Her name was Robin, she was a new hire and my boss had asked me to specifically take her under my wing and show her the ropes. I had noticed her sitting outside my bosses office when he called me in, surmising when I did that she was most likely one of the new employee's we'd recently hired on with the increase in workload we'd recently been experiencing.
At least I hoped she was, she was very attractive looking, though a bit on the slim side. I knocked and then entered Jim's office closing the door behind me.
"Wipe the smile off your face," he told me before I'd even managed to get a word out edgewise. He looked up through his window over towards where Robin was patiently waiting outside. "She's gay," he said simply enjoying the surprised expression on my face a second after he'd said that.
"Now how the hell do you know that?" I asked in response. "It's not one of the questions you can ask on the interview as far as I know," I told him still wondering how it was that he knew that. Jim laughed.
She was in the parking lot when I arrived, saw her get out of a car, but not before leaning over to kiss her girlfriend, partner, or whatever she was they call them these days," he told me.
"Maybe it was just a friend, or her sister," I questioned, once again seeing him smile and then laugh.
"Fuck Brad, even I don't kiss my own wife like that anymore," he informed me. "So unless things have changed since I grew up with my sister, I'd say it was someone she's obviously quite familiar with."
"Damn," I thought to myself. "A lesbian!"
It wasn't the fact that Robin was a lesbian, or appeared to be. There were a couple of others who worked here that were, and I was pretty good friends with both of them. Though admittedly, each of them looked more the part as opposed to the way Robin appeared. Though she was a bit on the slim side for my tastes at the time, and not having what one would call large breasts, which were in fact noticeably small, she was still a very attractive looking woman. She wore her light brown hair long in a ponytail, and stood at about five and a half feet tall. But her smile when I'd even glanced at her had immediately grabbed me and caught my interest in her in the first place. It was very alluring. So it was a bit of a bummer for me to hear she was gay when John told me that tid bit of information. It was the fact this was just one more woman who I now knew I couldn't even entertain thoughts towards that had put a damper on things, not that I had any real chance anyway. I was several years older than Robin was for one, another deterrent, but now even simple friendly flirtatious fun seemed to be out of the question.
I soon stepped outside Jim's office, introduced myself to her, and began showing Robin around. Another thing I liked about her was her bubbly, easy-going personality. It wasn't long before we were chatting away like we'd been friends for a long time. Lesbian or no, she seemed to take to me as a friend, and it wasn't long before the two of us were actually looking at it that way.
Several month's had passed. As we both smoked, we quite naturally went outside during our breaks together, and that led to taking lunches together as well. Before long, we really were pretty good friends, and that eventually opened the door to talking about anything and everything. I don't know what was said, or how the conversation turned in the direction it did one day, but we were discussing relationships (hers and mine with our partners) and I had learned she'd been involved with several women over a period of time. Unfortunately as I soon learned, that seemed to be very typical of a lot of lesbian relationships. She'd been in and out of many with several women, though also interestingly enough, had remained friends with each of them afterwards as well. But as I said ... somehow the conversation turned towards sex in general, and over time, this too got to be more and more open, intimate and uninhibited. Robin and I were soon able to discuss just about anything, which then led to what was mine (and probably ninety percent of the male population out there) regarding two women (or even more than two) being together sexually. Quite naturally of course, she laughed at that. But the most surprising thing came, when she admittedly told me, lesbian or no ... she found me interesting, and though she'd never really had any sexual interest in men, admittedly had found herself being a little curious about that lately. Her hint didn't go unnoticed, and our flirtation seemed to slowly escalate after that. It was still several weeks later though before things took a sudden dramatic and totally unexpected turn in our relationship. Since I didn't live too terribly far away from her, she'd asked me if I could come over on the weekend and help her move some furniture around at her place. Quite naturally, I had agreed to do so. By now of course, I had also met her partner who'd accepted me somewhat as a friend, though not nearly in the same way Robin had of course. Thankfully, I had learned that Tina wouldn't be there as she would be working, which is also why Robin needed my help to begin with.
They had just purchased a new entertainment center, which is why we had to move so much around, getting it set up and everything rearranged. It was during this that I happened to notice they had a stash of dirty movies as we went about replacing things. Oddly enough, most of them were heterosexual in nature. Which I was surprised at, figuring that lesbians would prefer seeing and watching other women together. And not that they didn't have a good deal of those movies too, they did ... but they had at least an equal amount of good old "fuck flicks" as we called them.
"I thought lesbians didn't enjoy looking at naked men," I said curiously. Robin of course laughed at that, answering.
"Just because I prefer being with women doesn't mean I can't enjoy looking at men too. I do find certain things about them interesting," she'd stated.
"Oh? Like what?" I pressed enjoying the direction this conversation was suddenly going in.
"Just because I haven't fucked a man, doesn't mean I haven't wondered about what it would feel like," she told me. "And ... I do enjoy watching it from time to time," she added, "though I've not actually seen it, outside of watching a few porn movies. But admittedly, it is sort of interesting to see a guy cum," she'd said simply, surprising me a little when she'd said that. "Maybe one day, I'll actually see a guy do that."
"You mean you've never actually seen a guy squirt? Aside from porn movies?" I questioned incredulously, to which she'd responded no, she actually hadn't.
"Why? You offering?"
We had joked around before, I didn't see this as any different than that, joking back, or so I thought anyway. "All you have to do is ask," I'd responded not at all expecting the look of surprise on her face as she took me quite seriously.
"Really? You would? You'd jerk off for me and let me watch?"
Now it was getting interesting. We'd just passed from joking around to actually considering it, or at least she was anyway. And though I didn't really think I'd be too terribly shy about doing that for her, I also didn't look forward to feeling awkward and uncomfortable while doing it either. But again, I was also still treating all this like an ongoing somewhat flirtatious topic of conversation rather than any of it becoming real.
"I'd have to have something to keep the interest up ... if you know what I mean," I laughed back.
"We could put on one of the movies for you to look at while you do," she suggested, which is when I realized, she really was being quite serious about all this.
"Well, that might help yes ... but,"
"If I'm actually seriously considering doing this, I'd much rather have something real to look at while I do," I told her, hinting at, and not at all expecting her to comply with my wishes. Which in a way, I was figuring would bring a rapid end to the direction we'd been heading in.
"So in other words ... you want to see me naked while you jerk off."
"Only fair," I responded back, once again not expecting her to do it.
"Ok, but ... no touching, just looking," she informed me.
I couldn't believe I'd just heard what I had. But in the next minute, I was actually following her into her bedroom where she proceeded to undress, first slipping out of her jeans, and then her wife-beater tee shirt as I slowly began undressing myself, still half expecting her to yell out "April fools" or some such thing, and make me feel like a total and complete idiot for believing her. That didn't happen however. Minutes later, I was looking at her totally naked now as she lay down on her bed, patting a place for me to sit closely next to her.
"So I can watch you," she informed me quite seriously. "I want to see how you do it, how a guy pleasures himself, and then watch you cum." She told me.
"I don't know. We'll see. See if I get horny watching you ... so maybe," was all she said though it was obvious she hadn't as yet made up her mind yet about pleasuring herself.
.... There is more of this story ...