A Most Unconventional Affair

Fuck. This has to be, hands down, one of the weirdest damn things that has ever happened to me. I guess I'll just rewind back to the very beginning. I'm a 40 year old married man working for a large engineering firm that's split between three sites. In my area we had Ellen, a beautiful 41 year old divorced brunette as our office admin or secretary if you prefer the old style terminology.

Ellen had overcome some difficult issues in her life including an abusive husband and some substance abuse issues but those issues were way back in her past though they did affect her demeanor around the office. She always had a bit of a "standoffish" attitude but that sort of melted away when you started to talk with her.

Whenever she'd send out those site wide emails detailing the usual office drivel about a coffee shortage or dirty refrigerator, I'd always respond with a snarky response. She'd always get a kick out of my replies and so we developed this banter between us. Later, I came to find out that, by her estimate, some 90% of men in the office were so intimidated by her that they pretty much avoided her. Well, as it turns out, their loss!

As the months wore on, things settled into a nice routine between us. The facilities folks, in all their infinite wisdom, moved our desks to within 10 feet of each other. Thus, I was able to gaze upon Ellen throughout the day. And being within talking -- hell whispering -- distance, meant that we could exchange the office gossip of the day. I was quite happy that our little work relationship had developed so nicely considering how freaked out some of our coworkers were by her seemingly harsh attitude.

"Hey, I want you to start to integrate Ellen into some of our day-to-day stuff. I cleared it with management already. This should lighten up your load a bit so you can devote more time to the Aries Project," proclaimed my boss bright and early one morning.

Fuck. This hit me like a bolt out of the blue. The sharing of people was not unheard of but I just didn't anticipate my good fortune.

"Uh, ok," I stammered. "Sure. I'll start training her right away."

The next day, I broke out the training manuals for our little task at hand. It was slightly on the complicated side but Ellen surprised my yet again with her technical prowess. She really was quite overqualified for her admin job. I was impressed.

Now, here's where I started down the "road to ruin" as they say. While showing Ellen the inner workings of one of our tasks, we hit a point where we need to pause so as to let a computer system refresh. We made idle chit chat while waiting, talking about the weather, vacations, even our finances.

"Shit, I can never manage my money," she laughed. "It's one of those things I just can't do. It runs though my hands."

I chuckled and then without really even thinking, blurted out, "Well, shit Ellen, if you need some cash, I'd be happy to lend you a few bucks. Of course, I wouldn't want repayment in the form of cash, though."

Uh oh. Did I just proposition the secretary...at work no less? Shit. I guess I'll see if she has a good sense of humor.

She laughed and looked up at me, "You know I should go to HR and lodge a complaint."

I could tell she wasn't bothered at all by my comment. Well, I thought, she's a coworker that I can deal with! As our training continued, I couldn't help notice that she started to have one of the more schizophrenic clothing wardrobes I had ever seen. One day a staid suit, the next a skin tight tee shirt and jeans. And, of course working in close quarters with her, I noticed every supple curve of her body. I wasn't really sure where this was going to go, but I was more than willing to go for the ride.

"So, how's the Aries project coming along?" asked my boss a few days later.

Fuck. I hadn't even looked at it. "Ah, pretty good. I'll have a summary regarding our staffing needs by the end of the week," I lied.

"Great! Carry on," he said. "Oh, and thanks again for training Ellen. I appreciate it."

"Well, the training schedule's a bit tight, but we'll get though it ok," I feigned.

Well, in the weeks that followed, I managed to coble together a report for the boss and get Ellen trained so that she was able to help us. Ellen and I became pretty close coworkers. We began emailing each other at home and at work, exchanging the usual things like jokes and comics but also the more personal details of our lives.

As it turned out, Ellen was casually dating. Nothing serious really, but she filled me in from time to time on the odd vacation getaway that she and her boyfriend might have had. Nothing really explicit but I could detect that she and her gentleman friend were not really that close. They didn't live with each other and pretty much saw each other only when she was free.

Now, fast forward this story to just a couple of months ago. Through a series of unfortunate events, Ellen and another employee had "words" with each other and a complaint was filed. Both Ellen and the other employee were actually put on suspension for a couple of weeks. This was serious but as I emailed Ellen to find out the details, I could see that it was really just an overzealous reaction by our new HR representative who was just following the "employee discipline manual" letter by letter.

Ellen was so disgusted with what was happening that she decided that she really couldn't go back to work. It would be too awkward, she thought. While she was on suspension, we had lunch a couple of times and shared a late afternoon coffee or two. At these meetings she pretty much decided that she needed to move on. She tendered her resignation and began to look for work.

"Hey, can I use you as a reference?" she asked one afternoon, about a week after she quit.

"Sure. Just give me a heads-up as to might be calling. Do the job prospects look good?" I asked.

"Fuck yeah," she gushed. "I have a lead on a great one right now."

Early the next day, I got a call from a major accounting firm. They were interested and asked some pretty detailed questions about Ellen. I was only too happy to let them know that she was the best damn employee I had ever seen! Well, that did the trick because shortly thereafter she ended up landing the job -- with two additional weeks of vacation and a $15,000.00 a year raise!

I was so relieved to see her land on her feet. But I must confess that I was quite sad to see her gone. I vowed to keep in contact with her but emailed her infrequently at best. About two months after she quit, our emails started to become more frequent. She chalked this up to some "grand alignment of the stars" or some such bullshit. I thought maybe it just a coincidence but she reminded me that there were no coincidences. Now, that made me think. Maybe she was on to something.

"So, how are things going with you this week," I asked her in my latest letter. "Hopefully okay. You know I get worried about you sometimes."

"Oh, I'm okay," she replied. "The job is great and I'm pretty happy here and only about 50% of the people are afraid of me," she laughed. "I'm still trying to get my finances back in order. That two week stand down kind of hit me in the checkbook."

And then the kicker.

"Oh, if I remember, you had a plan where I could fix my finances quite easily," she joked.

"Well," I replied, "if you're still interested, I'd be more than happy to help out. In fact, I've been reading some new books on the subject and I'd be more than happy to try out some of the stuff I've learned. So, wrap that dirty little thought around your pretty little mind! Talk with you later, beautiful!"

"Hmm. It's hard to see a downside to your offer, actually," she replied the next day. "I've been thinking about that all afternoon, into the evening, and now, into the night. Let me know how we might proceed. My schedule is a bit rough for the next few weeks and I bet yours is even rougher."

Fuck. You'd need a forklift to raise my jaw off the desk. Is she joking I wondered? Shit. Well, I wasn't going to let this situation just die a quiet death. I figured, "What the hell, let's take this as far as it's going to go."

So, I proceeded to write her a very detailed -- and very erotic -- letter that detailed how we might go about our little affair. In this letter, I basically detailed the seduction and ensuing passion we would experience. Prior to sending this letter, I told her I had some ideas but I didn't want to freak her out.

"Oh, I won't be freaked out. Go ahead and send it. I'll read it over the weekend," she said.

So, I sent the letter on a Friday evening. I didn't hear back from Ellen until Sunday night.

"Holy fuck," she exclaimed in her reply. "That was hands down one of the hottest fucking things I've ever read. I really haven't thought of anything else since I read it."

"Well," I asked, "should we ramp up our plans?" I couldn't believe I was asking her to start an affair with me. And in a bit of banter worthy of a Seinfeld episode, I spelled out some possible terms for our relationship. Basically, we would embark on a no strings attached, open ended, tryst. We would begin the affair when we were both comfortable, we would end it when either of us wanted to, and we would meet whenever it was desirable for us. Neither of us could spend the night due to situations at home but we both figured that we could meet on the occasional evening after work and, well, there's no polite way to say this, just fuck and suck ourselves silly. We'd part ways around midnight only to meet up a couple weeks later for a repeat, if we felt like it. Everything was staring to fall into place.

"Well, I'm a very sexual creature by nature," she replied. "I'm really looking forward to this. But, you forgot one little detail. Check your email tonight and you'll see."

Forgot something? Me? Shit. What did I forget? Well, I'd have to wait for the email I guess. Later that night, the message came in.

"You seemed to have forgotten how our little discussion started," she said. "It will be $2,500.00 to embark on this little adventure of ours. No checks please. Of course this includes absolute discretion, drug/disease free (can provide current documentation), no strings or nonsense or blackmail (emotional or otherwise), and of course it's ME - what can I say? No hunting around on the internet dealing with photo fraud and all other types of crazies and dead ends. So let me know . . . if you are agreeable to my terms, as I am to yours, then I am very much looking forward to our first meeting!!"

My heart skipped a beat and you could have heard my jaw hit the floor a mile away. Holy shit! What have I gotten myself into? Now, what do I do? Honestly, my first thought was that she had just played the greatest practical joke in the world on me. I'd been Punk'd just like on MTV. But, after regaining my composure, I realized she was serious.

Then for a split second or two, I actually wondered if she was some sort of escort on the side. But, an escort who's short of cash? Nah. Couldn't be. Well, there was no way I was going to counter offer -- that'd be crass. And if I turned her down, well, that would be equally bad since I would be saying that she's not worth it. That left only one option. Pay her the $2,500.00. Oh, and it was a one time payment. I did get up the nerve to ask that. While the Aries Project was paying me nicely, it wasn't SO nice as to allow me to pay her $2,500.00 a pop!

I emailed her back telling her that I had no issue with her terms and was ready to start our little adventure. She wrote back and mentioned that she was eager to begin as well. Luckily for me, I manage all the home finances and have money stashed away in at least three different accounts. So, I transferred funds from one account to another and then visited the bank with a withdrawal slip in the amount of $2,500.00. I left the bank with a wad of cash in my pocket. Next up, I made reservations for a hotel near work. I emailed Ellen to let her know the date. She replied that she was looking forward to it.

Two weeks later, "date night" rolled around and was upon us. As it turned out, Monday evenings worked out best for both of us. It was a riot. A total fuck and suck fest on a "school night" no less! The very thought of that had us both chuckling a bit. The plan was for us to meet up, enjoy ourselves, and part company around midnight.

As 4:30 rolled around, I bolted from the office so fast that if you blinked you would have missed me. I tore up the road to the hotel -- about a 2 minute drive. At the front desk, I checked in with a sob story about having to do some late night testing on the "Aries Project" or some such bullshit. That was my excuse as to why an "in state" resident might need a room for the night and it might explain why I might not be there ALL night long. I know, I was being paranoid but at this point we had reached the point of no return and it was a very classy hotel. No need to make the hotel detective suspicious.

I checked into the room and immediately called Ellen. "We're in room 343," I said. "I can't wait to see you!"

"I know," she said. "I'm leaving now. I'll be there by 5:15."

At 5:20, I heard a gentle rapping on the door. I bolted over to it and opened it right up. There she was. Ellen. Standing there in all her glory. She was wearing a nice, somewhat conservative blouse and a stylish pair of pants with some sensible shoes. I hadn't actually seen her for a month and a half and I was beside myself with anticipation. She stepped into the room and shut the door behind her. I pulled her close to me and we embraced. We just stood there, hugging and caressing each other.

We sort of stared at each other for a second and then we just melted together again, our lips lightly touching. We gently kissed each other for a minute or two and then separated and walked arm in arm over to the sitting area. The hotel room, at $350 a night, was fabulous. The king sized bed looked very inviting. We both sat down on the sofa and sort of stared at the TV. We both kicked off our shoes and just decompressed for a minute or two.

We made idle chit-chat for a few minutes, catching up on work and whatnot.

"Hey, do you want to order any room service," I asked.

"Um, no. I'm not really that hungry," she responded somewhat nervously.

"Well, before I forget, here is my part of the deal," I said as I reached into my pocket and pulled out the $2,500.00. "Feel free to count it. Hell, take it, dump it on the bed and roll around naked in it if you want."

She laughed at that and became more relaxed. She took the envelope and put it in her purse and, while standing by the dresser, began to unbutton her blouse.

"Going to join me?" she asked with a twinkle in her eye.

"Umm. Say no more," I said as I stood up and began to undress.

Soon we were both standing in front of each other, me in my boxers, and she in her bra and panties. I reached out and drew her close to me again. We stood there, kissing lightly and hugging. I caressed her back and reached down and cupped her ass. It felt so fucking unbelievable.

I moved around behind Ellen and unclasped her bra and pulled her close to me. I gently kissed her shoulders and cheeks from behind while I wrapped my arms around her waist. As I pulled away slightly, I lowered myself to my knees and put my thumbs inside the waistband of her panties and slowly slid them over her hips. As her panties slid down her legs, I lightly kissed her ass. I slowly spun her around so that she was facing me. I grasped her hips and pulled her close to me. I brought her beautiful pussy close to my mouth and began kissing her mound. I could feel a shiver course through her body.

"Man, you have no idea how long I've wanted to do this," I murmured.

"I know," she said. "I'm so fucking wet. Let's get in bed."

I stood up, slipped my boxers off, gently grabbed Ellen's bra straps and pulled her bra off. I led her to the bed and we lay down side by side. I pulled her close to me and kissed her full on the lips. We began to French kiss while she caressed my cock. I was hard as a rock at this point, barely able to contain myself.

"Fuck. I want you," whispered Ellen.

She eased me onto my back and straddled me and lowered herself down onto my cock. I reached up and gently pulled her forward. We began to slowly thrust against each other, moaning quietly. Ellen rose up just enough so that she could begin to French kiss me. Her long hair dangled around my face, shoulders, and chest, lightly grazing me and sending shivers and chills up and down my body. I could smell her perfume and it was driving me up the fucking wall.

"Oh, Ellen," I gently cooed.

"Mmm, yeah," she moaned.

We continued thrusting, our bodies softly slapping against each other. She slowly eased back, sat up straight, and began rocking back and forth, faster and faster. She reached down with one hand and began massaging her clit as she rode my cock.

"Oh," she let out an almost imperceptible little cry. I suddenly felt her pussy tighten around my cock. Her breathing became louder and she shuddered as her orgasm swept over her.

Well, that was simply too much for me to bear. I felt that familiar tingling in the pit of my stomach. I practically convulsed a few times as I shot jets of hot cum deep into her pussy.

"Oh my God, Ellen, you are so fucking hot," I gasped.

She smiled at me and literally collapsed onto me. I wrapped my arms around her back and gently kissed her lips, cheeks, and neck. We stayed like this for several minutes while we regained our composure.

She rolled off of me and lay on her back, legs slightly spread. I glanced over and, honestly, couldn't remember a more erotic sight in all my fucking life! We "cleaned up" a little and just lay there relaxing. Finally, we both got our second wind and were ready for "Round 2".

"I want to eat you," I said, with a slightly devilish grin on my face.

"Sure. I was hoping you would," she giggled.

I put a pillow under her ass and inched my way down between her open legs. I began to lick her pussy and suck on her clit. I flicked my tongue back and forth across her lips. Ellen began to rock her hips up and down gently. As I continued to kiss and lick her pussy, she reached down and pulled my face against her mound.

"Uh, uh, oh, man," she moaned. "Right there. Keep going."

I continued to suck and lick until she suddenly tensed up.

"Ooooh," she whispered, almost imperceptibly as her orgasm swept over her.

"Fuck," she exclaimed, "you know how to push my buttons. Wow. Well, it's my turn now. Give me that cock."

I got on my knees and she eased herself in front of me and began to suck on me. She grabbed the shaft and began to move her mouth back and forth, swirling her tongue around and the head. She'd occasionally massage my balls as she would bring her mouth out to the tip of my cock and then plunge back to the root.

In just a few minutes, I could feel myself on the verge once again.

"Oh, Ellen, I'm going to cum," I groaned.

"Mmmm," she grunted, with her mouth full of my cock.

My knees got weak as my climax swept over me. Ropes of hot cum shot into Ellen's open mouth. She greedily swallowed every drop. After I had recovered a bit, I glanced down to see Ellen staring up at me with one of the most passionate looks I have ever seen. As I looked at her, she became a little self conscious and blushed.

I got more comfortable on the bed and pulled her up next to me. I pulled the sheet up over us and wrapped my arms around her as she lay her head on my chest. We stayed like that for about an hour or so, just kissing and caressing each other.

Finally, the midnight hour rolled around and it was time for us to part company. We both got dressed and just sort of stared at each other. We both smiled at each other as we left the room, arm in arm. I walked Ellen to her car and gave her one last very long and passionate kiss before she drove off.