It was one of the rare occasions when me, Kayli, Jennifer, and Tara were all in our office together. We had just finished a team luncheons, eating food from a local restaurant while planning out the next few months for our real estate business. Kayli and I were also planning a weekend getaway, mostly to fuck, but also because she wanted to check out a vacation house she was thinking of buying. Her husband was unavailable to come, and I had quickly volunteered to keep her company.
While Tara and Jennifer were jealous of us being alone, it was Jennifer who said, “I think while y’all are down there, one of you should be the sex slave for the other.” Me and Kayli looked at each other and Kayli said, “Danny will already do whatever I want, where’s the fun in that?” Tara spoke up and said, “then expand it out. Not only sex, but everything else.” Jennifer said, “yeah, like that night I was free use for Danny. That was a blast, and not just the sex.”
I said I was down for it and Kayli said, “sure, why not? But, how do we decide who is in charge?” I instantly had an idea and said, “let’s have a quick competition. You get Jennifer, I get Tara. Whoever gets their girl to cum first, using only our fingers and mouth, gets to be in charge.” Kayli’s face lit up and she agreed, Tara was quick to agree, but Jennifer said, “now? I have a showing in a hour.” I said, “guess you better hope that Kayli is fast.”
After working out a few other details, I walked over to Tara’s desk and kneeled in front of her, while Kayli walked to Jennifer’s desk. Tara, the tall, blonde girl of the team, had on her usual leggings, a pink swirl design this time. I heard Kayli say, “so, who says go?” I said, “Jennifer, give a count down!” Jennifer quickly counted down from three and when she said go, I pulled Tara’s leggings and thong down and off, pulled her to the edge of the chair, and started to lick and kiss around her clean shaven pussy. As she got wetter and wetter, I kissed and lick more of her pussy lips, spreading them to flick my tongue in and out, taking her lips in my mouth and softly sucking on them.
Hearing Jennifer moaning, I brought my fingers up, slipping one inside Tara, making “come here” motion with it as I licked and sucked around her clit. Sliding my finger in and out of her, I stood up and whispered in her ear, “if you come first, when I get back, I’ll give you a real reward.” I heard Jennifer say something about cheating as I kneeled back down, my mouth and tongue joining my fingers and quickly bringing Tara to an orgasm, her hands pressing my head down into her pussy, her hips bucking up off the chair as she yelled out, “I’m coming!”
Right behind her, I heard Jennifer moaning out, “fuck, I’m coming!” I stood up after licking up Tara’s juices, Kayli standing up as well. She said, “what’s this about cheating?” Tara told her I said something dirty to her, and I said that it wasn’t against the rules. Kayli shrugged her shoulders and said, “true, guess that means you win.” I reached out, wrapped Kayli in my arms, and leaned down to kiss her, swapping Tara’s and Jennifer’s cum in our mouths.
That night, as I was packing to leave with Kayli the next day, I texted her, “by the way, you’re only allowed to wear sun dresses this weekend. No pants, slacks, or shorts. Only dresses. Underwear optional.”
The next day, Kayli picked me up in the early afternoon to make the two hour drive to Park City, a resort town to the south of us. As I got in the mini SUV with her, I noticed that she had pulled her black hair back into a pony tail, and was wearing a pale blue sundress, with spaghetti stings on her shoulders, a ruffle pattern around the chest, and it ended just above her knees. We hugged and kissed before I fully sat down, put on my seat belt and we took off.
She asked me, “so, why only sundresses?” I laughed and said, “because you look hot in them. And it’s easy access. How many did you pack?”
Kayli replied back, “five, including this one. And a few other options, in case you wanted me in something else. Only brought a few pairs of underwear and a lingerie set for the night time, if you want me to wear it.”
I told her that sounded amazing as I placed my hand on her thigh, and she reached down to take my hand in hers. We talked business and life for the first little bit of the drive, until during a break in our conversation, I placed my hand lower down on her thight, and slowly pushed it up, under her dress. Kayli, driving seventy miles an hour, quickly glanced down, and said, “what are you doing?” I laughed and said, “just was curious if you had anything on under this.”
She smiled and said, “you know, I almost had you drive so I could give you some road head. Is there such a thing for girls?”
Moving my hand to the upper part of her leg, she spread them wider for me as I found that she didn’t have any underwear on, and my fingers will soon playing with her clean shaven pussy lips. As she let out a low moan, I said, “I don’t know. Are you going to be able to keep your eyes on the road?” She smirked and said, “probably not. Can’t wait until we get to the hotel? Do I need to pull over somewhere?”
I told her, “Nah, I’ll just keep teasing you.”
And that’s how we finished the rest of the drive, my hand teasing Kayli’s pussy, getting her wetter and wetter, closer and closer, edging her just to the brink of an orgasm, then I would pull my hand away, leaving her to moan in her seat, begging me for more. When we arrived at the hotel a short time later, Kayli held my hand as we grabbed our bags and walked inside. She checked us into our room and as we walked to the elevator, she said, “it’s funny that everybody this weekend is going to assume we’re a couple.” I asked why that was funny and she responded, “I guess I just get turned on by it, people thinking we’re a couple, but in reality, you work for me, we fuck all the time, and I still have a husband at home, while you can fuck whoever you want to as well. Just crazy how life can be viewed by outsiders, yet they have no idea how it really is.”
Alone in the elevator, I pushed Kayli up against the wall, my hands grabbing at her ass under her dress, I said, “you mean that you don’t think that cute front desk clerk wasn’t thinking that we were going to go up to our room and I would have my cock down your throat minutes after she checked us in?”
“Oh God,” Kayli moaned, but I had to let go as the elevator stopped, another couple joining us on it. When we arrived at our floor and walked to our room, Kayli said, “if you’re going to shove your cock down my throat, I just need to remind you that we have dinner reservations for tonight we need to get ready for.” I said, “would you rather give me a blowjob now, or have me pick your outfit tonight, and do something super naughty during dinner?” She smiled, dropped to her knees, and said, “remember, I’m your slave this weekend, so why not both?”
After I face-fucked Kayli and shot my cum down her throat, she emptied out her suitcase, laying out all her outfits for me to pick from. She said, “while you pick, I’m going to go fix my make up and hair.” I gave her one request with her make-up, to which she kissed my cheek, said “ok,” and walked into the bathroom, carrying her make-up bag.
When she came back out a few minutes later, she had stripped off her dress, leaving her completely naked, had pulled her black hair out of the ponytail, leaving it loose around her head, and had on bright red lipstick, my one request for her make up. I looked her up and down, then glanced between her and the bed full of clothes. She asked if I had decided yet, and I told her I was choosing between a few.
I surprised her when, instead of handing her a dress, I picked out a black and red plaid mini-skirt, and a long sleeve, red, top wrap that tied in the lower front corner. She asked me about underwear and I told her none as she smiled and walked off to get dressed. As I finished putting on some nicer clothes for myself, she came up and twirled around, looking dead sexy, with her mini-skirt ending just below her groin, the red wrap low cut, showing her massive double D cleavage, and bright red lipstick. She smiled as she picked out a pair of high heels that she said completed the outfit.
I was a little worried that we wouldn’t fit in at the restaurant we were going to that night, dress wise. Much to my surprise, we actually didn’t look out of place at all. Kayli’s outfit was immediately drawing the eyes of everybody in the room, including our waiter, who kept looking her up and down. After he took our drink orders, I told Kayli, “flash him your tits when he comes back.” She smiled and said, “is this what you meant when you wanted to be naughty tonight?” I told her we were just getting started.
When the waiter brought out our drinks, his eyes went huge when Kayli “accidentally” untied her wrap, her massive breasts spilling out as she tried to cover up. After she tied it back in place, he took our food order, and before he could walk away, I said, “keep up the good service and maybe you’ll get another view.”
I told Kayli to continue to tease him, and she did, brushing up against him, leaning over when he came to check on us, and, my favorite, lifting up her skirt to flash us her ass when she got up to go to the bathroom as he refilled our drinks. With her gone, the waiter said, “you sir, are very lucky to be married to her.” I laughed and said, “actually, she’s my boss and my fuck buddy. So, yes, I am extremely lucky.” He just shook his head in disbelief as he walked away. I told Kayli what he said when she was gone and she asked, “so, what should I do as a finale for him?” We quickly came up with a plan as we finished our dinner.
When he dropped off our bill, the waiter about fell over when Kayli said, “hey, if you give me your phone number, I’ll send you a picture to remember me by. And maybe next time I’m in Park City, we can hook up?” He hurried and wrote down his number on a piece of paper as we paid our bill and left the restaurant.
Driving back to the hotel, my hands were all over Kayli as I told her all the dirty stuff I was going to do to her that night. My hand was up her skirt, feeling her soaking wet pussy as she pulled into the hotel parking lot. Before we got out of the car, I finally stuck my fingers inside her pussy, kissing her neck as I slide them in and out of her, her hips bucking up to meet my hand. As she got close to an orgasm, I pulled out of her, telling her she wasn’t allowed to finish yet.
She wanted to make out in the elevator, but I wouldn’t let her, instead I kept my hand on the outside of her skirt, my fingers teasing her ass and pussy. Once back in our room, I wrapped my arms around Kayli, grabbing her ass, and picking her up. We begun to kiss passionately, our tongues swirling together, as I walked us towards the bed. I sat her down on the edge of the bed, spreading her legs as I kneeled in front of her. I pushed her plaid skirt up, exposing her wet pussy, kissing all around as she begged me to lick her. I finally gave in, running my tongue up her pussy, flicking it in and out of her, as Kayli’s body shudder above me. I found her clit, sucking into my mouth as I brought my hand up, sliding two fingers in and out of her pussy. Kayli placed her hands on top of my head, pushing me down into her, as a massive orgasm finally hit her, her back arching off the bed as she moaned my name.
Standing up, I reached up, pulling her red wrap apart, pushing the sides off her, her double D breasts spilling out, falling to either side of her skinny body. I grabbed her phone, taking a picture of her body, tossing the phone to her and said, “send that to the guy from the restaurant. As she did so, I hurried and stripped off my clothes, my six inch long, thick cock springing free, hitting Kayli’s pussy.
I grabbed onto her legs, pulling her forward, my hard cock coming into contact with her wet pussy. After her orgasm, I had no problem slipping inside her and I was quickly thrusting in and out of her, watching as her breasts bounced on her chest, nearly hitting Kayli on the jaw as she moaned in pleasure. After a few minutes of pounding into her while I stood off the bed, I pulled out and climbed onto the bed. As Kayli rolled over and crawled up next to me, I said, “suck my cock, then ride me.”
Kayli eagerly scooted down to my cock, sticking straight up in the air, covered in her juices. She pulled off the rest of her red top, throwing it to the ground, then kneeled over my groin, swooping her black hair to one side, giving me a perfect view as her red lipstick covered mouth formed a perfect O and engulfed my cock, quickly swallowing my entire shaft. I put my hands under my head, lifting myself to watch as Kayli bobbed her head up and down my cock, her breasts bouncing under her, one of her hands softly squeezing my balls while the other hand rested on my leg.
Making eye contact with me, Kayli popped me out of her mouth, running her tongue up and down my shaft. She said, “may I ride you now?” I told her yes and watched she deep throated me one more time before sitting up. Kayli finished removing her skirt, rubbed her pussy with one hand, while grabbing my cock with her other hand, and put my tip into her entrance. She slowly guided herself down my shaft, moaning as my thick filled her.
Kayli leaned down to kiss me, her nipples brushing against my chest, her body slowly rocking back and forth. When she started to move her hips up and down, she broke the kiss, sitting up on my cock, and I reached forward, taking her breasts in my hands. I squeezed them, pinched her nipples, rolling them in my fingers as Kayli bounced up and down on my cock.
Wanting them in my mouth, I pulled Kayli down until her breasts were at my face. Kayli put her hands on both sides of my head as she continued to ride me, moaning out, “fuck, I love you sucking on my tits.” I had brought her left nipple to my mouth, flicking it with my tongue while I held her right breast in my hand. I sucked her nipple into my mouth, gently biting down on it. I kissed over to her right nipple, giving it the same treatment. I kept alternating between her nipples as she slide her wet pussy up and down my hard shaft.
I let go of her breasts as she sat up a little straighter on me, grabbing on to her hips. I started to buck my hips up as she came down, causing her to moan more and more as I got deeper into her. I told her I was getting close, making Kayli ride me faster and harder, moaning out how she wanted my cum.
I grabbed a tighter hold on her hips, pulling her down on me hard, as I pushed up in her, cum exploding out of my cock as I moaned out loud. Kayli threw her head back, her own orgasm hitting her as my cum filled her pussy. I continued to thrust up into her as she moaned out, “oh God, oh God, fuck me, fuck yes!”
When I was done and starting to go limp, Kayli rolled off me, and I pulled her into a cuddle with my arms. After kissing my cheek, she said, “that was amazing.” I told her that it was just the beginning and she asked, “what else do you have planned this weekend?” As I described to her all things I wanted to do to her, Kayli drifted off to sleep and I followed shortly after.
Source: reddit.com/r/eroticliterature/comments/12eryt8/working_in_real_estate_part_13_m35f30f32f34