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Jill At Last Ch. 01

By: Wudan69



I was a young attorney, working during my first year after law school at a small firm in Los Angeles. I stayed pretty busy most of the time, doing the normal lawyer thing. Jill was a legal secretary whose work station was just around the corner from my office. I got to know a few things about Jill through casual conversations here and there as I passed by on my way to another office, or the copy room, or wherever that gave me an excuse pass by and get a look at her. She was in her early-forties, which was nearly twice my age, but there was just something about her I found irresistibly attractive. It didn't hurt that she was tall with an incredible figure, not the least of which were her ample breasts that she always managed to show off just enough to make them impossible not to look at, and yet always came across as elegant and professional. 

Sometimes passing by Jill's station I would catch a glimpse down her partly open blouse and my hormones would be off and running. Some days it drove me so crazy that I would have to go to the bathroom and jack-off just so I could get back to concentrating on work. But there was something more to Jill than just her beauty; she had a way of making everyone feel as if she was very happy to have them around her. I also knew that she was a single mother of a 12-year old boy, which meant that she never stayed late at the office, much to my disappointment.

Being in a small office, it was rare that anyone besides me stayed late. The older attorneys who had better things to do rarely stuck around past 5:00. I often found thoughts of Jill coming to mind, and I would inevitably start to surf the web, looking for some porn that resembled Jill. I never found any, but the thoughts of Jill and the images that flashed ceaselessly across my screen would make me so horny that I had to stroke myself through my pants. When it got too much to bear, off to the bathroom I went to get some relief.

I usually kept my door closed during these sessions, but of course one night I just didn't think about it. My rock-hard shaft formed a huge bulge in pants, and the pre-cum had made a little wet spot on my khaki trousers. At the last second I heard someone walking toward my office and quickly minimized the porn on my computer screen, and tried to look busy. I was shocked to see Jill walk past my office, then stop and come back to the doorway. I quickly tried to assume a casual position while at the same time trying to hide the bulge in my pants that had just gotten even bigger.

"Hi James." she said in a less than happy voice. I had never seen Jill in casual clothes before. Despite the fact that we had "Casual Fridays" around the office, she always dressed professionally. That night though she was wearing a light summer dress that only came down about mid-thigh and had a low neckline, and stood out beautifully against her tan skin. 

"Hey Jill," I tried to respond in a cool voice, but I could feel my voice start to choke and my face was on fire. Partly from embarrassment at almost being caught, but mostly from the thousands of Jill-fantasies running through my head that had started out just like this. "What are you doing here so late?"

"Bill has me working on a big project, and I'm a bit behind. Today I had to leave early to help Derrick get ready to leave for a long weekend with his father. So now I'm back to try and play catch-up. What are you working on?" As she glanced down from my face toward my desk to see what I was working on, I could see that she notice my bulge and probably the wet spot too. She quickly looked away, with a mild look of embarrassment playing across her beautiful features. 

Damn it! My face burned even more. I quickly adjusted my position in my seat, and patted a pile of paperwork next to me. "Oh, you know. Just the usual."

"Right. Well, I'd better get to work," she said with smile, "and let you get back to yours." There was an odd emphasis on the last part of her statement as she turned away to head for her desk. I wasn't sure if she was encouraging me to get back to work, or get back to taking care of my now raging hard-on. The possibility that it was the latter sent my brain buzzing. 

I decided to wait a bout 15 minutes, then pretend to take something to the fax machine that would take me past Jill. She was leaning forward in her seat with her elbows on her desk, which pressed her breasts together and the caused the neckline of her loose dress fall open, giving me an unprecedented look at those gorgeous tits. Electricity shot from the top of my head strait down to my cock. She looked up as I walked by and smiled, but neither of us said a thing. My gaze had lingered longer than I had intended, and I knew she had noticed where I was looking.

I went to the fax machine and typed in the fax machine's own number. The fax started to go through and I racked my brain trying to figure out my next move. This was not like picking up a girl at a bar, or even at school. This was a whole new league, and I was a rookie player. I thought about offering to get us some dinner, but no doubt she had eaten before she came in. I decided to just jump into a conversation and see where it took me. On the way back to my office I stopped at Jill's desk.

"I hope this isn't too intrusive, but you didn't seem too happy when you first came in. Anything other than just not wanting to be at work on a Thursday night?"

She smiled softly as she looked down at her desk for a few seconds in silence. I was about to apologize for bothering her and leave, but she said, without looking up, "I'm alright. I just..." she stopped herself with a long sigh. She gave a light laugh and looked up, "You know, just old lady stuff. Nothing that would interest you." She carefully maintained her slightly strained but still sweet smile.

"In the first place," I answered quickly, "old lady" my ass."

"Ahhh, aren't you sweet" she said in a playfully condescending tone.

I decided to leave that one alone for the moment. "And on the contrary," I continued, "I've been working all day and the prospect of some human interaction sounds very interesting." After I had said it, I worried that I had made horrible choice of words. I thought I saw that Jill had caught the double meaning, but she just smiled slightly.

"So what's going on?" I asked again.

After another moments pause, she leaned back in her chair and said, "Oh, it's nothing in particular. It's just my life. I work and take care of Derrick. That's it. I mean, don't get me wrong. I'm pretty much happy with my situation, but..." Jill trailed off.

"Do you have any good friends that you hang out and relax with?"

"No. Ever since my divorce, our old friends have just seemed to fade away. I don't really have the time or much of an inclination to go looking for new ones."

"Dating?" I asked, expecting that I knew what the answer would be.

Jill just gave a short laugh. "Right. Old lady with a young kid at home. Not exactly a recipe for romance."

I let her words hang there for a moment, while I leaned against the wall, looking at her. "I was serious about the "old lady" thing," I said finally. "I'm pretty sure your drive every guy around here crazy." Jill took in a deep breath, and held it. I doubt she did it intentionally, but the swell it gave to her chest was magic. Silence hung in the air, and I didn't do anything to try to hide my growing erection. Jill couldn't look up to my face, and her gaze stopped at my waist, and froze.

After a moment, she looked down at her hands in her lap, her fingers beginning to play nervously with each other.

"What about you?" Jill asked finally. "Got a girlfriend yet?" 

I waited a few seconds, then simply said, "Nope." I knew this was going to sound lame, but I had no idea how to get to the next level, so I just plunged blindly ahead. "You look a bit tense, would you like me to rub your shoulders for a couple of minutes before we get back to work?"

Jill hesitated for a moment then let out a quick sigh. "Sure, that sounds great."

I moved away from the wall and started to walk around Jill's desk. Jill sat up straight in her chair and reached back with her hand and pulled her shoulder length, silky blond hair out of the way. I didn't realize it, but my hands had gotten cold during this time, and when I touched her warm skin, she sucked in a quick breath through her teeth.

"Sorry." I said. I quickly rubbed my hands together. Partially to warm them, but also to try to stop them from shaking so bad. I reached back up and slowly started to rub. I must admit that I am pretty good at giving massages, and I was determined to make this one my best ever. 

"Do you like it hard or soft?" I asked, this time fully intending the double entendre. 

"If it's my back and shoulders, I like it hard." 

I knew at that moment that things were going well. I also made a mental note that I should go gently when I got to any other areas of her body. As I applied more pressure to some of the knots in her neck and shoulders, she let out little moans of enjoyment. Those moans made my cock twitch with excitement. As I worked my way across her shoulders from her neck, my hand came in contact with her dress. Over or under, I asked myself? I decided to punt. 

I fumbled at the edges of the material, acting as if they were in my way and I didn't know how to handle it. Jill reached up with her free hand and pulled the material slightly further across her shoulders, just exposing the top of her satiny blue bra strap. I rubbed a bit longer, then acted as if the straps were in my way too. Not waiting for Jill to move them, I took the initiative and slid her bra straps over the edge of her shoulders. As I kneaded her shoulders and down the middle of her back, I pushed her dress further down her arms. Soon the tops of her round breasts were exposed, and a growing hunger was building in the pit of my stomach, making its way to my aching member.

I had gradually moved closer and as Jill rolled her head back to stretch her neck, the hand holding up her hair brushed against my cock. I involuntarily sucked in a quick breath. My hands stopped moving. Jill let her hair fall, its silky smoothness caressing my hands still resting on her shoulders. She rolled her head around again, more slowly this time, again brushing my cock with the back of her head. And again a third time. This time as her head came by, I pressed my cock in as I pulled back on her shoulders. 

We stayed like that for what seemed like hours, Jill moving her head back and forth against my prick. I slid my hands forward off her shoulders to massage her chest, just above her breasts, then slowly began to inch my way down under her dress and under her satin bra to knead handfuls of her breasts. Jill began to moan again, and as my fingers and thumb found her erect nipples, she gave a quiet gasp as I gently pinched and twisted.

I slid my hands back up Jill's chest, up her neck, and took her beautiful face in my hands. She opened her eyes and watched me as I leaned over and kissed her on the forehead, then on the nose. She licked her lips just as I brought my lips down gently against hers. The moist sweetness of her plush lips was electrifying. Slowly I let my tongue softly probe, and soon her tongue found mine.

"Where?" she asked.

I didn't need to ask what she meant. I had fantasized about taking her all over the office, but now none of that seemed right. "You said Derrick was with his dad. Can we go to your place?" Jill said sure. 

I pulled her chair out for her as she stood. She started to adjust her cloths, but I turned her and with one hand on her waist and the other sliding behind her neck, I pulled her close for another kiss. "I'll meet you in the parking garage and follow you to your place."

Jill At Last Ch. 02



About 20 minutes later, we pulled into the driveway of her house. I was a bit surprised at how nice it was, but figured that it must have been part of the divorce settlement or something. As I followed her inside, I noticed more sway in her hips than usual, and admired again her amazing figure. Once we were inside she asked softly, "Would you like something to drink?" 

"A glass of water would be great." She raised an eyebrow but kicked off her shoes and turned and walked back to the kitchen. I sat on a bar stool at the island in the kitchen as she got a bottled water out of the fridge poured it into a wine glass. She leaned across the counter and handed me the cup, affording me a remarkable view of her cleavage as her breasts hung in the dress, barely held in by her bra. I didn't try to hide the fact that I was looking anymore, and she kept leaning over, letting me look as long as I liked.

She smiled as I leaned in to give her a kiss. "What?' I asked.

"I'm happy that your here, that's all. And a bit nervous, if you want to know the truth. I haven't been with anyone since my divorce." It was my turn to raise an eyebrow, but I didn't say anything. I gave her a brief kiss, then said, "Do I get the grand tour?"

She slowly stood up strait and said, "Sure." She took me by the hand and led me past the dining room and living room, back to the entryway where a large staircase curved around to the second floor. Her summer dress swished back and forth as she walked up the stairs. I wanted to reach up and grab her ass, but I had to play it cool here. She pointed out some of the rooms as we walked down the hallway, back to the master suite. 

She turned before she opened the door and said, "I want you to promise that what happens in here stays in here."

I almost said, "Scouts honor," but didn't want to highlight our age difference, so I simply responded, "Of course. I promise." She kissed me lightly on the lips and opened the doors to her bedroom. The room was huge, with vaulted ceilings and large windows looking out over the backyard, and the woods beyond. The master bathroom was off to the left, and I could see a large shower and Jacuzzi bath on one side. I imagined we might be there later.

Jill walked over and sat down on the edge of the bed, and I leaned against the wall. "You're playing it pretty cool," she said. 

"I just want to look at you for a minute. You really are beautiful." Jill smiled and leaned to the side and put her feet up beside her on the bed. Her dress fell off her shoulder, revealing the top of her bra-covered breast. "You know, every day I have walked past your desk and tried to catch even a glimpse of... What I mean is..." 

I just didn't know what to say. Without taking her eyes off me, Jill stood up and slowly pulled her dress up over her head. She was simply stunning as she stood there in her satin blue bra and panties. I pushed myself away from the wall and went and stood close to her. I had kept my hands in my pocket so they wouldn't be cold this time when I touched her. I reached out and caressed her arm, then made my way to her waist, then across her flat stomach. I slid my hands back around her waist and pull her tight against my body as we kissed.

Soon I felt her press her pelvis against my cock, now pulsing in my pants. I pressed back, and we stood there, kissing and slowly grinding against one another. Her hands were trembling as she undid the buttons of my shirt. As my shirt fell to the floor I loosened my grip enough to let her ease onto the bed as I brought my weight gently down on top of her. I kissed my way down the side of her neck, as I eased her right breast out of her bra, then let my mouth find her once-again erect nipple. 

As I sucked and flicked it with my tongue, Jill began to moan and her hips were grinding against the air. I wanted to drive my shaft into her wet pussy right then and there, but I forced myself to go slow. I freed her left breast from the bra with my other hand and slowly rolled her nipple between my thumb and finger as I continued to suck on the other. I had to feel her wetness, so I moved my hand down her torso, stopping to play with her belly button for a moment before I moved further down. As my fingers reached her panties, I played with the little bit of short-cropped pubic hair that was just above the top edge of her panties. Then I slid my fingers under and made slow, gentle circles downward across her soft mound. 

At last I knew I was far enough in, and I parted her pussy lips with my fingers as I dipped the tip of my middle finger inside. It was so hot and wet, I thought I was going to cum just feeling it. I kissed her again, then kissed my way down her body as I slowly inserted my finger further and further inside. When I got down to her panties she lifter her ass off the bed so I could pull them off. I threw them on the floor and admired the sight as she slowly spread her legs wide open. 

As I moved in, the aroma of her hot juices filled my senses, and I eagerly dove in. "Gently," Jill moaned. I slowed myself down, and began to tenderly work my way around, only occasionally moving up to gently caress her clit with my tongue. My shaft was driving into the bed uncomfortably, but I didn't mind. I was in heaven. Her love juices tasted so clean and delicious. I could have gone on for hours, but as she began to push her pussy against my face, then thrust it with more force, I knew she wasn't going to last long. I moved up to give more attention to her clit. Three quick flicks across her clit sent her over the edge. Her back arched and she grabbed my head and just held it against her wet pussy, but she didn't make a sound. 

She held me there for so long that I thought I might suffocate, but soon she relaxed and let me go. "That was incredible," purred Jill. I stretched out next to her, an arm draped across her torso, waiting to see what came next. I was so horny I thought I might cum in my pants any second. 

After a few moments of lying quietly together, Jill turned on her side and caressed my faced with her hand, planting light kisses all over my face. Then she began to work her way slowly down my body, kissing my chest, my stomach. I kicked my shoes off onto the floor as she undid my belt and pants. I helped her pull them off with my boxers, and noticed Jill looking at my rock-hard cock. 

A slight smile played across her face as she slowly tickled my shaft with her fingernails. Other girls my own age that I had been with never took their time like this. I laid my head back and let Jill work her magic. I felt Jill's hair glide across my abs, and I knew she was about to take me into her mouth. She licked the tip, then all around the head as she slowly stoked my shaft. I didn't know if I was going to last much longer, as I let out a deep moan. "Ugghhh, that feels so good," I whispered.

"Do you want to me to make you cum like this, or do you want to cum inside me?" Despite what I might wish, or what is portrayed in all the porn I see, one shot and I'm done for a while, so it wasn't a tough decision. I said, "Do you mind if I do it from behind?"

"No, but not in my ass, right?" 

"No, I want to feel your warmth and your wetness."

Jill knelt in the middle of the bed with her face laying on the bed and her ass high in the air as I positioned myself behind her. I fumbled around a bit trying to find my way in. Jill reached up between her legs and guided me in. "Ugghhh!" I moaned as my shaft drove into her hot, slippery hole. I began to pump slowly, trying to make it last, but I was cumming too fast. I pulled out to try to stop my orgasm, but I grunted as white hot spurts of cum squirted clear up to her hair, then across her back, then all over her beautiful round ass. I leaned heavily against her, panting heavily. She waited patiently until I slid to the side to lie on the bed, then she stretched out on the bed next to me.

We gazed at each other for a few moments, then she leaned over and kissed me. "You were great," she said sweetly. "There aren't words to describe how you were," I answered as we lay together in the afterglow of our lovemaking.