Coworker Transformation

"I just want to feel you," she breathed. "Please, I just need to feel you inside me. It's our last chance. I want you to show me what you know."

We were just inside her hotel room. The door had barely closed behind us and her hands were fumbling at my belt, while I kissed her deeply between her words. It was late and we had been drinking for a while in the hotel bar. I could taste the cosmopolitans on her lips as they met mine and her tongue as it slid into my mouth.

When we got to the room, I had been dressed in a suit, but my jacket was now crumpled on the floor. My tie was next to it and my shirt was untucked and partially unbuttoned. Her skirt was hiked over her hips and my hands were on her ass, pulling her as close to me as I could. Her blouse was already partially unbuttoned and I could see the silky, lacy white bra underneath.

I knew this was wrong, but I didn't care. This was something I had wanted for a long time.

It had been several months since my breakup with Laura. I'd had sex with a couple of women since then, but I had been attracted to Melissa for years. I had dreamed of this moment.

At just about 5' 2", she was not tall by any standard, but her body was well proportioned. She had pale skin, the kind that burned after almost any sun exposure, and freckles on her nose and shoulders. Her eyes were a deep green and her hair was a simple reddish-brown shoulder length that she sometimes pulled back in a ponytail. She had a narrow waist and curvy hips, and her breasts were small and perky. A former tennis player, she was still pretty athletic, though perhaps not as muscular as she had been in college. Her smile was quick and genuine, and it lit up her eyes.

Melissa and I worked in the same department at a non-profit organization. One of our team of six's main duties was planning and executing the organization's annual week-long member conference, which was (at the time) the largest of its kind in our region of the country.

This was not a small task. It took a full year of planning, including a lot of late nights. As a result, my team became very close. When you spend that much time on a common goal, you're almost guaranteed to either adore or despise each other. Luckily, we all got along well and became genuine friends. None of us had kids at that point, so we hung out together a lot outside of work, as well. Despite the work, it was a fun time.

Melissa was engaged to a man she met in college. He was a very good guy and would later become very successful in his chosen career. She loved him very much. However, he was also the only man she had ever been with sexually. Before college, she was a virgin, never having given so much as a hand job. In more than one drunken late-night conversation, she had confessed that he was boring in bed and that she regretted not having more sexual experiences before settling down.

This particular year, in addition to helping plan our annual conference, she was also planning her wedding, which was scheduled for just three weeks after the close of our conference in January. The stress of planning both events was considerable and there had been times this year when many of us thought she might actually crack under the pressure.

Melissa and I had always been flirty and it intensified considerably when we had been drinking. When drunk, she would sometimes sit in my lap and tell me how much she loved me or wonder aloud why some lucky girl hadn't snatched me up. She always had her arms around me or would lay her head on my shoulder and snuggle in. This was considerably different than her sober demeanor. Under normal circumstances, she was quite reserved and was not physically affectionate at all.

One of our big traditions at the annual conference was that, on the last night of the conference, those of us who planned it would go out together to one of the hotel bars and, for lack of a better term, get really shitty. The conference attendees would have all gone home and all that was left for the next morning was to pack our supplies and materials onto the truck and hit the road. So our night out was our way of blowing off the steam from the stress of planning such a huge and complicated event. It was also our reward for not killing our boss, who is to this day one of the worst people I've ever known.

Given the dual stresses of wedding AND conference planning, Melissa was really letting go. She consumed several cosmopolitans (a lot for her size) and she was in rare form. As the night rolled on, our teammates slowly drifted off to their rooms to sleep. Finally, as 2 a.m. approached, it was just Melissa and me left in the bar.

We were in a semi-hidden booth toward the back of the room. She had been extremely flirty all evening, grabbing my ass twice when I got up to go to the bathroom and even whispering to me with her hand on my thigh how good I looked in my suit.

With everyone gone, she was leaning against me, her feet up on the cushion, arm around my shoulder. From past talks, she knew that I had played around a bit before any serious relationships. She had begun asking me about sexual partners and whether I thought it was important for someone to have a lot of experience before they married.

She again confessed that sex with her fiancé was boring and unfulfilling. She was worried that it would be that way for the rest of her life.

Suddenly she looked at me intensely, eyes locked to mine.

"You've been with a lot of different women," she said with a devious grin. "What's the dirtiest thing you've done?"

Despite my obvious writing for this sub, I'm not usually one to kiss and tell, and I was hesitant to just blurt out some of the things I've done, especially to someone for whom a blow job with swallowing was "out there."

I laughed nervously.

"Well, that's kinda complicated," I said. "What's dirty to one person is pretty normal to another."

I grinned back at her.

"Why don't you ask me some specific things, and I'll tell you whether I've done it or not."

She blushed immediately.

"Oh ... well ... I don't ... I don't even know where to begin," she stammered and looked away.

"C'mon ... ask me," I prodded. "I promise I'll be honest. And I promise I won't judge you."

Picking up her martini glass, she brought it to her lips and drained the last swallow. Looking at me again, I could see her blushing even harder. But I could see something else in her eyes. She wanted to hear about it. She wanted to know what I had done. The blush wasn't just about embarrassment. She was a little turned on.

"Umm ... ok ... have you ever ... ummm ... have you ever done it ... outside?" Her eyes darted down as she asked.

"I have!," I replied. "A few times while camping, a couple of times at outside parties, and once, on the hood of a car on the side of a road after a Grateful Dead concert."

"ON THE ROAD?!?!," she gasped? "What if someone had seen you?"

"Well, I think that's kinda the fun of it," I laughed. "Part of you ... I dunno ... WANTS to get caught, you know? It's part of the thrill."

She leaned in closer, then. Her face just inches from mine.

"You're very dirty," she accused, seriously. Then she smiled. "Keep talking."

"If you think THAT'S dirty, you ain't seen nothing yet," I said, with a devilish grin. "Ask me another."

"Have you ever ... you know ... had a ... threesome?"

I laughed again.

"I have," I said, matter-of-factly. "In fact, as of this date, I've had four threesomes. Three with two women and one with a girl and her boyfriend."

"OH MY GOD!," she yelled, forcing the bartender to look in our direction with a disapproving glance. "YOU HAD SEX WITH A GUY?"

"No, no, no, " I replied, laughing at the look of astonishment on her face. "It was a girl I knew who wanted to have sex with me and her boyfriend at the same time. The guy and I never touched each other ..." I looked at her hesitantly before finishing my sentence. "... except when our legs were touching when we were both inside her."

She sat back, stunned.

"How ... how could you BOTH be inside her at the same time?," she asked with real bewilderment in her eyes.

"Are you sure you want to hear this?," I asked. I could see that she did. She was breathing harder now and her blush had turned into a full-fledged flush.

"YES!"

"Ok ... well ... he was lying on the bed and she was riding him," I said. "He was in her ... you know ... in her pussy."

She winced slightly at the word, but also bit her lip. She was enjoying this, despite her discomfort.

"He was in her pussy, and I was in ... her ass," I said.

Talking about this with her was starting to get to me. I found I wanted to tell her more. I wanted to see how hot I could get her, how far we could take it. I was getting very hard, despite the alcohol I had consumed.

"JESUS!," she exclaimed. "YOU'RE REALLY FUCKING DIRTY!" She shoved me against the back of the booth, playfully, and leaned in close. She turned toward me and slid into my lap, straddling one of my legs. Her skirt pulled up slightly and I could feel heat radiating from between her legs.

Her right leg slid up my thigh, her knee pressing lightly into my crotch. There was no way for me to hide my hardness from her.

"Ohhhh ... you really ARE dirty," she whispered, rubbing her knee against my cock through the thin layer of my suit pants. "Keep talking."

Her mouth was just inches from mine and I could feel her breath on my lips. I decided to push it a little farther.

"You want more? I'll tell you more," I whispered back. "How about the time I fucked my girlfriend on the top of a parking garage during a thunderstorm? The lightning was flashing everywhere and the rain was drenching us. She was bent over the hood of my truck with her jeans around her ankles, and I fucked her from behind until I pulled out and came all over her ass."

For the first time, she actually moaned quietly and grinded on my leg a little.

"Ohhhhhh," she whisper-moaned. "That's soooo fucking hot."

"Mmmhmm. And what about the time I got a blowjob from a girl in my car outside a bar where my band was playing?," I asked, sliding my hands over her hips. "Do you want to hear about that?"

"Yes ... please." She was unabashedly rubbing her pussy against my leg now.

"She was such a dirty girl," I whispered, my lips brushing hers. "She pulled me out of the club between sets and sucked my cock in the back of my car while I played with her huge tits. I came in her mouth and she swallowed every drop."

Melissa moaned again. I was beginning to think she might cum right there in the bar.

"And then I went back inside and finished my show," I whispered in her ear. "Afterwards, I took her back to her place and fucked her until almost sunrise. When we woke up, I fucked her again in her bed and in her shower."

"Mmmm GOD," she moaned. "Keep talking."

"I have so many stories," I whispered, my lips brushing hers again. "Do you want to hear about the time I fucked my manager on her desk when I worked at the record store? Or maybe about the time my date jerked me off while we were standing in the crowd at an outdoor concert?"

"Yessss," she breathed. "I want to hear it all."

Suddenly, I became aware of another presence. Looking up, I saw the bartender standing next to our table. She looked uncomfortable, but also like she'd dealt with this before."

"Okay, folks ... I think it's time to take this party somewhere else, you know?"

Melissa jerked as if she'd been given an electric shock and stood quickly, pulling her skirt down.

"C'mon ... we need to go," she said, grabbing my hand and trying to drag me along with her. I pulled $100 out of my wallet and threw it on the table to cover our tab and allowed myself to be pulled out of the bar.

In the elevator, she was on me again, pushing me against the back wall. There were mirrors all around us.

"Keep talking," she said, smiling. "I want to be a dirty girl like that. I want you to make me dirty."

Then she kissed me, long, deep and slow. Her tongue found its way into my mouth and I welcomed it with my own. She reached down and started to massage my hard cock through my pants.

"I want ... this," she said as she squeezed.

And so I talked as the elevator took us to the 11th floor, where our rooms were. I gave her all the filthy details I could think of. With one arm around around my neck pulling my mouth to hers and her other hand groping my cock, she moaned with each new revelation.

When the doors opened, she pulled me quickly out and down the hall to her front door. As she worked to get the key card in the lock, I pushed her from behind into the door and slid my hand between her legs. Her panties were soaking wet.

"Ohh god, yes," she whimpered, pushing her ass against me as my fingers worked. And then the door was open and we were almost falling in.

My jacket came off quickly and her blouse was open almost magically. She pulled my tie loose and pulled it over my head. I hiked her skirt up over her hips and grabbed her ass, pulling her close. Her hands moved to my belt.

"I just want to feel you," she breathed. "Please, I just need to feel you inside me. It's our last chance. I want you to show me what you know."

With my belt undone, she pulled my pants to the floor. My underwear went with them and my cock stood rigid in the semi-darkness.

She dropped to her knees and took it in her hand. All semblances of her shyness were now gone. She looked up at me, her eyes locking to mine.

"Keep talking," she demanded. And then she slid my cock into her mouth, taking it all in one slow move.

And so I talked. I wracked my brain to remember every kinky and semi-kinky thing I'd ever done. She sucked my cock with abandon, moaning on it as the details of my sex life poured out. Occasionally, I would remind her that she was such a dirty girl, too. The first time I called her a slut, she moaned so loud that I was afraid the people in the next room would call security.

Finally, I pulled her up to me and kissed her again. I pulled her shirt over her head as she slipped out of her skirt. Her bra and panties were off quickly as I pulled off my own shirt and kicked off my shoes and socks. I brought her to the bed and laid her down on her back. I was on top of her quickly and my hands moved all over her.

I kissed down her body, lingering at her breasts. Her breath was coming hard now, her chest heaving. Her nipples were hard and she moaned as I sucked and teased them. Her hands were in my hair, pushing me into her breasts.

Pulling gently away, I moved down further, sliding my face between her legs. My tongue found her opening quickly and I started lapping gently at the juices there before sliding it inside her. She tensed up then and, when I moved to her clit, she came quickly and hard, her legs wrapping around my head to keep my tongue in place.

"Mmmmm, the dirty girl likes to have her pussy eaten, doesn't she?"

"Yes," she moaned. "God, yes. I'm your little slut tonight. I want to be your slut."

And then she was pulling me up to her. Our mouths met in a deep kiss. She reached down and stroked my throbbing cock, finally guiding me inside her and gasping loudly as I entered.

She was so tight, but so wet that I was in without any effort at all. I could feel her pulling at me, holding me there. Her grip was enormous as I moved in and out of her. She moved with me, grinding her pussy against my cock.

"Fuck me," she cried loudly. "Fuck me like a dirty girl."

I moved faster then, sensing that I was getting close to cumming. She matched my pace and I knew that she was close again, too. Plunging deep and with more force, I could feel her juices all over me, coating my cock. She was tensing and she moaned loudly as she came again.

"Ohhhh jesus fucking christ," she yelled. "Fuck, I'm cumming. I'm cumming."

And that was all it took to push me over the edge. As her orgasm rocked her body, I pushed inside her three more times before pulling out and exploding onto her stomach and chest. Her hand moved to her clit and she continued to cum, writhing as the hot ropes splashed onto her breasts.

I collapsed beside her on the bed and she rolled over on top of me, the cum running down her stomach and onto me.

We laid like that for a while, until I was hard again, and then I was inside her again. After we both came again, we cleaned up as best we could and slept, exhausted.

We fucked again in the morning in the enormous glass and tile shower. She begged me to cum in her mouth and I did. She swallowed it all and kissed me deeply afterward so I could taste us both.

And, when I dressed and went back to my room, that was the end of it. We helped to pack the truck and then headed home. She married her fiancé the following month and we never spoke again of that night.

I left that job a couple of years later. The team got me a nice card that everyone signed with wishes of good luck in the future, etc.

She signed it last. It read, simply, "Keep talking. Love, Melissa".