[M]y Girlfriend’s Roommate (LONG)

This is my first story; there are more to come if there is any interest.

This story begins during my sophomore year of college. I attended a community college while living at home during my freshman year, but moved into the dorms of a local university during my sophomore year. I had been dating Casey for about a year at this point and she was about to move into a new apartment with a high school friend, Alex.

I was a year older than both girls. I had taken a year off between high school and college, so I was 20 and both girls were 19. Casey was a brunette with brown eyes, about 5’5″ and a little on the curvy side, very cute with large C/small D cup boobs. She was a lot of fun, but could be very hot-tempered, which we shall see later in the story. Casey was attending cosmetology school, which started a bit later than my college courses.

Alex was blonde haired, blue-eyed and tan, about 5’7″ and athletic. She was your typical hot college age girl, a little full of herself but for good reason. She had a great body and large B to small C cup breasts. Alex decided to quit school after a year of college and was waiting tables at an upscale restaurant.

After getting myself moved into my dorm, I volunteered to help Casey move in. We took a day and made about a dozen trips from her house to the apartment, then spent some time shopping to outfit her new place. This was her first apartment so she was missing essentials like cookware, trash cans, shower curtains, and all of the other little household items that you don’t think about until you get your own place. It was a bi-level apartment, with the downstairs consisting of the kitchen, living room, and a small bathroom, with two bedrooms and a larger bathroom upstairs.

We were both exhausted by the end of the day, but I had a reading assignment due so was reading Plato’s Republic while Casey slept. Alex had been working a night shift and I heard the door open around 2 A.M. Her parents had dropped off some furniture while Casey and I were moving in, so the only thing Alex brought with her was an armful of clothes.

I was sitting in a chair in Casey’s bedroom with the door cracked open and had a view of the hallway and the entryway to Alex’s bedroom. Alex, believing us both to be sleeping, said quietly, “Okay, if you don’t want to see my pussy, look away.” She proceeded to strip out of her work uniform right in the entryway of her bedroom, where a mirror was fortuitously placed, giving me a great view of both the front and the back.

Her work uniform consisted of a white dress shirt and black pants. She unbuttoned the shirt and let it fall to the ground, revealing a black bra which quickly followed the shirt. She was more attractive than I had realized before, and I had always found her to be sexy. She was tan all over and fit, with perky boobs that had small brown nipples. Her stomach was taut and she looked tight all over, a nice contrast to Casey’s curves. She unbuttoned her pants, revealing that she had not been wearing any underwear while at work. They soon joined the shirt and bra on the floor, unveiling a neatly trimmed landing strip and a tight ass.

By this point, I was rock hard. Plato was forgotten and I was torn between ogling Alex and making sure that Casey stayed asleep. I didn’t want to be caught checking out my girlfriend’s roommate naked on my first night there. Luckily, Casey was dead to the world and I quietly started stroking myself through my gym shorts while getting an eyeful of Alex.

I realize now that Alex must have known that I was still awake somehow. At the time I thought I had just gotten lucky to see her naked, but after undressing, she began to check herself out in the mirror, cupping her boobs and turning from side to side to get a good view from all angles. Satisfied, she gave her reflection a smile and got into bed, without putting any pajamas on. I quietly finished stroking one out and finally got some sleep.

I returned to school the next day, feeling both guilty and excited about spying on Alex the night before. Casey was my first girlfriend, aside from some short flings in high school. I’ve always been a bit introverted and finding and maintaining relationships has never been a strong suit. With Casey, everything seemed to come easier than it had with other girls, so I had no thought of cheating on her or otherwise endangering our relationship. With that being said, I was 20 and constantly horny.

Over the next few weeks, I began to spend more and more time at Casey and Alex’s apartment. Eventually, I was there more than I was at my dorm. Most of my time there was spent with Casey, playing video games, watching movies, and, of course, having sex whenever Alex wasn’t around. Casey and Alex’s schedules were pretty different, with Casey having class during the day each weekday and Alex primarily working night shifts at the restaurant. I had organized my class schedule so that I didn’t have class on Wednesday or Friday with only one class on Monday.

We all hung out together occasionally, sometimes drinking when we could get beer, which wasn’t very often with all of us under legal age. Alex almost never wore a bra when she was at home, her perky nipples nearly always visible, which bothered Casey a little bit. I did my best to be a loyal boyfriend, but would definitely find myself staring.

Alex also never wore panties of any kind, a habit which Casey adopted. They both would wear short shorts around the house and I caught glimpses of both of their pussies on more than one occasion. Casey always kept hers shaved smooth, but Alex maintained that little landing strip. Again, the contrasts between the two intrigued me.

One activity that Casey and I took up during this time was renting porn movies and teasing each other while watching. Casey was terrified that Alex would walk in while my face was buried in her crotch or vice versa. Of course, this is exactly what happened one night. Casey was giving me head on the couch while I was watching a threesome on screen and we heard Alex’s key in the door. Casey panicked, swore, and hurriedly covered up my cock with a blanket.

Alex walked in, saying hi from the other room, and then entered the living room and saw what was on the screen. She turned to look at us and said, “Well, this looks like fun. I’ll be right back.” While she ran upstairs, Casey asked wondered what we should do and I didn’t have an answer for her. Before we could decide on a plan, Alex came back downstairs in her customary tank top sans bra and a tiny pair of white shorts that left little to the imagination. She laid down on her stomach, in front of us so that she could watch the movie and we could see her, but she couldn’t see us. She looked back, smiled, and said, “Carry on!”

Casey looked at me. I shrugged, not thinking very straight after having my blowjob interrupted. Casey thought for a second, then pulled the blanket that had not been concealing my bulge very well over her head. Soon, the blowjob resumed.

I didn’t know where to look. There was a mouth on my cock, covered by a blanket that bobbed up and down. There was a threesome on the TV. And there was an incredibly hot girl wearing next to nothing lying in front of me. My lust overcame my senses and I focused on Alex’s ass and pussy mound, not very well concealed by the skin tight shorts.

Casey was starting to make some slurping sounds, which caused me to moan. Then I saw that the view of Alex had changed slightly. Her hand had somehow fit into the skin tight shorts. She seemed to be rubbing her clit, at first slowly and softly. My cock was harder than it had ever been. As Casey made more dick gobbling noises, I became more vocal, which seemed to cause Alex’s shorts to become increasingly moist, until they were practically transparent. Alex’s slow and soft clit rubbing transitioned to faster and more insistent motions, until she began grinding her clit into her hand. Suddenly, she stopped the humping motion, her legs shook, and she let out a very quiet squeal. I had just watched Alex have an orgasm while getting blown by Casey and it was amazing.

Casey could tell that I was getting close and slowed down. When we watched porn together, she usually took me right to the edge without going over before we’d switch and I’d eat her out until she came. We’d repeat this process until the movie finished or we couldn’t take it anymore, usually the latter, before taking the party to the bedroom.

I wasn’t sure what was going to happen next now that Alex was here. Casey was a bit self-conscious around Alex, so I didn’t know if she would feel comfortable having me go down on her with Alex in the room. Fortunately, Alex solved the problem for us. “I’m tired. You guys have a good night!” She just about winked as she said it and headed back to her room.

Casey, now out from under the blanket, smiled at me mischieviously and said, “Let’s go upstairs.” I noticed that Alex’s door was cracked open as we headed to the bedroom. We hurriedly stripped our few remaining articles of clothing off and Casey pushed me onto the bed. I was still rock hard and she straddled me, guided me into her pussy, and slowly sank down onto me. It didn’t take long for her to pick up the pace.

Casey was louder than usual as she slammed herself onto me. My hands found my way to her amazing tits, lightly twisting and pinching her nipples. My mouth replaced my hands, tongue flicking against her nipples, causing her to moan ever louder. Very swiftly, Casey yelled out, “Holy fuck, I’m coming, I’m fucking coming.” Her vagina squeezed around me as her movements slowed and her legs quivered.

When she came down, I slipped out from under her and pushed her down so I could enter her from behind. I slowly filled her up before pulling out and repeating the process, gradually building up speed. At the apex of each thrust, Casey moaned. When the slow, hard fucking became hard, fast fucking, her hand found her way to her clit, making her even louder. I was getting close, but before I could finish, her pussy gripped me again and she nearly yelled out, “Holy fuck, your dick is so big, fuck!” That did the trick and I pulled out and sprayed one of the biggest loads I’ve ever had all over her ass, back, and even into her hair.

Though I was definitely not complaining, I was a bit curious about why Casey had been so vocal. She usually wasn’t that loud in bed. My answer came shortly as we both heard muffled moaning coming from Alex’s room. Casey grinned at me. “That did the trick.” She’d been putting on a show for her friend and it sounded like it worked.

Life continued after that night. I turned 21 and more often than not, we now had beer or booze around. I continued to be the loyal boyfriend while enjoying eyefuls of Alex and was practically living in their apartment at this point.

As I mentioned, Casey had a temper and was a little insecure around Alex. On one particular drunken night, we were taking turns playing video games. At one point, Casey asked me to follow her into the kitchen. She whispered to me, “I’m getting so horny.” She then pulled my dick out of her shorts, dropped to her knees, and started blowing me right in the middle of the kitchen. This lasted for a couple of minutes before Alex called out, “Casey, it’s your turn.” Casey got up, smiled, and left me to put my dick away.

As I walked back into the living room, Alex glanced at my shorts. There’s no way she could have not seen my bulge. “What were you guys doing?” She asked innocently.

I, being drunk, replied, “Casey was blowing me.” Casey smacked me playfully and giggled.

Alex looked at us. “That’s so hot.” She picked up her beer bottle. “Did she do it like this?”

She proceeded to give the best blowjob ever given to a bottle of Killian’s. She tongued around the lip of the bottle, licked down to the label, swirled her tongue around the sides of the neck, and inserted it into her mouth. Her lips and tongue formed a seal and she bobbed down until the label of the bottle reached her mouth, then backed it out and repeated the process a few times, before extracting the bottle from her mouth with an audible pop.

My dick, already hard from Casey’s ministrations, strained against my shorts. Alex was staring at my crotch and I was staring at Alex’s mouth. Neither of us was paying attention to Casey, who had stopped playing the video game when Alex began her demonstration.

“Fuck both of you guys,” Casey said, her voice low and dangerous. “Fuck you, we’re done,” she said, looking at me. “Alex, you’re such a bitch.”

Shocked at how quickly this fun night had turned into a shit storm, I followed Casey up to her room. “What’s wrong? What did I do?”

She glared at me. “I know you think Alex is hot. I’m tired of watching you stare at her. I just had my mouth on your dick, but you couldn’t look away from her for five seconds. Fuck you, we’re done, fuck you.”

Casey threw on some clothes, grabbed her purse and keys, and stormed out, yelling something about staying with her parents if anyone gave a shit.

I went back downstairs, not sure what to do. I was too drunk to drive back to school. Alex was no longer on the couch; she must have snuck into her room while Casey was yelling at me. Frustrated, I grabbed another beer, sat down on the couch, and started playing the video game again.

A short while later, Alex came back downstairs. She was wearing the same tight, white shorts that she had worn while fingering herself while we were watching the porno and a light blue tank top, complete with highbeam headlights. She sat down on the other side of the couch.

I asked her if she wanted to play and she said sure. I passed her the controller and she let her fingertips slide up my hand and forearm while grabbing it from me. She began playing, but spread her legs wide while doing so. The shorts were so tight that her labia were clearly outlined against the thin fabric.

Here was my dilemma. It was clear that Alex was into me and wanted something to happen. I could fool around with this girl who I had been eyefucking for months at this point or I could try to call Casey, the girl I’d been dating for nearly a year and a half, and try to work things out. Sober, I like to think that I would have made the smart decision and tried to work with Casey. Drunk and horny, I let the little head do the thinking.

I moved closer to her and rested my hand on her bare leg, then started slowly moving it higher and higher. I swear, I watched her pussy get wet enough to dampen the tiny white shorts. I slipped a finger under them, teasing the delicate skin between her pussy and her thigh. She dropped the controller.

My other hand grabbed her neck and pulled her face to mine. Our lips met, then our tongues. She was lightly moaning as my fingers danced around her pussy without touching it. I pulled my hand out of her shorts and lifted her tank top off, letting her perky boobs spring free. My hands cupped them as we continued to make out, my fingertips gently flitting over her nipples.

I pushed her back so she was reclining against the side of the couch and hooked my fingers into those white shorts, my tongue moving from her neck to her nipples and then down her flat stomach. I could smell her pussy and needed to taste it. I pulled the shorts off and kissed around her pussy, letting my tongue flick over the outside of her labia. Finally, I slowly licked her from the bottom to top, then top to bottom, then bottom to top one more time before letting my tongue flick over her clit. She moaned.

She was dripping wet. Her juices coated her pussy lips, her clit, and even the tops of her thighs. I continued flicking her clit with my tongue, occasionally travelling lower to taste her pussy before returning to her clit. I moved my finger to her hole and slid just the tip in, slowly circling, before sliding it all the way in. My finger continued to slowly fuck her while my mouth and tongue worshipped her clit. Then I inserted another finger into her while my mouth formed a tight seal around her clit and my tongue flicked across it. She grabbed my hair, pushed herself into me, and had a huge, shuddering orgasm.

She pushed me up, made me lay back, and crouched between my legs. She just sat there, looking at my manhood, before quietly saying, “You have a really nice dick.” I smiled, and she gently pulled her fingernails across the bottom of my cock. Her fingers circled around the head and she began lightly twisting, just barely touching. It was an amazing sensation, something that Casey had never done before. Her hand began working its way down my shaft and back up, just lightly touching and turning in a circular motion instead of the up and down that I was used to.

Her touch became more insistent and she suddenly bent down and slipped just the head into her mouth, her tongue swirling around while her hand pumped my shaft. She then took her hand off me, popped the head out and licked up and down my shaft, lubricating it with her saliva, before returning to my head. She looked up at me, somehow managed to smile with my cock in her mouth, and then formed a tight seal around my cock with her tongue and lips before beginning to bob.

Alex was much more experienced than Casey at giving head. She took me deeper than Casey ever had, held me in her throat, and then bobbed back up. She would alternate between swallowing my dick and using her tongue to lick my shaft and around my head. Then she moved even lower and began to flick her tongue over my balls. It felt amazing and to this day is one of the most memorable blowjobs I’ve ever received. Sober, I would have come very quickly, but alcohol makes men into champions. Eventually, though, I stopped her.

“I’m going to come if you keep that up.”

“But you haven’t even fucked me yet!” She was being playful, but finished up by lightly kissing my balls and my dick all over.

I sat up, pushed her back, and returned my fingers to her pussy. It was still soaking wet. I moved my cock into position and soaked it in her pussy juices while grinding it against her clit, then lowered and positioned it against her slit. I slowly pushed into her, savoring the intense feeling of her warm and wet pussy engulfing my dick. I slid all the way into her and she moaned, grabbing my shoulders. I began slowly pumping, pulling nearly all the way it before filling her up again. She loved it. I increased the pace and bent so that I could flick my tongue across her nipple while pounding her. This drove her crazy and she finished quickly, squeezing my cock with her pussy.

I repositioned without leaving her tightness so that I could fill her up and then grind against her clit while she was stuffed full of me. I started slowly again before increasing the tempo. It wasn’t long before her vagina squeezed me again and she had another intense orgasm.

Then I had her roll over so I could enter her from behind. That ass pointed up in the air and her slick pussy was a sight to behold. I pushed into her and she grabbed the arm of the couch. There was no slow build up this time. I just pounded her hard and fast, feeling her ass push back into me.

It wasn’t long before I was ready to finish. “I’m going to come. Do you want me to pull out?” I managed to gasp out between thrusts.

“No, fill me up.” This was too much to handle and I slammed into her and felt her pussy squeeze me as I shot my load deep into her. It seemed to last forever. Finally satisfied, I pulled out and sat back down.

“Fuck, that was amazing,” I said after catching my breath.

“Thank you, I needed that,” was Casey’s reply. She left to clean up while I didn’t move, exhausted. She came back out, still naked, and asked, “Would you like to sleep in my bed tonight?”

I said yes and followed her upstairs. We slept naked, her firm body pushed against mine.

When I woke up, she was gone. She left a note that said, “Had fun last night. Got called into work. Thanks!”

I’d like to say that Alex and I continued to fuck each other at every opportunity, or that Alex, Casey, and I had dozens of threesomes together. Unfortunately, that’s not what ended up happening. Casey called me later and apologized. We made up and got back together. I never mentioned my night with Alex to her and Alex must not have either. After that night, Alex was around the apartment far less often and I didn’t see much of her. At the end of their lease, they both decided to move out and ended up going separate ways. Casey and I stayed together for a few more months, but we eventually broke up.

Thank you for reading my first story. If you have any questions, comments, or constructive criticism, please feel free to leave a comment or send a PM. If it is well received, I may have more in the future!

Source: reddit.com/r/gonewildstories/comments/6j4bjc/my_girlfriends_roommate_long

13 comments on “[M]y Girlfriend’s Roommate (LONG)

  1. Hot story! In the future, you probably want to use a title that lets you weave in both an [M] and an [F] for stories involving you and a woman.

    That will ensure people don’t mistakenly pass it by.

  2. “Thank you, I needed that”, was Casey’s reply. You got your partners mixed up at the end bud. Very hot otherwise!

  3. God yes… love it! Would love to say Alex is my spirit animal, but I think I’m more of a Casey haha

  4. >She proceeded to give the best blowjob ever given to a bottle of Killian’s.

    There’s no way you can possibly know that.

  5. Very hot and well written, my friend! Can’t wait to read more. I’ve always landed the Caseys, but never an Alex. Good job!

  6. Wow amazing story!

    >> It wasn’t long before I was ready to finish. “I’m going to come. Do you want me to pull out?” I managed to gasp out between thrusts.
    >>”No, fill me up.” This was too much to handle and I slammed into her and felt her pussy squeeze me as I shot my load deep into her.

    I had that exact same exchange with a girl who wasn’t my significant other at the time, and it’s still the hottest moment of my life.

  7. Just the thought of two girls in short shorts with no panties was enough for me, but the part watching porn with Alex was incredible. Top 5 hottest story I’ve read on this sub

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