"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.
