This winter some of my coworkers started planning an unofficial work ski trip for those who can ski. I’m pretty new at my marketing agency having just joined from college maybe five months before. Naturally, I’m one of the youngest in the agency and I always get teased for it. Doesn’t matter how tall I am, I’m practically a baby at age 23.
About 12 or so had signed up and since I’m really good at skiing, I thought this would be a great opportunity to bond with my coworkers. Haley who is one of my desk mates was really excited about me joining and invited to take me in her car.
Haley was gorgeous much like many of the girls in marketing are. She had long legs, a beautiful shade of orange red hair, green eyes that make you melt, and the most confident footsteps you could ever hear walking down the hallway. Her bluntness and smarts have brought her a lot of respect within the agency and has become pretty important. When I started I was assigned a desk next to hers and she has always been really friendly with me.
I have daydreamed many times about what it would be like to see her on her knees looking up at me, the roles reversed, begging for me to release my cock so that she could suck it. I have also daydreamed of having her boss me around, putting me on my knees, riding my face, using me.
But I knew she was off-limits in many different ways—she was my coworker, much older than me, taken, and…by a girl. Most of these thoughts were innocent fantasies that took place when I was home and horny.
Friday came and she picked me up outside of my apartment after work. Haley’s girlfriend Cassie gave out a ”Woohoo!” at the site of the large case of beer that I brought along with my skis. And of course she was just as gorgeous as her girlfriend. Just as fit and skinny as Haley, but instead had black hair and blue eyes.
Haley seemed different, much more relaxed. She didn’t seem as serious and cut throat as she sometimes does while at the office. I had met Cassie before at a happy hour and she seems to have that effect on her. She’s more outgoing and very chill, really the perfect compliment to Haley.
It was snowing, and after a few hours of driving, we eventually made it to the mountains, but just as we did, the traffic came to a halt.
“A traffic jam? Why are there so many people?,” asked Cassie
“Oh man,” I added from the back. “This usually happens when there’s been an accident up the road. I came up with my dad once and it took hours for them to clear it up.”
“Change of plans then,” said Haley as she turned the steering wheel and drove onto the shoulder. “We’re not too far from an exit. We’ll take it and go to the nearest hotel for the night.”
She had such a way of taking command. I don’t think I would’ve ever drove onto the shoulder that quickly, much less backwards against traffic. Good thing she had decided to do so. The one hotel we found only had one room left—a king bed and a couch.
“Perfect!” said Cassie. “We’ll take it.”
The storm was intensifying. We grabbed a case of beer from the car along with a deck of cards. We weren’t going to let this set back mess up our night.
We got into our bedtime outfits for the night. I wore my grey sweat shorts and t-shirt. I had only brought so much underwear so I planned on sleeping commando. I figured they wouldn’t notice.
When I stepped out of the bathroom I see Cassie wearing a loose crop top with thin straps. Her nipples poked through the shirt very clearly. I could almost make out perfect shape of her breasts. Her cute belly button in full view. Below she had boxer shorts that she rolled up so that they gripped her pelvis. Meanwhile her thong straps poked up onto her hips.
Immediately, I realized that going commando was a bad idea. I could feel my dick engorging. I try to place my hand over it without indicating anything suspicious. I couldn’t believe that she would dress so boldly in front of me.
“Let’s play!” She said excitedly as she started to shuffle a deck of cards sitting on the floor.
The problem got worse when I saw Haley. She wasn’t wearing anything necessarily revealing—an oversized t-shirt draping over her breasts that tented the fabric. But the shirt was so long that it covered below as well and I realized as she sat down on the floor that she was wearing nothing but lacy panties underneath. Fuck me.
I couldn’t tell if this was their normal bedtime outfits or if they planned their night outfits to be intimate and they had to audible somehow.
I sat down as quickly as I could before my own tent became too visible.
The card games turned into drinking games. Cassie and Haley were very flirty with each other and sometimes that flirt spilled onto me. I would get a subtle lick of her upper lip from Cassie or Haley would caress my jaw line and call me her handsome colleague when it was my turn to drink.
At a few points they would give each other a quick kiss. Each time they would linger a little longer.
My cock was driven crazy at the sight of these two women getting increasingly flirtatious. I had managed to tuck it under my waist band but that didn’t necessarily make it unnoticeable.
The girls weren’t really holding back anymore. Cassie seemed to enjoy having me watch. Then, at one point when I lost and had to drink, they kissed again. A particularly longer kiss and while they had her eyes closed, Cassie moved her hand to the edge of her shirt and then lifted it all the way up to her chest fully exposing one of her tits at me. I nearly chocked on my beer and spit some out.
“Woah Cowboy!” Said Haley laughing, “maybe that’s the sign we should call it”
Obviously, Haley hadn’t noticed. Cassie couldn’t help her mischievous smile—biting her lower lip. She seemed proud of herself.
I needed to keep this going. I thought being horny in this situation was moot but this was becoming exciting. The way this game had gotten so raunchy and now I know what Cassie‘s tits looked like. I had to play this right. But before I could say anything, Cassie stepped in.
“Bedtime!”
Fuck. You’ve got to be kidding me. My cock was raging and it needed release. I was already contemplating sneaking into the bathroom and rubbing it out to the thought of Cassie’s tits while they fell asleep.
We all brushed our teeth together in the bathroom. I was so horny I couldn’t help but stare in the mirror at Haley‘s shirt. I could almost make out her breasts from the bouncing of her arm going back-and-forth as she brushed. Because her arm was raised, her shirt lifted ever so slightly revealing a peak of her round ass. Another save to the memory bank.
“Don’t worry about the couch. It’s way too uncomfortable. You can sleep with us.” Cassie smiled.
Oh boy. This girl’s gonna get me in trouble.
Haley looked at her, unsure for a second, but then shrugged her shoulders and continued brushing. We all got into bed. My plan was to wait until they fell asleep before sneaking out into the bathroom. I got in at the right side of the bed. Haley on the left. Cassie jumped into the middle eagerly.
After some late chatter, we went quiet and that’s when I could hear kissing noises. Cassie faced away from me, but I could see Haley‘s hand caressing her face. I guess me being in bed with them wasn’t gonna stop them from their romantic evening.
I couldn’t imagine they were gonna go very far with this, but the thought of it was making me so hard again. I couldn’t help it. I had to touch myself. I reached down and pulled my shorts off. The tip of my cock overflowed with pre-cum.
I started tugging at it very slowly making sure they would not notice any movements as I faced them. It felt so good to finally give into my temptations; each stroke felt so well earned rhythmically matching the sounds of their lips smacking.
Suddenly, I felt Cassie‘s foot grazing my leg. It felt cool against my skin. Her feet are incredibly soft. It went up slowly all the way up to my thigh. It wouldn’t be long before she could tell that I was no longer wearing my shorts. I didn’t stop what I was doing. Eventually she found what she was looking for. Her toes gently rested under my balls. The feeling was incredible. Her cold foot against my hot ballsack. Cassie wanted to make sure that I knew that she was including me. I started stroking a little faster.
The make out had also picked up the pace a little bit. I pressed my balls, a little bit more against her foot trying to see if she would get more involved. But after a few moments, Cassie removed her foot.
I stopped stroking in protest hoping that she would notice. Seconds later, I felt Cassie‘s bare ass hardly press against my groin, my cock against her smooth ass cheek.
My mind went crazy, how did this fun little night end up like this? Laying in bed with my hot older coworker, and her girlfriend who is making some pretty clear advances towards me. She adjusted her ass l until my cock was smothered in between her ass cheeks. They were still making out.
I couldn’t bear it. I needed it. I wanted it.
I placed my hand on her hip and slowly I moved it up under her shirt following the dip of her waist until I grabbed a handful of her breast. I moved my hips, teasing my cock up and down, feeling her asshole against my shaft. She moaned into Haley’s mouth.
Cassie then grabbed my hand, turned it around and guided it up Haley’s shirt and onto her tit. Haley’s were a lot more of a handful, but just a supple. I wondered if Haley could tell it was my hand. She moaned back into Cassie‘s mouth.
Somehow one of my wildest fantasies had come true. Two of the hottest girls I know were making out in bed with me and one of them was moaning to my cock.
I lifted my hips back and slid my cock in between Cassie‘s legs pressing my shaft against her pussy. As I moved my cock back-and-forth, her lips parted and her wet pussy, lubricated my shaft and tip. I continued massaging Haley‘s breast, playing with it and gently pulling at the tip of her nipple.
That’s when I feel Haley’s foot reach over Cassie and onto my leg. She knew. I was in bed with the hottest woman in the office.
I did not tease Cassie for long. As soon I as my cock was full of her wetness I found her opening and pressed the tip of my thick cock onto it. The opening was tight, trying to resist its separation, but its own lubrication betrayed it.
I wondered if a cock had ever graced this pussy before. I pressed the full tip inside.
“MMMMPH!” She moaned
My cock is thick and long. I pulled back a little before pressing 2 inches in—a moan. Then back, then 3 inches in—another moan. Then back and forth again and again until my cock was fully engulfed by Cassie’s pussy.
“Fuck!” She let out.
I pause to feel it struggle, tightening and releasing as it adjusted.
Haley grabbed her face and continued kissing her.
With each pump she would let out a little whimper into Haley‘s mouth. Haley giggled with excitement. Cassie had gone cock crazy.
She had played with me all night and finally got what she wanted and she was getting it over and over and over again. Her tight pussy, desperately squeezing at my cock and her juices overflowing down my shaft.
Haley put her fingers against Cassie‘s clit. Her whimpers turned into mindless groans. Haley was matching my tempo as I slammed my cock into her girlfriend‘s pussy. I reached back to Cassie‘s tits, squeezing them as all the attention in the room had turned to her.
The mindless groans turned to higher and higher pitched moans.
“Ohhh!!! Fffffffffuuuuck!”
Her body started lightly twitching. Her pussy started convulsing, squeezing hard, but being met immediately by the length of my rigid cock. Her body twitched harder as she whimpered in Haley’s arms.
When the dust settled, I slowly removed my cock from her tired pussy. Haley looked over at me with the same look her eyes that have seen be so cutthroat at work.
It was her turn now.
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