Walking into Keith’s house. It was really nice. My first impression of it was that it was very clean but plain. Not a lot of color, not much on the walls, very minimalist, but it felt open and organized. The front door opened into his living room and across the room, I could see a big open kitchen. His living room had a big leather couch, a couple of end tables, and a matching coffee table with a huge flat screen hung on the wall across from the couch. This was all sat next to a huge floor-to-ceiling window peering out towards the driveway with a lounge chair laying in front of it.

Knowing I still looked like a mess I asked where the bathroom was telling him I wanted to freshen up. He pointed me towards a hallway that split between the kitchen and living room. Telling me it was straight down the hall second door on the left. Keith then asked if I wanted a drink, I replied asking for a water and told him if he was going to make a drink to make me one too.

I grabbed my bag from his hand and made my way toward the bathroom heels clicking on the floor as I went. I made it to the bathroom flipping the lights on and closing the door behind me and locking it. I tossed my bag onto the double sink and looked up at the mirror, letting my eyes adjust to the light. Man was I a hot mess,

I’m glad he was still pawing at me on the walk from the car. My lipstick was smeared my eyeliner wasn’t the greatest. I had raccoon eyes from the mascara running and smearing from my tears. My eyelashes were separating and coming off. The front of my dress had my pre cum all over it from grinding my cock on his front seat. I tried wetting it and wiping it off with a rag I found in the cabinet drawer. But this just made wet spots all over and of course no hairdryer to be found in a guy’s house to dry them out. With this I decided to change into my other outfit, a little disappointed that I couldn’t continue in my cute little black dress.

Taking my dress off I realized too that my underwear was also a hot mess and my fishnet's little sticky band around the top edges was losing its effect. So I took my heels off and stripped down to nothing. Standing there, naked smooth as a baby in my coworker’s house felt weird and made me feel vulnerable. I just couldn’t believe where I was and what was happening.

Trying to not take too long I grabbed the rag I was using on my dress and wetted it some more adding some lavender soap I found in the shower. I started giving myself a quick whore’s bath, which felt fitting for the situation. Starting from the top wiping my makeup off and working my way down cleaning up my mess from earlier.

Mid-crotch cleaning Keith knocked on the door asking if everything was ok. Probably worried I was taking so long. I responded telling him I was cleaning up and going to change and redo my makeup. He understandingly said ok and told me he would be out on the couch with my drink waiting for me whenever I was ready. He followed up telling me to feel free to hop in the shower if I wanted and that towels were already in the bathroom hung on the towel rack next to the shower.

Knowing now that he was ok with me taking longer to clean up I took him up on his offer and hoped in the shower. I took my plug out and washed it off; setting it down on the shelf built into the wall. I made sure to clean up real good while also enjoying the cleansing feeling of the hot water running over my naked body.

After my shower, I got out and patted myself dry in front of the mirror. I gave the steam-covered mirror a quick wipe with my towel so I could start to get ready. Once again I started with my makeup putting on a light base blending it in and moving on to my eyes. This time I was able to focus on doing a better job. Applying my eyeliner first, drawing a nice accent around my eyelids adding a little extra in the corners elongating my eyes. I followed up by applying a new set of fake eyelashes.

I already have decently long lashes but I really love how much more feminine my eyes look with much longer and fuller lashes. It gives me the ability to bat my eyes to try and get what I want. I carefully placed my new lashes and used my crimper to properly join them to my own. I then applied my mascara to brush them out and help blend the lashes together and fill them out.

Still standing naked bent over leaning against the sink while applying my makeup. My cock was pressed against the cold stone countertops and had shrunken back down to normal. Starting to get cold I rummaged through my bag grabbing my second outfit of the night.

This was a more sensual dress. A dark blue mini dress. Very form-fitting all the way down, made of a stretchy material it went down to a few inches above my knee. But because of the material, it would always slowly ride up on me as I moved around making me pick at the bottom edge to pull it back down. The back on it is more open on this dress with a few strings of material crossing each other to help hold it tight to my body. Being an open-back, bras are out of the question while wearing it so no need to put one on this time. Though it’s not like I need a bra anyway.

Before putting the dress on I went back to the shower grabbing my plug debating on if I still wanted to use it. I landed on the decision to put it back in so it would help lube me up for the fun to come. I grabbed the lube from my bag applying a generous amount to the plug and pressed it back into my hole.

Next, I grabbed my spare pair of panties from my bag. These being dark blue similar to my dress so it kind of matched. This pair wasn’t as skimpy as my red ones, they were a lacey cheeky style thong with a bit more coverage. I love this pair because it really accents my ass showing off the curves of my butt cheeks.

I checked myself out in the mirror bending over and grabbing my ass cheeks. This pair actually better covered my plug, though you could still tell I was wearing it when I bent over from the obvious outline it made in the panties. I tucked my little cock bunching it up between my legs in the bottom of my panties.

I then slipped my dress on over my head pulling it down and adjusting it over my hips and straightening it out. By now the mirror was mostly clear of the leftover steam and I could better see myself in it. I put my wig back on, brushing my hair out and styling it down. I made sure to grab a hair tie and put it around my wrist for later.

I then sat down on the toilet and strapped my heels back on before standing up to give myself one final look over before joining Keith out in the living room. I felt hot as hell looking at myself in this form-fitting blue dress. Turning to the side seeing how short it was and how it hugged my ass as well as its open back, made me feel super sexy. And the fact that I was dressed up for my coworker really had me excited.

I unlocked the door grabbed my bag and made my way down the hall. Keith, I’m sure heard my heels because he was sitting up in his seat attentively looking in my direction as I walked out. He sat on the couch with our drinks sitting on the coffee table waiting. I apologized for taking so long and he told me it wasn’t a big deal and that I was worth the wait. He commented that I looked amazing and joked with me again about how prepared I was. I just brushed it off telling him, “Hey you never know what’s going to happen.”

I walked over and joined him setting my bag down to the side of the couch than sitting on the couch next to him. Knees together turned slightly toward him trying to be as ladylike as possible.

While I was getting cleaned up he had turned the TV on and began watching some movie to kill time while I got cleaned up. I looked at the drinks on the table in front of us and didn’t see a water, just a couple mix drinks in small whiskey glasses.

I told Keith, “What are you trying to get me drunk to take advantage of me?” Like I hadn’t already blown him on the car ride here.

He joked back, saying, “That’s the plan,” so I played along reaching for my drink and started to throw it back. I drank half of it before realizing how strong it was. Apparently, that really was the plan. I ended up coughing from the burn and making a sour face. He just laughed at me and apologized saying he liked his drinks strong. Which to be fair I did say to make me whatever he was drinking.

We just sat and talked for a couple of minutes awkwardly trying to figure out what to talk about, trying to get back to that same level of flirtatious grabbing and contact we had earlier. It was nice to clean up and make myself presentable again but it also kind of killed the mood.

Keith had moved closer to me and had his arm resting behind my back with his hand now on my hip. He slowly rubbed his fingers against me feeling the softness of my dress. I decided to be bold and asked if he would rub my back and neck. I joked that my neck was sore from the car ride. He laughed, acknowledging that he was the reason I would be sore, and agreed to massage me.

So I leaned over and grabbed the drink from his other hand and stood up and bent over to set both of our drinks back on the coffee table. Giving him a nice close-up of my legs and ass. This caused my dress to ride up on my hips closer to my ass cheeks. I pulled my hair to the side and looked back knowing he would be looking at my ass. I playfully arched my back and stuck my ass out further causing my dress to ride up more and was now showing some cheek.

Feeling my dress slip up on my hips I reached back to pull the bottom hem of my dress back down. My tease made him playfully reach out and grab my legs with both hands. His hands grasping my upper thigh he pulled me back towards him making me fall backwards. He directed me to land right between his legs.

His hands moved to my waist now as I sat at the forward edge of the couch with my butt resting within inches of his cock. I could feel his legs resting against my hips and with purpose, I leaned forward teasing him and wiggling and nuzzling my ass closer to his crotch.

He leaned back into the couch more and took his hand and rested it in the opening of my dress on my bare back. He ran his hand down my back, his fingers skipping over the strings of fabric that kept my dress tight to my body. He rubbed my lower back a few times working his hand under the strings taking in what lay before him. It was now his turn to tease me.

He sat up straight, now grabbing my neck and shoulders massaging them with a firm grip. He grasped my shoulders and pushed down, pulling me towards him while he scooted forward in the seat. With his legs wrapped around my hips and him thrusting into me. I could feel his hard-on pressing into my ass as he held my shoulders pulling me onto his cock. I greeted the feeling of his cock pressing into me by further arching my back and wiggling my ass more to increase the friction between us.

We sat grinding on each other while his hands continued to explore my back and shoulders. He slipped his arm around to the front of me rubbing my chest as he reached up towards my neck. His hand wrapped around the base of my neck as he pulled me back towards him. He started by kissing at my neck and then biting and nibbling. Slowly working his way up to my ear and nibbling on it.

I slid my hand back squeezing it between my ass and his thigh and started groping his cock through his pants. I groped and grabbed and ran my hand along his cock.  The combination of grinding on each other and him biting on my neck and ear while I held his cock rubbing it with my hand was driving me nuts. I couldn’t take it anymore, I wanted more.

I sat up and turned around kneeling in front of him pawing at his pants to quickly unclasp, unzip, and pulled them down. He met my enthusiasm bucking his hips and quickly helping me get his pants down. I grasped both his pants and the waistband of his briefs ripping them down letting his cock spring free. I leaned back against the coffee table with my ass resting on my heels and helped him kick off his pants from around his ankles. He scooted all the way to the edge of the couch with his cock sticking straight out at me. I flipped my hair to one side and dove into his crotch getting straight to work.

I sucked his cock for a couple of minutes as he reached over me grabbing and groping my ass and giving it a few smacks and slaps. After I had his cock was nice and wet with my saliva I pulled off of him and turned around. I pushed the drinks to the other end of the coffee table and laid myself over it hanging my ass off its edge. I let my weight rest onto the table with my knees apart and heels turned outwards. I spread my legs into an A shape. I reached back lifting at the bottom hem of my dress and slid it up over my ass.

He got up and knelt on the floor beside me again groping and slapping my ass, enjoying and taking it all in. He ran his hand over my panties and down my ass brushing against my plug. He gave it a push and began playing with it through my panties, pushing and pulling on it. My cock was laying off the edge pressed up against the table still trapped in my panties. Before long Keith worked his finger under them and ran it down pulling my panties to the side and freeing my little cock.

He continued groping and rubbing my ass and reached down with his other hand and played with my little cock. Grabbing and groping my balls and cock giving it a few tugs then letting go and slapping my ass. I responded with little moans of “oh yes” and small yelps when he would smack my ass.

He worked up to pulling my panties further to the side and exposing my plugged hole. At this point, he played with the plug some more giving it a couple of soft pulls before pulling hard enough for it to pop out. He continued playing with my cock and worked the plug back in.

Keith let it sit halfway in letting my hole adjust to its size. As I grew used to the thicker part of the plug he worked it in and out with small movements before letting it fall all the way back in. He began to pull it all the way out and back in until my hole was relaxed and readily accepting it.

I was so ready. It was so hot being bent over his coffee table, laying there getting my ass and cock played with dressed in a slutty little mini dress. As he used my plug to slowly fuck me I let out an “oh God yes” and some other noises to let him know I was really enjoying it.

He ended up getting up and sitting on the edge of the couch again because he was uncomfortable kneeling on the hard floor. I at least had the table to put my weight on. I took this as an opportunity to move off the table some more and scoot my ass closer to him on the couch. He took the hint and completely removed my plug. He ran his cock along my ass crack as I bounced my ass in a fucking motion.

He gave my ass a slap and smacked his cock against it. He tried pressing the tip against my hole but it didn’t slip in immediately. I moved away from in front of him and reached over and grabbed the lube out of my bag. Handing him the lube he squirted some along the length of his cock as I knelt back in front of him and continued bouncing my ass teasing at the thought of fucking.

He grabbed my ass stopping my motion and placed his cock back at my entrance. Once I felt it pressing against my hole I slowly moved my ass back letting the tip of his cock slide into me. It felt amazing. I was in ecstasy as I started to rock back and forth and let it slowly go deeper and deeper into me. Keith just sat still on the edge of the couch as I worked my way onto his cock. He started rubbing his hands along my back and hips and began to slowly grind his hips forward helping it push further and further into me. Before long I couldn’t go any further down on his cock because my ass was hitting the couch.

Keith let me bounce and control the pace until he could feel that I had gotten used to his cock. He reached forward like earlier and grabbed my shoulders. Grasping and massaging them as he pulled me back onto him. He scooted closer to the edge shoving his hard cock all the way in me until his hips were resting on my ass. He let our bodies press into each other and gave a couple of hard pulls on my shoulders. Really pressing his cock deep into me and letting me feel he was balls deep in my ass. I arched my back trying to match his lust and help him press all the way in.

He began fucking me bent over in front of him, panties pulled to the side as I played with my cock dangling out of my panties. We fucked for a couple of minutes picking up the pace with his hips clapping against my ass and his balls slapping against me. I laid there taking it and playing with myself and came really hard from the feeling of his cock inside me and his hips bouncing off my ass. Not cumming earlier in the car really had me built up and ready to explode. It didn’t take me very long before I was bucking wildly on his cock, cumming all over the floor.

Keith kept his pace pounding away but added more force behind it. He kept fucking me as I let go of my cock still orgasming. I continued cumming with my ass contracting around his cock and my cock flopping around and cumming all over. I gave myself to him as he fucked me and my cock grew soft still leaking cum and bouncing around from him pounding against my ass.

We kept fucking for a few minutes before he announced he was going to cum. He pressed his cock deep into my ass and I begged for it as he shoved it deep and left it there. I could feel it pulse as he shot spurts of cum deep into me. With each spurt, he pulled on my shoulders pressing his hips into me harder pumping his cum into me.

It felt so good, I was numb and tingling with pleasure. He let it grow soft while we both came down off our high and caught our breath. He pulled out and placed my plug back in and pulled my panties back over it. He gave my ass a slap and called me a good girl as he got up to get some towels to clean up.

I reached and grabbed my drink from earlier and downed what was left. It still burned to drink it but I wanted to keep my buzz and continue having more fun.

We talked more and made more drinks and ended up doing it again. But this time standing up bent over the kitchen countertop where we were talking and drinking. He hugged me from behind and I rubbed my ass against him getting him hard again. He kissed on my neck and we repeated what we did earlier.

We both were exhausted and spent. We took a shower together. Where we ended up rubbing and washing each other which led to more fun in the shower. He was spent and couldn’t cum again but I was still so riled up I came again in the shower as I sucked on his cock and played with my own.

It was well past midnight now and I slipped on a spare set of bra and panties before we crawled into bed and he cuddled up behind me. I laid there with my ass nested into his crotch and his arm around me as I drifted off thinking about what had happened. Thinking about what was going to happen at work between us. I grew hard at the thought and wanted to get fucked again but Keith was already passed out and I decided to be nice and let him rest for hopefully some more fun in the morning.

Thanks for reading. I hope you enjoyed this fantasy. Again we were actually co-workers but we found out about each other after we were no longer working with each other and no longer living in the same area. We talked about these fantasies and I will end up sending him this story so he can read through it and indulge himself in my what-if series about him and me. In part three I’ll go into details about our work situation and flirting and teasing and office fun that we fantasized about.