My Roommate’s Boss


It was a typical Friday night. The roommate in bed asleep and I was sitting in front of the television watching a movie. I was tired and probably would have gone to bed, but my roommate’s supervisor was coming buy to drop of the materials for a project that had to be finished by Monday. I had never met Cindy before, but my roommate, Emma, made her sound pretty laid back, so I wasn’t too worried about appearances.

It was around eleven when I heard a quiet knock on the front door. I answered it and was surprised to find a tall, leggy brunette wearing a short denim skirt, yellow stiletto heels and a yellow blouse that did nothing to hide her large breasts. “Hi,” she whispered, “I’m sorry I was so quiet, but I didn’t want to wake anyone up.”

“Don’t worry,” I said, “once she’s asleep nothing wakes her up.” I stepped aside, swept my arm inward and said, “Come on in.”

She smiled and I felt that familiar tingle down below. If she were my boss I would have been fired for harassment within a month. She walked past me and I was pleased to see that the view from the back was as good as the view from the front. Her ass was firm but plump, and it filled out her skirt perfectly.

She walked in and set the bag full of files she was carrying on the table. “So what are you watching?” She asked as she looked at the television.

“Doctor Who reruns,” I said.

“Which Doctor?” She asked.

“Matt Smith, but it is the early part of his run.” I could not believe she was a Whovian. It was hard to not drool.

She looked at the television, then the bag, and finally me before she said, “There are a couple of things I should probably show you so you can tell Allie in the morning. Is that okay with you?”

“Absolutely,” I said. It was not like I was going to pass up on an opportunity to spend more time looking at her. “Why don’t you sit on the couch and I’ll grab something to drink. Would you like something? I have beer, wine, water–.”

“Beer would be great,” she said.

I grabbed a couple of amber ales, popped the tops and made my way back to the living room. I sat down next to her, close enough to see what she needed to show me, but not close enough to make her uncomfortable. “Here you go,” I  said as I handed her the beer.

“Thank you,” she said. “I was supposed to go out with my girlfriends tonight, but work comes first you know?”

“Yes I do,” I said. I worked two jobs, so I was very aware of how much work could dominate life. “So, what do we have here?” I asked as I looked at the file folders she had laid out on the coffee table.

We spent the next half hour reviewing the information while she taught me how to do the reports that my roommate would spend the weekend working on. By the time she was finished we were sitting close enough to each other that our legs were touching. We sat back and watched the Doctor save the universe and finished our third beers. I was feeling good from the beer and from the heady scent of her perfume, but I knew the time was coming to an end.

The episode concluded and I was prepared to hear Cindy say her goodbyes. She placed her hand on my knee and said, “Why don’t you grab us another beer and I’ll start the next episode?”

The way her hand lingered on my knee sent a thrill through me. “Sounds like a plan.” I hopped up from my seat and headed to the kitchen. When I returned to the couch I was pleased to see that her skirt had creeped further up her legs. “Here you go,” I said as I handed her the perspiring bottle.

“Thank you,” she said before she took a drink from the bottle. “I really appreciate this, Michael.” She took the bottle from her lips and dropped her hand down so that her wrist rested upon her leg and the cold wet bottle rested against her inner thigh. “Mmmm, that feels good.”

“I bet it does,” I said as I licked my lips.

“Here, why don’t you feel?” Cindy reached over and held her bottle against my thigh. The cold, wet glass would have been enough to make me jump, but the way she slid it up my thigh made me moan. “I thought you might like that,” she said with a smile. She dragged the bottle over my shorts and across the increasingly obvious bulge at the top. She took another drink from the bottle then undid the top few buttons of her blouse. She slid the bottle between her breasts and spun it around. “Mmm,that feels delicious.”

“It can’t possibly feel as good as it looks,” I said.

“Why don’t you find out?” She said.


I smiled as I reached over and slid my hand over her breast. The cold left by the bottle quickly disappears under the heat of her skin. I moved my hand around until my fingers slid beneath the fabric of her yellow lace bra. She moaned when my fingers went over her nipple, so I pinched it and made her gasp. “You’re right,” I say, “this does feel delicious.” I used my other hand to undo the rest of her blouse buttons. “Now I think I’ll see if the taste matches.” I pulled her tit out and lowered my lips to the nipple. I sucked it into my mouth and ran my tongue back and forth across the tip.

Cindy moaned and put one hand on my head and held me tight against her breast. “Oh God, Michael.” She said as she arched her back and pulled out her other tit so that she could pinch the nipple. She panted and moaned as I went from one breast to the other. Before I knew it she had one hand between her legs rubbing her pussy through her panties. I reach down and place my hand on the back of hers and guide her fingers beneath the fabric. Our fingers spread her lips and slid inside her pussy with ease. Her legs spread wider and gave us more access so that we could stroke her faster and faster until she bites her lip and bucked her hips against our hands as she rode out an orgasm.

I pulled my lips from her breast and she said,”I am so glad that work interrupted my plans.”

“Me too,” I said as I pulled my finger from her pussy and stuck it in my mouth. “Like I thought: delicious.”

“Nasty boy,” she said with a laugh. She got up from the couch and slowly stripped out of her clothing, teasing me better than any Friday night stripper. When she was finished she stood before me wearing nothing but those fabulous heels.  “You’re not the only nasty one here you know,” she said as she pushed my knees apart with her own. She stepped forward and bent over. She kissed me while unbuckling my belt and unbuttoning my shorts. I lifted my ass off the couch and Cindy pulled down my shorts and boxers.

Cindy dropped to her knees and started stroking my cock with both hands. “It looks like I’ve got plenty to work with here,” she said as she looked up a me. I opened my mouth to respond, but she bobbed down and took the tip of my cock into her mouth and all thoughts of speech went right out the window. She did not suck on my cock so much as she held it in her mouth and moved her tongue about the tip. Drool slid down the length on to her hands. She used it while she stroked me and turned me into a slippery mess.


She licked down my shaft and sucked my balls into her mouth. I moaned and sat up so that I could put my hands in her hair. I did not guide her, I only held on for the ride that was coming. Cindy licked back up to the tip before plunging down, taking in as much of my length as she could. The blowjob was fast and messy. Spit covered my cock, balls, and legs within seconds as she tried to take me all the way in, but she gagged whenever I hit the back of her throat. She pulled off and said, “You’re just too big for my throat, but I know where you’d fit nicely.”

Cindy stood up and climbed into my lap. She straddled my hips and I pulled her against me. I sucked on one of her nipples while I groped at her other tit. She moaned and writhed against me until my spit slick dick slipped between her waiting lips. She lowered herself until her ass was resting on my thighs. “Mmm, I knew this would be a perfect fit,” she said before  rising up and lowering herself once more.

She fucked me like a woman possessed, grinding against my cock before slide up and crashing back down. I grabbed her ass and lifted my hips to meet her. It didn’t take long for her to call out, “I’m cumming.” She grabbed my head and pulled me against her while her pussy contracted around my cock. Cindy didn’t waist any time drinking in the pleasure. She went right back to riding me hard, as if there was something even bigger building inside her.


I pulled her off of me and pushed her to the floor. She got on her knees and pressed her face against the floor, knowing by instinct exactly what I had in mind. I knelt behind her and speared her cunt with my cock. Her assault left me ready to pop, but I intended to take her with me. I grabbed her hips and slammed my cock into her over and over again. Cindy moaned and cried out with each thrust, but I no longer cared if we woke up my roommate.


“Oh God. That’s it. Give it to me hard,” she called out, and then she gasped and shouted, “Oh fuck!” Her pussy gripped me tight and I was rewarded with a warm rush that pushed me over the edge. I grunted and shot my load deep inside her. I kept thrusting as long as I could and I’m sure Cindy came again before I finished.

When I pulled out of her, Cindy fell forward and laid there panting on the floor. I sat back on my heels enjoying the sight of her heart shaped ass before me. After a couple of minutes she rolled over and looked up at me. “And you’re not fucking Emma?” she asked.

“Nope,” I said.

“Why the hell not?” she sat up and pulled her hair away from her face. “She might loosen up a little if you did.”

I laughed. “You’re probably right, but that’s just never been a thing between us.” I shrugged and smiled. “Besides, if I was fucking her I wouldn’t have fucked you.”

Cindy stood up and cum dribbled down her thigh. “Never mind then,” she said. “If you started fucking her I might have to fire her.” she winked and grabbed her clothes from the floor.

I stood up and said, “Well we wouldn’t want that now.”

Cindy slipped on her skirt and her blouse, not bothering with the panties or bra. “I think I am going to go home and take a hot bath,” she said.

“Sounds like a good plan to me.” I picked up my beer from the end table and took a long drink. “I think I’ll be heading to bed myself.”

Cindy headed to the door before turning and saying, “Get my number from Emma and give me a call tomorrow.” she turned back to the door and left.

I stood in the living room, Doctor Who still playing on the television, with my dick hanging out, when Emma walked down the stair. She looked at me, looked at the beer, looked at the stack of folders on the table, and went back upstairs. I laughed, finished my beer and watched the rest of the episode. We’d have to have a talk in th morning, but I was feeling to good to worry about it now.

9 thoughts on “My Roommate’s Boss

  1. Hot ass post! I especially liked the gifs. The one of the couple in doggy. I’m reading this while sitting in the waiting room. I hope that I’m not called back anytime soon.

    Liked by 1 person

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