Jill At Last Ch. 01

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Attorney finally connects with gorgeous secretary.
2.2k words
65.6k
5
6

Part 1 of the 2 part series

Updated 10/29/2022
Created 10/11/2006
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Wudan69
Wudan69
3 Followers

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."

Wudan69
Wudan69
3 Followers
  • COMMENTS
6 Comments
AnonymousAnonymousover 17 years ago
So magnificent

That was incredible i really loved that story i hope you continue with the storie its magnificent.

Pat Murray

AnonymousAnonymousover 17 years ago
Good Start

Loved this story, and you have left the reader wanting more. Great 1st submission, I look forward to Chapter 2.

RomanCEisdeadRomanCEisdeadover 17 years ago
Simple yet beautiful

Great start to the story. Can't wait to read the next instalment.

ethanjones1943ethanjones1943over 17 years ago
continue

you must continue great so far

ethan

AnonymousAnonymousover 17 years ago
Pleasant Story.

Young man has fantasies about an older woman who works in the same office. One night - late they get together - hatch a plan for some after work erotic activity. Good Story! Interesting write!

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