Don’t Worry Buddy, It’ll Happen

 

 This story is told from the perspective of three characters. These include Justin the boyfriend, Stacy the girlfriend, and Sam the best friend. There will be a heading with that character's name whenever the story changes to their perspective.*

Justin

I felt bad for my best friend, Sam. He's a really good dude, but unlike me, he didn't have a girlfriend. We had both just turned 21 over the last couple of weeks. After a failed attempt to help him meet some girls at the bars, we stopped back at the apartment I shared with my girlfriend, Stacy.

"You boys are back already? No luck I take it?" Stacy asked.

"Nah, couldn't keep any of the girls talking to us." Sam said.

"Awe, that sucks! Don't worry though, you are such a cute and nice guy. You will totally meet a girl soon." Stacy said, resting a reassuring hand on Sam's shoulder. Stacy was a sweet girl and an amazing girlfriend. She was 20 years old, funny, kind, and undeniably beautiful. Long brown hair, her eyes were a mix of blue and green, fair skin with a few faint freckles that you would never find if you weren't looking for them, and an amazing body. Slender, cute and perky breasts, toned tummy and legs, and a perfect smooth pussy. She waxed regularly, so she was always smooth. I had gotten to know her body well. Over the last few months, we had been going further and further. We hadn't had sex yet, but we had seen each other naked, a lot. A lot of handjobs and fingering and we even discussed trying oral soon. Stacy wanted to take things slow. She said she felt her last couple boyfriends used her for sex, so she wanted to take her time. I didn't mind, I've gone 21 years in life without having sex. I could handle waiting until Stacy was ready.

I was at a dead end helping my pal, though. I'm the guy with the experience and I should be able to help, but maybe he just lacks something I have.

Stacy

I felt bad for Sam. I could tell he was getting frustrated. This wasn't his first trip out with Justin to meet a girl. To be fair, even though Justin is a wonderful boyfriend, he might not be the best wingman. He's not exactly smooth. He likes to think he's a suave ladies' man, but if I were being entirely honest, if I had met Sam first, there is a very good chance I would be his girlfriend, not Justin's. Instead, here is this handsome and great guy, who mysteriously keeps striking out.

"Maybe we aren't going to the right places?" Justin suggested.

"Or," I interjected. "Maybe it's not the place, but the company?"

Justin and Sam glanced at me and then at each other.

"I'm serious!" I said. "Did you stop to think two dudes approaching women might intimidate them? If I go with it might seem more disarming. And I can give you a woman's perspective."

Sam shrugged. "I guess it's worth a try. Justin, you wouldn't mind?"

"Nah," Justin replied, shaking his head. "I know I have nothing to worry about." At least he's confident.

"Perfect! So Sam, coffee tomorrow? We can figure out all the deets?" I asked.

"Sounds great! I'll even buy!" Sam said.

Sam

I walked up to Nikki's Coffee, a small coffee shop literally on the same block as Justin and Stacy's apartment. Stacy already had a table when I entered. She immediately noticed me, a warm smile appeared on her face. "Hey Sam, over here!"

"Hope you haven't been waiting for long," I told Stacy.

"I just got here myself, no worries. I already got us each a cup, single sugar and a splash of almond milk right?"

"Uh, wow. Yeah, that's exactly how I take it. How in the world did you know that?" I asked.

"From last time Justin and I met you here. I overheard you ordering. It's just like I take mine, so it stuck with me. I suppose great minds think alike." Stacy replied with a wink.

I joined Stacy at the table, taken aback by her kindness. "Thank you, you're amazing. But I thought I was going to buy?"

"I guess you'll just need to beat me to it next time." Stacy said. "So, Sam, you're a good-looking guy. You're chill, sweet, funny. Why are you single?"

I laughed, "thanks for saying that. Guess it's confidence. Was always the quiet skinny kid until a year ago when I started working out. Now that I'm actually fit and more confident, I just don't know where to start. Justin insisted he was going to take me out and get me laid. Said he's become somewhat of an expert on women."

Stacy mid-sip from her coffee brought her hand to her mouth and stifled a laugh. Barely avoiding spitting out her coffee. She swallowed and laughed. "Oh my god, he's gotten such a big ego. I'm Justin's first girlfriend. I wouldn't say he's any kind of expert."

I shrugged, "to be fair, he attracted you. That's a big accomplishment, if you ask me."

Stacy blushed.

I continued, "if you don't mind me asking. How did Justin first attract you?"

"Well, we had a class together fall semester. I noticed Justin stealing glances at me first day of class. When we were leaving, he asked if he could walk with me. He was cute, so I figured why not? We chatted, he asked for my number and we texted. Funny thing is, Justin isn't the typical guy I go for. I had just broken up with my high school boyfriend a few weeks before. We had this long distance thing going on throughout freshman year, but it was just too much. So by the time Justin was talking to me, I was ready to move on. He was a good-looking guy who came by at exactly the right time."

"Wow."

"Oh, but he's a great boyfriend! For real, aside from being a bit to full of himself and clumsy with certain.. activities, I'm happy I am with him." Stacy took another sip of her coffee. "But, we are here to talk about you. What exactly is happening when you go out with Justin?"

"I don't know where it's going wrong. The times we meet girls, things seem to start out well. I've even had some approach me, but they seem to lose interest within a couple minutes of conversation." Sam said with a shrug.

"I feel like there is something you aren't telling me." Stacy narrowed her eyes. "It's Justin, isn't it? He's making things weird and scaring them off, right?"

"Um..."

"It's ok, you can be honest!" Stacy said, reaching across the table putting her hand on mine to reassure me.

"Yeah, I feel bad saying it, because I know he's trying to help."

Stacy gave my hand a squeeze and smiled. "Let's get a fresh start. We're going to go out and do it right! It's a crime a guy like you is single."

God, Stacy was great. Justin was my best friend, but all I could think about was how much I wish Stacy was mine.

Stacy pulled her hand back to take a sip of coffee. Then with a chuckle she looked at me and said, "oh and it's no surprise about Justin. He's used all of his cheesy moves on me. Speaking of Justin, he's probably back at the apartment now. Why don't we head back and hang out?"

Justin

The door of our apartment opened and in walked Sam and my girlfriend. I had to restrain myself not to laugh. Stacy didn't know what she was getting herself into.

"Well? What did you guys figure out?"

"We're going to go clubbing tomorrow!" Stacy answered.

"Clubbing?" I asked. This would be good. I tried clubbing before meeting Stacy. You never get a girl going clubbing.

"Yes! Now, if you boys don't mind, I need to look through my closet and figure out what I'll be wearing."

"How about we get a beer? Stacy is going to take forever to look through her clothes." I suggested to Sam. I figured their clubbing attempt would be hopeless and I should throw Sam a bone. Maybe I could give him some last-minute advice.

"Sounds good to me." Sam said.

Stacy gave me a kiss, then started towards our room. "Enjoy yourselves boys. Just don't be too long, ok? It's already getting late."

Sam and I headed down to our local bar and ordered a couple of beers.

"Hey man, I appreciate you being cool with Stacy helping me out." Sam said.

"No problem, but just in case things don't go how you are expecting, I thought I should give you some advice. After all, I'm getting action on the regular here. I know a thing or two." I said, throwing back my drink. "When you are talking to these girls, you gotta act like you aren't interested. Give one-word answers. Ask them to repeat themselves as if you had something more important to do than listen. Girls crave that kind of stuff. And this is the most important thing. Once they take the bait, you need to be assertive. Tell them what they want, you know, boss them around a little. Chicks absolutely love that."

"Yeah, I'll keep that in mind. Thanks Justin, I appreciate the advice." Sam said. And boy would he be finding out how valuable my advice was after striking out a time or two with Stacy helping him out.

Sam finished up his drink, and we both headed home.

Stacy

I had just finished picking out my clothes for the next day. I had stripped down to my panties and was going to get ready for bed when Justin came home.

"Hey babe, hope that's not your outfit for clubbing!" Justin teased.

"Well, so what if it is?" I teased right back at him.

"I suppose I'd need to teach you a lesson." Justin said, pulling me in and kissing me.

As usual, Justin's hands went straight to my breasts. I needed to get around to teaching him some finesse. He tended to grope my chest wildly. He pulled my panties down and got himself undressed. We made our way to our bed, still making out. It was hard to get into things when he played with my pussy. Each time I felt like there was some rhythm going, he'd break it by switching between fingering me and rubbing my clit. Finally, after subtly moving his hand back into position and telling him not to move it, I got Justin to focus on my clit. At last, I had small orgasm. I wondered what I should try next. So far we'd only done things with hands. I was feeling like we should move further. I considered maybe giving Justin a blowjob. Then, as I started rubbing his dick, I was reminded about one of the things holding me back. His penis size was, well, less than impressive. Easily the smallest of the guys I've been with. Eventually I'd find a way to work with it, but for now I decided to stick with the handjobs. It didn't take long anyway. After about a minute of playing with his dick, Justin was grunting and cumming.

"I'll be right back with a towel!" I said. By the time I came back, a naked Justin was passed out on his back, snoring. I wiped up the cum and lied down on the bed next to him.

I wasn't ready to sleep yet, honestly my orgasm wasn't even that great. I felt a little unfulfilled. At any rate, I was bored and texted Sam.

Me - Hey Sam, I'm excited about clubbing tomorrow! =)

Sam - Me too Stacy! Thank you so much for going with me tomorrow. :)

Me - Don't mention it! Just think, this time tomorrow you might be sharing your bed with a lucky lady! ;)

I glanced over at Justin. He was still sound asleep. His now soft penis had receded into just a small nub sticking out. Not exactly a sexy image. Suddenly I found myself jealous of the Sam's hypothetical woman I just dreamt up!

Sam - Haha, well I hope so. Would be nice just to meet someone nice who I have fun with, a girl like you.

Sam - Sorry... I shouldn't have said that!

Me - No, it's fine. Actually, it's really sweet. Thank you! I should really be getting to sleep though. Goodnight Sam!

Sam - Goodnight Stacy!

Sam

"Tonight is the big night Sammy!" I said to myself in the mirror. Maybe I was aiming high. I've never had luck before, but maybe it would be different hitting the town with Stacy. At any rate, giving myself a pep talk wouldn't hurt.

I did a double take of myself in the mirror. I had grown very proud of my body. It represented a lot of hard work. After years of being 'the skinny kid' I was now a changed man. It was still fun checking out my muscles. After a bit of flexing, I looked down. Just having finished 'man-scaping' I was wondering if I should have left some hair. But the clean look did seem to emphasize everything, although I probably didn't need to. I have no actual life experience to judge by, but my dick was like what I'd seen in porn and I heard those guys are bigger than normal. Hopefully, I'd have a chance to show it off.

I was genuinely excited for tonight, but as much as I tried to ignore my own feelings, my thoughts weren't exactly where they should be. Spending the night with Stacy honestly had me more excited than hunting for women. Starting to touch myself, I thought about her. I looked at my hard cock and imagined Stacy wrapping her hand around it. Imagining what she must look like naked and stroked myself, faster and faster until I came.

After cleaning up I checked my phone, realized the time. Shit! Supposed to pick Stacy up in 15 minutes. Quickly, I got dressed and headed over to her apartment.

Luckily, I wasn't too late. Justin answered the door when I arrived. "Hey Sam, Stacy is just finishing up."

"Ok great! You really don't mind that your girlfriend is taking me to the club to try to get me laid?" I asked, just to make sure there would be no hard feelings.

Justin laughed and shakes his head, "Man, don't worry about it. Stacy would never want to cheat on me, I have no worries whatsoever. If anything I hope Stacy doesn't get jealous."

"I don't understand. Why would she be jealous?" I asked.

"Because I'm going out to the bars. I'm undoubtedly getting hit on tonight." Justin replied.

Just then Stacy walked out and oh man. She was a knockout. I only hoped Stacy and Justin didn't notice me checking out her ass in her tight and very short skirt.

Stacy

"Hey Sam! You are ready to hunt with the expert?" I asked.

"Um, yeah." Sam answered. He seemed a little distracted. In fact I think I caught him checking me out. Which honestly, flattered the hell out of me.

"Awesome! Justin honey, you going to be ok?" I asked my boyfriend.

"Heck yeah, I'm going drinking with Dennis and Wade." Justin replied.

"Ok, don't drink too much!" I kissed Justin and headed out with Sam.

The club was pretty wild and so much fun! I hadn't been clubbing in a long time. "Hey Sam, you want to make some of these girls jealous?"

"How would we do that? And what would that do?" Sam asked me.

"Trust me, women can be as competitive as men. Let's dance. Just take my lead!" I told Sam, taking him by the hand and leading him to the dance floor.

Sam was an amazing dancer! Time was a blur. We just kept drinking and dancing all night. At one point I was dancing in front of Sam, grinding my ass on him. I could feel his hard erection against me. Maybe this was too much with my boyfriend's best friend, but I reminded myself it was just dancing. It wasn't a big deal.

At one point, Justin texted me. He had drank a little too much and was spending the night at his friend Wade's place. I didn't mind, I was having so much fun! Maybe too much.. I was supposed to be helping Sam meet some girls, instead I was keeping him to myself. I couldn't help it though.

Eventually Sam and I figured we had drank too much as well and he helped me back to my apartment. We laughed and joked as we stumbled along. Finally we arrived at my apartment. "Can you help me to my room Sam?" I asked, trying hard to keep my balance as I spoke.

"Sure thing." Sam said, although he was barely in shape to even walk straight himself.

We got to my room. I gave Sam a small peck on the lips and said, "thank you." Then leaned in and kissed more. I meant it only to be a friend's kiss. Maybe there is no such thing, but in my drunken state I thought there was. Now we were beyond a tiny peck, our tongues were wrestling for dominance. I broke the kiss and told Sam, "I think I need to go to bed. You can sleep here too." Stumbling toward the bed and slipped my panties down. I was so drunk it didn't register as a bad idea. I still had my skirt on, anyway. Next thing I knew, I was sound asleep.

Sam

I couldn't believe I just made out with Stacy. What's more, she had just pulled down her panties, then passed out on her bed. When she did, her skirt hiked up. There she was, over the edge of the bed, legs spread, skirt up, and pussy on full display.

I couldn't believe I was looking at the pussy of my best friend's girl. It was a pretty slit, clean. If someone could be a pussy model, it would be Stacy. Her pussy glistened in the small amount of light coming from the door. Stacy must have been wet. In addition, her lips spread just enough to see her clit. I felt myself getting hard and tempted to reach out and touch her, but I knew that would be a mistake. I picked her up and moved her fully onto her bed. Then I stripped down to my boxers, which is how I always sleep, and laid down next to Stacy. Maybe not the best idea to strip to my boxers and go to my best friend's bed with his girlfriend, but sometimes things seem like a better idea when you are drunk. Besides, we were only going to be sleeping.

Stacy

I woke up a bit groggy. Confused about where I was and what was going on. I looked around the room then at Sam sleeping next to me. Then I remembered I was so hammered I stumbled into my room and fell asleep. Sam must've had a similar experience. He was just in boxers, sleeping on his back. He was a handsome guy for sure. My gaze moved downwards from his face over his fit body. I wouldn't mind if Justin had some muscles like his friend. Then my eyes moved further, stopping at his boxers. Sam must've had morning wood. There was a large tent in his boxers.

My curiosity was overcoming me, and I leaned in for a closer look. Instinctively I reached out and lightly touched the soft boxer material that covered end of Sam's erect penis. Confirming he was still asleep, I glanced up at his face. Satisfied he was sound asleep, I gently reached for his waistband and pulled them down, freeing Sam's penis and allowing it to flop onto his tummy. Quickly, I look at his face again to ensure it didn't wake him. Looking now at Sam's exposed genitals. Wow, he was much bigger than my boyfriend. His balls, probably a little bigger, I guess? Honestly, I don't usually pay as much attention to that part. In fact, I had never taken the time like this to just take my time and closely look at a guy's genitals in detail like this. Gently, I touched them cradling Sam's scrotum. It was soft. He had also shaved clean, which I thought was nice. I just slowly massaged his testicles and continued taking in the sight. Sam's penis seemed to get even larger yet. Damn, he was so much bigger than my boyfriend. Delicately, I felt his hardness with my fingers and moved one hand between my legs. Was I not wearing any panties!? I had forgotten I was so wasted I didn't even care that Sam was in the room with me when I pulled them down. Had he had seen anything? I mean, I still had my skirt on, so I was probably still covered. Then I smiled at myself. It was rather silly to be concerned about Sam seeing my pussy as I was stealing a look, and a feel, of his penis.

I started to moan as one had rubbed my clit and the other gingerly explored Sam's privates. The sound of my moan seemed to wake him a little. Quickly, I pulled his boxers back up and lied back down.

Seconds later, Sam woke up, rolled to his side and looked at me. I slowly opened my eyes, pretending like I had just woken too.

"Good morning," Sam says.

"Good morning. Sorry I passed out so fast when we got back." I said.

"No, it's fine. I passed out right after you. I guess we overdid it on the booze."

We both giggled.

"Yeah, maybe next time we drink a little less."

"So you'll still be my wing-girl then? I didn't make an ass of myself when I was drunk?" Sam asked.

"Are you kidding? I had a great time! It was so much fun hanging out and dancing. Sorry we didn't find you a girl though."

"That's ok, I still had a lot of fun too. Hey, you want to grab some breakfast? I'm still feeling affects from that alcohol and I'm sure some eggs and coffee would help. I'll buy, what do you think?" Sam asked.

"That would be amazing! But, I'll need to change out of my clubbing clothes. This skirt is just a little too short for breakfast. My clean clothes are in drier which is in the bathroom, so I'll get dressed in there." I said, sitting up on the bed and stretching. As I did so, I positioned myself just right to give Sam a view of my pussy. I had gotten to see his penis, seemed only fair. He did his best to not make it obvious he was looking.

"S-sounds good. I'm just going to throw my clothes back on from last night." Sam said.

Sam

I think we both felt better after getting some food in our stomachs. Stacy and I had chatted throughout breakfast. I was relieved that she wasn't upset about our dirty dancing the night before or the kiss. We had gotten around to talking about relationships. Stacy had just acknowledged that her and Justin hadn't gotten very far yet.

"Believe me, I'd love to go further," Stacy confided in me. "Yes, I wanted to take things slowly at first, but now I wish he were more proactive. I could be, but it's not really a turn on for me to be pushing for it, you know? Having a guy being confident and going for it is a lot sexier."

"Justin has got to be crazy! I couldn't imagine being with you and not going for it." Then, looking a little embarrassed, Sam backtracked. "Sorry, I'm being creepy."

"No! It's ok, you aren't being creepy. Actually.. If I'm being completely honest, if I were single, I would be the one who wouldn't be able to keep my hands off of you!" I replied.

Sam blushed. How adorable. "Well, a guy can always dream." He added with a handsome smile.

"Tell you what, next time out we'll definitely find you a girl, so you don't need to dream about one." I reassured Sam.

"Thanks Stacy."

"Anytime!" I said with a wink. "Anyway, ready to get out of here? I want to get home and take a shower."

Sam nodded. "Yeah, me too. Plus, I want to put on some fresh clothes."

"Why don't you stop over later and hang out? I'm sure Justin will be home." I suggested.

Sam agreed. "Sounds fun."

Justin

As I entered our apartment I hoped Stacy wouldn't be angry I was back so late. I was so hung over I slept straight through lunch. When I walked through the door I saw her on the couch chatting with Sam.

"Babe! You are finally home!" Stacy jumped up and gave me a hug. "Sam came over to hang out with us."

"Yeah, sorry Justin. Thought you'd be here by now." Sam said.

I chuckled, "Oh yeah.. I got pretty drunk last night and overslept."

Stacy smiled, "Guess big bad Justin can't handle his alcohol?"

"Oh, like you think you can handle it any better?" I asked.

"Um, yeah!"

"This is from the pickup artist that was going to help Sam, but obviously struck out?" I teased my girlfriend.

"Excuse me? And why do you assume we struck out?" Stacy asked.

I shook my head and laughed. "Sam wouldn't be here now if you had helped him find a girl. Don't be embarrassed. Not everyone has my magnetism."

"Magnetism?" Stacy questioned.

My sweet naive girlfriend. "Yup, do you have any idea how much I got hit on last night?" I gave Stacy a wink. "Turns out you are pretty blessed to be dating such a stud."

"We'll show you, mister stud!" Stacy sassed back, sticking out her tongue. "What do you think Sam? Try again tonight?"

"I'm game. You sure you're ok with us hanging out again Justin?" Sam asked me.

I shrugged. "You're welcome to strike out again my friend. I'll understand when you come up empty-handed."

Ignoring my last comment, Stacy spoke to Sam. "Do you know Brittany and her friends? They are having a house party. We should go! There will be lots of girls there."

I just shook my head. My silly girlfriend never learns.

Stacy

As soon as Sam and I arrived at the party, I set out to introduce him to as many girls as possible. Turns out, I didn't need to. They came flocking to him. I have to admit to being a little jealous. I had so much fun with Sam the night before and now all these other girls had his attention. Still, I did my best to have a good time. I mingled, caught up with some friends, and gave Sam some space to flirt.

About 15 minutes on, I spotted Sam by the pool talking to a group of three girls. I approached, thinking I might help him narrow it down a little. Unfortunately, one girl took a fast step back as I approached and accidentally knocked me into the pool.

Before the shock could even set in, two powerful hands reached under my arms and plucked me from the pool. It was Sam!

"Are you ok?" Sam asked.

I was still reeling, but nodded my head. "I think so." Then I remembered my phone was in my pocket! I pulled it out and checked it. I sighed in relief. "Whew, my phone still works, but I'm soaked. And freezing!"

"Let's get you home and out of those wet clothes." Sam said.

I shook my head. "No, I don't want to ruin your night."

"It's fine." Sam said reassuringly. "There will be other nights. Come on, let's go."

Sam put an arm around me and walked me back to my apartment. On the way Justin texted me, judging by his drunken poorly written texts, it was clear that yet again he wouldn't be making it home that night. By the time Sam and I got to my apartment, I was freezing and ran right to the bathroom. I quickly stripped off all my clothes and wrapped myself in a towel before heading back out to Sam.

Sam

"It feels much better being out of those wet clothes. Thanks for walking me home. Sorry no girls, hanging out with me must be so boring!" Stacy said.

"Boring? No way! I've had a lot of fun with you. And it's not all for nothing. After all, I got to see-." Just then, I cut myself off. Without thinking, I almost let it slip I saw Stacy's pussy. However, it occurred to me, Stacy was so amazing. It was clear that I needed to tell her the truth. "I've got to admit something. I saw your pussy."

"Really? When did you see it?" Stacy asked.

"This morning briefly and last night. You passed out in a way that I could see everything. Sorry, I should've said something earlier." I answered.

"You don't need to be sorry. I have to admit something too. I saw your dick."

"How?" I asked in shock.

"Well.." Stacy looked down. "I woke up before you. I noticed your, um, bulge and my curiosity got to me. And I took a peek." She buried her face in her hands in embarrassment.

"It's ok, I guess we're even then." I said, managing a small chuckle.

Stacy looked up, smiling. "This might be a weird question, but what did you think of what you saw?"

"I mean, you are super hot, Stacy. And it was so perfect, I would've given anything in that moment to see the rest of you." I admitted.

Stacy smiled. "Really?"

I nodded.

Stacy stood up and let her towel drop. My jaw must've hit the floor. She walked closer, glanced down and bit her lip. "Mind if I see it again?"

My eyes examined Stacy's naked body. My god, Stacy's body was perfect. Without a second thought, I unfastened my jeans and slid them down, along with my boxers. Standing there, Stacy watched as I stroked my already stiffening cock.

Stacy stepped closer, then reached down and placed her hand on my cock. I couldn't believe this was happening. Her small hand gently stroked me. I looked into her eyes. I wasn't able to help myself, I kissed by best friend's girlfriend.

Moments later, reality catches up with me, and I break the kiss. "I'm sorry for kissing you." I tell Stacy.

"No, it's ok." Stacy replies. She kisses me back, then got down on her knees. Her eyes closed as he took the head of my cock into her mouth.

Stacy's warm mouth felt like heaven on my cock. Never in my life had I felt anything so amazing. She pulled mouth away and looked up at me. "I like your dick." Stacy said as she moved her hand on my shaft. "It's just so like, genuinely nice looking and big! Seriously, I just love it." She returned her mouth to my cock. The stimulation was almost overwhelming. Finally, I had the biggest orgasm of my life. Stacy tightly sealed her mouth around my cock and swallowed my cum as it shot into her throat. After I was done, Stacy released my cock and took a deep breath. "Wow, that was so much cum."

"I've never had one that amazing before." I replied. Invigorated and filled with passion, I lifted Stacy and dropped her down on her couch where I had just been sitting. "And I'd like to return the favor."

I knelt down and Stacy spread her legs. Her aroma drew me in and I started to lick. Stacy reached down and gently applied pressure to my head, guiding me to the best spot until she said. "That's it, right there. You're on my clit."

There I was with Stacy, my best friend Justin's girlfriend. Yet he never felt her warm mouth on his bare cock like I just did. Not only that, Justin didn't know how Stacy's pussy tasted, but now I did.

Stacy's breathing grew heavy, her hands grabbed hold of my hair and her body tightened, "you are amazing, oh my god!"

Stacy's grip relaxed. After catching her breath, she said, "I can't believe that was your first time going down on a girl. You were amazing! Either that or it's just been so long since I had one that good."

I sat down next to Stacy and what we had just done began to sink in. "What about Justin? He's my best friend and your boyfriend. I can't believe we did that."

"I know, but I'm not sure that this was such a bad thing. I don't know about you, but I needed that release. And don't you think Justin had it coming somewhat with how cocky and smug he was? He was being a jerk, and now, you've gotten further with his girlfriend that he has."

Stacy and I laughed.

"Oh my god, I'm going to hell."

"Don't feel too bad." Stacy said. "Just think of it as practice. It's not cheating if I was just helping a friend, right?"

"Um," I raised an eyebrow. "I'm not sure Justin would feel the same way. We'll probably want to keep this between us."

Stacy nodded. "Agreed." Then she looked down at my now flaccid cock. She took hold of it. "You know you have a really big dick right?"

"I never really knew for sure." I answered. "Sort of suspected. You really think it's big?"

Stacy let out a small laugh. Still holding my cock she manipulated it and said. "Um, yeah, for sure. Like right now I can squeeze it and tell you are completely soft. And even with you totally soft, Justin would be lucky if he could even get close to this big." She traced a finger along the edge of my cock head where it met the shaft. "He'd maybe only come up to here on you when he's completely hard." Giving my cock a squeeze she continued. "When you finally fuck a girl she's going to be very lucky."

I smiled, "thank you Stacy. This was fun, but like you said, we probably should pretend nothing happened. And it wouldn't hurt to be extra nice to Justin." We both laughed.

"Agreed," Kate said. "Why don't you sleep here tonight. Justin won't be back until tomorrow anyway."

Justin

In a repeat of the day before I came back late, but I was excited to see how much my friend and girlfriend bombed.

"So superstars, where is Sam's new girlfriend?" I asked sarcastically as I walked through the door.

Stacy shrugged. "Maybe you were right babe," she said.

"Oh, really?" I asked, faking shock.

"Yeah dude. I don't know what it is that you've got, but I definitely don't have it." Sam acknowledged.

I smiled. It was nice to hear validation that when it came to attracting women, I was simply just better.

"I tried to tell the two of you. When it comes to the three of us, I am the only one who really knows anything about women." I pulled a beer from the fridge and opened it. "It's not your fault, though." I added as I sat down and took a sip. "Stacy, your experience is with boys, not women. Now of course I say boys, because before me those were like high school relationships. And Sam, buddy, don't feel bad about not knowing what to do. You haven't had the experience. I've touched a pussy. You don't even know what one feels like yet, which means you don't even know what you are missing."

Stacy laughed incredulously. "Babe, I don't think we are quite that hopeless."

"Please. Stacy, you are awesome, but let's be real. If you were a guy there would be no way you'd get a girl." I took another sip of beer. "Just face it, I'm the only one here that could get a chick."

"The only one, really?" Stacy asked.

"You are so cute when you get angry." I commented, winking for emphasis. "Relax, just admit I'm the only one here that can get a chick."

"We will so prove you wrong! Sam, meet me here tomorrow. Justin will be at his late class and we can get a game plan."

Sam agreed. I simply laughed at them and shook my head. This just kept getting more and more entertaining.

Stacy

I heard a knock at my apartment door. I knew it was Sam. After Justin had annoyed me so much the day before, I was looking forward to venting with Sam. I let him in and greeted him with a big hug. "Hi Sam!"

"Hey Stacy, how are you today?" Sam asked.

"Not bad, but still super annoyed from yesterday."

"Yeah, no kidding," agreed Sam. "I figured admitting defeat to him would satisfy his ego a little and he'd chill out."

"But instead he was a huge ass!" I replied.

"I just don't get how he thinks he's this gift to women and that literally he's the only one that could possibly get a woman." Sam added.

"Oh I know." I said, rolling my eyes. Then I thought crossed my mind, and I gave Sam a sly smile. "Because of course, only Justin can get a woman. Or for example get chick to make out with him, right?" I say sarcastically before putting my hands on either side of Sam's face and pulling him in for a deep kiss.

Rolling with the sarcasm, Sam pulls away. "Oh of course. And only Justin could possibly get a girl's top off." He pulled my t-shirt up over my head. Then, while kissing me, Sam unhooked my bra and let it drop from my shoulders.

I was about to respond when Sam moved his mouth down to my nipple, causing me to moan. I reached down and started undoing his belt. Once I had his belt off, I gave his pants and boxers a tug, allowing them to fall to the floor. "And only Justin could get a girl to play with his dick!" As I started stroking Sam's thick and hard cock.

Sam responded by pulling down my pants and panties, then took off his own shirt. I was now naked with my boyfriend's friend, kissing him and playing with his big dick. Sam now pushed me back and had me sit down. He gently spread my legs and I threw back my head as he started licking my pussy.

"I guess Justin can't do everyth- mmm," I was in too much pleasure to finish my thought. "Sam, that is so good. You are so good. Oh my god, yes!" I did my best to hold my legs open while trembling from an orgasm. I was squirting and I could feel it as I gushed on Sam's chin.

I regained my composure and sat up, taking Sam's big dick in my mouth. Once I was satisfied that Sam was totally rock hard I leaned back, pulling Sam between my legs. I looked at Sam seductively. "That's a lot only Justin can do." I reached down grabbing Sam's cock and pulled it in so the head parted my pussy lips. The large head of his cock was right at the entrance to my vagina. "Too bad Justin can't fuck his own girlfriend."

Sam smiled at me, then slowly pushed his hips forward. He was so large my body tensed at the intrusion. He paused with just the head inside me, then once my body relaxed, he pressed forward a little more. Sam proceeded to slowly thrust, only pushing about half his length into me each time.

"Sam, you are so big. This feels so good." This seemed to encourage Sam and he pushed in a little further, but I wanted to feel all of him. "I'm ready. Give me the rest of your cock, please."

Sam now pulled almost entirely out, now just the tip of his cock was inside of me. Then, in a single smooth motion, Sam sank his cock deeply into my pussy. Damn, his cock felt so good. "Guess we've found another thing that Justin can't do. You are so much bigger. He'll never ever be able to go that deep."

Sam smiled, then started fucking me fast and hard.

At first there was a mixture of pleasure and pain, but it didn't take long for the pain the fade away. Soon it was pure pleasure. "Your cock so so amazing. Fuck!" I started cumming, I had never gotten off so fast during sex. Sam was just that good.

Here I was, my boyfriend's best friend inside of me, filling me up and stretching me out. Justin hadn't even done oral with me yet, and Sam was fucking me with his bare cock. I wasn't even aware of how much time was passing anymore. I had several more orgasms. The hypnotic spell was only broken when I could sense Sam getting close to cumming. His cock got even harder. It felt like steel. His pace picked up and I wrapped my legs around him. He pushed himself in deep and my legs squeezed around him pulling him in even tighter. I felt his cock throb and pulsate while his warm cum hit my cervix.

My legs were still wrapped around Sam, I didn't want him pulling out yet. I looked up at him and we both smiled. I wasn't sure what to say to my boyfriend's friend who just so happened to have fucked me. "So um, should we call this dating practice?"

We both laughed. Sam nodded, "I'm always available for lessons."

"In that case, I think we need to schedule some study sessions. Maybe each week when Justin has his late class? In addition, of course, to regular outings as your wing girl." I suggested. Sam's cock was still inside of me. Even though I felt it slowly become flaccid, it was still big enough that I still felt full.

Sam nodded, "I promise to study very hard every time."

We both giggled. I released my legs from around Sam and told him. "Just pull out slowly. You put a lot of cum in me."

Sam

I just pulled my cock out of Stacy's pussy when we heard the door. It was Justin! We quickly pulled on our clothes. I had just seen my cum starting to drip from Stacy's pussy when she pulled her panties up. For the moment my seed wouldn't be going anywhere. We finished getting dressed just in time.

Justin strutted in, still smug. "Hey losers, talking about striking out again?" He chuckled to himself. "Before anyone gets their panties in a twist, I'm just joking by the way."

Stacy simply smiled and said. "Welcome home babe." She gave him a big kiss, with tongue. Little did Justin know that my cock had been in that mouth tonight. "I need you, in the bedroom, right now." Stacy said suggestively.

Justin winks at me then says, "hey buddy, can you wait a minute? I want to tell you something when I come back out." And with that, Stacy pulled Justin into their bedroom. I didn't know what she planned, but I loved the idea that Justin had no clue that his girlfriend's pussy was filled with my cum.

I didn't have to wait long. Only a few minutes later they both come back out. Justin had a cocky aura about him and I got a wink from Stacy.

Justin

I took Sam aside. Despite my teasing, I felt like I had to reassure the little guy. I knew he looked up to me, so I wanted to bestow some of my wisdom on him. "Hey buddy, I just wanted to tell you something. You don't need to worry. Things will work out for you, eventually." I told him. "I have the experience to know these things. One day you'll be able to do things with a girl like I do with Stacy. And guess what? You would never guess it, but she wants more from me all the time. For example, just now, she literally begged me to eat her pussy. First time I had ever done it, she said I was a pro. She'll probably let me do it every night now when I get back from my late class. And Stacy was so turned for me, you wouldn't believe how wet her pussy was." I noticed a smile on Sam's face, almost like a fellow man's admiration for what I had achieved. "Pussy tastes amazing, by the way. I could enjoy that taste all day long. You'll love it when you finally get to try, believe me."

 

"I can imagine."

I put a reassuring hand on Sam's should and told him. "My point is, it's ok you don't have a lot of sexual experience like me. It'll happen buddy."

"Thanks Justin, that means a lot."

"No problem, goodnight buddy."

Sam left and I returned to our room. Stacy and I crawled into bed and she snuggled up next to me.

"I think I'll need to spend a lot more time with Sam as his wing girl. As you pointed out we still have a lot of work to do." Stacy laughed, a cute little giggle.

I laughed, "you can spend all the time with Sam you feel is necessary." Little did Stacy or Sam know that I was letting them play their silly game for my benefit. See, I figured out that Stacy helping Sam strike out time and time again got her super horny. I can't say exactly what it was about failure that got Stacy so turned on by the time she came home to me. All I knew was that while poor Sam would be wallowing at home, not even having been to first base with a girl, I would be eating my girlfriend's wet pussy. The joke was on them!