Business Trip With My MILF Boss
- 4 years ago
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BUSINESS TRIP WITH MY BOSS - PT 2 free porn video
After my kids were out of the house, I went out and found a job in the insurance industry. This meant going to conventions several times a year with my boss, Matt. About a month after I started working for Matt, he took me to my first insurance conference, and we ended up fucking in the hotel. Just as Matt, my boss, finished cumming inside me, I heard my phone buzz. When I looked, I could see that it was Alan, my husband, calling to wish me a ‘goodnight’, so I had to answer it.
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So, with Matt still laying on top of me….his stiff cock still shoved deep inside my cunt…..I reached over to my purse on the night stand and pulled out my phone
Still trying to catch my breath, I tried to sound as normal as possible when I put the phone to my ear.
“Hey, Alan…..you caught me just as I got into my room,” I stammered.
“Oh, good….wow, you sound kind of out of breath,” he said with an implicit question in his voice.
“Yeah, I took the stairs up to my room. You wouldn’t believe how many people are at this convention. The elevators were packed,” I said, rather impressed with my improvisation skills.
As Alan and I fell into a typical “just called to say goodnight” conversation, Matt slowly pulled his softening prick from my pussy, then climbed onto the bed and knelt near my head, dangling his flaccid cock….still glistening from his cum and my pussy juices….just inches above my face. As I continued talking to Alan, I sucked the tip of Matt’s swinging dick into my mouth, then used my lips and tongue to clean it off whenever I had finished talking and was listening to Alan’s part of our conversation.
After about 10 minutes, my conversation with my husband was done and Matt’s cock was clean. Alan and I exchanged “I love you’s” and said our goodbyes, then I put the phone away and looked over at Matt.
“Holy shit, Matt…..I wasn’t expecting any of this….but, really…..holy shit!”
Matt toyed with one of my nipples, which was surprisingly still erect, and said, “Yeah, me neither, Jess. But what a fantastic surprise…..this is turning into the best insurance convention I’ve ever been to!”
After a few more minutes of laying around we ordered room service and, while we waited for it to be delivered, I moved all my stuff from my room into Matt’s. After we ate, we lounged around on his bed, naked, watching TV and fondling each other until we both fell asleep.
The next morning, Matt and I took a shower together, where he spent a lot of time soaping up my tits and tweaking my nipples, while I reached between us and stroked his morning hard-on. After playing with my boobs for a while, he spun me around to face the shower wall and used one hand to rub the head of his cock up and down my slit, looking for my fuck hole. I arched my back a little and spread my legs for him, leaving my pussy completely exposed….he quickly found the opening he was looking for and shoved his rigid pole into it. He pounded me from behind with his hands on my hips, making my heavy tits bounce into the glass wall of the shower stall, over and over.
With his thick shaft stretching out my cunt and his testicles slapping against my clitoris with every stroke, it didn’t take long before I let out a groan and creamed all over his cock. My God, that felt good! I continued pushing my ass backward into every one of his thrusts as I reveled in my early morning orgasm. After only a few more strokes, Matt reached around and grabbed my swaying boobs hard, then slammed his cock deep inside my pussy, blasting a huge load of cum into my cunt. I could hear him moan as he kept hammering his prick in and out of me, sending rope after rope of hot, creamy jizzm into my tingling pussy. Holy shit, I loved it.
After he finally stopped cumming, he pulled his softening dick out of me, and we finished cleaning each other up before heading downstairs to join the conference sessions.
The meetings went great….we got some promising new leads, and Matt leveraged his relationships with several associates to help expand his footprint in our local insurance space.
After the meetings were done for the day, Matt and I headed back upstairs to our room. We barely made it inside and closed the door before our clothes were in a pile on the floor, and I was kneeling on the bed….. straddling Matt’s face….grinding my clitoris against his mouth as I held onto the headboard and rocked my hips in rhythm with his licking tongue. This was one of my favorite positions for oral sex, and it didn’t take long before I was creaming all over Matt’s face. He kept licking and I kept cumming until my pussy juices were running down his chin and dripping onto the pillow beneath his head. I was in heaven!
While he ate me out, Matt had been using one hand to squeeze my boobs and pinch my nipples as they dangled above his head, while using his other hand to stroke his rigid cock to full erection. Once my climax was over, I slid down his chest, past his torso, and right onto his engorged prick. I was so wet from cumming, it slid into me effortlessly, and I began rocking my hips up and down on it….riding it to the very tip, then dropping down to the base, over and over. In the cowgirl position like this, I was able to rub my clit against the base of his shaft on every down stroke, and I could feel another orgasm building between my legs as I kept bouncing up and down on Matt’s stiff rod.
Just as I felt my second climax rip through my body, I heard Matt catch his breath and grab my hips….pulling me hard into his torso as he pushed the shaft of his cock as deep as he could into my cunt. As I reveled in the warm, tingly sensations of another orgasm, I felt Matt erupt inside my pussy, spewing streams of hot cum deep inside me….over and over, until his nutsack was finally empty.
When Matt finished cumming, I plopped down on top of him to catch my breath, while enjoying the aftermath of another fantastic climax.
And just like the night before…that is when my cell phone buzzed. And….again, like the night before….it was Alan calling to say ‘goodnight’.
I slid off to the side of Matt’s chest, grabbed my phone from my purse with one hand, and put it to my ear as I reached over with my other hand and began stroking Matt’s soft, glistening penis. While Alan and I had our usual ‘goodnight’ conversation, I toyed with Matt’s flaccid cock….rubbing the head and sliding my hand up and down his wet shaft.
About halfway through my ‘goodnight’ call with Alan, Matt’s prick started getting hard again. I was a bit surprised, but happily continued stroking his growing prick while trying to maintain a casual conversation with my husband at the same time. To Matt’s credit, he was able to muffle his moans with a pillow as I jerked him off with one hand and held the phone to my ear with the other. Just as Alan and I were finishing our call and exchanging “I love you’s”, Matt’s cock erupted with a stream of spunk shooting about a foot into the air from the tip of his dick. I kept stroking Matt’s pole….his jizzm splashing onto his stomach and dripping all over the fingers of my pumping fist….while I finished up with Alan and we said our “goodbye’s”.
The next morning started out the same as the previous day….with Matt fucking me in the shower. This time I had my back up against the tiles of the shower wall, with my legs spread wide, and Matt’s cock pounding my pussy while my tits bounced up and down between us.
Afterwards, we headed downstairs to our conference meetings. When the day was done, we ate dinner with a couple of Matt’s associates, then headed back up to our room for the night. Like the night before, we wasted little time getting naked, but this time Alan happened to call while Matt was kneeling behind me on the bed, slamming his cock in and out of my pussy doggystyle. Neither one of us had cum yet, so Matt stayed inside me, but slowed the pace of his strokes, as I grabbed the phone from the night stand and put it to my ear.
Still on my hands and knees, with my legs spread wide, I said, “Hey, Alan….is it that time already?”
“Yeah…just calling to say goodnight. How were your meetings today?” he asked.
“Really good, but busy as hell. I think we’re finding new business, though, so overall it’s been a great conference.” I said, then looked over my shoulder at Matt and added, “I’m learning a lot and really enjoying myself.”
Matt smiled at me, grabbed my dangling tits with both hands, then thrust his dick hard into my pussy, causing me to stifle a grunt.
Alan didn’t seem to notice, but I gave Matt a dirty look and shook my head. With a wry smile on his face, Matt winked at me, then – with his hands playfully squeezing my swaying boobs – continued slowly sliding his dick in and out of my wet cunt as I continued my ‘goodnight’ conversation with my husband.
Once Alan and I had exchanged “I love you’s” and hung up, I tossed the phone aside and started pushing back against Matt’s forward strokes. Talking to my husband with Matt’s cock sliding in and out of my pussy had aroused me much more than I expected. Matt got the message and started hammering away from behind, holding my hips in his hands and pumping his hard prick into me like a piston. My breasts were swinging wildly beneath me, slapping into each other and making a clapping sound…..sort of like the sound Matt’s hips were making as they slapped against my ass cheeks with every one of his thrusts.
I grunted and moaned as Matt picked up the pace and plowed my pussy from behind. Holy shit, I was in heaven…this felt amazing! My mind seemed to be in a haze as an orgasm ripped through my body, causing me to moan loudly into my pillow and my legs to tremble from climaxing. I pushed my hips back even harder against Matt’s forward thrusts, and very quickly felt another orgasm wash over me from nipple to clit.
As I enjoyed my latest climax washing over me like a warm blanket, I closed my eyes and rested my head on my pillow ….leaving my ass sticking straight up in the air so Matt could keep pounding away. After a few more strokes I heard Matt’s breath begin to catch, then felt him grab my hips and push deep into my cunt, releasing a stream of cum all over the inside of my pussy. When he had finished cumming, we both collapsed onto the bed to catch our breath….Matt laying on my back, but still gently rocking his hips and sliding his still hard cock in and out of my dripping wet cunt.
“Fuck, Matt….I think I’m really going to like coming to these insurance conferences,” I murmured between gasps for air.
After a few deep breaths, he laughed and said, “Well, I’m sure going to enjoy them a hell of a lot more than I used to….that’s for sure!”
The next morning we fucked again in the shower, then checked out of the hotel and jumped in Matt’s car, heading back to Seattle.
We weren’t on the road 10 minutes before I had Matt’s pants unzipped and his cock in my hand, sliding my fist up and down his shaft as we drove toward home. He got hard pretty quickly, and we hadn’t been driving thirty minutes before I could tell he was about to erupt. So, I leaned over and covered the tip of his prick with my lips and jerked him off into my mouth, splashing a stream of cum against the back of my throat. I swallowed all of it, then continued sucking and licking his dick as he finished emptying his nutsack into my mouth.
After I cleaned Matt’s glistening staff with my tongue, I kept fondling it with my hand as we continued our drive back toward Seattle. When we were still about an hour away from home, Matt’s prick started getting hard again. I leaned over and began sucking it, which made it fully erect within a few minutes. Our timing was perfect, since a highway rest stop was coming up about a mile further up the road. Matt pulled in, and we parked at the far end of the parking lot. As soon as we stopped moving, I threw my leg over Matt’s hips, straddling him right in front of the steering wheel. He used the lever by his hip to move the seat backward about ten inches so we had a little more room. Then I pulled my panties to the side, positioned myself directly over his engorged prick and dropped down onto his rigid hard-on. I started bouncing up and down on his stiff pole, grinding my clitoris against the base of his cock, while he pushed my shirt up to my chin and started squeezing my tits and sucking on my nipples. It didn’t take long before we both had explosive orgasms. I creamed all over Matt’s thick shaft as I bounced up and down on it, taking it as far inside my cunt as it could go, and he closed his eyes and let out a groan as he blasted another load of cum….his third of the day….deep inside my pussy.
I grabbed some tissues from my purse and cleaned us both up, while Matt re-adjusted his car seat and pulled back out onto the highway. He started to stuff his flaccid cock back inside his pants, but I told him to leave it out….I just really enjoyed looking at it…..even when it was soft, and draped over one of his thighs, or dangling directly down over the edge of the car seat. Every once in a while I’d reach over and play with it for a few minutes….I just couldn’t seem to keep my hands off it.
About an hour later he dropped me off at my house, helped me get my bag from the trunk, then surreptitiously squeezed one of my boobs and, with a sly smile said, “Great trip, Jess….see you on Monday at the office.”
I smiled back at him, pushed his hand off my tit and playfully shook my head at him, saying, “Yep. See you at the office.”
I stood and watched him drive off toward his home, then turned and walked up my sidewalk toward the front door.
When I got inside, I found Alan in the kitchen making a sandwich. He stopped when he saw me come in, and hurried over to welcome me home. We shared a nice, deep kiss as he ran his hands all over my body….squeezing, pressing, pinching….as always, it felt nice to have his hands all over me. I wrapped one of my arms around his neck, then reached between us with my other hand and found his erect penis through his pants….he was rock hard, and it felt great to have it in my hand again.
I unzipped Alan’s pants and pulled out his stiff prick and began slowly stroking it from base to tip, spending a little extra time rubbing the head, as Alan closed his eyes and moaned his pleasure.
“Aahhh, that feels good, Jess….I know it’s only been three days, but it feels like a lot longer,” he murmured.
I nuzzled his neck and said, “Yeah, three days does seem like a long time….it definitely feels good to be home.” Then I gave him another deep kiss, smiled at him and said, “Here’s a coming home present for you,” as I slid down to my knees in between his legs, and sucked the head of his cock into my warm mouth.
Alan leaned back against the kitchen counter and used one hand to grab the back of my head, as I started rocking my head back and forth on his engorged prick. With his hand in my hair directing the pace, I sucked his dick in and out of my mouth….using my tongue to stimulate the edge of the bulbous tip….and using one hand to stroke his shaft, while using the other to fondle his balls. As I continued giving Alan a “good to be home” blowjob, I couldn’t help but notice that he and Matt had pretty similar sized cocks. Matt’s was maybe a little thicker, but they were both beautiful, big dicks that felt great in my hand and sliding in and out of my mouth.
Alan moaned as he encouraged me to pick up the pace, then held the back of my head firmly as he shoved his hips forward, pushing the head of his cock all the way to the back of my throat, before blasting several ropes of cum into my mouth. I happily swallowed his entire load, then continued sucking and licking the length of his dick as he rocked his hips and spewed more cum onto my tongue. After swallowing the rest of his spunk, I cleaned off his cock with my mouth, then planted a small kiss on the tip of his prick before stuffing it back in his pants and pulling up the zipper.
I stood up, gave him another deep, tongue-filled kiss, as I patted his still semi-hard cock through his slacks and said, “God, it feels good to be home, hun. Now I need to take a shower and clean up….I worked really hard at the conference, and it was a long drive home.”
After that, Matt and I only got one room whenever we went to our industry conventions. We had to fly to some of them, but others we drove together in his car. When we drove, I had his pants unzipped and his cock in my hand from the time we pulled onto the highway, until the moment we pulled into the hotel parking lot.
Interestingly enough, Matt and I only fucked in the home office about three times per week…usually when one of us closed a sale or got a customer to sign a policy extension. I can’t really explain it, because on our convention trips, we typically fucked at least twice a day. But, I couldn’t really complain….the convention sex with Matt was amazing, and the ‘good to be home’ sex with Alan was fantastic, so between the two big dicks in my life, I was enjoying more orgasms than I could count. -->
Geraldine
- 18.10.2020
- 19
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