tagTranssexuals & CrossdressersBoth Sides Of The Coin

Both Sides Of The Coin


Jessica and I were back at the scene of the crime, so to speak.

Her work friend, Mike, hosted a costume party every year on the Saturday night 8 days before the Super Bowl, "Because there's never anything else going on that weekend." Last year, that tagline on the invite offered sufficient enough logic to get Jess and me out of our apartment and over to Mike's, and up until a week ago I was very much looking forward to the 2013 edition.

The thing was, last year we had won the contest going away. . .

[Cue the Wayne's World styled flashback sound effects]

...I was wearing a "Teacher Costume," otherwise known as my business casual work clothes, but Jess went all out as a naughty school girl. I certainly hadn't seen the skirt before, but it was rolled up high enough that there was plenty of naked leg showing before her knee-high socks got in the way. On top was the typical white button up shirt, which barely contained her healthy chest, and certainly did nothing to hide the fact that she was wearing a red lacy bra. With Jess just standing still, it was enough to make any man's blood rise. As you might expect, what with this being a sexytimes story, Jess was hardly ever standing still. She's generally an active participant in all things party-related, so that night she was dancing and twisting and spinning and clapping and jumping. And as you might further expect, any of those fun verbs gave most of the room a decent look up her skirt and at the pair of red panties that completed the set.

By overwhelming popular vote (in a room split 60/40 male/female) "we" won the contest. Many high-fives were thrown followed by celebratory sips of booze. A fine story all around, were it to wrap up here (but it won't, because you haven't cum yet dear readers).

The thing is, I remember noticing Jess's actions getting progressively stranger over the course of the night. It was if the costume had gone straight to her brain--She wouldn't stop with the schoolgirl act even when we had left the main room of the party and were heading for our quarters for the night--the spare bedroom.

"Have I been a bad girl?" She cooed into my ear.

"You've been...ummm...plenty bad" I replied awkwardly, pathetically trying to keep up with her innuendo and stay on board the don't-mess-this-up train making all stops between blowjobville and cowgirl junction.

She giggled back at me, and pushed me into a conveniently located desk chair. With her heels still on, she sunk to her knees. Continuously giggling, she undid my belt and pulled my cock out of my pants.

To this day it was the best head I've ever gotten in my life. Truly a mind-altering experience. Months later, I would consider changing the dating system in my journal to make that event count as day "1" of my life, with all things prior to that heavenly blowjob occurring in some hazy long-long ago that doesn't merit official record.

I can't say for sure how long she was down there, it was dark in the room and I couldn't see my own watch. I remember alternately having my hands on the back of her head, holding her pigtails, and desperately gripping the arms of the chair trying to make sure I didn't fall out. The sounds were new too--lewd. Jess was moaning--nothing I hadn't heard before, but this was...it was as if my cock had become filled with the very essence of eroticism, and her giving me pleasure shot reciprocal waves back through her body. I noticed briefly that she was alternating hands to hold my thighs, stomach and balls, and that her "off" hand was going to work on herself. She must have cum four-five times. My cock felt bigger in her mouth, or her mouth felt smaller. It was warm and for a moment, I thought she had grown a second tongue. A passing car out the window briefly illuminated the room and I caught her looking up at me.

"Cum in my mouth," her eyes pleaded with me. I raised one eyebrow, questioning if she was ready. She nodded yes and moaned without taking her lips off my cock, and began pumping my shaft with her hands and ferociously licking that one amazing spot right on the underside of the tip.

I came buckets. The intensity of it all jarred me from the semi-conscious state she had put me in. I stamped the ground with my left foot and smacked down hard on the right arm rest with an open palm as my left hand squeezed the roots of her hair. My balls contracted with a force heretofore unrealized, and I'm quite convinced that if loving Jessica's mouth hadn't been so appropriately positioned I may have hit the wall 12 feet away. Wave after wave left me, and she eventually was overwhelmed as cum began to leak out of her mouth and run down her chin.

Eventually I ran dry and melted into the chair. Still blinded by the dark, I was confused by the slurping sounds I heard coming from the floor.

We made it to the bed, I think, and passed out. The next day we beat a hasty exit from Mike's place.

[...Flash forward to just this past week]

So dear readers, you can see why I was excited about this year's party. For the past year, I couldn't recreate the magic from that one special night. Not that I didn't try, mind you, it just seemed like Jess never again got into that kind of mood again. We still had plenty of sex, and were generally doing well, but nothing in the bedroom was so earth shattering as to warrant a few hundred words of description. We tried anal once, but as you know, that nonsense never works half as well in real life as it does in the movies.

I'm digressing, my apologies.

APPARENTLY I wasn't the only one who had fond memories of Jess's antics that evening. My heart dropped when I read this year's invite and noticed the added clause that dashed my hopes of recreating our adventure:

"Due to last year's unfairness, absolutely no sexy Jessicas will be allowed to participate in the costume contest this year. -Your host, Mike"

I showed it to Jess, and gave a shrug.

"I guess we won't win this year," I quipped.

She read the note for a moment and then had one of those evil-looking smiles cross her face. Fuck if she wasn't famous for those smiles.

"I've got an idea."

[Lets flash forward some more, to basically the present moment]

So that's the back story of how I came to find myself standing outside Mike's apartment, listening to the bass thump on the other side of his door. I was petrified over how the night might go.

I was scared, of course, because of our costumes. Jess looked tame--no make up on, wearing my slightly oversized business clothes with her hair up in a bun. I on the other hand, was dressed up, garment-for-garment, in Jess's schoolgirl costume from the previous year.

It was...odd. The clothes pressed on my body in all the wrong ways. Tight in the seat, graspy around my chest, and doing nothing to cover my legs and midriff. Plus I was extremely conscious of my lack of leg, chest, face, and armpit hair. (But where'd all the hair go? You'd be surprised how convincing a woman can be when she's got her hand on your cock. Lesson one for negotiations with a hostile party, fellas: choose your setting wisely).

Jess had spared no effort on the accessory front either--she had my shaggy-ish hair styled as girly as possible, and spent over an hour doing my makeup. Walking out of our apartment I caught myself in the mirror. I wasn't going to fool anyone in daylight, but was struck by the thought that I looked "hot."


The door at the party swung open. Mike, who was half in the bag, stared at me for a moment with confusion. Then a second moment with understanding. Then a third moment with a...different kind of look. This was strange as hell. As a straight guy who had never even thought about other men in my entire life, this last kind of look was unnerving. I knew what Mike was thinking (to the extent that thoughts were being successfully formulated in his head), and it sent a shiver up my spine.

"Hi Mike!" said Jess, breaking the silence. This decidedly feminine voice coming from the "man" of the pair shook Mike enough to realize precisely what he was looking at.

"Oh hey Jess. I guess you really took my suggestion literally."

"Yes I did," said Jess, "But I still think we have a shot at winning."

Mike turned back to me.

"Maybe you do."


The party swirled on with usual debauchery. Dancing, drinking, bullshitting, joking, the usual stuff you get at one of these deals. I began to notice the reactions of the guys in the room to my costume. Most thought it was hilarious, and generally didn't make a second comment except maybe a joke or two about me acting girly. A bunch gave me a dirty look and let me know that they wouldn't be caught dead in a get-up like that. And the last few looked at me in the different sort of way in which Mike stared at me when we arrived.

Then there was Mike himself. I know I wasn't being paranoid, but I increasingly saw him staring at me over the course of the night. Once or twice, as he brushed passed me in the hallway, I felt his hand linger on my hip, or the inside of my elbow. It was always just enough to make me notice, but never enough for me to react, if that makes any sense.

And, strangely, I noticed Mike back. He was taller than me, by 3-4 inches. Not surprisingly he also was slightly more defined than me. He was supposed to be "James Bond," but he was basically just dressed in a decent suit. I thought to myself that he looked well put together generally, and that I should try and figure out how to look like that when I had to wear suits.

Then things got interesting.

I was behind the bar, fixing myself a drink. Mike saddled up next to me, and as was quickly becoming pattern, came maybe slightly closer than I thought he should have. Because I was pretty far into my cups at this point, I fumbled some ice onto the floor. While momentarily bent over to retrieve the errant cubes, I felt a quick smack on my panty-covered ass.

I snapped back up as quick as I could, and looked around the room, mortified.

No one had seen.

I turned to Mike "What the fuck was that?!"

"You were a bad girl," He replied, coolly. The words 'bad girl' seethed out of his lips and triggered a memory for me from some time in the past.

"Fuck you." I retorted, somewhat meekly.

"Relax, I'm just kidding around." shot back Mike, with an expression that indicated he was clearly not just kidding around.

I stalked off to the bathroom and locked the door. I stared at the mirror as my mind raced.

What the hell had just happened?

How had things escalated like that?

Was Mike actually hitting on me?

Why in the HELL was my own hairless cock half-hard in my panties?!

I resolved, of course, to find Jessica and get the fuck out of Dodge.

I was thwarted, of course, when I found Jessica passed out in what up to that point was my favorite guest room in the world. She was laying on top of the mattress without any sheets or a blanket.

I sat in the famous chair of amazingness and thought about how far things had fallen off this year. It was quite a step down from last year--not only was I not about to receive the world's best blowjob version 2.0, but I was stuck without linens heading for a pathetic drunk girlfriend cuddling session.

I sipped my drink and tried to relax.

Sitting back in the chair, I became present suddenly to the feeling of my hairless legs as they rubbed against each other. It was...nice. Alone for the first time since putting on my costume, I tried crossing my legs like a girl. I noticed that this pulled the skirt back a bit, and showed off a good portion of my thigh. Having never worn such revealing clothes, I found myself noticing the air as it moved across my legs and stomach.

I took a deep breath. I closed my eyes. I sipped my drink again.

The anger I had been feeling melted away. I felt calm. Happy. It was a goddamned good drink.

It was weird, I could still feel my ass tingling in the spot where Mike had slapped me. For no reason at all, I thought of what it would be like as a girl in a porn movie. In an outfit not unlike what I was wearing, bent over some convenient object with my ass pointed towards the sky. The word "submission" streaked through my brain, and I felt my cock hardening again. This time around, I didn't fight it right away, but rubbed my crotch through the panties. The feeling was electric. My lips parted and I inhaled sharply.

Whoa. That jolt shook me loose, and I realized my drink was empty and I needed pillows and that jerking off in the guest room would solve precisely none of my current problems.

I headed back out into the "party," though by this point it had died down. In the living room, the music was low, and some light conversation was happening. I swung by the bar and casually asked if anyone needed anything.

"I'll have a beer, honey" Mike called out. The other two conscious people in the room chuckled. I shot Mike a look that said "cut it out" and he shot me one back that said "make me."

As I walked over with drinks in tow, and asked Mike about the pillows and blankets.

"I'll show you those in a minute, just have your drink with us first."

Realizing I had no choice, I resigned myself to his terms. I assessed the seating situation: There were two random people in the only two chairs in the room, one passed out guy occupying the entire couch, and Mike suggestively off to one side of the love seat.


I slid in next to Mike, and a moment later noticed with some alarm that I had automatically crossed my legs "like a lady" as I had practiced in the bedroom.

The conversation was dull. I politely smiled and chuckled, hoping to get through it, get my pillows, and get to bed. The music played low in the background, matching the lighting and the energy of the room.

Mike's knee touched mine. I noticed it dreamily, but didn't pull away.

The conversation turned to sex. The two guys didn't add much, but Mike had something interesting to say that stuck with me.

"The key to it all, of course, is crossing threshholds," started Mike, "You have to find out what that next thing is that the girl wants to do, but hasn't figured it out herself to actually ask for it. For me, the hottest thing is being in control...pushing the girl across that next threshhold--maybe its a kink she didn't even know she had. But pushing her to enjoy, hedonistically, something she never would have considered previously. That's what gets me going."

With that, his knee gave slight pressure into my leg. I let it sit there.

Suddenly, random guy #1 turned to random guy #2, and showed a text message on his phone. Guy #2 said "Oh shit!" and they both ran out together.

"Deus ex SMS" joked Mike.

I chuckled.

We were alone in the room on the love seat with his leg touching mine.

We sat a long, long moment in silence.

"You know how this ends, right?" Mike asked. Breaking the lull.

I shook my head no.

Mike Sighed.

"Just relax," he said. I relaxed.

He put his hand on my thigh. I unrelaxed.

I looked at him, my mind racing with the fear and confusion that was probably written in my eyes.

"Close your eyes." he said. A beat passed, and I closed them.

"Good girl." He said. "Now here's what I want you to do. I want you to turn your mind off, and let your body drive for a little while." His hand began to very, very slowly slide up my leg. "There's a lot going on upstairs, in your confused, silly head."

He was right.

"I want you to let that go for a minute, and just relax." His hand rolled over and reversed course, and the backside of his fingers began a slow journey down my leg. My mind was numb, but the only thing I knew for sure was that my cock was just about as hard as it had ever been.

"You were a bad girl tonight." He said in a low voice. It was stated so simply--with such conviction. It stuck in my head. I swallowed hard once.

"I was a bad girl tonight," I whispered. Who's voice was that? Why had I said that?

He removed his hand from my thigh. For a moment, I was untouched, and free, and could run for it.

Then he stroked my hair. A light stroke, starting in front of my ear, pushing a lock back, continuing down onto my neck. My head craned towards the caress, and I let out of a soft coo.

"That's right. No need to be scared here. Just go with what feels right."

"I've been a bad girl..." I squeaked. My cock was rock hard in my panties, and I had to adjust. He had thrown me off balance. I reached out with my right hand and grabbed the arm rest. I reached out with my left hand and grabbed....his leg.

"Why don't you see what you can find?" My mind was lost now. My legs were spread apart to give my desperate cock room to breath. I reached my hand up his leg and found what I didn't know I was looking for.

Through his pants I could feel it. Hard. Long.

He moaned. I moaned.

"What do bad girls do?" He asked. His hand caressed my cheek. It slid down and off my face so that just his index finger was on my ruby red lips. They parted and his finger pulled down my lower lip.

My eyes opened. I looked at him. He was in control of the situation, he had the power. I had given it to him.

I wanted him to keep going.

His hand came to the nape of my neck and curled around. With the slightest pressure he steered me. One fluid motion, my hand never leaving his bulge as he persuaded me off the couch and onto the floor in front of him.

In my heels I sank to my knees. From here I looked up at the world, I looked up at him.

Without prompting, I unzipped his pants and boxers and slid it all down and off his ankles.

My hands rested on his naked knees, I sat there, trying to wrap my mind around what was happening.

"Here" he said. He took his hand in mine, and placed it on his cock. It was beautiful. Long, hard, veiny, a bulbous head. You've seen them in porn.

But you haven't been up close. It was warm--hot to the touch. It smelled, strongly. "It smells like a dick," was the odd thought to run across my mind.

"Say it." He said. Again, he was simple, no nonsense.

"I've been a bad girl." I intoned, in a voice that hazarded dangerously close to sultry.

"And what do bad girls do?" He asked, pulling me back the back of my head in closer....closer.

I gobbled up his cock. It felt at home in my mouth. I went to work--bobbing up and down as fast as I could. But I was too new. I tuckered myself out. For a breather, I rested with just the head in my mouth, teasing him with my tongue.

"Enjoy this. You're mine tonight, and I will get off knowing that you're loving this, like the slut that you are." My eyes opened and looked up at him as he was saying this. "Take your time. Touch yourself too."

I stared at him for a moment longer, hardly moving. This perfect situation, me on my knees, his cock in my mouth, staring at each other. I slowly reached down to my own dick, and rubbed it through my panties. Letting out a girlish moan, I began to explore.

I don't know how long I was down there. I remember licking his testicles, sucking one and then both into my mouth. I remember my eye makeup running and seeing lipstick smears on his shaft. I remember the feeling of absolute bliss as I worked him over.

I started a long, slow, building motion with my mouth and throat. Slow and shallow, heading towards fast and deep. He grasped my hair by the root, and I could feel his balls tightening with my hand. I was rubbing myself furiously.

I looked up at him. My eyes screamed at him: "Please cum in my mouth."

He stared down at me "Drink it all" he grunted, and exploded into me.

I swallowed as quickly as I could, and got the first few bursts down. He continued grunting and holding me by my hair. There was too much. I lost his cock from my lips, as he continued bursting and covered my face, splurting on my nose and cheek. My own cock exploded in my panties.

Report Story

byjamie23232© 14 comments/ 27463 views/ 21 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: