My freshman year of college, my roommate and I got along great. He had a gf (Heather) who lived in another city, going to a different college, but she came to visit us a lot. I became good friends with her and the three of us had a good time hanging out.

One weekend, she came down on a Friday afternoon, and she brought a friend. I immediately noticed that the friend was gorgeous. She had shoulder length brown hair, beautiful dark brown eyes, sort of medium sized tits, nice ass and legs. She was about 5’9”. If someone was to force me to pick a celebrity she resembled, I would say Dua Lipa.

I came back from the gym and they were hanging out in our dorm room already having some drinks.

Heather and my roommate, Matt, greeted me cheerfully. Heather got up to hug me, then introduced her friend, “This is my friend, Madison.”

Madison had this hot, bitchy look about her. Hard to describe, but there was an arrogance and I think she could tell I was eyeing her beauty. She knew she was hot and she looked quite fashionable, even in her casual clothes. Heather and Matt were from a wealthy town and Madison was from there too, so I’m sure she was rich too. I wasn’t sure what to do, but moved in for a hug. Madison changed that to a handshake, saying, “I have a boyfriend.”

It was kind of awkward the way she did that, but I guess she wanted to put me in my place right away. She could have just shook my hand and I would have figured she just didn’t want a hug, but it felt uneccessary to tell me she had a boyfriend right then. I pulled my hand away joking, “Maybe I shouldn’t shake your hand either. He might get jealous.”

She gave me a somewhat mixed expression of irritated and amused, “I’m just not a hugger, Sam.”

“That’s okay. I wouldn’t want my ridiculously hot girlfriend hugging a handsome devil like myself either.” Heather and Matt cracked up at that.

She gave me that same irritated and amused look again. We hung out drinking in our dorm room and then everyone wanted to go out for drinks.

I said, “Let me shower before we go.” I slipped off my tshirt and pants, then grabbed my towel. I saw Madison eyeing me a bit in my underwear, as I left the room. I went to the bathroom, which was a shared bathroom between 4 dorm rooms. It had three toilet stalls, two sinks and a big shower stall, with a couple of shower heads and a glass door. As I showered, I saw Madison walk by the glass door. I slid it open enough to poke my head out.

She looked back at me, as she opened the stall door. I said, “I hope everything comes out okay.”

Madison gave me that look again and muttered, “You ass,” as she shut the stall door.

I yelled, “Give a courtesy flush if it’s number two!”

I actually heard a small laugh echo in the bathroom. I finished showering and wrapped the towel around my waist. I combed my hair in the mirror a second while she washed her hands. We looked at each other in the mirror some. She smirked at me and shook her head. We went back into my dorm room and I slipped off my towel while digging for boxers, which amused Heather. It was sort of a joke with us that I would walk around naked. Heather squealed, “Freak.”

I turned to see Madison pretending to not look at me, and blushing a little as I stood there naked, digging in my dresser, before I slipped on some boxers.

We ended up in a dark bar, sitting at a small booth. I was next to Madison with Heather and Matt on the other side. It was loud and we had to lean in to hear each other. I saw a cute girl I knew up near the bar and went to talk to her. I looked over to see Heather and Matt were kissing and Madison was sitting there like a third wheel. The cute girl went to use the bathroom, so I went back to the table.

Madison sarcastically said, “Thanks for leaving me here as the third wheel.”

Heather apologized, “Sorry Madison, we just haven’t seen each other in a few weeks.”

I said, “Look, Madison, you’ve made it very clear you have a boyfriend and I’m looking to get laid tonight.”

Madison rolled her eyes, “Gross,” but she gave me that look.

“Just because you guys are in relationships and presumably getting laid all the time, don’t judge me. I’m single and having fun.”

Madison just looked at me, “You’ll just fuck that random girl?”

“Yeah, she is cute.”

Madison said in an almost defensive way, “I didn’t think she was that hot,” and looked away from me. I could see she was blushing and avoiding looking at me.

“Who do you think I should hook up with?”

She looked embarrassed and stammered, “I don’t care who you hook up with. I don’t even know you.”

“Right, but you seemed to disapprove of that girl.”

“I don’t know, all these girls are so…” I knew where Madison was going . She and Heather were rich and kinda almost glamorous compared to the other college girls. She was being snotty.

I looked at her and finished her sentence to knock her down a peg, “Fun?”

She gave me that look and said, “You’re such a dick.”

The cute girl came back from the bathroom and I started to get up from the booth. Madison put her hand on mine to stop me. She looked at her hand like she was surprised she did that. “Can’t you just hang out and not go hooking up for one night? It’s no fun being the third wheel here.”

I sat back down and grinned at her, “So, you think I’m entertaining?”

She gave me the look again, “Yeah, fine, you’re somewhat entertaining. I could be friends with you.” She emphasized friend obnoxiously.

I grinned and leaned into her, whispering, “You can’t friend zone me, if I’m not even trying to hook up with you. You just assume every guy is trying to hook up with you because you’re not bad looking.”

“Not bad…wow, thanks.”

“Well, I wouldn’t want to upset your boyfriend by complimenting you too hard. He probably wouldn’t like it if I told you, you have beautiful eyes or that your ass is amazing.”

“You couldn’t leave it at beautiful eyes…you just had to go there.”

I shrugged, “I don’t know your boyfriend. I’m probably never gonna meet him. And, you have a very nice ass. I’m sure you know that.” I sipped my beer.

She looked at me with the irritated/amused look again. “Thanks, I guess. Can we talk about something else?”

“Yeah, what do you think of that girl?" I pointed at a girl across the bar, "I mean she has a nice ass. I could go talk to her.”

“Do you just tell every girl they have a nice ass? Is that your gross pick up line?”

“I only say that to girls with particularly nice asses.”

I got the look again, but it morphed into us looking into each others eyes a little longer. She broke off the eye contact, “I have a boyfriend.”

“You’ve said that. Were you telling me again or yourself?”

She looked at me and said it again quietly, “I have a boyfriend,” almost like she was pleading with me.

“Okay, I’ll try to be less tempting for you, but it’s not easy.”

“Fucking prick,” but she smiled at me a little.

The cute girl from earlier came over to talk to me for a little bit and I stood up to talk to her. Everyone was ready to leave the bar. Madison climbed out of the booth and wrapped her arm around mine as I stood there talking to the cute girl. Madison had an evil grin on her face, as she said, “Are you ready to leave baby?” while looking at me.

I gave her an irritated look. Madison put out her hand to shake the cute girl’s hand. “Hi, I’m Sam’s gf, Madison.” The girl looked surprised and confused as she shook Madison’s hand.

As we waited for a cab, Madison was dying laughing.

“You complete cockblock Madison. What the hell?”

Heather, Matt, and Madison were dying laughing, “I’m sorry, I couldn’t help it. You weren’t serious about that girl anyway.”

“How could you tell? Maybe I wanted to date her.”

Madison gave me a more cute look and said in a more serious way, “I can tell. You weren’t that into her. You just wanted to hook up with her.”

We had to squeeze into the back of a cab, so Madison and I were pressed up together and kept looking at each other. She gave me a mischievous grin and I just shook my head. She patted my hand, “Poor baby.”

“That was not nice.”

“Do you want me to call her and tell her I was joking? Tell her you are madly in love with her?”

“No, don’t do that.”

“See, you’re not into her.”

We went back to my dorm room and it was late. We all got ready for bed. My roommate turned out the lights and put on some background music to somewhat obscure the fact that he and Heather were fucking under his comforter. It was really dark in our dorm room with the window shade down.

Madison and I were near my bed. I whispered, “You can sleep in my bed Madison. I’ll just fold out the futon over there for me.”

Madison looked scared, guilty, nervous and whispered out, “We can share your bed.”

I climbed into my bed with her and she said, “We’re not hooking up. I have a boyfriend. I just feel bad putting you on the futon.”

“Okay. Goodnight.” I rolled over away from her, with my face to the wall and my back to her.

I heard her sigh and flop around. I was wide awake and horny but pretended to be casually sleeping. I felt her press up against me aggressively, rolling me over and kissing me. I could just barely hear Matt and Heather fucking over the sound of the background music. She got on top of me, kissing me and grinding her crotch on my erection. My hands moved to feel her nice tits up inside the shirt she wore to bed. Then I moved them down to roam all over her magnificent ass. I even slid them into the back of her pants and into her underwear, feeling her bare ass. She continued grinding herself on my erection, but pulled back from kissing me. She had a worried expression in the dark, as she whispered, “Do you have a condom?” She was breathing hard like she was having a small panic attack.

“Yes, at the foot of the bed, in those shelves.”

She grabbed a condom out of a box I kept down there. Then she slid back up next to me and I could tell she was quickly taking off her flannel pajama pants and underwear. I slipped off the boxers I was sleeping in and quickly tore open the condom wrapper. I rolled the condom on and she pulled me on top of her in missionary. I slipped my dick into her and it was an aggressive fuck. I had just the right amount of alcohol that evening and with the condom, I lasted a long time. She had her legs spread wide and started grunting and moaning kind of loudly, as I banged her. I'll be honest that the fact she was cheating on her boyfriend probably made it even hotter for both of us and that made us bad people, but it was a great fuck. We kissed each other aggressively and I felt her drag her nails on my back as I fucked her hard. I pinned her arms up above her head, as I fucked her and we kissed some.

Heather and Matt were now quiet, but I heard whispering and then heard Matt quietly say, "oh shit, I think they are..." and giggled. Heather quietly said, "oh my god." We didn't care that they knew we were fucking, it was already happening and we were enjoying it. I finally came, grabbed the base of the condom and pulled out. I slipped off the condom and threw it in a trash can next to the bed.

My dick was still hard and my hands roamed around her body. She was still just in a tshirt and I reached up in it to feel her nice tits. She kissed me hard and we rolled around a bit, my erection pressed into her crotch. I felt her hand grip my dick and she stroked it some, then whispered in my ear, "get another condom." I grabbed another one and put it on. She moved herself into doggy, holding onto my bedframe, the covers sliding off. She still had her tshirt on, but her ass exposed. It was so dark in the room, that Heather and Matt would not have been able to see much. Maybe they could see our silhouttes and sort of tell we were in doggy.

I entered her from behind and we fucked hard in that position. She kept backing herself into me in time with my thrusts. I was holding her by the hips and slamming her. The bed was making a lot of noise and hitting the wall. She had her back arched down and butt up, while I fucked her hard. I don't know if Heather and Matt were fucking again or just listening in shock. I didn't care, I was enjoying Madison's nice ass, which I could just barely see, as my eyes adjusted to the dark. She spread her legs wider, while on her knees and I reached around front with one hand to rub her clit a litte while pounding her. We collapsed into prone, as I finished inside her, then carefully pulled out, while holding onto the condom. I threw it in the trashcan.

Madison got up and slipped on a pair of my flip flops to go out to the bathroom to pee. She came back into bed and snuggled up to me. We fell asleep spooning together. We woke up in the morning, with her in front of me and we were still spooning. She was still just in that tshirt with no panties on, and my hand started wandering around her bare ass and hip. Then down between her legs a little in the front. Our beds were oriented so that Matt and Heather were facing us across the room. The beds were oriented head to toe. They woke up too and I saw Heather give Madison a look. It was sort of a raised eyebrow, disapproving look.

Matt was looking over too with sort of wide eyes at me, like he didn't know what to think. Finally, Heather got out of bed and grabbed some things from her overnight bag, "I'm going to brush my teeth. Can you come with me Madison?"

Madison reached around in my bed to find her panties and then slid them under the covers. It was pretty obvious what she was doing and I saw Heather shake her head. They went into the hallway, but did not close the door all the way. I heard quiet whispering, then they got a little loud, "Madison, what the fuck are you doing?"

"Come on Heather..."

"Come on Heather, what?"

"Just...I dunno...I've been with Chris since sophomore year of high school. I never cheated on him."

"Until now."

"Look, Chris is the only guy I've been with. It's just this one time."

"Okay, well, I guess it's none of my business."

I heard them go into the bathroom and then could hear the sinks running. Matt whispered, "Dude," with wide eyes.

I shrugged in a guilty way.

"She's got a boyfriend."

"Yeah, I've been told that."

He chuckled a little, "The guy is kind of an ass. Not that it makes it right."

"You've met him?"

"Oh yeah, we all went to high school together."

"Shit. Look, she is the one who started it dude. It was not my idea."

He was shaking his head, "I can't believe you fucked her. Well, she is fucking hot. Can't say I blame you."

"Dude, she is hot and that was pretty wild."

The girls came back in and Madison and Heather seemed slightly irritated with each other. Heather and Matt got ready to go for a run together. Heather seemed to be thawing from her anger a bit and said, "Let's get breakfast when we get back," and they left us there alone.

We sat in bed, under the covers, drinking some coffee from the coffee maker we had in our room. We kept looking at each other. Madison cleared her throat awkwardly, "That was just a mistake last night. It was a one time thing I guess I needed to get out of my system."

"Yeah, okay, um...I'm sorry..."

"I was the one who initiated it. You were being a gentleman, surprisingly."

I laughed, "Surprisingly?"

"Yeah, you were flirting with me pretty hard earlier in the evening."

"That's not what it looks like when I flirt hard."

She gave me her irritated, but amused look.

Madison looked at me nervously and said, "That was really good last night though."

I chuckled, "Uh...yeah...I guess we got kind of loud."

She laughed a little, "So embarrassing. I guess Heather and Matt could hear it."

“I’m not sure how they wouldn’t have heard it.”

She laughed a little and blushed.

We started looking at each other some more and then she set her mug down on the shelves of my dorm bed headboard. She grabbed my mug and set it down to, then started making out with me. I protested briefly, "Are you sure about this, Madison?" and she kept kissing me.

She paused, "It's just this weekend."

We lost control and groped each other, kissing and rolling around in my bed. I slid down her body and pulled down on her panties. She lifted her butt to help me get them off. I kissed my way up her nice legs, then licked her slit. She whimpered, "Yes...", as I started licking her. I was enjoying eating her out, when the phone rang. This was in the land line days and we shared a phone. Madison said, "Fuck...I gave Chris the number here to call me."

She hopped out of bed and answered the phone. It was him. "Oh, hi baby...we're having fun...we went out to a bar last night...yeah, it was okay...oh, Matt's roommate let me have his bed and he slept on a futon...yeah, he is a nice guy...you would like him...yeah, you guys would get along great..." She was looking over at me. I had an erection under the covers, wishing she would hang up so I could go back to eating her out. She stood in front of our window and I could see her bare ass, while she talked on the phone in just a tshirt. "...I don't know what we're doing today...tour around the city some...do some day drinking..." I pushed down the covers to expose my erection and sat there with a grin. She turned around while talking on the phone and held back from laughing, as she saw my boner. "...okay, well I kind of need to get off the phone...yeah, I need to shower...yep, they're all waiting for me to get breakfast...I'll say hi to them...okay, love you..." She hung up the phone and hopped into bed.

Madison grabbed my dick and then plunged her mouth down on it. She bobbed her head up and down a few times, "You're bad, Sam."

"What?"

She sucked it some more.

"Showing me your boner while I'm on the phone with my boyfriend."

"He called at a bad time."

She snorted, laughing with my dick in her mouth. Then she got up on her knees and stripped off her shirt. I said, "Damn..." seeing her naked in the light of day for the first time.

"Where are the condoms?"

"Oh shit, I think I'm out."

She shrugged and climbed on my dick, "I'm on birth control."

Madison bounced up and down on my dick and my hands wandered all over her naked body. I grabbed her ass cheeks, "I want to fuck you doggy again...I couldn't see your ass last night."

She laughed and slipped off me, moving into doggy. Her ass was terrific and I couldn't help but lick her pussy from behind, then lightly licked her asshole. She squealed some when I did that, "Chris does not do that." I pulled my tongue off her asshole, "Well, Chris does not know what he is missing," and went back to licking it. I slipped my bare cock inside her from behind. I pulled her into my thrusts by her hips, "You've got a spectacular ass, Madison."

She whimpered out, "Thanks..."

As we banged, I kept looking down at her cheeks and her puckered anus, watching my dick go in and out of her pussy, "You like a finger in your ass, Madison?"

She laughed, "I don't know. Chris is not into anal stuff."

"I've got some lube here. Want to try it?"

She laughed and turned back to me, "Alright..."

I reached in front of her on my shelves and grabbed some lube, squirting it right on her sphincter, which cracked her up. I put some on my middle finger and started slowly working it into her butthole. I finally had my finger all the way in her butthole, while I fucked her doggystyle. She seemed to love it and laughed, "this is so wrong..."

I said the cheesy line, "If this is wrong, I don't want to be right."

She just grunted and moaned as I fingered her asshole while fucking her hard. She didn't seem to have any inhibitions with me and I said, "You want me to fuck your ass?"

She laughed, "What?!" and turned to look at me over her shoulder, while still in doggy.

"Do you want your ass fucked? Your boyfriend isn't into it. This is your chance." I had stopped moving, but still had my finger in her ass and my dick in her pussy. She was very slowly moving herself back and forth, as she thought.

She made a nervous laugh and whispered, "Yeah, why not." I grabbed the lube again and squirted some more near her sphincter. I worked two fingers into her butt. I squirted some on my hard dick and rubbed it, then started slowly pushing the head of my cock into her slippery asshole. Once I had the head in, I said, "Madison, you go ahead and back into it."

She giggled, "Oh my god," and then started slowly moving back and forth on my dick. Her ass swallowed more of my dick, until I was all the way in her. "Holy shit...you're fucking my ass..." She laughed a little more. I slowly pumped my dick in and out of her tight asshole. She breathed in through her teeth loudly, as she took my dick in. I put some more lube on my shaft and watched it go in and out of her tight hole. She put a hand between her legs to touch herself, with her other hand on the headboard to hold herself up. She was making animal noises that could probably be heard in the hallway. I couldn't take it anymore and came in her butt. I slowly removed my dick and saw some cum leak out of her sphincter. I grabbed a small towel to wipe up the cum and lube from between her cheeks. I loaned her a robe and we both went into the bathroom to shower.

After we showered, we went back in the room, and Heather and Matt were back from their run. Heather gave a disapproving look, then shook her head and laughed. Heather and Matt went to take a shower, while we got dressed. After we were dressed, we ended up hugging and kissing a bit fully clothed. She pulled back and gave me a very sexy look, grabbed my crotch, and said, "I'm not done with this."

Heather and Matt got dressed and we all headed out to brunch. When we sat down, Madison said, "Oh, I've got brunch guys...Chris said to treat you guys on his credit card." I felt really weird about it. I'd fucked this guys girlfriend in the ass and he was buying me brunch. Also, I couldn't believe she had his credit card. How rich was this guy? I could barely buy ramen.

We had brunch and got tipsy with mimosas. Madison got relaxed and more affectionate with me, leaning on me and putting her arm around me, caressing my back. She paid the check with Chris's card and I said, "Well, thank Chris for me." Heather muttered, "Yeah, it seems like you do owe him..." Madison actually snorted laughing at that. Matt went to use the bathroom and Heather dragged Madison a little away from me on the sidewalk. They were talking loud from the mimosas. "So, are you going to break up with Chris?"

"No, I mean, this is just a little fling..."

"Just a little fling? You've been dating Chris for more than three years and you're fucking some random dude."

"What about you last month?"

Heather looked around nervously, "Shhhhh...that was just a blowjob."

"It wasn't just a blowjob. You said that dude gave amazing oral."

"okay, but I didn't fuck him."

"You don't get to judge me."

"Fine." They both looked at each other and laughed. "Did you guys do it again while we were running?"

Madison just nodded yes and looked over at me. Then she whispered in Heather's ear. Pretty sure she told Heather I fucked her ass, because Heather let a loud "phssshhhh," of air escaping her lips laughing and said, "oh my god..."

We walked around the city and Madison and I were not discrete at all. We held hands, as we walked around. We would kiss sometimes. Heather and Matt were buzzed and mostly just trying to enjoy their time together. They stopped paying attention to us cheaters.