On the last night of our trip to Jackson Hole, we'd headed out for dinner and some shopping in town. I ended up buying a new bikini, but little else. Tori, my girlfriend, bought a pair of hot leather pants from Hide Out. When we were done, we returned to our hotel room, took all of our stuff out of our suitcases and repacked everything for my trip home on Saturday. We had plans for the night, so we got dolled up and headed off to Teton Village.
Having been raised in the area, I'd been back home in February for some skiing with a client, and had stopped in at the Mangy Moose, one of the more popular watering holes in town, to get a drink and a bite to eat. During that trip I'd been served by a waitress named Jessica, whom I'd found quite attractive. I went so far as to let her know I hoped she'd be around when I got back in November.
Being back in town, I was in the mood to play with her. I'd called the Moose earlier that evening and they told me Jessica would be working until midnight, so I was quite excited about the possibilities. I was a bit nervous as well. Who knew if she'd remember me or if we'd be successful at getting her to come back to the hotel with us for the night?
Tori and I were former lovers. We were each other's first real girlfriends during our junior year of high school, and came out to our parents together. Our age and the physical distance between us led us to split up at the end of that school year, but we've remained good friends and occasional sexual playmates ever since. After graduation I left for the big city, but she remained near home. She'd been looking forward to my return this Thanksgiving for a little play time, and had agreed that adding a third person to the mix held the potential for some serious excitement. I'd suggested we give Jessica a shot.
We got to the Mangy Moose at 10:30 and asked to be seated in Jessica's area. When she got to our table she looked at me funny. "You look familiar."
"I should. I was here about six months ago, with a gentleman. You waited on us and I spent some time flirting with you."
"Ahh, yes, you did. I remember now. You told me you were coming back. I see you kept your word."
"Always."
"What brings you back to town this time? The ski areas haven't even opened yet."
"I'm actually here visiting family and some friends for the Thanksgiving holiday." We spent a few more minutes in idle chit chat. She seemed to be genuinely flirting with the two of us, and that convinced me to be bold. "What are you doing when you get off tonight?"
"I guess I'm planning on going home. Why do you ask?"
"Well, I...we'd like for you to go back to the hotel with us for a bit of fun."
"Wow, you just don't beat around the bush, do you? You didn't even bother to offer to buy me a drink first like most everyone else does."
Gosh, I was embarrassed. "I've always pretty much gone right after what I wanted. Or who I wanted. I guess." My reply was about as sheepish as anything I'd ever said.
Now she was blushing. "Who's your friend?"
I reintroduced myself to her, introduced Tori, and tried to explain our relationship arrangement. Open, long-distance, itinerant relationships between bisexual women apparently aren't that common.
"Wow. That's unique."
"So, what do you think? Are you up for a little fun tonight? I'm leaving tomorrow morning, and we'd really love to spend some time with you."
"What makes you think I'm even interested in girls? Do I have a sign or something...?"
"Oh, I don't know. I get this vibe from you; I got in when I was here in February, actually. Something about you just tells me you're into women. At least...well, partially, anyway." How do you even answer that kind of question, I thought to myself.
She stood in silence for a few seconds, apparently unsure of how to process what I'd just said to her. "What would you two like to drink?"
I ordered a diet Coke and Tori ordered a strawberry daiquiri. Jessica left to get the drinks, and Tori and I discussed the possibility I may have come on too strong. I agreed with her I might have gone overboard, and hoped I hadn't fucked things up this early. I'd rarely failed, though, and I honestly felt like there was a possibility with Jessica. She was a lithe, stunning brunette with a tomboyish nature, and she'd triggered my gaydar the moment I met her in February. I was still getting that strong vibe from her, and that had pretty much led me to come onto her as strongly as I did. Tori agreed with me that she was definitely worth pursing.
Our server returned a few minutes later and sat our drinks on the table. "Where are you guys staying?"
"At the Homewood in town." Tori and Jessica kept eye contact with one another, which was incredibly arousing to watch.
"I get off around midnight. Are you guys going to stick around until then?"
"We can if you're interested." She just looked at me for a couple of seconds and then walked off. The look told me she was indeed interested. So we hung out, knocking back a few drinks and some elk sliders until shortly after midnight. Jessica came and sat down at our table, having gotten out of her waitress attire. We chatted for a few minutes and it became very clear to me that Jessica was really into Tori.