[MFM] That Time I Hooked Up with My Roommate’s Brother and His Friend (Part 1)

If you haven’t read the last two stories I wrote, about [how playing matchmaker](https://www.reddit.com/r/gonewildstories/comments/brqo2k/fm_playing_matchmaker_has_its_benefits/) for my college roommate and the guy she liked [got me some amazing sex](https://www.reddit.com/r/gonewildstories/comments/bws2nf/fm_playing_matchmaker_has_its_benefits_part_2/), I recommend checking them out. People seem to like them.

This is about something different though and it’ll hopefully be a bit shorter. (*Narrator voice*: It wasn’t)

That story happened about 10 years ago and a lot has happened to me since then. I’ve had a lot of great (and some not-so-great) relationships, met the man of my dreams and even gotten married.

But once I had my tryst with Chris, I came out of my shell. I realized that it wasn’t that I didn’t like sex, but rather that I just hadn’t experienced how amazing *good* sex is.

Throughout that whole time though, I’ve always had a pretty voracious sexual appetite. On top of that, I really like trying new things. Luckily, my husband does too. We’ve been together for almost 5 years so we’ve built up enough trust that we can both feel comfortable letting our freak flags fly in the bedroom. We’re both pretty willing to try whatever the other person suggests.

Recently, we’ve been telling each other stories from our past while we fool around. It’s been fun to learn about all the random hookups and dalliances that he’s hard over the years while I share my experiences with him.

Sharing all those experiences with my husband brought back a lot of fond memories, so that’s why I started writing them down.

Without further ado, I present, “*That Time I Hooked Up with My Roommate’s Brother and His Friend!*”

—

I stepped out of the shower and walked into the bedroom.

“What do you think?” I asked, twirling around naked in the middle of the room.

“I think you’re showing a little too much skin,” Samantha said. “My parents might not appreciate you stealing the spotlight away from my dad at his retirement party.”

“You’re no fun,” I said, giving him a pouty lipped disappointed face.

I walked over to the closet and picked out a simple sundress and pulled it over my head.

“Your hair does look good though,” Sam said.

I looked in the mirror again and grinned. My new pink hair streak had come out perfectly. It stood out against the rest of my dark hair and gave me a nice splash of color. The week before, I had shaved the left side of my head close so I looked pretty badass.

“I guess I should start a punk band now, right?” I joked.

“Come on, we gotta go!” Sam chided me.

I had taken a lot longer in the shower than I had expected. But I wanted to look good for today.

It was my second time meeting Sam’s older brother, Mike. He was four years older than us and she knew I had a schoolgirl crush on him from seeing his Facebook photos that would pop up in my feed when she liked them.

I had not so subtly asked if he was going to be there and she assured me he was. Our plan was to hang out at her parents’ retirement party and then meet up with some of Sam’s high school friends and go downtown for some drinks.

We spent the two hour drive to her parents’ house talking about all sorts of random things. If you’ve ever been on a long drive, you know how random things will come up. At some point we started talking about her latest crush. I still remember that it was a girl in her art class who had a massive Afro and super dark skin. She showed me a photo and I remember thinking she was pretty damn gorgeous.

She asked if I was into anyone. I was single and had been for a few months. She let me stammer and sputter for a minute, then she laughed.

“I know you’re into my brother,” she said. “It’s cool. He’s a good guy.”

“Really?” I asked. “I don’t know him that well, just from meeting him at Thanksgiving. Does he even remember me?”

“Well…” She intentionally drew out the pause, just to torture me. “Mike did ask if I was bringing you when my mom said we could both bring a friend.”

“Really?!” I repeated, with much more enthusiasm this time.

“I believe he referred to you as my ‘hot friend from Thanksgiving’,” she joked.

I could feel my face turning red.

Sam teased me for the rest of the ride. When we pulled up to her parents’ massive house, the driveway and street out front were packed with cars.

“I didn’t realize your dad was so popular!” I said.

“He’s one of those ‘respected businessmen in the community’ that you always read about,” Sam said.

When we walked through the front door, Sam’s parents gave her a big hug and then grabbed me too. They had always liked me and made me feel welcome in their home the few times I had been there.

Her mom pointed through the house onto the back porch, “Your brother got here a while ago. He and Will are out back.” Before Sam could respond, her parents were whisked away by other partygoers for what was, I’m sure, a very important conversation.

Sam, being the good friend that she was, lead the way to the backyard and through the crowd to the guest house out back.

“Mike always hangs out back here at these types of things,” she said as she opened the door to the guest house.

Sure enough, Mike was sitting on the couch with a beer in his hand. He turned his head at the sound of the door opening.

“Hey, sis!” he exclaimed when he saw Sam. He stood up and walked around the couch to give her a hug.

Mike wasn’t much taller than me, but he had a pretty nice body. He had the same curly, dark brown hair that Sam had. The beginnings of a six pack were visible through the tight t-shirt he was wearing. His eyes were a piercing blue and had a strong jawline that was covered by a few days worth of stubble. I could feel my heart flutter as I looked at him.

After they pulled apart, his eyes moved to me. “Hey…Andrea, right?” he asked.

Mike turned his head and shouted, “Hey, Will, get out here!”

A second later, Will came out of one of the other rooms. He was tall and lanky but with broad shoulders. He had a full black beard with a short, cropped haircut.

“Sorry, I was just looking through your DVDs,” Will offered in explanation.

He noticed us standing there and walked over. “Hey, Sam. Good to see you again!” He gave her a light kiss on the cheek.

“This is my sister’s friend Andrea,” Mike said.

“Nice to meet you,” Will said, offering me a hand. I took it. His grip was firm.

“So, did you already make the rounds with mom and dads’ friends? Will and I already did.” Mike asked. He motioned to a discarded suit jacket on the back of the couch.

“Not yet,” Sam said. “I figured I would stash Andrea here first and then go do my part.” She looked at me and asked, “I’m assuming you don’t want to walk around and smile at my mom’s friends with me?”

“Not if I don’t have to,” I said.

“I’ll be back soon then,” Sam said. She turned on her heels and let out a half sarcastic, half serious sigh before walking out of the door to the guesthouse.

I turned back to Mike and Will. There was a brief awkward pause before I turned to Will and asked, “So, how do you two know each other?”

“I grew up down the street and we’ve been friends as long as I can remember. We both went to the same college. I moved back here after graduation, so we hang out whenever Mike comes back to town,” he explained.

“It must be nice to go to school with your best friend,” I said. “When I moved to go to college, I didn’t know anyone. It’s taken me three years just to get new friends.”

“That’s why you have to keep the good ones,” Mike said, gently elbowing Will in the side.

The three of us made small talk and hung out for a while. Mike and Will seemed like genuinely nice guys, so the conversation flowed easily. I could feel myself relaxing as the three of us talked.

About 20 minutes later, Sam walked back in, looking somewhat annoyed.

“What’s wrong?” I asked.

“My stupid friends ditched out on plans tonight,” she said.

“It’s cool, we can still go downtown together,” I offered.

“I know…but they’re always doing this,” she grumbled.

“Will and I can keep you guys company if you want,” Mike said. “We didn’t have anything special planned tonight.”

“Why don’t we go to my place?” Will said. “I’ve got plenty of beer and it’s way cheaper than a bar.”

“That’d be great,” I said before Sam could disagree. The idea of spending a night with the guy I had been crushing on from afar sounded pretty good to me.

“Alright. Let’s get out of here then,” Sam said.

We headed out, telling Sam and Mikes’ mom that we would be back later.

After piling into Sam’s car and driving across town, the four of us made our way up the stairs to Will’s second floor apartment. Once we reached the end of the hallway, Will unlocked his front door and we filed into his apartment.

It was a nice, well decorated place. Definitely more “adult” looking than the places my friends or I had at the time.

Mike, Sam and I sat down on the couch while Will went into the kitchen to get us some beers.

We spent the rest of the evening drinking and talking. There were definitely strong flirtatious vibes between Mike and I, but I couldn’t help noticing that my eyes were drawn again and again to Will.

Mike was more my type physically but Will’s full, bushy beard kept popping into my mind. Every time he smiled, I felt a small tingle. I could tell from the looks Will was giving me that the feeling was mutual.

But Mike and I kept flirting as the night wore on and I could feel the tension growing between the three of us.

After a few hours of drinking, it was almost midnight.

“I’m ready to go home, I think,” Sam said.

“You sure?” I asked. I didn’t want my fun evening of flirting with Mike to end.

“You guys can keep going if you want. I don’t mind,” she said. “Just get a cab back to my parents’ place.”

“I’d offer to let you crash here but there’s no room with Mike crashing on the couch,” Will said.

“Andrea can borrow my key to get into the house,” Mike offered.

“Are you sure you don’t mind?” I asked Sam. I didn’t want her to think I was abandoning her or anything. She just nodded and headed toward the door.

“See ya later!” she shouted back to us as she left.

I noticed a coffee pot on the kitchen counter and said, “How about I make us all some coffee to sober up?”

“I think that’s probably a good idea,” Mike said as he and Will sat down on the couch.

After rummaging through some cabinets, I found the coffee grounds and mugs.

As I made the coffee, my phone buzzed. It was a message from Sam. It read, *Don’t worry about me. You just have fun tonight. I saw you and my brother flirting ;)*

Once I finished making us all coffee, I crossed the living room and handed Mike and Will their cups before joining them on the couch. We all sat, drinking our coffee in silence for a few minutes.

I could feel the tension in the air between Mike and I. We had been going back and forth all night. But it was also obvious that Will was interested. I didn’t want to disappoint either of them, since they both seemed like nice guys.

As the silence continued, Will got up and disappeared into his bedroom. I heard the sink turn on in the bathroom.

It was just Mike and I alone now. I was still conflicted. He was cute, smart and funny. The perfect trifecta. But did that matter? I wasn’t expecting a long term relationship out of this, just a fun night.

As those thoughts raced through my mind, Mike moved across the couch so that we were sitting right next to one another. His hand gently reached out and started rubbing my leg below my skirt line.

His hand touching my skin sent a static shock through my body and I jumped a little bit.

“Sorry,” he said before leaning in to give me a kiss.

It started as a sweet peck, but I reached up and grabbed him, pulling him into a deeper, more passionate kiss. His tongue slid into my mouth and mine into his. He knew what he was doing and it showed. The next thing I know, I was on my back. His hand slid behind my head and held my head up as we kept our lips locked together. There was a confidence to his movements that I found exhilarating.

“I’ve been waiting all night to do that,” Mike said. His hand slowly moved under my skirt, toward my crotch. I could feel the tingling growing between my legs as he moved close and closer.

“Am I interrupting?” Will’s sarcastic voice came from the doorway to the bedroom.

Mike snapped his hand away. Then he looked at me to answer.

I looked between the two of them, trying to figure out what to say. My brain was screaming at me to say “Yes!” and keep fooling around with Mike, but I knew that was a jerk move.

“Kind of…” I said sheepishly, looking at Mike.

I looked back to Will as he stood in the doorway. His head was almost at the top of the door frame. He had an embarrassed and disappointed look on his face. I felt the part of my brain that wanted sex flair up again. I had an instant flash of how hot that beard would feel against my skin. Then my brain hit me with the knockout blow…*How good would that beard feel against my thighs as he ate me out?*, I thought to myself. I shuddered in pleasure at the thought.

My sex drive was drawing me closer and closer to the solution. But my brain wasn’t quite ready to hear it yet.

“You okay?” Mike asked.

Finally, my brain caught up to my body and I slid out from under Mike, sitting next to him on the couch.

I gently patted the seat next to me. Will didn’t move from the doorway. Had I miscalculated? Were they both going to shoot me down now? After a few seconds, he shook his head. Apparently I wasn’t the only one who’s brain needed to play catch up.

Will walked over and sat next to me.

I was sitting in the middle of two gorgeous guys. I looked back and forth between them, almost in a daze. I couldn’t believe I was doing it. I had thought about it before, but never imagined actually being with two guys.

“Are you two…” I trailed off.

“Willing to share?” Mike asked.

I nodded.

Will nodded.

Mike nodded.

“Okay then…” I said.

I leaned over and started kissing Will. His tongue slid into my mouth and we started making out. He didn’t have the confidence in his movement that Mike did, but I think we were all entering new territory so I couldn’t blame him.

After a minute or two, I reached back and guided Mike’s hand to my leg. He slowly started rubbing it again, making his way up between my thighs. I readjusted slightly, spreading my legs to give him better access.

Then I felt Will’s hand on my other leg. His grip was much more firm as his hand slowly massaged my thigh.

I broke away from our kiss and fell back on the couch. Mike started kissing my neck and I felt shivers of pleasure shoot through my body. All of the touching was completely overwhelming my senses. Normally I’d welcome something like that, but my slight buzz from earlier just made me dizzy.

I pushed their hands away, gently closing my legs and slowly stood up in front of them.

“Just give me a minute,” I said. My legs were like jello and my brain was running a mile a minute from the sensory overload. “I need a glass of water.”

Will got up and brought me a bottle of water from the fridge. I chugged the whole thing down and water dripped down my chin, onto my dress.

“Oh no, I’ve spilled on my dress!” I said in a mocking, high pitch voice.

Mike and Will seemed to miss the sarcasm, as both of them were staring at me expectantly.

“Maybe I should take it off?” I asked, leading them on.

They both nodded enthusiastically, still not getting it. *Oh well*, I thought as I pulled my dress up slowly, revealing my cream colored underwear.

I lifted my dress over my head and tossed it to the floor, standing in front of them in just my panties.

I could feel both of their eyes scanning me up and down like they were a pair of T-800s. My cheeks burned with excitement and nervousness. I could feel myself getting more and more turned on as I thought about the fact that *two(!)* guys were staring at my topless body.

“Wow,” was all Mike could manage.

“Your breasts are amazing,” Will said through a sheepish grin.

“Really?” I asked as I walked over to him. I sat down on his lap, pulling his hand to my breasts. His hands gently played with my nipples as I leaned back and kissed him. He definitely knew what he was doing.

I broke away and stood up again, motioning toward the bedroom. They both stood up and I got a good look at how excited they were. I could tell I was in for a treat.

I slowly turned around and marched toward the bedroom, both Mike and Will in tow. I could tell they were staring at my ass as I sat down on the edge of the bed.

They started to sit down on either side of me but I stopped them.

“Not yet. I’m down to my underwear and you’re both fully clothed,” I said. This time they got the hint.

Mike quickly pulled his shirt up over his head and tossed it aside. I smiled as I took in his muscular chest. At the top of his pants were the beginnings of a nice v shape that I was extremely eager to explore.

Will took his time removing his shirt. Slowly lifting it up over his head. I knew he was teasing me because he kept his eyes locked on me as he did it.

After he finished pulling his shirt off, he tossed it at me. I batted it away and got my first view of his body. He didn’t have a super muscular stomach like Mike, but he had a pretty good body. His chest was covered in sexy dark hair that matched his beard and his flat stomach had a gorgeous treasure trail leading down to his pants.

Will flashed a smile at me, his white teeth contrasted with his dark beard and I said, “I can’t wait to feel that beard against my thighs while you eat me out.”

“The feeling’s mutual,” he laughed.

Mike slid his pants off, revealing a pair of boxers that were already being stretched by his hard cock. He kicked his pants away and I reached out my hand for his, intending to pull him closer. He stepped forward and his fabric covered cock pressed against my hand.

“Someone’s ready,” I said, gently rubbing his crotch.

I looked at Will, who had already taken his pants off. He was wearing a pair of tight underwear that made his bulge look amazing.

“Why don’t we all just take our underwear off?” I suggested.

They both nodded. We all slid our underwear down, everyone admiring one another at the same time. I smiled and grabbed Mike’s cock once his underwear was off. His penis was long and uncircumcised. His pubic hair was trimmed and neat, which is something most guys don’t think about but is a major turn on for me.

I gently stroked Mike’s cock as I turned to Will. His cock was circumcised, just as long as Mike’s but much thicker. His hair was trimmed too, but he had also taken the time to trim his whole undercarriage. I reached out a hand and started stroking his cock too.

Slowly, Mike climbed up onto the bed and leaned me back. He stood over me, his cock hovering over my face. I started gently licking the underside of his cock up and down and I could see him shudder with pleasure.

I felt Will’s strong hands spreading my legs apart and then I felt his hot breath as his beard started scratching against my thighs. His tongue gently licked my pubic mound as he slowly moved his tongue around my pussy. I let out a long, loud moan as his tongue slid into me. I wrapped my legs around his body. The feeling of his tongue inside me while his beard rubbed against my legs was even better than I imagined.

I lay there moaning for a few minutes. I managed to regain my composure enough to start gently licking up and down Mike’s cock again. He slowly pushed me to his balls and I started playing with them.

I had never given a guy a blowjob in that position before and it was super hot looking up at him. He looked so good towering above me.

Mike guided me back to the tip of his cock and I started sucking on it. I worked as much as I could into my mouth from beneath him. He moaned as I gave him a sloppy blowjob.

Will’s tongue was still working my pussy and sending electric shockwaves through my body. He pushed my legs off of him and brought his hands up to my crotch. His fingers started gently playing with my clitoris and I couldn’t help but squirm. I would have let out a scream of pleasure if my mouth wasn’t so full.

Will’s fingers and tongue were all over my lower body as Mike reached down and started playing with my breasts. He gently pinched my nipples and swirled his fingers around my areola.

Even through a mouthful of cock, I started groaning with pleasure. I felt the building wave of an orgasm from all of the stimulation. Having two guys to pleasure me wasn’t just twice the pleasure. It was so much better.

My brain was reaching overdrive again when it hit me.

“Oh fuck! Holy shit! Don’t stop!” I couldn’t help but cry out through a mouthful of cock.

I started bucking under the two of them. Grunting and moaning as they both played with my body. Despite my best efforts, Mike’s cock slid out of my mouth and I started screaming in pleasure.

I kept bucking beneath them as they both backed off, letting me ride out my orgasm. Will’s head slowly came up from between my legs. I could see my juices all over his beard and it just made me squirm in pleasure even more.

Once I managed to come back down from my orgasm high, Mike turned to Will and said, “Damn. Good job man.”

“I heartily second that sentiment,” I panted as I caught my breath.

They were both nice and gave me a few more minutes to get myself together before I slid off the bed and onto my knees. They immediately understood and moved to the edge of the bed.

I moved in front of Will and started stroking his cock. He was already pretty big, but I could tell he wasn’t completely hard yet. I bent down and started gently kissing my way down his treasure trail and began sucking his cock. It immediately started growing in my mouth.

There’s nothing quite like the feeling of a guy getting hard as you suck his cock. It’s just so much fun knowing that you’re the one that’s getting him so excited.

After about a minute, I came up for air and admired his fully erect cock. It wasn’t the longest cock I’d ever seen, but it was at least 7 inches and very thick. I could barely wrap my hand all the way around it.

It was a bit of work, but I managed to take most of his cock into my mouth as he put his hand under my chin, guiding me up and down on his cock.

I glanced over and saw Mike gently stroking his cock as I sucked his friend off and I decided it was his turn for a proper blowjob, but first I wanted to give Will a nice little surprise.

I came up from between Will’s legs and gave him a passionate kiss. Then I bent back down, wrapped my lips around his cock and slid it as deep as I could down my throat. I could feel his pubic hair against my nose as I managed to get most of it down and hold it for a few seconds before falling backwards, gasping.

I looked up at Will from the floor. I don’t think I’ve ever had that much cock in my mouth since then.

“I don’t know if anyone’s managed to take the whole thing before,” he said. He was clearly impressed. I’m not sure if he was telling the truth but I felt a small amount of pride.

I reached out and gently stroked Will’s cock, slippery with my saliva, as I moved over to Mike and started to give him a second blowjob.

Seeing that I could take a cock that size without problem, Mike was a little more aggressive. His hand was grabbing my hair within seconds. He moved my head up and down, my mouth working his cock as he picked up speed. Soon, his hips were moving too. My hand fell away from Will’s cock.

Mike’s cock never left my mouth as he stood up, pushing me back into a sitting position as he kept picking up steam. By now he was practically facefucking me. I’d never had a guy be quite that aggressive before, but I’d had one who had come close.

I just let him use my mouth how he wanted and enjoyed the ride. I looked up at him, making eye contact as he thrust his cock in and out of my mouth. Compared to Will, it wasn’t as much work to take Mike’s cock. While he was still decently sized both in terms of length and girth, it wasn’t a strain like Will’s cock had been.

All of the sudden, Mike pulled his cock out of my mouth and slapped it across my cheek. He started furiously stroking his cock for a second or two and then I felt a massive, warm load of cum on my face. He grunted and another load hit my forehead. I felt his cock rubbing against my face, his cum getting everywhere. His hands fell to his side and his body relaxed.

I gently licked the head of his cock clean and smiled up at him. I wasn’t sure how much cum there was on my face, but I could tell it was a lot. I felt it slowly drip of my chin and land on my knee.

I slowly got up and went into the bathroom, turning on the light as I entered. I saw myself in the mirror, completely naked. My face was indeed covered in cum. There was a lot of it too. I couldn’t help admire how I looked. I’d never seen myself like that, still so dirty after sex. I could feel myself getting excited as I grabbed a towel and started to clean Mike’s cum off my face. There was something exhilarating about knowing that I had just gotten a facial from a guy I had a puppy dog crush on for months.

I finished wiping the cum off and rinsed my face in the sink. I walked back into the bedroom to find Mike laying sideways across the bed. He looked spent.

But Will’s cock was still rock hard and I could tell my night wasn’t even close to being over.

Source: reddit.com/r/gonewildstories/comments/c0bhsz/mfm_that_time_i_hooked_up_with_my_roommates