Business Trip With My MILF Boss
- 4 years ago
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BUSINESS TRIP WITH MY BOSS - PT 1 free porn video
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. I couldn’t seem to move fast enough as I rushed around the bathroom with Alan’s cum dripping down the inside of my thighs and my naked boobs bouncing around and slapping into each other.
As it turned out, I had just finished applying my make-up when I heard Matt pull into the driveway, so the timing was perfect. I grabbed my bag, gave Alan a quick “goodbye” kiss, ran out the door and jumped into Matt’s car. The convention center was about three hours away, so Matt and I picked some music on the radio and settled in for a long drive.
It was actually a very pleasant trip….I found that I really liked Matt and enjoyed his company, which was nice, because….after all….he was my boss. Once we got to the convention center, we checked into our rooms, and Matt said we had a ‘meet-n-greet’ social function with the other insurance people in about 1 hour. So we headed up to our rooms to freshen up and change clothes.
I joined Matt in the lobby afterwards, and we headed over to the bar area where the socializing had already begun.
As we walked toward the crowded bar, Matt leaned over and whispered into my ear, “Wow, Jessica, you look fantastic!” I glanced at his face to thank him for the compliment and noticed that his eyes were locked onto my jiggling cleavage as we made our way to the area serving drinks. I was wearing the same wrap-around dress that I’d worn during my interview with Matt, so my boobs were clearly on display, and – with no bra on – my stiff nipples were creating obvious bumps through the thin material. Matt casually put a hand around my waist as we approached the bar area, then let it slip slightly lower to squeeze one of my ass cheeks….and left it there as we entered the pub. I didn’t react….I figured this was just the nature of insurance conventions, and I was both excited and overwhelmed by all the people and activity whirling around me.
The bar was loud, and packed with wall-to-wall insurance people….agents, underwriters, brokers, company reps, potential clients, etc….all talking loud, laughing even louder, and drinking like crazy. I was amazed at the sheer number of bodies crammed into the bar area. The convention didn’t start until the following day, so this was just a chance to meet people from the industry while racking up a big bar tab.
Matt got us both drinks and started introducing me to several of his industry counterparts as we edged our way through the crowd. I could feel my ass and tits getting constantly fondled by unseen hands as we worked our way through the packed room, greeting more people and drinking more drinks. After about 2 hours I was getting a bit worn down. I just wasn’t used to this much intense socializing and drinking. We pushed our way through the throngs of people and managed to find an empty chair off to the side of the bar near several people that Matt knew, so I took a seat while he stood next to me chatting and laughing with his associates.
As I sat there listening to Matt chat up his friends, I realized that….between all the tit groping, ass grabbing, and cocktail drinking….I was pretty flush, and I seemed to be getting kind of horny. I also noticed that Matt’s crotch was almost at my eye level…. constantly bumping into my shoulder and, if I turned just right, into one of my breasts, as well. I wasn’t sure, but I had the impression that his bulge was growing in his pants….every time it bumped up against me it seemed a little bit bigger.
I glanced up at Matt and caught him, once again, ogling my cleavage and nipple bumps, and I gently nudged his crotch with my elbow to get his attention. He shifted his gaze from my tits to my face with a sheepish grin, and I smiled up at him, then reached over with one of my hands to covertly massage his cock through his slacks. My gestures were hidden from the crowd by all the bodies crammed in around us. I found his shaft with my fingers, and began running my hand up and down the outline of his dick as it hung down one of his pant legs.
Matt gave me a big smile and, even though I couldn’t hear it over the din of the room, I’m pretty sure he moaned his appreciation for the gentle rubs his cock was getting through his slacks. As I surreptitiously prodded and rubbed his shaft through his trousers while he tried to carry on a normal conversation with his associates, I noticed with a smile that he was getting hard…..and that he was much bigger than I expected. If this kept up, we’d have a tough time staying undetected by Matt’s friends in our little discussion group.
Not surprisingly, I heard Matt start making ‘time to go’ noises to the people he was chatting with. Then we both offered everyone we’d been talking to handshakes and ‘see ya tomorrow’ salutations before shoving our way through the crowd and out of the bar area, heading for the elevators. By the time we got out of the room, my boobs were almost pulled out of my dress from all of the hands that groped and fondled them as we pushed our way through the mass of people.
I fixed the top of my dress as we stepped onto the elevator, but Matt stood very close behind me and reached around from the side so no one could see as he played with my right boob the whole ride up to our floor. He was standing so close behind me that I could feel his erection rubbing against my ass cheeks, which he was clearly doing on purpose. I casually used my hand closest to the elevator wall to reach behind me and gently squeeze his engorged shaft. It felt great in the palm of my hand, and I couldn’t wait to set it free from his slacks so I could get both of my hands…and mouth… on it.
When the elevator door opened, we tried to look casual as we hurried to Matt’s room. Once inside, he focused again on playing with my tits, while I untied my wrap-around dress and let it drop to the floor. Standing by the foot of Matt’s bed in only my thong panties, I unzipped Matt’s pants and pushed his slacks and boxers to the floor so he could step out of them while he peeled off his shirt and let it drop. Then he re-attached his hands to my jiggling boobs while I playfully slapped his nearly erect shaft to watch it swing back and forth between his legs. I gently nudged him backward until he was sitting on the end of the bed, then knelt between his legs and used one hand to fondle his balls as I sucked the mushroom tip of his prick into my mouth.
As I bobbed my head up and down on his rigid staff, it quickly became fully erect. I took a break from sucking it for a minute and, holding it straight up in the air, used one of my hands to stroke the entire length, from tip to base, while just appreciating its size and beauty. I pulled the tip back toward my mouth and began sucking again, this time using my tongue to focus on the ridge around the bulbous head, while continuing to use one of my hands to pump his shaft. Matt was lying back on the bed with his legs dangling over the edge of the mattress and his feet on the floor on either side of me. He lay there with his eyes closed and his hands clasped behind his head, moaning as I knelt between his legs, jerking and sucking his engorged staff.
I could hear him murmuring, “Mmmmm….Oh, my God, Jess….yes….yes….that feels great…..mmmmm….yes…..just like that…..mmmmm…..shit, I’m going to cum…..aaaahhh…”
In no time, I felt Matt’s hips jerk and heard him groan, as he blasted a huge load of cum against the back of my throat. I tried to swallow all of it, but some managed to spill out from the sides of my mouth, dripping onto my tits as they swayed and bounced from my bobbing head and pumping fist. I kept sucking and stroking, and Matt kept cumming, until his balls were finally empty and his breathing started to return to normal. I continued sliding my hand up and down his glistening shaft, as I licked away the final drops of jizzm seeping out from the tip of his cock. When he had finished cumming, I kissed the head of his dick, used a wash cloth from the bathroom to wipe my mouth, then plopped down on the bed next to him.
Wearing a big smile, he said, “That was absolutely amazing, Jess….I hardly imagined I would ever get my hands on those gorgeous tits of yours, let alone get a blowjob, too….holy, shit….I’m blown away….literally!”
I smiled back at him and said, “I’m a little surprised, too….this whole convention thing is new to me, so I’m a bit overwhelmed. Plus, I had no idea you had such a beautiful cock, and…with all the drinking and tit grabbing….I kind of got carried away.”
Matt raised up on one elbow, sucked a nipple into his mouth and gently nibbled on it, then released it with a “plop”, and said, “Now I’m going to return the favor.”
He climbed off the foot of the bed, knelt between my legs, pulled my panties down past my ankles and tossed them over by my dress on the floor. Then Matt grabbed my thighs and pulled my ass to the edge of the mattress, draping my legs over his shoulders. Once he had me in this position, he began using his tongue to lick and suck my labia, edging closer and closer to my clitoris, until he finally sucked my throbbing clit into his mouth and began flicking it with his tongue. My God, it felt good!
My vagina was already extremely wet, and Matt’s tongue was making it even wetter….. I could feel my pussy juices running down my ass crack and getting smeared all over Matt’s chin. Once he got a rhythm going, Matt reached up with both hands and began massaging my heavy breasts, squeezing the flesh and pinching the nipples with his fingers as he sucked and licked my pussy.
Matt’s tongue on my clit and his fingers pinching my nipples were having an electrifying effect on me, sending little shock waves from my boobs to my vagina. I grabbed the back of his head, and rocked my hips in rhythm with his mouth, grinding my aching clit against his tongue, until I suddenly exploded…..drenching Matt’s face with my cum juices, as an intense, tingling orgasm coursed through my entire body.
As I lay on my back near the edge of the bed, enjoying the throes of my amazing climax, Matt stood up with my legs still resting on his shoulders, and – to my surprise – it felt like he was poking my vagina opening with the head of his cock. I opened my eyes in surprise and looked down between my legs and…..holy shit!.....Matt was hard again….only about five minutes after he shot a huge load of cum down my throat! I watched in awe as his fully erect shaft stood straight out from this torso, nudging my dripping wet cunt with the tip, anxious to get inside me.
He took my legs that had been draped over his shoulders, spread them wide and held them apart by hooking them over each of his elbows. Then he lined up the head of his dick with my pussy and shoved it in. I was absolutely drenched from my orgasm, so his stiff rod slipped in easily. Matt began pounding his hips back and forth rather forcefully, slamming his cock deep into my pussy, over and over, making my tits bounce up and down like a wave pool, slapping against my chin with every lunge. Holy shit, it felt amazing!
I moaned and grunted with every thrust, “Uhnnn….Uhnnn….yes….oh, my God….yes….that….feels….so…..good…. Uhnnn …Uhnnn….shit….fuck, yes….Uhnnn…..Uhnnn…”
I saw Matt’s eyes were focused on my jiggling tits as he hammered his prick in and out of my cunt, so I just threw my hands above my head and let him enjoy the show…..watching my flailing boobs bounce around and slam into each other, as he continued to plow my pussy.
Almost without warning, another climax ripped through my body, causing me to arch my back and let out a loud, wailing moan, “Oh, my God…..yeeeessssss…..fuck, yeah……aaahhhhhhh……aaaahhhhhh…..yes…..keep going….. aahhhhh….yeeesssss…...uhmmmmmmmmm…..”
Just then, Matt grabbed both of my tits and slammed his cock as deep as he could go, let out a groan and erupted inside my cunt, blasting a huge load of cum all over the walls of my pussy. He kept pounding his dick in and out of me, as he continued to empty his nutsack with every thrust. When he was finally done cumming, he slowed down his strokes, then finally stopped thrusting altogether and just flopped on top of me as we caught our breath and enjoyed the throes of our orgasms.
Wouldn’t you know it…..that’s when my cell phone started buzzing. Of course it was Alan, calling to say goodnight, and of course I had to take it. -->
Geraldine
- 13.04.2021
- 13
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