Sam was a good-looking guy, tall and handsome and he had an affable personality and a charming smile. As a boss, he could be a bit demanding and even though he was very married, I could tell he could probably be charmed into doing anything I might want him to do.
I didn’t set out to entrap him, although I will admit, I had selfish desires. Because of our close working relationship, I had to be careful. I certainly didn’t want to appear whorish or “easy”, but at the same time, I was a young single girl and I was tired of the bar scene and one-night stands. I certainly didn’t want to steal Sam away from his marriage, but I also envied the relationship he had with his wife, whom he talked very dotingly about.
I dropped little hints, like winks and smiles, a quick flash of the cleavage, to see if he might bite, but he was either afraid, dumb as a box of rocks or simply not interested. I didn’t feel like he was dumb, or afraid.
Finally, one day as we were sitting in the corporate conference room preparing for a briefing, I slipped into a chair next to him. I purposefully allowed a little extra leg to show, just to see if he might notice. His quick glance at my “faux pas”, reassured me he wasn’t gay and he might be susceptible to the tease.
He didn’t say anything, but his shuffling of the papers in a folder reassured me that I had not missed my mark. I asked him if he was nervous and he reassured me that he wasn’t. I started to excuse myself back to my workstation, but he asked me to stay for the briefing, a sure sign, I thought, of my making headway.
The briefing went off as planned, with no unexpected issues cropping up. Afterward, as we each headed back to our respective workstations, mine being an office desk outside of his executive suite, he thanked me for staying in the briefing.
“It’s my job to help you out,” I replied. He smiled and disappeared into his office. About an hour later, as he was leaving for lunch, Sam casually asked if I’d like for him to bring me back anything. I told him I was skipping lunch and mentioned I was trying out a new diet. I really wasn’t on a diet, but I wanted him to think I was.
“You need a diet,” Sam replied, “Like I need a girlfriend.”
“Let’s not undercut girlfriends,” I quickly shot back, noting that “girlfriends make the world a little special.”
I didn’t want him to think I was making a play on him, so I quickly added that I had several girl-friends and that our time together was always very special.
“Do tell,” Sam replied, a wry smile crossing his face. It was the first time Sam had shown any real sense of humor in anything I may have said.
“I didn’t mean it THAT way,” I quickly shot back. Sam smiled.
“Hey,” he replied, “I am an open-minded guy. You do whatever you want to do. It’s a big world.”
Before I could respond, the executive suites elevator “toned” and Sam stepped on to it. I watched as the doors closed, pondering what he had just told me.
Sam returned about an hour later, handing me a deli sandwich and a Coke.
“Stay healthy,” he said as he sat the items on my desk and disappeared into his office.
I stepped into his office after a few minutes.
“Do you Snapchat?” I asked.
“Not really, why?” he asked.
“I was just thinking that if you did, the next time I need something, I can just ‘snap’ you,” I replied.
“Wouldn’t texting me work better?” he asked.
“I wouldn’t want the world to know I text my boss,” I replied. “Texts can be traced, snaps are more private.”
So in an instant, he agreed to set up a Snapchat account.
“Sit down,” he instructed, nodding to a chair in his office in front of his desk. I took up a seat and immediately crossed my legs, very ladylike in front of him. I waited as he downloaded the application on to his phone.
“Now how does this work?” he asked.
I closed my eyes and lowered my head. Did I really have to show him how Snapchat works? Yes.
“So, is this totally secure?” he asked.
“Yes,” I reassured him, “… and, the message disappears after a few seconds after the other person reads it.”
We exchanged Snapchat IDs.
“Send me a message,” I instructed.
I waited a few seconds and my phone beeped. I looked at the message.
“Show me your boobs.”
I laughed out loud, covering my mouth in surprise.
“I’m just kidding,” Sam remarked. “Is it gone?”
I showed him my phone to reassure him the message was gone. He seemed satisfied.
“OK,” Sam remarked. “How are we doing the Baker proposal?”
Damn. He was all business. I hated it. I retreated to my desk, a bit flustered but also reassured that I had partially broken through the “I am your boss” barrier. I focused on the Baker Report, all while debating and plotting in my mind, my next move.
That evening, tired and flustered, and not being able to find a guy to take me out, I opened a bottle of chilled wine and downed it. Sam came to my mind. I stripped out of my bra and snapped a selfie. I loaded it into snap chat and pushed it off to Sam, with the words, “thinking of you.”
A few seconds later and Sam replied, “Holy Moly! I was only kidding.”
Suddenly, reality hit me. I had just flashed my boss. Oh shit! I just knew I was ‘fired.”
I quickly snapped back an apology and explained I had been drinking. I waited for a response and when one didn’t come right away, I worried even more. I was about to doze off, since I was in a drunken stupor, when my phone “tinged” in a response.
“Nice boobs.”
I stared at Sam’s response for the longest time. I snapped back another apology and explained it wasn’t like me to show things off.
“Oh please,” Sam replied. “You’ve been teasing me for months. Keep it up and I’ll be forced to give you a pay raise.”
A pay-raise? Now, we were talking! I wanted to send Sam a full body shot but decided to hold back to see where things might be going. I sure wasn’t going to tip my hand in Snap Chat. The fact that Sam had commented about my boobs, excited me.
Getting up in the morning was tough. I had a huge hangover and thought about calling into work “stupid”, but then remembered I had to finish off the Baker Report. I showered and dressed, then undressed; well sort of undressed. I slipped out of my panties, leaving them on the credenza. My skirt almost reached the top of my knees, so I was pretty sure I wouldn’t be flashing anyone unless I really wanted to.
I have great looking legs and I love to go stockingless. I slipped into a pair of black six-inch pencil-heeled stilettos and headed off to work. I got there before Sam and quickly finished off the Baker Report, so he would have it as soon as he walked in the office.
Sam wondered in around 8:30. He was unusually chipper, tossing out a “good morning,” to ensure everyone in the office suite knew he had arrived. I smiled as he walked past my desk.
“How is your head this morning?” Sam asked. I smiled back.
“The head is fine,” I replied, “But my pussy aches.”
Sam chuckled out loud.
“Be careful,” he matter-of-factly replied, stepping into his executive office, closing the door behind himself. A few seconds later and my intercom light lit up.
“Thanks for the Baker Report,” Sam said.
“My pleasure,” I replied, very business-like.
“Do you want to go for lunch?” he asked.
“Sure,” I replied. I was ecstatic, yet still a little bit nervous. Eleven-thirty couldn’t come fast enough.
The minutes ticked by like an eternity. Sam was quiet. Finally, at about eleven-forty, he asked if I was ready for lunch. I was.
We headed down the executive suites elevator together and for the first time, I got to know Sam’s car. It was a two-seater sports car, one I had seen in the parking garage and marveled at. It was totally cool and so was Sam as he lowered the top and steered us out on to Executive Boulevard. I wasn’t prepared for the wind with the top down and had to hold my long hair in place, with one hand. My skirt inched up my legs. I noticed Sam glancing down at my well-toned thighs.
He asked where I wanted to go for lunch. My first thought was a burger place. He suggested a steakhouse. We valet parked and as we did, I unintentionally flashed the valet. I knew it because he turned blood-red in the face. Sam took note as we walked into the steakhouse.
“I think the valet guy liked what he saw,” Sam noted. Now it was my turn to be embarrassed.
“I guess I should make sure I wear my panties when I wear a short dress,” I jokingly replied.
“Maybe so,” Sam said.
The maître’d seated us at a booth. As I sat down, Sam started to take a seat across from me. I scooted down the leather-benched seat and patted the open space.
“Sit next to me,” I implored. Sam looked around, as if he was looking to see whether or not there was anyone in the restaurant who might tattle on him, and then seeing it was OK, he slipped on to the leather seat beside me. He took a deep breath and forcibly exhaled. I could tell he was nervous.
I grabbed Sam’s hand and squeezed it in mine.
“It’s OK,” I said. “We’re only having lunch.”
“I wished it was that simple,” Sam replied.
“It’s.. just… a… simple… lunch,” I reiterated very slowly.
Sam nodded his head in agreement. He then leaned over and asked,
“Are you wearing any underwear?”
“No,” I replied, “No, I am not.”
Sam’s hand trembled, as he slipped it on to my leg, slowly sliding it back and forth across my bare skin.
He swallowed hard.
“You are such a tease,” Sam whispered. “I’m not sure I should even be here with you.”
I reassured him everything was OK and that I wasn’t doing anything for any reason other than I liked him.
“But you know I am married,” Sam replied.
“Yes,” I whispered. I reassured him that it was not my intention to cause him any issues in his marriage.
“if you want or need a raise,” Sam replied, “I can talk to HR.”
I reassured Sam that while a raise would be nice, I had other unfulfilled needs. He said he didn’t think he could fulfill my needs. I reassured him he could, slipping my hand out of his and on to his leg. I leaned in and poured on the charm. It was now or never. I had my game face on and I was well prepared.
“Why don’t we just skip lunch?” I pressed.
Sam swallowed hard again.
“… and do what?” he asked.
I knew he had a boner. There was no way he couldn’t have one. I slipped my hand into his lap, feeling for it.
“Let’s go have some fun,” I said, squeezing his massive erection.
“I should probably say, ‘No’,” Sam replied, as I squeezed his cock, through the thin fabric of his trousers, “But I can’t.”
He scooted across the bench, holding on to my hand in his as a waiter approached. He quickly explained we had an ”emergency situation” that had to be handled. The waiter was very professional and said he understood. We quickly made out way back to the valet stand. The valet probably thought we were crazy, since we had just arrived. As we stood and waited for Sam’s car, he slipped his arm around my waist and pulled me in close to where we stood in the shadow of the restaurant building.
I was careful to not flash the valet a second time.
Sam drove to a nearby hotel. He asked me to wait in the car while he secured the room. I was so freaking nervous and horny, all at the same time. Finally, Sam appeared and we walked the hallway down to an executive suite. As soon as we entered the room, Sam was all over me.
I quickly dropped to my knees in front of him, unfastening his trousers and pulling them and his boxer shorts down to find what I had been longing for. His manhood was thick and hard, the veins popping out, their blood flow trapped. He was a bit larger than most of the guys I had been with, which worried me just a little.
I fingered his tool, studying it, before slipping it into my mouth. He let out a soft moan as I worked his manhood deeper and deeper into my oral cavity. I pulled it out and run my tongue the length of it, taking my time to gently provide equal attention to his testicles. Pre-cum leaked from the end, when I circled the head of it with my tongue, and as I used my thumb and fingers to gently massage his tool.
He pulled me back up into a standing position in front of him and pressed his lips to mine. His kisses practically drained me. I could barely stand up. Somehow, he managed to help me to the bed, where he finished stripping me. I invited him to dine at the “y” and he didn’t hesitate. Oh my God! He had the most wicked touch of any man I had ever been with. I think I climaxed several times over before we finally got down to taking things to the next level.
He slipped the head of his massive tool into my love box. I remember that much. After that, everything was a blur. I remember experiencing several deep orgasms and then, I think I passed out. When I awoke my head was resting on Sam’s bare chest, my hand on his shoulder and I had one leg tossed over him as we lie naked and spent beside each other.
“Don’t we need to get back to work?” I sheepishly asked.
“Don’t worry,” Sam replied, “I think they can handle things OK while we are out of the office for a bit.”
“I hope so,” I replied. the Baker Report was still on my mind.
“What about the Baker Report?” I asked.
“It was already sent and approved,” Sam replied. “All we have to do is wait for the response.”
“What do we do in the meantime?” I stupidly asked.
“I don’t know,” Sam replied, “but whatever we decide to do, let’s do it together.”
I had no problem with that request at all. The tease was complete. The raise was a nice bonus as well.
