Don’t Worry Buddy, It’ll Happen

"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."