BUSINESS TRIP WITH MY BOSS – PT 1

Once my two kids were grown and out of the house, I decided I needed a job to keep me busy and give me a sense of purpose. My husband, Alan, thought it was a good idea, too, so I began scouring the want ads in our local newspaper.

I found an ad by an independent insurance agent who needed an office assistant to help run his small firm. At the interview I saw that “small” was a bit of an understatement. It was a two-person operation….the owner – Matt – and his assistant….which would be me, if he hired me.

I had dressed to impress, wearing a low-cut, wrap-around dress that came to about mid-thigh, and left very little to the imagination up top. I had married early, and even after two kids, I was an attractive 39 year-old brunette, with a knock-out body. My big, 36DD tits were clearly my defining feature, and this dress really set them off nicely. If Matt was a boob guy, I was getting the job. Well….he was….and I did.

It was obvious during the interview that he couldn’t keep his eyes from straying down to my chest, where my heavy breasts swayed slightly and my nipples were making obvious bumps in the thin fabric of my dress. Matt explained the job requirements, which included a lot of cold calling, policy paperwork, and travel to insurance conventions about every three months. He explained the conventions typically lasted 3 days, and the company would cover all travel and registration costs.

Still struggling to keep his eyes above my neckline, he said, “Would that be a problem for you, Jessica?”

I smiled as I watched his gaze continue to slip down to my tits and said, “Not at all. My kids are all grown, and it’s just my husband and me now, so I can handle being out of town for a few days at a time.”

So, I was hired.

Knowing that Matt liked my boobs, I typically dressed for the office in a way that accentuated them – usually without a bra – giving him plenty to look at and enjoy as I bent over or reached high to open drawers and file paperwork. Matt was an attractive guy who appeared to be in pretty good shape, and the attention he was giving me was definitely feeding my ego. He even managed to casually bump into me, grab my ass or nudge my tits on occasion whenever we passed each other in the office.

About four weeks after I started working there, Matt informed me that we had a convention to attend in a nearby state.

He said, “Pack a bag for three days. I’ll bring all the company documents and hand-outs we need. It’d probably be easier if I pick you up at your house tomorrow morning and drive us both there. Sound OK to you, Jess?”

I said, “Sure, that sounds great. I’d rather not drive that far by myself, anyway.”

The next morning when I woke up, I looked at the bedside clock and figured, since I had packed my bag the night before, I had just enough time to shower and dress before Matt picked me up. As I was climbing out of bed, I felt Alan slip his arm around my waist and pull me back in. He pushed the covers to the foot of the bed, and reached up with his hands to grab both of my tits. As he pulled me back against him, I felt his morning wood slip in between my legs, rubbing up and down my vag lips in search of my pussy opening. It didn’t take long….this was a fairly common occurrence in the morning, so slipping his morning hard-on into my twat had become pretty automatic.

I spread my legs a little more to give him better access, then said over my shoulder, “You need to hurry, hon….Matt’s picking me up early this morning. We’re driving to that convention I told you about yesterday.”

Breathing heavily into my ear, he said, “No problem, babe,” and began rocking his hips, thrusting his rigid shaft in and out of my pussy in earnest, while fondling my boobs and pinching my nipples. It felt good, but with my mind elsewhere, I knew I wasn’t going to climax that morning, so I threw one leg over his hips and pushed my ass back against his torso, allowing him even better access to my cunt and, hopefully, encouraging him to cum quickly.

It worked….in just a few more strokes, I heard Alan’s breath begin to catch, followed by a low moan and soft grunts as his morning erection splashed several streams of spunk deep inside my pussy.

“Unh….Unh….yes….yes….Aahhhh….Aahhhh….God, that feels good….Hmmmm….,” he murmured into my ear, as he slammed his dick as far into me as it could go, holding it there for a few seconds while he unleashed his load of cum, then pulling it out to the tip and shoving it back in again….and again…and again….until his nut sack was finally empty.

I only gave him about 30 seconds to enjoy his orgasm, then I jumped out of bed and hurried into the shower to get ready.