We Have to Win!

byCharlieGG©

At some point (time is a blur, seriously, no idea) I went to the bar on my own to get another drink. Donna and her friend Jenna had bounced off somewhere to chat with a group of women and Roger, Dan and a number of other friends had retreated outdoors to smoke a cigar. I promised to join them as soon as I got another drink and there were "we could use some hot female companionship!" jokes all around as they laughed their way to the patio.

"Looking good, babe!" the bartender winked at me, continuing our rapport since we arrived.

"I don't know where you got the balls to do it," he laughed when I first introduced myself. "But I give you credit!"

Now, as he slid down the bar to grab the gin for my martini, a guy in his mid 20s sidled up next to me.

"You DO look gooood," he echoed and I could see the blur in his eyes and the swaying in his stance that gave away his a a-bit-too-high alcohol levels.

His arm crept around my waist and his hand fell on my opposite hip, just above my panty-covered ass. His fingers traced the faint line of the lace under my dress as he babbled on.

"Yur huzban' is a lucky man!" he slurred and then patted my ass.

Okay, what the hell was going on? My brain whirled, even in it's drunken state. I whipped my eyes around, thoroughly expecting to see Roger and company in the corner laughing as they watched. But instead I saw various people at tables, talking, seemingly oblivious to the ridiculous scene going on at the bar.

"He's cute, go for it!" the bartender whispered to me and gave me a tongue-out wink as he slid my drink in front of me.

"Where's your wife, baby?" I cooed, certain that at the sound of my voice he'd sober up in a hurry and scuttle away.

"Not feeling so good, went up to the room," he explained giving my ass a squeeze. "You have a room?"

"I... um... " I stammered, not ready for this game to continue.

"I'm sure we could find someplace to disappear to," he offered.

"Well, you see... " I smiled, letting my voice drop a bit lower...

But before I could figure out how to let my drunken friend down easy, my wife was by my side.

"Well there you are, Marilyn," she smiled with a look that said 'oh my God awesome!' and grabbed my hand. "We were wondering where you got off to!"

"She's such a little whore," Donna whispered to the crestfallen guy whose hand had slid away from my butt. "I swear I have to keep a constant eye on her!"

And with that, Donna pulled me away with a laugh.

"Holy shit, that guy was totally hitting on me!" I laughed with her

"I know I was WATCHING!" she said with a bounce. "You're lucky, half of me wanted to let it go on!"

"You're evil," I shook my head.

"Oh just wait!" She agreed, slapping me on the ass.

------------------------------

"... And I think we all know where this is heading!" Joanna Johnson said with a flourish.

She was announcing the winner of the costume contest and, yes, I knew exactly where it was heading. In the time (half-hour? hour? two hours?) since it happened, the bar incident spread like wildfire (with Donna fanning the flames more than anyone) and I legitimately felt bad for my 20-something would-be fling and the abuse he was going to catch the next day from friends. The result was, if we weren't already in the lead, we were now a virtual lock to take home the coveted costume prize.

"The winner of this year's best couples costume is... Joltin' Joe and Marilyn Monroe! Donna and Charlie!"

The place went wild. Cat calls and vulgur shouts filled the room as I strutted my way to the front of the room, Donna in tow. When we got up there, Joanna gave us both big hugs, making a big production out of grabbing my ass in front of everyone. I sure had a popular rear-end!

I blew kisses and Donna dipped me to give me a big kiss as the applause grew louder. Our friends gathered around us to laugh and Dan came through with a tray of full shot glasses.

"To the couple with the hottest gal we know!" He announced, once everyone had a shot in hand. "And Donna ain't bad either!"

"Cheers!" everyone chimed in and down went the shots. Because any of us needed more alcohol at that point.

-----------------------------------------

"Let's get out of here," Donna grabbed my hand several minutes later, pulling me towards the lobby and the bank of elevators.

"But how will the party go on without their beloved Marilyn?" I argued playfully, feeling my words slurring thanks to the night full of drinks.

"Who cares," Donna chided, her tie loosened and button down shirt falling open to reveal her cleavage, straining against the bundling she had done to contribute to her look. "I want to party with you alone!"

We got into the elevator and Donna pushed me against the wall as the doors closed.

"You are one attractive girl," she smiled at me, running her her hand gently over my face in her best impression of a wooing guy. "Want to come up to my room, baby?"

"I don't know if I should," I responded to the roleplay, batting my eyes. "I'm not really that kind of girl..."

"Oh," Donna licked her lips, sliding her hand down my side and pulled my hips to hers. "You will be..."

------------

It took Donna a couple of times to get the room keycard to work (and for the first time I realized she had left sober a long time ago) but when she did, she took my hand and walked me slowly into the room.

"Stay here, I'll be right back, I want to undress you..." She said lustily, giving me a look I'm not sure I had ever seen before. "Just give me one minute."

I walked over the window and looked out on the city below. I caught my reflection in the window and reached slowly under my dress and tweaked my nipple. I was sexy!

Donna came up moments later and wrapped her arms around me from behind and kissed my neck.

"I'm so fucking turned on," she whispered, into my ear and then let her tongue dart into it.

Her hands roamed my front, cupping my gel-supplied breasts.

"When that guy was hitting on you, I thought I was going to have to touch myself right there..." she breathed into my ear again.

"Really?" I asked, and was somewhat surprised to feel my already aching cock skip a beat.

"Oh my god yes," she exhaled and then turned me to face her. "Okay, Charlie, quick time out. I want to take control here and I don't know how comfortable you're going to be with this, well, this roleplay. If you ever get uncomfortable just say so, okay?"

I nodded, looking her in the eyes. She smiled.

"Get on your knees Marilyn..." she commanded softly.

I did as she asked, noticing that she was still wearing the slacks and button-down shirt.

With my face at waist level, she reached down and unzipped her pants. When she pushed them to the floor, I was face-to-face with a rather large dildo, strapped on to her body.

I have no idea what the look on my face must have been when I looked up at her, but she quickly continued.

"I wanted to see you with that guy at the bar so bad," Donna shook her head. "He was looking at you with such lust and you looked so beautiful... "

Her hand went down to pet my blonde wig and then she gently put her fingers on the back of my head.

"Suck my cock, Marilyn," she practically pleaded, pulling my lips towards her strap-on.

With little thought I took the hard dildo into my mouth, sucking on the tip before letting her slide it deeper into my mouth.

"Oh yes, THAT'S what I wanted to see," her breath getting heavier.

I looked up to see her hands sliding up her own body, invading her top and squeezing her breasts.

"Oh my God, fuck this," she said, in a frantic needy tone and pulled my mouth off the dildo. "I have to have you..."

We stumbled over the bed and fell on top of the mattress, my hands pushing her shirt off as she tore the strap-on from her body and chucked it across the room. With Donna suddenly naked, she reached to my dress and pulled it upwards to my waist, seeing for the first time the peach lace panties, my hard cock straining against the material.

"Fuck me that's so hot!" she moaned. "And I'm sooooo confused right now!"

We both laughed, the absurdity of the situation crashing over both of us.

"Let me get you out of those panties!" She giggled and slide them slowly down my legs. When she had peeled them off, she gathered them in her hand and stroked my rock-hard cock with them slowly.

"Don't panties feel fantastic?" she teased, looking up at me.

"They sure do right now!" I agreed, and then let out a moan as she lowered her lips to take my cock into her mouth, the lace panties still rubbing down my shaft.

"Oh god... yesss..." I threw my head back, an entire night's worth of pent up arousal finally being satisfied.

She bobbed her up and down, finally tossing the panties to the floor and taking my length entirely between her lips. I moaned and started to pull the dress up further, desperate to finally be out of the get-up.

"No! Don't!" she grabbed my hands. Without another word she rolled off the bed and grabbed my hand. "Come on..."

She led me to the vanity area. Only the light from the window in the bedroom provided some illumination, casting an uneven pale over the bathroom area.

"I want to get fucked by Marilyn Monroe," my wife smiled.

She turned away from me and bent over the vanity, her breasts pressing against the counter.

And as we both looked in the mirror, the tall blonde actress (actor?) in the white dress with perky boobs entered Donna from behind.

"Ohhhhhhhhhhh" she growled as my cock pushed inside her, her eyes not leaving the image in the mirror. "Fuck me Ms. Monroe. Fuck me hard!"

I moved in and out of her, slowly at first and then with more intensity. Her breasts bounced as she pushed her way up onto her hands, slamming herself back to meet my cock in full thrust.

"Uuuunnnnngggghhhhhhh" came the gutteral moan from my wife as I filled her insides.

After a minute or so, she had me pull out and pushed me to the floor. Without another word, she straddled me and lowered herself down on top, bucking her hips.

"Holy shit, holy shit, holy shit," she repeated as her hips ground into me.

She lowered her mouth to mine and our lips and tongues met. We made out frantically as she pulled the straps of my dress downward, pushing the gel-inserts away to the floor. Soon the dress, both top and bottom, was bunched at my waist and her breasts were pressing into my chest.

"God you're amazing," I whispered into her ear as shivers ran up and down my spine.

"I want you to fuck me forever," she responded, bouncing more feverishly on my cock.

I rolled her over and spread her legs further and began pistoning in and out of her now soaked pussy. The red rash that often accompanied her orgasm spread across her body, noticeable even in the pale light, and she let out a long, loud moan as her legs tensed around me. Seconds later, my own orgasm enveloped me and I poured out inside her, finally collapsing on top of her sweaty body.

"Fuck..." she managed, after a good 30 seconds. "We need to cross-dress more often!"

I snorted out a laugh that caused her to break into her own giggles while I rolled to her side.

"So, how long have you had strap-on, you perv?" I chided her.

"Ha ha, I bought it when I bought your wig, you sexy cocksucker," she poked back.

"Huh," I acknowledged.

"That was okay, right?" she questioned, one of those classic post-coital wonderings. "I actually bought it as a joke but then that guy was hitting on you and I pictured... Well... and it was hot... so... It was okay, right?"

I leaned over and gave her a long slow kiss.

"Of course it was okay," I smiled. "Anytime you want to explore something, you know I'm here for you. I mean, I just dressed up as a sexy, leggy, busty blonde in front of all our friends for you, so..."

Donna laughed that great laugh again.

"And you know what?" She said, looking at me with that goofy look that started this whole adventure. "We fucking WON!"

I laughed.

"We sure did. We sure fucking did."

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byCharlieGG© 22 comments/ 62288 views/ 8 favorites

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by Anonymous

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by beliabelle09/07/14

loved it.

Really an awesome story! Was wondering where it was was gonna go with the cross dressing! Loved the theme and the over all humor of the story! Really, a good read. xo.

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