Let me start by saying that I'm not gay. I had never been with a woman before this and, though I'll admit that I'd fantasized about it from time to time, I didn't think that anything like this would ever actually happen to me. I'd noticed fit bodies, of course, and had admired the womanly attributes of girls over the years. I'll even say that, at times, I'd been attracted to girls and had let my mind drift there sexually when I masturbated. I've had celebrity crushes on the girls that everyone had crushes on and have noticed the feminine qualities of some of my prettier friends, especially when we were laying out in bikinis together or were in the same room changing clothes. I'd be lying if I said I hadn't stole glances in some of those situations—but that doesn't make me a lesbian.
With that out of the way, I should start by saying that I work for an international PR firm and share an office with mostly women. With few exceptions, we all get along and it's a great job that I've learned a ton at. Each year the company puts on a training conference out of our headquarter building in New York and two people from every office across the country are selected to participate. This past year, me and my co-worker Alison were chosen to represent our office and would end up sharing a hotel room and spending three days learning about the latest trends from vendors and industry keynotes. I looked forward to the trip, partially just to get away and spend some time in Chicago and partially to hang and party with Alison, who was about my age and a lot of fun.
The flight had been a nightmare and when we finally made it there, we were six hours past our original arrival time. Weather delays and a mechanical issue in Phoenix had turned what was going to be a straight shot across the country together into an all-day affair. At least when we'd eventually made it, the cab ride from the airport wasn't too bad and when we finally got to the hotel, we we're both ready for a change of clothes and a glass of wine.
When we walked in we knew we were in the right place because the lobby was packed with women mostly our age and maybe slightly older and clearly, we were the last two people to arrive for the conference. Alison went to check us in and I sat with our bags, politely scanning the lobby for a bar and letting out a sigh of exhaustion that we were finally here.
After a few minutes Alison walked back towards me and she was smiling, with a you're-not-going-to-believe-this type of expression.
"Oh God, what now?" I asked with a laugh. "Tell me they didn't give away our room."
"Oh they didn't," she said, "but they're all out of doubles and roll-aways and our room has only a queen bed. It's now a slumber party...this trip gets better and better!"
"You know, as long as they have a room, I don't even care...besides, we're both little—we can share a queen bed."
"Agreed, it's fine," she laughed. "Plus, my husband will love it when I tell him we shared a bed since he really wants me to have sex with a girl."
I laughed with her when she said it but my stomach dropped. Maybe it was the long day or the fact that I was so tired but god, it sounded hot when she smiled it out of her mouth to me and held my eyes as she laughed.
"Want to sleep with a girl?" is pretty much what I'd heard. I'd never really looked at Alison like that but there was something in the way that she said "with a girl" that sounded erotic.
Don't get me wrong. Alison is pretty and sexy, with a tiny little body that's always made me a little jealous. She's an avid runner and it shows in her legs and she wears cute little dresses that accentuate her curves and toned lower body. I'd be lying if I said that I hadn't noticed her perfect little butt in jeans or the outline of her thong when she wore one of her clingy dresses.
We took the elevator up and found the room, dragging our bags in as we both laughed again upon seeing the one bed.
"The good news is that there are two bars in the lobby," I announced, "and I think that the plan should involve a change of clothes and another elevator ride to inspect them personally."
"Ding, ding," she said, as she unzipped her suitcase and started hanging up clothes. "I'd love a shower but I'd love a drink even more." "We can change before we go to dinner—let's just go."
We went back to the hallway, to the elevator, down the seven floors and into the bar that was just past the front desk. We both ordered white wine and exhaled again, as we started to relax and shake off the day.
"It's nice that we don't start until noon," Alison said. "We can have dinner and drinks and sleep in!" she said with mock enthusiasm, slapping my hand with hers.
"I know...good call coming in the day before—even if it almost literally killed us!'
There were a ton of people walking in and out and we were having fun watching it all go by. The wine was good and it felt like the day was behind us, as we caught up on nightmare clients and gossiped a little bit on our team back at the office. Alison said she was happy to be away from the routine for a few days and I completely agreed.
We kept laughing and ordered another glass of wine and I could feel it going through me. It was nice to be here, calm and away from home with someone who was just as happy to be out of town and escape for a bit. A nice glass of wine or three wasn't a bad thing, either.
As the wine kept going down, I was still thinking about what she said in the lobby and kept hearing my old college speech professor saying "every sarcastic remark has a bite of truth to it," like he did during his lectures.
Could she have been serious? Even a little bit? Could something happen between us in that bed? Whether it was the wine or my exhaustion, I couldn't stop thinking about it. That is, I couldn't stop thinking about the 'what if?'
She was talking and I was looking at her lips, at her tongue that moved as she spoke. She was really pretty. Could I kiss her? I thought that maybe I could. Did I want to kiss her? I was starting to think that maybe I did.
"Hellooooo?" she said, waving her hand in front of my face, as she'd clearly asked me a question that I hadn't heard. "Are you awake?" she smiled.
"Sorry," I stammered. "I was zoning... I'm not very good company after the day we had!"
"You're just fine," she smiled, as my stomach dropped again. "But I'm tired, too. Should we just get something to eat here and plan to go out tomorrow night?"
"I was hoping you'd say that...I'm done and the thought of actually going out seems impossible."
We ordered edamame, sushi, two salads and a couple more glasses of wine each. Halfway through, Alison got up to pee and I found myself watching her butt as she walked away from the table. It felt weird to think this way about her but I wasn't really trying to stop. I swear this wasn't normal for me. Like I said, I'd been attracted to girls before and had fantasized about having sex with them but the opportunity had never presented itself and I'd pretty much pushed it from my mind as something that would never happen.
And maybe it was still the wine but I kept thinking about sharing that bed with her, how we'd both get ready at the same time and I wondered what we'd both end up sleeping in.
She came back from the bathroom and sat down with another smile.
"What, I asked, like I'd been caught doing something I shouldn't have been doing.
"Nothing," she smiled. "What were you thinking about while I was gone?"
"I don't know...nothing, really, why?" I said as my face started to feel warm.
"Because...I'm freaking out that I told you what my husband said about wanting me to have sex with a woman."
