New Year's Eve Oops!

I was getting ready to go out to a New Year's Eve party with some of my closest friends, and it was to be costume party, which I was excited for, but didn't have a clue as to what I would dress up in.

But, as we sat around the table, having some wine, wonderful Michelle, my good friend Pete's beautiful wife, suggested I try something "off the hook" as she put it, and threw out an idea that later that night would change my whole perspective on myself.

Now, Michelle had some dirt on me, you could say; dirt that not even Pete, or any of my other friends knew about.

A FEW MONTHS BACK: Around Halloween, after I had broken up with my girlfriend Carol after disagreeing the stupidest shit that we just couldn't put up with each other anymore. Long story short, she moved out of my place, but left a bunch of her things; her dresses, skirts, nylons, lingerie, some heels and make-up.

Ironically, Carol and I were of similar size and build; both 5'7, around 150 lbs., practically the same shoe size, as I had rather small feet for a man, and so -- I got a little curious.

I got drunk one night, and after about an hour I found myself walking around my place in her gartered stockings and heels. She had a corset that clasped on the front and cinched my waist. I was wearing her lacy black thong and halter style brassiere that matched that thong and the garter belt and the black stockings.

I surprised myself that I could walk in the tall heels that she had left behind. The buckled around the ankle with a tiny little strap and they black and shiny and when I strolled through my place, I felt my hips adjust and find their fluidity and soon a strutted like a natural.

I was having this cathartic moment, and I was loving it.

I could feel my cock stretching out her panties, and I was just in this sexy mood, really giving myself to this new high I felt, so profoundly lost, that I didn't even hear the front door of my place open.

"Oh... my... God...," I heard the woman's voice breathe each word as if in slow motion.

I stopped, caught like a mouse gets caught by the cat. I peered over my shoulder, and saw Michelle, my best friend Pete's girlfriend, standing in the archway that led into the living with a bottle of wine with a bow on it, just staring at me, dumbfounded, nonplussed, her face a cock of, "What the fuck am I looking at, and who the hell is this?"

"Michelle!" I hollered, feeling now so utterly exposed, trying to hide myself, but that didn't help at all, if anything it only advanced the caught girl look I presently exuded.

I wanted to run, but where? I was already home, and plus I didn't think I would get that far in these heels.

But then Michelle gave me this strange yet understanding smirk. She set the bottle of wine down on a side table, and before she left, she turned back to me and said, "You look really sexy, James. I mean it. Really sexy. Didn't know you had such... feminine qualities."

And then she left.

What she didn't leave with was the knowledge that this wasn't the first, nor the last time that I had begun to experiment a little here, and there...

NOW: back to the beginning of the story.

Michelle had this dirt on me, yes, but she never weaponized it, but I know if she wanted to, she could have. And I knew she never told any of our friends about it, because knowing them they would have brought it up by now.

So, when around the table the question of what costume I should wear arose, I knew where Michelle was going to go with it.

"Maybe," Michelle said. "You just fool everyone tonight, and dress like a woman. No one would ever know, and you got the body for it, James. And I could help." She smiled directly at me with knowing, conspiratorial eyes, and I felt my face beginning to flush red.

"Oh yeah!" Pete chimed in. "That'd be hilarious. You should totally do that. And Michelle, ya know, she works in the beauty department at Macy's. She could make you the belle of the ball," he laughed.

"I don't think I want to do that," I said, feeling Michelle eyeing me now. She knew I would give in a matter of minutes if she put the pressure on me. It felt like blackmail, but when she shrugged her shoulders and let it go, I was surprised.

"Okay," she said. "Just thought that might be a bit of fun to bring in the new year, but you're right. It's a little over the top." She smiled at me as she sipped her beer; I knew what she was up to. She hadn't dropped it at all.

"Shit, I'll do it," Pete said, all excited, uncorking another a bottle of wine.

"Pete," Michelle chuckled, cocking a motherly eye of "be serious" to her man

"What? I could pull it off, and the fact that it would be obvious I was a man would make it that more hilarious, right James?"

"Yeah, that's true. You should do it," I laughed. "That would be funny."

"Hey," Pete excited, a sudden burst of enlightenment. "Let's both do it," he said, as if this bright idea suddenly popped up in his head.

I smelt collusion.

"No, I don't think so," I said. "I have an old zoot suit costume from Halloween. I'll just wear that. That should be good enough to get drunk in."

But, a few glasses later that night I had myself convinced, and I told Michelle that I would indeed like it for her to dress me up like a woman.

Pete backed out, which I had a feeling he would, but that didn't bother me one bit at this point. It was I and only I that would be dressed as a woman that night.

I was beyond game. Shoot, I was excited, ecstatic, and thrilled.

In just an hour, Michelle had done my make-up, had me dressed in a classy emerald green satin dress that wasn't low cut, thank the Lord, paired with matching strappy heels, and black opera gloves. Real classy, I thought. And she accentuated the outfit with jewelry that were her own, and they adorned my wrists and my neckline, simple silver here, and there, plus little clip-on earrings which hung from lobes.

Michelle had done a marvelous job.

Lastly, and she had no need to fit a wig on. I had medium length hair as it was. She just gave it the little flair that it needed, some bangs, some curls, and rightly I looked like an old show girl, as if I slept with hot rollers in my hair all night long; she had the talent to make it so.

Then, she stood me up in front of a full-length mirror, knowing very well that I would have no difficulty balancing in the four-inch black satin pumps with little twinkling brooches on the toes, which she had chosen, also which just so happened to fit my feet more perfectly that of Carols.

Again, I smelt collusion.

But I liked it, embraced it, and felt grateful for it. Plus, I could tell that Michelle was having the time of her life dressing me up. She planned this, I thought; all that precision.

"Just like old times," Michelle whispered into my ear, grinning at me in the mirror.

I turned back in time to see her leaving the room, and I knew what she meant.

But still, I shrugged it off, and stood there by myself, gazing at the dark-haired beauty in the emerald dress in the mirror gazing right back at me, and I didn't see myself one bit.

I saw a woman, one that was gorgeous enough to be any man's date for any occasion, a beauty that tonight was ready to have her evening out on the town.

"Her?" Was I already in character?

As we drove to the party, which was a little further uptown than I'm used to going, I sat in the back and secretly enjoyed something that was hidden beneath my dress and up my bum...

SIDE BAR: Since Carol had left me, I had begun to explore another side of my sexuality that I believe had lied dormant throughout our years together. Something I didn't explore, but I knew existed. Throughout our time I had just resisted the temptation of it all because of the person I was with. And because I was no longer with that person, I didn't have to worry about any judgment whatsoever.

BACK TO STORY: So! Discreetly, when I was in the bathroom slipping into my lingerie, adjusting my brassiere, lining up the seams of my semi-nude toned stockings, making sure the garters were fastened to the welts efficiently, I did something...

I slid a plug, about the size of a large strawberry, up my bum, all the way up until the bejeweled stopper was snugly pinched between my cheeks, then I pulled up my matching lace thong, nice and tight, the straps over my hips, and the stepped out of the bathroom and sat in the chair where Michelle waited for me to begin my make-up.

Sneaky right!

SO: Now, presently, in the back of the car, as we cruised to the party, I was starting to feel myself engorging slightly in the dress, but the fabric of the dress was so thick and my panties were so tight that my cock didn't even really have a chance of showing. And I knew the party was going to be poorly lit, and therefore the shadows along my lap would not betray me.

At least, that's what I thought.

We arrive at the party, and Pete, who could not stop smiling, or making little quips about how glamourous I looked, held out his hand to help me up the steps to the home we were about to enter.

"M'lady," he joked, grinning at Michelle, who wasn't laughing. "What?" he asked, a tad aghast.

"Leave her alone," she giggled. "She's in character right now, Pete."

"Her", once again "her". I heard this, and thought what lavishing feeling to be considered female. It sort of, eh, warmed me, made me want to make sure that I didn't disappoint Michelle that night. I noted then, that she was looking out for me, or at least the work that she'd done on me; she didn't want to me remind myself that I wasn't a woman. She is clever that way, I thought as straightened my posture, real poise like, let my legs do the talking as I took each stride forward, one heel in front of the other, careful yet firm, all the way up the stairs to the party.

"Okay fine, I'll leave her alone," Pete moaned. "But you gotta admit. She looks amazing."

I smiled at Pete, planted a kiss on his cheek, too deep into character I realized, but Pete didn't recoil in anyway, which warmed me, and in the daintiest of inflections that my voice could muster, I said to Pete, "Thank you."

Pete and Michelle did a double take, like holy shit.

She is in character.

Pete's costume, I noticed made me giggle on the inside, as it was exactly what I had suggested that I should wear for the party.

He wore a zoot suit, in comical yellow, with wide, high waisted trousers, classic, and with exaggerated sports coat shoulder pads, and with clean wingtips on his feet, as if he was about to star in a Warren Beatty film.

And Michelle, boy oh boy, she went all out; a really convincing Lara Croft get up, with the barely-there tan shorts, the blue tank tucked into a utility belt, boots, which had spiked heels, folded socks, and of course the iconic braid. She looked sexy.

As for me; I was dressed as a woman. That was it; a conceivable woman.

And when we three entered the party, it didn't feel like I was a wearing a costume compared to everyone else that was there. It just felt like I, this woman, had somehow wandered off from some gala, or fancy dinner party, and stumbled into this motley crew of randomly dressed people.

I stood out, and people noticed.

All of the eyes that were on me told me what I felt was true. But I liked it.

No one knew that I wasn't a woman, and the little secret I was holding within me tickled and plunged and pressed deeper with every step I took in those tall, tall heels.

I could feel my ass jiggle as I walked, and even though the fabric of the dress was thick enough to conceal my true nature, I was starting to doubt if I could hold myself back enough to not give myself away.

But I carried on, thought it best to relax myself, and take a seat at the bar and order a martini, as I figured a woman dressed as I was would most likely order a martini, I supposed.

But when I sat, good heavens, the plug pushed deeper, and as I shifted my weight in the high bar stool to shake off knowing it was there for the night, shoot - it only caused it to burrow deeper, and then deeper as shifted, until I realized, I'll just have to remain still.

Be a good girl, I told myself, with a giggle.

I crossed my legs to remain causal, feeling the hem of my dress revealing just a little bit more thigh, but not to the point where my stockings would reveal, just a little ride up I told myself. Just a little ride up never hurt.

The martini came, and I sipped it, and it was delicious.

I looked over each shoulder to see where Pete and Michelle had scampered off to, but they were nowhere to be found. Mingling, I supposed, and as I was enjoying myself, I thought to hell with them!

I'm a woman tonight, embrace it.

It took some nerve of me to come out here to a party like this, dressed like this, and not in the capacity of trying to fool anybody, but of trying to just... try it out, like an exercise, as if to ask myself can I really pull this off?

As I drank that sweet martini, a part of me really thought that I might actually get lucky. And if I did, if I was willing to indulge, which, clearly, I was prepping my bum for, would the one that chose me really still be interested when they discovered a little sissy boy like me?

That scared me.

But as I ordered my third martini, the prospect of being scared began to frighten me less, and less, and less.

I felt myself loosening up, letting the skirt ride up so to speak.

SIDE BAR: I laugh now as I write this, but it's that feeling I had, like an anxious yet excited feeling that I had that night at the party.

CUT TO: And then a stranger entered the scene. Remarkably handsome, good, stylish fitting suit, very tall; towered over my 5'7, and with a tan, but not too tan, and he was wearing a Kato mask like Bruce Lee from the Green Hornet, with the driver's cap, and everything.

He sat next to me.

He was ever so close, I thought, and I was right next to him all proud in my emerald green dress and the heels that I wore, with my stockings beneath, and my little friend getting more than acquainted inside of me.

The man turned to me, and he said, "So, who are you dressed up as?"

I didn't have an answer, because this wasn't a costume per se. So, I came up with something on the fly.

I said, in my best girly voice, as not to betray myself, "I'm the stand in for Jessica Rabbit. Turns out she need someone who was alive to make her next move."

The man laughed.

"That's a good line," he smiled.

"Thank you."

"Can I buy you a drink?"

"Isn't it an open bar?"

"It is," he smiled. "That was my joke."

I started to laugh, because yeah, he got me there. He felt warm to me, impeccably charming, and unassuming, and unnaturally sweet, I thought. It was disarming, as I was on the defense, still worried about how I would be perceived if I were discovered.

But that smile was devastating.

"Yes, thank you," I managed, finally. "But I'm having martinis, is that alright with you?"

He twirled to me his empty martini glass.

"That's all I've been having," he smiled. "I'm Malcom," he said, holding out a firm looking hand.

I took it, limply, and shook. "I'm Jame-" but, then I stop, as I realized that I never thought of name for my female form. Quickly, I added, - "ee. Jaimee," I stated. "Nice to meet you Malcom, and thank you for the drink."

"Pleasure to meet, Jaimee." Again, that charming smile, that could change you in an instant, make you want to do things you never dared to do, began once again it's corruption of me.

"Happy to oblige."

He turned to the bartender, and as he ordered another round, I looked down at his trousers, and the light of the party did not betray the bulge this man Malcom carried beneath.

It was as if he, no matter where walked, went, or slept, there would be a pet snake between his thighs.

The contours were baffling. I kept peeking, and I began to question whether or not if I could actually engage with such an anaconda-like entanglement.

This man, as I was currently imagining, would drive the breath right out of me.

"You know," he said, leaning in close. "I know this isn't a costume."

"Not hard to tell, is it?" I blushed. "My friends dared me, and I went for it."

"Dared you to do what?"

He really looked flummoxed.

"You mean you can't tell?" I asked, slightly amused, impressed with myself, feeling a cunning little grin on my face grow, as if I just bested the best of the best handsome men I'd seen in the place.

"Tell what?" He curiously questered on.

"Here," I said, feeling all the martini's inside of me coercing my honesty.

I did not want to fool this man. He seemed already fooled. No need to carry on the charade. No more salt in the wound, I thought.

I took his hand in my soft velvet gloved fingers, and guided him to my lap.

"This," I said.

And then, Malcom felt my bulge, but he didn't give me a look, no repulsiveness, di throw me now shame. He didn't shy away from it. In fact, he lingered, beholding even; and began to explore the contours withheld beneath my emerald dress, astonished he was as his hand remained, feeling, exploring, even after I pulled my gloved hand away. And then Malcom allowed his hand to rest as he registered the gravity of which I had spoken earlier.

The man was bewitched. He gazed up at me, and said:

"You decided to look this beautiful on a dare?"

I had no response.

All I could feel was his mighty big hands still holding, and caressing me through the emerald dress.

"Yes," finally, I breathed.

"Here," he said. "Feel mine."

Malcom took my hand and laid down over that monster inside of that cave of trousers, and let me feel his cock first hand. It was thick, long, and I knew by the thirst in his eyes as he watched me grip it through his pants that it was going to be a juicy one, too.

"I have a room upstairs," he said.

And that was all I needed to hear.

Malcom paid the bill, took me by my gloved hand, and led me skipping on my heels outside, and we only had to make a simple turn back into the building because the reception hall for the party was ground floor, and separate from the hotel suite upstairs that he led me to.

We rode the elevator, kissing, fondling, aggravating this lust we had for each other at the moment, anticipating, yet knowing what was to come.

In Malcom's suite, which was undeniably lavish, and well thought out, we began something that like I said in the beginning of this tale, due to my friends, Michelle, and Pete, who I think I now know understood who I was becoming and like good friends embraced it, that would become something remarkable.

I unfastened his belt as he unzipped the back of my dress, all the while kissing my neck and shoulders, branching down to my chest as the dress slid off and down my lithe frame, dropping to the floor until I stood completely exposed to him.

No shyness from either of us.

He unclasped my stockings, noting that my bulge was now free to push against my panties, and so near his face.

He slid the stockings off gently; intimately.

He left my jewelry on.

Half naked now in just my thong and brassiere, I got down on my knees and prepared myself mentally for the python that lurked as I pulled his trousers down, and suddenly, just like that, it was right there; staring point blank at my gaped mouth.

No hesitation.

I swallowed that behemoth the best I could, and kept gurgling, and squirming, and swallowing and sucking until I heard the sounds that I craved to hear from a man who in the thralls of insatiable pleasure.

The damn thing got so thick in my mouth as it grew that it nearly got stuck in my throat, and I almost suffocated to get my breath back, but Malcom sensed this.

He yanked himself off, disregarding my teeth scraping, and then at once picked me up like a little toy, dropped me on the bed.