Best Served Cold Chapter 6 The Party Best Laid Plans
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Best Laid Plans free porn video
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."
Deep down, I knew that a guy like Jake would never be satisfied with just
a blowjob, even if he came. But I had been unwilling to think about what
now seemed like an inevitability, giving my anal virginity over to my hunk
of a roommate. However, as the painfully swollen cock trapped underneath
my panties reminded me, I was still desperately horny. The combination of
having gone so long without sexual contact and having given up
crossdressing meant that I now couldn't control my lizard brain. I gave
him a silly smile.
In response, Jake leaned over and picked me up off the floor like I
weighed nothing, and I looped my arms around his muscular neck as he
princess-carried me to his room. While I wasn't particularly heavy, I was
shocked at the way he manhandled me like a child, and I was reminded once
again of the vast gap in our bodies. We were both technically guys, and
yet the differences between us were like those between an Alaskan Malamute
and a Chihuahua. Was I really expected to compete with this Herculean
specimen for female attention?
I surrendered to the realization that it had been futile all along, that
this was where I was destined to end up, sooner or later. At that
cathartic epiphany, I shuddered as a weak stream of semen pooled in my
panties. Gently lowering me onto his bed, Jake opened his nightstand
drawer to produce a bottle of lube and a condom.
"What are you doing, silly?" I giggled. "I can't get pregnant."
He grinned, and tossed the condom aside as he squeezed a generous amount
of lube on his still-erect cock. I expectantly got on all fours, arched my
back, and presented my ass to him. I could only imagine the erotic view he
was getting of my short dress riding up my hips, garter straps exposed,
and small wisp of black lace covering my puckered, hairless hole. I could
feel my cum from earlier dripping down my thighs.
"Somebody's wet," my roommate said as he slapped my ass, and I yelped
girlishly. I felt him slip my thong to one side as cold, slimy lube first
drizzled onto my asshole, and then made its way inside me as one, then two
fingers began warming me up. Unsurprisingly, he was no novice at anal.
I was no stranger to anal masturbation, but it was an entirely novel
sensation to have another human being play with my ass, especially one as
attractive and experienced as Jake. Soon, he was stroking the inside of my
hole with three fingers, and I knew it was time.
"I'm ready," I whispered.
Surprising me, Jake flipped me onto my back, and, grabbing my heels,
spread my legs apart.
"I want you to see me fuck you, Jennie," he growled. "I want you to watch
as my cock slides inside you."
I nodded eagerly as Jake positioned his hips and brought his engorged cock
to my eager and waiting ass. I gasped when he began pressing the spongy
mushroom head of his manhood into me, but with surprisingly little
resistance, it slipped inside me with a soft pop. For the first time, I
had a real cock inside me, and it was none other than my roommate's.
"Your ass is so fucking tight," he grunted, as he slowly began thrusting.
All I could do was moan wordlessly with feminine pleasure. With his grip
on my stilettos, I realized how he was in complete control of my body, but
this vulnerability, far from alarming me, only further increased my
arousal.
As Jake increased the speed and depth of his thrusts, I realized that when
I had been masturbating to Jake and Rachel fucking, it wasn't because I
wanted to fuck Rachel. I wanted to be Rachel: desirable, sexual, and both
pleasing and being pleasured by a real man. Now, impaled on my roommate's
massive cock, my subconscious fantasy became a reality.
With each thrust, I was unconsciously matching Jake's animalistic grunts
with girlish moaning of my own. With each thrust, I felt the final
vestiges of my masculinity being fucked out of me. The impossibly full
feeling of being penetrated by my roommate, along with sight of his
chiseled body, dripping with sweat, put my brain on autopilot. I was now
acting solely on primal, sexual, instinct, as I squirmed and bucked my
hips in time with his, trying to hit that elusive "p-spot."
Abruptly, I gasped when the combination of depth and angle aligned just
right, and Jake's cock began ramming my prostate. He sensed my pleasure
and redoubled his efforts, causing me to grab his muscular, iron-hard
forearms with my hands. My nails dug into his skin as I writhed in
pleasure, but he didn't seem to mind. Instead, his cocky grin turned feral
as he brought me closer and closer to orgasm.
"Are you going to cum for me, Jennie?" he growled. "Cum like a good little
slut while daddy breeds you."
In the back of my mind, I knew that I shouldn't be able to cum while my
small "clit," still safely nestled in my panties, was still barely
engorged. But the fuzzy, persistent warmth that was spreading outwards
from deep inside my ass was suggesting otherwise. I watched intently as my
ass seemed to swallow up, then disgorge, Jake's thick meat.
"Please don't stop," I panted. "I'm so close, I'm so close, I'msoclose,
I'msocl-"
Jake's cock pulsed and swelled inside me, releasing its second torrent of
molten seed that day, the knowledge that I had been the one that had
brought him such pleasure took me over the edge as well. Waves of liquid
euphoria poured over me and I screamed as I came.
As Jake and I continued to ride out our respective orgasms, each motion
sent immense ripples of pleasure radiating out from my abused hole.
Individually, they dwarfed even my most memorable orgasms up until that
point, and in the aggregate, well...there was no going back. I was well
and truly Jake's girl.
Finally, after what seemed like an eternity, Jake released my heels and
collapsed on top of me. I wrapped my legs around his waist to keep his
manhood lodged deep inside of me, and clenched my sphincter to massage his
slowly softening cock. He groaned in pleasure, and kissed my neck in
response. The unfamiliar sensation caused me to shiver delightfully.
"You're even hotter than I remembered," he mumbled into my collarbone.
"And you fuck better than I had hoped."
My jaw dropped in shock. So he hadn't blacked out that night he caught me.
Then why didn't he say anything? Was all of this truly a fateful
coincidence or merely an elaborate ploy that I had fallen for?
I was about to speak, then closed my mouth and smiled contentedly. It
didn't matter, did it? We had both gotten what we had deeply desired. As
for how this would change our relationship going forward, well, who knew
when the world would return to normal? Until then, I had plenty of sexy
outfits to try out. And more importantly, I thought, smiling to myself, I
had Jake all to myself.
Jennie's note: Returning to "feature length" stories! Please leave a
comment, as it encourages me to keep writing!
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