled back the top of his dress a bit to look at his bra and breasts. "Yeah, it seems like it," I stated. "I need to stop this, I knew it was a stupid, dumb, ridiculous thing, and I never should have done it!" "No, Jordan, you were right to do this. Your body is telling you something." "Telling me what? My body is telling me that it's lost it's mind?" he paused... Then laughed funnily enough. "God, that was kind of a dumb phrase..." He shook his head and closed his eyes. "What's..." he sighed.... "What's happening with me Alex? I don't understand. Nothing online has been helping... if anything I've just been getting more confused, and nobody is taking me seriously when I ask!" "Jordan, you need to give yourself time to figure that out. It's the only way to get to the bottom of this. Look... I'll talk to one of my friends from school, let him know what's going on, and he can get me a full description of what's happening. Maybe even write you a prescription if it's anything weird. Would that help?" "Yes," he nodded with closed eyes, "that would be amazing. In the meantime I need to stop everything related to this. It's been about a month." "Jordan, you can't do that now. You have to let your body and mind come to terms. Honestly, you can't ignore what your subconscious is screaming at you." I tried to smile at him as he opened his eyes, looking defeated, I took a bolder move forward, "I mean, Jordan... You can't deny that some part of you loved dressing like you are now, nobody looks as good as you do in that outfit without a little effort, and a little enjoyment. Right?" "I..." The male side of him was losing. "I don't know." "Tell me something," I inquired, "when you picked out that bra you're wearing, what were you thinking about? Was it just an article of clothing or was there more?" "It was just..." He looked down at the bra. I had seen enough of it most the night now, it was sexy, black satin, with some frilly little lace, and a long band to act kind of as a corset. It was a sexy bustier I had purchased for him. He continued, "I think I just... Picked it... But... also... I knew I'd be wearing a nice dress... And, I also wanted to look good.... And I thought, this is a special occasion, it deserves a nice bra." He looked at me, somewhat horrified with that admittance. I doubted he had thought any of that, but with my provoking he probably thought he had. "And?" I pushed. "I... When I put it on, I liked that it actually fit my chest... Because it's been weird to wear these clothes and not fill out the top, they don't fit right if they don't." He was on a roll now, seemingly convincing himself of all of this. "I put it on and thought I looked good in it. I was happy... I thought it looked sexy?" This was brilliant, Jordan seemed to be confusing his own sexual desires for the female body, with his own body, which was feminine enough to elicit him feeling turned on by the sight of it. He was in a rabbit hole. "I... Maybe you're right... I mean, look at me." He looked down at his body and ran his hands over his breasts, his thin satin covered waist, and hips, down to his legs. "I can't deny... I just can't deny that I look like I should be in this... I mean... Look at me Alex! I have breasts! Well not big like, breasts... But my pecs are... I mean look." "What if they were bigger?" "God knows they'll probably get there now!!" "Do you want bigger breasts?" "I don't know..." He stopped, processing what he said. "I don't know? Why don't I know? I should definitely know!" He looked down at his perky boobs again and stared. I was barely holding it together, it was a good thing there was a table between us or he'd be seeing something very ungentlemanly happening in my pants. "Maybe you're right, maybe I need to follow through, figure this out." "You're strong Jordan, you've faced worse things in your life." He smiled. "Thanks Alex. For everything." I smiled back... This was going great... And I was so evil... ---------------------------------- We drank a couple more glasses, and by the end of the night, Jordan let the conversation fade away to ponder on his own and we soon fell back into our regular conversations. When we finally returned back inside, it took all my will not to follow him into his room, but that would have ruined my plan. About an hour later, with me doing nothing but staring at my wall and fiddling with the syringe in my hand, I finally got up and headed for his room. He had to have been in a deep drunk sleep by now. I entered his room casually, holding a borrowed DVD just in case he awoke to see me, but he was clearly passed out. His sexy dress was on the floor and he was lying on his side on the bed, still dressed in his sexy black lingerie. I went around the bed to his cute little derri?re and raised my syringe. If I started this routine now there would be no going back for him, he would be stuck in a bra and panties forever. His male hormones would end, and those pills I'd been feeding him would certainly take a bigger effect. I stared. His body dressed as it was didn't help. It was already so feminine... To think this had all started over one silly comment. What would he dress as for next Halloween I wondered? That's the thought that got me. A mountain of sexy costume ideas came to mind and I wanted to see him in everyone of them. I stuck the needle into his cute little butt and bit the bullet. I had done it. She was going to be so beautiful by the end of this. ------------------ Hopefully you all enjoyed this story! It has been years since I posted anything new, I've mainly been busy doing my own thing lately, lots of photos and stuff for my fans. Hoping I can do more again! -- With Love, Ashley