Best Laid Plans

Over a year into COVID quarantine, my roommate Jake and I were bored out of our minds.

We had gone through the litany of pandemic hobbies, including bread baking, watercolors, hydroponics, knitting, jigsaw puzzles, and even a brief attempt at yoga that failed miserably. All of these activities and their associated paraphernalia increasingly cluttered our small apartment, and when Jake almost twisted his ankle on a misplaced bread pan, we decided that we needed to Marie Kondo our place and clear out some junk.

Jake took the kitchen and bathroom while I focused on the living room. We had a small "general purpose" storage closet in the living room, and I started there. Opening the door, I sighed as I was confronted by a haphazard mess of boxes and cleaning supplies.

"Uh, wanna trade?" I yelled hopefully.

"No thanks," Jake said from the kitchen. "I'm like halfway done."

Sighing again, I began by removing the larger items from the closet. Out came a vacuum cleaner, a guitar case, several family-sized packs of toilet paper, before I noticed a large cardboard box stuffed all the way in the back of the closet. Wrinkling my nose at the dust that now suffused the air, I grabbed the box and was surprised at how heavy it was. Unlike Jake, who had the muscular physique of a former college basketball player, I had always been pretty thin from a combination of genetics and distaste for the outdoors. Unfortunately, all of our bread baking meant that I had put on a few pandemic pounds, mostly around my hips, giving me an embarrassingly feminine figure. My thin arms struggled to lift the weight, but I felt too embarrassed to ask my roommate for help. I eventually managed to wrestle the box into the living room and dropped it with a loud thud.

"Hey, what's in that big box in the closet?" I asked, wiping the sweat from my forehead.

Jake poked his head out from the kitchen. "What box?"

I gestured at the ground in response, and Jake's face, normally sporting a cocky grin, abruptly fell.

"Oh, uh, those are Rachel's things."

"Oh."

Rachel was Jake's volatile ex-girlfriend. Smoking hot and with no employable skills, she was an "influencer" who had moved in with us when she was unable to make rent (she was okay being paid in sample products and clothing; her landlord was not). During that time, try as I might, I couldn't help but hear them fucking like rabbits through the thin walls of our apartment, and had ashamedly jerked off a few times in the privacy of my room to the loud moaning and sounds of wet flesh on flesh.

Being forced to spend more time with each other accelerated the inevitable demise of what was an incompatible relationship from the start. After a particularly nasty argument, Rachel abruptly dumped Jake and walked out with two suitcases in tow. Apparently she had left some stuff behind, and Jake had kept it. He must not have been as over her as he claimed to be, despite their obvious differences.

"Just throw it out," Jake said at last with a sigh.

"What? No!" I said without thinking.

Jake raised an eyebrow. "Why not? It's just her clothes and stuff."

I hesitated, unsure of how to justify my reaction. "I-I don't know, it seems like a waste," I said at last, lamely.

Jake grinned teasingly. "A waste? Keep them for yourself then."

The blood drained from my face. Could he possibly know?

For as long as I could remember, I've had a compelling urge to dress in female clothing. And not just clothing, but the whole nine yards: wigs, makeup, heels, and accessories. When I had finally had the money to begin experimenting with more than just the odd pair of panties pilfered from the laundry room, I began pushing myself to perfect my transformations. It became oddly rewarding to see myself slowly becoming more feminine each time I dressed up. At some point, I had become, even to my own critical eye, fairly passable, despite only ever dressing in secrecy. The abundance of resources available online meant that I didn't necessarily need feedback or guidance, especially because I was singularly obsessed with becoming the most convincing girl I could be. Occasionally, when dressed and masturbating, I would fantasize about the final step in becoming a girl—being penetrated by a faceless male—but it always remained just a fantasy. I was way too shy and private to even think about showing Jennie to someone else, much less doing anything sexual with them.

After Jake and I moved in together, I had occasionally caved to my desires and, despite the risk of being caught, brought out my small collection of girls' things from under my bed to transform into "Jennie." Since we shared a bathroom and I needed the bathroom to both put on and remove my makeup, it wasn't possible for me to just dress up in my room. I usually chose nights when Jake went out to party to indulge in my feminine side, as he wasn't prone to coming home before the bars closed, if he came home at all. However, one night I teetered into the living room in my tight, black minidress and stilettos and found a piss-drunk Jake reclined on the couch.

My roommate squinted at me as I froze like a dear in headlights. "Whareyew?" he had slurred drunkenly.

I dashed to my room in terror and locked the door behind me, on the verge of hyperventilating. While I was in my room tearfully envisioning how I would now be forced to move to a city far away from everyone I knew, I heard Jake stumbling around for a bit before he went to his room and passed out. I snuck out a few hours later to remove my makeup and put away my feminine toiletries. The next day, Jake sported a massive hangover and made no mention of the incident, and I assumed he had been blacked out when he saw me dressed up like some club slut. That night, I gathered up all my feminine things and threw them in the dumpster. I had come way too close to being caught, and didn't trust myself to not dress up again at some point.

But now, a windfall presented itself to me: a free cache of undoubtedly stylish and sexy clothing, picked and worn by Jake's hot ex-girlfriend. I didn't stand a chance.

"Maybe I'll hang onto them and donate everything with the clothes I'm throwing out to Goodwill," I suggested casually, heart pounding.

Jake shrugged and returned to the kitchen. "Knock yourself out, dude."

I didn't detect suspicion in his voice. And why would there be any? To most red-blooded males, women's clothing held no significance beyond being strangely overpriced. But to me, they allowed me to unleash a wild, sexual side of my personality that I kept carefully suppressed.

Hands shaking, I lugged the heavy box back to my room. Maybe just a quick peek. I quietly tore the tape off the bulging box, flipped open the cardboard, and gaped, flabbergasted, at the absolute trove of feminine treasures inside. From sky-high pumps to slinky thigh high boots, lacey lingerie sets to sporty yoga apparel, cute sweater dresses to indecently short leather skirts, there were at least two dozen gorgeous, head-to-toe outfits just begging to be tried on. Digging through the pleasantly floral-scented clothing, I found an overnight bag packed with makeup as well as a small box of accessories. The idea of owning all of this, of wearing it, was giving me a boner underneath my sweatpants.

My resolution to never crossdress again already forgotten, I was now desperately trying to recall when Jake said he would be out of the apartment next. During quarantine, it was uncommon for either of us to really go anywhere, but I did recall him saying he would be visiting his parents the next week. I put the box in my closet so that I wouldn't be tempted to jump the gun, and tried not to count the minutes until I'd have the apartment to myself.

* * * * *

"See ya next week!"

Jake was off to his parents', and before the apartment door had even closed, I was already dashing to my room to pick out my outfit. My heart pounding, I rifled through Rachel's things with a voyeuristic excitement. These were the beautiful clothes that that goddess had worn, some undoubtedly while Jake was fucking her. My fingers lingered over an expensive-looking, three-piece lingerie set: black lace bra, thong, and garter belt. It oozed of sexual femininity, and I just had to wear it, even if it meant limiting what I could wear for the rest of my outfit.

I eventually found a slinky black minidress, rouched at the sides and with thin spaghetti straps, that wasn't too different from the one I had been wearing when Jake "caught" me that one night. Little black dresses were my favorite, and eyeballing it, it was just barely long enough to cover the straps of the garter belt. Sheer, black thigh-highs, a dangerously thin, 5-inch black stiletto pumps, a few silver rings, a thin silver bangle, and large, silver hoop earrings, finished off my "date night" outfit. My date was, of course, with the cucumber in the fridge, but that was for later.

Giggling with anticipation, I brought my outfit along with Rachel's makeup bag to the bathroom. In preparation for this, I had already shaved every hair off my body save for my eyebrows, and my shoulder-length quarantine hair had been carefully conditioned and tied back in an androgynous ponytail.

I gingerly sifted through Rachel's makeup and picked out the items that I'd be using: full coverage foundation (porcelain), pale pink blush, cappuccino eyebrow gel, jet black eyeliner, red eyeshadow, mascara, false lashes, and a lipstick.

With familiar motions I began applying the makeup to my face, transforming from a nondescript boy into a seductive minx. Time flew by as I worked, and even though it only felt like minutes I knew I had been painting my face for at least an hour. I stepped back from the bathroom mirror and surveyed my handiwork with a critical eye: thick, dramatic lashes and razor-sharp eyeliner framed doe-like eyes; brows shaped into thin feminine arches; plump, pouty, blood-red lips—I hadn't lost my touch.

I blew myself a kiss and untied my hair. Adding some mousse, I used the blow-dryer to style it into loose, feminine waves. I then slowly slipped into Rachel's delicate lingerie, imagining that I was somehow borrowing more than just her clothes, but some part of her feminine beauty. Goosebumps ran up my skin as the soft lace of the bra caressed my body like a lover's touch. The sensation of being gently but firmly constricted by such gorgeous underwear was a feeling I had dearly missed, and couldn't be found in drab boys' clothes. Already, I was getting uncomfortably excited, and I quickly tucked my half-erect cock back between my legs before pulling up the wispy thong to keep everything in place. Clipping the garter belt around my waist, I threaded the straps under the thong (a girl always has to be ready to take off her panties), and carefully rolled up the sheer black stockings up my smooth legs before clipping them in place. I wiggled into the little black dress—which was a tight, but manageable—and struggled a little before zipping up the back. Finally, I stepped into the black pumps, which were again, a little small, but manageable. Teetering a bit at the unfamiliar height, I rolled a random perfume sample from Rachel's stash on my wrists and neck before taking small, mincing steps to the bathroom door. Now that my transformation was complete, I wanted to see the whole thing in front of the floor length mirror in my room and not the tiny bathroom mirror.

I opened the bathroom door and was greeted by Jake's comically shocked face. I shrieked.

"R-Rachel?" Jake asked hesitantly. "What are you doi-?"

I immediately tried to shut the door but Jake easily held it open with one arm. His eyes, already wide with shock, widened even further. "Wait a minute...DUDE."

Realizing there was no way I could outmuscle Jake, so I tried to dash past him. Unfortunately, it had been way too long since I had last worn heels, and I was vastly overconfident in my muscle memory. I immediately stumbled.

Reflexively, Jake caught me and the next thing I knew, I was pressed against his broad, muscled chest. I froze in terror. What could I do, or even say? I had just been caught, dead to rights, fully dressed in my roommate's ex-girlfriends' clothes. And not just her street clothes, but her sluttiest, come-hither lingerie, dress, and heels. I'd have to move out to a different apartment, if not a different city. My life was ruined.

"You smell just like her," Jake said over my head, still gently embracing me.

Blushing for some reason, I quickly pushed away from him. Looking up, I saw not disgust or anger, but that familiar crooked grin.

"I swear, I thought she had come back for a second," my roommate chuckled.

"I'm sorry, I know I said I'd donate her stuff but, I just..." Between the humiliation of finally being caught and the shock of Jake's unexpected presence, I couldn't find the right words. Tears of frustration began welling in my eyes.

Jake cut me off, "You don't have to apologize. I mean, it's not my stuff, anyway. I'm sure she wouldn't mind. Like, you look good. And I shouldn't even be here...I just forgot my driver's license."

I first realized he was babbling nervously, and then realized that he had said I looked good. Now, until that moment I had never really looked at Jake the way a girl might look at him. Sure, he was tall, athletic, handsome, kind, funny, and thoughtful...but we were both guys and so he was just a good roommate and better friend. But in that moment, dressed to the nines in Rachel's clothes, I didn't feel like a guy. I felt vulnerable, feminine, and most of all—if the swelling in my panties was any indicator—incredibly aroused.

"You think I look good?" I asked, unconsciously reverting to my soft "girl voice."

Jake eyed me incredulously, "Are you kidding me? You look fucking great." He chuckled. "If only I'd known I've been rooming with a fox for the past year."

I felt strangely empowered when I asked, "And if you had known? What would you have done?"

Jake deliberately brought his eyes down, then back up, slowly appraising my body like a piece of meat. "I'd have been enjoying that fox instead of baking all that fucking bread," he said slowly.

"Maybe you should make up for lost time," I whispered, heart in my throat.

Jake closed the distance between us in a flash, cupping my chin and tilting my unresisting face up towards his, before crushing his warm lips to mine. Immediately, his tongue began probing my lips before making its way into my mouth. It was my first time kissing another boy, but I could already tell it was going to be very different from what I was used to.

Jake's hands started around my waist, but now made their way south to cup my buttocks, squeezing hard as we made out. Pressed against his body, I was acutely aware of how small and soft I was compared to his ripped physique. And his muscles weren't the only thing that was hard; I felt a thick, hard bulge pressed against my belly through Jake's jeans. There was something perversely satisfying in knowing that I, in his ex-girlfriend's clothes, had caused that kind of arousal. In a feedback loop, Jake's obvious desire for me was breaking down any logical objections I had to what was happening. I had never thought about other men sexually, but in that moment it wasn't about whether I was a straight boy or not—I just desperately wanted to please this paragon of masculinity before me.

Still with my tongue entwined with my roommate's, my small hands began fumbling with Jake's belt. I had never taken off someone's belt before and the reversed motions were unfamiliar.

Jake broke away from passionately sucking on my face to tear his shirt off, unveiling the rippling muscles underneath. Now that I was able to see what I was doing, I undid his belt and pulled down his jeans. The thin material of Jake's boxer briefs could not conceal his raging 10-inch erection. I licked my ruby lips unconsciously.

My roommate began slipping the spaghetti straps of my dress off my shoulders, but I stopped him. "Is it okay if I keep Rachel's clothing on?" I asked softly. "It makes me feel more girly."

Jake grinned. "You little perv."

In response, I dropped to my knees and pulled down his boxer briefs in one motion, releasing his thick cock. It sprang forward stiffly, bulbous purple tip already dripping with pre-cum.

On my knees, I looked up at my roommate and smiled seductively as I leaned in towards his manhood. It emanated an intoxicating scent of soap and musky masculinity. This was the moment of truth. Were the two of us horny enough from over a year of sexual repression to take this next step? Making out was one thing: sucking a man's cock was another.

I shouldn't have wondered.

"Let's see that pretty little mouth of yours wrapped around my cock," Jake said, as one hand casually yet possessively patted the top of my head.

Being called "pretty" shut down the last rational part of my brain that was still weakly protesting this abrupt turn of events. Without breaking eye contact, I tucked my hair behind my ears and obliged my roommate and slipped his thick member into my mouth. The sweet pre-cum was like nectar. Recreating the thousands of blowjobs that I had seen in porn, I began bobbing my head while maintaining a tight seal with my painted lips as my hands worked his shaft and balls. I knew I was doing a good job when Jake groaned in pleasure and grabbed my head with both of his hands.

I knew what he wanted, and submissively put my hands in my lap, relaxed my throat, and continued to gaze up at him demurely.

Jake held my head still and took over, gently thrusting his hips. I could feel the thick shaft of his cock first fill my mouth, then my throat. Fighting the urge to gag, tears formed in the corners of my eyes as my roommate began steadily face-fucking me.

The sheer, erotic energy of our taboo coupling was overwhelming, but I fought the urge to jerk off. I didn't want to spoil the feminine illusion by suddenly producing a penis, small as it was. Instead, I focused on being a pleasure receptacle for Jake. His pubic hair was soon tickling my face, and I could feel his cock distending my throat with every thrust.

My efforts were rewarded, and I felt his cock swell and pulse as I recognized that he was about to cum. I surprised the both of us when I broke away from his grip, grabbed his monstrous shaft with both hands, and began stroking it rapidly.

With my tongue out, I maintained eye contact as I jerked my roommate off with both hands. It was a strange paradox of power. I was the one on my knees jerking off another man, but I knew that with one simple phrase I could give him the release he so desperately wanted. Jake groaned pleadingly, and I could tell he was very close.

"Please cum on my pretty little face, daddy," I begged, and Jake's cock immediately erupted. Thick, hot ropes of cum jetted from his engorged penis, spraying across my face. It would have ruined my makeup had my makeup not already been completely ruined by saliva, tears, and runny mascara. I instinctively tried to stop as much of it from dripping onto the floor as I could, instead scooping it with my fingers into my mouth.

"Oh fuck, that's fucking hot. Rachel would never let me cum on her face," Jake said weakly.

Slurping a stray bit of cum and licking my fingers clean, I said, "It's rude to bring up other girls in moments like these, you know."

"You're right, I'm sorry." Jake looked down sheepishly. "'Other' girls?"

I pouted. "You just came on my face, do I not look like a girl to you?"

"Fair enough," Jake grinned that lopsided grin. "And what's your girl name?"

"Jennie," I said softly. It was strange, just casually telling another living soul my deepest, darkest secret.

"A pretty name for a pretty girl." He was catching on quick. "And I know just how to make pretty girls feel good."