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[MF] Taking "Naps" With My Former Roommate's Girlfriend Was A Very Bad Idea

Mar 13, 2024

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When I first moved out of my hometown to the ~big city~ I couldn't afford to live on my own, so I had to search for a roommate. This was a terrible adventure for me, mostly because I'm awkward and don't like most people. I look at all these people who go to clubs every weekend and think, "Why? How?" -- I find myself being overwhelmed during a 20-minute shopping trip at Target.

Anyway, it took close to a month, but I finally connected with a dude (Travis) who was around my same age and was going to school to become a lawyer. We were very different. He came from wealth. I came from trash. He had muscles, and then those muscles also had muscles. I had a skinny frame and often struggled to open jars of peanut butter. He was outgoing and surfed. I was reserved and surfed... the internet.

But I knew he could cover rent and he was out of the apartment most of the time, so it seemed like a good enough match. Plus, I was desperate. When Travis and I first moved in together, he did not have a girlfriend, but around three months in, he brought a girl back to the apartment. This girl was named Jessica, and she became a permanent fixture. By month five, I saw her more than I saw him. She was basically living there, even though she allegedly had a place of her own. This probably should have annoyed me, considering we were splitting all the bills 50/50, and clearly they were using more of everything, but Jessica was super cool... and nice to look at.

She had dark hair, glasses, and a smile that kinda let you know she was trouble. It's like how rattlesnakes have a rattle to warn you. Jessica had her smile. She reminded me a little bit of a young Jordana Brewster.

She was already out of college and worked from home. I'm not sure what she did exactly, but she was on the phone a lot. At the time, I also worked part-time from home, so we would often have a little "office" type set up in the living room. It was honestly nice to have a co-worker. It made the days go by faster. Travis was home on Thursdays and Fridays, but on Monday, Tuesday and Wednesday it was just Jessica and I until like seven or eight at night.

I don't think Travis ever felt threatened by me being alone with his girlfriend. After all, he was taller, more muscular and had more money than me. Why would he feel threatened? Heck, I certainly didn't think I had any chance with Jessica. When I say I thought of her as just a friend, I truly mean it. Sure, she was incredibly attractive, but I genuinely enjoyed just hanging out with her. We surprisingly had a lot in common despite growing up on different sides of the country.

We developed this tradition of taking an hour break from work at 2:30 every afternoon. "It's the perfect time for a break," Jessica would say. "It's an hour or two after lunch, three hours before work ends... it's needed to make it through the rest of the day!"

"You don't need to convince me to take time off work," I told her the first few times she suggested it.

For the first couple weeks of this one hour break, we'd usually just talk, watch something on television, sit on the patio or even go for a walk. But then one afternoon, when Jessica was sick with a cold, she suggested we take a nap.

"A nap?" I laughed. "I haven't taken a nap in years."

"It's not hard," she joked. "I'll show you," she threw herself on the couch, grabbed a blanket from some fancy basket she bought weeks earlier, and covered herself up with it. She then closed her eyes and pretended to fall asleep.

"See?" she opened her eyes and smiled, "It's super simple."

"Wow, yeah. I remember it being much more complicated," I replied. Our living room was small, so there was only room for the one couch. I grabbed another blanket from the basket and spread it across the floor.

"What are you doing?" she asked me.

"Taking a nap?"

"On the floor?"

"Yeah? Is that against the rules?"

"Well, no, but it's uncomfortable. Just come up here with me. Don't be weird."

"Righty-o" I said, sounding like a complete dork.

"I said don't be weird," she laughed.

"I'm sorry! You're asking me to not be something I've been my entire life,"

She briefly stood up from the couch and motioned for me to slide to the back. Once firmly rested on my side, she moved in front of me. Jessica grabbed the blanket and draped it over our bodies. I was spooning her at this point. Her ass pressed against me. She was still in her pajamas. I was thankfully wearing jeans. She grabbed my arm and placed it over her body.

"Act like you've cuddled before,"

"I'm just --"

"Just what?"

"I don't want to be like a creep or anything," I told her.

"Alex. I invited you up here,"

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"I know, I know," I replied, feeling more comfortable with the situation. I wrapped my arm around her and pulled her in close. Her hair was pressed against my face. I remember it smelling like a fruit basket. It didn't take long for both of us to fall asleep. Of course, we forgot to set an alarm, so we didn't wake up until nearly five o'clock.

We both woke up at the same time, thanks to the neighbor's dog howling at sirens from a fire engine. When Jessica shifted just a little, I felt my hardness move against her. I had a bad case of afternoon wood. I know she had to feel it, but she didn't move.

"We forgot to set an alarm," she spoke softly, sniffling a bit.

"I noticed," I said while yawning.

"So, how was your first nap in years?"

"Really good," I replied.

"Feels like it," she laughed while moving off the couch.

"I can't help --" I was ready to plead my case, but she stopped me, "Relax, it's cool," she smiled, walking off toward the kitchen to drink a glass of water.

And that's how our naps began. We would nap nearly every afternoon we were alone together. And on days when she wasn't there, I'd still find myself getting sleepy at 2:30. It was tradition. I'd say 90% of the time, I'd wake up with her ass pressed firmly against my hardness. She never seemed to mind though, and a few times, I swear I'd feel her wiggling her ass against me during the nap.

It was all "innocent" until one afternoon when Jessica was wearing a little sundress. I was wearing a pair of grey sweatpants and a white t-shirt. Jessica was more dressed up than usual because she had an in-person meeting in the morning. Most of the time during our naps, she was wearing either pajama pants or jeans. This was the first time she wore a dress. She looked absolutely incredible in it.

Before I even fell asleep, I felt myself getting hard. The thin material of her dress pressed against the front of my sweatpants. She moved against me, I could feel the cheeks of her ass. I closed my eyes and attempted to pray the boner away, but apparently God was too busy trying to solve world hunger at the time to grant my wish.

Jessica moved again. This time it felt deliberate. It felt as if she dragged her ass against the outline of my cock. I was frozen. Unsure if she was moving in her sleep. "Should I wake her up?" I thought to myself.

She moved again, and now my cock was pressed between her cheeks... still covered by clothing of course, but I could feel everything.

"Are you awake?" I whispered.

"Shhh," she responded. She then brought hands down to her dress and lifted it up, revealing she wasn't wearing any panties. Her bare ass was pressed against me. She moved it in circles against the outline of my cock. I could hear her breathing increase. I slid my hand down to the top of her thigh and rubbed it gently, feeling the smoothness of her for the first time. She felt incredible. I moved my hand toward her ass, squeezing her cheeks, spreading them apart just a little.

She reached back, grabbing at the waistband of my sweats. It took a lot of effort, but I managed to pull them down to my knees without getting up. My cock bounced free, smacking firmly against her ass. I pulled her in close, running my hand across her tits. She moved her warm ass against my cock as I slid my hand down the top of her dress, running my fingers across her nipples. They were already hard. I pinched them gently and then squeezed her tits roughly.

My lips dragged against the back of her neck as she repositioned herself just a bit, so that the head of my cock was just inches away from her pussy. She reached down and grabbed my cock, moving it toward her warm entrance. She dragged the head up and down her slit, trying to collect as much wetness as possible before sliding it inside.

"Oh," we moaned at the same time. At first, neither one of us moved. My cock was just chilling in her pussy, but then she started moving her hips back and forth. It was a slight movement. Like, if there were a blanket over us, you might not even know we were fucking. I looked down, watching her ass gently bounce against me. My cock moving in and out of her pussy. The sight was breathtaking. I slid my hand down her stomach until I felt her clit.

"Mmm fuck," she moaned. I rubbed her clit with my middle finger as she continued to fuck me sweetly. My cock grew inside her, reaching limits I didn't even know were possible. I moved along with her, driving my hardness deeper inside. My mouth was open, just pressed against her neck, she seemed to like the sensation. "Oh," she whispered, moaning a little louder as my finger continued to rub her clit.

She moved her ass in circles. My cock feeling every inch of her pussy. She continued the circular movements, and they quickly became more and more desperate. Her moans grew louder, "Yes, yes," she whispered breathlessly as she came on my cock. Her hot ass moans and the sudden warmth on my cock made me nearly cum inside her, but luckily I was able to pull out just in time, unleashing an impressive load across her ass.

Cum was threatening to drip down on the couch cushions, so Jessica had to jump off and waddle toward the bathroom. I held my cock up with my hand, making sure the cum-covered head didn't drag against the cushion.

I could hear the shower turning on as I walked to the kitchen to clean myself up with a paper towel. She came out five or ten minutes later, a blue towel wrapped around her wet hair, "Back to work, huh?" she smiled, as if nothing happened.

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