I can still remember seeing Jill that first day. I had been going through a pretty tough time in my personal life and I was in no mood to train a new employee and deal with all the other stuff that entailed. My desk was piled high with work and my supervisor was breathing down my neck. All I knew before Jill walked in, was that she was in her mid-40's and had a teenaged daughter. If the truth be known, she looked great on paper, had a lot of experience and she was likely to make my job a whole lot easier.
My supervisor's voice broke my reverie. "Good morning, Rebecca, I'd like you to meet our new associate, Jill." I turned and started to speak. I still had a bit of a chip on my shoulder. I think my jaw probably dropped, but maybe I only imagined it. Even though we were close in age, Jill was one of those women who seem to manage to always look young. Physically, she was slim and petite. He thick, blonde hair was tied back and she had sparkling blue eyes. Her breasts were small and firm, her legs nicely shaped and toned. She wore a very tasteful suit. It was the kind of suit you wear on the first day to make a good impression. Most of all, there was a youthful eagerness and energy about her, not usually found in women our age.
I have always had a thing for younger women and I responded to Jill much the same way I would to someone much younger. Evidently, she liked me, too and we became almost instant colleagues and best friends. We ate lunch together nearly every day and talked a lot. Usually, we stopped for a drink after work a night or two each week. She was very proud of her daughter, Bethany, who was a senior in high school and had just turned 18.
As our friendship deepened, our talk became more intimate. I eventually admitted to her I was gay. Jill confided in me her struggles with men and relationships. She told me she was at a point in her life where she just wanted to concentrate on work and Bethany for awhile. After all, Bethany would be going to college next fall and she wanted to succeed at her new job and look toward the next phase in her life.
Things continued in this vein for quite some time. Our friendship seemed confined to our work hours and an occasional drink after work. Jill had turned me down a couple of times when I invited her over to my place. She had never invited me to her apartment and I guessed it was because she was both a private person and because she wanted to keep her social life separate from her time with Bethany.
We were enjoying our lunch and conversation one Friday about two months after we met. As our time drew to a close and we had to start thinking about getting our check and heading back to the office, Jill got a bit of an uncomfortable look on her face. I could tell she wanted to ask or tell me something. I was growing a bit impatient and pushed a little.
"We've got to hit the road. I can tell you have something on your mind."
"Well, it's just that Bethany is staying with a friend this weekend and I hate staying alone. I know, it sounds kind of stupid. I mean I....well.....if you aren't doing anything tonight, would you mind coming over and keep me company? I could make us something nice for dinner and I bought this wine I've been looking forward to trying..."
I eagerly accepted. I always enjoyed spending time with Jill and I was curious about her apartment and her "other" life. "Sounds like fun. I can go home, get ready and be over around 7. Would that work? Is there anything I can bring?"
Jill looked relieved, although her face was still a bit flushed. "Great. I'll email you directions. Make sure you have your cell in case you get lost or something. I'm glad you can come over."
The afternoon, seemed to drag, of course. I found myself eagerly looking forward to the evening and excited...more than excited than an evening with a friend really warranted. I wasn't sure what that was all about, but it was OK with me. I wasn't going to worry about it.
I laughed at my nervousness when I got home. I couldn't decide what to wear and changed several times before I decided on a pair of shorts, a short sleeve knit top with a scooped neck and casual sandals. I had just bought a pair with a one inch heel and I'd been dying for an excuse to wear them. I realized we'd always seen each other at work and I didn't even know what she wore for casual clothes. It was a hot, Florida summer day and I couldn't see wearing more than I had to!
I had no trouble finding Jill's apartment. It was upstairs in an old house and seemed to fit her to a "T." She seemed genuinely happy to see me and quickly invited me in. The interior was small, but cozy. Jill seemed to have a knack for decorating and a love of art and books. Besides the books and artwork, I noticed a collection of photographs on a lovely antique shelf. I made a mental note to check them out at the first opportunity. The only evidence I could see of Bethany, was a backpack hanging from a coat hook in the kitchen/dining area.
Jill led me down a narrow hallway. "Come on and I'll show the place. There isn't much to it, but it's home." She smiled.
The hallway led to two small bedrooms, separated by a bathroom. Jill's was the larger of the two and reflected her, being both comfortable and tasteful. Bethany's room looked like that of a teenager. She had packed for her weekend away in a hurry and left stuff strewn on her bed. There was a messy, overstuffed closet and posters on the wall.
"I should have just closed her door, " Jill stated, then led me back into the living area.
I told her it was a lovely little place. I sat down on the sofa while she opened a bottle of wine and returned from the kitchen with two glasses. It was my first opportunity that night to focus on Jill. Her blonde hair was tied back with a ribbon. She was a wearing a light knit, one piece, dress that to just a little above her knees. The cornflower blue was striking with her eyes. I noticed she was barefoot and her toenails newly poished a deep, crimson color.
As usual, our conversation flowed easily. The wine was good and I was pleasantly surprised by Jill's culinary skills. After dinner, we retired to the sofa with some more wine. The jazz music Jill put on was perfect.
I have to admit, as the night wore on, I began to think about Jill sexually more and more. It wasn't that the thought hadn't occurred to me before, it was just that we had become close friends and I didn't want to mess things up by coming on to her if she wasn't interested. Her friendship was more important to me than anything.
Still, I became very aware of the warmth of her body as we sat there chatting. She had put on some kind of after shower splash that smelled delicious. My eyes fell quite often to those smooth legs with the nicely defined calves. The soft knit of the dress had a tendency to cling to her small, firm breasts. I made a note to myself that I had plenty to "jill" about when I got home!
My sexual reverie was jarred by Jill's soft voice. I realized she had turned the conversation to sex and, more specifically to questions about me being gay. It was as though she had many weeks worth of pent-up questions that she had been dying to ask. I thought it was kind of cute. I'm a pretty open person and I had no problem answering her many questions.
I had been in situations like this before, with straight women, who were curious about sex with women. Jill's questions got more and more direct and more and more personal. If I didn't know better, I would almost swear she was getting aroused talking about this stuff. I know I certainly was!
Maybe it was my arousal, or maybe it was the wine....or perhaps it was combination of the two. The words seemed to roll off my tongue, immediately followed by one of those "Oh I wish I hadn't said that," thoughts. I blurted out, "You know, if you are that curious about it, I could show you what it's like to kiss a woman."
Jill seemed to weigh that for a moment. I think the wine and relaxation was having an effect on her, too. "Hmmm....." was all she managed to come out with. She sat up and tucked those pretty feet and legs underneath her. Her eyelids looked just a bit heavy. "Well, why not? If you're game, I guess I am. I mean, like you say, it shouldn't be that big of a deal."
To say I was stunned, is an understatement. Her lips looked moist and those beautiful, blue eyes were looking directly into mine. Then she giggled. "I feel like a teenager at a slumber party."
I reached over quickly, afraid she would change her mind, and pressed my lips against hers. Jill looked slightly startled. Her lips didn't respond to my touch and I pulled back, worried I had gone too far. "Hey, that's not fair!" she whimpered. "That didn't last long enough for me to know what it's like. I hope you can do better than that!"
I blushed and reached over again. This time I took her in my arms and held her close while I pressed my lips against hers. It is hard to describe how good the warmth of her body felt and how delicious the fragrance of her skin and hair was. Jill's lips were moist and parted slightly. My tongue slipped easily between them and I kissed her slowly and deeply.
I expected her to break our kiss, but she wrapped her arms around me and forced my tongue more deeply into her mouth. Her breathing was becoming a bit ragged and she was making some luscious little whimpers and moans. I was completely swept away by my desire for her. Clearly, she was enjoying our kissing and, I might add, she was very good at it!
My hand strayed from her back to her side. The soft knit material of her dress felt warm and smooth as I let it slide upward until I encountered the swell of her firm, little, breast. Although it took a lot of willpower, I paused for a few moments to see if Jill tensed or pushed me away.
When she didn't respond, I cupped her breast. Even through the bra and the dress, I could feel her hard nipple. From her reaction, I could tell she was quite sensitive. I noticed she seemed to be leaning into me, almost pressing her breast into my hand. With my free hand, I reached up and slowly slid down the zipper on the back of Jill's dress, which ended at her waist.
