The Office Affair

It was typical of me to do something nice for the women in my office on holidays, especially Valentine's Day. I wasn't the office boss or even any sort of manager, just a guy who liked to do small things out of the kindness of my heart to make the people around me feel a little better about the day. I worked for a small advertising consulting company in the suburbs of Chicago called Catenger Marketing. I was in the office most of the year, handling office operations and creating slide presentations, while most of the other men were out presenting to current and potential clients. All of the salesmen were also managers of the office, which didn't make much sense because they were hardly ever there.

You are probably thinking that there is no way I would randomly do nice things for the women I work with, unless I had an underlying agenda. Some of you are maybe you probably think I am gay. Or, maybe you actually believe that I am genuinely nice guy. Well, all those opinions may change once you read my Valentine's Day story of moral dilemmas and questionable decisions.

…………………

On this particular Valentine's Day, I stopped at a local supermarket on my way to work to grab several individual roses and some chocolates. I arrived at the office about an hour before starting time, so that I could anonymously place a yellow rose and some chocolates at each woman's desk for when they arrived. The clerk at the supermarket's floral shop informed me that yellow was a good neutral color because it was a symbol of friendship, otherwise I would have just bought a bunch of red roses. I gave a flower and candy to all 10 women that worked in the office; Betty, Linda, Faith, Bethany, Karen, Gina, Melissa, Tammy, Jamie and Alison.

Betty was the secretary to the entire office and the organizer of all in-office events. She was a grandmother of two, probably in her early to mid 60s, and her husband was a retired dentist.

Linda and Faith both worked in the financial department. Linda was the accountant and Faith was the financial manager. They also acted as the human resource department for the company as well. Linda was divorced, probably in her mid-40s, and a mother of three teenage children. Faith, also in her mid-40s, never married yet was very free spirited and easy going. Many of the other men in the office believed that she was a closet lesbian, but I didn't agree.

Bethany was the assistant to the financial department. Basically she answered phone calls for Linda and Faith, and helped out with all the paperwork. Bethany was an attractive woman in her early 30s, married and mother of a two year old girl.

Karen and Gina worked in the computer department as technical support for the office, as well as assistants the two male computer programmers. Karen, 28 years old, was the mother of two boys and engaged to an older man that was not the father of her children.

Karen had many attractive features, but never quite lost the weight that she gained during her pregnancies. Gina was fresh out of college, 22 years old, and still very wild in her ways. If ever we would meet for happy hour, Gina was the one who planned it. She was petite and cute with a smoking hot body. She was a bit of a flirt around the office, but I think it was more flaunting so she would get her way. Gina dated a football player from her college who was actually expected to be drafted into the NFL later that year.

Melissa, Tammy and Jamie all worked in the operations department with me. We were basically assistants for the six salesmen and a support team for all of our clients. Melissa was 28 years old and recently married. She had a 'girl-next-door' cuteness to her, but her obnoxious behavior made her unattractive to me. Tammy and Jamie, both 24 years old, were best friends since high school. Both women were very pretty in similar ways and they had almost identical personalities. Many people used to mistake them for being sisters. However, the glaring difference between the two was Jamie's enormous DD tits. Tammy was hired by the company first, but within a few months, she convinced management to hire Jamie. I don't think it took much convincing when Jamie came to her interview with her boobs smashed into a tight V-neck sweater. Back when Jamie started with the company, all the guys in the office would drool at the sight of her, but I would do my best to be a gentleman about it. Before I knew it, Jamie and I started dating. After a few months, we both realized that everything about the relationship was sexual, so we both agreed to break it off before it made it too awkward for us to work together. I was just happy knowing that I was the only person in the office that got to see her massive jugs naked…many, many times.

Then there was Alison. She was the owner's daughter who worked at the office part time while she finished her final courses to get her bachelor's degree. Alison was beautiful in every aspect. She had the most gorgeous facial features, sparkling hazel eyes, amazing bright smile, bronze toned skin and long curly blond hair. She was tall, to me anyway, being only 5'6. She was about 5'9. Her body features were thick and strong, curvy in the right places. Alison was the same age as me, 26 years old. Our birthdays were actually within a few days of each other. She had a great fashion sense, always wearing clothes, accessories and jewelry that perfectly accented her body. Her personality was just as stunning as her exterior beauty. Despite completely different backgrounds growing up, Alison and I shared a lot of common interests. The heartbreak of it was that Alison was 3 years married to a young successful real estate entrepreneur.

As everyone started to arrive between 8:20 and 8:30am, I wondered around the office to slyly get a glimpse of everyone's reaction to their gifts. Typically, all we ever did was stand around and bullshit for about the first half an hour of work anyway. The first reaction of most of the women was that the presents must have come from the owner or president of the company. I wasn't one to boast about my kindness, so I just played along and acted like I did not know who left the Valentine's gifts.

After several minutes of chit-chat, everyone finally dispersed to their office or desk. As soon as I sat down at my desk, I immediately received an instant message on my computer screen from Jamie…

JamBurk82: Thank u so much for the beautiful rose and chocolates!!!

TomFMorgan80: What makes you think it was me?

JamBurk82: Because u r the only 1 sweet enough in this office to do so.

TomFMorgan80: Well, you are very welcome. I just wanted to remind everyone that V-Day isn't just for lovers. I like to put smiles on all my friends' faces. Keep this between us, I want everyone to keep guessing who they were from.

JamBurk82: OK. U r way too cute. Nicky is a lucky girl. Thnx again.

Within five minutes I was bombarded by instant messages from most of the women, thanking me for the gifts. Some of them actually came to my office to thank me in person. I knew that Jamie wouldn't be able to keep the secret, but I didn't mind, I liked spreading some joy throughout the office through a simple act of kindness. It was a nice change from the monotonous crap we endure day in and day out.

Since Alison was part time and her father owned the company, she sort of had the luxury to show up and leave as she pleased. Around 9:45am, I heard Alison walk into the main entrance, saying hello to everyone along the way. A bit of nervousness set into my mind. I had a little more of a surprise hidden for her than just a rose and candy, so I was a little concerned for how she might react. It was not necessary for her to walk past my office to get to her desk, so I sat there in anticipation. I could hear her drop off her coat and hand bag at her desk, then make small talk with Jamie who she shared a large, open workspace with. My heart was racing until the moment Alison finally stepped into the doorway of my office.

"Good morning, Thomas." She said in her typical bubbly fashion. She always called me Thomas, Mr. Thomas, or Mr. Morgan, unlike everyone else in the office who simply called me Tom.

"Good morning. Happy Valentine's Day!" I must have had a smile on my face that went ear to ear. My day was already going well, and it immediately got a hundred times better once I saw her. She looked absolutely adorable, as usual. She was wearing a cute, pink half-sweater that exposed a small bit of her toned stomach and pierced naval. Her long hair, full of curls was still damp from her morning shower and hung lazily down the side of her face, onto her shoulders. She had on a tight black skirt that hugged her curves down to her lower thighs. The length of her tall, beautiful legs were snuggly covered by shear pink stockings that ran from the bottom of the skirt down to her designer, open toed, black shoes.

"Happy Valentine's Day to you too." She replied as she entered further into my office and leaned against the back of a chair that was in front of my desk.

"Wow, you look amazing today…As always." I said softly, as my forehead began to perspire a bit at my hairline.

"Thomas!!! Stop it." She replied softly with a big, blushing smile on her face. "I better get to my desk and get to work before I get yelled at again. Just wanted to say hi."

"Don't worry, Jeff (president of the company) and all the managers are out of the office today." I mentioned as she turned to walk out of my office into the hallway.

She stopped right outside the doorway, looked at me over her shoulder and said, "Yeah, my dad is coming in today either." Then she gave me a seductive wink and walked away towards her workspace.

My face must have been flushed red as my entire body began to tingle. I soon realized that Alison failed to mention anything about the flower and chocolates left at her desk, so I got up from my seat and ventured to the area where she worked. As I entered the opening to her workspace, Alison quickly turned around in her chair with the rose and candy in hand…

"This has you written all over it, Thomas."

Then Jamie spun around from her desk and replied, "Who else do you think would do such a thing? Tom is always doing nice things for everyone here."

"I know. That's why I know it was him. Thank you Thomas. You are way too sweet." Alison utter with a genuine look of appreciation on her face. I simply nodded as a response.

As I continued to chat with Jamie and Alison, I anticipated the discovery of my extra surprise for Alison. After a few minutes, Jamie's phone rang and I saw my window of opportunity. I grabbed a piece of paper off a filing cabinet and asked Alison if I could borrow a pen. When she turned and opened the top drawer of her desk, she quickly slammed it shut again. She turned around abruptly with a look of 'Oh My God' on her face and made sure Jamie did not see. Jamie had her back to both of us, so there was no way she saw what was in Alison's drawer.

Earlier that morning, before placing everyone else's gifts, I cleared the clutter out of Alison's desk drawer and lined it with white rose petals, then spelled out 'I (heart) U" with red rose petals. I also included a large heart shaped box of gourmet chocolates and a poetic card expressing my feelings. In the split second that Alison saw all of this, she freaked out a bit. She looked at me with a confused look of concern, then motioned for me to go back to my office so we could privately chat over instant messenger. I simply gave her that same seductive wink she gave me earlier, and returned to my office.

As soon as I got back to my desk, there was an instant message waiting…

AliCat80Meow: Ur alone, right?

TomFMorgan80: Yes, I am.

AliCat80Meow: U R Crazy! What if someone else would've seen that?

TomFMorgan80: I wasn't thinking about that. I just wanted to do something special for you to express my feelings. I'm sorry.

Just then I saw Jamie walking down the hallway past my office and I could hear Alison open the drawer again. There was about a 30 second pause, then…

AliCat80Meow: U have no reason 2 b sorry. That's 1 of the sweetest things any1 has ever done for me.

TomFMorgan80: I would do anything for you. You deserve it.

AliCat80Meow: U make me feel so good baby! Thank U sooooo much! I luv u 2!

TomFMorgan80: Did you read the card? And the chocolates are your favorite…Godiva dark chocolates with caramel center and silver almonds.

AliCat80Meow: U know me too well Thomas.

AliCat80Meow: I'm going 2 sneak 2 the restroom & read the card, so don't msg me til I get back.

As I am sure you can tell, this obviously was not the first romantic encounter or discussion that Alison and I ever had. Everything had started several months earlier around Halloween. Alison trusted me enough to inform me that her marriage was failing and she was going to seek a divorce her relationship with her husband did not turn around. Everyday, I was there to comfort her and help her through her tough times. We exchanged phoned numbers, and occasionally talked on weekends and the days she was not at work. As our bond grew stronger and her marriage got weaker, things really started to click between us. One thing led to another, and before we knew it, we had developed a mutual loving and sexual relationship with each other. We were not quite daring enough to meet for any secret rendezvous outside of work, but we did what we could with our time when nobody else was in the office.

Around Christmas and New Years, the pressures of family and friends constantly visiting and nagging wore on Alison mentally and emotionally. She requested that we stop the affair and rethink the morality of it all. I had no choice but to agree to her request and to keep my own feelings and emotions in check. Everything at work went back to normal for the most part from the middle of December until the end of January. The pressures of the holidays ended, but the struggles with her marriage had resurfaced. As soon as she emotionally opened up to me again, the bong between us solidified again. Though we restrained our physical connection over that period, the relationship continued to expand. Valentine's Day was my chance to do something for her that she had been neglected in her marriage.

I figured I would have at least 10 minutes before Alison returned from the restroom, so I sat at my desk doing my tedious morning tasks. About thirty minutes had past and I had already completed all my necessary work for the day. I became a bit concerned for Alison's delayed return until I stepped out into the hallway and saw that all of the women were at the far end of the office. They were all gathered around Bethany's desk admiring the gigantic brown teddy bear and floral arrangement she had just been delivered courtesy of her husband. I ignored the typical giggling and snickering coming from the group, that I hear every Valentine's Day, and returned to my office. I figured the day would be full of floral and gift deliveries, as it usually was, so it was easy to ignore. Before I could even get back to my chair, I heard someone swiftly making their way down the hall behind me. Just as I turned to sit, Alison darted into my office, threw a plastic bag onto my desk, wrapped her arms around me and gave a deep, passionate kiss.

"That card…the gifts…You have no idea how good those make me feel. I truly do love you with all my heart." She whispered in my ear before she returned to the doorway of my office.

My body and mind did not know how to react. I kind of just stood there in a daze for a few seconds before I slithered back into my seat. The excitement continued to grow between us, as we silently stared into each other's eyes. Finally, the silence broke….

"Aren't you going to look at your gift?" Alison uttered as she leaned into my office, then stepped back to view if anyone was coming down the hall.

I grabbed the bag from my desk and nearly choked on my saliva when I saw that there was a silky red thong and bra inside. I had not noticed right away, but Alison was no longer wearing a sweater, but a tight pink t-shirt, that was about the same length as the sweater. It was apparent that she was not wearing a bra because the shirt conformed firmly against her breasts, slightly displaying the erect nubs of her nipples.

Probably with a mild expression of confused excitement on my face, I looked towards Alison. She took a step into my office, turned around, dropped a folder to the floor of the hallway, then leaned over to pick it up. As she bent over through the doorway, she had full view of anyone walking in the hall. My eyes were 100% focused on her behind as she began to slide the tight black skirt up her legs. I could feel the bulge in my pants growing as she slowly slid the material over the curve of her hips, revealing her perfectly rounded ass and glistening pussy lips.

She looked back at me between her legs as if she was a longer snapper about to hike the ball to the punter. My face must have turned beet red when she ran her hand up the inside of her thigh, then slid a finger slowly through the folds of her wet twat. It was now apparent that the thong and bra in the bag were the ones she wore to work. She must have removed them when she went to the restroom to read my card. In a cheesy fashion, I blew her a kiss, then held the opening of the bag to my face and inhaled deeply. It was a familiar scent of pleasure that filled my nose and lungs. My hard-on grew stronger and stronger with each whiff.

She gave another quick glance down each end of the hallway to make sure nobody was coming. I sat the bag on the floor next to my chair as Alison stepped to the side of my desk. I rolled my chair next to Alison so I could rub my hand up and down the back of her legs, along the length of her silky stockings. She stared down into my eyes as she took the finger that she ran through her pussy and slipped it into my mouth. I sucked the flavored dampness from her finger as I continued to glide my hand along her legs. Pulling myself closer to her, I slowly worked my hand up the inside of her thigh. As I continued to the top of the stocking, her skin was becoming warm and moist. When I reached the top of her thigh, I teased her by moving my hand back down, then working it slowly up the other thigh in the same fashion. I moved my hand up to the firm cheeks of her ass and softly massaged each.

I could see the frustration in her face when she removed her finger from my mouth, leaned down close to my ear and said, "Would you stop with the torture and just finger fuck me already!"

That was the only invitation I needed. I positioned my arm between her legs and cupped my hand over her pussy. I worked my thumb through the slippery folds until I found her clit and massaged it softly. She was already dripping wet as I slid a finger deep into her waiting hole.

This was not the first time that I fingered Alison at my desk while other people where still working in the office. Even though there was a door on the individual offices, I always kept mine open when Alison was in there to avoid suspicion. There was a pane of glass directly beside the door anyway, so people could still see clearly into my office even if the door was closed. The floor of the hallway would creak so bad, you could hear anyone approaching from 20 feet away in either direction. If we heard footsteps, I would remove my hand from her skirt and act as though I was going over paperwork with her.